Perylene bisimides with rigid 2,2′-biphenoxy bridges

Patent metadata

Field	Value
Publication number	US-11021610-B2
Application number	US-201716069954-A
Country	US
Kind code	B2
Filing date	Jan 13, 2017
Priority date	Jan 14, 2016
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

The present invention relates to perylene bisimides with rigid 2,2′-biphenoxy bridges which are useful in a wide variety of applications and to novel to perylene bisimides with rigid 2,2′-biphenoxy bridges. The present invention also relates to the use of said compound(s) in color converters for improving the luminous efficacy of LEDs, to color converters and their use and to lighting devices comprising at least one LED or OLED and at least one color converter. The present invention also relates to a printing ink formulation for security printing comprising at least one perylene bisimide with rigid 2,2′-biphenoxy bridges and security documents.

First claim

The invention claimed is:

1. A color converter comprising in a polymeric matrix material a fluorescent dye,
wherein the fluorescent dye is a perylene bisimide compound of formula (I):

or a mixture thereof,
wherein
R 1 and R 2 , independently of each other, are selected from the group consisting of hydrogen, in each case unsubstituted or substituted C 1 -C 30 -alkyl, polyalkyleneoxy, C 1 -C 30 -alkoxy, C 1 -C 30 -alkylthio, C 3 -C 20 -cycloalkyl, C 3 -C 20 -cycloalkyloxy, C 6 -C 24 -aryl and C 6 -C 24 -aryloxy; and
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, —NE 1 E 2 , —NR Ar1 COR Ar2 , —CONR Ar1 R Ar2 , —SO 2 NR Ar1 R Ar2 , —COOR Ar1 , —SO 3 R Ar2 , in each case unsubstituted or substituted C 1 -C 30 -alkyl, polyalkyleneoxy, C 1 -C 30 -alkoxy, C 1 -C 30 -alkylthio, C 3 -C 20 -cycloalkyl, C 3 -C 20 -cycloalkoxy, C 6 -C 24 -aryl, C 6 -C 24 -aryloxy and C 6 -C 24 -arylthio,
wherein R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 and/or R 17 and R 18 together with the carbon atoms of the biphenylyl moiety to which they are bonded, also optionally form a further fused aromatic or non-aromatic ring system wherein the fused ring system is unsubstituted or substituted;
E 1 and E 2 , independently of each other, are hydrogen, unsubstituted or substituted C 1 -C 18 -alkyl, unsubstituted or substituted C 2 -C 18 -alkenyl, unsubstituted or substituted C 2 -C 18 -alkynyl, unsubstituted or substituted C 3 -C 20 -cycloalkyl or unsubstituted or substituted C 6 -C 10 -aryl; and
R Ar1 and R Ar2 , each independently of each, are hydrogen, unsubstituted or substituted C 1 -C 18 -alkyl, unsubstituted or substituted C 3 -C 20 -cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 6 -C 20 -aryl or unsubstituted or substituted heteroaryl.

2. The color converter as claimed in claim 1 ,
wherein R 1 and R 2 independently of each other are selected from the group consisting of C 1 -C 10 -alkyl, which is unsubstituted or substituted by C 6 -C 10 -aryl which in turn is unsubstituted or substituted by 1, 2 or 3 C 1 -C 10 -alkyl, C 3 -C 8 -cycloalkyl, which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 10 -alkyl, and C 6 -C 10 -aryl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 10 -alkyl.

3. The color converter as claimed in claim 1 ,
wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 independently of each other, are selected from the group consisting of hydrogen, halogen, C 1 -C 18 -alkyl, C 6 -C 10 -aryl, C 6 -C 10 -aryl-C 1 -C 10 -alkylene, C 6 -C 10 -aryloxy and C 6 -C 10 -arylthio, wherein the aryl moiety of C 6 -C 10 -aryl, C 6 -C 10 -aryl-C 1 -C 10 -alkylene, C 6 -C 10 -aryloxy and C 6 -C 10 -arylthio is unsubstituted or substituted by one or more C 1 -C 10 -alkyl, and in addition R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , and/or R 16 and R 17 together with the carbon atoms of the biphenylyl moiety to which they are bonded, also optionally form a further fused benzene ring system.

4. The color converter as claimed in claim 1 ,
wherein R 3 , R 10 , R 11 and R 18 are each hydrogen and R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 independently of each other, are selected from the group consisting of hydrogen and C 1 -C 18 -alkyl, and in addition R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 13 and R 14 , R 14 and R 15 , and/or R 15 and R 16 together with the carbon atoms of the biphenylyl moiety to which they are bonded, are also optionally a benzene ring system.

