CN118202006A

CN118202006A - Resin composition, cured product, optical member, ultraviolet absorber, compound, method for producing compound, and polymer

Info

Publication number: CN118202006A
Application number: CN202280074175.XA
Authority: CN
Inventors: 东笃志; 佐佐木大辅; 坂井优介
Original assignee: Fujifilm Corp
Current assignee: Fujifilm Corp
Priority date: 2021-12-02
Filing date: 2022-11-22
Publication date: 2024-06-14

Abstract

A resin composition comprising a compound represented by the formula (1) and a resin, wherein Q ¹ in the formula (1) represents a group represented by the formula (Q-1). Q ² represents=o, =s, =nr ^q1, or=cr ^q2R^q3,R^q1～R^q3 each independently represents a hydrogen atom or a substituent, and R ^q2 and R ^q3 may be bonded to each other to form a ring. Where R ^q2 and R ^q3 are bonded to form a ring, CR ^q2R^q3 and Q ¹ are not the same structure. R ¹ and R ² each independently represent a hydrogen atom or a substituent. X ¹～X⁴ each independently represents-S-or the like. A cured product, an optical member, an ultraviolet absorber, a compound, a method for producing the compound, and a polymer.

Description

Resin composition, cured product, optical member, ultraviolet absorber, compound, method for producing compound, and polymer

Technical Field

The present invention relates to a resin composition containing an ultraviolet absorber. The present invention also relates to a cured product and an optical member using the resin composition. The present invention also relates to an ultraviolet absorber, a compound, a method for producing the compound, and a polymer.

Background

The benzodithiol compound is excellent in ultraviolet absorptivity and is used for an ultraviolet absorber and the like. For example, patent document 1 describes the use of a specific benzodithiol as an ultraviolet absorber.

Technical literature of the prior art

Patent literature

Patent document 1: international publication No. 2009/022736

Disclosure of Invention

Technical problem to be solved by the invention

Among the ultraviolet absorbers, one of the required characteristics is required to have little coloration. In recent years, ultraviolet rays having a longer wavelength around 400nm are also required to have a high absorption capacity.

Further, the ultraviolet absorber may have its ultraviolet absorption performance degraded with time due to light irradiation. In particular, an ultraviolet absorber having a maximum absorption wavelength on a longer wavelength side of an ultraviolet region tends to be inferior in light resistance, and the ultraviolet absorption ability tends to be easily lowered with time. Therefore, in recent years, further improvement of the light resistance of the ultraviolet absorber has been desired.

Accordingly, an object of the present invention is to provide a resin composition which can produce a cured product or the like excellent in ultraviolet absorption ability in the vicinity of 400nm, less in coloration, and excellent in light resistance. The present invention also provides a cured product, an optical member, an ultraviolet absorber, a compound, a method for producing the compound, and a polymer.

Means for solving the technical problems

As a result of intensive studies on a compound having a skeleton represented by formula (1), the present inventors have found that a compound having a structure in which Q ¹ and Q ² in formula (1) are combined in a specific manner is a compound excellent in ultraviolet absorption ability in the wavelength region of 400nm, less in coloring, and excellent in light resistance, and have completed the present invention. Accordingly, the present invention provides the following.

<1> A resin composition comprising a compound represented by the formula (1) and a resin,

[ Chemical formula 1]

In formula (1), Q ¹ represents a group represented by formula (Q-1),

Q ² represents =o, =s, =nr ^q1, or =cr ^q2R^q3,R^q1～R^q3 each independently represents a hydrogen atom or a substituent, optionally R ^q2 and R ^q3 are bonded to each other to form a ring, wherein in the case where R ^q2 and R ^q3 are bonded to form a ring, =cr ^q2R^q3 is not the same structure as Q ¹,

R ¹ and R ² each independently represent a hydrogen atom or a substituent,

X ¹～X⁴ each independently represents-S-, -NR ^X1 -or-SO ₂-,R^X1 represents a hydrogen atom or an alkyl group,

[ Chemical formula 2]

In formula (Q-1), R ¹⁰¹ and R ¹⁰² each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond,

Wherein when either R ¹⁰¹ or R ¹⁰² is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group or a group containing a polymerizable group having an ethylenically unsaturated bond,

When either R ¹⁰¹ or R ¹⁰² is methyl, the other represents a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond,

When either R ¹⁰¹ or R ¹⁰² is phenyl, the other represents a hydrogen atom, an alkyl group, an aralkyl group, a substituted aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

<2> The resin composition according to <1>, wherein,

R ¹⁰¹ and R ¹⁰² each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a heterocyclic group,

When either R ¹⁰¹ or R ¹⁰² is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group,

When either R ¹⁰¹ or R ¹⁰² is methyl, the other represents a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group or a heterocyclic group,

When either R ¹⁰¹ or R ¹⁰² is phenyl, the other represents a hydrogen atom, an alkyl group, an aralkyl group, a substituted aryl group or a heterocyclic group.

<3> The resin composition according to <1> or <2>, wherein,

The compound represented by the formula (1) is a compound represented by the formula (3),

[ Chemical formula 3]

In the formula (3), Q ³ represents a group represented by the above formula (Q-1),

Q ⁴ represents=o, =s, =nr ^q11, or=cr ^q12R^q13,R^q11～R^q13 each independently represents a hydrogen atom or a substituent, R ^q12 and R ^q13 may be bonded to each other to form a ring, wherein in the case where R ^q12 and R ^q13 are bonded to form a ring, =cr ^q12R^q13 and Q ³ are not the same structure,

R ¹¹ and R ¹² each independently represent -OH、-O-Y¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹、-OSO₂-Y¹¹ or a group containing a polymerizable group having an ethylenically unsaturated bond, R ^y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group.

<4> The resin composition according to <3>, wherein,

R ¹¹ and R ¹² in the above formula (3) each independently represent-OH, -O-Y ¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹ or-OSO ₂-Y¹¹,R^y11, and each represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group.

<5> The resin composition according to <3>, wherein,

At least one of R ¹¹、R¹²、Q³ and Q ⁴ in the formula (3) contains a group containing a polymerizable group having an ethylenically unsaturated bond.

<6> The resin composition according to any one of <1> to <5>, wherein,

The resin is at least one selected from the group consisting of (meth) acrylic resins, polystyrene resins, polyester resins, polyurethane resins, thiourethane resins, polyimide resins, polyamide resins, epoxy resins, polycarbonate resins, phthalate resins, cellulose acylate resins, and cyclic olefin resins.

<7> A cured product obtained using the resin composition according to any one of <1> to <6 >.

<8> An optical member comprising the cured product of <7 >.

<9> An ultraviolet absorber comprising a compound represented by the formula (1),

[ Chemical formula 4]

In formula (1), Q ¹ represents a group represented by formula (Q-1),

Q ² represents=o, =s, =nr ^q1, or=cr ^q2R^q3,R^q1～R^q3 each independently represents a hydrogen atom or a substituent, R ^q2 and R ^q3 may be bonded to each other to form a ring, wherein in the case where R ^q2 and R ^q3 are bonded to form a ring, =cr ^q2R^q3 and Q ¹ are not the same structure,

R ¹ and R ² each independently represent a hydrogen atom or a substituent,

[ Chemical formula 5]

<10> The ultraviolet absorber according to <9>, wherein,

<11> The compound represented by the formula (3),

[ Chemical formula 6]

In formula (3), Q ³ represents a group represented by formula (Q-1),

R ¹¹ and R ¹² each independently represent -oH、-O-Y¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-R¹¹、-OSO₂-Y¹¹ or a group containing a polymerizable group having an ethylenically unsaturated bond, R ^y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group,

[ Chemical formula 7]

<12> The compound according to <11>, wherein,

R ¹¹ and R ¹² of the above formula (3) each independently represent-OH, -O-Y ¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹ or-OSO ₂-Y¹¹,R^y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group,

When either R ¹⁰¹ or R ¹⁰² is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group or a heterocyclic group,

<13> The compound according to <11>, wherein,

<14> A method for producing a compound represented by the formula (6) by reacting a compound represented by the formula (4) with a compound represented by the formula (5),

[ Chemical formula 8]

In formula (4), Q ⁵ represents a group represented by formula (Q-1),

Q ⁶ represents =o, =s, =nr ^q21 or =cr ^q22R^q23,

R ^q21～R^q23 each independently represents a hydrogen atom or a substituent, R ^q22 and R ^q23 may be bonded to each other to form a ring, wherein, in the case where R ^q22 and R ^q23 are bonded to form a ring, =CR ^q22R^q23 and Q ⁵ are not the same structure,

In the formula (5), the amino acid sequence of the compound, E ⁵¹ represents-COCl, -O (c=o) Cl, -NR ^e51 (c=o) Cl-NCO, -Cl, -Br, -I or-SO ₂R^e52,

R ^e51 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group,

R ^e52 represents-Cl or an alkoxy group,

Y ⁵¹ represents an alkyl group, an aralkyl group or an aryl group,

In formula (6), Q ⁵ represents a group represented by formula (Q-1),

Q ⁶ represents =o, =s, =nr ^q21 or =cr ^q22R^q23,

R ⁶¹ and R ⁶² each independently represent-O-Y ⁶¹、-OC(＝O)-Y⁶¹、-OC(＝O)O-Y⁶¹、-OC(＝O)NR^y61-Y⁶¹ or-OSO ₂-Y⁶¹,R^y61 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, Y ⁶¹ represents an alkyl group, an aralkyl group or an aryl group,

[ Chemical formula 9]

<15> The method for producing a compound according to <14>, wherein,

<16> A polymer comprising a structure derived from the compound of <13 >.

Effects of the invention

According to the present invention, a resin composition which can produce a cured product or the like having excellent ultraviolet absorption ability in the vicinity of 400nm, less coloration, and excellent light resistance can be provided. The present invention also provides a cured product, an optical member, an ultraviolet absorber, a compound, a method for producing the compound, and a polymer.

Detailed Description

The following describes the present invention in detail.

In the labeling of groups (atomic groups) in the present specification, the label which is not labeled with a substituted and unsubstituted includes a group having no substituent and a group having a substituent. For example, "alkyl" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).

In the present specification, the numerical range indicated by the term "to" refers to a range including numerical values described before and after the term "to" as a lower limit value and an upper limit value.

In the present specification, the total solid component means the total amount of components excluding the solvent from the total components of the resin composition.

In the present specification, "(meth) acrylate" means either or both of acrylate and methacrylate, "(meth) acrylic acid" means either or both of acrylic acid and methacrylic acid, "(meth) allyl" means either or both of allyl and methallyl, "(meth) acryl" means either or both of acryl and methacryl.

In the present specification, the term "process" means not only an independent process but also a process which is not clearly distinguished from other processes, and is included in the term as long as the intended function of the process is achieved.

In the present specification, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene equivalent values measured by Gel Permeation Chromatography (GPC).

< Resin composition >

The resin composition of the present invention is characterized by comprising a compound represented by formula (1) and a resin.

The compound represented by the formula (1) has excellent light resistance, which is excellent in the absorption ability of ultraviolet rays in the vicinity of 400nm, is less colored, and is less likely to be decomposed by light irradiation. Therefore, the resin composition of the present invention can produce a cured product or the like having excellent ultraviolet absorption ability in the vicinity of 400nm, less coloration, and excellent light resistance.

The resin composition of the present invention may be a composition in a solution state containing a solvent.

The resin composition of the present invention may be a kneaded product. In the present specification, the kneaded material means a material obtained by kneading a compound represented by the formula (1) with a resin. That is, the kneaded material in the present specification is a material obtained by mixing and dispersing a compound represented by the formula (1) in a resin, but is different from a solution obtained by dissolving or dispersing a compound represented by the formula (1) and a resin in a solvent.

The compound is also preferably a granulate. In the present specification, the term "pellet" means a material having a predetermined shape such as a sphere, an ellipse, a cylinder, or a prism, obtained by granulating (pelletizing) a kneaded product. The particles are also preferably master batches (master batches). The master batch (master batch) is a material in which an additive such as an ultraviolet absorber is dispersed in a resin at a high concentration, and is used by mixing with the resin or the like at a predetermined ratio when forming a molded article.

The components contained in the resin composition will be described below.

A compound (specific Compound) represented by the formula (1)

The resin composition of the present invention contains a compound represented by formula (1) (hereinafter, also referred to as a specific compound).

[ Chemical formula 10]

In formula (1), Q ¹ represents a group represented by formula (Q-1),

R ¹ and R ² each independently represent a hydrogen atom or a substituent,

[ Chemical formula 11]

R ¹、R² -

Examples of the substituent represented by R ¹ and R ² in formula (1) include an alkyl group, an aryl group, an aralkyl group, a heterocyclic group, a group 、-OH、-O-Y¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹、-OSO₂-Y¹¹、 cyano group containing a polymerizable group having an ethylenically unsaturated bond, a halogen atom, and a nitro group. R ^y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group.

The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. The alkyl group may be any of linear, branched and cyclic, and is preferably linear or branched. The alkyl group may have a substituent. Examples of the substituent include those described below as substituent T.

The number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aryl group may have a substituent. Examples of the substituent include those described below as substituent T.

The number of carbon atoms of the alkyl moiety in the aralkyl group is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. The number of carbon atoms of the aryl moiety in the above aralkyl group is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aralkyl group may have a substituent. Examples of the substituent include those described below as substituent T. Specific examples of the aralkyl group include benzyl group and the like.

The heterocycle in the above-mentioned heterocyclic group is preferably a saturated or unsaturated heterocycle including 5-or 6-membered. An aliphatic ring, an aromatic ring, or other heterocyclic ring may be condensed in the heterocyclic ring. Examples of the hetero atom constituting the heterocyclic ring include B, N, O, S, se and Te, and N, O and S are preferable. The heterocycle preferably has a free valence (monovalent) of carbon (the heterocyclyl is bonded to the carbon). The number of carbon atoms of the heterocyclic group is preferably 1 to 40, more preferably 1 to 30, and still more preferably 1 to 20. Examples of the saturated heterocyclic ring in the heterocyclic group include a pyrrolidine ring, a morpholine ring, a 2-boron-1, 3-dioxolane ring and a 1, 3-thiazolidine ring. Examples of the unsaturated heterocycle in the heterocyclic group include an imidazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzotriazole ring, a benzoselenazole ring, a pyridine ring, a pyrimidine ring and a quinoline ring.

Examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.

Examples of the polymerizable group having an ethylenically unsaturated bond in the group having a polymerizable group having an ethylenically unsaturated bond include a vinyl group, a (meth) allyl group, a (meth) acryl group, a (meth) acryloyloxy group, a (meth) acrylamido group, and a vinylphenyl group, and (meth) acryloyloxy group and a vinylphenyl group are preferable.

Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include a group represented by the following formula (T1).

*-X^T1-Y^T1-Z^T1......(T1)

In the formula (T1), X ^T1 represents a single bond, -O-, -OC (=O) O-, or-OC (=O) NRx ¹-,Rx¹ represents a hydrogen atom, an alkyl group, or an aryl group,

Y ^T1 represents a single bond or a 2-valent linking group,

Z ^T1 represents a polymerizable group having an ethylenically unsaturated bond.

The alkyl group represented by Rx ¹ is preferably an alkyl group having 1 to 30 carbon atoms. Specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, and the like. The aryl group represented by Rx ¹ is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Specific examples thereof include phenyl, p-tolyl, and naphthyl. Rx ¹ is preferably a hydrogen atom.

X ^T1 is preferably-O-, -OC (=o) -or-OC (=o) NH-, more preferably-OC (=o) -, from the viewpoint of synthesis.

Examples of the 2-valent linking group represented by Y ^T1 include a group in which a hydrocarbon group and 2 or more hydrocarbon groups are bonded by a single bond or a linking group. Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and aliphatic hydrocarbon groups are preferable. The number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The aliphatic hydrocarbon group may be any of straight chain, branched chain, and cyclic. The cyclic aliphatic hydrocarbon group may be a single ring or a condensed ring. The cyclic aliphatic hydrocarbon group may have a crosslinked structure. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include substituent T described below. Examples of the substituent include a hydroxyl group.

As the linking group linking the above 2 or more hydrocarbon groups, examples are-NH-, -S (=o) ₂ -, -O-, -C (=o) -, -OC (=o) -, -C (=o) O-, -NHC (=o) -and-C (=o) NH-, preferably-O-, -C (=O) -, -OC (=o) -, -C (=o) O-, -NHC (=o) -or-C (=o) NH-.

Examples of the polymerizable group having an ethylenically unsaturated bond represented by Z ^T1 include a vinyl group, an allyl group, a (meth) acryl group, a (meth) acryloyloxy group, a (meth) acryloylamino group, and a vinylphenyl group, and preferable examples thereof are a (meth) acryloyloxy group and a vinylphenyl group.

Specific examples of the group represented by the formula (T1) include the following groups represented by T-1 to T-28. Me in the following structural formula is methyl, and is a bond.

[ Chemical formula 12]

[ Chemical formula 13]

R ¹ and R ² of the formula (1) are preferably each independently -OH、-O-Y¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹、-OSO₂-Y¹¹ or a group comprising a polymerizable group having an ethylenically unsaturated bond.

One embodiment is one in which R ¹ and R ² in formula (1) are each independently-OH, -O-Y ¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹ or-OSO ₂-Y¹¹. In this embodiment, R ¹ and R ² are more preferably each independently-OC (=o) -Y ¹¹、-O-Y¹¹ or-OC (=o) NR ^y11-Y¹¹.R^y11 is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom, from the viewpoint of excellent stability. For reasons of excellent solubility, Y ¹¹ is preferably an alkyl group, more preferably a linear or branched alkyl group, and even more preferably a branched alkyl group.

As another embodiment, at least one of R ¹ and R ² is a group containing a polymerizable group having an ethylenically unsaturated bond. According to this aspect, an effect of suppressing bleeding in the resin can be obtained.

X ¹～X⁴ -

X ¹～X⁴ of the formula (1) each independently represents-S-, -NR ^X1 -or-SO ₂-,R^X1 represents a hydrogen atom or an alkyl group. Preferred ranges for the alkyl group represented by R ^X1 are the same as those described above. R ^X1 is preferably a hydrogen atom.

For the reason of more remarkably exerting the effect of the present invention, X ¹～X⁴ of formula (1) is preferably-S-.

About Q ¹ -

Q ¹ of formula (1) represents a group represented by formula (Q-1).

R ¹⁰¹ and R ¹⁰² in the formula (Q-1) each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

Wherein when either one of R ¹⁰¹ or R ¹⁰² is a hydrogen atom, the other represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond, when either one of R ¹⁰¹ or R ¹⁰² is a methyl group, the other represents a hydrogen atom, an alkyl group having 2 or more carbon atoms, an aralkyl group, an aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond, and when either one of R ¹⁰¹ or R ¹⁰² is a phenyl group, the other represents a hydrogen atom, an alkyl group, an aralkyl group, a substituted aryl group, a heterocyclic group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

The number of carbon atoms of the alkyl group represented by R ¹⁰¹ and R ¹⁰² is preferably 1 to 30. The upper limit is preferably 20 or less, more preferably 15 or less, still more preferably 10 or less, and still more preferably 8 or less. The lower limit is preferably 2 or more, more preferably 3 or more. The alkyl group may be any of linear, branched and cyclic, and is preferably linear or branched. The alkyl group may have a substituent. Examples of the substituent include those described below as substituent T.

The number of carbon atoms of the aryl group represented by R ¹⁰¹ and R ¹⁰² is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aryl group may have a substituent. Examples of the substituent include those described below as substituent T.

The number of carbon atoms of the alkyl moiety in the aralkyl group represented by R ¹⁰¹ and R ¹⁰² is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. The number of carbon atoms of the aryl moiety in the above aralkyl group is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aralkyl group may have a substituent. Examples of the substituent include those described below as substituent T.

Examples of the heterocyclic group represented by R ¹⁰¹ and R ¹⁰² include the heterocyclic groups described above.

Examples of the group containing a polymerizable group having an ethylenically unsaturated bond represented by R ¹⁰¹ and R ¹⁰² include groups represented by formula (V1).

*-X^V1-Y^V1-Z^V1......(V1)

In the formula (V1), X ^V1 represents a single bond, -O-, -C (=O) O-, or-C (=O) NRx ²,Rx² represents a hydrogen atom, an alkyl group or an aryl group,

Y ^V1 represents a single bond or a 2-valent linking group,

Z ^V1 represents a polymerizable group having an ethylenically unsaturated bond.

The alkyl group and the aryl group represented by Rx ² have the same meaning as the alkyl group and the aryl group represented by Rx ¹ of the group represented by formula (T1), and the preferable ranges are also the same. Rx ² is preferably a hydrogen atom.

X ^V1 is preferably a single bond or-C (=o) -, more preferably a single bond.

The 2-valent linking group represented by Y ^V1 is exemplified by the 2-valent linking group represented by Y ^T1 which is a group represented by the formula (T1), and the preferable ranges are the same.

Examples of the polymerizable group having an ethylenically unsaturated bond represented by Z ^V1 include a vinyl group, an allyl group, a (meth) acryl group, a (meth) acryloyloxy group, a (meth) acryloylamino group, and a vinylphenyl group, and preferable examples thereof are a (meth) acryloyloxy group and a vinylphenyl group.

Specific examples of the group represented by the formula (V1) include groups represented by the following V-1 to V-12. The following structural formula is a bond.

[ Chemical formula 14]

R ¹⁰¹ and R ¹⁰² each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a heterocyclic group as a means of R ¹⁰¹ and R ¹⁰² of the formula (Q-1),

R ¹⁰¹ and R ¹⁰² of formula (Q-1) are preferably each independently an alkyl group or an aralkyl group, more preferably an aralkyl group.

When R ¹⁰¹ and R ¹⁰² are alkyl groups, the alkyl groups represented by R ¹⁰¹ and R ¹⁰² are preferably each independently an alkyl group having 2 or more carbon atoms.

As another embodiment of R ¹⁰¹ and R ¹⁰² in the formula (Q-1), at least one of R ¹⁰¹ and R ¹⁰² in the formula (Q-1) is a group containing a polymerizable group having an ethylenically unsaturated bond. According to this aspect, an effect of suppressing bleeding in the resin can be obtained.

About Q ² -

Q ² of formula (1) represents =o, =s, =nr ^q1, or =cr ^q2R^q3,R^q1～R^q3 each independently represents a hydrogen atom or a substituent, and R ^q2 and R ^q3 may be bonded to each other to form a ring. Where R ^q2 and R ^q3 are bonded to form a ring, CR ^q2R^q3 and Q ¹ are not the same structure.

Examples of the substituent represented by R ^q1～R^q3 include cyano, carbamoyl, sulfamoyl, nitro, acyl, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, arylsulfinyl, alkoxycarbonyl, aryloxycarbonyl, alkyl, aryl, heterocyclic group, and a group containing a polymerizable group having an ethylenically unsaturated bond. These groups may further have a substituent. Examples of the substituent include those mentioned as substituents T described below.

The carbamoyl group is a carbamoyl group having 1 to 10 carbon atoms, preferably a carbamoyl group having 2 to 8 carbon atoms, more preferably a carbamoyl group having 2 to 5 carbon atoms.

