Recent Advances on Electronic Transport Materials in OLEDs

TANG Zhenyu; GUO Haoqing; XIAO Jing; CHEN Zhijian; XIAO Lixin

doi:10.37188/CJL.20220253

您当前的位置：

首页 >

文章列表页 >

Recent Advances on Electronic Transport Materials in OLEDs

Invited Paper | 更新时间：2023-02-16

- Recent Advances on Electronic Transport Materials in OLEDs
  增强出版
- Chinese Journal of Luminescence Vol. 44, Issue 1, Pages: 26-36(2023)
- 作者机构：
  
  1.北京大学物理学院，人工微结构和介观物理国家重点实验室，北京　100871
  2.泰山学院物理与电子工程学院，山东泰安　271000
- 作者简介：
- 基金信息：
  
  National Natural Science Foundation of China(61935016;52173153;12174013);Natural Science Foundation of Shandong Province(ZR2022MF271);Talent Introduction and Education Program for Youth Innovation teams in Shandong Colleges and Universities(2019)
- DOI：10.37188/CJL.20220253
  CLC： O482.31
- Published：05 January 2023，
  
  Received：25 June 2022，
  
  Revised：15 July 2022，
扫描看全文
唐振宇,郭浩清,肖静等.OLED电子传输材料研究进展[J].发光学报,2023,44(01):26-36.

TANG Zhenyu,GUO Haoqing,XIAO Jing,et al.Recent Advances on Electronic Transport Materials in OLEDs[J].Chinese Journal of Luminescence,2023,44(01):26-36.
唐振宇,郭浩清,肖静等.OLED电子传输材料研究进展[J].发光学报,2023,44(01):26-36. DOI： 10.37188/CJL.20220253.

TANG Zhenyu,GUO Haoqing,XIAO Jing,et al.Recent Advances on Electronic Transport Materials in OLEDs[J].Chinese Journal of Luminescence,2023,44(01):26-36. DOI： 10.37188/CJL.20220253.

摘要

有机电致发光（OLED）是目前最有竞争力的显示技术，市场占有量逐年攀升。高效、稳定的OLED，特别是深蓝光器件，性能仍需提升，其关键问题是高性能的电子传输材料的研发。这是由于有机分子难以获得较高电子迁移率，器件中的复合区域通常靠近电子传输层一侧，这就要求电子传输材料需要具有较高三线态能级来限域激子，尤其是高能量的蓝光激子。而高三线态（弱共轭）和高迁移率（强共轭）一直是有机分子设计中难以调和的矛盾，此外更宽的带隙也会导致较差的热稳定性，这些难题始终限制着OLED电子传输材料的发展。本文分类介绍了高性能的电子传输材料所需要具备的几点特性，包括热稳定性、光化学稳定性、电子迁移率、前线轨道能级和三重态能级等，并且综述了21世纪以来OLED小分子电子传输材料的重要研究进展，以期对未来开发理想的电子传输材料提供参考。

Abstract

Organic light emitting diodes （OLED） technology is considered to be the next generation of display technology， and has gradually occupied the mainstream of the market， but the performance of OLED is still largely limited by electron transport materials， especially in high-performance deep blue light devices. Because it is difficult for organic molecules to obtain high electron mobility， and the recombination zone in the device is usually close to the interface of the electron transport layer， which requires the electron transport material to have a high triplet energy level to confine the exciton， especially the blue light exciton with high energy. However， high triplet states （poor conjugation） and high mobility （strong conjugation） have always been difficult to reconcile in the design of organic molecules， and a wider band gap will also lead to poorer thermal stability. These problems have been affecting the development of OLED electronic transport materials. In this paper， several elements of high performance electronic transport materials are introduced， including thermal stability， photochemical stability， electron mobility， the frontier orbital and the triplet energy level and so on. And the important research progresses of the micromolecular electron transport materials in 21st century are summarized， in order to provide the reference for the development of the ideal electronic transfer materials in the future.

