Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11653558-B2
Application number	US-201916419337-A
Country	US
Kind code	B2
Filing date	May 22, 2019
Priority date	Dec 16, 2013
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

A compound having the formula (LA)mIr(LB)3-m, where LA isand LB is selected fromis disclosed. In the formula (LA)mIr(LB)3-m, LA and LB are different; each of X1 to X5 is C—RF or nitrogen; X is selected from O, S, and Se; each R1, R2, RB, RD, RE, and RF is hydrogen or a substituent; R3 is alkyl, cycloalkyl, or a combination thereof; and m is 1 or 2. OLEDs, consumer products, and formulations including the compound are also disclosed.

First claim

What is claimed is:

1. A compound having the formula
(L A ) m Ir(L B ) 3-m   (I);

wherein L A is

wherein L B is

wherein L A and L B are different;
wherein R 2 and R D are each independently mono, di, or ti-substitution, or no substitution;
wherein R 1 , R B , and R F are each independently mono, di, tri, or tetra-substitution, or no substitution;
wherein X 1 , X 2 , X 3 , X 4 , and X 5 are each independently CH or nitrogen, wherein the H in CH can be substituted by R F ;
wherein R 1 , R 2 , R B , R D , and R F are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, heteroalkyloxycarbonyl, arylalkyloxycarbonyl, alkenyloxycarbonyl, cycloalkenyloxycarbonyl, heteroalkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, cyano, carbylamino, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R 3 is selected from the group consisting of alkyl, cycloalkyl, and combinations thereof;
wherein R 3 is optionally partially or fully deuterated; and
wherein m is 1 or 2.

2. The compound of claim 1 , wherein m is 2.

3. The compound of claim 1 , wherein R 3 is an alkyl having at least 2 carbons.

4. The compound of claim 1 , wherein R 3 is a cycloalkyl.

5. The compound of claim 1 , wherein R 3 is selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, and cyclohexyl, wherein each is optionally partially or fully deuterated.

6. The compound of claim 1 , wherein R 1 is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

7. The compound of claim 1 , wherein R 2 represents no substitution.

8. The compound of claim 1 , wherein R F is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halogen, and combinations thereof.

9. The compound of claim 1 , wherein R F is fluorine.

10. The compound of claim 1 , wherein R D represents no substitution.

11. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:
(L A ) m Ir(L B ) 3-m   (I);

wherein L A is

wherein L B is

wherein L A and L B are different;
wherein R 2 and R D are each independently mono, di, or ti-substitution, or no substitution;
wherein R 1 , R B , and R F are each independently mono, di, tri, or tetra-substitution, or no substitution; wherein
wherein X 1 , X 2 , X 3 , X 4 , and X 5 are each independently CH or nitrogen, wherein the H in CH can be substituted by R F ;
wherein R 1 , R 2 , R B , R D , and R F are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, heteroalkyloxycarbonyl, arylalkyloxycarbonyl, alkenyloxycarbonyl, cycloalkenyloxycarbonyl, heteroalkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, cyano, carbylamino, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
wherein R 3 is selected from the group consisting of alkyl, cycloalkyl, and combinations thereof;
wherein R 3 is optionally partially or fully deuterated; and
wherein m is 1 or 2.

12. A formulation comprising a compound of claim 1 .

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

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

Assignees

• Universal Display Corp

Inventors

• Ma Bin
• Barron Edward
• Deangelis Alan
• Yeager Walter
• Elshenawy Zeinab
• Wendt Harvey
• Wang Ting-Chih
• Cheon Kwang-Ohk
• Xia Chuanjun

Classifications

• H10K85/342

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/6576

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

• Y02P70/50

  Manufacturing or production processes characterised by the final manufactured product · CPC title