Compound, a display panel and an electronic device

Patent metadata

Field	Value
Publication number	US-11649254-B2
Application number	US-202016874514-A
Country	US
Kind code	B2
Filing date	May 14, 2020
Priority date	Oct 31, 2019
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

The present disclosure provides a compound for a display panel. The compound includes elements selected from O, S or N, electron-donor groups and electron-accepting groups. The OLED device in the display panel includes an anode, a cathode, and at least one organic thin film layer between the anode and the cathode. The organic thin film layer includes a light emitting layer, the light emitting layer includes the compound of the present disclosure, and the compound is used to be any one of a host material, a doping material, and a co-doping material. The compound reduces energy level difference between singlet and triplet states ΔEST through design of the compound molecular structure. The compound realizes an efficient reverse intersystem crossing process, has typical TADF characteristics, and can be used as a light-emitting layer material of an OLED device to improve luminous efficiency and working life.

First claim

What is claimed is:

1. A compound, comprising a structure as shown in Formula I:

wherein each of n 1 and n 2 is independently set as 0 or 1, and each of n 3 and n 4 is independently set as 1;
wherein X 1 and X 2 each is independently selected from O, S or N;
when X 1 is O or S, n 1 is 0;
when X 2 is O or S, n 2 is 0;
wherein D 1 and D 2 each represents one donor in an electron-donating group, and is independently selected from any one of a C1 to C20 alkoxyl group, a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C3 to C40 heteroaryl group, and a substituted or unsubstituted C6 to C40 arylamine group;
wherein L 1 , L 2 , L 3 and L 4 each is independently selected from any one of a single bond, a C1 to C20 linear or branched alkylene group, a substituted or unsubstituted C6 to C30 arylene group, and a substituted or unsubstituted C3 to C30 heteroarylene group;
wherein A 1 and A 2 represent an electron-accepting group and each is independently selected from any one of a cyano group, a cyano-substituted C6 to C30 aromatic hydrocarbon group, a cyano-substituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 arylboron group, a substituted or unsubstituted C6 to C40 aryl keto group, a substituted or unsubstituted C4 to C40 heteroaryl keto group, a substituted or unsubstituted C6 to C30 arylsulfone group, and a substituted or unsubstituted C6 to C30 arylphosphonoxy group;
wherein when a substituent exists in the above groups, the substituent is selected from at least one of a C1 to C10 linear or branched alkyl group, a C6 to C20 aryl group, a C6 to C20 heteroaryl group, a C1 to C10 alkoxyl group, a C6 to C20 arylamino group, a C3 to C20 cycloalkyl group, and halogen; and
wherein m 1 and m 2 are both 0,
wherein the substituted or unsubstituted C6 to C40 aryl keto group or the substituted or unsubstituted C4 to C40 heteroaryl keto group is selected from any one of the following groups:

wherein, dotted line represents linking position of a group;
wherein R O1 -R O26 each is independently selected from any one of a C1 to C10 linear or branched alkyl group, a C6 to C20 aryl group, a C6 to C20 heteroaryl group, a C1 to C10 alkoxyl group, a C6 to C20 arylamino group, a C3 to C20 cycloalkyl group, and halogen;
wherein M 1 is an oxygen atom (O) or a surfer atom (S);
wherein M 2 is selected from O, S or R M1 —C—R M2 , and R M1 and R M2 each is independently selected from any one of hydrogen, a C1 to C10 linear or branched alkyl group, a C6 to C20 aryl group, a C6 to C20 heteroaryl group, a C1 to C10 alkoxyl group, a C6 to C20 arylamino group, a C3 to C20 cycloalkyl group, and halogen;
wherein R N1 -R N6 each is independently selected from any one of hydrogen, a C1 to C10 linear or branched alkyl group, a C6 to C20 aryl group, a C6 to C20 heteroaryl group, a C1 to C10 alkoxyl group, a C6 to C20 arylamino group, a C3 to C20 cycloalkyl group, and halogen;
wherein:
o 1 , o 3 , o 5 , o 61 , o 8 , and o 201 each is independently an integer of 0 to 5;
o 2 , o 4 , o 6 , o 7 , o 9 , o 10 , o 12 , o 13 , o 15 , o 17 , o 19 , o 20 , o 21 , and o 23 each is independently an integer of 0 to 4;
o 71 , o 11 , o 14 , o 16 , o 18 , o 191 , o 22 , o 24 , o 26 , and o 27 each is independently an integer of 0 to 3; and
o 25 is an integer of 0 to 2.

