KR20210134341A - Optical layer and laminate comprising the optical layer - Google Patents

Abstract

[식 (X) 중, 고리 W¹은, 고리의 구성 요소로서 적어도 하나의 이중 결합을 가지며, 또한 방향족성을 갖지 않는 고리 구조를 나타낸다. R³은, 복소환기, 할로겐 원자, 니트로기, 시아노기, 히드록시기, 티올기, 카르복시기, -SF₅, -SF₃, -SO₃H, -SO₂H, 치환기를 갖고 있어도 좋은 탄소수 1∼25의 지방족 탄화수소기 또는 치환기를 갖고 있어도 좋은 탄소수 6∼18의 방향족 탄화수소기를 나타낸다.] An optical layer formed from a composition containing a compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X).

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity. R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent.]

Description

Optical layer and laminate comprising the optical layer

The present invention relates to an optical layer and a laminate comprising the optical layer.

DESCRIPTION OF RELATED ART Various members, such as display elements, such as organic electroluminescent element and a liquid crystal cell, and optical films, such as a polarizing plate, are used for display apparatuses (FPD: flat panel display), such as an organic electroluminescent display and a liquid crystal display device. The organic EL compound and liquid crystal compound used in these members often use compounds with poor weather resistance among organic substances, so deterioration by not only ultraviolet (UV) but also short-wavelength visible light with a wavelength of 380 to 420 nm or less is a problem. easy to become In order to solve such a problem, for example, in patent document 1, the optical laminated body which provided the adhesive layer containing the compound represented by a following formula is described.

Patent Document 1: Japanese Patent Laid-Open No. 2017-48340

However, in the optical laminated body of patent document 1, suppression of deterioration of an organic element or a liquid crystal compound may not be enough yet.

The present invention includes the following inventions.

[1] An optical layer formed of a composition containing a compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X).

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.

R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

[2] The compound according to [1], wherein the compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X) is any of the compound represented by the formula (I) to the compound represented by the formula (VIII). optical layer.

[In formulas (I) to (VIII),

Rings W ¹ and R ³ have the same meanings as above.

Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently It represents a ring structure having at least one double bond as a component.

Ring W ¹¹¹ represents a ring having at least two nitrogen atoms as a component.

Ring W ¹¹² and ring W ¹¹³ each independently represent a ring having at least one nitrogen atom as a constituent element.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ^{112 .} are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, which may have a substituent represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= ^{contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -NR 12A} -, - SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- it may be good

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a heterocyclic group, a halogen atom, a nitro group, a cyano group, or a hydroxyl group , thiol group, carboxyl group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon having 6 to 18 carbon atoms which may have a substituent _{group and -CH 2} - or -CH= contained in this aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO -, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A are each independently a hydrogen atom or carbon number An alkyl group of 1-6 is represented.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ each independently represents an electron withdrawing group.

R ¹ and R ² may be bonded to each other to form a ring.

R ⁴¹ and R ⁴² may be bonded to each other to form a ring.

R ⁵¹ and R ⁵² may be bonded to each other to form a ring.

R ⁶¹ and R ⁶² may be bonded to each other to form a ring.

R ⁹¹ and R ⁹² may be bonded to each other to form a ring.

R ¹⁰¹ and R ¹⁰² may be bonded to each other to form a ring.

R ¹¹¹ and R ¹¹² may be bonded to each other to form a ring.

R ² and R ³ may be bonded to each other to form a ring.

R ¹² and R ¹³ may be bonded to each other to form a ring.

R ⁴² and R ⁴³ may be bonded to each other to form a ring.

R ⁵² and R ⁵³ may be bonded to each other to form a ring.

R ⁶² and R ⁶³ may be bonded to each other to form a ring.

R ⁷² and R ⁷³ may combine with each other to form a ring.

R ⁸² and R ⁸³ may be bonded to each other to form a ring.

R ⁹² and R ⁹³ may be bonded to each other to form a ring.

R ¹⁰² and R ¹⁰³ may be bonded to each other to form a ring.

R ¹¹² and R ¹¹³ may be bonded to each other to form a ring.

R ⁴ and R ⁵ may be bonded to each other to form a ring.

R ¹⁴ and R ¹⁵ may be bonded to each other to form a ring.

