Abstract:
The invention discloses new indolestyryl compounds and their uses for a high-density optical recording medium. The invention uses the new indolestyryl compounds to form the recording layer of a high-density recording medium. The new indolestyryl compounds are easy to prepare and purify, so they are cheaper when comparing to the compounds generally used in high-density optical recording media. The indolestyryl compounds have a maximum absorption for light wavelengths in the range of 500 nanometers to 700 nanometers. The indolestyryl compounds also have high sensitivity and chemical stability toward light and heat. Using the new indolestyryl compounds to form high-density optical recording media can match up with the short-wavelength laser beam for high-density optical recording media and have the advantage of a stable quality.

Description:
BACKGROUND OF THE INVENTION  
         [0001]    1. Field of Invention  
           [0002]    The invention relates to new indolestyryl compounds and, in particular, to new indolestyryl compounds and their uses in high-density optical recording media.  
           [0003]    2. Related Art  
           [0004]    With the coming of information and multimedia era, computer, communication and consumer electronics have higher demands for larger storage density and capacity. Due to the large amount of information exchange, it is desirable to develop a high-density, small and cheap storage medium. Conventional magnetic storage media are already insufficient for current uses; high-density optical information storage media are the main subject under study. There had been some proposed principles and methods for increasing the storage density in optical information storage media. Some of them are important and have already been successfully implemented. One method is to shorten the wavelength of the laser beam. For example, red lasers are replaced by blue lasers. One can also achieve the same goal by increasing the NA (Numerical Aperture) of the lens. Another method is to improve the digital signal coding means or to utilize optical disk recording with the so-called ultra-high resolution near-field optical structure. These methods can all effectively increase the storage density.  
           [0005]    On the other hand, another research field of optical information storage media is to replace the organic dyes used in optical recording layers by those with better optical properties. In recent years, one-time recording compact discs (CD-R) have become people&#39;s favorite storage media due to their cheap prices, fast burning speeds, convenience in carriage, and high compatibility among different personal computers. To achieve high-density storage, dyes for such media as one-time recording digital versatile discs (DVD-R) with 4.7 GB capacity have become an important subject under research. Since the laser for high-density storage media such as DVD-R&#39;s has a light wavelength of 650 nm, which is different from that of the laser for CD-R&#39;s (780 nm), the dyes cannot be shared between the two kinds of media. This is why developing new organic dyes for high-density storage media is an urgent need.  
         SUMMARY OF THE INVENTION  
         [0006]    It is an objective of the invention to provide new indolestyryl compounds and their uses in high-density recordable optical discs. Such indolestyryl compounds have a maximum absorption for light wavelengths in the range of 500 nanometers to 700 nanometers (λ=500 nm˜700 nm). The indolestyryl compounds also have high sensitivity, chemical stability toward light and heat and good solubility for organic solutions.  
           [0007]    To achieve the above objective, the invention provides new indolestyryl compounds which have the following graphical chemical structure (I).  
                         
