Metal-containing silyloxy compound, metal-containing silyloxy group-coated particles, method for producing the same, and dispersion composition

Abstract

To provide: a compound used as a capping agent which gives particles having excellent dispersibility and refractive indexes; particles surface-coated with the compound; a method for producing the same; and a dispersion composition containing the particles.SOLUTION: A compound according to the present invention has a structure represented by formula (1). In the formula, R1 represents an organic group having 1-30 carbon atoms, R2 represents a group represented by OR3 or a group represented by formula (2), R3 represents an organic group having 1-30 carbon atoms, n1 and n2 each represent an integer of 0 or more, n1+2×n2 represents a valence determined by the type of L, L represents aluminum, gallium, yttrium, titanium, zirconium, hafnium, bismuth, tin, vanadium, or tantalum, * represents a bond, R4 and R5 each represent an organic group having 1-30 carbon atoms, which may have an oxygen atom. Particles according to the present invention have a structure represented by formula (1) on the surface thereof.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a metal-containing silyloxy compound, metal-containing silyloxy group-coated particles, a method for producing the same, and a dispersion composition.

Background Art

[0002] For the formation of optical members, a high refractive index material is used. As the high refractive index material, for example, a composition in which metal oxide particles such as zirconium oxide are dispersed in an organic component is used. As a method for improving the dispersibility of metal oxide particles, a method of capping the surface of metal oxide particles with a capping agent is known. As the capping agent, for example, organosilanes such as n-propyltrimethoxysilane are known (see Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] In recent years, with the improvement in the performance required for optical members, the refractive index required for high refractive index materials has also been increasing.

[0005] The present invention has been made in view of such a conventional situation, and an object thereof is to provide a compound used as a capping agent that gives particles excellent in dispersibility and refractive index, particles whose surface is coated with the compound, a method for producing the same, and a dispersion composition containing the particles.

Means for Solving the Problems

[0006] The inventors of the present invention have conducted intensive research to solve the above problems. As a result, they have found that the above problems can be solved by a predetermined metal-containing silyloxy compound, and have completed the present invention. Specifically, the present invention provides the following.

[0007] The first aspect of the present invention is a compound having a structure represented by the following formula (1).

[0008] [Chemical formula] (In the formula, R 1 represents an organic group having 1 to 30 carbon atoms, R 2 represents a group represented by OR 3 or a group represented by the following formula (2), R 3 represents an organic group having 1 to 30 carbon atoms, n1 and n2 each independently represent an integer of 0 or more, provided that n1 + 2 × n2 is the valence determined by the type of L, L represents aluminum, gallium, yttrium, titanium, zirconium, hafnium, bismuth, tin, vanadium, or tantalum, * represents a bond.)

[0009] [Chemical formula] (In the formula, R 4 and R 5 represent an organic group having 1 to 30 carbon atoms which may have an oxygen atom.)

[0010] The second aspect of the present invention is a particle having a structure represented by the above formula (1) on its surface.

[0011] The third aspect of the present invention is a dispersion composition containing the above particles.

[0012] The fourth aspect of the present invention is a method for producing a particle having a structure represented by the above formula (1) on its surface, The manufacturing method is a particle coating step of reacting particles having a hydroxyl group on the surface with a compound represented by the following formula (30) to obtain particles having the structure represented by the above formula (1) on the surface or The manufacturing method is a first reaction step of reacting particles having a hydroxyl group on the surface with a compound represented by the following formula (4) to obtain particles having the structure represented by the following formula (5) on the surface, and a second reaction step of reacting the particles obtained in the first reaction step with a compound represented by the following formula (6) to obtain particles having the structure represented by the above formula (1) on the surface has Manufacturing method.

[0013] [Chemical formula] (In the formula, R 1 , R 2 , n1, n2, and L are as described above, and R 60 and R 70 represent an organic group having 1 to 30 carbon atoms.)

[0014] [Chemical formula] (In the formula, R 1 , R 60 , and R 70 are as described above, and R 8 represents an organic group having 1 to 30 carbon atoms.)

[0015] [Chemical formula] (In the formula, R 1 and R 8 are as described above.) R 9 O-L(R 2 ) n1 (O) n2 (6) (In the formula, R 2 , n1, n2, and L are as described above, and R 9represents an organic group having 1 to 30 carbon atoms. )

Advantages of the Invention

[0016] According to the present invention, it is possible to provide a compound used as a capping agent that gives particles excellent in dispersibility and refractive index, particles whose surfaces are coated with the compound, a method for producing the same, and a dispersion composition containing the particles.

