JP2001002783A - Composition for optical material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a composition having high Abbe number and high refractive index and useful for optical lens such as plastic lens for eyeglass by including an inorganic compound having a specific atom and a compound reactive with the inorganic compound. SOLUTION: This composition contains (A) an inorganic compound containing sulfur and/or selenium atoms in an amount of preferably >=30 wt.% (e.g. sulfur) and (B) a compound reactive with the component A and preferably containing a structure of the formula (R1 is a 1-10C hydrocarbon group; R2 to R4 are each H or a 1-10C hydrocarbon group; Y is O, S, Se or Te; (m) is 1-5; (n) is 0-5; (p) is 0 or 1) in the molecule [e.g. bis(β-epithiopropyl)sulfide]. Preferably, the contents of the component A and the component B are >=1 wt.% and >=10 wt.%, respectively, the sum of the components A and B is >=30 wt.% and the amount of the component A is 1-50 pts.wt. based on 100 pts.wt. of the component B.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a plastic lens,
The present invention relates to optical materials such as prisms, optical fibers, information recording substrates, and filters, and more particularly to optical lenses such as plastic lenses for eyeglasses.

[0002]

2. Description of the Related Art Plastic materials have been widely used in recent years for various optical materials, particularly for spectacle lenses, because they are lightweight, rich in toughness and easy to dye. Optical materials, especially the performance required especially for spectacle lenses, in addition to low specific gravity, high transparency and low yellowness, high refractive index and high Abbe number as optical performance, high refractive index reduces the thickness of the lens Enable, and a high Abbe number reduces the chromatic aberration of the lens. The present inventors have a refractive index having a small thickness and a low chromatic aberration.
Various compounds having an episulfide structure capable of producing an optical material having an Abbe number of 35 or more and an optical material of 7 or more have been found, and patent applications have been filed earlier (JP-A-9-71580, JP-A-9-110979, 9-2555781
JP-A-11-130771 and the like. However, in these inventions, since the refractive index is mainly determined by the chemical structure of various compounds having an episulfide structure, in order to further increase the refractive index, modification of the chemical structure,
That is, it required the development of a new compound. Since much time and effort is required to develop this new compound, a method for easily increasing the refractive index has been desired.

[0003]

The problem to be solved by the present invention is to develop a technology for easily increasing the refractive index, and to provide a composition for an optical material having a high Abbe number and a high refractive index. An object of the present invention is to provide an optical material obtained by polymerizing and curing a composition.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to achieve the above object, and have found that one or more inorganic compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom can be obtained. The present invention was completed by finding that a high refractive index optical material can be obtained by polymerizing and curing an optical material composition containing a compound capable of reacting with the compound.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, an inorganic compound and an organic compound are as described in "Dictionary of Standard Chemical Terms" (edited by The Chemical Society of Japan (1991) Maruzen). That is, in the present invention, as described in the book, the inorganic compound refers to a compound containing no carbon and a relatively simple compound containing carbon. For example, relatively simple compounds containing carbon, such as carbon disulfide and potassium thiocyanate, are treated as inorganic compounds. Therefore, the organic compound in the present invention means other than the above-mentioned inorganic compound.

The composition for an optical material used in the present invention is:
It is a mixture containing at least one inorganic compound selected from inorganic compounds having a sulfur atom and / or a selenium atom and a compound capable of reacting with the compound as an essential component. Compounds that can react with one or more inorganic compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom cannot be said unconditionally because the reaction varies depending on the type of the inorganic compound. It is known to cover a wide variety of compounds, including saturated hydrocarbons, aromatic compounds, and hetero-organic compounds (for example, "Реакции сер"
ы с органицеsкимц соеgцне
нцямц ”, М.Г. Воронков et al., Ноь
осибирск, 1979). The compound capable of reacting with one or more inorganic compounds selected from the inorganic compounds having a sulfur atom and / or a selenium atom of the present invention can be a transparent resin that can be used as an optical material by polymerization and curing. There is no particular limitation.

One or more compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom are used in the composition in an amount of at least 1 wt%, preferably 2 w%.
t% or more, more preferably 3 wt% or more. If it is less than 1 wt%, almost no change in the refractive index is observed.

The inorganic compound having a sulfur atom and / or selenium atom of the present invention includes all inorganic compounds having at least one sulfur atom and / or selenium atom. It is preferable that the ratio of the total weight of atoms is 30% or more.
When this proportion is less than 30%, the effect of increasing the refractive index of the resin is reduced because the increase in the proportion of the weight of sulfur atoms and / or selenium atoms in the composition for optical materials is small. .

Specific examples of the inorganic compound having a sulfur atom include sulfur, hydrogen sulfide, carbon disulfide, carbon selenosulfide,
Ammonium sulfide, sulfur dioxide, sulfur oxides such as sulfur trioxide, thiocarbonate, sulfuric acid and its salts, hydrogen sulfate, sulfite, hyposulfite, persulfate, thiocyanate, thiosulfate, sulfur dichloride And halides such as thionyl chloride and thiophosgene, boron sulfide, nitrogen sulfide, silicon sulfide, phosphorus sulfide, arsenic sulfide, metal sulfide, and metal hydrosulfide. Preferred among these are sulfur, carbon disulfide, phosphorus sulfide, selenium sulfide, metal sulfide and metal hydrosulfide, more preferably sulfur, carbon disulfide and selenium sulfide, and particularly preferably sulfur. .

Specific examples of the inorganic compound having a selenium atom include selenium, hydrogen selenide, selenium dioxide, carbon diselenide, except for carbon selenosulfide and selenium sulfide, which are mentioned as specific examples of the inorganic compound having a sulfur atom. Selenium oxides such as ammonium selenide and selenium dioxide, selenic acid and its salts, selenous acid and its salts, hydrogen selenate, selenosulfuric acid and its salts, selenopirosulfuric acid and its salts, selenium tetrabromide, selenium oxychloride Such as halides, selenocyanate, boron selenide, phosphorus selenide,
Arsenic selenide, metal selenide, and the like. Of these, preferred are selenium, carbon diselenide, phosphorus selenide, and metal selenides, and particularly preferred are selenium and carbon diselenide. These inorganic compounds having a sulfur atom, inorganic compounds having a selenium atom,
They may be used alone or in combination of two or more.

When the composition for an optical material of the present invention is polymerized and cured, various reactions such as addition, substitution, insertion, and cyclization occur. These reactions vary depending on the types and amounts of the compounds constituting the composition for optical materials, but a curing catalyst can be added as needed to sufficiently cure. Examples of the curing catalyst include amines, phosphines, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, mineral acids, Lewis acids, organic acids, silicic acids, and tetrafluoride. Boric acids, peroxides, azo compounds, condensates of aldehydes and ammonia compounds, guanidines, thioureas, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, acidic phosphoric acid Esters can be mentioned. The following are typical examples of these.

(1) ethylamine, n-propylamine, sec-propylamine, n-butylamine,
c-butylamine, i-butylamine, tert-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, laurylamine, mystyrylamine, 1,2-dimethylhexylamine, 3-pentylamine, 2-ethylhexylamine ,
Allylamine, aminoethanol, 1-aminopropanol, 2-aminopropanol, aminobutanol, aminopentanol, aminohexanol, 3-ethoxypropylamine, 3-propoxypropylamine, 3-
Isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 3- (2-
Ethylhexyloxy) propylamine, aminocyclopentane, aminocyclohexane, aminonorbornene,
Primary amines such as aminomethylcyclohexane, aminobenzene, benzylamine, phenethylamine, α-phenylethylamine, naphthylamine and furfurylamine; ethylenediamine, 1,2-diaminopropane,
1,3-diaminopropane, 1,2-diaminobutane,
1,3-diaminobutane, 1,4-diaminobutane,
1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, dimethylaminopropylamine, diethylaminopropylamine, bis- (3-aminopropyl) ether, 1,2 -Bis- (3-aminopropoxy) ethane,
1,3-bis- (3-aminopropoxy) -2,2′-
Dimethylpropane, aminoethylethanolamine,
1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- Or 1,4-bisaminopropylcyclohexane, hydrogenated 4,4'-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine, N-aminoethyl Piperidine, N-aminopropylpiperidine, N-aminoethylmorpholine, N-aminopropylmorpholine,
Isophoronediamine, menthanediamine, 1,4-bisaminopropylpiperazine, o-, m- or p-
Phenylenediamine, 2,4- or 2,6-tolylenediamine, 2,4-toluenediamine, m-aminobenzylamine, 4-chloro-o-phenylenediamine,
Tetrachloro-p-xylylenediamine, 4-methoxy-6-methyl-m-phenylenediamine, m- or p-xylylenediamine, 1,5- or 2,6
-Naphthalenediamine, benzidine, 4,4'-bis (o-toluidine), dianisidine, 4,4'-diaminodiphenylmethane, 2,2- (4,4'-diaminodiphenyl) propane, 4,4'-diaminodiphenyl ether , 4,4'-thiodianiline, 4,4'-diaminodiphenylsulfone, 4,4'-diaminoditolylsulfone, methylenebis (o-chloroaniline), 3,9
-Bis (3-aminopropyl) 2,4,8,10-tetraoxaspiro [5,5] undecane, diethylenetriamine, iminobispropylamine, methyliminobispropylamine, bis (hexamethylene) triamine,
Triethylenetetramine, tetraethylenepentamine,
Pentaethylenehexamine, N-aminoethylpiperazine, N-aminopropylpiperazine, 1,4-bis (aminoethylpiperazine), 1,4-bis (aminopropylpiperazine), 2,6-diaminopyridine, bis (3,4 Primary polyamines such as -diaminophenyl) sulfone; diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine, dihexylamine, octyl Amine, di (2-ethylhexyl) amine, methylhexylamine, diallylamine, pyrrolidine, piperidine, 2-, 3-, 4-
Picoline, 2,4-, 2,6-, 3,5-lupetidine,
Diphenylamine, N-methylaniline, N-ethylaniline, dibenzylamine, methylbenzylamine, dinaphthylamine, pyrrole, indoline, indole,
Secondary amines such as morpholine; N, N'-dimethylethylenediamine, N, N'-dimethyl-1,2-diaminopropane, N, N'-dimethyl-1,3-diaminopropane, N, N'-dimethyl- 1,2-diaminobutane,
N, N′-dimethyl-1,3-diaminobutane, N,
N'-dimethyl-1,4-diaminobutane, N, N'-
Dimethyl-1,5-diaminopentane, N, N'-dimethyl-1,6-diaminohexane, N, N'-dimethyl-1,7-diaminoheptane, N, N'-diethylethylenediamine, N, N'- Diethyl-1,2-diaminopropane, N, N′-diethyl-1,3-diaminopropane, N, N′-diethyl-1,2-diaminobutane,
N, N′-diethyl-1,3-diaminobutane, N,
N'-diethyl-1,4-diaminobutane, N, N'-
Diethyl-1,6-diaminohexane, piperazine, 2
-Methylpiperazine, 2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1-di- (4-piperidyl) methane, 1,2-di- (4-piperidyl) ethane, 1,3-di -(4-piperidyl) propane, 1,
Secondary polyamines such as 4-di- (4-piperidyl) butane and tetramethylguanidine; trimethylamine, triethylamine, tri-n-propylamine, tri-iso
-Propylamine, tri-1,2-dimethylpropylamine, tri-3-methoxypropylamine, tri-n-
Butylamine, tri-iso-butylamine, tri-s
ec-butylamine, tri-pentylamine, tri-3
-Pentylamine, tri-n-hexylamine, tri-
n-octylamine, tri-2-ethylhexylamine, tri-dodecylamine, tri-laurylamine, dicyclohexylethylamine, cyclohexyldiethylamine, tri-cyclohexylamine, N, N-dimethylhexylamine, N-methyldihexylamine, N,
N-dimethylcyclohexylamine, N-methyldicyclohexylamine, N, N-diethylethanolamine, N, N-dimethylethanolamine, N-ethyldiethanolamine, triethanolamine, tribenzylamine, N, N-dimethylbenzylamine, diethyl Benzylamine, triphenylamine, N, N-dimethylamino-p-cresol, N, N-dimethylaminomethylphenol, 2- (N, N-dimethylaminomethyl) phenol, N, N-dimethylaniline, N, N −
Tertiary amines such as diethylaniline, pyridine, quinoline, N-methylmorpholine, N-methylpiperidine, 2- (2-dimethylaminoethoxy) -4-methyl-1,3,2-dioxabornane; tetramethylethylenediamine, pyrazine, N, N'-dimethylpiperazine, N,
N'-bis ((2-hydroxy) propyl) piperazine, hexamethylenetetramine, N, N, N ', N'-
Tetramethyl-1,3-butanamine, 2-dimethylamino-2-hydroxypropane, diethylaminoethanol, N, N, N-tris (3-dimethylaminopropyl) amine, 2,4,6-tris (N, N- Tertiary polyamines such as dimethylaminomethyl) phenol and heptamethylisobiguanide; imidazole, N-methylimidazole, 2-methylimidazole, 4-methylimidazole, N-ethylimidazole, 2-ethylimidazole, 4-ethylimidazole, N -Butylimidazole, 2-butylimidazole, N-undecylimidazole, 2-undecylimidazole, N-phenylimidazole, 2-phenylimidazole, N-benzylimidazole, 2-benzylimidazole, 1-benzyl-2-methylimid Sol, N- (2'-cyanoethyl) -2-methylimidazole, N- (2'-cyanoethyl) -2-undecylimidazole, N- (2'-cyanoethyl) -2-phenylimidazole, 3,3-bis -(2-ethyl-4-methylimidazolyl) methane,
2-mercaptoimidazole, 2-mercapto-N-methylimidazole, 2-mercaptobenzimidazole, 3-mercapto-4-methyl-4H-1,2,4-
Various imidazoles such as triazole, 5-mercapto-1-methyl-tetrazole, 2,5-dimercapto-1,3,4-thiadiazole, adducts of alkylimidazole and isocyanuric acid, and condensates of alkylimidazole and formaldehyde; 1 , 8-Diazabicyclo (5,4,0) undecene-7,1,5-diazabicyclo (4,3,0) nonene-5,6-dibutylamino-
1,8-diazabicyclo (5,4,0) undecene-7
And other amine-based compounds.