关键词

有机电致发光电子传输材料稳定性电子迁移率三重态能级

Keywords

organic light-emitting diodeselectronic transport materialsstabilityelectron mobilitytriplet energy

references

TANG C W， VANSLYKE S A. Organic electroluminescent diodes ［J］. Appl. Phys. Lett.， 1987， 51（12）： 913-915. doi: 10.1063/1.98799http://dx.doi.org/10.1063/1.98799

KIDO J， IIZUMI Y. Fabrication of highly efficient organic electroluminescent devices ［J］. Appl. Phys. Lett.， 1998， 73（19）： 2721-2723. doi: 10.1063/1.122570http://dx.doi.org/10.1063/1.122570

MA Y G， ZHANG H Y， SHEN J C， et al. Electroluminescence from triplet metal-ligand charge-transfer excited state of transition metal complexes ［J］. Synth. Met.， 1998， 94（3）： 245-248. doi: 10.1016/s0379-6779(97)04166-0http://dx.doi.org/10.1016/s0379-6779(97)04166-0

BALDO M A， O'BRIEN D F， YOU Y， et al. Highly efficient phosphorescent emission from organic electroluminescent devices ［J］. Nature， 1998， 395（6698）： 151-154. doi: 10.1038/25954http://dx.doi.org/10.1038/25954

ENDO A， OGASAWARA M， TAKAHASHI A， et al. Thermally activated delayed fluorescence from Sn4+-porphyrin complexes and their application to organic light emitting diodes—A novel mechanism for electroluminescence ［J］. Adv. Mater.， 2009， 21（47）： 4802-4806. doi: 10.1002/adma.200900983http://dx.doi.org/10.1002/adma.200900983

UOYAMA H， GOUSHI K， SHIZU K， et al. Highly efficient organic light-emitting diodes from delayed fluorescence ［J］. Nature， 2012， 492（7428）： 234-239. doi: 10.1038/nature11687http://dx.doi.org/10.1038/nature11687

XU Z， TANG B Z， WANG Y， et al. Recent advances in high performance blue organic light-emitting diodes based on fluorescence emitters ［J］. J. Mater. Chem. C， 2020， 8（8）： 2614-2642. doi: 10.1039/c9tc06441ahttp://dx.doi.org/10.1039/c9tc06441a

ZHANG D D， DUAN L. TADF sensitization targets deep-blue ［J］. Nat. Photonics， 2021， 15（3）： 173-174. doi: 10.1038/s41566-021-00765-3http://dx.doi.org/10.1038/s41566-021-00765-3

HUSAIN A， KIM S M， KIM J H， et al. Thermal performance analysis and optimization of microjet cooling of high-power light-emitting diodes ［J］. J. Thermophys. Heat Transf.， 2013， 27（2）： 235-245. doi: 10.2514/1.t3931http://dx.doi.org/10.2514/1.t3931

GÄRDITZ C， WINNACKER A， SCHINDLER F， et al. Impact of Joule heating on the brightness homogeneity of organic light emitting devices ［J］. Appl. Phys. Lett.， 2007， 90（10）： 103506-1-3. doi: 10.1063/1.2711708http://dx.doi.org/10.1063/1.2711708

KIM J， LEE H H. Wave formation by heating in thin metal film on an elastomer ［J］. J. Polym. Sci. Part B Polym. Phys.， 2001， 39（11）： 1122-1128. doi: 10.1002/polb.1088http://dx.doi.org/10.1002/polb.1088

SAVVATE’EV V N， YAKIMOV A V， DAVIDOV D， et al. Degradation of nonencapsulated polymer-based light-emitting diodes： noise and morphology ［J］. Appl. Phys. Lett.， 1997， 71（23）： 3344-3346. doi: 10.1063/1.120332http://dx.doi.org/10.1063/1.120332

AZIZ H， POPOVIC Z D， HU N X， et al. Degradation mechanism of small molecule-based organic light-emitting devices ［J］. Science， 1999， 283（5409）： 1900-1902. doi: 10.1126/science.283.5409.1900http://dx.doi.org/10.1126/science.283.5409.1900

KONDAKOV D Y， LENHART W C， NICHOLS W F. Operational degradation of organic light-emitting diodes： mechanism and identification of chemical products ［J］. J. Appl. Phys.， 2007， 101（2）： 024512-1-7. doi: 10.1063/1.2430922http://dx.doi.org/10.1063/1.2430922

SCHOLZ S， CORTEN C， WALZER K， et al. Photochemical reactions in organic semiconductor thin films ［J］. Org. Electron.， 2007， 8（6）： 709-717. doi: 10.1016/j.orgel.2007.06.002http://dx.doi.org/10.1016/j.orgel.2007.06.002

WANG R， WANG Y L， LIN N， et al. Effects of ortho-linkages on the molecular stability of organic light-emitting diode materials ［J］. Chem. Mater.， 2018， 30（24）： 8771-8781. doi: 10.1021/acs.chemmater.8b03142http://dx.doi.org/10.1021/acs.chemmater.8b03142

BIAN M Y， ZHANG D D， WANG Y X， et al. Long-lived and highly efficient TADF-PhOLED with “（A）n-D-（A）n” structured terpyridine electron-transporting material ［J］. Adv. Funct. Mater.， 2018， 28（28）： 1800429-1-9. doi: 10.1002/adfm.201800429http://dx.doi.org/10.1002/adfm.201800429

