Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10964904-B2
Application number	US-201815862180-A
Country	US
Kind code	B2
Filing date	Jan 4, 2018
Priority date	Jan 20, 2017
Publication date	Mar 30, 2021
Grant date	Mar 30, 2021

Abstract

This invention relates to the development of heterocyclic materials for use as red, green, and blue phosphorescent materials in OLED devices. The materials are based in part on a pair of aromatic or psuedoaromatic rings bonded to one another and complexed to a transition metal. Azaborinane, borazine, and related aromatic structures including boron may be incorporated as fused rings, as pendant groups, or as bridging groups to tune color and improve chemical stability. Desirable structures may be selected by being determined computationally to have appropriate triplet energies for use as blue emitters and to possess sufficient chemical stability for use in devices.

First claim

We claim:

1. A compound comprising a first ligand L A having the structure selected from the group consisting of:

wherein rings A, B, and C are each independently a five-membered or six-membered carbocyclic ring or heterocyclic ring;
wherein ring A connects to ring B in Formula I through a chemical bond, and ring A connects to rings B and C in Formula II through a chemical bond;
wherein R A , R B , and R C each independently represent mono to the maximum possible substitution, or no substitution;
wherein Z 1 and Z 2 are each independently selected from the group consisting of carbon or nitrogen;
wherein each occurrence of R A , R B , and R C 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, borinane, azaborinane, borazine, azaborine, azaborinine, and combinations thereof;
at least one of R A or R B comprises a first structure, wherein the first structure is a monocyclic or polycyclic ring formed by a single bond between atoms selected from the group consisting of trivalent boron, trivalent nitrogen, divalent oxygen, divalent sulfur, and divalent selenium, and wherein the first structure has at least one trivalent boron; and
wherein any adjacent substituents are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M via the dashed lines;
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;
wherein, when the compound is represented by Formula I, the first structure is selected from the group consisting of:

wherein each occurrence of X is independently selected from the group consisting of N, O, S, and Se.

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 is represented by Formula II and the first structure is selected from the group consisting of:

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

4. The compound of claim 1 , wherein one of Z 1 and Z 2 is nitrogen, and the remaining one of Z 1 and Z 2 is carbon.

5. The compound of claim 1 , wherein one of Z 1 and Z 2 is a neutral carbene carbon, and the remaining one of Z 1 and Z 2 is a sp 2 anionic carbon.

6. The compound of claim 1 , wherein rings A, B, and C are each a six-membered aromatic ring.

7. The compound of claim 1 , wherein ring A is a five-membered aromatic ring, and rings B and C are each a six-membered aromatic ring.

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

wherein each occurrence of R D 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, borinane, azaborinane, borazine, azaborine, azaborinine, and combinations thereof.

9. A compound comprising a first ligand L A selected from the group consisting of:

R1
R2
R3
R4
R5
LA#

RA1
H
H
H
H
LA1

RA2
H
H
H
H
LA2

RA3
H
H
H
H
LA3

RA4
H
H
H
H
LA4

RA5
H
H
H
H
LA5

RA6
H
H
H
H
LA6

RA7
H
H
H
H
LA7

RA8
H
H
H
H
LA8

RA9
H
H
H
H
LA9

RA10
H
H
H
H
LA10

RA11
H
H
H
H
LA11

RA12
H
H
H
H
LA12

RA13
H
H
H
H
LA13

RA14
H
H
H
H
LA14

H
RA1
H
H
H
LA15

H
RA2
H
H
H
LA16

H
RA3
H
H
H
LA17

H
RA4
H
H
H
LA18

H
RA5
H
H
H
LA19

H
RA6
H
H

Assignees

• Universal Display Corp

Inventors

• Fitzgerald George
• Lahti Paul M
• Lin Chun

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H10K50/81

  Anodes · CPC title

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• C07F15/0086

  Platinum compounds · CPC title

• H01L51/5092

  Electricity · mapped topic