IP Library › Granted Patent US 11,871,653

Granted Patent B2

US 11,871,653 · App. 16/788,886 · Granted Jan 9, 2024

Organic electroluminescent materials and devices

Inventors: Jui-Yi Tsai (Newtown, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Alexey Borisovich Dyatkin (Ambler, PA); Jerald Feldman (Cherry Hill, NJ); Zhiqiang Ji (Chalfont, PA); Hsiao-Fan Chen (Lawrence Township, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/342 C07F5/027 C07F15/0033 C07F15/0086 C07F19/00 C09K11/06 H10K85/322 H10K85/622 H10K85/626 H10K85/6576 C09K2211/185 H10K50/11 H10K85/654 H10K2101/10

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Quick Facts

Patent No.: US 11,871,653
App. No.: 16/788,886
Granted: Jan 9, 2024
Kind: B2

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Abstract

Novel metal complexes incorporating boron-containing aromatic compounds useful as a phosphorescent OLED material are disclosed. The metal complex includes a first ligand L A having the following formula

Claims (471)

1. A compound comprising a first ligand L A ;

wherein L A has the following formula:

wherein,

A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

R 2 and R 3 represent mono, di, tri, tetra substitutions or no substitution;

each R 1 , R 2 , and R 3 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, boryl, and combinations thereof;

any two adjacent R 1 , R 2 , and R 3 can be joined to form a ring, which can be further substituted;

L A is bidentate and is coordinated to a metal M; and

L A does not include the following structure

but can include

wherein

ring J is a 5-membered or 6-membered heterocyclic ring;

X 3 to X 8 , X 10 , and X 12 are each independently C or N;

R 11 to R 14 represent mono to the maximum possible number of substitutions or no substitution;

each substituent in R 11 to R 14 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, boryl, and combinations thereof;

any two adjacent R 11 to R 14 can be joined to form a ring, which can be further substituted;

wherein one of R 2 or R 3 comprises a 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring and is coordinated to the metal M; and

wherein ring A or ring B is coordinated to M.

2. The compound of claim 1 , wherein each R 1 , R 2 , and R 3 is independently a 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, boryl, and combinations thereof.

3. The compound of claim 1 , wherein the metal M is a metal selected from the group consisting of Ir, Pt, Re, Os, Ru, Rh, Pd, Cu, Ag, and Au.

4. The compound of claim 1 , wherein two R 2 substituents or two R 3 substituents are joined together to form a fused aromatic ring.

5. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 comprises a chemical group selected from the group consisting of:

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

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

wherein R e and R f can be fused or joined to form a ring;

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

wherein each R a , R b , R c , R d , R e , and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;

wherein any two adjacent substituents of R a , R b , R c , and R d can be fused or joined to form a ring or form a multidentate ligand; and

wherein the dashed lines represent the bonds to metal M.

6. The compound of claim 1 , wherein the first ligand L A is selected from the group consisting of:

wherein ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

wherein ring J is a 5-membered or 6-membered heterocyclic ring;

wherein Z 1 is C or N;

wherein X 1 to X 8 , X 10 , X 12 are each independently C or N;

wherein R 1 to R 4 , R 11 to R 14 represent mono to the maximum possible number of substitutions or no substitution;

wherein each R 2 to R 4 , R 11 to R 14 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, boryl, and combinations thereof;

wherein any two adjacent R 1 to R 4 , R 11 to R 14 can be joined to form a ring, which can be further substituted;

wherein L A forms a 5-membered chelate ring upon complexation to M;

wherein L A can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein the dashed lines represent the bonds to metal M.

7. The compound of claim 1 , wherein the first ligand L A is selected from the group consisting of L An , wherein n is an integer from 1 to 21, 60 to 69, 85 to 105, that are defined as follows:

n in

Formula

L An

R 2A

R 4A

R 4B

R 1

R 3

CD 3

3-CD 3

CD 3

CD 2 CMe 3

CD 3

4-CD 3

CD 3

CD 2 CMe 3

CD 3

CD 2 CMe 3

CD 3

10.

CD 3

11.

CMe 2

12.

CD 3

CMe 2

13.

CD 3

CMe 2

14.

CD 3

CMe 2

4-CD 3

15.

CD 3

16.

CD 3

17.

CD 3

1-CD 3

18.

CD 3

2-CD 3

19.

CD 3

3-CD 3

20.

CD 3

4-CD 3

21.

CD 2 CMe 3

CD 3

60.

CH 3

—

61.

CH 3

CHMe 2

—

62.

