CN100465148C - High density compact disc and its recording compound - Google Patents
High density compact disc and its recording compound Download PDFInfo
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- CN100465148C CN100465148C CNB031035132A CN03103513A CN100465148C CN 100465148 C CN100465148 C CN 100465148C CN B031035132 A CNB031035132 A CN B031035132A CN 03103513 A CN03103513 A CN 03103513A CN 100465148 C CN100465148 C CN 100465148C
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- group
- aromatic series
- compound
- high density
- series base
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Abstract
The present invention provides compounds as record medium for high density CD. The present invention also provides the high density CD produced with the compounds and its production process.
Description
Technical field
The present invention relates to a kind of high density compact disc and recording compound thereof, refer to a kind of recording layer dye that is applicable to high-density optical store medium body and function especially.
Background technology
The lifting that development of science and technology is synchronous everybody to the requirement of audio-visual quality, high definition digital TV (High Definition Television Video) develops gradually with digital camera in recent years.With regard to HD-TV, store the storage volume that the about two hours film of HDTV need about 22GB, be that storage volume with the recordable Video CD of 4.7GB (DVD-R) has not met demand, thereby in recent years in the research of Storage Media, also stimulated the development of high density compact disc (HD-DVD) relatively.
Because high density compact disc must use the read-write optical maser wavelength of 405nm, so that the focusing of laser is more meticulous, and reaches highdensity record ability.And the former optical maser wavelength that is used in CD-R (CD-R) and DVD-R is respectively 780nm and 650nm, so recording layer organic materials of its use, be not suitable for high density compact disc as Cyanine, azo, phthalocyanin, must the suitable high density compact disc record layer dyestuff of exploitation.
Summary of the invention
Main purpose of the present invention is to provide a kind of high density compact disc and recording compound thereof, can be applicable to that main absorbing wavelength is 400 to 450nm blue laser read/write head, to use as the high density storage media.
Another object of the present invention is to provide a kind of high density compact disc, can be applicable to that main absorbing wavelength is 400 to 450nm blue laser read/write head, and use as the high density storage media.
Another purpose of the present invention is to provide a kind of making method of high density compact disc, can make to be applicable to that main absorbing wavelength is 400 to 450nm blue laser read/write head, to use as the high density storage media.
For achieving the above object, the present invention is for having the high density compact disc record compound as shown in the formula (1):
A wherein
1With A
2Be C
5To C
20Aromatic series base (aryl) or heterocyclic radical (heteroaryl), optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical; R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base; N is 1 to 4 integer; N ' is 0 to 4 integer.
The present invention provides a high density compact disc record compound that has as shown in the formula (2) simultaneously in addition:
A wherein
3With A
4Be C
5To C
20Aromatic series base (aryl) or heterocyclic radical (heteroaryl), optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical; B be Ar or
R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base.N is 1 to 4 integer; N ' is 0 to 4 integer.
High density compact disc of the present invention mainly comprises: one contains the substrate of at least one groove; One recording layer is positioned at a side of this substrate, and this recording layer contains the compound as shown in the formula (1) or formula (2):
A wherein
1, A
2, A
3, A
4Be C
5To C
20Aromatic series base (aryl) or heterocyclic radical (heteroaryl), optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical; R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base; B be Ar or
N is 1 to 4, and n ' is 0 to 4; And a protective layer, be positioned at a side of this recording layer; Wherein this recording layer is between this substrate and this protective layer.
The making method of high density compact disc of the present invention mainly may further comprise the steps: a substrate that contains at least one groove is provided earlier; One compound that has as shown in the formula (1) or formula (2) is provided thereupon:
A wherein
1, A
2, A
3, A
4Be C
5To C
20Aromatic series base (aryl) or heterocyclic radical (heteroaryl), optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical; R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base; B be Ar or
N is 1 to 4, and n ' is 0 to 4; Then this compound is dissolved in organic solvent or the macromolecular solution; Again with the also oven dry on this substrate of this solution coat, to form a recording layer; And at last on this recording layer the coating one protective layer.