R ²⁴ and R ²⁵ may be bonded to each other to form a ring.

R ³⁴ and R ³⁵ may be bonded to each other to form a ring.

R ⁷⁴ and R ⁷⁵ may be bonded to each other to form a ring.

R ⁸⁴ and R ⁸⁵ may be bonded to each other to form a ring.

R ⁶ and R ⁸ each independently represent a divalent linking group.

R ⁷ represents a single bond or a divalent linking group.

R ⁹ and R ¹⁰ each independently represent a trivalent linking group.

R ¹¹ represents a tetravalent linking group.]

[3] ^{At least one selected from R 4} and R ⁵ is a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group, a fluoroaryl group, - CO-OR ²²² , -SO ₂ -R ²²² or -CO-R ²²² (R ²²² is a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms. shown.), the optical layer according to [2].

[4] ^{At least one selected from R 4} and R ⁵ is a nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR ²²² or -SO ₂ -R ^The optical layer according to [2] or [3], wherein R ²²² represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

[5] ^{At least one selected from R 4} and R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom, an optionally substituted C1-C25 alkyl group, or The optical layer according to any one of [2] to [4], wherein an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent is represented.)

[6] The optical layer according to any one of [2] to [5], wherein at least one selected from ^{R 4} and R ^{5 is a cyano group.}

[7] R ⁴ is a cyano group,

R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic group having 6 to 18 carbon atoms It represents a hydrocarbon group.) The optical layer according to any one of [2] to [6].

[8] The optical layer according to any one of [2] to [7], wherein both ^{R 4} and R ^{5 are cyano groups.}

[9] The ^{optical layer according to any one of [2] to [8], wherein R 1} and R ² are each independently an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.

[10] The optical layer according to any one of [2] to [8], wherein ^{R 1} and R ^{2 are linked to each other to form a ring.}

[11] The optical layer according to [10], wherein the ring formed by connecting ^{R 1} and R ^{2 to each other is an aliphatic ring.}

[12] Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently The optical layer according to any one of [2] to [11], which is a ring having no aromaticity.

[13] R ³ is a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group, a fluoroaryl group, -CO-OR ^111A or -SO ₂ - The ^{optical layer according to any one of [1] to [12], wherein R 112A} (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom).

[14] R ³ is a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A are each independently The optical layer according to any one of [1] to [13], wherein an alkyl group having 1 to 24 carbon atoms which may have a halogen atom is represented.)

[15] The optical layer according to any one of [1] to [14], wherein ^{R 3 is a cyano group.}

[16] The optical layer according to any one of [1] to [15], which satisfies the following formula (a).

A(395)>0.5 (a)

[A (395) represents the absorbance at a wavelength of 395 nm of the optical layer.]

[17] The optical layer according to any one of [1] to [16], which satisfies the following formula (b).

A(395)/A(430)>10 (b)

[A(395) represents the absorbance at a wavelength of 395 nm of the optical layer, and A(430) represents the absorbance at a wavelength of 430 nm of the optical layer.]

[18] The optical layer according to any one of [1] to [17], wherein the film thickness is 1 to 500 µm.

[19] a compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X);

A resin having a glass transition temperature of 30° C. or less, and

The optical layer according to any one of [1] to [18], which is formed of a composition containing a crosslinking agent.

[20] a compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X);

a photocurable component,

The optical layer according to any one of [1] to [18], which is formed of a composition containing a photoinitiator.

[21] Any of [1] to [18] formed of a composition comprising a compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X), and at least one resin selected from the following group A The optical layer described in one.

Group A: Cellulose-based resins, (meth)acrylic-based resins, polyester-based resins, polyamide-based resins, polyimide-based resins and cycloolefin-based resins

[22] An optical laminate comprising the optical layer according to any one of [1] to [21] and a polarizer.

[23] An image display device comprising the optical laminate according to [22].

[24] A compound having a molecular weight of 3000 or less and having a partial structure represented by Formula (X);

A resin having a glass transition temperature of 30° C. or less, and

A composition comprising a crosslinking agent.

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.

R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

[25] A compound having a molecular weight of 3000 or less and having a partial structure represented by Formula (X);

a photocurable component,

A composition comprising a photoinitiator.

