Organopolysiloxane, organopolysiloxane-containing resin composition, cured product thereof, organopolysiloxane for near-infrared optical waveguide, organopolysiloxane-containing resin composition for near-infrared optical waveguide, cured product for near-infrared optical waveguide, near-infrared optical waveguide, near-infrared optical transmission member, and near-infrared optical waveguide production method

Abstract

Provided are: an organopolysiloxane for a near-infrared optical waveguide, the organopolysiloxane having a polymerizable alkenyl group-containing organic group, and a siloxane unit (D unit) represented by SiO2 / 2, wherein the proportion of aromatic groups among the total of all groups bonded to a silicon atom is 20 mol% or less; and a cured product containing a crosslinked structure derived from a polymerizable alkenyl group-containing organic group, and a siloxane unit (D unit) represented by SiO2 / 2, wherein the refractive index at a 1300-nm wavelength is 1.400-1.500 inclusive.

Description

Organopolysiloxane, organopolysiloxane-containing resin composition and cured product thereof, organopolysiloxane for near-infrared optical waveguide, organopolysiloxane-containing resin composition for near-infrared optical waveguide, cured product for near-infrared optical waveguide, near-infrared optical waveguide and near-infrared optical transmission component, and method for producing near-infrared optical waveguide

[0001] The present invention relates to an organopolysiloxane, an organopolysiloxane composition and a cured product thereof, an organopolysiloxane for a near-infrared optical waveguide, a cured product for a near-infrared optical waveguide, a near-infrared optical waveguide and a near-infrared optical transmission component, and a method for producing a near-infrared optical waveguide.

[0002] In recent years, with the increasing speed and capacity of information communications, optical interconnect technology, which replaces electrical wiring with optical wiring, has been attracting attention. Conventionally, electrical wiring that transmits electrical signals has been used for transmission between devices, within devices, between chips, etc. However, as the volume of information and the required transmission speeds increase, the use of electrical wiring that transmits electrical signals is approaching its limit due to issues of wiring density and increased power consumption. Optical interconnect technology is being developed as a technology to replace electrical wiring.

[0003] Optical interconnect technology uses optical wiring for data transmission between devices and circuits. The advantages of optical wiring include low power consumption, high-density wiring, and high-speed communication. As data communication capacity increases, optical waveguides that connect single-mode optical fibers and silicon photonics circuits are being developed as optical communication components in optical interconnect technology. Optical waveguides that use resist materials and do not require reactive dry etching processes are attracting attention due to their high productivity. In particular, optical waveguides that can be connected to near-infrared single-mode silica-based optical fibers are required for data center equipment, which requires high-speed transmission. From the perspective of efficiently forming fine optical waveguides, it is desirable to form optical waveguides using a cured resin composition.

[0004] An optical waveguide connected to an optical fiber has a central core and a cladding surrounding the core, similar to an optical fiber, and efficiently propagates light by total internal reflection. Therefore, it is required that the core constituting the waveguide has a higher refractive index than the cladding, and that the refractive index difference between the core and the cladding is appropriate. For example, Patent Document 1 discloses an organopolysiloxane having an aromatic hydrocarbon group as a material for an optical transmission component.

[0005] Japanese Patent Application Laid-Open No. 2005-163009

[0006] In optical waveguides, when light propagates, it is necessary to suppress transmission loss, which indicates the degree to which an optical signal attenuates over distance along a communication path. In addition, since optical waveguides are connected to optical fibers, it is also important to suppress the optical loss during connection, i.e., the connection loss. In the above-mentioned Patent Document 1, the refractive index difference between the core and clad can be adjusted by adjusting the molar ratio of aromatic hydrocarbon groups in the organopolysiloxane, but there is still room for improvement in transmission loss. Furthermore, with regard to materials for optical waveguides to date, as in Patent Document 1, increasing the refractive index difference between the core and clad has been the primary focus of reports. However, no consideration has been given to the connection loss when connected to an optical fiber.

[0007] In view of the above-mentioned problems, an object of the present invention is to provide an optical waveguide that has the properties generally required of an optical waveguide and in which connection loss is significantly reduced.

[0008] The present inventors have conducted extensive research to solve these problems. As a result, they have found that connection loss increases due to roughness of the end face of an optical waveguide, that is, that the condition of the end face of an optical waveguide significantly contributes to connection loss. They have also found that an organopolysiloxane having a specific structure and a cured product obtained by curing a composition thereof can solve the above problems, and have completed the present invention. Specifically, the present invention provides the following:

[0009] (1) An organopolysiloxane represented by the following general formula [1]: (R １ R ２ R３ SiO １／２ ) Ｍ１ (R ４ R ５ R ６ SiO １／２ ) Ｍ２ (R ７ R ８ SiO ２／２ ) Ｄ１ (R ９ R ６ SiO ２／２ ) Ｄ２ (R １０ SiO ３／２ ) Ｔ１ (R ６ SiO ３／２ ) Ｔ２ (SiO ４／２ ) Ｑ (O １／２ R １１ ) Ｙ１ (O １／２ R ６ ) Ｙ２ ... [1] [In the above formula [1], R １ ~R ５ , R ７ ~R １１ R are each independently one or more groups selected from an organic group, a reactive functional group, or a hydrogen atom. １ ~R ３ , R ７ , R ８ , R １０ and R １１ does not contain a polymerizable alkenyl group. ６are one or more organic groups containing a polymerizable alkenyl group, which may be the same or different, 0≦M1, 0≦Q, 0≦Y1, 0≦Y2, 0<D1+D2, 0<M2+D2+T2, M1+M2+D1+D2+T1+T2+Q=1, and the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol% or less.] (2) An organopolysiloxane according to item (1) above, wherein in formula [1], 0.1<D1+D2. (3) An organopolysiloxane according to item (1) or (2) above, wherein in formula [1], 0<D1. (4) An organopolysiloxane according to any one of items (1) to (3) above, wherein in formula [1], 0.02≦Y1≦0.25. (5) In the formula [1], R ７ ~R ９ (6) The organopolysiloxane according to any one of the above items (1) to (4), wherein R １ ~R １１ (7) The organopolysiloxane according to any one of the above items (1) to (5), wherein in the formula [1], the R ６ and wherein the organopolysiloxane according to any one of items (1) to (6) above has in one molecule one or more functional groups selected from the group represented by the following formulas [2] to [5]: (In the above formula, X is a divalent organic group, and may have a branched structure and / or a cyclic structure. When X is bonded to a silicon atom, the atom at the end of X that is directly bonded to the silicon is a carbon atom. When X is bonded to an oxygen atom that is directly bonded to the silicon, the atom at the end of X that is directly bonded to the oxygen atom is a carbon atom. * indicates a bond.) (8) In the formula [1], ６ (9) The organopolysiloxane according to any one of the above items (1) to (7), wherein in the general formula [1], R is an acryloyloxypropyl group and / or a methacryloyloxypropyl group. ７ , R ８are each independently an alkyl group having 1 to 20 carbon atoms. (10) An organopolysiloxane-containing resin composition comprising the organopolysiloxane according to any one of items (1) to (9) above and a polymerization initiator. (11) A cured product obtained by curing the organosiloxane-containing resin composition according to item (10) above. (12) A near-infrared optical waveguide produced using the organosiloxane-containing resin composition according to item (10) above. (13) A near-infrared optical waveguide comprising a core portion and a clad portion, both of which are produced using the organosiloxane-containing resin composition according to item (10) above. (14) A near-infrared optical transmission component comprising at least the near-infrared optical waveguide according to item (12). (15) A near-infrared light transmission component comprising at least the near-infrared light waveguide according to item (13).

[0010] (16) A method for producing a near-infrared optical waveguide, comprising, in this order: a step (i-1) of applying a first curable polymer composition to a substrate surface to form a first polymer layer; a step (i-2) of irradiating at least one selected region of the first polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and a step (i-3) of removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, wherein the first curable polymer composition is the organopolysiloxane-containing resin composition according to item (10). (17) A method for producing a near-infrared optical waveguide according to item (16), further comprising: a step (i-4) of coating the substrate surface and the core with a second curable polymer composition to form a second polymer layer; and a step (i-5) of curing the second polymer layer to form an upper clad. (18) The method for producing a near-infrared optical waveguide according to the above item (17), wherein the second curable polymer composition is the organopolysiloxane-containing resin composition according to the above item (10). (19) A method for producing a near-infrared optical waveguide, comprising the steps of: (ii-1) applying a third curable polymer composition to a substrate surface to form a third polymer layer; (ii-2) irradiating at least one selected region of the third polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (ii-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (ii-4) coating the substrate surface and the core with a fourth curable polymer composition to form a fourth polymer layer; and (ii-5) curing the fourth polymer layer to form an upper clad, in this order; wherein at least one of the third curable polymer composition and the fourth curable polymer composition is the organopolysiloxane-containing resin composition according to item (10).(20) The method for producing a near-infrared optical waveguide according to item (19), wherein both the third curable polymer composition and the fourth curable polymer composition are the organopolysiloxane-containing resin composition according to item (10). (21) A method for producing a near-infrared optical waveguide, comprising the steps of: (iii-1) applying a fifth curable polymer composition to a surface of a substrate to form a fifth polymer layer; (iii-2) curing the fifth polymer layer to form a lower clad; (iii-3) applying a sixth curable polymer composition onto the lower clad to form a sixth polymer layer; (iii-4) irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and (iii-5) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, in this order; wherein at least one of the fifth curable polymer composition and the sixth curable polymer composition is the organopolysiloxane-containing resin composition according to item (10). (22) The method for producing a near-infrared optical waveguide according to item (21), wherein both the fifth curable polymer composition and the sixth curable polymer composition are the organopolysiloxane-containing resin composition according to item (10).(23) A method for manufacturing a photoresist-receiving layer, comprising the steps of: (iv-1) applying a fifth curable polymer composition to a substrate surface to form a fifth polymer layer; (iv-2) curing the fifth polymer layer to form a lower clad; (iv-3) applying a sixth curable polymer composition onto the lower clad to form a sixth polymer layer; (iv-4) irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (iv-5) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (iv-6) coating the lower clad and the core with a seventh curable polymer composition to form a seventh polymer layer; and (iv-7) curing the seventh polymer layer to form an upper clad, A method for producing a near-infrared optical waveguide, wherein at least one of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition is the organopolysiloxane-containing resin composition according to item (10). (24) A method for producing a near-infrared optical waveguide according to item (23), wherein all of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition are the organopolysiloxane-containing resin compositions according to item (10).

[0011] (25) A polymerizable polymer having a crosslinked structure derived from an organic group containing a polymerizable alkenyl group and SiO ２／２ (26) The cured product according to item (25) above, which has a refractive index of 1.400 or more and 1.500 or less at a wavelength of 1,300 nm. (27) The cured product according to item (25) above, which has a refractive index of 1.400 or more and 1.500 or less at a wavelength of 589 nm. (28) The cured product according to item (25) or (26) above, which is obtained by curing an organopolysiloxane represented by the following general formula [1]. (R １ R ２ R ３ SiO １／２ ) Ｍ１ (R ４ R ５R ６ SiO １／２ ) Ｍ２ (R ７ R ８ SiO ２／２ ) Ｄ１ (R ９ R ６ SiO ２／２ ) Ｄ２ (R １０ SiO ３／２ ) Ｔ１ (R ６ SiO ３／２ ) Ｔ２ (SiO ４／２ ) Ｑ (O １／２ R １１ ) Ｙ１ (O １／２ R ６ ) Ｙ２ ... [1] [In the above formula [1], R １ ~R ５ , R ７ ~R １１ R are each independently one or more groups selected from an organic group, a reactive functional group, or a hydrogen atom. １ ~R ３ , R ７ , R ８ , R １０ and R １１ does not contain a polymerizable alkenyl group. ６ are one or more organic groups containing a polymerizable alkenyl group, which may be the same or different, 0≦M1, 0≦Q, 0≦Y1, 0≦Y2, 0<D1+D2, 0<M2+D2+T2, M1+M2+D1+D2+T1+T2+Q=1, and the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol% or less.] (28) A cured product according to item (27) above, wherein in formula [1], 0.1<D1+D2. (29) A cured product according to item (27) or (28) above, wherein in formula [1], 0<D1. (30) A cured product according to any one of items (27) to (29) above, wherein in formula [1], 0.02≦Y1≦0.25. (31) In formula [1], R １ ~R １１(32) The cured product according to any one of the above items (27) to (30), wherein in the formula [1], the R ６ The cured product according to any one of items (27) to (31), wherein the cured product has one or more functional groups selected from the group represented by the following formulas [2] to [5] in one molecule: (In the above formula, X is a divalent organic group, and may have a branched structure and / or a cyclic structure. When X is bonded to a silicon atom, the atom at the end of X that is directly bonded to the silicon is a carbon atom. When X is bonded to an oxygen atom that is directly bonded to the silicon, the atom at the end of X that is directly bonded to the oxygen atom is a carbon atom. * indicates a bond.) (33) In the formula [1], ６ (34) The cured product according to any one of the above items (27) to (32), wherein in the general formula [1], R is an acryloyloxypropyl group and / or a methacryloyloxypropyl group. ７ , R ８ are each independently an alkyl group having 1 to 20 carbon atoms. (35) A near-infrared optical waveguide comprising the cured product according to any one of items (25) to (34) above. (36) A near-infrared optical waveguide comprising a core portion and a clad portion, wherein both the core portion and the clad portion comprise the cured product according to any one of items (25) to (34) above. (37) A near-infrared optical transmission component comprising at least the near-infrared optical waveguide according to item (35) above. (38) A near-infrared optical transmission component comprising at least the near-infrared optical waveguide according to item (36).

[0012] (39) An organic group containing a polymerizable alkenyl group, and SiO ２／２ (40) An organopolysiloxane for a near-infrared optical waveguide according to item (39), which is represented by the following general formula [1]: (R １ R ２ R ３ SiO １／２ )Ｍ１ (R ４ R ５ R ６ SiO １／２ ) Ｍ２ (R ７ R ８ SiO ２／２ ) Ｄ１ (R ９ R ６ SiO ２／２ ) Ｄ２ (R １０ SiO ３／２ ) Ｔ１ (R ６ SiO ３／２ ) Ｔ２ (SiO ４／２ ) Ｑ (O １／２ R １１ ) Ｙ１ (O １／２ R ６ ) Ｙ２ ...[1] [In formula [1], R １ ~R ５ , R ７ ~R １１ R are each independently one or more groups selected from the group consisting of an organic group, a reactive functional group, and a hydrogen atom. １ ~R ３ , R ７ , R ８ , R １０ and R １１ does not contain a polymerizable alkenyl group. ６ represents one or more organic groups containing a polymerizable alkenyl group, and when a plurality of groups are present, they may be the same or different; R １ ~R １１the proportion of aromatic groups in the total of (a) and (b) is 20 mol % or less, 0≦M1, 0≦Q, 0≦Y1, 0≦Y2, 0<D1+D2, 0<M2+D2+T2, and M1+M2+D1+D2+T1+T2+Q=1.] (41) An organopolysiloxane for a near-infrared optical waveguide according to item (40) above, wherein in formula [1], 0.1<D1+D2. (42) An organopolysiloxane for a near-infrared optical waveguide according to item (40) or (41) above, wherein in formula [1], 0<D1. (43) An organopolysiloxane for a near-infrared optical waveguide according to any one of items (40) to (42) above, wherein in formula [1], 0.02≦Y1≦0.25. (44) In the formula [1], R ７ ~R ９ (45) The organopolysiloxane for a near-infrared optical waveguide according to any one of the above items (40) to (43), wherein in the formula [1], the R ６ and wherein the organopolysiloxane for near-infrared optical waveguides according to any one of items (40) to (44) above has one or more functional groups selected from the group represented by the following formulas [2] to [5] in one molecule: (In the above formula, X is a divalent organic group, and may have a branched structure and / or a cyclic structure. When X is bonded to a silicon atom, the atom at the end of X that is directly bonded to the silicon is a carbon atom. When X is bonded to an oxygen atom that is directly bonded to the silicon, the atom at the end of X that is directly bonded to the oxygen atom is a carbon atom. * indicates a bond.) (46) In the formula [1], ６ (47) The organopolysiloxane for a near-infrared optical waveguide according to any one of the above items (40) to (45), wherein R in the formula [1] is an acryloyloxypropyl group and / or a methacryloyloxypropyl group. １ ~R １１ The organopolysiloxane for a near-infrared optical waveguide according to any one of the above items (40) to (46), wherein the organopolysiloxane does not contain an aromatic group.