(2) Complexes of the amines of (1) with borane and boron trifluoride. (3) trimethylphosphine, triethylphosphine, tri-iso-propylphosphine, tri-n-
Butylphosphine, tri-n-hexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine, triphenylphosphine, tribenzylphosphine, tris (2-methylphenyl) phosphine, tris (3-methylphenyl) phosphine , Tris (4-methylphenyl) phosphine, tris (diethylamino) phosphine, tris (4-methylphenyl)
Phosphines such as phosphine, dimethylphenylphosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, ethyldiphenylphosphine, diphenylcyclohexylphosphine, and chlorodiphenylphosphine; (4) tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium acetate, tetraethylammonium chloride,
Tetraethylammonium bromide, tetraethylammonium acetate, tetra-n-butylammonium fluoride, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide,
Tetra-n-butylammonium iodide, tetra-
n-butylammonium acetate, tetra-n-butylammonium borohydride, tetra-n-butylammonium hexafluorophosphite, tetra-n
-Butylammonium hydrogensulfite, tetra-n-butylammonium tetrafluoroborate, tetra-n-butylammonium tetraphenylborate, tetra-n-butylammonium paratoluenesulfonate, tetra-n-hexylammonium chloride, tetra-n -Hexyl ammonium bromide, tetra-n-hexylammonium acetate,
Tetra-n-octylammonium chloride, tetra-n-octylammonium bromide, tetra-n-
Octyl ammonium acetate, trimethyl-n-octyl ammonium chloride, trimethyl decyl ammonium chloride, trimethyl dodecyl ammonium chloride, trimethyl cetyl ammonium chloride, trimethyl lauryl ammonium chloride, trimethyl benzyl ammonium chloride, trimethyl benzyl ammonium bromide, triethyl-n-octyl ammonium chloride, Triethylbenzylammonium chloride, triethylbenzylammonium bromide, tri-n-butyl-n-octylammonium chloride, tri-n-butylbenzylammonium fluoride, tri-n-butylbenzylammonium chloride, tri-n-butylbenzylammonium bromide, Bird -Butylbenzylammonium iodide, n-butyldimethylbenzylammonium chloride, n-octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, dodecyldimethylbenzylammonium chloride, cetyldimethylbenzylammonium chloride, lauryldimethylbenzylammonium chloride, methyltriphenyl Ammonium chloride, methyltribenzylammonium chloride, methyltriphenylammonium bromide, methyltribenzylammonium bromide, ethyltriphenylammonium chloride, ethyltribenzylammonium chloride, ethyltriphenylammonium bromide, ethyltribenzylammonium bromide n-butyltriphenylammonium chloride, n-butyltribenzylammonium chloride, n-butyltriphenylammonium bromide, n-butyltribenzylammonium bromide, 1-methylpyridinium chloride, 1-methylpyridinium bromide, 1-ethylpyridinium chloride, 1-ethylpyridinium bromide, 1-n-butylpyridinium chloride, 1
-N-butylpyridinium bromide, 1-n-hexylpyridinium chloride, 1-n-hexylpyridinium bromide, 1-n-octylpyridinium bromide, 1-n-dodecylpyridinium chloride, 1-
n-dodecylpyridinium bromide, 1-n-cetylpyridinium chloride, 1-n-cetylpyridinium bromide, 1-phenylpyridinium chloride, 1
-Phenylpyridinium bromide, 1-benzylpyridinium chloride, 1-benzylpyridinium bromide, 1-methylpicolinium chloride, 1-methylpicolinium bromide, 1-ethylpicolinium chloride, 1-ethylpicolinium bromide, 1-n-
Butylpicolinium chloride, 1-n-butylpicolinium bromide, 1-n-hexylpicolinium chloride, 1-n-hexylpicolinium bromide, 1
-N-octylpicolinium chloride, 1-n-octylpicolinium bromide, 1-n-dodecylpicolinium chloride, 1-n-dodecylpicolinium bromide, 1-n-cetylpicolinium chloride, 1-
quaternary ammonium salts such as n-cetylpicolinium bromide, 1-phenylpicolinium chloride, 1-phenylpicolinium bromide 1-benzylpicolinium chloride, 1-benzylpicolinium bromide; (5) tetramethylphosphonium chloride, tetramethylphosphonium bromide, tetraethylphosphonium chloride, tetraethylphosphonium bromide,
Tetra-n-butylphosphonium chloride, tetra-
n-butylphosphonium bromide, tetra-n-butylphosphonium iodide, tetra-n-hexylphosphonium bromide, tetra-n-octylphosphonium bromide, methyltriphenylphosphonium bromide, methyltriphenylphosphonium iodide, ethyltriphenylphosphonium bromide, Ethyltriphenylphosphonium iodide, n-butyltriphenylphosphonium bromide, n-butyltriphenylphosphonium iodide, n-hexyltriphenylphosphonium bromide, n-octyltriphenylphosphonium bromide, tetraphenylphosphonium bromide, tetrakishydroxymethylphosphonium chloride , Tetrakishydroxymethylphosphonium bromide, tetrakis Hydroxyethyl phosphonium chloride, phosphonium salts such as tetrakis hydroxybutyl phosphonium chloride. (6) trimethylsulfonium bromide, triethylsulfonium bromide, tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide, tri-n-butylsulfonium iodide, tri-
n-butylsulfonium tetrafluoroborate, tri-n-hexylsulfonium bromide, tri-n-
Sulfonium salts such as octylsulfonium bromide, triphenylsulfonium chloride, triphenylsulfonium bromide, and triphenylsulfonium iodide. (7) Iodonium salts such as diphenyliodonium chloride, diphenyliodonium bromide, and diphenyliodonium iodide. (8) Mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and carbonic acid and half esters thereof. (9) Lewis acids represented by boron trifluoride etherate of boron trifluoride. (10) Organic acids and their half esters. (11) Silicic acid, tetrafluoroboric acid.

(12) Cumyl peroxy neodecanoate, diisopropyl peroxy dicarbonate, diallyl peroxy dicarbonate, di-n-propyl peroxy dicarbonate, dimyristyl peroxy dicarbonate, cumyl peroxy neo hexanoate , Ter
t-hexylperoxy neodecanoate, tert-
Butyl peroxy neodecanoate, tert-hexyl peroxy neohexanoate, tert-butyl peroxy neohexanoate, 2,4-dichlorobenzoyl peroxide, benzoyl peroxide, dicumyl peroxide, di-ter- Peroxides such as butyl peroxide; peroxides such as cumene hydroperoxide and tert-butyl hydroperoxide; (13) 2,2′-azobis (4-methoxy-2,4-
Dimethylvaleronitrile), 2,2'-azobis (2-
Cyclopropylpropionitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-
Methylbutyronitrile), 1,1'-azobis (cyclohexane-1-carbonitrile), 1-[(1-cyano-1-methylethyl) azo] formamide, 2-phenylazo-4-methoxy-2,4- Dimethyl-valeronitrile 2,2'-azobis (2-methylpropane) 2,
Azo compounds such as 2′-azobis (2,4,4-trimethylpentane). (14) Reactant of acetaldehyde and ammonia, condensate of formaldehyde and paraylidine, condensate of acetaldehyde and paraylidine, reactant of formaldehyde and aniline, reactant of acetaldehyde and aniline, reactant of butyraldehyde and aniline, formaldehyde and acetaldehyde Aniline reactant, acetaldehyde / butyraldehyde / aniline reactant, butyraldehyde / monobutylamine condensate, butyraldehyde / butylideneaniline reactant, heptaldehyde / aniline reactant, tricrotonylidene-tetramine reaction And condensates of aldehydes and amine compounds, such as condensates of α-ethyl-β-propyl acrolein and aniline, and condensates of formaldehyde and alkylimidazole. (15) diphenyl guanidine, phenyl tolyl guanidine, phenyl xylyl guanidine, tolyl xylyl guanidine, diortolyl guanidine, ortho tolyl guanide, diphenyl guanidine phthalate, tetramethyl guanidine, ditotolyl guanidine salt of dicatechol boric acid, etc. Guanidines. (16) Thioureas such as thiocarbanilide, diortitolylthiourea, ethylenethiourea, diethylthiourea, dibutylthiourea, dilaurylthiourea, trimethylthiourea, dimethylethylthiourea, and tetramethylthiourea. (17) 2-mercaptobenzothiazole, dibenzothiazyldisulfide, cyclohexylamine salt of 2-mercaptobenzothiazole, 2- (2,4-dinitrophenylthio) benzothiazole, 2- (morpholinodithio) benzothiazole, 2- ( 2,6-dimethyl-4-
Morpholinothio) benzothiazole, N, N-diethylthiocarbamoyl-2-benzothiazolyl sulfide,
1,3-bis (2-benzothiazolylmercaptomethyl) urea, benzothiadiazylthiobenzoate, 2-
Thiazoles such as mercaptothiazoline, sodium salt of 2-mercaptobenzothiazole, zinc salt of 2-mercaptobenzothiazole, and complex salt of dibenzothiazyldisulfide and zinc chloride. (18) N-cyclohexyl-2-benzothiazylsulfenamide, N-tert-butyl-2-benzothiazylsulfenamide, N-tert-octyl-2-
Benzothiazylsulfenamide, N-oxydiethylene-2-benzothiazylsulfenamide, N, N-diethyl-2-benzothiazylsulfenamide, N, N
Sulfenamides such as diisopropyl-2-benzothiazylsulfenamide, N, N-dicyclohexyl-2-benzothiazylsulfenamide; (19) Tetramethylthiuram monosulfide, tetraethylthiuram monosulfide, tetrabutylthiuram monosulfide, dipentamethylenethiuram monosulfide, tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetrabutylthiuram disulfide, N, N'-dimethyl-N, N'-diphenylthiuram disulfide, N, N'-diethyl-N, N'-
Thiurams such as diphenylthiuram disulfide, dipentamethylenethiuram disulfide, dipentamethylenethiuram tetrasulfide, and cyclic thiuram. (20) sodium dimethyldithiocarbamate, sodium diethyldithiocarbamate, sodium dibutyldithiocarbamate, sodium pentamethylenedithiocarbamate, sodium cyclohexylethyldithiocarbamate, potassium dimethyldithiocarbamate, lead dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc diethyldithiocarbamate, Zinc dibutyldithiocarbamate, zinc dibenzyldithiocarbamate, zinc pentamethylenedithiocarbamate, zinc dimethylpentamethylenedithiocarbamate,
Zinc ethylphenyldithiocarbamate, bismuth dimethyldithiocarbamate, cadmium diethyldithiocarbamate, cadmium pentamethylenedithiocarbamate, selenium dimethyldithiocarbamate, selenium diethyldithiocarbamate, tellurium dimethyldithiocarbamate, tellurium diethyldithiocarbamate, iron dimethyldithiocarbamate, dimethyldithiocarbamate Copper, diethylammonium diethyldithiocarbamate, N, N-cyclohexylammonium dibutyldithiocarbamate, piperidine pentamethylenedithiocarbamate, cyclohexylethylammonium sodium cyclohexylethyldithiocarbamate, pipecoline methylpentamethylenedithiocarbamate, pentamethylenedithiocarbamilate Dithiocarbamates of the complex compounds of zinc and piperidine. (21) Xanthates such as sodium isopropylxanthogenate, zinc isopropylxanthogenate, zinc butylxanthogenate, dibutylxanthogenate disulfide and the like. (22) Mono- and / or dimethylphosphoric acid, mono-
And / or diethyl phosphate, mono- and / or dipropyl phosphate, mono- and / or dibutyl phosphate, mono- and / or dihexyl phosphate, mono- and / or dioctyl phosphate, mono- and / or didecyl phosphate, mono- Acidic phosphate esters such as-and / or didodecyl phosphate, mono- and / or diphenyl phosphate, mono- and / or dibenzyl phosphate, mono- and / or didecanol phosphate.

The polymerization catalyst for polymerizing and curing the composition for optical materials has been described above, but the compounds are not limited to these listed compounds as long as they exhibit polymerization curing. These may be used alone or as a mixture of two or more. The amount of the polymerization catalyst to be added depends on the composition of the optical material 1.
It is 0.0001 to 10.0 parts by weight, preferably 0.0005 to 5.0 parts by weight, based on 00 parts by weight.

In the present invention, the compound capable of reacting with one or more inorganic compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom includes a sulfur atom and / or a selenium atom.
Alternatively, it is preferable to use one or more organic compounds selected from organic compounds having a selenium atom in order to make the optical material obtained by polymerization and curing to have a higher refractive index.

When one or more organic compounds selected from organic compounds having a sulfur atom and / or a selenium atom are used, the composition for an optical material is preferably selected from inorganic compounds having a sulfur atom and / or a selenium atom. 1
It is preferable that the total of at least one kind of inorganic compound and the organic compound having a sulfur atom and / or a selenium atom is 30% by weight or more. When the content is less than 30% by weight, the increase in the content of sulfur atoms and / or selenium atoms in the composition for optical materials is small, and it is difficult to increase the refractive index of the resin.
Further, the ratio of the total weight of the inorganic compound having a sulfur atom and / or selenium atom to the total weight of the organic compound having a sulfur atom and / or selenium atom in the composition for an optical material is in the range of 0.001 to 2. Preferably, there is. More preferably, it is in the range of 0.005 to 1.5, and still more preferably in the range of 0.01 to 1. If this value is less than 0.001, the increase in the content of sulfur atoms and / or selenium atoms in the composition for optical materials will be small, making it difficult to increase the refractive index of the resin. If it exceeds 1, it becomes impossible to maintain the balance of various characteristics required for optical materials such as color tone, transparency, uniformity, heat resistance, light resistance and specific gravity. Further, the organic compound having a sulfur atom and / or a selenium atom includes all the organic compounds having a sulfur atom and / or a selenium atom, and is a proportion of the total weight of the sulfur atom and / or the selenium atom in the organic compound. Is preferably 5% or more.
If it is less than 5%, the solubility in an inorganic compound having a sulfur atom and / or a selenium atom will be low, and the effect of increasing the refractive index of the resin will be reduced.

Specific examples of the compound containing a sulfur atom include:
Mercaptans, sulfides except episulfide,
Polysulfides, thioketones, thioisocyanates, thiolsulfinates, thiolsulfonates, sulfilimines and derivatives thereof, sulfonium salts, sulfonium ylides, sulfones, sulfoxyimines and derivatives thereof, sulfinic acids and derivatives thereof Derivatives, sulfonic acids and their derivatives, and episulfide compounds can be mentioned. Specific examples of these are shown below.

