Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11780865-B2
Application number	US-201715843710-A
Country	US
Kind code	B2
Filing date	Dec 15, 2017
Priority date	Jan 9, 2017
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

Abstract

Novel ligands for metal complexes that are useful as phosphorescent emitters in OLEDs are disclosed. The ligands contain an aryl covalently bonded to the coordinating metal where the aryl group has at least two different alkyl side chains that are linked ortho and para compared to the linkage of the coordinating metal on that aryl group.

First claim

We claim:

1. A compound having a formula M(L A ) x (L B ) y (L C ) z :
wherein the ligand L A has Formula I,

wherein the ligand L B has Formula II,

wherein the ligand L C has Formula III,

wherein M is a metal having an atomic weight 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 X 1 to X 5 are each independently a carbon or nitrogen;
wherein ring A is a ring selected from furan, pyrazole, imidazole, selenophene, oxazole, and thiazole that is fused to the ring having X 1 ;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R 3 represents mono-substitution up to a maximum possible number of substitutions;
wherein R 4 , R C , and R D each independently represents no substitutions up to a maximum possible number of substitutions;
wherein each of R 3 , R 4 , R C , and R D , R X , R Y , and R Z 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 at least one R 3 is not hydrogen or deuterium;
wherein any adjacent substituents of R C and R D can be fused into an aryl or heteroaryl ring, but cannot be fused into a non-aromatic ring, and R X , R Y , and R Z can be joined or fused into a ring, and adjacent substituents of R 3 cannot be joined or fused into a ring;
wherein R 1 and R 2 are each independently selected from the group consisting of alkyl, cycloalkyl, silyl, germanyl, and substituted variants thereof;
wherein at least one of X 1 or X 2 and X 4 is N; and
wherein R 1 is different from R 2 , and R 2 has more carbon atoms than R 1 .

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 the compound has a formula M(L A ) 2 (L C ) or M(L A )(L B ) 2 .

4. The compound of claim 1 , wherein X 1 is C and X 2 is N.

5. The compound of claim 1 , wherein R 2 has at least two more carbon atoms than R 1 .

6. The compound of claim 1 , wherein each of R 3 , R 4 , R C , R D , R X , R Y , and R Z is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

7. The compound of claim 1 , wherein the ligand L B 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′, 0, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ can be fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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 substituents of R a , R b , R c , and R d can be fused into an aryl or heteroaryl ring, but cannot be fused into a non-aromatic ring; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a multidentate ligand.

8. The compound of claim 1 , wherein the ligand L C is selected from the group consisting of:

9. The compound of claim 1 , wherein the compound has a structure of formula Ir(L A ) 2 (L C );
wherein L A is selected from the group consisting of

wherein Y is selected from the group consisting of O and Se, and N(CH 3 ); and
wherein L C is selected from the group consisting of:

10. The compound of claim 1 , wherein the compound has a formula Ir(L A ) 2 (L C ); wherein each R 4 is hydrogen.

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

wherein Y is selected from the group consisting of O and Se.

12. The compound of claim 1 , wherein ring A is selenophene.

13. The compound of claim 1 , wherein ring A is furan.

14. The compound of claim 1 , wherein R 2 comprises alkyl with at least four carbon atoms.

15. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula M(L A ) x (L B ) y (L C ) z :
wherein the ligand L A has Formula I,

wherein the ligand L B has Formula II,

wherein the ligand L C has Formula III,

wherein M is a metal having an atomic weight 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 X 1 to X 5 are each independently a carbon or nitrogen;
wherein ring A is a ring selected from furan, pyrazole, imidazole, selenophene, oxazole, and thiazole that is fused to the ring having X 1 ;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R 3 represents mono-substitution up to a maximum possible number of substitutions;
wherein R 4 , R C , and R

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Alleyne Bert
• Joseph Scott
• Wendt Harvey

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/81

  Anodes · CPC title

• H10K50/82

  Cathodes · CPC title

• H10K85/342

  comprising iridium · CPC title