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Molecular Orientation and Emission

Characteristics of Ir Complexes and
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Springer Theses
Recognizing Outstanding Ph.D. Research

Chang-Ki Moon

Molecular Orientation
and Emission
Characteristics of
Ir Complexes and
Exciplex in Organic
Thin Films
Springer Theses

Recognizing Outstanding Ph.D. Research

Aims and Scope

The series “Springer Theses” brings together a selection of the very best Ph.D.
theses from around the world and across the physical sciences. Nominated and
endorsed by two recognized specialists, each published volume has been selected
for its scientific excellence and the high impact of its contents for the pertinent field
of research. For greater accessibility to non-specialists, the published versions
include an extended introduction, as well as a foreword by the student’s supervisor
explaining the special relevance of the work for the field. As a whole, the series will
provide a valuable resource both for newcomers to the research fields described,
and for other scientists seeking detailed background information on special
questions. Finally, it provides an accredited documentation of the valuable
contributions made by today’s younger generation of scientists.

Theses are accepted into the series by invited nomination only

and must fulfill all of the following criteria
• They must be written in good English.
• The topic should fall within the confines of Chemistry, Physics, Earth Sciences,
Engineering and related interdisciplinary fields such as Materials, Nanoscience,
Chemical Engineering, Complex Systems and Biophysics.
• The work reported in the thesis must represent a significant scientific advance.
• If the thesis includes previously published material, permission to reproduce this
must be gained from the respective copyright holder.
• They must have been examined and passed during the 12 months prior to
nomination.
• Each thesis should include a foreword by the supervisor outlining the signifi-
cance of its content.
• The theses should have a clearly defined structure including an introduction
accessible to scientists not expert in that particular field.

More information about this series at http://www.springer.com/series/8790

Chang-Ki Moon

Molecular Orientation
and Emission Characteristics
of Ir Complexes and Exciplex
in Organic Thin Films
Doctoral Thesis accepted by
Seoul National University, Seoul, Korea
(Republic of)

123
Author Supervisor
Dr. Chang-Ki Moon Prof. Jang-Joo Kim
Department of Materials Science Department of Materials Science
and Engineering, The Graduate School and Engineering
Seoul National University Seoul National University
Seoul, Korea (Republic of) Seoul, Korea (Republic of)

ISSN 2190-5053 ISSN 2190-5061 (electronic)

Springer Theses
ISBN 978-981-13-6054-1 ISBN 978-981-13-6055-8 (eBook)
https://doi.org/10.1007/978-981-13-6055-8

Library of Congress Control Number: 2018967419

© Springer Nature Singapore Pte Ltd. 2019

This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part
of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations,
recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission
or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar
methodology now known or hereafter developed.
The use of general descriptive names, registered names, trademarks, service marks, etc. in this
publication does not imply, even in the absence of a specific statement, that such names are exempt from
the relevant protective laws and regulations and therefore free for general use.
The publisher, the authors and the editors are safe to assume that the advice and information in this
book are believed to be true and accurate at the date of publication. Neither the publisher nor the
authors or the editors give a warranty, express or implied, with respect to the material contained herein or
for any errors or omissions that may have been made. The publisher remains neutral with regard to
jurisdictional claims in published maps and institutional affiliations.

This Springer imprint is published by the registered company Springer Nature Singapore Pte Ltd.
The registered company address is: 152 Beach Road, #21-01/04 Gateway East, Singapore 189721,
Singapore
Supervisor’s Foreword

Molecular orientation and electronic structure of organic semiconductors are

important factors influencing the electrical and optical properties of the materials.
This thesis describes Dr. Moon’s fundamental work during his Ph.D. in the
Department of Materials Science and Engineering at Seoul National University to
understand the origin of the preferred orientation of doped molecules and electronic
structure of intermolecular charge transfer complex, which are important in organic
electronics. Simulations and calculations along with experiments provide clues to
the analysis of molecular orientation and film properties. Dr. Moon has pioneered
the analysis of the emission properties of solids according to the molecular orien-
tation using molecular dynamics simulations and quantum chemical calculations.
This thesis describes Dr. Moon’s works on the molecular orientation and resulting
film properties. Dr. Moon’s first research interest in this area was to develop the
optical simulation of luminescence from thin films and organic light-emitting
diodes (OLEDs). Birefringence resulted from molecular orientations made it diffi-
cult to analyze thin-film luminescence. He established an optical model of the
dipole radiation in an anisotropic medium and proved the model by experiments. It
turns out that the model describes the emission characteristics of OLEDs very well.
The same model was also utilized to analyze the emitting dipole orientation of
iridium complexes, the most important emitting dyes used for OLEDs, to get
accurate orientation of the emitting dipoles. It was known that many of iridium
complexes used in OLEDs, even though they have globular shape, have preferred
emitting dipole orientations as doped in organic amorphous layers, which is ben-
eficial for OLEDs efficiency, but the reason of the orientation was ambiguous in
those days. Dr. Moon simulated vacuum deposition process using molecular
dynamics to understand the origin of the orientation of iridium complexes doped in
organic layers and to predict the emitting dipole orientation. His experimental and
calculation results improved the understanding of the alignment and distribution of
iridium complexes and showed that intermolecular interactions between hosts and
dopant molecules play a pivotal role to induce preferred orientation of dopant
molecules during the vacuum process.

v
vi Supervisor’s Foreword

Dr. Moon combined the simulation method and orientation of emitting dipoles to
understand the electronic structure of exciplex in solid. Exciplexes in solid states
exhibit extraordinary characteristics including broad emission spectra, multi-
exponential photoluminescence (PL) decay curves, and spectral redshifts as time
delays in transient PL, whose origin was not fully understood at the time. Dr. Moon
presented experimental and theoretical evidences that all of the emission charac-
teristics of solid-state exciplexes originate from differences in their dimer configu-
rations, which have different charge transfer rates, emission energies, singlet–triplet
energy gaps, kinetic rate constants, and emitting dipole orientations. This conclusion
is based on experimental observations, quantum chemical calculations, and molec-
ular dynamics simulations. These results enabled us to develop a model of the
electronic structure of an exciplex in a solid state. This comprehensive model
accommodates all of the characteristics of the exciplex and can be used to further our
understanding of solid-state charge transfer complexes playing important roles in
OPVs and OLEDs.
This thesis covers the most advanced theories and analytical methods of the
emission characteristics of doped organic films and electronic structures of inter-
molecular charge transfer complexes in solid in organic thin films. It is recom-
mended for readers who desire to understand the orientation of molecules in organic
amorphous films, its effects on optical properties of thin films as well as the elec-
tronic structure of intermolecular charge transfer complexes, which play important
roles in organic electronics, especially in OLEDs and OPVs.

Seoul, Korea (Republic of) Prof. Jang-Joo Kim

November 2018
Abstract

Organic light-emitting diodes (OLEDs) have drawn great attention in lighting and
display technologies with the advantages of high color purity, large-area process-
ability, low cost, and flexibility. Development of the materials and the device
structures is still demanded because the power efficiency of OLEDs is low to
replace other lighting sources. The key importance of emitting materials for OLEDs
is utilizing the non-radiative triplet excitons as photons and the increase of the
outcoupling efficiency. The triplet excitons can be harvested as photons by
employing phosphorescent or delayed fluorescent emitters. Control of the molecular
orientation in organic thin films is one of the methods to enhance the outcoupling
efficiency of OLEDs. Horizontal alignment of the emitting dipole moment to the
substrate largely enhances the outcoupling efficiency of light in OLEDs.
The optical model of OLEDs interprets dipole radiation in a microcavity
structure. It predicts external quantum efficiency and electroluminescence spectrum
of OLEDs very precisely. In addition, the model has been recently applied to the
method of determining the emitting dipole orientation (EDO) of an emissive layer.
The preferred molecular orientations in organic thin films lead to optical birefrin-
gence so that the development of the optical model of OLEDs with consideration
of the birefringence is required.
Ir(III) complex is one of the phosphorescent dyes for highly efficient OLEDs
with high radiative quantum efficiency and various emission color spectrum. In
general, Ir complexes have octahedral structures with three cyclometalating
bidentate ligands and only small amount of them are doped in an organic host in the
emissive layer. Therefore, their molecular orientations have been regarded as iso-
tropic for a decade. However, the preferred horizontal orientation of the emitting
dipole moment was investigated from a heteroleptic Ir complex in 2011. Optical
simulation predicts over 46% of external quantum efficiency from the OLEDs using
the Ir complexes with the perfect horizontal alignment of the emitting dipole
moment. Now, the molecular orientation of Ir complex is an important topic of
OLEDs.

