# US 11,441,036 B2 · 2-phenylphenoxy-substituted perylene bisimide compounds and their use

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- Number: US 11,441,036 B2
- Document ID: US11441036B2
- Status: Granted
- Kind: B2
- Application number: 16/339,653
- Filed: 2017-10-05
- Published: 2020-03-05
- Granted: 2022-09-13
- Earliest claimed: 2016-10-06
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Martin Koenemann; Gerhard Wagenblast; Sorin Ivanovici; Martina Mitgude
- Web page: https://patentgrep.com/patent/US11441036B2

## CPC

- C07D 471/06: Peri-condensed systems
- C09B 5/62: Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
- C09B 67/0033: {Blends of pigments; Mixtured crystals; Solid solutions}
- C09B 67/0034: {Mixtures of two or more pigments or dyes of the same type}
- C09D 11/037: characterised by the pigment
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/06: containing organic luminescent materials
- F21K 9/64: using wavelength conversion means distinct or spaced from the light-generating element, e.g. a remote phosphor layer
- H10H 20/8512: {Wavelength conversion materials}
- C09K 2211/1018: Heterocyclic compounds
- F21Y 2115/10: Light-emitting diodes [LED]
- H10H 20/8511: {characterised by their material, e.g. binder}
- Y02B 20/00: Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- F21K: NON-ELECTRIC LIGHT SOURCES USING LUMINESCENCE; LIGHT SOURCES USING ELECTROCHEMILUMINESCENCE; LIGHT SOURCES USING CHARGES OF COMBUSTIBLE MATERIAL; LIGHT SOURCES USING SEMICONDUCTOR DEVICES AS LIGHT-GENERATING ELEMENTS; LIGHT SOURCES NOT OTHERWISE PROVIDED FOR
- H10H: INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
- F21Y: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES F21K, F21L, F21S and F21V, RELATING TO THE FORM OR THE KIND OF THE LIGHT SOURCES OR OF THE COLOUR OF THE LIGHT EMITTED
- Y02B: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS

## Abstract

The present invention relates to a perylene bisimide compound of formula (I) or a mixture thereof. The present invention also relates to the use of the compound in color converters, to the color converters and their use, and to lighting devices containing at least one LED and at least one of the color converters. The present invention also relates to a printing ink formulation for security printing containing at least one of the phenoxy-substituted perylene bisimide compounds.

## Claims

### Claim 1

A perylene bisimide compound of formula (I)
wherein
R1 and R2, independently of each other, are hydrogen, an unsubstituted or a substituted C1-C30-alkyl, an unsubstituted or a substituted polyalkyleneoxy, an unsubstituted or a substituted C1-C30-alkoxy, an unsubstituted or a substituted C1-C30-alkylthio, an unsubstituted or a substituted C3-C20-cycloalkyl, an unsubstituted or a substituted C3-C20-cycloalkyloxy, an unsubstituted or a substituted C6-C24-aryl, or an unsubstituted or a substituted C6-C24-aryloxy;
R3, R10, R11, and R18, independently of each other, are phenyl or phenyl substituted by one, two, three, four or five radicals L, wherein L is halogen, cyano, hydroxyl, mercapto, —NRAr1CORAr2, 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 or C6-C24-arylthio;
R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, R16, and R17 independently of each other, are hydrogen, halogen, cyano, hydroxyl, mercapto, —NRAr1CORAr2, —CONRAr1RAr2, —SO2NRAr1RAr2, —COORAr1, —SO3RAr2, an unsubstituted or a substituted C1-C30-alkyl, an unsubstituted or a substituted polyalkyleneoxy, an unsubstituted or a substituted C1-C30-alkoxy, an unsubstituted or a substituted C1-C30-alkylthio, an unsubstituted or a substituted C3-C20-cycloalkyl, an unsubstituted or a substituted C3-C20-cycloalkoxy, an unsubstituted or a substituted C6-C24-aryl, an unsubstituted or a substituted C6-C24-aryloxy or an unsubstituted or a substituted C6-C24-arylthio,
where R4 and R5, R5 and R6, R7 and R8, R8 and R9, R12 and R13, R13 and R14, R14 and R15, R15 and R16, and/or R16 and R17 together with the carbon atoms to which they are bonded, are optionally form a fused aromatic or non-aromatic carbon ring system wherein the fused ring system is unsubstituted or substituted;
where RAr1 and RAr2, independently of each other, are hydrogen, an unsubstituted or a substituted C1-C18-alkyl, an unsubstituted or a substituted C3-C20-cycloalkyl, an unsubstituted or a substituted heterocyclyl, an unsubstituted or a substituted C6-C20-aryl or an unsubstituted or a substituted heteroaryl.

