# US 2006/0186376 A1 · Fluorescent diketopyrrolopyrroles

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2006/0186376 A1
- Document ID: US20060186376A1
- Status: Published application
- Kind: A1
- Application number: 11/409,694
- Filed: 2006-04-24
- Published: 2006-08-24
- Earliest claimed: 2001-06-29
- Assignees: Ciba Specialty Chemicals Corporation
- Inventors: Hiroshi Yamamoto; Norihisa Dan; Olof Wallquist
- Web page: https://patentgrep.com/patent/US20060186376A1

## CPC

- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C07D 487/04: Ortho-condensed systems
- C09B 57/004: {Diketopyrrolopyrrole dyes}
- C09K 11/06: containing organic luminescent materials
- H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y10S 428/917: Electroluminescent
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

The present invention relates to fluorescent diketopyrrolopyrroles (“DPPs”) of the formula A1 and A2 independently from each other stand for characterized in that that at least two adjacent substituents R5 to R11 form an aromatic or aliphatic fused ring system, or at least one substituent R5 to R11 is cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, a hydroxyl group, a mercapto group, alkylthio, an aryl thioether group, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, a nitro group, a silyl group, a siloxanyl group, a substituted or unsubstituted vinyl, arylamino or diarylamino group; a process for their preparation and their use for the preparation of inks, colorants, pigmented plastics for coatings, non-impact-printing material, color filters, cosmetics, or for the preparation of polymeric ink particles, toners, dye lasers and electroluminescent devices. The fluorescent diketopyrrolopyrroles (“DPPs”) of the formula I exhibit a high lightfastness, a high heat stability, especially in plastics. A luminescent device comprising a DPP compound of formula I is high in the efficiency of electrical energy utilisation, high in luminance and high in colour purity.

## Claims

### Claim 1

A fluorescent diketopyrrolopyrrole of the formula I
wherein R1 and R2 may be the same or different and are selected from a C1-C25alkyl group, an allyl group, which can be substituted one to three times with C1-C3alkyl, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a ketone or aldehyde group, an ester group, a carbamoyl group, a silyl group, a siloxanyl group, A3 or —CR3R4—(CH2)m-A3 wherein R3 and R4 independently from each other stand for hydrogen or C1-C4alkyl, or phenyl which can be substituted one to three times with C1-C3alkyl, A3 stands for aryl which can be substituted one to three times with C1-C8alkyl and/or C1-C8alkoxy, and m stands for 0, 1, 2, 3 or 4, wherein C1-C25alkyl or —CR3R4—(CH2)m-A3, can be substituted with a functional group capable of increasing the solubility in water,
A1 and A2 independently from each other stand for
wherein R5 to R11 may be the same or different and are selected from hydrogen, C1-C25alkyl group, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, a mercapto group, alkoxy, alkylthio, an aryl ether group, an aryl thioether group, aryl, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, an alkylamino group, a di(alkyl)amino group, a nitro group, a silyl group, a siloxanyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted arylamino group and a substituted or unsubstituted diarylamino group, or at least two adjacent substituents R5 to R11 form an aromatic or aliphatic fused ring system,
wherein at least one substituent R5 to R11 is a group —NR27R28, wherein R27 and R28 are independently of each other
wherein R29, R30 and R31 are independently of each other hydrogen, C1-C8alkyl, C1-C8alkoxy or a group —NR32R33, wherein R32 and R33 are independently of each other
wherein R34 is hydrogen, C1-C8alkyl or C1-C8alkoxy.

