Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2024190901-A1
Application number	US-202318493040-A
Country	US
Kind code	A1
Filing date	Oct 24, 2023
Priority date	Oct 25, 2022
Publication date	Jun 13, 2024
Grant date	—

Abstract

Provided are compounds comprising as a central moiety a 6-membered aromatic ring which is fused to a 5-membered heterocyclic ring comprising at least two nitrogen atoms. Also provided are formulations comprising these compounds. Further provided are organic light emitting devices (OLEDs) as well as related consumer products that utilize these compounds.

First claim

What is claimed is:

1 . A compound of Formula I:

wherein X 0 is C;
X 1 to X 4 are each independently C or N;
R A is mono to the maximum allowable substitution or no substitution;
each R A and R G is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
at least one of R A and R G is Formula II to Formula V or a substituted or unsubstituted tercarbazole,

wherein
X 5 to X 7 are each independently CR B′ or N
X 8 to X 18 are each independently C or N;
at least one of X 5 to X 7 is N;
R D are each independently a substituted or unsubstituted aryl or heteroaryl group;
R C and R D are joined together to form a 5-membered heterocyclic ring, with the proviso that RC and R D are not joined to form an indolocarbazole;
Y 1 and Y 2 are each independently selected from the group consisting of O, S, Se, SiRR′, and GeRR′;
R M , R E and R F are each mono to the maximum allowable substitution or no substitution;
L 1 is a direct bond or is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO 2 , CR′R″, P(O)R′, SiR′R″, GeR′R″, aryl, heteroaryl, alkyl, cycloalkyl, heteroalkyl, and combinations thereof,
each R′, R″, R B , R B′ , R C , R E , R F , R M and R N is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, imino, and combinations thereof;
with the proviso that if L 1 is attached to X 0 then L 1 is selected from the group consisting of a direct bond, SiR′R″, GeR′R″, carbazole, phenyl, pyridine, pyrimidine, pyrazine, or triazine;
Z is C, Si or Ge;
L 2 is a direct bond or is selected from the group consisting of carbazole, pyridine, pyrimidine, pyrazine, or triazine;
A 1 and A 2 are each independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
A 3 is a substituted or unsubstituted aryl or heteroaryl, with the proviso that A 3 is not benzimidazole;
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 5 membered ring;
wherein the dashed line ( ) in each of Formulae II-V indicates the bond to the structure of Formula I;
with the proviso that when R A is Formula V and attached to Formula I at X 0 , R G is not selected from the group consisting of 1-naphtyl, 2-anthryl, 3-phenanthryl, 2-pyrenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, triphenoxyphosphoryl, diphenylphosphoryl, 3-trifluoromethylphenyl, 4-diphenylmethanoyl, 2-diphenylmethanyol, diphenylsulphonyl, dipyridoyl, benzooxazoyl, 5-quinolyl, 6-quinolyl, 2-quinoxalyl, 6-quinoxalyl, 1, 5-napthyridinyl, 1, 10-phenanthrolinyl, N-phenylbenzimidazolyl and 3-phenylquinoxalinyl; and
with the proviso that the compound does not comprise a group selected from cycloalkenyl, oxazole, oxadiazole, or an uncyclized diphenyl amine, and the compound is not

2 . The compound of claim 1 , wherein each R′, R″, R A , R B′ , R D , R E , R F , R M , R N , R G , A 1 , and A 2 is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3 . The compound of claim 1 , wherein all of X 1 -X 4 are C.

4 . The compound of claim 1 , wherein all R A bonded to X 1 -X 4 are hydrogen.

5 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula II, and all of X 5 -X 7 are N.

6 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula II, and R B is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, triazine, carbazole, and benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), any of which may be further substituted.

7 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula III, and all of X-X 18 are C.

8 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula III, and at least one of Y 1 and Y 2 is O.

9 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula III, and all of R E and R F are hydrogen.

10 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula III, and L 1 is directly bonded to X 9 .

11 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula IV, and A 1 -A 3 each are phenyl.

12 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula IV, and L 2 is a direct bond.

13 . The compound of claim 1 , wherein at least one R A or R G is selected from Formula V, and each R N and R G , when R G is not selected from Formula V, is independently selected from the group consisting of

wherein each R C′ —R Q′ is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
X 1′ -X 59′ are each independently C or N;
each Y 1′ and Y 2′ is independently selected from the group consisting of O, S, Se, NR′, BR′, CR′R″, SiR′R″, and GeR′R″;
each R′ and R″ is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and
any two substituents may be joined or fused to form a ring.

14 . The compound of claim 1 , wherein when R A is Formula V, each R N and R G independently comprise a structure selected from the group consisting of

wherein X is selected from the gr

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Ma Bin
• Jradi Fadi M
• Sheina Elena
• Talluri Siva Kumar
• Horwitz Noah
• Paudyal Mahesh

Classifications

• H10K85/346

  comprising platinum · CPC title

• H10K85/654

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

• H10K85/6572

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

• C07F7/0812 Primary

  comprising a heterocyclic ring · CPC title

• C07F5/02

  Boron compounds · CPC title