### Claim 2 (depends on 1)

The compound of claim 1, where R1 and R2 in formula (I) independently of each other are
C1-C10-alkyl, which is unsubstituted or substituted by C6-C10-aryl which in turn is unsubstituted or substituted by 1, 2 or 3 C1-C10-alkyl,
C3-C8-cycloalkyl, which is unsubstituted or substituted by 1, 2 or 3 C1-C10-alkyl, and
C6-C10-aryl which is unsubstituted or substituted by 1, 2 or 3 C1-C10-alkyl.

### Claim 3 (depends on 1)

The compound of claim 1, where in R3, R10, R11 and R18, independently of each other, are phenyl or phenyl which is substituted by 1 or 2 radicals selected from the group consisting of C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl and C1-C6-alkoxy.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, R16 and R17, independently of each other, are hydrogen, halogen, C1-C18-alkyl, C6-C10-aryl, C6-C10-aryl-C1-C10alkylene, C6-C10-aryloxy or C6-C10-arylthio, where the aryl moiety of C6-C10-aryl, C6-C10-aryl-C1-C10-alkylene, C6-C10-aryloxy and C6-C10-arylthio is unsubstituted or substituted by one or more C1-C10-alkyl.

### Claim 5 (depends on 4)

The compound of claim 4, wherein R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, R16 and R17, independently of each other, are hydrogen, C1-C6-alkyl or C6-C10-aryl.

### Claim 6 (depends on 1)

A color converter, comprising
at least one compound of the formula (I) of claim 1 as fluorescent dye and
at least one polymer as a matrix, wherein the polymer is selected from the group consisting of polystyrene, polycarbonate, polymethyl methacrylate, polyvinylpyrrolidone, polymethacrylate, polyvinyl acetate, polyvinyl chloride, polybutene, silicone, polyacrylate, epoxy resin, polyvinyl alcohol, poly(ethylene vinylalcohol)-copolymer, polyacrylonitrile, polyvinylidene chloride, poly(styrene-acrylonitrile), polybutylene terephthalate, polyethylene terephthalate, polyvinyl butyrate, polyvinyl chloride, polyamides, polyoxymethylenes, polyimides, polyetherimides and a mixture thereof.

### Claim 7 (depends on 6)

The color converter of claim 6, further comprising
at least one inorganic white pigment as a scattering body.

