Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12239018-B2
Application number	US-202117182611-A
Country	US
Kind code	B2
Filing date	Feb 23, 2021
Priority date	Feb 28, 2020
Publication date	Feb 25, 2025
Grant date	Feb 25, 2025

Abstract

An organic electroluminescent material is disclosed. The organic electroluminescent material is novel dehydro-fused-ring compounds with a structure of B(A)2, which may be used as charge transporting materials, charge injection materials, and the like in organic electroluminescent devices. Such novel compounds have very deep LUMO energy level, so they are excellent electron acceptor materials and charge transfer materials. They also have the potential to be excellent hole injection materials and p-dopant materials, and have broad industrial application prospects. An electroluminescent device and a compound formulation are also disclosed.

First claim

The invention claimed is:

1. A compound having a structure of B(A) 2 , wherein A has a structure of Formula 1:

wherein,
X is, at each occurrence identically or differently, selected from the group consisting of O, S, Se, NR′ and CR″R′″;
Y is N;
W is, at each occurrence identically or differently, selected from the group consisting of O, S, Se and NR N ;
wherein, B is selected from a substituted or unsubstituted conjugated unsaturated fused aryl ring having 10 to 30 ring atoms, or a substituted or unsubstituted conjugated unsaturated fused heteroaryl ring having 10 to 30 ring atoms, or selected from the structure represented by one of Formula 2 to Formula 8, or combinations thereof:

wherein B is fused with each of A through a single bond and a double bond;
wherein Z is, at each occurrence, identically or differently, selected from the group consisting of CR and N;
n is, at each occurrence, identically or differently, selected from 0, 1, or 2;
wherein, R, R′, R″, R′″ and R N are, at each occurrence, identically or differently, selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, a carboxylic acid group, an ester group, cyano, isocyano, SCN, OCN, SF 5 , boranyl, sulfinyl, sulfonyl, phosphoroso, sulfanyl, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof;
wherein at least one of R, R′, R″, R′″ and R N is a group having at least one electron-withdrawing group;
any two adjacent substituents R, R′, R″, R″ and R N can be optionally joined to form a ring.

2. The compound according to claim 1 , wherein when B is selected from Formula 2 or Formula 3, the compound is selected from the structure of Formula I or Formula II:

wherein, Z 1 and Z 2 are, at each occurrence identically or differently, selected from the group consisting of CR and N;
wherein, X is, at each occurrence identically or differently, selected from the group consisting of O, S, Se, NR′ and CR″R′″;
wherein, Y is N;
wherein, W is, at each occurrence identically or differently, selected from the group consisting of O, S, Se and NR N ;
wherein, R, R′, R″, R′″ and R N are, at each occurrence identically or differently, selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, a carboxylic acid group, an ester group, cyano, isocyano, SCN, OCN, SF 5 , boranyl, sulfinyl, sulfonyl, phosphoroso, sulfanyl, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof;
wherein at least one of R, R′, R″, R′″ and R N is a group having at least one electron-withdrawing group; and
any two adjacent substituents R, R′, R″, R′″ and R N can be optionally joined to form a ring;
or wherein when B is selected from a substituted or unsubstituted conjugated unsaturated fused aryl ring having 10 to 30 ring atoms, or a substituted or unsubstituted conjugated unsaturated fused heteroaryl ring having 10 to 30 ring atoms, the compound is selected from the structure of any one of Formula III to Formula XVIII:

wherein,
X is, at each occurrence identically or differently, selected from the group consisting of O, S, Se, NR′ and CR″R′″;
Y is N;
W is, at each occurrence identically or differently, selected from the group consisting of O, S, Se and NR N ;
wherein Z 1 to Z 6 are, at each occurrence identically or differently, selected from the group consisting of CR and N;
wherein, R, R′, R″, R′″ and R N are, at each occurrence identically or differently, selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, a carboxylic acid group, an ester group, cyano, isocyano, SCN, OCN, SF 5 , boranyl, sulfinyl, sulfonyl, phosphoroso, sulfanyl, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof;
wherein at least one of R, R′, R″, R′″ and R N is a group having at least one electron-withdrawing group;
any two adjacent substituents R, R′, R″, R′″ and R N can be optionally joined to form a ring;
or wherein when B is selected from Formula 4 to Formula 8, n is 0 or 1, and the compound has the structure of any one of Formula XIX to Formula XXIV:

wherein,
X is, at each occurrence identically or differently, selected from the group consisting of O, S, Se, NR′ and CR″R′″;
Y is N;
W is, at each occurrence identically or differently, selected from the group consisting of O, S, Se and NR N ;
wherein Z 1

Assignees

• Beijing Summer Sprout Tech Co Ltd

Inventors

• Cui Zhihao
• Ding Hualong
• Kwong Chi Yuen Raymond
• Xia Chuanjun
• Hu Juntao
• Chen Xiao

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/657 Primary

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title