Organic electroluminescent materials and device

Patent metadata

Field	Value
Publication number	US-2018337342-A1
Application number	US-201815944348-A
Country	US
Kind code	A1
Filing date	Apr 3, 2018
Priority date	May 18, 2017
Publication date	Nov 22, 2018
Grant date	—

Abstract

useful as an emitter in OLEDs is disclosed.

First claim

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

wherein ring A is a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein each of R A and R B independently represents none to a maximum possible number of substitutions;
wherein each of R 1 , R 2 , R A , and R B is 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 Z 1 is carbon or nitrogen;
wherein any R 1 , R 2 , R A , and R B are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.

2 . The compound of claim 1 , wherein each of R 1 , R 2 , R A , and R B is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

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 .- 8 . (canceled)

9 . The compound of claim 1 , wherein ring A is a benzene ring.

10 . The compound of claim 1 , wherein Z 1 is an anionic coordinating atom selected from the group consisting of C, N, and O.

11 . (canceled)

12 . The compound of claim 1 , wherein two R B are fused into an aromatic ring.

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

wherein X and Y are each independently selected from the group consisting of O, S, Se, NR 3 and CR 4 R 5 ; and wherein R 3 , R 4 , and R 5 have the same definition as R′.

14 . The compound of claim 1 , wherein the first ligand L A is selected from the group consisting of:
L A1 through L A20 having the structure

wherein in L A1 , R 1 ═R 2 =Me, in L A2 , R 1 ═R 2 =Et, in L A3 , R 1 ═R 2 =iPr, in L A4 , R 1 =Me, R 2 =Et, in L A5 , R 1 =Me, R 2 =iPr, in L A6 , R 1 =Et, R 2 =iPr, in L A7 , R 1 =Me, R 2 =Ph, in L A8 , R 1 =Et, R 2 =Ph, in L A9 , R 1 ═R 2 =Ph, in L A10 , R 1 ═R 2 ═F, in L A11 , R 1 =Me, R 2 ═CH 2 CF 3 , in L A12 , R 1 ═R 2 =CD 3 , in L A13 , R 1 ═R 2 =CD 2 CD 3 , in L A14 , R 1 ═R 2 =CD(CH 3 ) 2 ,
in L A15 , R 1 =CD 3 , R 2 =CD 2 CD 3 , in L A16 , R 1 =CD 3 , R 2 =CD(CH 3 ) 2 , in L A17 , R 1 =CD 2 CD 3 , R 2 =CD(CH 3 ) 2 ,
in L A18 , R 1 =CD 3 , R 2 =Ph, in L A19 , R 1 =CD 2 CD 3 , R 2 =Ph, and in L A20 , R 1 =CD 3 , R 2 =CD 2 CF 3 ,

L A41 through L A60 having the structure

wherein in L A41 , R 1 ═R 2 =Me, in L A42 , R 1 ═R 2 =Et,
in L A43 , R 1 ═R 2 =iPr, in L A44 , R 1 =Me, R 2 =Et, in L A45 , R 1 =Me, R 2 =iPr, in L A46 , R 1 =Et, R 2 =iPr,
in L A47 , R 1 =Me, R 2 =Ph, in L A48 , R 1 =Et, R 2 =Ph, in L A49 , R 1 ═R 2 =Ph, in L A50 , R 1 ═R 2 ═F,
in L A51 , R 1 =Me, R 2 ═CH 2 CF 3 , in L A52 , R 1 ═R 2 =CD 3 , in L A53 , R 1 ═R 2 =CD 2 CD 3 , in L A54 , R 1 ═R 2 =CD(CH 3 ) 2 ,
in L A55 , R 1 =CD 3 , R 2 =CD 2 CD 3 , in L A56 , R 1 =CD 3 , R 2 =CD(CH 3 ) 2 , in L A57 , R 1 =CD 2 CD 3 , R 2 =CD(CH 3 ) 2 ,
in L A58 , R 1 =CD 3 , R 2 =Ph, in L A59 , R 1 =CD 2 CD 3 , R 2 =Ph, and in L A60 , R 1 =CD 3 , R 2 =CD 2 CF 3 ,