LIU Z G， PINTO J， SOARES J， et al. Efficient multilayer organic light emitting diode ［J］. Synth. Met.， 2001， 122（1）： 177-179. doi: 10.1016/s0379-6779(00)01374-6http://dx.doi.org/10.1016/s0379-6779(00)01374-6

MATSUSHIMA T， ADACHI C. Extremely low voltage organic light-emitting diodes with p-doped alpha-sexithiophene hole transport and n-doped phenyldipyrenylphosphine oxide electron transport layers ［J］. Appl. Phys. Lett.， 2006， 89（25）： 253506-1-3. doi: 10.1063/1.2410236http://dx.doi.org/10.1063/1.2410236

CHANG C C， CHEN J F， HWANG S W， et al. Highly efficient white organic electroluminescent devices based on tandem architecture ［J］. Appl. Phys. Lett.， 2005， 87（25）： 253501-1-3. doi: 10.1063/1.2147730http://dx.doi.org/10.1063/1.2147730

LUO J X， XIAO L X， CHEN Z J， et al. Highly efficient organic light emitting devices with insulator MnO as an electron injecting and transporting material ［J］. Appl. Phys. Lett.， 2008， 93（13）： 133301-1-3. doi: 10.1063/1.2960349http://dx.doi.org/10.1063/1.2960349

PU Y J， MIYAMOTO M， NAKAYAMA K I， et al. Lithium phenolate complexes for an electron injection layer in organic light-emitting diodes ［J］. Org. Electron.， 2009， 10（2）： 228-232. doi: 10.1016/j.orgel.2008.11.003http://dx.doi.org/10.1016/j.orgel.2008.11.003

CHIBA T， PU Y J， IDE T， et al. Addition of lithium 8-quinolate into polyethylenimine electron-injection layer in OLEDs： not only reducing driving voltage but also improving device lifetime ［J］. ACS Appl. Mater. Interfaces， 2017， 9（21）： 18113-18119. doi: 10.1021/acsami.7b02658http://dx.doi.org/10.1021/acsami.7b02658

ZHENG X Y， WU Y Z， SUN R G， et al. Efficiency improvement of organic light-emitting diodes using 8-hydroxy-quinolinato lithium as an electron injection layer ［J］. Thin Solid Films， 2005， 478（1-2）： 252-255. doi: 10.1016/j.tsf.2004.08.020http://dx.doi.org/10.1016/j.tsf.2004.08.020

BIN Z Y， DONG G F， WEI P C， et al. Making silver a stronger n-dopant than cesium via in situ coordination reaction for organic electronics ［J］. Nat. Commun.， 2019， 10（1）： 866-1-7. doi: 10.1038/s41467-019-08821-xhttp://dx.doi.org/10.1038/s41467-019-08821-x

XIAO L X， CHEN Z J， QU B， et al. Recent progresses on materials for electrophosphorescent organic light-emitting devices ［J］. Adv. Mater.， 2011， 23（8）： 926-952. doi: 10.1002/adma.201003128http://dx.doi.org/10.1002/adma.201003128

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

DUAN K， ZHU Y H， LIU Z， et al. A wide-bandgap， high-mobility electron-transporting material containing a 9，9'-spirobithioxanthene skeleton ［J］. Chem. Eng. J.， 2022， 429： 132215. doi: 10.1016/j.cej.2021.132215http://dx.doi.org/10.1016/j.cej.2021.132215

BRINKMANN M， GADRET G， MUCCINI M， et al. Correlation between molecular packing and optical properties in different crystalline polymorphs and amorphous thin films of mer-tris（8-hydroxyquinoline）aluminum（Ⅲ）［J］. J. Am. Chem. Soc.， 2000， 122（21）： 5147-5157. doi: 10.1021/ja993608khttp://dx.doi.org/10.1021/ja993608k

YEH S J， WU M F， CHEN C T， et al. New dopant and host materials for blue-light-emitting phosphorescent organic electroluminescent devices ［J］. Adv. Mater.， 2005， 17（3）： 285-289. doi: 10.1002/adma.200401373http://dx.doi.org/10.1002/adma.200401373

LI Y Q， FUNG M K， XIE Z Y， et al. An efficient pure blue organic light-emitting device with low driving voltages ［J］. Adv. Mater.， 2002， 14（18）： 1317-1321. doi: 10.1002/1521-4095(20020916)14:18<1317::aid-adma1317>3.0.co;2-shttp://dx.doi.org/10.1002/1521-4095(20020916)14:18<1317::aid-adma1317>3.0.co;2-s