The sulfamoyl group is a sulfamoyl group having 0 to 10 carbon atoms, preferably a sulfamoyl group having 2 to 8 carbon atoms, and more preferably a sulfamoyl group having 2 to 5 carbon atoms.

Examples of the acyl group include an acyl group having 1 to 20 carbon atoms, preferably an acyl group having 1 to 12 carbon atoms, and more preferably an acyl group having 1 to 8 carbon atoms.

The alkylsulfonyl group is preferably an alkylsulfonyl group having 1 to 20 carbon atoms, more preferably an alkylsulfonyl group having 1 to 10 carbon atoms, and still more preferably an alkylsulfonyl group having 1 to 8 carbon atoms.

Examples of the arylsulfonyl group include arylsulfonyl groups having 6 to 20 carbon atoms, and arylsulfonyl groups having 6 to 10 carbon atoms are preferable.

The alkylsulfinyl group is preferably an alkylsulfinyl group having 1 to 20 carbon atoms, more preferably an alkylsulfinyl group having 1 to 10 carbon atoms, and still more preferably an alkylsulfinyl group having 1 to 8 carbon atoms.

The arylsulfinyl group includes arylsulfinyl groups having 6 to 20 carbon atoms, and preferably arylsulfinyl groups having 6 to 10 carbon atoms.

The alkoxycarbonyl group includes an alkoxycarbonyl group having 2 to 20 carbon atoms, preferably an alkoxycarbonyl group having 2 to 12 carbon atoms, and more preferably an alkoxycarbonyl group having 2 to 8 carbon atoms.

Examples of the aryloxycarbonyl group include aryloxycarbonyl groups having 6 to 20 carbon atoms, preferably aryloxycarbonyl groups having 6 to 12 carbon atoms, and more preferably aryloxycarbonyl groups having 6 to 8 carbon atoms.

The alkyl group is preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and still more preferably an alkyl group having 1 to 5 carbon atoms.

The aryl group is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 15 carbon atoms, and still more preferably an aryl group having 6 to 10 carbon atoms.

The heterocycle in the heterocyclyl group preferably includes a 5-or 6-membered saturated or unsaturated heterocycle. An aliphatic ring, an aromatic ring, or other heterocyclic ring may be condensed in the heterocyclic ring. Examples of the hetero atom constituting the heterocyclic ring include B, N, O, S, se and Te, and N, O and S are preferable. The heterocycle preferably has a free valence (monovalent) of carbon (the heterocyclyl is bonded to the carbon). The number of carbon atoms of the heterocyclic group is preferably 1 to 40, more preferably 1 to 30, and still more preferably 1 to 20.

Examples of the group containing a polymerizable group having an ethylenically unsaturated bond include a group represented by the formula (U1).

*-X^U1-Y^U1-Z^U1......(U1)

In the formula (U1), X ^U1 represents a single bond, -C (=O) -, -C (=O) O-, or-C (=O) NRx ³-,Rx³ represents a hydrogen atom, an alkyl group, or an aryl group,

Y ^U1 represents a single bond or a 2-valent linking group,

Z ^U1 represents a polymerizable group having an ethylenically unsaturated bond.

The alkyl group and the aryl group represented by Rx ³ have the same meaning as the alkyl group and the aryl group represented by Rx ¹ of the group represented by formula (T1), and the preferable ranges are also the same. Rx ³ is preferably a hydrogen atom.

X ^U1 is preferably-C (=o) O-or-C (=o) NRx ³ -, from the viewpoint of synthesis, it is more preferably-C (=O) O-.

The 2-valent linking group represented by Y ^U1 is exemplified by the 2-valent linking group represented by Y ^T1 which is a group represented by the formula (T1), and the preferable ranges are the same.

Examples of the polymerizable group having an ethylenically unsaturated bond represented by Z ^U1 include a vinyl group, an allyl group, a (meth) acryl group, a (meth) acryloyloxy group, a (meth) acryloylamino group, and a vinylphenyl group, and preferable examples thereof are a (meth) acryloyloxy group and a vinylphenyl group.

Specific examples of the group represented by the formula (U1) include groups represented by the following U-1 to U-11. The following structural formula is a bond.

[ Chemical formula 15]

For reasons of more remarkably exerting the effects of the present invention, Q ² of formula (1) is preferably=cr ^q2R^q3. At least one of R ^q2 and R ^q3 is preferably an electron withdrawing group, and R ^q2 and R ^q3 are more preferably electron withdrawing groups.

At least one of R ^q2 and R ^q3 is also preferably a group containing a polymerizable group having an ethylenically unsaturated bond. In this embodiment, it is also preferable that one of R ^q2 and R ^q3 is a group containing a polymerizable group having an ethylenically unsaturated bond, and the other is an electron-withdrawing group.

Examples of the electron withdrawing group include a substituent having a Hammett substituent constant σp of 0.2 or more. The Hammett substituent constant σ value is described. The Hammett's rule of thumb, proposed by L.P.Hammett in 1935, is currently widely accepted as rational for quantitative discussion of the effect of substituents on the reaction or equilibrium of benzene derivatives. The substituent constants found by the Hammett's law have σp and σm values, which can be found in many general books. For example, they are described in detail in J.A.dean, 12 th edition, "Lange's Handbook of Chemistry", 1979 (Mc Graw-Hill) or "chemical area" journal, 122, pages 96 to 103, 1979 (Nangu), chem.Rev.,1991, volume 91, pages 165 to 195, etc. In the present specification, a substituent having a Hammett substituent constant σp value of 0.2 or more represents an electron withdrawing group. The electron withdrawing group is preferably a group having a Hammett substituent constant σp of 0.25 or more, more preferably a group having a Hammett substituent constant σp of 0.3 or more, and still more preferably a group having a Hammett substituent constant σp of 0.35 or more.

Specific examples of the group having a Hammett substituent constant σp value of 0.2 or more include cyano group (σp value=0.66), carboxyl group (-COOH: σp value=0.45), alkoxycarbonyl group (-COOMe: σp value=0.45), aryloxycarbonyl group (-COOPh: σp value=0.44), carbamoyl group (-CONH ₂: σp value=0.36), alkylcarbonyl group (-COMe: σp value=0.50), arylcarbonyl group (-COPh: σp value=0.43), alkylsulfonyl group (-SO ₂ Me: σp value=0.72), arylsulfonyl group (-SO ₂ Ph: σp value=0.68), and the like. Me represents methyl, ph represents phenyl. The values in brackets are values obtained by picking up σp values of representative substituents from chem.rev.,1991, volume 91, pages 165 to 195.

R ^q2 and R ^q3 are each preferably independently a hydrogen atom, a cyano group, a carbamoyl group, a sulfamoyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a nitro group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a group containing a polymerizable group having an ethylenically unsaturated bond.

As one embodiment, R ^q2 and R ^q3 are each independently a hydrogen atom, a cyano group, a carbamoyl group, a sulfamoyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a nitro group, an alkoxycarbonyl group, or an aryloxycarbonyl group. Wherein at least one of R ^q2 and R ^q3 is preferably cyano, alkoxycarbonyl, nitro or alkylsulfonyl, and R ^q2 and R ^q3 are more preferably each independently cyano or alkoxycarbonyl. A preferable embodiment is an embodiment in which R ^q2 and R ^q3 are cyano groups. Another preferable embodiment is one in which one of R ^q2 and R ^q3 is cyano and the other is alkoxycarbonyl.

As another embodiment, at least one of R ^q2 and R ^q3 is also preferably a group containing a polymerizable group having an ethylenically unsaturated bond. R ^q2 and R ^q3 may each independently be a group containing a polymerizable group having an ethylenically unsaturated bond, and one of R ^q2 and R ^q3 may be a group containing a polymerizable group having an ethylenically unsaturated bond, and the other may be an electron-withdrawing group.

In this specification, "when R ^q2 and R ^q3 are bonded to form a ring, the structure of =cr ^q2R^q3 and Q ¹ is not the same" includes not only the case of forming a ring other than the structure represented by formula (Q-1) but also the case of forming a ring having a structure represented by formula (Q-1), but the types of Rq ¹ and Rq ² in formula (Q-1) are different from the type of Q ¹. That is, Q ² is a group of a different structure from Q ¹.

When R ^q2 and R ^q3 of = CR ^q2R^q3 are bonded to each other to form a ring, the ring formed is preferably a ring other than the structure represented by formula (Q-1) for reasons of more significantly exerting the effects of the present invention. Examples of the ring other than the structure represented by the formula (Q-1) include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a pyrrolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, an oxazoline ring, a thiazoline ring, a pyrroline ring, a pyrazoline ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a piperazine ring, a pyran ring and the like. These may have a substituent at any position.

At least one of R ¹、R²、Q¹ and Q ² of formula (1) preferably contains a group containing a polymerizable group having an ethylenically unsaturated bond, and one or both of R ¹、R²、Q¹ and Q ² more preferably contains a group containing a polymerizable group having an ethylenically unsaturated bond.

Further, Q ² in formula (1) is at least one of=cr ^q2R^q3,R¹、R²、R^q3、R^q3、R¹⁰¹ and R ¹⁰², preferably a group containing a polymerizable group having an ethylenically unsaturated bond, and one or both of R ¹、R²、R^q2、R^q3、R¹⁰¹ and R ¹⁰² more preferably a group containing a polymerizable group having an ethylenically unsaturated bond.

The number of polymerizable groups having an ethylenically unsaturated bond contained in the formula (1) is preferably 1 to 2.

The specific compound is preferably a compound represented by formula (3). The compound represented by the formula (3) is a compound of the present invention.

[ Chemical formula 16]

Q ⁴ represents=o, =s, =nr ^q11, or=cr ^q12R^q13,R^q11～R^q13 each independently represents a hydrogen atom or a substituent, and R ^q12 and R ^q13 may be bonded to each other to form a ring, wherein in the case where R ^q12 and R ^q13 are bonded to form a ring, the structure of =cr ^q12R^q13 and Q ³ is not the same.

Q ³ and Q ⁴ in the formula (3) have the same meaning as Q ¹ and Q ² in the formula (1), and the preferable ranges are also the same. The preferable ranges of R ^y11 and Y ¹¹ in formula (3) are the same as those of R ^y11 and Y ¹¹ described in formula (1).

One embodiment is one in which R ¹¹ and R ¹² in formula (3) are each independently-OH, -O-R ¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹ or-OSO ₂-Y¹¹. In this embodiment, R ¹¹ and R ¹² are preferably each independently-OC (=o) -Y ¹¹、-O-Y¹¹ or-OC (=o) NR ^y11-Y¹¹.

As another embodiment, at least one of R ¹¹ and R ¹² is a group containing a polymerizable group having an ethylenically unsaturated bond.

At least one of R ¹¹、R¹²、Q³ and Q ⁴ of formula (3) preferably contains a group containing a polymerizable group having an ethylenically unsaturated bond, and one or both of R ¹¹、R¹²、Q³ and Q ⁴ more preferably contains a group containing a polymerizable group having an ethylenically unsaturated bond.

Further, Q ⁴ in formula (3) is at least one of=cr ^q12R^q13,R¹¹、R¹²、R^q12、R^q13、R¹⁰¹ and R ¹⁰², preferably a group containing a polymerizable group having an ethylenically unsaturated bond, and one or both of R ¹¹、R¹²、R^q12、Rq¹³、R¹⁰¹ and R ¹⁰² more preferably a group containing a polymerizable group having an ethylenically unsaturated bond.

The number of polymerizable groups having an ethylenically unsaturated bond contained in the formula (3) is preferably 1 to 2.

The specific compound is preferably a compound represented by formula (6).

[ Chemical formula 17]

In the formula (6), Q ⁵ represents a group represented by the above formula (Q-1),

Q ⁶ represents =0, =s, =nr ^q21 or =cr ^q22R^q23,

R ^q21～R^q33 each independently represents a hydrogen atom or a substituent, and R ^q22 and R ^q23 may be bonded to each other to form a ring, wherein in the case where R ^q22 and R ^q23 are bonded to form a ring, =cr ^q22R^q23 and Q ⁵ are not the same structure.

R ⁶¹ and R ⁶² each independently represent-O-Y ⁶¹、-OC(＝O)-Y⁶¹、-OC(＝O)O-Y⁶¹、-OC(＝O)NR^y61-Y⁶¹ or-OSO ₂-Y⁶¹,R^y61 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and Y ⁶¹ represents an alkyl group, an aralkyl group or an aryl group.

Q ⁵ and Q ⁶ in the formula (6) have the same meaning as Q ¹ and Q ² in the formula (1), and the preferable ranges are also the same. The preferable ranges of R ^y61 and Y ⁶¹ in formula (6) are the same as those of R ^y11 and Y ¹¹ described in formula (1).

R ⁶¹ and R ⁶² of formula (6) are preferably each independently-OC (=o) -Y ¹¹、-O-Y¹¹ or-OC (=o) NR ^y11-Y¹¹.

(Substituent T)

Examples of the substituent T include the following groups.

Halogen atoms (e.g., chlorine atom, bromine atom, iodine atom);

Alkyl [ straight chain, branched, cyclic alkyl. Specifically, a linear or branched alkyl group (preferably a linear or branched alkyl group having 1 to 30 carbon atoms, for example, methyl, ethyl, n-propyl, isopropyl, tert-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl, 2-ethylhexyl), a cycloalkyl group (preferably a cycloalkyl group having 3 to 30 carbon atoms, for example, cyclohexyl, cyclopentyl, 4-n-dodecylcyclohexyl), a bicycloalkyl group (preferably a bicycloalkyl group having 5 to 30 carbon atoms, that is, a monovalent group having one hydrogen atom removed from a bicycloalkane having 5 to 30 carbon atoms, for example, bicyclo [1, 2] heptan-2-yl, bicyclo [2, 2] octan-3-yl), and further, a tricyclic structure having a large number of ring structures, and the like are included. The alkyl group (e.g., alkyl group of alkylthio group) in the substituents described below also represents an alkyl group of this concept. The ];

Alkenyl [ straight chain, branched, cyclic alkenyl. Specifically, a straight-chain or branched alkenyl group (preferably a straight-chain or branched alkenyl group having 2 to 30 carbon atoms, for example, vinyl, allyl, prenyl, geranyl, oleyl), a cycloalkenyl group (preferably a cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a cycloolefin having 3 to 30 carbon atoms, for example, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl), a bicycloalkenyl group (preferably a bicycloalkenyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a bicycloalkene having one double bond, for example, bicyclo [2, 1] hept-2-en-1-yl, bicyclo [2, 2] oct-2-en-4-yl) are included. The ];

alkynyl (preferably straight-chain or branched alkynyl having 2 to 30 carbon atoms, for example, ethynyl, propargyl);

Aryl (preferably, aryl having 6 to 30 carbon atoms, for example, phenyl, p-tolyl, naphthyl, m-chlorophenyl, o-hexadecylaminophenyl);

Heterocyclyl (preferably a monovalent group in which one hydrogen atom is removed from a 5-or 6-membered aromatic or non-aromatic heterocyclic compound, more preferably a 5-or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms, for example, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl);

Cyano group;

A hydroxyl group;

A nitro group;

A carboxyl group;

Alkoxy (preferably straight-chain or branched alkoxy having 1 to 30 carbon atoms, for example, methoxy, ethoxy, isopropoxy, tert-butoxy, n-octoxy, 2-methoxyethoxy);

Aryloxy (preferably, aryloxy having 6 to 30 carbon atoms such as phenoxy, 2-methylphenoxy, 4-tert-butylphenoxy, 3-nitrophenoxy, 2-tetradecylaminophenoxy);

heteroepoxy groups (preferably, heterocyclyloxy groups having 2 to 30 carbon atoms, for example, 1-phenyltetrazol-5-oxy, 2-tetrahydropyranoxy);

acyloxy (preferably formyloxy, alkylcarbonyloxy having 2 to 30 carbon atoms, arylcarbonyloxy having 6 to 30 carbon atoms, for example, formyloxy, acetoxy, pivaloyloxy, stearyloxy, benzoyloxy, p-methoxyphenylcarbonyloxy);

Carbamoyloxy (preferably carbamoyloxy having 1 to 30 carbon atoms, e.g., N, N-dimethylcarbamoyloxy, N, N-diethylcarbamoyloxy, morpholinylcarbonyloxy, N, N-di-N-octylaminocarbonyloxy, N-N-octylcarbamoyloxy);

alkoxycarbonyloxy (preferably alkoxycarbonyloxy having 2 to 30 carbon atoms, for example, methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, n-octylcarbonyloxy);

aryloxy carbonyloxy (preferably, aryloxy carbonyloxy having 7 to 30 carbon atoms, for example, phenoxycarbonyloxy, p-methoxyphenoxycarbonyloxy, p-n-hexadecyloxyphenoxycarbonyloxy);

Amino group (preferably amino group, alkylamino group having 1 to 30 carbon atoms, or phenylamino group having 6 to 30 carbon atoms, for example, amino group, methylamino group, dimethylamino group, phenylamino group, N-methyl-phenylamino group, diphenylamino group);

Amido (preferably, formylamino, alkylcarbonylamino having 2 to 30 carbon atoms, arylcarbonylamino having 6 to 30 carbon atoms, for example, formylamino, acetamido, pivaloylamino, laurylamino, benzoylamino, 3,4, 5-tri-n-octyloxyphenylcarbonylamino);

aminocarbonylamino (preferably aminocarbonylamino having 1 to 30 carbon atoms, for example, carbamoylamino, N-dimethylaminocarbonylamino, N-diethylaminocarbonylamino, morpholinylcarbonylamino);

Alkoxycarbonylamino (preferably alkoxycarbonylamino having 2 to 30 carbon atoms, for example, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, N-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino);

Aryloxycarbonylamino group (preferably aryloxycarbonylamino group having 7 to 30 carbon atoms, for example, phenoxycarbonylamino group, p-chlorophenoxycarbonylamino group, m-n-octyloxyphenoxycarbonylamino group);

Sulfamoylamino group (preferably sulfamoylamino group having 0 to 30 carbon atoms, for example, sulfamoylamino group, N-dimethylaminosulfonylamino group, N-N-octylamino sulfonylamino group);

Alkyl or arylsulfonylamino groups (preferably alkylsulfonylamino groups having 1 to 30 carbon atoms, arylsulfonylamino groups having 6 to 30 carbon atoms, for example, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, 2,3, 5-trichlorophenylsulfonylamino, p-methylphenylsulfonylamino);

A mercapto group;

Alkylthio (preferably alkylthio having 1 to 30 carbon atoms, such as methylthio, ethylthio, n-hexadecylthio);

Arylthio (preferably arylthio having 6 to 30 carbon atoms, for example, phenylthio, p-chlorophenylthio, m-methoxyphenylthio);

heterocyclic thio (preferably heterocyclic thio having 2 to 30 carbon atoms, for example, 2-benzothiazolylthio, 1-phenyltetrazol-5-ylthio);

Sulfamoyl (preferably, sulfamoyl having 0 to 30 carbon atoms, for example, N-ethylsulfamoyl, N- (3-dodecyloxypropyl) sulfamoyl, N-dimethylsulfamoyl, N-acetylsulfamoyl, N-benzoylsulfamoyl, N- (N' -phenylcarbamoyl) sulfamoyl);

A sulfo group;

Alkyl or arylsulfinyl (preferably, alkylsulfinyl having 1 to 30 carbon atoms, arylsulfinyl having 6 to 30 carbon atoms, for example, methylsulfinyl, ethylsulfinyl, phenylsulfinyl, p-methylphenyl sulfinyl);

Alkyl or arylsulfonyl (preferably alkylsulfonyl having 1 to 30 carbon atoms, arylsulfonyl having 6 to 30 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, p-methylphenylsulfonyl);

Acyl (preferably, formyl, alkylcarbonyl having 2 to 30 carbon atoms, arylcarbonyl having 7 to 30 carbon atoms, or heterocyclocarbonyl bonded to carbonyl through a carbon atom having 4 to 30 carbon atoms, for example, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, p-n-octyloxyphenylcarbonyl, 2-pyridylcarbonyl, 2-furylcarbonyl);

aryloxycarbonyl (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms, for example, phenoxycarbonyl, o-chlorophenoxycarbonyl, m-nitrophenoxycarbonyl, p-tert-butylphenoxycarbonyl);

Alkoxycarbonyl (preferably alkoxycarbonyl having 2 to 30 carbon atoms, for example, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl);

Carbamoyl (preferably carbamoyl having 1 to 30 carbon atoms, for example, carbamoyl, N-methylcarbamoyl, N-dimethylcarbamoyl, N-di-N-octylcarbamoyl, N- (methylsulfonyl) carbamoyl);

Aryl or heterocyclic azo (preferably, aryl azo having 6 to 30 carbon atoms, heterocyclic azo having 3 to 30 carbon atoms, for example, phenylazo, p-chlorophenyl azo, 5-ethylthio-1, 3, 4-thiadiazol-2-ylazo);

Imide groups (preferably N-succinimidyl, N-phthalimidyl);

phosphino (preferably phosphino having 2 to 30 carbon atoms, for example, dimethylphosphino, diphenylphosphino, methylphenylphosphino)

Phosphinyl (preferably phosphinyl having 2 to 30 carbon atoms, for example, phosphinyl, dioctyloxyphosphinyl, diethoxyphosphinyl);

phosphinyloxy (preferably phosphinyloxy having 2 to 30 carbon atoms, for example, diphenoxyphosphinyloxy and dioctyloxyphosphinyloxy);

Phosphinylamino (preferably phosphinylamino having 2 to 30 carbon atoms, for example, dimethoxyphosphinylamino, dimethylaminophosphinylamino);

Of the above-mentioned groups, regarding the group having a hydrogen atom, 1 or more hydrogen atoms may be substituted with the above-mentioned substituent T. Examples of such substituents include alkylcarbonylaminosulfonyl, arylcarbonylaminosulfonyl, alkylsulfonylaminocarbonyl and arylsulfonylaminocarbonyl. Specific examples thereof include methylsulfonylaminocarbonyl, p-methylphenyl sulfonylaminocarbonyl, acetaminosulfonyl, and benzoylaminosulfonyl.

Specific examples of the specific compound include compounds having the following structures. In the structural formulae shown below, et is ethyl, me is methyl, ⁿ Bu is n-butyl, ^t Bu is t-butyl, and Ph is phenyl.

[ Chemical formula 18]

[ Chemical formula 19]

[ Chemical formula 20]

[ Chemical formula 21]

[ Chemical formula 22]

[ Chemical formula 23]

[ Chemical formula 24]

[ Chemical formula 25]

[ Chemical formula 26]

[ Chemical formula 27]

[ Chemical formula 28]

[ Chemical formula 29]

[ Chemical formula 30]

[ Chemical formula 31]

[ Chemical formula 32]

[ Chemical formula 33]

[ Chemical formula 34]

[ Chemical formula 35]

[ Chemical formula 36]

[ Chemical formula 37]

[ Chemical formula 38]

[ Chemical formula 39]

[ Chemical formula 40]

[ Chemical formula 41]

[ Chemical formula 42]

[ Chemical formula 43]

[ Chemical formula 44]

[ Chemical formula 45]

[ Chemical formula 46]

[ Chemical formula 47]

[ Chemical formula 48]

[ Chemical formula 49]

[ Chemical formula 50]

[ Chemical formula 51]

[ Chemical formula 52]

[ Chemical formula 53]

[ Chemical formula 54]

[ Chemical formula 55]

[ Chemical formula 56]

[ Chemical formula 57]

[ Chemical formula 58]

The specific compound is preferably used as an ultraviolet absorber.

