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Metallocenyl Phthalocyanine Compounds and Use Thereof

a technology of phthalocyanine and phthalocyanine, which is applied in the field of metalocenyl phthalocyanine compounds and derivatives, can solve the problems of increasing writing power, limiting the maximum achievable writing speed at a given laser point, and jitter value, and achieves excellent recording sensitivity, small jitter, and simple process

Inactive Publication Date: 2010-07-15
ORGCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013] Under the above circumstances, the present inventors have conducted investigation of the structure of phthalocyanine compounds and their synthesis and found that novel metallocenyl phthalocyanine compounds / mixtures obtained on connecting phthalocyanine with metallocene through a linker containing one carbon atom through a Friedel-Crafts reaction exhibit excellent recording sensitivity and small jitter, and are thus suitable for use in high-speed rewritable recording media. Moreover, these novel metallocenyl phthalocyanine compounds / mixtures can be prepared with a simple process so that their production cost can be moderate. Especially, because the linker connecting phthalocyanine with metallocene contains only one carbon atom, the solubility in non-polar solvents is satisfactory, so resolving the problems of aggregation and precipitation.

Problems solved by technology

When a CD-R operates at a large writing speed, the jitter value at short pits or lands can be decreased with a relatively thin recording layer, but this thin layer requires an increased writing power at a given writing speed, which once again limits the maximum achievable writing speed at a given laser point.
Recording materials are, however, unable to meet fully the increased requirements at great writing speeds.
A thin layer requires, undesirably, an increased writing power at a given writing speed, which once again limits the maximum achievable writing speed at a given laser point.
The disadvantages of phthalocyanine are (1) lack of light sensitivity, (2) poor solubility, (3) a high temperature required for recording, and (4) a small reflectivity.
Although the phthalocyanines disclosed in this patent can decrease the decomposition temperature, and possess excellent writing decomposability, increased solubility in the solvent and increased reflectivity, these phthalocyanines also result in an increased Block Error Rate (BLER) when a greater writing speed is required; thus its writing property is also diminished.
EP-A 600427 disclosed a dye for a recording layer in an optical recording medium that is based on phthalocyanines with a few additives, for example, a combustion aid such as ferrocenyl derivatives, or an antiknocking agent to improve the heat decomposability and recording property, but it is still unsatisfactory for recycling because of the solubility difference between the phthalocyanines and the additives.
WO 97 / 23354 disclosed a method to solve the problem of the disparate solubility by binding the metallocenyl and the phthalocyanines, but its recording property is still unsatisfactory.
Currently, only altering the specificity of the phthalocyanine structures themselves can not achieve a great sensitivity ratio (C / N, carrier to noise), optimal recording power and recording properties (such as small jitter) required in recording media.
Also, from relevant papers and patent publications, it is pointed out that the compound obtained on bonding phthalocyanines and metallocene can greatly improve its sensitivity and recording properties when it is used as a dye in a recording layer for recording media, but the preparation of metallocenyl phthalocyanines requires multiple steps so that its cost of production becomes increased.

Method used

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  • Metallocenyl Phthalocyanine Compounds and Use Thereof
  • Metallocenyl Phthalocyanine Compounds and Use Thereof
  • Metallocenyl Phthalocyanine Compounds and Use Thereof

Examples

Experimental program
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Effect test

example 1

[0106] Tetra-(α-2,4-dimethyl-3-pentyloxy) copper phthalocyanine (CuPc, 30.0 g) was dissolved in 1,2-dichloroethane (300 mL) and stirred for 0.5 h in a dry flask. Chloromethylferrocene (FcCH2Cl, 12.2 g) (FcCH2Cl was prepared by the known method described in J. Am. Chem. Sodc 1966, 88, 3442-3444) was added, and subsequently aluminium chloride (1.56 g) was crushed and added promptly. The mixture was stirred for 10 min, warmed up to 80 AC for another 4 h and then cooled to room temperature.