NAKA S， OKADA H， ONNAGAWA H， et al. High electron mobility in bathophenanthroline ［J］. Appl. Phys. Lett.， 2000， 76（2）： 197-199. doi: 10.1063/1.125701http://dx.doi.org/10.1063/1.125701

WU I W， WANG P S， TSENG W H， et al. Correlations of impedance-voltage characteristics and carrier mobility in organic light emitting diodes ［J］. Org. Electron.， 2012， 13（1）： 13-17. doi: 10.1016/j.orgel.2011.09.016http://dx.doi.org/10.1016/j.orgel.2011.09.016

SU S J， CHIBA T， TAKEDA T， et al. Pyridine-containing triphenylbenzene derivatives with high electron mobility for highly efficient phosphorescent OLEDs ［J］. Adv. Mater.， 2008， 20（11）： 2125-2130. doi: 10.1002/adma.200701730http://dx.doi.org/10.1002/adma.200701730

SU S J， TAKAHASHI Y， CHIBA T， et al. Structure-property relationship of pyridine-containing triphenyl benzene electron-transport materials for highly efficient blue phosphorescent OLEDs ［J］. Adv. Funct. Mater.， 2009， 19（8）： 1260-1267. doi: 10.1002/adfm.200800809http://dx.doi.org/10.1002/adfm.200800809

SU S J， GONMORI E， SASABE H， et al. Highly efficient organic blue-and white-light-emitting devices having a carrier- and exciton-confining structure for reduced efficiency roll-off ［J］. Adv. Mater.， 2008， 20（21）： 4189-4194.

DAISAKU T D， TAKASHI T， TAKAYUKI C， et al. Novel electron-transport material containing boron atom with a high triplet excited energy level ［J］. Chem. Lett.， 2007， 36（2）： 262-263. doi: 10.1246/cl.2007.262http://dx.doi.org/10.1246/cl.2007.262

TANAKA D， SASABE H， LI Y J， et al. Ultra high efficiency green organic light-emitting devices ［J］. Jpn. J. Appl. Phys.， 2007， 46（1L）： L10-L12. doi: 10.1143/jjap.46.l10http://dx.doi.org/10.1143/jjap.46.l10

SASABE H， CHIBA T， SU S J， et al. 2-Phenylpyrimidine skeleton-based electron-transport materials for extremely efficient green organic light-emitting devices ［J］. Chem. Commun.， 2008，（44）： 5821-5823. doi: 10.1039/b812270ahttp://dx.doi.org/10.1039/b812270a

SASABE H， TANAKA D， YOKOYAMA D， et al. Influence of substituted pyridine rings on physical properties and electron mobilities of 2-methylpyrimidine skeleton-based electron transporters ［J］. Adv. Funct. Mater.， 2011， 21（2）： 336-342. doi: 10.1002/adfm.201001252http://dx.doi.org/10.1002/adfm.201001252

SASABE H， NAKANISHI H， WATANABE Y， et al. Extremely low operating voltage green phosphorescent organic light-emitting devices ［J］. Adv. Funct. Mater.， 2013， 23（44）： 5550-5555. doi: 10.1002/adfm.201301069http://dx.doi.org/10.1002/adfm.201301069

XIAO L X， LAN H， KIDO J. Highly efficient electron-transporting phenanthroline derivatives for electroluminescent devices ［J］. Chem. Lett.， 2007， 36（6）： 802-803. doi: 10.1246/cl.2007.802http://dx.doi.org/10.1246/cl.2007.802

XIAO L X， SU S J， AGATA Y， et al. Nearly 100% internal quantum efficiency in an organic blue-light electrophosphorescent device using a weak electron transporting material with a wide energy gap ［J］. Adv. Mater.， 2009， 21（12）： 1271-1274. doi: 10.1002/adma.200802034http://dx.doi.org/10.1002/adma.200802034

XIAO L X， QI B Y， XING X， et al. A weak electron transporting material with high triplet energy and thermal stability via a super twisted structure for high efficient blue electrophosphorescent devices ［J］. J. Mater. Chem.， 2011， 21（47）： 19058-19062. doi: 10.1039/c1jm13488dhttp://dx.doi.org/10.1039/c1jm13488d

XING X， ZHANG L P， LIU R， et al. A deep-blue emitter with electron transporting property to improve charge balance for organic light-emitting device ［J］. ACS Appl. Mater. Interfaces， 2012， 4（6）： 2877-2880. doi: 10.1021/am300685bhttp://dx.doi.org/10.1021/am300685b

