Polymer, method for producing polymer, and non-photosensitive liquid composition

Abstract

To provide a polymer capable of yielding a molded body with high refractive index and superior heat resistance, a production method of the polymer, a non-photosensitive liquid composition comprising the polymer, a method for producing a molded body using the non-photosensitive liquid composition, a molded body of the non-photosensitive liquid composition, an optical component composed of the molded body, and an optical element provided with the optical component.SOLUTION: The problem is solved by introducing a terminal group of a specific structure into a molecular chain of a polymer that comprises a constitutional unit including a structure in which an aromatic group, having a hydroxyl group protected by a tert-butoxycarbonyl oxy group, a tert-butoxycarbonyl amino group, or an acetal protecting group, or having a carboxyl group protected by an acid-dissociable group, is bonded to a triazine ring via a specific linking group, and further comprises a structure in which an aromatic group is bonded to the triazine ring via a specific linking group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polymer containing a structural unit of a specific structure, a method for producing the polymer, a non-photosensitive liquid composition containing the polymer, a method for producing a molded article using the non-photosensitive liquid composition, a molded article from the non-photosensitive liquid composition, an optical component made of the molded article, and an optical element including the optical component. [Background technology]

[0002] Conventionally, solid-state imaging devices have been used in cameras, video cameras, etc. These solid-state imaging devices include CCD (charge-coupled device) image sensors and CMOS (complementary metal-oxide semiconductor) image sensors. The image sensors are equipped with minute focusing lenses (hereinafter referred to as microlenses) to improve the light collection efficiency.

[0003] In recent years, CCD image sensors and CMOS image sensors have become increasingly finer. This has led to the miniaturization of microlenses. Even with a small microlens diameter, the microlens material must have a high refractive index in order to efficiently focus light onto the photodiodes in the image sensor. For example, a known highly refractive material that can be molded into various shapes is a curable composition containing a photopolymerizable monomer (A) with a specific structure, metal oxide nanoparticles (B), and a photopolymerization initiator (C) (see Patent Document 1). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2022-190405 Summary of the Invention [Problem to be solved by the invention]

[0005] By using the curable composition described in Patent Document 1, microlenses with a high refractive index can be formed. However, in order to cope with further reduction in the diameter of microlenses, there is a demand for compositions capable of forming materials with even higher refractive indices. In addition, high refractive index materials are also required to have excellent heat resistance, i.e., transparency is not reduced even when exposed to high temperatures for a long period of time.

[0006] The present invention has been made in view of the above circumstances, and aims to provide a polymer that gives a molded article having a high refractive index and excellent heat resistance, a method for producing the polymer, a non-photosensitive liquid composition containing the polymer, a method for producing a molded article using the non-photosensitive liquid composition, a molded article from the non-photosensitive liquid composition, an optical component made of the molded article, and an optical element equipped with the optical component. [Means for solving the problem]

[0007] The present inventors have found that the above-mentioned problems can be solved by bonding an end group of a specific structure to a polymer containing a structural unit having a structure in which an aromatic group having a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group, is bonded to a triazine ring via a specific linking group, and have arrived at the present invention. Specifically, the present invention provides the following.

[0008] The first aspect of the present invention is a compound represented by the following formula (A1): [ka] (In formula (A1), Ar 1 , and Ar 2 is an aromatic group-containing group, R a1 represents a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group, The acetal protecting group is -CHR A1 -ORA2 is a group represented by R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, R A1 , and R A2 may be bonded to each other to form a ring, X 1 , and X 2 are each independently -NR a2 -, -O-, or -S-; R a2 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 Ar 1 and the aromatic ring in the aromatic group-containing group is X 2 Ar 2 It bonds to an aromatic ring in the aromatic group-containing group. Contains a constitutional unit represented by At least a part of the ends of the molecular chain contains a compound represented by the following formula (A1-1): -X 2 -X 3 -X 4 ···(A1-1) (In formula (A1-1), X 2 is X in formula (A1) 2 is the same as X 3 is a divalent hydrocarbon group, X 4 -OR a3 , or -N(R a3 )2, R a3 represents a hydrogen atom or an alkyl group which may have a substituent, X 3 When the hydrocarbon group as X is an aromatic group-containing group, 4 is not an amino group.) It is a polymer having a group represented by the formula:

[0009] A second aspect of the present invention is a compound comprising a dihalotriazine compound and a compound represented by the following formulae (A5-1) to (A5-3): Ar 2 -(NR a2 H)2···(A5-1) Ar 2 -(OH)2···(A5-2) Ar 2 -(SH)2···(A5-3) (In formulas (A5-1) to (A5-3), Ar 2 is an aromatic group-containing group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. with a compound represented by any one of The dihalotriazine compound is represented by the following formula (A3): [ka] (In formula (A3), Hal is a halogen atom, Ar 1 is an aromatic group-containing group, R a1 represents a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group, The acetal protecting group is -CHR A1 -OR A2 is a group represented by R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, R A1 , and R A2 may be bonded to each other to form a ring, X 1 are each independently -NR a2 -, -O-, or -S-; R a2 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X1 Ar 1 It bonds to an aromatic ring in the aromatic group-containing group. The compound includes a compound represented by Condensation of a dihalotriazine compound with a compound represented by any one of formulas (A5-1) to (A5-3) is carried out using the following formulas (A7-1) to (A7-3): X 4 -X 3 -NR a2 H···(A7-1) X 4 -X 3 -OH···(A7-2) X 4 -X 3 -SH···(A7-3) (In formulas (A7-1) to (A7-3), X 3 , and X 4 is X in formula (A1-1) 3 , and X 4 is the same as R a2 is R in Equation (1). a2 is the same as or in the presence of a compound represented by A method for producing a polymer according to the first aspect, comprising reacting a condensation product of a dihalotriazine compound and a compound represented by any one of formulas (A5-1) to (A5-3) with a compound represented by any one of formulas (A7-1) to (A7-3).

[0010] A third aspect of the present invention is a method for producing a composition comprising a triazine ring-containing polymer (A) and an organic solvent (S), the triazine ring-containing polymer (A) is the polymer according to the first aspect, R a1 is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid-dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0011] A fourth aspect of the present invention is a method for producing a non-photosensitive liquid composition according to the third aspect, comprising: and removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0012] A fifth aspect of the present invention is a molded article of the non-photosensitive liquid composition according to the fourth aspect.

[0013] A sixth aspect of the present invention is an optical component made of the molded article according to the fifth aspect.

[0014] A seventh aspect of the present invention is an optical element comprising the optical component according to the sixth aspect. [Effects of the Invention]

[0015] According to the present invention, it is possible to provide a polymer that gives a molded article having a high refractive index and excellent heat resistance, a method for producing the polymer, a non-photosensitive liquid composition containing the polymer, a method for producing a molded article using the non-photosensitive liquid composition, a molded article from the non-photosensitive liquid composition, an optical component made of the molded article, and an optical element equipped with the optical component. DETAILED DESCRIPTION OF THE INVENTION

[0016] Polymer The polymer contains a structural unit represented by the following formula (A1): The polymer may contain a structural unit other than the structural unit represented by the following formula (A1): The other structural unit is preferably a structural unit represented by the following formula (2): The polymer contains a group represented by the following formula (A1-1): -X 2 -X 3 -X 4 ···(A1-1) (In formula (A1-1), X 2 is X in formula (A1) 2 is the same as X 3 is a divalent hydrocarbon group, X 4 -OR a3 , or -N(R a3 )2, R a3 represents a hydrogen atom or an alkyl group which may have a substituent, X 3 When the hydrocarbon group as X is an aromatic group-containing group, 4 is not an amino group.) The compound has a group represented by the formula: The above polymers exhibit a high refractive index and are resistant to a decrease in light transmittance even when exposed to high temperatures for a long period of time. Hereinafter, the structural unit represented by formula (A1) will also be referred to as "unit (A1)." The structural unit represented by formula (A2) will also be referred to as "unit (A2)."

[0017] [ka]

[0018] In formula (A1), Ar 1 , and Ar 2 is an aromatic group-containing group. a1 is a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group. An acetal protecting group is -CHR A1 -OR A2 R A1 is a hydrogen atom or an alkyl group. A2 is an alkyl group. A1 , and R A2 may be bonded to each other to form a ring. 1 , and X 2 are each independently -NR a2 -, -O-, or -S-. a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. 1 Ar 1 The aromatic group is bonded to the aromatic ring in the aromatic group-containing group. X 2 Ar 2 The aromatic group bonded to the aromatic ring in the aromatic group-containing group.

[0019] [ka]

[0020] In formula (A2), Ar 2 , and Ar 3 is an aromatic group-containing group. 1 , and X 2 are each independently -NR a2 -, -O-, or -S-. a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. 1 Ar 3 The aromatic group is bonded to the aromatic ring in the aromatic group-containing group. X 2 Ar 2 The aromatic group bonded to the aromatic ring in the aromatic group-containing group.

[0021] The polymer containing the unit (A1) has a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group. Such polymers are soluble in various organic solvents, such as nitrogen-containing polar organic solvents and ketone-based solvents. However, when a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group is deprotected, or when a carboxyl group protected by an acid-labile group is deprotected, the polymer becomes poorly soluble in organic solvents. The deprotected polymer having a hydroxyl group, an amino group, or a carboxyl group becomes even more poorly soluble in organic solvents when crosslinked with a polymerizable monomer capable of reacting with the hydroxyl group, the amino group, or the carboxyl group. Examples of the polymerizable monomer include the crosslinkable compound (B) described below.

[0022] Therefore, the above polymers are easily processed as solutions.On the other hand, molded articles produced using the above polymer solutions under conditions in which hydroxyl groups protected by tert-butoxycarbonyloxy groups, tert-butoxycarbonylamino groups, or acetal protecting groups, or carboxyl groups protected by acid-labile groups, are deprotected, are poorly soluble in organic solvents.

[0023] The mass ratio of the units (A1) to the mass of the polymer is not particularly limited as long as the desired effect is not impaired. The mass ratio of the units (A1) to the mass of the polymer may be 10 mass% or more, 20 mass% or more, 30 mass% or more, 50 mass% or more, 70 mass% or more, 80 mass% or more, 90 mass% or more, or 100 mass%.

[0024] When the polymer contains the units (A1) and the units (A2), the ratio of the number of moles of the units (A1) to the total number of moles of the units (A1) and the number of moles of the units (A2) is preferably from 10 mol % to 70 mol %, more preferably from 20 mol % to 70 mol %, and particularly preferably from 30 mol % to 60 mol %.

[0025] <Unit (A1)> In formula (A1), Ar 1 , and Ar 2 is an aromatic group-containing group. The aromatic group-containing group may be a group consisting of only aromatic groups, or may contain non-aromatic groups in addition to aromatic groups. The aromatic group-containing group may contain only one aromatic group, or may contain two or more aromatic groups. The aromatic group contained in the aromatic group-containing group may be an aromatic hydrocarbon group or an aromatic heterocyclic group. The aromatic group contained in the aromatic group-containing group is preferably an aromatic hydrocarbon group.

[0026] The aromatic group contained in the aromatic group-containing group may be a monocyclic group or a polycyclic group. The polycyclic group may be a fused cyclic group, or a group in which one or more rings selected from monocyclic groups and polycyclic groups are connected by a single bond. The fused cyclic group may be a group in which an aromatic group is fused, or a group in which an aromatic group is fused with an aliphatic cyclic group.

[0027] The number of aromatic monocycles contained in the aromatic group-containing group is not particularly limited as long as the desired effect is not impaired.In addition, when the aromatic group-containing group is an aromatic condensed ring group, the number of monocycles constituting the aromatic condensed ring is the number of aromatic monocycles contained in the aromatic group-containing group.Specifically, when the aromatic group-containing group is a naphthalenediyl group, the number of aromatic monocycles contained in the aromatic group-containing group is 2. The number of aromatic monocycles contained in the aromatic group-containing group is preferably 1 or more and 4 or less, more preferably 1 or more and 3 or less, and even more preferably 1 or 2.

[0028] Suitable examples of the aromatic group-containing group include groups represented by the following formulae (a-1) to (a-11). [ka]

[0029] In formulas (a-1) to (a-11), R a01 are each independently a group selected from the group consisting of a halogen atom, a sulfonic acid group, an alkyl group having from 1 to 10 carbon atoms, and an alkoxy group having from 1 to 10 carbon atoms. R a02 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms. W a1 , and W a2 are each independently a single bond, -CR a03 R a04 a carbonyl group, -O-, -S-, -SO-, -SO2-, or -NR a05 - is a group represented by the formula: R a03 , and R a04 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. a03 R a04 In the group represented by -, R a03 , and R a04 may be bonded to each other to form a ring. R a05 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. X a1 , and X a2 are each independently a single bond, an alkylene group having 1 to 10 carbon atoms, or -Y a1 -Ph-Y a2 - is a group represented by the formula: Ph is a phenylene group which may have 1 to 4 substituents. The substituents which the phenylene group may have are groups selected from the group consisting of halogen atoms, sulfonic acid groups, alkyl groups having 1 to 10 carbon atoms, and alkoxy groups having 1 to 10 carbon atoms. Y a1 , and Y a2 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms. n1 is an integer between 0 and 4 inclusive. n2 and n3 each independently represent an integer of 0 or more and 3 or less. n4 is an integer between 0 and 2 inclusive. n5 is an integer between 0 and 3 inclusive. n6 and n7 each independently represent an integer of 0 or more and 3 or less. n8 is an integer between 0 and 3 inclusive. n9 is an integer between 0 and 5 inclusive. n10 and n11 each independently represent an integer of 0 or more and 3 or less. n12 is an integer between 0 and 3 inclusive. n13 is an integer between 0 and 4 inclusive. n14, n15, and n16 each independently represent an integer of 0 or more and 4 or less. n17 is an integer between 0 and 3 inclusive. n18 is an integer between 0 and 4 inclusive. n19 is an integer between 0 and 5 inclusive. n20 and n21 are integers of 0 or more and 4 or less. n22 and n23 are integers of 0 or more and 4 or less.

[0030] R a01 Examples of the halogen atom as the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, and a bromine atom are preferred.

[0031] R a01 The alkyl group having 1 to 10 carbon atoms as R may be linear or branched. a01 Specific examples of the alkyl group having 1 to 10 carbon atoms as the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, a 2-ethyl-n-hexyl group, an n-nonyl group, and an n-decyl group.

[0032] R a01 The alkoxy group having 1 to 10 carbon atoms as R may be linear or branched. a01 Specific examples of the alkoxy group having 1 to 10 carbon atoms as the alkoxy group include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an isopentyloxy group, a tert-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, a 2-ethyl-n-hexyloxy group, an n-nonyloxy group, and an n-decyloxy group.

[0033] R a02 The alkyl group having 1 to 10 carbon atoms as R a01 The alkyl group has 1 to 10 carbon atoms.

[0034] R a02 Specific examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms as the aryl group include a phenyl group, a naphthalene-1-yl group, a naphthalene-2-yl group, a 4-phenylphenyl group, a 3-phenylphenyl group, and a 2-phenylphenyl group.

[0035] Specific examples of the aralkyl group having from 7 to 13 carbon atoms include a benzyl group, a phenethyl group, a 3-phenyl-n-propyl group, a naphthalen-1-ylmethyl group, and a naphthalen-2-ylmethyl group.

[0036] W a1 , and W a2 are each independently a single bond, -CR a03 R a04 a carbonyl group, -O-, -S-, -SO-, -SO2-, or -NR a05 - is a group represented by the formula: W a1 , and W a2 But, -CR a03 R a04 -, R a03 , and R a04 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. R a03 , and R a04 The alkyl group having 1 to 10 carbon atoms as R a01 The alkyl group has 1 to 10 carbon atoms. R a03 , and R a04 may be bonded to each other to form a ring. W a1 , and W a2 But, -NR a05 -, R a05 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. R a05 The alkyl group having 1 to 10 carbon atoms as R a01The alkyl group has 1 to 10 carbon atoms.

