TW591646B - Optical recording material and optical recording media using the same - Google Patents

Abstract

The present invention provides an optical recording material made of an indocyanine compound, which is particularly suitable for DVD-R and CD-R standards conformed with an optical recording medium by a laser having a wavelength of 620 to 830 nm. The feature of the present invention is to have the optical recording material made by a compound represented by the following formula (wherein a ring A and a ring B are each a benzene ring or a naphthalene ring which may have a substituent, a ring C is an organic group which may contain an oxygen, a sulfur or a nitrogen atom of 3 to 6-membered ring or may contain a substituent, R1 and R2 are each a 1-4C alkyl group or a group which may form a ring by coupling, R1 and R2 and the ring formed of carbon atoms bonding with them and the ring C may be the same or different, Q is a bond group (I) or (II), X is a hydrogen atom or a halogen atom, Y is independently organic group, Anm- is a m-value anion, m is an integer of 1 or 2, and p is a coefficient for holding neural in charge).

Description

591646 V. Description of the invention (1) " '------- [Technical Field of Invention] ~ Record = The information pattern that gives intelligence to the heat is recorded in the record system :: 的 光 录 执 #, in detail That is to say, there are optical recording materials with high-density optical recording and reproduction optics such as wavelengths in the near-field and out-of-work areas, and M and X. # 生 之 先 子 3 [Previous technology] Optical recording media used on self-recorded media is generally widely used because of its large memory capacity, two ΓΛ advances, and other excellent features. The characteristics of the recording layer are recorded === the characteristics of the recording layer are recorded, which is different from the unrecorded portion Λ and is reproduced. The layer of the optical recording medium represented by the Dao Han disc is the formation of Lu Jilu, a contract in Putian, which uses organic pigments, especially the indocyanine (Undocyanine) -based compound Weiyang K under discussion. The sensitivity of the sensor is higher than that of the south, which can correspond to the high speed. It is different from the above-mentioned optical discs. The semiconducting target range used for recording and reproduction is 620 ~ 830 millimeters, laser beam meters, 650 nanometers. The specification of 3η + column ^ 咄 is 635 nanometers, and the size of CD_R is 780 nanometers. Correspondence to the bow of this net disc, .. 98/34988, newspaper, JP 7-329424, W〇ηΛΛΛ JP 1 1-34499, JP 2 00 0- 1 085 It has been reported in bulletin No. 10. …, And the absorption wavelength of the indomethacin-based compound is described above.

591646

V. Description of the invention (2) As far as the specifications of optical discs are concerned, they are staggered in terms of short wavelengths and cannot be said to be consistent. The recording layer of the indomethacin-based compound used in the optical disc is made of a thin film by a spin coating method or the like. In the absorption spectrum of 400 to 800 nm, there are two absorption peaks in the short-wavelength front. The long-wavelength peaks of the molecules obtained by multi-quantized interactions can be said to be obtained by molecules without multi-quantized molecules. 'In the recording layer, for the laser wavelength used in recording, it must have sufficient intensity absorption. These are related to peaks in long wavelengths. In the past, a recording layer using an indolesaining compound has been problematic in that it has a small sensitivity for recording light in this field due to insufficient absorption of light of 6200 to 830 nm. Therefore, the object of the present invention is to provide an optical recording medium conforming to a laser of 62 to 8300 nm, which is particularly suitable for an optical recording material made of an indolesaining compound of the DVD-R and CD-R specifications. [Solutions to solve the problem] The Yayoi people consider that the sensitivity of 620 to 830 nanometers of light can be reduced: the interaction between the two meshes, the ratio of multiple quantized molecules to the long wavelength, and the effective absorption of all In terms of long-wavelength shifts, such as instability, etc., it was found that indole too, which has a specific molecular structure: 昍, σ, ', 疋 can solve the above problems and reach the invention. Based on the above-mentioned knowledge based on the general formula, it provides an optical recording medium characterized by the following-an optical recording material formed of the composition, and a film formed of M and β 'on a substrate; . 591646