Embodiments for Carrying Out the Invention

[0017] <Compound having a structure represented by formula (1)> The compound according to the present invention has a structure represented by the above formula (1). The above compound can be used as a capping agent that gives particles excellent in dispersibility and refractive index.

[0018] In the above formula (1), R 1 The organic group having 1 to 30 carbon atoms represented is not particularly limited, and examples thereof include an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an alkoxyalkyl group having 2 to 30 carbon atoms. Among them, from the viewpoint of the dispersibility of the obtained particles, etc., an alkyl group having 1 to 30 carbon atoms or an alkoxyalkyl group having 2 to 30 carbon atoms is preferable.

[0019] R 1 The alkyl group having 1 to 30 carbon atoms represented is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an n-octyl group, an n-decyl group, an n-dodecyl group, an n-octadecyl group, an n-icosyl group, etc. From the viewpoints of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an alkyl group having 6 to 24 carbon atoms is preferable, and an alkyl group having 8 to 20 carbon atoms is more preferable.

[0020] R 1The cycloalkyl group having 3 to 30 carbon atoms represented by is not particularly limited, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, a cyclododecyl group, a cyclooctadecyl group, a cycloeicosyl group, etc. In terms of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., a cycloalkyl group having 6 to 24 carbon atoms is preferable, and a cycloalkyl group having 8 to 20 carbon atoms is more preferable.

[0021] R 1 The alkenyl group having 2 to 30 carbon atoms represented by is not particularly limited, and examples thereof include a vinyl group, an allyl group, etc. In terms of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an alkenyl group having 6 to 24 carbon atoms is preferable, and an alkenyl group having 8 to 20 carbon atoms is more preferable.

[0022] R 1 The aryl group having 6 to 30 carbon atoms represented by is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, etc. In terms of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an aryl group having 8 to 24 carbon atoms is preferable, and an aryl group having 10 to 20 carbon atoms is more preferable.

[0023] R 1 The alkoxyalkyl group having 2 to 30 carbon atoms represented by is not particularly limited, and examples thereof include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group, etc. In terms of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an alkoxyalkyl group having 6 to 24 carbon atoms is preferable, and an alkoxyalkyl group having 8 to 20 carbon atoms is more preferable.

[0024] In the above formula (1), when n1 represents an integer of 2 or more, a plurality of R 2 may be the same as or different from each other.

[0025] In the above formula (1), R 2 is represented by, for example, OR 3 and R 3Examples of the group represented by R include an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms. In addition, an alkyl acetoacetate group having 5 to 30 carbon atoms, a 2,4-pentanedionato group (i.e., an acetylacetonato group), and a 2,2,6,6-tetramethyl-3,5-heptanedionato group are also included.

[0026] R 2 The alkyl acetoacetate group having 5 to 30 carbon atoms represented by R is not particularly limited, and examples thereof include a methyl acetoacetate group and an ethyl acetoacetate group. From the viewpoints of ease of synthesis and stability, an ethyl acetoacetate group is preferable.

[0027] R 2 From the viewpoint of the dispersibility of the obtained particles, etc., the group represented by the above formula (2) is preferable.

[0028] In the above formula (1), L is preferably yttrium, titanium, zirconium, or hafnium from the viewpoint of the refractive index of the obtained particles, etc., and titanium or zirconium is more preferable.

[0029] In the above formula (2), R 4 or R 5 The organic group having 1 to 30 carbon atoms represented by is not particularly limited, and examples thereof include an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an alkoxyalkyl group having 2 to 30 carbon atoms. From the viewpoint of the dispersibility of the obtained particles, etc., an alkyl group having 1 to 30 carbon atoms or an alkoxyalkyl group having 2 to 30 carbon atoms is preferable. R 4 or R 5When it has an oxygen atom, it is preferable that the oxygen atom is directly bonded to P in P(=O) in formula (2), that is, it is preferable that an organic group having 1 to 30 carbon atoms is bonded to the P through the oxygen atom, and the above-mentioned organic group is preferably an alkyl group having 1 to 30 carbon atoms or an alkoxyalkyl group having 2 to 30 carbon atoms. In formula (2), R 4 and R 5 may both have an oxygen atom directly bonded to P in P(=O), or only one of R 4 and R 5 may have the oxygen atom.