[0037] X a1 , and X a2 are each independently a single bond, an alkylene group having 1 to 10 carbon atoms, or -Y a1 -Ph-Y a2 - is a group represented by the formula: X a1 , and X a2 Specific examples of the alkylene group having 1 to 10 carbon atoms as the alkylene group include a methylene group, an ethane-1,2-diyl group (ethylene group), an ethane-1,1-diyl group, a propane-1,3-diyl group, a propane-1,2-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, and a decan-1,10-yl group. X a1 , and X a2 Ga-Y a1 -Ph-Y a2 When Ph is a group represented by -, Ph is a phenylene group which may have 1 to 4 substituents. The substituent which the phenylene group may have is a group selected from the group consisting of a halogen atom, a sulfonic acid group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms. The alkyl group having 1 to 10 carbon atoms and the alkoxy group having 1 to 10 carbon atoms as the substituent that the phenylene group may have are R a01 The same applies to the alkyl group having 1 to 10 carbon atoms and the alkoxy group having 1 to 10 carbon atoms as mentioned above. Y a1 , and Y a2 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms. Y a1 , and Y a2 The alkylene group having 1 to 10 carbon atoms as X a1 , and X a2The alkylene group having 1 to 10 carbon atoms is the same as the alkylene group having 1 to 10 carbon atoms.

[0038] Specific examples of the groups represented by formulae (a-1) to (a-11) include the following groups. [ka]

[0039] [ka]

[0040] Among the above groups, the following groups are preferred: [ka]

[0041] In formula (A1), R a1 is a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group. A tert-butoxycarbonyloxy group and a tert-butoxycarbonylamino group can be deprotected by heating alone. On the other hand, deprotection by heating alone of a hydroxyl group protected by an acetal protecting group and a carboxy group protected by an acid-dissociable group is difficult. To deprotect a hydroxyl group protected by an acetal protecting group and a carboxy group protected by an acid-dissociable group by heating, it is advantageous to heat the protected hydroxyl group or the protected carboxy group in the presence of a thermal acid generator (C) described below. In this case, the action of the acid generated by the thermal acid generator (C) by heating easily deprotects the hydroxyl group protected by an acetal protecting group and the carboxy group protected by an acid-dissociable group. As mentioned above, R a1As the alkyl group, a tert-butoxycarbonyloxy group and a tert-butoxycarbonylamino group are preferred, and a tert-butoxycarbonylamino group is more preferred.

[0042] The acetal protecting group is -CHR A1 -OR A2 It is a group represented by the following formula: R A1 is a hydrogen atom or an alkyl group. A2 is an alkyl group. A1 , and R A2 may be bonded to each other to form a ring. R A1 , and R A2 The number of carbon atoms in the alkyl group represented by R is preferably 1 or more and 6 or less, and more preferably 1 or more and 4 or less. A1 , and R A2 The alkyl group as may be linear or branched, and is preferably linear. R A1 , and R A2 Specific preferred examples of the alkyl group as include a methyl group, an ethyl group, an n-propyl group, and an n-butyl group.

[0043] -CHR A1 -OR A2 Specific examples of the group represented by the formula (I) include a methoxymethyl group, an ethoxymethyl group, an n-propyloxymethyl group, an n-butyloxymethyl group, a 1-methoxyethyl group, a 1-ethoxymethyl group, a 1-n-propyloxyethyl group, a 1-n-butyloxyethyl group, a tetrahydropyran-2-yl group, and a tetrahydrofuran-2-yl group.

[0044] The acid-dissociable group is not particularly limited as long as it is a group that is well known in the technical fields of organic synthesis, photoresist, etc. and can protect a carboxy group. Suitable examples of the acid-dissociable group include an acetal protecting group and a tertiary carbon atom-containing group.

[0045] The acetal protecting group is the aforementioned -CHR A1 -ORA2 A group represented by the following formula is preferred. Tertiary carbon atom-containing groups include -C(R A3 )(R A4 )(R A5 ) is preferred. R A3 , R A4 , and R A5 are each independently an alkyl group having 1 to 6 carbon atoms, a fluorinated alkyl group having 1 to 6 carbon atoms, or an aliphatic cyclic group having 5 to 20 carbon atoms. R A3 , R A4 , and R A5 Specific examples of the alkyl group as include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, and an n-hexyl group. R A3 , R A4 , and R A5 The fluorinated alkyl group as defined above is a group in which some or all of the hydrogen atoms of the alkyl group have been substituted with fluorine atoms. R A3 , R A4 , and R A5 Specific examples of the aliphatic cyclic group include groups in which one or more hydrogen atoms have been removed from polycycloalkanes such as monocycloalkanes, bicycloalkanes, tricycloalkanes, and tetracycloalkanes. Specific examples include groups in which one hydrogen atom has been removed from monocycloalkanes such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane, and polycycloalkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane. Particularly preferred are groups in which one hydrogen atom has been removed from cyclohexane and adamantane (which may further have a substituent).

[0046] -C(R A3 )(R A4 )(R A5 Specific examples of the group represented by the formula (I) include the following groups. [ka]

[0047] In formula (A1), X 1 , and X 2 are each independently -NR a2 -, -O-, or -S-. a2 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.

[0048] R a2 The number of carbon atoms in the alkyl group R is not particularly limited. a2 The number of carbon atoms in the alkyl group represented by R is preferably 1 or more and 6 or less, and more preferably 1 or more and 4 or less. a2 The alkyl group as may be linear or branched, and is preferably linear. R a2 Specific examples of the alkyl group as include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group. R a2 The substituents that the alkyl group may have include a halogen atom, a hydroxyl group, an alkoxy group, a mercapto group, and a cyano group.

[0049] R a2 The number of carbon atoms in the aromatic hydrocarbon group R is not particularly limited. a2 The alkyl group preferably has 6 or more and 12 or less carbon atoms. R a2 Specific examples of the aromatic hydrocarbon group as include a phenyl group, a naphthalene-1-yl group, a naphthalene-2-yl group, a 4-phenylphenyl group, a 3-phenylphenyl group, and a 2-phenylphenyl group. R a2 The substituents that the aromatic hydrocarbon group may have include a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a mercapto group, and a cyano group.

[0050] X in formula (A1) 1 Ar 1 The X in formula (A1) is bonded to the aromatic ring in the aromatic group-containing group. 2 Ar 2 The aromatic group bonded to the aromatic ring in the aromatic group-containing group.

[0051] The above-described X 2 is -NR a2 - or -O-, and -NR a2 - is more preferable. X 2 But, -NR a2 -, in the structural unit represented by formula (A1), the triazine ring and Ar 2 The twist with respect to the structural unit represented by formula (A1) is small. As a result, the planarity of the structural unit represented by formula (A1) is high. It is believed that when the planarity of the structural unit represented by formula (A1) is high, the refractive index of a polymer having the structural unit represented by formula (A1) is high.

[0052] Preferred specific examples of the unit (A1) include the following structural units. Structural units in which the amino group bonded to the triazine ring in the following structural units is replaced with -O- or -S- are also preferred. Structural units in which the tert-butoxycarbonylamino group in the following structural units is replaced with a tert-butoxycarbonyloxy group are also preferred. Structural units in which the tert-butoxycarbonyl group in the following structural units is replaced with a methoxymethyl group, ethoxymethyl group, n-propyloxymethyl group, n-butyloxymethyl group, 1-methoxyethyl group, 1-ethoxymethyl group, 1-n-propyloxyethyl group, 1-n-butyloxyethyl group, tetrahydropyran-2-yl group, or tetrahydrofuran-2-yl group are also preferred.

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] <Units (A2)> As described above, the polymer may contain units (A2) as structural units other than units (A1). The unit (A2) is a structural unit represented by the following formula (A2).

[0058] [ka]

[0059] In formula (A2), Ar 2 , and Ar 3 is an aromatic group-containing group. 1 , and X 2 are each independently -NR a2 -, -O-, or -S-. a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. 1 Ar 3 The aromatic group is bonded to the aromatic ring in the aromatic group-containing group. X 2 Ar 2 The aromatic group bonded to the aromatic ring in the aromatic group-containing group.

[0060] Unit (A2) does not fall under unit (A1). Therefore, Ar 3 The aromatic group-containing group as defined above does not have, as a substituent, a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, a hydroxyl group protected by an acetal protecting group, or a carboxyl group protected by an acid-labile group.

[0061] In formula (A2), X1 , X 2 , and Ar 2 are the same as those in formula (A1). In formula (A2), Ar 3 is an aromatic group which may have a substituent. 3 The aromatic group as Ar may be an aromatic hydrocarbon group or an aromatic heterocyclic group. 3 The aromatic group as is preferably an aromatic hydrocarbon group. Ar 3 Specific examples of the aromatic hydrocarbon group as include a phenyl group, a naphthalene-1-yl group, a naphthalene-2-yl group, a 4-phenylphenyl group, a 3-phenylphenyl group, and a 2-phenylphenyl group. Ar 3 The substituents that the aromatic hydrocarbon group may have include a halogen atom, an alkyl group, an alkoxy group, and a cyano group.

[0062] The polymer has a group represented by the following formula (A1-1) at least at some of the ends of the molecular chain. -X 2 -X 3 -X 4 ···(A1-1) In formula (A1-1), X 2 is X in formula (A1) 2 X 3 is a divalent hydrocarbon group. 4 -OR a3 , or -N(R a3 )2. R a3 is a hydrogen atom or an alkyl group which may have a substituent. a3 )2, two R a3 The two R a3 Preferably, one of X is a hydrogen atom. 3 When the hydrocarbon group as X is an aromatic group-containing group, 4 is not an amino group.

[0063] In formula (A1-1), X 3The type and number of carbon atoms of the divalent hydrocarbon group X are not particularly limited as long as the desired effect is not impaired. 3 The divalent hydrocarbon group as may be an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group.

[0064] X 3 The divalent hydrocarbon group as the alkyl group preferably has 1 or more and 20 or less carbon atoms, more preferably 1 or more and 16 or less carbon atoms, and even more preferably 1 or more and 12 or less carbon atoms.

[0065] X 3 When the divalent hydrocarbon group as the alkyl group is an aliphatic hydrocarbon group, suitable examples of the aliphatic hydrogen group include a methylene group, an ethane-1,2-diyl group, an ethane-1,1-diyl group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, and a decane-1,10-diyl group.

[0066] X 3 When the divalent hydrocarbon group as the aromatic hydrocarbon group, suitable examples of the hydrocarbon group include a p-phenylene group, an m-phenylene group, an o-phenylene group, a naphthalene-1,4-diyl group, a naphthalene-2,6-diyl group, a naphthalene-2,7-diyl group, a biphenyl-4,4'-diyl group, and a biphenyl-3,4'-diyl group.

[0067] X 3When the divalent hydrocarbon group as the group (I) is a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group, suitable examples of the divalent hydrocarbon group as the aliphatic hydrocarbon group include -CH2-pPh-, -CH2-mPh-, -CH2-oPh-, -CH2CH2-pPh-, -CH2CH2-mPh-, -CH2CH2-oPh-, -pPh-CH2-pPh-, -mPh-CH2-mPh-, -pPh-CH2-mPh-, -pPh-C(CH3)2-pPh-, -mPh-C(CH3)2-mPh-, and -pPh-C(CH3)2-mPh-. pPh is a p-phenylene group. mPh is an m-phenylene group. oPh is an o-phenylene group.

[0068] X 4 R in a3 The alkyl group as the group may have a substituent. Examples of the substituent that the alkyl group may have include a hydroxyl group, a mercapto group, an alkoxy group such as a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, and an n-butyloxy group, an alkylthio group such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, and an n-butylthio group, an amino group, a mono-substituted amino group such as a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group, an n-butylamino group, a 2-hydroxyethylamino group, and a 3-hydroxypropylamino group, a di-substituted amino group such as a dimethylamino group, a diethylamino group, a di-n-propylamino group, a diisopropylamino group, a di-n-butylamino group, an N-methyl-N-ethylamino group, an N-methyl-N-(2-hydroxyethyl)amino group, an N-ethyl-N-(2-hydroxyethyl)amino group, and a di(2-hydroxyethyl)amino group, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a cyano group.

[0069] R a3 The number of carbon atoms in the alkyl group R is not particularly limited. a3 The number of carbon atoms in the alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 12 or less, even more preferably 1 or more and 8 or less, and particularly preferably 1 or more and 4 or less.

[0070] R a3 Specific examples of the alkyl group as the aryl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-ethylhexyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, and an icosyl group.

[0071] Suitable examples of the group represented by the above formula (A1-1) include: hydroxyalkylamino groups such as a 2-hydroxyethylamino group, a 3-hydroxypropylamino group, and a 4-hydroxybutylamino group; hydroxyalkyloxy groups such as a 2-hydroxyethyloxy group, a 3-hydroxypropyloxy group, and a 4-hydroxybutyloxy group; hydroxyalkylthio groups such as a 2-hydroxyethylthio group, a 3-hydroxypropylthio group, and a 4-hydroxybutylthio group; alkoxyalkylamino groups such as a 2-methoxyethylamino group, a 3-methoxypropylamino group, and a 4-methoxybutylamino group; alkoxyalkyloxy groups such as a 2-methoxyethyloxy group, a 3-methoxypropyloxy group, and a 4-methoxybutyloxy group; alkoxyalkylthio groups such as a 2-methoxyethylthio group, a 3-methoxypropylthio group, and a 4-methoxybutylthio group; aminoalkylamino groups such as a 2-aminoethylamino group, a 3-aminopropylamino group, and a 4-aminobutylamino group; aminoalkyloxy groups such as a 2-aminoethyloxy group, a 3-aminopropyloxy group, and a 4-aminobutyloxy group; aminoalkylthio groups such as a 2-aminoethylthio group, a 3-aminopropylthio group, and a 4-aminobutylthio group; alkylaminoalkylamino groups such as a 2-methylaminoethylamino group, a 3-methylaminopropylamino group, a 4-methylaminobutylamino group, a 2-ethylaminoethylamino group, a 3-ethylaminopropylamino group, and a 4-ethylaminobutylamino group; alkylaminoalkyloxy groups such as a 2-methylaminoethyloxy group, a 3-methylaminopropyloxy group, a 4-methylaminobutyloxy group, a 2-ethylaminoethyloxy group, a 3-ethylaminopropyloxy group, and a 4-ethylaminobutyloxy group; alkylaminoalkylthio groups such as a 2-methylaminoethylthio group, a 3-methylaminopropylthio group, a 4-methylaminobutylthio group, a 2-ethylaminoethylthio group, a 3-ethylaminopropylthio group, and a 4-ethylaminobutylthio group; hydroxyalkylaminoalkylamino groups such as a 2-(2-hydroxyethylamino)ethylamino group, a 3-(2-hydroxyethylamino)propylamino group, or a 4-(2-hydroxyethylamino)butylamino group; hydroxyalkylaminoalkyloxy groups such as a 2-(2-hydroxyethylamino)ethyloxy group, a 3-(2-hydroxyethylamino)propyloxy group, and a 4-(2-hydroxyethylamino)butyloxy group; hydroxyalkylaminoalkylthio groups such as a 2-(2-hydroxyethylamino)ethylthio group, a 3-(2-hydroxyethylamino)propylthio group, and a 4-(2-hydroxyethylamino)butylthio group; 2-Dimethylaminoethylamino group, 3-dimethylaminopropylamino group, 4-dimethylaminobutylamino group, 2-diethylaminoethylamino group, 3-diethylaminopropylamino group, 4-diethylaminobutylamino group, 2-(N-methyl-N-ethylamino)ethylamino group, 3-(N-methyl-N-ethylamino)propylamino group, 4-(N-methyl-N-ethylamino)butylamino group, 2-(N-methyl-N-2-hydroxyethylamino)ethylamino group, 3-(N-methyl-N-2-hydroxyethylamino)propyl di-substituted aminoalkylalkylamino groups such as an amino group, a 4-(N-methyl-N-2-hydroxyethylamino)butylamino group, a 2-(N-ethyl-N-2-hydroxyethylamino)ethylamino group, a 3-(N-ethyl-N-2-hydroxyethylamino)propylamino group, a 4-(N-ethyl-N-2-hydroxyethylamino)butylamino group, a 2-[di(2-hydroxyethyl)amino]ethylamino group, a 3-[di(2-hydroxyethyl)amino]propylamino group, and a 4-[di(2-hydroxyethyl)amino]butylamino group; 2-Dimethylaminoethyloxy group, 3-dimethylaminopropyloxy group, 4-dimethylaminobutyloxy group, 2-diethylaminoethyloxy group, 3-diethylaminopropyloxy group, 4-diethylaminobutyloxy group, 2-(N-methyl-N-ethylamino)ethyloxy group, 3-(N-methyl-N-ethylamino)propyloxy group, 4-(N-methyl-N-ethylamino)butyloxy group, 2-(N-methyl-N-2-hydroxyethylamino)ethyloxy group, 3-(N-methyl-N-2-hydroxyethylamino)propyl di-substituted aminoalkylalkyloxy groups such as an oxy group, a 4-(N-methyl-N-2-hydroxyethylamino)butyloxy group, a 2-(N-ethyl-N-2-hydroxyethylamino)ethyloxy group, a 3-(N-ethyl-N-2-hydroxyethylamino)propyloxy group, a 4-(N-ethyl-N-2-hydroxyethylamino)butyloxy group, a 2-[di(2-hydroxyethyl)amino]ethyloxy group, a 3-[di(2-hydroxyethyl)amino]propyloxy group, and a 4-[di(2-hydroxyethyl)amino]butyloxy group; 2-Dimethylaminoethylthio group, 3-dimethylaminopropylthio group, 4-dimethylaminobutylthio group, 2-diethylaminoethylthio group, 3-diethylaminopropylthio group, 4-diethylaminobutylthio group, 2-(N-methyl-N-ethylamino)ethylthio group, 3-(N-methyl-N-ethylamino)propylthio group, 4-(N-methyl-N-ethylamino)butylthio group, 2-(N-methyl-N-2-hydroxyethylamino)ethylthio group, 3-(N-methyl-N-2-hydroxyethylamino)propylthio group di-substituted aminoalkylalkylthio groups such as an oxy group, a 4-(N-methyl-N-2-hydroxyethylamino)butylthio group, a 2-(N-ethyl-N-2-hydroxyethylamino)ethylthio group, a 3-(N-ethyl-N-2-hydroxyethylamino)propylthio group, a 4-(N-ethyl-N-2-hydroxyethylamino)butylthio group, a 2-[di(2-hydroxyethyl)amino]ethylthio group, a 3-[di(2-hydroxyethyl)amino]propylthio group, and a 4-[di(2-hydroxyethyl)amino]butyloxy group; hydroxyarylamino groups such as a 4-hydroxyphenylamino group, a 3-hydroxyphenylamino group, and a 2-hydroxyphenylamino group; alkoxyarylamino groups such as a 4-methoxyphenylamino group, a 3-methoxyphenylamino group, and a 2-methoxyphenylamino group; alkylaminoarylamino groups such as a 4-methylaminophenylamino group, a 3-methylaminophenylamino group, and a 2-methylaminophenylamino group; hydroxyaryloxy groups such as a 4-hydroxyphenyloxy group, a 3-hydroxyphenyloxy group, and a 2-hydroxyphenyloxy group; alkoxyaryloxy groups such as a 4-methoxyphenyloxy group, a 3-methoxyphenyloxy group, and a 2-methoxyphenyloxy group; alkylaminoaryloxy groups such as a 4-methylaminophenyloxy group, a 3-methylaminophenyloxy group, and a 2-methylaminophenyloxy group; hydroxyarylthio groups such as a 4-hydroxyphenylthio group, a 3-hydroxyphenylthio group, and a 2-hydroxyphenylthio group; alkoxyarylthio groups such as a 4-methoxyphenylthio group, a 3-methoxyphenylthio group, and a 2-methoxyphenylthio group; alkylaminoarylthio groups such as a 4-methylaminophenylthio group, a 3-methylaminophenylthio group, and a 2-methylaminophenylthio group; Di-substituted amino groups such as dimethylamino, diethylamino, methylethylamino, N-methyl-N-(2-hydroxyethyl)amino, N-ethyl-N-(2-hydroxyethyl)amino, and di(2-hydroxyethyl)amino groups etc.

