JP2005255923A - Electrooptical composition and optical material for optical waveguide - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an electrooptical composition which serves both as a material such as a clad layer constituting an optical waveguide and as a material having functions such as optical modulation and optical switching and has excellent heat resistance, transmission characteristics (low transmission loss), crack resistance and the like. <P>SOLUTION: The electrooptical composition comprises a hydrolysate of hydrolyzable silane compounds expressed by general formula: (R<SP>1</SP>)<SB>p</SB>(R<SP>2</SP>)<SB>q</SB>Si(X)<SB>4-p-q</SB>(wherein, R<SP>1</SP>is a fluorine atom-containing non-hydrolyzable organic group; R<SP>2</SP>is a non-hydrolyzable organic group containing no fluorine atom; X is a hydrolyzable group; p is 1 or 2; q is 0 or 1) or a fluorine-containing polysiloxane comprising a condensate of the hydrolysate or an electrooptical organic compound. When the composition is used for a material for an upper clad layer 6 of the waveguide 1, the refractive index of the composition changes by the impression of voltage by electrodes 3, 7, which can be utilized for light modulation, optical switch and the like. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to an optical material for an optical waveguide whose refractive index changes due to a change in electric field, and an electro-optical composition for forming the material.

In the multimedia era, in response to demands for large capacity and high speed information processing in optical communication systems and computers, transmission systems using light as a transmission medium are public communication networks, LAN (local area networks), FA (factory automation). ), Being used for interconnects between computers, home wiring, and the like.
Among the elements constituting such a transmission system, the optical waveguide is an optical device, an optoelectronic integrated circuit (OEIC), an optical integrated circuit ( This is a basic component in an optical IC).

As one application example of an optical waveguide, it is provided in a core part made of a low refractive index change material with a small change in refractive index with respect to changes in the surrounding environment and a small light propagation loss, and a part around the core part. A high-refractive-index changing part made of a high-refractive-index changing material (specifically, a material exhibiting an electro-optic effect) having a refractive index change coefficient larger than that of the low-refractive index changing material with respect to the surrounding environment change; Clad part provided around the high refractive index changing part, etc., and a functional part (specifically, upper and lower electrodes to which a voltage is applied) for causing a change in the surrounding environment provided in a part around the clad part, etc. There has been proposed a waveguide-type optical functional device having the following (Patent Document 1).
This waveguide type optical functional device is for performing optical modulation, optical switching, etc. using an optical waveguide formed on a substrate.
As an example of the high refractive index changing material used in the waveguide type optical functional device, an organic material in which an azo dye is added to polymethyl methacrylate is described.
JP-A-9-318978

The waveguide-type optical functional device described in the above literature includes a high refractive index changing portion formed of a material different from these portions in addition to the core portion and the cladding portion. Therefore, compared to a normal optical waveguide consisting only of a core part and a clad part, a large number of types of materials and manufacturing processes are required. In this respect, if the types of materials and the number of manufacturing steps can be reduced, it is possible to improve the manufacturing efficiency, which is advantageous.
On the other hand, it is generally difficult for a polymer-based material (for example, polymethyl methacrylate) for forming a cladding part or the like to be excellent in all physical properties such as heat resistance, transmission characteristics, and crack resistance. Therefore, a material excellent in heat resistance, transmission characteristics, crack resistance and the like is required.
Therefore, an object of the present invention is a composition that can be used as a material for a portion such as a clad layer constituting an optical waveguide and a material for functions such as optical modulation and optical switch, and has a heat resistance. Another object of the present invention is to provide an electro-optical composition having excellent transmission characteristics (low transmission loss), crack resistance and the like.

The present inventors have found that the above-mentioned problems can be achieved by using an electro-optical composition containing an electro-optical organic compound in a specific polymerizable compound, and completed the present invention.
That is, the electro-optical composition of the present invention is characterized by containing a fluorine-containing polysiloxane and an electro-optical organic compound.
As a preferred example of the electro-optical composition, the fluorine-containing polysiloxane is represented by the following general formula (1):
(R ¹ ) _p (R ² ) _q Si (X) _4-pq (1)
[Wherein R ¹ is a non-hydrolyzable organic group having 1 to 12 carbon atoms containing a fluorine atom, and R ² is a non-hydrolyzable organic group having 1 to 12 carbon atoms (however, fluorine Excluding those containing atoms.), X is a hydrolyzable group, p is an integer of 1 or 2, and q is an integer of 0 or 1. ]
The thing which is at least 1 or more types chosen from the group which consists of the hydrolyzate of the hydrolysable silane compound represented by these, and the condensate of this hydrolyzate is mentioned.

［式中、Ｒ^３はフッ素原子を含有する炭素数が１〜１２である非加水分解性の有機基、Ｒ^４はフッ素原子を含んでいてもよい炭素数が１〜１２である非加水分解性の有機基であって、Ｒ^３と同じでもよい。］
また、前記含フッ素ポリシロキサンは、さらに下記一般式（４）及び（５）からなる群より選ばれる少なくとも一種以上の構造を有することができる。

［式中、Ｒ^５はフェニル基又はフッ素化フェニル基、Ｒ^６はフッ素原子を含んでいてもよい炭素数が１〜１２である非加水分解性の有機基であって、Ｒ^５と同じでもよい。］
前記電気光学性有機化合物は、好ましくは、電子供与性基及び電子求引性基を有するものである。
このような２つの基を有する電気光学性有機化合物の好ましい例としては、電子供与性基が、アミノ、ジアルキルアミノ、ヒドロキシアルキルアミノまたはアルコキシアルキルアミノであり、かつ、電子求引性基が、ニトロ、ジシアノビニルまたはトリシアノビニルであるものが挙げられる。
このような２つの基を有する電気光学性有機化合物は、好ましくは、芳香環等を主骨格とするものであり、具体的には、アニリン誘導体、スチルベン誘導体、アゾベンゼン誘導体、イミン誘導体等である。
本発明の電気光学性組成物は、好ましくは、光酸発生剤を含むことができる。
本発明の光導波路用光学材料は、電場の変化により屈折率が変化する光導波路用光学材料であって、前記電気光学性組成物の硬化物からなることを特徴とする。 Here, the fluorine-containing polysiloxane may have at least one structure selected from the group consisting of the following general formulas (2) and (3).

[Wherein R ³ is a non-hydrolyzable organic group containing 1 to 12 carbon atoms containing a fluorine atom, and R ⁴ is a non-hydrolyzed carbon group having 1 to 12 carbon atoms which may contain a fluorine atom. An organic group which may be the same as R ³ . ]
The fluorine-containing polysiloxane may further have at least one structure selected from the group consisting of the following general formulas (4) and (5).

