Cyanated naphthalenebenzimidazole compounds

Patent metadata

Field	Value
Publication number	US-9790423-B2
Application number	US-201414910078-A
Country	US
Kind code	B2
Filing date	Aug 4, 2014
Priority date	Aug 5, 2013
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

The present invention relates to cyanated naphthalenebenzimidazole compounds of the formula (I) and mixtures thereof, in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently hydrogen, cyano or aryl which is unsubstituted or has one or more identical or different substituents R Ar , where R Ar is as defined in the claims and in the description, with the proviso that the compounds of the formula I comprise at least one cyano group. The invention further relates to color converters comprising at least one polymer as a matrix material and at least one cyanated naphthalenebenzimidazole compound or mixtures thereof as a fluorescent dye, to the use of the 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 naphthalenebenzimidazole compound of the formula I

or mixture of these,
in which
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently hydrogen, cyano or aryl which is unsubstituted or has one or more identical or different substituents R Ar , where
each R A r is independently selected from the group consisting of cyano, hydroxyl, mercapto, halogen, C 1 -C 20 -alkoxy, C 1 -C 20 -alkylthio, nitro, —NR Ar2 R Ar3 , —NR Ar2 COR Ar3 , —CONR Ar2 R Ar3 , SO 2 NR Ar2 R Ar3 , —COOR Ar2 , —SO 3 R Ar2 ,
C 1 -C 30 -alkyl, C 2 -C 30 -alkenyl, C 2 -C 30 -alkynyl, where the three latter radicals are unsubstituted or bear one or more R a groups,
C 3 -C 8 -cycloalkyl, 3- to 8-membered heterocyclyl, where the two latter radicals are unsubstituted or bear one or more R b groups,
aryl, U-aryl, heteroaryl and U-heteroaryl, where the four latter radicals are unsubstituted or bear one or more R b groups,
where
each R a is independently selected from the group consisting of cyano, hydroxyl, oxo, mercapto, halogen, C 1 -C 20 -alkoxy, C 1 -C 20 -alkylthio, nitro, —NR Ar2 R Ar3 , —NR Ar2 COR Ar3 , —CONR Ar2 R Ar3 , —SO 2 NR Ar2 R Ar3 , —COOR Ar2 , —SO 3 R Ar2 , C 3 -C 8 -cycloalkyl, 3- to 8-membered heterocyclyl, aryl and heteroaryl, where the cycloalkyl, heterocyclyl, aryl and heteroaryl radicals are unsubstituted or bear one or more R b groups;
each R b is independently selected from the group consisting of cyano, hydroxyl, oxo, mercapto, halogen, C 1 -C 20 -alkoxy, C 1 -C 20 -alkylthio, nitro, —NR Ar2 R Ar3 , —NR Ar2 COR Ar3 , —CONR Ar2 R Ar3 , —SO 2 NR Ar2 R Ar3 , —COOR Ar2 , —SO 3 R Ar2 , C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl, C 3 -C 8 -cycloalkyl, 3- to 8-membered heterocyclyl, aryl and heteroaryl, where the four latter radicals are unsubstituted or bear one or more R b1 groups,
each R b1 is independently selected from the group consisting of cyano, hydroxyl, mercapto, oxo, nitro, halogen, —NR Ar2 R Ar3 , —NR Ar2 COR Ar3 , —CONR Ar2 R Ar3 , —SO 2 NR Ar2 R Ar3 , —COOR Ar2 , —SO 3 R Ar2 , —SO 3 R Ar2 , C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylthio,
U is an —O—, —S—, —NR Ar1 —, —CO—, —SO— or —SO 2 — moiety;
R Ar1 , R Ar2 , R Ar3 are each independently hydrogen, C 1 -C 15 -alkyl, 3- to 8-membered cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where alkyl is unsubstituted or bears one or more R a groups, where 3- to 8-membered cycloalkyl, 3- to 8-membered heterocyclyl, aryl and heteroaryl are unsubstituted or bear one or more R b groups;

with the proviso that one, two or three of the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 are cyano and 1, 2, 3, 4, 5, 6 or 7 of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 radicals is/are aryl which is unsubstituted or has one or more identical or different substituents R Ar .

