Cyanated benzoxanthene and benzothioxanthene compounds

Patent metadata

Field	Value
Publication number	US-10125143-B2
Application number	US-201615561218-A
Country	US
Kind code	B2
Filing date	Mar 24, 2016
Priority date	Mar 26, 2015
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

Abstract

Disclosed herein are cyanated compounds of the formula (I) wherein at least one of the radicals R 2 , R 3 , R 4 and R 5 is CN, and the remaining radicals are selected from hydrogen, chlorine and bromine; X is O, S, SO or SO 2 ; m is 0, 1, 2, 3 or 4; R 1 is selected from 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 24 -aryl, C 6 -C 24 -aryloxy, C 6 -C 24 -aryl-C 1 -C 10 -alkylene, etc.; A is a diradical selected from diradicals of the general formulae (A.1), (A.2), (A.3), and (A.4) wherein R 6 , (R 7 ) n , (R 8 ) o and (R 9 ) p are as defined in the claims and in the description. Also disclosed are color converters containing at least one polymer as a matrix material and at least one cyanated compound of formula (I) or mixtures thereof as a fluorescent dye, the use of the color converters, and lighting devices containing an LED and at least one color converter.

First claim

The invention claimed is:

1. A cyanated compound of formula (I):

wherein:
m is 0, 1, 2, 3 or 4;
each R 1 independently from each other is bromine, chlorine, cyano, a C 1 -C 24 -alkyl, a C 1 -C 24 -haloalkyl, a C 1 -C 24 -alkoxy, a C 1 -C 24 -haloalkoxy, a C 3 -C 24 -cycloalkyl, a heterocycloalkyl, a heteroaryl, a C 6 -C 24 -aryl, a C 6 -C 24 -aryloxy, or a C 6 -C 24 -aryl-C 1 -C 10 -alkylene, where rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl, aryloxy and-aryl-alkylene 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 the C 6 -C 24 -aryl-C 1 -C 10 -alkylene are optionally interrupted by at least one of O, S or NR c ;
at least one of the radicals R 2 , R 3 , R 4 and R 5 is CN, and remaining radicals, independently from each other, are hydrogen, chlorine or bromine;
X is O, S, SO or SO 2 ;
A is a diradical of formulae (A.1), (A.2), (A.3), or (A.4);

* in each case denotes the point of attachments to the remainder of the molecule;
n is 0, 1, 2, 3 or 4;
o is 0, 1, 2 or 3;
p is 0, 1, 2 or 3;
R 6 is hydrogen, a C 1 -C 24 -alkyl, a C 1 -C 24 -haloalkyl, a C 3 -C 24 -cycloalkyl, a C 6 -C 24 -aryl or a C 6 -C 24 -aryl-C 1 -C 10 -alkylene, where rings of cycloalkyl, aryl, and aryl-alkylene 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 the C 6 -C 24 -aryl-C 1 -C 10 -alkylene are optionally interrupted by one or more heteroatoms or heteroatomic groups of O, S and NR c ;
each R 7 independently from each other is bromine, chlorine, cyano, —NR a R b , a C 1 -C 24 -alkyl, a C 1 -C 24 -haloalkyl, a C 1 -C 24 -alkoxy, a C 1 -C 24 -haloalkoxy, a C 3 -C 24 -cycloalkyl, a heterocycloalkyl, a heteroaryl, a C 6 -C 24 -aryl, a C 6 -C 24 -aryloxy, or a C 6 -C 24 -aryl-C 1 -C 10 -alkylene, where rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R 7a and where C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl, C 1 -C 24 -alkoxy, C 1 -C 24 -haloalkoxy, and the alkylene moiety of the C 6 -C 24 -aryl-C 1 -C 10 -alkylene are optionally interrupted by at least one of O, S and NR c ;
each R 8 independently from each other is bromine, chlorine, cyano, NR a R b , a C 1 -C 24 -alkyl, a C 1 -C 24 -haloalkyl, a C 1 -C 24 -alkoxy, a C 1 -C 24 -haloalkoxy, a C 3 -C 24 -cycloalkyl, a heterocycloalkyl, a heteroaryl, a C 6 -C 24 -aryl, a C 6 -C 24 -aryloxy, or a C 6 -C 24 -aryl-C 1 -C 10 -alkylene, where rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R 8a and where C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl, C 1 -C 24 -alkoxy, C 1 -C 24 -haloalkoxy, and the alkylene moiety of the C 6 -C 24 -aryl-C 1 -C 10 -alkylene are optionally interrupted by at least one of O, S and NR c ;
each R 9 independently from each other is bromine, chlorine, cyano, NR a R b , a C 1 -C 24 -alkyl, a C 1 -C 24 -haloalkyl, a C 1 -C 24 -alkoxy, a C 1 -C 24 -haloalkoxy, a C 3 -C 24 -cycloalkyl, a heterocycloalkyl, a heteroaryl, a C 6 -C 24 -aryl, a C 6 -C 24 -aryloxy, or a C 6 -C 24 -aryl-C 1 -C 10 -alkylene, where rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R 9a and where C 1 -C 24 -alkyl, C 1 -C 24 -haloalkyl, C 1 -C 24 -alkoxy, C 1 -C 24 -haloalkoxy and the alkylene moiety of the C 6 -C 24 -aryl-C 1 -C 10 -alkylene are optionally interrupted by at least one of O, S and NR c ;
R 1a , R 6a , R 7a , R 8a , R 9a are independently of one another a C 1 -C 24 -alkyl, a C 1 -C 24 -fluoroalkyl, a C 1 -C 24 -alkoxy, fluorine, chlorine or bromine;
R a , R b , R c are independently of one another hydrogen, a C 1 -C 20 -alkyl, a C 3 -C 24 -cycloalkyl, a heterocycloalkyl, a hetaryl or a C 6 -C 24 -aryl.