[Wherein, R ⁵ is a phenyl group or a fluorinated phenyl group, R ⁶ is a non-hydrolyzable organic group having 1 to 12 carbon atoms which may contain a fluorine atom, and the same as R ⁵ Good. ]
The electro-optical organic compound preferably has an electron donating group and an electron withdrawing group.
As a preferable example of the electro-optical organic compound having such two groups, the electron donating group is amino, dialkylamino, hydroxyalkylamino or alkoxyalkylamino, and the electron withdrawing group is nitro. , Dicyanovinyl or tricyanovinyl.
Such an electro-optical organic compound having two groups is preferably an aromatic ring or the like as a main skeleton, and specifically, an aniline derivative, a stilbene derivative, an azobenzene derivative, an imine derivative, or the like.
The electro-optical composition of the present invention can preferably contain a photoacid generator.
The optical material for an optical waveguide according to the present invention is an optical material for an optical waveguide whose refractive index changes due to a change in electric field, and is characterized by comprising a cured product of the electro-optical composition.

According to the electro-optical composition of the present invention, two portions that have heretofore been formed of different materials can be formed of the same material. For example, when the composition of the present invention is used as a material for a cladding layer of an optical waveguide, it has functions such as optical modulation and optical switch, and is excellent without causing adverse effects due to containing an electro-optical organic compound. High heat resistance, transmission characteristics (low transmission loss), etc. can be exhibited.
Moreover, the electro-optical composition of the present invention can exhibit excellent patterning properties when it contains a photoacid generator.
In addition, the electro-optical composition of the present invention can have excellent crack resistance, long-term reliability, and the like when a specific fluorine-containing polysiloxane is used.
Further, the electro-optical composition of the present invention is a material whose refractive index changes due to a change in electric field, in addition to optical waveguide components (cladding layers, etc.), as well as optical switch couplings interposed between optical waveguides. It can be widely applied as an optical material for an optical waveguide, such as a portion.
In the present specification, the term “optical waveguide optical material” is used to include the material of the optical waveguide itself and the material of the peripheral structure of the optical waveguide (material of the portion related to the optical waveguide).

The electro-optical composition of the present invention contains (A) a fluorine-containing polysiloxane, (B) an electro-optical organic compound, (C) a photoacid generator, and (D) an organic solvent. In addition, a component (C) and a component (D) are components mix | blended as needed. Hereinafter, each component will be described in detail.
[A. Fluorine-containing polysiloxane]
The fluorine-containing polysiloxane used in the present invention is one containing two or more —Si—O— structural units (mainly oligomers).
A preferred example of the component (A) (fluorinated polysiloxane) is at least one selected from the group consisting of a hydrolyzate of a hydrolyzable silane compound represented by the following general formula (1) and a condensate of the hydrolyzate. It consists of the above, Preferably, the silanol group content is 1-10 mmol / g. Here, the hydrolyzate of the hydrolyzable silane compound means, for example, a product in which an alkoxy group is changed to a silanol group by a hydrolysis reaction, but also a part of silanol groups or silanol groups and alkoxy groups. It also means a partial condensate obtained by condensing.

(R ¹ ) _p (R ² ) _q Si (X) _4-pq (1)
[In General Formula (1), R ¹ is a non-hydrolyzable organic group having 1 to 12 carbon atoms, and R ² is a non-hydrolyzable organic group having 1 to 12 carbon atoms. , X is a hydrolyzable group, p is an integer of 1 or 2, and q is an integer of 0 or 1. ]

The component (A) can be generally obtained by heating a hydrolyzable silane compound represented by the general formula (1) or a mixture of this with a hydrolyzable silane compound other than the general formula (1). . The hydrolyzable silane compound is hydrolyzed by heating to become a hydrolyzate, or the hydrolyzate undergoes a condensation reaction to produce component (A).

(1) Organic group R ¹
R ¹ in the general formula (1) is a non-hydrolyzable organic group having 1 to 12 carbon atoms and containing a fluorine atom. Here, the term “non-hydrolyzable” means that it is a property that exists stably as it is under the condition that the hydrolyzable group X is hydrolyzed. Examples of such non-hydrolyzable organic groups include fluorinated alkyl groups and fluorinated aryl groups. Specific examples of the fluorinated alkyl group include a trifluoromethyl group, a trifluoropropyl group, a heptadecafluorodecyl group, a tridecafluorooctyl group, and a nonafluorohexyl group. Specific examples of the fluorinated aryl group include a pentafluorophenyl group.
Of these, C _n F _{2n + 1} C _m H _2m [m is an integer of 0 to 5, n is an integer of 1 to 12, and m + n is 1 to 12. A fluorinated alkyl group represented by the formula (1), having a large fluorine content such as a heptadecafluorodecyl group, a tridecafluorooctyl group, a nonafluorohexyl group, etc., and having a long chain is particularly preferable.
The subscript p in the general formula (1) is an integer of 1 or 2, but is preferably 1.

(2) Organic group R ²
R ² in the general formula (1) is a non-hydrolyzable organic group having 1 to 12 carbon atoms (excluding those containing a fluorine atom). As R ² , either a non-polymerizable organic group or a polymerizable organic group may be selected.
Here, examples of the non-polymerizable organic group include an alkyl group, an aryl group, an aralkyl group, or a deuterated or halogenated group thereof. These may be linear, branched, cyclic, or combinations thereof.
Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, a cyclohexyl group, and an octyl group. Preferred halogen atoms include fluorine, chlorine, bromine, iodine and the like.
Specific examples of the aryl group include phenyl group, tolyl group, xylyl group, naphthyl group, biphenyl group, deuterated aryl group, and halogenated aryl group.
Specific examples of the aralkyl group include a benzyl group and a phenylethyl group.
Further, a group having a structural unit containing a hetero atom may be used as the non-polymerizable organic group. Examples of the structural unit include an ether bond, an ester bond, and a sulfide bond. Moreover, when it contains a hetero atom, it is preferable that it is non-basic.

On the other hand, the polymerizable organic group is preferably an organic group having one or both of a radical polymerizable functional group and a cationic polymerizable functional group in the molecule. By introducing such a functional group, radical polymerization or cationic polymerization can be caused to cure the composition more effectively.
Further, among the radical polymerizable functional group and the cationic polymerizable functional group in the polymerizable organic group, a more preferable one is a cationic polymerizable functional group. This is because the photoacid generator can cause not only a curing reaction in a silanol group but also a curing reaction in a cationic polymerizable functional group at the same time.
Here, the subscript q in the general formula (1) is an integer of 0 or 1, but is preferably 0.

