Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10033000-B2
Application number	US-201414521281-A
Country	US
Kind code	B2
Filing date	Oct 22, 2014
Priority date	Nov 15, 2013
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

According to one embodiment, a compound comprising a ligand L A of Formula I

is described. In the structure of Formula I, A 1 through A 8 are independently carbon or nitrogen, with at least one being nitrogen; X 1 is selected from the group consisting of O, S, and Se; X 2 and X 3 are independently selected from the group consisting of C, N, O, P, and S; ring A is a 5- or 6-membered heterocyclic ring bonded to ring B through a X 2 —C bond and bonded to M through a metal-carbene bond; any adjacent substitutions in R 1 and R 2 are optionally linked together to form a ring; the ligand L A is coordinated to a metal M; and the ligand L A is optionally linked with other ligands to comprise up to a hexadentate ligand. Formulations and devices, such as an OLEDs, that include the compound comprising ligand L A of formula I are also described.

First claim

We claim:

1. A compound having a formula M(L A ) m (L B ) n , having a structure:

wherein M is a metal;
wherein m is an integer from 1 to the maximum number of ligands that may be coordinated to the metal M;
m+n is the maximum number of ligands that may be coordinated to the metal M;
wherein each A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is independently carbon or nitrogen;
wherein at least one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , or A 8 is nitrogen;
wherein X 1 is selected from the group consisting of O, S, and Se;
wherein X 2 and X 3 each independently comprise an atom selected from the group consisting of C, N, O, P, and S;
wherein ring A is bonded to ring B through a X 2 —C bond;
wherein ring A is a 5- or 6-member heterocyclic ring;
wherein R 1 and R 2 each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein adjacent substitutions in R 2 are optionally linked together to form a phenyl or pyridyl ring fused to ring A, and the phenyl or pyridyl ring may be further substituted;
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 M is coordinated to ring A through a metal-carbene bond and to ring B through a M-C bond; and
wherein the ligand L A is optionally linked with one or two L B ligands to comprise a tetradentate or hexadentate ligand; and
wherein ligand L B is selected from the group consisting of:

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 X 1 is O.

5. The compound of claim 1 , wherein only one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , or A 8 is nitrogen.

6. The compound of claim 1 , wherein each one of A 1 , A 2 , A 3 , and A 4 is carbon.

7. The compound of claim 1 , wherein each one of A 1 , A 2 , A 3 , and A 4 is carbon, and exactly one of A 5 , A 6 , A 7 , or A 8 is nitrogen.

8. The compound of claim 1 , wherein R 2 forms a phenyl or pyridyl ring fused to ring A; and wherein the phenyl or pyridyl ring may be further substituted.

9. The compound of claim 1 , wherein ring A is selected from the group consisting of:

wherein the wave line indicates the bond to ring B;
wherein R 3 is 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.

10. The compound of claim 1 , wherein the ligand L A is:

wherein R 3 is 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.

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

12. A formulation comprising the compound of claim 1 .

13. The compound of claim 1 , wherein the ligand L A is:

wherein R 10 is 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.

14. The compound of claim 13 , wherein the ligand L A is:

15. A compound having a structure selected from the group consisting of:

wherein m and n are integers and m+n=3;
wherein each A 5 , A 6 , A 7 , and A 8 is independently carbon or nitrogen;
wherein at least one of A 5 , A 6 , A 7 , or A 8

Assignees

• Universal Display Corp

Inventors

• Xia Chuanjun
• Lin Chun
• Kottas Gregory
• Elshenway Zeinab

Classifications

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title