Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity

Patent metadata

Field	Value
Publication number	US-11245078-B2
Application number	US-201916279145-A
Country	US
Kind code	B2
Filing date	Feb 19, 2019
Priority date	Aug 25, 2015
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

Thermally activated delayed fluorescent compounds and uses thereof are described. The thermally activated delayed fluorescent compounds are an analogues of 9,10-dihydro-9,9-dimethylacridine compounds.

First claim

The invention claimed is:

1. A thermally activated delayed fluorescent compound represented by Formula I, Formula II, Formula III, or Formula IV:

wherein:

represents n acceptor moieties A, where A is a nitrogen-containing heteroaryl group, a R q MO group, where M is C, S, P, or As, or a R q SO 2 group, or any combination thereof; and n=1, 2, or 3, such that the compound includes a single acceptor moiety (A 1 ), two acceptor moieties (A 1 and A 2 ), or three acceptor moieties (A 1 , A 2 , and A 3 ), and wherein each acceptor moiety is substituted with R q ;
L 1 , and L 2 , and L 3 are each independently —CR 2 -, —CO—, or —SiR 2 -; and
R m , R n , R p , and R q each independently represent mono-, di-, tri, or tetra-substitution, valency permitting; and
each R, R m , R n , R p , and R q independently represents mono-, di-, tri, or tetra-substitution, valency permitting, and each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an —SH group, a nitro group, a cyano group, an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, a mono- or dialkylamino group, a mono- or diarylamino group, an alkoxy group, an aryloxy group, a heteroaryl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof;
wherein the alkyl group, haloalkyl group, aralkyl group, alkenyl group, alkynyl group, aryl group, amino group, mono- or dialkylamino group, alkoxy group, aryloxy group, and heteroaryl group is optionally substituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, an SH group, a nitro group, a cyano group, an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, a mono- or dialkylamino group, a mono- or diarylamino group, an alkoxy group, an aryloxy group, a heteroaryl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, and a polymeric group;
with the proviso that when the compound is represented by Formula III, R m and R n are not pyridyl.

2. The compound of claim 1 , wherein A is:

3. The compound of claim 2 , wherein A is a nitrogen-containing heteroaryl group comprising 1 to 3 nitrogen atoms.

4. The compound of claim 1 , wherein A is

where U, U 1 , and U 2 each independently represents N or C with the proviso that when U, U 1 and U 2 are present at least one of them is N.

5. The compound of claim 4 , wherein A is

6. The compound of claim 5 , wherein the compound is:

7. The compound of claim 6 , wherein the compound is:

or

8. The compound of claim 6 , wherein the compound is:

or

9. The compound of claim 1 , wherein n is 2 and the compound has the structure selected from the group consisting of:

where:
R u represents mono-, di-, tri, or tetra-substitution, valency permitting;
and each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an —SH group, a nitro group, a cyano group, an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, a mono- or dialkylamino group, a mono- or diarylamino group, an alkoxy group, an aryloxy group, a heteroaryl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof;
wherein the alkyl group, haloalkyl group, aralkyl group, alkenyl group, alkynyl group, aryl group, amino group, mono- or dialkylamino group, alkoxy group, aryloxy group, and heteroaryl group is optionally substituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, an SH group, a nitro group, a cyano group, an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, a mono- or dialkylamino group, a mono- or diarylamino group, an alkoxy group, an aryloxy group, a heteroaryl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, and a polymeric group.

10. The compound of claim 9 , wherein n=3, and the compound has the structure selected from the group consisting of:

where
R v represents mono-, di-, tri, or tetra-substitution, valency permitting;
and each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an —SH group, a nitro group, a cyano group, an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, a mono- or dialkylamino group, a mono- or diarylamino group, an alkoxy group, an aryloxy group, a heteroaryl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof;
wherein the alkyl group, haloalkyl group, aralkyl group, alkenyl group, alkynyl group, aryl g

Assignees

• Univ Arizona
• Univ Arizona State

Inventors

• Li Jian
• Feng Diajun

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07F9/6561

  containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1048

  with oxygen · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title