(3) Hydrolyzable group X
X in the general formula (1) is a hydrolyzable group. Here, the hydrolyzable group is usually a silanol group that is hydrolyzed by heating in a temperature range of 0 to 150 ° C. for 1 to 10 hours in the presence of a catalyst and excess water at 1 atm. Or a group capable of forming a siloxane condensate.
Here, examples of the catalyst include an acid catalyst and an alkali catalyst. Examples of the acid catalyst include monovalent or polyvalent organic acids, inorganic acids, Lewis acids, and the like. Specific examples of the organic acid include formic acid, acetic acid, oxalic acid and the like. Specific examples of the Lewis acid include metal compounds, inorganic salts such as Ti, Zr, Al, and B, alkoxides, and carboxylates. Specific examples of the alkali catalyst include alkali metal or alkaline earth metal hydroxides, amines, acidic salts, basic salts, and the like. The addition amount of the catalyst necessary for the hydrolysis is preferably 0.001 to 5%, more preferably 0.002 to 1% with respect to the total silane compound.

Specific examples of the hydrolyzable group X include a hydrogen atom, an alkoxy group having 1 to 12 carbon atoms, a halogen atom, an amino group, and an acyloxy group.
Here, preferred specific examples of the alkoxy group having 1 to 12 carbon atoms include methoxy group, ethoxy group, propoxy group, butoxy group, phenoxybenzyloxy group, methoxyethoxy group, acetoxyethoxy group, and 2- (meth) acryloxy. In addition to ethoxy group, 3- (meth) acryloxypropoxy group, 4- (meth) acryloxybutoxy group, etc., epoxy group-containing alkoxy groups such as glycidyloxy group, 2- (3,4-epoxycyclohexyl) ethoxy group, Examples thereof include oxetanyl group-containing alkoxy groups such as methyl oxetanyl methoxy group and ethyl oxetanyl methoxy group, and alkoxy groups having a 6-membered ring ether group such as oxacyclohexyloxy.
Preferred halogen atoms include fluorine, chlorine, bromine and iodine.

(4) Specific examples of hydrolyzable silane compounds represented by general formula (1) Specific examples of hydrolyzable silane compounds represented by general formula (1) include trifluoromethyltrimethoxysilane and trifluoromethyl. Triethoxysilane, 3,3,3-trifluoropropyltrichlorosilane, methyl-3,3,3, -trifluoropropyldichlorosilane, dimethoxymethyl-3,3,3, -trifluoropropylsilane, 3,3 3-trifluoropropyltrimethoxysilane, 3,3,3-trifluoropropylmethyldichlorosilane, 3,3,4,4,5,5,5,6,6,6-nonafluorohexyltrichlorosilane, 3, 3,4,4,5,5,5,6,6,6-nonafluorohexylmethyldichlorosilane, 3,3,4,4,5,5,6,6,7,7 8,8,8-heptadecafluorodecyltrichlorosilane, 3,3,4,4,5,5,6,7,7,8,8,8-heptadecafluorodecyltrimethoxysilane, 3,3 , 4,4,5,5,6,6,7,7,8,8,8-heptadecafluorodecyltriethoxysilane, 3,3,4,4,5,5,6,6,7,7 , 8,8,8-heptadecafluorodecylmethyldichlorosilane, 3-heptafluoroisopropoxypropyltriethoxysilane, pentafluorophenylpropyltrimethoxysilane, pentafluorophenylpropyltrichlorosilane and the like. Among these, 3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorodecyltriethoxysilane and 3,3,4,4,5,5 6,6,7,7,8,8,8-heptadecafluorodecyltrimethoxysilane, 3,3,4,4,5,5,5,6,6,6-nonafluorohexyltrichlorosilane, etc. preferable.

(5) Other hydrolyzable silane compounds As other hydrolyzable silane compounds, tetrachlorosilane, tetraaminosilane, tetraacetoxysilane, tetramethoxysilane, tetraethoxysilane, tetrabutoxysilane, tetraphenoxysilane, tetrabenzyloxysilane Silane compounds having four hydrolyzable groups such as trimethoxysilane and triethoxysilane; methyltrichlorosilane, methyltrimethoxysilane, methyltriethoxysilane, methyltributoxysilane, ethyltrimethoxysilane, ethyltriisopropoxy It has three hydrolyzable groups such as silane, ethyltributoxysilane, butyltrimethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, deuterated methyltrimethoxysilane, etc. Or a silane compound having two hydrolyzable groups such as dimethyldichlorosilane, dimethyldiaminosilane, dimethyldiacetoxysilane, dimethyldimethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, and dibutyldimethoxysilane. .

(6) Preparation of component (A)
The method for obtaining the component (A) by heating the hydrolyzable silane compound represented by the general formula (1) is not particularly limited as long as the silanol group content described below is not excessively or excessively reduced. The method which consists of the process of 1) -3) shown to can be mentioned. However, in the hydrolyzate of the hydrolyzable silane compound represented by the general formula (1), a partially unhydrolyzed hydrolyzable group may remain. In that case, the hydrolyzable silane compound and the hydrolyzate It becomes a mixture with things.
1) The hydrolyzable silane compound and acid catalyst represented by the general formula (1) are accommodated in a container equipped with a stirrer.
2) Next, an organic solvent is further accommodated in the container while adjusting the viscosity of the obtained solution to obtain a mixed solution.
3) After stirring the obtained mixed solution at a temperature not higher than the boiling point of the organic solvent or hydrolyzable silane compound in an air atmosphere, at 0 to 150 ° C. for 1 to 24 hours. Stir with heating. In addition, during heating and stirring, it is also preferable to concentrate the mixed solution by distillation or replace the organic solvent as necessary. Here, in order to adjust the refractive index of the final cured product, the curability of the composition, the viscosity, and the like, a hydrolyzable silane compound other than the hydrolyzable silane compound represented by the general formula (1) is mixed. Thus, a siloxane oligomer can also be prepared. In this case, after adding and mixing the hydrolyzable silane compound of general formula (1) and the other hydrolyzable silane compound in the step 1), the reaction can be carried out by heating.