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.

R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

[26] A composition comprising a compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X), and at least one resin selected from the following group A.

Group A: Cellulose-based resins, (meth)acrylic-based resins, polyester-based resins, polyamide-based resins, polyimide-based resins and cycloolefin-based resins

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.

R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

The present invention provides an optical layer having good weather resistance.

BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic sectional drawing which shows typically an example of the optical laminated body of this invention.
It is a schematic sectional drawing which shows typically an example of the optical laminated body of this invention.
It is a schematic sectional drawing which shows typically an example of the optical laminated body of this invention.
It is a schematic sectional drawing which shows typically an example of the optical laminated body of this invention.
It is a schematic sectional drawing which shows typically an example of the optical laminated body of this invention.
It is a schematic sectional drawing which shows typically an example of the optical laminated body of this invention.

"(meth)acryloyl group" in this specification means at least one chosen from an acryloyl group and a methacryloyl group. It is the same also about "(meth)acryloyloxy group", "(meth)acryl", "(meth)acrylate", etc.

<Optical layer>

The optical layer of the present invention is a layer that absorbs and/or transmits light. The optical layer may be a layer included in an optical member such as a display device or an imaging device. The optical layer of the present invention exhibits high absorptivity for short-wavelength visible light near a wavelength of 395 nm, while low absorptivity for light near a wavelength of 430 nm, and can suppress the influence on the color of the display device.

The optical layer of the present invention is formed from a composition containing a compound (hereinafter, sometimes referred to as compound (X)) having a molecular weight of 3000 or less and having a partial structure represented by formula (X).

By including the compound (X), an optical layer having good weather resistance and high absorption selectivity for visible light with a short wavelength of around 390 nm can be obtained.

It is preferable that the optical layer of this invention satisfy|fills following formula (a).

A(395)≥0.5 (a)

[A (395) represents the absorbance at a wavelength of 395 nm of the optical layer.]

A larger value of A(395) indicates that absorption at a wavelength of 395 nm is higher. When the value of A (395) is less than 0.5, absorption at a wavelength of 395 nm is low, and the effect of suppressing deterioration of a display device such as a retardation film or an organic EL element in short-wavelength visible light is small. The value of A (395) is preferably 0.6 or more, more preferably 0.8 or more, and particularly preferably 1.0 or more from the viewpoint of suppressing weathering deterioration. Although there is no upper limit in particular, it is 10.0 or less normally.

It is more preferable that the optical layer of this invention satisfy|fills following formula (b).

A(395)/A(430)≥10 (b)

[A(395) represents the absorbance at a wavelength of 395 nm of the optical layer, and A(430) represents the absorbance at a wavelength of 430 nm of the optical layer.]

The value of A(395)/A(430) represents the ratio of the size of light absorption at a wavelength of 395 nm to the size of light absorption at a wavelength of 430 nm, and as this value increases, absorption specific to a wavelength region around 395 nm indicates that there is, and the effect of color on the display device can be suppressed. The value of A(395)/A(430) is preferably 15 or more, more preferably 20 or more, and particularly preferably 30 or more.

The thickness of the optical layer of this invention is 1-500 micrometers normally, Preferably it is 2-100 micrometers, More preferably, it is 2.5-50 micrometers, More preferably, it is 3-30 micrometers.

As an optical layer of this invention, a polarizer, a protective film, retardation film, an adhesive layer, an adhesive bond layer, surface treatment layers, such as a hard coat, a brightness improving film, etc. are mentioned, for example. The optical layer of the present invention can be obtained by, for example, molding a composition containing compound (X) into a sheet shape. Moreover, another optical layer may be laminated|stacked on the optical layer of this invention, and it can also be set as an optical laminated body. When laminating|stacking optical layers, the optical layers of this invention may be laminated|stacked, and the optical layer of this invention and the layer which does not contain a compound (X) may be laminated|stacked.

<Compound (X)>

The optical layer of this invention contains the compound which molecular weight is 3000 or less, and has a partial structure represented by Formula (X).

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.

R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

In this specification, carbon number does not include carbon number of a substituent, When -CH ₂ - or -CH= is substituted, for example as above, it means carbon number before substitution.