[0030] R 4 or R 5 The alkyl group having 1 to 30 carbon atoms represented by is not particularly limited. For example, the groups specifically exemplified for R 1 etc. can be mentioned. From the viewpoints of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an alkyl group having 4 to 18 carbon atoms is preferable, and an alkyl group having 6 to 12 carbon atoms is more preferable.

[0031] R 4 or R 5 The cycloalkyl group having 3 to 30 carbon atoms represented by is not particularly limited. For example, the groups specifically exemplified for R 1 etc. can be mentioned. From the viewpoints of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., a cycloalkyl group having 4 to 18 carbon atoms is preferable, and a cycloalkyl group having 6 to 12 carbon atoms is more preferable.

[0032] R 4 or R 5 The alkenyl group having 2 to 30 carbon atoms represented by is not particularly limited. For example, the groups specifically exemplified for R 1 etc. can be mentioned. From the viewpoints of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an alkenyl group having 4 to 18 carbon atoms is preferable, and an alkenyl group having 6 to 12 carbon atoms is more preferable.

[0033] R 4 or R 5The aryl group having 6 to 30 carbon atoms represented by is not particularly limited. For example, R 1 The groups specifically exemplified for etc. can be mentioned. From the viewpoints of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an aryl group having 6 to 18 carbon atoms is preferable, and an aryl group having 6 to 12 carbon atoms is more preferable.

[0034] R 4 Or R 5 The alkoxyalkyl group having 2 to 30 carbon atoms represented by is not particularly limited. For example, R 1 The groups specifically exemplified for etc. can be mentioned. From the viewpoints of the ease of synthesis of the above compound and the dispersibility of the obtained particles, etc., an alkoxyalkyl group having 4 to 18 carbon atoms is preferable, and an alkoxyalkyl group having 6 to 12 carbon atoms is more preferable.

[0035] The compound having the structure represented by the above formula (1) is preferably represented by the above formula (3) and more preferably represented by the above formula (30) from the viewpoints of the ease of synthesis and the reactivity as a capping agent, etc.

[0036] In the above formula (3), R 6 Or R 7 The organic group having 1 to 30 carbon atoms represented by is not particularly limited. For example, an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxyalkyl group having 2 to 30 carbon atoms can be mentioned. Each of the groups specifically exemplified for R 1 can be mentioned. Among them, an alkyl group having 1 to 30 carbon atoms is preferable.

[0037] R 6 Or R 7 The alkyl group having 1 to 30 carbon atoms represented by is not particularly limited. For example, R 1Specific examples of the base or the like are given, and in terms of reactivity as a capping agent, an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, or a tert-hexyl group is preferable.

[0038] In the above formula (30), R 60 or R 70 The organic group having 1 to 30 carbon atoms represented is the same as that described for the organic group having 1 to 30 carbon atoms represented by R 6 or R 7 in the above formula (3).

[0039] Examples of the compound represented by the above formula (3) include the following compounds. [Chemical formula] (In the formula, R 1 , R 2 , n1, n2, L, R 60 , and R 70 are as described above.)

[0040] Specific examples of the compound having the structure represented by the above formula (1) are as follows, but are not limited thereto. [Chemical formula] (In the formula, R represents an alkylene group having 1 to 3 carbon atoms, R' represents an alkyl group having 1 to 3 carbon atoms, and n represents a number of 0 or more, for example, a number of 0 or more and 10 or less, preferably a number of 0 or more and 5 or less.)

[0041] The compound having the structure represented by the above formula (1) can be produced using any organic synthesis reaction, and for example, it can be produced according to the following Scheme 1.

[0042] [Scheme 1] [Chemical formula] (In the formula, R 1 , R 2 , n1, n2, L, R 8 , R 9 , and * are as described above.)

[0043] In Scheme 1, a compound having the structure represented by the above formula (5) and a compound represented by the above formula (6) are subjected to hydrolysis condensation in water or a mixed solvent (referring to a mixture of water and an organic solvent; the same applies hereinafter) in the absence or presence of a catalyst to obtain a compound having the structure represented by the above formula (1).