vii
viii Abstract

Exciplex is a charge transfer complex formed by charge transfer between dif-

ferent molecules at the exciplex state. Exciplex has a very low singlet–triplet energy
gap by spatial separation of the frontier orbitals, enabling delayed fluorescence with
electron exchange between singlet and triplet states at the room temperature.
Exciplex has been highlighted as an emitter of OLEDs because it also can harvest
the non-radiative triplet state as delayed fluorescence. Many kinds of exciplexes
have been reported with radiative quantum efficiency, but understanding the elec-
tronic structure and the emission mechanism of the exciplex is still insufficient. We
need more concentration on the dimer arrangements and the charge transfer process
in a solid-state blend to understand the emission mechanism of the exciplex.
This thesis analyzes three subjects: (1) modeling of dipole radiation from an
anisotropic microcavity, (2) the origin of molecular orientation in organic thin films,
and (3) electronic structure and emission process of exciplex in a solid state.
Chapter 1 introduces the molecular orientation in thin films, the optical mod-
eling, the iridium complexes, and the exciplex related to OLEDs.
Chapter 2 describes optical modeling of the luminescence from an oriented
emitting dipole moment in an anisotropic microcavity, and the model is expanded
for optical analysis of OLEDs. The dipole radiation in an anisotropic microcavity is
solved as functions of the dipole orientation and direction of the polarization using
the classical dipole theory. As a result, the optical model enables to analyze the
far-field radiation from an Ir complex doped in a birefringent layer. In addition, it
successfully analyzed the angular emission emission spectra and external quantum
efficiency of OLEDs employing the birefringent emissive layer.
Chapter 3 analyzes host effect on the orientation of the iridium complexes in
organic amorphous film and furthers the intermolecular interactions between the Ir
complexes and host molecules on organic surfaces during vacuum deposition via
quantum chemical calculation and molecular dynamics simulations. Most resear-
ches have tried to control the molecular orientation by a change of the molecular
structure of Ir complexes. However, this thesis investigates that the preferred ori-
entation of the emitting dipole moment is able to vary from horizontal, isotropic, to
rather vertical directions depending on host materials. The local attraction between
the host–aromatic ligand of the dopant on the surface induces the horizontal EDO.
Furthermore, molecular dynamics (MD) simulations were demonstrated to
simulate the vacuum deposition processes and observe the molecular configurations
with various host–dopant combinations. As a result, the emitting dipole orientation
is determined by the alignment of the aromatic ligands parallel to the substrate
rather than the alignment of aliphatic ligands. Therefore, the host–dopant aromatic–
aromatic interactions whose direction is parallel to the substrate is attributed to the
origin of the preferred molecular orientation of heteroleptic iridium complexes in
vacuum-deposited organic thin films. Energetic analysis indicated that the disper-
sion interaction is the major force for the orientation of iridium complexes, but the
local electrostatic attraction induces further alignment if a polar host is used.
Chapter 4 analyzes the electronic structure and emission process of the exciplex
in a solid-state blend employing the hybridized local and charge transfer excited
state. The exciplex energy spectrum is calculated by a product of the exciplex
Abstract ix

energy and density of the molecule as functions of distance between the hetero-
dimer. As a result, a variety of properties such as singlet and triplet levels,
orientation of the transition dipole moment, and fluorescent rate, depend on the
donor–acceptor binding geometry in the solid. Superposition of the fast-decaying
high-energy exciplex and slow-decaying low-energy exciplex is attributed to a
reason of the spectral redshift as time delays of the solid-state exciplex.

Keywords Organic light-emitting materials
Organic light-emitting diodes

Molecular orientation Emitting dipole orientation Vacuum deposition





Iridium complex Exciplex Optical modeling Quantum chemical calculation

Molecular dynamics simulation
List of Publications

1st Author

1. Chang-Ki Moon, Jin-Suk Huh, Jae-Min Kim, and Jang-Joo Kim*, “Electronic
structure and emission process of excited charge transfer states in solids”,
Chemistry of Materials, 30, 5648–5654 (2018). A most downloaded paper on
August 2018.
2. Chang-Ki Moon, Kwon-Hyeon Kim, and Jang-Joo Kim*, “Unraveling the
orientation of phosphors doped in organic semiconducting layers”, Nature
Communications, 8, 791 (2017).
3. Chang-Ki Moon, Katsuaki Suzuki, Katsuyuki Shizu, Chihaya Adachi, Hironori
Kaji*, Jang-Joo Kim*, “Combined Inter- and Intramolecular Charge-Transfer
Processes for Highly Efficient Fluorescent Organic Light-Emitting Diodes with
Reduced Triplet Exciton Quenching”, Advanced Materials, 29, 1606448
(2017).
4. Chan Seok Oh(+), Chang-Ki Moon(+), Jeong Min Choi, Jin-Suk Huh, Jang-Joo
Kim, Jun Yeob Lee*, “Relationship between molecular structure and dipole
orientation of thermally activated delayed fluorescent emitters”, Organic
Electronics, 42, 337–342 (2017). (+: equal contribution)
5. Chang-Ki Moon, Kwon-Hyeon Kim, Jin Woo Lee, and Jang-Joo Kim*,
“Influence of host molecules on emitting dipole orientation of phosphorescent
iridium complexes”, Chemistry of Materials, 27 (8), 2767–2769 (2015).
6. Chang-Ki Moon, Sei-Yong Kim, Jeong-Hwan Lee, and Jang-Joo Kim*,
“Luminescence from oriented emitting dipoles in a birefringent medium” Optics
Express, 23, A279–A291 (2015).
7. Jeong-Hwan Lee(+), Ganguri Sarada(+), Chang-Ki Moon(+), Woosum Cho,
Kwon-Hyeon Kim, Young Geun Park, Jin Yong Lee, Sung-Ho Jin*, and Jang-Joo
Kim*, “Finely Tuned Blue Iridium Complexes with Varying Horizontal Emission
Dipole Ratios and Quantum Yields for Phosphorescent Organic Light-Emitting
Diodes”, Advanced Optical Materials, 3, 211–220 (2014).

Other Publications

1. Jinouk Song, Kwon-Hyeon Kim, Eunhye Kim, Chang-Ki Moon, Yun-Hi Kim,
Jang-Joo Kim, and Seunghyup Yoo*, “Lensfree OLEDs with over 50%
external quantum efficiency via external scattering and horizontally oriented
emitters”, Nature Communications, In press.
2. Jin-Suk Huh, Kwon-Hyeon Kim, Chang-Ki Moon, Jang-Joo Kim*,
“Dependence of Pt(II) based phosphorescent emitter orientation on host
molecule orientation in doped organic thin films”, Organic Electronics, 45,
279–284 (2017).

