IP Library › Granted Patent US 12,575,314
Granted Patent B2
US 12,575,314 · App. 18/731,922 · Granted Mar 10, 2026

Organic electroluminescent materials and devices

Inventors: Jui-Yi Tsai (Newtown, PA); Lichang Zeng (Lawrenceville, NJ); Zhiqiang Ji (Chalfont, PA); Alexey Borisovich Dyatkin (Ambler, PA); Walter Yeager (Yardley, PA); Edward Barron (Hamilton, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H10K85/342C07F15/0033C09K11/06C09K2211/1029C09K2211/1088C09K2211/185H10K50/11H10K85/622H10K85/631H10K85/654H10K85/6576H10K2101/10H10K2101/90
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Quick Facts
Patent No.
US 12,575,314
App. No.
18/731,922
Granted
Mar 10, 2026
Kind
B2
Abstract

A compound having the formula: is disclosed. The compound is useful as emitters in OLEDs.

Claims (52)

1 . A compound having the formula [L A ] 3-n Ir[L B ] n , having the structure:

wherein R 1 , R 2 , and R 3 each independently represents mono, to a maximum possible number of substitutions, or no substitutions;

wherein X 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 each R′, R″, R 1 , R 2 , R 3 , R B1 , R B2 , R B3 , and R B4 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;

wherein at least one of R B1 , R B2 , R B3 , or R B4 is selected from the group consisting of methyl, ethyl, isopropyl, —CH 2 CH(CH 3 ) 2 , tert-butyl, —CH 2 C(CH 3 ) 3 , partially or fully deuterated variants thereof, partially fluorinated variants thereof, and combinations thereof;

wherein any substitutions are optionally joined or fused into a ring;

wherein n is 1 or 2;

wherein R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof; and

wherein R has at least five carbon atoms.

2 . The compound of claim 1 , wherein each R′, R″, R 1 , R 2 , R 3 , R B1 , R B2 , R B3 , and R B4 is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

3 . The compound of claim 1 , wherein R has at least six carbon atoms.

4 . The compound of claim 1 , wherein R has at least seven carbon atoms.

5 . The compound of claim 1 , wherein n is 2.

6 . The compound of claim 1 , wherein X is O.

7 . The compound of claim 1 , wherein R comprises a branched alkyl, cycloalkyl or heterocycloalkyl.

8 . The compound of claim 1 wherein each R B1 , R B2 , R B3 , and R B4 is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, nitrile, and combinations thereof.

9 . The compound of claim 1 wherein R B1 is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, silyl, nitrile, and combinations thereof.

10 . The compound of claim 1 wherein R B2 is selected from the group consisting of hydrogen, deuterium, alkyl, aryl, heteroaryl, nitrile, and combinations thereof.

11 . The compound of claim 1 wherein R B3 is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, silyl, aryl, heteroaryl, and combinations thereof.

12 . The compound of claim 1 wherein R B4 is selected from the group consisting of hydrogen, deuterium, alkyl, silyl, aryl, heteroaryl, and combinations thereof.

13 . The compound of claim 1 , wherein at least one of the following is true: (1) R B1 is methyl, (2) R B3 is tert-butyl, or (3) R B4 is methyl.

14 . The compound of claim 1 , wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, aryloxy, silyl, alkenyl, aryl, heteroaryl, nitrile, and combinations thereof.

15 . The compound of claim 1 , wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, and combinations thereof.

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

wherein at least one of R B1 or R B4 is selected from the group consisting of methyl, ethyl, isopropyl, —CH 2 CH(CH 3 ) 2 , tert-butyl, —CH 2 C(CH 3 ) 3 , partially or fully deuterated variants thereof, partially fluorinated variants thereof, and combinations thereof:

wherein R 6 independently represents mono, to a maximum possible number of substitutions, or no substitutions;

wherein 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.

17 . 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 having the formula:

wherein R 1 , R 2 , and R 3 each independently represents mono, to a maximum possible number of substitutions, or no substitution;

wherein X 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 each R′, R″, R 1 , R 2 , R 3 , R B1 , R B2 , R B3 , and R B4 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;

wherein at least one of R B1 , R B2 , R B3 , or R B4 is selected from the group consisting of methyl, ethyl, isopropyl, —CH 2 CH(CH 3 ) 2 , tert-butyl, —CH 2 C(CH 3 ) 3 , partially or fully deuterated variants thereof, partially fluorinated variants thereof, and combinations thereof;

wherein any substitutions are optionally joined or fused into a ring;

wherein n is 1 or 2;

wherein R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combination thereof; and

wherein R has at least five carbon atoms.

18 . The OLED of claim 17 , 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, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

19 . 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 having the formula:

wherein R 1 , R 2 , and R 3 each independently represents mono, to a maximum possible number of substitutions, or no substitutions;

wherein X 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 each R′, R″, R 1 , R 2 , R 3 , R B1 , R B2 , R B3 , and R B4 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;

wherein at least one of R B1 , R B2 , R B3 , or R B4 is selected from the group consisting of methyl, ethyl, isopropyl, —CH 2 CH(CH 3 ) 2 , tert-butyl, —CH 2 C(CH 3 ) 3 , partially or fully deuterated variants thereof, partially fluorinated variants thereof, and combinations thereof;

wherein any substitutions are optionally joined or fused into a ring;

wherein n is 1 or 2;

wherein R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combination thereof; and

wherein R has at least five carbon atoms.

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Jun 3, 2024
From: TSAI, JUI-YI; ZENG, LICHANG; JI, ZHIQIANG; DYATKIN, ALEXEY BORISOVICH; YEAGER, WALTER; BARRON, EDWARD
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 067600/0911 →
Continuity (6)
Continuation 18301353 · Apr 17, 2023
Continuation 17320422 · May 14, 2021
Continuation 15918179 · Mar 12, 2018
Provisional Application 62479730 · Mar 31, 2017
Provisional Application 62478072 · Mar 29, 2017
Related Publication 20240341165A1 · Oct 10, 2024
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