L A67 through L A86 having the structure

wherein in L A67 , R 1 ═R 2 =Me, in L A68 , R 1 ═R 2 =Et,
in L A69 , R 1 ═R 2 =iPr, in L A70 , R 1 =Me, R 2 =Et, in L A71 , R 1 =Me, R 2 =iPr, in L A72 , R 1 =Et, R 2 =iPr, in L A73 , R 1 =Me, R 2 =Ph, in L A74 , R 1 =Et, R 2 =Ph, in L A75 , R 1 ═R 2 =Ph, in L A76 , R 1 ═R 2 ═F, in L A77 , R 1 =Me, R 2 ═CH 2 CF 3 , in L A78 , R 1 ═R 2 =CD 3 , in L A79 , R 1 ═R 2 =CD 2 CD 3 , in L A80 , R 1 ═R 2 =CD(CH 3 ) 2 ,
in L A81 , R 1 =CD 3 , R 2 =CD 2 CD 3 , in L A82 , R 1 =CD 3 , R 2 =CD(CH 3 ) 2 , in L A83 , R 1 =CD 2 CD 3 , R 2 =CD(CH 3 ) 2 ,
in L A84 , R 1 =CD 3 , R 2 =Ph, in L A85 , R 1 =CD 2 CD 3 , R 2 =Ph, and in L A86 , R 1 =CD 3 , R 2 =CD 2 CF 3 ,

L A93 through L A112 having the structure

wherein in L A93 , R 1 ═R 2 =Me, in L A94 , R 1 ═R 2 =Et,
in L A95 , R 1 ═R 2 =iPr, in L A96 , R 1 =Me, R 2 =Et, in L A97 , R 1 =Me, R 2 =iPr, in L A98 , R 1 =Et, R 2 =iPr,
in L A99 , R 1 =Me, R 2 =Ph, in L A100 , R 1 =Et, R 2 =Ph, in L A101 , R 1 ═R 2 =Ph, in L A102 , R 1 ═R 2 ═F,
in L A103 , R 1 =Me, R 2 ═CH 2 CF 3 , in L A104 , R 1 ═R 2 =CD 3 , in L A105 , R 1 ═R 2 =CD 2 CD 3 ,
in L A106 , R 1 ═R 2 =CD(CH 3 ) 2 , in L A107 , R 1 =CD 3 , R 2 =CD 2 CD 3 , in L A108 , R 1 =CD 3 , R 2 =CD(CH 3 ) 2 ,
in L A109 , R 1 =CD 2 CD 3 , R 2 =CD(CH 3 ) 2 , in L A110 , R 1 =CD 3 , R 2 =Ph, in L A111 , R 1 =CD 2 CD 3 , R 2 =Ph, and
in L A112 , R 1 =CD 3 , R 2 =CD 2 CF 3 ,

L A119 through L A138 having the structure

wherein in L A119 , R 1 ═R 2 =Me, in L A120 , R 1 ═R 2 =Et,
in L A121 , R 1 ═R 2 =iPr, in L A122 , R 1 =Me, R 2 =Et, in L A123 , R 1 =Me, R 2 =iPr, in L A124 , R 1 =Et, R 2 =iPr,
in L A125 , R 1 =Me, R 2 =Ph, in L A126 , R 1 =Et, R 2 =Ph, in L A127 , R 1 ═R 2 =Ph, in L A128 , R 1 ═R 2 ═F,
in L A129 , R 1 =Me, R 2 ═CH 2 CF 3 , in L A130 , R 1 ═R 2 =CD 3 , in L A131 , R 1 ═R 2 =CD 2 CD 3 ,
in L A132 , R 1 ═R 2 =CD(CH 3 ) 2 , in L A133 , R 1 =CD 3 , R 2 =CD 2 CD 3 , in L A134 , R 1 =CD 3 , R 2 =CD(CH 3 ) 2 ,
in L A135 , R 1 =CD 2 CD 3 , R 2 =CD(CH 3 ) 2 , in L A136 , R 1 =CD 3 , R 2 =Ph, in L A137 , R 1 =CD 2 CD 3 , R 2 =Ph, and
in L A138 , R 1 =CD 3 , R 2 =CD 2 CF 3 ,

Assignees

• Universal Display Corp

Inventors

• Su Mingjuan
• Feldman Jerald

Classifications

• H01L51/0067

  Electricity · mapped topic

• H01L51/5008

  Electricity · mapped topic

• H01L51/0071 Primary

  Electricity · mapped topic

• H01L51/0068

  Electricity · mapped topic

• H01L51/0065

  Electricity · mapped topic