5. The color converter as claimed in claim 1 ,
wherein the polymeric matrix material consists essentially of at least one polymer selected from the group consisting of polystyrene, polycarbonate, polymethylmethacrylate, polyvinylpyrrolidone, polymethacrylate, polyvinyl acetate, polyvinyl chloride, polybutene, silicone, polyacrylate, epoxy resin, polyvinyl alcohol, poly(ethylene vinylalcohol)-copolymer, polyacrylonitrile, polyvinylidene chloride, polystyrene acrylonitrile, polybutylene terephthalate, polyethylene terephthalate, polyvinyl butyrate, polyvinyl chloride, a polyamide, a polyoxymethylene, a polyimide, and a polyetherimide.

6. The color converter as claimed in claim 1 ,
wherein the color converter additionally comprises an inorganic white pigment as a scattering body.

7. The color converter as claimed in claim 1 , comprising at least one additional organic fluorescent dye selected from the group consisting of
(i) a cyanated naphthalene benzimidazole compound of formula II:

wherein
R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 210 are each independently hydrogen, cyano or aryl which is unsubstituted or has one or more identical or different substituents R 2Ar ,
wherein each R 2Ar is independently selected from the group consisting of cyano, hydroxyl, mercapto, halogen, C 1 -C 20 -alkoxy, C 1 -C 20 -alkylthio, nitro, —NR 2Ar2 R 2Ar3 , —NR 2Ar2 COR 2Ar3 , —CONR 2Ar2 R 2Ar3 , —SO 2 NR 2Ar2 R 2Ar3 , —COOR 2Ar2 , —SO 3 R 2Ar2 , C 1 -C 30 -alkyl, C 2 -C 30 -alkenyl, C 2 -C 30 -alkynyl, wherein the three latter radicals are unsubstituted or bear one or more R 2a groups, C 3 -C 8 -cycloalkyl, 3- to 8-membered heterocyclyl, wherein the two latter radicals are unsubstituted or bear one or more R 2b groups, aryl, U-aryl, heteroaryl and U-heteroaryl, wherein the four latter radicals are unsubstituted or bear one or more R 2b groups,
each R 2a 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 2Ar2 R Ar3 , —NR 2Ar2 COR 2Ar3 , —CONR 2Ar2 R Ar3 , —SO 2 NR 2Ar2 R Ar3 , —COOR 2Ar2 , —SO 3 R 2Ar2 , C 3 -C 8 -cycloalkyl, 3- to 8-membered heterocyclyl, aryl and heteroaryl, wherein the cycloalkyl, heterocyclyl, aryl and heteroaryl radicals are unsubstituted or bear one or more R 2b groups;
each R 2b 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 2Ar2 R 2Ar3 , —NR 2Ar2 COR 2Ar3 , —CONR 2Ar2 R 2Ar3 , —SO 2 NR 2Ar2 R 2Ar3 , —COOR 2Ar2 , —SO 3 R 2Ar2 , 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, wherein the four latter radicals are unsubstituted or bear one or more R 2b1 groups,
each R 2b1 is independently selected from the group consisting of cyano, hydroxyl, mercapto, oxo, nitro, halogen, —NR 2Ar2 R 2Ar3 , —NR 2Ar2 COR 2Ar3 , —CONR 2Ar2 R 2Ar3 , —SO 2 NR 2Ar2 R 2Ar3 , —COOR 2Ar2 , —SO 3 R 2Ar2 , —SO 3 R 2Ar2 , C 1-18 -alkyl, C 2 -C 18 -alkenyl, C 2 -C 18 -alkynyl, C 1 -C 12 -alkoxy, and C 1 -C 12 -alkylthio,
U is an —O—, —S—, —NR 2Ar1 —, —CO—, —SO— or —SO 2 — moiety;
R 2Ar1 , R 2Ar2 and R 2Ar3 are each independently hydrogen, C 1 -C 18 -alkyl, 3- to 8-membered cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, wherein alkyl is unsubstituted or bears one or more R 2a groups, wherein 3- to 8-membered cyclo

Assignees

• Basf Se

Inventors

• Koenemann Martin
• Wagenblast Gerhard
• Ivanovici Sorin
• Mitgude Martina

Classifications

• C09K11/77348

  Silicon Aluminium Nitrides or Silicon Aluminium Oxynitrides · CPC title

• C09K11/7774

  Aluminates · CPC title

• C09K11/77342

  Silicates · CPC title

• H10H20/8512

  Wavelength conversion materials · CPC title

• C09K2211/1037

  with sulfur · CPC title