Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10991896-B2
Application number	US-201816129152-A
Country	US
Kind code	B2
Filing date	Sep 12, 2018
Priority date	Jul 1, 2013
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

A compound having an ancillary ligand L 1 having the formula:

Formula I is disclosed. The ligand L 1 is coordinated to a metal M having an atomic number greater than 40, and two adjacent substituents are optionally joined to form into a ring. Such compound is suitable for use as emitters in organic light emitting devices.

First claim

We claim:

1. 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 a formula of Ir(L 1 ) x (L 2 ) y ,
wherein x is 1 or 2;
wherein y is 1 or 2;
wherein x+y is 3;
wherein the first ligand L 1 has the formula:

wherein the second ligand L 2 has a formula selected from the group consisting of

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from group consisting of alkyl and cycloalkyl;
wherein each of R 1 , R 2 , R 3 , and R 4 has at least two C;
wherein R a and R b can represent mono, di, tri, or tetra substitution, or no substitution;
wherein each of R a , R b , and R 5 is selected from 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 two adjacent substituents of R a and R b are optionally joined to form a fused ring or form a multidentate ligand; and
wherein R 1 and R 2 or R 3 and R 4 can be joined to form into a ring.

2. The first device of claim 1 , wherein R 5 is selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

3. The first device of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are alkyl.

4. The first device of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are 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, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof.

5. The first device of claim 1 , wherein the compound has the formula of Ir(L 1 )(L 2 ) 2 .

6. The first device of claim 1 , wherein L 1 is selected from group consisting of:

7. The first device of claim 6 , wherein L 2 is selected from group consisting of:

8. The first device of claim 7 wherein the compound has a formula of M(L 1 )(L 2 ) 2 and is selected from the group consisting of Compound 1 to Compound 133, Compound 267 to Compound 399, Compound 533 to Compound 665, Compound 799 to Compound 931, Compound 1065 to Compound 1330, and Compound 1597 to Compound 1729 defined in the table below:

Compound

number
L 1
L 2

1.
L A1
L Q1

2.
L A1
L Q2

3.
L A1
L Q3

4.
L A1
L Q4

5.
L A1
L Q5

6.
L A1
L Q6

7.
L A1
L Q7

8.
L A1
L Q8

9.
L A1
L Q9

10.
L A1
L Q10

11.
L A1
L Q11

12.
L A1
L Q12

13.
L A1
L Q13

14.
L A1
L Q14

15.
L A1
L Q15

16.
L A1
L Q16

17.
L A1
L Q17

18.
L A1
L Q18

19.
L A1
L Q19

20.
L A1
L Q20

21.
L A1
L Q21

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Dyatkin Alexey
• Li David Zenan
• Joseph Scott
• Xia Chuanjun
• Yamamoto Hitoshi
• Weaver Michael S
• Alleyne Bert
• Fiordeliso James

Classifications

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K85/342

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H10K85/6576

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

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title