The high density compact disc record of the present invention A of compound
1, A
2, A
3With A
4For having one or more substituent C
5To C
20Aromatic series base (aryl) or heterocyclic radical (heteroaryl), for example phenyl, benzoyl, fluorenyl, naphthyl, indyl, thienyl, benzene indyl or phenolic group, and one or more substituting groups are arranged on it can be C
1-C
10Alkyl, C1-C10 alkoxyl group, nitro, halogen, diethoxymethyl, dialkyl amino, cycloalkyl or cyano group; Be preferably phenyl, methoxyphenyl, aminomethyl phenyl, isopropyl phenyl, isobutyl phenenyl, fluorenyl, diethoxymethyl phenyl, ethyl aminocarbonyl phenyl, N-2-aminomethyl phenyl, t-butyl phenyl, cyclohexyl phenyl, cyano-phenyl, naphthyl or thienyl.High density compact disc of the present invention record is 1 to 4 integer with the n of compound; Be preferably 1 to 2.High density compact disc of the present invention record is 0 to 4 integer with the n ' of compound; Be preferably 0 to 2.The employed organic solvent of the making method of high density compact disc of the present invention is unrestricted, can be alcohols, ketone, ethers, alkene class, alkanes or ester class, is preferably alcohols or ketone.The making method of high density compact disc of the present invention mainly may further comprise the steps:
(A) provide a substrate that contains at least one groove.
(B) provide a compound that has as shown in the formula (1) or (2):
Formula (2)
A wherein
1, A
2, A
3, A
4Be C
5To C
20Aromatic series base (aryl) or heterocyclic radical (heteroaryl), optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical; R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base; B be Ar or
N is 1 to 4, and n ' is 0 to 4.
(C) this compound is dissolved in organic solvent or the macromolecular solution, forms a solution;
(D) with the also oven dry on this substrate of this solution coat, to form a recording layer; And
(E) this recording layer is coated with a protective layer.
Before or after step (D), preferably also comprise a step (D ') and on this substrate, form a reflecting layer.
Wherein be formed with a reflecting layer between recording layer and this protective layer.
The method that wherein forms this reflecting layer is a sputter.
The high density compact disc record of the present invention A of compound formula (2)
3, A
4For optionally having one or more substituent C
5To C
20Aromatic series base (aryl) or heterocyclic radical (heteroaryl), being preferably has the substituent benzoyl of alkane on phenyl or the phenyl ring.
Description of drawings
Fig. 1 is the NMR figure of The compounds of this invention 1.
Fig. 2 is the UV figure of The compounds of this invention 1.
Fig. 3 is the NMR figure of The compounds of this invention 10.
Fig. 4 is the UV figure of The compounds of this invention 10.
Fig. 5 is the NMR figure of The compounds of this invention 14.
Fig. 6 is the UV figure of The compounds of this invention 14.
Fig. 7 is high-density blue light compact disk structure figure of the present invention.
Fig. 8 is high-density blue light cd-recordable of the present invention (DVR) structure iron.
Embodiment
For more understanding technology contents of the present invention, as follows especially exemplified by following preferred embodiment and accompanying drawings.
Embodiment 1:1-(4-methoxyl group-phenyl)-5-phenyl-five-2,4-diene-1-ketone (compound 1) synthetic
Under room temperature, get 2 milliliters of trans-cinnamic aldehyde and 2.5 gram 4-methoxyacetophenones are dissolved in 50 milliliters of ethanol, the aqueous sodium hydroxide solution that adds 10 milliliters then, stirring makes its reaction 12 hours, can generate the yellow solid precipitation, and filtration can get the compound 1 of productive rate 72%, purity 96.3%.Fig. 1 and Fig. 2 are respectively its NMR and UV figure, can learn that compound 1 maximum absorption wavelength is 345nm, and specific absorbance e is 4.5 * 10
4Also one be listed in table 1.
Embodiment 2:1-(2-benzothienyl)-4-amyl group-5-phenyl-five-2,4-diene-1-ketone (compound 10) synthetic
Getting 2.5 gram amyl group cinnamic aldehyde and 2 under room temperature restrains 2-phenyl methyl ketone thiophthenes and is dissolved in 50 milliliters of ethanol, the aqueous sodium hydroxide solution that adds 10 milliliters then, stirring reaction 12 hours can generate the yellow solid precipitation, and filtration can get the compound 10 of productive rate 63%, purity 93%.Fig. 3 and Fig. 4 are respectively the NMR and the UV figure of compound 10, and compound 10 maximum absorption wavelengths are 358.5nm as can be known, and specific absorbance e is 4.2 * 10
4Also one be listed in table 1.
Synthesizing of embodiment 3:3-(4-methoxyl group-phenyl)-1-naphthalene-2-base-acrylketone (compound 14)
Getting 2 gram 4-methoxybenzaldehydes and 2 under room temperature restrains the 2-acetonaphthones and is dissolved in 50 milliliters of ethanol, the aqueous sodium hydroxide solution that adds 10 milliliters then, stirring reaction 12 hours can generate the yellow solid precipitation, and filtration can get the compound 14 of productive rate 70%, purity 85%.Fig. 5 and Fig. 6 are respectively the NMR and the UV figure of compound 14, and compound 14 maximum absorption wavelengths are 347.5nm as can be known, and one is listed in table 1.