［式中、Ｒ^３はフッ素原子を含有する炭素数が１〜１２である非加水分解性の有機基、Ｒ^４はフッ素原子を含んでいてもよい炭素数が１〜１２である非加水分解性の有機基であって、Ｒ^３と同じでもよい。］

成分（Ａ）が上記構造を有していると、本発明の電気光学性組成物を用いて作製される光導波路等の硬化物の耐クラック性等の物性をより一層向上させることができる。
さらに、前記一般式（１）のＲ^１が、ＣＦ_３（ＣＦ_２）_ｎ（ＣＨ_２）_ｍ［ｍは０〜５の整数、ｎは１〜１１の整数であり、ｍ＋ｎは１〜１１である。］であることが好ましい。Ｒ^１がこのような構造であると、本発明の組成物を用いてフォトリソグラフィー法により光導波路等を製造する際のパターニング性、該光導波路等の耐クラック性、および材料損失（導波路損失）等をより一層向上させることができる。
Ｒ^１が上記構造である場合において、（Ａ）成分はさらに、下記一般式（４）及び（５）からなる群のうち少なくとも一種以上の構造を有することが好ましい。 (7) Preferred Embodiment of Component (A) The component (A) preferably has at least one structure selected from the group consisting of the following general formulas (2) and (3).

[Wherein R ³ is a non-hydrolyzable organic group containing 1 to 12 carbon atoms containing a fluorine atom, and R ⁴ is a non-hydrolyzed carbon group having 1 to 12 carbon atoms which may contain a fluorine atom. An organic group which may be the same as R ³ . ]

When the component (A) has the above structure, physical properties such as crack resistance of a cured product such as an optical waveguide produced using the electro-optical composition of the present invention can be further improved.
Further, the ^{R 1} of the general formula (1) _{is, CF 3 (CF 2) n} (CH 2) m [m is an integer of 0 to 5, n is an integer of 1 to 11, m + n is 1 to 11 is there. ] Is preferable. When R ¹ has such a structure, patterning properties when producing an optical waveguide or the like by photolithography using the composition of the present invention, crack resistance of the optical waveguide or the like, and material loss (waveguide loss) ) And the like can be further improved.
In the case where R ¹ has the above structure, the component (A) preferably further has at least one structure selected from the group consisting of the following general formulas (4) and (5).

［式中、Ｒ^５はフェニル基、あるいはフッ素化フェニル基、Ｒ^６はフッ素原子を含んでいてもよい炭素数が１〜１２である非加水分解性の有機基であってＲ^５と同じでもよい。］

これらの一般式（４）または一般式（５）の構造を有する加水分解性化合物の具体例としては、上述の一般式（１）、または一般式（１）以外の加水分解性シラン化合物の具体例のうち、フェニル基またはフッ素化フェニル基を有する化合物が挙げられる。これらのうち、フェニルトリメトキシシラン、フェニルトリエトキシシラン、ペンタフルオロフェニルトリメトキシシラン等が特に好ましい。
成分（Ａ）が上記構造を有していると、本発明の組成物を用いて形成される光導波路等の耐熱性やパターニング性をより一層向上させることができる。

[Wherein, R ⁵ is a phenyl group or a fluorinated phenyl group, R ⁶ is a non-hydrolyzable organic group having 1 to 12 carbon atoms which may contain a fluorine atom, and may be the same as R ⁵ Good. ]

Specific examples of the hydrolyzable compound having the structure of the general formula (4) or the general formula (5) include specific examples of the hydrolyzable silane compounds other than the above general formula (1) or the general formula (1). Among the examples, compounds having a phenyl group or a fluorinated phenyl group can be mentioned. Of these, phenyltrimethoxysilane, phenyltriethoxysilane, pentafluorophenyltrimethoxysilane and the like are particularly preferable.
When the component (A) has the above structure, the heat resistance and patterning properties of an optical waveguide or the like formed using the composition of the present invention can be further improved.

[B. Electro-optical organic compound]
Component (B) (electro-optical organic compound) is a compound having an electro-optical effect.
By using the component (B), the refractive index of the cured product of the electro-optical composition of the present invention can be reversibly changed when the electric field is changed.
Component (B) is not particularly limited as long as it is a compound having an electro-optic effect, but it has a conjugated skeleton having delocalized electrons and an electron donating group and an electron seeking group bonded to this main skeleton. A compound having an attractive group is preferred.
Here, examples of a conjugated skeleton having delocalized electrons include aromatic compounds such as benzene, naphthalene, anthracene, biphenyl, and indene, furan, pyrrole, thiophene, oxazal, thiazole, imidazole, pyrazole, γ -Heterocyclic compounds such as pyran, pyridine, piperidine, pyridazine, pyrimidine, pyrazine, quinoline, and aromatic compounds were bonded to each other via an unsaturated bond-containing structure such as -CH = CH-, -N = N- And conjugated polyenes such as butadiene.

Examples of electron donating groups include amino, dialkylamino, hydroxyalkylamino, alkoxy.
Cialkylamino and the like can be mentioned.
Examples of the electron withdrawing group include nitro, dicyanovinyl, and tricyanovinyl.
Examples of component (B) include aniline derivatives such as p-dibutylaminonitrobenzene, stilbene derivatives such as 4-nitro-4′-aminostilbene, 1- [p- (dibutylamino) phenylvinyl-4-tricia Novinyl] thiophene, 1- (p-dibutylaminophenyl) -4-tricyanovinyl-ethylene, 1- (p-dibutylaminophenyl) -4-tricyanovinyl-1,3-butadiene and other styrene derivatives, 4-nitro-4 ′-(N-ethyl-N-hydroxyethyl) aminoazobenzene, 4-dicyanovinyl-4 ′-(N-ethyl-N-hydroxyethyl) aminoazobenzene, 4-dicyanovinyl-4 ′-( Azobenzene derivatives such as N, N-dimethyl) aminoazobenzene and N- (p-dibutylamino) benzylidene-p-to Examples include imine derivatives such as licyanovinylaniline.
The amount of component (B) is preferably 0.1 to 10 parts by weight, more preferably 0.5 to 5 parts by weight per 100 parts by weight of component (A). If the amount is less than 0.1 part by weight, it is difficult to obtain a sufficient electro-optical effect. When the blending ratio exceeds 10 parts by weight, the transparency is lowered, and the transmission characteristics may be lowered when used as a material for an optical waveguide.

[C. Photoacid generator]
Component (C) (photoacid generator) is decomposed by irradiation with radiation to release an acidic active substance that photocures component (A).
Here, examples of the radiation include visible light, ultraviolet rays, infrared rays, X-rays, electron beams, α rays, and γ rays. However, it is preferable to use ultraviolet rays from the viewpoint of having a constant energy level, a high curing rate, and a relatively inexpensive and compact irradiation apparatus.
Examples of the component (C) include an onium salt having a structure represented by the following general formula (6), a sulfonic acid derivative having a structure represented by the following general formula (7), and the like.