[0107] The mixture aforementioned was poured into a solution mixed with ice (180 g) and water (180 mL) in a beaker (1 L), and stirred; the temperature was controlled about 10° C. for 1 h. The solution was poured into a separatory funnel and extracted with water (300 mL) twice. The organic layers were collected, concentrated to approximately 70 g, and poured into a methanol (900 mL) solution with stirring by a mechanical agitator at a temperature about 10° C. The precipitate was formed and filtered. T...

example 2

[0108] Tetra-(α-2,4-dimethyl-3-pentyloxy) copper phthalocyanine (CuPc, 30.0 g) was dissolved in 1,2-dichloroethane (300 mL) and stirred for 0.5 h in a d flask. Chloromethylferrocene (FcCH2Cl, 12.2 g) was added, and then sulfuric acid (98%, 0.86 g) was slowly added. The mixture was stirred for 10 min, warmed to 90° C. for another 3 h, and then cooled to room temperature.

[0109] The solution aforementioned was poured into a beaker equipped with a magnetic stirrer, and charged with a mixture of ice (60 g) and water (300 mL). The mixture was stirred and the temperature was controlled at 10˜15° C. for 0.5 h. The solution was poured into a separatory funnel, and extracted with water (300 mL) twice. The organic layers were collected, concentrated to approximately 70 g, and poured into a methanol (900 mL) solution with stirring by a mechanical agitator at a temperature about 10° C. A precipitate was formed and filtered. The filtered cake was washed with methanol (30 mL) three times to give ...

example 3

[0110] Tetra-(α-2,4-dimethyl-3-pentyloxy) copper phthalocyanine (CuPc, 30.0 g) was dissolved in 1,2-dichloroethane (300 mL) in a dry flask and stirred for 0.5 h. Chloromethylferrocene (FcCH2Cl, 12.2 g) was added, and subsequently aluminium chloride (2.33 g) was crushed and added promptly. The mixture was stirred for 10 min, warmed to 80° C. for another 6 h and then cooled to room temperature.

[0111] The solution aforementioned was poured into a beaker equipped with a magnetic stirrer, and charged with a mixture of ice (180 g) and water (180 mL). The mixture was stirred, and the temperature was controlled at 10° C. for 1 h The solution was poured into a separatory funnel, and extracted with water (300 mL) twice. The organic layers were collected, concentrated to approximately 100 g, and poured into a methanol (900 mL) solution with stirring by a mechanical agitator with the temperature controlled at 10° C. A precipitate was formed and filtered. The filtered cake was washed with metha...

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Abstract

This invention relates to a novel metallocenyl phthalocyanine compound represented by the following general formula (I), in which at least one of the four benzene rings of phthalocyanine is connected with the organometallic complex group through a linker having one carbon atom. This invention also relates to the use of the phthalocyanine compounds in optical recording media. wherein all symbols are defined in the specification.

Description

TECHNICAL FIELD [0001] This invention relates to novel metallocenyl phthalocyanine compounds and derivatives thereof, and their use for the recording layers of optical recording media. BACKGROUND OF THE INVENTION [0002] With the rapid growth of our digital world, the technology for optical storage is being highly developed. The advantages of an optical medium disk are that data are easily recorded on such a medium, it is suitable for enduring storage, and it has a modest cost. This recording data medium is now becoming an accepted way to store information because of its large storage capacity. [0003] The field of this invention is directed to dyes used in the recording layer on a writable optical disk, because such dyes exhibit varied optical properties upon irradiation. There are optical disks of several kinds as follows: (I) Write Once, Read Many (WORM); (2) Read Only Memory (ROM); (3) Erasable Direct Read after Write (EDRW). In a disk of WORM type, the recording material uses mai...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G03F7/004C07F1/08C07F15/00
CPCC09B47/12G11B7/248C09B47/18
Inventor SHA, CHINYANG, CHENGCHENG, PINGCHANG, CHINGYEN, KUANGHONG, AN
Owner ORGCHEM TECH
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