[0072] The method for introducing the group represented by formula (A1-1) into at least a part of the terminals of the molecular chain of the polymer will be described later.

[0073] The weight-average molecular weight of the polymer is not particularly limited as long as the desired effect is not impaired. The weight-average molecular weight is preferably 500 or more and 100,000 or less. From the viewpoint of high solvent resistance of the polymer in a heated state, the weight-average molecular weight is preferably 2,000 or more. From the viewpoint of high solubility of the polymer in various solvents, the weight-average molecular weight is preferably 30,000 or less. The weight average molecular weight is a molecular weight measured by gel permeation chromatography (GPC) in terms of polystyrene.

[0074] <Polymer manufacturing method> The method for producing the polymer described above is not particularly limited as long as the resulting polymer has the unit (A1) and a terminal group represented by formula (A1-1). Typically, the polymer is produced by condensing a dihalotriazine compound with an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (A5-2), or an aromatic dithiol represented by the following formula (A5-3). Alternatively, a group represented by formula (A1-1) can be introduced at the end of the polymer molecular chain by condensing a dihalo triazine compound with a compound represented by any one of formulas (A5-1) to (A5-3) in the presence of a compound represented by any one of formulas (A7-1) to (A7-3) below, or by reacting a condensation product of a dihalo triazine compound with a compound represented by any one of formulas (A5-1) to (A5-3) with a compound represented by any one of formulas (A7-1) to (A7-3).

[0075] The dihalo triazine compound used in producing the polymer includes a compound represented by the following formula (A3). The compound represented by formula (A3) gives unit (1) by condensation with a compound represented by any one of formulas (A5-1) to (A5-3). When the polymer contains unit (2), the dihalo triazine compound includes a compound represented by the following formula (A6). The compound represented by formula (A6) gives unit (2) by condensation with a compound represented by any one of formulas (A5-1) to (A5-3).

[0076] [ka]

[0077] In formula (A3), Hal is a halogen atom. 1 is an aromatic group-containing group. a1 is a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group. An acetal protecting group is -CHR A1 -OR A2 R A1 is a hydrogen atom or an alkyl group. A2 is an alkyl group. A1 , and R A2 may be bonded to each other to form a ring. 1 are each independently -NR a2 -, -O-, or -S-. a2is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. 1 Ar 1 The aromatic group bonded to the aromatic ring in the aromatic group-containing group.

[0078] In formula (A3), Ar 1 , X 1 , and R a1 are the same as those in formula (A1). Hal is a halogen atom. Examples of Hal include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a chlorine atom and a bromine atom are preferred, and a chlorine atom is more preferred.

[0079] [ka] In formula (A6), Hal is a halogen atom. 3 is an aromatic group-containing group. 1 are each independently -NR a2 -, -O-, or -S-. a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. 1 Ar 3 The aromatic group bonded to the aromatic ring in the aromatic group-containing group.

[0080] In formula (A6), Ar 3 , and X 1 are the same as those in formula (A2).

[0081] Ar 2 -(NR a2 H)2···(A5-1) Ar 2 -(OH)2···(A5-2) Ar 2 -(SH)2···(A5-3)

[0082] In formulas (A5-1) to (A5-3), Ar 2 , and R a2 are the same as those in formula (A1).

[0083] Specific examples of the aromatic diamine compound represented by formula (A5-1) include p-phenylenediamine, m-phenylenediamine, 2,4-diaminotoluene, 4,4'-diaminobiphenyl, 3,3'-diaminobiphenyl, 3,4'-diaminobiphenyl, 1,4-diaminonaphthalene, 1,5-diaminonaphthalene, 2,6-diaminonaphthalene, 2,7-diaminonaphthalene, 9,10-diaminoanthracene, 9,10-bis(4-aminophenyl)anthracene, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl ... ,4'-Diaminobenzophenone, 3,3'-diaminobenzophenone, 3,4'-diaminobenzophenone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 2,2-bis(4-aminophenyl)propane, 2, 2-Bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 4,4'-diaminobenzanilide, 3,3'-diaminobenzanilide, 1,4-bis(4-aminophenyl)benzene, 1,3-bis(4-aminophenyl)benzene, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene benzene, 1,3-bis(3-aminophenoxy)benzene, 1,2-bis(4-aminophenoxy)ethane, 1,3-bis(4-aminophenoxy)propane, 1,4-bis(4-aminophenoxy)butane, 1,5-bis(4-aminophenoxy)pentane, 1,6-bis(4-aminophenoxy)hexane, bis[4-(4-aminophenoxy)phenyl]ether, bis[4-(3-aminophenoxy)phenyl]ether, 4,4'-bis(4-aminophenoxy)biphenyl, 3,4'-bis(4-aminophenoxy)biphenyl, 3,3'-bis(4-aminophenoxy)biphenyl, bis(4-aminophenoxyphenyl)sulfone, bis(3-aminophenoxyphenyl)sulfone, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]sulfone, bis[4-(4-aminophenoxy)phenyl]ketone, 2,2-bis[4-{4-amino-2-(trifluoromethyl)phenoxy}phenyl]hexafluoropropane, 9,9-bis(4-amino phenyl)fluorene, 9,9-bis(4-amino-3-methylphenyl)fluorene, 2,7-diaminofluorene, 2-(4-aminophenyl)-5-aminobenzoxazole, 2-(3-aminophenyl)-5-aminobenzoxazole, 2-(4-aminophenyl)-6-aminobenzoxazole, 2-(3-aminophenyl)-6-aminobenzoxazole, 1,4-bis(5-amino-2-benzoxazolyl)benzene, 1,4-bis(6-amino-2 -benzoxazolyl)benzene, 1,3-bis(5-amino-2-benzoxazolyl)benzene, 1,3-bis(6-amino-2-benzoxazolyl)benzene, 2,6-bis(4-aminophenyl)benzobisoxazole, 2,6-bis(3-aminophenyl)benzobisoxazole, bis[(3-aminophenyl)-5-benzoxazolyl], bis[(4-aminophenyl)-5-benzoxazolyl], bis[(3-aminophenyl)-6-benzoxazol zolyl], bis[(4-aminophenyl)-6-benzoxazolyl], 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 4,4'-[1,4-phenylenebis(1-methylethane-1,1-diyl)]dianiline, 4-aminobenzoic acid 4-aminophenyl ester, 1,3-bis(4-anilino)tetramethyldisiloxane, 1,4-bis(3-aminopropyldimethylsilyl)benzene, ortho-tolidine sulfone, etc.

[0084] Specific examples of the aromatic diol represented by formula (A5-2) include hydroquinone, resorcinol, 2,4-dihydroxytoluene, 4,4'-dihydroxybiphenyl, 3,3'-dihydroxybiphenyl, 3,4'-dihydroxybiphenyl, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 9,10-dihydroxyanthracene, 9,10-bis(4-hydroxyphenyl)anthracene, 4,4'-dihydroxy-2 ,2'-bis(trifluoromethyl)biphenyl, 4,4'-dihydroxybenzophenone, 3,3'-dihydroxybenzophenone, 3,4'-dihydroxybenzophenone, 4,4'-dihydroxydiphenyl sulfone, 3,3'-dihydroxydiphenyl sulfone, 3,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfide, 3,3'-dihydroxydiphenyl sulfide, 3,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenylmethane, 3,3' -Diaminodiphenylmethane, 3,4'-dihydroxydiphenylmethane, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), 2,2-bis[4-(4-hydroxyphenoxy)phenyl]propane, 2,2-bis[4-(4-hydroxyphenoxy)phenyl]hexafluoropropane, 4,4'-dihydroxydiphenyl ether, 3,4'-dihydroxydiphenyl ether, 3,3'-dihydroxydiphenyl ether, 4,4'-dihydroxybenzanilide, 3,3'-dihydro Xybenzanilide, 1,4-bis(4-hydroxyphenyl)benzene, 1,3-bis(4-hydroxyphenyl)benzene, 1,4-bis(4-hydroxyphenoxy)benzene, 1,3-bis(4-hydroxyphenoxy)benzene, 1,3-bis(3-hydroxyphenoxy)benzene, 1,2-bis(4-hydroxyphenoxy)ethane, 1,3-bis(4-hydroxyphenoxy)propane, 1,4-bis(4-hydroxyphenoxy)butane, 1,5-bis(4-hydroxyphenoxy)pentane, 1,6-bis(4-hydroxyphenoxy)hexane, bis[4-(4-hydroxyphenoxy)phenyl]ether, bis[4-(3-hydroxyphenoxy)phenyl]ether, 4,4'-bis(4-hydroxyphenoxy)biphenyl, 3,4'-bis(4-hydroxyphenoxy)biphenyl, 3,3'-bis(4-hydroxyphenoxy)biphenyl, bis(4-hydroxyphenoxyphenyl)sulfone, bis(3-hydroxyphenoxyphenyl)sulfone, bis[4-(4-hydroxyphenoxy)phenyl]sulfone, bis[4 -(3-hydroxyphenoxy)phenyl]sulfone, bis[4-(4-hydroxyphenoxy)phenyl]ketone, 2,2-bis[4-{4-hydroxy2-(trifluoromethyl)phenoxy}phenyl]hexafluoropropane, 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 2,7-dihydroxyfluorene, 2-(4-hydroxyphenyl)-5-hydroxybenzoxazole, 2-(3-hydroxyphenyl)-5-hydroxybenzoxazole, 2 -(4-hydroxyphenyl)-6-hydroxybenzoxazole, 2-(3-hydroxyphenyl)-6-hydroxybenzoxazole, 1,4-bis(5-hydroxy-2-benzoxazolyl)benzene, 1,4-bis(6-hydroxy-2-benzoxazolyl)benzene, 1,3-bis(5-hydroxy-2-benzoxazolyl)benzene, 1,3-bis(6-hydroxy-2-benzoxazolyl)benzene, 2,6-bis(4-hydroxyphenyl)benzobisoxazole, 2,6-bis(3-hydroxyphenyl)benzene Bisoxazole, bis[(3-hydroxyphenyl)-5-benzoxazolyl], bis[(4-hydroxyphenyl)-5-benzoxazolyl], bis[(3-hydroxyphenyl)-6-benzoxazolyl], bis[(4-hydroxyphenyl)-6-benzoxazolyl], 3,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenyl sulfide, 4,4'-[1,4-phenylenebis(1-methylethane-1,1-diyl)]dianiline, 4-hydroxybenzoic acid 4-hydroxyphenyl ester, 1,Examples include 3-bis(4-anilino)tetramethyldisiloxane.

