Host materials for electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11834459-B2
Application number	US-201916682126-A
Country	US
Kind code	B2
Filing date	Nov 13, 2019
Priority date	Dec 12, 2018
Publication date	Dec 5, 2023
Grant date	Dec 5, 2023

Abstract

A compound of Formula I

wherein
X 1 and X 2 are independently CR X or N, and at least one of X 1 or X 2 is CR X ;
Y is selected from the group consisting of O, S, Se, NR′, BR′, CR′R″, and SiR′R″;
R′, and R″ are each independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof;
R is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R A , and R C each independently represent mono to the maximum allowable substitution, or no substitution; and
each R X , R A , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two substituents R X , R A , and R C may be optionally joined to form a ring, with the proviso that R does not join with R A to form a ring.

First claim

We claim:

1. A compound of Formula II:

wherein
ring B is a 5-membered heterocyclic ring or a 6-membered carbocyclic ring;
X 1 and X 2 are independently CR X or N, and at least one of X 1 or X 2 is CR X ;
Y is selected from the group consisting of O, S, Se, NR′, BR′, CR′R″, and SiR′R″;
R′, and R″ are each independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof;
R is a substituted or unsubstituted aryl or heteroaryl;
R A , R B , and R C each independently represent mono to the maximum allowable substitution, or no substitution; and
each R X , R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two substituents R X , R A , R B , and R C may be optionally joined to form a ring, with the proviso that R does not join with R A to form a ring.

2. The compound of claim 1 , wherein each R X , R A , R B , and R C is independently a hydrogen or a sub stituent 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 R comprises a chemical group selected from the group consisting of carbazole, aza-carbazole, dibenzofuran, aza-dibenzofuran, dibenzothiophene, aza-dibenzothiophene, benzene, pyrimidine, and triazine.

4. The compound of claim 1 , wherein Y is O or S.

5. The compound of claim 1 , wherein X 1 is N and X 2 is CR X .

6. The compound of claim 1 , wherein X 1 and X 2 are both CR X .

7. The compound of claim 1 , wherein ring B is a 5-membered heteroaromatic ring.

8. The compound of claim 1 , wherein ring B is a 6-membered carbocyclic ring.

9. The compound of claim 1 , wherein two adjacent R B substituents join to form a 5-membered or 6-membered aromatic ring that is fused to ring B.

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

wherein
each Y A is selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″;
R D and R E independently represent mono to the maximum allowable substitution, or no substitution; and
each R D and R E is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two substituents R D or R E may be optionally joined to form a ring.

11. The compound of claim 1 , wherein the compound is Compound X selected from the group consisting of

Structure
R 1 , R 2 , Ar
x equal to
Compound x

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 2500
Compound 2501-5000

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 5000
Compound 5001-7500

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 7500
Compound 7501-10000

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 10000
Compound 10001-12500

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 12500
Compound 12501-15000

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 15000
Compound 15001-17500

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 17500
Compound 17501-20000

Ar = Ai R 1 = Rj i and j are each independently an integer from 1 to 50
50(i − 1) + j + 20000
Compound 20001-22500

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Wolohan Peter
• Chen Hsiao-Fan

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• C07D491/147

  the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom · CPC title