(π) (In the formula, 'Αί 哀 and B ring can represent the percentage of f or benzene ring or naphthalene coat with T substituent, C% represents the right ring of the 3 to 6 member ring. ≪ Organic group, which may contain oxygen, sulfur, and nitrogen :: may have a substituent I; R1 and 1 represent an alkyl group having a carbon number of 4 or a 7 ring-forming group; R1 and a carbon atom bonded thereto The formed ring is the same as or different from 裒 y by 疋; Q represents a linking group (丨) or (丨 丨); X represents & a hydrogen atom or a halogen atom; Y represents an independent organic group; Anm _ 表 七 Table seven

m-valent anions, m represents an integer of 1 or 2; p represents the coefficient of charge retention neutrality). [Embodiments of the invention] Hereinafter, embodiments of the present invention will be described in detail. The optical recording material of the present invention, as shown in the above general formula, is characterized by being made of an indolesaining compound having a spiro ring C introduced into the molecule. According to the present invention, the citrate compound is based on the effect of the above-mentioned spiral ring, and uses a DVD-R and CD-R wavelength laser to impart an appropriate optical recording layer on the optical recording medium. The structure of this molecule is selected appropriately for the laser 'wavelength used in optical recording. In the above general

591646 V. Explanation of the invention (4) In the formula, 'Q is the absorption wavelength of the trimethylindolindioning compound shown by the linking group (I), which is suitable for the DVD-R specification, and q is the linking group (π). As shown, the absorption wavelength of the methylindoline compound is suitable for the CD_R specification. f In the above general formula, as the ring A and β ring may have a substituent ^ benzene ring or a naphthalene ring substituent, examples include fluorine, chlorine, bromine, iodomethanyl, methyl , Ethyl, propyl, isopropyl, butyl, second butadiene, tributyl, isobutyl, pentyl, isopentyl, third pentyl, hexyl, yl, heptyl, isoheptyl Alkyl, tertiary heptyl, n-octyl, isooctyl dioctyl, 2-ethylhexyl, etc. alkyl, phenyl, naphthyl, 2-fluorenyl 3-methylphenyl, 4-methyl Phenyl, 4-monovinylphenyl, 3-isodiphenyl, t-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, benzidine, 9-ylphenyl, 4-hexylbenzene Base, 4-cyclohexylphenyl, 2,3-dioxoyl, 2,4-dimethylbenzyl, 2 5——benzyl, ethyl, 3-methylbenzyl, 2, 6-dimethyl Group = fluorene 3,4-dimethylphenyl, 3,5-dimethylA, jasmine,? 4 mono-dibutylbenzyl, 2 chloro-methylbenzyl, 2, 4--second butyl 2,4-diphenyl, di & 1-butylphenyl, 2,6-diphenyl Tributylphenyl, di-americyl basic group, 24-1-yl group: monoyl, phenylene, 4-diyl basic group, diphenyl, fluorenyl group, Cylinder-2-yl, diphenylmethyl, Tribenzylpropoxy, Zantu Temple has three groups: square group, methoxy group, ethoxy group, alkoxy group Λ, methyl group, butoxy group, second butoxy group, third butoxy group, etc. Base, 2nd butyl sulfide :: Di Qiao ;. Sulfur, isopropylthio, butyl sulfide, organic odors with substituents, lice, sulfur, nitrogen and < organic groups, such as cyclopropane 591646