(1) Methyl mercaptan, ethyl mercaptan, n-propyl mercaptan, n-butyl mercaptan, allyl mercaptan, n-hexyl mercaptan, n-octyl mercaptan, n-decyl mercaptan, n-dodecyl mercaptan, n-tetradecyl mercaptan , N-hexadecyl mercaptan, n-octadecyl mercaptan, cyclohexyl mercaptan, i
-Propyl mercaptan, t-butyl mercaptan, t
-Nonylmercaptan, t-dodecylmercaptan, phenylmercaptan, benzylmercaptan, 3-methylphenylmercaptan, 4-methylphenylmercaptan, 4-chlorobenzylmercaptan, 4-vinylbenzylmercaptan, 3-vinylbenzylmercaptan, methylmercaptopropionate 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 2-mercapto-1,3-propanediol, mercaptoacetic acid, mercaptoglycolic acid, mercaptopropionic acid, methanedithiol, 1,2-dimercaptoethane, 1,2-dimercaptopropane, 1,3-dimercaptopropane, 2,2-dimercaptopropane, 1,
4-dimercaptobutane, 1,6-dimercaptohexane, bis (2-mercaptoethyl) ether, bis (2
-Mercaptoethyl) sulfide, 1,2-bis (2-
Mercaptoethyloxy) ethane, 1,2-bis (2-
Mercaptoethylthio) ethane, 2,3-dimercapto-1-propanol, 1,3-dimercapto-2-propanol, 1,2,3-trimercaptopropane, 2-
Mercaptomethyl-1,3-dimercaptopropane, 2
-Mercaptomethyl-1,4-dimercaptobutane, 2
-(2-mercaptoethylthio) -1,3-dimercaptopropane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,4-dimercaptomethyl-1,5-dimercapto-3- Thiapentane,
4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5, 7-dimercaptomethyl-1,
11-dimercapto-3,6,9-trithiaundecane, 1,1,1-tris (mercaptomethyl) propane, tetrakis (mercaptomethyl) methane, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3- Mercaptopropionate),
Diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1,4-butanediol bis (2-mercaptoacetate), 1,4-butanediol bis (3
-Mercaptopropionate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate),
Pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), 1,2-dimercaptocyclohexane, 1,3-dimercaptocyclohexane, 1,
4-dimercaptocyclohexane, 1,3-bis (mercaptomethyl) cyclohexane, 1,4-bis (mercaptomethyl) cyclohexane, 2,5-bis (mercaptomethyl) -1,4-dithiane, 2,5-bis ( 2-mercaptoethyl) -1,4-dithiane, 2,5-bis (2-mercaptoethylthiomethyl) -1,4-dithiane, 2,5-bis (mercaptomethyl) -1-thiane,
2,5-bis (2-mercaptoethyl) -1-thiane,
Aliphatic mercaptans such as 2,5-bis (mercaptomethyl) thiophene and 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,3-bis (mercapto Methyl) benzene, 1,4-bis (mercaptomethyl) benzene,
2,2′-dimercaptobiphenyl, 4,4′-dimercaptobiphenyl, bis (4-mercaptophenyl) methane, 2,2-bis (4-mercaptophenyl) propane, bis (4-mercaptophenyl) ether, bis (4-mercaptophenyl) sulfide, bis (4-mercaptophenyl) sulfone, bis (4-mercaptomethylphenyl) methane, 2,2-bis (4-mercaptomethylphenyl) propane, bis (4-mercaptomethylphenyl) ether , Bis (4-mercaptomethylphenyl) sulfide, 4-hydroxythiophenol,
Aromatic cyclic mercaptans such as mercaptobenzoic acid; mercaptans such as; (2) dimethyl sulfide, diethyl sulfide, dipropyl sulfide, dibutyl sulfide, dipentyl sulfide, dicyclohexyl sulfide, diphenyl sulfide, methyl ethyl sulfide, methyl butyl sulfide, methyl Phenyl sulfide, alkyl sulfides such as ditrifluoromethyl sulfide, divinyl sulfide, diallyl sulfide,
Dipropargyl sulfide, distyryl sulfide, vinyl ethyl sulfide, vinyl phenyl sulfide, allyl phenyl sulfide, propargyl phenyl sulfide, 3- or 4-vinylphenyl thioethanol, 3
-Or 4-vinylbenzylthioethanol, sulfur-containing vinyl compounds such as 2-hydroxythioethyl acrylate, 2-hydroxythioethyl methacrylate, dithiirane, thiethane, 1,2-dithiethane, 1,3-dithiethane, trithiethane, thiolan, , 2-dithiolane,
1,3-dithiolane, 1,2,3-trithiolane, 1,
2,4-trithiolane, tetrathiolane, thiane, 1,
2-dithiane, 1,3-dithiane, 1,4-dithiane,
1,2,3-trithiane, 1,2,4-trithiane,
1,3,5-trithiane, 1,2,3,4-tetrathiane, 1,2,4,5-tetrathiane, pentathiane, tiepan, 1,2-dithiane, 1,3-dithiane,
1,4-dithiepane, 1,2,3-trithiepane, 1,
2,4-trithiepane, 1,2,5-trithiepane,
1,3,5-trithiepan, 1,2,3,4-tetrathiepan, 1,2,3,5-tetrathiepan, 1,2,2
4,5-tetrathiepan, 1,2,4,6-tetrathiepan, 1,2,3,4,5-pentathiepan, 1,2,2
Sulfur-containing cyclic sulfides excluding episulfide compounds, such as 3,4,6-pentathiepane, 1,2,3,5,6-pentatiepane, hexathiepanne, and sulfur-containing cyclic sulfides having a skeleton structure of the above cyclic compound; Ethylthioethanol, bis (2-hydroxyethyl) sulfide, 1,2-bis (2-hydroxyethylthio) ethane, 2- (2-hydroxyethylthio) -1,3-dihydroxypropane, 4-hydroxymethyl-1 , 8-Dihydroxy-3,6-dithiaoctane, 2,4-dihydroxymethyl-1,5-dihydroxy-3-thiapentane, 4,8-dihydroxymethyl-1,11-dihydroxy-3,6,9-trithiaundecane , 4,7-dihydroxymethyl-1,11-dihydroxy-3,6,9
-Trithiaundecane, 5,7-dihydroxymethyl-
Sulfur-containing alcohols such as 1,11-dihydroxy-3,6,9-trithiaundecane, 2,2′-thiodiphenol, 4,4′-thiodiphenol, 2,2′-thiodiglycolic acid, 3,3′-thiodipropionic acid, 2,2 ′
-Thiodibenzoic acid, sulfur-containing carboxylic acids such as 4,4'-thiodibenzoic acid, and further, acid anhydrides, acid halides,
Esters, amides, hydrazides, hydrazones, azides,
Derivatives such as alkali metal salts and alkaline earth metal salts,
Bis (β-epoxypropyl) sulfide, bis (β-
Epoxypropylthio) methane, 1,2-bis (β-epoxypropylthio) ethane, 1,3-bis (β-epoxypropylthio) propane, 1,2-bis (β-epoxypropylthio) propane, 1- (Β-epoxypropylthio) -2- (β-epoxypropylthiomethyl)
Propane, 1,4-bis (β-epoxypropylthio)
Butane, 1,3-bis (β-epoxypropylthio) butane, 1- (β-epoxypropylthio) -3- (β-
Epoxypropylthiomethyl) butane, 1,5-bis (β-epoxypropylthio) pentane, 1- (β-epoxypropylthio) -4- (β-epoxypropylthiomethyl) pentane, 1,6-bis (β -Epoxypropylthio) hexane, 1- (β-epoxypropylthio) -5- (β-epoxypropylthiomethyl) hexane, 1- (β-epoxypropylthio) -2-[(2-
β-epoxypropylthioethyl) thio] ethane, 1-
(Β-epoxypropylthio) -2-[[2- (2-β
-Epoxypropylthioethyl) thioethyl] thio] ethane, tetrakis (β-epoxypropylthiomethyl)
Methane, 1,1,1-tris (β-epoxypropylthiomethyl) propane, 1,5-bis (β-epoxypropylthio) -2- (β-epoxypropylthiomethyl)
-3-Thiapentane, 1,5-bis (β-epoxypropylthio) -2,4-bis (β-epoxypropylthiomethyl) -3-thiapentane, 1- (β-epoxypropylthio) -2,2- Bis (β-epoxypropylthiomethyl) -4-thiahexane, 1,5,6-tris (β
-Epoxypropylthio) -4- (β-epoxypropylthiomethyl) -3-thiahexane, 1,8-bis (β
-Epoxypropylthio) -4- (β-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epoxypropylthio) -4,5bis (β-epoxypropylthiomethyl) -3 , 6-Dithiaoctane, 1,8-bis (β-epoxypropylthio) -4,
4-bis (β-epoxypropylthiomethyl) -3,6
-Dithiaoctane, 1,8-bis (β-epoxypropylthio) -2,4,5-tris (β-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epoxypropylthio) -2,5-bis (β-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,9-bis (β-epoxypropylthio) -5
(Β-epoxypropylthiomethyl) -5-[(2-β
-Epoxypropylthioethyl) thiomethyl] -3,7
-Dithianonane, 1,10-bis (β-epoxypropylthio) -5,6-bis [(2-β-epoxypropylthioethyl) thio] -3,6,9-trithiadecane,
1,11-bis (β-epoxypropylthio) -4,8
-Bis (β-epoxypropylthiomethyl) -3,6
9-trithiaundecane, 1,11-bis (β-epoxypropylthio) -5,7-bis (β-epoxypropylthiomethyl) -3,6,9-trithiaundecane,
1,11-bis (β-epoxypropylthio) -5,7
-[(2-β-epoxypropylthioethyl) thiomethyl] -3,6,9-trithiaundecane, 1,11-bis (β-epoxypropylthio) -4,7-bis (β-
(Epoxypropylthiomethyl) -3,6,9-trithiaundecane, 1,3 and 1,4-bis (β-epoxypropylthio) cyclohexane, 1,3 and 1,4-
Bis (β-epoxypropylthiomethyl) cyclohexane, bis [4- (β-epoxypropylthio) cyclohexyl] methane, 2,2-bis [4- (β-epoxypropylthio) cyclohexyl] propane, bis [4-
(Β-epoxypropylthio) cyclohexyl] sulfide, 2,5-bis (β-epoxypropylthiomethyl) -1,4-dithiane, 2,5-bis (β-epoxypropylthioethylthiomethyl) -1,4 -Dithiane,
1,3 and 1,4-bis (β-epoxypropylthio) benzene, 1,3 and 1,4-bis (β-epoxypropylthiomethyl) benzene, bis [4- (β-epoxypropylthio) phenyl] Methane, 2,2-bis [4- (β-epoxypropylthio) phenyl] propane, bis [4- (β-epoxypropylthio) phenyl] sulfide, bis [4- (β-epoxypropylthio) phenyl] sulfone , Sulfur-containing epoxies such as 4,4′-bis (β-epoxypropylthio) biphenyl, thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, bis [(4-isocyanatomethyl) phenyl] sulfide,
2,5-diisocyanato-1,4-dithiane, 2,5-
Sulfides excluding the episulfide compounds listed above, such as sulfur-containing isocyanates such as diisocyanatomethyl-1,4-dithiane, 2,5-diisocyanatomethylthiophene, dithiodiethyldiisocyanate, and dithiodipropyldiisocyanate; (3) Polysulfides in which a part or all of the sulfide bond of the compound of (1) and the compound of (2) having a sulfide bond is replaced by a polysulfide bond such as disulfide or trisulfide;
(4) dimethylthioketone, diethylthioketone, dibutylthioketone, dicyclohexylthioketone, diphenylthioketone, methylethylthioketone, methylbutylthioketone, methylphenylthioketone, vinylphenylthioketone, allylphenylthioketone, propargyl Phenyl thioketone, ditrifluoromethyl thioketone, cyclopropanethione, cyclobutanethione, cyclopentanethione, cyclohexanethione, cyclopropanethione, bismuthiol 2, ε-thiocaprolactam, thiourea, 2-imidazolidinthione, 1,1′-
Thioketones such as thiocarbonyldiimidazole, diethyltrithiocarbonate, diphenyltrithiocarbonate,