2. The cyanated compound of formula (I) according to claim 1 , wherein X is O or S.

3. The cyanated compound of formula (I) according to claim 1 , wherein R 2 and R 4 are each cyano, and R 3 and R 5 are each hydrogen.

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

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

# represents the bonding site to the nitrogen atom;
R d and R e , in the formula (B.1), independently from each other are a C 1 -C 23 -alkyl, where the sum of the carbon atoms of the R d and R e radicals is an integer from 2 to 23; and
R f , R g and R h , in the formula (B.2) are independently a C 1 - to C 20 -alkyl, where the sum of the carbon atoms of the R f , R g and R h radicals is an integer from 3 to 23.

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

# represents the bonding side to the nitrogen atom;
B where present, is a C 1 -C 10 -alkylene group optionally interrupted by one or more nonadjacent groups selected from —O— and —S—;
y is 0 or 1;
R i is independently of one another a C 1 -C 24 -alkyl, a C 1 -C 24 -fluoroalkyl, fluorine, chlorine or bromine;
R k is independently a C 1 -C 24 -alkyl;
x in formulae C.2 and C.3 is 1, 2, 3,4 or 5.

7. The cyanated compound according to claim 1 , wherein m is zero or one.

8. A color converter, comprising at least one polymer as a matrix and at least one cyanated compound of claim 1 or a mixture thereof as a fluorescent dye,
wherein the at least one polymer comprises a polystyrene, a polycarbonate, a polymethylmethacrylate, a polyvinylpyrrolidone, a polymethacrylate, a polyvinyl acetate, a polyvinyl chloride, a polybutene, a silicone, a polyacrylate, an epoxy resin, a polyvinyl alcohol, a poly(ethylene vinylalcohol)-copolymer (EVA, EVOH), a polyacrylonitrile, a polyvinylidene chloride (PVDC), a polystyreneacrylonitrile (SAN), a polybutylene terephthalate (PBT), a polyethylene terephthalate (PET), a polyvinyl butyrate (PVB), a polyvinyl chloride (PVC), a polyamide, a polyoxymethylene, a polyimide, a polyetherimide or mixtures thereof.

9. The color converter according to claim 8 , further comprising at least one inorganic white pigment as a scattering body.

10. The color converter according to claim 8 , further comprising at least one fluorescent dye of formulae (IV), (V) or (VI):

wherein:
q is 1 to 4,
R 11 , R 12 are each independently a C 1 -C 30 -alkyl, a C 3 -C 8 -cycloalkyl, an aryl, a hetaryl, or an aryl-C 1 -C 10 -alkylene, where aromatic rings are unsubstituted or mono- or polysubstituted by a C

Assignees

• Basf Se

Inventors

• Koenemann Martin
• Wagenblast Gerhard
• Ivanovici Sorin
• Mattern Gabriele
• Mitgude Martina
• Weber Gerd

Classifications

• C09B57/08

  Naphthalimide dyes; Phthalimide dyes · CPC title

• C07D493/06 Primary

  Peri-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1037

  with sulfur · CPC title

• H05K999/99

  Electricity · mapped topic