The ring W ¹ is not particularly limited as long as it is a ring having one or more double bonds as a component of the ring, and is a ring having no aromaticity. Ring W ¹ may be a monocyclic ring or a condensed ring may be sufficient as it.

The ring W ¹ may be a heterocyclic ring containing a hetero atom (eg, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a component of the ring, or an aliphatic hydrocarbon ring composed of a carbon atom and a hydrogen atom.

Ring W ¹ has at least one double bond as a component of the ring, but the ^{number of double bonds contained in ring W 1} is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2; It is more preferable that there is only one.

Ring W ¹ is usually a ring having 5 to 18 carbon atoms, preferably a 5 to 7 membered ring structure, and more preferably a 6 membered ring structure.

It is preferable that ring W<^{1> is monocyclic.}

Ring W ¹ may have a substituent. As said substituent, Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; an alkyl group having 1 to 12 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a nonyl group; Fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoro a halogenated alkyl group having 1 to 12 carbon atoms, such as a roethyl group and a 1,1,2,2,2-pentafluoroethyl group; an alkoxy group having 1 to 12 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; Fluorination of 1 to 12 carbon atoms, such as monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group alkoxy group; an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms, such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, and methylethyl; an alkylcarbonyloxy group having 2 to 12 carbon atoms, such as a methylcarbonyloxy group and an ethylcarbonyloxy group; an alkylsulfonyl group having 1 to 12 carbon atoms, such as a methylsulfonyl group and an ethylsulfonyl group; an arylsulfonyl group having 6 to 12 carbon atoms such as a phenylsulfonyl group; cyano group; nitro group; hydroxyl group; thiol group; carboxyl group; -SF ₃ ; -SF ₅ etc. are mentioned.

The substituent which the ring W ¹ may have is preferably an amino group which may be substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. .

The ring W ¹ includes, for example, the groups described below.

[In the formula, *1 represents the number of bonds with a nitrogen atom, and *2 represents the number of bonds with a carbon atom.]

Examples ^{of the heterocyclic group represented by R 3} include a pyridyl group, a pyrrolidyl group, a tetrahydrofurfuryl group, a tetrahydrothiophene group, a pyrrole group, a furyl group, a thiopheno group, a piperidine group, a tetrahydropyranyl group, and tetrahydro thiopyranyl group, thiapyranyl group, imidazolino group, pyrazole group, oxazole group, thiazolyl group, dioxanyl group, morpholino group, thiazinyl group, triazole group, tetrazole group, dioxolanyl group, pyridazinyl group, Pyrimidinyl group, pyrazinyl group, indolyl group, isoindolyl group, benzoimidazolyl group, purinyl group, benzotriazolyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, cinnolinyl group , pteridinyl group, benzopyranyl group, anthryl group, acridinyl group, xanthenyl group, carbazolyl group, tetracenyl group, porphinyl group, chlorinyl group, collinyl group, adenyl group, guanyl group, sheet aliphatic heterocyclic groups having 3 to 16 carbon atoms and aromatic heterocyclic groups having 3 to 16 carbon atoms, such as a sil group, a thyminyl group, a uracil group, a quinolyl group, a thiophenyl group, an imidazolyl group, an oxazolyl group, and a thiazolyl group; , pyrrolidyl group, piperidyl group, tetrahydrofurfuryl group, tetrahydropyranyl group, tetrahydrothiopheno group, tetrahydrothiopyranyl group or pyridyl group is preferable.

Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ³ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, isopene Tyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, undecyl group, la A linear or branched alkyl group having 1 to 25 carbon atoms, such as uryl group, myristyl group, cetyl group, and stearyl group: cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. having 3 to 25 carbon atoms cycloalkyl group; C4-C25 cycloalkylalkyl groups, such as a cyclohexylmethyl group, etc. are mentioned.

It is preferable that it is a C1-C15 alkyl group, and, as for the C1-C25 aliphatic hydrocarbon group represented by R<^{3>, it is more preferable that it is a C1-C12 alkyl group.}

The aliphatic hydrocarbon group which may have substituents represented by R ^3, there may be mentioned a halogen atom, a hydroxyl group, a nitro group, a cyano group, such as -SO ₃ H.

