Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10971687-B2
Application number	US-201816208830-A
Country	US
Kind code	B2
Filing date	Dec 4, 2018
Priority date	Dec 14, 2017
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

An organic light emitting diode/device (OLED) with an organic layer disposed between an anode and a cathode. The organic layer includes a compound of Formula I or Formula II. The OLED can be incorporated into one or more of a consumer product, an electronic component module, and/or a lighting panel.

First claim

We claim:

1. A compound selected from the group consisting of

wherein
at least one of R G , or at least one of R J , of Formula II includes a structure of Formula III, wherein the structure of Formula II forms a direct bond to Formula III through a carbon of one of X 21 to X 24 , a carbon of one of X 25 to X 28 , or R N , or optionally, the structure of Formula II is linked to Formula III through a carbon of one of X 21 to X 24 , a carbon of one of X 25 to X 28 , or R N , by an aromatic linker;

Ar is selected from aryl or heteroaryl, each of which is optionally substituted;
X 1 to X 24 are independently selected from C or N;
L 1 and L 2 is selected from a direct bond or an aromatic linker;
Y 1 , Y 2 , and Y 3 are independently selected from CR Y or N, and at least one of Y 1 , Y 2 , or Y 3 is N;
R A , R B , R C , R D , R E , R F , R G , R H , R I , and R J represent mono to the maximum allowable substitution, or no substitution;
wherein each R Y , R A , R B , R C , R D , R E , R F , R G , R H , R I , and R J are independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; or optionally, any two adjacent substituents of R E , R F , R G , R H , R I , and R J join to form a fused ring; and wherein R B and R E do not comprise carbazole; and
R N is a direct bond or is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, and combinations thereof;
wherein the compounds of Formula I do not include compounds of the formulae

2. The compound of claim 1 , wherein R Y , R A , R B , R C , R D , R E , R F , R G , R H , R I , and R J are independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein Ar is selected from a 6-membered aromatic ring, or a fused aromatic, carbocyclic, or heterocyclic ring containing from 10 to 26 carbon atoms; each of which is optionally substituted with deuterium, nitrile, alkyl, cycloalkyl, amino, silyl, aryl, or heteroaryl.

4. The compound of claim 3 , wherein the optionally substituted, 6-membered aromatic ring is selected from the group consisting of phenyl, pyridyl, pyrimidinyl, pyrazinyl, and triazole, and the optionally substituted, fused aromatic, carbocyclic, or heterocyclic ring is selected from the group consisting of naphthalene, anthracene, quinazoline, fluorene, dibenzofuran, and dibenzothiophene.

5. The compound of claim 1 , wherein Ar of Formula I is selected from the group consisting of naphthyl, quinazoline, biphenyl, and terphenyl, each of which is optionally substituted with deuterium, nitrile, alkyl, cycloalkyl, amino, silyl, aryl, or heteroaryl; or one R F of Formula II is selected from the group consisting of naphthyl, quinazoline, biphenyl, and terphenyl; each of which is optionally substituted with deuterium, nitrile, alkyl, cycloalkyl, amino, silyl, aryl, or heteroaryl.

6. The compound of claim 1 , wherein for the compounds of Formula II: Y 1 and Y 2 are N, and Y 3 is CR Y ; or Y 1 and Y 3 are N, and Y 2 is CR Y .

7. The compound of claim 5 , wherein Y 3 is CR Y , and R Y of Y 3 is a 6-membered aromatic ring, or a fused aromatic, carbocyclic, or heterocyclic ring containing from 10 to 26 carbon atoms; each of which is optionally substituted with deuterium, nitrile, alkyl, cycloalkyl, amino, silyl, aryl, or heteroaryl.

8. The compound of claim 1 , wherein for the compounds of Formula II, one of R G includes a structure of Formula III, or one of R G and one of R J includes a structure of Formula III.

9. The compound of claim 1 , wherein if L 1 is a direct bond and each R A is H, or one R A is phenyl, then Ar is a fused aromatic ring containing from 10 to 26 carbon atoms.

10. The compound of claim 1 , wherein one to six of X 1 to X 22 is N, wherein no 6-membered ring has more than two N.

11. The compound of claim 1 , wherein one to four of X 21 to X 28 is N, wherein no 6-membered ring has more than two N.

12. The compound of claim 1 , wherein L 1 or L 2 is a 6-membered, carbocyclic or heterocyclic, aromatic ring; each of which is optionally substituted.

13. The compound of claim 1 , wherein the compound is selected from the group consisting of

wherein R K and R L represent mono to the maximum allowable substitution, or no substitution; and wherein each R K and R L are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

14. The compound of claim 1 , wherein the compound is selected from the group consisting of

Assignees

• Universal Display Corp

Inventors

• Ma Bin
• Adamovich Vadim
• Feldman Jerald

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• C07D421/14

  containing three or more hetero rings · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D403/14 Primary

  containing three or more hetero rings · CPC title