xi
xii List of Publications

3. Hyun-Gu Kim, Kwon-Hyeon Kim, Chang-Ki Moon, Jang-Joo Kim*,

“Harnessing Triplet Excited States by Fluorescent Dopant Utilizing Codoped
Phosphorescent Dopant in Exciplex Host for Efficient Fluorescent Organic
Light Emitting Diodes”, Advanced Optical Materials, 5 (3), 1600749 (2017).
4. Bomi Sim, Chang-Ki Moon, Kwon-Hyeon Kim, Jang-Joo Kim*, “Quantitative
Analysis of the Efficiency of OLEDs”, ACS Applied Materials & Interfaces, 8
(48), 33010–33018 (2016).
5. Ganguri Sarada(+), Bomi Sim(+), Chang-Ki Moon, Woosum Cho,
Kwon-Hyeon Kim, Vijaya Gopalan Sree, Eunju Park, Jang-Joo Kim*,
Sung-Ho Jin*, “Synthesis and characterization of highly efficient blue Ir(III)
complexes by tailoring b-diketonate ancillary ligand for highly efficient
PhOLED applications”, Organic Electronics, 39, 91–99 (2016).
6. Kwon-Hyeon Kim(+), Jang Yeol Baek(+), Chan Woo Cheon, Chang-Ki Moon,
Bomi Sim, Myeong Yong Choi, Jang-Joo Kim*, Yun-Hi Kim*, “Highly efficient
non-doped deep blue fluorescent emitters with horizontal emitting dipoles using
interconnecting units between chromophores”, Chemical Communications,
52 (73), 10956–10959 (2016).
7. Jae-Min Kim, Seung-Jun Yoo, Chang-Ki Moon, Bomi Sim, Jae-Hyun Lee*,
Heeseon Lim, Jeong Won Kim, Jang-Joo Kim*, “N-type Molecular Doping in
Organic Semiconductors: Formation and Dissociation Efficiencies of Charge
Transfer Complex”, The Journal of Physical Chemistry C, 120 (17),
9475–9481 (2016).
8. Hyun Shin(+), Jeong-Hwan Lee(+), Chang-Ki Moon, Jin-Suk Huh, Bomi Sim,
Jang-Joo Kim*, “Sky-Blue Phosphorescent OLEDs with 34.1% External
Quantum Efficiency Using a Low Refractive Index Electron Transporting
Layer”, Advanced Materials, 28 (24), 4920–4925 (2016).
9. Jin Won Sun, Kwon-Hyeon Kim, Chang-Ki Moon, Jeong-Hwan Lee, Jang-Joo
Kim*, “Highly efficient sky-blue fluorescent organic light emitting diode based
on mixed co-host system for thermally activated delayed fluorescence emitter
(2CzPN)”, ACS Applied Materials & Interfaces, 8 (15), 9806–9810 (2016).
10. Kwon-Hyeon Kim, Jia-Ling Liao, Si Woo Lee, Bomi Sim, Chang-Ki Moon,
Gene-Hsiang Lee, Hyo Jung Kim, Yun Chi*, Jang-Joo Kim*, “Crystal Organic
Light-Emitting Diodes with Perfectly Oriented Non-Doped Pt-Based Emitting
Layer”, Advanced Materials, 28 (13), 2526–2532 (2016).
11. Hyun-Sub Shim, Chang-Ki Moon, Jihun Kim, Chun-Kai Wang, Bomi Sim,
Francis Lin, Ken-Tsung Wong, Yongsok Seo, Jang-Joo Kim*, “Efficient
Vacuum-Deposited Ternary Organic Solar Cells with Broad Absorption,
Energy Transfer, and Enhanced Hole Mobility”, ACS Applied Materials &
Interfaces, 8 (2), 1214–1219 (2016).
12. Jin Won Sun(+), Jang Yeol Baek(+), Kwon-Hyeon Kim, Chang-Ki Moon,
Jeong-Hwan Lee, Soon-Ki Kwon, Yun-Hi Kim*, Jang-Joo Kim*, “Thermally
Activated Delayed Fluorescence from Azasiline Based Intramolecular
Charge-Transfer Emitter (DTPDDA) and a Highly Efficient Blue Light
Emitting Diode”, Chemistry of Materials, 27 (19), 6675–6681 (2015).
List of Publications xiii

13. Hyun-Sub Shim, Francis Lin, Jihun Kim, Bomi Sim, Tae-Min Kim, Chang-Ki
Moon, Chun-Kai Wang, Yongsok Seo*, Ken-Tsung Wong*, and Jang-Joo
Kim*, “Efficient Vacuum-Deposited Tandem Organic Solar Cells with Fill
Factors Higher Than Single-Junction Subcells”, Advanced Energy Materials,
5 (13), 1500228 (2015).
14. Kwon-Hyeon Kim(+), Jae-Yeol Ma(+), Chang-Ki Moon, Jeong-Hwan Lee,
Jang Yeol Baek, Yun-Hi Kim*, and Jang-Joo Kim*, “Controlling Emitting
Dipole Orientation with Methyl Substituents on Main Ligand of Iridium
Complexes for Highly Efficient Phosphorescent Organic Light-Emitting
Diodes”, Advanced Optical Materials, 3 (9), 1191–1196 (2015).
15. Sohee Jeon, Jeong-Hwan Lee, Jun-Ho Jeong, Young Seok Song, Chang-Ki
Moon, Jang-Joo Kim, and Jae Ryoun Youn*, “Vacuum Nanohole Array
Embedded Phosphorescent Organic Light Emitting Diodes” Scientific Reports,
5, 8685 (2015).
16. Kwon-Hyeon Kim, Chang-Ki Moon, Jin Won Sun, Bomi Sim, and Jang-Joo
Kim*, “Triplet Harvesting by a Conventional Fluorescent Emitter Using
Reverse Intersystem Crossing of Host Triplet Exciplex”, Advanced Optical
Materials, 3, 895–899 (2015).
17. Jung-Bum Kim, Jeong-Hwan Lee, Chang-Ki Moon, Kwon-Hyeon Kim, and
Jang-Joo Kim*, “Highly enhanced light extraction from organic light emitting
diodes with little image blurring and good color stability”, Organic
Electronics, 17, 115–120 (2015).
18. Dae-Ho Kim, Kyu-Sik Kim, Hyun-Sub Shim, Chang-Ki Moon, Yong Wan Jin,
and Jang-Joo Kim*, “A high performance semitransparent organic photode-
tector with green color selectivity”, Applied Physics Letters, 105, 213301
(2014).
19. Kwon-Hyeon Kim, Sunghun Lee, Chang-Ki Moon, Sei-Yong Kim, Young-Seo
Park, Jeong-Hwan Lee, Jin Woo Lee, June Huh, Youngmin You, Jang-Joo
Kim*, “Phosphorescent dye-based supramolecules for high-efficiency organic
light-emitting diodes”, Nature Communications, 5, 4769 (2014).
20. Jung-Bum Kim, Jeong-Hwan Lee, Chang-Ki Moon, Kwon-Hyeon Kim,
Jang-Joo Kim*, “Highly efficient inverted top emission organic light emitting
diodes using a horizontally oriented green phosphorescent emitter”, Organic
Electronics, 15, 2715–2718 (2014).
21. Thota Giridhar(+), Jeong-Hwan Lee(+), Woosum Cho, Hyunyoung Yoo,
Chang-Ki Moon, Jang-Joo Kim*, Sung-Ho Jin*, “Highly efficient bluish green
phosphorescent organic light-emitting diodes based on heteroleptic iridium(III)
complexes with phenylpyridine main skeleton”, Organic Electronics, 15,
1687–1694 (2014).
22. Jin Won Sun(+), Jeong-Hwan Lee(+), Chang-Ki Moon, Kwon-Hyeon Kim,
Hyun Shin and Jang-Joo Kim*, “A Fluorescent Organic Light Emitting Diode
with 30% External Quantum Efficiency”, Advanced Materials, 26, 5684–5688
(2014).
xiv List of Publications

23. Hyun Shin(+), Sunghun Lee(+), Kwon-Hyeon Kim, Chang-Ki Moon,

Seung-Jun Yoo, Jeong-Hwan Lee and Jang-Joo Kim*, “Blue Phosphorescent
Organic Light Emitting Diodes using an Exciplex Forming Co-host with the
External Quantum Efficiency of Theoretical Limit”, Advanced Materials, 26,
4730 (2014).
24. Kwon-Hyeon Kim, Chang-Ki Moon, Jeong-Hwan Lee, Sei-Yong Kim and
Jang-Joo Kim*, “Highly Efficient Organic Light-Emitting Diodes with
Phosphorescent Emitters Having High Quantum Yield and Horizontal
Orientation of Transition Dipole Moments”, Advanced Materials, 26, 3844
(2014).
25. Jung-Bum Kim(+), Jeong-Hwan Lee(+), Chang-Ki Moon, Jang-Joo Kim*,
“Highly efficient inverted top emitting organic light emitting diodes using a
transparent top electrode with color stability on viewing angle”, Applied
Physics Letters, 104, 073301 (2014).
26. Seung-Jun Yoo, Jung-Hung Chang, Jeong-Hwan Lee, Chang-Ki Moon, Chih-I
Wu, and Jang-Joo Kim*, “Formation of perfect ohmic contact at indium tin
oxide/N,N9-di(naphthalene-1-yl)-N,N9-diphenyl-benzidine interface using
ReO3”, Scientific Reports, 4, 3902 (2014).
27. Jung-Bum Kim, Jeong-Hwan Lee, Chang-Ki Moon, Sei-Yong Kim, Jang-Joo
Kim “Highly Enhanced Light Extraction from Surface Plasmonic Loss
Minimized Organic Light-Emitting Diodes”, Advanced Materials, 25, 3571–
3577 (2013).
28. Sei-Yong Kim, Won-Ik Jeong, Christian Mayr, Yong-Seo Park, Kwon-Hyeon
Kim, Jeong-Hwan Lee, Chang-Ki Moon, Wolfgang Brutting and Jang-Joo
Kim, “Organic Light-Emitting Diodes with 30% External Quantum Efficiency
Based on a Horizontally Oriented Emitter”, Advanced Functional Materials,
23, 3896 (2013).

