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CN-121991118-A - Indolo carbazole compound composition and organic electroluminescent device

CN121991118ACN 121991118 ACN121991118 ACN 121991118ACN-121991118-A

Abstract

The invention provides an indolocarbazole compound, a composition and an organic electroluminescent device. The indolocarbazole compound has a structure shown in a formula I. The structure of the indolocarbazole compound is designed, so that the indolocarbazole compound is suitable for being used as a main material of a luminescent layer of an organic electroluminescent device, and the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life.

Inventors

  • WANG ZHANQI
  • LI ZHIQIANG
  • GUO JINTAO
  • SONG BIN
  • HONG HAOZHI
  • LU JINBO
  • HUANG CHANGGANG

Assignees

  • 阜阳欣奕华新材料科技股份有限公司

Dates

Publication Date
20260508
Application Date
20241106

Claims (10)

  1. 1. The indolocarbazole compound is characterized by having a structure shown in the following formula I: Wherein Ar 1 、Ar 2 、Ar 3 is independently selected from C6-C40 aryl or C6-C30 heteroaryl, and any two of Ar 1 、Ar 2 、Ar 3 are linked by a single bond to form a ring; A 1 、A 2 、A 3 is independently selected from N or CR, and at least one is selected from N, R is selected from any one of H, C-C20 aryl or C1-C12 alkyl; Ar 11 is selected from the group of structures represented by the following formula A-1~A-10, ar 12 is selected from the group of structures represented by the following formulas A-1~A-2 and A-4~A-10, wherein ". Times. -indicates the attachment position: Ar 4 、Ar 5 、Ar 6、 Ar 7 is independently selected from C6-C40 aryl or C6-C30 heteroaryl; Y is selected from Si; The hydrogen atoms in the compounds of formula I may each independently be substituted with at least one of-D, -F, -CN, C6-C20 aryl, C1-C12 alkyl or C1-C12 alkoxy.
  2. 2. The indolocarbazole compound according to claim 1, wherein the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, triphenylenyl, and fluoranthenyl; Preferably, the C6-C30 heteroaryl is selected from any one of carbazolyl, dibenzothienyl or dibenzofuranyl; Preferably, the C6-C20 aryl is selected from any one of phenyl, biphenyl, terphenyl or naphthyl; preferably, the C1-C12 alkyl is selected from any one of methyl, ethyl, propyl, tertiary butyl or cyclohexyl; Preferably, the C1-C12 alkoxy is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy or hexoxy.
  3. 3. The indolocarbazole compound according to claim 1 or 2, wherein each Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 、Ar 6、 Ar 7 is independently selected from any one of phenyl, carbazolyl, biphenyl, naphthyl, triphenylene, dibenzothienyl or dibenzofuranyl; Preferably, each Ar 1 、Ar 2 、Ar 3 is independently selected from any one of phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl, and more preferably any one of phenyl, naphthyl or biphenyl; Preferably, each Ar 4 、Ar 5 、Ar 6、 Ar 7 is independently selected from any one of phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and further preferably phenyl; Preferably, ar 11 is selected from any one of a group shown in a formula A-1 to a group shown in a formula A-8; ar 4 、Ar 5 、Ar 6 、Ar 7 is selected from phenyl; Preferably, ar 11 is selected from the group represented by formula A-3; preferably, ar 12 is selected from any one of a group shown in a formula A-2, a group shown in a formula A-7 and a group shown in a formula A-10.
  4. 4. An indolocarbazole according to any of claims 1-3, wherein a 1 、A 2 、A 3 is selected from N; Preferably, the a 1 is selected from CR, R is selected from H, a 2 、A 3 is selected from N; preferably, the a 1 、A 3 is selected from CR, R is selected from H, a 2 is selected from N; Preferably, the hydrogen atoms in the indolocarbazoles are each independently substituted with at least one of-D, -F, -CN, phenyl, naphthyl, biphenyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, or butoxy; Preferably, the hydrogen atoms in the indolocarbazole compound can be substituted by at least one of-D, -F, -CN, phenyl, naphthyl, methyl, ethyl, tertiary butyl, methoxy and propoxy independently; Preferably, the hydrogen atoms in the indolocarbazole compound are each independently substituted with at least one of-D, -F, -CN, phenyl, naphthyl or biphenyl; Preferably, the hydrogen atoms in the compounds of formula I may each independently be substituted by —cn.
  5. 5. The indolocarbazole compound according to any one of claims 1 to 4, wherein the indolocarbazole compound has any one of structures represented by the following formulas I-1 to I-6: Wherein Ar 11 has the same definition as in claim 1.
  6. 6. The indolocarbazole compound according to any one of claims 1 to 5, wherein the indolocarbazole compound is selected from any one of the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the indolocarbazole compounds can be substituted by deuterium atoms independently.
  7. 7. A composition comprising, as a main ingredient, the composition comprises a first component and a second component; the first component comprising an indolocarbazole compound of any one of claims 1-6; The second component includes a compound having a structure represented by formula II: Wherein Ar 31 、Ar 32 is independently selected from any one of a single bond, a C6-C40 arylene group or a C6-C30 heteroarylene group; Ar 33 is any one of H, C-C40 aryl or C6-C30 heteroaryl; p1, p2 are each independently selected from 0, 1,2,3 or 4; The hydrogen atom in the compound of formula II may be substituted with at least one of deuterium atom, -F, -CN, C6-C20 aryl, C1-C12 alkyl, C1-C12 alkoxy, trimethylsilyl, triphenylsilyl, tetraphenylmethyl.
  8. 8. The composition of claim 7, wherein the compound of formula II is selected from any one of the following substituted or unsubstituted compounds: the substitution means that the hydrogen atoms in the above compounds may each independently be substituted with deuterium atoms.
  9. 9. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode; The organic thin film layer material comprises an indolocarbazole-based compound according to any one of claims 1 to 6 and/or a composition according to claim 7 or 8.
  10. 10. The organic electroluminescent device according to claim 9, wherein the organic thin film layer comprises a light-emitting layer, and a host material of the light-emitting layer comprises the indolocarbazole-based compound according to any one of claims 1 to 6; Preferably, the light emitting layer is a phosphorescent light emitting layer; preferably, the organic electroluminescent device is a green organic electroluminescent device.

