Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12575314-B2
Application number	US-202418731922-A
Country	US
Kind code	B2
Filing date	Jun 3, 2024
Priority date	Mar 29, 2017
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

Abstract

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

First claim

What is claimed is:

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, cycl

Assignees

• Universal Display Corp

Inventors

• Tsai Jui-Yi
• Zeng Lichang
• Ji Zhiqiang
• Dyatkin Alexey Borisovich
• Yeager Walter
• Barron Edward

Classifications

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/631

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title