Cyanated perylene compounds

Patent metadata

Field	Value
Publication number	US-9919999-B2
Application number	US-201515309631-A
Country	US
Kind code	B2
Filing date	May 8, 2015
Priority date	May 9, 2014
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

The present invention relates to a cyanated perylene compound of the formula I

in which

one of the Z substituents and one of the Z* substituents are cyano and the other Z substituent and the other Z* substituent are each independently CO 2 R 9 , CONR 10 R 11 , optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or C 6 -C 14 -aryl, where R 9 , R 10 and R 11 are each as defined in the claims;

and mixtures thereof.

The present invention further relates to a composition comprising a cyanated perylene compound of the formula I or mixtures thereof and to a process for preparation thereof; to color converters comprising at least one polymer as matrix material and at least one cyanated perylene compound or mixtures thereof or a composition comprising at least one cyanated perylene compound or mixtures thereof as fluorescent dye; to the use of these color converters and to lighting devices comprising at least one LED and at least one color converter.

First claim

The invention claimed is:

1. A cyanated perylene compound of the formula I

in which
one of the Z substituents is cyano and the other Z substituent is CO 2 R 9 , CONR 10 R 11 , C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl, where
C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl are unsubstituted or bear one or more identical or different Z a substituents,
C 3 -C 12 -cycloalkyl is unsubstituted or bears one or more identical or different Z b substituents, and
C 6 -C 14 -aryl is unsubstituted or bears one or more identical or different Z Ar substituents;

one of the Z* substituents is cyano and the other Z* substituent is CO 2 R 9 , CONR 10 R 11 , C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl, where
C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl are unsubstituted or bear one or more identical or different Z a substituents,
C 3 -C 12 -cycloalkyl is unsubstituted or bears one or more identical or different Z b substituents, and
C 6 -C 14 -aryl is unsubstituted or bears one or more identical or different Z Ar substituents;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from hydrogen, cyano, bromine and chlorine,
with the proviso that 1, 2, 3, 4, 5, 6, 7 or 8 of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 substituents are cyano;
where

R 9 is hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl, where
C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl are unsubstituted or bear one or more identical or different R a substituents,
C 3 -C 12 -cycloalkyl is unsubstituted or bears one or more identical or different R b substituents and
C 6 -C 14 -aryl is unsubstituted or bears one or more identical or different R Ar substituents;

R 10 and R 11 are each independently hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl, where
C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl are unsubstituted or bear one or more identical or different R a substituents,
C 3 -C 12 -cycloalkyl is unsubstituted or bears one or more identical or different R b substituents and
C 6 -C 14 -aryl is unsubstituted or bears one or more identical or different R Ar substituents;
each Z a is independently halogen, hydroxyl, NR 10a R 11a , C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 3 -C 12 -cycloalkyl, C 6 -C 14 -aryl, C(═O)R 9a , C(═O)OR 9a or C(O)NR 10a R 11a , where
C 3 -C 12 -cycloalkyl is unsubstituted or bears one or more identical or different R b substituents and
C 6 -C 14 -aryl is unsubstituted or bears one or more identical or different R Ar substituents;

each Z b and each Z Ar is independently halogen, hydroxyl, NR 10a R 11a , C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C(═O)R 9a , C(═O)OR 9a or C(O)NR 10a R 11a ;
each R a is independently halogen, hydroxyl, C 1 -C 10 -alkoxy, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl;
each R b is independently halogen, hydroxyl, C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl;
each R Ar is independently halogen, hydroxyl, C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl;
R 9a is hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl; and
R 10a , R 11a are each independently hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl,

and mixtures thereof.

2. A cyanated perylene compound of the formula I according to claim 1 , in which 1, 2, 3 or 4 of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 substituents are cyano.

3. A cyanated perylene compound of the formula I according to claim 1 , in which none of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 substituents are bromine or chlorine.

4. A cyanated perylene compound of the formula I according to
claim 1 ,
in which one or two of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 substituents are cyano and the other R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 substituents are hydrogen.

5. A cyanated perylene compound of the formula I according to
claim 1 , in which one of the Z substituents and one of the Z* substituents are independently selected from C 1 -C 10 -alkyl, CO 2 R 9 , phenyl-C 1 -C 10 -alkyl and phenyl, where phenyl and the phenyl moiety of phenyl-C 1 -C 10 -alkyl are unsubstituted or bear one or more substituents selected from C 1 -C 6 -alkyl, and where R 9 is as defined above.

6. A cyanated perylene compound of the formula I according to claim 1 , selected from compounds of the formulae (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), and (20)

in which
Z is selected from C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, phenyl, and phenyl bearing 1, 2 or 3 C 1 -C 4 -alkyl groups; and
Z* is selected from C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, phenyl, and phenyl bearing 1, 2 or 3 C 1 -C 4 -alkyl groups;
and mixtures thereof.

7. A composition comprising at least one cyanated perylene compound of the formula I according to claim 1 .

8. The composition according to claim 7 , comprising at least one cyanated perylene compound of the formula I-A

in which
one of the Z substituents is cyano and the other Z substituent is C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl, where
C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl are unsubstituted or bear one or more identical or different Z a substituents, where Z a is as defined above,
C 3 -C 12 -cycloalkyl is unsubstituted or bears one or more identical or different Z b substituents, where Z b is as defined above; and
C 6 -C 14 -aryl is unsubstituted or bears one or more identical or different Z Ar substituents, where Z Ar is as defined above;

one of the Z* substituents is cyano and the other Z* substituent is C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl, C 3 -C 12 -cycloalkyl or C 6 -C 14 -aryl, where
C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl are unsubstituted or bear one or more identical or different Z a substituents, where Z a is as defined above,
C 3 -C 12 -cycloalkyl is unsubstituted or bears one or more identical or different Z b substituents, where Z b is as defined above; and
C 6 -C 14 -aryl is unsubstituted or bears one or more identical or different Z Ar substituents, where Z Ar is as defined above;

R 1 , R 4 , R 5 and R 8 are each hydrogen;
two of the R 2 , R 3 , R 6 or R 7 substituents are hydrogen; and the other R 2 , R 3 , R 6 or R 7 substituents are cyano;

Assignees

• Basf Se

Inventors

• Koenemann Martin
• Wagenblast Gerhard
• Ivanovici Sorin
• Send Robert
• Mattern Gabriele
• Weber Gerd

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C07C255/57 Primary

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07C255/52 Primary

  to carbon atoms of six-membered aromatic rings being part of condensed ring systems · CPC title

• C09K11/7774

  Aluminates · CPC title