， 4 ， 五 ， Explanation of the invention (5) -1,1-diyl, cyclobutane-1,1-one 丞 ... t dimethylcyclobutanediyl, 3-dimethylcyclobutane-diyl , Cyclopentane, Dimei, Hexyl-1,1-diyl, Tetrahydro-0 Bikounan-4,4-diyl, —Visiting — Soil u / · — 石 爪 杂 见 —44— Yiji (Thian -4, 4-diyl), butadiene-4, 4-bis its M-diyl, morpholine-2, 2-diyl, morpholine-3,3 ~ di-1, etc. A person who takes the 4th generation base can be exemplified as the ring A. As a & and alkyl group, examples of the alkyl group include methyl, ethyl, inverse, second butyridine-butyl AS / propyl, isopropyl, butyl tert-butyl , Isobutyl, etc. As a member of & and anti-linker, the ring may also contain an organic group of oxygen and nitrogen atoms. "Lian Ke 1… exemplified. As the ytterbium atom shown again ..., bromine, iodine, etc. In addition, γ indicates two types: limit: for example, methyl, ethyl, propyl, isopropyl, butyl, tertiary i, s: yl, isobutyl, pentyl, isopentyl Base, third pentyl base: " yi! 4-base, hexylmethyl, 2-cyclohexylethyl, heptyl, isoheptyl, second heptyl, n-octyl, isooctyl, base nonyl = nonyl, decyl, dodecyl, ten Triyl, tetradecyl and ten ^ ^ Earth 17-yl, 18-yl, and other alkyl, vinyl, 1-methylocenyl, hexyl: vinyl vinyl, propenyl, butenyl, isobutenyl, ί: Propyl, / alkenyl, octyl, decyl, pentadecyl, "metyl", 4 methyl clay, phenyl, naphthyl, 2-methylphenyl, 3 ~ / Benzoyl, ^ vinylphenyl, 3-isopropylphenyl, 4-yl 4-phenyl, 4: isobutylphenyl, 4-tert-butylbenzyl) 1% Hexyl benzyl, 4-octylphenyl, 4- (2-ethylhexyl) benzyl, 4-monostearic acid. Phenyl, 2,3-dimethylphenyl, 2,4-591646 (6) Methylphenyl, 2,5 ~ dimethyl, and its depletion A. Its qr basic group, 2, 6-dimethylphenyl, 34 basic group, 3, 5-dimethylphenyl, 24 a Alkylaryl, benzyl, benzyl, diphenyl, cyclohexyldiphenylmethyl, triphenylmethyl A tyl 2-benzylpropane-2-yl, Soil T base, Ethylene, cinnamyl, etc., these are interrupted by the combination of aryl alkane and thioether in ethereum, such as 2-methoxyethyl, 3-methyl For example, it can be listed as the following: propyl, methoxy, propyl, 4-methoxybutyl, 2 ~ yl: yl = ylethoxyethyl, methoxyethoxy2: milk 3-methylmilk Butyl butyl, lactyl ethyl, $. Lactyl ethyl, 2-monomethylthioethyl, 2-! And its moieties: both radicals can be: radical: radical, halogen atom, etc. It is replaced by ^ sign continuous base, chaos, and as the ridge private 7 4 ^ indicated by A nm, you. The anion who does not wear clothes, for example, as a monovalent, one hundred examples such as chaotic anion, desert anion, moth anion , Qi yinzi ion; peroxy acid anion, qi acid risk you in Cizisi halogen anion milk absorption anion, thiocyanate anion, > Zan = ion, palladium anion, quaternary boron = ion, benzene Sulfuric acid anion, phenylbenzyl anion, anion; octylphosphonic acid anion: =: = ion, decapenyl sulfonium anion, phenyl sulfonium anion, nonyl ==, 2,2, -methylbis (4,6_ Di-tert-butylphenyl acid : Ions, etc., as the divalent ones can be listed, such as phenyldiphosphine gold, nephrosphosphonic acid anion, etc ... Corresponding requirements can also use the quencher anion of the europium compound. Jealousy, those who quench the anion, can As an example, the anions shown in JP-A-Sho 60-234892 ^ ^ ^-such as the following-general formulas 阴离子 and ⑻ are shown below.

591646 V. Description of Invention (7)

(In the formula, R3 & R4 represent independent alkyl or halogen atoms, a and b represent 0 to 3 each, and R5, R6, R7, and 1 to 8 represent independent alkyl and alkylphenyl groups. , Alkoxyphenyl, or halogenated phenyl.) In the above general formula, as for the C ring, there is a cyclohexane-1,1-diyl group, but it is preferable because it is easy to introduce and has low cost. As far as X is concerned, it is better to optically read the recording layer to maintain a stable hydrogen atom. In the above general formula related to the present invention, as specific examples of the trimethine cyanine compound of the linking group (I) represented by Q, the following compounds No. 1 to 24 and the like can be listed, and, In the following examples, cyanine pigment cations are shown in which anions are omitted. Compound No. 1 Compound "Νο · 2

Page 11 591646 V. Description of the invention (8)

IH1I Page 12 591646 V. Description of the invention (9) Chemical sleeve No · 13 Chemical composition 《Νο · 14

liHI Page 13 591646 V. Description of the Invention (ίο)

Moreover, in the present general formula, specific examples of the trimethine cyanine compound of the linking group (II) represented by Q in the above general formula include the following compounds No. 25 to 48, etc. In the following examples, cyanine pigment cations are shown to eliminate anions. 591646 V. Description of the invention (11) Chemical compound «Ν〇 · 2 5 Chemical compound #} No · 2 6

3 1 ft: joint start No. 3 2

ΙΗϋ Page 15 591646 V. Description of the invention (12) Chemically containing ttNo · 3 3 ο. Ϋ Λ

