Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9493698-B2
Application number	US-201213584483-A
Country	US
Kind code	B2
Filing date	Aug 13, 2012
Priority date	Aug 31, 2011
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

Novel phosphorescent tetradentate platinum (II) compounds are provided. The compounds contain an isoimidazole moiety, optionally further substituted with a twisted aryl. These compounds may be advantageously used in OLEDs.

First claim

The invention claimed is:

1. A compound having the formula:

wherein A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein L 1 and L 3 are independently selected from the group consisting of a single bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein L 2 is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein n 1 is 0 or 1;
wherein n 2 is 0 or 1;
wherein n 1 +n 2 is at least equal to 1;
wherein Z 1 and Z 2 are independently a nitrogen atom or a carbon atom;
wherein R 1 , R 2 , R 3 , and R 4 may represent mono-, di-, tri-, or tetra-substitutions;
wherein R, R′, R 1 , R 2 , R 3 , R 4 , and R 5 are 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 R 1 is optionally fused to A;
wherein R 3 is optionally fused to B;
wherein R 4 is optionally fused to C;
wherein R 3 and R 4 are optionally joined to form into a ring;
wherein R 3 and L 2 are optionally joined to form into a ring;
wherein R 4 and L 2 are optionally joined to form into a ring; and
wherein at least one of the following (i)-(vi) is true:
(i) n 1 =0 and n 2 =1;
(ii) wherein R 5 is

wherein R′ 1 and R′ 2 are independently selected from the group consisting of 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, partially or fully deuterated variations thereof, and combinations thereof;
wherein D is 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted with R′ 3 ; and
wherein R′ 3 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;
(iii) wherein the compound has the structure of Formula IIA,

(iv) wherein the compound has the structure of Formula IIIA,

(v) wherein the compound has the structure of Formula VIA,

and
(vi) wherein the compound has the structure of Formula VIIA,

2. The compound of claim 1 , wherein R 5 is a 2,6-disubstituted aryl.

3. The compound of claim 1 , wherein R 5 is

wherein R′ 1 and R′ 2 are independently selected from the group consisting of 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 D is 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted with R′ 3 ; and
wherein R′ 3 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.

4. The compound of claim 3 , wherein each of R′ 1 and R′ 2 is an alkyl.

5. The compound of claim 3 , wherein each of R′ 1 and R′ 2 is an alkyl containing at least 2 carbons.

6. The compound of claim 3 , wherein each of R′ 1 and R′ 2 is an aryl.

7. The compound of claim 3 , wherein the compound has the formula:

8. The compound of claim 3 , wherein the compound has the formula:

9. The compound of claim 3 , wherein the compound has the formula:

10. The compound of claim 3 , wherein the compound has the formula:

11. The compound of claim 1 , wherein L 1 or L 3 is selected from the group consisting of O, S, CH 2 , CR′ 2 , NR′, SiR′ 2 or BR′; and
wherein R′ is alkyl or aryl.

12. The compound of claim 1 , wherein L 2 is selected from the group consisting of O, S, CH 2 , CR′ 2 , NR′, and SiR′ 2 ;
wherein R′ is alkyl or aryl; and
wherein R′ is optionally bonded to B or C.

13. The compound of claim 1 , wherein R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, aryl, cyclic alkyl, branched alkyl, heteroaryl, and fused aryl.

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

Assignees

• Beers Scott
• Xia Chuanjun
• Brooks Jason
• Kottas Gregg
• Universal Display Corp

Inventors

• Beers Scott
• Xia Chuanjun
• Brooks Jason
• Kottas Gregg

Classifications

• C09K2211/185

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

• H05B33/18

  characterised by the nature or concentration of the activator · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title