Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10144867-B2
Application number	US-201615013559-A
Country	US
Kind code	B2
Filing date	Feb 2, 2016
Priority date	Feb 13, 2015
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

A compound having a Pt tetradentate structure selected from the group consisting of

is provided. In the structures of Formula 1 and Formula 2, rings C and D each independently represent 5- or 6-membered carbocyclic or heterocyclic ring; L 1 , L 2 , and L 3 are each independently a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , SiRR′, GeRR′, alkyl, cycloalkyl, or a combination thereof; the sum of n1 and n2 is 1 or 2; X is selected from NR E , O, S, and Se; X 3 and X 4 each independently carbon or nitrogen; and one of Q 1 , Q 3 , and Q 4 is oxygen, and the remaining two of Q 1 , Q 3 , and Q 4 each represents a direct bond. Formulations and devices, such as an OLEDs, that include the compound of Formulas 1 and 2 are also described.

First claim

We claim:

1. A compound having a Pt tetradentate structure, having the formula selected from the group consisting of:

wherein rings C and D each independently represents aryl or heteroaryl;
wherein R A , R B1 , R C , and R D each independently represents mono, di, tri, tetra-substitution, or no substitution;
wherein R B2 represents mono, di-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 , SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
wherein n1 and n2 are each independently an integer of 1 or 0; the sum of n1 and n2 is at least 1; when n1 is 0, L 1 is not present; and when n2 is 0, L 2 is not present;
wherein X is selected from the group consisting of NR E , O, S, and Se;
wherein R A , R B1 , R B2 , R C , R D , R E , 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, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent R A , R B , R C , R D , R E , R, and R′ are optionally joined to form a ring;
wherein X 3 and X 4 each independently selected from the group consisting of carbon and nitrogen; and
wherein one of Q 1 , Q 3 , and Q 4 is oxygen, and the remaining two of Q 1 , Q 3 , and Q 4 each represents a direct bond.

2. The compound of claim 1 , wherein Q 1 is oxygen, and Q 3 and Q 4 each represents a direct bond.

3. The compound of claim 1 , wherein n1 is 1, and n2 is 0.

4. The compound of claim 1 , wherein n1 is 0, and n2 is 1.

5. 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, SiRR′, alkyl, cycloalkyl, and combinations thereof.

6. The compound of claim 1 , wherein L 1 , L 2 , and L 3 each independently represents a direct bond.

7. The compound of claim 1 , wherein at least one of L 1 , L 2 , and L 3 is SiRR′ or GeRR′, and 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.

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

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

10. The compound of claim 1 , wherein X is NR E .

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

wherein Y is selected from the group consisting of CR 1 R 2 , SiR 1 R 2 , NR 1 , O, S, and Se;
wherein R 1 , and R 2 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 each X is selected from the group consisting of NR E , O, S, and Se; and
wherein any adjacent R 1 , and R 2 are optionally joined to form a ring.

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

wherein Y is selected from the group consisting of CR 1 R 2 , SiR 1 R 2 , NR 1 , O, S, and Se;
wherein R 1 , and R 2 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; and
wherein any adjacent R 1 , and R 2 are optionally joined to form a ring.

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

14. A first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed betwe

Assignees

• Universal Display Corp

Inventors

• Ma Bin
• Su Mingjuan
• Deangelis Alan
• Barron Edward
• Xia Chuanjun

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• H01L51/0067

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title