Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2015137096-A1
Application number	US-201414521281-A
Country	US
Kind code	A1
Filing date	Oct 22, 2014
Priority date	Nov 15, 2013
Publication date	May 21, 2015
Grant date	—

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

1 . A compound comprising a ligand L A of Formula I:

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 , and 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 any adjacent substitutions in R 1 and R 2 are optionally linked together to form a ring;
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 the ligand L A is coordinated to a metal M;
wherein M is coordinated to ring A through a metal-carbene bond; and
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

2 . The compound of claim 1 , wherein the compound has the formula M(L A ) m (L B ) n , having the structure:

wherein L B is a different ligand from L A ;
wherein m is an integer from 1 to the maximum number of ligands that may be coordinated to the metal M; and
m+n is the the maximum number of ligands that may be coordinated to the metal M.

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

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

5 . The compound of claim 1 , wherein X 1 is O.

6 . The compound of claim 1 , wherein M is coordinated to ring B through a M-C bond.

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

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

9 . 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 , and A 8 is nitrogen.

10 . 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.

11 . 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, sulfonyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

12 . 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.

13 . The compound of claim 2 , wherein the compound has the formula Ir(L A ) m (L B ) n , having the structure:

wherein m+n=3; and
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.

14 . The compound of claim 13 , wherein the compound is selected from the group consisting of:

wherein R 4 represents mono, di-substitution, or no substitution;
wherein R 6 , R 8 and R 9 each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , and Y 8 comprise carbon or nitrogen;
wherein R 4 , R 5 , R 6 , R 7 , R 8 and R 9 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; and
wherein any adjacent substitutions in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are optionally linked together to form a ring.

15 . The compound of claim 14 , wherein the compound is selected from the group consisting of:

16 .- 24 . (canceled)

25 . The compound of claim 14 , wherein Y 5 , Y 6 , Y 7 , and Y 8 comprise carbon; and wherein only one of Y 1 , Y 2 , Y 3 , Y 4 is nitrogen.

26 .- 27 . (canceled)

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

wherein R 10 is selected from the group consisting of 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.

29 . The compound of claim 28 , wherein the ligand L A is:

30 .- 33 . (canceled)

34 . The compound of claim 2 , wherein L A is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

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

Classifications

• C07D491/048

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

• C07F15/0033 Primary

  Iridium compounds · CPC title

• 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

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/185

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