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CN-121991048-A - Compound and light-emitting element

CN121991048ACN 121991048 ACN121991048 ACN 121991048ACN-121991048-A

Abstract

The invention provides a compound, a photoelectric conversion element and a light-emitting element containing the compound. The compound has specific structures of an azabenzene main body and a dibenzoheterocycle main body, and the specific structures are shown in a general formula 1: According to the present invention, an organic thin film light-emitting element that achieves high light-emitting efficiency, low driving voltage, and long durability at the same time can be provided.

Inventors

  • CHEN MIAO
  • SUN BINGZHU
  • LI PING
  • NAGAO KAZUMASA
  • TOKITA TAKASHI

Assignees

  • 东丽先端材料研究开发（中国）有限公司

Dates

Publication Date
20260508
Application Date
20241108

Claims (17)

  1. 1. A compound represented by the following formula 1, Wherein X 1 、X 2 、X 3 、X 4 or X 5 are the same or different and are each independently a nitrogen atom or CR 1 、CR 2 or CR 3 , and wherein at least two are nitrogen atoms; l is independently selected from aryl groups with 6-60 carbon atoms which can be substituted or heteroaryl groups with 2-60 carbon atoms which can be substituted; n is 4, 5, 6 or 7; Either Q 1 、Q 2 、Q 3 、Q 4 、Q 5 、Q 6 、Q 7 or Q 8 is attached to the L, and the others are CR 4 、CR 5 、CR 6 、CR 7 、CR 8 、CR 9 or CR 10 ; The R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 , or R 10 is independently selected from hydrogen, deuterium, cyano, alkyl that may be substituted, cycloalkyl that may be substituted, heterocyclyl that may be substituted, alkenyl that may be substituted, cycloalkenyl that may be substituted, alkynyl that may be substituted, alkoxy that may be substituted, alkylthio that may be substituted, aryl ether that may be substituted, aryl thioether that may be substituted, aryl that may be substituted, heteroaryl that may be substituted, carbonyl that may be substituted, carboxyl that may be substituted, oxycarbonyl that may be substituted, carbamoyl that may be substituted, silyl that may be substituted, alkylamino that may be substituted, or arylamino that may be substituted; Y is an oxygen atom or a sulfur atom; The groups which may be substituted are each independently selected from one or more of hydrogen, deuterium, cyano, alkyl which may be substituted, cycloalkyl which may be substituted, heterocyclyl which may be substituted, alkenyl which may be substituted, cycloalkenyl which may be substituted, alkynyl which may be substituted, alkoxy which may be substituted, alkylthio which may be substituted, aryl ether which may be substituted, aryl thioether which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, carbonyl which may be substituted, carboxyl which may be substituted, oxycarbonyl which may be substituted, carbamoyl which may be substituted, silane which may be substituted, alkylamino which may be substituted or arylamino which may be substituted.
  2. 2. The compound of claim 1, wherein one of Q 2 、Q 3 、Q 6 or Q 7 is attached to the L.
  3. 3. The compound of claim 1, wherein X 1 、X 3 and X 5 are nitrogen atoms and X 2 or X 4 are CR 1 or CR 2 , respectively.
  4. 4. The compound of claim 1, wherein either two of X 1 、X 3 or X 5 are nitrogen atoms, the remaining one is CR 3 , and X 2 or X 4 is CR 1 or CR 2 , respectively.
  5. 5. The compound of claim 1, wherein n is equal to 4 or 5.
  6. 6. The compound according to claim 5, wherein n is equal to 4, formula 1 is represented by the following formula 2, Wherein L 1 、L 2 、L 3 or L 4 are each independently selected from phenyl which may be substituted, pyridyl which may be substituted or pyrimidinyl which may be substituted.
  7. 7. The compound of claim 6, wherein each of L 1 、L 2 or L 4 is independently selected from the group consisting of optionally substituted phenyl, optionally substituted pyridinyl, and optionally substituted pyrimidinyl; The L 3 is selected from phenylene, pyridylene or pyrimidinylene.
  8. 8. The compound of claim 7, wherein either L 1 、L 2 、L 3 or L 4 is phenylene.
  9. 9. The compound of claim 8, wherein the attachment site of either L 1 、L 2 、L 3 or L 4 to its adjacent group is ortho or para.
  10. 10. A compound according to claim 5, wherein, N is equal to 5, formula 1 is represented by formula 3, Wherein L 5 、L 6 、L 7 、L 8 or L 9 are each independently selected from phenyl which may be substituted, pyridyl which may be substituted or pyrimidinyl which may be substituted.
  11. 11. The compound of claim 10, wherein L 5 、L 6 、L 7 、L 8 or L 9 is independently selected from phenylene, pyridylene or pyrimidinylene.
  12. 12. The compound of claim 11, wherein either L 5 、L 6 、L 7 、L 8 or L 9 is phenylene.
  13. 13. The compound of claim 1, wherein Y is an oxygen atom.
  14. 14. The compound of claim 1, wherein each R 4 、R 5 、R 6 、R 7 、R 8 、R 9 , or R 10 is independently selected from hydrogen, deuterium, cyano, or phenyl.
  15. 15. The compound of claim 14, wherein R 4 、R 5 、R 6 、R 7 、R 8 、R 9 , or R 10 is selected from hydrogen.
  16. 16. A light-emitting element comprising an organic layer between an anode and a cathode, wherein the compound according to any one of claims 1 to 15 is contained in the organic layer.
  17. 17. The light-emitting element according to claim 16, wherein the organic layer comprises an electron-transporting layer containing the compound according to any one of claims 1 to 15.