Embodiment 4
In the mode identical with embodiment 1 to 3, get synthetic other compound listed of different reactants respectively, and measure its NMR and UV collection of illustrative plates as table 1, can learn the maximum absorption wavelength of each compound.
NMR collection of illustrative plates by gained can be confirmed the synthetic compound structure, and can find out that by its UV collection of illustrative plates the absorption region of compound of the present invention all includes the employed read-write optical maser wavelength of HD-DVD 405nm, can be used as the record compound of high density compact disc really.
Embodiment 5: the high-density blue light cd-recordable method for making of conventional optical disc structure
Compound 2.0 grams of at first getting table 1 are dissolved in organic solvent, as: 2,2,3,3-C3-Fluoroalcohol (2,2,3,3-tetrafluoropropanol), in dimethyl cyclohexane (dimethyl cyclohexane), valerone or the macromolecular solution (Dye-In-Polymer), and be mixed with the solution of 100g.With above-mentioned soln using coating method, coat on the substrate 1, as shown in Figure 7, the thickness of substrate 1 is that 0.6mm, gauge (track pitch) they are 0.3～0.4 μ m, and has ditch rail (land) and groove (groove) 11.Drying processing procedure afterwards, can get thickness is the recording layer 2 of 50nm～200nm, amount that can coating solution is adjusted its thickness.Then with the reflector material sputter on dye coating 2 to form reflecting layer 3, the blank transparency carrier 5 that with another sheet thickness is 0.6mm then is fitted on the reflecting layer 3, laminating type can be method of spin coating, wire mark method, hot melt adhesive method or the like, and after forming a laminating layer 4 between reflecting layer 3 and the blank transparency carrier 5, promptly becoming a slice thickness is the high-density blue light cd-recordable (HD-DVD-R) of 120mm.
The high-density blue light cd-recordable method for making of embodiment 6:DVR compact disk structure
See also Fig. 8, at first with the reflector material sputter on substrate 10 to form reflecting layer 20.Substrate 10 has ditch rail (land) and groove (groove) 101, and its thickness is that 1.1mm, gauge (trackpitch) are 0.3～0.4 μ m.Compound 2.0 grams of then getting table 1 are dissolved in organic solvent, as: 2,2,3,3-C3- Fluoroalcohol 2,2,3, in 3-tetrafluoro-propanol, dimethyl cyclohexane (dimethylcyclohexane), valerone or the macromolecular solution (Dye-In-Polymer), and be mixed with the solution of 100g, and with this soln using coating method, coat on the substrate 10 in above-mentioned sputter reflecting layer 20, form recording layer 30.The transparent dielectric material layer 40 of the about 5nm～50nm of sputter one layer thickness on recording layer 30 more afterwards; the protective membrane (Cover Layer) 50 of the about 0.1mm of coating one layer thickness on dielectric materials layer 40 is promptly finished a blue-light high-density cd-recordable (DVR) then.
High-density blue light cd-recordable of the present invention is under the 405nm at wavelength, and the disc reflectivity can reach more than 45%, has highdensity record ability really compared to traditional CD, and the capacity of recording medium also greatly promotes.
The foregoing description is only given an example for convenience of description, and the interest field that the present invention advocated should be as the criterion so that claim is described certainly, but not only limits to the foregoing description.
The maximum absorption wavelength of table 1, compound
The maximum absorption wavelength of table 1 (continuing) compound
The maximum absorption wavelength of table 1 (continuing) compound
Claims (15)
1, a kind of high density compact disc record compound that has as shown in the formula (1):
A wherein
1With A
2Be C
5To C
20Aromatic series base or heterocyclic radical, optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical, it is selected from by having the group that one or more substituent phenyl, fluorenyl, naphthyl, indyl, benzene indyl, thienyl and phenolic group are formed, and this substituting group is selected from by C
1-C
10Alkyl, C
1-C
10The group that alkoxyl group, nitro, halogen, diethoxymethyl, dialkyl amino, cycloalkyl and cyano group are formed; R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base; N is 1 to 4 integer; N ' is 0,2 or 4 integer.
2, compound used in high density compact disc record as claimed in claim 1, and wherein n is 1 to 2 integer.
3, compound used in high density compact disc record as claimed in claim 1, and wherein n ' is 0 or 2 integer.