[0044] The catalyst may be an acid catalyst or an alkali catalyst. Examples of the acid catalyst include inorganic acids, aliphatic sulfonic acids, aromatic sulfonic acids, aliphatic carboxylic acids, aromatic carboxylic acids, etc. Specifically, hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, perchloric acid, phosphoric acid, methanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, maleic acid, fumaric acid, benzoic acid, etc. may be mentioned. Examples of the alkali catalyst include methylamine, ethylamine, propylamine, butylamine, ethylenediamine, hexamethylenediamine, dimethylamine, diethylamine, ethylmethylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, cyclohexylamine, dicyclohexylamine, monoethanolamine, diethanolamine, dimethylmonoethanolamine, monomethyldiethanolamine, triethanolamine, diazabicyclooctane, diazabicyclononene, diazabicycloundecene, hexamethylenetetramine, aniline, N,N-dimethylaniline, pyridine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N-(β-aminoethyl)ethanolamine, N-methylethanolamine, N-methyldiethanolamine, N-ethylethanolamine, N-n-butylethanolamine, N-n-butyldiethanolamine, N-tert-butylethanolamine, N-tert-butyldiethanolamine, N,N-dimethylaminopyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, tetramethylammonium hydroxide, choline hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, ammonia, lithium hydroxide, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, etc.

[0045] The amount of the catalyst used is preferably 10 -6 mol to 10 mol, more preferably 10 -5 mol to 5 mol, still more preferably 10 -4 mol to 1 mol with respect to 1 mol of the compound represented by the above formula (6).

[0046] The amount of water used is preferably 0.01 to 100 moles, more preferably 0.05 to 50 moles, still more preferably 0.1 to 30 moles, and particularly preferably 0.5 to 5 moles per mole of the group represented by OR in the compound represented by the above formula (6). 9 The amount of water used is preferably 0.01 to 100 moles, more preferably 0.05 to 50 moles, still more preferably 0.1 to 30 moles, and particularly preferably 0.5 to 5 moles per mole of the group represented by OR in the compound represented by the above formula (6).

[0047] Examples of the organic solvent include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, acetone, acetonitrile, tetrahydrofuran, toluene, hexane, ethyl acetate, cyclohexanone, methyl amyl ketone, butanediol monomethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, butanediol monoethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monoethyl ether acetate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, tert-butyl acetate, t-butyl propionate, propylene glycol mono-t-butyl ether acetate, γ-butyrolactone, acetylacetone, methyl acetoacetate, ethyl acetoacetate, propyl acetoacetate, butyl acetoacetate, methyl pivaloyl acetate, methyl isobutyroyl acetate, methyl caproyl acetate, methyl lauroyl acetate, 1,2-ethanediol, 1,2-propanediol, 1,2-butanediol, 1,2-pentanediol, 2,3-butanediol, 2,3-pentanediol, glycerin, diethylene glycol, hexylene glycol and the like, and mixtures of two or more of these are preferred.

[0048] The amount of the organic solvent used is preferably 0 to 1,000 ml, and particularly preferably 0 to 500 ml, per mole of the compound represented by the above formula (6).

[0049] The reaction temperature is preferably 0 to 100 °C, more preferably 5 to 80 °C, and the reaction time is preferably 10 minutes to 3 hours, more preferably 20 minutes to 1 hour.

[0050] Among them, the compound represented by the above formula (3) can be produced, for example, according to the following Scheme 2.

[0051] [Scheme 2] [Chemical formula] (In the formula, R 1 , R 2 , n1, n2, L, R 6 , R 7 , R 60 , R 70 , R 8 , and R 9 are as described above.)

[0052] In Scheme 2, the compound represented by the above formula (4) and the compound represented by the above formula (6) are hydrolytically condensed in the same manner as in Scheme 1 to obtain the compound represented by the above formula (3).

[0053] In the above formula (5), the organic group having 1 to 30 carbon atoms represented by R 8 is the same as that described for the organic group having 1 to 30 carbon atoms represented by R 6 or R 7 in the above formula (3).

[0054] In the above formula (6), the organic group having 1 to 30 carbon atoms represented by R 9 is not particularly limited, and examples thereof include an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an alkoxyalkyl group having 2 to 30 carbon atoms. Specifically, the groups exemplified for R 1 can be mentioned. Among them, an alkyl group having 1 to 30 carbon atoms is preferred.

