WO2014208994A1 - Polymerizable composition for highly refractive optical material, photochromic composition thereof, and method for preparing high-refractive optical material using compositions - Google Patents

Abstract

The present invention relates to a polymerizable composition for a highly refractive optical material, a photochromic composition thereof, and a method for preparing a highly refractive optical material using the compositions. In the present invention, provided is a polymerizable composition for a highly refractive optical material, the polymerizable composition containing at least one of compounds represented by chemical formulas 1 and 2, and provided is a photochromic composition further containing a photochromic compound in addition to the polymerizable composition. According to the present invention, a fluorene acryl based optical material can be obtained that has excellent photochromic performance and optical characteristics while being highly refractive.

Description

Polymeric composition for high refractive optical material, photochromic composition thereof and method of manufacturing high refractive optical material using same

The present invention relates to a novel polymerizable composition for high refractive optical materials, a photochromic composition thereof and a method for producing a high refractive optical material using the same.

Korean Patent Nos. 10-0496911, 10-0498896, and the like disclose a composition for an acrylic optical material having a high refractive index and a high Abbe number and excellent optical properties such as transparency, light weight, and heat resistance. However, acrylic monomers have a problem of inferior deformability when producing a lens by casting polymerization due to their high adhesive strength. In order to make a high refractive index lens with an acrylic monomer, a substituent may be substituted with Br. In this case, adhesiveness becomes higher. In addition, although the acrylic monomer substituted with Br has a high refractive index, there is a problem of yellowing at high temperature.

In general, the phenomenon of changing to a specific color when it is transparent to ultraviolet rays is called photochromic, and the material causing such photochromic is called photochromic (photoreversible discoloring compound or photochromic compound). When the photochromic compound is applied to the spectacle lens, it is possible to produce a photochromic lens (dimension lens) having a characteristic that the color before and after light irradiation is changed differently. Photochromic lenses, especially acrylic photochromic lenses, are usually prepared by making a photochromic polymerizable composition in which a photochromic compound is mixed with a polymerizable monomer and curing the composition. Conventional photochromic lenses manufactured in this way can produce lenses with good discoloration performance and optical properties at medium refraction, but at high refractive index, the discoloration performance is poor, the variable color life is very short, and the commercialization is poor due to the color difference according to the lens thickness. There was a problem.

[Preceding technical literature]

[Patent Documents]

(Patent Document 1) Republic of Korea Patent Publication 10-0496911

(Patent Document 2) Republic of Korea Patent Registration 10-0498896

(Patent Document 3) Republic of Korea Patent Publication No. 10-2008-0045267

(Patent Document 4) Republic of Korea Patent Publication 10-2005-0026650

An object of the present invention is to provide a novel polymerizable composition for acrylic high refractive optical material and a method for producing a high refractive optical material. In particular, a novel polymerizable composition for high refractive optical material of fluorene acrylic having good transparency, thermal stability and light resistance and It is an object of the present invention to provide a method for producing a high refractive optical lens.

In addition, an object of the present invention is to provide a polymerizable composition for an optical material having a high refractive index and excellent optical properties, and a method for producing a photochromic high refractive optical material, in particular, having excellent photochromic colorability, transparency, and thermal stability. And a polymerizable composition for a fluorene acrylic photochromic high refractive optical material having good light resistance and a method of manufacturing a photochromic high refractive optical lens using the same.

In the present invention,

Provided is a polymerizable composition for a high refractive optical material comprising at least one of a compound represented by Formula 1 and a compound represented by Formula 2. The polymerizable composition may further include one or two or more compounds selected from compounds represented by Formula 3 below, compounds represented by Formula 4, compounds represented by Formula 5, and other acrylic monomers.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

 (n = 3-10)

[Formula 5]

In the present invention,

(a) any one or more of the compound represented by Formula 1 and the compound represented by Formula 2,

(b) Provided is a polymerizable composition for photochromic high refractive optical materials comprising a photochromic compound. The photochromic polymerizable composition may further include one or two or more compounds selected from the compound represented by Formula 3, the compound represented by Formula 4, the compound represented by Formula 5, and other acrylic monomers.

In the present invention,

Provided are a method for producing a fluorene acrylic high refractive optical material comprising casting a polymerizable polymerizable composition for a high refractive optical material and a fluorene acrylic high refractive optical material obtained by molding a polymerizable polymerizable composition.

