通过拓展D⁃π⁃A结构中的π桥实现高效紫蓝光有机发光器件（CIE<italic style="font-style: italic"><sub>y</sub></italic>=0.046）

崔江峰; 孙静; 王国良; 王智恒; 杨晓东; 许慧侠; 苗艳勤; 王龙; 于军胜; 王华

doi:10.37188/CJL.20220093

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通过拓展D⁃π⁃A结构中的π桥实现高效紫蓝光有机发光器件（CIE_y=0.046）

器件制备及器件物理 | 更新时间：2022-08-01

- 通过拓展D⁃π⁃A结构中的π桥实现高效紫蓝光有机发光器件（CIE_y=0.046）
  增强出版
- Achieving Efficient Violet-blue Organic Light Emitting Devices （CIE_y=0.046） by Extending π-conjugation in D-π-A Structure
- 发光学报 2022年43卷第7期页码：1102-1113
- 作者机构：
  
  1.太原理工大学新材料界面科学与工程教育部重点实验室，山西太原　030024
  2.山西⁃浙大先进材料与化学工程研究所，山西太原　030024
  3.电子科技大学光电信息学院电子薄膜与集成器件国家重点实验室，四川成都　610054
- 作者简介：
  
  [ "崔江峰（1995-），男，河北沧州人，硕士研究生，2018年于河北科技大学获得学士学位，主要从事有机光电材料与器件的研究。Email: 1689813420@qq. com" ]
  [ "孙静（1987-），女，山东潍坊人，博士，讲师，2016年于太原理工大学获得博士学位，主要从事有机光电功能材料的研究。Email: sunjing@tyut.edu.cn" ]
  [ "王华（1977-），男，山西平定人，博士，教授，博士生导师，2007 年于太原理工大学获得博士学位，主要从事有机半导体光电材料与器件的研究 Email: wanghua001@tyut.edu.cn" ]
- 基金信息：
  
  国家自然科学基金(62074109;6207031407);山西省自然科学基金(201901D211090;201901D111108);国家自然科学基金联合基金(U21A20492);Research Project Supported by Shanxi Scholarship Council of China(2020⁃049)
- DOI：10.37188/CJL.20220093
  中图分类号： TN312.8
- 纸质出版日期：2022-07-05，
  
  收稿日期：2022-03-18，
  
  修回日期：2022-04-05，
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崔江峰,孙静,王国良等.通过拓展D⁃π⁃A结构中的π桥实现高效紫蓝光有机发光器件（CIE_y=0.046）[J].发光学报,2022,43(07):1102-1113.

CUI Jiang-feng,SUN Jing,WANG Guo-liang,et al.Achieving Efficient Violet-blue Organic Light Emitting Devices （CIE_y=0.046） by Extending π-conjugation in D-π-A Structure[J].Chinese Journal of Luminescence,2022,43(07):1102-1113.
崔江峰,孙静,王国良等.通过拓展D⁃π⁃A结构中的π桥实现高效紫蓝光有机发光器件（CIE_y=0.046）[J].发光学报,2022,43(07):1102-1113. DOI： 10.37188/CJL.20220093.

CUI Jiang-feng,SUN Jing,WANG Guo-liang,et al.Achieving Efficient Violet-blue Organic Light Emitting Devices （CIE_y=0.046） by Extending π-conjugation in D-π-A Structure[J].Chinese Journal of Luminescence,2022,43(07):1102-1113. DOI： 10.37188/CJL.20220093.

摘要

紫蓝光有机发光材料在全彩显示和照明领域具有广阔的应用前景。但是该类材料需要宽能隙，因此开发高效的紫蓝色材料是一项巨大的挑战。本文利用10H⁃吩噻嗪5，5⁃二氧化物（2OPTZ）作为弱受体、N⁃苯基⁃2⁃萘胺（PNA）作为供体，设计合成了两个具有D⁃π⁃A型结构的紫蓝色材料，命名为2OPTZ⁃PNA和2OPTZ⁃BP⁃PNA。通过延长给受体之间的π共轭长度，使局域态和电荷转移态被优化，并且薄膜中的绝对量子产率从14%提高到33%。此外，利用2OPTZ⁃BP⁃PNA制备的非掺杂器件呈现紫蓝光（436 nm）发射，半峰全宽为54 nm，色坐标为（0.155，0.046），外量子效率为4.1%。鉴于此，本文提供了一种制备高质量紫蓝发光材料的有效策略。