2. The cyanated naphthalenebenzimidazole compound or a mixture of these according to claim 1 , in which each R Ar is independently cyano, C 1 -C 12 -alkoxy, hydroxyl, halogen, nitro, —NR Ar2 R Ar3 , NR Ar2 COR Ar3 , —CONR Ar2 R Ar3 , —SO 2 NR Ar2 R Ar3 , —COOR Ar2 , —SO 3 R Ar2 , C 1 -C 18 -alkyl which is unsubstituted or mono- or polysubstituted by hydroxyl, halogen, cyano, nitro or —NR Ar2 R Ar3 , or C 3 -C 8 -cycloalkyl or phenyl, where the two latter radicals are in turn unsubstituted or mono- or polysubstituted by C 1 -C 18 -alkyl, C 1 -C 12 -alkoxy or cyano.

3. The cyanated naphthalenebenzimidazole compound or a mixture of these according to claim 1 , in which at least one of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 radicals is phenyl which is unsubstituted or has one or more identical or different R Ar radicals.

4. The cyanated naphthalenebenzimidazole compound or a mixture of these according to claim 3 , in which at least one of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 radicals is phenyl which is unsubstituted or bears a cyano group.

5. The cyanated naphthalenebenzimidazole compound or a mixture of these according to claim 3 , in which at least one of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 radicals is phenyl, which is unsubstituted or carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl.

6. The cyanated naphthalenebenzimidazole compound or a mixture of these 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 , R 8 , R 9 and R 10 radicals is/are cyano.

7. The cyanated naphthalenebenzimidazole compound or a mixture of these according to claim 1 , in which
one or two of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 radicals is/are phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl and the other R 1 , R 2 , R 3 , R 4 , R 5 , R 6 radicals are hydrogen; and
zero, one or two of the R 7 , R 8 , R 9 and R 10 radicals is/are phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl and the other R 7 , R 8 , R 9 and R 10 radicals are hydrogen or cyano.

8. The cyanated naphthalenebenzimidazole compound according to claim 1 , in which one or two of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 radicals is/are phenyl, 4-cyanophenyl, cyano or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl and the other R 1 , R 2 , R 3 , R 4 , R 5 , R 6 radicals are hydrogen; and
zero, one, two or three of the R 7 , R 8 , R 9 and R 10 radicals is/are phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl and the other R 7 , R 8 , R 9 and R 10 radicals are hydrogen or cyano.

9. The cyanated naphthalenebenzimidazole compound or a mixture of these according to claim 1 , wherein the cyanated napthalenebenzimidazole compound corresponds to the formula I-A

or a mixture of these
in which
R 3 and R 4 are each independently cyano, phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl; and
R 7 , R 8 , R 9 and R 10 are each independently hydrogen, cyano, phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl.

10. The cyanated naphthalenebenzimidazole compound according to claim 9 ,
wherein the cyanated napthalenebenzimidazole compound corresponds to the formula I-Aa

in which
R 4 is phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl; and
two of the radicals R 7 , R 8 , R 9 and R 10 are each independently, phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl and the other radicals R 7 , R 8 , R 9 and R 10 are hydrogen.

11. A mixture of cyanated naphthalenebenzimidazole compounds according to claim 9 , wherein the cyanated naphthalenebenzimidazole compounds correspond to the formula I-Ab and I-Ab′

in which
R 4 is phenyl, 4-cyanophenyl or phenyl which carries 1, 2 or 3 substituents selected from C 1 -C 10 -alkyl; and
zero, one or two of the radicals R 7 , R 10 , R 8 and R 9 , if present, are each independently, phenyl,

Assignees

• Basf Se

Inventors

• Könemann Martin
• Mattern Gabriele
• Wagenblast Gerhard
• Ivanovici Sorin
• Send Robert

Classifications

• H01L31/02322

  Electricity · mapped topic

• Y02E10/52

  PV systems with concentrators · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• H01L51/5262

  Electricity · mapped topic

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title