### Claim 8 (depends on 7)

The color converter of claim 7, further comprising
at least one further organic fluorescent dye selected from the group consisting of
(i) a cyanated naphthoylbenzimidazole compound of formula II
and a mixture thereof,
wherein
R21, R22, R23, R24, R25, R26, R27, R28, R29 and R210 are each independently hydrogen, cyano or aryl which is unsubstituted or has one or more identical or different substituents R2Ar,
where
each R2Ar is independently cyano, hydroxyl, mercapto, halogen, C1-C20-alkoxy, C1-C20-alkylthio, nitro, —NR2Ar2R2Ar3, —NR2Ar2COR2Ar3, —CONR2Ar2R2Ar3, —SO2NR2Ar2R2Ar3, —COOR2Ar2, —SO3R2Ar2, C1-C30-alkyl, C2-C30-alkenyl, C2-C30-alkynyl, C3-C8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl, U-aryl, heteroaryl, or U-heteraryl, where C1-C30-alkyl, C2-C30-alkenyl, and C2-C30-alkynyl are unsubstituted or bear one or more R2a groups, C3-C8-cycloalkyl and 3- to 8-membered heterocyclyl are unsubstituted or bear one or more R2b groups, and aryl, U-aryl, heteroaryl and U-heteroaryl are unsubstituted or bear one or more R2b groups,
where
each R2a is independently cyano, hydroxyl, oxo, mercapto, halogen, C1-C20-alkoxy, C1-C20-alkylthio, nitro, —NR2Ar2R2Ar3, —NR2Ar2COR2Ar3, —CONR2Ar2R2Ar3, —SO2NR2Ar2R2Ar3, —COOR2Ar2, —SO3R2Ar2, C3-C8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl, or heteroaryl, where the cycloalkyl, heterocyclyl, aryl and heteroaryl radicals are unsubstituted or bear one or more R2b groups,
each R2b is independently cyano, hydroxyl, oxo, mercapto, halogen, C1-C20-alkoxy, C1-C20-alkylthio, nitro, —NR2Ar2R2Ar3, —NR2Ar2COR2Ar3, —CONR2Ar2R2Ar3, —SO2NR2Ar2R2Ar3, —COOR2Ar2, —SO3R2Ar2, C1-C18-alkyl, C2-C18-alkenyl, C2-C18-alkynyl, C3-C8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl, or heteroaryl, where C3-C8-cycloalkyl, 3- to 8-memberd heterocyclyl, aryl, and heteroaryl are unsubstituted or bear one or more R2b1 groups,
each R2b1 is independently cyano, hydroxyl, mercapto, oxo, nitro, halogen, —NR2Ar2R2Ar3, —NR2Ar2COR2Ar3, —CONR2Ar2R2Ar3, —SO2NR2Ar2R2Ar3, —COOR2Ar2, —SO3R2Ar2, —SO3R2Ar2, C1-C18-alkyl, C2-C18-alkenyl, C2-C18-alkynyl, C1-C12-alkoxy, or C1-C12-alkylthio,
U is an —O—, —S—, —NR2Ar1, —CO—, —SO— or —SO2— moiety,
R2Ar1, R2Ar2, R2Ar3 are each independently hydrogen, C1-C18-alkyl, 3- to 8-membered cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where alkyl is unsubstituted or bears one or more R2a groups, where 3- to 8-membered cycloalkyl, 3- to 8-membered heterocyclyl, aryl and heteroaryl are unsubstituted or bear one or more R2b groups,
with the proviso that the compound of the formula II comprises at least one cyano group,
(ii) a cyanated perylene compound of (III)
and a mixture thereof,
wherein
one of the Z3 substituents is cyano and the other Z3 substituent is CO2R39, CONR310R311, C1-C18-alkyl, C2-C18-alkenyl, C2-C18-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl, where
C1-C18-alkyl, C2-C18-alkenyl, and C2-C18-alkynyl are unsubstituted or bear one or more identical or different Z3a substituents,
C3-C12-cycloalkyl is unsubstituted or bears one or more identical or different Z3b substituents, and
C6-C14-aryl is unsubstituted or bears one or more identical or different Z3Ar substituents;
one of the Z3* substituents is cyano and the other Z3* substituent is CO2R39, CONR310R311, C1-C18-alkyl, C2-C18-alkenyl, C2-C18-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl, where
C1-C18-alkyl, C2-C18-alkenyl, and C2-C18-alkynyl are unsubstituted or bear one or more identical or different Z3a substituents,
C3-C12-cycloalkyl is unsubstituted or bears one or more identical or different Z3b substituents, and
C6-C14-aryl is unsubstituted or bears one or more identical or different Z3Ar substituents;
R31, R32, R33, R34, R35, R36, R37 and R38 are each independently hydrogen, cyano, bromine or chlorine,
with the proviso that 1, 2, 3, 4, 5, 6, 7 or 8 of the R31, R32, R33, R34, R35, R36, R37 or R38 substituents are cyano;
where
R39 is hydrogen, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl, where
C1-C10-alkyl, C2-C10-alkenyl, and C2-C10-alkynyl are unsubstituted or bear one or more identical or different R3a substituents,
C3-C12-cycloalkyl is unsubstituted or bears one or more identical or different R3b substituents and
C6-C14-aryl is unsubstituted or bears one or more identical or different R3Ar substituents;
R310 and R311 are each independently hydrogen, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl, where
C1-C10-alkyl, C2-C10-alkenyl, and C2-C10-alkynyl are unsubstituted or bear one or more identical or different R3a substituents,
C3-C12-cycloalkyl is unsubstituted or bears one or more identical or different R3b substituents and
C6-C14-aryl is unsubstituted or bears one or more identical or different R3Ar substituents;
each Z3a is independently halogen, hydroxyl, NR310aR311a, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C3-C12-cycloalkyl, C6-C14-aryl, C(═O)R39a; C(═O)OR39a or C(O)NR310aR311a where
C3-C12-cycloalkyl is unsubstituted or bears one or more identical or different R3b substituents and
