Phosphorescent emitters with phenylimidazole ligands

Patent metadata

Field	Value
Publication number	US-9978958-B2
Application number	US-201313798668-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Aug 24, 2012
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

Phosphorescent materials are provided, where the materials comprise a coordination compound having at least one ligand L 3 having Formula (I):

wherein A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; wherein R A , R B , R C , and R D each represent mono, di, tri, tetra substitutions, or no substitution; wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 are each selected from N or C; wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 is N; wherein one of Z 1 , Z 2 , Z 3 , and Z 4 is C that is bonded to N of A; wherein Z is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′; wherein R, R′, R A , R B , R C , and R D are described herein; wherein L 3 is coordinated to a metal M 1 ; and wherein L 3 may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand. Devices, such as organic light emitting devices, comprising such compounds are also provided.

First claim

The invention claimed is:

1. A compound having a structure of Formula (III):

wherein Z 9 -Z 19 is a bidentate ligand;
wherein n is 1, 2, or 3;
wherein R B and R D each represent mono, di, tri, tetra substitutions, or no substitution;
wherein R A represents mono, di, or no substitution;
wherein R C represents mono, di, tri, or no substitution;
wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 are each selected from N or C;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 is N;
wherein one of Z 1 , Z 2 , Z 3 , and Z 4 is C that is bonded to N of A;
wherein Z is selected from the group consisting of BR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein R, R′, R A , R B , R C , and R D 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, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two adjacent R, R A , R C , and R D are optionally joined to form a ring, which may be further substituted;
wherein the ligands may be linked with other ligands to form a tetradentate or hexadentate ligand;
wherein:
if Z 1 is bonded to N of ring A, then Z 2 is CR″;
if Z 2 is bonded to N of ring A, then both Z 1 and Z 3 are CR″;
if Z 3 is bonded to N of ring A, then both Z 2 and Z 4 are CR″; or
if Z 4 is bonded to N of ring A, then Z 3 is CR″; and

wherein R″ is alkyl, cycloalkyl, aryl, or substituted aryl.

2. The compound of claim 1 , wherein the compound is homoleptic.

3. The compound of claim 1 , wherein the compound is heteroleptic.

4. The compound of claim 1 , wherein only one of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 is N.

5. The compound of claim 1 , wherein Z is O or S.

6. The compound of claim 1 , wherein R″ 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, cyclohexyl, phenyl, and combinations thereof.

7. The compound of claim 1 , wherein Z 9 Z 10 is selected from the group consisting of 1-phenylimidazole, 2-phenylpyridyl, 1-(4-dibenzofuran)imidazole, and 1-(4-dibenzothiophene)imidazole, each of which is optionally substituted one or more times by substituents selected independently from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

8. The compound of claim 1 selected from the group consisting of:

wherein R C1 , R C2 , R C3 and R C4 are each independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; and X and Z are O or S.

9. The compound of claim 8 , wherein R C1 , R C2 , R C3 and R C4 are each independently 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, phenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,6-diisopropylphenyl, and combinations thereof; and
wherein any group is optionally partially or fully deuterated.

10. The compound of claim 1 , which is selected from the group consisting of:

11. The compound of claim 1 , wherein Z is selected from the group consisting of BR, PR, O, S, Se, C═O, S═O, SO 2 , SiRR′, and GeRR′.

12. The compound of claim 1 , wherein one of Z 1 , Z 2 , Z 3 , and Z 4 is N.

13. The compound of claim 1 , wherein Z 9 Z 10 is selected from the group consisting of 1-phenylimidazole, 2-phenylpyridyl, 1-(4-dibenzofuran)imidazole, and 1-(4-dibenzothiophene)imidazole, each of which is optionally substituted one or more times by substituents selected independently from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

14. A first device comprising a first organic light emitting device, which further comprises:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, which comprises a compound having a structure of Formula (III):

wherein Z 9 -Z 19 is a bidentate ligand;
wherein n is 1, 2, or 3;
wherein R B and R D each represent mono, di, tri, tetra substitutions, or no substitution;
wherein R A represents mono, di, or no substitution;
wherein R C represents mono, di, tri, or no substitution;
wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 are each selected from N or C;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 is N;
wherein one of Z 1 , Z 2 , Z 3 , and Z 4 is C that is bonded to N of A;
wherein Z is selected from the group consisting of BR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein R, R′, R A , R B , R C , and R D 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, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two adjacent R, R A , R C , and R D are optionally joined to form a ring, which may be further substituted;
wherein the ligands may be linked with other ligands to form a tetradentate or hexadentate ligand;
wherein:
if Z 1 is bonded to N of ring A, then Z 2 is CR″;
if Z 2 is bonded to N of ring A, then both Z 1 and Z 3 are CR″;
if Z 3 is bonded to N of ring A, then both Z 2 and Z 4 are CR″; or
if Z 4 is bonded to N of ring A, then Z 3 is CR″; and

wherein R″ is alkyl, cycloalkyl, aryl, or substituted aryl.

15. The first device of claim 14 , wherein the first device is a consumer product selected from the group consisting of flat panel displays, computer monitors, medical monitors, televisions, billboards, lig

Assignees

• Xia Chuanjun
• Lin Chun
• Kottas Gregg
• Elshenawy Zeinab
• Universal Display Corp

Inventors

• Xia Chuanjun
• Lin Chun
• Kottas Gregg
• Elshenawy Zeinab

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D491/048 Primary

  the oxygen-containing ring being five-membered · CPC title