Granted Patent B2

US 12,319,653 · App. 18/430,974 · Granted Jun 3, 2025

Inventors: Bin Ma (Plainsboro, NJ); Ting-Chih Wang (Lawrenceville, NJ); Vadim Adamovich (Yardley, PA)

C07D209/88H10K50/11H10K50/14H10K50/81H10K50/82H10K50/18

Abstract

Claims (89)

1. A composition comprising a first compound and a second compound;

wherein the first compound has a formula selected from the group consisting of:

wherein,

R E to R U each independently represents mono to the maximum allowable substitutions, or no substitution;

each R 4 , R 5 , and R E to R U is independently 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;

any two substituents may be joined or fused together to form a ring;

Y is O or S; and

Ar 3 is a substituted or unsubstituted aryl ring;

wherein the second compound has a formula having the structure:

wherein,

R DD , R EE , R FF , and R GG each independently represent mono to the maximum allowable substitutions, or no substitution;

each R DD , R EE , R FF , and R GG is independently 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;

Ar 7 and Ar 8 are each independently a substituted or unsubstituted aryl ring;

X 10 , X 11 , and X 12 are each independently N or CH;

at least two of X 10 , X 11 , and X 12 are N;

any two substituents may be joined or fused together to form a ring; and

L is either an aromatic linker or a direct bond.

2. The composition of claim 1 , wherein each R 4 , R 5 , and R E to R U is 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 composition of claim 1 , wherein each R DD , R EE , R FF , and R GG is 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.

4. The composition of claim 1 , wherein the first compound has the structure of

5. The composition of claim 4 wherein the first compound has the structure of:

and the first compound comprises at least two or more non-fused phenyl rings, wherein said at least two or more non-fused phenyl rings is inclusive of the phenyl ring containing R E and/or the phenyl ring containing R G .

6. The compound of claim 4 wherein the first compound has the structure of:

and

at least one of R 4 and R 5 comprise at least two or more non-fused phenyl rings.

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

and partially or fully deuterated variants thereof.

8. The compound of claim 1 , wherein X 10 , X 11 , and X 12 are N.

9. The composition of claim 1 , wherein L is a direct bond.

10. The composition of claim 1 , wherein L is an aromatic linker.

11. The composition of claim 10 , wherein the aromatic linker is phenyl.

12. The composition of claim 11 , wherein the phenyl linker bonds to the ring containing Ar 7 and Ar 8 at a para position relative to the bond to the nitrogen atom of the N-carbazolyl-carbazole.

13. The composition of claim 1 , wherein at least one of Ar 7 and Ar 8 comprises at least two phenyl rings.

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

and partially or fully deuterated variants thereof.

15. The composition of claim 1 , wherein the first compound is selected from the group consisting of:

and partially or fully deuterated variants thereof; and

wherein the second compound is selected from the group consisting of:

and partially deuterated or fully deuterated variants thereof.

16. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a composition, the composition comprising a first compound and a second compound,

wherein the first compound has a formula selected from the group consisting of:

wherein,

R E to R U each independently represents mono to the maximum allowable substitutions, or no substitution;

each R 4 , R 5 , and R E to R U is independently 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;

any two substituents may be joined or fused together to form a ring;

Y is O or S; and

Ar 3 is a substituted or unsubstituted aryl ring;

wherein the second compound has a formula having the structure:

wherein,

R DD , R EE , R FF , and R GG each independently represent mono to the maximum allowable substitutions, or no substitution;

each R DD , R EE , R FF , and R GG is independently 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;

Ar 7 and Ar 8 are each independently a substituted or unsubstituted aryl ring;

X 10 , X 11 , and X 12 are each independently N or CH;

at least two of X 10 , X 11 , and X 12 are N;

any two substituents may be joined or fused together to form a ring; and

L is either an aromatic linker or a direct bond.

17. The OLED of claim 16 , wherein the organic layer is an emissive layer and the composition is a host material.

18. The OLED of claim 16 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

wherein,

each Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen;

Y′ is selected from the group consisting of B R e , N R e , P R e , O, S, S e , C═O, S═O, SO 2 , CR c R f , SiR e R f , and GeR e R f ;

R e and R f are optionally fused or joined to form a ring;

each R a , R b , R c , and R a independently represents from mono substitution to the maximum allowable substitutions, or no substitution;

each R a , R b , R c , R a , R e and R f is independently 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 adjacent substituents of R a , R b , R c , and R a can be fused or joined to form a ring or form a multidentate ligand.

19. The OLED of claim 16 , wherein the organic layer is a blocking layer and the composition is a blocking material in the organic layer; or the organic layer is a transporting layer and the composition is a transporting material in the organic layer.

20. A consumer product comprising an organic light-emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a composition, the composition comprising a first compound and a second compound,

wherein the first compound has a formula selected from the group consisting of:

wherein,

R E to R U each independently represents mono to the maximum allowable substitutions, or no substitution;

each R 4 , R 5 , and R E to R U is independently 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;

any two substituents may be joined or fused together to form a ring;

Y is O or S; and

Ar 3 is a substituted or unsubstituted aryl ring;

wherein the second compound has a formula having the structure:

wherein,

R DD , R EE , R FF , and R GG each independently represent mono to the maximum allowable substitutions, or no substitution;

each R DD , R EE , R FF , and R GG is independently 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;

Ar 7 and Ar 8 are each independently a substituted or unsubstituted aryl ring;

X 10 , X 11 , and X 12 are each independently N or CH;

at least two of X 10 , X 11 , and X 12 are N;

any two substituents may be joined or fused together to form a ring; and

L is either an aromatic linker or a direct bond.

Assignments (1)

Continuity (4)

References Cited (204)