Granted Patent B2

US 12,459,955 · App. 17/397,373 · Granted Nov 4, 2025

Inventors: Chuanjun Xia (Lawrenceville, NJ); Lichang Zeng (Lawrenceville, NJ); Walter Yeager (Yardley, PA); Zhiqiang Ji (Hillsborough, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

C07D495/04C09K11/025C09K11/06H10K85/342H10K85/657H10K85/6572C09K2211/185H10K50/11H10K50/15H10K50/16H10K50/18H10K2101/10

Abstract

Claims (64)

1 . A compound having a formula selected from the group consisting of:

wherein X is selected from the group consisting of O, S, and Se;

wherein X 1 to X 10 are each independently selected from the group consisting of carbon and nitrogen;

wherein at least one of X 1 to X 6 is nitrogen;

wherein R and R′ each independently represent from mono to the possible maximum number of substitutions, or no substitution;

wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any adjacent substitutions on the same ring are optionally joined or fused into a ring;

wherein at least one pair of adjacent substitutions on the same ring are joined or fused into a ring; and

wherein at least one of the following is true:

(i) an R′ is bonded to X 1 , X 2 , or X 3 and comprises aryl or heteroaryl, and two adjacent R′ are joined or fused to form a ring;

(ii) the compound has a structure of Formula 1-1 or Formula 1-2, and at least one of an R′ is bonded to X 4 and comprises aryl or heteroaryl or an R is bonded to X 5 and comprises aryl or heteroaryl;

(iii) the compound has a structure of Formula 1-3, and at least one of an R′ is bonded to X 4 and comprises aryl or heteroaryl or an R is bonded to X 7 and comprises aryl or heteroaryl;

(iv) (a) at least one pair of adjacent substitutions on the same ring are joined or fused into a 6-membered ring and (b) an R is bonded to X 6 , X 7 , X 8 , X 9 , or X 10 and comprises aryl or heteroaryl, and the R does not comprise anthracene and if an amino is present, the amino is part of a substituted or unsubstituted carbazole; or

(v) the compound has a structure of Formula 1-3 and an R is bonded to X 5 and comprises aryl or heteroaryl, and the R does not comprise anthracene and if an amino is present, the amino is part of a substituted or unsubstituted carbazole;

provided that when adjacent substitutions on X 5 and X 6 in Formula 1-1 and 1-3 fuse into a six-membered ring, this ring and the ring having X 1 to X 10 can not be pyridine at the same time, and

provided that when adjacent substitutions on X 5 and X 6 in Formula 1-1 fused into phenyl, exactly one of X 1 to X 4 is N.

2 . The compound of claim 1 , wherein at least one of X 5 and X 6 is nitrogen.

3 . The compound of claim 1 , wherein the adjacent substitutions on X 5 and X 6 are not joined or fused into a ring.

4 . The compound of claim 1 , wherein X 1 to X 4 are all carbon.

5 . The compound of claim 1 , wherein at least one of X 1 to X 4 is nitrogen, and at least one of X 5 and X 6 is nitrogen.

6 . The compound of claim 1 , wherein at least one of R and R′ comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

7 . The compound of claim 1 , wherein the compound has at least five aromatic rings fused together.

8 . The compound of claim 1 , wherein the compound comprises a group selected from the group consisting of:

wherein the dotted lines represent a possible substitution.

9 . A compound comprising a formula A i D j , wherein A i comprises a group selected from the group consisting of:

wherein the dotted lines represent a bond to a substitution;

wherein the substitution D′ is selected from the group consisting of:

10 . The compound of claim 9 , wherein the compound is Compound x(Label) having the formula A i D j ;

wherein x=144j+i−144, where i is an integer from 24 to 144, j is an integer from 1 to 244; and

wherein Label is the X in the corresponding A i .

11 . A first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having a formula selected from the group consisting of:

wherein X is selected from the group consisting of O, S, and Se;

wherein X 1 to X 10 are each independently selected from the group consisting of carbon and nitrogen;

wherein at least one of X 1 to X 6 is nitrogen;

wherein R and R′ each independently represent from mono to the possible maximum number of substitutions, or no substitution;

wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any adjacent substitutions on the same ring are optionally joined or fused into a ring;

wherein at least one pair of adjacent substitutions on the same ring are joined or fused into a ring; and

wherein at least one of the following is true:

(i) an R′ is bonded to X 1 , X 2 , or X 3 and comprises aryl or heteroaryl, and two adjacent R′ are joined or fused to form a ring;

(ii) the compound has a structure of Formula 1-1 or Formula 1-2, and at least one of an R′ is bonded to X 4 and comprises aryl or heteroaryl or an R is bonded to X 5 and comprises aryl or heteroaryl;

(iii) the compound has a structure of Formula 1-3, and at least one of an R′ is bonded to X 4 and comprises aryl or heteroaryl or an R is bonded to X 7 and comprises aryl or heteroaryl;

(iv) (a) at least one pair of adjacent substitutions on the same ring are joined or fused into a 6-membered ring and (b) an R is bonded to X 6 , X 7 , X 8 , X 9 , or X 10 and comprises aryl or heteroaryl, and the R does not comprise anthracene and if an amino is present, the amino is part of a substituted or unsubstituted carbazole; or

(v) the compound has a structure of Formula 1-3 and an R is bonded to X 5 and comprises aryl or heteroaryl, and the R does not comprise anthracene and if an amino is present, the amino is part of a substituted or unsubstituted carbazole;

provided that when adjacent substitutions on X 5 and X 6 in Formula 1-1 and 1-3 fuse into a six-membered ring, this ring and the ring having X 7 to X 10 can not be pyridine at the same time, and provided that when adjacent substitutions on X 5 and X 6 in Formula 1-1 fused into phenyl, exactly one of X 1 to X 4 is N.

12 . The first organic light emitting device of claim 11 , wherein the organic layer is an emissive layer and the compound is a host.

13 . The first organic light emitting device of claim 11 , 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 X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;

wherein Z is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;

wherein R′, R″, R a , R b , R c , and R d are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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; and

wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

14 . The first organic light emitting device of claim 11 , wherein the organic layer is a charge carrier blocking layer and the compound is a charge carrier blocking material in the organic layer, or the organic layer is a charge carrier transporting layer and the compound is a charge carrier transporting material in the organic layer.

15 . The first organic light emitting device of claim 11 , wherein the device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

16 . The first organic light emitting device of claim 11 , wherein the organic layer is an emissive layer and the compound is an emitter.

17 . The first organic light emitting device of claim 16 , wherein the first organic light emitting device emits a luminescent radiation at room temperature when a voltage is applied across the first organic light emitting device, and wherein the luminescent radiation comprises a delayed fluorescence process.

18 . The first organic light emitting device of claim 16 , wherein the emissive layer further comprises a first phosphorescent emitting material.

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

wherein each of Z 1 to Z 12 is independently C or N.

20 . A formulation comprising a compound of claim 1 .

Assignments (1)

Continuity (3)

References Cited (226)