 
           [0008]    As shown in the structure (I), R 1 , R 2 , R 3 , R 4 , R 5  and Y −  represent groups connected to different positions on the chemical structure. In particular, when R 1  is CH 2 C 6 H 4 CO 2 R 6 , (CH 2 ) n SO 3 R 7 , or (CH 2 ) n CO 2 R 7 , Y −  can be any anions such as (TCNQ − ) n  (teteacyano-p-quinodimethane) and (TCNE − ) n  (tetracyanoetyleiie)(n=0,1), ClO 4   31  , SbF 6   − , PF 6   − , BF 4   −  and halide ions (X − ) etc.. R 2  and R 3  are same or different groups selected from hydrogen atoms, alkyl groups with one to eight carbons (C 1-8 ), alkyl-oxygen groups with one to eight carbons (C 1-8 ) and alkyl-ester groups one to eight carbons (—CO 2 R 8 ). R 2  and R 3  can be connected to form a pyrrolidine ring, R 2  and R 3  can be connected to benzene ring to form a julolidine ring. R 4  and R 5  are same or different groups selected from hydrogen atoms, alkyl groups with one to eight carbons (C 1-8 ), trifluoromethyl groups, alkyl-oxygen group, carboxyl groups, nitric groups, amide groups (CONR 9 R 10 ), sulfonic groups, SO 3 R 11 , alkyl-ester groups with one to eight carbons (C 1-8 ), and halide ions (X − ).  
           [0009]    When the choice of Y −  needs to match R 1  and R 1  is an alkyl group with one to eight carbons (C 1-8 ), Y −  must be one of TCNQ −  (teteacyano-p-quinodimethane) and TCNE −  (tetracyanoetylene). Moreover, when R 1  is one of CH 2 C 6 H 4 CO 2 R 6 , (CH 2 ) n SO 3 R 7 , and (CH 2 ) n CO 2 R 7 , Y −  can be one of TCNQ −  (teteacyano-p-quinodimethane), TCNE −  (tetracyanoethylene), ClO 4   − , SbF 6   − , PF 6   − , BF 4  and halide ions.  
           [0010]    When R 1  of the new indolestyryl compound is CH 2 C 6 H 4 CO 2 R 6 , (CH 2 ) n SO 3 R 7 , or (CH 2 ) n CO 2 R 7 , R 6  and R 7  can be an alkyl group with one to eight carbons or alkyl fluoride (C 2 F 4 , CF 3  etc.).  
           [0011]    When R 4  and R 5  in the new indolestyryl compound is an alkyl-ester group (—CO 2 R 8 ) with one to eight carbons (C 1-8 ), R 8  can be an alkyl group with one to eight carbons or alkyl fluoride (C 2 F 4 , CF 3 ). If R 4  and R 5  are amide groups (—CONR 9 R 10 ), R 9  and R 10  may be same or different groups. R 9  and R 10  can be hydrogen atoms or alkyl groups with one to six carbons. When R 4  and R 5  are —SO 3 R 11  groups, R 11  may be hydrogen atoms or alkyl groups with one to six carbons. The above choices of groups can be selectively applied to the chemical formula (I).  
           [0012]    Furthermore, the manufacturing method of the new indolestyryl compounds requires the reaction between the compound (II) and the compound (III) in an organic solution. The manufacturing method of the new indolestyryl compounds is explicitly as follows:  
           [0013]    Mix the compound (II) and the compound (III) in an organic solution. They undergo a reaction to obtain an indolestyryl compound (IV) with halide ions (X − ).  
                         
 
           [0014]    Finally, as shown in the following reaction formula, the indolestyryl compound (IV) with halide ions and one of the lithium, sodium and potassium salt (LiY, NaY, KY) are mixed in an organic solution to exchange ions, obtaining a new chemical compound with the chemical formula (I).  
                         
 
           [0015]    The disclosed indolestyryl compounds can be directly applied to usual DVD&#39;s and the recording layers of other high-density data storage media.  
           [0016]    It is another objective of the invention to provide a high-density data storage medium using the new indolestyryl compound dyes in its recording layer. Since this kind of indolestyryl compounds can be easily synthesized and purified, they are cheaper than other usual dyes. In addition, the high-density data storage media using the disclosed indolestyryl compounds have good light sensitivity and superior chemical stability in the recording layer.  
           [0017]    It is yet another objective of the invention to use the new indolestyryl compounds as the recording layer of a recordable optical disc to form a high-density optical recording medium. The recordable optical disc comprises: a first substrate, which is a transparent substrate with grooves, a recording layer, which is formed on the first substrate surface using the new indolestyryl compounds, a reflective layer formed on the recording layer, a second substrate, which is a transparent substrate with grooves connected to the reflective layer with an attachment layer. One feature of the invention is that the new indolestyryl compounds are used as dyes in the recording layer. 
       