[0085] Specific examples of the aromatic dithiol represented by formula (A5-3) include 1,4-dimercaptobenzene, 1,3-dimercaptobenzene, 2,4-dimercaptotoluene, 4,4'-dimercaptobiphenyl, 3,3'-dimercaptobiphenyl, 3,4'-dimercaptobiphenyl, 1,4-dimercaptonaphthalene, 1,5-dimercaptonaphthalene, 2,6-dimercaptonaphthalene, 2,7-dimercaptonaphthalene, 9,10-dimercaptoanthracene, 9,10-bis(4-mercaptophenyl)anthracene, 4, 4'-Dimercapto-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-dimercaptobenzophenone, 3,3'-dimercaptobenzophenone, 3,4'-dimercaptobenzophenone, 4,4'-dimercaptodiphenyl sulfone, 3,3'-dimercaptodiphenyl sulfone, 3,4'-dimercaptodiphenyl sulfone, 4,4'-dimercaptodiphenyl sulfide, 3,3'-dimercaptodiphenyl sulfide, 3,4'-dimercaptodiphenyl sulfide, 4,4'-dimercaptodiphenyl Methane, 3,3'-diaminodiphenylmethane, 3,4'-dimercaptodiphenylmethane, 2,2-bis(4-mercaptophenyl)propane (bisphenol A), 2,2-bis[4-(4-mercaptophenoxy)phenyl]propane, 2,2-bis[4-(4-mercaptophenoxy)phenyl]hexafluoropropane, 4,4'-dimercaptodiphenyl ether, 3,4'-dimercaptodiphenyl ether, 3,3'-dimercaptodiphenyl ether, 4,4'-dimercaptobenzanilide, 3,3'- Dimercaptobenzanilide, 1,4-bis(4-mercaptophenyl)benzene, 1,3-bis(4-mercaptophenyl)benzene, 1,4-bis(4-mercaptophenoxy)benzene, 1,3-bis(4-mercaptophenoxy)benzene, 1,3-bis(3-mercaptophenoxy)benzene, 1,2-bis(4-mercaptophenoxy)ethane, 1,3-bis(4-mercaptophenoxy)propane, 1,4-bis(4-mercaptophenoxy)butane, 1,5-bis(4-mercaptophenoxy)pentane, 1,6-bis(4-mercaptophenoxy)hexane, bis[4-(4-mercaptophenoxy)phenyl]ether, bis[4-(3-mercaptophenoxy)phenyl]ether, 4,4'-bis(4-mercaptophenoxy)biphenyl, 3,4'-bis(4-mercaptophenoxy)biphenyl, 3,3'-bis(4-mercaptophenoxy)biphenyl, bis(4-mercaptophenoxyphenyl)sulfone, bis(3-mercaptophenoxyphenyl)sulfone, bis[4-(4-mercaptophenoxy)phenyl]sulfone, bis[ 4-(3-mercaptophenoxy)phenyl]sulfone, bis[4-(4-mercaptophenoxy)phenyl]ketone, 2,2-bis[4-{4-mercapto2-(trifluoromethyl)phenoxy}phenyl]hexafluoropropane, 9,9-bis(4-mercaptophenyl)fluorene, 9,9-bis(4-mercapto3-methylphenyl)fluorene, 2,7-dimercaptofluorene, 2-(4-mercaptophenyl)-5-mercaptobenzoxazole, 2-(3-mercaptophenyl)-5-mercaptobenzoxazole, 2 -(4-mercaptophenyl)-6-mercaptobenzoxazole, 2-(3-mercaptophenyl)-6-mercaptobenzoxazole, 1,4-bis(5-mercapto-2-benzoxazolyl)benzene, 1,4-bis(6-mercapto-2-benzoxazolyl)benzene, 1,3-bis(5-mercapto-2-benzoxazolyl)benzene, 1,3-bis(6-mercapto-2-benzoxazolyl)benzene, 2,6-bis(4-mercaptophenyl)benzobisoxazole, 2,6-bis(3-mercaptophenyl)benzene Bisoxazole, bis[(3-mercaptophenyl)-5-benzoxazolyl], bis[(4-mercaptophenyl)-5-benzoxazolyl], bis[(3-mercaptophenyl)-6-benzoxazolyl], bis[(4-mercaptophenyl)-6-benzoxazolyl], 3,4'-dimercaptodiphenyl sulfide, 4,4'-dimercaptodiphenyl sulfide, 4,4'-[1,4-phenylenebis(1-methylethane-1,1-diyl)]dianiline, 4-mercaptobenzoic acid 4-mercaptophenyl ester, 1,Examples include 3-bis(4-anilino)tetramethyldisiloxane.

[0086] X 4 -X 3 -NR a2 H···(A7-1) X 4 -X 3 -OH···(A7-2) X 4 -X 3 -SH···(A7-3)

[0087] In formulas (A7-1) to (A7-3), X 3 , and X 4 is X in formula (A1-1) 3 , and X 4 Similar to R a2 is R in Equation (1). a2 is the same as:

[0088] The compound represented by formula (A7-1) is hydroxyalkylamines such as 2-hydroxyethylamine, 3-hydroxypropylamine, and 4-hydroxybutylamine groups; alkoxyalkylamines such as 2-methoxyethylamine, 3-methoxypropylamine, and 4-methoxybutylamine; aminoalkylamines (alkanediamines) such as 2-aminoethylamine (ethylenediamine), 3-aminopropylamine (1,3-diaminopropane), and 4-aminobutylamine (1,4-diaminobutane); alkylaminoalkylamines such as 2-methylaminoethylamine, 3-methylaminopropylamine, 4-methylaminobutylamine, 2-ethylaminoethylamine, 3-ethylaminopropylamine, and 4-ethylaminobutylamine groups; hydroxyalkylaminoalkylamine groups such as 2-(2-hydroxyethylamino)ethylamine group, 3-(2-hydroxyethylamino)propylamine, and 4-(2-hydroxyethylamino)butylamine; (2-aminoethyl)dimethylamine, (3-aminopropyl)dimethylamine, (4-aminobutyl)dimethylamine, (2-aminoethyl)diethylamine, (3-aminopropyl)diethylamine group, (4-aminobutyl)diethylamine, 2-(N-methyl-N-ethylamino)ethylamine, 3-(N-methyl-N-ethylamino)propylamine, 4-(N-methyl-N-ethylamino)butylamine, 2-(N-methyl-N-2-hydroxyethylamino)ethylamine, 3-(N-methyl-N-2-hydroxyethylamino)ethylamine di-substituted aminoalkyl alkylamines such as 2-(N-ethyl-N-2-hydroxyethylamino)propylamine, 4-(N-methyl-N-2-hydroxyethylamino)butylamine, 2-(N-ethyl-N-2-hydroxyethylamino)ethylamine, 3-(N-ethyl-N-2-hydroxyethylamino)propylamine, 4-(N-ethyl-N-2-hydroxyethylamino)butylamine, 2-[di(2-hydroxyethyl)amino]ethylamine, 3-[di(2-hydroxyethyl)amino]propylamine, and 4-[di(2-hydroxyethyl)amino]butylamine; hydroxyarylamines such as 4-hydroxyaniline group, 3-hydroxyaniline group, and 2-hydroxyaniline; alkoxyarylamines such as 4-methoxyaniline, 3-methoxyaniline, and 2-methoxyaniline; alkylaminoarylamines such as 4-methylaminoaniline group, 3-methylaminoaniline group, and 2-methylaminoaniline; hydroxyarylalkylamines such as 4-hydroxybenzylamine, 3-hydroxybenzylamine, 2-hydroxybenzylamine, 4-hydroxyphenethylamine, 3-hydroxyphenethylamine, and 2-hydroxyphenethylamine; alkoxyarylalkylamines such as 4-methoxybenzylamine, 3-methoxybenzylamine, 2-methoxybenzylamine, 4-methoxyphenethylamine, 3-methoxyphenethylamine, and 2-methoxyphenethylamine; aminoarylalkylamines such as 4-aminobenzylamine, 3-aminobenzylamine, 2-aminobenzylamine, 4-aminophenethylamine, 3-aminophenethylamine, and 2-aminophenethylamine; methylaminoarylalkylamines such as 4-methylaminobenzylamine, 3-methylaminobenzylamine, 2-methylaminobenzylamine, 4-methylaminophenethylamine, 3-methylaminophenethylamine, and 2-methylaminophenethylamine; Disubstituted amino groups such as dimethylamine, diethylamine, methylethylamine, N-methyl-N-(2-hydroxyethyl)amine, N-ethyl-N-(2-hydroxyethyl)amine, and di(2-hydroxyethyl)amine (diethanolamine) etc.

[0089] The compound represented by formula (A7-2) is Alkanediols such as ethylene glycol, 1,3-propanediol, and 1,4-propanediol; monoalkyl ethers of alkanediols such as ethylene glycol monomethyl ether, 1,3-propanediol monomethyl ether, and 1,4-butanediol monomethyl ether; aminoalkanols such as 2-aminoethanol, 3-aminopropanol, and 4-aminobutanol; alkylaminoalkanols such as 2-methylaminoethanol, 3-methylaminopropanol, and 4-methylaminobutanol, 2-ethylaminoethanol, 3-ethylaminopropanol, and 4-ethylaminobutanol; hydroxyalkylaminoalkanols such as 2-(2-hydroxyethylamino)ethanol, 3-(2-hydroxyethylamino)propanol, and 4-(2-hydroxyethylamino)butanol; 2-Dimethylaminoethanol, 3-dimethylaminopropanol, 4-dimethylaminobutanol, 2-diethylaminoethanol, 3-diethylaminopropanol, 4-diethylaminobutanol, 2-(N-methyl-N-ethylamino)ethanol, 3-(N-methyl-N-ethylamino)propanol, 4-(N-methyl-N-ethylamino)butanol, 2-(N-methyl-N-2-hydroxyethylamino)ethanol, 3-(N-methyl-N-2-hydroxyethylamino)propanol di-substituted aminoalkyl alkanols such as 4-(N-methyl-N-2-hydroxyethylamino)butanol, 2-(N-ethyl-N-2-hydroxyethylamino)ethanol, 3-(N-ethyl-N-2-hydroxyethylamino)propanol, 4-(N-ethyl-N-2-hydroxyethylamino)butanol, 2-[di(2-hydroxyethyl)amino]ethanol, 3-[di(2-hydroxyethyl)amino]propanol, and 4-[di(2-hydroxyethyl)amino]butanol groups; dihydroxyarenes such as 4-hydroxyphenol (hydroquinone), 3-hydroxyphenol (resorcinol), and 2-hydroxyphenol (catechol); alkoxyphenols such as 4-methoxyphenol, 3-methoxyphenol, and 2-methoxyphenol; alkylaminophenols such as 4-methylaminophenol, 3-methylaminophenol, and 2-methylaminophenol; hydroxyarylalkanols such as 4-hydroxybenzyl alcohol, 3-hydroxybenzyl alcohol, 2-hydroxybenzyl alcohol, 4-hydroxyphenethyl alcohol, 3-hydroxyphenethyl alcohol, and 2-hydroxyphenethyl alcohol; alkoxyarylalkanols such as 4-methoxybenzyl alcohol, 3-methoxybenzyl alcohol, 2-methoxybenzyl alcohol, 4-methoxyphenethyl alcohol, 3-methoxyphenethyl alcohol, and 2-methoxyphenethyl alcohol; aminoarylalkanols such as 4-aminobenzyl alcohol, 3-aminobenzyl alcohol, 2-aminobenzyl alcohol, 4-aminophenethyl alcohol, 3-aminophenethyl alcohol, and 2-aminophenethyl alcohol; methylaminoarylalkanols such as 4-methylaminobenzyl alcohol, 3-methylaminobenzyl alcohol, 2-methylaminobenzyl alcohol, 4-methylaminophenethyl alcohol, 3-methylaminophenethyl alcohol, and 2-methylaminophenethyl alcohol; etc.

[0090] The compound represented by formula (A7-3) is mercaptoalkanols such as 2-mercaptoethanol, 3-mercaptopropanol, and 4-mercaptobutanol; Alkyl ethers of mercaptoalkanols such as 1-mercapto-2-methoxyethane, 1-mercapto-3-methoxypropane, and 1-mercapto-4-methoxybutane; mercaptoalkylamines such as 1-mercapto-2-aminoethane, 1-mercapto-3-aminopropane, and 1-mercapto-4-aminobutane; N-(alkylmercapto)alkylamines such as 1-mercapto-2-methylaminoethane, 1-mercapto-3-methylaminopropane, and 1-mercapto-4-methylaminobutane, 1-mercapto-2-ethylaminoethane, 1-mercapto-3-ethylaminopropane, and 1-mercapto-4-ethylaminobutane; mercapto(hydroxyalkylamino)alkanes such as 1-mercapto-2-(2-hydroxyethylamino)ethane, 1-mercapto-3-(2-hydroxyethylamino)propane, and 1-mercapto-4-(2-hydroxyethylamino)butane; 1-mercapto-2-dimethylaminoethane, 1-mercapto-3-dimethylaminopropane, 1-mercapto-4-dimethylaminobutane, 1-mercapto-2-diethylaminoethane, 1-mercapto-3-diethylaminopropane, 1-mercapto-4-diethylaminobutane, 1-mercapto-2-(N-methyl-N-ethylamino)ethane, 1-mercapto-3-(N-methyl-N-ethylamino)propane, 1-mercapto-4-(N-methyl-N-ethylamino)butane, 1-mercapto-2-(N-methyl-N-2-hydroxyethylamino)ethane, 1-mercapto-3-(N-methyl-N-2-hydroxyethylamino)ethane N-(alkylmercapto)-N,N-disubstituted-alkylamines such as 1-mercapto-4-(N-methyl-N-2-hydroxyethylamino)propane, 1-mercapto-2-(N-ethyl-N-2-hydroxyethylamino)ethane, 1-mercapto-3-(N-ethyl-N-2-hydroxyethylamino)propane, 1-mercapto-4-(N-ethyl-N-2-hydroxyethylamino)butane, 1-mercapto-2-[di(2-hydroxyethyl)amino]ethane, 1-mercapto-3-[di(2-hydroxyethyl)amino]propane, and 4-[di(2-hydroxyethyl)amino]butane; mercapto-substituted hydroxyarenes such as 4-mercaptophenol, 3-mercaptophenol, and 2-mercaptophenol; alkoxythiophenols such as 4-methoxythiophenol, 3-methoxythiophenol, and 2-methoxythiophenol; alkylaminothiophenols such as 4-methylaminothiophenol, 3-methylaminothiophenol, and 2-methylaminothiophenol; hydroxyarylalkyl mercaptans such as 4-hydroxybenzyl mercaptan, 3-hydroxybenzyl mercaptan, 2-hydroxybenzyl mercaptan, 4-hydroxyphenethyl mercaptan, 3-hydroxyphenethyl mercaptan, and 2-hydroxyphenethyl mercaptan; alkoxyarylalkyl mercaptans such as 4-methoxybenzyl mercaptan, 3-methoxybenzyl mercaptan, 2-methoxybenzyl mercaptan, 4-methoxyphenethyl mercaptan, 3-methoxyphenethyl mercaptan, and 2-methoxyphenethyl mercaptan; aminoarylalkyl mercaptans such as 4-aminobenzyl mercaptan, 3-aminobenzyl mercaptan, 2-aminobenzyl mercaptan, 4-aminophenethyl mercaptan, 3-aminophenethyl mercaptan, and 2-aminophenethyl mercaptan; methylaminoarylalkyl mercaptans such as 4-methylaminobenzyl mercaptan, 3-methylaminobenzyl mercaptan, 2-methylaminobenzyl mercaptan, 4-methylaminophenethyl mercaptan, 3-methylaminophenethyl mercaptan, and 2-methylaminophenethyl mercaptan; etc.

[0091] The dihalotriazine compound represented by formula (A3) can be produced by condensing a cyanuric halide with an aromatic amine compound represented by formula (A3-1) below, a hydroxy aromatic compound represented by formula (A3-2) below, or a mercapto aromatic compound represented by formula (A3-3) below. R a1 -Ar 1 -NR a2 H···(A3-1) R a1 -Ar 1 -OH···(A3-2) R a1 -Ar 1 -SH···(A3-3)

[0092] In formulas (A3-1) to (A3-3), Ar 1 , R a1 , and R a2 are the same as those in formula (A1).

[0093] Cyanuric halides include cyanuric fluoride, cyanuric chloride, and cyanuric bromide. Of these, cyanuric chloride is preferred.

[0094] In producing the dihalotriazine compound represented by formula (A3), the amount of the aromatic amine compound represented by formula (A3-1), the hydroxy aromatic compound represented by formula (A3-2), or the mercapto aromatic compound represented by formula (A3-3) used is preferably 0.8 mol or more and 1.2 mol or less, more preferably 0.9 mol or more and 1.1 mol or less, and even more preferably 0.95 mol or more and 1.05 mol or less, per 1 mol of cyanuric halide.

[0095] The reaction of a cyanuric halide with an aromatic amine compound represented by formula (A3-1), a hydroxy aromatic compound represented by formula (A3-2), or a mercapto aromatic compound represented by formula (A3-3) is usually carried out by mixing the two in an organic solvent. The organic solvent used in this reaction is not particularly limited as long as the reaction proceeds smoothly. As the organic solvent, a solvent having no hydroxyl group, mercapto group, or amino group is preferred, since it does not react with cyanuric halide. Specific examples of organic solvents include ethers such as tetrahydrofuran and 1,4-dioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone, diethyl ketone, methyl isobutyl ketone, methyl n-butyl ketone, and cyclohexanone; aromatic hydrocarbons such as toluene, p-xylene, o-xylene, m-xylene, ethylbenzene, and styrene; monoalkyl ether acetates of glycols such as ethylene glycol methyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and diethylene glycol monoethyl ether acetate; dialkyl ethers of glycols such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and triethylene glycol dimethyl ether; esters such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, and isobutyl acetate; and lactones such as γ-butyrolactone. The amount of organic solvent used is not particularly limited as long as the reaction proceeds smoothly, and is preferably 100 parts by mass or more and 5,000 parts by mass or less, and more preferably 200 parts by mass or more and 4,000 parts by mass or less, relative to 100 parts by mass of the reaction raw materials.