List of Presentations

1. Chang-Ki Moon, Kwon-Hyeon Kim, Jang-Joo Kim, “Origin of the Orientation

of Ir Complexes Doped in Organic Semiconducting Layers” MRS Spring 2018,
April 2–6 (April 3), 2018, USA (Poster).
2. Chang-Ki Moon, Jin-Suk Huh, Jae-Min Kim, Jang-Joo Kim, “Electronic
Structures and Emission Processes of Exciplex depending on Dimer
Geometries in Solid States”, The 17th International Meeting on Information
Display (iMiD 2017), August 28–31 (August 31), 2017, Korea (Oral).
3. Chang-Ki Moon, Kwon-Hyeon Kim, Jang-Joo Kim, “Unraveling origin of
phosphors doped in organic semiconducting layers”, SPIE Optics+Photonics
2017, August 6–10 (August 8), 2017, USA (Oral).
4. Chang-Ki Moon, Jin-Suk Huh, Jae-Min Kim, Jang-Joo Kim, “Electronic
structures and emission processes of exciplex depending on dimer
List of Publications xv

configurations”, 2nd International TADF Workshop, July 19–21 (July 19),

2017, Japan (Poster).
5. Chang-Ki Moon, Kwon-Hyeon Kim, Jang-Joo Kim, “Unraveling the orienta-
tion of phosphors doped in organic semiconducting layers”, The 28th
International Conference on Molecular Electronics and Devices 2017 (IC
ME&D 2017), May 18–19 (May 19), 2017, Korea (Poster).
6. Chang-Ki Moon, Katsuaki Suzuki, Katsuyuki Shizu, Chihaya Adachi, Hironori
Kaji, Jang-Joo Kim, “Combination of an exciplex host and a TADF dopant for
efficient fluorescent OLEDs with low roll-off”, The 8th Asian Conference on
Organic Electronics (A-COE 2016), December 5–7 (December 6), 2016, Japan
(Poster).
7. Chang-Ki Moon, Katsuaki Suzuki, Katsuyuki Shizu, Hironori Kaji, Jang-Joo
Kim, “Combined Inter- and Intra-molecular Charge Transfer Processes for
Highly Efficient Fluorescent Organic Light-emitting Diodes with Reduced
Triplet Exciton Quenching”, International Conference on Electronic Materials
and Nanotechnology for Green Environment (ENGE 2016), November 6–9
(November 07), 2016, Korea (Poster).
8. Chang-Ki Moon, Sei-Yong Kim, Jeong-Hwan Lee, Jang-Joo Kim,
“Luminescence from oriented emitting dipoles in a birefringent medium”, The
International Symposium on Recent Advances and Future Issues in Organic
Electroluminescence (ISOEL2016), February 17–19 (February 18), 2016,
Korea (Poster).
9. Chang-Ki Moon, Kwon-Hyeon Kim, Jin Woo Lee, Jang-Joo Kim, “Influence
of Host Molecules on Emitting Dipole Orientation of Phosphorescent Iridium
Complexes”, The International Symposium on Recent Advances and Future
Issues in Organic Electroluminescence (ISOEL2016), February 17–19
(February 18), 2016, Korea (Poster).
10. Chang-Ki Moon, Kwon-Hyeon Kim, Jin Woo Lee, Jang-Joo Kim, “Influence
of Host Molecules on Emitting Dipole Orientation of Phosphorescent Iridium
Complexes”, A-COE 2015, October 29–31 (October 30), 2015, China (Poster).
11. Chang-Ki Moon, Sei-Yong Kim, Jeong-Hwan Lee and Jang-Joo Kim,
“Luminescence from oriented emitting dipoles in a birefringent thin film and
OLEDs”, The International Workshop on Flexible & Printable Electronics 2014
(IWEFE 2014), November 5–7, 2014, Korea. (Poster).
12. Chang-Ki Moon, Sei-Yong Kim, Jung-Bun Kim, Jeong-Hwan Lee, and
Jang-Joo Kim, “Optical analysis of external quantum efficiency & total
extractable light amount in OLEDs with different electrode types”,
KJF-ICOMEP 2013 (KJF International Conference on Organic Materials for
Electronics and Photonics), August 28–31 (August 30), 2013, Korea (Poster).
13. Chang-Ki Moon, Sei-Yong Kim, Jung-Bun Kim, Jeong-Hwan Lee, and
Jang-Joo Kim, “Optical analysis of external quantum efficiency & total
extractable light amount in OLEDs with different electrode types”, IMID 2013
(The 13th International Meeting on Information Display), August 26–29
(August 29), 2013, Korea (Poster).
xvi List of Publications

List of Patents

1. Jang-Joo Kim, Chang-Ki Moon, Sei-Yong Kim, Jeong-Hwan Lee, “Apparatus

for angular dependent measurement of photoluminescence emission spectrum”,
10-1468065 (2014.11.26).
2. Jang-Joo Kim, Chang-Ki Moon, Sei-Yong Kim, Jeong-Hwan Lee, “Apparatus
for angular dependent measurement of photoluminescence emission spectrum”,
PCT/KR2014/011785 (2014.12.03).
3. Jang-Joo Kim, Chang-Ki Moon, “Apparatus for testing”, Application
No. 16-48961 (2016.04.21).
4. Jang-Joo Kim, Chang-Ki Moon, “Apparatus for testing”, PCT/KR2016/004535
(2016.04.29).
Acknowledgements

Thanks to the people who helped me, I was able to finish my degree. It was the
most valuable experience of my life.
Professor Jang-Joo Kim was my advisor and an exemplary scientist. I greatly
appreciate his support in my graduate school life. I will always think of his passion
and conviction as a scientist.
I am grateful to my mentor, Dr. Sei-Yong Kim. His optical theory and simulation
program are the basis of all my research. I would like to acknowledge Prof. Jun Yeob
Lee in Sungkyunkwan University, Prof. Hironori Kaji in Kyoto University, and
Dr. Jin Woo Lee from Samsung Total Petrochemicals. It was a pleasure doing won-
derful collaborations and discussions with them. Dr. Andrienko kindly supported me
during my three-month visit at Max Planck Institute for Polymer Research.
I appreciate it, and I could start to do molecular dynamics simulations with his
help. Prof. Youn Joon Jung in Seoul National University also gave me lots of advice
on the molecular dynamics simulation. I especially thank Dr. Matthew D. Halls and
Dr. Shaun H. Kwak from Schrodinger Inc. for their kind and helpful discussions in
calculations and simulations. I could enjoy laboratory life thanks to the smart and
friendly laboratory members.
Finally, I would like to thank my family who always give me love and support.

xvii
Contents

1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
1.1 Molecular Orientation in Organic Electronics . . . . . . . . . . . . . . . . 1
1.1.1 History . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
1.1.2 Importance of the Molecular Orientation . . . . . . . . . . . . . . 1
1.1.3 Estimation of Molecular Orientations . . . . . . . . . . . . . . . . 4
1.2 Optical Models of OLEDs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
1.3 Iridium Complex . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9
1.4 Exciplex . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10
1.5 Outline of the Thesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
2 Modeling of the Dipole Radiation in an Anisotropic Microcavity . . . 17
2.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
2.2 Theoretical Background . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18
2.2.1 Dipole Radiation in a Birefringent Medium . . . . . . . . . . . . 18
2.2.2 Efficiency of OLEDs with a Birefringent Emissive
Layer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
2.2.3 Far-Field Radiation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
2.2.4 Experimental . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
2.3 Results and Discussion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25
2.3.1 Optical Birefringence and the Dipole Orientation . . . . . . . . 25
2.3.2 Emission Spectra of OLEDs . . . . . . . . . . . . . . . . . . . . . . . 26
2.3.3 Efficiency of OLEDs . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
2.3.4 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28
2.3.5 Appendix . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30

xix
xx Contents

3 The Orientation of Ir Complexes Doped in Organic Amorphous

Layers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 33
3.1 Influence of Host Materials on the Emitting Dipole Orientation
of Ir Complexes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
3.1.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
3.1.2 Results and Discussion . . . . . . . . . . . . . . . . . . . . . . . . . . 34
3.1.3 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
3.2 Unraveling the Orientation of Ir Complexes via Vacuum
Deposition Simulation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
3.2.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
3.2.2 Results . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40
3.2.3 Discussion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
3.2.4 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53
3.2.5 Methods . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57
4 Analysis of the Electronic Structure and Emission Process
of Exciplex in Solids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59
4.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59
4.2 Results and Discussion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
5 Summary and Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
Curriculum Vitae . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
List of Figures