[0055] R 9The alkyl group having 1 to 30 carbon atoms represented by is not particularly limited. For example, groups specifically exemplified for R 6 or R 7 and the like can be mentioned. In terms of ease of synthesis and reactivity with the group represented by OR 8 , an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group is preferable.

[0056] <Particles having the structure represented by formula (1) on the surface> The particles according to the present invention have the structure represented by the above formula (1). Since the above particles are excellent in dispersibility and refractive index, they can be suitably used for high refractive index materials.

[0057] The particles having the structure represented by the above formula (1) on the surface have, for example, a form in which the structure represented by the above formula (1) is introduced on the surface of particles not having the structure represented by the above formula (1) on the surface. The particles not having the structure represented by the above formula (1) on the surface are not particularly limited, and examples thereof include particles having a hydroxyl group on the surface. The particles having a hydroxyl group on the surface are not particularly limited, and examples thereof include metal oxide particles such as titanium oxide particles, zirconium oxide particles, hafnium oxide; and other particles having a high refractive index such as Si particles.

[0058] The particle size of the particles according to the present invention is not particularly limited, and in terms of dispersibility and the like, it is preferably 1 to 20 nm, more preferably 2 to 15 nm, and even more preferably 4 to 10 nm. In this specification, the particle size of the particles refers to the particle size measured by observing the particles with TEM.

[0059] When measuring the average diameter of the particles in the dispersion composition according to the present invention, the average diameter can be measured by a dynamic light scattering (DLS) device such as Malvern Zetasizer Nano S. For example, when the particles according to the present invention are dispersed in a dispersion medium such as PGMEA at a concentration of 5% by mass or less, they have monodispersity and the range of the average diameter is 20 nm or less.

[0060] The dispersion composition according to the present invention has, for example, a combination of the particles according to the present invention and a known organic solvent or a known liquid monomer, etc., and in this combination, the dispersibility of the particles according to the present invention is maintained.

[0061] The structure represented by the above formula (1) binds to the particles through at least one of the bonds. The form of the bond between the structure represented by the above formula (1) and the particles is not particularly limited, and examples include the following forms (F1a) and (F1b). In the following form (F1a), the structure represented by the above formula (1) binds to the particles through both of the bonds. On the other hand, in the following form (F1b), the structure represented by the above formula (1) binds to the particles through one of the bonds.

[0062] [Chemical formula] (In the formula, R 1 , R 2 , n1, n2, L are as described above, and p represents a particle.)

[0063] [Method for producing particles having the structure represented by formula (1) on the surface] The particles having the structure represented by formula (1) on the surface can be produced, for example, by a production method having a particle coating step (hereinafter, also referred to as "production method 1") as described above, or a production method having a first reaction step and a second reaction step (hereinafter, also referred to as "production method 2").

[0064] The particle coating step, the first reaction step, and the second reaction step can be carried out, for example, in water or a mixed solvent, in the absence or presence of a catalyst. Examples of the catalyst, examples of the organic solvent, the reaction temperature, and the reaction time are the same as those described in Scheme 1.

[0065] Production method 1 can be carried out, for example, according to the following Scheme 3 or 4.

[0066] [Scheme 3] [Chemical formula] (In the formula, R 1 , R 2 , n1, n2, L, R 6 , R 7 , and p are as described above.)

[0067] In Scheme 3, particles having a hydroxyl group on the surface and the compound represented by the above formula (3) are subjected to hydrolysis and condensation in water or a mixed solvent, in the absence or presence of a catalyst, to obtain particles having the structure represented by the above formula (1) on the surface in the above form (F1a). Examples of the catalyst, examples of the organic solvent, the reaction temperature, and the reaction time are the same as those described in Scheme 1.

[0068] The amount of the catalyst used is preferably 10 -6 mol to 10 mol, more preferably 10 -5 mol to 5 mol, still more preferably 10 -4 mol to 1 mol, per 1 mol of the compound represented by the above formula (3).

[0069] The amount of water used is preferably 0.01 to 100 mol, more preferably 0.05 to 50 mol, still more preferably 0.1 to 30 mol, and particularly preferably 1 to 5 mol, per 1 mol of the total of the groups represented by OR 6 and OR 7 in the compound represented by the above formula (3).