In addition, in the present invention, a method of producing a fluorene acrylic photochromic high refractive optical material comprising casting the polymerizable polymerizable composition for a photochromic high refractive optical material and the photochromic polymerizable composition and a flu obtained An orene acrylic photochromic high refractive optical material is provided.

The high refractive optical material or the photochromic high refractive optical material includes optical lenses such as spectacle lenses.

The present invention provides a novel high refractive optical material and a new photochromic high refractive optical material of fluorene acrylic. The high refractive optical material or photochromic high refractive optical material of the present invention includes optical lenses such as spectacle lenses, and has excellent optical properties such as transparency, thermal stability, and light resistance. In addition, the photochromic high refractive optical material of the present invention has a high refractive index and excellent photochromic ability than the existing medium refractive lens level.

The polymerizable composition for high refractive optical material of the present invention includes any one or more of the compound represented by Formula 1 and the compound represented by Formula 2. The polymerizable composition is a compound represented by the following formula (3), a compound represented by the formula (4), a compound represented by the formula (5), diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol as another acrylic monomer Dimethacrylate. Butanediol dimethacrylate, hexamethylene dimethacrylate, bisphenol A dimethacrylate, 2,2-bis (4-methacryloyloxyethoxy-3,5-dibromophenyl) propane, 2,2 -Bis- (4-methacryloyloxyethoxyphenyl) propane, 2,2-bis- (4-ethacryloyloxyethoxyphenyl) propane, 2,2-bis- (4-methacryloyl Oxypentaethoxyphenyl) propane, bis-4-vinyl ether, bis-4-vinyl sulfide, 1,2- (p-vinylbenzyloxy) ethane, 1,2- (p-vinylbenzylthio) ethane, bis- (p-vinyleneoxy ethyl) sulfide, 2,2-bis-4-bis-4-vinylbenzyl sulfide, pentaerythritol triacrylate, pentaerythritol tetraacrylate, propoxylated glycerol triacylate, trimethyl All propane triacrylate, dipentaerythritol hexaacrylate, bisphenol A- diglycidyl ether diacrylate type, bisphenol A- diglycidyl ether dimeth One or two or more compounds selected from the group consisting of taacrylate, tetrabromo bisphenol A-diglycidyl ether diacrylate, tetrabromobisphenol A-diglycidyl ether dimethacrylate, and the like It may further include.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

 In Formula 4 n is 3 ~ 10.

[Formula 5]

The polymerizable composition of the present invention may further include a compound represented by Formula 6 below.

[Formula 6]

The polymerizable composition of the present invention may further include a reactive diluent. As a reactive diluent, preferably styrene, divinylbenzene, alphamethylstyrene, alphamethylstyrenedimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxy styrene, monobenzyl maleate, dibenzyl maleate, monobenzyl Fumarate, dibenzyl fumarate, methylbenzyl malate, dimethyl malate, diethyl malate, dibutyl malate, dibutyl fumarate, monobutyl malate, monopentyl malate, dipentyl malate, monopentyl fumarate One or two or more compounds selected from the group consisting of, dipentyl fumalate and diethylene glycol bisaryl carbonate can be used.

The polymerizable composition of the present invention may further include any one or more of a thermal stabilizer, an internal mold release agent, a UV absorber, a polymerization initiator (catalyst).

The heat stabilizer can be used for all of the heat stabilizer surfaces that can be used for optical lenses such as phosphorus heat stabilizers, metal fatty acid salts, lead compounds, and organic tin compounds.

When the phosphorus thermal stabilizer is used, yellowing at high temperatures, in particular, yellowing at the time of secondary polymerization, yellowing at the time of hard or multi-coating, and yellowing at the time of lens storage can be effectively suppressed. As a phosphorus heat stabilizer, Preferably, a triphenyl phosphite, a diphenyldecyl phosphite, a diphenyl isodecyl phosphite, a phenyl didecyl phosphite, a diphenyl dodecyl phosphite, a trinoyl phenyl phosphite, a diphenyl isooctyl phosphate One or two or more compounds selected from the group consisting of pit, tributyl phosphite, tripropyl phosphite, triethyl phosphite, trimethyl phosphite, tris (monodecyl phosphite) and tris (monophenyl) phosphite Can be.