Abstract

Organic violet-blue luminescent materials have exhibited great potential in full-color displaying and lighting fields. However， it is a huge challenge to develop efficient violet-blue emitters because of the inherently wide energy gap. In this work， two violet-blue emitters with donor （D）-π-acceptor （A） type using 10H-phenothiazine 5，5-dioxide （2OPTZ） as a weak acceptor and N-（2-naphthyl） aniline （PNA） as the donor， namely 2OPTZ-PNA and 2OPTZ-BP-PNA， were designed and synthesized. By extending π-conjugation length between donor and acceptor， local excited states and charge transfer excited states were adjusted， and absolute photoluminescence quantum yields （PLQYs） values in the evaporated film increased from 14% to 33%. Notably， non-doped device based 2OPTZ-BP-PNA exhibits violet-blue light at 436 nm with a narrow full width at half-maximum （FWHM） of 54 nm， Commission Internationale de l’Eclairage （CIE） coordinates of （0.155， 0.046） and external quantum efficiency （EQE） of 4.1%. Given this， our results provide an efficient design strategy for the high-quality violet-blue luminescent materials.

关键词

有机发光二极管紫蓝色二氧化吩噻嗪D-π-A结构π共轭长度

Keywords

organic light-emitting diodes（OLED）violet-bluephenothiazine dioxideD-π-A structureπ-conjugation length

references

LIN C W，HAN P B，XIAO S，et al. Efficiency breakthrough of fluorescence OLEDs by the strategic management of “hot excitons” at highly lying excitation triplet energy levels ［J］. Adv. Funct. Mater.， 2021，31（48）：2106912-1-8. doi: 10.1002/adfm.202106912http://dx.doi.org/10.1002/adfm.202106912

XU R P，LI Y Q，TANG J X. Recent advances in flexible organic light-emitting diodes ［J］. J. Mater. Chem. C， 2016，4 （39）：9116-9142. doi: 10.1039/c6tc03230chttp://dx.doi.org/10.1039/c6tc03230c

YANG Z Y，MAO Z，XIE Z L，et al. Recent advances in organic thermally activated delayed fluorescence materials ［J］. Chem. Soc. Rev.， 2017，46（3）：915-1016. doi: 10.1039/c6cs00368khttp://dx.doi.org/10.1039/c6cs00368k

GUO X M，YUAN P S，FAN J Z，et al. Unraveling the important role of high-lying triplet-lowest excited singlet transitions in achieving highly efficient deep-blue AIE-based OLEDs ［J］. Adv. Mater.， 2021，33（11）：2006953-1-8. doi: 10.1002/adma.202006953http://dx.doi.org/10.1002/adma.202006953

贾钧森，王飞，赵波，等. D-π-A-π-D型小分子红光材料的制备及其性能［J］. 发光学报， 2020，41（1）：9-15. doi: 10.3788/fgxb20204101.0009http://dx.doi.org/10.3788/fgxb20204101.0009

JIA J S，WANG F，ZHAO B，et al. Design，synthesis and properties of D-π-A-π-D type organic red light luminogens ［J］. Chin. J. Lumin.， 2020，41（1）：9-15. （in Chinese）. doi: 10.3788/fgxb20204101.0009http://dx.doi.org/10.3788/fgxb20204101.0009

ZHANG Y M，WANG Y F，SONG J，et al. Near-infrared emitting materials via harvesting triplet excitons：molecular design，properties，and application in organic light emitting diodes ［J］. Adv. Opt. Mater.， 2018，6（18）：1800466-1-19. doi: 10.1002/adom.201800466http://dx.doi.org/10.1002/adom.201800466

CHEN W C，YUAN Y，NI S F，et al. Achieving efficient violet-blue electroluminescence with CIEy <0.06 and EQE>6% from naphthyl-linked phenanthroimidazole-carbazole hybrid fluorophores ［J］. Chem. Sci.， 2017，8（5）：3599-3608. doi: 10.1039/c6sc05619ahttp://dx.doi.org/10.1039/c6sc05619a

CHEN Z，LIU X K，ZHENG C J，et al. High performance exciplex-based fluorescence-phosphorescence white organic light-emitting device with highly simplified structure ［J］. Chem. Mater.， 2015，27（15）：5206-5211. doi: 10.1021/acs.chemmater.5b01188http://dx.doi.org/10.1021/acs.chemmater.5b01188