化 食品 Νο · 3 7 Chemical combination ttNo. 3 8

nil p. 16 591646 V. Description of the invention (13)

Compound No. 4 S

Compound No. 4 S

ΙΗΗ 591646 V. Description of the invention (14) Initial method The compound represented by the above general formula related to the present invention is derived from its system. There is no restriction on power generation, and the bond is made to $ β according to a conventionally known method. For example, a cyclic compound having this structure and a compound for the introduction of a tertiary methyl group are reacted by a reactant. It can be synthesized by changing the demand, for example, by the following methods. Synthesis of Compounds of False H and H (i n d ο 1 e n i n e)

Synthesis of indomethacin compounds

(In the formula, ring A, ring B, ring C, ratio, R2, x, Y, Anm_, and P are the same as those of the general formula (I) or (Π), and D represents halogen and sulfur oxidation.

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Sulfur: ΐΐΓ / indicator, such as gas, bromine, angstrom; as 4 > Interview can be listed such as phenylthiosulfide oxide, 4-methylthiosulfide emulsion, 4-gasthiosulfide oxide Wait. The compound described in id is suitable for use as an optical recording medium's green layer, and the recording drawer θ ^ ^ is generally used by & 铉 = 成 疋 to use conventionally known methods. Suxindi = cellulosic alcohols, methylcellulosic ketones ... ketones, fluorenyl isofibers: hexanols, propyl ethyl esters, butyl acrylates, etc.

The gasification alcohols, ΠΓΓ purpose classes, 2,2,3,3-tetrakipropanol, etc. Second gas Yiyuan, three: A :; gas :: f and other carbon gases. The gas phase is burned and coated on the substrate, which can easily form a solution in an organic solvent such as Slices. The order of the above-mentioned recording layer, the range of SA micron is more appropriate. , And the system is 0 · 0 1 ~ 5, for example, it can be generally used. The formation method is not particularly limited / inventive optics = clever. The recording layer contained in the recording layer is suitable for the recording layer of the sub-recording medium. The use of Xia is based on the requirement of 50 to 100% by weight, ii: layer it: Ming except for optical recording materials, corresponding Substances, phthalocyanine compounds, etc .: Man 2 uses cyanine compounds, • nitrogen-based compound vinegar, polystyrene, tree with polyethylene glycol, poly-tree moon, and the like may also contain interfacial activity 591646 V. Description of the invention (16) Sex agents, antistatic agents, lubricants, flame retardants, self-mark formation promotion properties, dent control properties, dispersants, agents, light resistance imparting agents, etc. In addition, the above-mentioned recording layer is used as one weight As the item of oxygen, there are aromatic nitroso compounds, amine gun compounds, imine tweezer compounds, transition metal chelate compounds, etc., and the use range is preferably between 0 and 50% by weight. The substrate material mentioned above can be used as long as there is a substantially transparent material, and resins such as polyfluorenyl acrylate, polyterephthalate, and glass can be used. Moreover, the shape is corresponding to the tape Shape, drum shape, belt shape, disc, etc. On the above-mentioned recording layer, a reflective film may be formed using gold, a vapor deposition method or a sacrifice method, or a protective layer may be formed using grease, ultraviolet curable resin, etc. The optical recording material of the present invention is used for optical recording. Optical discs with wavelengths of 620 to 830 nanometers 3 LD, CD, DVD, CD-R, DVD-R, etc. are used for media insertion and reproduction. [Examples] The following describes the present invention in more detail with reference to manufacturing examples and examples. It is not limited to the following examples only. [Production Example 1] < Production of Compound No. 3 rhenium hexafluoride > (Step 1)-A base capturing agent, a depression preventing agent, and a cross-linking quencher are also included. It can contain amine gun compounds, double light input light and read light for recording layer. It is especially made of m, for example, ethyl acetate, polycarbonate. For example, it can be used. D silver, aluminum, steel, etc. can be used by acrylic resin. Yu Chuan is especially suitable for the present invention. However, 591646 V. Description of the invention (17) In a reaction bottle filled with nitrogen, 34.5 g of 4-chlorobenzidine sulfate, 42.1 g of ethanol, and warm After reaching 70 ° C, drop 23.9 g of acetamidine in 15 minutes Then, 2.7 g of sulfuric acid was added to the reaction for 4 hours, and then ethanol was distilled off. 200 ml of toluene was added. The solution was washed with water to neutrality, and dried over sodium sulfate to remove toluene. 40.2 g of intermediate (A!). (Step 2) Fill a reaction flask filled with nitrogen with 2 3 4 g of intermediate (Aj) and 19.8 g of iodized isopentane. After reacting at 25 ° C for 3 hours, 92.4 g of ethyl acetate was dropped, and the solution was allowed to flow for 30 minutes and cooled. The solid phase was filtered and removed, and the intermediate (B!) 16 · 0 was obtained. (Step 3) In a nitrogen-filled reaction bottle, put 8.6 grams of intermediate (Bi), 2.0 grams of N, N'-diphenylhydrazone, 15.8 grams of pyridine, and 3.1 grams of anhydrous acetic anhydride. After reacting at 120 ° C for 2 hours, a solution of 14.7 g of dimethylformamide in 7.4 g of potassium hexafluoride was added at 80. (: Medium reaction for 2 hours, after cooling the reaction solution, add 100 ml of aerosol and 100 ml of water, oil-water separation to obtain the oil phase, washed with 5% potassium hexafluoride aqueous solution, and washed with water Net. The solvent was distilled off, and the resulting residue was crystallized from a mixed solvent of 45.8 g of aerosol and 92.1 g of methanol to obtain crystals, washed with methanol, and dried to obtain No. 3 red gold crystals of the object 5. 0 g (yield 22.6%). (Analysis) 1) Structural analysis " H-NMR measurement (chemical shift ppm; multiple number / proton number)