The maximum absorption wavelength of the specific compound is preferably present in the wavelength range of 380 to 420nm, more preferably in the wavelength range of 390 to 410 nm.

The specific compound preferably has a ratio of absorbance at 440nm at a wavelength of less than 0.02 when absorbance at 400nm is 1.

The molar absorptivity of the specific compound at the maximum absorption wavelength is preferably 80000L/mol cm or more, more preferably 85000L/mol cm or more, and still more preferably 90000L/mol cm or more.

The molar absorptivity at a wavelength of 400nm is preferably 30000L/mol/cm or more, more preferably 40000L/mol/cm or more, and even more preferably 50000L/mol/cm or more.

The molar absorptivity at the wavelength of 440nm is preferably 1000L/mol cm or less, more preferably 800L/mol cm or less, and still more preferably 600L/mol cm or less.

The absorbance, the maximum absorption wavelength, and the molar absorptivity of the specific compound can be obtained by measuring the spectroscopic spectrum of a solution prepared by dissolving the specific compound in ethyl acetate at room temperature (25 ℃) using a 1cm quartz cell. Examples of the measuring device include a spectrophotometer (manufactured by UV-1800PC, SHIMADZU CORPORATION).

Specific compounds can be produced according to the method described in International publication No. 2009/022736.

In addition, the compound represented by the formula (6) can be produced by reacting the compound represented by the formula (4) with the compound represented by the formula (5) for a specific compound.

[ Chemical formula 59]

In the formula (4), Q ⁵ represents a group represented by the above formula (Q-1),

Q ⁶ represents =o, =s, =nr ^q21 or =cr ^q22R^q23,

R ^q21～R^q23 each independently represents a hydrogen atom or a substituent, and R ^q22 and R ^q23 may be bonded to each other to form a ring, wherein in the case where R ^q22 and R ^q23 are bonded to form a ring, =cr ^q22R^q23 and Q ⁵ are not the same structure.

R ^e52 represents-Cl or an alkoxy group,

Y ⁵¹ represents an alkyl group, an aralkyl group or an aryl group.

Q ⁵ and Q ⁶ in the formula (4) have the same meaning as Q ⁵ and Q ⁶ in the formula (6), and the preferable ranges are also the same.

The number of carbon atoms of the alkyl group represented by Y ⁵¹ of the formula (5) is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. The alkyl group may be any of linear, branched and cyclic, and is preferably linear or branched. The alkyl group may have a substituent. Examples of the substituent include those described for the substituent T.

The number of carbon atoms of the aryl group represented by Y ⁵¹ of formula (5) is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aryl group may have a substituent. Examples of the substituent include those described for the substituent T.

The number of carbon atoms of the alkyl moiety in the aralkyl group represented by Y ⁵¹ of the formula (5) is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3. The number of carbon atoms of the aryl moiety in the above aralkyl group is preferably 6 to 30, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 10, and most preferably 6 to 8. The aralkyl group may have a substituent. Examples of the substituent include those described for the substituent T.

Y ⁵¹ of formula (5) is preferably alkyl.

The alkyl group, aralkyl group and aryl group represented by R ^e51 in E ⁵¹ of formula (5) are the same as the groups described in Y ⁵¹ of formula (5).

The carbon number of the alkoxy group represented by R ^e52 in E ⁵¹ of formula (5) is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.

The reaction of the compound represented by formula (4) and the compound represented by formula (5) can be carried out in an organic solvent. The organic solvent is not particularly limited, and is preferably an amide solvent such as dimethylformamide, dimethylacetamide, and N-methyl-2-pyrrolidone, tetrahydrofuran, acetonitrile, toluene, methanol, ethanol, isopropanol, or a mixture thereof, and particularly preferably dimethylformamide or dimethylacetamide. The reaction ratio of the compound represented by the formula (4) to the compound represented by the formula (5) is appropriately set according to the desired structure of the compound represented by the formula (6). The reaction temperature is not particularly limited, and is preferably, for example, 0 to the boiling point of the reaction solvent. The reaction time is not particularly limited, and may be, for example, 1 to 48 hours.

The content of the specific compound in the total solid content of the resin composition is preferably 0.01 to 50 mass%. The lower limit is preferably 0.05 mass% or more, more preferably 0.1 mass% or more. The upper limit is preferably 40 mass% or less, more preferably 30 mass% or less, and still more preferably 20 mass% or less.

The content of the specific compound is preferably 0.01 to 50 parts by mass relative to 100 parts by mass of the resin. The lower limit is preferably 0.05 parts by mass or more, more preferably 0.1 parts by mass or more. The upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and still more preferably 20 parts by mass or less.

The resin composition may contain only one specific compound, or may contain two or more kinds. When two or more specific compounds are contained, the total amount of these is preferably within the above range.

Resin

The resin composition of the present invention contains a resin. The resin may be appropriately selected from resins satisfying various physical properties such as transparency, refractive index, and processability required according to the application, purpose, and the like.

Examples of the resin include (meth) acrylic resins, alkene-thiol resins, polyester resins, polycarbonate resins, and vinyl polymers [ for example, polydiene resins, polyolefin resins, polystyrene resins, polyvinyl ether resins, polyvinyl alcohol resins, polyvinyl ketone resins, polyvinyl fluoride resins, polyvinyl bromide resins, etc. ], polythioether resins, polystyrene resins, polyurethane resins, polysulfonate resins, nitroso polymer resins, polysiloxane resins, polysulfide resins, polythioester resins, polysulfone resins, polysulfonamide resins, polyamide resins, polyimide resins, polyurea resins, polyphosphazene resins, polysilane resins, polysilazane resins, polyfuran resins, polybenzoxazole resins, polyoxadiazole resins, polybenzothiazine phenothiazine resins, polybenzothiazole resins, polypyrazinoquinoxaline resins, polyquinoxaline resins, polybenzimidazole resins, polyoxoisoindoline resins, polydioxoisoindoline resins, polytriazine resins, polypyrazin resins, polypyridine resins, polypyridinone resins, polydicyclononane resins, polydibenzofuran resins, polydiphthalone resins, polyacetal resins, polyimide resins, cyclic olefin resins, polyimide resins, etc.

The (meth) acrylic resin may be a polymer containing a constituent unit derived from (meth) acrylic acid and/or an ester thereof. Specifically, a polymer obtained by polymerizing at least one compound selected from the group consisting of (meth) acrylic acid, (meth) acrylic acid ester, (meth) acrylamide and (meth) acrylonitrile is exemplified.

Examples of the polyester resin include a polymer obtained by reacting a polyhydric alcohol (for example, ethylene glycol, propylene glycol, glycerin, and trimethylolpropane) with a polybasic acid (for example, an aromatic dicarboxylic acid (for example, terephthalic acid, isophthalic acid, and naphthalene dicarboxylic acid, and the like, and dicarboxylic acids in which hydrogen atoms of the aromatic rings are substituted with methyl groups, ethyl groups, phenyl groups, and the like), an aliphatic dicarboxylic acid having 2 to 20 carbon atoms (for example, adipic acid, sebacic acid, and dodecanedicarboxylic acid), an alicyclic dicarboxylic acid (for example, cyclohexane dicarboxylic acid, and the like), and a polymer obtained by ring-opening polymerization of a cyclic ester compound such as a caprolactone monomer (for example, polycaprolactone). Specific examples of the polyester resin include polyethylene terephthalate and polyethylene naphthalate.

Examples of the epoxy resin include bisphenol a type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, aliphatic epoxy resin, and the like. The epoxy resin may be commercially available, and examples of the commercially available products include the following resins.

Examples of commercial products of bisphenol a epoxy resins include jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, and jER1010 (manufactured by Mitsubishi Chemical Corporation above), and EPICLON860, EPICLON1050, EPICLON1051, and EPICLON1055 (manufactured by DIC Corporation above), and the like. Examples of commercial products of bisphenol F epoxy resins include jER806, jER807, jER4004, jER4005, jER4007 and jER4010 (manufactured by Mitsubishi Chemical Corporation, supra), EPICLON830 and EPICLON (manufactured by DIC Corporation, supra), LCE-21 and RE-602S (manufactured by Nippon Kayaku co., ltd, supra), and the like. Examples of the commercial products of the phenol novolac type epoxy resins include jER152, jER154, jER157S70 and jER157S65 (manufactured by Mitsubishi Chemical Corporation above), EPICLON N-740, EPICLON N-770 and EPICLON N-775 (manufactured by DIC Corporation above), and the like. Examples of the commercially available cresol novolac type epoxy resins include EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690 and EPICLON N-695 (manufactured by DIC Corporation, above), and EOCN-1020 (manufactured by Nippon Kayaku co., ltd.). Examples of commercial products of aliphatic epoxy resins include ADEKA RESIN EP series (for example, EP-4080S, EP-4085S and EP-4088S; ADEKA CORPORATION), celoxide2021P, celoxide2081, celoxide2083, celoxide2085, EHPE3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (Daicel Corporation above), denacol EX-212L, EX-214L, EX-216L, EX-321L and EX-850L (Nagase ChemteX Corporation above), and, ADEKA RESIN EP series (for example, EP-4000S, EP-4003S, EP-4010S, EP-4011S, etc.; ADEKA CORPORATION), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501 and EPPN-502 (manufactured by ADEKA CORPORATION above), and jER1031S (manufactured by Mitsubishi Chemical Corporation), and the like. Examples of other commercially available epoxy resins include Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100 and G-01758 (the above is a polymer containing an epoxy group manufactured by NOF CORPORATION).

As the cellulose acylate resin, cellulose acylate described in paragraphs 0016 to 0021 of japanese unexamined patent publication No. 2012-215689 can be preferably used. As the polyester resin, commercially available products such as Byron series (for example, byron 500) manufactured by tolbo co., ltd. As a commercial product of the (meth) acrylic resin, a SK Dyne series (for example, SK Dyne-SF2147, etc.) of Soken Chemical & Engineering co.

The polystyrene resin is preferably a resin containing 50 mass% or more of a repeating unit derived from a styrene-based monomer, more preferably a resin containing 70 mass% or more of a repeating unit derived from a styrene-based monomer, and even more preferably a resin containing 85 mass% or more of a repeating unit derived from a styrene-based monomer.

Specific examples of the styrene monomer include styrene and its derivatives. Among them, the styrene derivative is a compound having other groups bonded to styrene, and examples thereof include alkylstyrenes such as o-methylstyrene, m-methylstyrene, p-methylstyrene, 2, 4-dimethylstyrene, o-ethylstyrene and p-ethylstyrene, and substituted styrenes such as hydroxystyrenes, tertiary Ding Yangben ethylene, vinylbenzoic acid, o-chlorostyrene and p-chlorostyrene in which a hydroxyl group, an alkoxy group, a carboxyl group, a halogen or the like is introduced into the styrene core.

The polystyrene resin may contain a repeating unit derived from a monomer other than the styrene monomer. Examples of the other monomer include alkyl (meth) acrylates such as methyl (meth) acrylate, cyclohexyl (meth) acrylate, methyl phenyl (meth) acrylate, and isopropyl (meth) acrylate; unsaturated carboxylic acid monomers such as methacrylic acid, acrylic acid, itaconic acid, maleic acid, fumaric acid, cinnamic acid, and the like; anhydride, i.e., unsaturated dicarboxylic anhydride monomers such as maleic anhydride, itaconic acid, ethylmaleic acid, methyl itaconic acid, chloromaleic acid, and the like; unsaturated nitrile monomers such as acrylonitrile and methacrylonitrile; conjugated dienes such as 1, 3-butadiene, 2-methyl-1, 3-butadiene (isoprene), 2, 3-dimethyl-1, 3-butadiene, 1, 3-pentadiene, and 1, 3-hexadiene.

Examples of the commercially available polystyrene resin include NIPPON STEEL CHEMICAL & Material Co., ltd. AS-70 (acrylonitrile-styrene copolymer resin) manufactured by Nippon STEEL CHEMICAL, KAWAHARA PETROCHEMICAL CO., LTD' S SMA2000P (styrene-maleic acid copolymer), denka Company limited. CLEAREN 530L, CLEAREN L manufactured by Denka Company, ASAHI KASEI Corporation TUFPRENE 126S, ASAPRENE T411, KRATON POLYMERSJAPAN LTD manufactured by KRATON D1102A, KRATON D1116A, STYROLUTION, styrolux S manufactured by Styrolux T, asaflex 840 manufactured by ASAHI KASEI Corporation, asaflex 860, 679 manufactured by PS Japan Corporation, HF77, SGP-10, 475D, H0103, HT478, DICK STYRENE XC-515 manufactured by DIC Corporation, DICK STYRENE-535, DICK STYRENE GH-8300-5, and the like. Further, commercial products of hydrogenated polystyrene resins include Tuftec H series manufactured by ASAHI KASEI Corporation, KRATON G series manufactured by Shell Japan Limited, DYNARON (hydrogenated styrene-butadiene random copolymer) manufactured by JSR Corporation, kuraray co. Further, commercial products of the modified polystyrene resin include Tuftec M series manufactured by ASAHI KASEI Corporation, epofriend manufactured by Daicel Corporation, polar group modified DYNARON, TOAGOSEI CO manufactured by JSR Corporation, RESEDA manufactured by LTD.

Examples of the cyclic olefin resin include (R1) a polymer containing a structural unit derived from a norbornene compound, (R2) a polymer containing a structural unit derived from a monocyclic olefin compound other than the norbornene compound, (R3) a polymer containing a structural unit derived from a cyclic conjugated diene compound, (R4) a polymer containing a structural unit derived from a vinyl alicyclic hydrocarbon compound, and (R1) a hydride of a polymer containing a structural unit derived from each of the compounds (R4). In the present specification, a ring-opened polymer including each compound among polymers including structural units derived from norbornene compounds and polymers including structural units derived from monocyclic cyclic olefin compounds.

The cyclic olefin resin is not particularly limited, and a polymer having a structural unit derived from a norbornene compound represented by the formula (A-II) or the formula (A-III) is preferable. The polymer having a structural unit represented by the formula (A-II) is an addition polymer of a norbornene compound, and the polymer having a structural unit represented by the formula (A-III) is a ring-opened polymer of a norbornene compound.

[ Chemical formula 60]

In the formulae (A-II) and (A-III), m is an integer of 0 to 4, preferably 0 or 1.

R ³～R⁶ in the formula (A-II) and the formula (A-III) each independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.

Examples of the hydrocarbyl group denoted by R ³～R⁶ include an alkyl group, an alkenyl group, an alkynyl group, and an aryl group, and is preferably an alkyl group or an aryl group.

X ², X ³、Y² and Y ³ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms substituted with a halogen atom 、-(CH₂)_nCOOR¹¹、-(CH₂)_nOCOR¹²、-(CH₂)_nNCO、-(CH₂)_nNO₂、-(CH₂)_nCN、-(CH₂)_nCONR¹³R¹⁴、-(CH₂)_nNR¹³R¹⁴、-(CH₂)_n0Z¹、-(CH₂)_n]W¹ or (-CO) ₂ O or (-CO) ₂NR¹⁵ formed by bonding X ² and Y ² or X ³ and Y ³ to each other.

R ¹¹～R¹⁵ in the above groups X ²、X³、Y² and Y ³ each independently represents a hydrogen atom OR a hydrocarbon group having 1 to 20 carbon atoms, Z ¹ represents a hydrocarbon group OR a hydrocarbon group substituted with halogen, and W ¹ represents Si (R ¹⁶)_pD_(3-p)(R¹⁶ represents a hydrocarbon group having 1 to 10 carbon atoms, D represents a halogen atom, -OCOR ¹⁷ OR-OR ¹⁷(R¹⁷ represents a hydrocarbon group having 1 to 10 carbon atoms). p is an integer of 0 to 3). n is an integer of 0 to 10, preferably 0 to 8, more preferably 0 to 6.

R ³～R⁶ in the formulae (A-II) and (A-III) is preferably a hydrogen atom or-CH ₃ independently of each other, and is more preferably a hydrogen atom from the viewpoint of moisture permeability.

X ² and X ³ are each preferably a hydrogen atom, -CH ₃、-C₂H₅, and more preferably a hydrogen atom from the viewpoint of moisture permeability.

Y ² and Y ³ are preferably each independently a hydrogen atom, a halogen atom (especially a chlorine atom) or- (CH ₂)_nCOOR¹¹ (especially-COOCH ₃), and more preferably a hydrogen atom from the viewpoint of moisture permeability.

Other groups may be appropriately selected.

The polymer having a structural unit represented by the formula (A-II) or the formula (A-III) may further comprise one or more structural units represented by the formula (A-I).

[ Chemical formula 61]

In the formula (A-I), R ¹ and R ² each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and X ¹ and Y ¹ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, a hydrocarbon group 、-(CH₂)_nCOOR¹¹、-(CH₂)_nOCOR¹²、-(CH₂)_nNCO、-(CH₂)_nNO₂、-(CH₂)_nCN、-(CH₂)_nCONR¹³R¹⁴、-(CH₂)_nNR¹³R¹⁴、-(CH₂)_nOZ¹、-(CH₂)_nW¹ having 1 to 10 carbon atoms substituted with a halogen atom, or a (-CO) ₂ O or (-CO) ₂NR¹⁵ formed by bonding X ² and Y ² or X ³ and Y ³ to each other. R ¹¹～R¹⁵ in the above groups X ¹ and Y ¹ each independently represents a hydrogen atom OR a hydrocarbon group having 1 to 20 carbon atoms, Z ¹ represents a hydrocarbon group OR a hydrocarbon group substituted with halogen, W ¹ represents Si (R ¹⁶)_pD_(3-p)(R¹⁶ represents a hydrocarbon group having 1 to 10 carbon atoms, D represents a halogen atom, -OCOR ¹⁷ OR-OR ¹⁷(R¹⁷ represents a hydrocarbon group having 1 to 10 carbon atoms). p is an integer of 0 to 3). n represents an integer of 0 to 10.

The content of the structural unit represented by the formula (A-II) or the formula (A-III) in the cyclic polyolefin resin is preferably 90% by mass or less, more preferably 30 to 85% by mass, still more preferably 50 to 79% by mass, and still more preferably 60 to 75% by mass.

Cyclic olefin resins are described in JP-A-10-007732, JP-A-2002-504184, international publication No. 2004/070463, etc., and these are appropriately referred to.

The cyclic olefin resin can be obtained by addition-polymerizing norbornene compounds (for example, polycyclic unsaturated compounds of norbornene) with each other.

Examples of the commercially available cyclic olefin resins include ARTON series (e.g., ARTON G, F, RX 4500) manufactured by JSR Corporation, ZEONOR ZF14, ZF16, ZEONEX 250, 280 manufactured by Zeon Corporation, and the like.

Examples of the cyclic olefin resin include copolymers obtained by addition-copolymerizing a norbornene compound with an olefin such as ethylene, propylene, or butylene, butadiene, a conjugated diene such as isoprene, a non-conjugated diene such as ethylidene norbornene, acrylonitrile, acrylic acid, methacrylic acid, maleic anhydride, acrylic acid ester, methacrylic acid ester, maleimide, vinyl acetate, or vinyl chloride, or other ethylenically unsaturated compounds. Among them, a copolymer with an ethylene group is preferable. Examples of such addition (co) polymers of norbornene compounds are sold under the product name APEL by Mitsui Chemicals, inc. And differ from each other in glass transition temperature (Tg), and include APL8008T (Tg 70 ℃), APL6011T (Tg 105 ℃), APL6013T (Tg 125 ℃) and APL6015T (Tg 145 ℃). Granules such as TOPAS8007, TOPAS6013, TOPAS6015 and the like are commercially available from Polyplastics co. Further, appear3000 was commercially available from Ferrania.

The hydrogenated product of the cyclic olefin resin can be synthesized by addition polymerization or ring-opening polymerization of a norbornene compound or the like, followed by hydrogenation. The synthesis method is described in, for example, JP-A-01-240517, JP-A-07-196736, JP-A-60-026024, JP-A-62-019801, JP-A-2003-159767, JP-A-2004-309979, etc.

The weight molecular weight of the cyclic olefin resin is preferably 5000 to 500000, more preferably 8000 to 200000, and still more preferably 10000 to 100000.

The polycarbonate resin may be a reaction product of a polyphenol compound and phosgene or a carbonate compound.

Examples of the polyhydric phenol compound include hydroquinone, resorcinol, 4 '-dihydroxydiphenyl, bis (4-hydroxyphenyl) methane, 1-bis (4-hydroxyphenyl) ethane, 1-bis (4-hydroxyphenyl) -1-phenylethane, bisphenol A, bisphenol C, bisphenol E, bisphenol F, bisphenol M, bisphenol P, bisphenol S, bisphenol Z, 2-bis (3-methyl-4-hydroxyphenyl) propane, 1-bis (4-hydroxyphenyl) cyclohexane, 2-bis (3-phenyl-4-hydroxyphenyl) propane, 2-bis (3-isopropyl-4-hydroxyphenyl) propane, 2-bis (4-hydroxyphenyl) butane 2, 2-bis (3, 5-dimethyl-4-hydroxyphenyl) propane, 2-bis (3, 5-dibromo-4-hydroxyphenyl) propane, 4' -dihydroxydiphenyl sulfone, 4 '-dihydroxydiphenyl sulfoxide, 4' -dihydroxydiphenyl sulfide, 3 '-dimethyl-4, 4' -dihydroxydiphenyl sulfide, 4 '-dihydroxydiphenyl ether and the like, preferably hydroquinone, resorcinol, 4' -dihydroxydiphenyl, bisphenol A.

Examples of the carbonate compound include phosgene, diphenyl carbonate, bis (chlorophenyl) carbonate, dinaphthyl carbonate, bis (diphenyl) carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and the like, and preferably bis (diphenyl) carbonate, dimethyl carbonate, and diethyl carbonate.

Examples of the commercial products of the polycarbonate resin include PANLITE L to 1250WP, PANLITE SP to 1516, MITSUBISHI GAS CHEMICAL COMPANY, iupizeta EP to 5000, iupizeta EP to 4000, and Sumika Polycarbonate Ltd.

Examples of the thiourethane resin include a reactant of an isocyanate compound and a polythiol compound, a reactant of a precursor of the thiourethane resin, and the like. As the commercial products of the thiourethane resin precursor, MR-7, MR-8, MR-10, MR-174 and the like manufactured by Mitsui Chemicals, inc. can be mentioned.