As the metal fatty acid salt type, one or two selected from compounds such as calcium stearate, barium stearate, zinc stearate, cadmium stearate, lead stearate, magnesium stearate, aluminum stearate, potassium stearate and zinc octoate The above compounds can be used.

The lead-based heat stabilizer is selected from compounds such as, for example, 3PbO.PbSO4.4H ₂ O, 2PbO.Pb (C ₈ H ₄ O ₄ ), 3PbO.Pb (C ₄ H ₂ O ₄ ) .H ₂ O and the like. Species or two or more species may be used.

The organotin type is, for example, dibutyltin diaurate, dibutyltin malate, dibutyltin bis (isooctyl maleate), dioctyltin malate, dibutyltin bis (monomethylmaleate), dibutyltin bis (Lauryl mercaptide), dibutyltin bis (isooxyl mercaptoacetate), monobutyltin tris (isooctyl mercaptoacetate), dimethyltinbis (isooctyl mercaptoacetate), methyltin tris (isooctylmer Captoacetate), dioctyl tin bis (isooctyl mercaptoacetate), dibutyl tin bis (2-mercaptoethyl laurate), monobutyl tin tris (2- mercapto ethyrate), dimethyl tin bis (2- Mercaptoethylate) and monomethyltin tris (2-mercaptoethylorate) and the like.

The heat stabilizer may preferably be included in the composition at 0.01 to 5% by weight. When the thermal stabilizer is used at less than 0.01% by weight, the yellowing inhibitory effect is weak, and when the thermal stabilizer is used at more than 5% by weight, the polymerization failure rate during curing is high and the thermal stability of the cured product is lowered.

The polymerizable composition of the present invention may further include an internal release agent. Internal mold release agents can be used as long as they can be used in optical lenses. The internal mold release agent can be used alone or in combination of two or more, for example, a phosphate ester compound, a silicone surfactant, or a fluorine surfactant. The phosphate ester compound is, for example, polyoxyethylene nonyl phenol ether phosphate (5% by weight of 5 mole of ethylene oxide added, 80% by weight of 4 mole added, 10% by weight of 3 mole added, 1 mole added 5 % By weight), polyoxyethylene nonylphenol ether phosphate (3% by weight of 9 mole of ethylene oxide, 80% by weight of 8 mole added, 5% by weight of 9 mole added, 6% by weight of 7 mole added, 6 mol added 6 wt%), polyoxyethylene nonylphenol ether phosphate (13 mol added ethylene oxide 3 wt%, 12 mol added 80 wt%, 11 mol added 8 wt%, 9 mol added 3 weight percent, 4 mol added 6 weight percent), polyoxyethylene nonylphenol ether phosphate (17 weight added ethylene oxide 3 weight%, 16 mol added 79 weight%, 15 mol added 10 weight%, 14 mol added 4 weight%, 13 mol added 4 weight%), polyoxyethylene nonylphenol ether phosphate 5% by weight of 21 mole added ethylene oxide, 78% by weight 20 mole added, 19% added 7% by weight, 18% added 6% by weight, 17 moles added 4% by weight), gelle The UN ™ may be used alone or in combination of two or more thereof. The internal mold release agent may be included at 0.001 to 10% by weight, preferably in the polymerizable composition.

The polymerizable composition of the present invention may further include organic dyes, inorganic pigments, colorants, antioxidants, light stabilizers, and the like as in the conventional polymerizable compositions.

The polymerizable composition for photochromic high refractive optical material of the present invention further includes a photochromic compound together with any one or more of the compound represented by Formula 1 and the compound represented by Formula 2. Description of the remaining configuration is the same as the polymerizable composition for high refractive optical material.