### Claim 2

(canceled)

### Claim 3 (depends on 1)

The fluorescent diketopyrrolopyrrole according to claim 1, wherein A1 and A2 independently of each other stand for
wherein at least one of A1 or A2 is
R21, R22, R23, R25 and R26 are independently of each other hydrogen, C1-C8alkyl, a hydroxyl group, a mercapto group, C1-C8alkoxy, C1-C8alkylthio, halogen, halo-C1-C8alkyl, a cyano group, an aldehyde group, a ketone group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group,
R24 is a C1-C6alkyl group and
R27 and R28 are independently of each other
wherein R29, R30 and R31 are independently of each other hydrogen, C1-C8alkyl, C1-C8alkoxy or a group —NR32R33, wherein R32 and R33 are independently of each other
wherein R34 is hydrogen, C1-C8alkyl or C1-C8alkoxy.

### Claim 4 (depends on 3)

The fluorescent diketopyrrolopyrrole according to claim 3, wherein A1 and A2 independently of each other stand for
wherein at least one of A1 or A2 is
and R21 is hydrogen, C1-C8alkyl or C1-C8alkoxy.

### Claim 5 (depends on 4)

The fluorescent diketopyrrolopyrrole according to claim 4, of of the formula
wherein R1 is allyl, C1-C8alkyl, tri(C1-C8alkyl)silyl, —CH2-A3′, —CHCH3-A3 or —CH2—CH2-A3, wherein A3 stands for phenyl, which can be substituted one or two times with C1-C8alkyl, and
R21 is hydrogen, C1-C4alkyl or C1-C4alkoxy.

### Claim 6 (depends on 1)

An electroluminescent device, comprising a fluorescent compound of formula I according to claim 1.

### Claim 7 (depends on 1)

A composition comprising
(a) 0.01 to 50% by weight, based on the total weight of a colored high molecular weight organic material, of the fluorescent compound of formula I according to claim 1, and
(b) 99.99 to 50% by weight, based on the total weight of the colored high molecular weight organic material, of a high molecular organic material, and
(c) optionally, customary additives in effective amounts.

### Claim 8 (depends on 7)

The composition according to claim 7, wherein the high molecular weight organic material is a polyamide, a polystyrene, polymethylmethacrylate or an ABS copolymer.

### Claim 9 (depends on 1)

A method of coloring a high molecular weight organic material by incorporating therein a fluorescent compound of formula I according to claim 1.

### Claim 10

(canceled)

### Claim 11 (depends on 5)

The fluorescent diketopyrrolopyrrole according to claim 5, wherein R1 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, n-hexyl, n-heptyl, n-octyl, 1,1,3,3-tetramethylbutyl and 2-ethylhexyl.

### Claim 12 (depends on 1)

The fluorescent diketopyrrolopyrrole according to claim 1, wherein A1 and A2 independently of each other stand for
wherein R27 and R28 are independently of each other phenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, which may be unsubstituted or substituted by C1-C8alkyl, C1-C8alkoxy or a group —NR12aNR13a, wherein R12a and R13a are independently of each other phenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, which may be unsubstituted or substituted by C1-C8alkyl, or C1-C8alkoxy, or
R12a and R13a form together with the nitrogen atom to which they are bonded a five or six membered heterocyclic ring, or said ring which also contains a group X, wherein
X is O, S or NR40, wherein R40 is hydrogen or C1-C8alkyl.

### Claim 13 (depends on 1)

The fluorescent diketopyrrolopyrrole according to claim 1:

### Claim 14 (depends on 1)

An ink, comprising a fluorescent compound of formula I according to claim 1.

### Claim 15 (depends on 1)

A colorant, comprising a fluorescent compound of formula I according to claim 1.

### Claim 16 (depends on 1)

A pigmented plastics for coatings, comprising a fluorescent compound of formula I according to claim 1.

### Claim 17 (depends on 1)

A non-impact-printing material, comprising a fluorescent compound of formula I according to claim 1.

### Claim 18 (depends on 1)

A color filter, comprising a fluorescent compound of formula I according to claim 1.

### Claim 19 (depends on 1)

Cosmetics, comprising a fluorescent compound of formula I according to claim 1.

### Claim 20 (depends on 1)

A dye laser, comprising a fluorescent compound of formula I according to claim 1.