_{^{[R 7 a R 8 b R}} 9 c R 10 d W] + m [MZ m + n] -m (6)
[In General Formula (6), the cation is an onium ion, W is S, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, or —N≡N, and R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are the same or different organic groups, a, b, c and d are each an integer of 0 to 3, and (a + b + c + d) is equal to the valence of W. M is a metal or metalloid constituting the central atom of the halide complex [MZ _{m + n} ], for example, B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, and Co. Z is, for example, a halogen atom or an aryl group such as F, Cl, Br, etc., m is the net charge of the halide complex ion, and n is the valence of M. ]

Q _s- [S (= O) ₂ -R ¹¹ ] _t (7)
[In the general formula (7), Q is a monovalent or divalent organic group, R ¹¹ is a monovalent organic group having 1 to 12 carbon atoms, the subscript s is 0 or 1, and the subscript t is 1 or 2. is there. ]

(1) Onium salt Specific examples of the anion [MZ _{m + n} ] in the general formula (6) include tetrafluoroborate (BF ₄ ⁻ ), hexafluorophosphate (PF ₆ ⁻ ), hexafluoroantimonate (SbF ₆ ⁻ ), Examples include hexafluoroarsenate (AsF ₆ ⁻ ), hexachloroantimonate (SbCl ₆ ⁻ ), tetraphenyl borate, tetrakis (trifluoromethylphenyl) borate, tetrakis (pentafluoromethylphenyl) borate and the like.
Further, instead of the anion _{[MZ m + n]} in the general formula (6), the general formula ^- it is also preferable to use the anion represented by _[MZ n OH]. Furthermore, perchlorate ion (ClO ₄ ⁻ ), trifluoromethane sulfonate ion (CF ₃ SO ₄ ⁻ ), fluorosulfonate ion (FSO ₄ ⁻ ), toluene sulfonate ion, trinitrobenzene sulfonate anion, trinitrotoluene sulfonate Onium salts having other anions such as anions can also be used.

［一般式（８）中、Ｒ^１２およびＲ^１３は、それぞれ独立して水素又はアルキル基、Ｒ^１４は水酸基または−ＯＲ^１５（但し、Ｒ^１５は１価の有機基である。）を示し、ａは４〜７の整数、ｂは１〜７の整数である。ナフタレン環への各置換基の結合位置は特に限定されない。］

［Ｒ^１６−Ｐｈ^１−Ｉ^＋−Ｐｈ^２−Ｒ^１７］［Ｙ⁻］ （９）
［一般式（９）中、Ｒ^１６およびＲ^１７は、それぞれ１価の有機基であり、同一でも異なっていてもよく、Ｒ^１６およびＲ^１７の少なくとも一方は、炭素数が４以上のアルキル基を有しており、Ｐｈ^１およびＰｈ^２はそれぞれ芳香族基であり、同一でも異なっていてもよく、Ｙ⁻は１価の陰イオンであり、周期律表３族、５族のフッ化物陰イオンもしくは、ＣｌＯ_４ ⁻、ＣＦ_３ＳＯ_３ ⁻から選ばれる陰イオンである。］ The onium salt is preferably an aromatic onium salt, particularly preferably a triarylsulfonium salt, a compound represented by the following general formula (8), a diaryl iodonium salt represented by the following general formula (9) or a triaryl iodonium. It is salt.

[In General Formula (8), R ¹² and R ¹³ each independently represent hydrogen or an alkyl group, R ¹⁴ represents a hydroxyl group or —OR ¹⁵ (where R ¹⁵ is a monovalent organic group), a is an integer of 4 to 7, and b is an integer of 1 to 7. The bonding position of each substituent to the naphthalene ring is not particularly limited. ]

^{[R 16 -Ph 1 -I + -Ph} 2 -R 17] [Y -] (9)
[In General Formula (9), R ¹⁶ and R ¹⁷ are each a monovalent organic group and may be the same or different, and at least one of R ¹⁶ and R ¹⁷ is an alkyl group having 4 or more carbon atoms. And Ph ¹ and Ph ² are each an aromatic group, which may be the same or different, Y ⁻ is a monovalent anion, and is a group 3 or group 5 fluoride anion in the periodic table. An ion or an anion selected from ClO ₄ ⁻ and CF ₃ SO ₃ ^— . ]

Examples of the compound represented by the general formula (8) include 4-hydroxy-1-naphthyltetrahydrothiophenium trifluoromethanesulfonate, 4-butoxy-1-naphthyltetrahydrothiophenium trifluoromethanesulfonate, 1- (4,7- And dihydroxy) -naphthyltetrahydrothiophenium trifluoromethanesulfonate, 1- (4,7-di-t-butoxy) -naphthyltetrahydrothiophenium trifluoromethanesulfonate, and the like.
Further, as the diaryl iodonium salt, specifically, (4-n-decyloxyphenyl) phenyl iodonium hexafluoroantimonate, [4- (2-hydroxy-n-tetradecyloxy) phenyl] phenyl iodonium hexafluoroantimonate [4- (2-hydroxy-n-tetradecyloxy) phenyl] phenyliodonium trifluorosulfonate, [4- (2-hydroxy-n-tetradecyloxy) phenyl] phenyliodonium hexafluorophosphate, [4- (2 -Hydroxy-n-tetradecyloxy) phenyl] phenyliodonium tetrakis (pentafluorophenyl) borate, bis (4-t-butylphenyl) iodonium hexafluoroantimonate, bis (4-t-butylphenyl) Iodonium hexafluorophosphate, bis (4-t-butylphenyl) iodonium trifluorosulfonate, bis (4-t-butylphenyl) iodonium tetrafluoroborate, bis (dodecylphenyl) iodonium hexafluoroantimonate, bis (dodecylphenyl) Examples thereof include one or a combination of two or more of iodonium tetrafluoroborate, bis (dodecylphenyl) iodonium hexafluorophosphate, bis (dodecylphenyl) iodonium trifluoromethylsulfonate, and the like.