Photochromic compounds are well known, including inorganic compounds such as silver halides, spiropyrans, spiroxazines, chromenes, fulguides, azos, and fulgimides. Organic compounds, such as a diaryl pietene type | system | group and a diarylethene type | system | group, are known. In the present invention, all known photochromic compounds may be used, and among them, appropriate ones may be selected in consideration of colors and the like. Specifically, for example, Reversacol Platinate Purple (Spiroxazine) (manufactured by James Robinson), Reversacol Sea Green (Spiropyran) (manufactured by James Robinson), Reversacol Solar Yellow (Chromene) (manufactured by James Robinson), Reversacol Berry Red ( Spiroxazine) (manufactured by James Robinson), benzopyran, naphthopyran (naphtho [1,2b], naphtho [2,1-b]), spiro-9-fluoreno [1,2-b] pyran, Phenantropin, quinopy, indeno-fused naphthopyrans, benzoxazines, naphthoxazines, spiro (indolin) pyridobenzoxazines and the like can be used.

Hereinafter, in the present invention, "(photochromic) polymerizable composition" is defined as referring to both the polymerizable composition for high refractive optical material and the polymerizable composition for photochromic high refractive optical material. "(Photochromic) high refractive optical material" is defined to refer to a high refractive optical material and a photochromic high refractive optical material together.

The fluorene acryl-based (photochromic) high refractive optical material of the present invention can be produced by casting polymerization of the (photochromic) polymerizable composition. According to a preferred embodiment, prior to mold polymerization, the purity of all the raw materials is checked to purify low purity compounds and use high purity compounds without purification. Preferably, high purity compounds up to 70-99.99% purity are used. According to a preferred embodiment, after the compound of Formula 1 or 2 and the compound of Formula 3 are mixed, the reaction catalyst is added and stirred, and then the polymerizable composition is injected into the mold through vacuum degassing. The mold into which the polymerizable composition was injected is placed in a forced circulation oven and gradually heat-cured from 30 ° C. to 100 ° C., and then cooled to about 70 ± 10 ° C. to detach and remove the mold to obtain a lens.

The (photochromic) high refractive optical material obtained according to the present invention can be used in various applications such as optical lenses including spectacle lenses, as well as prismatic lenses, prism film coating agents, LED lenses, automotive headlights, and the like.

EXAMPLE

Hereinafter, the present invention will be described in more detail with reference to specific examples. However, these examples are only for illustrating the present invention in more detail, the scope of the present invention is not limited by these examples.

Compounds Used in the Examples

Component (I) Compound

A fluorene-based acrylic resin having an average molecular weight of 546 g was used, and the structural formula is shown in Formula 11 below.

[Formula 11]

Component (II) Compound :

A fluorene-based acrylic resin having an average molecular weight of 561 g was used, and the structural formula is shown in Chemical Formula 12 below.

[Formula 12]

Component (III) Compound:

A compound having an average molecular weight of 308 g was used by introducing acrylic acid into a polyethyleneglycol having a homogeneous molecular weight of 200 g, and the structural formula is shown in Formula 13 below.

[Formula 13]

Component (IV) Compound

A compound having an average molecular weight of 486 g obtained by introducing methacrylic acid into an alcohol resin to which ethylene oxad was added to bisphenol A having an average molecular weight of 350 g was used, and the structural formula is shown in Chemical Formula 14.

[Formula 14]

Component (V) Compound

A 2-phenoxyethyl acrylate compound having a molecular weight of 192.21 g was used, and the structural formula is shown in Formula 15 below.

[Formula 15]

Property test method

The physical properties of the prepared optical lens were measured by the following method, and the results are shown in Table 1 .

1) Refractive index and Abbe number: It was measured using an Abbe refractometer, a DR-M4 model of Atago.

2) Specific gravity: It was measured by an underwater substitution method using an analytical balance.

3) Deformation: The epoxy acrylic resin composition was thermally cured at the time of manufacturing the optical lens and marked with "O" and "X" according to the breakage of the lens or the mold when the optical lens and the mold were separated at 70 ° C. "O" means that the lens or mold is not broken at all or one is broken during separation of 100 optical lenses and molds, and "X" means that 4 or more lenses or molds are separated during separation of 100 optical lenses and molds. It is shown as a broken case.

4) Transparency: 100 sheets of lens are visually observed under a Mercury Arc Lamp, a USHIO USH-10D, marked as "O" if less than 3 optical lenses are found. If these are found in more than two, they are marked with "X".

5) Thermal Stability: The cured optical lens was kept at 100 ° C for 10 hours, and when the change in color was indicated by "O" if the APHA value did not change by more than 2, it changed to "X" when the APHA changed by 2 or more Indicated.

