Bis-styryl dye and method for manufacturing the same and its...

Details Bis-styryl dye and method for manufacturing the same and its... Bis-styryl dye and method for manufacturing the same and its...

2003-06-09

2004-07-13

Mulvaney, Elizabeth (Department: 1774)

Stock material or miscellaneous articles

Circular sheet or circular blank

C428S064400, C428S064800, C430S270140

Reexamination Certificate

active

06761952

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention generally relates to a dye for a high-density optical disc recording medium. More particularly, the present invention relates to a bis-styryl dye and method for manufacturing the same and its use for a high-density optical disc recording medium.
2. Description of the Related Art
With the rapid advancement of information communication and the development of computer capabilities, a variety of information need to be stored in a more compact storage medium having higher storage density, higher storage capacity and low cost. The storage capacity, density and cost of a conventional magnetic storage medium do not meet the demand of the current development of information technology. The trend of development and research of the storage medium, particularly an optical storage medium is a very interesting topic. For an optical storage medium, the development of a dye for manufacturing the recording layer is the most interesting breakthrough. Presently, a dye having a functional pigment manufactured through organic chemical synthesis and photochemistry having optical characteristics is used in a variety of devices in the industrial field and for further development in the industrial field, such as nonlinear optical element, recording and displaying of information on a disc, photoresistor, thermal/photo/electric sensing and indicator, transformation and storage of energy, medical treatment and biological technology.
In 1981, a 3,3′-diethyl-12-acetyl-thiatetracyanine perchlorate has been originally used in the manufacturing of a disc by Law et al. (K. Y. Law, P. S. Vincett, and G. E. Johnson, Appl. Phys. Lett., 39, 718 (1981)). The major reason for using such an organic pigment is due to its maximum light absorbance property in the near infrared (“NIR”) region. The recording disc may be manufactured by mixing the 3,3′-diethyl-12-acetyl-thiatetracyanine perchlorate with PVAc and spin coated onto the disc. With the successful application of the organic pigment on an optical storage medium, a variety of dyes having different structures are used in the development of optical storage medium, such as the Japanese Patent Nos. 072,254,167, 09,193,545, 09,194,545, 09,226,250, 09,274,732, 10,044,066 and 11,310,728 etc. The major reason for using such an organic dye as a storage media is that the organic dye material can be coated on the substrate by using a conventional spin coating method, other than using a vacuum evaporation method, thus the manufacturing process can be simplified and the cost can also be reduced. Therefore, the stability and the solubility of the organic dye in organic solvent are important factors in choosing the organic dye.
SUMMARY OF THE INVENTION
Accordingly, the purpose of the present invention is to provide a bis-styryl dye, and a structure and a manufacturing method of high-density storage medium using thereof.
As embodied and broadly described herein, the present invention provides a bis-styryl dye derivative including a following chemical structure (I):
In the above chemical structure, Y represents oxygen atom, sulfate atom, carbon atom with substitutes or nitrogen atom with or without substitutes.
R
1
represents an alkyl group having carbon number one to eighteen with or without substitutes or ether group, p-alkyl benzyl group with or without substitutes.
R
2
, R
3
, R
5
, R
6
, R
7
can be same or different groups including hydrogen atom, halogen atom, boronic acid, nitro group, cyano group, adamantyl group, sulfo group, sulfonyl group, amide group which each contain oxygen, sulfur or nitrogen, sulalkyl group with carbon number one to eight, alkoxyl group with carbon number one to eight, carboxy group with carbon number one to eight, alkoxycarbonyl group with carbon number one to eight, hydroxyl group, ferrocenyl group or heterocyclic group.
R
4
can be hydrogen atom, halogen atom, nitro group, alkyl group, sulfonyl group, benzene ring with or without substitutes.
X can be halogen atom, C1O4
−
, BF4
−
, PF6
−
, SbF6
−
, TCNQ
−
, TCNE
−
, naphthalenesulfonic acid or organometallic complex.
In a preferred embodiment of the present invention, a manufacturing method of the bis-styryl dye is provided. The manufacturing method of the bis-styryl dye having the chemical structure (I) includes the following three steps:
Step (a): a compound having the chemical structure (IV) is synthesized from the compounds having a chemical structure (II) and chemical structure (III) as shown below:
Step (b): the compound having the chemical structure (II) is synthesized from the compounds having a chemical structure (V) and chemical structure (VI) by the following reaction:
In which Y includes oxygen atom, sulfate atom, carbon atom with substitutes (i.e. C—R
5
) or nitrogen atom with or without substitutes (i.e. C—R
6
); R
1
includes alkyl group having carbon number one to eighteen with or without substitutes or ether group, p-alkyl benzyl group with or without substitutes. Hereinafter, the compounds having the chemical structure (III), (V) and (VI) will be described in the following, but the invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth hereinafter.
As to the compound having the chemical structure (III) is shown below:
First, when R
3
is a hydrogen atom, the compound having the chemical an be one of the compounds having the structure (III-1) shown below:
Secondly, when the R
3
is an alkyl group, alkoxy group or alkylate group, the compound having the chemical structure (III) can be one of the compounds having the structure (III-2) shown below:
Thirdly, when the R
3
is a halogen atom, the compound having the chemical structure (III) can be one of the compounds having the structure (III-3) shown below:
As to the compound having the chemical structure (V) is shown below:
First, when Y is a carbon atom having substitutes, the compound having the chemical structure (V) can be one of the compounds having the structure (V-1) shown below:
Secondly, when Y is an oxygen atom or a sulfate atom, the compound having the chemical structure (V) can be one of the compounds having the structure (V-2) shown below:
Thirdly, when Y is a nitrogen atom, the compound having the chemical structure (V) can be one of the compounds having the structure (V-3) shown below:
As to the compound having the chemical structure (VI) is shown below:
I—R
1
—I  (VI)
Firstly, when R
1
is an alkyl group with or without substitutes, the compound having the chemical structure (VI) can be one of the compounds having the structure (VI-1) shown below:
Secondly, when R
1
is a p-alkyl benzyl group with or without substitutes, the compound having the chemical structure (VI) can be one of the compounds having the structure (VI-2) shown below:
Step (c): the compound having the chemical structure (I) is synthesized from the ion exchange reaction of the compound having a chemical structure (IV) and NaX, KX or organometallic complex, in organic solvent as shown below:
In the chemical structures described above, X includes a halogen atom, C1O4
−
, BF4
−
, PF6
−
, SbF6
−
, TCNQ
−
, TCNE
−
, naphthalenesulfonic acid or organometallic complex.
As shown below, if X is an organometallic complex, X can be one of the compounds having the structure (X-1) shown below:
Accordingly, the bis-styryl dyes of the present invention is suitable material for making an optical storage medium since the bis-styryl dyes of the present invention have high absorptions, high sensitivity and high writing speed in a wavelength range of about 300 nm to about 800 nm. Moreover, the bis-styryl dyes of the present invention can be dissolved in organic solvents, thus the bis-styryl dyes can be coated on a substrate by using a simple coating method including, but not limited to, inkjet printing, roll-pressing coating, dip coating or spin coating method.
It is to be understood that both the foregoing genera

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