Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11937503-B2
Application number	US-201816168077-A
Country	US
Kind code	B2
Filing date	Oct 23, 2018
Priority date	Nov 30, 2017
Publication date	Mar 19, 2024
Grant date	Mar 19, 2024

Abstract

A composition comprising a first compound capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature is disclosed. The first compound has at least one aromatic ring with at least one substituent R of Formula IIn the structure of Formula I, R′ includes at least one fluorine atom; R′ represents mono to a maximum possible number of substitutions, or no substitution; each R2 is a hydrogen or one of a variety of substituents; L is an organic linker or direct bond; any two R1, R2 substituents may be joined or fused together to form a ring; the dashed line of Formula I is a bond to a first aromatic ring of the at least one aromatic ring; and n is an integer from 1 to 10. Organic light emitting devices and consumer products containing the compounds are also disclosed.

First claim

We claim:

1. A composition comprising a first compound;
wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;
wherein the first compound has a formula of M(L 1 ) x (L 2 ) y (L 3 ) z ;
wherein L 1 , L 2 , and L 3 can be the same or different;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein L 1 , L 2 , and L 3 are each bidentate ligands, and L 1 is selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form an aromatic ring;
wherein each R a , R a′ , R b , R c , and R d may represent from mono substitution to a maximum possible number of substitutions, or no substitution;
wherein R′, R″, R a , R a′ , R b , R c , and R d are each independently a hydrogen or a substituent selected from the group consisting of 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 substitutents of R a , R b , R c , and R d are optionally fused or joined to form an aromatic ring or form a multidentate ligand;
wherein no two substituents R a′ are fused or joined to form a ring; and
wherein at least one R a , R a′ , R b , R c , or R d present in the first compound includes at least one substituent R of Formula I:

wherein the dashed line represents a single bond;
wherein R 1 is fluorine or a partially or fully fluorinated moiety selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof;
wherein R 2 represents mono to a maximum possible number of substitutions;
wherein each R 2 is a hydrogen or a substituent selected from the group consisting of 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;
at least one R 2 comprises at least one fluorine atom;
wherein L is an organic linker or direct bond;
wherein any two R 1 , R 2 substituents may be joined or fused together to form a ring; and
wherein n is an integer from 2 to 10.

2. The composition of claim 1 , wherein the first compound is capable of emitting light from a triplet excited state to a ground singlet state at room temperature.

3. The composition of claim 1 , wherein the metal is Ir or Pt.

4. The composition of claim 1 , wherein the cycloalkyl moiety of at least one substituent R is separated from the first aromatic ring by one carbon atom.

5. The composition of claim 1 , wherein n is 3 or 4.

6. The composition of claim 1 , wherein at least one R 2 is a fluorine atom.

7. The composition of claim 1 , wherein L 2 and L 3 are each independently selected from the group consisting of:

8. The composition of claim 7 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ), wherein L 1 has the formula selected from the group consisting of:

wherein L 2 has the formula:

9. The composition of claim 7 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ); and wherein L 1 and L 2 are different and each independently selected from the group consisting of:

10. The composition of claim 7 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ); and wherein L 1 and L 2 are each independently selected from the group consisting of:

11. The composition of claim 1 , wherein the first compound has a structure of the formula Ir(L 1 ) 2 (L Cj ), wherein j is an integer from 1 to 1260; and
wherein L C1 through L C1260 are based on a structure of Formula X,

 in which R 1 , R 2 , and R 3 are defined as:

Ligand
R 1
R 2
R 3

L C1
R D1
R D1
H

L C2
R D2
R D2
H

L C3
R D3
R D3
H

L C4
R D4
R D4
H

L C5
R D5
R D5
H

L C6
R D6
R D6
H

L C7
R D7
R D7
H

L C8
R D8
R D8
H

L C9
R D9
R D9
H

L C10
R D10
R D10
H

L C11
R D11
R D11
H

L C12
R D12
R D12
H

L C13
R D13

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Joseph Scott

Classifications

• H10K59/90

  Assemblies of multiple devices comprising at least one organic light-emitting element · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K85/622

  containing four rings, e.g. pyrene · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title