(2) Sulfonic acid derivatives The sulfonic acid derivatives represented by the general formula (7) include disulfones, disulfonyldiazomethanes, disulfonylmethanes, sulfonylbenzoylmethanes, imidosulfonates, benzoinsulfonates, 1-oxy Examples include sulfonates of 2-hydroxy-3-propyl alcohol, pyrogallol trisulfonates, benzyl sulfonates, and the like.
Among these, imide sulfonates are preferable, and trifluoromethyl sulfonate derivatives are more preferable.
Although the compounding quantity of a component (C) (photo-acid generator) is not restrict | limited in particular, Usually, it is 0-15 weight part per 100 weight part of component (A).
However, when the electro-optical composition is photocured with ultraviolet rays or the like, the amount of component (C) is preferably 0.1 to 15 parts by weight, more preferably 0.1 to 100 parts by weight of component (A). ~ 5 parts by weight. If the blending amount is less than 0.1 parts by weight, the photocurability is lowered and a sufficient curing rate tends not to be obtained. On the other hand, when the blending amount exceeds 15 parts by weight, the weather resistance and heat resistance of the resulting cured product tend to decrease.

[D. Organic solvent]
By blending the component (D) (organic solvent), the storage stability of the electro-optical composition can be improved and an appropriate viscosity can be imparted, and a cured product having a uniform thickness (for example, an optical waveguide) ) Can be formed.
Examples of the component (D) include ether organic solvents, ester organic solvents, ketone organic solvents, hydrocarbon organic solvents, alcohol organic solvents, and the like. Usually, it is preferable to use an organic solvent having a boiling point under atmospheric pressure in the range of 50 to 200 ° C. and capable of uniformly dissolving each component.
Examples of such organic solvents include aliphatic hydrocarbon solvents, aromatic hydrocarbon solvents, monoalcohol solvents, polyhydric alcohol solvents, ketone solvents, ether solvents, ester solvents, nitrogen-containing solvents. A sulfur-containing solvent or the like can be used. These organic solvents are used singly or in combination of two or more.
Among these (C) organic solvents, alcohols and ketones are preferable. This is because the storage stability of the composition can be further improved.
More preferable organic solvents include at least one compound selected from the group consisting of propylene glycol monomethyl ether, ethyl lactate, methyl isobutyl ketone, methyl amyl ketone, toluene, xylene, and methanol.

The type of component (D) (organic solvent) is preferably selected in consideration of the coating method of the electro-optical composition. For example, since a thin film having a uniform thickness can be easily obtained, it is preferable to use a spin coating method as a coating method. Examples of the organic solvent used in this case include ethylene glycol monoethyl ether and propylene glycol monomethyl ether. Glycol ethers such as ethyl cellosolve acetate, propylene glycol methyl ether acetate, ethylene glycol alkyl ether acetates such as propylene glycol ethyl ether acetate; esters such as ethyl lactate and ethyl 2-hydroxypropionate; diethylene glycol monomethyl ether, diethylene glycol dimethyl ether Diethylene glycols such as diethylene glycol ethyl methyl ether; methyl isobutyl ketone, 2-heptanone, It is preferable to use ketones such as rhohexanone and methyl amyl ketone, and it is particularly preferable to use propylene glycol monomethyl ether, ethyl cellosolve acetate, propylene glycol methyl ether acetate, ethyl lactate, methyl isobutyl ketone and methyl amyl ketone. .
The compounding quantity of a component (D) is 0-300 weight part per 100 weight part of a component (A), Preferably it is 1-300 weight part, More preferably, it is 2-200 weight part. When the blending amount is 1 to 300 parts by weight, the storage stability of the composition can be improved and an appropriate viscosity can be imparted, and an optical waveguide having a uniform thickness can be formed.
In addition, although the addition method in particular of component (D) is not restrict | limited, For example, when manufacturing component (A), you may add, and when mixing components (A)-(C). You may add to.

[Silanol group content in the composition]
The content of silanol groups in the bonding groups on all Si in the electro-optical composition of the present invention is preferably 10 to 50%, more preferably 20 to 40%. Within this range, the patterning property during alkali development is particularly good, and material loss can be reduced when an optical waveguide is formed.

[Other ingredients]
Furthermore, within the range that does not impair the object and effect of the present invention, an acid diffusion controller, a reactive diluent, a radical generator (photopolymerization initiator), a photosensitizer, a metal alkoxide, inorganic fine particles, a dehydrating agent, and a leveling agent. , Polymerization inhibitors, polymerization initiation assistants, wettability improvers, surfactants, plasticizers, UV absorbers, antioxidants, antistatic agents, silane coupling agents, polymer additives, and the like are also preferably added. .
The viscosity of the electro-optical composition of the present invention is preferably 5 to 5,000 mPa · s, more preferably 10 to 1,000 mPa · s at 25 ° C. If the viscosity exceeds 5,000 mPa · s, it may be difficult to form a uniform coating film. The viscosity can be appropriately adjusted by adjusting the blending amount of the organic solvent.

[Method for Fabricating Optical Waveguide Using Electro-Optic Composition]
Next, a method for producing an optical waveguide using the electro-optical composition of the present invention will be described with reference to FIG. FIG. 1 is a cross-sectional view showing an example of an optical waveguide produced using the electro-optical composition of the present invention.
(1) Formation of lower clad layer First, the electrode 3 is formed on the upper surface of the substrate 2 by ion sputtering. Then, the fluorine-containing polysiloxane composition for forming a lower clad layer is apply | coated to the surface of the board | substrate 2, and it dries or prebakes, and forms the thin film for lower clad layers. Then, the lower clad layer thin film is irradiated with light such as ultraviolet rays and cured to form the lower clad layer 4.
In addition, although it does not restrict | limit especially as a kind of board | substrate, In view of adhesiveness with the electro-optical composition of this invention, etc., it is preferable to use a silicon substrate, a glass substrate, etc., for example.
Moreover, as a method for forming the electrode on the upper surface of the substrate, for example, an ion sputtering method or the like can be used.
As an electrode material, a transparent electrode such as ITO (tin-doped indium oxide), IWO, ICO, InTiO, ZnU, AZO, GZO or the like is preferably used. Of these, ITO is preferably used.