2. The compound according to claim 1 , wherein the cyano-substituted C6 to C30 aromatic hydrocarbon group and the cyano-substituted C3 to C30 heteroaryl group are selected from any one of the following groups:

wherein, dotted line represents linking position of a group;
wherein R C1 , R C2 and R C3 each is independently selected from at least one of an unsubstituted or halogenated C1 to C10 linear or branched alkyl group, a C6 to C20 aryl group, a C6 to C20 heteroaryl group, a C1 to C10 alkoxyl group, a C6 to C20 arylamino group, a C3 to C20 cycloalkyl group, and halogen;
and wherein:
c 1 is an integer of 0 to 4, c 2 is an integer of 1 to 3, and c 1 +c 2 ≤5;
c 3 is an integer of 0 to 3, c 4 is an integer of 1 to 3, and c 3 +c 4 ≤4; and
c 5 is an integer of 0 to 2, c 6 is an integer of 1 to 3 and c 5 +c 6 ≤3.

3. The compound according to claim 2 , wherein the cyano-substituted C6 to C30 aromatic hydrocarbon group and the cyano-substituted C3 to C30 heteroaryl group are selected from any one of the following groups:

wherein, dotted line represents linking position of a group.

4. The compound according to claim 1 , wherein the C6 to C30 arylboron group is selected from any one of the following groups:

wherein, dotted line represents linking position of a group;
wherein R B1 -R B10 each is independently selected from any one of a C1 to C10 linear or branched alkyl group, a C6 to C20 aryl group, a C6 to C20 heteroaryl group, a C1 to C10 alkoxyl group, a C6 to C20 arylamino group, a C3 to C20 cycloalkyl group, and halogen;
wherein Z 1 -Z 7 each is independently selected from O, S, N—R Z1 or B—R Z2 , R Z1 and R Z1 each is independently selected from any one of hydrogen, a C6 to C40 aryl group, a C1 to C10 linear or branched alkyl group, a C1 to C20 alkoxyl group, a C3 to C20 cycloalkyl group, a C3 to C20 heterocycloalkyl group, and a C3 to C40 heteroaryl group; and wherein:
b 1 -b 6 each is independently an integer of 0 to 4;
b 7 and b 8 each is independently an integer of 0 to 2; and
b 9 and b 10 each is independently an integer of 0 to 3.

5. The compound according to claim 4 , wherein the C6 to C30 arylboron group is selected from any one of the following groups:

wherein, dotted line represents linking position of a group.

6. The compound according to claim 1 , wherein the C6 to C40 aryl keto group and the substituted or unsubstituted C4 to C40 heteroaryl keto group are selected from any one of the following groups:

wherein, dotted line represents linking position of a group.

7. The compound according to claim 1 , wherein the C6 to C30 arylsulfone group is selected from any one of the following groups:

wherein, dotted line represents linking position of a group;
wherein R S1 -R S14 each is independently selected from any one of a C1 to C10 linear or branched alkyl group, a C6 to C20 aryl group, a C6 to C2

Assignees

• Wuhan Tianma Micro Electronics Co Ltd
• Wuhan Tianma Microelectronics Co Ltd Shanghai Branch

Inventors

• Gao Wei
• Dai Wenpeng
• Zhang Lei
• Xiao Wenjing
• Niu Jinghua
• Lin Sha

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K59/10

  OLED displays · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• C07F5/02 Primary

  Boron compounds · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title