Ml Page 21 591646

V. Description of the invention (18) (0.96-0.99; d; 12) — (1.53 ~ 2.13; m + m + ra + m + m; 26) (4 · 13 ~ 4 · 17; t; 4) (6 · 37 ~ 6 · 42; d; 2) (7.53 ~ 7.58; d; 2) (7.58 ~ 7.61; d; 2) (7.98; s; 1) (8 · 62 ~ 8.69; t; 1) 2) Optical properties: UV spectrum Amax measured in chloroform solution; 572 nm, ε; 1. 75 X 105 [Production Example 2] < Manufacturing> (Step 1) In a reaction bottle filled with nitrogen, 30.1 g of 2-naphthylhydrazine sulfate, 94.8 g of ethanol were charged, and after heating to 70 ° C, 48.0 g The acetamidine has been dripped in 5 minutes. After adding 39.2 g sulfuric acid for 3 hours, the ethanol is distilled off, 500 ml of toluene is added, and 200 g of a 20% aqueous sodium hydroxide solution is added to separate the oil and water. Wash with water until it is neutral, dry with sodium sulfate, and dissolve the solvent-removing residue with 6 to 9 grams of methylbenzene. Add 94 grams of N-hexane to the solution for crystallization, filter and crystallize, and dry. 31.6 g of intermediate (A2) were obtained. (Step 2) In a reaction bottle filled with nitrogen, 25.0 g of the intermediate (a2) and 2 3 g of iodinated isopentane were reacted. After 4 hours of reaction in 丨 丨, 1 02 · was dropped. 4 g of ethyl acetate was allowed to flow for 30 minutes, cooled, and the solid phase portion was removed by filtration, washed and dried to obtain intermediate (B2) 3 1.6 g. (Step 3)-

Page 22 591646 V. Description of the invention (19) In a reaction bottle filled with nitrogen, [3.5 grams of intermediate ^), 3.0 grams of N, N'-diphenylhydrazone, and 23.8 grams of pyridine 4, 6 g of helmet water acetic anhydride, after reacting at 120 ° C for 2 hours, add 20.2 g of ethanol solution in which 50 g of sodium peroxy monohydrate is dissolved, and react for 2 hours in 80 t. After cooling the reaction solution, crystals were precipitated in 10 · 0 g of ethanol, washed with methanol, and then dried to obtain 5.2 g of the objective No. 9 green crystal (yield: 10.7%). (Analysis) ^ ° 1) Structural analysis " H-NMR measurement (chemical shift ppm; multiple number; proton number) (0.93-0.96; d; 12) (1.54 ~ 2 · 20; m + m + m + m + m; 26) (4.2-4.47; t; 4) (6.656 ~ 6.70; d; 2) (7.52 ~ 7.57; m; 2) (Ί. 63-7.8〇; m + m; 6) (8. 05-8.14; m + s; 5) (8.31 ~ g.34; d; 2) 2) Optical characteristics: UV measurement in aerobic solution Spectrum; 615 nm, ε; 0.899 x 105 [Production Example 3] < Production of peroxyacid salt of Compound No. 10 > In a reaction bottle filled with nitrogen, 13.8 g of the above intermediate was charged. (B2), 23.7 g of pyridine, and 3.1 g of anhydrous acetic anhydride heated to 50 ° C, dissolve 5.1 g of the raw material compound of the following formula, and drop the solution within 30 minutes. The reaction was carried out in 70t for 2 hours. To this system was added 3.4 g of sodium peroxymonohydrate, 35.6 g of methanol, and the solution was further flowed for 1 hour. After cooling the reaction system, the crystals were precipitated, and thin water was used. After washing, drying to obtain the target