Fig. 1.1 A molecular structure of ter(9,9-diarylfluoreene) (TDAF 1)

and optical constants of the TDAF 1 film . . . . . . . . . . . . . . . . .. 2
Fig. 1.2 Organic molecules have preferred orientations in
vacuum-deposited films . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 2
Fig. 1.3 a Radiation from horizontal and vertical dipoles in OLED
stacks. b Theoretical calculation of EQE as functions of the
ratio of horizontal dipole moment and radiative quantum
efficiency . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 3
Fig. 1.4 Estimation of the molecular orientation in thin films using the
transition dipole moment . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 4
Fig. 1.5 a An experimental setup of angle-dependent PL measurement.
b Angular p-polarized emission profiled of Ir(ppy)2tmd and fit
by optical simulation of film luminescence . . . . . . . . . . . . . . . .. 6
Fig. 1.6 An environment of horizontal and dipoles embedded in a alyer
sandwiched by two layers . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 8
Fig. 1.7 Molecular structures of some iridium complexes . . . . . . . . . . .. 10
Fig. 1.8 a Charge transfer between donor and acceptor upon excitation
to form an exciplex. b The emission spectrum of exciplex
which is red-shifted in compared to absorption and emission of
monomers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 11
Fig. 1.9 a Energy state of exciplex. The low energy gap between the
singlet and triplet excited states allow fast intersystem crossing
(ISC) and reverse intersystem crossing (RISC), thereby
delayed fluorescence. b A typical transient PL decay curve of
an exciplex consisting of fast prompt decay and slow delayed
decay . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 12
Fig. 2.1 Dipole embedded in an anisotropic medium sandwiched by
two layers. The y-axis is perpendicular to the x-z plane.
Arrows represent the relation between wave vector
components for different electric field polarizations . . . . . . . . .. 19

xxi
Another random document with
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The Project Gutenberg eBook of Splashes of
red
This ebook is for the use of anyone anywhere in the United States
and most other parts of the world at no cost and with almost no
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you are located before using this eBook.

Title: Splashes of red

Author: J. Frank Davis

Release date: May 13, 2024 [eBook #73618]

Language: English

Original publication: New York: Street & Smith Corporation, 1925

Credits: Roger Frank and Sue Clark

*** START OF THE PROJECT GUTENBERG EBOOK SPLASHES OF

RED ***
 Splashes of Red
By J. Frank Davis
Author of “Unwritten Law,” “Whoso Diggeth a Pit,” Etc.

West comes East—and proves that its own methods for

crime detection work as well in the big city as they do
in the God’s country.

That star rodeo performer, but as bad an egg as ever moonlit a

bronc, the “Oklahoma Kid,” wrestled his steer to a quick fall, and the
voice of “Foghorn” McNamara, holding his horse quiet to face the
crowded grand stand at Speedway Park, came booming across the
field to where Millie Wayne, in her cowgirl clothes, stood waiting to
participate in the next event on the program.
“That bulldogger was Jack Marling, the Oklahoma Kid. Time,
seventeen seconds flat. Next and last contestant in today’s
bulldogging is ‘Curly’ Bratton.”
Preston Campbell, the rodeo judge, gray-mustached Texan of the
old school, raised a hand toward the chute where the next steer
waited, and the red beast plunged wildly across the arena, desperate
to leave behind him the lithe youngster with the blazing neckerchief
who galloped on his flank.
Opposite the middle of the grand stand the horse overtook the
steer, swerved in, and Curly leaped and got the horns with not one
lost motion. Feet braced, he slid backward for two seconds, then
man and steer came to a struggling stop. For one more second they
might have been a statue.
The animal’s head, then, twisted slowly, grotesquely, as though it
cocked its startled eyes to squint sidewise at the sky. Its feet went
out from under it. Down together to the ground crashed bulldogger
and bulldogged, and the youth’s right hand shot upward in signal to
the judge.
The Oklahoma Kid, who meantime had been returning across the
field, out of the public picture, stopped beside Millie Wayne.
“Can you beat it?” he demanded. “Drop that hombre into a
dipping vat and he’d come up with a pocket full of oil wells! If I
could ever get luck to break for me that-a-way——”
Millie was not listening. A bit breathlessly she was looking toward
where Curly and the steer were rising out of the dust. It had been a
wonderful throw. After exhibitions like that it had been Curly’s habit
to wave his hand at her—until the previous day.
A messenger, cantering over from where old Pres Campbell sat on
his horse in the center of the field, handed a slip of paper to
Foghorn McNamara, who glanced at it and made due
announcement:
“That bulldogger was Curly Bratton. Time, eleven and two fifths
seconds. The world’s record is seven and two fifths seconds. Curly
Bratton wins today’s bulldogging. Jack Marling, second. Billy Toms,
third. The next event is the cowgirls’ trick-riding contest. The ladies
taking part——”

Millie’s teeth shut tightly over her lower lip. Curly had not looked at
her at all. He had waved his hand toward the stand—toward one
spot in the stand, the same spot he had waved to yesterday
afternoon, the spot where a brilliant toque hat made a splash of
violent red. And under the crimson splash a feminine hand waved
back.
It was a soft, pinkly manicured hand, quite different from Millie’s
not unbeautiful but hard, competent ones. Millie had not failed to
note the contrast when its owner—her name was Florrine—had been
introduced to a lot of the performers by one of the resident
managers of the show after the first afternoon’s contests. Millie had
closely observed the face, too; an oval, olive face, artistically tinted,
with languishing dark eyes. And the clothes.
Miss Florrine wore modish clothes; Millie, even at the moment
when Curly, shaking hands with the city girl, had awkwardly
murmured his delight at meeting her, had realized how they looked
in comparison with her own picturesque but simple working garb. At
the same moment she had sensed that the girl was attracted by
Curly—as who wouldn’t be?—and that Curly was tremendously
flattered and impressed.
Then, not much later, Curly and Miss Florrine had spoken together
at the edge of the group, and Curly, that evening, carefully attired in
his most striking raiment, had left the hotel immediately after dinner
and was still absent when Millie went to bed. The previous day he
had waved toward the red hat instead of at Millie. And now again on
this day.
Millie would be the second on the cowgirl program, and the first
contestant rode out to do her stuff. Millie cinched her horse, which
did not need it, and only half heard the Oklahoma Kid as he came
closer, having observed Curly’s gesture toward the stand as well as
she, and suggested:
“Let’s you and me do a show or something in town tonight. Huh?
Whatya say, Miss Wayne? Let’s.”
Nothing in the world was farther from Millie’s mind than going to a
show or anywhere else with Jack Marling, but she was angry and her
pride was hurt. She and Curly Bratton were not engaged, but
everybody expected them to be. His attention had been solely for
her in half a dozen Western rodeos and chance had again brought
them together at this, one of the first real rodeos, and not a wild-
West show, ever given on the Atlantic seaboard outside New York.
For the first day, Curly had been as attentive to her as ever—and
then he had met that handsome, sophisticated girl of the red hat.
“Huh?” urged the Oklahoma Kid.
“Whatya say, Miss Wayne? A show and some good eats,
somewheres.”
That was precisely what she had promised to do, that night, with
Curly. Promised it on the opening day of the show, before he had
seen the Florrine girl. Millie was conscious, as she straightened, that
Curly was approaching now, on his way to the dressing tents. Just as
he arrived within hearing, “Red” Peeks, the clown, came riding on
his donkey and stopped to pass Curly a .45 caliber pistol.
“Thanky kindly,” the clown said. “No more shootin’ for today and I
won’t need it tomorrow. My own’ll be fixed.”