_{-CH 2} - or -CH= contained in the C1-C25 aliphatic hydrocarbon group represented by R ³ is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O -CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

_{When -CH 2} - or -CH= included in the C1-C25 aliphatic hydrocarbon group is substituted, it is preferably substituted with -O-, -S-, -CO-O- or -SO _{2 -.}

_{When -CH 2} - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -O-, the aliphatic hydrocarbon group is -O-R'(R' is a carbon number 1 which may have a halogen atom) It is preferable that it is an alkoxy group represented by the alkyl group of -24). Moreover, polyalkyleneoxy groups, such as a polyethyleneoxy group and a polypropyleneoxy group, may be sufficient. Examples of the alkoxy group represented by -O-R' include a methoxy group, an ethoxy group, and a -OCF ₃ group.

_{When -CH 2} - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -S-, the aliphatic hydrocarbon group is -S-R'(R' is a carbon number 1 which may have a halogen atom) It is preferable that it is an alkylthio group represented by the alkyl group of -24). Moreover, polyalkylenethio groups, such as a polyethylenethio group and a polypropylenethio group, may be sufficient. Examples of the alkylthio group represented by -S-R' include a methylthio group, an ethylthio group, a -SCF ₃ group, a polyethylenethio group, and a polypropylenethio group.

_{When -CH 2} - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -COO-, the aliphatic hydrocarbon group is -COO-R'(R' may have a halogen atom; -24 alkyl group) is preferable, and -SO ₂ CHF ₂ group, -SO ₂ CH ₂ F group, etc. may be sufficient.

_{When -CH 2} - or -CH= contained in the C1-C25 aliphatic hydrocarbon group _{is substituted with -SO 2} -, the aliphatic hydrocarbon group is -SO ₂ -R'(R' may have a halogen atom It is preferable that it is a group represented by a C1-C24 alkyl group).

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^{11A include a methyl group, an ethyl group, n-} Straight or branched C1-C6 groups such as propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n-hexyl group, 1-methylbutyl group and alkyl groups.

Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ³ include a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, a pentacenyl group, a phenanthryl group, a chrysenyl group, a triphenylenyl group, a tetraphenyl group, and a pyrenyl group. , an aryl group having 6 to 18 carbon atoms, such as a perylenyl group, a colonnyl group, and a biphenyl group; and an aralkyl group having 7 to 18 carbon atoms, such as a benzyl group, a phenylethyl group, and a naphthylmethyl group. An aryl group having 6 to 18 carbon atoms is preferable, and a phenyl group or a benzyl group is more preferable.

Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ^{3 may have include a halogen atom;} hydroxyl group; thiol group; amino group; nitro group; cyano group; -SO ₃ H group, and the like.

_{-CH 2} - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ³ is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O -CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

_{When -CH 2} - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted, it is preferably substituted with _{-O- or -SO 2 -.}

_{When -CH 2} - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -O-, the aromatic hydrocarbon group may include an aryloxy group having 6 to 17 carbon atoms such as a phenoxy group; It is preferable that they are an aryl alkoxy group of a phenoxyethyl group, a phenoxydiethylene glycol group, a phenoxy polyalkylene glycol group, etc.

_{When -CH 2} - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms _{is substituted with -SO 2} -, the aromatic hydrocarbon group is -SO ₂ -R"(R" is an aryl having 6 to 17 carbon atoms. group or an aralkyl group having 7 to 17 carbon atoms).

A fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned as a halogen atom represented by R<^3>.

R ³ is a nitro group; cyano group; halogen atom; -OCF ₃ ; -SCF ₃ ; -SF ₅ ; -SF ₃ ; a fluoroalkyl group (preferably having 1 to 25 carbon atoms); a fluoroaryl group (preferably having 6 to 18 carbon atoms); -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.)

cyano group; fluorine atom; chlorine atom; -OCF ₃ ; -SCF ₃ ; a fluoroalkyl group (preferably having 1 to 12 carbon atoms); It is more preferable that -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.)

It is especially preferable that it is a cyano group.

The molecular weight of compound (X) becomes like this. Preferably it is 2500 or less, More preferably, it is 2000 or less, More preferably, it is 1500 or less, Especially preferably, it is 1000 or less.

Moreover, Preferably it is 100 or more, 150 or more, and 200 or more.