Page 23 591646 V. Description of the invention (20) 2.6 grams of purple crystals (yield: 37.6%)

(Analysis) 1) Structural analysis " H-NMR measurement (0.92-0. 96 (1.38-1.49 (1. 74-2. 01 (4. 36-4.41 (6. 76-6. 80 (7. 67- 7. 80 (8. 27-8. 57 t; 3) (1.09-1.14; d; 6) tm; 1) m + m + m + m; 2 2) m; 4) (6 · 68 ~ 6 · 72; d; 2) d; 2) (7.35 ~ 7.57; m; 2) m + m; 4) (8.06 ~ 8.16; m; 4) m; 3) 2) Optical properties: in chloroform solution Measurement of UV spectrum; 605 nm, e; 1. 20 X 105 [Production Example 4] Φ < Production of Compound No. 20 phosphorous hexafluoride salt > (Step 1) In a reaction bottle filled with nitrogen 11.7 g of the above-mentioned intermediate (8 丨), 13.8 g of benzoic acid monophenylpropyl S, and 25.5 g of diethylacetamide were reacted at 1 2 5 ° C for 3 hours, and then dropped. 50.1 g of ethyl acetate was left for 30 minutes and cooled. The solid portion was filtered and removed, washed and dried.

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13.0 g of intermediate (B3) was obtained (yield 50.8%). (Step 2) Fill a nitrogen-filled reaction bottle with 5.j grams of 1,1,3,3-tetramethoxypropane, 158 grams of pyridine, 0.8 reaction for 6 hours, and add 30 grams of gas 2. 8 g of potassium hexafluoride was used to separate oil and water in JO: C. #Wash three times with 30 grams of water, steam 0 grams of water, add 30 grams of aerosol to heat and dissolve, add 60 grams of methanol to cold and prepare the oil to take out the solid phase, wash with ethanol, and dry to obtain Green '= transition (yield 25.0%). ° Day · 1g (Analysis)

1) Structural analysis & H-NMR measurement (1.556 to 2.18; m + m + m + m + m; 24) (2. 70 to 2.74; t; 4) (4.16 to 4. 20; t; 4) (6.19 to 6.22; d; 2) (6.64 to 6.52; t; 1) (7. 14-7. 31; m + m; 10) (7.41 -7.55; d + d; 4) (7.91; s; 2) (8 · 16 ~ 8 · 22; t; 2) 2) Optical characteristics: UV spectrum measured in methanol solution; 664 nm, ε; 2 48 X 105 eight max

[Manufacturing example 5] < Production of compound No. 21 phosphorous hexafluoride salt > (Step 1) In a reaction bottle filled with nitrogen, 23.4 g of the above intermediate and 25.1 g of monoisopentylbenzenesulfonic acid were charged. Ester and 46.2 g of diethylacetamide, reacted at 125 C for 3 hours, '-dripped 92.4 g of ethyl acetate'

Page 25 591646 V. Description of the invention (22) Return the solution for 30 minutes, cool it, filter out the solid phase, wash and dry to obtain 19.1 g of intermediate (B4) (yield 41.3%). (Step 2) Fill a nitrogen-filled reaction bottle with 9.9 grams of intermediate (β4), 2.6 grams of propionaldehyde bisphenylimine, 15.8 grams of pyridine, and 3.1 grams of anhydrous acetic anhydride.