(5) methylthioisocyanate, ethylthioisocyanate, propylthioisocyanate, i
so-propylthioisocyanate, n-butylthioisocyanate, sec-butylthioisocyanate, t
tert-butylthioisocyanate, pentylthioisocyanate, hexylthioisocyanate, octylthioisocyanate, dodecylthioisocyanate, cyclohexylthioisocyanate, phenylthioisocyanate, toluylthioisocyanate, ethylenedithioisocyanate, tetramethylenedithioisocyanate, hexamethylenedithioisocyanate, cyclohexanedithio Isocyanate, 1,3-bis (thioisocyanatomethyl) cyclohexane, 1,4-bis (thioisocyanatomethyl) cyclohexane, isophorone dithioisocyanate, 2,6-bis (thioisocyanatomethyl) decahydronaphthalene, lysine trithio Isocyanate, 1,3-phenylenedithioisocyanate, 1,
4-phenylenedithioisocyanate, 4,4′-dithioisocyanatobiphenyl, 4,4′-dithioisocyanato-3,3′-dimethylbiphenyl, 1,1′-methylenebis (4-thioisocyanatobenzene), 1, 1 '
-Methylenebis (3-methyl-4-thioisocyanatobenzene), m-xylylenedithioisocyanate, p-
Xylylenedithioisocyanate, 1,3-bis (2-
Thioisocyanato-2-propyl) benzene, 2,6-
Thiosocyanates such as bis (thioisocyanatomethyl) naphthalene, dimers and cyclized trimers of these polythioisocyanates by a Bullet-type reaction, and addition of alcohols or thiols with these polythioisocyanates Polythioisocyanates,
(6) dimethylthiol sulfinate, diethylthiol sulfinate, dibutylthiol sulfinate, dicyclohexylthiol sulfinate, diphenylthiol sulfinate, methylethylthiol sulfinate, methylbutylthiol sulfinate,
Methylphenylthiol sulfinate, vinylphenylthiol sulfinate, allylphenylthiol sulfinate, 1,2-dithiolan-1-oxide,
Thiol sulfinates such as 1,2-dithiane-1-oxide, (7) dimethylthiol sulfonate, diethylthiol sulfonate, dibutylthiol sulfonate, dicyclohexylthiol sulfonate, diphenylthiol sulfonate, methylethylthiol sulfonate , Methylbutylthiol sulfonate, methylphenylthiol sulfonate, vinylphenylthiol sulfonate, allylphenylthiol sulfonate, 1,2-dithiolan-1,1-dioxide, 1,2
Thiolsulfonates such as -dithiane-1,1-dioxide; (8) dimethylsulfoxide, diethylsulfoxide, dibutylsulfoxide, dicyclohexylsulfoxide, diphenylsulfoxide, dibenzylsulfoxide, dip-tolylsulfoxide, bis (4-chlorophenyl) sulfoxide , Methylethylsulfoxide, methylmethylthiomethylsulfoxide, methylbutylsulfoxide, methylphenylsulfoxide, vinylphenylsulfoxide, allylphenylsulfoxide,
Propargyl phenyl sulfoxide, thiirane oxide,
Thietane oxide, thiolane oxide, thiane oxide, 1,4-dithiane oxide, 1,4-dithiane-
Sulfoxides such as 1,4-dioxide, (9) sulfilimines such as dimethylsulfilimine, dibutylsulfilimine, diphenylsulfilimine, ditolylsulfonium butylide, and N-alkyl-substituted products thereof; Derivatives such as betaine, (10) trimethylsulfonium bromide, trimethylsulfonium iodide, trimethisulfonium hydroxide, triethylsulfonium bromide, tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide, tri-n-butylsulfonium ioda , Tri-n-butylsulfonium tetrafluoroborate, tri-n-hexylsulfonium bromide, tri-n-octylsulfonium bromide, triphenylsulfonium Sulfonium salts such as muchloride, triphenylsulfonium bromide, triphenylsulfonium iodide, triphenylsulfonium tetrafluoroborate, (2-carboxyethyl) dimethylsulfonium chloride, 2-carboxyethyl) dimethylsulfonium bromide, and (11) dimethylsulfonium methylide , Sulfonium ylides such as dimethyloxosulfonium methylide, diphenylsulfonium methylide, diphenylsulfonium butylide, (1
2) dimethyl sulfone, diethyl sulfone, dibutyl sulfone, dicyclohexyl sulfone, diphenyl sulfone, methyl ethyl sulfone, methyl butyl sulfone, methyl phenyl sulfone, vinyl phenyl sulfone, allyl phenyl sulfone, propargyl phenyl sulfone, episulfone, trimethylene sulfone, sulfolane, Sulfolene, tetramethylene sulfone, 1,4-dithiane-
Sulfones such as 1,1-dioxide and 1,4-dithianetetraoxide, (13) dimethylsulfoximine,
Diethylsulfoximine, dibutylsulfoximine, dicyclohexylsulfoximine, diphenylsulfoximine, methylethylsulfoximine, methylbutylsulfoximine, methylphenylsulfoximine, vinylphenylsulfoximine, allylphenylsulfoximine, Sulfoximines such as propargylphenylsulfoximine, and N-
Alkyl-substituted products and derivatives such as betaine, (14) methanesulfinic acid, ethanesulfinic acid, butanesulfinic acid, dodecanesulfinic acid, hydroxymethanesulfinic acid, benzenesulfinic acid, o-toluenesulfinic acid, m-toluenesulfinic acid, p -Toluenesulfinic acid, ethylbenzenesulfinic acid, butylbenzenesulfinic acid, dodecylbenzenesulfinic acid, vinylbenzenesulfinic acid, p-phenolsulfinic acid, o-cresolsulfinic acid, p-chlorobenzenesulfinic acid, p-acetamidobenzenesulfinic acid, biphenyl Sulfinic acids such as sulfinic acid, α-naphthalenesulfinic acid and β-naphthalenesulfinic acid; and acid anhydrides, acid halides, esters, amides, hydrazides and hydrazides of these. Derivatives such as drazone, azide, alkali metal salts and alkaline earth metal salts, (1
5) methanesulfonic acid, ethanesulfonic acid, butanesulfonic acid, dodecanesulfonic acid, hydroxymethanesulfonic acid, benzenesulfonic acid, o-toluenesulfonic acid,
m-toluenesulfonic acid, p-toluenesulfonic acid, ethylbenzenesulfonic acid, butylbenzenesulfonic acid,
Dodecylbenzenesulfonic acid, vinylbenzenesulfonic acid, p-phenolsulfonic acid, o-cresolsulfonic acid, p-chlorobenzenesulfonic acid, p-acetamidobenzenesulfonic acid, metanilic acid, sulfanilic acid,
Sulfonic acids such as 4B-acid, diaminostilbene sulfonic acid, biphenyl sulfonic acid, α-naphthalene sulfonic acid, β-naphthalene sulfonic acid, peric acid, lauric acid, and phenyl J acid; further, acid anhydrides, acid halides, Derivatives such as esters, amides, hydrazides, hydrazones, azides, alkali metal salts and alkaline earth metal salts.

The following compounds are exemplified as episulfide compounds. Compound having at least one structure represented by the following formula (1) in one molecule

[0022]

Embedded image (Wherein, R ¹ is a hydrocarbon having 1 to 10 carbon atoms, R ² , R ³
And R ⁴ each represent a hydrocarbon group having 1 to 10 carbon atoms or hydrogen. Y represents O, S, Se or Te.
m = 1 to 5, n = 0 to 5, p = 0 or 1. The compound having at least one structure represented by the above formula (1) per molecule used in the present invention exhibits a high refractive index, a high Abbe number and a good balance between the two when used as an optical material. It is. R ¹ in the formula (1) is preferably methylene or ethylene, and R ² , R ³ and R ⁴ in the formula (1) are preferably hydrogen or a methyl group. More preferably, R ¹ is methylene, and R ² , R ³ and R
⁴ is hydrogen. Y represents O, S, Se, or Te, but S, Se, or Te is preferable if a higher refractive index is desired. m represents 1 to 5, preferably m
Is 1 or 2, more preferably m is 1. n is 0
5, preferably n is from 0 to 4, more preferably n
Is 0 or 1. p represents 0 or 1, but is preferably 1.

The compound of the present invention having at least one structure represented by the formula (1) in one molecule includes all organic compounds satisfying this condition.
The following are mentioned. (A) Organic compound having epithio group (B) Organic compound having epithioalkyloxy group (C) Organic compound having epithioalkylthio group (D) Organic compound having epithioalkyl seleno group (E) Epithioalkyl Organic compound having telluro group The above organic compounds (A), (B), (C), (D) and (E) are chain compounds, branched compounds, aliphatic cyclic compounds, aromatic compounds, or nitrogen. , Oxygen, sulfur, selenium,
Having a heterocyclic compound containing a tellurium atom as a main skeleton and having an epithio group, an epithioalkyloxy group, an epithioalkylthio group, an epithioalkylseleno group, and an epithioalkyltelluro group simultaneously in one molecule. It doesn't matter. Further, these compounds may contain a bond such as sulfide, selenide, telluride, ether, sulfone, ketone, ester, amide, or urethane in the molecule.

A preferred specific example of (A) an organic compound having one or more epithio groups is a compound having one or more epoxy groups substituted by an epithio group in a compound having an epoxy group (not a glycidyl group). I can give it. Taking a more specific example method, the following can be given as typical examples. Organic compound having a chain aliphatic skeleton: 1,1-bis (epithioethyl) methane 1- (epithioethyl) -1- (β-epithiopropyl) methane 1,1-bis (β-epithiopropyl) methane 1- (Epithioethyl) -1- (β-epithiopropyl) ethane, 1,2-bis (β-epithiopropyl) ethane 1- (epithioethyl) -3- (β-epithiopropyl) butane, 1,3-bis (Β-epithiopropyl) propane, 1- (epithioethyl) -4- (β-epithiopropyl) pentane 1,4-bis (β-epithiopropyl) butane, 1- (epithioethyl) -5- (β- Epithiopropyl) hexane, 1- (epithioethyl) -2
-(Γ-epithiobutylthio) ethane, 1- (epithioethyl) -2- [2- (γ-epithiobutylthio) ethylthio] ethane, tetrakis (β-epithiopropyl)
Methane, 1,1,1-tris (β-epithiopropyl)
Propane, 1,3-bis (β-epithiopropyl) -1
-(Β-epithiopropyl) -2-thiapropane, 1,
5-bis (β-epithiopropyl) -2,4-bis (β
-Epithiopropyl) -3-thiapentane and the like. Compound having an aliphatic cyclic skeleton: 1,3 or 1,4-
Bis (epithioethyl) cyclohexane, 1,3 or 1,4-bis (β-epithiopropyl) cyclohexane, 2,5-bis (epithioethyl) -1,4-dithiane, 2,5-bis (β-epithiopropyl ) -1,4-
Compounds having one aliphatic cyclic structure such as dithiane, 4-epithioethyl-1,2-cyclohexene sulfide, 4-epoxy-1,2-cyclohexene sulfide, and 2,2-bis [4- (epithioethyl) cyclohexyl] Propane, 2,2-bis [4- (β-epithiopropyl) cyclohexyl] propane, bis [4- (epithioethyl) cyclohexyl] methane, bis [4- (β
Compounds having two aliphatic cyclic structures, such as -epithiopropyl) cyclohexyl] methane, bis [4- (β-epithiopropyl) cyclohexyl] sulfide, bis [4- (epithioethyl) cyclohexyl] sulfide, and the like. Compounds having an aromatic skeleton: compounds having one aromatic skeleton such as 1,3 or 1,4-bis (epithioethyl) benzene, 1,3 or 1,4-bis (β-epithiopropyl) benzene, , Bis [4- (epithioethyl)
Phenyl] methane, bis [4- (β-epithiopropyl) phenyl] methane, 2,2-bis [4- (epithioethyl) phenyl] propane, 2,2-bis [4- (β
-Epithiopropyl) phenyl] propane, bis [4-
(Epithioethyl) phenyl] sulfide, bis [4-
(Β-epithiopropyl) phenyl] sulfide, bis [4- (epithioethyl) phenyl] sulfone, bis [4- (β-epithiopropyl) phenyl] sulfone, 4,4′-bis (epithioethyl) biphenyl,
4,4′-bis (β-epithiopropyl) biphenyl,
And other compounds having two aromatic skeletons. Further, compounds in which at least one hydrogen of the epithio group of these compounds is substituted with a methyl group are also exemplified.

Preferred specific examples of the organic compound (B) having one or more epithioalkyloxy groups include one of the glycidyl groups of an epoxy compound derived from epihalohydrin.
Compounds in which at least one is substituted with an epithioalkyloxy group (thioglycidyl group) can be mentioned as a typical example. Specific examples of the epoxy compound include those produced by condensing epihalohydrin with polyhydric phenol compounds such as hydroquinone, catechol, resorcinol, bisphenol A, bisphenol F, bisphenol sulfone, bisphenol ether, bisphenol sulfide, halogenated bisphenol A, and novolak resin. Phenolic epoxy compounds; ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, Pentyl glycol, glycerin, trimethylolpropane trimethacrylate, pentaerythritol, 1,3- Is a polyhydric alcohol compound such as 1,4-cyclohexanediol, 1,3- or 1,4-cyclohexanedimethanol, hydrogenated bisphenol A, bisphenol A / ethylene oxide adduct, bisphenol A / propylene oxide adduct, and epihalohydrin. Alcoholic epoxy compounds produced by condensation; adipic acid, sebacic acid, dodecanedicarboxylic acid, dimer acid, phthalic acid, iso, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, hexahydroisophthalic acid, Hexahydroterephthalic acid, hetonic acid, nadic acid, maleic acid, succinic acid, fumaric acid, trimellitic acid, benzenetetracarboxylic acid, benzophenonetetracarboxylic acid,
Glycidyl ester epoxy compounds produced by condensation of polyhalocarboxylic acid compounds such as naphthalene dicarboxylic acid and diphenyl dicarboxylic acid with epihalohydrin; ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, bis-
(3-aminopropyl) ether, 1,2-bis- (3
-Aminopropoxy) ethane, 1,3-bis- (3-aminopropoxy) -2,2'-dimethylpropane, 1,
2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- or 1 4,4-bisaminopropylcyclohexane, hydrogenated 4,4'-diaminodiphenylmethane, isophoronediamine, 1,4-bisaminopropylpiperazine, m- or p-phenylenediamine,
2,4- or 2,6-tolylenediamine, m- or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylether, 2,2
Primary diamines such as-(4,4'-diaminodiphenyl) propane, N, N'-dimethylethylenediamine, N,
N'-dimethyl-1,2-diaminopropane, N, N '
-Dimethyl-1,3-diaminopropane, N, N′-dimethyl-1,2-diaminobutane, N, N′-dimethyl-1,3-diaminobutane, N, N′-dimethyl-1,
4-diaminobutane, N, N'-dimethyl-1,5-diaminopentane, N, N'-dimethyl-1,6-diaminohexane, N, N'-dimethyl-1,7-diaminoheptane, N, N '-Diethylethylenediamine, N,
N'-diethyl-1,2-diaminopropane, N, N '
-Diethyl-1,3-diaminopropane, N, N′-diethyl-1,2-diaminobutane, N, N′-diethyl-1,3-diaminobutane, N, N′-diethyl-1,
4-diaminobutane, N, N′-diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine,
2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1-di- (4-piperidyl) -methane,
1,2-di- (4-piperidyl) -ethane, 1,3-di- (4-piperidyl) -propane, 1,4-di- (4-
Amine-based epoxy compounds produced by condensation of a secondary diamine such as piperidyl) -butane and epihalohydrin,
Urethane-based epoxy compounds produced from the above-mentioned polyhydric alcohols, phenol compounds, diisocyanates, glycidol and the like can be mentioned. If a more specific example method is used, the following can be given as typical examples.

