Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10135008-B2
Application number	US-201414565576-A
Country	US
Kind code	B2
Filing date	Dec 10, 2014
Priority date	Jan 7, 2014
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

A novel Pt tetradentate complexes having Pt—O bond is disclosed. These complexes are useful as emitters in phosphorescent OLEDs.

First claim

What is claimed is:

1. A compound having a Pt tetradentate structure, having the formula:

Formula I;
wherein rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R A , R B , R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;
wherein when n is 1, L 4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;
when n is 0, L 4 is not present;
wherein R A , R B , R C , R D , R, and R′ are each 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, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof;
wherein any adjacent R A , R B , R C , R D , R, and R′ are optionally joined to form a ring;
wherein X 1 , X 2 , X 3 , and X 4 each independently selected from the group consisting of carbon and nitrogen;
wherein one of Q 1 , Q 2 , Q 3 , and Q 4 is oxygen, the remaining three of Q 1 , Q 2 , Q 3 , and Q 4 each represents a direct bond so that Pt directly bonds to three of X 1 , X 2 , X 3 , and X 4 ; and
wherein when L 1 , L 2 , L 3 , or L 4 represents a direct bond, the direct bond is not a C—C bond.

2. The compound of claim 1 , wherein two of X 1 , X 2 , X 3 , and X 4 that directly bond to Pt are carbon thus forming Pt—C bonds, and one of X 1 , X 2 , X 3 , and X 4 that directly bond to Pt is nitrogen.

3. The compound of claim 2 , wherein the two Pt—C bonds are in cis configuration.

4. The compound of claim 1 , wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, NR, O, CRR′, SiRR′, and combinations thereof; and
wherein when n is 1, L 4 is selected from the group consisting of a direct bond, NR, O, CRR′, SiRR′, and combinations thereof.

5. The compound of claim 1 , wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, 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, phenyl, and combinations thereof.

6. The compound of claim 1 , wherein the compound has at least one Pt-carbene bond.

7. The compound of claim 1 , wherein n is 0.

8. The compound of claim 1 , wherein n is 1.

9. The compound of claim 1 , wherein one of the rings A, B, C, and D is phenyl when said ring is bonded to one of the Q 1 , Q 2 , Q 3 and Q 4 that is oxygen.

10. The compound of claim 1 , wherein the rings A, B, C, and D are each independently selected from the group consisting of phenyl, pyridine, and imidazole.

11. The compound of claim 1 , wherein when L 1 , L 2 , L 3 , or L 4 represents a direct bond, the direct bond is a C—N bond.

12. The compound of claim 1 , wherein at least one of L 1 , L 2 , L 3 , and L 4 is not a direct bond.

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

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

15. A device comprising one or more organic light emitting devices, at least one of the organic light emitting devices comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a Pt tetradentate structure, having the formula:

Formula I;
wherein rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R A , R B , R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;
wherein when n is 1, L 4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;
when n is 0, L 4 is not present;
wherein R A , R B , R C , R D , R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycl

Assignees

• Universal Display Corp

Inventors

• Lin Chun
• Xia Chuanjun
• Tsai Jui-Yi

Classifications

• C07F15/0093 Primary

  without a metal-carbon linkage · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D233/54

  having two double bonds between ring members or between ring members and non-ring members · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• H01L51/5016

  Electricity · mapped topic