[0096] The temperature at which a cyanuric halide is reacted with an aromatic amine compound represented by Formula (A3-1), a hydroxy aromatic compound represented by Formula (A3-2), or a mercapto aromatic compound represented by Formula (A3-3) is, for example, preferably −20° C. or higher and 150° C. or lower, more preferably −10° C. or higher and 50° C. or lower. The aromatic amine compound represented by formula (A3-1), the hydroxy aromatic compound represented by formula (A3-2), or the mercapto aromatic compound represented by formula (A3-3) is R a1When the protecting group has a tert-butoxycarbonyloxy group or a tert-butoxycarbonylamino group, the reaction temperature is preferably −10° C. or higher and 50° C. or lower to prevent thermal deprotection of the tert-butoxycarbonyloxy group or the tert-butoxycarbonylamino group. The reaction time is not particularly limited. For example, the reaction time is preferably 30 minutes or more and 50 hours or less, and more preferably 1 hour or more and 30 hours or less.

[0097] Specific preferred examples of the aromatic amine compound represented by formula (A3-1), the hydroxy aromatic compound represented by formula (A3-2), and the mercapto aromatic compound represented by formula (A3-3) include the following compounds. a1 is R in formula (A1) a1 is the same as: [ka]

[0098] [ka]

[0099] [ka]

[0100] The method for condensing the dihalo triazine compound represented by formula (A3) and the dihalo triazine compound optionally containing the dihalo triazine compound represented by formula (A6) with the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), or the aromatic dithiol represented by formula (A5-3) is not particularly limited. Typically, the polymer can be produced by mixing a dihalo triazine compound represented by formula (A3) and optionally a dihalo triazine compound including a dihalo triazine compound represented by formula (A6) with an aromatic diamine compound represented by formula (A5-1), an aromatic diol represented by formula (A5-2), or an aromatic dithiol represented by formula (A5-3) in an organic solvent.

[0101] In the above condensation reaction, by adding a compound represented by any one of formulas (A7-1) to (A7-3), a group represented by formula (1-1) is formed at the end of the molecular chain of the resulting polymer. In this case, the compound represented by any one of formulas (A7-1) to (A7-3) may be added to the reaction system at the start of the condensation reaction, or may be added to the reaction system during the condensation reaction.

[0102] Alternatively, the polymer produced by the above condensation reaction may be reacted with a compound represented by any one of formulas (A7-1) to (A7-3) to introduce the group represented by formula (1-1) into the terminal of the polymer molecular chain. In this case, the reaction conditions may be the same as the conditions for condensing a dihalotriazine compound with an aromatic diamine compound represented by formula (A5-1), an aromatic diol represented by formula (A5-2), or an aromatic dithiol represented by formula (A5-3).

[0103] The organic solvent used in the condensation reaction is preferably an organic solvent in which the resulting polymer is soluble. Examples of such organic solvents include N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylformamide, N-methylformamide, N,N-dimethylpropionic acid amide, N,N-dimethylisobutyramide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-methyl-2-piperidone, N-acetylpyrrolidine, N,N'-dimethylethyleneurea (1,3-dimethyl-2-imidazolidinone), N,N'-dimethylpropyleneurea, N,N, Examples of suitable organic solvents include nitrogen-containing polar organic solvents such as N',N'-tetramethylmalonic acid amide, N-methylcaprolactam, N,N,N',N'-tetramethylurea, 3-methoxy-N,N-dimethylpropanamide, and 3-butoxy-N,N-dimethylpropanamide; sulfoxides such as dimethyl sulfoxide; hexamethylphosphoric triamide; ketone solvents such as cyclopentanone, cyclohexanone, and methyl isobutyl ketone; and ethers such as tetrahydrofuran and dioxane. The amount of organic solvent used is not particularly limited as long as the reaction proceeds smoothly, and is preferably 100 parts by mass or more and 5,000 parts by mass or less, and more preferably 200 parts by mass or more and 4,000 parts by mass or less, relative to 100 parts by mass of the reaction raw materials.

[0104] In producing the polymer, the amount of the aromatic diamine compound represented by Formula (A5-1), the aromatic diol represented by Formula (A5-2), or the aromatic dithiol represented by Formula (A5-3) used is preferably 0.8 mol or more and 2.0 mol or less, more preferably 0.9 mol or more and 1.8 mol or less, still more preferably 0.95 mol or more and 1.6 mol or less, and particularly preferably 1.0 mol or more and 1.5 mol or less, per 1 mol of the dihalo triazine compound represented by Formula (A3) and optionally the dihalo triazine compound including the dihalo triazine compound represented by Formula (A6).

[0105] The amount of the compound represented by any one of formulas (A7-1) to (A7-3) used is not particularly limited as long as the desired effect is not impaired. The amount of the compound represented by any one of formulas (A7-1) to (A7-3) used is preferably 0.1 mol or more and 2 mol or less, more preferably 0.2 mol or more and 1.8 mol or less, and even more preferably 0.5 mol or more and 1.5 mol or less, per 1 mol of the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), or the aromatic dithiol represented by formula (A5-3). By using the compound represented by any one of formulas (A7-1) to (A7-3) in an amount within the above range, a sufficient amount of the group represented by formula (A1-1) can be introduced to the terminal of the polymer, and an increase in molecular weight during storage can be suppressed.

[0106] The reaction temperature when polymerizing the polymer is, for example, preferably 0°C or higher and 200°C or lower, and more preferably 20°C or higher and 150°C or lower. The reaction temperature when the polymer ends are blocked is, for example, preferably 0°C or higher and 200°C or lower, more preferably 20°C or higher and 150°C or lower, and even more preferably 20°C or higher and 60°C or lower. The reaction temperature during polymerization of the polymer is preferably higher than the reaction temperature during terminal blocking of the polymer. The reaction time for polymerizing the polymer and for blocking the ends of the polymer is not particularly limited. For example, the reaction time for polymerizing the polymer is preferably 5 minutes to 48 hours, more preferably 10 minutes to 40 hours, and even more preferably 30 minutes to 30 hours. The reaction time for blocking the ends of the polymer is preferably from 5 minutes to 12 hours, more preferably from 10 minutes to 6 hours, and even more preferably from 30 minutes to 3 hours. The reaction time for polymerizing the polymer is preferably longer than the reaction time for capping the ends of the polymer.

[0107] <Non-photosensitive liquid composition> The non-photosensitive liquid composition contains the above-mentioned polymer (A) and an organic solvent (S). The aforementioned polymer (A) is R a1When the non-photosensitive liquid composition has a hydroxyl group protected with an acetal protecting group or a carboxyl group protected with an acid-dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0108] Such a non-photosensitive liquid composition is molded into a desired shape by a method such as coating or casting, and then the non-photosensitive liquid composition is heated to remove the organic solvent (S), thereby obtaining a molded article. In this process, the hydroxyl groups protected with tert-butoxycarbonyloxy groups, tert-butoxycarbonylamino groups, or acetal protecting groups are deprotected by heating to generate hydroxyl groups or amino groups, making the polymer components contained in the molded product less soluble in organic solvents. In addition, the polymer (A) may be R a1 When the non-photosensitive liquid composition has a hydroxyl group protected with an acetal protecting group or a carboxyl group protected with an acid-dissociable group as the protecting group, the non-photosensitive liquid composition further contains a thermal acid generator (C). When such a non-photosensitive liquid composition is heated, the hydroxyl group protected by the acetal protecting group or the carboxyl group protected by the acid-dissociable group is deprotected by the action of the acid generated by the thermal acid generator (C), resulting in the generation of a hydroxyl group or a carboxyl group, making the polymer component contained in the molded product less soluble in an organic solvent.

[0109] The non-photosensitive liquid composition preferably contains a crosslinkable compound (B). When the polymer (A) is heated, a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group is deprotected, or a carboxyl group protected by an acid-dissociable group is deprotected, thereby generating a hydroxyl group, an amino group, or a carboxyl group. The deprotected polymer (A) is crosslinked by the crosslinkable compound (B) capable of reacting with a hydroxyl group, an amino group, or a carboxyl group, thereby curing the non-photosensitive liquid composition and forming a cured product that is poorly soluble in organic solvents.

[0110] <Polymer (A)> The polymer (A) is the aforementioned polymer containing a structural unit represented by formula (A1).

[0111] <Crosslinkable compound (B)> The crosslinkable compound (B) is not particularly limited as long as it is a compound having two or more crosslinkable groups capable of reacting with a hydroxyl group, an amino group, or a carboxy group. In terms of the high refractive index of the cured product formed by heating the non-photosensitive liquid composition, the crosslinkable compound (B) is preferably an aromatic compound (Bi) containing two or more crosslinkable groups and a triazine ring, a fluorene ring which may have a substituent, or a binaphthalene ring which may have a substituent, a sulfur-containing compound (Bii) containing two or more crosslinkable groups, or an isocyanate compound (Biii) containing two or more isocyanate groups. The sulfur-containing compound (Bii) is a compound that does not fall under the category of the aromatic compound (Bi). The isocyanate compound (Biii) is a compound that does not fall under the category of the aromatic compound (Bi) or the sulfur-containing compound (Bii).

[0112] The crosslinkable group is a group capable of reacting with a phenolic hydroxyl group, an amino group, or a carboxyl group to form a crosslink. Suitable examples of the crosslinkable group include an epoxy group, an episulfide group, and an isocyanate group.

[0113] The crosslinkable compound (B) crosslinks the polymer (A') having a phenolic hydroxyl group, an amino group, or a carboxyl group, which is derived from the polymer (A) and is generated by deprotection, thereby forming a cured product having a high refractive index using a non-photosensitive liquid composition. In particular, when the crosslinkable compound (B) is an isocyanate compound (Biii), it is preferable in that the refractive index does not decrease because the compound has a carbonyl group at the crosslinking site.

[0114] Hereinafter, a compound containing two or more crosslinkable groups and a triazine ring will also be referred to as a "crosslinkable triazine compound (Bi-1)." A compound containing two or more crosslinkable groups and a fluorene ring will also be referred to as a "crosslinkable fluorene compound (Bi-2)." A compound containing two or more crosslinkable groups and a binaphthalene ring will also be referred to as a "crosslinkable binaphthalene compound (Bi-3)."

[0115] [Crosslinkable triazine compound (Bi-1)] The crosslinkable triazine compound is preferably a compound represented by the following formula (b1). [ka]

[0116] In formula (b1), Ar b1 , Ar b2 , and Ar b3 are each independently an aromatic group-containing group. b1 , R b2 , and R b3 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, a cyano group, -O-CO-NH-X b4 X is a group represented by —NCO, a glycidyloxy group, or a thiiran-2-ylmethyloxy group. b1 , X b2 , and X b3 are each independently -NR b4 -, -O-, or -S-. X b4 is a divalent organic group. b1 , R b2 , and R b3 Two or three of R are glycidyloxy groups or thiiran-2-ylmethyloxy groups. b4 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. b1 Ar b1 The aromatic group is bonded to the aromatic ring in the aromatic group-containing group. X b2 Ar b2 The aromatic group is bonded to the aromatic ring in the aromatic group-containing group. X b3 Ar b3 The aromatic group bonded to the aromatic ring in the aromatic group-containing group.

[0117] In formula (b1), Ar b1 , Ar b2 , and Ar b3 The aromatic group-containing group as Ar1 The aromatic group-containing group is the same as Ar b1 , Ar b2 , and Ar b3 are preferably the same aromatic group-containing group. In formula (b1), R b4 is R in the above formula (A1). a2 is the same as:

[0118] R b1 , R b2 , and R b3 The number of carbon atoms in the alkyl group R is not particularly limited. b1 , R b2 , and R b3 The alkyl group preferably has 1 or more and 6 or less carbon atoms, and more preferably has 1 or more and 4 or less carbon atoms. R b1 , R b2 , and R b3 Specific examples of the alkyl group as include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.

[0119] R b1 , R b2 , and R b3 The number of carbon atoms in the alkoxy group as R is not particularly limited. b1 , R b2 , and R b3 The alkoxy group as the alkyl group preferably has 1 or more and 6 or less carbon atoms, and more preferably has 1 or more and 4 or less carbon atoms. R b1 , R b2 , and R b3 Specific examples of the alkoxy group as include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, and an n-hexyloxy group.

[0120] R b1 , R b2 , or Rb3 But -O-CO-NH-X b4 When the group is represented by —NCO, it is —O—CO—NH—X b4 The group represented by -NCO is Ar b1 , Ar b2 , and Ar b3 The hydroxyl group bonded to the aromatic group-containing group as shown in formula (b1) can be introduced into the compound represented by formula (b1) by reacting an excess amount of a diisocyanate compound with the hydroxyl group bonded to the aromatic group-containing group as shown in formula (b1). X b4 is a divalent organic group. b4 is a divalent organic group, typically a residue obtained by removing two isocyanate groups from a diisocyanate compound.

[0121] -O-CO-NH-X b4 Examples of diisocyanate compounds that can be used to introduce a group represented by -NCO include 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, and chain aliphatic diisocyanates such as dimer acid diisocyanate; 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexylisocyanate (isophorone diisocyanate), bis-(4-isocyanatocyclohexyl)methane, and norethoxysilane. Alicyclic diisocyanates such as bornane diisocyanate; and aromatic diisocyanates such as 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, crude diphenylmethane diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 3,3'-dimethyl-4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatodiphenylmethane, 1,5-naphthylene diisocyanate, 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, and α,α,α',α'-tetramethylxylylene diisocyanate.

[0122] R b1 , R b2 , and R b3 The group -X is a crosslinkable group. b4 -CO-NH-X b5 A group represented by -NCO, a glycidyloxy group, and a thiiran-2-ylmethyloxy group are preferred, and a glycidyloxy group and a thiiran-2-ylmethyloxy group are more preferred.

[0123] Suitable examples of the compound represented by formula (b1) include the following compounds: [ka]

[0124] [ka]

[0125] [ka]

[0126] [ka]

[0127] [Bridgeable fluorene compound (Bi-2)] As the crosslinkable fluorene compound (Bi-2), a compound represented by the following formula (b2) is preferred, since it is easy to synthesize and obtain, has good crosslinking reactivity, and easily gives a cured product with a high refractive index. [ka] (In formula (b2), W 1 and W 2 are each independently represented by the following formula (b2-1): [ka] is a group represented by In formula (b2-1), ring Z represents an aromatic hydrocarbon ring, X represents a single bond or a group represented by -S-, and R 1 represents a single bond, an alkylene group having 1 to 4 carbon atoms, or an alkyleneoxy group having 1 to 4 carbon atoms, and R 1 is an alkyleneoxy group, the oxygen atom in the alkyleneoxy group is bonded to the ring Z, and R 2 is a monovalent hydrocarbon group, a hydroxyl group, -OR 4a a group represented by -SR 4b groups represented by the formula (I), acyl groups, alkoxycarbonyl groups, halogen atoms, nitro groups, cyano groups, mercapto groups, carboxy groups, amino groups, carbamoyl groups, -NHR 4c a group represented by -N(R 4d ) a group represented by the formula (2), a sulfo group, or a monovalent hydrocarbon group, -OR 4a a group represented by -SR 4b groups represented by the formula (I), acyl groups, alkoxycarbonyl groups, -NHR 4c or -N(R 4d At least some of the hydrogen atoms bonded to carbon atoms in the group represented by formula (2) are monovalent hydrocarbon groups, hydroxyl groups, -OR 4a a group represented by -SR 4b groups represented by the formula (I), acyl groups, alkoxycarbonyl groups, halogen atoms, nitro groups, cyano groups, mercapto groups, carboxy groups, amino groups, carbamoyl groups, -NHR 4c a group represented by -N(R 4d )2, a group substituted with a mesyloxy group or a sulfo group, and R 4a ~R 4d each independently represents a monovalent hydrocarbon group, m represents an integer of 0 or more, and R 3 is -CO-NH-X b4 -NCO group, a thiiran-2-ylmethyl group, or a glycidyl group; Ring Y 1 and ring Y 2 represent the same or different aromatic hydrocarbon rings, R 3a and R 3b each independently represents a cyano group, a halogen atom, or a monovalent hydrocarbon group, and n1 and n2 each independently represent an integer of 0 to 4.