[0070] The amount of the organic solvent used is preferably 0 to 1,000 ml, particularly preferably 0 to 500 ml, per 1 mol of the compound represented by the above formula (3).

[0071] [Scheme 4]

Chemical formula

[0072] In Scheme 4, the particles having a hydroxyl group on the surface and the compound represented by the above formula (3) are subjected to hydrolysis condensation in water or a mixed solvent in the absence or presence of a catalyst to obtain particles having the structure represented by the above formula (1) on the surface in the above form (F1b). Examples of the catalyst, the amount of the catalyst used, examples of the organic solvent, the amount of the organic solvent used, the reaction temperature, and the reaction time are the same as those described in Scheme 3.

[0073] 6 In Scheme 4, R 2 is preferably a group represented by L(R n1 )(O) n2 .

[0074] The amount of water used is preferably 0.01 to 100 moles, more preferably 0.05 to 50 moles, and still more preferably 0.1 to 30 moles, per mole of the group represented by OR 7 in the compound represented by the above formula (3).

[0075] Production method 2 can be carried out, for example, according to the following Scheme 5.

[0076] [Scheme 5]

Chemical formula

[0077] In Scheme 5, particles having a hydroxyl group on the surface and the compound represented by the above formula (4) are subjected to hydrolysis condensation in water or a mixed solvent in the absence or presence of a catalyst to obtain particles having the structure represented by the above formula (5) on the surface in the above form (F5a) (first reaction step), and the particles and the compound represented by the above formula (6) are subjected to hydrolysis condensation in water or a mixed solvent in the absence or presence of a catalyst to obtain particles having the structure represented by the above formula (1) on the surface in the above form (F1a) (second reaction step). Examples of the catalyst and examples of the organic solvent are the same as those described in Scheme 1.

[0078] The amount of the catalyst used is preferably 10 -6 mol to 10 mol, more preferably 10 -5 mol to 5 mol, still more preferably 10 -4 mol to 1 mol, per 1 mol of the compound represented by the above formula (4) in the case of the first reaction step, or per 1 mol of the compound represented by the above formula (6) in the case of the second reaction step.

[0079] The amount of water used is preferably 0.01 to 100 mol, more preferably 0.05 to 50 mol, still more preferably 0.1 to 30 mol, and particularly preferably 1 to 5 mol, per 1 mol of the total of the groups represented by OR 60 and OR 70 in the compound represented by the above formula (4) in the case of the first reaction step, or per 1 mol of the group represented by OR 9 in the compound represented by the above formula (6) in the case of the second reaction step.

[0080] The amount of the organic solvent used is preferably 0 to 1,000 ml, particularly preferably 0 to 500 ml, per 1 mol of the compound represented by the above formula (4) in the case of the first reaction step, or per 1 mol of the compound represented by the above formula (6) in the case of the second reaction step.

[0081] In each of the first reaction step and the second reaction step, the reaction temperature is preferably 0 to 100 °C, more preferably 5 to 80 °C, and the reaction time is preferably 10 minutes to 3 hours, more preferably 20 minutes to 1 hour.

Examples

[0082] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

[0083] [Preparation of the compound having the structure represented by formula (1)] The compound represented by the following 4-A (hereinafter also referred to as "compound 4-A") and the compound represented by the following 6-A (hereinafter also referred to as "compound 6-A") were subjected to hydrolysis condensation at room temperature for 60 minutes. The molar ratio of compound 4-A to compound 6-A was 1:1. When the reaction mixture after hydrolysis condensation was subjected to gel permeation chromatography (GPC), a new peak that was not observed when compound 4-A or compound 6-A was placed alone under the above conditions and then subjected to GPC appeared. When the number average molecular weight in terms of polystyrene was calculated for this new peak, it was 1300. From the above results and 1 the results of 1H-NMR measurement, it was confirmed that the compound represented by the following 3-A was obtained as the product corresponding to the above new peak. The above new peak has a shoulder, and it was also confirmed that the compound represented by the following 3-B was generated from the number average molecular weight in terms of polystyrene calculated based on the shoulder. Further, when the product was 13 subjected to 13C-NMR measurement, peaks corresponding to (CH 3 O) 1 , (CH 3 O) 2 , or SiCH 2 were confirmed in the region of 5 to 7 ppm where no peak appeared when the raw material was subjected to the same measurement.