Examples of the polyamide resin include aliphatic polyamide resins and aromatic polyamide resins. Examples of the aliphatic polyamide resin include nylon 6, nylon 11, nylon 12, nylon 46, nylon 66, nylon 666, nylon 610, nylon 612, and the like. Examples of the aromatic polyamide resin include resins that are polymerized by dehydration condensation of a diamine and a dicarboxylic acid, and that contain an aromatic ring in at least one of the diamine and the dicarboxylic acid. Specific examples of the aromatic polyamide resin include polycondensates of m-xylylenediamine and adipic acid or adipoyl halide.

The resin may have an acid group. Examples of the acid group include a carboxyl group, a phosphate group, a sulfonate group, and a phenolic hydroxyl group. The acid group may be one kind or two or more kinds. Resins having acid groups can be used as alkali-soluble resins, and can also be used as dispersants.

As the resin having an acid group, reference can be made to the description of paragraphs 0558 to 0571 of japanese patent application laid-open No. 2012-208494 (paragraphs 0685 to 0700 of the corresponding us patent application publication No. 2012/0235099) and the description of paragraphs 0076 to 0099 of japanese patent application laid-open No. 2012-198408, and these are incorporated herein by reference. Also, ACRYBASE FF to 426 (NIPPON SHOKUBAI co., ltd.) can be used as the resin having an acid group.

The acid value of the resin having an acid group is preferably 30 to 200mgKOH/g. The lower limit of the acid value is preferably 50mgKOH/g or more, more preferably 70mgKOH/g or more. The upper limit of the acid value is preferably 150mgKOH/g or less, more preferably 120mgKOH/g or less. The acid value of the resin was measured in accordance with JIS K0070 (1992), and was calculated in terms of 1 mmol/g=56.1 mgKOH/g.

The resin may have a curable group. Examples of the curable group include an ethylenically unsaturated bond-containing group, an epoxy group, a hydroxymethyl group, and an alkoxysilyl group. Examples of the ethylenically unsaturated bond-containing group include vinyl, styryl, allyl, methallyl, and (meth) acryl. Examples of the alkoxysilyl group include a monoalkoxysilyl group, a dialkoxysilyl group, and a trialkoxysilyl group.

As commercial products of the curable group-containing resin, dianal BR series (polymethyl methacrylate (PMMA), for example, manufactured by Dianal BR-80, BR-83 and BR-87;Mitsubishi Chemical Corporation) are mentioned; photomer 6173 (polyurethane acrylic oligomer containing COOH; diamond Shamrock Co., ltd.); viscoat R-264 and KS resin 106 (both manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD); CYCLOMER P series (e.g., ACA230 AA), PLACCEL CF series (both manufactured by Daicel Corporation), ebecryl 3800 (manufactured by Daicel UCB Co., ltd.), acrycure-RD-F8 (manufactured by NIPPON SHOKUBAI CO., LTD.), and the like. Further, for example, the products described in the above epoxy resins are commercially available products.

In the case where the resin composition of the present invention is used for a lens (for example, a spectacle lens), the resin is preferably a thermoplastic resin such as a carbonate resin or a (meth) acrylic resin or a thermosetting resin such as a urethane resin.

Adhesives and binders can also be used as the resin. Examples of the binder include an acrylic binder, a rubber binder, and a silicone binder. The acrylic adhesive refers to an adhesive comprising a polymer of (meth) acrylic monomers ((meth) acrylic polymer). Examples of the binder include urethane resin binders, polyester binders, acrylic resin binders, ethylene vinyl acetate resin binders, polyvinyl alcohol binders, polyamide binders, and silicone binders. Among them, from the viewpoint of high adhesive strength, a urethane resin adhesive or a silicone adhesive is preferable as the adhesive. As the binder, commercially available products can be used, and examples of the commercially available products include TOYO INK CO., urethane resin binders (LIS-073-50U: product name), acrylic Chemical & Engineering Co., ltd., acrylic binders (SK Dyne-SF2147: product name), and the like.

The resin is preferably at least one selected from the group consisting of (meth) acrylic resins, polystyrene resins, polyester resins, polyurethane resins, thiourethane resins, polyimide resins, polyamide resins, epoxy resins, polycarbonate resins, phthalate resins, cellulose acylate resins, and cyclic olefin resins, and more preferably at least one selected from the group consisting of (meth) acrylic resins, polystyrene resins, polyester resins, polyurethane resins, and cyclic olefin resins, from the viewpoint of good compatibility with a specific compound and easy obtainment of a cured product with suppressed surface morphology unevenness.

The weight average molecular weight (Mw) of the resin is preferably 2000 to 2000000. The lower limit of Mw of the resin is preferably 5000 or more, more preferably 10000 or more, and still more preferably 50000 or more. The upper limit of the Mw of the resin is preferably 1000000 or less, more preferably 500000 or less, and further preferably 200000 or less. When an epoxy resin is used, the weight average molecular weight (Mw) of the epoxy resin is preferably 100 or more, more preferably 200 to 2000000. The upper limit of the Mw of the epoxy resin is preferably 1000000 or less, more preferably 500000 or less. The lower limit of Mw of the epoxy resin is preferably 2000 or more.

The weight average molecular weight (Mw) is a value measured by Gel Permeation Chromatography (GPC). In the measurement by GPC, HLC (registered trademark) -8020GPC (manufactured by TOSOH CORPORATION) was used as a measuring device, 3 TSKgel (registered trademark) Super Multipore HZ-H (manufactured by 4.6 mmID. Times.15 cm, TOSOH CORPORATION) was used as a column, and THF (tetrahydrofuran) was used as an eluent. The measurement conditions were that the sample concentration was 0.45 mass%, the flow rate was 0.35ml/min, the sample injection amount was 10. Mu.l, and the measurement temperature was 40℃and the RI detector was used. The calibration curve is defined by TOSOH CORPORATION "standard TSK STANDARD, polystyrene": the samples "F-40", "F-20", "F-4", "F-1", "A-5000", "A-2500", "A-1000" and "n-propylbenzene" were prepared.

The total light transmittance of the resin is preferably 80% or more, more preferably 85% or more, and still more preferably 90% or more. In the present specification, the total light transmittance of the resin is measured according to the content described in "4 th edition of experimental chemistry lecture 29 high molecular material medium" (pill, 1992) pages 225 to 232.

The content of the resin in the total solid content of the resin composition is preferably 1 to 99.9 mass%. The lower limit is preferably 30 mass% or more, more preferably 50 mass% or more, and still more preferably 70 mass% or more. The upper limit is preferably 95 mass% or less, more preferably 90 mass% or less, and still more preferably 80 mass% or less. The resin composition may contain one kind of resin or two or more kinds of resin. When two or more resins are contained, the total amount of these is preferably within the above range.

Other ultraviolet absorbers

The resin composition of the present invention may contain an ultraviolet absorber (hereinafter, also referred to as other ultraviolet absorbers) other than the above specific compounds. According to this aspect, a cured product that blocks light having a wavelength in the ultraviolet region can be formed over a wide range.

The maximum absorption wavelength of the other ultraviolet absorber is preferably in the range of 300 to 380nm, more preferably in the range of 300 to 370nm, even more preferably in the range of 310 to 360nm, and particularly preferably in the range of 310 to 350 nm.

The other ultraviolet absorber is also preferably a compound having a polymerizable group. Examples of the polymerizable group include vinyl, allyl, (meth) acryl, (meth) acryloyloxy, (meth) acryloylamino, and vinylphenyl.

Examples of the other ultraviolet absorber include an amino butadiene-based ultraviolet absorber, a dibenzoylmethane-based ultraviolet absorber, a benzotriazole-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, a salicylic acid-based ultraviolet absorber, an acrylic ester-based ultraviolet absorber, and a triazine-based ultraviolet absorber, and the like, preferably a benzotriazole-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, and a triazine-based ultraviolet absorber, and more preferably a benzotriazole-based ultraviolet absorber and a triazine-based ultraviolet absorber. Specific examples of the other ultraviolet absorbers include the compounds described in examples described below. And, in addition, the processing unit, other ultraviolet absorbers can be used as the ultraviolet absorber in Japanese patent application laid-open No. 2009-263616, the 0065 section of International publication No. 2017/122503, the Japanese patent application laid-open No. 2003-128730, the Japanese patent application laid-open No. 2003-129033, the Japanese patent application laid-open No. 2014-077076, the Japanese patent application laid-open No. 2015-164994, the Japanese patent application laid-open No. 2015-168822, the Japanese patent application laid-open No. 2018-135282, the Japanese patent application laid-open No. 2018-168889, the Japanese patent application laid-open No. 2018-168478, the Japanese patent application laid-open No. 2018-188589, the Japanese patent application laid-open No. 2019-001767, the Japanese patent application laid-open No. 2020-023697; japanese patent application laid-open No. 2020-04013, japanese patent No. 5518613, japanese patent No. 5868465, japanese patent No. 6301526, japanese patent No. 6354665, japanese patent application laid-open No. 2017-503905, international publication No. 2015/064674, international publication No. 2015/064675, international publication No. 2017/102675, international publication No. 2018/190281, international publication No. 2018/216750, international publication No. 2019/087983, european patent No. 2379512, european patent No. 2951163, etc.

When the resin composition contains another ultraviolet absorber, the content of the other ultraviolet absorber in the total solid content of the resin composition is preferably 0.01 to 50% by mass. The lower limit is preferably 0.05 mass% or more, more preferably 0.1 mass% or more. The upper limit is preferably 40 mass% or less, more preferably 30 mass% or less, and still more preferably 20 mass% or less.

The total content of the specific compound and the other ultraviolet absorber in the total solid content of the resin composition is preferably 0.01 to 50 mass%. The lower limit is preferably 0.05 mass% or more, more preferably 0.1 mass% or more. The upper limit is preferably 40 mass% or less, more preferably 30 mass% or less, and still more preferably 20 mass% or less.

The resin composition may contain only one kind of other ultraviolet absorber, or may contain two or more kinds. When two or more other ultraviolet absorbers are contained, the total amount of these is preferably within the above range.

Polymerizable Compound

The resin composition of the present invention may contain a polymerizable compound. As the polymerizable compound, a compound that can be polymerized and cured by applying energy can be used without limitation. The polymerizable compound may be a radical polymerizable compound or a cation polymerizable compound. Examples of the radical polymerizable compound include a compound having a group containing an ethylenically unsaturated bond. The polymerizable compound is preferably a compound having a group containing an ethylenically unsaturated bond, more preferably a compound having 2 or more groups containing an ethylenically unsaturated bond. The upper limit of the number of the ethylenically unsaturated bond-containing groups contained in the polymerizable compound is preferably 15 or less, more preferably 10 or less, and still more preferably 6 or less. Examples of the ethylenically unsaturated bond-containing group included in the polymerizable compound include a vinyl group, an allyl group, and a (meth) acryloyl group.

The polymerizable compound may be any of a monomer, a prepolymer (that is, a dimer, a trimer or an oligomer), a mixture of these, a (co) polymer of a compound selected from the group consisting of a monomer and a prepolymer, and the like, but is preferably a monomer.

The molecular weight of the polymerizable compound is preferably 100 to 3000. The upper limit is preferably 2000 or less, more preferably 1500 or less. The lower limit is preferably 150 or more, more preferably 250 or more.

(Radical polymerizable Compound)

Examples of the radical polymerizable compound include a compound having a group containing an ethylenically unsaturated bond.

Examples of the radical polymerizable compound include unsaturated carboxylic acids (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), esters of unsaturated carboxylic acids and amides of unsaturated carboxylic acids, and (co) polymers of unsaturated carboxylic acids or esters or amides thereof. Among them, esters of unsaturated carboxylic acids and aliphatic polyols, amides of unsaturated carboxylic acids and aliphatic polyamines, and homopolymers or copolymers of these are preferable.

As the radical polymerizable compound, an addition reactant of an unsaturated carboxylic acid ester or an unsaturated carboxylic acid amide having a nucleophilic substituent (for example, a hydroxyl group, an amino group, a mercapto group, or the like) and a monofunctional or polyfunctional isocyanate compound or an epoxy compound can also be used; dehydration condensation reactants of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having nucleophilic substituents with mono-or polyfunctional carboxylic acids; addition reactants of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having electrophilic substituents (e.g., isocyanate groups, epoxy groups, etc.) with monofunctional or polyfunctional alcohols, amines, or thiols; substitution reactants of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having a releasable substituent (e.g., halo, tosyloxy, etc.) with mono-or polyfunctional alcohols, amines, or thiols; etc. In addition, a compound obtained by substituting the unsaturated carboxylic acid with an unsaturated phosphonic acid, styrene, vinyl ether, or the like can also be used.

The radical polymerizable compound may be used in combination of a plurality of compounds having different functional groups or a plurality of compounds having different kinds of polymerizable groups (for example, an acrylate, a methacrylate, a styrene compound, a vinyl ether compound, etc.).

The radical polymerizable compound is preferably a (meth) acrylate compound, more preferably a 2-functional or more (meth) acrylate compound, still more preferably a 2-15-functional (meth) acrylate compound, still more preferably a 2-10-functional (meth) acrylate compound, and particularly preferably a 2-6-functional (meth) acrylate compound.

Specific examples of the radical polymerizable compound include pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tris ((meth) acryloyloxyethyl) isocyanurate, pentaerythritol tetra (meth) acrylate ethylene oxide EO (ethylene oxide) modified, dipentaerythritol hexa (meth) acrylate EO (ethylene oxide) modified, benzyl (meth) acrylate, and the like.

Examples of the commercially available products of the radical polymerizable compounds include KAYARAD series (e.g., D-330, D-320, D-310, PET-30, TPA-330, DPHA, etc.), shin-Nakamura Chemical co, NK Ester series (e.g., a-DPH-12E, A-TMMT, a-TMM-3, etc.), KYOEISHA CHEMICAL co, LIGHT ACRYLATE series (e.g., DCP-a, etc.), TOAGOSEI co, aromix series (e.g., M-305, M-306, M-309, M-450, M-402, T0-1382, etc.), osaka Organic Chemical Industry co, viscoat series (e.g., v#802, etc.), etc., manufactured by ltd.

As the radical polymerizable compound, those described as a photocurable monomer or oligomer in JP-A-48-064183, JP-B-49-043191 and JP-B-52-030490, journal of the Adhesion Society of Japan vol.20, no.7, and pages 300 to 308 (1984) can be used.

(Cationically polymerizable Compound)

Examples of the cationically polymerizable compound include compounds having a cationically polymerizable group. Examples of the cationically polymerizable group include cyclic ether groups such as epoxy group and oxetanyl group, vinyl ether groups, and the like, and the cyclic ether groups are preferable. The cation polymerizable compound is preferably a multifunctional cation polymerizable compound having 2 or more cation polymerizable groups.

Examples of the cationically polymerizable compound include a polyfunctional alicyclic epoxy compound, a polyfunctional heterocyclic epoxy compound, a polyfunctional oxetane compound, an alkylene glycol diglycidyl ether, and an alkylene glycol monovinyl monoglycidyl ether.

Specific examples of the cationically polymerizable compound include 3',4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, 3, 4-epoxycyclohexylmethyl-3 ',4' -epoxycyclohexane carboxylate, l, 2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2, 2-bis (hydroxymethyl) -1-butanol, dimethylbenzene dioxetane, 3-ethyl-3-hydroxymethyl oxetane, 3-ethyl-3- { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane, cyclohexanedimethanol divinyl ether, 2-ethylhexyl vinyl ether, cyclohexanedimethanol monovinyl ether, 4-hydroxybutyl vinyl ether, and compounds described in paragraphs 0029 to 0058 of Japanese patent application laid-open No. 2012-046577.

Among the cationically polymerizable compounds, (meth) acrylate compounds having a cationically polymerizable group can also be used. Specific examples of the (meth) acrylate compound having a cationically polymerizable group include methyl 3, 4-epoxycyclohexylmethacrylate and the like. Examples of the commercial products include CYCLOMER M100 manufactured by Daicel Corporation.

As the cationically polymerizable compound, use can also be made of TOAGOSEI co., aron oxetane series (next-101, next-121, next-221, etc.) manufactured by ltd. And Celoxide series (2021P) manufactured by Daicel Corporation, NIPPON CARBIDE INDUSTRIES co., alkyl divinyl ether CHDVE, alkyl monovinyl ether EHVE, hydroxyalkyl vinyl ether CHMVE, hydroxyalkyl vinyl ether HBVE, etc. manufactured by inc. Further, an epoxy resin exemplified as a specific example of the epoxy resin described later can also be used.

When the resin composition contains a polymerizable compound, the content of the polymerizable compound in the total solid content of the resin composition is preferably 0.1 to 90% by mass. The lower limit is preferably 1 mass% or more, more preferably 5 mass% or more. The upper limit is preferably 80 mass% or less, more preferably 70 mass% or less. The resin composition may contain only one kind of polymerizable compound, or may contain two or more kinds. When two or more polymerizable compounds are contained, the total amount of these is preferably within the above range.

Polymerization initiator

The resin composition can contain a polymerization initiator. The polymerization initiator may be a compound capable of generating an initiating species required for polymerization reaction by imparting energy thereto. The polymerization initiator may be a radical polymerization initiator or a cationic polymerization initiator. When a radical polymerizable compound is used as the polymerizable compound, the polymerization initiator is preferably a radical polymerization initiator. In the case where a cationically polymerizable compound is used as the polymerizable compound, the polymerization initiator is preferably a cationic polymerization initiator.

The polymerization initiator may be appropriately selected from, for example, a photopolymerization initiator and a thermal polymerization initiator, and is preferably a photopolymerization initiator. The photopolymerization initiator is a compound that is sensitized by exposure to light and starts or accelerates the polymerization of the polymerizable compound. The photopolymerization initiator may be a photo radical polymerization initiator or a photo cation polymerization initiator, and is preferably a photo radical polymerization initiator. The photo radical polymerization initiator is preferably a compound which generates radicals upon being induced by an activating light having a wavelength of 300nm or more.

(Photo radical polymerization initiator)

Examples of the photo radical polymerization initiator include oxime compounds, halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, and the like), oxadiazole compounds, carbonyl compounds, ketal compounds, benzoin compounds, acridine compounds, organic peroxides, azo compounds, coumarin compounds, azide compounds, metallocene compounds, hexaarylbisimidazole compounds, organoboric acid compounds, disulfonic acid compounds, onium salt compounds, acetophenone compounds, acylphosphine compounds, and benzophenone compounds.

Examples of the acetophenone compound include an aminoacetophenone compound and a hydroxyacetophenone compound. Examples of the acetophenone compound include acetophenone compounds described in JP 2009-191179A and JP 10-291969A. Examples of commercial products of the aminoacetophenone compound include Omnirad 907, omnirad 369E, omnirad EG (manufactured by IGM RESINS B.V. above), and the like. Commercial products of hydroxyacetophenone compounds include Omnirad 184, omnirad 1173, omnirad 2959, omnirad 127 (manufactured by IGM RESINS b.v. above), and the like.

The acylphosphine compound includes those described in Japanese patent publication No. 4225898. Examples of commercial products of the acylphosphine compound include Omnirad 819 and Omnirad TPO (manufactured by IGM RESINS b.v. above).

Examples of the benzophenone compound include benzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methoxybenzophenone, 2-chlorobenzophenone, 4-bromobenzophenone, 2-carboxybenzophenone, 2-ethoxycarbonylbenzophenone, benzophenone tetracarboxylic acid or its tetramethyl ester, 4' -bis (dialkylamino) benzophenone (for example, 4,4' -bis (dimethylamino) benzophenone, 4' -bis (dicyclohexylamino) benzophenone, 4' -bis (diethylamino) benzophenone, 4' -bis (dihydroxyethylamino) benzophenone), 4-methoxy-4 ' -dimethylaminobenzophenone, 4' -dimethoxybenzophenone, 4-dimethylaminobenzophenone, 4-dimethylaminoacetophenone and the like are preferable from the viewpoints of sensitivity and light resistance of the obtained cured product.

Examples of the oxime compound include a compound described in Japanese patent application laid-open No. 2001-233836, a compound described in Japanese patent application laid-open No. 2000-080068, a compound described in Japanese patent application laid-open No. 2006-342166, and a compound described in paragraphs 0073 to 0075 of Japanese patent application laid-open No. 2016-006475. Among the oxime compounds, oxime ester compounds are preferable. Examples of the commercial products of the oxime compounds include Irgacure OXE01, irgacure OXE02 (manufactured by BASF corporation), and Irgacure OXE03 (manufactured by BASF corporation).

Examples of halogenated hydrocarbon derivatives include compounds described in "Bull chem. Soc. Japan"42, 2924 (1969), U.S. Pat. No. 3905815, japanese patent publication No. 46-004605, japanese patent application publication No. 48-036281, japanese patent application publication No. 55-032070, japanese patent application publication No. 60-239736, japanese patent application publication No. 61-169835, japanese patent application publication No. 61-169837, japanese patent application publication No. 62-058241, japanese patent application publication No. 62-212401, japanese patent application publication No. 63-070243, japanese patent application publication No. 63-298339, and M.P.Hutt "Journal of Heterocyclic Chemistry"1 (No. 3), (1970), and the like, and preferably trihalomethyl-substituted oxazole compounds or triazine compounds.

Examples of the hexaarylbisimidazole compound include those described in Japanese patent publication No. H06-029285, U.S. Pat. No. 3479185, U.S. Pat. No. 4311783 and U.S. Pat. No. 4622286. Specifically, 2' -bis (o-chlorophenyl) -4,4', 5' -tetraphenylbisimidazole, 2' -bis (o-bromophenyl)) 4,4', 5' -tetraphenylbisimidazole, 2' -bis (o, p-dichlorophenyl) -4,4', 5' -tetraphenyl bisimidazole, 2' -bis (o-chlorophenyl) -4,4', 5' -tetrakis (m-methoxyphenyl) bisimidazole, 2' -bis (o, o ' -dichlorophenyl) -4,4', 5' -tetraphenyl bisimidazole, 2' -bis (o-nitrophenyl) -4,4', 5' -tetraphenyl bisimidazole, 2' -bis (o-methylphenyl) -4,4',5,5' -tetraphenyl bisimidazole, 2' -bis (o-trifluorophenyl) -4,4', 5' -tetraphenyl bisimidazole, and the like.

(Photo cationic polymerization initiator)

The photo-cation polymerization initiator is not particularly limited as long as it is a compound that generates a protonic acid or a lewis acid in order to receive light irradiation. The photoacid generator is preferably a compound that generates an acid by sensing an activating light having a wavelength of 300nm or more, more preferably 300 to 450 nm. The photoacid generator is preferably a compound that generates an acid having a pKa of 4 or less by light irradiation, more preferably a compound that generates an acid having a pKa of 3 or less, and still more preferably a compound that generates an acid having a pKa of 2 or less.

Examples of the photo-cation polymerization initiator include oxime sulfonate compounds, triazine compounds, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, sulfone compounds, sulfonate compounds, iminosulfonate compounds, carboxylate compounds, and sulfonimide compounds.