C6-C14-aryl is unsubstituted or bears one or more identical or different R3Ar substituents;
each Z3b and each Z3Ar is independently halogen, hydroxyl, NR310aR311a, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C(═O)R39a; C(═O)OR39a or C(O)NR310aR311a;
each R3a is independently halogen, hydroxyl, C1-C10-alkoxy, C3-C12-cycloalkyl or C6-C14-aryl;
each R3b is independently halogen, hydroxyl, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C2-C10-alkenyl, C2-C10-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl;
each R3Ar is independently halogen, hydroxyl, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C2-C10-alkenyl, C2-C10-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl;
R39a is hydrogen, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl; and
R310a, R311a are each independently hydrogen, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C12-cycloalkyl or C6-C14-aryl,
(iii) a cyanated compound of formula (IV)
and a mixture thereof,
wherein
m4 is 0, 1, 2, 3 or 4;
each R41 independently is bromine, chlorine, cyano, —NR4aR4b, C1-C24-alkyl, C1-C24-haloalkyl, C1-C24 alkoxy, C1-C24-haloalkoxy, C3-C24-cycloalkyl heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, or C6-C24-aryl-C1-C10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl, aryloxy in C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, and C6-C24 aryl-C1-C10-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R41a and where C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, and the alkylene moieties of C6-C24-aryl-C1-C10-alkylene are optionally interrupted by one or more groups selected from the group consisting of O, S and NR4c;
at least one of the radicals R42, R43, R44 and R45 is CN, and the remaining radicals, independently from each other, are hydrogen, chlorine or bromine;
X40 is O, S, SO or SO2;
A is a diradical of formulae (A.1), (A.2), (A.3), or (A.4)
wherein
* in each case denotes a point of attachment to the remainder of the molecule;
n4 is 0, 1, 2, 3 or 4;
o4 is 0, 1, 2 or 3;
p4 is 0, 1, 2 or 3;
R46 is hydrogen, C1-C24-alkyl, C1-C24-haloalkyl, C3-C24-cycloalkyl, C6-C24-aryl or C6-C24-aryl-C1-C10-alkylene, where the rings of cycloalkyl, aryl, and aryl-alkylene in C3-C24-cycloalkyl, C6-C24-aryl, and C6-C24-aryl-C1-C10-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R46a, and where C1-C24-alkyl, C1-C24-haloalkyl and the alkylene moieties of C6-C24-aryl-C1-C10-alkylene are optionally interrupted by one or more heteroatoms or heteroatomic groups selected from the group consisting of O, S and NR4c;
each R47 independently is bromine, chlorine, cyano, —NR4aR4b, C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, C1-C24-haloalkoxy, C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, or C6-C24-aryl-C1-C10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene in C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, and C6-C24-aryl-C1-C10-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R47a and where C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, C1-C24-haloalkoxy, and the alkylene moieties of C6-C24-aryl-C1-C10-alkylene are optionally interrupted by one or more groups selected from the group consisting of O, S and NR4c;
each R48 independently is bromine, chlorine, cyano, NR4aR4b, C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, C1-C24-haloalkoxy, C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, or C6-C24-aryl-C1-C10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene in C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, and C6-C24-aryl-C1-C10-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R48a and where C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, C1-C24-haloalkoxy, and the alkylene moieties of C6-C24-aryl-C1-C10-alkylene are optionally interrupted by one or more groups selected from the group consisting of O, S and NR4c;
each R49 independently is selected from bromine, chlorine, cyano, NR4aR4b, C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, C1-C24-haloalkoxy, C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, or C6-C24-aryl-C1-C10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene in C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl, C6-C24-aryl, C6-C24-aryloxy, and C6-C24-aryl-C1-C10-alkylene are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R49a and where C1-C24-alkyl, C1-C24-haloalkyl, C1-C24-alkoxy, C1-C24-haloalkoxy, and the alkylene moieties of C6-C24-aryl-C1-C10-alkylene are optionally interrupted by one or more groups selected from the group consisting of O, S and NR4c;
R41a, R46a, R47a, R48a, R49a are independently C1-C24-alkyl, C1-C24-fluoroalkyl, C1-C24-alkoxy, fluorine, chlorine or bromine;
R4a, R4b, R4c are independently hydrogen, C1-C20-alkyl, C3-C24-cycloalkyl, heterocycloalkyl, heteroaryl or C6-C24-aryl;
(iv) a benzoxanthene compound of formula (V)
and a mixture thereof,
wherein
R51 is phenyl which is unsubstituted or carries 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, R511, OR552, NHR552 and NR552R557;
R52, R53, R54, R55, R56, R57, R58 and R59 are independently hydrogen, halogen, R553, OR553, NHR553 or NR553R554,