CHOU H H，CHEN Y H，HSU H P，et al. Synthesis of diimidazolylstilbenes as n-type blue fluorophores：alternative dopant materials for highly efficient electroluminescent devices ［J］. Adv. Mater.， 2012，24（43）：5867-5871. doi: 10.1002/adma.201202222http://dx.doi.org/10.1002/adma.201202222

SUN J，JIA J S，ZHAO B，et al. A purely organic D-π-A-π-D emitter with thermally activated delayed fluorescence and room temperature phosphorescence for near-white OLED ［J］. Chin. Chem. Lett.， 2021，32（4）：1367-1371. doi: 10.1016/j.cclet.2020.09.060http://dx.doi.org/10.1016/j.cclet.2020.09.060

CHEN W C，WU G F，YUAN Y，et al. A meta-molecular tailoring strategy towards an efficient violet-blue organic electroluminescent material ［J］. RSC Adv.， 2015，5（23）：18067-18074. doi: 10.1039/c4ra16954ahttp://dx.doi.org/10.1039/c4ra16954a

SHINAR J，SHINAR R. Organic light-emitting devices （OLEDs） and OLED-based chemical and biological sensors：an overview ［J］. J. Phys. D：Appl. Phys.， 2008，41（13）：133001-1-26. doi: 10.1088/0022-3727/41/13/133001http://dx.doi.org/10.1088/0022-3727/41/13/133001

TONGE C M，ZENG J J，ZHAO Z J，et al. Bis （hexamethylazatriangulene）sulfone：a high-stability deep blue-violet fluorophore with 100% quantum yield and CIEy < 0.07 ［J］. J. Mater. Chem. C， 2020，8（15）：5150-5155. doi: 10.1039/c9tc05938ehttp://dx.doi.org/10.1039/c9tc05938e

GAO Z，LIU Y L，WANG Z M，et al. High-efficiency violet-light-emitting materials based on phenanthro［9，10-d］imidazole ［J］. Chem. Eur. J.， 2013，19（8）：2602-2605. doi: 10.1002/chem.201203335http://dx.doi.org/10.1002/chem.201203335

THAKARE D S，OMANWAR S K，MUTHAL P L，et al. UV-emitting phosphors：synthesis，photoluminescence and applications ［J］. Phys. Status Solidi A， 2004， 201（3）：574-581. doi: 10.1002/pssa.200306720http://dx.doi.org/10.1002/pssa.200306720

LY K T，CHEN-CHENG R W，LIN H W，et al. Near-infrared organic light-emitting diodes with very high external quantum efficiency and radiance ［J］. Nat. Photonics， 2017，11（1）：63-68. doi: 10.1038/nphoton.2016.230http://dx.doi.org/10.1038/nphoton.2016.230

IM Y，BYUN S Y，KIM J H，et al. Recent progress in high-efficiency blue-light-emitting materials for organic light-emitting diodes ［J］. Adv. Funct. Mater.， 2017，27（13）：1603007-1-24. doi: 10.1002/adfm.201603007http://dx.doi.org/10.1002/adfm.201603007

WANG Z Q，YANG T T，DONG S F，et al. Anthracene and carbazole based asymmetric fluorescent materials for high-efficiency deep-blue non-doped organic light emitting devices with CIEy=0.06 ［J］. Dyes Pigments， 2022，199：110047. doi: 10.1016/j.dyepig.2021.110047http://dx.doi.org/10.1016/j.dyepig.2021.110047

WANG S M，ZHANG H Y，ZHANG B H，et al. Towards high-power-efficiency solution-processed OLEDs：material and device perspectives ［J］. Mater. Sci. Eng.：R：Rep.， 2020，140：100547-1-61. doi: 10.1016/j.mser.2020.100547http://dx.doi.org/10.1016/j.mser.2020.100547

HAN P B，LIN C W，MA D G，et al. Violet-blue emitters featuring aggregation-enhanced emission characteristics for nondoped OLEDs with CIEy smaller than 0.046 ［J］. ACS Appl. Mater. Interfaces， 2020，12（41）：46366-46372. doi: 10.1021/acsami.0c12722http://dx.doi.org/10.1021/acsami.0c12722

XIA G Q，QU C，ZHU Y L，et al. A TADF emitter featuring linearly arranged spiro-donor and spiro-acceptor groups：efficient nondoped and doped deep-blue OLEDs with CIEy <0.1 ［J］. Angew. Chem. Int. Ed.， 2021，60（17）：9598-9603. doi: 10.1002/anie.202100423http://dx.doi.org/10.1002/anie.202100423

