Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2022231237-A1
Application number	US-202217711313-A
Country	US
Kind code	A1
Filing date	Apr 1, 2022
Priority date	Apr 13, 2016
Publication date	Jul 21, 2022
Grant date	—

Abstract

Ligands with fused spirocyclic substitutions and metal complexes formed with such ligands and having improved performance in OLED applications are disclosed.

First claim

1 . A compound comprising a first ligand L A having a structure according to Formula 1:

wherein rings A and B are each a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R A and R B each independently represent a mono substitution or up to the maximum possible number of substitutions, or no substitution;
wherein Z 1 and Z 2 are each independently selected from the group consisting of carbon or nitrogen;
wherein Z 1 is a neutral donor atom;
wherein each R A and R B is 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 adjacent substituents are optionally joined or fused into a ring;
wherein at least one pair of R B are joined or fused into an aromatic ring;
wherein at least one R A comprises (1) a spiro polycyclic alkyl fused to an aromatic ring; or (2) a spiro polycyclic alkyl fused to ring A;
wherein the ligand L A is coordinated to a metal M;
wherein the metal M can be coordinated to other ligands; 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 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 or Pt.

4 . The compound of claim 1 , wherein Z 1 is a neutral nitrogen donor atom or a neutral carbene donor atom.

5 . The compound of claim 1 , wherein ring B is benzene.

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

wherein X is selected from the group consisting of O, S, Se, C, Si and N.

7 . The compound of claim 1 , wherein the spiro polycyclic alkyl group is selected from the group consisting of:

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

9 . The compound of claim 1 , wherein the compound has a formula of M(L A ) n (L B ) m-n ;
wherein M is Ir or Pt; L B is a bidentate ligand; wherein when M is Ir, m is 3, and n is 1, 2, or 3; and wherein when M is Pt, m is 2, and n is 1, or 2.

10 . The compound of claim 9 , wherein the compound has a formula of Ir(L A ) 3 , Ir(L A )(L B ) 2 or Ir(L A ) 2 (L B ), wherein L B is different from L A ; or the compound has a formula of Pt(L A )(L B ), wherein L A and L B can be same or different.

11 . The compound of claim 9 , wherein 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′, 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 a ring;
wherein each R a , R b , R c , and R d may represent from a mono substitution up to the maximum possible number of substitutions, 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; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

12 . The compound of claim 8 , wherein the compound is Compound Ax having the formula Ir(L Ai )(L Bj ) 2 , wherein x=300i+j−300; i is an integer from 120 to 131, and j is an integer from 1 to 300; or
the compound is Compound By having the formula Ir(L Ai ) 2 (L Bj ), wherein y=300i+j−300; i is an integer from 120 to 131, and j is an integer from 1 to 300; or
the compound is Compound Cz having the formula Ir(L Ai ) 3 , wherein z=i; i is an integer from 1 to 131; and wherein L B is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Layek Suman
• Xia Chuanjun
• Ji Zhiqiang
• Barron Edward

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/07 Primary

  having chemically-interreactive components, e.g. reactive chemiluminescent compositions · CPC title