Organic compounds having a chain aliphatic skeleton: bis (β-epithiopropyloxy) ether, bis (β-epithiopropyloxy) methane, 1,2-bis (β-epithiopropyloxy) ethane, 1,3-bis (β-epithiopropyloxy) propane, 1,2-bis (β-epithiopropyloxy) propane, 1- (β-epithiopropyloxy) -2- (β-epithiopropyloxymethyl ) Propane, 1,4-bis (β-epithiopropyloxy) butane, 1,3-bis (β-epithiopropyloxy) butane, 1- (β-epithiopropyloxy)
-3- (β-epithiopropyloxymethyl) butane,
1,5-bis (β-epithiopropyloxy) pentane, 1- (β-epithiopropyloxy) -4- (β-
Epithiopropyloxymethyl) pentane, 1,6-bis (β-epithiopropyloxy) hexane, 1- (β
-Epithiopropyloxy) -5- (β-epithiopropyloxymethyl) hexane, 1- (β-epithiopropyloxy) -2-[(2-β-epithiopropyloxyethyl) oxy] ethane, 1 -(Β-epithiopropyloxy) -2-[[2- (2-β-epithiopropyloxyethyl) oxyethyl] oxy] ethane, tetrakis (β-epithiopropyloxymethyl) methane,
1,1,1-tris (β-epithiopropyloxymethyl) propane, 1,5-bis (β-epithiopropyloxy) -2- (β-epithiopropyloxymethyl)-
3-Thiapentane, 1,5-bis (β-epithiopropyloxy) -2,4-bis (β-epithiopropyloxymethyl) -3-thiapentane, 1- (β-epithiopropyloxy) -2, 2-bis (β-epithiopropyloxymethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3-thiahexane, 1 , 8
-Bis (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy)-
4,5 bis (β-epithiopropyloxymethyl)-
3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -4,4-bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-
Bis (β-epithiopropyloxy) -2,4,5-tris (β-epithiopropyloxymethyl) -3,6-
Dithiaoctane, 1,8-bis (β-epithiopropyloxy) -2,5-bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,9-bis (β
-Epithiopropyloxy) -5- (β-epithiopropyloxymethyl) -5-[(2-β-epithiopropyloxyethyl) oxymethyl] -3,7-dithianonane, 1,10-bis (β -Epithiopropyloxy)-
5,6-bis [(2-β-epithiopropyloxyethyl) oxy] -3,6,9-trithiadecane, 1,11
-Bis (β-epithiopropyloxy) -4,8-bis (β-epithiopropyloxymethyl) -3,6,9-
Trithiaundecane, 1,11-bis (β-epithiopropyloxy) -5,7-bis (β-epithiopropyloxymethyl) -3,6,9-trithiaundecane,
1,11-bis (β-epithiopropyloxy) -5
7-[(2-β-epithiopropyloxyethyl) oxymethyl] -3,6,9-trithiaundecane, 1,1
1-bis (β-epithiopropyloxy) -4,7-bis (β-epithiopropyloxymethyl) -3,6,9
-Trithiaundecane and the like. Compound having an aliphatic cyclic skeleton: 1,3 or 1,4-
Bis (β-epithiopropyloxy) cyclohexane,
1,3 or 1,4-bis (β-epithiopropyloxymethyl) cyclohexane, bis [4- (β-epithiopropyloxy) cyclohexyl] methane, 2,2-bis [4- (β-epithiopropyl) Oxy) cyclohexyl] propane, bis [4- (β-epithiopropyloxy) cyclohexyl] sulfide, 2,5-bis (β-
Epithiopropyloxymethyl) -1,4-dithiane,
2,5-bis (β-epithiopropyloxyethyloxymethyl) -1,4-dithiane and the like. Compound having an aromatic skeleton: 1,3 or 1,4-bis (β-epithiopropyloxy) benzene, 1,3 or 1,4-bis (β-epithiopropyloxymethyl)
A compound having one aromatic skeleton such as benzene, bis [4- (β-epithiopropyl) phenyl] methane,
2,2-bis [4- (β-epithiopropylthio) phenyl] propane, bis [4- (β-epithiopropylthio) phenyl] sulfide, bis [4- (β-epithiopropylthio) phenyl] Compounds having two aromatic skeletons such as sulfone and 4,4′-bis (β-epithiopropylthio) biphenyl are exemplified. Further, compounds in which at least one hydrogen of the epithio group of these compounds is substituted with a methyl group are also exemplified.

(C) Preferred specific examples of the organic compound having one or more epithioalkylthio groups include a compound having a mercapto group and an epoxyalkylthio group of an epoxy compound derived from epihalohydrin (specifically, β-
Compounds in which one or more of (epoxypropylthio groups) are substituted with epithioalkylthio groups can be mentioned as typical examples. If a more specific example method is used, the following can be given as typical examples. Organic compound having a linear aliphatic skeleton: bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide, bis (β-epithiopropyl) trisulfide, bis (β-epithiopropylthio) Methane, bis (β-epithiopropyldithio) methane, bis (β-epithiopropyldithio) ethane, bis (β-epithiopropyldithioethyl) sulfide, bis (β-
Epithiopropyldithioethyl) disulfide, 1,2
-Bis (β-epithiopropylthio) ethane, 1,3-
Bis (β-epithiopropylthio) propane, 1,2-
Bis (β-epithiopropylthio) propane, 1- (β
-Epithiopropylthio) -2-([beta] -epithiopropylthiomethyl) propane, 1,4-bis ([beta] -epithiopropylthio) butane, 1,3-bis ([beta] -epithiopropylthio) butane, 1- (β-epithiopropylthio) -3- (β-epithiopropylthiomethyl) butane, 1,5-bis (β-epithiopropylthio) pentane, 1- (β-epithiopropylthio)- 4- (β-epithiopropylthiomethyl) pentane, 1,6-bis (β-epithiopropylthio) hexane, 1- (β-epithiopropylthio) -5- (β-epithiopropylthiomethyl) Hexane, 1- (β-epithiopropylthio) -2-[(2-β-epithiopropylthioethyl)
Thio] ethane, 1- (β-epithiopropylthio) -2
-[[2- (2-β-epithiopropylthioethyl) thioethyl] thio] ethane tetrakis (β-epithiopropylthiomethyl) methane, tetrakis (β-epithiopropyldithiomethyl)
Methane, 1,1,1-tris (β-epithiopropylthiomethyl) propane, 1,2,3-tris (β-epithiopropyldithio) propane, 1,5-bis (β-epithiopropylthio) -2- (β-epithiopropylthiomethyl) -3-thiapentane, 1,5-bis (β-epithiopropylthio) -2,4-bis (β-epithiopropylthiomethyl) -3-thiapentane, 1,6-bis (β-epithiopropyldithiomethyl) -2- (β-epithiopropyldithioethylthio) -4-thiahexane, 1- (β-epithiopropylthio) -2,2-bis (β -Epithiopropylthiomethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropylthio)
-4- (β-epithiopropylthiomethyl) -3-thiahexane, 1,8-bis (β-epithiopropylthio)
-4- (β-epithiopropylthiomethyl) -3,6-
Dithiaoctane, 1,8-bis (β-epithiopropylthio) -4,5bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio)- 4,4-bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8
-Bis (β-epithiopropylthio) -2,4,5-tris (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -2, 5-bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,9-bis (β-epithiopropylthio) -5- (β-epithiopropylthiomethyl) -5-[(2 -Β-epithiopropylthioethyl) thiomethyl] -3,7-dithianonane, 1,10
-Bis (β-epithiopropylthio) -5,6-bis [(2-β-epithiopropylthioethyl) thio]-
3,6,9-trithiadecane, 1,11-bis (β-epithiopropylthio) -4,8-bis (β-epithiopropylthiomethyl) -3,6,9-trithiaundecane, 1,11 -Bis (β-epithiopropylthio)-
5,7-bis (β-epithiopropylthiomethyl)-
3,6,9-trithiaundecane, 1,11-bis (β
-Epithiopropylthio) -5,7-[(2-β-epithiopropylthioethyl) thiomethyl] -3,6,9-
Trithiaundecane, 1,11-bis (β-epithiopropylthio) -4,7-bis (β-epithiopropylthiomethyl) -3,6,9-trithiaundecane and the like can be mentioned. Chain compound having an ester group and an epithioalkylthio group: tetra [2- (β-epithiopropylthio) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylthio) acetylmethyl ] Propane, tetra [2- (β-epithiopropylthiomethyl) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylthiomethyl) acetylmethyl] propane and the like. Compound having an aliphatic cyclic skeleton: 1,3 or 1,4-
Bis (β-epithiopropylthio) cyclohexane,
1,3 or 1,4-bis (β-epithiopropylthiomethyl) cyclohexane 2,5-bis (β-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis (β-epithio Propyldithiomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4-dithiane, and other compounds having one aliphatic cyclic skeleton; (Β-epithiopropylthio) cyclohexyl] methane, 2,2-bis [4-
(Β-epithiopropylthio) cyclohexyl] propane, bis [4- (β-epithiopropylthio) cyclohexyl] sulfide, 2,2-bis [4- (β-epithiopropylthio) cyclohexyl] propane, bis [ 4
-(Β-epithiopropylthio) cyclohexyl] sulfide and the like, and compounds having two aliphatic cyclic skeletons. Compound having an aromatic skeleton: 1,3 or 1,4-bis (β-epithiopropylthio) benzene, 1,3 or 1,4-bis (β-epithiopropylthiomethyl) benzene, 1,3 or Compounds having one aromatic skeleton such as 1,4-bis (β-epithiopropyldithiomethyl) benzene, and bis [4- (β-epithiopropylthio)
Phenyl] methane, 2,2-bis [4- (β-epithiopropylthio) phenyl] propane, bis [4-
(Β-epithiopropylthio) phenyl] sulfide,
Bis [4- (β-epithiopropylthio) phenyl]
Compounds having two aromatic skeletons such as sulfone and 4,4′-bis (β-epithiopropylthio) biphenyl are exemplified. Further, specific examples thereof include compounds in which at least one hydrogen of the β-epithiopropyl group of these compounds is substituted with a methyl group.

(D) Preferred specific examples of the organic compound having an epithioalkylseleno group include selenium compounds such as metal selenium, alkali metal selenide, alkali metal selenol, alkyl (aryl) selenol, hydrogen selenide and epihalohydrin. A typical example is a compound in which one or more epoxyalkylseleno groups (specifically, β-epoxypropylseleno groups) of an epoxy compound are substituted with epithioalkylseleno groups.
If a more specific example method is used, the following can be given as typical examples. Organic compounds having a linear aliphatic skeleton: bis (β-epithiopropyl) selenide, bis (β-epithiopropyl)
Diselenide, bis (β-epithiopropyl) triselenide, bis (β-epithiopropylseleno) methane, 1,
2-bis (β-epithiopropylseleno) ethane, 1,
3-bis (β-epithiopropylseleno) propane,
1,2-bis (β-epithiopropylseleno) propane, 1- (β-epithiopropylseleno) -2- (β-
Epithiopropylselenomethyl) propane, 1,4-bis (β-epithiopropylseleno) butane, 1,3-bis (β-epithiopropylseleno) butane, 1- (β-
Epithiopropylseleno) -3- (β-epithiopropylselenomethyl) butane, 1,5-bis (β-epithiopropylseleno) pentane, 1- (β-epithiopropylseleno) -4- (β- Epithiopropylselenomethyl) pentane, 1,6-bis (β-epithiopropylseleno) hexane, 1- (β-epithiopropylseleno)
-5- (β-epithiopropylselenomethyl) hexane, 1- (β-epithiopropylseleno) -2-[(2
-Β-epithiopropylselenoethyl) thio] ethane,
1- (β-epithiopropylseleno) -2-[[2-
(2-β-epithiopropylselenoethyl) selenoethyl] thio] ethane, tetrakis (β-epithiopropylselenomethyl) methane, 1,1,1-tris (β-epithiopropylselenomethyl) propane, 1,5 -Bis (β-epithiopropylseleno) -2- (β-epithiopropylselenomethyl) -3-thiapentane, 1,5-
Bis (β-epithiopropylseleno) -2,4-bis (β-epithiopropylselenomethyl) -3-thiapentane, 1- (β-epithiopropylseleno) -2,2-
Bis (β-epithiopropylselenomethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropylseleno) -4- (β-epithiopropylselenomethyl)
-3-Thiahexane, 1,8-bis (β-epithiopropylseleno) -4- (β-epithiopropylselenomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylseleno) -4,5 bis (β-epithiopropylselenomethyl) -3,6-dithiaoctane, 1,
8-bis (β-epithiopropylseleno) -4,4-bis (β-epithiopropylselenomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylseleno) -2,4 , 5-Tris (β-epithiopropylselenomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylseleno) -2,5-bis (β-
Epithiopropylselenomethyl) -3,6-dithiaoctane, 1,9-bis (β-epithiopropylseleno)-
5- (β-epithiopropylselenomethyl) -5
[(2-β-epithiopropylselenoethyl) selenomethyl] -3,7-dithianonane, 1,10-bis (β-
Epithiopropylseleno) -5,6-bis [(2-β-
Epithiopropylselenoethyl) thio] -3,6,9-
Trithiadecane, 1,11-bis (β-epithiopropylseleno) -4,8-bis (β-epithiopropylselenomethyl) -3,6,9-trithiaundecane, 1,1
1-bis (β-epithiopropylseleno) -5,7-bis (β-epithiopropylselenomethyl) -3,6,9
-Trithiaundecane, 1,11-bis (β-epithiopropylseleno) -5,7-[(2-β-epithiopropylselenoethyl) selenomethyl] -3,6,9-trithiaundecane, 1, 11-bis (β-epithiopropylseleno) -4,7-bis (β-epithiopropylselenomethyl) -3,6,9-trithiaundecane, tetra [2- (β-epithiopropylseleno) acetyl Methyl] methane, 1,1,1-tri [2- (β-epithiopropylseleno) acetylmethyl] propane, tetra [2
-(Β-epithiopropylselenomethyl) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylselenomethyl) acetylmethyl] propane, bis (5,6-epithio-3-seleno) Hexyl) selenide,
2,3-bis (6,7-thioepoxy-1-selena-4
-Selenoheptyl) -1- (3,4-thioepoxy-1
-Selenobutyl) propane, 1,1,3,3-tetrakis (4,5-thioepoxy-2-selenopentyl)-
2-Selenapropane, bis (4,5-thioepoxy-2
-Selenopentyl) -3,6,9-triselenaundecane-1,11-bis (3,4-thioepoxy-1-selenobutyl), 1,4-bis (3,4-thioepoxy-1)
-Selenobutyl) -2,3-bis (6,7-thioepoxy-1-selena-4-selenoheptyl) butane, tris (4,5-thioepoxy-2-selenopentyl) -3-
Selena-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-selenobutyl), bis (5,6-epithio-3-selenohexyl) telluride, 2,3-bis (6,7-thioepoxy- 1-tellura-4-selenoheptyl) -1- (3,4-thioepoxy-1-selenobutyl) propane, 1,1,3,3-tetrakis (4,5
-Thioepoxy-2-selenopentyl) -2-tellurapropane, bis (4,5-thioepoxy-2-selenopentyl) -3,6,9-tritereoundecane-1,11
-Bis (3,4-thioepoxy-1-selenobutyl),
1,4-bis (3,4-thioepoxy-1-selenobutyl) -2,3-bis (6,7-thioepoxy-1-tellura-4-selenoheptyl) butane, tris (4,5-thioepoxy-2-) Selenopentyl) -3-tellura-6
Thiaoctane-1,8-bis (3,4-thioepoxy-
1-selenobutyl) and the like. Compound having an aliphatic cyclic skeleton: (1, 3 or 1,
4) -Bis (β-epithiopropylseleno) cyclohexane, (1,3 or 1,4) -bis (β-epithiopropylselenomethyl) cyclohexane, bis [4- (β
-Epithiopropylseleno) cyclohexyl] methane,
2,2-bis [4- (β-epithiopropylseleno) cyclohexyl] propane, bis [4- (β-epithiopropylseleno) cyclohexyl] sulfide, 2,5-
Bis (β-epithiopropylselenomethyl) -1,4-
Dithiane, 2,5-bis (β-epithiopropylselenoethylthiomethyl) -1,4-dithiane, (2,3,
2,5 or 2,6) -bis (3,4-epithio-1-)
Selenobutyl) -1,4-diselenane, (2,3,2,
(5 or 2,6) -bis (4,5-epithio-2-selenopentyl) -1,4-diselenane, (2,4,2,5
Or 5,6) -bis (3,4-epithio-1-selenobutyl) -1,3-diselenane, (2,4,2,5 or 5,6) -bis (4,5-epithio-2-seleno) (Pentyl) -1,3-diselenane, (2,3,2,5,2,
6 or 3,5) -bis (3,4-epithio-1-selenobutyl) -1-thia-4-selenane, (2,3,2,
5,2,6 or 3,5) -bis (4,5-epithio-
2-selenopentyl) -1-thia-4-selenane,
(2,4 or 4,5) -bis (3,4-epithio-1
-Selenobutyl) -1,3-diselenolane, (2,4 or 4,5) -bis (4,5-epithio-2-selenopentyl) -1,3-diselenolane, (2,4,2,5 or 4 , 5) -Bis (3,4-epithio-1-selenobutyl) -1-thia-3-selenolan, (2,4,2,5
Or 4,5) -bis (4,5-epithio-2-selenopentyl) -1-thia-3-selenolane, 2,6-bis (4,5-epithio-2-selenopentyl-1,3,5
-Triselenane, bis (3,4-epithio-1-selenobutyl) tricycloselenaoctane, bis (3,4-epithio-1-selenobutyl) dicycloselennanan,
(2,3,2,4,2,5 or 3,4) -bis (3,
4-epithio-1-selenobutyl) selenophane,
(2,3,2,4,2,5 or 3,4) -bis (4
5-epithio-2-selenopentyl) selenophane, 2
-(4,5-thioepoxy-2-selenopentyl) -5
-(3,4-thioepoxy-1-selenobutyl) -1-
Selenacyclohexane, (2,3,2,4,2,5,
2,6,3,4,3,5 or 4,5) -bis (3,4
-Thioepoxy-1-selenobutyl) -1-selenacyclohexane, (2,3,2,4,2,5,2,6,3
4,3,5 or 4,5) -bis (4,5-thioepoxy-2-selenopentyl) -1-selenacyclohexane, (2,3,2,5 or 2,6) -bis (3,4-
Epithio-1-selenobutyl) -1,4-ditelluran,
(2,3,2,5 or 2,6) -bis (4,5-epithio-2-selenopentyl) -1,4-ditellurane,
(2,4,2,5 or 5,6) -bis (3,4-epithio-1-selenobutyl) -1,3-ditellurane,
(2,4,2,5 or 5,6) -bis (4,5-epithio-2-selenopentyl) -1,3-ditellurane,
(2,3,2,5,2,6 or 3,5) -bis (3,
4-epithio-1-selenobutyl) -1-thia-4-telluran, (2,3,2,5,2,6 or 3,5) -bis (4,5-epithio-2-selenopentyl) -1 -Thia-4-tellurane, (2,4 or 4,5) -bis (3,4-epithio-1-selenobutyl) -1,3-ditellurolane, (2,4 or 4,5) -bis (4, 5-
Epithio-2-selenopentyl) -1,3-ditellolane, (2,4,2,5 or 4,5) -bis (3,4-
Epithio-1-selenobutyl) -1-thia-3-tellurolan, (2,4,2,5 or 4,5) -bis (4,5
-Epithio-2-selenopentyl) -1-thia-3-tellurolan, 2,6-bis (4,5-epithio-2-selenopentyl-1,3,5-tritellurane, bis (3,4
-Epithio-1-selenobutyl) tricyclotelluraoctane, bis (3,4-epithio-1-selenobutyl) dicyclotelluranonane, (2,3,2,4,2,5 or 3,4) -bis (3 , 4-Epithio-1-selenobutyl) tellurophan, (2,3,2,4,2,5 or 3,4) -bis (4,5-epithio-2-selenopentyl) tellurophan, 2- (4,5 -Thioepoxy-2-
Selenopentyl) -5- (3,4-thioepoxy-1-
Selenobutyl) -1-telluracyclohexane, (2
3,2,4,2,5,2,6,3,4,3,5 or 4,5) -bis (3,4-thioepoxy-1-selenobutyl) -1-telluracyclohexane, (2,3, 2,
4, 2, 5, 2, 6, 3, 4, 3, 5 or 4, 5)-
Bis (4,5-thioepoxy-2-selenopentyl)-
1-telluracyclohexane and the like. Compound having an aromatic skeleton: (1,3 or 1,4)-
Bis (β-epithiopropylseleno) benzene, (1,
3 or 1,4) -bis (β-epithiopropylselenomethyl) benzene, bis [4- (β-epithiopropylseleno) phenyl] methane, 2,2-bis [4- (β-
Epithiopropylseleno) phenyl] propane, bis [4- (β-epithiopropylseleno) phenyl] sulfide, bis [4- (β-epithiopropylseleno) phenyl] sulfone, 4,4′-bis (β- (Epithiopropylseleno) biphenyl and the like. Moreover,
Compounds in which at least one hydrogen of the β-epithiopropyl group of these compounds is substituted with a methyl group are also specific examples.

