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US 11,021,610 B2Granted
Perylene bisimides with rigid 2,2′-biphenoxy bridges
AssigneeBASF SE
InventorsMartin Koenemann, Gerhard Wagenblast, Sorin Ivanovici, Martina Mitgude
Life of this patent
Estimating the term…
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.
Claims18
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
- R1 and R2, independently of each other, are selected from the group consisting of hydrogen, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkyloxy, C6-C24-aryl and C6-C24-aryloxy;
- and
- R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, —NE1E2, —NRAr1CORAr2, —CONRAr1RAr2, —SO2NRAr1RAr2, —COORAr1, —SO3RAr2, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkoxy, C6-C24-aryl, C6-C24-aryloxy and C6-C24-arylthio,
- wherein R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R11 and R12, R12 and R13, R13 and R14, R14 and R15, R15 and R16, R16 and R17 and/or R17 and R18 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;
- E1 and E2, independently of each other, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C2-C18-alkenyl, unsubstituted or substituted C2-C18-alkynyl, unsubstituted or substituted C3-C20-cycloalkyl or unsubstituted or substituted C6-C10-aryl;
- and
- RAr1 and RAr2, each independently of each, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C3-C20-cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C6-C20-aryl or unsubstituted or substituted heteroaryl.
7 more elements
A compound of formula (I):
- or a mixture thereof,
- wherein
- R1 and R2, independently of each other, are selected from the group consisting of hydrogen, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkyloxy, C6-C24-aryl and C6-C24-aryloxy;
- and
- R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, —NE1E2, —NRAr1CORAr2, —CONRAr1RAr2, —SO2NRAr1RAr2, —COORAr1, —SO3RAr2, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkoxy, C6-C24-aryl, C6-C24-aryloxy and C6-C24-arylthio,
- wherein R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R11 and R12, R12 and R13, R13 and R14, R14 and R15, R15 and R16, R16 and R17 and/or R17 and R18 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;
- E1 and E2, independently of each other, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C2-C18-alkenyl, unsubstituted or substituted C2-C18-alkynyl, unsubstituted or substituted C3-C20-cycloalkyl or unsubstituted or substituted C6-C10-aryl;
- and
- RAr1 and RAr2, each independently of each, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C3-C20-cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C6-C20-aryl or unsubstituted or substituted heteroaryl.
6 more elements
A security ink for security printing, comprising perylene bisimide compound of formula (I):
- or a mixture thereof,
- wherein
- R1 and R2, independently of each other, are selected from the group consisting of hydrogen, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkylthio, C20-cycloalkyl, C3-C20-cycloalkyloxy, C6-C24-aryl and C6-C24-aryloxy;
- and
- R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, —NE1E2, —NRAr1CORAr2, —CONRAr1RAr2, —SO2NRAr1RAr2, —COORAr1, —SO3RAr2, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkoxy, C6-C24-aryl, C6-C24-aryloxy and C6-C24-arylthio,
- wherein R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R11 and R12, R12 and R13, R13 and R14, R14 and R15, R15 and R16, R16 and R17 and/or R17 and R18 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;
- E1 and E2, independently of each other, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C2-C18-alkenyl, unsubstituted or substituted C2-C18-alkynyl, unsubstituted or substituted C3-C20-cycloalkyl or unsubstituted or substituted C6-C10-aryl;
- and
- RAr1 and RAr2, each independently of each, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C3-C20-cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C6-C20-aryl or unsubstituted or substituted heteroaryl.
6 more elements
A printing ink formulation for security printing, comprising:
- a perylene bisimide compound of formula (I):
- or a mixture thereof,
- wherein
- R1 and R2, independently of each other, are selected from the group consisting of hydrogen, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkyloxy, C6-C24-aryl and C6-C24-aryloxy;
- and
- R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, —NE1E2, —NRAr1CORAr2, —CONRAr1RAr2, —SO2NRAr1RAr2, —COORAr1, —SO3RAr2, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkoxy, C6-C24-aryl, C6-C24-aryloxy and C6-C24-arylthio,
- wherein R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R11 and R12, R12 and R13, R13 and R14, R14 and R15, R15 and R16, R16 and R17 and/or R17 and R18 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;
- E1 and E2, independently of each other, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C2-C18-alkenyl, unsubstituted or substituted C2-C18-alkynyl, unsubstituted or substituted C3-C20-cycloalkyl or unsubstituted or substituted C6-C10-aryl;
- and
- RAr1 and RAr2, each independently of each, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C3-C20-cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C6-C20-aryl or unsubstituted or substituted heteroaryl.
7 more elements
A compound of formula (I):
- or a mixture thereof,
- wherein
- R1 and R2, independently of each other, are selected from the group consisting of hydrogen, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkyloxy, C6-C24-aryl and C6-C24-aryloxy;
- and
- R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, —NE1E2, —NRAr1CORAr2, —CONRAr1RAr2, —SO2NRAr1RAr2, —COORAr1, —SO3RAr2, in each case unsubstituted or substituted C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkoxy, C6-C24-aryl, C6-C24-aryloxy and C6-C24-arylthio,
- wherein R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R11 and R12, R12 and R13, R13 and R14, R14 and R15, R15 and R16, R16 and R17 and/or R17 and R18 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;
- E1 and E2, independently of each other, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C2-C18-alkenyl, unsubstituted or substituted C2-C18-alkynyl, unsubstituted or substituted C3-C20-cycloalkyl or unsubstituted or substituted C6-C10-aryl;
- and
- RAr1 and RAr2, each independently of each, are hydrogen, unsubstituted or substituted C1-C18-alkyl, unsubstituted or substituted C3-C20-cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C6-C20-aryl or unsubstituted or substituted heteroaryl, and
- wherein the compound is not a compound of formula (I) wherein R1 and R2 are each n-C4H9 and R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 are each hydrogen.
7 more elements
Dependencies are inferred from the claim text.