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Fluorescent diketopyrrolopyrroles

A technology of diketopyrrolopyrrole and radicals, applied in diketopyrrolopyrrole dyes, optics, optical filters, etc.

Inactive Publication Date: 2008-10-08
CIBA SPECIALTY CHEM HLDG INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no teaching about the fluorescence of DPP-compounds and how to get DPP-compounds with red or orange fluorescence

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0203] 24.6 g (0.22 mol) of potassium tert-butoxide, 41 g (0.20 mol) of 9-cyanophenanthrene and 200 ml of t-amyl alcohol were heated to a maximum of 100° C. under a nitrogen atmosphere. Once this temperature was reached, a solution of 23 g (0.10 mol) of di-n-butylsuccinate and 70 ml of t-amyl alcohol was added within 1 hour using a dropping funnel. When the addition was complete, the reaction mixture was maintained at 100°C for 16 hours, cooled to 65°C, neutralized with 20 ml of glacial acetic acid and boiled briefly at reflux temperature. The resulting pigment suspension was filtered at room temperature. The filter cake was suspended in 300 ml of methanol and the pigment was isolated by filtration, finally washed with methanol and water until the washings became colorless, and then dried under vacuum at 100° C. to yield 8.5 g of 1,4-diketone-3 , 6-bis-(9-phenanthrenyl)-pyrrolo-(3,4-c)-pyrrole.

[0204] 2.2g (4.5mmol) 1,4-diketone-3,6-bis-(9-phenanthrenyl)-pyrrolo-(3,4-c)-py...

Embodiment 2

[0206] Example 1 was repeated except that 3,5-di-t-butylbenzyl bromide was used as an alkylating agent, thus obtaining a red solid (yield: 36%).

Embodiment 3

[0208] Example 1 was repeated except that methyl iodide was used as an alkylating agent, thus obtaining an orange solid (yield: 48%).

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Abstract

The present invention relates to fluorescent diketopyrrolopyrroles (''DPPs'') of Formula (I), wherein A<1> and A<2> independently from each other stand for (II) wherein R<1>, R<2> and R<5> to R<11> are as defined in claim 1, a process for their preparation and their use for the preparation of inks, colorants, pigmented plastics for coating, 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 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.

Description

[0001] This application is a divisional application of an invention patent application. The application date of the parent application is June 20, 2002, the application number is 02813102.9 (PCT / EP02 / 06846), and the invention name is "fluorescent diketopyrrolopyrrole" . technical field [0002] The present invention relates to fluorescent diketopyrrolopyrroles ("DPPs") of formula I, a process for their preparation and their use in the preparation of inks, colorants, colored plastics for coatings, non-impact-printing materials, color filters Photosheets, cosmetics, or for the preparation of polymeric ink particles, toners, dyes for laser and electroluminescent device applications. Fluorescent diketopyrrolopyrroles ("DPPs") of formula I have high light fastness as well as high thermal stability, especially in plastics. A light-emitting device comprising a DPP compound having the formula I has high power utilization efficiency, high brightness and high color purity. Background...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09B57/00C09K11/06G03G9/08B41M5/00B41M5/385B41M5/388B41M5/39C08K5/353C08L101/00G02B5/20G02B5/22H10K99/00
CPCC09K2211/1011H01L51/0058C09K11/06H01L51/006Y10S428/917H01L2251/308C09K2211/1014C07D487/04C09B57/004H01L51/0072C09K2211/1044H01L51/0053H10K85/621H10K85/626H10K85/633H10K85/6572H10K2102/103
Inventor H·亚马莫托N·丹O·瓦尔奎斯特
Owner CIBA SPECIALTY CHEM HLDG INC
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