6) Light resistance: Q-Lab's QUV / SE model Accelerlated Weathering Tester was used. The QUV test was performed using a 1.2 mm thick flat lens under UVA-340 (340 nm), light 0.76 W / m ² , 4 hours BPT (Blank Panel Temperature) (60 ℃), 4 hours condensation (50 ℃) After irradiation, the color change was measured as "O" if the APHA value did not change more than 3, and "X" if the change in APHA value was 3 or more.

< Example 1>

According to the composition shown in Table 1, to 60 g of component (I), 7 g of component (III), 16 g of component (IV) and 7 g of component (IV), 10 g of divinylbenzene and 0.5 g of alphamethylstyrene dimer were added as a molecular weight regulator, Stir for about 30 minutes. Then filtered with a filter paper of 0.45㎛ or less, 0.3g of V-65 (2,2-azobis (2,4-dimethylpentanenitrile) and DPC (1,1-di- (tert-butylperoxy) as a catalyst ), 3,3,5-dimethylcyclohexane) 0.03 g was added and mixed to prepare a polymerizable composition for an optical lens, and an optical lens was prepared by the following method and the physical properties of the lens were measured. Is shown in Table 1 .

(1) The prepared polymerizable composition was stirred for 1 hour, degassed under reduced pressure for 10 minutes, filtered, and then poured into a glass mold assembled with a polyester adhesive tape.

(2) The glass mold into which the polymerizable composition was injected was heat-cured in a forced circulation oven from 35 ° C. to 110 ° C. over 20 hours, and then cooled to 70 ° C. to remove the glass mold to obtain a lens. The resulting lens was processed to a diameter of 72 mm and then ultrasonically washed with an alkaline aqueous washing solution, followed by annealing at 120 ° C. for 2 hours. The physical properties were measured by the following method, and the results are shown in Table 1 .

< Examples 2-3

In the same manner as in Example 1, according to the composition shown in Table 1 , the composition and the optical lens were prepared and tested for physical properties, respectively, and the results are shown in Table 1 .

< Example 4>

According to the composition shown in Table 1, 60 g of component (I), 8 g of component (III), 13 g of component (IV), and 5 g of component (V) of the fluorene epoxy acrylate compound were 14 g of divinylbenzene and 0.4 alpha-methylstyrene dimer. g and 0.03 g of a photochromic coloring agent manufactured by JAMES ROBINSON were added, and the resultant was stirred for about 30 minutes. Thereafter, the resultant was filtered using a filter paper of 0.45 µm or less, and 0.3 g of V-65 (2,2-azobis (2,4-dimethylpentanenitrile) and DPI (1,1-di- (tert-butylperoxy) were used as a catalyst. ), 3,3,5-dimethylcyclohexane) 0.03 g was added and mixed to make a polymerizable composition for an optical lens. Then, an optical lens was manufactured in the same manner as in Example 1 and the physical properties of the lens were measured. The results are shown in Table 1 .

< Examples 5-7>

Example 4 was prepared for each composition and the optical lens according to the proportion described in Table 1, without the photochromic coloring agent in the same manner as the experiment with the physical properties, the results are shown in Table 1.

As can be seen from the results of Table 1 below, the spectacle lens manufactured according to the present invention suppressed the phenomenon of polymerization imbalance, and exhibited good deforming, transparency, thermal stability, and light resistance.

Table 1

ingredient		Example
		One	2	3	4	5	6	7
Basic resin (g)	Component I (Formula 1)	60		48	60		55	55
	Component II (Formula 2)		55			50
	Component III (Formula 3)	7	13	15	8	14	10	10
	Component IV (Formula 4)	16	10	10	13	15	15	17
	Component V (Formula 5)	7	6	9	5	7	5	5
Polymerization regulator (g)	DVB	10	16	18	14	14	15	13
Photochromic colorant (g)	C1				0.03
	C2					0.03
	C3						0.03
	C4							0.03
Radical initiator (g)	M3	0.03	0.03	0.03	0.03	0.03	0.03	0.03
	DPC	0.3	0.3	0.3	0.3	0.3	0.3	0.3
Optical properties	Refractive index (nE, 20 ℃)	1.6053	1.5976	1.5895	1.6015	1.5970	0.5976	1.5988
	Abbe water (υd, 20 ℃)	29.9	29.8	30.2	29.8	30.1	29.9	29.6
	importance	1.201	1.198	1.190	1.199	1.196	1.198	1.197
	Tg (℃)	89	93	84	89	90	86	88
	Dysplasia	0	0	0	0	0	0	0
	Thermal stability	0	0	0	0	0	0	0
	Light resistance	0	0	0	0	0	0	0