    
    
     BRIEF DESCRIPTION OF THE DRAWINGS  
       [0018]    The invention will become more fully understood from the detailed description given hereinbelow illustration only, and thus are not limitative of the present invention, and wherein:  
         [0019]    [0019]FIG. 1 is a schematic view of the chemical formula (I) of the disclosed indolestyryl compounds;  
         [0020]    [0020]FIG. 2 is a schematic view of an embodiment of the invention using the new indolestyryl compound dyes in high-density recordable optical discs; and  
         [0021]    [0021]FIG. 3 shows the spectrum of the reflective index versus the wavelength for the disclosed high-density recordable optical discs. 
     
    
     DETAILED DESCRIPTION OF THE INVENTION  
       [0022]    This specification discloses new indolestyryl compounds and their uses in high-density recordable optical discs. The indolestyryl compounds have the structure in the chemical formula (I) with different group combinations.  
         [0023]    To explain the invention, we illustrate in the following paragraphs the synthesis procedure and the chemical formula of the new indolestyryl compounds. FIG. 1 shows the general chemical structure of the indolestyryl compounds.  
         [0024]    In a first embodiment, 5 g of initial material (II) with an R 1  being —CH 2 C 6 H 4 CO 2 CH 3  and 2.4 g of material (III) with the same R 2  and R 3  (—C 2 H 5 ) are dissolved in 120 ml alcohol. The system is heated to the backflow temperature of the alcohol for reaction for eleven hours. After the reaction is completed, the system is filtered and dried to obtain a green solid crystal (A) with a chemical formula (IV), where R 4  and R 5  are hydrogen atoms (H), X −  is an iodine ion, and the reaction yield is 83%. After material analysis, we find that the compound (A) has an absorption wavelength of 566 nm (UV max =566 nm). The compound (A) further undergoes an ion exchange reaction with one of the lithium, sodium and potassium ionic compounds in an organic solution, forming various kinds of new compounds with the chemical formula (I). The following lists the manufacturing procedure and properties of the new compounds (A) formed from the ion exchange reaction:  
         [0025]    (1) Take 2.84 g of the solid crystal of compound (A) and 1.5 g of NaSbF 6  and dissolve them in 50 ml alcohol. Heat them up to perform ion exchanges. After the reaction, the products are filtered and dried to obtain dark green solid crystal of compound (B) with the chemical formula (I), R 4  and R 5 ═H, and Y═SbF 6 . The reaction yield is computed to be 89%. The material analysis indicates that the compound (B) has an absorption wavelength of 566 nm (UV max =566 nm) and the absorption coefficient ε=1.09×10 5 .  
         [0026]    (2) Take 2.84 g of the solid crystal of compound (A) and 1.6 g of LiTCNQ and dissolve them in 50 ml alcohol. Heat them up to perform ion exchanges. After the reaction, the products are filtered and dried to obtain gold green solid crystal of compound (C) with the chemical formula (I), R 4  and R 5 ═H, and Y=TCNQ − . The reaction yield is computed to be 86%. The material analysis indicates that the compound (C) has an absorption wavelength of 566 nm (UV max =566 nm) and the absorption coefficient ε=1.26×10 5 .  
         [0027]    A second embodiment of the invention also has new compounds with the chemical formula (I). The side group R 1  is selected to be —(CH 2 ) 4 CO 2 CH 3 . Take 9 g compound with the chemical formula (II) as the initial material, where R 1  is —(CH 2 ) 4 CO 2 CH 3 , and 4.3 g compound with the chemical formula (III), where R 2  and R 3  are connected into a pyrrolidine ring, and dissolve them into 100 ml alcohol. Heat up the alcohol to its reflux temperature for reaction for eleven hours. After the reaction is completed, the products are filtered and dried to obtain green solid crystals of the compound (G), with a chemical formula (IV), R 4  and R 5 ═H, X═I − , and a reaction yield of 86%. The material analysis indicates that the compound (G) has an absorption wavelength of 557 nm (UV max =557 nm). The compound (G) and different lithium, sodium, and potassium ionic compounds are mixed in an organic solution for ion exchanges, forming various kinds of new compounds with the chemical formula (I). The following lists the manufacturing procedure and properties of the new compounds (G) formed from the ion exchange reaction:  
         [0028]    (3) Take 2.5 g of the solid crystal of compound (G) and 1.4 g of NaSbF 6  and dissolve them in 50 ml alcohol. Heat them up to perform ion exchanges. After the reaction, the products are filtered and dried to obtain dark green solid crystal of compound (H) with the chemical formula (I), R 4  and R 5 =═H, and Y═SbF 6   − . The reaction yield is computed to be 93%. The material analysis indicates that the compound (H) has an absorption wavelength of 557 nm (UV max =557 nm).  
         [0029]    The compounds (A) and (G) formed in the first and second embodiments are indolestyryl compounds with iodine ions. They are mixed with lithium, sodium and potassium salts in an organic solution for ion exchanges. After the reaction is completed, the products are filtered and dried to obtain the disclosed indolestyryl compounds (B), (C), (D), (E), (F), (H), (I) and (J). The chemical formulas and the maximal absorption wavelengths of the various new compounds are listed in Table 1.  
                                 TABLE 1                           The chemical formulas and the maximal absorption wavelengths of new       indolestyryl compounds.            No   Compound structure   λmax(nm)   ε                                   A                                 566   —               B                                 566   1.09 × 10 5                 C                                 566   1.26 × 10 5                 D                                 566   9.82 × 10 4                 E                                 568   —               F                                 567   8.78 × 10 4                 G                                 557   6.7 × 10 4                 H                                 557   —               I                                 555   7.52 × 10 4                 J                                 556   6.35 × 10 4                 K                                                
 