A copolymer may be sufficient as compound (X) as long as molecular weight is 3000 or less, However, It is preferable that it is a monomer.

The compound (X) preferably exhibits a maximum absorption wavelength at a wavelength of 370 nm or more and 420 nm or less. When the compound (X) exhibits a maximum absorption wavelength at a wavelength of 370 nm or more and 420 nm or less, it can efficiently absorb ultraviolet to near-ultraviolet light having a wavelength of 380 nm or more and 400 nm or less. The maximum absorption wavelength (λmax) of the compound (X) is preferably a wavelength of 375 nm or more and 415 nm or less, more preferably a wavelength of 375 nm or more and 410 nm or less, and still more preferably a wavelength of 380 nm or more and 400 nm or less. .

The compound (X) preferably has a gram extinction coefficient ε at λmax of 0.5 or more, more preferably 0.75 or more, particularly preferably 1.0 or more. Although the upper limit in particular is not restrict|limited, Generally, it is 10 or less. In addition, λmax represents the maximum absorption wavelength of compound (X).

When the gram extinction coefficient ? at ?max of the compound (X) is 0.5 or more, even a small amount can efficiently absorb ultraviolet to near-ultraviolet light with a wavelength in the range of 380 to 400 nm.

As for compound (X), it is preferable that ε(λmax)/ε(λmax+30 nm) is 5 or more, more preferably 10 or more, and particularly preferably 20 or more. Although the upper limit in particular is not restrict|limited, Generally, it is 1000 or less. ε(λmax) represents the gram extinction coefficient at the maximum absorption wavelength [nm] of the compound (X), and ε(λmax+30 nm) is the (maximum absorption wavelength [nm] + 30 nm) of the compound (X) shows the extinction coefficient in grams at the wavelength [nm] of

When ε(λmax)/ε(λmax+30 nm) is 5 or more, since sub-absorption at a wavelength of 420 nm or more can be minimized, coloration is difficult to occur.

In addition, the unit of the gram extinction coefficient is L/(g*cm).

The compound (X) is preferably any of the compound represented by the formula (I) to the compound represented by the formula (VIII), and more preferably a compound represented by the formula (I).

[In formulas (I) to (VIII),

Rings W ¹ and R ³ have the same meanings as above.

Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently It represents a ring structure having at least one double bond as a component.

Ring W ¹¹¹ represents a ring having at least two nitrogen atoms as a component.

Ring W ¹¹² and ring W ¹¹³ each independently represent a ring having at least one nitrogen atom as a constituent element.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ^{112 .} are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, which may have a substituent represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= ^{contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -NR 12A} -, - SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- it may be good

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a heterocyclic group, a halogen atom, a nitro group, a cyano group, or a hydroxyl group , thiol group, carboxyl group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon having 6 to 18 carbon atoms which may have a substituent _{group and -CH 2} - or -CH= contained in this aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO -, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A are each independently a hydrogen atom or carbon number An alkyl group of 1-6 is represented.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ each independently represents an electron withdrawing group.

R ¹ and R ² may be bonded to each other to form a ring.

R ⁴¹ and R ⁴² may be bonded to each other to form a ring.

R ⁵¹ and R ⁵² may be bonded to each other to form a ring.

R ⁶¹ and R ⁶² may be bonded to each other to form a ring.

R ⁹¹ and R ⁹² may be bonded to each other to form a ring.

R ¹⁰¹ and R ¹⁰² may be bonded to each other to form a ring.

R ¹¹¹ and R ¹¹² may be bonded to each other to form a ring.

R ² and R ³ may be bonded to each other to form a ring.

R ¹² and R ¹³ may be bonded to each other to form a ring.

R ⁴² and R ⁴³ may be bonded to each other to form a ring.

R ⁵² and R ⁵³ may be bonded to each other to form a ring.

R ⁶² and R ⁶³ may be bonded to each other to form a ring.

R ⁷² and R ⁷³ may combine with each other to form a ring.

R ⁸² and R ⁸³ may be bonded to each other to form a ring.

R ⁹² and R ⁹³ may be bonded to each other to form a ring.

R ¹⁰² and R ¹⁰³ may be bonded to each other to form a ring.

R ¹¹² and R ¹¹³ may be bonded to each other to form a ring.

