IP Library › Granted Patent US 12,006,333

Granted Patent B2

US 12,006,333 · App. 18/178,189 · Granted Jun 11, 2024

Organic electroluminescent materials and devices comprising imidazole-containing metal complexes

Inventors: Scott Beers (Flemington, NJ); Woo-Young So (Richboro, PA); Hsiao-Fan Chen (Lawrence Township, NJ)

C07F15/006 C07F15/0033 C07F15/0086 H10K59/12 H10K85/342 H10K85/346 H10K85/40 H10K85/622 H10K85/654 H10K85/6572 H10K85/6576 H10K50/11 H10K2101/10 H10K2101/40

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Quick Facts

Patent No.: US 12,006,333
App. No.: 18/178,189
Granted: Jun 11, 2024
Kind: B2

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Abstract

A compound comprising a first ligand L A of Formula I or Formula II: wherein A 1 and A 2 are each independently C or Si; wherein each R A , and R B independently represents mono to the maximum allowable substitution, or no substitution; wherein each X 1 , X 2 , and X 3 is independently C or N; wherein each R, R 1 , R 2 , R 3 , R 4 and R A is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein L A is complexed to a metal M; wherein M is optionally coordinated to one or more other ligands; wherein the ligand L A is optionally linked with the one or more other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and wherein any two substituents are optionally joined or fused together to form a ring.

Claims (661)

1. A compound comprising a first ligand L A of Formula I:

wherein A 1 and A 2 are each independently C or Si;

wherein each R A independently represents mono to the maximum allowable substitution, or no substitution;

wherein each R, R 1 , R 2 , R 3 , R 4 and R A is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein L A is complexed to a metal M;

wherein M is optionally coordinated to one or more other ligands;

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

wherein any two adjacent substituents are optionally joined or fused together to form a ring.

2. The compound of claim 1 , wherein each R, R 1 , R 2 , R 3 , R 4 and R A is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein A 1 and A 2 are each C.

4. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen and alkyl.

5. The compound of claim 1 , wherein R is selected from the group consisting of hydrogen, alkyl, and aryl.

6. The compound of claim 1 , wherein M is Pt, Pd, or Jr.

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

8. The compound of claim 1 , wherein the first ligand L A is selected from the group consisting of L A1 -L A64 ;

wherein of L A1 -L A36 are ligands of Formula III:

wherein A 1 , A 2 , R, R A , R 1 , R 2 , R 3 , R 4 are defined aS follows:

L A

A 1

R 1

R 2

A 2

R 3

R 4

R A

L A1

2,6-di-iPr—Ph

CH 3

L A2

2,6-di-iPr—Ph

CH 3

2,6-di-iPr—Ph

L A3

CH 3

2,6-di-iPr—Ph

L A4

CH 3

L A5

CH 3

L A6

2,6-di-iPr—Ph

CH 3

L A7

2,6-di-iPr—Ph

isopropyl

CH 3

L A8

CH 3

L A9

CH 3

2,6-di-iPr—Ph

L A10

2,6-di-iPr—Ph

CH 3

2,6-di-iPr—Ph

L A11

isopropyl

CH 3

L A12

CH 3

2,6-di-iPr—Ph

L A13

CH 3

L A14

CH 3

2,6-di-iPr—Ph

L A15

2,6-di-iPr—Ph

CH 3

2,6-di-iPr—Ph

L A16

2,6-di-iPr—Ph

CH 3

L A17

CH 3

i-Pr

L A18

CH 3

i-Pr

2,6-di-iPr—Ph

L A19

2,6-di-iPr—Ph

CH 3

i-Pr

2,6-di-iPr—Ph

L A20

CD 3

L A21

CD 3

2,6-di-iPr—Ph

L A22

Phenyl

CD 3

L A23

CD 3

Phenyl

L A24

2,6-di-iPr—Ph

CD 3

L A25

CD 3

isopropyl

L A26

CD 3

CH 3

L A27

CD 3

L A28

Phenyl

CH 3

L A29

Phenyl

CD 3

CH 3

L A30

Phenyl

CH 3

CD 3

Phenyl

L A31

isopropyl

CH 3

Phenyl

L A32

CD 3

CH 3

t-Butyl

L A33

Phenyl

CH 3

t-Butyl

L A34

Phenyl

CD 3

isopropyl

L A35

Phenyl

CD 3

t-Butyl

L A36

CD 3

t-Butyl

wherein of L A37 -L A64 are ligands of Formula IV:

wherein A 1 , A 2 , R, R A , R 1 , R 2 , R 3 , and R 4 are defined as follows:

L A

A 1

R 1

R 2

A 2

R 3

R 4

R A

L A37

CH 3

L A38

Phenyl

CH 3

L A39

2,6-di-

CH 3

iPr—Ph

L A40

CD 3

CH 3

L A41

CD 3

L A42

Phenyl

CD 3

L A43

2,6-di-

CD 3

iPr—Ph

L A44

CD 3

L A45

CH 3

L A46

Phenyl

CH 3

L A47

2,6-di-

CH 3

iPr—Ph

L A48

CD 3

CH 3

L A49

CD 3

CH 3

L A50

Phenyl

CD 3

CH 3

L A51

2,6-di-

CD 3

CH 3

iPr—Ph

L A52

CD 3

CH 3

L A53

CH 3

L A54

Phenyl

CH 3

L A55

2,6-di-

CH 3

iPr—Ph

L A56

CD 3

CH 3

L A57

CH 3

CD 3

L A58

Phenyl

CH 3

CD 3

L A59

2,6-di-

CH 3

CD 3

iPr—Ph

L A60

CD 3

CH 3

CD 3

L A61

isopropyl

CH 3

L A62

Phenyl

isopropyl

CH 3

L A63

2,6-di-

isopropyl

CH 3

iPr—Ph

L A64

CD 3

isopropyl

CH 3

and wherein 2,6-di-iPr-Ph is

9. The compound of claim 8 wherein the compound is the Compound Ax having the formula Ir(L Ai ) 3 ; or the Compound By having the formula Ir(L Ai )(L Bk ) 2 ;

wherein x=i and y=468i+k−468;

wherein i is an integer from 1 to 64 and k is an integer from 1 to 468;

wherein L Bk is selected from the group consisting of the following structures:

10. The compound of claim 1 , wherein the compound has a formula of 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.

11. The compound of claim 10 , 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 )(L B )(L C ), wherein L A , L B , and L C are different from each other; or the compound has a formula of Pt(L A )(L B ), wherein L A and L B are the same or different.

12. The compound of claim 10 , wherein L B and L C are each independently 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 are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d independently represents 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, 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, 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.

13. 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 of Formula I:

wherein A 1 and A 2 are each independently C or Si;

wherein each R A independently represents mono to the maximum allowable substitution, or no substitution;

wherein L A is complexed to a metal M;

wherein M is optionally coordinated to one or more other ligands;

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

wherein any two adjacent substituents are optionally joined or fused together to form a ring.

14. The OLED of claim 13 , wherein the organic layer further comprises a host, wherein the 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.

15. The OLED of claim 14 , wherein the host is selected from the group consisting of:

and combinations thereof.

16. A consumer product comprising 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 of Formula I:

wherein A 1 and A 2 are each independently C or Si;

wherein each R A independently represents mono to the maximum allowable substitution, or no substitution;

wherein L A is complexed to a metal M;

wherein M is optionally coordinated to one or more other ligands;

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

wherein any two adjacent substituents are optionally joined or fused together to form a ring.

17. The consumer product of claim 16 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign.

18. A formulation comprising a compound of claim 1 .

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2024

From: BEERS, SCOTT; SO, WOO-YOUNG; CHEN, HSIAO-FAN

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 066280/0504 →

Continuity (3)

Continuation 16854193 · Apr 21, 2020

Provisional Application 62840625 · Apr 30, 2019

Related Publication 20230203076A1 · Jun 29, 2023