(2) Formation of core portion Next, a fluorine-containing polysiloxane composition (having a refractive index larger than that of the clad layer after curing) is applied onto the lower clad layer 4 and dried or dried. Further, pre-baking is performed to form a thin film for the core part.
Thereafter, the upper surface of the core thin film is irradiated with light such as ultraviolet rays through a photomask having a predetermined line pattern, for example, according to a predetermined pattern.
As a result, only the portion irradiated with light is cured. Therefore, if other uncured portions are developed and removed with a developer, the core portion 5 made of a patterned cured film is formed on the lower cladding layer. The
(3) Formation of upper clad layer The upper clad layer composition made of the electro-optical composition of the present invention is applied to the surface of the lower clad layer 4 with the core portion 5 formed on the upper side, and dried or prebaked. Next, when the light is irradiated and cured, the upper clad layer 6 is formed.
It is preferable to further post-bake the upper cladding layer 6 as necessary. By post-baking, an upper clad layer having excellent hardness and heat resistance can be obtained.
Thereafter, when an electrode 7 for applying voltage is formed on the upper surface of the upper cladding layer 6, the optical waveguide 1 having the electro-optic effect is completed.
In addition, as a material of the electrode 7, a metal having high conductivity and high thermal conductivity such as Au, Ag, Cu, Co, Ta, Mo, Ti, Pt, Cr, and Al is preferably used. Among these, Au (gold) is preferably used.

In the optical waveguide 1, the refractive index value of the core portion 5 needs to be larger than the refractive indexes of the lower cladding layer 4 and the upper cladding layer 6. Specifically, in order to obtain more excellent waveguide characteristics, the refractive index of the core portion 5 is 1.450 to 1.650, and the lower cladding layer 4 with respect to light having a wavelength of 1,300 to 1,600 nm. In addition, the refractive index of the upper cladding layer 6 is set to 1.400 to 1.648, and the refractive index of the core portion 5 is set to 0.002 to 0.5 larger than the refractive indexes of the lower cladding layer 4 and the upper cladding layer 6. It is preferable.
The electro-optical composition of the present invention can be used not only as a material for a clad layer or the like constituting an optical waveguide, but also as an optical modulation or optical switch material such as an optical switch coupling member interposed between optical waveguides. Can be widely applied.

Hereinafter, the present invention will be described based on experimental examples.
[Preparation of component (A)]
[Preparation Example 1]
In a flask equipped with a stirrer and a reflux tube, methyltrimethoxysilane (2.97 g), phenyltrimethoxysilane (29.01 g), 3,3,4,4,5,5,6,6,7,7, 8,8,8-heptadecafluorodecyltriethoxysilane (25.64 g), propylene glycol monomethyl ether (1-methoxy-2-propanol) (31.00 g), and oxalic acid (0.04 g) were added and stirred. After that, the temperature of the solution was heated to 60 ° C. Then, distilled water (11.35 g) was added dropwise, and after completion of the addition, the solution was stirred at 120 ° C. for 6 hours. Finally, a 1-methoxy-2-propanol solution containing a siloxane oligomer having a solid content adjusted to 70% by weight was obtained. This is designated as “siloxane oligomer solution 1”.

[Preparation Example 2]
In a flask equipped with a stirrer and a reflux tube, phenyltrimethoxysilane (30.79 g), 3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorodecyl Triethoxysilane (22.64 g), tetraethoxysilane (4.62 g), propylene glycol monomethyl ether (29.93 g), and oxalic acid (0.04 g) were added and stirred, and then the temperature of the solution was brought to 60 ° C. Heated. Then, distilled water (11.98 g) was added dropwise, and after completion of the addition, the solution was stirred at 90 ° C. for 6 hours. And the 1-methoxy-2-propanol solution containing the siloxane oligomer which finally adjusted solid content to 65 weight% was obtained. This is designated as “siloxane oligomer solution 2”.

[Preparation of electro-optical composition]
[Composition 1]
To 100 g of siloxane oligomer solution 2 (solid content and organic solvent), 0.3 g of photoacid generator (DBNST) and 8.0 g of propylene glycol monomethyl ether are added and mixed uniformly to obtain a solid content concentration of 65 wt. The composition 1 adjusted to% was obtained.
[Composition 2]
To 100 g of siloxane oligomer solution 1 (solid content and organic solvent), 1.0 g of 4-dibutylaminonitrobenzene and 8.2 g of propylene glycol monomethyl ether are added and mixed uniformly to obtain a solid content concentration of 65% by weight. An adjusted composition was obtained.
[Composition 3]
To 100 g of siloxane oligomer solution 1 (solid content and organic solvent), 1.0 g of 4-dibutylaminonitrobenzene, 0.2 g of dibutyltin dilaurate, and 8.3 g of propylene glycol monomethyl ether were added and mixed uniformly. A composition having a concentration adjusted to 65% by weight was obtained.
[Composition 4]
To 100 g of siloxane oligomer solution 1 (solid content and organic solvent), 1.0 g of 4-dibutylaminonitrobenzene, 0.1 g of aminoethylaminopropyltrimethoxysilane, and 8.3 g of propylene glycol monomethyl ether are added and mixed uniformly. Thus, a composition having a solid content concentration adjusted to 65% by weight was obtained.
[Composition 5]
To 100 g of siloxane oligomer solution 1 (solid content and organic solvent), 1.0 g of 4-dibutylaminonitrobenzene, 0.32 g of photoacid generator (DBNST), and 8.4 g of propylene glycol monomethyl ether are added and mixed uniformly. Thus, a composition having a solid content concentration adjusted to 65% by weight was obtained.
[Composition 6]
A composition consisting only of 100 g of siloxane oligomer solution 1 (solid content and organic solvent) was designated as composition 6.
Table 1 shows the component compositions of Compositions 1-6.

[Example 1]
The siloxane oligomer solution 1 is applied on the surface of a glass substrate with a transparent electrode on which ITO has been sputtered by a spin coater, dried at 120 ° C. for 10 minutes, and then exposed to ultraviolet light having a wavelength of 365 nm and an illuminance of 6 mW / cm ² using an exposure machine. Irradiated for 1 minute. Furthermore, by heating at 200 ° C. for 1 hour, a lower cladding layer having a thickness of 15 μm was formed. The refractive index of light having a wavelength of 1,550 nm in this lower cladding layer was 1.439.
Next, the composition 1 was applied onto the lower clad layer with a spin coater, dried at 100 ° C. for 5 minutes, and then using a photomask engraved with an optical waveguide pattern having a width of 9 μm, a wavelength of 365 nm and an illuminance of 6 mW / cm ^2. The exposure was carried out by irradiating the ultraviolet rays of 1 min with an exposure machine for 1 minute. Thereafter, the substrate was heated at 100 ° C. for 1 minute, and then immersed in a developer composed of a 5% tetramethylammonium hydroxide (TMAH) aqueous solution to dissolve unexposed portions and washed with water. Then, after irradiating with ultraviolet rays for 3 minutes, a core part having a thickness of 8 μm was formed by heating at 200 ° C. for 1 hour. The refractive index of light having a wavelength of 1,550 nm in the core portion was 1.445.
Further, the composition 2 is applied to the upper surface of the lower clad layer having the core portion by a spin coater, dried at 100 ° C. for 10 minutes, and then heated at 200 ° C. for 1 hour to form an upper clad layer having a thickness of 10 μm. Formed. An Au (gold) electrode was formed on the upper surface of the upper clad layer by vapor deposition to complete an optical waveguide with an electrode.