卢国婧，廖小青，李璐，等. 基于扭曲A-π-D-π-A构型的蓝色荧光材料的π-共轭桥与光物理特性间的关系［J］. 发光学报， 2019，40（11）：1334-1347. doi: 10.3788/fgxb20194011.1334http://dx.doi.org/10.3788/fgxb20194011.1334

LU G J，LIAO X Q，LI L，et al. Relationship between π-conjugated bridge and photophysical properties of blue light-emitting fluorescent materials with twisting A-π-D-π-A configuration ［J］. Chin. J. Lumin.， 2019，40（11）：1334-1347.（in English）. doi: 10.3788/fgxb20194011.1334http://dx.doi.org/10.3788/fgxb20194011.1334

HAN C M，ZHAO F C，ZHANG Z，et al. Constructing low-triplet-energy hosts for highly efficient blue PHOLEDs：controlling charge and exciton capture in doping systems ［J］. Chem. Mater.， 2013，25（24）：4966-4976. doi: 10.1021/cm403160phttp://dx.doi.org/10.1021/cm403160p

FISHER A L，LINTON K E，KAMTEKAR K T，et al. Efficient deep-blue electroluminescence from an ambipolar fluorescent emitter in a single-active-layer device ［J］. Chem. Mater.， 2011，23（7）：1640-1642. doi: 10.1021/cm103314thttp://dx.doi.org/10.1021/cm103314t

RAJAMALLI P，CHEN D Y，SURESH S M，et al. Planar and rigid pyrazine-based TADF emitter for deep blue bright organic light-emitting diodes ［J］. Eur. J. Org. Chem.， 2021，2021（16）：2285-2293. doi: 10.1002/ejoc.202100086http://dx.doi.org/10.1002/ejoc.202100086

ZHANG J，YE H R，JIN Y X，et al. Recent progress in near-infrared organic electroluminescent materials ［J］. Top. Curr. Chem.， 2022，380（1）：6-1-40. doi: 10.1007/s41061-021-00357-3http://dx.doi.org/10.1007/s41061-021-00357-3

OUYANG X H，LI X L，ZHANG X Y，et al. Effective management of intramolecular charge transfer to obtain from blue to violet-blue OLEDs based on a couple of phenanthrene isomers ［J］. Dyes Pigments， 2015，122：264-271. doi: 10.1016/j.dyepig.2015.06.036http://dx.doi.org/10.1016/j.dyepig.2015.06.036

LI Z Q，LI C L，XU Y C，et al. Nonsymmetrical connection of two identical building blocks：constructing donor-acceptor molecules as deep blue emitting materials for efficient organic emitting diodes ［J］. J. Phys. Chem. Lett.， 2019，10（4）：842-847. doi: 10.1021/acs.jpclett.9b00300http://dx.doi.org/10.1021/acs.jpclett.9b00300

CHEN S，ZHANG C Y，XU H. Achieving host-free near-ultraviolet electroluminescence via electronic state engineering with phosphine oxide ［J］. Chem. Eng. J.， 2022，429：132327. doi: 10.1016/j.cej.2021.132327http://dx.doi.org/10.1016/j.cej.2021.132327

SHI J J，XU L，CHEN C，et al. Efficient and color-purity blue electroluminescence by manipulating the coupling forms of D-A hybrids with phenothiazine as the strong donor ［J］. Dyes Pigments， 2019，160：962-970. doi: 10.1016/j.dyepig.2018.08.055http://dx.doi.org/10.1016/j.dyepig.2018.08.055

CHEN Z，HO C L，WANG L Q，et al. Single-molecular white-light emitters and their potential WOLED applications ［J］. Adv. Mater.， 2020，32（11）：1903269-1-45. doi: 10.1002/adma.201903269http://dx.doi.org/10.1002/adma.201903269

WEI J B，LIANG B Y，DUAN R H，et al. Induction of strong long-lived room-temperature phosphorescence of N-Phenyl-2-naphthylamine molecules by confinement in a crystalline dibromobiphenyl matrix ［J］. Angew. Chem. Int. Ed.， 2016，55（50）：15589-15593. doi: 10.1002/anie.201607653http://dx.doi.org/10.1002/anie.201607653

XIANG S P，HUANG Z，SUN S Q，et al. Highly efficient non-doped OLEDs using aggregation-induced delayed fluorescence materials based on 10-phenyl-10H-phenothiazine 5，5-dioxide derivatives ［J］. J. Mater. Chem. C， 2018，6（42）：11436-11443. doi: 10.1039/c8tc03648ahttp://dx.doi.org/10.1039/c8tc03648a