         [0030]    After the new indolestyryl compounds obtained from the disclosed embodiments are appropriately diluted and processed, we then obtain dyes for high-density optical discs. One can also mix more than one kinds of indolestyryl compounds or other dyes in order to obtain required properties for high-density optical discs.  
         [0031]    We further apply the new indolestyryl compounds to form the recording layer of high-density recordable optical discs. With reference to FIG. 2, the high-density recordable optical disc is comprised of: a first substrate  10 , which is a transparent substrate, a recording layer  20 , which is indolestyryl compounds formed on the surface of the first substrate  10 , and a reflective layer  30 , which is formed on the recording layer  20  and coated with a resin protection layer  40 , a second substrate  60 , which is a transparent substrate, and an attachment layer, which connects the resin protection layer  40  and the second substrate  60 .  
         [0032]    The indolestyryl compounds mentioned here has the structure shown in the chemical formula (I) and can be combined with different ion groups. The material selection and manufacturing method of the indolestyryl compound dyes can be understood from the following text.  
         [0033]    The steps of the manufacturing method are as follows: First, dissolve 1.8 g of the new indolestyryl compounds in 2,2,3,3-tetrafluoropropanol and make a 100 g solution. This solution is applied on the first substrate  10  by coating. Afterwards, a drying procedure is employed to form a recording layer  20  of the new indolestyryl compounds on the substrate surface. The recording layer  20  is formed with a reflective layer  30  by sputtering a metal material, followed by the application of a resin protection layer  40 . Finally, a second substrate is provided to combine with the resin protection layer  40  using an attachment layer. This completes the manufacturing of a high-density recordable optical disc.  
         [0034]    The first substrate and the second substrate are transparent substrates with lands and grooves. The track pitch is between 0.3 μm and 0.8 μm. The groove depth is between 70 nm and 200 nm. The material of the substrate can be polyesters, polycarbonates (PC), PMMA, MCOC, etc.  
         [0035]    The formation method of the recording layer can be spin coating, vacuum evaporation, jet coating, rolling coating, or soaking. It is preferably to use spin coating, forming a recording layer of 70 nm to 250 nm thick.  
         [0036]    The organic solution for coating can be selected from alcohols with one to six carbons (C 1-6 ), ketones with one to six carbons, ethers with one to six carbons, halide compounds, cyclanes and amides. The alcohols can be methanol, ethanol, isopropanol, diacetonalchol (DAA), 2,2,3,3-tetrafluoropropanol, trichloroethanol, 2-chloroethanol, octafluoropentanol, or hexafluorobutanol. The ketones can be acetone, methyl isobutyl ketone (MIBK), methyl ethyl ketone (MEK), and 3-hydroxy-3-methyl-2-butanone. The suitable halide compounds include chloroform, dichloromethane, and 1-chlorobutane. The amides include dimethylformamide (DMF) and dimethylacetamide (DMA). The cyclane is methylcyclohexane (MCH).  