[0128] In the above formula (b2-1), examples of ring Z include a benzene ring, a fused polycyclic aromatic hydrocarbon ring [for example, a fused bicyclic hydrocarbon ring (for example, a C naphthalene ring, etc.] 8-20 Fused bicyclic hydrocarbon rings, preferably C 10-16 Examples of the ring Z include fused dicyclic to tetracyclic aromatic hydrocarbon rings such as fused bicyclic hydrocarbon rings, fused tricyclic aromatic hydrocarbon rings (for example, anthracene ring, phenanthrene ring, etc.). Ring Z is preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring. 1 and W 2 are each independently a group represented by formula (b2-1), and therefore W 1 and W 2 Each contains the ring Z. 1 Rings Z and W contained in 2 and the rings Z contained in may be the same or different. For example, one ring may be a benzene ring and the other ring may be a naphthalene ring, but it is particularly preferred that both rings are naphthalene rings.

[0129] Also, W 1 and W 2 The substitution position of ring Z bonded via X to the carbon atom to which both of are directly bonded is not particularly limited. For example, when ring Z is a naphthalene ring, the group corresponding to ring Z bonded to the carbon atom may be a 1-naphthyl group, a 2-naphthyl group, etc.

[0130] In formula (b2-1), X independently represents a single bond or a group represented by -S-, and is typically a single bond.

[0131] In formula (b2-1), R 1 Examples of the alkylene groups include a single bond; an alkylene group having 1 to 4 carbon atoms, such as a methylene group, an ethylene group, a trimethylene group, a propylene group, and a butane-1,2-diyl group; and an alkyleneoxy group having 1 to 4 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, and a propyleneoxy group. 2-4 Alkylene group (especially C such as ethylene group, propylene group, etc.)2-3 alkylene group); C 2-4 Alkyleneoxy group (especially C such as ethyleneoxy group, propyleneoxy group, etc.) 2-3 An alkylene group is preferred, and a single bond is more preferred. 1 When W is an alkyleneoxy group, the oxygen atom in the alkyleneoxy group bonds to the ring Z. 1 and W 2 are each independently a group represented by formula (b2-1), and therefore W 1 and W 2 are divalent groups R 1 Includes: W 1 R included in 1 and W 2 R included in 1 may be the same or different.

[0132] In formula (b2-1), R 2 Examples of the alkyl group include alkyl groups (e.g., C groups such as methyl, ethyl, propyl, isopropyl, and butyl groups). 1-12 Alkyl groups, preferably C 1-8 Alkyl groups, more preferably C 1-6 alkyl group, cycloalkyl group (cyclohexyl group, etc.) 5-10 Cycloalkyl groups, preferably C 5-8 Cycloalkyl groups, more preferably C 5-6 cycloalkyl groups, etc.), aryl groups (e.g., phenyl, tolyl, xylyl, naphthyl groups, etc.) 6-14 Aryl groups, preferably C 6-10 an aryl group, more preferably C 6-8 aryl group, etc.), aralkyl group (benzyl group, phenethyl group, etc.) 6-10 Aryl-C 1-4 Monovalent hydrocarbon groups such as alkyl groups; hydroxyl groups; alkoxy groups (C groups such as methoxy, ethoxy, propoxy, and butoxy groups) 1-12 Alkoxy groups, preferably C 1-8 Alkoxy groups, more preferably C 1-6 alkoxy groups, etc.), cycloalkoxy groups (cyclohexyloxy groups, etc.) 5-10cycloalkoxy groups, etc.), aryloxy groups (phenoxy groups, etc.) 6-10 aryloxy group), aralkyloxy group (e.g., C 6-10 Aryl-C 1-4 -OR (e.g., alkyloxy group) 4a [wherein R 4a represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above); an alkylthio group (such as a methylthio group, an ethylthio group, a propylthio group, or a butylthio group); 1-12 Alkylthio groups, preferably C 1-8 Alkylthio groups, more preferably C 1-6 alkylthio groups, cycloalkylthio groups (cyclohexylthio groups, etc.) 5-10 cycloalkylthio groups, arylthio groups (phenylthio groups, etc.) 6-10 arylthio group), aralkylthio group (e.g., C 6-10 Aryl-C 1-4 -SR (e.g., alkylthio group) 4b [wherein R 4b represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above); an acyl group (such as an acetyl group) 1-6 acyl group, etc.); alkoxycarbonyl group (C such as methoxycarbonyl group) 1-4 Alkoxy-carbonyl group, etc.; halogen atoms (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.); nitro group; cyano group; mercapto group; carboxy group; amino group; carbamoyl group; alkylamino group (methylamino group, ethylamino group, propylamino group, butylamino group, etc. C 1-12 Alkylamino groups, preferably C 1-8 Alkylamino groups, more preferably C 1-6 alkylamino group, etc.), cycloalkylamino group (cyclohexylamino group, etc.) 5-10 cycloalkylamino group, etc.), arylamino group (phenylamino group, etc. C 6-10 arylamino group), aralkylamino group (e.g., C 6-10 Aryl-C 1-4 -NHR (e.g., alkylamino group) 4c[wherein R 4c represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above); a dialkylamino group (such as a dimethylamino group, a diethylamino group, a dipropylamino group, or a dibutylamino group); 1-12 alkyl)amino groups, preferably di(C 1-8 alkyl)amino group, more preferably di(C 1-6 alkyl)amino group, dicycloalkylamino group (dicyclohexylamino group, etc.), 5-10 cycloalkyl)amino group, diarylamino group (diphenylamino group, etc.) 6-10 aryl)amino group), diaralkylamino group (e.g., di(C 6-10 Aryl-C 1-4 -N(R alkyl)amino group) 4d )2 [wherein R 4d each independently represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above); a (meth)acryloyloxy group; a sulfo group; the above monovalent hydrocarbon groups, -OR 4a a group represented by -SR 4b groups represented by the formula (I), acyl groups, alkoxycarbonyl groups, -NHR 4c or -N(R 4d At least some of the hydrogen atoms bonded to carbon atoms in the group represented by formula (2) are the above monovalent hydrocarbon group, hydroxyl group, -OR 4a a group represented by -SR 4b groups represented by the formula (I), acyl groups, alkoxycarbonyl groups, halogen atoms, nitro groups, cyano groups, mercapto groups, carboxy groups, amino groups, carbamoyl groups, -NHR 4c a group represented by -N(R 4d ) 2, a group substituted with a (meth)acryloyloxy group, a mesyloxy group, or a sulfo group [for example, an alkoxyaryl group (e.g., a C group such as a methoxyphenyl group] 1-4 Alkoxy C 6-10 aryl group), alkoxycarbonylaryl group (e.g., methoxycarbonylphenyl group, ethoxycarbonylphenyl group, etc. 1-4 Alkoxy-carbonyl C 6-10aryl group, etc.)].

[0133] Among these, the representative is R 2 is a monovalent hydrocarbon radical, -OR 4a a group represented by -SR 4b groups represented by the formula (I), acyl groups, alkoxycarbonyl groups, halogen atoms, nitro groups, cyano groups, -NHR 4c a group represented by -N(R 4d ) 2, etc.

[0134] Preferred R 2 Examples of the alkyl group include monovalent hydrocarbon groups [e.g., alkyl groups (e.g., C 1-6 alkyl groups), cycloalkyl groups (e.g., C 5-8 cycloalkyl groups), aryl groups (e.g., C 6-10 aryl groups), aralkyl groups (e.g., C 6-8 Aryl-C 1-2 alkyl group), etc.], alkoxy group (C 1-4 Alkoxy groups, etc. In particular, R 2a and R 2b is an alkyl group [C 1-4 alkyl groups (especially methyl groups), etc.], aryl groups [e.g., C 6-10 It is preferably a monovalent hydrocarbon group (particularly an alkyl group) such as an aryl group (particularly a phenyl group).

[0135] When m is an integer of 2 or more, multiple R 2 may be different from each other or may be the same. 1 R included in 2 and W 2 R included in 2 may be the same or different.

[0136] In formula (b2-1), R 2 The number m can be selected depending on the type of ring Z, and may be, for example, 0 to 4, preferably 0 to 3, and more preferably 0 to 2. 1 m and W in 2The m's in the formula may be the same or different.

[0137] In the above formula (b2-1), R 3 is -CO-NH-X b4 The group represented by -NCO, a thiiran-2-ylmethyl group, or a glycidyl group. Among these groups, a thiiran-2-ylmethyl group and a glycidyl group are preferred. -CO-NH-X b4 With respect to the group represented by —NCO, —O—CO—NH—X b4 It is the same as the group represented by —NCO.

[0138] W 1 R included in 3 and W 2 R included in 3 and may be the same or different. 1 R included in 3 and W 2 R included in 3 and preferably both are a thiiran-2-ylmethyl group or a glycidyl group, and more preferably both are the same group selected from the group consisting of a thiiran-2-ylmethyl group and a glycidyl group.

[0139] In the above formula (b2), ring Y 1 and ring Y 2 Examples of the aromatic hydrocarbon ring include a benzene ring, a fused polycyclic aromatic hydrocarbon ring [e.g., a fused bicyclic hydrocarbon ring (e.g., a C naphthalene ring, etc.] 8-20 Fused bicyclic hydrocarbon rings, preferably C 10-16 condensed bicyclic hydrocarbon rings, condensed tricyclic aromatic hydrocarbon rings (for example, anthracene ring, phenanthrene ring, etc.), and other condensed dicyclic to tetracyclic aromatic hydrocarbon rings. 1 and ring Y 2 is preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring. 1 and ring Y 2 may be the same or different, and for example, one ring may be a benzene ring and the other ring may be a naphthalene ring.

[0140] In the above formula (b2), R 3a and R 3b The substituents are usually non-reactive substituents such as a cyano group, a halogen atom (such as a fluorine atom, a chlorine atom, or a bromine atom), a monovalent hydrocarbon group [such as an alkyl group, an aryl group (C such as a phenyl group)], 6-10 Examples of the alkyl group include a cyano group or an alkyl group, and particularly preferably an alkyl group. Examples of the alkyl group include a C aryl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a t-butyl group. 1-6 Alkyl groups (e.g., C 1-4 Examples include alkyl groups, particularly methyl groups. When n1 is an integer of 2 or more, R 3a may be different from each other or may be the same. When n2 is an integer of 2 or more, R 3b may be different from each other or may be the same. 3a and R 3b and may be the same or different. 1 and ring Y 2 R 3a and R 3b The bonding positions (substitution positions) of are not particularly limited. The substitution numbers n1 and n2 are preferably 0 or 1, particularly 0. Note that n1 and n2 may be the same or different.

[0141] Among the compounds represented by the above formula (b2), particularly preferred specific examples include epoxy group-containing fluorene compounds such as 9,9-bis[4-[2-(glycidyloxy)ethoxy]phenyl]-9H-fluorene, 9,9-bis[4-[2-(glycidyloxy)ethyl]phenyl]-9H-fluorene, 9,9-bis[4-(glycidyloxy)-3-methylphenyl]-9H-fluorene, 9,9-bis[4-(glycidyloxy)-3,5-dimethylphenyl]-9H-fluorene, 9,9-bis(6-glycidyloxynaphthalen-1-yl)-9H-fluorene and 9,9-bis(5-glycidyloxynaphthalen-2-yl)-9H-fluorene; and compounds represented by the following formula:

[0142] [ka]

[0143] [ka]

[0144] [ka]

[0145] [ka]

[0146] [ka]

[0147] [Bridgeable binaphthalene compound (Bi-3)] The crosslinkable binaphthalene compound (Bi-3) is a compound having a bond of -O-CO-NH-X on binaphthalene such as 1,1'-binaphthalene. b4 A compound having two or more groups selected from the group represented by —NCO, a glycidyloxy group, and a thiiran-2-ylmethyloxy group bonded thereto is preferred. b4 Among the group represented by --NCO, the glycidyloxy group, and the thiiran-2-ylmethyloxy group, the glycidyloxy group and the thiiran-2-ylmethyloxy group are preferred. -O-CO-NH-X b4 With respect to the group represented by —NCO, —O—CO—NH—X b4 It is the same as the group represented by —NCO. The number of groups selected from glycidyloxy groups and thiiran-2-ylmethyloxy groups contained in the crosslinkable binaphthalene compound (Bi-3) is preferably 2 or more and 4 or less, more preferably 2 or 3, and even more preferably 2.

[0148] Specific preferred examples of the crosslinkable binaphthalene compound (B3) include 2,2'-diglycidyloxy-1,1'-binaphthalene, 2,2'-diglycidyloxy-3,3'-diglycidyloxycarbonyl-1,1'-binaphthalene, 2,2'-diglycidyloxy-6,6'-diglycidyloxycarbonyl-1,1'-binaphthalene, 2,2'-di(thiiran-2-ylmethyl)oxy-1,1'-binaphthalene, 2,2'-di(thiiran-2-ylmethyl)oxy-3,3'-di(thiiran-2-ylmethyl)oxycarbonyl-1,1'-binaphthalene, and 2,2'-di(thiiran-2-ylmethyl)oxy-6,6'-di(thiiran-2-ylmethyl)oxycarbonyl-1,1'-binaphthalene.

[0149] [Sulfur-containing compound (Bii)] The sulfur-containing compound (Bii) is a sulfur-containing compound containing two or more crosslinkable groups. The crosslinkable groups are as described above. However, a compound that does not contain any sulfur atoms other than the sulfur atom contained in the episulfide group does not fall under the category of the sulfur-containing compound (Bii).

[0150] The crosslinkable group contained in the sulfur-containing compound (Bii) is preferably a glycidyl group or a thiiran-2-ylmethyl group, more preferably a thiiran-2-ylmethyl group.

[0151] A suitable example of the sulfur-containing compound (Bii) is a compound represented by the following formula (b4-1). R b5 -CH2-S-[-(CH2) p -S-] q -CH2-R b5 ···(b4-1) In formula (b4-1), R b5 is a thiiran-2-yl group. p is an integer of 0 or more and 4 or less. q is an integer of 0 or more and 2 or less. Specific examples of the compound represented by formula (b4-1) include bis(thiiran-2-ylmethyl)sulfide, bis(thiiran-2-ylmethyl)methane, 1,2-bis(thiiran-2-ylmethyl)ethane, 1,3-bis(thiiran-2-ylmethyl)propane, 1,4-bis(thiiran-2-ylmethyl)butane, and bis(thiiran-2-ylmethylthioethyl)sulfide.

[0152] A suitable example of the sulfur-containing compound (Bii) is a compound represented by the following formula (b4-2). R b5 -CH2-S-(CH2) r -CHX-(CH2) s -S-CH2-R b5 ···(b4-2) In formula (b4-2), R b5 is a thiiran-2-yl group. CHX is a cyclohexanediyl group. r and s are each independently an integer of 0 to 4. Specific examples of the compound represented by formula (b4-2) include 1,3-bis(thiiran-2-ylmethylthio)cyclohexane, 1,4-bis(thiiran-2-ylmethylthio)cyclohexane, 1,3-bis(thiiran-2-ylmethylthiomethyl)cyclohexane, and 1,4-bis(thiiran-2-ylmethylthiomethyl)cyclohexane.

[0153] A suitable example of the sulfur-containing compound (Bii) is a compound represented by the following formula (b4-3). R b5 -CH2-S-(CH2) t -DTA-(CH2) u -S-CH2-R b5 ···(b4-3) In formula (b4-3), R b5 is a thiiran-2-yl group. DTA is a 1,4-dithianediyl group. t and u are each independently an integer of 0 to 4. Specific examples of the compound represented by formula (b4-3) include 2,5-bis(thiiran-2-ylmethylthio)-1,4-dithiane and 2,5-bis(thiiran-2-ylmethylthiomethyl)-1,4-dithiane.

[0154] A suitable example of the sulfur-containing compound (Bii) is a compound represented by the following formula (b4-4). R b5 -CH2-S-(CH2) v -Ph-(CH2) w -S-CH2-R b5 ···(b4-4) In formula (b4-4), R b5 is a thiiran-2-yl group. Ph is a phenylene group. v and w are each independently an integer of 0 to 4. Specific examples of the compound represented by formula (b4-4) include 1,3-bis(thiiran-2-ylmethylthio)benzene, 1,4-bis(thiiran-2-ylmethylthio)benzene, 1,3-bis(thiiran-2-ylmethylthiomethyl)benzene, and 1,4-bis(thiiran-2-ylmethylthiomethyl)benzene.

