Fluorescent diketopyrrolopyrroles

• US 20060186376A1
• Filed: 04/24/2006
• Published: 08/24/2006
• Est. Priority Date: 06/29/2001
• Status: Active Grant

• Current Assignee: Hiroshi Yamamoto, Norihisa Dan, Olof Wallquist
• Original Assignee: Hiroshi Yamamoto, Norihisa Dan, Olof Wallquist
• Inventors: Dan, Norihisa, Yamamoto, Hiroshi, Wallquist, Olof
• Granted Patent: US 7,749,404 B2
• Time in Patent Office: Days
• US Class Current: 252/301.160
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C09B 57/004 Diketopyrrolopyrrole dyes
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y10S 428/917 Electroluminescent

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

1. A fluorescent diketopyrrolopyrrole of the formula I

3. The fluorescent diketopyrrolopyrrole according to claim 1, wherein A¹ and A² independently of each other stand for

4. The fluorescent diketopyrrolopyrrole according to claim 3, wherein A¹ and A² independently of each other stand for

5. The fluorescent diketopyrrolopyrrole according to claim 4, of of the formula

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

7. 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.

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

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

11. 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.

12. The fluorescent diketopyrrolopyrrole according to claim 1, wherein A¹ and A² independently of each other stand for

13. The fluorescent diketopyrrolopyrrole according to claim 1:

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

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

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

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

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

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

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

2. (canceled)

10. (canceled)