Specific examples of the photo-cationic polymerization initiator include compounds described in paragraphs 0061 to 0108 of JP-A2012-046577, paragraphs 0029 to 0030 of JP-A2002-122994, compounds described in paragraphs 0037 to 0063 of JP-A2002-122994, oxime sulfonate compounds described in paragraphs 0081 to 0108 of JP-A2013-210616, and the like. Commercially available products of the photo-cationic polymerization initiator include WPAG-469 (manufactured by FUJIFILM Wako Pure Chemical Corporation), CPI-100P (manufactured by San-Apro Ltd.), CPI-210S (manufactured by San-Apro Ltd.), irgacure290 (BASF Japan Ltd.), and the like.

(Thermal polymerization initiator)

The thermal polymerization initiator is not particularly limited, and a known thermal polymerization initiator can be used. For example, the number of the cells to be processed, examples thereof include 2,2 '-azobis (isobutyric acid) dimethyl, 2' -azobisisobutyronitrile, 2 '-azobis (2, 4-dimethyl-4-methoxyvaleronitrile), 2' -azobis (2, 4-dimethylvaleronitrile), dimethyl-2, 2 '-azobis (2-methylpropionate), 2' -azobis (2-methylbutyronitrile), and azo compounds such as1, 1 '-azobis (cyclohexane-1-carbonitrile), 2' -azobis (N-butyl-2-methylpropanamide), dimethyl 1,1 '-azobis (1-cyclohexane carboxylate), and 2,2' -azobis [2- (2-imidazolin-2-yl) propane ]2 hydrochloride;

Organic peroxides such as 1, 1-di (t-hexylperoxy) cyclohexane, 1-di (t-butylperoxy) cyclohexane, 2-di (4, 4-di- (t-butylperoxy) cyclohexyl) propane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3, 5-trimethylhexanoate, t-butylperoxylaurate, dicumyl peroxide, di (t-butyl) peroxide, t-butylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, cumene hydroperoxide, t-butyl hydroperoxide, and the like;

inorganic peroxides such as potassium persulfate, ammonium persulfate, and hydrogen peroxide;

Etc.

When the resin composition contains a polymerization initiator, the content of the polymerization initiator in the total solid content of the resin composition is preferably 0.1 to 20 mass%. The lower limit is preferably 0.3 mass% or more, more preferably 0.4 mass% or more. The upper limit is preferably 15 mass% or less, more preferably 10 mass% or less. The resin composition may contain only one kind of polymerization initiator, or may contain two or more kinds. When two or more polymerization initiators are contained, the total amount of these is preferably within the above range.

Catalyst

The resin composition of the present invention can contain a catalyst. Examples of the catalyst include acid catalysts such as hydrochloric acid, sulfuric acid, acetic acid, and propionic acid, and base catalysts such as sodium hydroxide, potassium hydroxide, and triethylamine. When the resin composition contains a catalyst, the content of the catalyst is preferably 0.1 to 100 parts by mass, more preferably 0.1 to 50 parts by mass, and even more preferably 0.1 to 20 parts by mass, relative to 100 parts by mass of the resin. The resin composition may contain only one kind of catalyst, or may contain two or more kinds. When two or more catalysts are contained, the total amount of these is preferably within the above range.

Silane coupling agent

The resin composition of the present invention can contain a silane coupling agent. According to this aspect, the adhesion between the obtained film and the support can be further improved. In the present invention, the silane coupling agent refers to a silane compound having a hydrolyzable group and functional groups other than the hydrolyzable group. The hydrolyzable group is a substituent that is directly bonded to a silicon atom and can form a siloxane bond through at least one of hydrolysis and condensation. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a urea group, a thioether group, an isocyanate group, and a phenyl group, and amino groups, a (meth) acryl group, and an epoxy group are preferable. Specific examples of the silane coupling agent include compounds described in paragraphs 0018 to 0036 of JP-A2009-288703 and compounds described in paragraphs 0056 to 0066 of JP-A2009-242604, and these are incorporated herein by reference. As a commercially available product of the silane coupling agent, there may be mentioned Soken Chemical & Engineering Co., ltd. A-50 (organosilane) and the like. The content of the silane coupling agent in the total solid content of the resin composition is preferably 0.1 to 5 mass%. The upper limit is preferably 3 mass% or less, more preferably 2 mass% or less. The lower limit is preferably 0.5 mass% or more, more preferably 1 mass% or more. The silane coupling agent may be one kind or two or more kinds. In the case of two or more kinds, the total amount is preferably within the above range.

Surfactant(s)

The resin composition of the present invention may contain a surfactant. Examples of the surfactant include surfactants described in paragraphs 0060 to 0071 of JP-A-4502784, paragraph 0017 and JP-A-2009-237362.

The surfactant is preferably a nonionic surfactant, a fluorine-based surfactant or a silicone-based surfactant.

Examples of the commercially available fluorine-based surfactant include those manufactured by DIC Corporation of MEGAFACE F-171、F-172、F-173、F-176、F-177、F-141、F-142、F-143、F-144、F-437、F-475、F-477、F-479、F-482、F-551-A、F-552、F-554、F-555-A、F-556、F-557、F-558、F-559、F-560、F-561、F-565、F-563、F-568、F-575、F-780、EXP、MFS-330、R-41、R-41-LM、R-01、R-40、R-40-LM、RS-43、TF-1956、RS-90、R-94、RS-72-K、DS-21( or more), FLUORAD FC430, FC431, FC171 (manufactured by Sumitomo 3M Limited) Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (manufactured by AGC Inc. above), polyFox PF636, PF656, PF6320, PF6520, PF7002 (manufactured by OMNOVA Solutions Inc. manufactured by OMNOVA solution Inc. manufactured by )、Footgent 710FM、610FM、601AD、601ADH2、602A、215M、245F、251、212M、250、209F、222F、208G、710LA、710FS、730LM、650AC、681( or more NEOS COMPANY LIMITED), and the like.

The fluorine-based surfactant can also preferably use an acrylic compound containing a molecular structure having a functional group containing a fluorine atom, and when heated, a portion of the functional group containing a fluorine atom is cleaved to volatilize the fluorine atom. Examples of such a fluorine-based surfactant include MEGAFACE DS series (THE CHEMICAL DAILY (day 22 of 2016), NIKKEI BUSINESS DAILY (day 23 of 2016), for example MEGAFACE DS-21, manufactured by DIC Corporation.

The fluorine-based surfactant is also preferably a polymer of a vinyl ether compound containing a fluorine atom and having a fluorinated alkyl group or a fluorinated alkylene ether group, and a hydrophilic vinyl ether compound.

Fluorine-based surfactants can also be used as the end-capped polymer.

The fluorine-containing surfactant may be a fluorine-containing polymer compound containing a repeating unit derived from a (meth) acrylate compound having a fluorine atom and a repeating unit derived from a (meth) acrylate compound having 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy group or propyleneoxy group).

The fluorine-based surfactant may be a fluoropolymer having an ethylenically unsaturated bond-containing group in a side chain. Commercially available products include MEGAFACE RS-101, RS-102, RS-718K, RS-72-K (manufactured by DIC Corporation, supra), and the like.

Further, since there is concern about the environmental suitability of a compound having a linear perfluoroalkyl group having 7 or more carbon atoms, a surfactant using a substitute material of perfluorooctanoic acid (PFOA) or perfluorooctane sulfonate (PFOS) is preferably used as the fluorine-based surfactant.

The silicone surfactant includes a linear polymer formed of a siloxane bond and a modified siloxane polymer having an organic group introduced into a side chain or a terminal. Examples of the commercially available silicone surfactant include DOWSIL 8032 ADDITIVE、Toray Silicone DC3PA、Toray Silicone SH7PA、Toray Silicone DC11PA、Toray Silicone SH21PA、Toray Silicone SH28PA、Toray Silicone SH29PA、Toray Silicone SH30PA、Toray Silicone SH8400( or more of Dow Corning Toray Co., ltd. Manufactured by Shin-Etsu Chemical Co., ltd. Manufactured by )、X-22-4952、X-22-4272、X-22-6266、KF-351A、K354L、KF-355A、KF-945、KF-640、KF-642、KF-643、X-22-6191、X-22-4515、KF-6004、KP-341、KF-6001、KF-6002( or more of F-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials Inc. manufactured by BYK-307, BYK323, BYK330 (manufactured by BYK Chemie Co., ltd.).

Examples of the nonionic surfactant include glycerin, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (for example, glycerin propoxylate, glycerin ethoxylate), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, and sorbitan fatty acid esters. Examples of the commercial products of the nonionic surfactants include PLURONIC L10, L31, L61, L62, 10R5, 17R2, 25R2 (manufactured by BASF corporation, above), TETRONIC 304, 701, 704, 901, 904, 150R1 (manufactured by BASF corporation, above), SOLSPERSE 20000 (manufactured by Lubrizol Japan Ltd., above), NCW-101, NCW-1001, NCW-1002 (manufactured by FUJIFILM Wako Pure Chemical Corporation, above), PIONIN D-6112, D-6112-W, D-6315 (manufactured by TAKEMOTO OIL FAT & CO., LTD, above), OLFINE 1010, surfynol 104, 400, 440 (manufactured by NISSIN CHEMICAL Industry Co., above), ltd.

The content of the surfactant in the total solid content of the resin composition is preferably 0.01 to 3.0 mass%, more preferably 0.05 to 1.0 mass%, and even more preferably 0.10 to 0.80 mass%. The surfactant may be one kind or two or more kinds. In the case of two or more kinds, the total amount is preferably within the above range.

Solvent (S)

The resin composition preferably further comprises a solvent. The solvent is not particularly limited, and examples thereof include water and an organic solvent. The solvent is preferably an organic solvent.

Examples of the organic solvent include alcohol solvents, ester solvents, ether solvents, ketone solvents, amide solvents, hydrocarbon solvents, and halogen solvents.

Specific examples of the alcohol-based solvent include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 1-methoxy-2-propanol, 2-ethoxyethanol, 2-butoxyethanol, ethylene glycol, propylene glycol, glycerin, and the like.

Specific examples of the ester-based solvent include methyl acetate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, alkyl alkoxyacetate (examples include methyl alkoxyacetate, ethyl alkoxyacetate, butyl alkoxyacetate (specifically, methyl methoxyacetate, ethyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.), alkyl 3-oxopropionate, alkyl 2-oxopropionate, methyl 2-oxo-2-methylpropionate, ethyl 2-oxo-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl acetoacetate, ethyl 2-oxobutyrate, ethyl methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethyl 3-ethoxymethyl propionate, ethyl carbonate, and the like.

Specific examples of the ether-based solvent include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether, polyethylene glycol, polypropylene glycol, ethylene glycol dialkyl ether, propylene glycol dialkyl ether, polyethylene glycol dialkyl ether, polypropylene glycol dialkyl ether, dioxane, and the like.

Specific examples of the amide-based solvent include N-methylpyrrolidone, dimethylformamide, dimethylacetamide, and the like.

Specific examples of the ketone solvent include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, and 3-heptanone.

Specific examples of the hydrocarbon solvent include toluene and xylene.

Specific examples of the halogen-based solvent include chloroform and methylene chloride.

These organic solvents may be used in combination of two or more.

The organic solvent preferably includes at least one selected from the group consisting of 3-ethoxymethyl propionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate.

The content of the solvent in the resin composition is preferably 10 to 90% by mass, more preferably 30 to 90% by mass, and even more preferably 50 to 90% by mass. The resin composition may contain one solvent or two or more solvents. When two or more solvents are contained, the total amount of these is preferably within the above range.

When the resin composition of the present invention is used as a kneaded material, the content of the organic solvent in the resin composition is preferably 0.1% by mass or less, more preferably 0.01% by mass or less.

Plasticizer(s)

When the resin composition of the present invention is used as a kneaded material, the resin composition of the present invention may contain a plasticizer. Examples of the plasticizer include phthalate plasticizers, phosphate plasticizers, trimellitate plasticizers, fatty acid ester plasticizers, polyester plasticizers, glycerin plasticizers, and polyalkylene glycol plasticizers, and phthalate plasticizers and phosphate plasticizers are preferable.

Examples of the phthalate plasticizer include dimethyl phthalate, diethyl phthalate, diisopropyl phthalate, dibutyl phthalate, diisobutyl phthalate, dihexyl phthalate, dicyclohexyl phthalate, diphenyl phthalate, bis (2-ethylhexyl) phthalate, diisononyl phthalate, diisodecyl phthalate, and heneicosyl phthalate.

Examples of the phosphate plasticizer include trimethyl phosphate, triethyl phosphate, tributyl phosphate, triphenyl phosphate, and tricresyl phosphate.

Examples of the trimellitate plasticizer include tributyl trimetaphosphate and tri (2-ethylhexyl) trimellitate.

Examples of the fatty acid ester plasticizer include dimethyl adipate, diethyl adipate, dipropyl adipate, diisopropyl adipate, dibutyl adipate, diisobutyl adipate, dimethyl laurate, dibutyl maleate, and ethyl oleate.

Examples of the polyester plasticizer include polyesters between acid components such as adipic acid, sebacic acid, terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, diphenyl dicarboxylic acid, and rosin and hydroxycarboxylic acids such as polyester formed from glycol components such as propylene glycol, 1, 3-butanediol, 1, 4-butanediol, 1, 6-hexanediol, ethylene glycol, and diethylene glycol, and polycaprolactone. These polyesters may be end-capped with a monofunctional carboxylic acid or a monofunctional alcohol, or may be end-capped with an epoxy compound or the like.

Examples of the glycerin plasticizer include glycerin monoacetylmonolaurate, glycerin diacetyl monolaurate, glycerin monoacetylmonostearate, glycerin diacetyl monooleate, and glycerin monoacetylmontan acid glyceride.

Examples of the polyalkylene glycol plasticizer include polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, bisphenol ethylene oxide addition polymer, bisphenol propylene oxide addition polymer, bisphenol tetrahydrofuran addition polymer, and the like, and terminal epoxy-modified compounds, terminal ester-modified compounds, terminal ether-modified compounds, and the like thereof.

The molecular weight of the plasticizer is preferably less than 3000, more preferably 2000 or less, and even more preferably 1500 or less.

The content of the plasticizer in the resin composition is preferably 0.001 to 30 mass%. The lower limit is preferably 0.005 mass% or more, more preferably 0.01 mass% or more. The upper limit is preferably 20 mass% or less, more preferably 10 mass% or less.

The kneaded material may contain only one kind of plasticizer, or may contain two or more kinds. When two or more plasticizers are contained, the total amount of these is preferably within the above range.

Other additives

The resin composition may contain any additives such as antioxidants, light stabilizers, processing stabilizers, anti-aging agents, compatibilizers, and the like as needed. By properly containing these components, various properties of the obtained cured product can be properly adjusted.

< Use of resin composition >

The resin composition of the present invention can also be suitably used for applications where exposure to light including sunlight or ultraviolet rays is possible. Specific examples thereof include a coating material or film for window glass of houses, facilities, transportation facilities, and the like; interior and exterior materials for houses, facilities, transportation facilities, etc., and interior and exterior paint; a light source member for emitting ultraviolet rays, such as a fluorescent lamp and a mercury lamp; solar cells, precision machinery, electronic and electrical equipment, and components for display devices; containers or packaging materials for foods, chemicals, pharmaceuticals, etc.; sheets for agricultural industry; fiber products and fibers for clothing such as sportswear, stockings and hats; plastic lenses, contact lenses, glasses, artificial eyes, and the like, or coating materials thereof; optical articles such as filters, prisms, mirrors, photo materials, etc.; stationery such as adhesive tape, ink, etc.; marking plates, markers, etc., and surface coating materials thereof, etc. For these details, reference is made to paragraphs 0158 to 0218 of japanese patent application laid-open publication No. 2009-263617 and paragraphs 0161 to 0194 of japanese patent application laid-open publication No. 2009-096971, and these are incorporated herein by reference.

The resin composition of the present invention can be preferably used for optical parts and the like. For example, it is preferably used as a resin composition for an ultraviolet cut filter, a lens or a protective material. The form of the protective material is not particularly limited, and examples thereof include a film, a sheet, and the like. The resin composition of the present invention can also be used as an adhesive, a binder, or the like.

The resin composition of the present invention can also be used for various components of a display device. For example, in the case of a liquid crystal display device, the liquid crystal display device can be used for various members constituting the liquid crystal display device, such as an antireflection film, a polarizing plate protective film, an optical film, a retardation film, an adhesive, and a binder. In the case of an organic electroluminescent display device, the organic electroluminescent display device can be used as each component constituting the organic electroluminescent display device, such as an optical film, a polarizer protective film for a circularly polarizing plate, a retardation film such as a 1/4 wave plate, and an adhesive or a binder.

< Ultraviolet absorber >

The ultraviolet absorber of the present invention comprises the compound (specific compound) represented by the above formula (1). The compound represented by the formula (1) is the same as described above. The ultraviolet absorber can be preferably used for a purpose that is likely to be exposed to light including sunlight or ultraviolet rays. As specific examples, the above-mentioned examples are given. The ultraviolet absorber of the present invention can be used for packaging materials, containers, paints, coating films, inks, fibers, building materials, recording media, image display devices, solar cell covers, glass films, and the like. In addition, an optical member described later can be used.

< Cured product and use thereof >

The cured product of the present invention can be obtained by using the resin composition of the present invention. The term "cured product" as used herein includes a dried product obtained by drying and curing a resin composition, and a cured product obtained by curing a resin composition by a curing reaction when the resin composition is subjected to the curing reaction.

The cured product of the present invention can be obtained as a molded article obtained by molding a resin composition into a desired shape. The shape of the molded article can be appropriately selected according to the application and purpose. Examples thereof include a film, a sheet, a plate, a lens, a tube, and a fiber.

The cured product of the present invention is preferably used as an optical member. Examples of the optical member include an ultraviolet cut filter, a lens, and a protective material. And can also be used for a polarizing plate and the like.

The ultraviolet cut filter can be used for, for example, an optical filter, a display device, a solar cell, a window glass, or the like. The type of the display device is not particularly limited, and examples thereof include a liquid crystal display device and an organic electroluminescent display device.

When the cured product of the present invention is used for a lens, the cured product of the present invention itself may be formed into a lens shape and used. The cured product of the present invention can be used for a coating film on the surface of a lens, an intermediate layer (adhesive layer) for joining lenses, or the like. Examples of the bonding lens include lenses described in paragraphs 0094 to 0102 of international publication No. 2019/131572, and the contents of these are incorporated herein.

The type of the protective material is not particularly limited, and examples thereof include a protective material for a display device, a protective material for a solar cell, a protective material for a window glass, an organic electroluminescent display device, and the like. The shape of the protective material is not particularly limited, and examples thereof include a film, a sheet, and the like.

< Optical Member >

The optical member of the present invention comprises a cured product obtained by using the resin composition of the present invention. The cured product of the present invention can be obtained as a molded article obtained by molding the resin composition of the present invention into a desired shape. The shape of the molded article can be appropriately selected according to the application and purpose. Examples thereof include a film, a sheet, a plate, a lens, a tube, and a fiber.

Examples of the type of the optical member include an ultraviolet cut filter, a lens, and a protective material.

Examples of the lens include a lens in which the cured product of the present invention itself is formed into a lens shape; a lens using the cured product of the present invention for a coating film on the surface of the lens, an intermediate layer (adhesive layer or adhesive layer) for joining the lens, or the like.

The type of the protective material is not particularly limited, and examples thereof include a protective material for a display device, a protective material for a solar cell, a protective material for a window glass, and the like. The shape of the protective material is not particularly limited, and examples thereof include a film, a sheet, and the like.

Further, as one embodiment of the optical member, a resin film is given. The resin film can be formed using the resin composition of the present invention. The resin used in the resin composition for forming a resin film may be the above-mentioned resin, and is preferably a (meth) acrylic resin, a polyester fiber, a cyclic olefin resin, or a cellulose acylate resin, and more preferably a cellulose acylate resin. The cellulose acylate-resin-containing resin composition may contain additives described in paragraphs 0022 to 0067 of Japanese patent application laid-open No. 2012-215689. Examples of such additives include sugar esters. By adding the sugar ester compound to the resin composition containing the cellulose acylate resin, the total haze and internal haze can be reduced without impairing the appearance of the optical characteristics and without performing heat treatment before the stretching step. Further, a resin film (cellulose acylate film) using a resin composition containing a cellulose acylate resin can be produced by the method described in paragraphs 0068 to 0096 of japanese patent application laid-open No. 2012-215689. The resin film may be further laminated with a hard coat layer described in paragraphs 0097 to 0113 of JP 2012-215689A.

Another embodiment of the optical member is an optical member having a laminate of a support and a resin layer. In the optical member, at least one of the support and the resin layer contains the cured product of the present invention.

The thickness of the resin layer in the laminate is preferably 1 μm to 2500 μm, more preferably 10 μm to 500 μm.

As the support in the laminate, a material having transparency within a range not impairing optical performance is preferable. The transparency of the support means that the support is optically transparent, specifically that the total light transmittance of the support is 85% or more. The total light transmittance of the support is preferably 90% or more, more preferably 95% or more.

As the support, a resin film is preferably used. Examples of the resin constituting the resin film include ester resins (e.g., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), and polycyclohexane dimethyl terephthalate (PCT)), olefin resins (e.g., polypropylene (PP), polyethylene (PE), and the like), polyvinyl chloride (PVA), and cellulose Triacetate (TAC). Among them, PET is preferable in terms of versatility.

The thickness of the support can be appropriately selected according to the application, purpose, and the like. In general, the thickness is preferably 5 μm to 2500. Mu.m, more preferably 20 μm to 500. Mu.m.

The support may be a releasable support. Such a laminate is preferably used for a polarizing plate or the like. The releasable support herein refers to a support that can be released from the resin film. The stress at the time of peeling the support from the resin film is preferably 0.05N/25mm or more and 2.00N/25mm or less, more preferably 0.08N/25mm or more and 0.50N/25mm or less, still more preferably 0.11N/25mm or more and 0.20N/25mm or less. After bonding and fixing the surface of the laminate cut into a laminate having a width of 25mm and a length of 80mm by an acrylic pressure-sensitive adhesive sheet on a glass substrate, one end (one side of 25mm in width) of the test piece in the longitudinal direction was held by a tensile tester (RTF-1210 manufactured by A & D Company, limited), and a 90℃peeling test (adhesive-peeling adhesive strength test method-part 1: 90℃peeling) was performed at a crosshead speed (holding moving speed) of 200 mm/min under an atmosphere having a temperature of 23℃and a relative humidity of 60% (according to Japanese Industrial Standards (JIS) K6854-1:1999), whereby the stress at peeling the support from the resin film was evaluated.

The releasable support is preferably a support containing polyethylene terephthalate (PET) as a main component (a component having the largest content in terms of mass among components constituting the support). From the viewpoint of mechanical strength, the weight average molecular weight of PET is preferably 20000 or more, more preferably 30000 or more, and further preferably 40000 or more. The support can be dissolved in Hexafluoroisopropanol (HFIP) and the weight average molecular weight of the PET can be determined by the GPC method. The thickness of the support is not particularly limited, but is preferably 0.1 to 100. Mu.m, more preferably 0.1 to 75. Mu.m, still more preferably 0.1 to 55. Mu.m, particularly preferably 0.1 to 10. Mu.m. The support may be subjected to a corona treatment, a glow discharge treatment, a primer treatment, or the like, which are known surface treatments.