[0013] (48) An organopolysiloxane-containing resin composition for near-infrared optical waveguides, comprising the organopolysiloxane for near-infrared optical waveguides according to any one of items (39) to (47) above and a polymerization initiator. (49) A cured product for near-infrared optical waveguides, obtained by curing the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48) above. (50) A near-infrared optical waveguide produced using the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48) above. (51) A near-infrared optical waveguide comprising a core portion and a clad portion, wherein both the core portion and the clad portion are produced using the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48) above. (52) A near-infrared light transmission component comprising at least the near-infrared light waveguide according to the above item (50). (53) A near-infrared light transmission component comprising at least the near-infrared light waveguide according to the above item (51).

[0014] (54) A method for producing a near-infrared optical waveguide, comprising the steps of: (i-1) applying a first curable polymer composition to a substrate surface to form a first polymer layer; (i-2) irradiating at least one selected region of the first polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and (i-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, in this order, wherein the first curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48). (55) A method for producing a near-infrared optical waveguide according to item (54), further comprising: (i-4) coating the substrate surface and the core with a second curable polymer composition to form a second polymer layer; and (i-5) curing the second polymer layer to form an upper clad. (56) The method for producing a near-infrared optical waveguide according to the above item (55), wherein the second curable polymer composition is the organopolysiloxane-containing resin composition for a near-infrared optical waveguide according to the above item (48). (57) A method for producing a near-infrared optical waveguide, comprising the steps of: (ii-1) applying a third curable polymer composition to a substrate surface to form a third polymer layer; (ii-2) irradiating at least one selected region of the third polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (ii-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (ii-4) coating the substrate surface and the core with a fourth curable polymer composition to form a fourth polymer layer; and (ii-5) curing the fourth polymer layer to form an upper clad, in this order; wherein at least one of the third curable polymer composition and the fourth curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48).(58) The method for producing a near-infrared optical waveguide according to item (57), wherein both the third curable polymer composition and the fourth curable polymer composition are the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48). (59) A method for producing a near-infrared optical waveguide, comprising the steps of: (iii-1) applying a fifth curable polymer composition to a surface of a substrate to form a fifth polymer layer; (iii-2) curing the fifth polymer layer to form a lower clad; (iii-3) applying a sixth curable polymer composition onto the lower clad to form a sixth polymer layer; (iii-4) irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and (iii-5) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, in this order; wherein at least one of the fifth curable polymer composition and the sixth curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48). (60) The method for producing a near-infrared optical waveguide according to item (59), wherein both the fifth curable polymer composition and the sixth curable polymer composition are the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to item (48).(61) A method for manufacturing a photoresist-receiving layer, comprising the steps of: (iv-1) applying a fifth curable polymer composition to a substrate surface to form a fifth polymer layer; (iv-2) curing the fifth polymer layer to form a lower clad; (iv-3) applying a sixth curable polymer composition onto the lower clad to form a sixth polymer layer; (iv-4) irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (iv-5) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (iv-6) coating the lower clad and the core with a seventh curable polymer composition to form a seventh polymer layer; and (iv-7) curing the seventh polymer layer to form an upper clad, A method for producing a near-infrared optical waveguide, wherein at least one of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguides described in item (48) above. (62) A method for producing a near-infrared optical waveguide according to item (61) above, wherein all of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition are the organopolysiloxane-containing resin compositions for near-infrared optical waveguides described in item (48) above.

[0015] According to the present invention, it is possible to provide an optical waveguide that has the properties generally required of an optical waveguide and that has significantly reduced connection loss. More specifically, it is possible to provide an optical waveguide that has significantly reduced connection loss, low transmission loss, and a controlled refractive index difference between the core and clad. Optical waveguides made from the organopolysiloxane of the present invention and a cured product obtained by curing a composition thereof are particularly useful as near-infrared optical waveguides and near-infrared optical transmission components.

[0016] Fig. 1 is a schematic cross-sectional view of an optical waveguide in which a core is formed on a substrate. Fig. 2 is a schematic cross-sectional view of an optical waveguide in which a core and an upper clad are formed on a substrate. Fig. 3 is a schematic cross-sectional view of an optical waveguide in which a lower clad and a core are formed on a substrate. Fig. 4 is a schematic cross-sectional view of an optical waveguide in which a lower clad, a core, and an upper clad are formed on a substrate.

[0017] Hereinafter, an embodiment of the present invention (hereinafter sometimes referred to as the present embodiment) will be described in detail, but the following description is an example of an embodiment, and the present invention is not limited to these in any way.

[0018] [Organopolysiloxane] The organopolysiloxane according to the first embodiment of the present invention (hereinafter sometimes referred to as the first embodiment) comprises an organic group containing a polymerizable alkenyl group and SiO ２／２ In the organopolysiloxane of this embodiment, the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol % or less.

[0019] Organopolysiloxanes containing aromatic groups have been reported for use in multimode optical waveguides with a large difference in refractive index between the core and clad regions. However, the present inventors have discovered that the connection loss of near-infrared optical waveguides obtained using organopolysiloxanes in which the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol % or less can be reduced.

[0020] Without being bound by any particular theory, the following is thought to be the influence of aromatic groups. That is, if the aromatic group content of the organopolysiloxane is 20 mol % or less, the interaction between aromatic rings is weakened, and the cured product obtained by curing the organopolysiloxane-containing resin composition is less likely to become brittle and crack, which is thought to make the end face of the waveguide less rough when cut. It is thought that suppressing the roughness of the waveguide end face also suppresses light scattering, thereby reducing connection loss.

[0021] In the organopolysiloxane of this embodiment, the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol% or less, thereby preventing roughness of the end face of an optical waveguide obtained using this organopolysiloxane and reducing connection loss. In this embodiment, the proportion of aromatic groups in all groups bonded to silicon atoms in the organopolysiloxane is preferably 15 mol% or less, more preferably 10 mol% or less, even more preferably 5 mol% or less, and even more preferably 1 mol% or less. As described above, the organopolysiloxane of this embodiment can have both an aromatic group and an aromatic group-free form. When the organopolysiloxane has aromatic groups, the lower limit is not limited as long as it does not impair the effects of the present invention, but may be, for example, 0.01 mol% or 0.1 mol%. According to one aspect of the present invention, it is also preferable that the organopolysiloxane has no aromatic groups bonded to silicon atoms. The aromatic group content is １ H-NMR, ２９ This can be confirmed by Si-NMR. "Nothing at all" means that there is no clear peak in the NMR chart that can be identified as an aromatic group.

[0022] In this specification, the "transmission loss" and "connection loss" of an optical waveguide are defined as follows. Optical loss is measured by bringing an optical fiber close to the end face of a straight optical waveguide, illuminating light, and measuring the intensity of light emitted from the other end face of the waveguide. The optical loss value (dB) is calculated using the following formula [6].

[0023]

[0024] [In formula [6], P １ denotes the incident light intensity, and P ２ indicates the emitted light intensity.]

[0025] Next, when a graph is drawn with the horizontal axis representing the waveguide length (cm) and the vertical axis representing the attenuation (dB), the slope of the linear approximation is defined as the transmission loss (dB / cm), and the intercept is defined as the connection loss (dB).

[0026] The splice loss obtained as an intercept from the linear approximation represents the optical loss that occurs when light enters the optical waveguide from the optical fiber. The inventors have found that the physical shape (roughness) of the end face of the optical waveguide has a significant effect on the splice loss.

[0027] In this embodiment, since the organopolysiloxane contains polymerizable alkenyl groups in its structure, a cured product can be easily obtained using a polymerization initiator. In other words, this is suitable for forming a core by photolithography. By adjusting the content of polymerizable alkenyl groups in the organopolysiloxane of this embodiment, the density of the obtained cured product can be controlled, and the refractive index of the cured product at near-infrared wavelengths can be controlled to 1.400 to 1.500. Furthermore, when the organopolysiloxane contains SiO ２／２ By containing siloxane units (D units) represented by the formula (I), the refractive index of the cured product at near-infrared wavelengths is maintained at 1.400 to 1.500, and the resin has reflow resistance, and optical loss, particularly transmission loss, is kept low while being imparted with toughness, thereby suppressing roughness of the end face when the waveguide is cut, and thus significantly suppressing connection loss.

[0028] [Organopolysiloxane] In the first embodiment, the organopolysiloxane is characterized by having a structure represented by the following formula [1]: (R １ R ２ R ３ SiO １／２ ) Ｍ１ (R ４ R ５ R ６ SiO １／２ ) Ｍ２ (R ７ R ８ SiO ２／２ ) Ｄ１ (R ９ R ６ SiO ２／２ ) Ｄ２ (R １０ SiO ３／２ ) Ｔ１ (R ６ SiO ３／２ ) Ｔ２ (SiO ４／２ ) Ｑ (O １／２ R１１ ) Ｙ１ (O １／２ R ６ ) Ｙ２ ...[1] [In formula [1], R １ ~R ５ , R ７ ~R １１ R are each independently one or more groups selected from the group consisting of an organic group, a reactive functional group, and a hydrogen atom. １ ~R ３ , R ７ , R ８ , R １０ and R １１ does not contain a polymerizable alkenyl group. ６ represents one or more organic groups containing a polymerizable alkenyl group, and when a plurality of organic groups are present, they may be the same or different; R １ ~R １１ the proportion of aromatic groups in the total of (a) and (b) is 20 mol % or less, 0≦M1, 0≦Q, 0≦Y1, 0≦Y2, 0<D1+D2, 0<M2+D2+T2, and M1+M2+D1+D2+T1+T2+Q=1.

[0029] In the general formula [1], M1 and M2 are so-called M units (SiO １／２ Similarly, D1 and D2 represent the proportion (molar basis) of D units (SiO ２／２ ) (hereinafter sometimes simply referred to as "D units") (molar ratio), and T1 and T2 represent the ratio of T units (SiO ３／２ ) (hereinafter, may be simply referred to as "T units") (molar ratio), and Q represents the number of Q units (SiO ４／２ As described above, in the first embodiment, the organopolysiloxane represented by general formula [1] has an aromatic group ratio of 20 mol % or less of the total of all groups bonded to silicon atoms.

[0030] M2, D2, and T2 are silicon atoms with R ６ Y1 represents the ratio of M units, D units, and T units to which an organic group containing a polymerizable alkenyl group is bonded when M1+M2+D1+D2+T1+T2+Q=1, and represents the ratio of a structure (O) that does not have a polymerizable alkenyl group and has a group selected from the group consisting of an organic group, a reactive functional group, and a hydrogen atom. １／２ R １１ ), specifically, the relative proportion of structures having an alkoxy group or a silanol group, and Y2 represents a structure having an organic group containing a polymerizable alkenyl group (O １／２ R ６ ) means the relative proportion of

[0031] 0≦M1, 0≦Q, 0≦Y1, 0≦Y2 means that M1, Q, Y1, and Y2 are each 0 or greater, and may be 0, i.e., these structural units may be absent. 0<D1+D2 means that the organopolysiloxane has D units, and 0<M2+D2+T2 means that the organopolysiloxane has at least one of M units, D units, and T units, each of which has an organic group containing a polymerizable alkenyl group. In this embodiment, the organopolysiloxane preferably has a branched structure. This means that at least one of T units and Q units is present.

[0032] <Coefficient M2 + D2 + T2> As described above, in the organopolysiloxane of this embodiment, 0<M2 + D2 + T2. That is, the organopolysiloxane of this embodiment contains a polymerizable alkenyl group, making it possible to easily obtain a cured product using a composition containing a polymerization initiator, as described below. The value of M2 + D2 + T2 is preferably 0.10≦M2 + D2 + T2, more preferably 0.12≦M2 + D2 + T2, even more preferably 0.15≦M2 + D2 + T2, and even more preferably 0.20≦M2 + D2 + T2. Within this range, the cured product will be sufficiently cured when produced, and will have good compatibility with other components added to the organopolysiloxane-containing resin composition, as described below.

[0033] There is no particular upper limit for M2 + D2 + T2, but it is preferably M2 + D2 + T2 ≦ 0.75, more preferably M2 + D2 + T2 ≦ 0.60, and even more preferably M2 + D2 + T2 ≦ 0.55. Within this range, the amount of polymerizable alkenyl groups contained in the organopolysiloxane is appropriate, and a cured product having a crosslinking density that is not brittle can be obtained. As described above, it is preferable that 0.10 ≦ M2 + D2 + T2 ≦ 0.75, more preferably 0.12 ≦ M2 + D2 + T2 ≦ 0.60, and even more preferably 0.15 ≦ M2 + D2 + T2 ≦ 0.55.

[0034] <O １／２ R １１ > (O １／２ R １１ ) has a structure that does not contain a polymerizable alkenyl group but contains a group selected from the group consisting of an organic group, a reactive functional group, and a hydrogen atom, specifically an alkoxy group and / or a silanol group bonded to silicon. This structural unit allows the viscosity of the organopolysiloxane to be controlled and adjusted to a viscosity suitable for molding. The silanol group has the effect of increasing the viscosity, while the alkoxy group has the effect of decreasing the viscosity. When the content of alkoxy groups or silanol groups is low, the amount of highly mobile terminal groups is low and the siloxane skeleton becomes a rigid cage structure, resulting in an increased viscosity. Conversely, when the content of alkoxy groups or silanol groups is high, the amount of highly mobile terminal groups is high and the siloxane skeleton becomes a flexible random structure or ladder structure rather than a cage structure, resulting in a decreased viscosity.

[0035] <Coefficient Y1> (O １／２ R １１ Y1, which indicates the content ratio of R １１From the definition of (I), it indicates the total content of silanol groups and alkoxy groups in the organopolysiloxane. The range of coefficient Y1 is usually 0 or more, preferably 0.02 or more, more preferably 0.025 or more, even more preferably 0.03 or more, and even more preferably 0.035 or more, from the viewpoints of the synthesis of organopolysiloxane, the viscosity adjustment necessary for the preparation of organopolysiloxane-containing resin compositions, and the toughness of the cured product, as described below. On the other hand, from the viewpoints of storage stability and handleability, the upper limit of coefficient Y1 is usually 0.30 or less, preferably 0.25 or less, more preferably less than 0.25, even more preferably 0.2 or less, still more preferably 0.20 or less, especially preferably 0.15 or less, and particularly preferably 0.10 or less. As a preferred range in formula [1], 0.02≦Y1≦0.30 is preferable, 0.02≦Y1≦0.25 is more preferable, 0.025≦Y1<0.25 is even more preferable, and 0.03≦Y1≦0.20 is even more preferable. Y1 represents a relative value with respect to M1+M2+D1+D2+T1+T2+Q=1.

[0036] <Coefficient Y2> Y2 is the coefficient of the organic group containing a polymerizable alkenyl group bonded to silicon via an oxygen atom in the organopolysiloxane (O １／２ R ６ ) content ratio. Y2 is 0 or a positive value. Preferably, Y2 > 0.25, more preferably Y2 > 0.30, and even more preferably Y2 > 0.35. When Y2 > 0.25, compatibility with other resins is improved. Organic groups containing polymerizable alkenyl groups are easily hydrolyzed and eliminated by water, which can lead to a high water absorption rate. Therefore, it is preferable to use them in a manner that is less susceptible to moisture. On the other hand, in environments affected by moisture, if Y2 is large, the cured product is likely to become brittle due to moisture, so Y2 < 0.4 is preferable, Y2 < 0.3 is more preferable, and Y2 < 0.2 is even more preferable. It is also preferable that Y2 is 0. Y2 represents a relative value to M1 + M2 + D1 + D2 + T1 + T2 + Q = 1.

[0037] <Coefficient M1> R having a polymerizable alkenyl group ６Although M units not having any of the formula (I) are not an essential constituent element of the organopolysiloxane of this embodiment, they may be included. That is, M1 may be greater than 0, and by substituting either the alkoxy groups or the silanol groups of the organopolysiloxane with M units, the storage stability of the organopolysiloxane can be improved and the viscosity can be reduced. If there are too many M units, the amount of polymerizable alkenyl groups contained in one molecule of the organopolysiloxane decreases, making curing defects more likely to occur. Therefore, M1 is usually ≦0.6, preferably M1 ≦0.55, more preferably M1 ≦0.5, and even more preferably M1 ≦0.4.

[0038] <Coefficient D1 + D2> As described above, in the organopolysiloxane of this embodiment, 0<D1 + D2. That is, since the organopolysiloxane of this embodiment has D units and flexible moieties are introduced, a cured product obtained from the organopolysiloxane of this embodiment is less likely to crack when cut. In particular, a near-infrared optical waveguide produced using the organopolysiloxane of this embodiment has less rough end faces when cut, resulting in lower connection loss. The value of D1 + D2 is preferably 0.1 <D1 + D2, more preferably 0.20 ≦D1 + D2, even more preferably 0.25 ≦D1 + D2, and even more preferably 0.30 ≦D1 + D2. Within this range, the resulting cured film has superior toughness and is less likely to crack when cut. There is no particular upper limit to the value of D1 + D2, but it is preferably D1 + D2 ≦ 0.80, more preferably D1 + D2 ≦ 0.75, and even more preferably D1 + D2 ≦ 0.70. Within this range, the content of the softening component in the organopolysiloxane is appropriate, and a cured product that maintains heat resistance can be obtained.