Polymerization regulator

DVB: Divinylbenzene

Photochromic colorants

C1: Reversacol Platinate Purple (Spiroxazine) from James Robinson

C2: Reversacol Sea Green (Spiropyran) from James Robinson

C3: Reversacol Solar Yellow (Chromene) from James Robinson

C4: Reversacol Berry Red (Spiroxazine) from James Robinson

Polymerization initiator

V65: 2,2'-azobis (2,4-dimethylbarrenonitrile) (2,2'-azobis (2,4-dimethylvaleronitrile)

DPC: 1,1-di- (tert-butylperoxy) -3,3,5-dimethylcyclohexane (1,1-Di- (tert-butylperoxy) -3,3,5-trimethylcyclohexane)

According to the present invention, a fluorene acrylic optical material having high refractive index and excellent photochromic performance and optical characteristics can be obtained. The excellent fluorene acrylic optical lens of the present invention has excellent photochromic colorability and transparency, thermal stability, and light resistance, and thus has high refractive index and excellent photochromic performance and optical properties over conventional medium refractive lens, and thus, existing photochromic high refractive index It can be widely used to replace the optical material. In particular, the (photochromic) high refractive optical material of the present invention can be used in various applications such as optical lenses, including prism lenses, prismatic lenses, prism film coating agents, LED lenses, automotive headlights and the like.

Claims (20)

1. A polymerizable composition for a high refractive optical material comprising at least one of a compound represented by Formula 1 and a compound represented by Formula 2.

   [Formula 1]

   

   [Formula 2]

   
2. According to claim 1, wherein the compound represented by the following formula (3), the compound represented by the formula (4), the compound represented by the formula (5), diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacryl Rate. Butanediol dimethacrylate, hexamethylene dimethacrylate, bisphenol A dimethacrylate, 2,2-bis (4-methacryloyloxyethoxy-3,5-dibromophenyl) propane, 2,2 -Bis- (4-methacryloyloxyethoxyphenyl) propane, 2,2-bis- (4-ethacryloyloxyethoxyphenyl) propane, 2,2-bis- (4-methacryloyl Oxypentaethoxyphenyl) propane, bis-4-vinyl ether, bis-4-vinyl sulfide, 1,2- (p-vinylbenzyloxy) ethane, 1,2- (p-vinylbenzylthio) ethane, bis- (p-vinyleneoxy ethyl) sulfide, 2,2-bis-4-bis-4-vinylbenzyl sulfide, pentaerythritol triacrylate, pentaerythritol tetraacrylate, propoxylated glycerol triacylate, trimethyl All propane triacrylate, dipentaerythritol hexaacrylate, bisphenol A- diglycidyl ether diacrylate type, bisphenol A- diglycidyl ether dimeth One or two or more compounds selected from the group consisting of taacrylate, tetrabromo bisphenol A-diglycidyl ether diacrylate, and tetrabromobisphenol A-diglycidyl ether dimethacrylate A polymerizable composition for high refractive optical material further comprising.

   [Formula 3]

   

   [Formula 4]

   

    (n = 3-10)

   [Formula 5]

   
3. The polymerizable composition of claim 1, further comprising a compound represented by the following Chemical Formula 3.

   [Formula 3]

   
4. The polymerizable composition for high refractive optical material according to claim 1 or 2, further comprising a compound represented by the following formula (6).

   [Formula 6]

   
5. The styrene, divinylbenzene, alpha methyl styrene, alpha methyl styrene dimer, benzyl methacrylate, chlorostyrene, bromo styrene, methoxy styrene, monobenzyl maleate, dibenzyl maleate according to claim 1 or 2. , Monobenzyl fumarate, dibenzyl fumarate, methylbenzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, dipentyl maleate, mono A polymerizable composition for high refractive optical materials further comprising one or two or more reactive diluents selected from the group consisting of pentyl fumarate, dipentyl fumarate, diethylene glycol bisaryl carbonate.
6. The polymerizable composition for high refractive optical material according to claim 1 or 2, further comprising any one or more of a thermal stabilizer, an internal mold release agent, an ultraviolet absorber, and a polymerization initiator.
7. (a) any one or more of the compounds represented by Formula 1 below and the compounds represented by Formula 2,

   (b) A polymerizable composition for photochromic high refractive optical materials comprising a photochromic compound.

