IP Library › Patent Application 18982362
Patent Application
App. No. 18/982,362

Organic Electroluminescent Materials and Devices

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Patent No.
US None
App. No.
18/982,362
Abstract

This invention discloses iridium complexes containing phenylpyridine ligand wherein there is an aryl or heterocyclic ring fused into phenyl ring. The iridium complexes showed desired device performance.

Claims (77)

1 .- 23 . (canceled)

24 . A compound comprising a ligand L A of Formula I:

wherein R has the following structure and is fused to ring A:

wherein each Z 1 to Z 8 is nitrogen or carbon;

wherein the wave lines indicate the bonds to two of the adjacent Z 1 to Z 4 of ring A;

wherein when two of the adjacent Z 1 to Z 4 are used to fuse to R, those two of the adjacent Z 1 to Z 4 are carbon;

wherein R 1 and R 4 each independently represent mono, di, tri, or tetra substitutions, or no substitution;

wherein R 2 and R 3 each independently represent mono, or di substitutions, or no substitution;

wherein X is O or S;

each R 1 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 2 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 3 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 4 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

R 5 is selected from the group consisting of hydrogen, deuterium, halide, 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;

R 6 is selected from the group consisting of hydrogen, deuterium, halide, 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,

wherein any two adjacent substituents are optionally joined to form a ring, which can be further substituted;

wherein the ligand L A is coordinated to a metal M;

wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand; and

wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is not hydrogen or deuterium.

25 . The compound of claim 24 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

26 . The compound of claim 24 , wherein at least one of Z 1 , Z 2 , Z 3 , and Z 4 is nitrogen or at least one of Z 5 and Z 6 is nitrogen.

27 . The compound of claim 24 , wherein each R 1 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, aryl, heteroaryl, nitrile, and combinations thereof.

28 . The compound of claim 24 , wherein each R 1 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof.

29 . The compound of claim 24 , wherein each R 2 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, aryl, heteroaryl, nitrile, and combinations thereof.

30 . The compound of claim 24 , wherein each R 3 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, aryl, heteroaryl, nitrile, and combinations thereof.

31 . The compound of claim 24 , wherein each R 3 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof.

32 . The compound of claim 24 , wherein each R 4 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, aryl, heteroaryl, nitrile, and combinations thereof.

33 . The compound of claim 24 , wherein each R 4 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof.

34 . The compound of claim 24 , wherein each R 5 and R 6 are independently selected from the group consisting of 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.

35 . The compound of claim 33 , wherein R 5 and R 6 join to form a ring, which is optionally further substituted.

36 . The compound of claim 24 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is selected from the group consisting of deuterium, halide, 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, partially deuterated versions thereof, fully deuterated versions thereof, and combinations thereof.

37 . The compound of claim 35 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is selected from the group consisting of halide, alkyl, cycloalkyl, silyl, alkenyl, aryl, heteroaryl, nitrile, partially deuterated versions thereof, and fully deuterated versions thereof, and combinations thereof.

38 . The compound of claim 24 , wherein the ligand L A is selected from the group consisting of:

39 . The compound of claim 24 , wherein the ligand L A is selected from the group consisting of:

40 . The compound of claim 24 , wherein the ligand L A is selected from the group consisting of:

41 . The compound of claim 24 , wherein the compound is selected from the group consisting of Compound 1 through Compound 114,300;

where each Compound x has the formula Ir(L Ai ) (L Bj ) 2 ;

wherein x=508j+i−508, i is an integer from 1 to 508, and j is an integer from 1 to 225;

wherein L Bj has the following formula:

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

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L A of Formula I:

wherein R has the following structure and is fused to ring A:

wherein each Z 1 to Z 8 is nitrogen or carbon;

wherein the wave lines indicate the bonds to two of the adjacent Z 1 to Z 4 of ring A;

wherein when two of the adjacent Z 1 to Z 4 are used to fuse to R, those two of the adjacent Z 1 to Z 4 are carbon;

wherein R 1 and R 4 each independently represent mono, di, tri, or tetra substitutions, or no substitution;

wherein R 2 and R 3 each independently represent mono, or di substitutions, or no substitution;

wherein X is O or S;

each R 1 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 2 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 3 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 4 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

R 5 is selected from the group consisting of hydrogen, deuterium, halide, 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;

R 6 is selected from the group consisting of hydrogen, deuterium, halide, 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;

wherein any two adjacent substituents are optionally joined to form a ring, which can be further substituted;

wherein the ligand L A is coordinated to a metal M; and

wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand; and

wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is not hydrogen or deuterium.

43 . A formulation comprising a compound comprising a ligand L A of Formula I:

wherein R has the following structure and is fused to ring A:

wherein each Z 1 to Z 8 is nitrogen or carbon;

wherein the wave lines indicate the bonds to two of the adjacent Z 1 to Z 4 of ring A;

wherein when two of the adjacent Z 1 to Z 4 are used to fuse to R, those two of the adjacent Z 1 to Z 4 are carbon;

wherein R 1 and R 4 each independently represent mono, di, tri, or tetra substitutions, or no substitution;

wherein R 2 and R 3 each independently represent mono, or di substitutions, or no substitution;

each R 1 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 2 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 3 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

each R 4 is independently selected from the group consisting of hydrogen, deuterium, halide, 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;

R 5 is selected from the group consisting of hydrogen, deuterium, halide, 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;

R 6 is selected from the group consisting of hydrogen, deuterium, halide, 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,

wherein any two adjacent substituents are optionally joined to form a ring, which can be further substituted;

wherein the ligand L A is coordinated to a metal M;

wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand; and

wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is not hydrogen or deuterium.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2025
From: MA, BIN; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 070635/0958 →