Another embodiment of the optical member is a laminate in which a hard coat layer, a transparent support, and an adhesive layer or a tie layer are laminated in this order. Such a laminate can be preferably used as an ultraviolet cut filter, a protective material (protective film, protective sheet). In the optical member of this embodiment, any of the support, the hard coat layer, the adhesive layer, and the adhesive layer may contain the cured product of the present invention.

As the hard coat layer, for example, a hard coat layer described in japanese patent application laid-open publication nos. 2013-045045, 2013-043352, 2012-232459, 2012-128157, 2011-131409, 2011-131404, 2011-126162, 2011-075705, 2009-286981, 2009-263567, 2009-075248, 2007-164206, 2006-096811, 2004-075970, 2002-156505, 2001-272503, 2012/087, 2012/098967, 2012/6659, and 2011/105594 can be applied. The thickness of the hard coat layer is preferably 5 to 100 μm from the viewpoint of further improving scratch resistance.

The optical member of this embodiment has an adhesive layer or a tie layer on the side of the support substrate opposite to the side having the hard coat layer. The kind of the adhesive or binder used for the adhesive layer or the tie layer is not particularly limited, and a known adhesive or binder can be used. The adhesive or binder preferably contains an acrylic resin described in paragraphs 0056 to 0076 of JP-A2017-142412 and a crosslinking agent described in paragraphs 0077 to 0082 of JP-A2017-142412. The adhesive or binder may contain an adhesion improver (silane compound) described in paragraphs 0088 to 0097 of JP-A2017-142412 and an additive described in paragraph 0098 of JP-A2017-142412. The adhesive layer or the tie layer can be formed by the method described in paragraphs 0099 to 0100 of JP-A2017-142412. From the viewpoint of both adhesion and handleability, the thickness of the adhesive layer or tie layer is preferably 5 μm to 100 μm.

The optical member of the present invention can be preferably used as a component of a display such as a Liquid Crystal Display (LCD) or an organic electroluminescence display (OLED).

As a liquid crystal display device, a liquid crystal display device including the cured product of the present invention in a member such as an antireflection film, a polarizing plate protective film, an optical film, a retardation film, an adhesive, or a binder can be given. The optical member containing the cured product of the present invention may be disposed on either the viewer side (front side) or the backlight side in the liquid crystal cell, and may be disposed on either the side (outside) away from the liquid crystal cell or the side (inside) closer to the liquid crystal cell in the polarizer.

Examples of the organic electroluminescent display device include an organic electroluminescent display device in which the cured product of the present invention is contained in a member such as an optical film, a polarizer protective film in a circularly polarizing plate, a retardation film such as a 1/4 wave plate, an adhesive, or a binder. By using the cured product of the present invention in the above-described structure, deterioration of the organic electroluminescent display device due to external light can be suppressed.

< Polymer >

The polymer of the present invention includes a structure (hereinafter, also referred to as structure (3)) derived from a compound in which at least one of R ¹¹、R¹²、Q³ and Q ⁴ is a group including a polymerizable group having an ethylenically unsaturated bond in the compound represented by the above formula (3). Among the compounds represented by the above formula (3), a compound having a structure in which at least one of R ¹¹、R¹²、Q³ and Q ⁴ is a group including a polymerizable group having an ethylenically unsaturated bond is also referred to as a specific compound (3).

The polymer of the present invention may contain, in addition to the structure derived from the specific compound (3), a structure derived from a compound having an ethylenically unsaturated bond-containing group other than the specific compound (3) (hereinafter, also referred to as other polymerizable compound). That is, the polymer of the present invention may be a copolymer formed from the specific compound (3) and other polymerizable compounds. Examples of the other polymerizable compound include a polymerizable compound described as a material used in the resin composition of the present invention, a compound having a polymerizable group described as a material used as another ultraviolet absorber, and the like.

The content of the structure derived from the specific compound (3) in the polymer of the present invention is preferably 0.01 to 100% by mass. The upper limit is more preferably 50 mass% or less, and still more preferably 10 mass% or less. The lower limit is more preferably 0.02 mass% or more, and still more preferably 0.1 mass% or more.

The number-average molecular weight of the polymer of the present invention is preferably 5000 to 80000, more preferably 10000 to 60000, and even more preferably 10000 to 40000.

The polymer of the present invention can be used for an ultraviolet absorber, an optical member, or the like.

The polymer of the present invention can also be used in combination with a resin. The resin may be the one described in the above item of the resin composition of the present invention.

Examples

The present invention will be described in more detail with reference to examples. The materials, amounts used, proportions, treatment contents, treatment steps and the like shown in the following examples can be appropriately changed without departing from the gist of the present invention. Accordingly, the scope of the present invention is not limited to the specific examples shown below. In the structural formulae shown below, me is methyl, et is ethyl, ⁿ Bu is n-butyl, ^t Bu is t-butyl, ph is phenyl, and Ac is acetyl.

Synthesis example

Synthesis example 1 Synthesis of intermediates 1 to 3

Intermediate 1-1 was synthesized according to the following scheme. In the following scheme, in the synthesis of intermediate 1-1, referring to the methods described in paragraphs 0222 and 0223 of Japanese patent application laid-open No. 2009-263617, 1, 2-dibenzyl pyrazoline-3, 5 dione was used instead of 1, 2-dibutyl pyrazoline-3, 5 dione, to obtain 77g (yield 78%) of intermediate 1-1.

[ Chemical formula 62]

Then, the intermediate 1-2 was synthesized according to the following synthesis scheme. 50g of intermediate 1-1, 24.5g of 2, 3-dichloro-5, 6-dicyano-p-benzoquinone and 500ml of tetrahydrofuran were added and mixed, followed by stirring at 20℃for 1 hour. After completion of the reaction, 500mL of hexane was added, and after the precipitated solid was collected by filtration, it was washed with 150mL of hexane, whereby 42g (yield: 84%) of intermediate 1-2 was obtained.

[ Chemical formula 63]

Next, intermediates 1-3 were synthesized according to the following synthesis scheme. 30g of intermediate 1-2, 8g of piperidinium pentamethylene dithiocarbamate, 360mL of N-methyl-2-pyrrolidone, 160mL of acetic acid and 54mL of acetone were added and mixed, followed by stirring at 60℃for 1 hour. After the precipitated solid was collected by filtration, it was washed with 300ml of acetone, whereby 8.0g of intermediate 1-3 was obtained (yield 36%).

[ Chemical formula 64]

Synthesis example 2 Synthesis of Compound A-104

Compound a-104 was synthesized according to the following synthesis scheme. 3.0g of intermediate 1-3, 0.58g of malononitrile and 150ml of N-methyl-2-pyrrolidone were added and mixed, followed by stirring at 80℃for 1 hour. After cooling to room temperature, 1mL of hydrochloric acid and 150mL of water were added and stirred for 30 minutes. After the precipitated solid was collected by filtration, 200ml of acetonitrile was added thereto, and the mixture was refluxed under nitrogen for 1 hour. After cooling to room temperature, stirring at room temperature for 1 hour, the solid was collected by filtration and washed with 100ml of acetonitrile, whereby 2.1g of compound A-104 was obtained (yield 79%). In addition, in proton nuclear magnetic resonance (¹ H-NMR, solvent: deuterated dimethyl sulfoxide (dDMSO)) of the obtained compound A-104, the chemical shifts δ were 11.6 (s, 2H), 7.29 (m, 10H), and 4.80 (s, 4H).

[ Chemical formula 65]

Synthesis example 3 Synthesis of Compound A-1

Compound a-1 was synthesized according to the following synthesis scheme. 1.5g of Compound A-104, 0.76g of triethylamine, 1.0g of 2-ethylhexanoyl chloride and 30ml of dimethylacetamide were added and mixed, followed by stirring at 20℃for 1 hour. After the reaction was completed, 30ml of water was added thereto and stirred for 30 minutes. After the precipitated solid was collected by filtration, it was washed with 30ml of methanol and then purified by silica gel column chromatography to obtain 1.6g (yield: 75%) of Compound A-1. In proton nuclear magnetic resonance (¹ H-NMR, solvent: deuterated chloroform (CDCl ₃)) of the obtained compound A-1, the chemical shift δ was 7.27 (m, 6H), 7.10 (m, 4H), 4.75 (s, 4H), 2.69 (m, 2H), 1.8 to 1.6 (m, 8H), 1.5 to 1.3 (m, 8H), 1.10 (m, 6H), 0.94 (m, 6H).

[ Chemical formula 66]

Synthesis of Compound A-105

In synthesis example 2, 0.71g of compound A-105 (yield 60%) was obtained in the same manner as in synthesis example 2 except that n-butyl cyanoacetate was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.28(m、10H)、4.80(s、4H)、4.24(t、2H)、1.62(m、2H)、1.37(m、2H)、0.92(t、3H)

[ Chemical formula 67]

Synthesis example 5 Synthesis of Compound A-2

In Synthesis example 3, 0.61g of Compound A-2 (yield 74%) was obtained in the same manner as in Synthesis example 3 except that Compound A-105 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、4.28(t、2H)、2.69(m、2H)、1.91～1.71(m、10H)、1.60～1.44(m、10H)、1.15(m、6H)、0.96(m、9H)

[ Chemical formula 68]

Synthesis of Compound A-106

In synthesis example 2, 1.0g of compound a-106 was obtained (yield 78%) in the same manner as in synthesis example 2 except that 2-ethylhexyl cyanoacetate was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.24(m、10H)、4.80(s、4H)、4.16(d、2H)、1.63(m、1H)、1.29(m、8H)、0.88(m、6H)

[ Chemical formula 69]

Synthesis of Compound A-3

In Synthesis example 3, 0.42g of Compound A-3 (yield 68%) was obtained in the same manner as in Synthesis example 3 except that Compound A-106 was used instead of Compound A-104.

¹H-NMR(CDCl3)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、4.19(m、2H)、2.69(m、2H)、1.90～1.66(m、9H)、1.47～1.31(m、16H)、1.14(m、6H)、1.01～0.90(m、12H)

[ Chemical formula 70]

Synthesis of Compound A-18

In Synthesis example 7, 0.33g of Compound A-18 (yield 79%) was obtained in the same manner as in Synthesis example 7 except that 3, 5-trimethylhexanoyl chloride was used instead of 2-ethylhexanoyl chloride.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.76(s、4H)、4.19(m、2H)、2.77(m、2H)、2.56(m、2H)、2.24(m、2H)、1.67(m、1H)、1.55～1.32(m、12H)、1.18(m、6H)、0.98～0.90(m、24H)

[ Chemical formula 71]

Synthesis of Compound A-107

In synthesis example 2, 1.1g of compound a-107 (yield 76%) was obtained in the same manner as in synthesis example 2 except that trimethylacetyl acetonitrile was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.29(m、10H)、4.80(s、4H)、1.34(s、9H)

[ Chemical formula 72]

Synthesis of Compound A-4 (Synthesis example 10)

In Synthesis example 3, 0.43g of Compound A-4 (yield 62%) was obtained in the same manner as in Synthesis example 3 except that Compound A-107 was used instead of Compound A-104.

¹H-NMR(CDCl3)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、2.71(m、2H)、1.8～1.6(m、8H)、1.48～1.45(m、8H)、1.39(s、9H)、1.15(m、6H)、0.99(m、6H)

[ Chemical formula 73]

Synthesis of Compound A-108

In synthesis example 2, 0.68g of compound A-108 (yield 75%) was obtained in the same manner as in synthesis example 2 except that 2-cyanoacetamide was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.3(s、2H)、7.65(m、2H)、7.29(m、10H)、4.80(s、4H)

[ Chemical formula 74]

Synthesis of Compound A-5 (Synthesis example 12)

In Synthesis example 3, 0.41g of Compound A-5 (yield 58%) was obtained in the same manner as in Synthesis example 3 except that Compound A-108 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：67.27(m、6H)、7.10(m、4H)、6.00(br、1H)、5.46(br、1H)、4.75(s、4H)、2.69(m、2H)、1.92～1.71(m、8H)、1.55～1.43(m、8H)、1.16(m、6H)、0.98(m、6H)

[ Chemical formula 75]

Synthesis of Compound A-109

In synthesis example 1, intermediate 2-3 was obtained in the same manner as in synthesis example 1 except that dimethyl malonate was used instead of 1, 2-dibenzylpyrazoline-3, 5-dione.

Next, compound A-109 was synthesized according to the following synthesis scheme. 2.0g of intermediate 2-3, 1.1g of 1, 2-dibenzyl pyrazoline-3, 5-dione and 100ml of N-methyl-2-pyrrolidone were added and mixed, followed by stirring at 100℃for 1 hour. After cooling to room temperature, 1mL of hydrochloric acid, 150mL of water were added and stirred for 30 minutes. After the precipitated solid was collected by filtration, 100ml of acetonitrile was added thereto, and the mixture was refluxed under nitrogen for 1 hour. After cooling to room temperature, stirring at room temperature for 1 hour, the solid was collected by filtration and washed with 50ml of acetonitrile, whereby 1.3g of A-109 (yield 52%) of compound was obtained.

¹H-NMR(dDMSO)：δ11.2(s、2H)、7.29(m、10H)、4.80(s、4H)、3.79(s、6H)

[ Chemical formula 76]

Synthesis of Compound A-6 (Synthesis example 14)

In Synthesis example 3, 0.45g of Compound A-6 (yield 65%) was obtained in the same manner as in Synthesis example 3 except that Compound A-109 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：67.27(m、6H)、7.10(m、4H)、4.75(s、4H)、3.88(s、6H)、2.71(m、2H)、1.95～1.73(m、8H)、1.59～1.41(m、8H)、1.16(m、6H)、0.99(m、6H)

[ Chemical formula 77]

Synthesis of Compound A-110 (Synthesis example 15)

In Synthesis example 13, 1.2g of Compound A-110 (yield 84%) was obtained in the same manner as in Synthesis example 13 except that methanesulfonylacetonitrile was used instead of dimethyl malonate and intermediate 3-3 was used instead of intermediate 2-3.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.29(m、10H)、4.80(s、4H)、3.36(s、3H)

[ Chemical formula 78]

Synthesis of Compound A-7

In Synthesis example 3, 0.63g of Compound A-7 (yield 57%) was obtained in the same manner as in Synthesis example 3 except that Compound A-110 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、3.19(s、3H)、2.68(m、2H)、1.91～1.74(m、8H)、1.50～1.40(m、8H)、1.13(m、6H)、0.97(m、6H)

[ Chemical formula 79]

Synthesis of Compound A-46

In Synthesis example 3, 0.48g of Compound A-46 (yield 60%) was obtained in the same manner as in Synthesis example 3, except that lauroyl chloride was used instead of 2-ethylhexanoyl chloride.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.77(s、4H)、2.73(t、2H)、1.82(dd、4H)、1.53～1.22(m、32H)、0.88(t、6H)

[ Chemical formula 80]

Synthesis of Compound A-47

In Synthesis example 3, 0.35g of Compound A-47 (yield 61%) was obtained in the same manner as in Synthesis example 3, except that 2-acetoxyisobutyryl chloride was used instead of 2-ethylhexanoyl chloride.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、2.23(s、6H)、1.78(s、12H)

[ Chemical formula 81]

Synthesis of Compound A-44

Compound a-44 was synthesized according to the following synthesis scheme. 0.50g of Compound A-104, 0.42g of triethylamine, 0.60g of 2-hexyldecanoic acid, 0.28g of thionyl chloride and 20ml of dimethylacetamide were added and mixed, followed by stirring at 20℃for 1 hour. After the reaction was completed, 30ml of water was added thereto and stirred for 30 minutes. After the precipitated solid was collected by filtration, it was washed with 30ml of methanol, and then purified by column chromatography to obtain 0.60g of Compound A-44 (yield: 67%).

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、2.74(m、2H)、1.81～1.60(m、8H)、1.52～1.26(m、40H)、0.86(m、12H)

[ Chemical formula 82]

Synthesis of Compound A-45

In Synthesis example 19, 0.50g of Compound A-45 (yield 44%) was obtained in the same manner as in Synthesis example 19 except that 2,4,8, 10, 10-hexamethylundecane-5-carboxylic acid was used instead of 2-hexyldecanoic acid.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.74(s、4H)、2.64(m、2H)、2.15(m、1H)、1.96(m、1H)、1.83～1.68(m、4H)、1.52～1.15(m、22H)、1.13～1.05(m、22H)、0.98～0.89(m、18H)

[ Chemical formula 83]

Synthesis example 21 Synthesis of Compound A-26

In Synthesis example 19, 0.38g of Compound A-26 (yield 58%) was obtained in the same manner as in Synthesis example 19 except that Compound A-106 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.74(s、4H)、4.19(m、2H)、2.74(m、2H)、1.85(m、4H)、1.69(m、5H)、1.52～1.26(m、48H)、0.92～0.84(m、18H)

[ Chemical formula 84]

Synthesis of Compound A-111

In synthesis example 2, 0.97g of compound a-111 (yield 80%) was obtained in the same manner as in synthesis example 2 except that 2-ethoxyethyl cyanoacetate was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.28(m、10H)、4.80(s、4H)、4.35(t、2H)、3.64(t、2H)、3.50(q、2H)、1.12(t、3H)

[ Chemical formula 85]

Synthesis of Compound A-19

In Synthesis example 3, 0.32g of Compound A-19 (yield 78%) was obtained in the same manner as in Synthesis example 3 except that Compound A-111 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、4.41(t、2H)、3.72(t、2H)、3.56(q、2H)、2.70(m、2H)、1.92～1.71(m、8H)、1.60～1.44(m、8H)、1.22～1.13(m、9H)、0.98(m、6H)

[ Chemical formula 86]

Synthesis example 24 (Synthesis of Compound A-25)

In Synthesis example 7, 0.28g of Compound A-25 (yield 74%) was obtained in the same manner as in Synthesis example 7 except that 2, 2-dimethylbutyryl chloride was used instead of 2-ethylhexanoyl chloride.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.76(s、4H)、4.19(m、2H)、1.89～1.69(m、3H)、1.44～1.25(m、20H)、1.10(m、6H)、0.94(m、6H)

[ Chemical formula 87]

Synthesis of Compound A-112 (Synthesis example 25)

In synthesis example 2, 0.31g of compound a-112 (yield 39%) was obtained in the same manner as in synthesis example 2 except that tert-butyl cyanoacetate was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.28(m、10H)、4.80(s、4H)、1.51(t、9H)

[ Chemical formula 88]

Synthesis of Compound A-20

In Synthesis example 3, 0.28g of Compound A-20 (yield 65%) was obtained in the same manner as in Synthesis example 3 except that Compound A-112 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、4.75(s、4H)、2.69(m、2H)、1.88～1.76(m、8H)、1.54～1.44(m、17H)、1.13(m、6H)、0.99(m、6H)

[ Chemical formula 89]

Synthesis of Compound A-128 (Synthesis example 27)

In Synthesis example 7, compound A-128 (yield 48%) of 0.24 was obtained in the same manner as in Synthesis example 7 except that methacryloyl chloride was used instead of 2-ethylhexanoyl chloride.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、6.52(d、2H)、6.00(d、2H)4.76(s、4H)、4.19(m、2H)、2.13(d、6H)、1.69(m、1H)、1.44～1.25(m、6H)、0.94(m、6H)

[ Chemical formula 90]

Synthesis of Compound A-196

In synthesis example 2, 0.35g of compound a-196 (yield 81%) was obtained in the same manner as in synthesis example 2 except that allyl cyanoacetate was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.28(m、10H)、5.96(m、1H)、5.32(m、2H)、4.80(m、6H)

[ Chemical formula 91]

Synthesis of Compound A-141

In Synthesis example 3, 0.30g of Compound A-141 (yield 74%) was obtained in the same manner as in Synthesis example 3 except that Compound A-196 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：δ7.27(m、6H)、7.10(m、4H)、5.96(m、1H)、5.32(m、2H)、4.75(m、6H)、4.28(t、2H)、2.69(m、2H)、1.8～1.6(m、8H)、1.5～1.3(m、8H)、1.10(m、6H)、0.94(m、6H).

[ Chemical formula 92]

Synthesis of Compound A-197

In synthesis example 2, 0.35g of compound a-196 (yield 93%) was obtained in the same manner as in synthesis example 2 except that ethyl cyanoacetate methacrylate was used instead of malononitrile.

¹H-NMR(dDMSO)：δ11.5(s、2H)、7.28(m、10H)、6.05(s、1H)、5.70(s、1H)、4.80(s、4H)、4.50(m、2H)、4.38(m、2H)、1.88(s、3H)

[ Chemical formula 93]

Synthesis of Compound A-143

In Synthesis example 3, 0.20g of Compound A-143 (yield 45%) was obtained in the same manner as in Synthesis example 3, except that Compound A-197 was used instead of Compound A-104.

¹H-NMR(CDCl₃ ): Delta is 7.27(m、6H)、7.10(m、4H)、6.17(s、1H)、5.60(s、1H)、4.75(s、4H)、4.50(m、2H)、4.43(m、2H)、2.69(m、2H)、1.8～1.6(m、11H)、1.5～1.3(m、8H)、1.10(m、6H)、0.94(m、6H).

[ Chemical formula 94]

Synthesis of Compound A-142

In synthesis example 31, 2.1g of compound a-143 (yield 60%) was obtained in the same manner as in synthesis example 3, except that 3, 5-trimethylhexanoyl chloride was used instead of 2-ethylhexanoyl chloride.

¹H-NMR(CDCl₃ ): Delta is 7.27(m、6H)、7.10(m、4H)、6.17(s、1H)、5.60(s、1H)、4.75(s、4H)、4.50(m、2H)、4.43(m、2H)、2.77(m、2H)、2.56(m、2H)、2.24(m、2H)、1.95(s、3H)、1.5～1.3(m、6H)、1.25(m、6H)、0.98(s、18H).

[ Chemical formula 95]

Synthesis of Compound A-245 (Synthesis example 33)

In synthesis example 2, 3.0g of compound a-245 (yield 45%) was obtained in the same manner as in synthesis example 2 except that 2, 6-bis (1, 1-dimethylethyl) -4-methylcyclohexylcyanoacetate was used instead of malononitrile.

1H-NMR(dDMSO)：δ11.5(s、2H)、7.24(m、10H)、5.73(s、1H)、4.80(s、4H)、1.6～1.2(m、7H)、0.99(m、3H)、0.85(s、18H)

[ Chemical formula 96]

Synthesis of Compound A-201

In Synthesis example 3, 2.1g of Compound A-201 (yield 53%) was obtained in the same manner as in Synthesis example 3 except that Compound A-245 was used instead of Compound A-104.

¹H-NMR(CDCl3)：δ7.27(m、6H)、7.10(m、4H)、5.80(s、1H)、4.75(s、4H)、2.69(m、2H)、1.9～1.0(m、29H)、0.98(m、9H)、0.87(s、18H)

[ Chemical formula 97]

Synthesis of Compound A-251

In synthesis example 1, intermediate 3-3 was obtained in the same manner as in synthesis example 1 except that 1, 2-butylpyrazoline-3, 5-dione was used instead of 1, 2-dibenzylpyrazoline-3, 5-dione.