R ⁴ and R ⁵ may be bonded to each other to form a ring.

R ¹⁴ and R ¹⁵ may be bonded to each other to form a ring.

R ²⁴ and R ²⁵ may be bonded to each other to form a ring.

R ³⁴ and R ³⁵ may be bonded to each other to form a ring.

R ⁷⁴ and R ⁷⁵ may be bonded to each other to form a ring.

R ⁸⁴ and R ⁸⁵ may be bonded to each other to form a ring.

R ⁶ and R ⁸ each independently represent a divalent linking group.

R ⁷ represents a single bond or a divalent linking group.

R ⁹ and R ¹⁰ each independently represent a trivalent linking group.

R ¹¹ represents a tetravalent linking group.]

Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently It is not particularly limited as long as it is a ring having one or more double bonds as a component. Each of the rings W ² to W ¹² may be a monocyclic ring or a condensed ring. Further, the ring W ~ ² W ¹² ring is good even aliphatic ring may be a ring.

The ring W ² - the ring W ¹² may be a heterocyclic ring containing a hetero atom (eg, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a component of the ring.

Each of the rings W ² to W ¹² has at least one double bond as a component of the ring, but ^{the double bonds contained in the rings W 2} to W ¹² are each independently usually 1 to 4, preferably 1 to 3, respectively. And, it is more preferable that it is 1 or 2, and it is still more preferable that it is one.

Each of the rings W ² to W ¹² is each independently usually a ring having 5 to 18 carbon atoms, preferably a 5 to 7 membered ring structure, and more preferably a 6 membered ring structure.

It is preferable that the ring W ² - the ring W ^{12 are each independently monocyclic.} In addition, ring W ~ ² W ¹² ring is preferably a ring having no aromaticity independently.

Ring W ² - Ring W ¹² may have a substituent. Examples of the substituent include the same substituents as the substituents that the ring W ¹ may have.

As a ^{substituent which the ring W 2} -ring W ¹² may have, it may be substituted by a C1-C12 alkyl group, a C1-C12 alkoxy group, a C1-C12 alkylthio group, or a C1-C6 alkyl group. It is preferable that it is an amino group.

Specific examples of the ring W ² to the ring W ¹² include the same as the specific examples of the ring W ¹ .

Ring W ¹¹¹ is a ring containing two nitrogen atoms as a component of the ring. The ring W ¹¹¹ may be monocyclic or may be condensed, but is preferably monocyclic.

Ring W ¹¹¹ is usually a 5- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring.

Ring W ¹¹¹ may have a substituent. Examples of the substituent that the ring W ¹¹¹ may have include a hydroxyl group; thiol group; aldehyde group; C1-C6 alkyl groups, such as a methyl group and an ethyl group; C1-C6 alkoxy groups, such as a methoxy group and an ethoxy group; C1-C6 alkylthio groups, such as a methylthio group and an ethylthio group; an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms, such as an amino group, a methylamino group, a dimethylamino group, and methylethyl; -CONR ^1f R ^2f (R ^1f and R ^2f each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms); -COSR ^3f (R ^3f represents an alkyl group having 1 to 6 carbon atoms); -CSSR ^4f (R ^4f represents an alkyl group having 1 to 6 carbon atoms); -CSOR ^5f (R ^5f represents an alkyl group having 1 to 6 carbon atoms); -SO ₂ R ^6f (R ^5f represents an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms which may have a fluorine atom.) and the like.

Examples of the ring W ¹¹¹ include the rings described below.

Ring W ¹¹² and ring W ¹¹³ are each independently a ring including one nitrogen atom as a component of the ring. The ring W ¹¹² and the ring W ¹¹³ may each independently be monocyclic or condensed, but preferably monocyclic.

Each of the ring W ¹¹² and the ring W ¹¹³ is each independently usually a 5 to 10 membered ring, preferably a 5 to 7 membered ring, more preferably a 5 or 6 membered ring.

Ring W ¹¹² and ring W ¹¹³ may have a substituent. Examples of the ^{substituent that the ring W 112} and the ring W ¹¹³ may have include the same substituents as the substituent of the ring W ^{1 .}

Examples of the ring W ¹¹² and the ring W ¹¹³ include the rings described below.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ And ^{the electron withdrawing group represented by R 85} includes, for example, a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, an aryl halogenated group, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO _{3 H, -SO 2 H, -SO} 2 CF 3, -SO 2 CHF 2, -SO 2 CH 2 F, there may be mentioned a group represented by the formula (X-1).

