Cyanoaryl substituted benz(othi)oxanthene compounds

Patent metadata

Field	Value
Publication number	US-11236101-B2
Application number	US-201816954931-A
Country	US
Kind code	B2
Filing date	Dec 18, 2018
Priority date	Dec 19, 2017
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

The present invention relates to a cyanoaryl substituted compound of formula (I), (I) wherein m is 0-4; R2, R3, R4 and R5 are selected from hydrogen, chlorine, bromine and C6-C24-aryl, which carries one to three cyano; each R1 independently from each other is selected from bromine, chlorine, cyano, —NRaRb, C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, C1-C24-haloalkoxy, C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, C6-C24-aryl-C1-C10-alkylene, etc., with the proviso that at least one of the radicals R1, R2, R3, R4 and R5 is C6-C24-aryl, which carries one to three cyano; X is O, S, SO or SO2; A is a diradical of the formulae (A.1), (A.2), (A.3), or (A.4) wherein *, R6, (R7)n, (R8)o and (R9)p are as defined in the claims and in the description. The invention also relates to the use of said compound(s) in color converters, to said color converters and their use, to lighting devices, to a backlight unit for liquid crystal displays; a liquid crystal display device and a self-emissive display device comprising at least one compound (I).

First claim

The invention claimed is:

1. A cyanoaryl substituted compound of formula (I)

wherein
m is 0, 1, 2, 3 or 4;
each R 1 is independently from each other selected from the group consisting of bromine, chlorine, cyano, —NR a R b , C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl, C 1 -C 24 -alkoxy, C 1 -C 24 -haloalkoxy, C 3 -C 24 -cycloalkyl, heterocycloalkyl, heteroaryl, C 6 -C 10 -aryl, C 6 -C 10 -aryloxy and C 6 -C 10 -aryl-C 1 -C 10 -alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl, aryloxy and aryl-alkylene in the six last-mentioned radicals are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R 1a , and where C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl, C 1 -C 24 -alkoxy and the alkylene moiety of C 6 -C 10 -aryl-C 1 -C 10 -alkylene may be interrupted by one or more groups selected from the group consisting of O, S and NR c ;
R 2 , R 3 , R 4 and R 5 are selected from the group consisting of hydrogen, chlorine, bromine and C 6 -C 10 -aryl, which comprises one, two or three cyano groups;
with the proviso that at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 is C 6 -C 10 -aryl, which comprises one, two or three cyano groups;
X is O, S, SO or SO 2 ; and
A is a diradical selected from the group consisting of diradicals of formulae (A.1) and (A.2),

wherein
* in each case denotes a point of attachment to the remainder of the molecule;
R 6 is hydrogen, C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl, C 3 -C 24 -cycloalkyl, C 6 -C 10 -aryl or C 6 -C 10 -aryl-C 1 -C 10 -alkylene, where the rings of cycloalkyl, aryl and aryl-alkylene in the three last-mentioned radicals are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R 6a , and where C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl and the alkylene moiety of C 6 -C 10 -aryl-C 1 -C 10 -alkylene may be interrupted by one or more heteroatoms or heteroatomic groups selected from the group consisting of O, S and NR c ;
R 1a and R 6a are independently from each other selected from the group consisting of C 1 -C 24 -alkyl, C 1 -C 24 -fluoroalkyl, C 1 -C 24 -alkoxy, fluorine, chlorine, bromine and cyano; and
R a , R b and R c are independently from each other selected from the group consisting of hydrogen, C 1 -C 20 -alkyl, C 3 -C 24 -cycloalkyl, heterocycloalkyl, hetaryl and C 6 -C 10 -aryl.

2. The cyanoaryl substituted compound of formula (I) according to claim 1 , in which X is O.

3. The cyanoaryl substituted compound of formula (I) according to claim 1 , where R 2 and R 4 are each phenyl, which comprises 1, 2 or 3 cyano groups, and R 3 and R 5 are each hydrogen.

4. The cyanoaryl substituted compound of formula (I) according to claim 1 , wherein A is a radical of formula (A.2).

5. The cyanoaryl substituted compound of formula (I) according to claim 4 , wherein R 6 is selected from the group consisting of linear C 1 -C 24 -alkyl, a radical of formula (B.1), a radical of formula (B.2) and a radical of formula (B.3)

wherein
# represents the bonding site to the nitrogen atom;
R d and R e , in the formula (B.1), are independently from each other selected from the group consisting of C 1 -C 22 -alkyl, where a sum of the carbon atoms of the R d and R e radicals is an integer from 2 to 23;
R f , R g and R h , in the formula (B.2), are independently from each other selected from the group consisting of C 1 - to C 21 -alkyl, where a sum of the carbon atoms of the R f , R g and R h radicals is an integer from 3 to 23; and
R i and R k , in the formula (B.3), are independently from each other selected from the group consisting of C 1 - to C 21 -alkyl, where a sum of the carbon atoms of the R i and R k radicals is an integer from 2 to 22.