Dressed for bulldogging and hence with no holster, Curly held the
weapon in his hand as he stopped beside Millie and the Oklahoma
Kid. Curly did not like the Kid, but, more, he did not like to see him
talking to Millie. That he himself was thinking less of her, these days,
than of the girl whose bright headdress set off her olive skin, did not
alter this feeling; man in such matters is not consistent.
He hesitated a second, looked from one to the other and said:
“We got a date tonight, Millie. Will you be ready ’bout seven?”
This casual taking it for granted that he could do what he had
done and not suffer her resentment stirred Millie into cold anger, but
she came of a stock trained not to exhibit emotion and merely
smiled as she replied:
“You must have got your nights mixed, Curly. Because tonight I’ve
got an engagement with Mr. Marling.”
Curly’s face fell almost comically. He stared from her to the
grinning Oklahoma Kid and opened his mouth as though to protest.
Then he swallowed, turned away and walked toward the chutes.
“What time tonight, little one?” Marling asked.
 He was staggered by her answer and the flash of her eyes that
accompanied it.
“Not any time,” she said. “I’ve changed my mind.”
“Next contestant,” bellowed Foghorn McNamara, “is Miss Millie
Wayne!”
She sprang into her saddle and was off toward the stand, while
Marling, who understood some kinds of women very well but her
kind not at all, gazed open-mouthed after her. Turning, he also
tramped toward the chutes and found Curly Bratton, his face harshly
set, standing a little apart from the other cowboys, waiting.
Curly’s voice was very low and his normal drawl was exaggerated.
“If you’ll excuse me, suh,” he said to Marling, “I’d admire to have
you not meddle wi’ that lady.”
“Well, what the——”
“I don’t want to have no quarrel with you, suh, but there ain’t no
reason why we shouldn’t understand each other. She don’t happen
to know you very well, I reckon, and of course I ain’t the one to tell
her—and I don’t go round shootin’ off any backcapping talk to ladies
or any one else—but she ain’t the kind——”
The Oklahoma Kid recovered from his astonishment.
“You got some nerve, telling me who’ll I’ll take out and who I
won’t take out. If it wasn’t for the rules o’——”
“Sh-h-h, if you please, suh. There ain’t no reason for anybody else
to know——”
Marling raised his voice even louder.
“Anybody in the wide world can know as far as I’m concerned,
hombre! I pick my own girls and my own girls pick me, Millie Wayne
or anybody else.”
The group at the chutes had fallen silent, ears pricked.
Bratton spoke through his teeth, hardly more than a whisper.
“I’d rather you didn’t mention no ladies’ names.”
“Who the blazes are you, to be telling me——”
A shadow fell upon them and Pres Campbell, ex-Texas Ranger,
quietly wheeled his horse. His voice was level but authoritative.
 “If you boys got any quarreling to do, wait till after the show. You
know the rule about rowdyism. Well, I’ll enforce it against both of
you if I have to. What’s it all about? If you’re kicking about your
bulldogging time, Marling, you’re plumb wrong. I fined you five
seconds because there wa’n’t no daylight showing between you and
the steer at the dead line, but that didn’t change the result; even if
you hadn’t lost that five seconds Bratton still beat you.”
“Aw, that’s all right, judge,” Marling said.
“And you, Bratton, what you got that gun in your hand for? You
know there’s a rule against carrying a gun except where they’re
called for in the show.”
“I lent it to Red Peeks. His was busted. He just give it back to me.”
“All right. Go put it up. And don’t let me hear any more ruckuses
startin’ on this field.”
Fully master of the rodeo and its contestants, old Pres turned and
cantered back to the center of the field. The Oklahoma Kid had
disappeared into a tent and Curly, with not much time before the
calf-roping event, hastened to his own.

Millie Wayne, unable to sleep, although the cowgirl in bed with her
was piling up strength for the morrow like a child, heard the knock,
not far from midnight, on the door on the next room, heard Pres
Campbell’s quick call of “Who is it?” and the voice of one of the local
rodeo committeemen in the hotel corridor, saying:
“Sorry to wake you up, Mr. Campbell, but one of your men’s been
killed, downtown, and the police have just come and got another
one for doing it.”
“What’s that?” Millie heard Campbell’s feet hit the floor, his room
door open. “Who’s killed? How?”
“Marling. Curly Bratton did it, it seems. Shot him. The cops came
out and found the pistol in his room. Recently fired. They had a
quarrel this afternoon.”
“Come in while I get dressed. I know about that quarrel—it was
over the bulldogging win. At least I thought it was; come to think of
it, I didn’t hear a word of it. Where did they get to fighting? Which
one went after his gun first?”
“It don’t seem to have been a fight,” the local man said. “Marling
was shot in the back of the head.”
Wide-eyed, Millie swung around to sit on the edge of her bed. She
heard Pres Campbell exclaim:
“The thunder he was! I’d ’a’ swore Bratton wa’n’t that kind of a
boy. Does he admit it?”
“No. He says he hasn’t seen Marling since this afternoon’s show.
But he can’t prove where he was this evening. Says he was
downtown till ten o’clock and didn’t see anybody he knew that can
alibi him.”
“Come in,” Pres invited, and she heard the door close.
A murmur of indistinguishable words followed while the Texan
dressed. His close to sixty years had not lost him his habit of taking
command of a situation or his ability to get into his clothes quickly,
and barely five minutes had elapsed before Millie heard his decisive:
“All right, Mr. Taylor. Let’s go!”
She had thrown on a kimono and stood in her doorway as
committeeman and one-time ranger came out.
“Uncle Pres!” she cried. “I couldn’t help hearing. He didn’t do it.”
“How do you know?” the local man demanded, before Campbell
could speak.
“I know him. He’d never shoot anybody from behind.”
“Just what I said,” agreed the ex-ranger. “But what he seems to
need is an alibi. Maybe, if you and he were together any——”
“I haven’t seen him since he went out right after supper, and then
I don’t think he saw me; I just noticed him going through the lobby,”
the girl said. “But it’s nonsense to charge him——”
“He and Marling quarreled this afternoon,” put in Taylor. “Over one
of Mr. Campbell’s decisions.”
Millie knew nothing of the quarrel, of course. She could only say
again, stubbornly:
 “But he didn’t do it. You’re going to try to get him out, aren’t you,
Uncle Pres?”
“Going to do everything I can,” the old man replied. “I don’t guess
we’ll be able to get him turned loose tonight, but first thing in the
mawnin’, if we have luck—— You go back to bed, Millie, and get your
sleep. I’ll let you know how things stand first thing in the mawnin’.”
He and Taylor passed down the corridor and were standing at the
elevator when Millie called him back and spoke too low for the local
man to hear.
“Curly never would bring any lady’s name into a thing where it
might get into the newspapers unless he was sure it wouldn’t hurt
her,” she said. “He went—— I don’t know it, but there’s a girl——”
“I’ve sort of suspected there might be, noticing you two the last
day or so,” Campbell remarked dryly. “Wa’n’t none of my business, of
course, but I couldn’t help noticin’. Some city lady, is it?”
“She’s sat in the same place in the grand stand every day, wearing
a red hat——”
“Me, I don’t notice ladies’ hats much,” Pres said. “Maybe, if you
could give me a better description——”
“I was introduced to her, at the same time Curly was. Miss
Florrine, her name is. She’s—she’s very pretty and well-dressed and
city-acting.”
“H’mph!” grunted the ex-ranger. “And boys don’t have sense
enough to know when they’re well off. Any more,” he conceded,
“then they did when I was one. Who is she?”
“I don’t know. Nothing except her name. But if his alibi had to
include her, and for any reason he thought she ought to be
protected, he’d never tell.”
“Florrine,” said Pres. “That isn’t a common name, or hard to
remember. When I get to see him, I’ll know what to ask about.”
In the detective room at police headquarters, while Taylor
remained discreetly silent, Pres Campbell met a character new in his
experience—the plain-clothes man promoted from pounding a beat,
who had never been outside a big city, never wanted to be, and
oozed contempt for every one and everything that was not
metropolitan.
“You bozos with big hats,” he remarked heavily, “think you can get
away with murder. Nothing to it, mister; nothing to it. This Bratton
guy did it and we’ve got him. You and your gang of cowboys can’t
come into this town and pull your rough stuff.”

