Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12466844-B2
Application number	US-202117246885-A
Country	US
Kind code	B2
Filing date	May 3, 2021
Priority date	May 13, 2020
Publication date	Nov 11, 2025
Grant date	Nov 11, 2025

Abstract

Provided are organoboron compounds. Also provided are formulations comprising these organoboron compounds. Further provided are OLEDs and related consumer products that utilize these organoboron compounds.

First claim

What is claimed is:

1 . A compound of

wherein:
moiety A is a monocyclic or multicyclic fused ring system comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;
X 1 -X 13 are each independently C or N;
Y is N or CR;
R is a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R A , R B , R C , and R D each independently represents zero, mono, or up to maximum allowed substitutions to its associated ring;
each of R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of R A , R B , R C , and R D being a ring or ring structure G;
any two adjacent R, R A , R B , R C , or R D can be joined or fused together to form a ring,
one R B and one R C can be joined or fused together to form a ring and
wherein at least one of the following is true:
i) moiety A comprises three fused rings, wherein one of the three fused rings is a 6-membered ring that is fused to the ring containing Y and a 5-membered ring fuses to said 6-membered ring;
ii) at least one of R B and R C is a substituted or unsubstituted group selected from the group consisting of phenyl, triphenylsilyl, naphthalene, fluorene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-naphthalene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene and at least one of R A and R D is 1,3-diisopropyl benzene;
iii) moiety A and moiety D are each a monocyclic ring system comprising a 6-membered ring, any two adjacent R, R B , or R C , can be joined or fused together to form a ring, and at least one of R A and R D is a pendant heteroaryl group; or
iv) at least one R A and at least one R D is carbazole or one of R A or R D is carbazole and the other of R A and R D is 1,3-diisopropyl benzene.

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

3 . The compound of claim 1 , wherein moiety A is monocyclic.

4 . The compound of claim 1 , wherein moiety A contains two fused rings, or three fused rings.

5 . The compound of claim 1 , wherein the ring or ring structure G is a substituted or unsubstituted 5-membered or 6-membered carbocyclic or heterocyclic ring.

6 . The compound of claim 1 , wherein the ring or ring structure G is a substituted or unsubstituted aromatic ring, or a multicyclic fused ring moiety.

7 . The compound of claim 1 , wherein X 1 -X 13 are each C.

8 . The compound of claim 1 , wherein at least one of X 1 -X 13 is N.

9 . The compound of claim 1 , wherein Y is N.

10 . The compound of claim 1 , wherein one or more of R A , R B , R C , and R D are independently a substituted or unsubstituted group selected from the group consisting of phenyl, triphenylsilyl, naphthalene, fluorene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-naphthalene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

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

wherein ring A 1 , ring A 2 , and ring A 3 are each independently 5-membered or 6-membered aromatic rings; and X 14 -X 17 are each independently C or N.

12 . The compound of claim 1 , wherein the compound of Formula I is selected from the group consisting of:

Compound name
Structure

Compound I-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 47 to 64, 107 to 124, and 167 to 184, wherein Compound I- [(A1)(A47)] to Compound I- [(A365)(A184)] having the structure

Compound II-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound II-[(A1)(A16)] to Compound II-[(A365)(A365)] having the structure

Compound III-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound III-[(A1)(A16)] to Compound III-[(A365)(A365)] having the structure

Compound IV-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound IV-[(A1)(A16)] to Compound IV-[(A365)(A365)] having the structure

Compound V-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 47 to 64, 107 to 124, and 167 to 184, wherein Compound V-[(A1)(A47 to Compound V-[(A365)(A184)] having the structure

Compound VI-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound VI-[(A1)(A1)] to Compound VI-[(A365)(A365)] having the structure

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Fleetham Tyler
• Hamze Rasha
• Beers Scott

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title