wherein
R511 is C2-C18-alkyl, C6-C24-aryl or heteroaryl;
R552 and R557 are independently C1-C18-alkyl, C6-C24-aryl or heteroaryl; and
R553 and R554 are independently C1-C18-alkyl, C6-C24-aryl or heteroaryl;
(v) a fluorescent compound comprising at least one structural unit of formula (VI)
where one or more CH groups of the six-membered ring of the benzimidazole structure shown are optionally replaced by nitrogen and where
n6 is a number from 0 to (10-p6) for each structural unit of the formula (VT); where p6 is the number of CH units replaced by nitrogen in the six-membered ring of the benzimidazole structure,
X6 is a chemical bond, O, S, SO, SO2, or NR61; and
R is an aliphatic radical, cycloaliphatic radical, aryl, or heteroaryl, each of which optionally bears substituents,
is an aromatic or heteroaromatic ring or ring system, each of which is fused to other aromatic rings of the structural unit of the formula (VI), or
is F, Cl, Br, CN, or H when X6 is not a chemical bond;
where two R radicals are optionally joined to give one cyclic radical and
where X6 and R, when n6>one, are the same or different;
each R61 is independently hydrogen, C1-C18-alkyl or cycloalkyl, the carbon chain of which optionally comprises one or more of —O—, —S—, —CO—, —SO— and —SO2— moieties and which are optionally mono- or polysubstituted; or
is aryl or heteroaryl which is optionally mono- or polysubstituted; and a mixture thereof;
(vi) a perylene compound of formulae (VII), (VIII), (IX) or (X)
where
p7 is 2,
R71, R72 are each independently C1-C30-alkyl, C3-C8-cycloalkyl, aryl, heteroaryl, or aryl-C1-C10-alkylene, where the aromatic ring in aryl, heteroaryl, and aryl-C1-C10-alkylene is unsubstituted or mono- or polysubstituted by C1-C10-alkyl;
R73 is aryloxy which is unsubstituted or mono- or polysubstituted by C1-C10-alkyl or C6-C10-aryl, where the R73 radicals are at the positions indicated by *;
p8 is 2,
R81, R82 are each independently C1-C30-alkyl, C3-C8-cycloalkyl, aryl, heteroaryl, or aryl-C1-C10-alkylene, where the aromatic ring in aryl, heteroaryl, and aryl-C1-C10-alkylene is unsubstituted or mono- or polysubstituted by C1-C10-alkyl;
R83 is aryloxy which is unsubstituted or mono- or polysubstituted by C1-C10-alkyl or C6-C10-aryl, where the R83 radicals are at the positions indicated by *;
R92 is C1-C30-alkyl, C3-C8-cycloalkyl, aryl, heteroaryl, or aryl-C1-C10-alkylene, where the aromatic ring in aryl, heteroaryl, and aryl-C1-C10-alkylene is unsubstituted or mono- or polysubstituted by C1-C10-alkyl;
R101, R102 are each independently C1-C30-alkyl, C3-C8-cycloalkyl, aryl, heteroaryl, or aryl-C1-C10-alkylene, where the aromatic ring in aryl, heteroaryl, and aryl-C1-C10-alkylene is unsubstituted or mono- or polysubstituted by C1-C10-alkyl;
(vii) a perylene bisimide compound of formula (XI)
and a mixture thereof,
wherein
R111 and R112, independently are hydrogen, an unsubstituted or a substituted C1-C30-alkyl, an unsubstituted or a substituted polyalkyleneoxy, an unsubstituted or a substituted C1-C30-alkoxy, an unsubstituted or a substituted C1-C30-alkylthio, an unsubstituted or a substituted C3-C20-cycloalkyl, an unsubstituted or a substituted C3-C20-cycloalkyloxy, an unsubstituted or a substituted C6-C24-aryl or an unsubstituted or a substituted C6-C24-aryloxy;
R113, R114, R115, R116, R117, R118, R119, R1110, R1111, R1112, R1113, R1114, R1115, R1116, R1117 and R1118 independently are hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, —NE111E112, —NRAr111CORA11r2, —CONRAr111RAr112, —SO2NRAr111RAr112, —COORAr111, —SO3RAr112, an unsubstituted or a substituted C1-C30-alkyl, an unsubstituted or a substituted polyalkyleneoxy, an unsubstituted or a substituted C1-C30-alkoxy, an unsubstituted or a substituted C1-C30-alkylthio, an unsubstituted or a substituted C3-C20-cycloalkyl, an unsubstituted or a substituted C3-C20-cycloalkoxy, an unsubstituted or a substituted C6-C24-aryl, an unsubstituted or a substituted C6-C24-aryloxy or an unsubstituted or a substituted C6-C24-arylthio,
where R113 and R1144, R114 and R115, R115 and R116, R116 and R117, R117 and R118, R118 and R119, R119 and R1110, R1111 and R1112, R1112 and R1113, R1113 and R1114, R1114 and R1115, R1115 and R1116, R1116 and R1117 and/or R1117 and R1118 together with the carbon atoms of the biphenylyl moiety to which they are bonded, optionally form a further fused aromatic or non-aromatic ring system wherein the fused ring system is unsubstituted or substituted;
where
E111 and E112, independently are hydrogen, an unsubstituted or a substituted C1-C18-alkyl, an unsubstituted or a substituted C2-C18-alkenyl, an unsubstituted or a substituted C2-C18-alkynyl, an unsubstituted or a substituted C3-C20-cycloalkyl, or an unsubstituted or a substituted C6-C10-aryl;
RAr111 and RAr112, each independently are hydrogen, an unsubstituted or a substituted C1-C18-alkyl, an unsubstituted or a substituted C3-C20-cycloalkyl, an unsubstituted or a substituted heterocyclyl, an unsubstituted or a substituted C6-C20-aryl or an unsubstituted or a substituted heteroaryl;
and
a mixture thereof.