CH 3

—

63.

CH 3

CMe 3

—

64.

CH 3

—

65.

CH 3

—

2-CH 3

66.

CH 3

—

3-CH 3

67.

CH 3

—

4-CH 3

68.

CH 3

—

69.

CH 3

—

85.

CH 3

—

2-CH 3

86.

CH 3

—

3-CH 3

87.

CH 3

—

4-CH 3

88.

CH 3

—

5-CH 3

89.

CH 3

—

6-CH 3

90.

CH 3

—

91.

CH 3

—

92.

—

93.

—

94.

—

95.

CH 3

—

CH 3

96.

CH 3

—

CHMe 2

97.

CH 3

—

98.

CH 3

—

CH 3

99.

CH 3

—

CHMe 2

100.

CH 3

—

101.

CH 3

—

102.

CH 3

—

103.

CH 3

—

104.

—

CD 3

—

105.

—

CD 2 CMe 3

CD 3

—

wherein Formulae 1 to 3, 10, 11, 15 to 20 are defined as:

8. The compound of claim 7 , wherein the compound has the formula M(L A ) x (L B ) y (L C ) z , wherein L B and L C are each a bidentate ligand; and wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.

9. The compound of claim 8 , wherein the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), Ir(L A ) 2 (L C ), and Ir(L A )(L B )(L C ); and wherein L A , L B , and L C are different from each other.

10. The compound of claim 8 , wherein L B and L C are each independently selected from the group consisting of:

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

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

wherein R e and R f can be fused or joined to form a ring;

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

wherein each R a , R b , R c , R d , R e , and R f is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;

wherein any two adjacent substituents of R a , R b , R c , and R d can be fused or joined to form a ring or form a multidentate ligand; and

wherein the dashed lines represent the bonds to metal M.

11. The compound of claim 9 , wherein the compound is the Compound Ax having the formula Ir(L An ) 3 , or the Compound By having the formula Ir(L An )(L Bk ) 2 ;

wherein x=n, y=263n+k−263;

wherein n is an integer from 1 to 21, 60 to 69, 85 to 105, and k is an integer from 1 to 263, and j is an integer from 1 to 768;

wherein L Bk is selected from the group consisting of L B1 to L B263 having the following structures:

wherein the dashed lines represent the bonds to metal M.

12. 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 first ligand L A ;

wherein L A has the following formula:

wherein,

A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

R 2 and R 3 represent mono, di, tri, tetra substitutions or no substitution;

any two adjacent R 1 , R 2 , and R 3 can be joined to form a ring, which can be further substituted;

L A is bidentate and is coordinated to a metal M; and

L A does not include the following structure

but can include

wherein

ring J is a 5-membered or 6-membered heterocyclic ring;

X 3 to X 8 , X 10 , and X 12 are each independently C or N;

R 11 to R 14 represent mono to the maximum possible number of substitutions or no substitution;

any two adjacent R 11 to R 14 can be joined to form a ring, which can be further substituted;

wherein one of R 2 or R 3 comprises a 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring and is coordinated to the metal M; and

wherein ring A or ring B is coordinated to M.

13. The OLED of claim 12 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

14. The OLED of claim 12 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

15. 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 compound comprising a first ligand L A ;

wherein L A has the following formula:

wherein,

A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

R 2 and R 3 represent mono, di, tri, tetra substitutions or no substitution;

any two adjacent R 1 , R 2 , and R 3 can be joined to form a ring, which can be further substituted;

L A is bidentate and is coordinated to a metal M; and

L A does not include the following structure

but can include

wherein

ring J is a 5-membered or 6-membered heterocyclic ring;

X 3 to X 8 , X 10 , and X 12 are each independently C or N;

R 11 to R 14 represent mono to the maximum possible number of substitutions or no substitution;

any two adjacent R 11 to R 14 can be joined to form a ring, which can be further substituted;

wherein one of R 2 or R 3 comprises a 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring and is coordinated to the metal M; and

wherein ring A or ring B is coordinated to M.

Assignments (1)

NUNC PRO TUNC ASSIGNMENT Recorded Feb 12, 2020

From: TSAI, JUI-YI; BOUDREAULT, PIERRE-LUC T.; DYATKIN, ALEXEY BORISOVICH; FELDMAN, JERALD; JI, ZHIQIANG; CHEN, HSIAO-FAN

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 051802/0146 →

Continuity (2)

Provisional Application 62809216 · Feb 22, 2019

Related Publication 20200274079A1 · Aug 27, 2020