[0039] As described above, the value of D1 + D2 is preferably 0.1 < D1 + D2 ≦ 0.80, more preferably 0.20 ≦ D1 + D2 ≦ 0.80, even more preferably 0.25 ≦ D1 + D2 ≦ 0.75, and even more preferably 0.30 ≦ D1 + D2 ≦ 0.70. Since D unit structures that do not have polymerizable alkenyl groups and do not serve as crosslinking points have a greater effect of imparting toughness, D2 may be 0 within the above range of D1 + D2. From the same perspective, it is also preferable that D1 is 0 < D1, more preferably 0.1 < D1, even more preferably 0.20 ≦ D1, even more preferably 0.25 ≦ D1, and particularly preferably 0.30 ≦ D1. There is no particular upper limit for D1, but it is preferably D1 ≦ 0.80, more preferably D1 ≦ 0.75, and even more preferably D1 ≦ 0.70.

[0040] <Coefficient T1> In the organopolysiloxane of this embodiment, T units not having a polymerizable alkenyl group are not an essential constituent, but the inclusion of such units can improve compatibility with other components added to the organopolysiloxane-containing resin composition described below. That is, T1 may be 0, and when T1 > 0, preferably T1 ≧ 0.01, more preferably T1 ≧ 0.05, and even more preferably T1 ≧ 0.1. On the other hand, if the content ratio of T units not having a polymerizable alkenyl group is too high, steric hindrance of the introduced organic group tends to cause poor curing. Therefore, the content ratio T1 of T units not having a polymerizable alkenyl group is preferably T1 ≦ 0.5, more preferably T1 ≦ 0.4, and even more preferably T1 ≦ 0.3.

[0041] <Coefficient Q> In the organopolysiloxane of this embodiment, the Q unit is not an essential constituent element, but it represents the most oxidized form of silicon, and its inclusion in the structure of the organopolysiloxane can improve the heat resistance of the cured product. Q units are also contained in quartz, and it is possible to obtain a cured product having a refractive index close to that of the core material of a near-infrared single-mode silica-based optical fiber using an organopolysiloxane-containing resin composition having Q units, as described below. Q, which indicates the content ratio of Q units, may be 0 or greater, i.e., Q≧0. The coefficient Q is preferably Q≧0.04, more preferably Q≧0.10, even more preferably Q≧0.15, and even more preferably Q≧0.20. On the other hand, if the Q unit is too large, the product will become solid or its viscosity will increase, tending to reduce handleability. Therefore, Q≦0.65 is usually preferred, Q≦0.6, more preferably Q≦0.45, and even more preferably Q≦0.40.

[0042] From the above, it is preferable that the coefficients in the above formula [1] are 0.10≦M2+D2+T2≦0.75, 0.02≦Y1≦0.25, Y2<0.4, M1≦0.6, 0.1<D1+D2≦0.80, T1≦0.5, Q≦0.65, it is more preferable that the coefficients are 0.10≦M2+D2+T2≦0.75, 0.02≦Y1≦0.25, Y2<0.4, M1≦0.6, 0.20≦D1+D2≦0.80, T1≦0.5, Q≦0.65, it is more preferable that the coefficients are 0.12≦M2+D2+T2≦0.60, 0.025≦Y1≦0.25, Y2<0.3, M1≦0.55, 0.25≦D1+D2≦0.75, It is more preferable that T1≦0.4, Q≦0.6, and even more preferable that 0.15≦M2+D2+T2≦0.55, 0.03≦Y1≦0.20, Y2<0.2, M1≦0.4, 0.30≦D1+D2≦0.70, T1≦0.3, Q≦0.45.

[0043] <R ６ In this embodiment, R ６is an organic group containing a polymerizable alkenyl group. Specific examples include groups containing an acryloyl group, a methacryloyl group, a vinyl group, a styryl group, etc. In the organopolysiloxane of this embodiment, the proportion of aromatic groups in all groups bonded to silicon atoms must be 20 mol % or less. Therefore, R ６ is preferably a group having a polymerizable alkenyl group and not having an aromatic group. ６ It is more preferable that the compound has at least one functional group selected from the group represented by the following formulas [2] to [5] in one molecule.

[0044] (In the above formula, * indicates a bond.)

[0045] More preferably, R ６ has at least one functional group selected from the group consisting of an acryloyloxypropyl group, an acryloyloxyoctyl group, a methacryloyloxypropyl group, and a methacryloyloxyoctyl group in one molecule, and among these, it is particularly preferred that the compound has an acryloyloxypropyl group and / or a methacryloyloxypropyl group in one molecule.

[0046] In the above formulas [3] and [5], X is a divalent organic group and may have a branched structure and / or a cyclic structure. In addition to carbon and hydrogen, X may contain at least one element selected from the group consisting of oxygen, nitrogen, phosphorus, sulfur, and a halogen. When X is bonded to a silicon atom, the atom at the end of X and directly bonded to the silicon is a carbon atom. When X is bonded to an oxygen atom directly bonded to the silicon, the atom at the end of X and directly bonded to the oxygen atom is a carbon atom. For example, a divalent branched structure having 1 to 20 carbon atoms, a hydrocarbon group which may have a non-aromatic cyclic structure, or a group derived from a polyalkylene glycol are preferably used as the group represented by X.

[0047] In the present invention, it is not necessary that the units constituting the M unit, D unit, and T unit are all the same. For example, the unit (R １ R ２ R ３ SiO １／２), for example, a certain R １ is a hydrogen atom, and a certain R １ may have different structures, such as R being a methyl group. ２ ~R １０ , X, and the unit (O １／２ R １１ ), (O １／２ R ６ ) in R １１ , R ６ is also common.

[0048] <R １ ~R ５ , R ７ ~R １１ > R １ ~R ５ , R ７ ~R １１ R are each independently one or more groups selected from the group consisting of an organic group, a reactive functional group, and a hydrogen atom. １ ~R ５ , R ７ ~R １１ When R is an organic group, it is preferably an organic group having 1 to 20 carbon atoms. Specifically, it is preferably an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an octyl group, or a cyclohexyl group, or a polyether group such as a furanyl group or a polyalkylene glycol group, and more preferably a methyl group. For example, R in the coefficient D1 portion ７ , R ８ are each independently an alkyl group having 1 to 20 carbon atoms. ７ , R ８ is an alkyl group having 1 to 20 carbon atoms, the D unit is non-aromatic and has small steric hindrance, making it easy to adjust the refractive index of the cured product to a desired range and increasing the toughness of the cured product, thereby suppressing connection loss.

[0049] R １ ~R ５ , R ７ ~R １１When R is a reactive functional group, it is preferably a hydrogen atom, a hydroxyl group such as an alcohol, a carboxyl group, an aldehyde group, an epoxy group, or the like. １ ~R ３ , R ７ , R ８ , R １０ does not contain a polymerizable alkenyl group as a reactive functional group. １ ~R ３ is an organic group containing a polymerizable alkenyl group, the coefficient M1 portion and the coefficient M2 portion cannot be distinguished from each other. ４ , R ５ Since such a problem does not occur even when the organic group contains a polymerizable alkenyl group, the coefficient D1 portion and the coefficient T1 portion are not subject to this limitation. ７ , R ８ , R １０ is defined as not containing polymerizable alkenyl groups.

[0050] As described above, in the organopolysiloxane represented by formula [1] of this embodiment, the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol % or less. １ ~R １１ The proportion of aromatic groups in the total of R in the organopolysiloxane must be 20 mol % or less. Here, the aromatic group includes an aromatic structure such as a benzene ring, an aromatic polycycle, or an aromatic heterocycle, and may include a substituent structure, an alkylene structure, a salt structure, etc., and represents a group in which the silicon atom and the aromatic structure do not necessarily have to be directly bonded. In this embodiment, if the organopolysiloxane contains too many aromatic structures, the rigidity of the aromatic structures will make the resulting cured product brittle. １ ~R １１ The proportion of aromatic groups in the total is preferably 15 mol % or less, more preferably 10 mol % or less, even more preferably 5 mol % or less, and even more preferably 1 mol % or less.

[0051] In this embodiment, the organopolysiloxane represented by formula [1] may have either an aromatic group or no aromatic group, as described above. When the organopolysiloxane has an aromatic group, R １ ~R １１ The lower limit of the total of R is not limited as long as the effects of the present invention are not impaired, but may be, for example, 0.01 mol % or 0.1 mol %. According to one aspect of the present invention, the organopolysiloxane has no aromatic groups bonded to silicon atoms, i.e., R １ ~R １１ It is also preferable that the aromatic group is not contained. １ H-NMR, ２９ This can be confirmed by Si-NMR.

[0052] In the organopolysiloxane of this embodiment, M units (optional), D units, T units, and Q units (optional) are preferably randomly polymerized. For example, a preferred embodiment is one in which D units and T units do not regularly repeat. The random polymerization of each unit tends to impart toughness to the resulting cured product.

[0053] Generally, organopolysiloxanes suitable for use in optical waveguides use organopolysiloxanes having aromatic groups directly attached to silicon atoms in the core portion to achieve a sufficient refractive index difference between the core portion and the clad portion. The organopolysiloxane of this embodiment has the unique effect of being able to be used as both a core member and a clad member, even if it does not have an aromatic group directly attached to the silicon atom, due to the specific structure described above. The organopolysiloxane of this embodiment may have an aromatic group directly attached to the silicon atom, but as described above, in order to suppress connection loss when used as an optical waveguide, the proportion of aromatic groups in the total of all groups attached to the silicon atom must be 20 mol% or less. That is, even if the proportion of aromatic groups is at this level, the organopolysiloxane of this embodiment can be suitably used as both a core member and a clad member.

[0054] The organopolysiloxane of this embodiment may contain a halogen group such as fluorine, but preferably does not contain such a group. By not containing a halogen substituent, the refractive index of the cured product obtained from the organopolysiloxane having the above specific structure can be stably controlled within a desired range.

[0055] The organopolysiloxane of the above embodiment is particularly suitable for use in near-infrared optical waveguides. Therefore, in another embodiment of the present invention, an organopolysiloxane for near-infrared optical waveguides is also provided. The various aspects and requirements of the organopolysiloxane for near-infrared optical waveguides are as described above for the organopolysiloxane of the first embodiment. Hereinafter, when referring to "organopolysiloxane," it is intended to mean both the organopolysiloxane and the organopolysiloxane for near-infrared optical waveguides.

[0056] <Method for Producing Organopolysiloxane> The method for producing the organopolysiloxane of this embodiment is not particularly limited, as long as it can produce an organopolysiloxane having an organic group containing a polymerizable alkenyl group and a D unit, and in which the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol% or less. Among these, it is preferable to produce an organopolysiloxane represented by the formula [1]. For example, any of the following production methods may be used: a method of simultaneously condensing one or more disiloxane compounds, disilazane compounds, and their hydrolysates; alkoxysilane compounds, and their hydrolysates; and partial hydrolyzed condensates; a method of condensing chlorosilane compounds, and their hydrolysates; a method of ring-opening polymerizing a cyclic siloxane compound; and chain polymerization, including anionic polymerization. A combination of these production methods may also be used. The method for introducing the polymerizable alkenyl group is not particularly limited, and any method may be used, such as a method of simultaneously condensing one or more alkoxysilane compounds, disiloxane compounds, or disilazane compounds having a polymerizable alkenyl group, or their hydrolysates or partial hydrolysis condensates, or a method of converting a reactive organic group introduced into an organopolysiloxane into a polymerizable alkenyl group by a chemical method, or a combination of these methods. Hereinafter, examples of raw materials that can be used in the production of organopolysiloxane by hydrolysis condensation in this embodiment are given below.

[0057] (Source of M Units) Examples of sources of M units include trimethylsilanol, trimethylmethoxysilane, hexamethyldisiloxane, hexamethyldisilazane, dimethylsilanol, dimethylmethoxysilane, tetramethyldisiloxane, tetramethyldisilazane, dimethylvinylsilanol, dimethylvinylmethoxysilane, 1,3-divinyltetramethyldisiloxane, 1,3-divinyltetramethyldisilazane, dimethyl(meth)acryloyloxypropylsilanol, dimethyl(meth)acryloyloxypropylmethoxysilane, 1,3-di(meth)acryloyloxypropyltetramethyldisiloxane, dimethylglycidyloxypropylmethoxysilane, 1,3-bis(3-glycidyloxypropyl)methyldisiloxane, dimethylglycidyloxypropylmethyl ...dimethylvinylsilanol, dimethylvinylmethoxysilane, 1,3-bis(3-glycidyloxypropyl)methyldisiloxane, dimethylvinylsil Examples of suitable compounds include 1,3-bis((meth)acryloyloxypropyl)-1,1,3,3-tetramethyldisiloxane, tetramethyldisiloxane, methoxytriphenylsilane, triphenylsilanol, 1,3-diphenyltetramethyldisiloxane, 1,3-diphenyltetramethyldisilazane, dimethylphenylsilanol, dimethylmethoxyphenylsilane, 1,4-bis(dimethylmethoxysilyl)benzene, and 1,4-bis(dimethylethoxysilyl)benzene. Among the compounds listed above, compounds containing a silanol hydroxyl group or an alkoxy group can be replaced with compounds in which a halogen is bonded to the silanol hydroxyl group or the alkoxy group. For the reasons mentioned above, it is preferable to use compounds that do not contain an aromatic structure, and hexamethyldisiloxane is particularly suitable.

[0058] (Source of D Units) Examples of the D unit source include dimethyldisilanol, dimethyldimethoxysilane, diphenyldisilanol, diphenyldimethoxysilane, 3-(meth)acryloyloxypropyldimethoxymethylsilane, 3-glycidoxypropylmethyldimethoxysilane, methyldimethoxyphenylsilane, diethoxymethylphenylsilane, methylphenyldisilanol, 1,4-bis(methyldimethoxysilyl)benzene, 1,4-bis(methyldiethoxysilyl)benzene, and dimethoxy(methyl)(3,3,3-trifluoropropyl)silane. Compounds in which halogen atoms are bonded in place of the silanol hydroxyl groups or alkoxy groups of the above-listed compounds, and polymers thereof, etc., can be used. For the reasons mentioned above, it is preferable to use a compound that does not contain an aromatic structure, and dimethyldimethoxysilane is particularly suitable.

[0059] (T Unit Source) Examples of T unit sources include trimethoxysilane, trimethoxysilanes modified with a C1 to C20 long-chain alkoxy group, such as trimethoxysilane, methyltrimethoxysilane, ethyltrimethoxysilane, propyltrimethoxysilane, hexyltrimethoxysilane, and decyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, 3-(meth)acryloyloxypropyltrimethoxysilane, 8-(meth)acryloyloxyoctyltrimethoxysilane, 1,4-bis(trimethoxysilyl)benzene, p-styryltrimethoxysilane, 3-glycidyloxypropyltrimethoxysilane, 8-glycidyloxyoctyltrimethoxysilane, and 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane. In addition to these methoxysilane compounds, alkoxysilane compounds such as ethoxysilane, silanol compounds, chlorosilane compounds, hydrosilylsilane compounds, and polymers thereof can also be used. For the reasons mentioned above, it is preferable to use a compound that does not contain an aromatic structure, and in particular, 3-methacryloyloxypropyltrimethoxysilane, 8-methacryloyloxyoctyltrimethoxysilane, 3-acryloyloxypropyltrimethoxysilane, and 8-acryloyloxyoctyltrimethoxysilane can be suitably used.

[0060] (Q Unit Source) Examples of Q unit sources include tetrachlorosilane, tetramethoxysilane, tetraethoxysilane, tetraisopropoxysilane, tetrapropoxysilane, tetrabutoxysilane, tetrapentyloxysilane, tetraphenyloxysilane, trimethoxymonoethoxysilane, dimethoxydiethoxysilane, triethoxymonomethoxysilane, trimethoxymonopropoxysilane, monomethoxytributoxysilane, monomethoxytripentyloxysilane, monomethoxytriphenyloxysilane, dimethoxydipropoxysilane, tripropoxymonomethoxysilane, trimethoxymonobutoxysilane, dimethoxydibutoxysilane, triethoxymonopropoxysilane, diethoxydipropoxysilane, tributoxymonopropoxysilane, dimethoxymono Examples of suitable alkoxysilanes include monoethoxymonobutoxysilane, diethoxymonomethoxymonobutoxysilane, diethoxymonopropoxymonobutoxysilane, dipropoxymonomethoxymonoethoxysilane, dipropoxymonomethoxymonobutoxysilane, dipropoxymonoethoxymonobutoxysilane, dibutoxymonomethoxymonoethoxysilane, dibutoxymonoethoxymonopropoxysilane, and monomethoxymonoethoxymonopropoxymonobutoxysilane, as well as aryloxysilanes and tetramethoxysilane oligomers such as Methyl Silicate MS51, MS56, MS57, and MS60 manufactured by Mitsubishi Chemical Corporation, and tetraethoxysilane oligomers such as Ethyl Silicate Oligomer ES40 and ES48 manufactured by Tama Chemicals Co., Ltd. Methyl Silicate MS51 is particularly preferred. The above M, D, T and Q unit sources may be used singly or in combination of two or more.