### Claim 9 (depends on 8)

The color converter of claim 8, wherein the at least one further organic fluorescent dye is a fluorescent compound comprising at least one structural unit of formula (VI).

### Claim 10 (depends on 6)

A method for converting light, the method comprising:
converting light generated by a blue LED with a center wavelength of emission between 420 nm and 480 nm via the color converter of claim 6 into light of a second, longer wavelength.

### Claim 11 (depends on 6)

A method for converting light, the method comprising:
converting light generated by a cool white LED having a correlated color temperature between 6000 K and 20000 K via the color converter of claim 6 so as to provide white light having a lower correlated color temperature.

### Claim 12 (depends on 6)

A lighting device, comprising:
at least one light emitting diode (LED) selected from the group consisting of a blue LED with a center wavelength of emission from 420 nm to 480 nm and a cool white LED having a correlated color temperature between 6000 K and 20000 K; and
(ii) at least one color converter of claim 6,
wherein the at least one color converter is in a remote arrangement from the at least one LED.

### Claim 13 (depends on 1)

A color converter, comprising:
the perylene bisimide compound of the formula I of claim 1 or a mixture thereof.

### Claim 14 (depends on 1)

A security ink, comprising
the perylene bisimide compound of the formula (I) of claim 1 or a mixture thereof.

### Claim 15 (depends on 1)

A printing ink formulation for security printing, comprising
at least one compound of the formula (I) of claim 1 or a mixture thereof.

### Claim 16 (depends on 15)

A printing ink formulation of claim 15, further comprising
a polymeric binder;
optionally an organic solvent;
optionally at least one colorant; and
optionally at least one further additive.