[0084]

Chemical formula

[0085] [Preparation and Evaluation of Coated Particles] [Preparation of Titanium Oxide Particles] Referring to Example 8 of International Publication No. 2020 / 106860, titanium oxide particles were recovered. When the titanium oxide particles were observed by TEM, the shape was spherical and the particle size was 7 nm. In Table 1, the above titanium oxide particles are denoted as "TiO 2 ".

[0086] [Preparation of Coated Particles] In a 20 cc vial, the above titanium oxide particles and Compound 4-A were mixed at the ratios shown in Table 1, and then stirred at 110 °C for 30 minutes. Then, Compound 6-A was further added to the vial and stirred at 110 °C for 20 minutes to obtain coated particles. In Comparative Example 1, gelation occurred at this stage and subsequent evaluation could not be performed. Also, the above reaction was carried out in PGMEA. Also, the washing conditions of the coated particles were classified as follows. 1. n-Heptane was added to the reaction system containing PGMEA to precipitate the coated particles, followed by centrifugation. (Shown as 1 in the row of washing conditions in Table 1.) 2. Next, after collecting the centrifuged coated particles, they were dispersed in tetrahydrofuran (THF), heptane was added to precipitate the coated particles, and then centrifuged. (Shown as 2 in the row of washing conditions in Table 1.) 3. Again, after collecting the centrifuged coated particles, they were dispersed in tetrahydrofuran (THF), heptane was added to precipitate the coated particles, and then centrifuged. (Shown as 3 in the row of washing conditions in Table 1.)

[0087] [Evaluation of Coated Particles] ·Dispersibility Regarding the filtered coated particles, attempts were made to wash with washing liquid: n-heptane, dry at 25 °C after filtration, redisperse in dispersion medium: PGMEA, and filter. The dispersibility of the coated particles was evaluated according to the following criteria. The results are shown in Table 1. +(Good): All of washing, drying, redispersion, and filtration were possible. -(Defective): The coated particles were gelled, making at least one of washing, drying, redispersion, and filtration impossible, and subsequent measurements could not be performed.

[0088] ·XPS For the prepared coated particles, X-ray photoelectron spectroscopy (XPS analysis) was performed to calculate the molar ratio of phosphorus to silicon contained in the coated particles, and further, based on this, the molar ratio of the portion derived from Compound 6-A to the portion derived from Compound 4-A in the coated particles was calculated. The results are shown in Table 1.

[0089] ·Coating rate The filtered coated particles were redispersed in a dispersion medium: PGMEA to prepare a 50% by mass dispersion. For this dispersion, thermogravimetric analysis (TGA) was performed to calculate the total ratio of the portion derived from Compound 6-A and the portion derived from Compound 4-A in the solid content of the dispersion, and this was taken as the coating rate (mass%) of the coated particles. The results are shown in Table 1.

[0090] ·Refractive index In the portion of the coated particles where the titanium oxide particles are coated (i.e., the total of the portion derived from Compound 6-A and the portion derived from Compound 4-A), the higher the titanium content, the more easily the refractive index of the coated particles is improved. Since titanium is contained in the portion derived from Compound 6-A, it can be reasonably understood that the higher the amount of the portion derived from Compound 6-A, the more easily the refractive index of the coated particles is improved. Therefore, the refractive index of the coated particles was evaluated according to the following criteria using the molar ratio of the portion derived from Compound 6-A to the portion derived from Compound 4-A by XPS (hereinafter also referred to as "Compound 6-A / Compound 4-A"). The results are shown in Table 1. ++(Extremely good): Compound 6-A / Compound 4-A was 0.5 or more. +(Good): Compound 6-A / Compound 4-A was more than 0 and less than 0.5. -(Defective): Compound 6-A / Compound 4-A was 0. Or, the dispersibility of the coated particles was poor.

[0091] ·Particle size in the dispersion composition The coated particles of each of Examples 1 to 5 were dispersed in a dispersion medium such as PGMEA at a concentration of 5% by mass or less to obtain a dispersion composition, and the average diameter of the coated particles in the dispersion composition was measured using a Malvern Zetasizer Nano S (dynamic light scattering (DLS) apparatus). As a result, the average diameter was 20 nm or less for any of Examples 1 to 5.