[0061] As a catalyst for hydrolyzing and condensing these silicon raw materials, an acid catalyst, a base catalyst, or an inorganic salt can be used. In particular, an acid catalyst is preferably used. Examples of acid catalysts include hydrochloric acid, sulfuric acid, trifluoroacetic acid, acetic acid, methacrylic acid, and acrylic acid. In particular, hydrochloric acid is preferably used. Examples of base catalysts include ammonia, hexamethyldisilazane, triethylamine, tetraethylammonium hydroxide, diazabicycloundecene, potassium hydroxide, sodium hydroxide, barium hydroxide, potassium carbonate, and sodium carbonate. In particular, potassium hydroxide is preferred. Examples of inorganic salts include sodium chloride, potassium chloride, magnesium chloride, calcium chloride, sodium bromide, potassium bromide, magnesium bromide, and calcium bromide. In particular, sodium chloride is preferred.

[0062] Examples of solvents used during hydrolysis and condensation include tetrahydrofuran, toluene, methanol, ethanol, isopropanol, hexane, and heptane. Tetrahydrofuran is particularly preferred. Depending on the solubility of the product, two or more solvents may be used, and a mixture of toluene and methanol, or a mixture of tetrahydrofuran and methanol is particularly preferred.

[0063] The alkoxy groups and silanol groups remaining without hydrolysis and condensation may be substituted with an organic acid or alcohol, as necessary. Examples of the organic acid include acetic acid, acrylic acid, and methacrylic acid. Examples of the alcohol that do not contain a polymerizable alkenyl group include methanol, ethanol, propanol, butyl alcohol, pentanol, hexanol, heptanol, and structural isomers thereof. Examples of the alcohol that contains a polymerizable alkenyl group include 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate, with 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate being preferred from the viewpoint of stability.

[0064] If the organopolysiloxane has a rigid structure such as a complete cage silsesquioxane, the cured product will be hard and brittle, so it is preferable that the organopolysiloxane does not have a complete cage structure. As long as it is not a complete cage silsesquioxane, for example, it may contain a random structure or a ladder structure as a higher-order structure, as long as the effects of the present invention are not impaired.

[0065] <Water> The amount of water used for hydrolysis is preferably 0.5 equivalents or more, more preferably 0.8 equivalents or more, and even more preferably 1.1 equivalents or more, relative to the total amount of alkoxy groups contained in the MDTQ unit source. The water is not particularly limited, and may be water contained in commercially available hydrochloric acid or the like, or water purified by distillation or ion exchange resin.

[0066] [Organopolysiloxane-Containing Resin Composition] The organopolysiloxane-containing resin composition of this embodiment is used to form a near-infrared optical waveguide. In addition to the organopolysiloxane described above, the composition may contain a monofunctional polymerizable alkenyl compound, a polyfunctional polymerizable alkenyl compound, and / or an alkenyl polymer, etc., to an extent that does not impair the properties of the cured product obtained from the composition, as described below. Furthermore, a polymerization initiator may be contained to polymerize and easily cure the organopolysiloxane and polymerizable alkenyl compound. While it is possible to cure an organopolysiloxane or an organopolysiloxane-containing resin composition by electron beam irradiation or the like without using a polymerization initiator, a large amount of energy is required for curing. Therefore, in a preferred embodiment of this embodiment, the organopolysiloxane-containing resin composition contains at least a polymerization initiator in addition to the organopolysiloxane. The composition of the present embodiment may contain chain transfer agents, antioxidants, ultraviolet absorbers, light stabilizers, leveling agents, rheology modifiers, adhesion aids such as silane coupling agents, other components such as dyes, antifoaming agents, and sensitizers, solvents, and the like, to the extent that the properties of the cured product described below are not impaired.

[0067] This organopolysiloxane-containing resin composition (curable composition) is particularly suitable for use in near-infrared optical waveguides. Therefore, in another embodiment of the present invention, an organopolysiloxane-containing resin composition for near-infrared optical waveguides is also provided. The various aspects and requirements of the organopolysiloxane-containing resin composition for near-infrared optical waveguides are as described above for the organopolysiloxane-containing resin composition. Hereinafter, when referring to an "organopolysiloxane-containing resin composition," this refers to both the organopolysiloxane-containing resin composition and the organopolysiloxane-containing resin composition for near-infrared optical waveguides.

[0068] Components that may be contained in the organopolysiloxane-containing resin composition will be described below.

[0069] <Monofunctional Polymerizable Alkenyl Compound> Specific examples of the monofunctional polymerizable alkenyl compound include (meth)acrylates containing a carboxy group, such as (meth)acrylic acid, 2-(meth)acryloyloxyethyl succinate, 2-(meth)acryloyloxyethyl maleate, 2-(meth)acryloyloxyethyl phthalate, and 2-(meth)acryloyloxyethyl hexahydrophthalate; (meth)acrylates having a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and 6-hydroxyhexyl (meth)acrylate; Alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, i-butyl (meth)acrylate, tert-butyl (meth)acrylate, pentyl (meth)acrylate, heptyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, n-nonyl (meth)acrylate, isononyl (meth)acrylate, decyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, and stearyl (meth)acrylate; (meth)acrylates containing an alicyclic structure, such as cyclohexyl (meth)acrylate, dicyclopentenyl (meth)acrylate, 2-dicyclopentenoxyethyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, adamantyl (meth)acrylate, and 4-tert-butylcyclohexyl (meth)acrylate;(Meth)acrylates containing an aromatic ring structure such as phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate, phenoxypolypropylene glycol (meth)acrylate, phenylphenyl (meth)acrylate, phenylphenoxyethyl (meth)acrylate, phenoxybenzyl (meth)acrylate, phenylbenzyl (meth)acrylate, naphthyl (meth)acrylate, and (1-naphthyl)methyl (meth)acrylate; (meth)acrylates containing a heterocyclic structure such as tetrahydrofurfuryl (meth)acrylate, glycidyl (meth)acrylate, and (meth)acryloylmorpholine; alkoxy (meth)acrylates such as methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, and butoxyethyl (meth)acrylate; Examples of suitable compounds include 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 2-(meth)acryloyloxyethyl acid phosphate, trifluoroethyl (meth)acrylate and heptadecafluorodecyl (meth)acrylate, and 2-(meth)acryloyloxyethyl isocyanate; styrene derivatives such as styrene, α-methylstyrene, 2-vinylpyridine, 4-vinylpyridine, 1,1-diphenylethylene, and aromatic ring hydrogen-substituted derivatives thereof; and vinyl compounds such as vinyl acetate, vinyl octanoate, vinyl decanoate, vinyl hexanoate, acrylonitrile, and vinyl benzoate. It is preferable to use compounds that do not contain an aromatic structure, as this increases the refractive index of the cured product and makes it brittle.

[0070] <Polyfunctional Polymerizable Alkenyl Compound> Specific examples of the polyfunctional polymerizable alkenyl compound include alkylene glycol di(meth)acrylates such as ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, and neopentyl glycol di(meth)acrylate; polyalkylene glycol di(meth)acrylates such as polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, and polybutylene glycol di(meth)acrylate; Di(meth)acrylates containing an alicyclic structure such as cyclohexanedimethanol di(meth)acrylate, tricyclodecanedimethanol di(meth)acrylate, ethoxylated hydrogenated bisphenol A di(meth)acrylate, propoxylated hydrogenated bisphenol A di(meth)acrylate, and adamantanediol di(meth)acrylate; bifunctional (meth)acrylates such as polycarbonate diol di(meth)acrylate, polyester diol di(meth)acrylate, ethoxylated bisphenol A di(meth)acrylate, propoxylated bisphenol A di(meth)acrylate, 9,9-bis(4-acryloyloxyethoxyphenyl)fluorene, and polyurethane di(meth)acrylate; Examples of suitable monomers include trifunctional (meth)acrylates such as trimethylolpropane tri(meth)acrylate, ethoxylated isocyanuric acid tri(meth)acrylate, and ε-caprolactone-modified tris((meth)acryloxyethyl)isocyanurate; tetrafunctional (meth)acrylates such as ditrimethylolpropane tetra(meth)acrylate; pentafunctional (meth)acrylates such as dipentaerythritol penta(meth)acrylate; and polyfunctional monomers such as hexafunctional (meth)acrylates such as dipentaerythritol hexa(meth)acrylate; 1,4-divinylbenzene, 1,3-divinylbenzene, and the like. Since the refractive index of the cured product increases and the product becomes brittle, it is preferable to use a monomer that does not contain an aromatic structure.

[0071] <Alkenyl Polymer> An alkenyl polymer is a polymer containing 50% by mass or more of alkenyl monomer units. In this specification, "unit" refers to a repeating unit constituting a polymer. An alkenyl polymer may be monofunctional or polyfunctional. Furthermore, it is preferable that the alkenyl polymer does not contain an aromatic structure, as this would increase the refractive index of the cured product and make it brittle. The alkenyl polymer may contain one or more types of alkenyl monomer units. The polymerization method for obtaining an alkenyl polymer is not particularly limited, and can be, for example, a known method such as solution polymerization, suspension polymerization, emulsion polymerization, or partial polymerization. In this embodiment, suspension polymerization is preferred because it is relatively easy to control the polymerization reaction and separate the produced polymer.

[0072] The alkenyl polymer may be modified by introducing a double bond-containing functional group, such as a (meth)acryloyl group or a vinyl group, into the side chain by chemical modification. Examples of chemical modification methods include a reaction between a carboxy group and a glycidyl group, and a reaction between a hydroxyl group and an isocyanate group. When the reaction between a carboxy group and a glycidyl group is used as the chemical modification method, for example, an alkenyl polymer containing an alkenyl monomer unit having a carboxy group is produced, and the resulting alkenyl polymer is reacted with a compound having a glycidyl group and a double bond, such as glycidyl (meth)acrylate.

[0073] In order to shorten the reaction time, it is preferable to use a reaction catalyst when reacting an alkenyl polymer containing an alkenyl monomer unit having a carboxy group with a compound having a glycidyl group and a double bond. Examples of the reaction catalyst include quaternary ammonium salts such as tetrabutylammonium bromide, quaternary phosphonium salts such as ethyltriphenylphosphonium bromide, and phosphine compounds such as triphenylphosphine. Quaternary ammonium salts are particularly preferred because they are less likely to discolor the organopolysiloxane-containing resin composition of this embodiment.

[0074] The weight-average molecular weight (Mw) of the alkenyl polymer is preferably 5,000 to 500,000, more preferably 10,000 to 200,000, and even more preferably 20,000 to 150,000. When the weight-average molecular weight is 5,000 or more, the strength of the cured product is improved. When the weight-average molecular weight is 500,000 or less, the viscosity of the organopolysiloxane-containing resin composition of this embodiment is reduced, thereby improving workability.

[0075] <Polymerization initiator> Examples of the polymerization initiator include a photopolymerization initiator, a thermal polymerization initiator, a peroxide used in redox polymerization, etc. The type of polymerization initiator can be appropriately selected depending on the polymerization method.

[0076] (Photopolymerization initiator) The photopolymerization initiator is a radical polymerization initiator used for photopolymerization. Specific examples of the photopolymerization initiator include benzophenone-type compounds such as benzophenone, 4-methylbenzophenone, 2,4,6-trimethylbenzophenone, methyl 2-benzoylbenzoate, and 4-phenylbenzophenone; anthraquinone-type compounds such as tert-butylanthraquinone and 2-ethylanthraquinone; 2-hydroxy-2-methyl-1-phenylpropan-1-one, oligo{2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone}, benzyl dimethyl ketal, Alkylphenone compounds such as 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, 2-methyl-[4-(methylthio)phenyl]-2-morpholino-1-propanone, and 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)benzyl]phenyl}-2-methylpropan-1-one; thioxanthone compounds such as 2-benzyl-2-dimethylamino-4'-morpholinobutyrophenone, diethylthioxanthone, and isopropylthioxanthone; 2,4,6-trimethylthioxanthone; acylphosphine oxide compounds such as bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide; phenyl glyoxylate compounds such as phenyl glyoxylic acid methyl ester; N-acetoxy-N-{4-acetoxyimino-4-[9-ethyl-6-(o-toluoyl)-9H-carbazol-3-yl]butane-2- yl}acetamide, N-acetoxy-N-{3-(acetoxyimino)-3-[9-ethyl-6-(1-naphthoyl)-9H-carbazol-3-yl]-1-methylpropyl}acetamide, 4-acetoxyimino-5-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-5-oxopentanoate, methyl 4-acetoxyimino-5-oxo-5-(4-(phenylthio)phenyl)pentanoate, and other oxime ester compounds, as well as combinations thereof.

[0077] Among these, alkylphenone-type compounds are preferred in terms of their ability to suppress discoloration of the cured product, and 2-hydroxy-2-methyl-1-phenylpropan-1-one or 1-hydroxycyclohexyl phenyl ketone is more preferred. Acylphosphine oxide-type compounds are preferred in terms of their ability to facilitate sufficient curing deep into the cured product, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide is more preferred in terms of their ability to suppress discoloration of the cured product. Furthermore, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and methyl 4-acetoxyimino-5-oxo-5-(4-(phenylthio)phenyl)pentanoate are more preferred, as they have high sensitivity to light with longer wavelengths. 2-benzyl-2-dimethylamino-4'-morpholinobutyrophenone is also preferred in terms of its high reactivity to light with a wavelength of around 365 nm. These photopolymerization initiators may be used alone, or two or more may be used in combination.

[0078] In this embodiment, when the organopolysiloxane-containing curable resin composition (hereinafter sometimes simply referred to as the "curable resin composition") is photopolymerized to obtain a cured product, the wavelength of the light irradiated onto the curable resin composition is not particularly limited, but it is preferable to irradiate it with ultraviolet light having a wavelength of 200 to 500 nm. Specific examples of ultraviolet light sources include ultra-high pressure mercury lamps, high pressure mercury lamps, metal halide lamps, high-power metal halide lamps, UV-LED lamps, chemical lamps, and black lights. After photopolymerization of the curable resin composition, an aftercure may be further performed. By performing the aftercure, the amount of unreacted polymerizable alkenyl groups remaining in the cured product can be reduced, thereby further increasing the strength of the cured product. Examples of aftercure conditions include a temperature of 50°C to 200°C for several tens of seconds to 60 minutes, or a temperature of 80°C to 150°C for several tens of seconds to 60 minutes.

[0079] (Thermal Polymerization Initiator) The thermal polymerization initiator is a radical polymerization initiator used in thermal polymerization. Examples of the thermal polymerization initiator include organic peroxides and azo compounds. Specific examples of organic peroxides include ketone peroxides such as methyl ethyl ketone peroxide; peroxyketals such as 1,1-di(tert-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-di(tert-hexylperoxy)cyclohexane, and 1,1-di(tert-butylperoxy)cyclohexane; hydroperoxides such as 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, and p-menthane hydroperoxide; dicumyl peroxide, di-tert-butyl peroxide, etc. diacyl peroxides such as dilauroyl peroxide and dibenzoyl peroxide; peroxydicarbonates such as di(4-tert-butylcyclohexyl)peroxydicarbonate and di(2-ethylhexyl)peroxydicarbonate; and peroxyesters such as tert-butylperoxy-2-ethylhexanoate, tert-hexylperoxyisopropyl monocarbonate, tert-butylperoxybenzoate, and 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate.

[0080] Specific examples of azo compounds include 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 1,1'-azobis-1-cyclohexanecarbonitrile, dimethyl-2,2'-azobisisobutyrate, 4,4'-azobis-4-cyanovaleric acid, and 2,2'-azobis-(2-amidinopropane) dihydrochloride.

[0081] These thermal polymerization initiators may be used alone or in combination of two or more. As the thermal polymerization initiator, an organic peroxide is preferred because it is less likely to generate bubbles in the cured product. Considering the balance between the curing time and pot life of the curable resin composition, the 10-hour half-life temperature of the organic peroxide is preferably 35 to 80°C, more preferably 40 to 75°C, and even more preferably 45 to 70°C. If the 10-hour half-life temperature is 35°C or higher, the curable resin composition is less likely to gel at room temperature, resulting in a good pot life. On the other hand, if the 10-hour half-life temperature is 80°C or lower, the curing time of the curable resin composition can be shortened.