The reaction was carried out at 70 ° C for 4 hours. 30 g of aeroform, 5.5 g of potassium hexafluoride and 30 g of water were added to separate oil and water. It was washed with 30 g of water three times, and the solvent was removed by distillation to obtain an oily substance. 15.8 g of dimethylformamide was added to heat and dissolve. 60 g of methanol was added to cool, and the solid phase was removed by filtration. After washing with alcohol and drying to obtain 4.7 g of cyan crystals (yield: 60. 0%). (Analysis) 1) Structural analysis " H-NMR measurement (〇. 97--0.999 d; 12) (1. 50--2.19 m + m + m + m + m; 26) (4. _4 · 14 t; 4) (6. 26 ~ 6. 29; d; 2) (6. 6L ·-6. 70 t; 1) (7. 45-7.47; d; 2) (7 · 54- ^ 7. 56 d; 2) (7 · 92; s; 2) (8. 15 · -8 · 21 t; 2)

2) Optical characteristics: Measured UV spectrum λ max in methanol solution; 662 μm, £ 2.78 × 105 [Production Example 6] < Production of peroxy acid salt of Compound No. 22 > (Step 1) In a nitrogen-filled reaction bottle, fill-in 87 · 3 g of 4-methoxyhydrazine salt

Page 26 W1646, description of the invention (23) = current, 100 · g ethanol, after heating to 60 ° C, pay attention to the heat while heating: 66 · 2g yihexylmethyl_, still flowing for 2 hours After that, 2.00 g of the sample was added: 2 water 20 0.0 g for 3 times of oil-water separation, f benzene phase was still dehydrated 4 and solvent was removed to obtain an intermediate (108. 7 g (yield 94.8) %). (Step 2) Fill a reaction bottle filled with nitrogen with 22.9 grams of intermediate (a4), 27.4 grams of benzoic acid monoisoamyl ester and 45.8 grams of diethylacetamide. After 2 hours of reaction in 1 C, 91.5 g of ethyl acetate was added dropwise, the solution was allowed to flow for 30 minutes, and cooled to room temperature. The solid portion was removed by filtration, washed and dried to obtain 36.1 g of intermediate (B5) ( Yield: 73.4%) (Step 3) In a reaction bottle filled with nitrogen, 19.7g of intermediate (B5), 5.2g of propionaldehyde bisphenylimine hydrochloride, and 31.6 A gram of pyridine and 6.7 grams of anhydrous acetic anhydride were reacted in 70 t for 3 hours. 60 grams of aeroform, 6.1 grams of sodium perchlorate monohydrate, and 60 grams of water were added to separate the oil from water. Grams of water washed 3 times, distilled off The solvent was obtained as an oil, and 40.0 g of dimethylformamide was added to heat and dissolve. 80.0 g of methanol was added to cool it. The solid portion was removed by filtration, washed with methanol, and dried to obtain green crystals 6.0. Gram (yield 40 · 8%). (Analysis) 1) Structural analysis: 1H-NMR measurement (97 · 99 ~ 99; d; 12) (1 · 5 1 ~ 2 · 19; m + m + m + m + m; 2 6) (4.08 to 4.12; t; 4) (6.16-6.19; d; 2) (6.50 to 6.56; t; 1) (7.Ό3 to 7. 6; d; 2)

591646 V. Description of the invention (24) (7.40; s; 2) (7 · 34 ~ 7 · 36; d; 2) (8 · 03 ~ 8 · 10; t; 2) 2) Optical properties: in methanol solution ψ I was drunk, and the combined spectrum was deleted. The maximum spectrum was 679 μm, £ 2.09 μm [Example 1] < Manufacturing and Evaluation of Recording Media > π 5 二 Ϊ f Waterjet Solution Bottom layer (0.01 micron) diameter of 12 cm polydecomposition acid = on the substrate of the plate 'coated titanium chelate compound (τ_5. Compound No. 3 hexafluoride hafnium salt, No. 9 and. Pass by

And the comparative compounds 1 and 2 shown below were coated with 2,2,3,3-tetrabenzidine 2β by a spin coating method to form an optical recording medium having a thickness of 100 nm and a recorded layer. :, These optical recording media and t, by the measurement of the absorption spectrum of vv. # 算 疋 The λ_intensity for each recording medium is relative. When this value is smaller than 0 ″ 5, the recording input and reading characteristics are poor. When it exceeds 4, the light resistance of the recording layer is deteriorated, and the recording The storage stability is deteriorated, and the value range is preferably from 0.15 to 0.45. The results are shown in Table} and Table 2 ′. Those with appropriate ranges in the table are indicated by 0.