Next, in Synthesis example 2, 1.20g of Compound A-251 (yield 91%) was obtained in the same manner as in Synthesis example 2 except that ethyl cyanoacetate methacrylate was used instead of malononitrile and intermediate 3-3 was used instead of intermediate 1-3.

¹H-NMR(dDMSO)：δ11.4(s、2H)、6.05(s、1H)、5.70(s、1H)、4.80(s、4H)、4.50(m、2H)、4.38(m、2H)、3.62(m、4H)、1.88(s、3H)、1.44(m、4H)、1.23(m、4H)、0.87(m、6H)、

[ Chemical formula 98]

Synthesis of Compound A-232

In Synthesis example 3, 0.70g of Compound A-232 (yield 68%) was obtained in the same manner as in Synthesis example 3 except that Compound A-251 was used instead of Compound A-104.

¹H-NMR(CDCl₃)：6.14(s、1H)、5.60(s、1H)、4.52(m、2H)、4.43(m、2H)、3.65(m、4H)、2.69(m、2H)、1.8～1.6(m、11H)、1.5～1.4(m、18H)、1.26(m、6H)、1.10(m、6H)、0.98(m、6H)、0.91(m、6H).

[ Chemical formula 99]

Test example 1 ]

Sample solutions 101 to 147 were prepared by dissolving 2mg of the compounds (exemplified compounds (1) to (44) and comparative compounds (1) to (3)) described in the following table in 100mL of ethyl acetate, and then diluting the solution with ethyl acetate until the absorbance of the solution was in the range of 0.6 to 1.2.

The absorbance and molar absorptivity of each sample solution were measured by a 1cm quartz cell using a spectrophotometer (manufactured by UV-1800PC, SHIMADZU CORPORATION). The maximum absorption wavelength (λ _max) was measured from the absorption spectrum of each sample solution, and the long-wavelength ultraviolet absorption capacity was evaluated according to the following criteria.

Further, for each sample solution, the ratio of absorbance at 440nm (absorbance ratio A ₄₄₀) was calculated when the absorbance at 400nm was 1, and the colorability was evaluated on the basis of the following criteria. The smaller the value of absorbance ratio A ₄₄₀, the less staining.

The evaluation results are shown in the following table. The values in brackets in the column of long wavelength ultraviolet absorption capacity are values of lambda _max, and the values in brackets in the column of colorability are values of absorbance ratio a ₄₄₀. In the following table, the molar absorptivity values at the maximum absorption wavelength are shown in the molar absorptivity columns.

Evaluation criterion for the absorption ability of long-wavelength ultraviolet rays

A: lambda _max is 390nm or more

B: lambda _max is 370nm or more and 390nm or less

C: lambda _max is less than 370nm

Evaluation criterion for colorability

A: absorbance ratio A ₄₄₀ is less than 0.02

B: the absorbance ratio A ₄₄₀ is above 0.02

[ Chemical formula 100]

[ Chemical formula 101]

[ Chemical formula 102]

[ Chemical formula 103]

[ Chemical formula 104]

[ Chemical formula 105]

[ Chemical formula 106]

TABLE 1

TABLE 2

As shown in the above table, the sample solutions 101 to 144 using the exemplified compounds (1) to (44) were excellent in evaluation of long-wavelength ultraviolet absorption ability and colorability.

< Test example 2>

Resin compositions were prepared by dissolving the compounds described in the following table (exemplified compounds (1) to (44) and comparative compounds (1) to (3)) in 7.6g of chloroform and 1.1g of a (meth) acrylic resin (produced by Dianal BR-80, mitsubishi Chemical Corporation and containing 60% by mass or more of methyl methacrylate and Mw95000 as monomer units). The obtained resin composition was spin-coated on a glass substrate to form a coating film, and the obtained coating film was dried at 110 ℃ for 2 minutes to prepare resin films 201 to 251.

(Evaluation of spectroscopic characteristics)

The absorbance of the resin films 201 to 251 was measured using a spectrophotometer (manufactured by UV-1800PC, SHIMADZU CORPORATION). Regarding each resin film, the maximum absorption wavelength (λ _max) was measured from the obtained spectrogram, and the long-wavelength ultraviolet absorption ability was evaluated on the same basis as in test example 1.

Further, the ratio of absorbance at 440nm (absorbance ratio A ₄₄₀) was calculated for each resin film, and the colorability was evaluated on the same basis as in test example 1, assuming that the absorbance at 400nm was 1.

The evaluation results are shown in the following table. The values in brackets in the column of long wavelength ultraviolet absorption capacity are values of lambda _max, and the values in brackets in the column of colorability are values of absorbance ratio a ₄₄₀.

(Evaluation of light resistance)

Under the following condition 1, the resin films 201 to 251 were subjected to a light resistance test, and the maintenance ratio of absorbance at the maximum absorption wavelength (λ _max) was obtained, and the light resistance was evaluated. Specifically, after measuring the absorbance of the resin film at λ _max using a spectrophotometer (manufactured by UV-1800PC, SHIMADZU CORPORATION), the resin film was subjected to a light resistance test under condition 1 for 3 weeks, and the absorbance at λ _max was measured for the resin film after the light resistance test. Next, the absorbance maintenance rate (%) was calculated by the following formula using the values of absorbance at λ _max of the resin film before and after the light resistance test, and the light resistance was evaluated according to the following criteria. The higher the absorbance maintenance ratio, the more excellent the light resistance. The evaluation results are shown in the following table. The values in brackets in the columns for light fastness are values for absorbance maintenance.

Absorbance maintenance ratio (%) = (absorbance at λ _max of resin film after light resistance test/absorbance at λ _max of resin film before light resistance test) ×100

Evaluation criterion-

AA: the absorbance maintenance rate is more than 90 percent

A: the absorbance maintenance rate is more than 85 percent

B: the absorbance maintenance rate is 80% or more and less than 85%

C: the absorbance maintenance rate is less than 80 percent

(Condition 1)

The device comprises: low temperature cycle xenon lamp weathering tester (XL 75, suga Test Instruments Co., ltd.)

Illuminance: 90klx (40 w/m ²)

Time: 3 weeks

Environment: 23 ℃ and relative humidity 50%

TABLE 3

TABLE 4

As shown in the above table, the resin films 201 to 248 using the exemplified compounds (1) to (44) were excellent in evaluation of long-wavelength ultraviolet absorption ability, colorability, and light resistance.

< Test example 3>

The following components were mixed to prepare a resin composition (photopolymerizable composition).

Ultraviolet absorber (compound shown in the following Table) (0.6 parts by mass)

Polymerizable compound (KAYARAD DPHA (compound having 2 or more ethylenically unsaturated bond-containing groups manufactured by Nippon Kayaku Co., ltd.). 2.8 parts by mass

Resin (Dianal BR-80 (Mitsubishi Chemical Corporation manufactured)) 14.8 parts by mass

Photopolymerization initiator (compound shown in the following Table) (2.4 parts by mass)

Solvent (propylene glycol monomethyl ether acetate) & lt & gt79.4 parts by mass

TABLE 5

Resin composition No.	Ultraviolet absorber	Photopolymerization initiator
			301	Exemplary Compound (1)	V-1
302	Exemplary Compound (1)	V-2
			303	Exemplary Compound (1)	V-3
304	Exemplary Compound (18)	V-1
			305	Exemplary Compound (18)	V-2
306	Exemplary Compound (18)	V-3
			307	Exemplary Compound (28)	V-3
308	Exemplary Compound (29)	V-3
			309	Exemplary Compound (30)	V-3
310	Exemplary Compound (32)	V-3
			311	Exemplary Compound (33)	V-1
312	Exemplary Compound (33)	V-2
			313	Exemplary Compound (33)	V-3
314	Exemplary Compound (40)	V-3
			315	Exemplary Compound (41)	V-3
316	Exemplary Compound (42)	V-1
			317	Exemplary Compound (42)	V-2
318	Exemplary Compound (42)	V-3
			319	Exemplary Compound (43)	V-1
320	Exemplary Compound (43)	V-2
			321	Exemplary Compound (43)	V-3
322	Comparative Compound (1)	V-1
			323	Comparative Compound (1)	V-2
324	Comparative Compound (1)	V-3
			325	Comparative Compound (2)	V-1
326	Comparative Compound (2)	V-2
			327	Comparative Compound (2)	V-3
328	Comparative Compound (3)	V-1
			329	Comparative Compound (3)	V-2
330	Comparative Compound (3)	V-3

The details of the raw materials described by abbreviations in the above tables are as follows.

(Ultraviolet absorber)

Compounds (1), (18), (28), (29), (30), (32), (33), (40), (41), (42), (43) and comparative compounds (1) to (3) are exemplified: compounds of the above structure

(Photopolymerization initiator)

V-1: irgacure OXE01 (manufactured by BASF corporation, oxime Compound, photo radical polymerization initiator)

V-2: omnirad 2959 (IGM RESINS B.V. manufactured, hydroxyacetophenone compound, photo radical polymerization initiator)

V-3: omnirad TPO (IGM RESINS B.V. manufactured, acylphosphine compound, photo radical polymerization initiator)

< Production of resin film >

The resin composition was spin-coated on a glass substrate (1737, corning Incorporated co., ltd.) of 50mm×50mm to a film thickness of 1.5 μm, and dried at 120 ℃ for 5 minutes to form a resin composition layer. Then, the resin composition layer was subjected to full-face exposure at an exposure amount of 1000mJ/cm ² using an i-ray stepper exposure apparatus (UX-1000 SM-EH04, manufactured by Ushio Inc.), to thereby manufacture resin films 301 to 330.

Regarding the resin compositions 301 to 327, the degree of change in transmittance (degree of change in transmittance 1) of the resin composition layer before and after exposure at the maximum absorption wavelength (λ _max) is 5% or less.

(Evaluation of light resistance)

Under the following condition 2, the light resistance was evaluated by obtaining the maintenance ratio of absorbance at the maximum absorption wavelength (λ _max) for the resin films 301 to 330. Specifically, after measuring absorbance of the resin film at λ _max using a spectrophotometer (manufactured by UV-1800PC, SHIMADZU CORPORATION), the resin film was subjected to a light resistance test under condition 2 for 3 days, and absorbance at λ _max was measured for the resin film after the light resistance test. Next, the absorbance maintenance rate (%) was calculated by the following formula using the values of absorbance at λ _max of the resin film before and after the light resistance test, and the light resistance was evaluated according to the following criteria. The higher the absorbance maintenance ratio, the more excellent the light resistance. The evaluation results are shown in the following table. The values in brackets in the columns for light fastness are values for absorbance maintenance.

Evaluation criterion-

AA: the absorbance maintenance rate is above 75%

A: the absorbance maintenance rate is 65% or more

B: the absorbance maintenance rate is more than 50% and less than 65%

C: the absorbance maintenance rate is less than 50 percent

(Condition 2)

Illuminance: 90klx (40 w/m ²)

Time: for 3 days

Environment: 23 ℃ and relative humidity 50%

TABLE 6

As shown in the above table, the resin films 301 to 321 using the exemplified compounds (1), (18), (28), (29), (30), (32), (33), (40), (41), (42), (43) are excellent in light resistance. The resin films 301 to 321 have excellent absorption ability of ultraviolet rays having a wavelength of around 400nm and are less colored.

After the resin films 301 to 321 were stored at 40℃and 50% humidity for 1 week, the films were left at room temperature for 1 day, and the presence or absence of bleeding and precipitation was visually observed. No bleeding and deposition were observed in any of the resin films 301 to 321.

Test example 4 ]

(Preparation of compositions 401 to 424 and 432 to 437)

The following components were mixed to prepare compositions (photopolymerizable compositions) 401 to 424 and 432 to 437.

Ultraviolet absorber (compound shown in the following Table) (2.0 parts by mass)

Polymerizable compound (compound) (2.6 parts by mass) shown in the following Table

Resin (resin described in the following Table) (12.9 parts by mass)

Photopolymerization initiator (compound shown in the following Table) (2.5 parts by mass)

Solvent (propylene glycol monomethyl ether acetate) & 40.0 parts by mass

Solvent (cyclopentanone) 40.0 parts by mass

Surfactant (KF-6001, shin-Etsu Chemical Co., ltd., both terminal methanol-modified polydimethylsiloxane, hydroxyl value 62 mgKOH/g) & 0.02 parts by mass

TABLE 7

Composition No.	Ultraviolet absorber	Polymerizable compound	Resin composition	Photopolymerization initiator
					401	Exemplary Compound (1)	T-1	U-2	V-1
402	Exemplary Compound (1)	T-1	U-2	V-2
					403	Exemplary Compound (1)	T-1	U-2	V-5
404	Exemplary Compound (18)	T-1	U-2	V-1
					405	Exemplary Compound (18)	T-1	U-1	V-1
406	Exemplary Compound (18)	T-1	U-2	V-2
					407	Exemplary Compound (18)	T-1	U-2	V-3
408	Exemplary Compound (18)	T-1	U-2	V-4
					409	Exemplary Compound (18)	T-1	U-2	V-5
410	Exemplary Compound (18)	T-1	U-2	V-6
					411	Exemplary Compound (18)	T-1	U-2	V-7
412	Exemplary Compound (18)	T-1	U-2	V-8
					413	Exemplary Compound (18)	T-1	U-2	V-1
414	Exemplary Compound (18)	T-2	U-2	V-1
					415	Exemplary Compound (18)	T-3	U-2	V-1
416	Exemplary Compound (18)	T-4	U-2	V-1
					417	Exemplary Compound (18)	T-5	U-2	V-1
418	Exemplary Compound (18)	T-6	U-2	V-1
					419	Exemplary Compound (33)	T-1	U-2	V-1
420	Exemplary Compound (33)	T-1	U-2	V-2
					421	Exemplary Compound (33)	T-1	U-2	V-5
422	Exemplary Compound (42)	T-1	U-2	V-1
					423	Exemplary Compound (42)	T-1	U-2	V-2
424	Exemplary Compound (42)	T-1	U-2	V-5
					432	Exemplary Compound (43)	T-1	U-2	V-1
433	Exemplary Compound (43)	T-1	U-2	V-2
					434	Exemplary Compound (43)	T-1	U-2	V-5
435	Comparative Compound (1)	T-1	U-2	V-1
					436	Comparative Compound (2)	T-1	U-2	V-2
437	Comparative Compound (3)	T-1	U-2	V-5

(Preparation of composition 425)

A composition (photopolymerizable composition) 425 was prepared by mixing the following components.

Ultraviolet absorber (exemplified compound (1)). 2.0 parts by mass

0.5 Part by mass of a polymerizable compound T-2

1.5 Parts by mass of a polymerizable compound T-4

Resin U-3 & lt & gt 13.5 parts by mass

Photopolymerization initiator V-8 & lt & gt & lt 2.5 parts by mass

80.0 Parts by mass of a solvent (toluene)

(Preparation of composition 426)

A composition (photopolymerizable composition) 426 was prepared by mixing the following components.

Ultraviolet absorber (exemplified compound (1)). 2.0 parts by mass

10.5 Parts by mass of a polymerizable compound T-6

5.0 Parts by mass of a polymerizable compound T-1

Photopolymerization initiator V-1 & lt2.2 parts by mass

0.3 Part by mass of a photopolymerization initiator V-5

Solvent (ethyl acetate) 40.0 parts by mass

Solvent (cyclopentanone) 40.0 parts by mass

(Preparation of composition 427)

A composition (photopolymerizable composition) 427 was prepared by mixing the following components.

Ultraviolet absorber (exemplified compound (1)). 2.0 parts by mass

5.0 Parts by mass of a polymerizable compound T-5

4.0 Parts by mass of a polymerizable compound T-4

Resin U-1 & lt & gt 6.5 parts by mass

Photopolymerization initiator V-1 & lt2.0 parts by mass

0.5 Part by mass of a photopolymerization initiator V-6

Solvent (ethyl acetate) 40.0 parts by mass

Solvent (cyclopentanone) 40.0 parts by mass

(Preparation of composition 428)

The following components were mixed to prepare a composition (photopolymerizable composition) 428.

Ultraviolet absorber (exemplified compound (1)). 2.0 parts by mass

60 Parts by mass of a polymerizable compound T-7

25 Parts by mass of a polymerizable compound T-8

15 Parts by mass of a polymerizable compound T-9

Photopolymerization initiator V-9 & lt/EN & gt 8.0 parts by mass

(Preparation of compositions 429 to 431)

Compositions 429 to 431 were prepared in the same manner as in composition 428, except that the ultraviolet absorber was changed to the same amount of exemplified compound (18), exemplified compound (33) or exemplified compound (42) in composition 428.

The details of the raw materials described in the above abbreviations are as follows.

(Ultraviolet absorber)

Compounds (1), (18), (33), (42), (43), comparative compounds (1), (2), (3) are exemplified: compounds of the above structure

(Polymerizable Compound)

T-1: KAYARAD DPHA (Nippon Kayaku Co., ltd., a compound having 2 or more ethylenically unsaturated bond-containing groups)

T-2: NK ESTER A-DPH-12E (Shin-Nakamura Chemical Co., ltd.) compound having 2 or more ethylenically unsaturated bond-containing groups

T-3: LIGHT ACRYLATE DCP-A (KYOEISHA CHEMICAL Co., LTD. Manufactured compound having 2 or more ethylenically unsaturated bond-containing groups)

T-4: benzyl methacrylate

T-5: beamset577 (3-6 functional urethane acrylate, ARAKAWA CHEMICAL Industries, ltd.)

T-6: FA-512M (dicyclopentenyloxyethyl methacrylate, showa Denko Materials Co., ltd.)

T-7: CYCLOMER M100 (3, 4-epoxycyclohexylmethyl methacrylate, daicel Corporation.)

T-8: OXT-221: 3-ethyl-3- { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetan, 2-functional oxetan, toagnosi co., ltd

T-9: celoxide2021P (3 ',4' -epoxycyclohexylmethyl 3, 4-epoxycyclohexane carboxylate, 2-functional epoxy, daicel Corporation)

(Resin)

U-1: 40% by mass propylene glycol monomethyl ether acetate solution of copolymer (weight average molecular weight 12000) of benzyl methacrylate/methacrylic acid (75/25 [ mass ratio ])

U-2: dianal BR-80 (Mitsubishi Chemical Corporation manufactured)

U-3: ARTON RX4500 (cyclic polyolefin resin having Tg of 140 ℃ C. Manufactured by JSR Corporation)

(Photopolymerization initiator)

V-1: omnirad TPO (IGM RESINS B.V. manufactured, photo radical polymerization initiator, acylphosphine compound)

V-2: omnirad 2959 (IGM RESINS B.V. manufactured, photo radical polymerization initiator, hydroxyacetophenone compound)

V-3:4,4' -bis (diethylamino) benzophenone (photo radical polymerization initiator, diphenyl ketone compound)

V-4:2,2 '-bis (2-chlorophenyl) -4,4',5 '-tetraphenyl-1, 2' -bisimidazole (o-Cl-HABI) (photo radical polymerization initiator, hexaarylbisimidazole compound)

V-5: IRGACURE-OXE01 (photo radical polymerization initiator, oxime Compound manufactured by BASF Co., ltd.)

V-6 Omnirad 907 (IGM RESINS B.V. manufactured, photo radical polymerization initiator, aminoacetophenone compound)

V-7 Omnirad 369 (IGM RESINS B.V. manufactured, photo radical polymerization initiator, aminoacetophenone compound)

V-8 Omnirad 819 (IGM RESINS B.V. manufactured, photo radical polymerization initiator, acylphosphine Compound)

V-9: CPI-210S (San-Apro Ltd. Photo cationic polymerization initiator, sulfonium salt)

(Production of resin film)

Production example 4-1 production of resin film Using compositions 401 to 435

The compositions 401 to 435 were spin-coated on a 50mm×50mm glass substrate (1737, corning Incorporated co., ltd.) to a film thickness of 1.5 μm, and dried at 100 ℃ for 2 minutes to form a composition layer. The composition layer was then subjected to full-face exposure using an i-ray stepper exposure apparatus (UX-1000 SM-EH04, manufactured by Ushio Inc.) at an exposure dose of 1000mJ/cm ². Next, the resin films 401 to 432 were produced by heating (post baking) at 200 ℃ for 8 minutes using a heating plate.

Regarding the resin films 401 to 435 obtained using the compositions 401 to 435, the degree of change in transmittance (degree of change 1 in transmittance) of the composition layer before and after exposure at the maximum absorption wavelength (λ _max) and the degree of change in transmittance (degree of change 2 in transmittance) of the composition layer before and after post baking at the maximum absorption wavelength (λ _max) were each 1% or less.

Transmittance of composition layer before exposure at λ _max -transmittance of composition layer after exposure at λ _max

Transmittance of the composition layer before post-baking at λ _max -transmittance of the composition layer after post-baking at λ _max |

PREPARATION EXAMPLE 4-2 preparation of resin film Using compositions 436 and 437

Resin films 436 and 437 were produced in the same manner as in production example 4-1, except that the film thickness of the composition layer was adjusted so that the transmittance of the composition layer before exposure was 5 to 20% at the maximum absorption wavelength (λ _max) using the compositions 436 and 437.

(Evaluation of light resistance)

Regarding the resin film obtained above, a light resistance test was performed under the following condition 3, and the degree of decrease in transmittance at the maximum absorption wavelength (λ _max) was calculated. Specifically, after the transmittance of the resin film at the maximum absorption wavelength (λ _max) was measured, the light resistance test was performed on the resin film under condition 3. The transmittance of the resin film after the light resistance test at the maximum absorption wavelength (λ _max) was measured, and the degree of decrease in transmittance was calculated by the following formula.

Degree of decrease (%) = (transmittance of resin film after light resistance test at λ _max) - (transmittance of resin film before light resistance test at λ _max)

(Condition 3)

The device comprises: xenon lamp weather resistance tester (Suga Test Instruments Co., ltd., manufactured by XL 75)

Illuminance: 90klx

During the test: 50 hours

Environment: 23 ℃ and relative humidity 50%

The degree of change in coloration of the resin film after the light resistance test was visually confirmed, and the presence or absence of coloration was evaluated according to the following criteria.

A: no coloring

B: slightly colored, but at a practical level

TABLE 8

As shown in the above table, the resin films 401 to 434 using the exemplified compounds (1), (18), (33), (42), (43) are excellent in light resistance. The resin films 401 to 434 have excellent absorption ability of ultraviolet rays having a wavelength of around 400nm and are less colored.

< Synthesis of Polymer >

Synthesis example 101 Synthesis of Polymer P-1

[ Chemical formula 107]

In a200 mL three-day flask, 100mg of Compound A-142 (maximum absorption wavelength (in ethyl acetate solution): 394 nm) obtained in Synthesis example 32, 9.9g of methyl methacrylate, 40.0g of propylene glycol monomethyl ether acetate were added, and the mixture was stirred under a nitrogen stream at 80℃for 30 minutes. To this solution, 200mg of dimethyl 2,2' -azobis (isobutyric acid) (manufactured by V-601, FUJIFILM Wako Pure Chemical Corporation (hereinafter referred to as V-601)) was added, and after stirring at 80℃for 6 hours, the solution was cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140mL of hexane and 60mL of isopropanol and left to stand for 1 night. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder, 140mL of hexane and 60mL of isopropyl alcohol were added, and after stirring at room temperature for 1 hour, the mixture was left at room temperature for 1 night. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50℃to obtain 7.0g of the target polymer P-1. The number average molecular weight of the obtained polymer P-1 was 27500 (in terms of polystyrene).