[0082] Examples of such organic peroxides include 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, tert-butylperoxy-2-ethylhexanoate, and di(4-tert-butylcyclohexyl)peroxydicarbonate. Commercially available 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate includes, for example, Perocta O (trade name, manufactured by NOF Corporation, 10-hour half-life temperature: 65.3°C). Commercially available tert-butylperoxy-2-ethylhexanoate includes, for example, Perbutyl O (trade name, manufactured by NOF Corporation, 10-hour half-life temperature: 72.1°C). Commercially available di(4-tert-butylcyclohexyl)peroxydicarbonate includes, for example, Peroyl TCP (trade name, manufactured by NOF Corporation, 10-hour half-life temperature: 40.8°C).

[0083] When a curable resin composition is cured by thermal polymerization to obtain a cured product, the curing conditions are not particularly limited. However, from the viewpoint of easily obtaining a resin for optical components with suppressed coloration, the curing temperature is preferably 40 to 200°C, more preferably 60 to 150°C. The curing time (heating time) varies depending on the curing temperature, but is preferably 1 to 120 minutes, more preferably 1 to 60 minutes. After thermal polymerization of the curable resin composition, it is preferable to further perform after-cure. Examples of after-cure conditions include a temperature of 50°C to 200°C for several tens of seconds to 60 minutes, or a temperature of 80°C to 150°C for several tens of seconds to 60 minutes.

[0084] (Redox Polymerization) Redox polymerization typically uses a redox polymerization initiator. A redox polymerization initiator is a polymerization initiator that uses a peroxide and a reducing agent in combination. Examples of peroxides used in redox polymerization include dibenzoyl peroxide and hydroperoxide. These peroxides may be used alone or in combination of two or more. When using the above-mentioned peroxides as redox polymerization initiators, examples of combinations with reducing agents include the following: (1) A combination of dibenzoyl peroxide (peroxide) with an aromatic tertiary amine (reducing agent) such as N,N-dimethylaniline, N,N-dimethyl-p-toluidine, or N,N-bis(2-hydroxypropyl)-p-toluidine. (2) A combination of a hydroperoxide (peroxide) with a metal soap (reducing agent). (3) A combination of a hydroperoxide (peroxide) with a thiourea (reducing agent).

[0085] When a curable resin composition is cured by redox polymerization to obtain a cured product, the use of a redox polymerization initiator allows curing at a temperature of 5 to 40°C. The curing temperature is preferably 15 to 40°C, as this reduces the amount of unreacted (meth)acryloyl groups remaining in the resulting resin for optical components and further increases the strength of the resin for optical components. Because the curable resin composition is less likely to gel and can be handled stably, a preferred method involves dissolving a reducing agent in the curable resin composition in advance and then adding a peroxide to the composition to carry out curing. When curing the curable resin composition, it is preferable to cure the curable resin composition in a sealed state to prevent curing inhibition by oxygen. Examples of sealing methods include sandwiching the curable resin composition between glass or PET film.

[0086] <Chain Transfer Agent> When a curable resin composition is subjected to a curing reaction in air, oxygen traps active radicals as peroxide radicals, inhibiting polymerization. However, by adding a chain transfer agent that donates hydrogen, polymerization inhibition by oxygen can be suppressed. Examples of the chain transfer agent include methyl mercaptoacetate, methyl 3-mercaptopropionate, 2-ethylhexyl 3-mercaptopropionate, 3-methoxybutyl 3-mercaptopropionate, n-octyl 3-mercaptopropionate, stearyl 3-mercaptopropionate, 1,4-bis(3-mercaptopropionyloxy)butane, 1,4-bis(3-mercaptobutyryloxy)butane, trimethylolethane tris(3-mercaptopropionate), ... trimethylolpropane tris(3-mercaptobutyrate), trimethylolpropane tris(3-mercaptopropionate), trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), dipentaerythritol hexakis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptobutyrate), tris[2-(3- mercaptocarboxylic acid esters such as tris[2-(3-mercaptopropionyloxy)ethyl]isocyanurate and tris[2-(3-mercaptobutyryloxy)ethyl]isocyanurate; alkyl thiols such as ethanethiol, 2-methylpropane-2-thiol, n-dodecanethiol, 2,3,3,4,4,5-hexamethylhexane-2-thiol (tert-dodecanethiol), ethane-1,2-dithiol, propane-1,3-dithiol, and benzylthiol; benzenethiol Examples of thiol compounds include aromatic thiols such as 2-mercaptoethanol, 3-methylbenzenethiol, 4-methylbenzenethiol, naphthalene-2-thiol, pyridine-2-thiol, benzimidazole-2-thiol, and benzothiazole-2-thiol; mercaptoalcohols such as 2-mercaptoethanol and 4-mercapto-1-butanol; and silane-containing thiols such as 3-(trimethoxysilyl)propane-1-thiol and 3-(triethoxysilyl)propane-1-thiol.Among these, from the viewpoint of the reactivity and storage stability of the curable composition, it is preferable to use a secondary thiol compound. When a chain transfer agent is added, the chain transfer agent may be used alone or in combination of two or more. The amount added is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and even more preferably 0.5 to 10 parts by mass, per 100 parts by mass of the total amount of the polymerizable components. When two or more types are used in combination, the total amount of the chain transfer agent falls within the above range.

[0087] <Solvent> The curable resin composition in this embodiment may contain a solvent for the purpose of diluting the organopolysiloxane and other ingredients. The type of solvent is not particularly limited as long as it does not impair the physical properties required for the organopolysiloxane and the curable resin composition cured product. Examples of the solvent include aromatic hydrocarbons (e.g., toluene, xylene, ethyl benzoate, ethylbenzene, benzyl alcohol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, diacetone alcohol), esters (e.g., methyl acetate, ethyl acetate, butyl acetate, sec-butyl acetate, methoxybutyl acetate, amyl acetate, normal propyl acetate, ethyl lactate, methyl lactate, butyl lactate, propylene glycol monomethyl ether acetate, γ-butyrolactone), and ethers ( For example, isopropyl ether, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, 1,4-dioxane, methyl tert-butyl ether, tetrahydrofuran), alcohols (e.g., methanol, ethanol, normal propanol, isopropanol, butanol, sec-butanol, tert-butanol, normal pentanol), halogenated solvents (e.g., methylene chloride, trichloroethylene, tetrachloroethylene, bromopropane, chloroform), and others (e.g., dimethyl sulfoxide, N,N-dimethylformamide, water), and two or more types of solvents may be used.

[0088] The content of the solvent in the curable resin composition is not particularly limited as long as it does not impair the physical properties required for the cured product of the curable resin composition, but when it is desired to reduce the viscosity while keeping the volatile content low, it is preferably more than 0% by mass and not more than 25% by mass of the entire curable resin composition. Furthermore, when a thin-film cured product is to be obtained, it is preferably 75% by mass or more and less than 100% by mass of the organopolysiloxane or the entire curable resin composition.

[0089] (Antioxidant) The curable resin composition preferably further contains an antioxidant. When the curable resin composition contains an antioxidant, discoloration of the cured product due to heat, such as heating during soldering of the cured product or heat generation in a device, can be suppressed. Specific examples of the antioxidant include phenols such as 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-p-cresol, n-octadecyl-3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate, tetrakis-[methylene-3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate]methane, triethylene glycol bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], and 1,6-hexanediol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. Examples of such antioxidants include phosphorus-based antioxidants such as triphenyl phosphite, trisisodecyl phosphite, tristridecyl phosphite, tris(2,4-di-tert-butylphenyl)phosphite, and tetra(C12-15 alkyl)-4,4'-isopropylidenediphenyl diphosphite; and sulfur-based antioxidants such as dilauryl-3,3'-thiodipropionate, ditridecyl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearic-3,3'-thiodipropionate, and pentaerythritol tetrakis(β-laurylthiopropionate). These antioxidants may be used alone or in combination of two or more.

[0090] (Other Components) The curable resin composition of this embodiment may contain other components such as a filler, a curing regulator, or a viscosity modifier. These components can be appropriately contained within a range that does not affect the heat resistance or refractive index of the cured product of the organopolysiloxane-containing curable resin composition of this embodiment. The organopolysiloxane-containing resin composition (curable composition) of this embodiment is particularly suitable for near-infrared optical waveguide applications. Therefore, in another embodiment of the present invention, an organopolysiloxane composition for near-infrared optical waveguides is also provided. The various aspects and requirements of the organopolysiloxane composition for near-infrared optical waveguides are as described above for the organopolysiloxane composition. In this specification, the term "organopolysiloxane composition" refers to both the organopolysiloxane composition and the organopolysiloxane composition for near-infrared optical waveguides.

[0091] <Cured Product of First Aspect> In a first aspect of the present invention (hereinafter sometimes referred to as the present first aspect), a cured product is provided, obtained by curing the organopolysiloxane-containing resin composition of the first embodiment described above with heat or light. The curing conditions for the organopolysiloxane-containing resin composition of this embodiment are not particularly limited, and the composition can be cured under conditions that are appropriately used for curing silicone resins, depending on the type of polymerization initiator, etc.

[0092] <Cured Product of Second Aspect> In the second aspect of the present invention (hereinafter, sometimes referred to as the present second aspect), a cured product is obtained by curing a cured product of a crosslinked structure derived from an organic group containing a polymerizable alkenyl group and a SiO ２／２ and a siloxane unit (D unit) represented by the following formula: wherein the refractive index at a wavelength of 1300 nm is 1.400 or more and 1.500 or less.

[0093] Near-infrared optical waveguides made of cured organopolysiloxanes containing aromatic groups, whose refractive index in the near-infrared wavelength region is greater than 1.5, have been reported for use as multimode optical waveguides with a large difference in refractive index between the core and cladding regions. However, the present inventors have discovered that the connection loss of near-infrared optical waveguides is reduced when the refractive index in the near-infrared wavelength region of a cured product obtained by curing a resin composition containing a specific organopolysiloxane is 1.400 to 1.500. Note that in this second aspect, the "transmission loss" and "connection loss" of the optical waveguide have the same meanings as defined above.

[0094] Without being bound by any particular theory, the following is thought to be the influence of the refractive index of a cured material used for a near-infrared optical waveguide. That is, when the refractive index in the near-infrared wavelength region of a cured material obtained by curing a composition containing an organopolysiloxane is 1.400 to 1.500, the cured material contains fewer rigid structures derived from aromatic structures, etc., and the cured material has toughness and is less likely to crack. It is thought that when an optical waveguide made of the cured material is cut, the end surface is less likely to become rough. This suppression of roughness on the end surface of the waveguide is thought to suppress light scattering and reduce connection loss.

[0095] The cured product of this second embodiment has a refractive index of 1.400 to 1.500 in the near-infrared wavelength region, resulting in less rigid structures derived from aromatic structures contained in the cured product. This suppresses roughness of the end surface of an optical waveguide made from the cured product, thereby suppressing light scattering and reducing connection loss. Furthermore, an optical waveguide having a core made from the cured product exhibits a small refractive index difference with the core of a near-infrared single-mode silica-based optical fiber, thereby reducing interfacial reflection and thereby reducing connection loss. For single-mode optical waveguide applications, the refractive index difference between the core and cladding constituting the optical waveguide must be approximately 0.01 to 0.02. For such applications, the refractive index of the core must be 1.4 to 1.5, while the cladding must also have a refractive index of approximately 1.4 to 1.5. Therefore, the cured product of this second embodiment is also suitable as a cladding material for a core having a refractive index of 1.4 to 1.5 in single-mode optical waveguide applications. In the second embodiment, the refractive index of the cured product is 1.400 to 1.500, preferably 1.420 to 1.490, more preferably 1.430 to 1.480 at 589 nm and 1300 nm.

[0096] The cured product of the second aspect is preferably obtained by curing an organopolysiloxane-containing resin composition containing the organopolysiloxane of the above-described embodiment 1. Examples of the organopolysiloxane, the method for producing the organopolysiloxane, the organopolysiloxane-containing resin composition (curable resin composition) containing a monofunctional polymerizable alkenyl compound, a polyfunctional polymerizable alkenyl compound, and / or an alkenyl polymer, etc., and other components, and the curing conditions for the composition, include those described above, and preferred ones and preferred combinations also apply similarly to the second aspect.

[0097] <Characteristics of the cured product> A polymerizable alkenyl-containing organic group and SiO ２／２ and an organopolysiloxane in which the proportion of aromatic groups in all groups bonded to silicon atoms is 20 mol % or less. The cured products of the first and second embodiments (hereinafter sometimes referred to as "both embodiments"), which are obtained by curing, as described above, an organopolysiloxane-containing resin composition containing an organopolysiloxane having siloxane units (D units) represented by the following formula:

[0098] Heat resistance: A cured product with high reflow resistance can be obtained, with a 5% weight loss temperature of preferably 330°C or higher, more preferably 333°C or higher, and even more preferably 340°C or higher. High reflow resistance can also prevent an increase in light propagation loss due to high-temperature solder reflow when mounting on electronic components, etc. The weight loss temperature is measured by the method described in the examples below.

[0099] Refractive Index: When used as a core material and / or cladding material for a near-infrared optical waveguide, the refractive index of the cured product at 589 nm and 1300 nm is in the range of 1.400 to 1.500, preferably 1.420 to 1.490, and more preferably 1.430 to 1.480, which reduces the content of rigid aromatic groups in the cured product, thereby exhibiting the toughness derived from the D units contained in the cured product, suppressing roughness of the end face when the waveguide is cut, reducing light scattering at the end face, and reducing connection loss. Furthermore, when the refractive index of the core material of the near-infrared optical waveguide is in the above range, the difference in refractive index between the core and the single-mode quartz optical fiber is small, and interface reflection is suppressed, leading to reduced connection loss.

[0100] [Near-infrared light waveguide and near-infrared light transmission component] In another embodiment of the present invention, there are provided a near-infrared light waveguide containing the cured products of both of the above aspects, and a near-infrared light transmission component at least comprising the near-infrared light waveguide. The near-infrared light waveguide of the present invention comprises a core and / or cladding formed from at least the cured products of both aspects, and may also comprise a substrate. It is preferable that both the core and the cladding are formed from the cured products of both of the above aspects, as this further suppresses roughness of the end face during cutting. The near-infrared light transmission component of this embodiment may also comprise, in addition to the near-infrared light waveguide described above, a connecting component such as a mirror or a connector to connect to an optical fiber or a silicon photonics optical circuit.

[0101] The cured products of both of the above embodiments can be used as both a cladding material for forming the cladding portion of an optical waveguide and a core material for forming the core portion, provided that the refractive index of the core material for forming the core portion is higher than the refractive index of the cladding material for forming the cladding portion.

[0102] The refractive index of the cured product can be controlled by changing the proportion of the organopolysiloxane structural units contained in the organopolysiloxane or the organopolysiloxane-containing resin composition. For example, increasing the value of M2 + D2 + T2 in the above formula [1], i.e., increasing the proportion of polymerizable alkenyl groups, increases the density of the resulting cured product and increases the refractive index. Conversely, decreasing the value of M2 + D2 + T2, i.e., decreasing the proportion of polymerizable alkenyl groups, decreases the density of the resulting cured product and decreases the refractive index. Alternatively, the refractive index of the cured product can be controlled by changing the component proportions of the organopolysiloxane-containing resin composition. Furthermore, adjusting the content (volume %) of polymerizable alkenyl groups in the polymerizable alkenyl compound and / or alkenyl polymer contained in the organopolysiloxane-containing resin composition can control the crosslink density of the cured product, as in the above case, thereby controlling the refractive index. In addition, the refractive index can be increased by increasing the aromatic group content (volume %) of the cured product, and decreased by increasing the fluorine content (volume %). Furthermore, the refractive index of the cured product can be controlled by combining these methods. For near-infrared single-mode optical signals, the difference in refractive index between the core material and the clad material is preferably 0.01 to 0.05, more preferably 0.01 to 0.04, and even more preferably 0.01 to 0.03.

[0103] When connecting to a near-infrared single-mode silica-based optical fiber in a device, a smaller difference in refractive index between the core material of the silica-based optical fiber and the core material of the optical waveguide reduces interfacial reflection of light at the connection portion and can further reduce connection loss. Generally, the refractive index of the core material of a near-infrared single-mode silica-based optical fiber is 1.4 to 1.5 at near-infrared wavelengths. If the refractive index of the core material of the optical waveguide is 1.400 to 1.500 at a wavelength of 589 nm and 1.400 to 1.500 at a wavelength of 1300 nm, more preferably 1.430 to 1.490 at a wavelength of 589 nm and 1.420 to 1.480 at a wavelength of 1300 nm, and even more preferably 1.435 to 1.480 at a wavelength of 589 nm and 1.425 to 1.470 at a wavelength of 1300 nm, the difference in refractive index between the two materials can be reduced, and connection loss can be further reduced.