Comparative compound 1 Comparative compound 2

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[Table 1] Evaluation of pseudo-indole-based three-dimensional formazan J 1 卩 arches 丨 赛 赛 Saining compound optical recording material λ max 620 nm relative strength 635 nm relative strength compound No. 3 phosphorus hexafluoride Salt 588 0.20 〇0.15 〇Comparative Compound 1 576 0.11 0.08 From Table 1 above, it can be confirmed that the optical hexahedron material using the compound No. 6 hexafluorinium salt has excellent characteristics in a wavelength range of 620 to 635 ¾ microns

[Table 2] Evaluation of the pseudo-indole-based pentamethylindole Saining compound Optical record λ max 650 nm 660 nm 690 nm Material relative strength relative strength relative intensity compound No. 9 631 0.67 0.40 0.16 Perchlorate 〇 Compound No. 10 622 0.35 0.23 0.12 Peroxy acid salt 〇Comparative Compound 2 611 0.15 〇 0.12 0.07 From Table 2 above, the optical record of Compound No. 9 peroxy acid salt can be confirmed The media shows excellent characteristics in the wavelength range of 660 to 690 nm. In addition, it was confirmed that the optical recording medium 'using the peroxy acid salt of Compound No. 10 exhibited excellent characteristics in a wavelength region of 650 to 660 nm. At the same time, at 650 nm, comparative compound 2 and compound No. 1 were used.

Page 29 591646 V. When comparing the optical recording material of the peroxy acid salt No. 26 of the invention description "" From its relative strength, it is better to use the peroxy acid salt of compound No. 10 . [Example 2] < Production and Evaluation of Recording Media > The same operations as in Example 1 were performed, using peroxy acid salts of Compound Nos. 22, 23, and 27, and using Comparative Compound 3 described below. And 4, optical recording media were prepared, and these optical recording media were evaluated by measuring UV spectral absorption. The results are shown in Table 3.

[table 3]

Evaluation of Sjslf-based indomethacin compounds Optical recording material λ max 780 nm relative strength of nanometer compound No. 22 719 0.28 Peroxy acid salt 0 Compound 23 723 0.31 Peroxy acid salt 0 Compound No. 725 0.40 Peroxyacids 0 Comparative Compound 3 710 0.14 Comparative Compound 4 ^ 712 .. 0.14

Page 30 591646 V. Description of the invention (27) From Table 3 above, it can be confirmed that the optical recording media using compounds No. 22, No. 23, and No. 27 perchlorate have a CD-R specification of 78 mm. The micron wavelength region shows excellent characteristics. [Effects of the Invention] According to the present invention, it is possible to provide an optical recording material made of an indolesaining compound in accordance with an optical recording medium.

Page 591646 Schematic Description

Page 32 (The above columns are filled in by the Office) Name of the inventor Applicant Chinese name in English (Chinese) Name (English) Name of residence in the country of origin 8 Magic 4 ± Name of representative in China (Chinese) Name of Representative (English) Invention Patent Specification Optical Recording Material 591646 material and optical recording media using-the 1. Yano Hiroshi 2. Takada Yide 3. Oya &:

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l.HIROYUKI NAKAJIMA

O: \ 71 \ 7i389-921229.ptc Page 1

Claims (1)

591646 f positive replacement page Case No. 90113363 Amendment 1 · An optical recording material characterized by a compound represented by the following general formula, Linker ⑴ (Π) (In the formula, ring A and ring B represent a benzene ring or a naphthalene ring which may have a substituent; ring C represents an organic group of 3 to 6 members, which may contain oxygen, sulfur, and nitrogen atoms, and may have Substituents; h and 1? 2 represent alkyl groups of carbon number 4 or groups that can be linked to form a ring; the ring formed by Ri, R2 and the carbon atom bonded thereto may be the same or different from the C ring Q represents a linking group (I) or (II); X represents a hydrogen atom or a halogen atom; Y represents an independent organic group; Anm_ represents an anion of m valence, m represents an integer of 1 or 2; p represents The charge remains neutral. 2. The optical recording material according to item 1 of the patent application, wherein Q is a linker (I). 3. The optical recording material according to item 1 of the scope of patent application, wherein the above Q is a linking group (I I). 4. The optical recording material according to any one of claims 1 to 3, wherein X is a hydrogen atom. 5. If the optical recording material of any one of the items 1 to 3 of the scope of patent application, O: \ 71 \ 71389-921229.ptc Page 33 591646 O: \ 71 \ 71389-921229.ptc Page 34