Campbell, whose competency in crime detection could be attested

by thousands of Texans, was here unfamiliar with the laws,
unacquainted with police procedure and at sea as to his rights. One
more familiar with Southwestern characteristics than was Detective
Moore would have noted a glint in his eye and set of his jaw at the
sneer. After the slightest hesitation, to be certain that he had his
temper quite under command, the ex-ranger said:
“If you would be willing to tell me a little, perhaps, about how you
know Bratton done it—that is, if it ain’t defeatin’ the ends of justice
any way to tell—— You see, suh, I’m in a sort of way the head of
this outfit of ours, being the contest judge and so forth. If there isn’t
any reason why you should be afraid to tell me——”
“Say, what would make you think I might be afraid of anybody in
your gang?” the detective demanded truculently. “Not any, cowboy,
not any! I don’t know how your constables out West go clean up a
murder, but me—first thing when a guy gets bumped off like this
man of yours, I look for the frail.”
“Frail?” queried Pres.
“The skirt; the jane; the woman. And this time it was easy. This
Bratton quarrels with Marling only this afternoon over her—and you
know that cussed well, because you stopped ’em.”
“Me? I thought they were having words over one of my decisions.”
“Yes, you did!” scoffed the detective. “Well, they wasn’t. Half a
dozen men heard the girl’s name when Marling spoke it.”
“I didn’t. What was the name?”
“Say, are you trying to kid me? You know blame well it was Wayne
—Millie Wayne. One of them roughneck women with your show.”
 “Mr. Moore,” said Pres, very mildly, “Miss Wayne’s a right nice
young lady, suh. I’d admire not to have you speak like that about
her.”
“You’d ‘admire’ for me not to speak like that about a ‘right nice’
young lady,” mimicked Moore. “Listen, fella! You ain’t out in the
brush now. You’re in a town with bright lights in it. And I talk about
women that get mixed up in murders like they’re supposed to be
talked about. Get me?”
The briefest second Pres Campbell fought for self-control and
achieved it.
“Yes, suh,” he said. “Well, if there ain’t anythin’ I can do to help
——”
“When we need any help from yap deputy sheriffs, we’ll broadcast
for it,” Moore answered.
“Yes, suh,” said Pres, and turned toward the door, observing that
of the three or four other detectives in the room, at least two were
grinning broadly. “I’ll bid you good night, suh.”
Out on the street, the local committeeman said: “Well, that’s that.
I told you my being with you would probably do you more harm than
good, my not being tied up with this city administration—but I don’t
know as you’d have done any better if you’d gone alone. It’s never a
bad idea to have a witness along when you’re talking to a man like
that Moore.”
“I wanted to see Curly and I’d have liked to see Marling’s body,
too,” the ex-ranger replied, “but there wa’n’t any use asking after he
got so plumb insulting.”

They were walking slowly and now became conscious that footsteps
behind them were quickening. As they turned a corner and passed
out of sight of the police headquarters entrance, a husky voice called
cautiously:
“Go on past that street light and stop.”
Campbell, over his shoulder, recognized a thickset, elderly man as
having been one of the audience during his interview with Detective
Moore.
 Taylor whispered: “Detective Graney. One of the old-timers on the
force.”
They stopped in the shadow halfway down the block and Graney
came ponderously heavy-footed to stand beside them.
“Kind of a raw deal Moore give you, back there,” he remarked. “He
don’t know nothing about folks from Texas, Moore don’t.”
“Do you, suh?” Campbell asked courteously.
“Well, a little,” replied the detective. “And here all I pounded after
you guys for was because I got kinda used to Texas fellas in the
Spanish War, and most of ’em that I run into was good sports.” He
added, ingeniously: “And because this Moore—you don’t need to go
repeating it, either of you, though it ain’t any secret to him I think so
—is a bonehead, right.”
“He didn’t seem to consult the rest of you much,” Pres remarked
tactfully.
“He never does; he knows it all himself,” said Graney. “It ain’t like
he was the chief, you know. It just happens, the chief being out of
town and the cap’n off duty tonight, that he’s sitting in at the top.”
Graney concluded bitterly:
“He’s a wise guy—I don’t think.”
The ex-ranger wasted no time seeking to learn what ancient
departmental feud between Graney and Moore might be at the
bottom of this bitterness, but asked practically:
“What can we do, friend?”
“What,” inquired the detective, “do you want to do—short of
getting your man out?”
“I want to talk with him—and I want to see the man that was
killed.”
“Fair enough,” Graney commented. “We’ll do the second thing first
—over at the morgue. After that we’ll come back and you can see
Bratton in his cell.” He explained this order of procedure by saying:
“Moore goes off duty at two o’clock. The fella that takes charge then
don’t like him much more’n I do.”
 Taylor at this point intimated that morgues had never entered into
his life and he hoped they never would. Campbell was entirely willing
to excuse him from further participation in the night’s wanderings.
The ex-ranger and Detective Graney, presently, were viewing the
body of the reckless and once handsome Oklahoma Kid, awaiting the
official autopsy that would take place in the morning.

At his first glance, the Texan spoke with relief.