[0104] The method for producing the near-infrared optical waveguide of this embodiment is not particularly limited. For example, an optical waveguide can be formed through a process of curing the above-mentioned organopolysiloxane or organopolysiloxane-containing resin composition by exposure (photocuring) or heating (thermocuring). As a typical example, an optical waveguide can be formed through an etching process and a development process using a lithography technique using a photomask. When producing an optical waveguide by photolithography, it is preferable to use a composition containing at least an organopolysiloxane and a photopolymerization initiator, and if necessary, a composition containing further added solvents, chain transfer agents, etc. can be used. It is also possible to produce the optical waveguide by a method such as nanoimprinting. The above-mentioned method for forming an optical waveguide using photolithography is particularly preferable because it allows the production of optical waveguides with small line widths and pitches.

[0105] The substrate of the near-infrared optical waveguide can be a silicon wafer, a silicon wafer with an oxide film, a polyimide resin, an epoxy resin, a PEEK resin, a liquid crystal polymer, glass, a glass epoxy substrate, or the like. When using photolithography, the core of the optical waveguide can be prepared on the substrate by a coating process in which an organopolysiloxane-containing resin composition is applied to the substrate, an exposure process through a photomask, and a washing process in which the unexposed composition is washed away with a solvent. Furthermore, an overclad can be prepared by applying and curing an organopolysiloxane or an organopolysiloxane-containing resin composition to the core prepared on the substrate. Before preparing the core, an underclad may be prepared in advance by applying and curing an organopolysiloxane or an organopolysiloxane-containing resin composition to the substrate. Alternatively, after the core and clad of the optical waveguide are prepared on the substrate, the waveguide may be peeled off from the substrate.

[0106] In this embodiment, the transmission loss and splice loss of the optical waveguide can be measured, for example, by the method described in the Examples below. The transmission loss is preferably 0.4 dB / cm or less, more preferably 0.35 dB / cm or less, and even more preferably 0.32 dB / cm or less. The splice loss is preferably 1.35 dB or less, more preferably 1.30 dB or less, and even more preferably 1.20 dB / cm or less.

[0107] In another embodiment, the present invention provides the following method for producing a near-infrared optical waveguide (sometimes referred to as the present production method). A first aspect of the present production method comprises the following steps, in this order: step (i-1) of applying a first curable polymer composition to a surface of a substrate to form a first polymer layer; step (i-2) of irradiating at least one selected region of the first polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and step (i-3) of removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, wherein the first curable polymer composition is the organopolysiloxane-containing resin composition or an organopolysiloxane-containing resin composition for a near-infrared optical waveguide.

[0108] In the first aspect, it is preferable to further include a step (i-4) of coating the substrate surface and the core with a second curable polymer composition to form a second polymer layer, and a step (i-5) of curing the second polymer layer to form an upper clad. The second curable polymer composition is not particularly limited as long as it is a curable composition, but is preferably the organopolysiloxane-containing resin composition.

[0109] A second aspect of the present production method comprises the steps of: (ii-1) applying a third curable polymer composition to a substrate surface to form a third polymer layer; (ii-2) irradiating at least one selected region of the third polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (ii-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (ii-4) coating the substrate surface and the core with a fourth curable polymer composition to form a fourth polymer layer; and (ii-5) curing the fourth polymer layer to form an upper clad, in this order; and it is necessary that at least one of the third curable polymer and the fourth curable polymer composition is the organopolysiloxane-containing resin composition.

[0110] As described above, as long as at least one of the third curable polymer composition and the fourth curable polymer composition is the organopolysiloxane-containing resin composition, the other curable polymer composition is not particularly limited as long as it is a curable composition. In this aspect, it is preferable that both the third curable polymer composition and the fourth curable polymer composition are the organopolysiloxane-containing resin compositions.

[0111] A third aspect of the present production method comprises the following steps, in this order: (iii-1) applying a fifth curable polymer composition to a substrate surface to form a fifth polymer layer; (iii-2) curing the fifth polymer layer to form a lower cladding; (iii-3) applying a sixth curable polymer composition onto the lower cladding to form a sixth polymer layer; (iii-4) irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and (iii-5) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; wherein at least one of the fifth curable polymer composition and the sixth curable polymer composition is the organopolysiloxane-containing resin composition.

[0112] As described above, as long as at least one of the fifth curable polymer composition and the sixth curable polymer composition is the organopolysiloxane-containing resin composition, there are no particular restrictions on the other curable polymer composition as long as it is a curable composition. In this aspect, it is preferable that both the fifth curable polymer composition and the sixth curable polymer composition are the organopolysiloxane-containing resin compositions.

[0113] A fourth aspect of the present manufacturing method comprises the steps of: (iv-1) applying a fifth curable polymer composition to a substrate surface to form a fifth polymer layer; (iv-2) curing the fifth polymer layer to form a lower cladding; (iv-3) applying a sixth curable polymer composition onto the lower cladding to form a sixth polymer layer; (iv-4) irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (iv-5) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (iv-6) coating the lower cladding and the core with a seventh curable polymer composition to form a seventh polymer layer; and (iv-7) curing the seventh polymer layer to form an upper cladding. The requirement is that at least one of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition is the organopolysiloxane-containing resin composition. In this aspect, it is preferable that all of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition are the organopolysiloxane-containing resin compositions.

[0114] The substrate used in this manufacturing method can be the substrate described above as the substrate for the near-infrared optical waveguide. The surface of the substrate to be used is preferably subjected to ozone treatment, plasma treatment, corona treatment, or the like in advance to remove any deposits on the surface, prevent the curable polymer composition to be applied from being repelled, and improve adhesion. Similarly, before forming the core and the upper clad, the surfaces on which the core and upper clad will be formed are preferably subjected to ozone treatment, plasma treatment, corona treatment, or the like in advance.

[0115] As described above, in each embodiment, at least a portion of the first to seventh curable polymer compositions must be the organopolysiloxane-containing resin composition, but the other curable polymer compositions may be any other polymer compositions that form the core, lower clad, or upper clad.

[0116] Examples of optional other polymer compositions include, but are not limited to, curable silicone compositions other than the organopolysiloxane-containing resin compositions described above; curable polyolefin compositions; curable polyamide compositions; curable epoxy resin compositions; curable amino resin compositions; curable polyurethane compositions; curable polyimide compositions; curable polyester compositions; and curable acrylic resin compositions.

[0117] The curable polymer composition can be applied to a substrate using any common method, such as spin coating, die coating, gravure coating, dipping, spraying, brushing, or screen printing. The curable polymer composition is typically applied by spin coating. The spin speed and spin time, as well as the solids content and viscosity of the curable polymer composition, can be adjusted so that the polymer layer has a desired thickness.

[0118] When the curable polymer composition contains a solvent, the production method may further include a step of removing at least a portion of the solvent from the formed polymer layer. The solvent can be removed by heating the polymer layer at a temperature of 50°C to 200°C for several tens of seconds to 60 minutes, or at a temperature of 80°C to 150°C for several tens of seconds to 60 minutes. Alternatively, the solvent may be removed under reduced pressure, or the solvent may be removed under reduced pressure and then further removed by heating.

[0119] The polymer layer can be cured by various means depending on the curing mechanism of the curable polymer composition. Such means include heating, exposure (to active energy rays such as radiation or ultraviolet radiation), and exposure to steam. The conditions for each can be selected appropriately. For example, curing can be performed using an exposure device with a high-pressure mercury lamp light source. The exposure atmosphere may be air or an inert atmosphere. Exposure in an inert atmosphere can reduce the amount of uncured layer formed on the surface of the polymer layer. However, the polymer layer forming the core is prepared by irradiating at least one selected region with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region. Similarly, the polymer layer forming the cladding may be prepared by irradiating at least one selected region with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region. After curing the polymer layer, the cured layer may be further heated or re-exposed. These treatments may promote curing, improve adhesion between the polymer layer and the substrate, and improve adhesion between polymer layers themselves. Conditions for the heat treatment include, for example, a temperature of 50°C to 200°C for several tens of seconds to 60 minutes, or a temperature of 80°C to 150°C for several tens of seconds to 60 minutes.

[0120] In the step of forming the core, after curing the curable polymer composition, a so-called development process is performed in which the non-exposed region is removed with a solvent to remove the non-exposed region. There are no limitations on the solvent or development method used for development. Any solvent may be used as long as the curable polymer composition is soluble in the solvent, and the curable polymer composition in the non-exposed region is dissolved by any method such as dipping or spraying. In the step of forming the clad, after curing the curable polymer composition, a so-called development process may be performed in which the non-exposed region is removed with a solvent to remove the non-exposed region. There are no limitations on the solvent or development method used for development. Any solvent may be used as long as the curable polymer composition is soluble in the solvent, and the curable polymer composition in the non-exposed region is dissolved by any method such as dipping or spraying. Furthermore, in the step of forming the core or the upper and lower clads, a process similar to the above-mentioned development may be used to remove the uncured layer on the surface of the polymer layer. After removing the non-exposed region with a solvent, it is preferable to remove the solvent by air drying or heating.

[0121] Generally, the lower cladding and upper cladding have a thickness of about 1 to 100 μm, and the core has a thickness of 1 to 50 μm. The refractive index of the core is preferably higher than that of the cladding, and light can be transmitted in a desired propagation mode depending on the size and refractive index of the core.

[0122] This fabrication method can be expanded to a high-throughput manufacturing method. Multiple optical waveguides can be simultaneously fabricated on a single substrate. Furthermore, this method can utilize conventional wafer fabrication techniques (e.g., coating, exposing, developing, and curing) and equipment. Optical waveguides fabricated according to this fabrication method have superior microfabrication properties, heat resistance, low transmission loss at near-infrared wavelengths, and reduced connection loss due to reflection at the optical fiber / optical waveguide interface compared to optical waveguides containing other known materials.

[0123] The present invention will be described in more detail by the following examples, but the present invention is not limited thereto.

[0124] [Evaluation method] (1) １H-NMR Measurement Method: Apparatus: AVANCE NEO 400, BBFO Probe (5 mm diameter), manufactured by Bruker Japan Co., Ltd. Measurement Conditions: Pulse repetition time / 5 seconds, Scan count / 16 times, Measurement mode / single pulse, Measurement temperature / 25°C, Flip angle / 30°, Spin / 20 Hz, Measurement temperature 25°C Sample Preparation: 60 mg of the organopolysiloxane to be measured was weighed out, and 12 mg of N,N-dimethylformamide was added as an internal standard. Further, deuterated chloroform was added to dissolve the sample to a total mass of 1 g, and the solution was placed in an NMR sample tube. Calculation of Functional Group Content: The functional group content was estimated from the ratio of the signal intensity of each component to the signal intensity of the internal standard N,N-dimethylformamide, and the weighed value.

[0125] (2) ２９ Si-NMR measurement method Sample preparation: Tris(2,4-pentanedionato)chromium(III) was added to deuterated chloroform to a concentration of 0.5 mass %. ２９ A solvent for Si-NMR measurement was obtained. 1.5 g of the organopolysiloxane to be measured was weighed out and ２９ 2.5 ml of a solvent for Si-NMR measurement was added to dissolve the solution, which was then placed in an NMR sample tube. ２９ Si-NMR Measurement Apparatus: JNM-ECS400 manufactured by JEOL Ltd., TUNABLE Probe (10 mm diameter): Si-free, AT10 probe Measurement conditions: Pulse repetition time / 16 seconds, Scan number / 1024 times, Measurement mode / non-gated decoupled pulse method (NNE), Flip angle / 90°, Spin / none, Measurement temperature / 25°C (2)-2: Organopolysiloxanes b, e to g described below ２９ Si-NMR Measurement Apparatus: AVANCE NEO 600, BBO Cryo Probe (5 mm diameter), manufactured by Bruker Japan Co., Ltd. Measurement conditions: Pulse repetition time / 16 seconds, number of scans / 1024 times, measurement mode / inverse gate decoupling measurement, flip angle / 90°, spin / none, measurement temperature / 25°C <Calculation of constitutional units> The signal intensity of each unit of silicon was measured, and the above １The constituent ratio of silicon units was calculated from the ratio of the signal intensity measured by H-NMR and the ratio of the functional group content.

[0126] (3) Measurement of refractive index of cured product (3)-1: Measurement of refractive index at 589 nm wavelength Using a Kalnew Precision Refractometer KPR2000 manufactured by Shimadzu Corporation, the refractive index of a cured product prepared by the method described below was measured at a wavelength of 589 nm (visible light region) at a temperature of 23° C. using a mixture of diiodomethane, monobromonaphthalene, and liquid paraffin as an intermediate liquid. (3)-2: Measurement of refractive index at 1300 nm wavelength Using a Metricon Model 2010 / M Prism Coupler (manufactured by Pneum Co., Ltd.), the refractive index of a thin film cured product prepared on a substrate by the method described below was measured at a wavelength of 1300 nm (near-infrared light region).

[0127] (4) Thermal Gravity Loss Temperature of Cured Product: The thermal weight loss temperature of the cured product was measured in air at a temperature increase rate of 10° C. / min using a NEXTA STA200 differential scanning calorimeter (TG-DSC) manufactured by Hitachi High-Tech Corporation.

[0128] (5) Fabrication of Optical Waveguide An optical waveguide was fabricated by forming an underclad, a core, and an overclad in this order on a silicon substrate using photolithography. The detailed procedure will be described later.

[0129] (6) Method for Measuring Waveguide Transmission Loss and Connection Loss: The silicon substrate side of the waveguide was scratched and then manually cut to expose the end faces, and single-mode fibers were spliced ​​to both ends. The input single-mode fiber was connected to a temperature-controlled fiber-output high-power LD stabilized light source (LDS1005) manufactured by Precise Gauge, and the output single-mode fiber was connected to a power meter (MT9810B) manufactured by Anritsu via matching oil with a refractive index of 1.51 at a wavelength of 589 nm, and loss was measured. Loss was measured at two or more points on waveguide samples with different optical path lengths, and the slope of the approximation line plotting loss versus optical path length was taken as the transmission loss (dB / cm), and the intercept was taken as the connection loss (dB).

[0130] [Method of synthesizing organopolysiloxane] [Synthesis Example 1] Method of synthesizing organopolysiloxane a Using 210.00 g of 3-methacryloyloxypropyltrimethoxysilane KBM503 manufactured by Shin-Etsu Chemical Co., Ltd. and 101.80 g of dimethyldimethoxysilane KBM22 manufactured by Shin-Etsu Chemical Co., Ltd. as organopolysiloxane raw materials, 155.90 g of toluene and 155.90 g of methanol as solvents, and a mixture of 104.33 g of 1N hydrochloric acid and 104.33 g of methanol as catalyst and water, hydrolysis and condensation were carried out while maintaining the temperature at 15° C. to 40° C. Thereafter, the reaction liquid was neutralized and washed with demineralized water, and then the solvent and water were removed and filtered, yielding 200 g of the target liquid organopolysiloxane a.

[0131] [Synthesis Example 2] Method for synthesizing organopolysiloxanes b and e Organopolysiloxanes b and e were obtained in the same manner as in Synthesis Example 1, except that the amounts of the organopolysiloxane raw materials were changed so that the proportions of the structural units were as shown in Table 1.

[0132] Synthesis Example 3 Method for Synthesizing Organopolysiloxane c With reference to JP-A-2014-510159, organopolysiloxane c was obtained using 3-methacryloyloxypropyltrimethoxysilane KBM503 manufactured by Shin-Etsu Chemical Co., Ltd. and diphenylsilanediol manufactured by Tokyo Chemical Industry Co., Ltd. as organopolysiloxane raw materials.

[0133] Synthesis Example 4 Method for Synthesizing Organopolysiloxane d Organopolysiloxane d was obtained in the same manner as in Synthesis Example 3, except that 3-methacryloyloxypropyltrimethoxysilane KBM503 manufactured by Shin-Etsu Chemical Co., Ltd., diphenylsilanediol manufactured by Tokyo Chemical Industry Co., Ltd., and trimethoxy(3,3,3-trifluoropropyl)silane manufactured by Tokyo Chemical Industry Co., Ltd. were used as organopolysiloxane raw materials.

[0134] Synthesis Example 5 Method for Synthesizing Organopolysiloxane f Organopolysiloxane f was obtained in the same manner as in Synthesis Example 1, except that 3-methacryloyloxypropylmethyldimethoxysilane KBM502 manufactured by Shin-Etsu Chemical Co., Ltd. and trimethoxymethylsilane manufactured by Tokyo Chemical Industry Co., Ltd. were used as organopolysiloxane raw materials.