[0155] [Isocyanate compound (Biii)] The isocyanate compound (Biii) is a compound having two or more isocyanate groups in one molecule. The isocyanate compound (Biii) is a compound that does not fall under the category of the aromatic compound (Bi) or the sulfur-containing compound (Bii).

[0156] In order to ensure good stability over time of the non-photosensitive liquid composition, it is preferable that the isocyanate compound (Biii) is used as a blocked isocyanate compound obtained by reacting it with a known blocking agent. In the blocked isocyanate compound, the highly reactive isocyanate group is blocked with a blocking agent, and therefore the non-photosensitive liquid composition containing the blocked isocyanate compound has good stability over time.

[0157] The isocyanate compound (Biii) is not particularly limited as long as it is a compound having two or more isocyanate groups. Known isocyanate compounds (Biii) include linear aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and modified polyisocyanates thereof. The aromatic polyisocyanate is a polyisocyanate having an aromatic group. In the aromatic polyisocyanate, the isocyanate group may be bonded to either an aromatic group or an aliphatic group. These isocyanate compounds (Biii) may be used alone or in combination of two or more.

[0158] Examples of the chain aliphatic polyisocyanate include 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, and dimer acid diisocyanate.

[0159] Examples of alicyclic polyisocyanates include 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexane (isophorone diisocyanate), bis-(4-isocyanatocyclohexyl)methane, and norbornane diisocyanate.

[0160] Examples of aromatic polyisocyanates having an isocyanate group bonded to an aromatic group include 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, crude diphenylmethane diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 3,3'-dimethyl-4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatodiphenylmethane, and 1,5-naphthylene diisocyanate.

[0161] Examples of aromatic polyisocyanates having an isocyanate group bonded to an aliphatic group include 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, and α,α,α',α'-tetramethylxylylene diisocyanate.

[0162] Examples of blocking agents include alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, 2-ethylhexanol, and butyl cellosolve; phenols such as phenol, cresol, and 2-hydroxypyridine; amines such as diisopropylamine; lactams such as ε-caprolactam, δ-valerolactam, and γ-butyrolactam; oximes such as formaldehyde oxime, acetaldehyde oxime, acetone oxime, methyl ethyl ketoxime, and methyl isobutyl ketoxime; ketoenols such as acetylacetone; pyrazoles such as 1,2-pyrazole and 3,5-dimethylpyrazole; and triazoles such as triazole. Among these blocking agents, lactams, oximes, and pyrazoles are preferred, and ε-caprolactam, methyl ethyl ketoxime, and 3,5-dimethylpyrazole are more preferred.

[0163] [Aliphatic compound (Biv)] The aliphatic compound (Biv) is an aliphatic compound containing two or more crosslinkable groups. The aliphatic compound (Biv) is a compound that does not fall under the category of the sulfur-containing compound (Bii) or the isocyanate compound (Biii).

[0164] The structure of the aliphatic compound (Biv) may be a chain structure, a cyclic structure, or a combination of a chain structure and a cyclic structure. The crosslinkable group contained in the aliphatic compound (Biv) is preferably a glycidyl group or a thiiran-2-ylmethyl group.

[0165] Examples of the aliphatic compound (Biv) include compounds in which the hydrogen atoms in two or more hydroxyl groups among the hydroxyl groups of various aliphatic polyols are substituted with glycidyl groups or thiiran-2-ylmethyl groups. Suitable examples of polyols that provide the aliphatic compound (Biv) include ethylene glycol, propylene glycol (propane-1,2-diol), propane-1,3-diol, butane-1,4-diol, pentane-1,5-diol, hexane-1,6-diol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, glycerin, diglycerin, triglycerin, trimethylolpropane, pentaerythritol, dipentaerythritol, 1,4-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, sorbitol, and isosorbide.

[0166] Specific preferred examples of the aliphatic compound (Biv) having an epoxy group include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, propane-1,3-diol diglycidyl ether, butane-1,4-diol diglycidyl ether, pentane-1,5-diol diglycidyl ether, hexane-1,6-diol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, and dipropylene glycol diglycidyl ether. ether, tripropylene glycol diglycidyl ether, glycerin-1,3-diglycidyl ether, glycerin-1,2-diglycidyl ether, diglycerin diglycidyl ether, diglycerin triglycidyl ether, diglycerin tetraglycidyl ether, triglycerin diglycidyl ether, triglycerin triglycidyl ether, triglycerin tetraglycidyl ether, triglycerin pentaglycidyl ether, triglycerin, triglycerin hexaglycidyl ether Examples of the glycidyl ether include glyceryl ether, trimethylolpropane diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol diglycidyl ether, pentaerythritol triglycidyl ether, pentaerythritol tetraglycidyl ether, dipentaerythritol diglycidyl ether, dipentaerythritol triglycidyl ether, dipentaerythritol tetraglycidyl ether, dipentaerythritol pentaglycidyl ether, dipentaerythritol hexaglycidyl ether, 1,4-cyclohexanediol diglycidyl ether, 1,3-cyclohexanediol diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, 1,3-cyclohexanedimethanol diglycidyl ether, sorbitol diglycidyl ether, sorbitol triglycidyl ether, sorbitol tetraglycidyl ether, sorbitol pentaglycidyl ether, sorbitol hexaglycidyl ether, and isosorbide diglycidyl ether.

[0167] Suitable specific examples of the aliphatic compound (Biv) having an episulfide group include compounds in which the glycidyl group in the compounds listed above as specific examples of the aliphatic compound (Biv) having an epoxy group is substituted with a thiiran-2-ylmethyl group.

[0168] The amount of the crosslinkable compound (B) used in the non-photosensitive liquid composition is not particularly limited as long as the desired effect is not impaired. In terms of good curability of the non-photosensitive liquid composition and excellent solvent resistance of the cured product, the amount of the crosslinkable compound (B) used in the non-photosensitive liquid composition is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 30 parts by mass or more and 150 parts by mass or less, relative to 100 parts by mass of the polymer (A).

[0169] <Organic solvent (S)> As the organic solvent (S), a solvent capable of dissolving the polymer (A) can be preferably used. Examples of the organic solvent (S) include N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylformamide, N-methylformamide, N,N-dimethylpropionic acid amide, N,N-dimethylisobutyramide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-methyl-2-piperidone, N-acetylpyrrolidine, N,N'-dimethylethyleneurea (1,3-dimethyl-2-imidazolidinone), N,N'-dimethylpropyleneurea, N,N,N'-dimethylethyleneurea, ... Nitrogen-containing polar organic solvents such as ',N'-tetramethylmalonamide, N-methylcaprolactam, N,N,N',N'-tetramethylurea, 3-methoxy-N,N-dimethylpropanamide, and 3-butoxy-N,N-dimethylpropanamide; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone, diethyl ketone, methyl isobutyl ketone, methyl n-butyl ketone, cyclopentanone, and cyclohexanone; tetrahydrofuran, and 1,4-dioxane aromatic hydrocarbons such as toluene, p-xylene, o-xylene, m-xylene, ethylbenzene, and styrene; glycol monoalkyl ether acetates such as ethylene glycol methyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and diethylene glycol monoethyl ether acetate; glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, and 1-methoxy-2-butanol;Dialkyl ethers of glycols such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and triethylene glycol dimethyl ether; glycols such as ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, hexylene glycol, and diethylene glycol; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, 1-pentanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 2-methyl-1-pentanol, 1-octanol, 2-ethylhexanol, allyl alcohol, cyclohexanol, diacetone alcohol, furfuryl alcohol, tetrahydrofurfuryl alcohol, and benzyl alcohol; esters such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, and isobutyl acetate; and lactones such as γ-butyrolactone. The organic solvent (S) preferably contains a ketone, a nitrogen-containing polar organic solvent, a glycol monoalkyl ether acetate, or a glycol monoalkyl ether, since the polymer (A) is particularly likely to dissolve therein.

[0170] The amount of organic solvent (S) used is not particularly limited as long as the non-photosensitive liquid composition can be molded into a desired shape. The organic solvent (S) is used so that the solids concentration of the non-photosensitive liquid composition is preferably 1% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 40% by mass or less.

[0171] <Thermal acid generator (C)> The polymer (A) is R a1 When the non-photosensitive liquid composition has a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid-dissociable group as the non-photosensitive liquid composition, the non-photosensitive liquid composition further contains a thermal acid generator (C). The thermal acid generator (C) is not particularly limited as long as it is a compound that generates an acid when heated, and any known thermal acid generator can be appropriately selected as the thermal acid generator (C). As the thermal acid generator (C), an onium salt-type thermal acid generator is preferred in terms of its ability to generate acid upon heating. Examples of onium salts include sulfonium ions, ammonium ions, iodonium ions, and phosphonium ions. These are preferred because they are stable and easy to handle. Among these onium salts, sulfonium ions and iodonium ions are more preferred, with sulfonium ions being even more preferred.

[0172] The amount of the thermal acid generator (C) used is not particularly limited as long as the desired effect is not impaired. The amount of the thermal acid generator (C) used is preferably 0.1% by mass or more and 15% by mass or less, and more preferably 0.5% by mass or more and 10% by mass or less, based on the mass of the solid content of the non-photosensitive liquid composition.

[0173] <Surfactant (D)> The non-photosensitive liquid composition may further contain a surfactant (surface conditioner) to improve film-forming properties, coating properties, defoaming properties, leveling properties, etc. The surfactant may be used alone or in combination of two or more. Examples of the surfactant include silicone-based surfactants, fluorine-based surfactants, and polymeric wetting and dispersing agents, and polymeric wetting and dispersing agents are particularly preferred from the viewpoint of improving film-forming properties.

[0174] Specific examples of silicone surfactants include BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341, BYK-344, BYK-345, BYK-346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, and BYK-390 (manufactured by BYK Chemie).

[0175] Specific examples of fluorine-based surfactants include F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, and MCF-350. SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF-1132, TF-1027SF, TF-1441, TF-1442 (manufactured by DIC Corporation); Polyfox series PF-636, PF-6320, PF-656, PF-6520 (manufactured by Omnova Corporation);

[0176] Specific examples of polymeric wetting and dispersing agents include BYK-140, BYK-145, BYK-161, BYK-162, BYK-163, BYK-164, BYK-167, BYK-168, BYK-170, BYK-171, BYK-174, BYK-180, BYK-182, BYK-184, BYK-185, BYK-2050, BYK-2055, BYK-2015, and BYK-9077 (manufactured by BYK Chemie).

[0177] The amount of the surfactant used is not particularly limited. In view of the film-forming property, coating property, defoaming property, leveling property, etc. of the non-photosensitive liquid composition, the amount of the surfactant used is, for example, preferably 0.01% by mass or more and 2% by mass or less, and more preferably 0.05% by mass or more and 1% by mass or less, relative to the mass of the solid content of the non-photosensitive liquid composition.

[0178] <Other ingredients> The non-photosensitive liquid composition may contain additives such as a defoaming agent, a silane coupling agent, a colorant (pigment, dye), a crosslinking agent, etc. Any of these additives may be a conventionally known compound.

[0179] <Method for producing non-photosensitive liquid composition> The non-photosensitive liquid composition can be produced by mixing the above-described essential components with optional components as needed, and then dissolving each component uniformly in an organic solvent (S). The non-photosensitive liquid composition may be filtered using a filter with a desired mesh size as needed.

[0180] <Method for manufacturing molded body> molding the non-photosensitive liquid composition; and removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating, thereby producing a molded article.

[0181] The molding method is not particularly limited and can be appropriately selected depending on the shape of the molded product. Examples of molding methods include coating and casting into a mold. In addition, the non-photosensitive liquid composition can be molded into a desired three-dimensional shape using a so-called 3D printing method. Hereinafter, a method for producing a film will be described as a typical example of a method for producing a molded article.

[0182] First, the non-photosensitive liquid composition is applied onto a desired substrate to form a coating film.

[0183] The method for applying the non-photosensitive liquid composition onto a substrate is not particularly limited. For example, the non-photosensitive liquid composition can be applied to a substrate to a desired film thickness using a contact transfer type coating device such as a roll coater, a reverse coater, a bar coater, or a slit coater, or a non-contact type coating device such as a spinner (rotary coating device) or a curtain flow coater, to form a coating film.

[0184] The coating film is then heated to remove the organic solvent (S) from the coating film. The heating temperature is appropriately determined taking into consideration the boiling point of the organic solvent (S) and the temperature at which the acid generator (C) generates an acid. The temperature to which the coating film is heated is, for example, preferably from 100° C. to 400° C., more preferably from 150° C. to 300° C. The heating time is preferably from 30 seconds to 30 minutes, more preferably from 1 minute to 20 minutes.

[0185] The molded article thus obtained exhibits a high refractive index. Specifically, the refractive index of the molded article is preferably 1.74 or more, more preferably 1.75 or more, as the refractive index of light with a wavelength of 550 nm. Molded articles exhibiting such a high refractive index are preferably used as various optical components. The optical components are preferably films or microlenses. Optical components made from molded articles of non-photosensitive liquid compositions are preferably used in various optical elements. Molded articles in the form of films can be used as high refractive index films in various optical elements. Molded articles in the form of microlenses can be particularly preferably used in optical elements such as CCDs and CMOSs.

[0186] As described above, the present inventors provide the following (1) to (18). (1) Formula (A1) below: [ka] (In formula (A1), Ar 1 , and Ar 2 is an aromatic group-containing group, R a1 represents a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group, The acetal protecting group is -CHR A1 -OR A2 is a group represented by R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, R A1 , and R A2 may be bonded to each other to form a ring, X 1 , and X 2 are each independently -NR a2 -, -O-, or -S-; R a2represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 Ar 1 and the aromatic ring in the aromatic group-containing group is X 2 Ar 2 It bonds to an aromatic ring in the aromatic group-containing group. Contains a constitutional unit represented by At least a part of the ends of the molecular chain contains a compound represented by the following formula (A1-1): -X 2 -X 3 -X 4 ···(A1-1) (In formula (A1-1), X 2 is X in formula (A1) 2 is the same as X 3 is a divalent hydrocarbon group, X 4 -OR a3 , or -N(R a3 )2, R a3 represents a hydrogen atom or an alkyl group which may have a substituent, X 3 When the hydrocarbon group as X is an aromatic group-containing group, 4 is not an amino group.) A polymer having a group represented by the formula: (2)R a1 is a tert-butoxycarbonylamino group or a tert-butoxycarbonyloxy group. (3)X 2 But, -NR a2 -, or -O-. (4)X 3 The polymer according to any one of (1) to (3), wherein the divalent hydrocarbon group is an alkylene group. (5) Formula (A2) below: [ka] (In formula (A2), Ar2 , and Ar 3 is an aromatic group-containing group, X 1 , and X 2 are each independently -NR a2 -, -O-, or -S-; R a2 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 Ar 3 and the aromatic ring in the aromatic group-containing group is X 2 Ar 2 It bonds to an aromatic ring in the aromatic group-containing group. The polymer according to any one of (1) to (4), which contains a structural unit represented by (6) A dihalotriazine compound and a compound represented by the following formulas (A5-1) to (A5-3): Ar 2 -(NR a2 H)2···(A5-1) Ar 2 -(OH)2···(A5-2) Ar 2 -(SH)2···(A5-3) (In formulas (A5-1) to (A5-3), Ar 2 is an aromatic group-containing group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. with a compound represented by any one of The dihalotriazine compound is represented by the following formula (A3): [ka] (In formula (A3), Hal is a halogen atom, Ar 1 is an aromatic group-containing group, R a1represents a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group, The acetal protecting group is -CHR A1 -OR A2 is a group represented by R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, R A1 , and R A2 may be bonded to each other to form a ring, X 1 are each independently -NR a2 -, -O-, or -S-; R a2 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 Ar 1 It bonds to an aromatic ring in the aromatic group-containing group. The compound includes a compound represented by Condensation of a dihalotriazine compound with a compound represented by any one of formulas (A5-1) to (A5-3) is carried out using the following formulas (A7-1) to (A7-3): X 4 -X 3 -NR a2 H···(A7-1) X 4 -X 3 -OH···(A7-2) X 4 -X 3 -SH···(A7-3) (In formulas (A7-1) to (A7-3), X 3 , and X 4 is X in formula (A1-1) 3 , and X 4 is the same as R a2 is R in Equation (1). a2 is the same as or in the presence of a compound represented by A method for producing a polymer according to (1), comprising reacting a condensation product of a dihalotriazine compound and a compound represented by any one of formulas (A5-1) to (A5-3) with a compound represented by any one of formulas (A7-1) to (A7-3). (7) The dihalotriazine compound is represented by the following formula (A6): [ka] (In formula (A6), Hal is a halogen atom, Ar 3 is an aromatic group-containing group, X 1 are each independently -NR a2 -, -O-, or -S-; R a2 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 Ar 3 It bonds to an aromatic ring in the aromatic group-containing group. The method according to (6), comprising the compound represented by the formula: (8) A method for producing a solvent comprising a triazine ring-containing polymer (A) and an organic solvent (S), The triazine ring-containing polymer (A) is a polymer according to any one of (1) to (5), R a1 is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid-dissociable group, the non-photosensitive liquid composition further comprising a thermal acid generator (C). (9) The non-photosensitive liquid composition according to (8), further comprising a crosslinkable compound (B). (10) The crosslinkable compound (B) is an aromatic compound (Bi) containing two or more crosslinkable groups and a triazine ring, a fluorene ring which may have a substituent, or a binaphthalene ring which may have a substituent, or a sulfur-containing compound (Bii) containing two or more crosslinkable groups, or an isocyanate compound (Biii) containing two or more isocyanate groups, or an aliphatic compound (Biv) containing two or more crosslinkable groups, The sulfur-containing compound (Bii) is a compound that does not fall under the category of the aromatic compound (Bi), The isocyanate compound (Biii) is a compound that does not fall under the category of the aromatic compound (Bi) or the sulfur-containing compound (Bii), The non-photosensitive liquid composition according to (9), wherein the aliphatic compound (Biv) is a compound that does not fall under the category of the sulfur-containing compound (Bii) and the isocyanate compound (Biii). (11) The non-photosensitive liquid composition according to (10), wherein the crosslinkable group is an epoxy group, an episulfide group, or an isocyanate group. (12) The non-photosensitive liquid composition according to any one of (8) to (11), wherein the organic solvent (S) is a ketone, a nitrogen-containing polar organic solvent, a glycol monoalkyl ether acetate, or a glycol monoalkyl ether. (13) Molding the non-photosensitive liquid composition according to any one of (8) to (12); and removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating. (14) The method for producing a molded article according to (13), wherein the non-photosensitive liquid composition is formed into a film by applying the non-photosensitive liquid composition onto a substrate. (15) A molded article of the non-photosensitive liquid composition according to any one of (8) to (12). (16) An optical component made of the molded article according to (15). (17) The optical component according to (16), which is a film or a microlens. (18) An optical element comprising the optical component according to (16). [Example]