[0092]

Table 1

[0093] As can be seen from Table 1, it was confirmed that the particles obtained in the examples were excellent in dispersibility and refractive index, while the particles obtained in the comparative examples were inferior in dispersibility or refractive index.

Claims

**Claim 1** A compound represented by the following formula (3). 【Chemical 1】 (In the formula, R1 represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms, R2 represents a group represented by OR3 or a group represented by the following formula (2), R3 represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxyalkyl group having 2 to 30 carbon atoms, an alkyl acetoacetate group having 5 to 30 carbon atoms, a 2,4-pentanedionato group, or a 2,2,6,6-tetramethyl-3,5-heptanedionato group, n1 and n2 each independently represent an integer of 0 or more, provided that n1 + 2×n2 is the valence determined by the type of L, L represents aluminum, gallium, yttrium, titanium, zirconium, hafnium, bismuth, tin, vanadium, or tantalum, R ６ and R ７ each independently represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxyalkyl group having 2 to 30 carbon atoms, or L(R ２ ), ｎ１ (O) ｎ２ a group represented by.). [Chemical 2] (In the formula, R4 and R5 represent an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms, which may have an oxygen atom.) **Claim 2** The compound according to claim 1, wherein the compound is represented by the following formula (30). 【Chemical Formula 3】 (wherein, R １ , R ２ , n1, n2, and L are as described above, and R ６０ and R ７０ each represent an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms.) **Claim 3** Particles having a structure represented by the following formula (1) on the surface. 【Chemical Formula 4】 (In the formula, R １ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms, R ２ represents a group represented by OR ３ or a group represented by the following formula (2). R ３ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxyalkyl group having 2 to 30 carbon atoms, an alkyl acetoacetate group having 5 to 30 carbon atoms, a 2,4-pentanedionato group, or a 2,2,6,6-tetramethyl-3,5-heptanedionato group, n1 and n2 each independently represent an integer of 0 or more, provided that n1 + 2×n2 is the valence determined by the type of L, L represents aluminum, gallium, yttrium, titanium, zirconium, hafnium, bismuth, tin, vanadium, or tantalum, * represents a bond.) 【Chemical Formula 5】 (wherein, R ４ and R ５ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms, which may have an oxygen atom.) **Claim 4** A dispersion composition containing the particles according to claim 3. **Claim 5** A method for producing particles having a structure represented by the following formula (1) on the surface, wherein the production method has a particle coating step of reacting particles having a hydroxyl group on the surface with a compound represented by the following formula (30) to obtain particles having a structure represented by the following formula (1) on the surface or, the production method has a first reaction step of reacting particles having a hydroxyl group on the surface with a compound represented by the following formula (4) to obtain particles having a structure represented by the following formula (5) on the surface, A second reaction step of reacting the particles obtained in the first reaction step with a compound represented by the following formula (6) to obtain particles having a structure represented by the following formula (1) on the surface, having manufacturing method. 【Chemical Formula 6】 (In the formula, R １ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms, R ２ represents a group represented by OR ３ or a group represented by the following formula (2), R ３ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxyalkyl group having 2 to 30 carbon atoms, an alkyl acetoacetate group having 5 to 30 carbon atoms, a 2,4-pentanedionato group, or a 2,2,6,6-tetramethyl-3,5-heptanedionato group, n1 and n2 each independently represent an integer of 0 or more, provided that n1 + 2×n2 is a valence determined by the type of L, L represents aluminum, gallium, yttrium, titanium, zirconium, hafnium, bismuth, tin, vanadium, or tantalum, * represents a bond.) 【Chemical Formula 7】 (In the formula, R ４ and R ５ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms, which may have an oxygen atom.) [Chemical Formula 8] (wherein R １ , R ２ , n1, n2, and L are as defined above, and R ６０ and R ７０ represent an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms.) 【Chemical Formula 9】 (wherein, R １ , R ６０ , and R ７０ are as described above, and R ８ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms.) 【Chemical Formula 10】 (wherein, R １ and R ８ are as described above.) R ９ O - L(R ２ ) ｎ１ (O) ｎ２ (6) (wherein, R ２ , n1, n2, and L are as defined above, and R ９ represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an alkoxyalkyl group having 2 to 30 carbon atoms.)

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