[0135] Synthesis Example 6 Method for Synthesizing Organopolysiloxane g Organopolysiloxane g was obtained in the same manner as in Synthesis Example 1, except that organopolysiloxane raw materials were 3-methacryloyloxypropyltrimethoxysilane KBM503 manufactured by Shin-Etsu Chemical Co., Ltd., dimethyldimethoxysilane KBM22 manufactured by Shin-Etsu Chemical Co., Ltd., and dimethoxy(methyl)(3,3,3-trifluoropropyl)silane manufactured by Tokyo Chemical Industry Co., Ltd.

[0136] Synthesis Example 7 Method for Synthesizing Organopolysiloxanes h and i Organopolysiloxanes h and i were obtained by synthesis in the same manner as in Synthesis Example 1, except that the organopolysiloxane raw materials were changed to the proportions of structural units shown in Table 1, using methyl silicate MS51 manufactured by Mitsubishi Chemical Corporation, 3-methacryloyloxypropyltrimethoxysilane KBM503 manufactured by Shin-Etsu Chemical Co., Ltd., and hexamethyldisiloxane manufactured by Nacalai Tesque, Inc.

[0137] [Method for Producing a Cured Product] 2.0 parts by mass (when organopolysiloxanes a, b, e to i were used) or 0.5 parts by mass (when organopolysiloxanes c and d were used) of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, manufactured by iGM Resins B.V.) as a photopolymerization initiator was added to 100 parts by mass of organopolysiloxane, and the mixture was stirred to dissolve the photopolymerization initiator, thereby preparing a composition. Furthermore, 100 parts by mass of organopolysiloxane b was mixed with 2.0 parts by mass of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, manufactured by iGM Resins B.V.) as a photopolymerization initiator. A composition was also prepared by adding 2.0 parts by mass of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369) manufactured by Co., Ltd. and 10 parts by mass of pentaerythritol tetrakis(3-mercaptobutyrate) (PE1, manufactured by Resonac Co., Ltd.) as a chain transfer agent. In addition, a composition was prepared in which 2.0 parts by mass of 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Omnirad TPO H, manufactured by iGM Resins B.V.) was added as a photopolymerization initiator instead of Omnirad 369 per 100 parts by mass of organopolysiloxane b, and a composition was also prepared in which 2.0 parts by mass of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad 819, manufactured by iGM Resins B.V.) was added as a photopolymerization initiator instead of Omnirad 369 per 100 parts by mass of organopolysiloxane b. The resulting composition was sandwiched between two pieces of glass via a 1 mm thick silicone spacer and exposed to an LED with a wavelength of 365 nm (integrated light intensity: 6000 mJ / cm). ２ Using this test piece, the refractive index at a wavelength of 589 nm and the 5% weight loss temperature were measured.

[0138] [Method for Producing a Thin Film Cured on a Substrate] To 100 parts by weight of organopolysiloxane, 2.0 parts by mass (when organopolysiloxane a or b was used) or 0.5 parts by mass (when organopolysiloxane c or d was used) of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, manufactured by iGM Resins B.V.) as a photopolymerization initiator and 60 parts by mass of propylene glycol monomethyl ether acetate as an organic solvent were added and stirred at room temperature. A composition containing the organopolysiloxane b was also prepared by further adding 10 parts by mass of pentaerythritol tetrakis(3-mercaptobutyrate) (PE1, manufactured by Resonac Co., Ltd.) as a chain transfer agent. As compositions containing the organopolysiloxane b, a composition in which 2.0 parts by mass of 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Omnirad TPO H, manufactured by iGM Resins B.V.) was added as the photopolymerization initiator instead of Omnirad 369, a composition in which 2.0 parts by mass of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Omnirad 819, manufactured by iGM Resins B.V.) was added as the photopolymerization initiator instead of Omnirad 369, and a composition in which 2.0 parts by mass of methyl 4-acetoxyimino-5-oxo-5-(4-(phenylthio)phenyl)pentanoate (photopolymerization initiator-1) was added as the photopolymerization initiator instead of Omnirad 369 were also prepared. The obtained composition was spin-coated onto a glass substrate, and the solvent was removed by reduced pressure treatment. After that, the composition was photocured (integrated light amount at a wavelength of 365 nm: 1000 mJ / cm ２ ), and then heated in a heating furnace at 150° C. for 3 hours to form a thin film cured product on the substrate.

[0139] [Preparation of Composition A to be Used for Forming Optical Waveguide Core] 100 parts by mass of organopolysiloxane a, 2 parts by mass of Omnirad 369, and 20 parts by mass of propylene glycol monomethyl ether acetate were placed in a container and stirred for 2 hours to obtain Composition A to be used for forming an optical waveguide core.

[0140] [Preparation of Composition H to be Used for Forming Optical Waveguide Core] 100 parts by mass of organopolysiloxane h, 2 parts by mass of Omnirad 369, 10 parts by mass of PE1, and 20 parts by mass of propylene glycol monomethyl ether acetate were placed in a container and stirred for 2 hours to obtain Composition H to be used for forming an optical waveguide core.

[0141] [Preparation of Composition C Used to Form Optical Waveguide Core] Composition C was obtained in the same manner as in the preparation of composition A, except that organopolysiloxane c was used instead of organopolysiloxane a and the amount of Omnirad 369 was changed to 0.5 parts by mass.

[0142] [Preparation of Composition B Used for Forming Optical Waveguide Cladding] Composition B was obtained in the same manner as in the preparation of composition A, except that organopolysiloxane b was used instead of organopolysiloxane a.

[0143] [Preparation of Composition D Used for Forming Optical Waveguide Cladding] Composition D was obtained in the same manner as in the preparation of composition A, except that organopolysiloxane d was used instead of organopolysiloxane a and 0.5 parts by mass of Omnirad 369 was used.

[0144] [Preparation of Composition I Used for Forming Optical Waveguide Cladding] Composition I was obtained in the same manner as in the preparation of composition A, except that organopolysiloxane i was used instead of organopolysiloxane a.

[0145] [Example 1] [Fabrication of Optical Waveguide] Composition B was applied by spin coating to an ozone-treated silicon wafer, the solvent was removed by reduced pressure treatment, and the wafer was exposed using an exposure machine (intensity 40 mW / cm at a wavelength of 365 nm). ２ , cumulative light intensity 1000 mJ / cm ２After heating at 130°C for 10 minutes, insufficiently cured portions of the coating surface were washed away using propylene glycol monomethyl ether acetate and then 2-propanol, and the coating was heated in a heating furnace at 130°C for 30 seconds to form an underclad of about 10 μm in thickness on the silicon wafer substrate. Next, the surface of the silicon wafer substrate on which the underclad had been formed was plasma treated, and then Composition A was spin-coated thereon, after which the solvent was removed by reduced pressure treatment and the coating was exposed to light using a mask in an exposure machine (intensity 500 mW / cm at a wavelength of 365 nm). ２ , cumulative light amount: 2000 mJ / cm ２ After heating at 130°C for 10 minutes, the composition in the unexposed areas was washed away using propylene glycol monomethyl ether acetate and then using 2-propanol, and the substrate was heated in a heating furnace at 130°C for 30 seconds to form a core on the underclad on the silicon wafer substrate. Subsequently, the surface of the silicon wafer substrate on which the underclad and core had been formed was plasma treated, and Composition B was spin-coated, after which the solvent was removed by reduced pressure treatment and the substrate was exposed using an exposure machine (intensity 40 mW / cm at a wavelength of 365 nm). ２ , cumulative light amount: 1000 mJ / cm ２ After heating at 130°C for 10 minutes, insufficiently cured portions of the coating surface were washed away with propylene glycol monomethyl ether acetate and then with 2-propanol, and the coating was heated in a heating furnace at 130°C for 30 seconds and further heated in a heating furnace at 150°C for 1 hour to form an overclad on the underclad and core on the silicon wafer substrate, thereby obtaining an optical waveguide X.

[0146] [Comparative Examples 1 and 2] As in the above examples, a waveguide Y of Comparative Example 2 was obtained by using composition C to form the core and composition D to form the cladding, and a waveguide Z of Comparative Example 1 was obtained by using composition H to form the core and composition I to form the cladding.

[0147] [Evaluation of Molecular Composition Ratio of Organopolysiloxane, Cured Product, and Optical Waveguide] １ H-NMR and ２９The molecular composition ratio of the organopolysiloxane before curing calculated by Si-NMR measurement and the evaluation results of the cured product are shown in Table 1. Table 2 also shows the evaluation results of the optical waveguides of the examples and comparative examples.

[0148]

[0149]

[0150] Example 2 [Method 1 for Producing an Optical Waveguide Having a Core on a Substrate] To 100 parts by mass of the organopolysiloxane a, 2.0 parts by mass of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, manufactured by iGM Resins B.V.) as a photopolymerization initiator and 20 parts by mass of propylene glycol monomethyl ether acetate as an organic solvent were added, and the mixture was stirred at room temperature. This composition was designated as a first curable polymer composition. The first curable polymer composition was spin-coated onto a silicon wafer substrate whose surface had been treated with ozone, after which the solvent was removed by reduced pressure treatment and the composition was exposed to light using a mask in an exposure machine (intensity at a wavelength of 365 nm: 500 mW / cm ２ , cumulative light intensity: 2,000 mJ / cm ２ After heating at 130°C for 10 minutes, the composition in the unexposed areas was washed away using propylene glycol monomethyl ether acetate and then 2-propanol, and the substrate was heated in a heating furnace at 130°C for 30 seconds and then further heated in a heating furnace at 150°C for 1 hour to produce an optical waveguide core on the silicon wafer substrate. Figure 1 is a schematic cross-sectional view of the optical waveguide produced in Example 2.

[0151] Example 3 [Method 2 for Producing an Optical Waveguide Having a Core / Upper Cladding on a Substrate] To 100 parts by mass of the organopolysiloxane b, 2.0 parts by mass of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, manufactured by iGM Resins B.V.) as a photopolymerization initiator and 20 parts by mass of propylene glycol monomethyl ether acetate as an organic solvent were added, and the mixture was stirred at room temperature. This composition was designated as a second curable polymer composition. The surface of the silicon wafer substrate on which the optical waveguide core had been produced, obtained in Example 2, was plasma-treated, and the second curable polymer composition was spin-coated. After that, the solvent was removed by reduced pressure treatment, and the substrate was exposed with an exposure machine (intensity at a wavelength of 365 nm: 40 mW / cm ２ , cumulative light intensity: 1,000 mJ / cm ２ After heating at 130°C for 10 minutes, insufficiently cured portions of the coating surface were washed away with propylene glycol monomethyl ether acetate and then with 2-propanol, and the coating was heated in a heating furnace at 130°C for 30 seconds and then further heated in a heating furnace at 150°C for 1 hour to produce an optical waveguide having a core and an upper clad on a silicon wafer substrate. Figure 2 is a schematic cross-sectional view of the optical waveguide produced in Example 3.

[0152] Example 4 Method 3 for Producing an Optical Waveguide Having a Lower Cladding / Core on a Substrate To 100 parts by mass of the organopolysiloxane b, 2.0 parts by mass of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, manufactured by iGM Resins B.V.) as a photopolymerization initiator and 20 parts by mass of propylene glycol monomethyl ether acetate as an organic solvent were added, and the mixture was stirred at room temperature. This composition was designated as a fifth curable polymer composition. The fifth curable polymer composition was spin-coated onto a silicon wafer substrate whose surface had been treated with ozone, followed by removing the solvent by reduced pressure treatment and exposing the composition to light using an exposure machine (intensity at a wavelength of 365 nm: 40 mW / cm). ２ , cumulative light intensity: 1,000 mJ / cm ２After heating at 130°C for 10 minutes, insufficiently cured portions of the coating surface were washed away using propylene glycol monomethyl ether acetate and then 2-propanol, and the coating was heated in a heating furnace at 130°C for 30 seconds to produce a lower clad made of the fifth curable polymer composition on a silicon wafer substrate. To 100 parts by mass of the organopolysiloxane a, 2.0 parts by mass of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, iGM Resins B.V.) as a photopolymerization initiator and 20 parts by mass of propylene glycol monomethyl ether acetate as an organic solvent were added, and the mixture was stirred at room temperature. This composition was designated the sixth curable polymer composition. The surface of the silicon wafer substrate on which the lower cladding was formed was subjected to plasma treatment, and the sixth curable polymer composition was spin-coated thereon. After that, the solvent was removed by reduced pressure treatment, and the resulting layer was exposed to light using a mask in an exposure machine (intensity at a wavelength of 365 nm: 500 mW / cm ２ , cumulative light intensity: 2,000 mJ / cm ２ After heating at 130°C for 10 minutes, the composition in the unexposed areas was washed away using propylene glycol monomethyl ether acetate and then 2-propanol, and the substrate was heated in a heating furnace at 130°C for 30 seconds and further heated in a heating furnace at 150°C for 1 hour to produce an optical waveguide having a lower cladding made of the fifth curable polymer composition and a core made of the sixth curable polymer composition on a silicon wafer substrate. Figure 3 is a schematic cross-sectional view of the optical waveguide produced in Example 4.

[0153] Example 5 [Method 4 for Producing an Optical Waveguide Having Lower Cladding / Core / Upper Cladding on a Substrate] To 100 parts by mass of the organopolysiloxane b, 2.0 parts by mass of 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (Omnirad 369, manufactured by iGM Resins B.V.) as a photopolymerization initiator and 20 parts by mass of propylene glycol monomethyl ether acetate as an organic solvent were added, and the mixture was stirred at room temperature. This composition was designated as the seventh curable polymer composition. The surface of the silicon wafer substrate on which the lower cladding and core had been produced in Example 4 was plasma-treated, and the seventh curable polymer composition was spin-coated. After that, the solvent was removed by reduced pressure treatment, and the mixture was exposed with an exposure machine (intensity at a wavelength of 365 nm: 40 mW / cm ２ , cumulative light intensity: 1,000 mJ / cm ２ After heating at 130°C for 10 minutes, insufficiently cured portions of the coating surface were washed away using propylene glycol monomethyl ether acetate and then 2-propanol, and the coating was heated in a heating furnace at 130°C for 30 seconds and further heated in a heating furnace at 150°C for 1 hour to produce an optical waveguide having a lower cladding made of the fifth curable polymer composition, a core made of the sixth curable polymer composition, and an upper cladding made of the seventh curable polymer composition on a silicon wafer substrate. Figure 4 is a schematic cross-sectional view of the optical waveguide produced in Example 5.

[0154] From Tables 1 and 2, the organic group containing a polymerizable alkenyl group and SiO ２／２ In the waveguide X prepared using organopolysiloxanes a and b, which have siloxane units (D units) represented by the formula: and in which the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol % or less, the refractive indices of the core at wavelengths of 589 nm and 1300 nm are 1.476 and 1.463, respectively, and it can be seen that when connected to a single-mode quartz optical fiber, the refractive index difference between the cores is small and interface reflection is suppressed. Furthermore, measurement results showed that the transmission loss was 0.4 dB / cm or less and the connection loss was also a low loss of 1.20 dB or less. On the other hand, in the waveguide X prepared using organopolysiloxanes a and b, which have an organic group containing a polymerizable alkenyl group and SiO ２／２In the waveguide Y prepared using organopolysiloxanes c and d, which have siloxane units (D units) represented by the formula: but in which the proportion of aromatic groups in the total of all groups bonded to silicon atoms exceeds 20 mol%, the refractive indices of the cores at wavelengths of 589 nm and 1300 nm are 1.558 and 1.538, respectively, and when connected to a single-mode silica optical fiber, the refractive index difference between the cores is large and interfacial reflection cannot be suppressed. Furthermore, as a result of measurement, the transmission loss was 0.4 dB / cm or less, but the connection loss was 1.30 dB or more. Although the waveguide Y has an organic group containing a polymerizable alkenyl group and the proportion of aromatic groups is 20 mol% or less, the refractive index of the cores is 1.558 and 1.538, respectively, and when connected to a single-mode silica optical fiber, the refractive index difference between the cores is large and interfacial reflection cannot be suppressed. ２／２ In the waveguide Z produced using organopolysiloxanes h and i which do not have siloxane units (D units) represented by the formula (I), the transmission loss and connection loss increased, and this result indicates that D units are necessary to reduce the transmission loss and connection loss.

[0155] The refractive index of the cured organopolysiloxane of this embodiment is only slightly different from that of a silica optical fiber core. Therefore, when used as a core material for a near-infrared optical waveguide, interfacial reflection is suppressed when connecting to a near-infrared single-mode silica optical fiber. Furthermore, in the case of a near-infrared optical waveguide using this core material, the difference in refractive index between the core and clad portions is small, making the cured organopolysiloxane of this embodiment useful as a clad material for the near-infrared optical waveguide. Furthermore, the cured organopolysiloxane of this embodiment has toughness, and optical waveguides formed from this cured product are less likely to develop cracks at their end faces when cut, resulting in low connection loss. Therefore, the organopolysiloxane of this embodiment is useful as a material for forming a near-infrared optical waveguide. It has also been confirmed that the addition of a chain transfer agent improves curability and the heat resistance of the cured product. In addition, from the viewpoints of optical properties, heat resistance, and lithographic patterning ability, it is expected to be used as an optical waveguide connected to a non-silica optical fiber whose core material has a refractive index of approximately 1.4 to 1.5, or as an optical adhesive used in the connection between an optical waveguide and an optical fiber.