[0187] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples.

[0188] Example 1 Cyanuric chloride (3.69 g, 20 mmol) dissolved in 30 mL of THF was added to a 200 mL three-neck flask, and the liquid in the flask was cooled to 0° C. in an ice bath. Next, while stirring the liquid in the flask, 3-tert-butoxycarbonylaminoaniline (4.17 g, 20 mmol) dissolved in 90 mL of THF was added dropwise to the flask. After the dropwise addition, the reaction solution in the flask was stirred for 2 hours. A potassium carbonate solution prepared by dissolving potassium carbonate (1.66 g, 12 mmol) in 30 mL of purified water was added to the reaction solution, and the mixture was stirred at room temperature for 20 minutes. The reaction mixture and 150 mL of ethyl acetate were placed in a separatory funnel, and the aqueous phase was removed by separation. THF and ethyl acetate were removed from the collected organic phase, yielding a solid residue. The resulting residue was purified by silica gel chromatography to obtain 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine, which is a dihalotriazine compound having the following structure. [ka]

[0189] A 500 mL three-neck flask was charged with m-phenylenediamine (3.90 g, 36.1 mmol). 150 mL of N,N-dimethylacetamide (DMAc) was added to the flask, and m-phenylenediamine was dissolved in the DMAc. The solution in the flask was heated to 70 °C, and then 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine (5.15 g, 14.4 mmol) and 2,4-dichloro-6-(4-cyanophenyl)amino-1,3,5-triazine (5.76 g, 21.7 mmol) dissolved in 150 mL of DMAc were added to the flask to initiate the polymerization reaction. After continuing polymerization at 70°C for 24 hours, the reaction mixture was cooled to room temperature, and 2-aminoethanol (2.2 mL, 36.1 mmol) was added to the cooled reaction mixture, followed by stirring at room temperature for 1 hour. The reaction solution was then mixed with a mixture of 10 mL of 28% by mass aqueous ammonia, 750 mL of water, and 250 mL of methanol to precipitate the resulting polymer A-1. The precipitate was collected by filtration and washed with 1000 mL of water and 20 mL of hexane. The washed precipitate was then dried in a vacuum dryer at 100°C for 24 hours to obtain 11.4 g of polymer A-1. The weight-average molecular weight (Mw, polystyrene equivalent) of the resulting polymer A-1 measured by GPC was 5,700. The two types of units constituting polymer A-1 are shown below. Polymer A-1 has a 2-hydroxyethylamino group as a terminal group represented by formula (A1-1). [ka]

[0190] Example 2 9.1 g of Polymer A-2 was obtained in the same manner as in Example 1, except that the amount of m-phenylenediamine was changed from 3.90 g (36.1 mmol) to 3.00 g (27.8 mmol). The weight average molecular weight (Mw, polystyrene equivalent) of the obtained polymer A-2 measured by GPC was 4,500.

[0191] Example 3 7.8 g of Polymer A-3 was obtained in the same manner as in Example 1, except that the amount of m-phenylenediamine was changed from 3.90 g (36.1 mmol) to 2.60 g (24.1 mmol). The weight average molecular weight (Mw, polystyrene equivalent) of the obtained polymer A-3 measured by GPC was 4,000.

[0192] [Synthesis Example 1] 11.2 g of polymer A-4 was obtained in the same manner as in Example 1, except that 36.1 mmol of 2-aminoethanol was changed to 36.1 mmol of propylamine. The weight average molecular weight (Mw, polystyrene equivalent) of the obtained polymer A-4 measured by GPC was 5,700. Polymer A-4 has a propylamino group as a terminal group.

[0193] [Synthesis Example 2] 11.5 g of polymer A-5 was obtained in the same manner as in Example 1, except that 36.1 mmol of aniline was used instead of 36.1 mmol of 2-aminoethanol. The weight average molecular weight (Mw, polystyrene equivalent) of the obtained polymer A-5 measured by GPC was 5,700. Polymer A-5 has a phenylamino group as a terminal group.

[0194] [Examples 4 to 6, Comparative Examples 1 and 2] 2.0 parts by mass of a polymer of the type shown in Table 1, 0.4 parts by mass of a crosslinkable compound having the structure shown below, and 0.001 parts by mass of a surfactant (BYK-310, manufactured by BYK Chemie) were dissolved in 6.5 parts by mass of an organic solvent (cyclopentanone) to obtain non-photosensitive liquid compositions for each of the Examples and Comparative Examples. [ka]

[0195] Table 1 shows the weight average molecular weight (Mw) and dispersity (Mw / Mn) of the polymers used in the examples and comparative examples.

[0196] Using the obtained non-photosensitive liquid compositions of Examples 4 to 6, Comparative Example 1, and Comparative Example 2, heat resistance was evaluated according to the following method.

[0197] <Heat resistance evaluation method> The non-photosensitive liquid composition was applied onto a glass substrate using a spin coater, and the resulting coating film was heated at 100°C for 1 minute and then at 200°C for 10 minutes to obtain a cured film. The resulting cured film was heated in an oven at 220°C for 5 hours. The light transmittance T1 (%) at a light wavelength of 400 nm of the cured film before heating and the light transmittance T2 (%) at a light wavelength of 400 nm of the cured film after heating were measured. The decrease in light transmittance ΔT (%) due to heating was calculated using the following formula: ΔT(%)=T1(%)-T2(%) The heat resistance of the cured film was evaluated according to the following criteria, with A representing a good evaluation result. A: ΔT is less than 5%. B: ΔT is 5% or more.

[0198] <Refractive index measurement> The refractive index of the cured film formed by the above method at a light wavelength of 550 nm was measured using a spectroscopic ellipsometer (M-2000UI manufactured by J.A. Woollam Japan, Inc.). As a result, the refractive index of the cured films formed using the non-photosensitive liquid compositions of Examples 4 to 6, Comparative Example 1, and Comparative Example 2 was all 1.75 or higher.

[0199] [Table 1]

[0200] Examples 4 to 6 show that a non-photosensitive liquid composition containing a polymer having a unit (A1) represented by formula (A1) and a terminal group represented by formula (A1-1) provides a cured film having a high refractive index and excellent heat resistance. On the other hand, Comparative Examples 1 and 2 show that a non-photosensitive liquid composition containing a polymer that includes a unit (A1) represented by formula (A1) but does not have a terminal group represented by formula (A1-1) does not provide a cured film with excellent heat resistance.

Claims

1. The following formula (A1): 【Chemical 1】 (In formula (A1), Ar １ , and Ar ２ is an aromatic group-containing group, R ａ１ represents a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group, The acetal protecting group is —CHR Ａ１ -O-R Ａ２ is a group represented by R Ａ１ is a hydrogen atom or an alkyl group, R Ａ２ is an alkyl group, The R Ａ１ , and the R Ａ２ may be bonded to each other to form a ring, X １ , and X ２ are each independently -NR ａ２ -, -O-, or -S-; R ａ２ represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X １ is Ar １ and the aromatic group-containing group is bonded to an aromatic ring in the aromatic group-containing group as X ２ is Ar ２ and bonded to the aromatic ring in the aromatic group-containing group as Contains a constitutional unit represented by At least a part of the ends of the molecular chain contains a compound represented by the following formula (A1-1): -X ２ -X ３ -X ４ ・・・(A1-1) (In formula (A1-1), X ２ represents X in formula (A1). ２ is the same as X ３ is a divalent hydrocarbon group, X ４ is -OR ａ３ , or -N(R ａ３ ) ２ and R ａ３ represents a hydrogen atom or an alkyl group which may have a substituent, X ３ When the hydrocarbon group as X is an aromatic group-containing group, ４ is not an amino group.) A polymer having a group represented by the formula:

2. R ａ１ The polymer of claim 1, wherein is a tert-butoxycarbonylamino group or a tert-butoxycarbonyloxy group.

3. The X ２ But, -NR ａ２ The polymer according to claim 1, wherein the aryl group is - or -O-.

4. The X ３ The polymer according to claim 1 , wherein the divalent hydrocarbon group is an alkylene group.

5. The following formula (A2): 【Chemistry 2】 (In formula (A2), Ar ２ , and Ar ３ is an aromatic group-containing group, X １ , and X ２ are each independently -NR ａ２ -, -O-, or -S-; R ａ２ represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X １ is Ar ３ and the aromatic group-containing group is bonded to an aromatic ring in the aromatic group-containing group as X ２ is Ar ２ and bonded to the aromatic ring in the aromatic group-containing group as The polymer according to claim 1, comprising a structural unit represented by

6. A dihalotriazine compound and a compound of the following formulas (A5-1) to (A5-3): <h2 style=";text-align:left;direction:ltr">Ar<h2 style=";text-align:left;direction:ltr"> ２ <h2 style=";text-align:left;direction:ltr"> -(NR<h2 style=";text-align:left;direction:ltr"> ａ２ <h2 style=";text-align:left;direction:ltr"> H)<h2 style=";text-align:left;direction:ltr"> ２ <h2 style=";text-align:left;direction:ltr"> I'm sorry(A5-11) <h2 style=";text-align:left;direction:ltr">Ar<h2 style=";text-align:left;direction:ltr"> ２ <h2 style=";text-align:left;direction:ltr"> -(OH)<h2 style=";text-align:left;direction:ltr"> ２ <h2 style=";text-align:left;direction:ltr"> I'm sorry(A5-22) <h2 style=";text-align:left;direction:ltr">Ar<h2 style=";text-align:left;direction:ltr"> ２ <h2 style=";text-align:left;direction:ltr"> -(SH)<h2 style=";text-align:left;direction:ltr"> ２ <h2 style=";text-align:left;direction:ltr"> I'm sorry (In formulas (A5-1) to (A5-3), Ar ２ is an aromatic group-containing group, and R ａ２ represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. with a compound represented by any one of The dihalotriazine compound is represented by the following formula (A3): 【Chemistry 3】 (In formula (A3), Hal is a halogen atom, Ar １ is an aromatic group-containing group, R ａ１ represents a hydroxyl group protected by a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or an acetal protecting group, or a carboxyl group protected by an acid-labile group, The acetal protecting group is —CHR Ａ１ -O-R Ａ２ is a group represented by R Ａ１ is a hydrogen atom or an alkyl group, R Ａ２ is an alkyl group, The R Ａ１ , and the R Ａ２ may be bonded to each other to form a ring, X １ are each independently -NR ａ２ -, -O-, or -S-; R ａ２ represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X １ is Ar １ and bonded to the aromatic ring in the aromatic group-containing group as The compound includes a compound represented by The condensation of the dihalotriazine compound with the compound represented by any one of formulas (A5-1) to (A5-3) is carried out by reacting the compound represented by formulas (A7-1) to (A7-3) below: X ４ -X ３ -NR ａ２ H・・・(A7-1) X ４ -X ３ -OH・・・(A7-2) X ４ -X ３ -SH・・・(A7-3) (In formulas (A7-1) to (A7-3), X ３ , and X ４ represents X in formula (A1-1). ３ , and X ４ is the same as R ａ２ is R in formula (1). ａ２ (Similar to the above.) or in the presence of a compound represented by 2. The method for producing a polymer according to claim 1, wherein a condensation product of the dihalotriazine compound and the compound represented by any one of formulas (A5-1) to (A5-3) is reacted with the compound represented by any one of formulas (A7-1) to (A7-3).

7. The dihalotriazine compound is represented by the following formula (A6): 【Chemistry 4】 (In formula (A6), Hal is a halogen atom, Ar ３ is an aromatic group-containing group, X １ are each independently -NR ａ２ -, -O-, or -S-; R ａ２ represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X １ is Ar ３ and bonded to the aromatic ring in the aromatic group-containing group as The method according to claim 6, wherein the compound is represented by the formula:

8. A solvent containing a triazine ring-containing polymer (A) and an organic solvent (S), The triazine ring-containing polymer (A) is the polymer according to claim 1 , The R ａ１ is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid-dissociable group, the non-photosensitive liquid composition further comprising a thermal acid generator (C).

9. The non-photosensitive liquid composition according to claim 8 , further comprising a crosslinkable compound (B).

10. the crosslinkable compound (B) is an aromatic compound (Bi) containing two or more crosslinkable groups and a triazine ring, a fluorene ring which may have a substituent, or a binaphthalene ring which may have a substituent, a sulfur-containing compound (Bii) containing two or more crosslinkable groups, an isocyanate compound (Biii) containing two or more isocyanate groups, or an aliphatic compound (Biv) containing two or more crosslinkable groups, The sulfur-containing compound (Bii) is a compound that does not fall under the category of the aromatic compound (Bi), The isocyanate compound (Biii) is a compound that does not fall under the category of the aromatic compound (Bi) or the sulfur-containing compound (Bii), The non-photosensitive liquid composition according to claim 9 , wherein the aliphatic compound (Biv) is a compound that does not fall under the category of the sulfur-containing compound (Bii) or the isocyanate compound (Biii).

11. The non-photosensitive liquid composition according to claim 10, wherein the crosslinkable group is an epoxy group, an episulfide group, or an isocyanate group.

12. 9. The non-photosensitive liquid composition according to claim 8, wherein the organic solvent (S) is a ketone, a nitrogen-containing polar organic solvent, a monoalkyl ether acetate of a glycol, or a monoalkyl ether of a glycol.

13. A method of molding the non-photosensitive liquid composition according to claim 8; and removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

14. The method for producing a molded article according to claim 13, wherein the non-photosensitive liquid composition is formed into a film by applying the non-photosensitive liquid composition onto a substrate.

15. A molded article made from the non-photosensitive liquid composition according to claim 8.

16. An optical component comprising the molded article according to claim 15.

17. 17. The optical component according to claim 16, which is a film or a microlens.

18. An optical element comprising the optical component according to claim 16.

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