Preferred specific examples of (E) an organic compound having an epithioalkyltelluro group include a tellurium compound such as metal tellurium, alkali metal telluride, alkali metal tellurol, alkyl (aryl) tellurol, hydrogen telluride and epihalohydrin. A typical example is a compound in which one or more epoxyalkyltelluro groups (specifically, β-epoxypropyltelluro group) of an epoxy compound are substituted with epithioalkyltelluro groups.
If a more specific example method is used, the following can be mentioned as typical examples. Organic compounds having a linear aliphatic skeleton: bis (β-epithiopropyl) telluride, bis (β-epithiopropyl)
Ditelluride, bis (β-epithiopropyl) tritelluride, bis (β-epithiopropyltelluro) methane, 1,
2-bis (β-epithiopropyltelluro) ethane, 1,
3-bis (β-epithiopropyltelluro) propane,
1,2-bis (β-epithiopropyltelluro) propane, 1- (β-epithiopropyltelluro) -2- (β-
Epithiopropyltelluromethyl) propane, 1,4-bis (β-epithiopropyltelluro) butane, 1,3-bis (β-epithiopropyltelluro) butane, 1- (β-
Epithiopropyltelluro) -3- (β-epithiopropyltelluromethyl) butane, 1,5-bis (β-epithiopropyltelluro) pentane, 1- (β-epithiopropyltelluro) -4- (β- Epithiopropyltelluromethyl) pentane, 1,6-bis (β-epithiopropyltelluro) hexane, 1- (β-epithiopropyltelluro)
-5- (β-epithiopropyltelluromethyl) hexane, 1- (β-epithiopropyltelluro) -2-[(2
-Β-epithiopropyltelluroethyl) thio] ethane,
1- (β-epithiopropyltelluro) -2-[[2-
(2-β-epithiopropyltelluroethyl) telluroethyl] thio] ethane, tetrakis (β-epithiopropyltelluromethyl) methane, 1,1,1-tris (β-epithiopropyltelluromethyl) propane, 1,5 -Bis (β-epithiopropyltelluro) -2- (β-epithiopropyltelluromethyl) -3-thiapentane, 1,5-
Bis (β-epithiopropyltelluro) -2,4-bis (β-epithiopropyltelluromethyl) -3-thiapentane, 1- (β-epithiopropyltelluro) -2,2-
Bis (β-epithiopropyltelluromethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropyltelluro) -4- (β-epithiopropyltelluromethyl)
-3-Thiahexane, 1,8-bis (β-epithiopropyltelluro) -4- (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyltelluro) -4,5 bis (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,
8-bis (β-epithiopropyltelluro) -4,4-bis (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyltelluro) -2,4 , 5-Tris (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyltelluro) -2,5-bis (β-
Epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,9-bis (β-epithiopropyltelluro)-
5- (β-epithiopropyltelluromethyl) -5-
[(2-β-epithiopropyltelluroethyl) selenomethyl] -3,7-dithianonane, 1,10-bis (β-
Epithiopropyltelluro) -5,6-bis [(2-β-
Epithiopropyltelluroethyl) thio] -3,6,9-
Trithiadecane, 1,11-bis (β-epithiopropyltelluro) -4,8-bis (β-epithiopropyltelluromethyl) -3,6,9-trithiaundecane, 1,1
1-bis (β-epithiopropyltelluro) -5,7-bis (β-epithiopropyltelluromethyl) -3,6,9
-Trithiaundecane, 1,11-bis (β-epithiopropyltelluro) -5,7-[(2-β-epithiopropyltelluroethyl) selenomethyl] -3,6,9-trithiaundecane, 1, 11-bis (β-epithiopropyltelluro) -4,7-bis (β-epithiopropyltelluromethyl) -3,6,9-trithiaundecane, tetra [2- (β-epithiopropyltelluro) acetyl Methyl] methane, 1,1,1-tri [2- (β-epithiopropyltelluro) acetylmethyl] propane, tetra [2
-(Β-epithiopropyltelluromethyl) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropyltelluromethyl) acetylmethyl] propane, bis (5,6-epithio-3-tellulohexyl) ) Selenide,
2,3-bis (6,7-thioepoxy-1-selena-4
-Telluroheptyl) -1- (3,4-thioepoxy-1
-Tellurobutyl) propane, 1,1,3,3-tetrakis (4,5-thioepoxy-2-tellulopentyl)-
2-Selenapropane, bis (4,5-thioepoxy-2
-Telluropentyl) -3,6,9-triselenaundecane-1,11-bis (3,4-thioepoxy-1-tellurobutyl), 1,4-bis (3,4-thioepoxy-1)
-Tellurobutyl) -2,3-bis (6,7-thioepoxy-1-selena-4-telluroheptyl) butane, tris (4,5-thioepoxy-2-tellulopentyl) -3-
Selena-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-tellurobutyl), bis (5,6-epithio-3-tellurohexyl) telluride, 2,3-bis (6,7-thioepoxy-1) -Tellura-4-telluroheptyl) -1- (3,4-thioepoxy-1-tellurobutyl) propane, 1,1,3,3-tetrakis (4,5
-Thioepoxy-2-telluropentyl) -2-tellurapropane, bis (4,5-thioepoxy-2-telluropentyl) -3,6,9-tritereoundecane-1,11
-Bis (3,4-thioepoxy-1-tellurobutyl),
1,4-bis (3,4-thioepoxy-1-tellurobutyl) -2,3-bis (6,7-thioepoxy-1-tellura-4-telluroheptyl) butane, tris (4,5-thioepoxy-2-tellulopentyl) ) -3-tellura-6
Thiaoctane-1,8-bis (3,4-thioepoxy-
1-tellurobutyl) and the like. Compound having an aliphatic cyclic skeleton: (1, 3 or 1,
4) -Bis (β-epithiopropyltelluro) cyclohexane, (1,3 or 1,4) -bis (β-epithiopropyltelluromethyl) cyclohexane, bis [4- (β
-Epithiopropyltelluro) cyclohexyl] methane,
2,2-bis [4- (β-epithiopropyltelluro) cyclohexyl] propane, bis [4- (β-epithiopropyltelluro) cyclohexyl] sulfide, 2,5-
Bis (β-epithiopropyltelluromethyl) -1,4-
Dithiane, 2,5-bis (β-epithiopropyltelluroethylthiomethyl) -1,4-dithiane, (2,3,
2,5 or 2,6) -bis (3,4-epithio-1-)
Tellurobutyl) -1,4-diselenane, (2,3,2,
(5 or 2,6) -bis (4,5-epithio-2-telluropentyl) -1,4-diselenane, (2,4,2,5
Or 5,6) -bis (3,4-epithio-1-tellurobutyl) -1,3-diselenane, (2,4,2,5 or 5,6) -bis (4,5-epithio-2-telluropentyl) ) -1,3-diselenane, (2,3,2,5,2,
6 or 3,5) -bis (3,4-epithio-1-tellurobutyl) -1-thia-4-selenane, (2,3,2,
5,2,6 or 3,5) -bis (4,5-epithio-
2-telluropentyl) -1-thia-4-selenane,
(2,4 or 4,5) -bis (3,4-epithio-1
-Tellurobutyl) -1,3-diselenolane, (2,4 or 4,5) -bis (4,5-epithio-2-telluropentyl) -1,3-diselenolane, (2,4,2,5 or 4, 5) -bis (3,4-epithio-1-tellurobutyl) -1-thia-3-selenolan, (2,4,2,5
Or 4,5) -bis (4,5-epithio-2-tellulopentyl) -1-thia-3-selenolane, 2,6-bis (4,5-epithio-2-tellulopentyl-1,3,5)
-Triselenane, bis (3,4-epithio-1-tellurobutyl) tricycloselenaoctane, bis (3,4-epithio-1-tellurobutyl) dicycloselenanane,
(2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-epithio-1-tellurobutyl) selenophane, (2,3,2,4,2,5 or 3,4) -Bis (4,5-epithio-2-telluropentyl) selenophane, 2- (4,5-thioepoxy-2-telluropentyl) -5- (3,4-thioepoxy-1-tellurobutyl) -1-selenacyclohexane, ( 2,3,2,4,
2,5,2,6,3,4,3,5 or 4,5) -bis (3,4-thioepoxy-1-tellurobutyl) -1-selenacyclohexane, (2,3,2,4,2, 5, 2,
6,3,4,3,5 or 4,5) -bis (4,5-thioepoxy-2-tellulopentyl) -1-selenacyclohexane, (2,3,2,5 or 2,6) -bis (3 , 4-Epithio-1-tellurobutyl) -1,4-ditellurane, (2,3,2,5 or 2,6) -bis (4,5-epithio-2-tellulopentyl) -1,4-
Ditellurane, (2,4,2,5 or 5,6) -bis (3,4-epithio-1-tellurobutyl) -1,3-ditellurane, (2,4,2,5 or 5,6) -bis (4,5-epithio-2-telluropentyl) -1,3-
Ditellurane, (2,3,2,5,2,6 or 3,5)
-Bis (3,4-epithio-1-tellurobutyl) -1-
Thia-4-tellurane, (2,3,2,5,2,6 or 3,5) -bis (4,5-epithio-2-telluropentyl) -1-thia-4-telluran, (2,4 or 4,
5) -Bis (3,4-epithio-1-tellurobutyl)-
1,3-ditellolane, (2,4 or 4,5) -bis (4,5-epithio-2-tellulopentyl) -1,3-
Ditellrolan, (2,4,2,5 or 4,5) -bis (3,4-epithio-1-tellurobutyl) -1-thia-
3-tellurolan, (2,4,2,5 or 4,5) -bis (4,5-epithio-2-tellulopentyl) -1-thia-3-tellurolan, 2,6-bis (4,5-epithio -2-tellulopentyl-1,3,5-tritellurane, bis (3,4-epithio-1-tellurobutyl) tricyclotelluraoctane, bis (3,4-epithio-1-tellurobutyl) dicyclotelluranonane, 3, 2, 4,
2,5 or 3,4) -bis (3,4-epithio-1-
Tellurobutyl) tellurophane, (2,3,2,4,2,
5 or 3,4) -bis (4,5-epithio-2-telluropentyl) tellurophan, 2- (4,5-thioepoxy-2-tellulopentyl) -5- (3,4-thioepoxy-1-tellurobutyl) -1 -Telluracyclohexane,
(2,3,2,4,2,5,2,6,3,4,3,5 or 4,5) -bis (3,4-thioepoxy-1-tellurobutyl) -1-telluracyclohexane, (2 , 3,
2,4,2,5,2,6,3,4,3,5 or 4,
5) -bis (4,5-thioepoxy-2-tellulopentyl) -1-telluracyclohexane and the like. Compound having an aromatic skeleton: (1,3 or 1,4)-
Bis (β-epithiopropyltelluro) benzene, (1,
3 or 1,4) -bis (β-epithiopropyltelluromethyl) benzene, bis [4- (β-epithiopropyltelluro) phenyl] methane, 2,2-bis [4- (β-
Epithiopropyltelluro) phenyl] propane, bis [4- (β-epithiopropyltelluro) phenyl] sulfide, bis [4- (β-epithiopropyltelluro) phenyl] sulfone, 4,4′-bis (β- Epithiopropyl telluro) biphenyl and the like. Moreover,
Compounds in which at least one hydrogen of the β-epithiopropyl group of these compounds is substituted with a methyl group are also specific examples.

