Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9847497-B2
Application number	US-201514616438-A
Country	US
Kind code	B2
Filing date	Feb 6, 2015
Priority date	Feb 18, 2014
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

A compound having a structure of Formula M(L A ) x (L B ) y (L C ) z , where ligand L A is

ligand L B is

and ligand L C is

is disclosed. In Formula M(L A ) x (L B ) y (L C ) z , M is a metal having an atomic number greater than 40; x is 1, 2, or 3; y and z are 0, 1, or 2; x+y+z is the oxidation state of metal M; Z 1 -Z 6 are each C or N; Z D is N or a carbene carbon; rings C and D are independently a 5 or 6-membered carbocyclic or heterocyclic ring; R 4 is substituted, while each of R 1 , R 2 , R 3 , R C , R D , R 11 , R 12 , and R 13 are selected from hydrogen and a variety of moieties; and any adjacent substituents of R 1 , R 2 , R 3 , R 4 , R C , R D , R 11 , R 12 , and R 13 are optionally joined to form a ring. Formulations and devices, such as an OLEDs, that include the compound of formula M(L A ) x (L B ) y (L C ) z are also described.

First claim

We claim:

1. A compound having a structure of formula M(L A ) x (L B ) y (L C ) z :
wherein the ligand L A is

wherein the ligand L B is

wherein the ligand L C is

wherein M is a metal having an atomic number greater than 40;
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 Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each independently selected from C and N;
wherein Z D is selected from N and a carbene carbon;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R 3 represents mono, or di-substitutions, or no substitutions;
wherein R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein R 1 and R 2 each independently represent mono, di, or tri-substitution, or no substitutions;
wherein R 4 is 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 each of R 1 , R 2 , R 3 , R C , R D , R 11 , R 12 , and R 13 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 any adjacent substituents of R 1 , R 2 , R 3 , R 4 , R C , R D , R 11 , R 12 , and R 13 are optionally joined to form a ring; and
wherein at least one of the following:
(i) Z 1 is N,
(ii) Z 2 is N,
(iii) Z 3 is N,
(iv) Z 5 is N,
(v) R 1 is no substitutions, or
(vi) R 1 is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, alkynyl, aryl, furan, thiophene, acyl, carbonyl, carboxylic acids, ester, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1 , wherein M is Ir.

4. The compound of claim 1 , wherein the compound has the formula M(L A ) 2 (L C ).

5. The compound of claim 1 , wherein the compound has the foil iula M(L A )(L B ) 2 .

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

7. The compound of claim 1 , wherein the aryl or heteroaryl of R 4 is substituted by one or more substituent selected from the group consisting of 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, cyclobutyl, cyclopentyl, cyclohexyl, and combinations thereof.

8. The compound of claim 1 , wherein R 4 is phenyl substituted at both ortho positions by a substituent selected from the group consisting of 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, cyclobutyl, cyclopentyl, cyclohexyl, and combinations thereof.

9. The compound of claim 1 , wherein ligand L A has the structure:

wherein R 2′ represents mono, or di-substitutions, or no substitutions;
wherein R 2′ 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; and
wherein any adjacent substituents of R 2′ , and R 5 are optionally joined to form a ring.

10. The compound of claim 9 , wherein R 4 and R 5 are the identical.

11. The compound of claim 1 , wherein L C has the formula:

wherein R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;
wherein at least one of R 6 , R 7 , R 8 , R 9 , or R 10 has at least two C atoms.

12. The compound of claim 1 , wherein ring C is benzene, and ring D is pyridine.

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

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

wherein X 1 , X 2 , X 3 , X 4 , X 1′ , X 2′ , and X 3′ are each independently selected from the group consisting of N and CR″,
wherein each R, R′, and R″ is independently selected from the group consisting of H, alkyl, aryl, heteroaryl, and combinations thereof, and
wherein adjacent R, R′, and R″ substituents are optionally joined to form a fused or unfused ring.

15. The compound of claim 1 , where L C is selected from the group consisting of

Assignees

• Universal Display Corp
• Univ Southern California

Inventors

• Szigethy Geza
• Brooks Jason
• Thompson Mark E
• Saris Patrick
• Djurovich Peter I

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C07F15/02

  Iron compounds · CPC title

• H01L51/5016

  Electricity · mapped topic

• H01L51/0085 Primary

  Electricity · mapped topic

• H10K50/12

  comprising dopants · CPC title