US-12624047-B2 - Organic compound and application thereof

US12624047B2US 12624047 B2US12624047 B2US 12624047B2US-12624047-B2

Abstract

Provided are an organic compound and an application thereof. The compound has a relatively deep LUMO energy level, which may reduce a potential barrier of electron transport, improve an electron injection capability and effectively reduce a voltage of an OLED device. The compounds each have a relatively deep HOMO energy level, which may effectively block holes so that more holes and electrons are recombined in a light-emitting region, achieving relatively high luminescence efficiency. An electron transport layer material and/or a hole blocking layer material suitable for the OLED device can reduce the voltage and power consumption of the device, improve the luminescence efficiency and extend a working lifetime so that the OLED device has better comprehensive performance.

Inventors

Quan RAN
Xinyuan ZHENG
Mingzhi Dai
YuHao LIU
Shuang CHENG
Ji NAN
Xiaolei PANG
Qingsong YUAN

Assignees

WUHAN TIANMA MICROELECTRONICS CO., LTD.
Wuhan Tianma Microelectronics Co., Ltd. Shanghai Branch

Dates

Publication Date: 20260512
Application Date: 20220218
Priority Date: 20211126

Claims (15)

1 . An organic compound having a structure represented by Formula I: wherein the ring A is any one of phenylene, biphenylene, naphthylene, terphenylene, pyridinylene or phenylene-naphthylene; wherein L is selected from a single bond, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C5-C30 heteroaryl; wherein X 1 to X 3 are independently selected from a C atom or a N atom, and at least one of X 1 to X 3 is N; wherein R 1 and R 2 are independently selected from substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C5-C30 heteroaryl; and wherein n 1 is an integer from 1 to 3.
2 . The organic compound according to claim 1 , wherein the organic compound has a structure represented by Formula II:
3 . The organic compound according to claim 1 , wherein when substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C5-C30 heteroaryl contains a substituent, the substituent is selected from at least one of deuterium, cyano, halogen, unsubstituted or halogenated C1-C10 linear or branched alkyl, unsubstituted or halogenated C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C5-C20 heteroaryl or C6-C18 arylamine.
4 . The organic compound according to claim 1 , wherein L is selected from any one of a single bond, phenylene, biphenylene, naphthylene, terphenylene, or pyridinylene.
5 . The organic compound according to claim 1 , wherein two of X 1 to X 3 are N or each of X 1 to X 3 is N.
6 . The organic compound according to claim 1 , wherein R 1 and R 2 are independently selected from any one of the following groups: wherein the dashed line represents a linkage site of the group; wherein L 1 is selected from any one of a single bond or substituted or unsubstituted C6-C20 arylene; wherein X 4 is selected from O, S or NR N1 ; wherein X 5 is selected from O, S, NR N2 or CR C3 R C4 ; wherein R N1 , R N2 , R C3 and R C4 are each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C5-C20 heteroaryl; wherein R 11 and R 12 are each independently selected from any one of deuterium, cyano, halogen, unsubstituted or halogenated C1-C10 linear or branched alkyl, unsubstituted or halogenated C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C5-C20 heteroaryl or C6-C18 arylamine; wherein m 1 is selected from an integer from 0 to 5; wherein m 2 is selected from an integer from 0 to 6; wherein m 3 is selected from an integer from 0 to 9; wherein m 4 and m 6 are each independently selected from an integer from 0 to 4; and wherein m 5 is selected from an integer from 0 to 3.
7 . The organic compound according to claim 6 , wherein R 1 and R 2 are independently selected from any one of the following groups, or any one of the following groups substituted with a substituent: wherein the dashed line represents a linkage site of the group; and wherein the substituted substituents are each independently selected from at least one of deuterium, cyano, halogen, unsubstituted or halogenated C1-C10 linear or branched alkyl, unsubstituted or halogenated C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl or C6-C18 arylamine.
8 . The organic compound according to claim 1 , wherein the organic compound is selected from any one of the following compounds:
9 . An electron transport layer material comprising the organic compound according to claim 1 .
10 . A hole blocking layer material comprising the organic compound according to claim 1 .
11 . An organic light-emitting diode (OLED) device, comprising an anode, a cathode and an organic thin film disposed between the anode and the cathode, wherein a material of the organic thin film comprises the organic compound according to claim 1 .
12 . The OLED device according to claim 11 , wherein the organic thin film comprises an electron transport layer, wherein a material of the electron transport layer comprises the organic compound.
13 . The OLED device according to claim 12 , wherein the organic thin film comprises a hole blocking layer, wherein a material of the hole blocking layer comprises the organic compound.
14 . A display panel, comprising the OLED device according to claim 11 .
15 . An electronic device, comprising the display panel according to claim 14 .