Further, organic compounds having an unsaturated group are also included in the above (A) to (E). Preferred specific examples of these include vinylphenylthioglycidyl ether, vinylbenzylthioglycidyl ether, thioglycidyl methacrylate, thioglycidyl acrylate, and allylthioglycidyl ether.

Among these, (B) an organic compound having an epithioalkyloxy group, (C) an organic compound having an epithioalkylthio group, (D) an organic compound having an epithioalkylseleno group, (E) An organic compound having an epithioalkyltelluro group, and particularly preferred are (C) an organic compound having an epithioalkylthio group, and (D) an organic compound having an epithioalkylseleno group. Specific examples of particularly preferable ones are a chain compound having a β-epithiopropylthio group or a β-epithiopropylseleno group, a branched compound, an aliphatic cyclic compound, an aromatic compound, and a heterocyclic ring having the above-described specific examples. And most preferably a compound represented by the following formula (2).

[0032]

Embedded image (Wherein, R ^{5 to} R ¹⁰ each represent a hydrocarbon group having 1 to 10 carbon atoms or hydrogen. X represents S or O, and the number of S is the sum of S and O constituting a three-membered ring. For 5
0% or more. Y represents O, S, Se or Te;
p represents 1 to 6, and s represents 0 to 4. )

An inorganic compound having a sulfur atom and / or a selenium atom and a structure represented by the formula (1) may be used in one molecule.
In a composition containing a compound having at least one compound represented by Formula (1), a compound having at least one structure represented by Formula (1) in one molecule is used in an amount of 10 wt% or more, and preferably 20 wt% or more.
wt% or more, more preferably 30 wt% or more. If it is less than 10 wt%, the balance between high refractive index and high Abbe number cannot be maintained. The ratio of the compound having one or more structures represented by the formula (1) in one molecule to the inorganic compound having a sulfur atom and / or a selenium atom is such that the structure represented by the formula (1) is one molecule. It is used in an amount of 1 to 50 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the compound having one or more compounds.

The compound having one or more structures represented by the formula (1) used in the present invention can be synthesized by a known method. Specifically, JP-A-9-71580, JP-A-9-110979, and JP-A-9-255781
And Japanese Patent Application No. 2000-20627.

Specific examples of the organic compound containing a selenium atom include compounds in which part or all of the sulfur atoms of the above-mentioned organic compound containing a sulfur atom such as selenols, selenides, and polyselenides are replaced with a selenium atom. No.

While the organic compounds having a sulfur atom and / or selenium atom have been exemplified above, the present invention includes all organic compounds having one or more sulfur atoms and / or selenium atoms, and is limited to these listed compounds. Not something. These organic compounds having a sulfur atom and a selenium atom may be used alone or as a mixture of two or more.

Many researches have been reported on a method for synthesizing an organic compound having a sulfur atom and a selenium atom from a long time ago, and can be easily synthesized by these known synthesis methods. Examples of many review books on these synthesis methods include “Organic Sulfur Chemistry -Synthesis Reaction-” (ed. By Dai Famo, Kagaku Dojin, 1982) and “Organosele”.
Num Chemistry "(Dennis Li
otta, John Wiley & Sons, 19
1987), "Chemical Special Issue 115 Organic Chemistry of Hetero Elements"
(Naoki Inamoto et al., Chemistry Dojin, 1988), "4th Edition Experimental Chemistry Course, Organic Synthesis IV" (Chemical Society of Japan, Maruzen, 1
992).

The composition for an optical material of the present invention contains, in addition to one or more inorganic compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom and a compound capable of reacting with the compound, oxidation resistance and weather resistance. For the purpose of improving various properties such as dyeability, dyeability, strength, etc., it is also possible to carry out curing polymerization by adding a compound capable of reacting partially or entirely with the compound of the composition component. In this case, a known polymerization curing catalyst can be separately added as necessary for the reaction.

As compounds capable of reacting with part or all of the components, epoxy compounds, isocyanates, carboxylic acids, carboxylic anhydrides, phenols, amines, which do not contain a sulfur atom and / or a selenium atom, Examples include vinyl compounds, allyl compounds, acrylic compounds, methacryl compounds, and the like. The following are typical examples of these.

(1) Monoepoxy compounds such as ethylene oxide and propylene oxide, polyhydric phenol compounds such as hydroquinone, catechol, resorcinol, bisphenol A, bisphenol F, bisphenol ether, halogenated bisphenol A, and novolak resin, and epihalohydrin Phenolic epoxy compounds produced by condensation, methanol, ethanol, propanol, butanol, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-propanediol, 1,4 -Butanediol, 1,6-hexanediol, neopentyl glycol, glycerin, trimethylolpropane, pen Erythritol, 1,3- and 1,4-cyclohexanediol, 1,3- and 1,4-cyclohexane dimethanol, hydrogenated bisphenol A, Bisufenoru A · ethylene oxide adduct,
Alcohol-based epoxy compounds produced by condensation of an alcohol compound such as bisphenol A-propylene oxide adduct with epihalohydrin, urethane-based epoxy compounds produced from the above-mentioned alcohol and phenol compounds and diisocyanate, acetic acid, propionic acid, benzoic acid, Adipic acid, sebacic acid, dodecanedicarboxylic acid, dimer acid, phthalic acid, iso, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, hetonic acid, nadic acid, maleic acid, succinic acid, fumaric acid, Trimellitic acid, benzenetetracarboxylic acid, benzophenonetetracarboxylic acid,
Glycidyl ester-based epoxy compounds produced by condensation of epihalohydrin with carboxylic compounds such as naphthalene dicarboxylic acid, diphenyl dicarboxylic acid, acrylic acid, methacrylic acid, maleic acid, fumaric acid, ethylenediamine, 1,2-diaminopropane, 1,3 -Diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8- Diaminooctane, bis- (3-aminopropyl) ether, 1,2-bis- (3-aminopropoxy) ethane, 1,3-bis- (3-aminopropoxy) -2,2′-dimethylpropane, 2-,
1,3- or 1,4-bisaminocyclohexane,
1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- or 1,4-bisaminopropylcyclohexane, hydrogenated 4,4'-diamino Diphenylmethane, isophoronediamine, 1,4-bisaminopropylpiperazine, m- or p-phenylenediamine, 2,4- or 2,6-tolylenediamine, m
-Or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylether, 2,2- (4,4'-diaminodiphenyl ) Propane, N, N′-dimethylethylenediamine, N, N ′
-Dimethyl-1,2-diaminopropane, N, N'-dimethyl-1,3-diaminopropane, N, N'-dimethyl-1,2-diaminobutane, N, N'-dimethyl-
1,3-diaminobutane, N, N'-dimethyl-1,4
-Diaminobutane, N, N'-dimethyl-1,5-diaminopentane, N, N'-dimethyl-1,6-diaminohexane, N, N'-dimethyl-1,7-diaminoheptane, N, N ' -Diethylethylenediamine, N, N '
-Diethyl-1,2-diaminopropane, N, N'-diethyl-1,3-diaminopropane, N, N'-diethyl-1,2-diaminobutane, N, N'-diethyl-
1,3-diaminobutane, N, N'-diethyl-1,4
-Diaminobutane, N, N'-diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine,
2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1-di- (4-piperidyl) -methane,
1,2-di- (4-piperidyl) -ethane, 1,3-di- (4-piperidyl) -propane, 1,4-di- (4-
Amine-based epoxy compounds produced by condensation of (piperidyl) -butane and epihalohydrin, 3,4-epoxycyclohexyl-3,4-epoxycyclohexanecarboxylate, vinylcyclixane dioxide, 2
Alicyclic epoxy compounds such as-(3,4-epoxycyclohexyl) -5,5-spiro-3,4-epoxycyclohexane-meta-dioxane, bis (3,4-epoxycyclohexyl) adipate, cyclopentadiene epoxide, epoxy Compounds produced by epoxidation of unsaturated compounds such as oxidized soybean oil, epoxidized polybutadiene, and vinylcyclohexene epoxide; unsaturated groups such as vinylphenyl glycidyl ether, vinylbenzyl glycidyl ether, glycidyl methacrylate, glycidyl acrylate, and allyl glycidyl ether Epoxy compounds such as epoxy compounds having the formula (2),
Methyl isocyanate, ethyl isocyanate, propyl isocyanate, iso-propyl isocyanate,
Monoisocyanates such as n-butyl isocyanate, sec-butyl isocyanate, tert-butyl isocyanate, pentyl isocyanate, hexyl isocyanate, octyl isocyanate, dodecyl isocyanate, cyclohexyl isocyanate, phenyl isocyanate, toluyl isocyanate, diethylene diisocyanate, tetramethylene diisocyanate, hexamethylene Diisocyanate, trimethylhexamethylene diisocyanate, cyclohexane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, isophorone diisocyanate, 2,6-bis (isocyanatomethyl) decahydronaphthalene , Lysine triisocyanate, 2, - tolylene diisocyanate,
2,6-tolylene diisocyanate, o-tolidine diisocyanate, 4,4'-diphenylmethane diisocyanate, diphenyl ether diisocyanate, 3-
(2′-isocyanatocyclohexyl) propyl isocyanate, tris (phenylisocyanate) thiophosphate, isopropylidenebis (cyclohexylisocyanate), 2,2′-bis (4-isocyanatophenyl) propane, triphenylmethane triisocyanate, bis (diisocyanate tolyl) ) Phenylmethane, 4,4 ′, 4 ″ -triisocyanate-2,5-
Dimethoxyphenylamine, 3,3′-dimethoxybenzidine-4,4′-diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 4,4′-diisocyanatobiphenyl, 4,
4'-diisocyanato-3,3'-dimethylbiphenyl, dicyclohexylmethane-4,4'-diisocyanato, 1,1'-methylenebis (4-isocyanatobenzene), 1,1'-methylenebis (3-methyl-4- Isocyanatobenzene), m-xylylenediisocyanate, p-xylylenediisocyanate, 1,3-bis (1-isocyanate-1-methylethyl) benzene,
1,4-bis (1-isocyanate-1-methylethyl) benzene, 1,3-bis (2-isocyanato-2-
Propyl) benzene, 2,6-bis (isocyanatomethyl) naphthalene, 1,5-naphthalenediisocyanate, bis (isocyanatomethyl) tetrahydrodicyclopentadiene, bis (isocyanatomethyl) dicyclopentadiene, bis (isocyanatomethyl) tetrahydrothiophene, Polyisocyanates such as 2,5-diisocyanatomethylnorbornene, bis (isocyanatomethyl) adamantane, diisocyanate diisocyanate, and 1,3,5-tri (1-isocyanatohexyl) isocyanuric acid, and a bullet reaction of these polyisocyanates (3) isocyanates such as cyclized trimers of these polyisocyanates and adducts of these polyisocyanates with alcohols;
(1) Carboxylic acids exemplified as a partner material to be reacted with epihalohydrin described for the epoxy compound, (4) Carboxylic anhydride exemplified as a partner material to be reacted with the epihalohydrin described for the epoxy compound of (1) (5) Phenols exemplified as a partner material to be reacted with epihalohydrin described in (1) Epoxy compound, (6) exemplified as a partner material to be reacted with epihalohydrin described in (1) Epoxy compound Amines, (7)
Vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, phenyl vinyl ether, benzyl vinyl ether, 2-
Chloroethyl vinyl ether, cyclohexyl vinyl ether, vinyl glycidyl ether, vinyl alcohol, methyl vinyl carbinol, ethylene glycol monovinyl ether, ethylene glycol divinyl ether, diethylene glycol monovinyl ether, diethylene glycol divinyl ether, tetramethylene glycol monovinyl ether, methyl vinyl ketone, divinyl dicarbonate , Vinyl diglycol carbonate, vinylene carbonate, vinyl acetate, vinyl chloroacetate, vinyl propionate, vinyl butyrate, vinyl hexanoate, vinyl 2-ethylhexanoate, divinyl adipate, vinyl benzoate, vinyl salicylate, vinyl acrylate, methacryl Vinyl acid, vinyl bromide, vinyl iodide, vinyl Phosphate, vinylurea, styrene,
2-methylstyrene, 3-methylstyrene, 4-methylstyrene, α-methylstyrene, 2,4,6-trimethylstyrene, 4-t-butylstyrene, stilbene, vinylphenol, 3-vinylbenzylalcohol, 4-
Vinylbenzyl alcohol, 2- (4-vinylbenzylthio) ethanol, 2- (3-vinylbenzylthio) ethanol, 1,3-bis (4-vinylbenzylthio)-
2-propanol, 1,3-bis (3-vinylbenzylthio) -2-propanol, 2,3-bis (4-vinylbenzylthio) -1-propanol, 2,3-bis (3
-Vinylbenzylthio) -1-propanol, cinnamyl alcohol, cinnamaldehyde, 1,3-divinylbenzene, 1,4-divinylbenzene, trivinylbenzene, divinylphthalate, 2-chlorostyrene, 3-
Chlorostyrene, 4-chlorostyrene, 3-chloromethylstyrene, 4-chloromethylstyrene, 4-aminostyrene, 3-cyanomethylstyrene, 4-cyanomethylstyrene, 4-vinylbiphenyl, 2,2′-divinylbiphenyl, 4,4'-divinylbiphenyl, 2,2-
Vinyl compounds such as bis (4-vinylphenyl) propane, bis (4-vinylphenyl) ether and 2,2-bis (4-vinyloxyphenyl) propane; (8) (7)
Allyl compounds in which some or all of the vinyl groups of the compounds exemplified by the vinyl compounds have been replaced with allyl groups,
(9) methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, cyclohexyl acrylate, 2-hydroxyethyl acrylate,
3-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 3-phenoxy-2-hydroxypropyl acrylate, trimethylolpropane monoacrylate, 2-hydroxyethyl isocyanurate monoacrylate, 2-hydroxyethyl isocyanurate diacrylate, 2-hydroxyethyl Cyanurate monoacrylate, 2-hydroxyethyl cyanurate diacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, 1,3-butylene glycol diacrylate, triethylene glycol diacrylate, polyethylene glycol diacrylate, propylene glycol diacrylate, 1, 3
-Propanediol diacrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate,
Neopentyl glycol diacrylate, polypropylene glycol diacrylate, 2-hydroxy-1,3
-Diacryloxypropane, 2,2-bis [4- (acryloxyethoxy) phenyl] propane, 2,2-bis [4- (acryloxyethoxy) cyclohexyl] propane, 2,2-bis [4- (2 -Hydroxy-3-acryloxypropoxy) phenyl] propane, 2,2-bis [4- (acryloxydiethoxy) phenyl] propane, 2,2-bis [4- (acryloxypolyethoxy) phenyl] propane, trimethylolpropane Triacrylate, pentaerythritol monoacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaacrylate of bis (2,2,2-trimethylolethyl) ether, bis (2
Acrylic compounds such as hexaacrylate of 2,2-trimethylolethyl) ether and methacrylic compounds in which some or all of the acrylic groups of the compounds exemplified as the acrylic compounds of (10) and (9) are replaced by methacrylic groups.