   [Formula 1]

   

   [Formula 2]

   
8. According to claim 7, Compound represented by the following formula (3), compound represented by the formula (4), compound represented by the formula (5), diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacryl Rate. Butanediol dimethacrylate, hexamethylene dimethacrylate, bisphenol A dimethacrylate, 2,2-bis (4-methacryloyloxyethoxy-3,5-dibromophenyl) propane, 2,2 -Bis- (4-methacryloyloxyethoxyphenyl) propane, 2,2-bis- (4-ethacryloyloxyethoxyphenyl) propane, 2,2-bis- (4-methacryloyl Oxypentaethoxyphenyl) propane, bis-4-vinyl ether, bis-4-vinyl sulfide, 1,2- (p-vinylbenzyloxy) ethane, 1,2- (p-vinylbenzylthio) ethane, bis- (p-vinyleneoxy ethyl) sulfide, 2,2-bis-4-bis-4-vinylbenzyl sulfide, pentaerythritol triacrylate, pentaerythritol tetraacrylate, propoxylated glycerol triacylate, trimethyl All propane triacrylate, dipentaerythritol hexaacrylate, bisphenol A- diglycidyl ether diacrylate type, bisphenol A- diglycidyl ether dimeth One or two or more compounds selected from the group consisting of taacrylate, tetrabromo bisphenol A-diglycidyl ether diacrylate, and tetrabromobisphenol A-diglycidyl ether dimethacrylate A polymerizable composition for photochromic high refractive optical materials, further comprising.

   [Formula 3]

   

   [Formula 4]

   

    (n = 3-10)

   [Formula 5]

   
9. The polymerizable composition for photochromic high refractive optical material according to claim 7, further comprising a compound represented by the following Chemical Formula 3.

   [Formula 3]

   
10. The polymerizable composition for photochromic high refractive optical material according to claim 7 or 8, further comprising a compound represented by the following formula (6).

    [Formula 6]

    
11. The method according to claim 7 or 8, wherein styrene, divinylbenzene, alpha methyl styrene, alpha methyl styrene dimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxy styrene, monobenzyl maleate, dibenzyl maleate , Monobenzyl fumarate, dibenzyl fumarate, methylbenzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, dipentyl maleate, mono A polymerizable composition for a photochromic high refractive optical material further comprising one or two or more reactive diluents selected from the group consisting of pentyl fumarate, dipentyl fumarate, diethylene glycol bisaryl carbonate.
12. The polymerizable composition for photochromic high refractive optical material according to claim 7 or 8, further comprising any one or more of a thermal stabilizer, an internal mold release agent, an ultraviolet absorber, and a polymerization initiator.
13. A method for producing a fluorene acrylic high refractive optical material comprising casting a polymerizable polymerizable composition according to claim 1 or 2.
14. A fluorene acrylic high refractive optical material obtained by casting a polymer of the polymerizable composition of claim 1 or 2.
15. 15. The fluorene acrylic high refractive optical material according to claim 14, wherein the optical material is an optical lens including an spectacle lens.
16. 15. The fluorene acrylic high refractive optical material according to claim 14, wherein the optical material is any one of a prism lens, a prism film coating agent, an LED lens, and an automobile headlight.
17. A method for producing a fluorene acrylic photochromic high refractive optical material comprising casting a polymerizable polymerizable composition according to claim 7 or 8.
18. A fluorene acrylic photochromic high refractive optical material obtained by casting a polymer of the polymerizable composition of claim 7 or 8.
19. 19. The fluorene acrylic photochromic high refractive optical material according to claim 18, wherein the optical material is an optical lens including an spectacle lens.
20. The fluorene acrylic photochromic high refractive optical material according to claim 18, wherein the optical material is any one of a prism lens, a prism film coating agent, an LED lens, and an automobile headlight.