         [0037]    The material of the reflective layer sputtered on the recording layer is selected from gold, silver, aluminum, silicon, copper, silver-titanium alloys, silver-chromium alloys, and silver-copper alloys. The combination of the first substrate and the second substrate can be achieved using spin coating, half-tone printing, hot gluing, and double-sided tapes.  
         [0038]    The thickness of the recording layer on the substrate in this embodiment is between 70 nm and 250 nm. A reflective layer of 50 nm to 200 nm thick is directly coated on the recording layer. Finally, the substrate formed with the reflective layer and the recording layer is combined with another blank substrate with a thickness of 0.6 mm. (As described before, the connection can be achieved using spin coating, half-tone printing, hot gluing, and double-sided tapes.) A high-density recordable optical disc of 120 mm thick can be thus formed. FIG. 3 shows the optical spectrum of the reflective index of the high-density recordable optical disc versus the wavelength in accordance with the invention. As shown in the drawing, the reflective index is greater than 45% for wavelength between 635 nm and 650 nm.  
         [0039]    We further use in the embodiment a PULSTEC DDU-1000 evaluation test machine to write and read the test results.  
         [0040]    The recording conditions are: the constant linear velocity (CLV) is 3.5 m/s, the wavelength is 658 nm, the numerical aperture (NA) is 0.6, and the writing power is 7˜14 mW. The reading conditions are: the CLV is 2.5 m/s, the wavelength is 658 nm, the NA is 0.6, and the reading power is 0.5˜1.5 mW. Table 2 has the CNR values under different writing powers in the embodiment.  
                                                                                                   TABLE 2                                       Writing Power           (mW)                7   8   9   10   11   12   13   14                        3T CNR (dB)   39.0   44.5   50.2   55.5   57.2   58.9   59.2   59.2                  
 
         [0041]    From Table 2, we see that when the writing power is above 9 mW, the CNR value is greater than 50 dB. This means that the high-density optical disk according to the invention has the advantages of high sensitivity and chemical stability of light and heat.  
         [0042]    Effects of the Invemtion  
         [0043]    The disclosed new indolestyryl compounds are easy to synthesize and purify. Therefore, they are much cheaper than normal dye compounds used in DVD optical discs. The R1 side group in the structure of new indolestyryl compounds can enhance its photosensitivity and stability to light and heat. These indolestyryl compounds have extremely good solubility in organic solutions, which is ideal for the spin coating procedure for the optical discs. Thus, it is of great advantage to use the new indolestyryl compounds in the recording layer of high-density recordable optical discs. The disclosed recordable optical discs in comparison with conventional one made of normal dye compounds will be cheaper in price, while having better stability under the shorter laser beam used for high-density recordable media.  
         [0044]    Although the invention has been described with reference to specific embodiments, this description is not meant to be construed in a limiting sense. Various modifications of the disclosed embodiments, as well as alternative embodiments, will be apparent to persons skilled in the art. It is, therefore, contemplated that the appended claims will cover all modifications that fall within the true scope of the invention.