As described above, the compounds capable of reacting with some or all of the components used for the purpose of improving various performances have been exemplified, but the compounds are not limited to these listed compounds.
In addition, these compounds may be used alone or as a mixture of two or more.

The ratio of the above-mentioned physical properties improving agent is determined within a range that does not impair the optical physical properties and mechanical physical properties, and cannot be univocally determined by the chemical structure and the like.
The following is preferred.

In the production method of the optical material of the present invention, it is of course possible to further improve the practicality of the obtained material by adding known additives such as antioxidants and ultraviolet absorbers. When the optical material of the present invention is easily peeled from the mold during polymerization, it is also effective to add a known external and / or internal adhesion improver to improve the adhesion between the obtained cured material and the mold. It is. When it is difficult to peel off from the mold during the polymerization, it is also effective to add a known external and / or internal mold releasability improver to improve the mold releasability between the obtained cured material and the mold.

In the present invention, the method for producing an optical material includes, as necessary, one or more compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom as raw materials and a compound capable of reacting with the compound. Addition of compounds, catalysts, adhesion improvers, antioxidants, ultraviolet absorbers, radical polymerization initiators, various performance improvers, etc. that can react with some or all of the composition used for the purpose of improving various performances used After mixing and homogenizing the agent (auxiliary material), the mixture is poured into a glass or metal mold, and the polymerization and curing reaction is advanced by heating.

Before casting, one or more compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom and a part or the whole of a composition containing a compound capable of reacting with the compound are added to the catalyst before casting. In the presence or absence, with or without stirring, at −100 to 160 ° C .;
After preliminarily polymerizing over time, the composition can be prepared and cast. The preliminary polymerization conditions are:
Preferably, it is carried out at -10 to 120 ° C for 0.1 to 240 hours, more preferably at 0 to 100 ° C for 0.1 to 120 hours.

The method for producing the optical material of the present invention will be described in more detail below. As described above, the main raw material and the auxiliary raw material are mixed and then injection-hardened to produce a mold. Compounds that can react with some or all of the components used for the purpose of improving various performances used according to the conditions, catalysts, adhesion improvers or release improvers, antioxidants, bluing agents, ultraviolet absorbers Additives such as various performance-improving additives can be mixed in the same container at the same time with stirring, or even if each raw material is added and mixed stepwise, after mixing several components separately, further in the same container You may mix again. The raw materials, additives, and the like may be mixed in any order. Upon mixing, the set temperature, the time required for the mixing, etc. may be basically any conditions under which each component is sufficiently mixed, but an excessive temperature and time may cause an undesired reaction between each raw material and additive, Further, it is not appropriate, for example, because the viscosity increases and the casting operation becomes difficult. The mixing temperature should be in the range of about -50 to 100 ° C, and the preferred temperature range is -30 to
70 ° C, more preferably -5 to 50 ° C. The mixing time is about 1 minute to 12 hours, preferably about 5 minutes to 10 hours, and most preferably about 5 minutes to 6 hours. Each raw material,
Performing a degassing operation under reduced pressure before, during or after mixing of the additives is a preferable method from the viewpoint of preventing the formation of bubbles during the subsequent casting polymerization curing. At this time, the degree of pressure reduction is about 0.1 to 700 mmHg, and preferably 0.5 to 300 mmHg. Further, it is preferable from the standpoint of further improving the quality of the optical material of the present invention that the mixture or the main and auxiliary raw materials before mixing is purified by filtering impurities or the like with a filter having a pore size of about 0.05 to 3 μm. . After pouring into a glass or metal mold, polymerization curing is performed by an electric furnace or the like. The curing time is 0.1 to 100 hours, usually 1 to 72 hours, and the curing temperature is -10 to 16
0 ° C, usually 0 to 140 ° C. The polymerization is held at a predetermined polymerization temperature for a predetermined time, a temperature rise of 0.1 to 100 ° C./h,
The cooling can be performed at a temperature of 0.1 to 100 ° C./h or a combination thereof. After the curing is completed, the material is
Performing an annealing treatment at a temperature of 150 ° C. for about 10 minutes to 5 hours is a preferable treatment for removing distortion of the optical material of the present invention. Further, if necessary, surface treatment such as dyeing, hard coating, anti-reflection, anti-fogging property and impact resistance can be performed.

[0047]

According to the composition of the present invention, one or more inorganic compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom and a composition for an optical material containing a compound capable of reacting with the compound can be easily prepared. It has become possible to provide an optical material that has a higher refractive index.

[0048]

EXAMPLES The present invention will now be described specifically with reference to examples, but the present invention is not limited to these examples. In addition, evaluation of the obtained lens was performed by the following method. Refractive index, Abbe number (nD, νD) Measured at 25 ° C. using an Abbe refractometer.

Example 1 1,2-bis (β-epithiopropylthio) ethane 90
To a total of 100 parts by weight of 10 parts by weight of sulfur and 10 parts by weight of sulfur, 0.1 part by weight of tetrabromophosphonium bromide was mixed as a catalyst to obtain a uniform liquid. Then, this was poured into a mold for a flat lens having a thickness of 2.5 mm.
The temperature was raised to 80 ° C. over 10 hours to polymerize and cure to produce a lens. The resulting lens exhibited good heat resistance and physical properties, good transparency and surface condition, and almost no striae or surface deformation. Table 1 shows the measurement results of the refractive index and Abbe number of the lens.

Examples 2 to 20 Example 1 was repeated except that the compositions shown in Table 1 were used. Table 1 shows the measurement results of the refractive index and Abbe number of the lens.

Comparative Examples 1 to 8 Example 1 was repeated except that the compositions shown in Table 2 were used. Table 2 shows the measurement results of the refractive index and Abbe number of the lens.

[0052]

[Table 1]

[0053]

[Table 2]

Example 21 Under a nitrogen atmosphere, 85 parts by weight of bis (β-epithiopropyl) sulfide and 15 parts by weight of sulfur were mixed and stirred at 100 ° C. for 1 hour. After cooling, 0.05 parts by weight of tetrabutylammonium bromide was mixed as a catalyst to obtain a uniform liquid.
Then, this was filtered through a 0.5 μm PTFE filter, poured into a 2.5 mm-thick flat lens mold, heated in an oven from 10 ° C. to 120 ° C. over 22 hours, and polymerized and cured to produce a lens. The resulting lens exhibited good heat resistance and physical properties, good transparency and surface condition, and almost no striae or surface deformation. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Examples 22 to 24 Example 21 was repeated except that the compositions shown in Table 3 were used. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Example 25 In a nitrogen atmosphere, 32 parts by weight of 1,3-dimercaptobenzene and 10 parts by weight of sulfur were mixed and stirred at 100 ° C. for 1 hour. After cooling, 62 parts by weight of divinylbenzene, 0.02 part by weight of triethylbenzylammonium chloride as a catalyst, and 0.3 part by weight of 1,1-azobis (cyclohexane-1-carbonitrile) as a radical initiator were mixed to form a uniform liquid. . This was then filtered through a 0.5 μm PTFE filter, poured into a 2.5 mm thick plate lens mold, and heated in an oven at 10 ° C. for 22 hours.
The temperature was raised to ℃ to polymerize and cure to produce a lens. The resulting lens exhibited good heat resistance and physical properties, good transparency and surface condition, and almost no striae or surface deformation. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Examples 26-27 Example 25 was repeated except that the compositions shown in Table 3 were used. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Example 28 Under a nitrogen atmosphere, 45 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5 parts by weight of sulfur and 1 part by weight of selenium sulfide were mixed and stirred at 100 ° C. for 1 hour. . After cooling, 49 parts by weight of 1,3-bis (isocyanomethyl) benzene, 0.01 part by weight of cetyldimethylbenzylammonium chloride as a catalyst, and 0.005 parts by weight of dibutyltin laurylate as a urethane initiator,
Further, 0.05 part by weight of dioctyl phosphoric acid was mixed as an internal release agent to obtain a uniform liquid. Next, this was added to a 0.5 μm P
The mixture was filtered through a TFE filter, poured into a 2.5 mm-thick flat lens mold, heated from 10 ° C. to 120 ° C. in an oven for 22 hours, and polymerized and cured to produce a lens. The resulting lens exhibited good heat resistance and physical properties, good transparency and surface condition, and almost no striae or surface deformation. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Examples 29-31 Example 89 was repeated except that the compositions shown in Table 3 were used. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Example 32 Example 21 was repeated except that the compositions shown in Table 3 were used. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Example 33 Under a nitrogen atmosphere, 65 parts by weight of bis (β-epithiopropyl) sulfide and 35 parts by weight of sulfur, and 0.2 parts by weight of dibenzothiazyl disulfide as a catalyst for preliminary polymerization were added to 50 parts by weight.
The mixture was stirred at 24 ° C. for 24 hours. At the beginning of mixing, the bis (β-
Although the sulfur was not completely dissolved in (epithiopropyl) sulfide, it was completely dissolved after about 12 hours. After cooling, 0.02 parts by weight of tetrabutylammonium bromide was mixed as a catalyst to obtain a uniform liquid. This was then filtered through a 0.5 μm PTFE filter,
The mixture was poured into a mold for a flat lens having a thickness of 1 mm, heated from 10 ° C. to 120 ° C. in an oven for 22 hours, and polymerized and cured to produce a lens. The resulting lens exhibited good heat resistance and physical properties, good transparency and surface condition, and almost no striae or surface deformation. Table 3 shows the measurement results of the refractive index and Abbe number of the lens.

Comparative Examples 9 to 19 Examples 21 to 31 were repeated, except that the inorganic compounds having a sulfur atom and / or a selenium atom were excluded from the compositions in Examples 21 to 31. The refractive index of the lens,
Table 4 shows the Abbe number measurement results.

[0063]

[Table 3]

[0064]

[Table 4]

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification FI FI Theme Court ゛ (Reference) G02B 1/04 G02B 1/04 G02C 7/02 G02C 7/02 (72) Inventor Junya Hayakawa Katsushika-ku, Tokyo 6-1-1 Shinjuku, Tokyo Research Laboratory Mitsubishi Gas Chemical Co., Ltd. (72) Inventor Teruo Kamura 6-1-1, Shinjuku, Katsushika-ku, Tokyo F-term in Tokyo Research Laboratory Mitsubishi Gas Chemical Co., Ltd. 4J002 CN011 CN021 DA046 DA116 DB006 DG026 DG036 DG046 DG066 EN027 EN037 EN047 EN067 EN077 EU077 EU117 EU177 EW177 GP01 GP02 4J030 BA03 BA05 BB03 BC21 BC22 BC37 BG25

Claims (7)

[Claims] An optical material composition comprising at least one inorganic compound selected from inorganic compounds having a sulfur atom and / or a selenium atom and a compound capable of reacting with the compound. 2. An optical system comprising one or more inorganic compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom and an organic compound having a sulfur atom and / or a selenium atom capable of reacting with the compound. Material composition. 3. A compound containing at least one compound represented by the following formula (1) in one molecule and one or more inorganic compounds selected from inorganic compounds having a sulfur atom and / or a selenium atom. A composition for an optical material comprising: Embedded image (Wherein, R ¹ is a hydrocarbon having 1 to 10 carbon atoms, R ² , R ³
And R ⁴ each represent a hydrocarbon group having 1 to 10 carbon atoms or hydrogen. Y represents O, S, Se or Te.
m = 1 to 5, n = 0 to 5, p = 0 or 1. ) 4. The composition for an optical material according to claim 1, wherein the inorganic compound having a sulfur atom and / or a selenium atom is sulfur, carbon disulfide, selenium, lead selenide and selenium sulfide. 5. An optical material obtained by polymerizing and curing the composition according to claim 1, 2, 3 or 4. 6. An optical lens comprising the optical material according to claim 5. 7. A method for obtaining an optical material by polymerizing and curing the composition according to claim 1, 2, 3 or 4.