Description

CROSS-REFERENCE TO RELATED APPLICATION(S) This application claims priority to Chinese Patent Application No. CN 202111423743.6 filed Nov. 26, 2021, the disclosure of which is incorporated herein by reference in its entirety. TECHNICAL FIELD The present disclosure belongs to the technical field of organic electroluminescent materials and, in particular, to an organic compound and an application thereof. BACKGROUND An electron transport material used in a conventional electroluminescent device is Alq3. However, Alq3 has a relatively low electron mobility (of about 10−6 cm2/Vs), such that Alq3 cannot achieve a balance between electron transport and hole transport in the device. With the commercialization and practical application of electroluminescent devices, it is desired to obtain an ETL material with higher transport efficiency and better performance. In this field, researchers have made a large amount of exploratory work. WO 2007/011170 A1 and CN 101003508A of LG Chem disclose a series of derivatives of naphthoimidazole and pyrene, respectively, which are used as electron transport and injection materials in an electroluminescent device and improve luminescence efficiency of the device. In Publication Nos. US 2006/0204784 and US 2007/0048545, Eastman Kodak Company discloses an organic electroluminescent device using a hybrid electron transport material obtained by doping the following materials: (a) a first compound having a lowest LUMO energy level in the layer, (b) a second compound having a higher LUMO energy level than the first compound and a low turn-on voltage, and a metal material having a work function of less than 4.2 eV. However, the above electron transport material has a planar molecular structure and a large intermolecular attractive force, which are not conducive to evaporation and application. Further, the electron transport material has the disadvantages of relatively low mobility, poor energy level matching, poor thermal stability, a short lifetime, doping and the like, which limit the further development of OLED display devices. Therefore, to design and develop stable and efficient electron transport materials and/or electron injection materials that can have both high electron mobility and a high glass transition temperature and be effectively doped with a metal Yb or Liq has very important practical application value in reducing a threshold voltage, improving device efficiency and extending the lifetime of the device. In the market, commonly used electron transport materials such as batho-phenanthroline (BPhen), bathocuproine (BCP) and TmPyPB can generally meet market requirements for an organic electroluminescent panel. However, they have a relatively low glass transition temperature which is generally less than 85° C. When the device is working, generated Joule heat causes molecular degradation and a change in molecular structure, resulting in relatively low panel efficiency and relatively poor thermal stability. Moreover, the molecular structure has a very regular symmetry and is easy to crystallize after a long time. Once the electron transport material crystallizes, an intermolecular charge transition mechanism differs from the mechanism of the normally working amorphous film, resulting in poorer performance of the electron transport, an imbalance between electron mobility and hole mobility of the entire device and significantly reduced formation efficiency of excitons. Further, the formed excitons are concentrated at an interface between an electron transport layer and a light-emitting layer, resulting in significantly reduced device efficiency and a significantly shortened lifetime. Therefore, it is urgent to develop electron transport material with more types and better performance in the art to meet application requirements of the OLED display devices. SUMMARY In view of the deficiencies in the related art, an object of the present disclosure is to provide an organic compound and an application thereof. To achieve this object, the present disclosure adopts technical solutions described below. A first aspect of the present disclosure is to provide an organic compound having a structure represented by Formula I: The ring A is selected from a substituted or unsubstituted C6-C30 aryl ring or a substituted or unsubstituted C5-C30 heteroaryl ring. L is selected from a single bond, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C5-C30 heteroaryl. X1 to X3 are independently selected from a C atom or a N atom, and at least one of X1 to X3 is N. R1 and R2 are independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C5-C30 heteroaryl. n1 is an integer from 0 to 3. In the present disclosure, C5-C30 may each independently be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29 or the like. C6-C30 may each independently be C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28,