Description

Indolo carbazole compound composition and organic electroluminescent device Technical Field The invention belongs to the technical field of organic electronic materials, and particularly relates to an indolocarbazole compound, a composition and an organic electroluminescent device. Background The organic electroluminescent device has a structure comprising an anode, a cathode and an organic layer therebetween. In order to improve efficiency and stability of the organic electroluminescent element, the organic material layer includes a plurality of layers having different materials, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a hole blocking layer, a light emitting layer, an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). Currently, organic electroluminescence has become a mainstream display technology, and accordingly, various novel OLED materials have been developed. The electron transport material, the hole injection material, the hole transport material or the hole blocking layer is a great obstacle to the comprehensive practical application of the OLED technology, and directly limits the luminous efficiency, the service life, the operating voltage and the like of the device. In order to meet the higher demands of OLED devices, there is a need in the art to develop more kinds of materials to improve the performance of OLED devices in terms of current efficiency, lifetime, etc. Disclosure of Invention Aiming at the defects of the prior art, the invention aims to provide an indolocarbazole compound, a composition and an organic electroluminescent device. The structure of the indolocarbazole compound is designed, so that the indolocarbazole compound is suitable for being used as a main material of a phosphorescence luminescent layer of an organic electroluminescent device, and the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life. To achieve the purpose, the invention adopts the following technical scheme: in a first aspect, the present invention provides an indolocarbazole compound, where the indolocarbazole compound has a structure shown in formula I below: Wherein Ar 1、Ar2、Ar3 is independently selected from C6-C40 aryl or C6-C30 heteroaryl, and any two of Ar 1、Ar2、Ar3 are linked by a single bond to form a ring; A 1、A2、A3 is independently selected from N or CR, and at least one is selected from N, R is selected from any one of H, C-C20 aryl or C1-C12 alkyl; Ar 11 is selected from the group of structures represented by the following formula A-1~A-10, ar 12 is selected from the group of structures represented by the following formulas A-1~A-2 and A-4~A-10, wherein ". Times. -indicates the attachment position: Ar 4、Ar5、Ar6、Ar7 is independently selected from C6-C40 aryl or C6-C30 heteroaryl; Y is selected from Si; The hydrogen atoms in the compounds of formula I may each independently be substituted with at least one of deuterium atoms (-D), -F, -CN, C6-C20 aryl, C1-C12 alkyl or C1-C12 alkoxy. The structure of the indolocarbazole compound is designed, so that the indolocarbazole compound is suitable for being used as a main material of a phosphorescence luminescent layer of an organic electroluminescent device, and the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life. In the present invention, C6-C40 may be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, C40, or the like. C6-C30 may be C6, C8, C10, C12, C16, C20, C24, C28, C30, etc. C6-C20 may be C6, C8, C10, C12, C16 or C20, etc. C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12. In the present invention, "-D" represents a deuterium atom, and the same applies to the following. The following is a preferred technical scheme of the present invention, but not a limitation of the technical scheme provided by the present invention, and the following preferred technical scheme can better achieve and achieve the objects and advantages of the present invention. As a preferable embodiment of the present invention, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, triphenylenyl and fluoranthenyl. As a preferable technical scheme of the invention, the C6-C30 heteroaryl is selected from any one of carbazolyl, dibenzothienyl and dibenzofuranyl. As a preferable technical scheme of the invention, the C6-C20 aryl is selected from any one of phenyl, biphenyl, terphenyl and naphthyl. As a preferable technical scheme of the invention, the C1-C12 alkyl is selected from any one of methyl, ethyl, propyl, tertiary butyl and cyclohexyl. As a preferable embodiment of the present invention, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy and hexoxy groups. As a preferred embodiment of the present invention, each of Ar 1、Ar2、Ar3、Ar4、Ar5、Ar6、Ar7 is independently selected fr