The obtained 100mg of Polymer P-1 was dissolved in 100mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of the polymer P-1 was 399nm (absorbance 1.61).

The polymer P-1 was able to sufficiently shield light having a wavelength around 400 nm. Moreover, the polymer P-1 is less colored.

Synthesis example 102 Synthesis of Polymer P-2

[ Chemical formula 108]

Into a 200mL three-necked flask, 100mg of Compound A-142 (maximum absorption wavelength (in ethyl acetate solution): 394 nm) obtained in Synthesis example 32, 100mg of 2- [ 2-hydroxy-5- (2-methacryloyloxyethyl) phenyl ] 2H-benzo [ d ] [1,2,3] triazole (maximum absorption wavelength (in ethyl acetate solution): 338 nm) as an ultraviolet absorber, 9.8g of methyl methacrylate, 40.0g of propylene glycol monomethyl ether acetate were added, and the mixture was stirred under a nitrogen stream at 80℃for 6 hours and then cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140mL of hexane and 60mL of isopropanol and left to stand for 1 night. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder, 140mL of hexane and 60mL of isopropyl alcohol were added, and after stirring at room temperature for 1 hour, the mixture was left at room temperature for 1 night. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50℃to obtain 5.0g of the target polymer P-2. The number average molecular weight of the obtained polymer P-2 was 33400 (in terms of polystyrene).

The obtained 150mg of Polymer P-2 was dissolved in 100mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelengths of the polymer P-2 were 399nm (absorbance 1.45) and 343nm (absorbance 0.83). The polymer P-2 was able to sufficiently shield light having a wavelength around 400 nm. Furthermore, the light having a wavelength shorter than 350nm is also excellent in shielding properties. And, the coloration of the polymer P-2 is small.

Synthesis example 103 Synthesis of Polymer P-3

[ Chemical formula 109]

Into a 200mL three-necked flask, 180mg of Compound A-142 (maximum absorption wavelength: 394nm in ethyl acetate solution) obtained in Synthesis example 32, 20mg of 2- (1, 2-dibenzyl-3, 5-dioxopyrazolin-4-ylidene) -5-methylbenzo [ d ] [1,3] dithiol-4, 7-diylbis ((2- (methacryloyloxy) ethyl) succinate) (maximum absorption wavelength: 380 nm) 9.8g of methyl methacrylate, 40.0g of propylene glycol monomethyl ether acetate as an ultraviolet absorber were charged, and after stirring at 80℃for 6 hours under a nitrogen stream, the mixture was cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140mL of hexane and 60mL of isopropanol and left to stand for 1 night. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder, 140mL of hexane and 60mL of isopropyl alcohol were added, and after stirring at room temperature for 1 hour, the mixture was left at room temperature for 1 night. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50℃to obtain 6.1g of the target polymer P-3. The number average molecular weight of the obtained polymer P-3 was 38200 (in terms of polystyrene).

The obtained 150mg of Polymer P-3 was dissolved in 100mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelengths of the polymer P-3 were 399nm (absorbance 2.12) and 383nm (absorbance 0.80). The polymer P-3 was able to sufficiently shield light having a wavelength around 400 nm. Furthermore, the light having a wavelength shorter than 350nm is also excellent in shielding properties. And, the coloration of the polymer P-3 is small.

Synthesis example 104 Synthesis of Polymer P-4

[ Chemical formula 110]

In a 200mL three-necked flask, 180mg of Compound A-142 (maximum absorption wavelength (in ethyl acetate solution): 394 nm) obtained in Synthesis example 32, 20mg of bis (2- (methacryloyloxy) ethyl) 4,4' - ((2- (1, 2-dibenzyl-3, 5-dioxopyrazolin-4-ylidene) -5-methylbenzo [ d ] [1,3] dithiol-4, 7-diyl) bis (oxy)) dibutyrate (maximum absorption wavelength (in ethyl acetate solution): 387 nm), 9.8g of methyl methacrylate, 40.0g of propylene glycol monomethyl ether acetate) as an ultraviolet absorber were charged, and after stirring under a nitrogen stream at 80℃for 6 hours, the mixture was cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140mL of hexane and 60mL of isopropanol and left to stand for 1 night. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder, 140mL of hexane and 60mL of isopropyl alcohol were added, and after stirring at room temperature for 1 hour, the mixture was left at room temperature for 1 night. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50℃to obtain 5.8g of the target polymer P-4. The number average molecular weight of the obtained polymer P-4 was 31900 (in terms of polystyrene).

The obtained 150mg of Polymer P-4 was dissolved in 100mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of the polymer P-4 was 399nm (absorbance 2.31) and 390nm (absorbance 0.78). The polymer P-4 is capable of sufficiently shielding light having a wavelength of around 400 nm. Furthermore, the light having a wavelength shorter than 350nm is also excellent in shielding properties. And, the coloration of the polymer P-4 is small.

Synthesis of Polymer P-5 (Synthesis example 105)

[ Chemical formula 111]

Into a 200mL three-necked flask, 100mg of Compound A-232 (maximum absorption wavelength: 391nm in ethyl acetate solution) obtained in Synthesis example 36, 9.9g of methyl methacrylate and 40.0g of propylene glycol monomethyl ether acetate were charged, and the mixture was stirred under a nitrogen flow at 80℃for 30 minutes. To this solution, 200mg of dimethyl 2,2' -azobis (isobutyric acid) (manufactured by V-601, FUJIFILM Wako Pure Chemical Corporation (hereinafter referred to as V-601)) was added, and after stirring at 80℃for 6 hours, the solution was cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140mL of hexane and 60mL of isopropanol and left to stand for 1 night. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder, 140mL of hexane and 60mL of isopropyl alcohol were added, and after stirring at room temperature for 1 hour, the mixture was left at room temperature for 1 night. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50℃to obtain 7.4g of the target polymer P-5. The number average molecular weight of the obtained polymer P-5 was 29500 (in terms of polystyrene).

The obtained 100mg of Polymer P-5 was dissolved in 100mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of the polymer P-5 was 397nm (absorbance 1.57).

The polymer P-5 was able to sufficiently shield light having a wavelength around 400 nm. And, the coloration of the polymer P-5 is small.

Comparative Synthesis example 1 Synthesis of Polymer P-6

[ Chemical formula 112]

Into a 200mL three-necked flask, 104mg of 2- [ 2-hydroxy-5- (2-methacryloyloxyethyl) phenyl ] 2H-benzo [ d ] [1,2,3] triazole, 9.9g of methyl methacrylate, 40.0g of propylene glycol monomethyl ether acetate were charged, and the mixture was stirred under a nitrogen stream at 80℃for 30 minutes. To this solution was added 135mg of V-601 and stirred at 80℃for 4 hours. 37mg of V-601 was further added, and after stirring at 90℃for 2 hours, it was cooled to room temperature. The reaction mixture obtained was slowly added to a mixture of 140mL of hexane, 60mL of isopropanol. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. To the obtained powder, 140mL of hexane and 60mL of isopropyl alcohol were added, and after stirring at room temperature for 3 hours, the precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50℃to obtain 8.1g of the target polymer P-6. The number average molecular weight of the obtained polymer P-5 was 14100 (in terms of polystyrene). An absorption spectrum was measured by dissolving 150mg of polymer P-6 in 100mL of chloroform. The maximum absorption wavelength of the polymer P-6 was 339nm (absorbance 0.91). The polymer P-6 has low shielding properties against light at a wavelength of 380 to 400 nm.

< Test example 5>

Example 501 production of resin film 501

A resin composition (resin solution) containing 500mg of Polymer P-1, 7.6g of chloroform and 1.1g of polymethyl methacrylate resin (Dianal BR-80 containing 60% by mass or more of methyl methacrylate as a monomer unit, produced by weight average molecular weight: 95000, acid value: omgKOH/g, mitsubishi Chemical Corporation) was prepared, and the obtained resin composition was spin-coated on a glass substrate, and the coating film was dried at 60℃for 2 minutes to form a resin film 501 containing Polymer P-1 and having a thickness of about 10. Mu.m. The resin film 501 was hardly colored, and the light-shielding property at a wavelength of around 400nm was excellent.

Example 502 manufacture of resin film 502

In example 501, a resin film 502 was formed in the same manner as in example 501, except that 500mg of the polymer P-1 was changed to 500mg of the polymer P-2. The resin film 502 is hardly colored, and has excellent shielding properties against light having a wavelength in the vicinity of 400 nm. Furthermore, the light having a wavelength shorter than 350nm is also excellent in shielding properties.

Example 503 manufacture of resin film 503

In example 501, a resin film 503 was formed in the same manner as in example 501, except that 500mg of the polymer P-1 was changed to 500mg of the polymer P-3. The resin film 503 is hardly colored, and has excellent shielding properties against light having a wavelength in the vicinity of 400 nm. Furthermore, the light having a wavelength shorter than 350nm is also excellent in shielding properties.

Example 504 production of resin film 504

In example 501, a resin film 504 was formed in the same manner as in example 501, except that 500mg of the polymer P-1 was changed to 500mg of the polymer P-4. The resin film 504 is hardly colored, and has excellent shielding properties against light having a wavelength in the vicinity of 400 nm. Furthermore, the light having a wavelength shorter than 350nm is also excellent in shielding properties.

Example 505 production of resin film 505

In example 501, a resin film 505 was formed in the same manner as in example 501, except that 500mg of the polymer P-1 was changed to 500mg of the polymer P-5. The resin film 505 is hardly colored, and has excellent shielding properties against light having a wavelength in the vicinity of 400 nm. Furthermore, the light having a wavelength shorter than 350nm is also excellent in shielding properties.

(Comparative example 501) production of resin film 506

In example 501, a resin film 506 was formed in the same manner as in example 501, except that 500mg of the polymer P-1 was changed to 1063mg of the polymer P-6. The resin film of the resin film 506 has low shielding property against light having a wavelength of 380 to 400 nm.

(Evaluation of light resistance)

Under the following condition 4, the resin films 501 to 506 formed in examples 501 to 505 and comparative example 501 were subjected to a light resistance test, and the absorbance maintenance ratio at the maximum absorption wavelength (λ _max) was obtained, and the light resistance was evaluated. Specifically, after measuring the absorbance of the resin film at λ _max, the light resistance test was performed on the resin film under the following condition 4, and the absorbance at λ _max was measured on the resin film after the light resistance test. From the values of absorbance at λ _max before and after irradiation, the absorbance maintenance rate (%) was calculated by the following formula. The absorbance maintenance rate is shown in the following table. The absorbance was obtained from the absorbance of the light using a spectrophotometer UV-1800PC (SHIMADZU CORPORATION).

Absorbance maintenance (%) = (absorbance at λ _max after irradiation/absorbance at λ _max before irradiation) ×100

Further, the larger the absorbance maintenance ratio, the more excellent the light resistance.

(Condition 4)

The device comprises: low temperature circulation xenon lamp weather resistance tester (Suga Test Instruments company: XL 75)

Illuminance: 90klx (40 w/m ²)

Time: 3 weeks

Environment: 23 ℃ and relative humidity 5%

TABLE 9

The resin films 501 to 505 (examples 501 to 505) are excellent in light resistance. The resin films 501 to 505 have excellent ultraviolet absorption ability around 400nm wavelength and little coloration.

After the resin films 501 to 505 were stored at 40℃and 50% humidity for 1 week, the films were left at room temperature for 1 day, and the presence or absence of bleeding and precipitation was visually observed. No bleeding and deposition were observed in any of the resin films 501 to 505.

< Test example 6>

(Production of resin film)

1Kg of a polycarbonate resin (Sumika Polycarbonate Ltd., SD POLYCA-30, glass transition point 145-150 ℃ C.) and 0.8g of an ultraviolet absorber described in the following table were stirred with a stainless steel tube for 1 hour to obtain a mixture. The obtained mixture was melt-kneaded for 1 minute using a twin-screw kneading extruder (manufactured by TECHNOVEL CORPORATION, KZW15TW-45/60 MG-NH) at 280 to 320 ℃ (temperature of 280℃at the raw material inlet side and temperature of 320℃at the discharge side of the kneaded product), to obtain a pellet-shaped kneaded product. After the obtained pellet-shaped kneaded material was dried at 80℃for 3 hours, resin films (molded plates) 601 to 608 having a thickness of 0.15mm were produced by molding with a press.

(Evaluation of light resistance)

Under the following condition 5, the resin films 601 to 608 were subjected to a light resistance test to obtain the absorbance maintenance ratio at the maximum absorption wavelength (λ _max), and the light resistance was evaluated. Specifically, after measuring the absorbance of the resin film at λ _max using a spectrophotometer (manufactured by UV-1800PC, SHIMADZU CORPORATION), the resin film was subjected to a light resistance test under condition 5, and the absorbance of the resin film after the light resistance test was measured at λ _max. Next, the absorbance maintenance rate (%) was calculated by the following formula using the values of absorbance at λ _max of the resin film before and after the light resistance test, and the light resistance was evaluated according to the following criteria. The higher the absorbance maintenance ratio, the more excellent the light resistance. The evaluation results are shown in the following table. The values in brackets in the columns for light fastness are values for absorbance maintenance.

Evaluation criterion-

AA: the absorbance maintenance rate is more than 90 percent

A: the absorbance maintenance rate is more than 85 percent

B: the absorbance maintenance rate is 80% or more and less than 85%

C: the absorbance maintenance rate is less than 80 percent

(Condition 5)

Illuminance: 90klx (40 w/m ²)

Time: 24 hours

Environment: 23 ℃ and relative humidity 50%

TABLE 10

As shown in the above table, the resin films 601 to 605 using the exemplified compounds (1), (18), (33), (42), (43) are excellent in light resistance. The resin films 601 to 605 are excellent in ultraviolet absorption ability around 400nm wavelength and less in coloration.

After the resin films 601 to 605 were stored at 40℃and 50% humidity for 1 week, the films were left at room temperature for 1 day, and the presence or absence of bleeding and precipitation was visually observed. No bleeding out and deposition were observed in any of the resin films 601 to 605.

Test example 7 ]

(Production of resin films 701 to 705)

1Kg of polymethyl methacrylate resin (PMMA) and 0.8g of the ultraviolet absorber described in the following Table were stirred with a stainless steel tube for 1 hour. The mixture was melt-mixed at 230 to 240℃by using a vented extruder, and molding pellets were produced by a conventional method. After the pellets were dried at 80℃for 3 hours, a resin film having a thickness of 0.15mm was produced by molding with a press machine. The light resistance of the obtained resin film was evaluated by the same method as in test example 6.

(Production of resin films 706 to 710)

1Kg of polyethylene terephthalate (PET) pellets dried at 130℃for 6 hours and 0.8g of an ultraviolet absorber described in the following Table were stirred with a stainless steel cylinder for 1 hour. The mixture was melt-mixed at 265 to 280℃with a vented extruder, and pellets for molding were produced by a conventional method. After the pellets were dried at 80℃for 3 hours, a resin film having a thickness of 0.15mm was produced by molding with a press machine. The light resistance of the obtained resin film was evaluated by the same method as in test example 6.

(Production of resin films 711 to 715)

1Kg of particles of cycloolefin polymer (COP) dried at 100℃for 6 hours and 0.8g of an ultraviolet absorber described in the following Table were stirred with a stainless steel cylinder for 1 hour. The mixture was melt-mixed at 260 to 290℃using a vented extruder, and pellets for molding were produced by a conventional method. After the pellets were dried at 80℃for 3 hours, a resin film having a thickness of 0.15mm was produced by molding with a press machine. The light resistance of the obtained resin film was evaluated by the same method as in test example 6.

(Production of resin films 716 to 720)

1Kg of nylon-66 (PA-66) particles dried at 80℃for 16 hours and 0.8g of the ultraviolet absorber described in the following table were stirred with a stainless steel cylinder for 1 hour. The mixture was melt-mixed at 270 to 290℃using a vented extruder, and pellets for molding were produced by a conventional method. After the pellets were dried at 80℃for 3 hours, a resin film having a thickness of 0.15mm was produced by molding with a press machine. The light resistance of the obtained resin film was evaluated by the same method as in test example 6.

(Resin films 72l to 725)

1Kg of polypropylene (PP) pellets and 0.8g of the ultraviolet absorber described in the following Table were stirred with a stainless steel cylinder for 1 hour. The mixture was melt-mixed at 230 to 250℃using a vented extruder, and pellets for molding were produced by a conventional method. After the pellets were dried at 80℃for 3 hours, a resin film having a thickness of 0.15mm was produced by molding with a press machine. The light resistance of the obtained resin film was evaluated by the same method as in test example 1.

TABLE 11

As shown in the above table, the resin films 701 to 725 using the exemplified compounds (1), (18), (33), (42), (43) are excellent in light resistance. The resin films 701 to 725 have excellent ultraviolet light absorption ability around 400nm wavelength and little coloration.

After the resin films 701 to 725 were stored at 40℃and 50% humidity for 1 week, the films were left at room temperature for 1 day, and the presence or absence of bleeding and precipitation was visually observed. No bleeding out and deposition were observed in any of the resin films 701 to 725.

< Test example 8>

The resin compositions were prepared by dissolving the compounds (exemplified by compounds (1), (18), (33), (42), (43) and compounds C-1 to C-3) described in the following tables in 7.6g of chloroform and 1.1g of (meth) acrylic resin (produced by Dianal BR-80, mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, and having a weight average molecular weight of 95000). The obtained resin composition was spin-coated on a glass substrate to form a coating film, and the obtained coating film was dried at 110℃for 2 minutes to produce resins 801 to 815.

Under the following condition 6, the resin films 801 to 815 were subjected to a light resistance test to obtain the absorbance maintenance ratio at a wavelength of 400nm, and the light resistance was evaluated. Specifically, after measuring the absorbance of the resin film at λ _max using a spectrophotometer (manufactured by UV-1800PC, SHIMADZU CORPORATION), the resin film was subjected to a light resistance test under condition 6 for 3 weeks, and the absorbance at λ _max was measured for the resin film after the light resistance test. Next, the absorbance maintenance rate (%) was calculated by the following formula using the values of absorbance at λ _max of the resin film before and after the light resistance test, and the light resistance was evaluated according to the following criteria. The higher the absorbance maintenance ratio, the more excellent the light resistance. The evaluation results are shown in the following table. The values in brackets in the columns for light fastness are values for absorbance maintenance.

Evaluation criterion-

AA: the absorbance maintenance rate is more than 90 percent

A: the absorbance maintenance rate is more than 85 percent

B: the absorbance maintenance rate is 80% or more and less than 85%

C: the absorbance maintenance rate is less than 80 percent

(Condition 6)

Illuminance: 90klx (40 w/m ²)

Time: 3 weeks

Environment: 23 ℃ and relative humidity 50%

TABLE 12

The resin films 801 to 815 have large absorption of light in the vicinity of 400nm and excellent absorption of ultraviolet light on the long wavelength side. And also has a good absorbance maintenance ratio at 400nm after the light resistance test, and excellent light resistance.

The exemplary compounds (1), (18), (33), (42) and (43) in the above table are compounds having the above structures. The compounds C-1 to C-3 have the following structures.

[ Chemical formula 113]

Claims

1. A resin composition comprising a compound represented by the formula (1) and a resin,

In formula (1), Q ¹ represents a group represented by formula (Q-1),

R ¹ and R ² each independently represent a hydrogen atom or a substituent,

2. The resin composition according to claim 1, wherein,

3. The resin composition according to claim 1 or 2, wherein,

In the formula (3), Q ³ represents a group represented by the formula (Q-1),

Q ⁴ represents =o, =s, =nr ^q11, or =cr ^q12R^q13,R^q11～R^q13 each independently represents a hydrogen atom or a substituent, optionally R ^q12 and R ^q13 are bonded to each other to form a ring, wherein in the case where R ^q12 and R ^q13 are bonded to form a ring, =cr ^q12R^q13 is not the same structure as Q ³,

4. The resin composition according to claim 3, wherein,

R ¹¹ and R ¹² of formula (3) each independently represent-OH, -O-Y ¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹ or-OSO ₂-Y¹¹,R^y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group.

5. The resin composition according to claim 3, wherein,

6. The resin composition according to any one of claims 1 to 5, wherein,

7. A cured product obtained by using the resin composition according to any one of claims 1 to 6.

8. An optical member comprising the cured product according to claim 7.

9. An ultraviolet absorber comprising a compound represented by the formula (1),

In formula (1), Q ¹ represents a group represented by formula (Q-1),

R ¹ and R ² each independently represent a hydrogen atom or a substituent,

10. The ultraviolet light absorber according to claim 9, wherein,

11. A compound represented by the formula (3),

In formula (3), Q ³ represents a group represented by formula (Q-1),

Q ⁴ represents=0, =s, =nr ^q11 or=cr ^q12R^q13,R^q11～R^q13 each independently represents a hydrogen atom or a substituent, optionally R ^q12 and R ^q13 are bonded to each other to form a ring, wherein in the case where R ^q12 and R ^q13 are bonded to form a ring, =cr ^q12R^q13 is not the same structure as Q ³,

R ¹¹ and R ¹² each independently represent -OH、-O-Y¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹、-OSO₂-Y¹¹ or a group containing a polymerizable group having an ethylenically unsaturated bond, R ^y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group,

12. The compound according to claim 11, wherein,

R ¹¹ and R ¹² of the formula (3) each independently represent-OH, -O-Y ¹¹、-OC(＝O)-Y¹¹、-OC(＝O)O-Y¹¹、-OC(＝O)NR^y11-Y¹¹ or-OSO ₂-Y¹¹,R^y11 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, Y ¹¹ represents an alkyl group, an aralkyl group or an aryl group,

13. The compound according to claim 11, wherein,

14. A method for producing a compound represented by formula (6) by reacting a compound represented by formula (4) with a compound represented by formula (5),

In formula (4), Q ⁵ represents a group represented by formula (Q-1),

Q ⁶ represents =o, =s, =nr ^q21 or =cr ^q22R^q23,

R ^q21～R^q23 each independently represents a hydrogen atom or a substituent, optionally R ^q22 and R ^q23 are bonded to each other to form a ring, wherein, in the case where R ^q22 and R ^q23 are bonded to form a ring, =CR ^q22R^q23 and Q ⁵ are not the same structure,

R ^e52 represents-Cl or alkoxy, Y ⁵¹ represents alkyl, aralkyl or aryl,

In formula (6), Q ⁵ represents a group represented by formula (Q-1),

Q ⁶ represents =o, =s, =nr ^q21 or =cr ^q22R^q23,

15. The method for producing a compound according to claim 14, wherein,

16. A polymer comprising a structure derived from the compound of claim 13.