Description

Compound and light-emitting element Technical Field The invention relates to the technical field of organic electroluminescence, in particular to a compound and a light-emitting element containing the compound, wherein the light-emitting element can convert electric energy into light. Background An OLED device is an organic thin film light emitting element that contains an anode, a cathode, and an organic layer therebetween. The light emitting element emits light when electrons injected from the cathode and holes injected from the anode are recombined in an organic light emitting body sandwiched between the two electrodes, and is characterized by a small thickness and capable of emitting light with high luminance at a low driving voltage, and is capable of realizing multicolor light emission by selecting a light emitting material. In recent years, OLED devices have been used for display screens of televisions, smartphones, and the like, and have gradually entered a practical stage. However, many technical problems still exist with existing OLED devices. Among them, it has been a major problem to achieve a low driving voltage, high luminous efficiency and long life of the OLED at the same time. The OLED must meet the improvement of luminous efficiency, the reduction of driving voltage, and the improvement of durability. Among them, realization of both luminous efficiency and durability life is a big problem. However, it is difficult to sufficiently reduce the driving voltage of the element while securing the luminous efficiency and the durability life of the element using the prior art (patent documents 1 to 6). On the other hand, as the trend of fully replacing LCDs in OLED's increases market share in the display industry is increasing, simpler processes to reduce overall plant operation difficulty and cost are also important technical indicators. [ Prior Art literature ] [ Patent literature ] [ Patent document 1] International publication No. 2008/059713 [ Patent document 2] International publication No. 2007/100010 [ Patent document 3] International publication No. 2012/108388 [ Patent document 4] International publication No. 2013/065213 [ Patent document 5] International publication No. 2014/057874 [ Patent document 6] International publication No. 2015/182547. Disclosure of Invention The present invention has been made to solve the above-mentioned problems occurring in the prior art, and an object of the present invention is to provide an organic thin film light-emitting device having improved light-emitting efficiency, driving voltage, and durability, and having a simple manufacturing process. The invention realizes the control of the quantity of electrons with transmission capacity in molecules by adjusting the connection group and the connection mode between the aza-benzene main body and the dibenzoheterocycle main body in the compound and adjusting the nitrogen content of the groups of the transmission electrons, thereby adjusting the luminous efficiency, the driving voltage and the durable service life. In order to solve the above problems, the present invention is constituted as follows: [1] a compound represented by the following formula 1, Wherein X 1、X2、X3、X4 or X 5 are the same or different and are each independently a nitrogen atom or CR 1、CR2 or CR 3, and wherein at least two are nitrogen atoms; l is independently selected from aryl groups with 6-40 carbon atoms which can be substituted or heteroaryl groups with 2-40 carbon atoms which can be substituted; n is 4, 5, 6 or 7; Either Q 1、Q2、Q3、Q4、Q5、Q6、Q7 or Q 8 is attached to the L, and the others are CR 4、CR5、CR6、CR7、CR8、CR9 or CR 10; The R 1、R2、R3、R4、R5、R6、R7、R8、R9, or R 10 is independently selected from hydrogen, deuterium, cyano, alkyl that may be substituted, cycloalkyl that may be substituted, heterocyclyl that may be substituted, alkenyl that may be substituted, cycloalkenyl that may be substituted, alkynyl that may be substituted, alkoxy that may be substituted, alkylthio that may be substituted, aryl ether that may be substituted, aryl thioether that may be substituted, aryl that may be substituted, heteroaryl that may be substituted, carbonyl that may be substituted, carboxyl that may be substituted, oxycarbonyl that may be substituted, carbamoyl that may be substituted, silyl that may be substituted, alkylamino that may be substituted, or arylamino that may be substituted; Y is an oxygen atom or a sulfur atom; The groups which may be substituted are each independently selected from one or more of hydrogen, deuterium, cyano, alkyl which may be substituted, cycloalkyl which may be substituted, heterocyclyl which may be substituted, alkenyl which may be substituted, cycloalkenyl which may be substituted, alkynyl which may be substituted, alkoxy which may be substituted, alkylthio which may be substituted, aryl ether which may be substituted, aryl thioether which may be substituted, aryl which may be substituted, heteroaryl which may b