[Example 2]
An optical waveguide with an electrode was produced in the same manner as in Example 1 except that the composition 3 was used for the upper clad layer.
[Example 3]
An optical waveguide with an electrode was produced in the same manner as in Example 1 except that the composition 4 was used for the upper clad layer.
[Example 4]
As a method of forming the upper clad layer, the composition 5 is applied by a spin coater, dried at 100 ° C. for 10 minutes, irradiated with ultraviolet light having a wavelength of 365 nm and an illuminance of 6 mW / cm ² for 1 minute with an exposure machine, and then heated to 200 ° C. An optical waveguide with an electrode was produced in the same manner as in Example 1 except that the method of heating for 1 hour was adopted.
[Comparative Example 1]
An optical waveguide with an electrode was produced in the same manner as in Example 1 except that the composition 6 (siloxane oligomer solution 1) was used as the upper clad layer material.

[Evaluation]
[Measurement of insertion loss and material loss]
Both ends of the obtained optical waveguide are cut into a length of 10 mm by dicing, and light emitted from the other end when light of 1,550 nm is incident from one end of the waveguide is measured by a light amount power meter (MT9810A manufactured by Anritsu Corporation). The insertion loss (dB) was determined by measurement. Moreover, the material loss (dB / cm) was calculated from the inclination by measuring the loss at each length by cutting the waveguide by cleaving and plotting the loss against the length (cut) Back method).
[Voltage response]
The obtained optical waveguide was heated to 80 ° C. with a heating furnace, a voltage of 1 kV or more was applied, and insertion loss was measured. A case where the insertion loss increased by 0.3 dB or more was judged as ◯, and a case where the insertion loss was increased by 0.1 dB or less was judged as x.
[Interface peeling]
The end face obtained by cleaving the produced optical waveguide is observed with a scanning electron microscope (SEM), and the substrate / lower clad layer, lower clad layer / core portion, core portion / upper clad layer, and lower clad layer / upper clad layer are observed. The presence or absence of peeling was determined. Furthermore, the presence or absence of peeling on the core line was observed from above the optical waveguide with an optical microscope. In either case, the case where no peeling was observed was indicated as “◯”, and the case where peeling was observed in any case was indicated as “x”.
[Crack resistance]
The produced optical waveguide is heated at 300 ° C. for 1 hour and naturally cooled, and the optical microscope is observed for the presence of cracks in the entire optical waveguide. When it was confirmed by any of the above, it was set as “x”.
[Long-term reliability]
The produced optical waveguide is left for 2,000 hours at 85 ° C. and 85% relative humidity, then left for 24 hours at 25 ° C. and 50% relative humidity, and the insertion loss is measured to calculate the material loss. did. The case where the material loss was 0.5 dB / cm or less at both wavelengths of 1,310 nm and 1,550 nm was “◯”, and the others were “X”.
The results are shown in Table 2.

[Evaluation results]
As shown in Table 2, in Examples 1 to 4, when there is no electric field, the insertion loss is 0.6 dB or less, exhibits good transmission characteristics, is excellent in crack resistance, etc., and voltage application When an electric field is generated by, the insertion loss increases by 0.3 dB or more, and responsiveness to changes in the electric field is recognized, which indicates that it can be applied to an optical switch or the like.
On the other hand, in Comparative Example 1, when an electric field is generated by applying a voltage, the insertion loss hardly increases, and it can be seen that it cannot be applied to an optical switch or the like.

It is sectional drawing which shows an example of the optical waveguide produced using the electro-optical composition of this invention.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Optical waveguide 2 Board | substrate 3 Board | substrate side electrode 4 Lower clad layer 5 Core part 6 Upper clad layer 7 Upper clad layer side electrode

Claims (9)

  An electro-optical composition comprising a fluorine-containing polysiloxane and an electro-optical organic compound. The fluorine-containing polysiloxane has the following general formula (1):
(R ¹ ) _p (R ² ) _q Si (X) _4-pq (1)
[Wherein R ¹ is a non-hydrolyzable organic group having 1 to 12 carbon atoms containing a fluorine atom, and R ² is a non-hydrolyzable organic group having 1 to 12 carbon atoms (however, fluorine Excluding those containing atoms.), X is a hydrolyzable group, p is an integer of 1 or 2, and q is an integer of 0 or 1. ]
The electro-optical composition according to claim 1, which is at least one selected from the group consisting of a hydrolyzate of a hydrolyzable silane compound represented by formula (I) and a condensate of the hydrolyzate. The electro-optical composition according to claim 2, wherein the fluorine-containing polysiloxane has at least one structure selected from the group consisting of the following general formulas (2) and (3).

[Wherein R ³ is a non-hydrolyzable organic group containing 1 to 12 carbon atoms containing a fluorine atom, and R ⁴ is a non-hydrolyzed carbon group having 1 to 12 carbon atoms which may contain a fluorine atom. An organic group which may be the same as R ³ . ] The electro-optical composition according to claim 3, wherein the fluorine-containing polysiloxane further has at least one structure selected from the group consisting of the following general formulas (4) and (5).

[Wherein, R ⁵ is a phenyl group or a fluorinated phenyl group, R ⁶ is a non-hydrolyzable organic group having 1 to 12 carbon atoms which may contain a fluorine atom, and the same as R ⁵ Good. ]   The electro-optical composition according to claim 1, wherein the electro-optical organic compound has an electron donating group and an electron withdrawing group.   The electron donating group is a group selected from the group consisting of amino, dialkylamino, hydroxyalkylamino and alkoxyalkylamino, and the electron withdrawing group is a group consisting of nitro, dicyanovinyl and tricyanovinyl. 6. The electro-optical composition according to claim 5, which is a group selected from the above.   The electro-optical composition according to claim 6, wherein the electro-optical organic compound is selected from the group consisting of aniline derivatives, stilbene derivatives, styrene derivatives, azobenzene derivatives, and imine derivatives.   The electro-optical composition according to claim 1, comprising a photoacid generator. An optical material for an optical waveguide whose refractive index changes with a change in an electric field, wherein the optical waveguide optical material is a cured product of the electro-optical composition according to any one of claims 1 to 8. material.

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