ROUT Y，MONTANARI C，PASCIUCCO E，et al. Tuning the fluorescence and the intramolecular charge transfer of phenothiazine dipolar and quadrupolar derivatives by oxygen functionalization ［J］. J. Am. Chem. Soc.， 2021，143（26）：9933-9943. doi: 10.1021/jacs.1c04173http://dx.doi.org/10.1021/jacs.1c04173

YAO L，SUN S H，XUE S F，et al. Aromatic S-heterocycle and fluorene derivatives as solution-processed blue fluorescent emitters：structure-property relationships for different sulfur oxidation states ［J］. J. Phys. Chem. C， 2013，117（27）：14189-14196. doi: 10.1021/jp403463khttp://dx.doi.org/10.1021/jp403463k

GAO Y，ZHANG S T，PAN Y Y，et al. Hybridization and de-hybridization between the locally-excited （LE） state and the charge-transfer （CT） state：a combined experimental and theoretical study ［J］. Phys. Chem. Chem. Phys.， 2016，18（35）：24176-24184. doi: 10.1039/c6cp02778dhttp://dx.doi.org/10.1039/c6cp02778d

HOU M N，WANG H，MIAO Y Q，et al. Highly efficient deep-blue electroluminescence from a A‑π‑D‑π‑A structure based fluoresence material with exciton utilizing efficiency above 25% ［J］. ACS Appl. Energy Mater.， 2018，1（7）：3243-3254. doi: 10.1021/acsaem.8b00461http://dx.doi.org/10.1021/acsaem.8b00461

LI Y C，LI X L，CAI X Y，et al. Deep blue fluorophores incorporating sulfone-locked triphenylamine：the key for highly efficient fluorescence-phosphorescence hybrid white OLEDs with simplified structure ［J］. J. Mater. Chem. C， 2015，3（27）：6986-6996. doi: 10.1039/c5tc01373ahttp://dx.doi.org/10.1039/c5tc01373a

SHOER L E，EATON S W，MARGULIES E A，et al. Photoinduced electron transfer in 2，5，8，11-tetrakis-donor-substituted Perylene-3，4：9，10-bis （dicarboximides）［J］. J. Phys. Chem. B， 2015，119（24）：7635-7643. doi: 10.1021/jp511624shttp://dx.doi.org/10.1021/jp511624s

YU M X，ZHU X Y，ZENG J J，et al. Comparative study on the impact of through-space charge transfer over the electroluminescence performance of delayed fluorescence molecules ［J］. J. Mater. Chem. C， 2021，9（41）：14808-14814. doi: 10.1039/d1tc03564ahttp://dx.doi.org/10.1039/d1tc03564a

ZHANG Y，LAI S L，TONG Q X，et al. High efficiency nondoped deep-blue organic light emitting devices based on imidazole-π-triphenylamine derivatives ［J］. Chem. Mater.， 2012，24（1）：61-70. doi: 10.1021/cm201789uhttp://dx.doi.org/10.1021/cm201789u

TANG X Y，SHAN T，BAI Q，et al. Efficient deep-blue electroluminescence based on phenanthroimidazole-dibenzothiophene derivatives with different oxidation states of the sulfur atom ［J］. Chem. Asian J.， 2017，12（5）：552-560. doi: 10.1002/asia.201601626http://dx.doi.org/10.1002/asia.201601626

DU C Y，LIU F T，LIU H，et al. Non-doped organic light-emitting diodes based on phenanthroimidazole-triphenylamine derivatives with a low efficiency roll-off of 9% at a high luminance of 10 000 cd·m-2 ［J］. J. Mater. Chem. C， 2020，8（41）：14446-14452. doi: 10.1039/d0tc03379khttp://dx.doi.org/10.1039/d0tc03379k

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通过拓展D⁃π⁃A结构中的π桥实现高效紫蓝光有机发光器件（CIEy=0.046）

Achieving Efficient Violet-blue Organic Light Emitting Devices （CIEy=0.046） by Extending π-conjugation in D-π-A Structure

DOI：10.37188/CJL.20220093

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Abstract

关键词

Keywords

references

通过拓展D⁃π⁃A结构中的π桥实现高效紫蓝光有机发光器件（CIE_y=0.046）

Achieving Efficient Violet-blue Organic Light Emitting Devices （CIE_y=0.046） by Extending π-conjugation in D-π-A Structure