BIAN M Y， WANG Y X， GUO X， et al. Positional isomerism effect of spirobifluorene and terpyridine moieties of “（A）n-D-（A）n” type electron transport materials for long-lived and highly efficient TADF-PhOLEDs ［J］. J. Mater. Chem. C， 2018， 6（38）： 10276-10283. doi: 10.1039/c8tc03796ehttp://dx.doi.org/10.1039/c8tc03796e

GUO X， BIAN M Y， LV F， et al. Increasing electron transporting properties and horizontal molecular orientation via meta-position of nitrogen for “（A）n‐D‐（A）n” structured terpyridine electron-transporting material ［J］. J. Mater. Chem. C， 2019， 7（37）： 11581-11587. doi: 10.1039/c9tc03787jhttp://dx.doi.org/10.1039/c9tc03787j

GUO X， LV F， ZHAO Z F， et al. Spirobifluorene-based oligopyridine derivatives as electron-transporting materials for green phosphorescent organic light-emitting diodes ［J］. Org. Electron.， 2020， 77： 105498-1-8. doi: 10.1016/j.orgel.2019.105498http://dx.doi.org/10.1016/j.orgel.2019.105498

GUO X， TANG Z Y， YU W J， et al. A high thermal stability terpyridine derivative as the electron transporter for long-lived green phosphorescent OLED ［J］. Org. Electron.， 2021， 89： 106048-1-7. doi: 10.1016/j.orgel.2020.106048http://dx.doi.org/10.1016/j.orgel.2020.106048

ZHANG D D， QIAO J， ZHANG D Q， et al. Ultrahigh-efficiency green PHOLEDs with a voltage under 3 V and a power efficiency of nearly 110 lm·W-1 at luminance of 10 000 cd·m-2 ［J］. Adv. Mater.， 2017， 29（40）： 1702847-1-8. doi: 10.1002/adma.201702847http://dx.doi.org/10.1002/adma.201702847

ZHANG D D， WEI P C， ZHANG D Q， et al. Sterically shielded electron transporting material with nearly 100% internal quantum efficiency and long lifetime for thermally activated delayed fluorescent and phosphorescent OLEDs ［J］. ACS Appl. Mater. Interfaces， 2017， 9（22）： 19040-19047. doi: 10.1021/acsami.7b04391http://dx.doi.org/10.1021/acsami.7b04391

WANG F F， HU J， CAO X D， et al. A low-cost phenylbenzoimidazole containing electron transport material for efficient green phosphorescent and thermally activated delayed fluorescent OLEDs ［J］. J. Mater. Chem. C， 2015， 3（21）： 5533-5540. doi: 10.1039/c5tc00350dhttp://dx.doi.org/10.1039/c5tc00350d

JEON S O， JANG S E， SON H S， et al. External quantum efficiency above 20% in deep blue phosphorescent organic light-emitting diodes ［J］. Adv. Mater.， 2011， 23（12）： 1436-1441. doi: 10.1002/adma.201004372http://dx.doi.org/10.1002/adma.201004372

HUNG W Y， FANG G C， LIN S W， et al. The first tandem， all-exciplex-based WOLED ［J］. Sci. Rep.， 2015， 4： 5161-1-6. doi: 10.1038/srep05161http://dx.doi.org/10.1038/srep05161

SHIN H， LEE J H， MOON C K， et al. Sky-blue phosphorescent OLEDs with 34.1% external quantum efficiency using a low refractive index electron transporting layer ［J］. Adv. Mater.， 2016， 28（24）： 4920-4925. doi: 10.1002/adma.201506065http://dx.doi.org/10.1002/adma.201506065

Views

554

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

CJL | OLED: the advances for ETL

Effect of Aqueous Electrolyte Ions on Electrochromic Properties of Amorphous WO₃

Progress of Two-dimensional Perovskite Solar Cells Based on Aromatic Organic Spacers

Degradation Mechanism of Organic Light-emitting Diodes

In-situ Synthesis and Performance of Sodium Chloride/ Cesium Lead Bromide Perovskite Composite Film

Related Author

Zhenyu Tang

Haoqing Guo

Zhijian Chen

Lixin Xiao

Jing Xiao

XING Kaixiao

LYU Zhe

LI Yantao

Related Institution

State Key Laboratory for Artificial Microstructures and Mesoscopic Physics， Department of Physics， Peking University

School of Mathematics， Jilin University

University of Chinese Academy of Sciences

State Key Laboratory of Luminescence and Applications， Changchun Institute of Optics， Fine Mechanics and Physics， Chinese Academy of Sciences

Institute of Polymer Chemistry， College of Chemistry， Nankai University

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