“Yes,” he said. “There ain’t any doubt about his being shot from
behind. I was afraid some mistake had been made about that and if
it had been done from in front, it might ’a’ been a fight. Where’s the
bullet?”
“We never found it,” Graney said. “The killing, you see, was out of
doors. In that alley that leads up to the side door of the Monaco
Cabaret.”
“I hope it gets found. Because I’m sure Curly Bratton ha’n’t got
any gun except a .45. All the pistols in our outfit are that caliber. And
there ain’t any way of proving it without that piece of lead, because
bullets don’t always act just the same in all cases—but I’d gamble
the best hawse I’ve got that this hole wasn’t made by any Colt.
Looks to me as if it was too small going in and too big coming out.
When you find that bullet, if it isn’t busted so its weight don’t prove
anything, I’m sayin’ it’ll be a .38 at the biggest, and perhaps a .32.”
His eyes fell upon the pile of clothing that had been stripped from
the body.
“Say, Mr. Graney!” he demanded. “Are you sure all these clothes
were Marling’s?”
“Bound to be,” the detective said. “The system they’ve got here,
there’s no chance of a mix-up.”
“I took ’em off him myself,” put in the morgue attendant who
accompanied them. “Don’t touch ’em. The coroner ain’t looked ’em
over yet.”
“I wasn’t aiming to,” Pres assured him. “I’ve been a peace officer
myself.”
“What’s the matter with ’em?” Graney asked.
 “Nothing. Only he didn’t usually wear a red handkerchief around
his neck. Let’s go!”
Through steel bars, Pres talked with Curly Bratton. Detective
Graney was kind enough to stand back out of earshot.
“Right off, firsthand,” Campbell said, “I’ll tell you, son, I don’t
believe you did it. And Millie, she was right positive. Wouldn’t make
any difference how much evidence these police thought they had,
she’d know better.”
“They haven’t told me all the details of what they think,” Curly
remarked, “but they’ve got hold of that quarrel the Kid and me had
this afternoon. I don’t know how much the boys heard—I don’t think
they heard anything I said—but I was declaring myself to him after I
found out him and her were going out to supper together.”
“They were?” exclaimed Pres. “They didn’t.”
It was Curly’s turn to exhibit astonishment.
“She told me they were going to,” he said. “If she hadn’t—— Tell
you the truth, judge, she and me had a date for supper tonight and
when you come up on the Kid and me, that-a-way, she had just a
few minutes before turned me down and said she was going with
him—told me with him present. And while I didn’t so much care right
at that minute about her going with me, thinking of her going out
with him got me mad.”
“Why didn’t you want her to go with you? If she didn’t, were you
going to meet the Florrine lady?”
“Oh, judge! Her name isn’t going to get into it, too, is it?”
“How are you going to stop these police digging up all sorts of
things?” Pres countered. “And if Miss Florrine can alibi you——”
“But she can’t,” Curly protested. “I haven’t seen her since this
afternoon at the rodeo and then I didn’t see her to speak to.” He
hesitated a second, then said: “We don’t want to drag any nice
lady’s name into this, judge, but between you and me I was looking
for her, Millie having turned me down and all that. But she wasn’t
where she and I met last night. So I looked round a while and then
went home and went to bed.”
He explained further. “Being kind of upset, one way and another, I
forgot to clean my pistol like I’d intended to. Red Peeks had used it
for the show, you know. And the police, finding it had been fired—
telling ’em about Peek’s firing it made no difference, because it
wouldn’t be no dirtier if I had fired it afterward——”
“I know,” interrupted Campbell. “You didn’t call on Miss Florrine at
her home, I take it.”
“She thought her folks might object, me being a cowboy and all,”
Curly confided. “So we met at one of these cabaret dance places—
the Monaco is the name of it.”
“The Monaco, eh? Who did you see there you knew—not last night
when you were with Miss Florrine, but tonight, when you couldn’t
find her?”
“Nobody,” declared Curly with obvious sincerity. “Not a soul. I
went in and looked around and she wasn’t there, so I bought me a
drink for manners, and pretty soon I went out and looked in a
couple other places and then I beat it home to the hotel.”
“Was there anybody in the alley when you came out of the
Monaco?”
“Alley?” Curly queried. “What alley?”
“Where the side door is.”
“I never noticed any side door on any alley. Me, I went in at the
front—tonight and the other two times I’ve been there. I went there
the first time with Pearl—I mean Miss Florrine——”
“Got real well acquainted for three days, didn’t you, son? Quite a
few folks must have noticed it, one place and another. And it never
occurred to you, I s’pose, that when Millie said she wa’n’t going to
supper with you, it might be because she thought prob’ly you’d
rather be out again with the new girl. I don’t know that, but I don’t
guess it’s a bad shot in the dark.
“Girls are fussy that a way about dividing their time with new
ladies,” he went on. “Millie didn’t tell me either that or anything else
about it all, but I gathered from something she said that you had
trompled on her feelings. That didn’t stop her saying she knew you
didn’t kill him, though.”
 “Who do you suppose did, judge?”
“No more idea’n the man in the moon,” Pres had to admit. “But we
aim to do some investigatin’ between now and sunup, me and this
friend of mine that’s a detective. I see you’re wearing the usual red
handkerchief.”
Curly’s fingers went to it.
“What’s that got to do with things?”
“I dunno,” the ex-ranger replied. “I dunno as it’s got anything to
do with ’em a-tall. I only happened to notice it. Have you happened,
escortin’ her round to one place and another, to meet any of Miss
Florrine’s friends?”
“I don’t remember any names. Just folks we met there in the
Monaco and another dance place we went into.”
“All seem to be well-dressed, up-to-date folks?”
“Yes. Look here, judge, there ain’t no reason to go ringing her or
her friends in on a mess of trouble like this. Her folks are kinda old-
fashioned and don’t like her to go round to dance halls where it’s
lively——”
“Lots of old folks are that a way. Did you say they were father and
mother both?”
“I didn’t say. I don’t know as I ever heard her mention. What
difference does it make? I didn’t find her tonight.”
“That’s so; so you didn’t. Well, I’m sorry to leave you here, son,
but I’ve got to. We’ll be doing all we can.”
“A habeas corpus and reasonable bail and——” Curly began, but
Campbell shook his head.
“This ain’t Texas. Up in this country they don’t fix reasonable bail
for homicide. But keep smilin’. Your friends are all on the job—
especially Millie.”
“Say, judge,” said the cowboy with some embarrassment. “I been
kinda foolish, maybe. These new folks I met are right nice folks, but
I didn’t really—— I don’t s’pose anything can be done to square it,
but sitting here I’ve been thinking that our own kind o’ folks is our
own kind o’ folks. If Millie could sort o’ forgive——”
 “Curly,” said the older man, “Millie’s daddy and me were friends as
long as he lived—such good friends that she’s been callin’ me ‘uncle’
ever since she was old enough to talk. I aim, when she gets
married, to do anythin’ an old-timer like me can do to see she gets a
fairish sort of husband.
“Personally,” he continued, “I’d rather she took a kid that had
made a few kinds of fool of himself and got over it than one that city
glitter was going to get some time after he married, maybe. Millie’s
got a heap o’ sense. She might see it the same way—and then,
again, she mightn’t, dependin’ upon whether the fool kid acted like
he’d got over it or not.”

“Listen, judge,” said Curly. “From the minute she ’lowed she was
going to eat with Jack Marling, I’ve been looking at things different.
I don’t s’pose she could understand that starting right out to try to
find another lady was a sort of—a sort of getting square, as you
might say.”
“I don’t suppose she could—not right away,” Pres replied. “But
time and good fruits of repentance has given her confidence in many
a hawse that was a right bad bronc when she first forked him. So
long, son! Don’t go to frettin’ too much—about anything.”
Out on the street again, Campbell said to Graney:
“What sort of place is that Monaco Cabaret?”
“Bum!” the detective answered. “But prosperous. The gang that
hangs out there has plenty money, these days.”
“Bootleggers among ’em, maybe?”
“And hijackers and a few other things. And sports that like to
travel with ’em.”
“Just between ourselves, did you ever hear of a young lady named
Pearl Florrine?”
“‘The Red Pearl?’” Graney replied promptly. “Some stepper!”
“Red?”
“Fits her two or three ways. For one thing, she always wears it.
Another, she trains with Reds, anarchists, or communists or sump’n
—I don’t pretend to know just which kind they belong to. Her
regular married name is Ricotti, although Angelo don’t go by it.”
“Angelo?”
“Her husband. He calls his last name ‘Rich.’ ‘Quick’ Rich is how the
gang knows him. Got it—though we’ve never been able to convict
him—by his speed in pulling a gat.”
“A gunman?”
“Sure. What’s all this got——”
“Where is he?”
“He’s been out o’ town the last week or so, but I seen a report
from one of our railroad station men that he got back, unexpected,
about six o’clock tonight—last night, I mean; it’s morning now.”
“Mr. Graney,” promised Campbell with confidence, “you take me to
Angelo Ricotti, and think up a good way to get him mad and
talkative, and I’ll give you a laugh on Mr. Detective Moore that he
won’t get over till Texas is annexed back to Mexico.”

Briefly, he went into details. Unhesitatingly, enthusiastically,

Detective Graney agreed with him.
It was a little past three o’clock when they found Quick Rich in the
back room of a hang-out whose sentry they and the policeman on
the beat had succeeded in suppressing without any alarm being
given. One other man was present and Campbell seized and
disarmed him while Graney jammed a pistol into Rich’s midriff and
took from his coat a .38 automatic with its barrel powder stained.
“It’s no good, Quick,” the detective said, when the handcuffs were
on. “We know all about the killing. The Pearl turned you in.”
“So she was there, was she?” raved Angelo. “If I’d seen her, I’d ’a’
made a double job of it. Well, I got him anyway, the whelp! Waving
his hand at her every day in the grand stand in front of five
thousand people—and her waving back! And the nerve to take her
out and make a fool of me to the whole gang! And Pearl—just
because we had some words—kidding him along, with his big hat
and cowboy clothes and red handkerchief!”
 “You identified him by his red handkerchief, of course, just as he
was heading into the side door of The Monaco,” Pres suggested
mildly.
“Sure I did! They told me he was the only one of that wild-West
crowd that ever wore one. Who are you?”
“Mr. Campbell,” said Detective Graney unctuously, “is a guy from
Texas that used to be a Roughrider. And him and me is going to do
some more roughridin’—with a certain know-it-all gent to be rode—
along about court time in the mornin’.”
“Moore was right at that, in a way,” murmured the ex-ranger as
the patrolman left to ring for the patrol. “‘Look for the woman;’
that’s as good a rule in some killin’s in Texas as it is here in the East.
And I followed his hunch and did the same thing. But down in my
part of the country we use words some different. When we say
women, we usually don’t mean ladies.”

Transcriber’s Note: This story appeared in the September 20,

1925 issue of The Popular Magazine.
*** END OF THE PROJECT GUTENBERG EBOOK SPLASHES OF RED
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give you a second opportunity to receive the work electronically in
lieu of a refund. If the second copy is also defective, you may
demand a refund in writing without further opportunities to fix the
problem.

1.F.4. Except for the limited right of replacement or refund set forth
in paragraph 1.F.3, this work is provided to you ‘AS-IS’, WITH NO
OTHER WARRANTIES OF ANY KIND, EXPRESS OR IMPLIED,