6. The cyanoaryl substituted compound of formula (I) according to claim 4 , in which R 6 is selected from the group consisting of a radical of formula (C.1), a radical of formula (C.2) and a radical of formula (C.3)

wherein
# represents the bonding side to the nitrogen atom;
B where present, is a C 1 -C 10 -alkylene group which may be interrupted by one or more nonadjacent groups selected from —O— and —S—;
y is 0 or 1;
each R m is independently from each other selected from the group consisting of C 1 -C 24 -alkyl, C 1 -C 24 -fluoroalkyl, fluorine, chlorine and bromine;
each R n is independently from each other selected from the group consisting of C 1 -C 24 -alkyl; and
x in formulae (C.2) and (C.3) is 1, 2, 3, 4 or 5.

7. The cyanoaryl substituted compound of formula (I) according to claim 1 , wherein m in formula (I) is 0, 1 or 2 and when m is 1 or 2, each R 1 is selected from the group consisting of linear C 1 -C 24 -alkyl, a radical of formula (D.1), a radical of formula (D.2), a radical of formula (D.3), a radical of formula (D.4) and a radical of formula (D.5)

wherein
# represents the bonding site to the remainder of the cyanoaryl substituted compound of formula (I)
R o and R p , in formula (D.1), are independently from each other selected from the group consisting of C 1 -C 22 -alkyl, where a sum of the carbon atoms of the R o and R p radicals is an integer from 2 to 23;
R q , R r and R s , in formula (D.2), are independently from each other selected from the group consisting of C 1 - to C 21 -alkyl, where a sum of the carbon atoms of the R q , R r and R s radicals is an integer from 3 to 23;
R t and R u , in formula (D.3), are independently from each other selected from the group consisting of C 1 - to C 21 -alkyl, where a sum of the carbon atoms of the R t and R u radicals is an integer from 2 to 22;
B where present, is a C 1 -C 10 -alkylene group which may be interrupted by one or more nonadjacent groups selected from the group consisting of —O— and —S—;
y in formulae (D.4) and (D.5) is 0 or 1;
x in formula (D.5) is 1, 2 or 3; and
R 1a is selected from the group consisting of cyano, C 1 -C 24 -alkyl and C 1 -C 24 -alkoxy.

8. The cyanoaryl substituted compound of formula (I) according to claim 7 , wherein m in formula (I) is 0 or 1 and when m is 1, R 1 is a radical of formula (D.1), in which R o and R p are each independently C 1 -C 12 -alkyl or R 1 is a radical of formula (D.2), in which R q and R s are each independently C 1 -C 6 -alkyl and R r is branched C 4 -C 21 -alkyl or R 1 is a radical of formula (D.5), where R 1a is cyano or C 1 -C 12 -alkyl, y is 0 and x is 1 or 2.

9. A color converter comprising at least one cyanoaryl substituted compound of formula (I) according to claim 1 as a fluorescent dye and a polymer matrix,
wherein the polymer matrix is selected from the group consisting of a polystyrene, a polycarbonate, a polyacrylate, a polymethyl methacrylate, a polymethacrylate, a polyvinylpyrrolidone, a polyvinyl acetate, a polyvinyl chloride, a polybutene, a silicone, an epoxy resin, a vinyl ester resin, a polyvinyl alcohol, a poly(ethylene vinylalcohol)-copolymer, a polyacrylonitrile, a polyvinylidene chloride, a polystyrene acrylonitrile,

Assignees

• Basf Se

Inventors

• Koenemann Martin
• Wagenblast Gerhard
• Ivanovici Sorin
• Mangold Hannah Stephanie
• Kura Hisatoshi
• Matsunaga Mamiko

Classifications

• H10F77/45

  Wavelength conversion means, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements · CPC title

• H10F99/00

  Subject matter not provided for in other groups of this subclass · CPC title

• H10H20/8512

  Wavelength conversion materials · CPC title

• H10H20/8515

  not being in contact with the bodies · CPC title

• C09B5/62

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title