[0156] 10 Substrate 20 Lower cladding layer 30 Upper cladding layer 40 Core

Claims

1. An organopolysiloxane represented by the following general formula [1]. (R １ R ２ R ３ SiO １／２ ) Ｍ１ (R ４ R ５ R ６ SiO １／２ ) Ｍ２ (R ７ R ８ SiO ２／２ ) ＋ (R ９ R ６ SiO ２／２ ) Ｄ２ (R １０ SiO ３／２ ) Ｔ１ (R ６ SiO ３／２ ) Ｔ２ (SiO ４／２ ) Ｑ (O １／２ R １１ ) Ｙ１ (O １／２ R ６ ) Ｙ２ [In the above formula [1], R １ ~R ５ , R ７ ~R １１ R is independently one or more groups selected from an organic group, a reactive functional group, or a hydrogen atom. １ ~R ３ , R ７ , R ８ , R １０ and R １１ does not contain a polymerizable alkenyl group. ６ are one or more organic groups containing a polymerizable alkenyl group, which may be the same or different from each other, 0≦M1, 0≦Q, 0≦Y1, 0≦Y2, 0<D1+D2, 0<M2+D2+T2, M1+M2+D1+D2+T1+T2+Q=1, and the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol % or less.

2. The organopolysiloxane according to claim 1, wherein in the formula [1], 0.1 < D1 + D2.

3. The organopolysiloxane according to claim 1, wherein in formula [1], 0<D1.

4. The organopolysiloxane according to claim 1, wherein in the formula [1], 0.02≦Y1≦0.

25.

5. In the formula [1], R ７ ~R ９ The organopolysiloxane of claim 1 , wherein the organopolysiloxane is free of aromatic groups.

6. In the formula [1], R １ ~R １１ The organopolysiloxane of claim 1 , wherein the organopolysiloxane is free of aromatic groups.

7. In the formula [1], ６ The organopolysiloxane according to claim 1, wherein each molecule contains one or more functional groups selected from the group represented by the following formulas [2] to [5]: (In the above formula, X is a divalent organic group, which may have a branched structure and / or a cyclic structure. When X is bonded to a silicon atom, the atom at the end of X that is directly bonded to the silicon is a carbon atom. When X is bonded to an oxygen atom directly bonded to the silicon, the atom at the end of X that is directly bonded to the oxygen atom is a carbon atom. * indicates a bond.) 8. In the formula [1], the R ６ 2. The organopolysiloxane according to claim 1, wherein is an acryloyloxypropyl group and / or a methacryloyloxypropyl group.

9. In the general formula [1], R ７ , R ８ The organopolysiloxane according to claim 1, wherein each independently represents an alkyl group having 1 to 20 carbon atoms.

10. An organopolysiloxane-containing resin composition comprising the organopolysiloxane according to any one of claims 1 to 9 and a polymerization initiator.

11. A cured product obtained by curing the organosiloxane-containing resin composition according to claim 10.

12. A near-infrared optical waveguide produced using the organosiloxane-containing resin composition according to claim 10.

13. A near-infrared optical waveguide having a core portion and a clad portion, wherein both the core portion and the clad portion are made using the organosiloxane-containing resin composition according to claim 10.

14. A near-infrared light transmission component comprising at least the near-infrared light waveguide according to claim 12.

15. A near-infrared light transmission component comprising at least the near-infrared light waveguide according to claim 13.

16. A method for producing a near-infrared optical waveguide, comprising the steps of: (i-1) applying a first curable polymer composition to a surface of a substrate to form a first polymer layer; (i-2) irradiating at least one selected region of the first polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and (i-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, in this order; wherein the first curable polymer composition is the organopolysiloxane-containing resin composition according to claim 10.

17. The method for producing a near-infrared optical waveguide according to claim 16, further comprising: a step (i-4) of coating the substrate surface and the core with a second curable polymer composition to form a second polymer layer; and a step (i-5) of curing the second polymer layer to form an upper clad.

18. A method for producing a near-infrared optical waveguide according to claim 17, wherein the second curable polymer composition is the organopolysiloxane-containing resin composition according to claim 10.

19. A method for producing a near-infrared optical waveguide, comprising the steps of: (ii-1) applying a third curable polymer composition to a surface of a substrate to form a third polymer layer; (ii-2) irradiating at least one selected region of the third polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (ii-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (ii-4) coating the surface of the substrate and the core with a fourth curable polymer composition to form a fourth polymer layer; and (ii-5) curing the fourth polymer layer to form an upper clad, in this order; wherein at least one of the third curable polymer composition and the fourth curable polymer composition is the organopolysiloxane-containing resin composition according to claim 10.

20. A method for producing a near-infrared optical waveguide as described in claim 19, wherein both the third curable polymer composition and the fourth curable polymer composition are the organopolysiloxane-containing resin composition described in claim 10.

21. A method for producing a near-infrared optical waveguide, comprising the steps of: applying a fifth curable polymer composition to a surface of a substrate to form a fifth polymer layer; curing the fifth polymer layer to form a lower clad; applying a sixth curable polymer composition onto the lower clad to form a sixth polymer layer; irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, in this order; wherein at least one of the fifth curable polymer composition and the sixth curable polymer composition is the organopolysiloxane-containing resin composition according to claim 10.

22. A method for producing a near-infrared optical waveguide as described in claim 21, wherein both the fifth curable polymer composition and the sixth curable polymer composition are the organopolysiloxane-containing resin composition as described in claim 10.

23. A method for manufacturing a semiconductor device comprising the steps of: applying a fifth curable polymer composition onto a substrate surface to form a fifth polymer layer; curing the fifth polymer layer to form a lower cladding; applying a sixth curable polymer composition onto the lower cladding to form a sixth polymer layer; irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; covering the lower cladding and the core with a seventh curable polymer composition to form a seventh polymer layer; and curing the seventh polymer layer to form an upper cladding, in this order; The method for producing a near-infrared optical waveguide, wherein at least one of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition is the organopolysiloxane-containing resin composition according to claim 10.

24. A method for producing a near-infrared optical waveguide as described in claim 23, wherein the fifth curable polymer composition, the sixth curable polymer composition and the seventh curable polymer composition are all organopolysiloxane-containing resin compositions as described in claim 10.

25. Crosslinked structure derived from organic group containing polymerizable alkenyl group and SiO ２／２ and a siloxane unit (D unit) represented by the following formula: wherein the refractive index at a wavelength of 1,300 nm is 1.400 or more and 1.500 or less.

26. The cured product according to claim 25, having a refractive index at a wavelength of 589 nm of 1.400 or more and 1.500 or less.

27. The cured product according to claim 25, which is obtained by curing an organopolysiloxane represented by the following general formula [1]. (R １ R ２ R ３ SiO １／２ ) Ｍ１ (R ４ R ５ R ６ SiO １／２ ) Ｍ２ (R ７ R ８ SiO ２／２ ) Ｄ１ (R ９ R ６ SiO ２／２ ) Ｄ２ (R １０ SiO ３／２ ) Ｔ１ (R ６ SiO ３／２ ) Ｔ２ (SiO ４／２ ) Ｑ (O １／２ R １１ ) Ｙ１ (O １／２ R ６ ) Ｙ２ [In the above formula [1], R １ ~R ５ , R ７ ~R １１ R is independently one or more groups selected from an organic group, a reactive functional group, or a hydrogen atom. １ ~R ３ , R ７ , R ８ , R １０ and R １１ does not contain a polymerizable alkenyl group. ６ are one or more organic groups containing a polymerizable alkenyl group, which may be the same or different from each other, 0≦M1, 0≦Q, 0≦Y1, 0≦Y2, 0<D1+D2, 0<M2+D2+T2, M1+M2+D1+D2+T1+T2+Q=1, and the proportion of aromatic groups in the total of all groups bonded to silicon atoms is 20 mol % or less.

28. The cured product according to claim 27, wherein in formula [1], 0.1 < D1 + D2.

29. The cured product according to claim 27, wherein in formula [1], 0<D1.

30. The cured product according to claim 27, wherein in formula [1], 0.02≦Y1≦0.

25.

31. In the formula [1], R １ ~R １１ The cured product of claim 27 , wherein the is no aromatic group.

32. In the formula [1], the R ６ The cured product according to claim 27, wherein the cured product has one or more functional groups selected from the group represented by the following formulas [2] to [5] in one molecule: (In the above formula, X is a divalent organic group, which may have a branched structure and / or a cyclic structure. When X is bonded to a silicon atom, the atom at the end of X that is directly bonded to the silicon is a carbon atom. When X is bonded to an oxygen atom directly bonded to the silicon, the atom at the end of X that is directly bonded to the oxygen atom is a carbon atom. * indicates a bond.) 33. In the formula [1], the R ６ The cured product according to claim 27, wherein is an acryloyloxypropyl group and / or a methacryloyloxypropyl group.

34. In the general formula [1], R ７ , R ８ The cured product according to claim 27, wherein each independently represents an alkyl group having 1 to 20 carbon atoms.

35. A near-infrared optical waveguide comprising the cured product according to any one of claims 25 to 34.

36. A near-infrared waveguide having a core portion and a clad portion, wherein both the core portion and the clad portion comprise the cured product according to any one of claims 25 to 34.

37. A near-infrared light transmission component comprising at least the near-infrared light waveguide according to claim 35.

38. A near-infrared light transmission component comprising at least the near-infrared light waveguide according to claim 36.

39. An organic group containing a polymerizable alkenyl group, and SiO ２／２ and a ratio of aromatic groups to the total of all groups bonded to silicon atoms is 20 mol % or less.

40. The organopolysiloxane for near-infrared optical waveguide according to claim 39, which is represented by the following general formula [1]: (R １ R ２ R ３ SiO １／２ ) Ｍ１ (R ４ R ５ R ６ SiO １／２ ) Ｍ２ (R ７ R ８ SiO ２／２ ) Ｄ１ (R ９ R ６ SiO ２／２ ) Ｄ２ (R １０ SiO ３／２ ) Ｔ１ (R ６ SiO ３／２ ) Ｔ２ (SiO ４／２ ) Ｑ (O １／２ R １１ ) Ｙ１ (O １／２ R ６ ) Ｙ２ ...[1] [In formula [1], R １ ~R ５ , R ７ ~R １１ R is independently one or more groups selected from the group consisting of an organic group, a reactive functional group, and a hydrogen atom. １ ~R ３ , R ７ , R ８ , R １０ and R １１ does not contain a polymerizable alkenyl group. ６ R represents one or more organic groups containing a polymerizable alkenyl group, and when a plurality of organic groups are present, they may be the same or different; １ ~R １１ The proportion of aromatic groups in the total of the above is 20 mol % or less, 0≦M1, 0≦Q, 0≦Y1, 0≦Y2, 0<D1+D2, 0<M2+D2+T2, and M1+M2+D1+D2+T1+T2+Q=1.

41. The organopolysiloxane for use in a near-infrared optical waveguide according to claim 40, wherein in the formula [1], 0.1<D1+D2.

42. The organopolysiloxane for use in a near-infrared optical waveguide according to claim 40, wherein in the formula [1], 0<D1.

43. The organopolysiloxane for use in a near-infrared optical waveguide according to claim 40, wherein, in the formula [1], 0.02≦Y1≦0.

25.

44. In the formula [1], R ７ ~R ９ The organopolysiloxane for use in a near-infrared optical waveguide according to claim 40, which does not contain an aromatic group.

45. In the formula [1], the R ６ The organopolysiloxane for near-infrared optical waveguide according to claim 40, wherein the organopolysiloxane has one or more functional groups selected from the group represented by the following formulas [2] to [5] in one molecule: (In the above formula, X is a divalent organic group, which may have a branched structure and / or a cyclic structure. When X is bonded to a silicon atom, the atom at the end of X that is directly bonded to the silicon is a carbon atom. When X is bonded to an oxygen atom directly bonded to the silicon, the atom at the end of X that is directly bonded to the oxygen atom is a carbon atom. * indicates a bond.) 46. ​​In the formula [1], the R ６ The organopolysiloxane for a near-infrared optical waveguide according to claim 40, wherein is an acryloyloxypropyl group and / or a methacryloyloxypropyl group.

47. In the formula [1], R １ ~R １１ The organopolysiloxane for use in a near-infrared optical waveguide according to claim 40, which does not contain an aromatic group.

48. An organopolysiloxane-containing resin composition for near-infrared optical waveguides, comprising the organopolysiloxane for near-infrared optical waveguides according to claim 39 or 40, and a polymerization initiator.

49. A cured product for near-infrared optical waveguide, obtained by curing the organopolysiloxane-containing resin composition for near-infrared optical waveguide according to claim 48.

50. A near-infrared optical waveguide produced using the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to claim 48.

51. A near-infrared waveguide having a core portion and a clad portion, wherein both the core portion and the clad portion are made using the organopolysiloxane-containing resin composition for near-infrared optical waveguides described in claim 48.

52. A near-infrared light transmission component comprising at least the near-infrared light waveguide according to claim 50.

53. A near-infrared light transmission component comprising at least the near-infrared light waveguide according to claim 51.

54. A method for producing a near-infrared optical waveguide, comprising the steps of: (i-1) applying a first curable polymer composition to a surface of a substrate to form a first polymer layer; (i-2) irradiating at least one selected region of the first polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and (i-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, in this order; wherein the first curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to claim 48.

55. A method for producing a near-infrared optical waveguide according to claim 54, further comprising: a step (i-4) of coating the substrate surface and the core with a second curable polymer composition to form a second polymer layer; and a step (i-5) of curing the second polymer layer to form an upper cladding.

56. A method for producing a near-infrared optical waveguide according to claim 55, wherein the second curable polymer composition is the organopolysiloxane-containing resin composition for a near-infrared optical waveguide according to claim 48.

57. A method for producing a near-infrared optical waveguide, comprising the steps of: (ii-1) applying a third curable polymer composition to a surface of a substrate to form a third polymer layer; (ii-2) irradiating at least one selected region of the third polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; (ii-3) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; (ii-4) coating the surface of the substrate and the core with a fourth curable polymer composition to form a fourth polymer layer; and (ii-5) curing the fourth polymer layer to form an upper clad, in this order; wherein at least one of the third curable polymer composition and the fourth curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguides according to claim 48.

58. A method for producing a near-infrared optical waveguide as described in claim 57, wherein both the third curable polymer composition and the fourth curable polymer composition are organopolysiloxane-containing resin compositions for near-infrared optical waveguides as described in claim 48.

59. A method for producing a near-infrared optical waveguide, comprising the steps of: (iii-1) applying a fifth curable polymer composition to a surface of a substrate to form a fifth polymer layer; (iii-2) curing the fifth polymer layer to form a lower clad; (iii-3) applying a sixth curable polymer composition onto the lower clad to form a sixth polymer layer; (iii-4) irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; and (iii-5) removing the unexposed region of the partially exposed layer with a solvent to form a patterned core, in this order; wherein at least one of the fifth curable polymer composition and the sixth curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguide according to claim 48.

60. A method for producing a near-infrared optical waveguide as described in claim 59, wherein both the fifth curable polymer composition and the sixth curable polymer composition are organopolysiloxane-containing resin compositions for near-infrared optical waveguides as described in claim 48.

61. A method for manufacturing a semiconductor device comprising the steps of: applying a fifth curable polymer composition onto a substrate surface to form a fifth polymer layer; curing the fifth polymer layer to form a lower cladding; applying a sixth curable polymer composition onto the lower cladding to form a sixth polymer layer; irradiating at least one selected region of the sixth polymer layer with active energy rays having a wavelength of 150 to 800 nm to produce a partially exposed layer having at least one exposed region and at least one unexposed region; removing the unexposed region of the partially exposed layer with a solvent to form a patterned core; covering the lower cladding and the core with a seventh curable polymer composition to form a seventh polymer layer; and curing the seventh polymer layer to form an upper cladding.

49. A method for producing a near-infrared optical waveguide, wherein at least one of the fifth curable polymer composition, the sixth curable polymer composition, and the seventh curable polymer composition is the organopolysiloxane-containing resin composition for near-infrared optical waveguide according to claim 48.

62. A method for producing a near-infrared optical waveguide as described in claim 61, wherein all of the fifth curable polymer composition, the sixth curable polymer composition and the seventh curable polymer composition are organopolysiloxane-containing resin compositions for near-infrared optical waveguides as described in claim 48.

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