Optical information-recording medium, novel oxonol compound and method of recording information

a technology of optical information and recording medium, applied in the direction of recording strategies, instruments, thermography, etc., can solve the problems of difficult to obtain dyes with complex refractive indexes in real part n, short of practically sufficient performance in respect of modulation factor and reflectivity, etc., to achieve satisfactory recording characteristics, excellent recording characteristics, and excellent recording characteristics

Inactive Publication Date: 2006-12-21
FUJIFILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0009] The present Inventors used various cyanine dye compounds and oxonol dye compounds as disclosed in the documents cited above in optical information-recording media of DVD-R type and studied performance capabilities of the resulting recording media. As a result, it has been found that while the DVD-R type of optical information-recording media containing those dye compounds in their respective recording layers showed very excellent recording characteristics in the low-speed recording at equivalent or double speed, they fell short of delivering practically sufficient performances in respects of modulation factor and reflectivity although they can show comparatively excellent recording characteristics at the time of high-speed recording at quadruple or higher speed. The use of a dye having an optical characteristic that the complex refractive index (n+ik) of the dye is greater in the real part n than those of dyes for low-speed recording use and its imaginary part k is almost the same as or smaller than those of dyes for low-speed recording use can serve the purpose of obtaining an optical information-recording medium which can maintain satisfactory recording characteristics in the recording at a low speed such as an equivalent or double speed and, at the same time, can satisfy recording performances, including sufficient reflectivity and modulation factor in particular, even in the recording at a high speed such as a quadruple or higher speed. However, it was very difficult to obtain dyes showing complex refractive indexes great in real part n and almost equal or small in imaginary part k, compared with those of dyes for low-speed recording use, while maintaining satisfactory low-speed recording characteristics. Therefore, an object of the invention is to provide a dye having a complex refractive index great in real part n and almost equal or small in imaginary part k, compared with those of dyes for low-speed recording use, and thereby ensuring a high reflectivity and a high modulation factor even in high-speed recording at quadruple or higher speed as it maintains satisfactory recording characteristics in low-speed recording at equivalent to double speed. Another object of the invention is to provide a dye attaining sufficiently low jitter at a wide range of recording speeds covering from equivalent- to octuple-speed recording.

Problems solved by technology

As a result, it has been found that while the DVD-R type of optical information-recording media containing those dye compounds in their respective recording layers showed very excellent recording characteristics in the low-speed recording at equivalent or double speed, they fell short of delivering practically sufficient performances in respects of modulation factor and reflectivity although they can show comparatively excellent recording characteristics at the time of high-speed recording at quadruple or higher speed.
However, it was very difficult to obtain dyes showing complex refractive indexes great in real part n and almost equal or small in imaginary part k, compared with those of dyes for low-speed recording use, while maintaining satisfactory low-speed recording characteristics.

Method used

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  • Optical information-recording medium, novel oxonol compound and method of recording information
  • Optical information-recording medium, novel oxonol compound and method of recording information
  • Optical information-recording medium, novel oxonol compound and method of recording information

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Compound (3):

[0085] The present compound was synthesized in accordance with the reaction scheme illustrated hereinbefore.

[Synthesis of Linkage Part (Compound (1-I))]

[0086] 1,4-Cyclohexanedione (22.43 g, 0.2 mol) and malonic acid (41.62 g, 0.4 mol) were dissolved in acetic anhydride (85 ml), and thereto concentrated sulfuric acid (7.0 ml, 0.12 mol) was added. The resulting admixture was stirred in an ice bath. As the reaction progressed, light brown crystals separated out. These crystals were filtered off, washed with ice-cold distilled water, and dried. Thus, 8.8 g of the intended Compound (1-I) was obtained as light brown crystals (in a 15.5% yield.

[Synthesis of Dye Part (Compound (3-II))]

[0087] Malonic acid (5.2 g, 0.05 mol) and concentrated sulfuric acid (0.5 ml) were added to acetic anhydride (10 ml), and therein the source compound was dissolved thoroughly while stirring at room temperature. Thereto, 4-ethylcyclohexanone (6.31 g, 0.05 mol) was slowly added dr...

example 2

Syntheses of Compounds (1), (13) and (14):

[0091] Synthesis was carried out under the same reaction scheme as the synthesis of Compound (3) in Example 1, except for the scheme (3) wherein cyclohexanone was used in place of 4-ethylcyclohexanone; as a result, the purification by column chromatography on silica gel in the scheme (3) effected resolution into the compound corresponding to the dye anion of Compound (1) and the compound corresponding to the dye anion common to Compounds (13) and (14). And in the scheme (4), the thus resolved compounds corresponding to the dye anions were converted into their respective salts, thereby giving the desired Compound (1), Compound (13) and Compound (14).

[0092]1H-NMR (DMSO-d6) of Compound (1): 1.40(s, 4H), 1.54(s, 8H), 1.83 (s, 8H), 1.98(s, 8H), 7.09-7.79(m, 24H), 7.92(s, 2H), 9.00(s, 4H), 9.69(s, 4H)

[0093]1H-NMR (DMSO-d6) of Compounds (13): 1.41(s, 4H), 1.53(s, 8H), 1.82(s, 8H), 1.98 (s, 24H), 7.13(t, 8H), 7.27(d, 4H), 7.38-7.79(m, 40H), 7.91...

example 3

Synthesis of Compound (2):

[0094] Compound (2) was synthesized under the same reaction scheme as Compound (3) in Example 1, except that 4-methylcyclohexanone was used in place of 4-ethylcyclohexanone.

[0095]1H-NMR (DMSO-d6): 0.91(d, 6H), 1.20(q, 4H), 1.47(s, 2H), 1.65(m, 8H), 2.01(m, 12H), 7.10(q, 4H), 7.28(d, 2H), 7.39-7.86(m, 18H), 7.89(s, 2H), 9.01(d, 4H), 9.67(d, 4H), 10.71(s, 2H)

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Abstract

An optical information-recording medium which contains a dye having at least two chromophores bonded to each other without any conjugated bond intervening between those chromophores.

Description

BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] The present invention relates to a heat-mode information recording medium and an information recording method which enable write (record) and read (playback) of information by use of high energy density laser light. More specifically, the invention relates to a heat-mode information recording medium, such as a recordable digital versatile disc (DVD-R), which is suitable for recording information by use of visible laser light. [0003] 2. Description of the Related Art [0004] Information recording media on which information is recordable only once by use of laser light (optical discs) have been long known. The information recording media of such a type are referred to as recordable CDs (the so-called CD-R) as well. These disc shave an advantage in that they can be rapidly delivered in low quantities at reasonable prices, compared with traditional CDs, and the demand for them has been growing as personal computers have ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): B32B3/02C07D493/10C07D519/00B41M5/26C09B23/00C09B23/08G11B7/244G11B7/247
CPCC09B23/00Y10S430/146C09B23/083C09B69/04G11B7/00456G11B7/24038G11B7/244G11B7/245G11B7/246G11B7/2467G11B7/247G11B7/2472G11B7/2475G11B7/2478G11B7/248G11B7/249G11B7/2534G11B7/2542G11B7/2578G11B7/259G11B2007/24612C09B23/0075
Inventor AKIBA, MASAHARUMORISHIMA, SHIN-ICHIINAGAKI, YOSHIOMIKOSHIBA, HISASHISHIBATA, MICHIHIRO
Owner FUJIFILM CORP
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