Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11795385-B2
Application number	US-202217982828-A
Country	US
Kind code	B2
Filing date	Nov 8, 2022
Priority date	Feb 13, 2015
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

A compound having a Pt tetradentate structure of Formula 1,is provided. In the structure of Formula 1, rings C and D each independently represent 5- or 6-membered carbocyclic or heterocyclic ring; L1, L2, and L3 are each independently a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, SiRR′, GeRR′, alkyl, cycloalkyl, or a combination thereof; the sum of n1 and n2 is 1 or 2; X is selected from NRE, O, S, and Se; X3 and X4 each independently carbon or nitrogen; and one of Q1, Q3, and Q4 is oxygen, and the remaining two of Q1, Q3, and Q4 each represents a direct bond. Formulations and devices, such as an OLEDs, that include the compound of Formula 1 are also described.

First claim

The invention claimed is:

1. A first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a host and 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 represent 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;
wherein one of Q 1 , Q 3 , and Q 4 is oxygen, the remaining two of Q 1 , Q 3 , and Q 4 each represents a direct bond; and
wherein the host comprises at least one chemical group selected from the group consisting of

wherein:
each of R 1 and R 101 to R 108 is 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 when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above;
k is an integer from 1 to 20;
k′″ is an integer from 0 to 20;
each of X 101 to X 108 is independently selected from the group consisting of C and N; and
each of Z 101 and Z 102 is selected from the group consisting of NR 101 , O, and S.

2. The first organic light emitting device of claim 1 , wherein at least one of R 1 , R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , or R 108 is present and is selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, heteroaromatic analogs thereof,

3. The first organic light emitting device of claim 1 , wherein the host comprises at least one chemical group selected from the group consisting of

4. The first organic light emitting device of claim 3 , wherein at least one of R 1 , R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , or R 108 is present and is selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, heteroaromatic analogs thereof,

5. The first organic light emitting device of claim 1 , wherein the Pt tetradentate structure has the structure of Formula 1,

6. The first organic light emitting device of claim 1 , wherein the Pt tetradentate structure has the structure of Formula 2,

7. The first organic light emitting device of claim 1 , wherein the first organic light emitting device is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

8. The first organic light emitting device of claim 1 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

9. The first organic light emitting device of claim 1 , 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, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

10. The first organic light emitting device of claim 1 , wherein X is NR E .

11. The first organic light emitting device of claim 1 , wherein the host is selected from the group consisting of:

and combinations thereof.

12. The first organic light emitting device of claim 1 , wherein Q 1 is oxygen, and Q 3 and Q 4 each represents a direct bond.

13. The first organic light emitting device 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.

14. The first organic light emitting device of claim 1 , wherein L 1 , L 2 , and L 3 each independently represents a direct bond.

15. The first organic light emitting device of claim 1 , wherein the rings of C and D are each independently selected from the group consisting of phenyl, pyridine, benzimidazole, and imidazole.

16. The first organic light emitting device 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

Assignees

• Universal Display Corp

Inventors

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

Classifications

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C07F15/0086

  Platinum compounds · CPC title

• C09K11/06

  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