4, a kind of making method of high density compact disc mainly may further comprise the steps:
(A) provide a substrate that contains at least one groove;
(B) provide a compound that has as shown in the formula (1):
Formula (1)
A wherein
1, A
2Be C
5To C
20Aromatic series base or heterocyclic radical, optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical, it is selected from by having the group that one or more substituent phenyl, fluorenyl, naphthyl, indyl, benzene indyl, thienyl and phenolic group are formed, and this substituting group is selected from by C
1-C
10Alkyl, C
1-C
10The group that alkoxyl group, nitro, halogen, diethoxymethyl, dialkyl amino, cycloalkyl and cyano group are formed; R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base; N is 1 to 4, and n ' is 0,2 or 4;
(C) this compound is dissolved in organic solvent or the macromolecular solution, forms a solution;
(D) with the also oven dry on this substrate of this solution coat, to form a recording layer; And
(E) coating one protective layer on this recording layer.
5, making method as claimed in claim 4 is characterized in that, wherein n is 1 to 2.
6, making method as claimed in claim 4 is characterized in that, wherein n ' is 0 or 2.
7, making method as claimed in claim 4 is characterized in that, wherein this organic solvent is alcohols or ketone.
8, making method as claimed in claim 4 is characterized in that, wherein also comprised a step (D ') and form a reflecting layer before or after step (D) on this substrate.
9, making method as claimed in claim 8 is characterized in that, wherein step (D ') forms this reflecting layer for the mode with sputter.
10, a kind of high density compact disc mainly comprises:
One contains the substrate of at least one groove;
One recording layer is positioned at a side of this substrate, and this recording layer contains the compound as shown in the formula (1):
A wherein
1, A
2Be C
5To C
20Aromatic series base or heterocyclic radical, optionally have one or more substituting groups on the ring of this aromatic series base or heterocyclic radical, it is selected from by having the group that one or more substituent phenyl, fluorenyl, naphthyl, indyl, benzene indyl, thienyl and phenolic group are formed, and this substituting group is selected from by C
1-C
10Alkyl, C
1-C
10The group that alkoxyl group, nitro, halogen, diethoxymethyl, dialkyl amino, cycloalkyl and cyano group are formed; R
1With R
2Be hydrogen atom, halogen or C
1To C
10Alkyl or aromatic series base; N is 1 to 4, and n ' is 0,2 or 4; And
One protective layer is positioned at a side of this recording layer;
Wherein this recording layer is between this substrate and this protective layer.
11, CD as claimed in claim 10 is characterized in that, wherein n is 1 to 2.
12, CD as claimed in claim 10 is characterized in that, wherein n ' is 0 or 2.
13, CD as claimed in claim 10 is characterized in that, wherein is formed with a reflecting layer between this substrate and this recording layer.
14, CD as claimed in claim 10 is characterized in that, wherein is formed with a reflecting layer between this recording layer and this protective layer.
15, CD as claimed in claim 14 is characterized in that, the method that wherein forms this reflecting layer is a sputter.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031035132A CN100465148C (en) | 2003-01-28 | 2003-01-28 | High density compact disc and its recording compound |
| CNB2004100979808A CN100522913C (en) | 2003-01-28 | 2003-01-28 | High density optical disk and its compound for recording |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031035132A CN100465148C (en) | 2003-01-28 | 2003-01-28 | High density compact disc and its recording compound |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100979808A Division CN100522913C (en) | 2003-01-28 | 2003-01-28 | High density optical disk and its compound for recording |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1521156A CN1521156A (en) | 2004-08-18 |
| CN100465148C true CN100465148C (en) | 2009-03-04 |
Family
ID=34282037
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031035132A Expired - Fee Related CN100465148C (en) | 2003-01-28 | 2003-01-28 | High density compact disc and its recording compound |
| CNB2004100979808A Expired - Fee Related CN100522913C (en) | 2003-01-28 | 2003-01-28 | High density optical disk and its compound for recording |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100979808A Expired - Fee Related CN100522913C (en) | 2003-01-28 | 2003-01-28 | High density optical disk and its compound for recording |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN100465148C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415621A (en) * | 1980-02-25 | 1983-11-15 | Eastman Kodak Company | Use of α,α-bis(dialkylaminobenzylidene) ketone dyes in optical recording elements |
-
2003
- 2003-01-28 CN CNB031035132A patent/CN100465148C/en not_active Expired - Fee Related
- 2003-01-28 CN CNB2004100979808A patent/CN100522913C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415621A (en) * | 1980-02-25 | 1983-11-15 | Eastman Kodak Company | Use of α,α-bis(dialkylaminobenzylidene) ketone dyes in optical recording elements |
Non-Patent Citations (2)
| Title |
|---|
| "β-唑基烯基酮的合成、反应机理及生物活性研究. 黄文芳等.有机化学，第14期. 1994 |
| "β-唑基烯基酮的合成、反应机理及生物活性研究. 黄文芳等.有机化学，第14期. 1994 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1521156A (en) | 2004-08-18 |
| CN1651385A (en) | 2005-08-10 |
| CN100522913C (en) | 2009-08-05 |
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