Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2024190900-A1
Application number	US-202318489013-A
Country	US
Kind code	A1
Filing date	Oct 18, 2023
Priority date	Oct 19, 2022
Publication date	Jun 13, 2024
Grant date	—

Abstract

Provided are organic compounds comprising at least two 6-membered rings which are connected to each other so to form a 5-membered ring comprising O, S, or Se in between the two 6-membered rings, wherein the compound comprises at least one Si or Ge substituent. Also provided are formulations comprising these compounds. Further provided are organic light emitting devices (OLEDs) and related consumer products that utilize these compounds.

First claim

What is claimed is:

1 . A compound of Formula I;

wherein Y 1 is selected from the group consisting of O, S, and Se;
wherein X 1 to X 8 are each independently C or N;
wherein at least two of X 1 to X 8 are N;
wherein R A is mono to the maximum allowable substitution;
wherein at least one R A is -L-ZAr 1 Ar 2 Ar 3 ;
wherein each R A , and Ar 1 —Ar 3 is independently a hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein Z is Si or Ge;
wherein L is a direct bond, a substituted or unsubstituted nonfused carbazole, or a substituted or unsubstituted 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole;
wherein, if L is a substituted nonfused carbazole, Z is directly attached to the carbazole group of the substituted nonfused carbazole;
when Y 1 is O or S, Z is Si, and L is a direct bond, at least one of the following conditions is true:
1) X 5 is N and one of X 1 to X 3 is N
2) the compound comprises at least 1 carbazole or 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole
3) the compound comprises two Si containing groups on one ring
4) at least one R A adjacent to each N is different from hydrogen;
5) at least one Ar 1 —Ar 3 is not an unsubstituted phenyl
6) at least one of R A comprises at least one deuterium any two groups may be joined or fused to form a ring with the proviso that two R A are not joined to form a benzene ring fused to Formula 1.

2 . The compound of claim 1 , wherein each R A is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3 . The compound of claim 1 , wherein exactly two of X 1 to X 8 are N.

4 . The compound of claim 1 , wherein X 2 and X 4 are N.

5 . The compound of claim 1 , wherein at least one of X 1 to X 4 , and at least one of X 5 to X 8 is N.

6 . The compound of claim 1 , wherein Y 1 is S.

7 . The compound of claim 1 , wherein Z is Si.

8 . The compound of claim 1 , wherein L is a direct bond.

9 . The compound of claim 1 , wherein Ar 1 —Ar 3 is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, aryl, heteroaryl, nitrile, fully or partially deuterated variants thereof, fully or partially fluorinated variants thereof, and combinations thereof.

10 . The compound of claim 1 , wherein Ar 1 —Ar 3 are all phenyl.

11 . The compound of claim 1 , which comprises at least two carbazole groups.

12 . The compound of claim 1 , which is not

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

wherein R A′ , R B′ , R C′ , R D′ , R E′ are each independently mono to the maximum allowable substitution;
wherein each R A′ , R C′ , and R B′ is independently a hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein each R A1 , R A2 , and R B′ is independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein each R D′ is independently selected from the group consisting of deuterium, deuterated alkyl, deuterated heteroalkyl, deuterated cycloalkyl, deuterated heterocycloalkyl, deuterated aryl, deuterated heteroaryl, and combinations thereof, which may each be further substituted or unsubstituted;
wherein L 1 is a direct bond or an organic linker;
wherein Ar H is selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, amino, or combinations thereof, which may be substituted or unsubstituted.
wherein at least one R A1 , R A2 , and R E′ is ZAr 1 Ar 2 Ar; and
any two groups may be joined or fused to form a ring with the proviso that two R A′ or two R E′ are not joined to form a benzene ring fused to Formula 1.

14 . The compound of claim 13 , wherein each R A′ , R C′ , and R E′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

15 . The compound of claim 13 , wherein each R A1 , R A2 , and R B′ is independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

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

wherein all Si can be replaced with Ge, or all H can be replaced with D to obtai

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Wolohan Peter
• Talluri Siva Kumar
• Paudyal Mahesh
• Hamze Rasha

Classifications

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07F7/0812 Primary

  comprising a heterocyclic ring · CPC title