[In formula (X-1),

X ¹ represents -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO ₂ -, -NR ²²³ CO- or -CONR ²²⁴ -.

R ²²² represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

R ²²³ and R ²²⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

* indicates the number of bonds.]

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

Examples of the halogenated alkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, and a perfluorotert-butyl group. fluoroalkyl groups, such as group, perfluoropentyl group, and perfluorohexyl group, etc. are mentioned, It is preferable that it is a perfluoroalkyl group. The number of carbon atoms in the halogenated alkyl group is usually 1 to 25, preferably 1 to 12 carbon atoms. The halogenated alkyl group may be linear or branched.

A fluorophenyl group, a chlorophenyl group, a bromophenyl group etc. are mentioned as a halogenated aryl group, It is preferable that it is a fluoroaryl group, and it is more preferable that it is a perfluoroaryl group. The number of carbon atoms in the aryl group containing a halogen atom is usually 6 to 18, preferably 6 to 12 carbon atoms.

X ¹ is preferably -COO- or -SO _{2 -.}

Examples of the alkyl group having 1 to 25 carbon atoms represented by R ²²² include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n-hexyl group and straight-chain or branched-chain alkyl groups having 1 to 25 carbon atoms, such as a real group, 1-methylbutyl group, 3-methylbutyl group, n-octyl group, n-decyl and 2-hexyl-octyl group. R ²²² is preferably alkyl having 1 to 12 carbon atoms.

A good which may have alkyl group of 1 to 25 carbon atoms represented by R ^222, there may be mentioned a halogen atom, a hydroxy group or the like.

Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ²²² include aryl groups having 6 to 18 carbon atoms, such as a phenyl group, a naphthyl group, an anthracenyl group, and a biphenyl group; and an aralkyl group having 7 to 18 carbon atoms, such as a benzyl group, a phenylethyl group, and a naphthylmethyl group.

Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ^{222 may have include a halogen atom and a hydroxyl group.}

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ²²³ and R ²²⁴ include a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n-hexyl group, 1-methylbutyl group, 3-methylbutyl group, etc. are mentioned.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ And ^{the electron withdrawing group represented by R 85} is, each independently, a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group (preferably having 1 to carbon atoms) 25), a fluoroaryl group (preferably having 6 to 18 carbon atoms), -CO-OR ²²² , -SO ₂ -R ²²² or -CO-R ²²² (R ²²² is a hydrogen atom or 1 carbon atom which may have a substituent) It is preferable that it is a C6-C18 aromatic hydrocarbon group which may have a -25 alkyl group or a substituent.),

A nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom or carbon number which may have a substituent) It represents a C6-C18 aromatic hydrocarbon group which may have a 1-25 alkyl group or a substituent.) is more preferable, and it is still more preferable that it is a cyano group.

It is preferable that at least one of R ⁴ and R ^{5 is a cyano group, R 4} is a cyano group, and R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is each independently represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a halogen atom, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a halogen atom).

R ⁴ and R ⁵ may be bonded to each other to form a ring. The ^{ring formed by combining R 4} and R ⁵ with each other may be monocyclic or condensed, but is preferably monocyclic. Further, ^{the ring formed by bonding R 4} and R ⁵ to each other may contain a hetero atom (nitrogen atom, oxygen atom, sulfur atom) or the like as a component of the ring.

The ^{ring formed by combining R 4} and R ⁵ with each other is usually a 3 to 10 membered ring, preferably a 5 to 7 membered ring, and more preferably a 5 or 6 membered ring.

Examples of the ring formed by bonding R ⁴ and R ⁵ to each other include the structures described below.

[In the formula, * represents the number of bonds with a carbon atom. R ^1E to ^{R 16E} each independently represent a hydrogen atom or a substituent.]

The ^{ring formed by combining R 4} and R ⁵ with each other may have a substituent (R ^{1E to R 16E} in the above formula). Examples of the substituent include the same substituents as the substituents that the ring W ¹ may have. R ^1E to ^{R 16E} are each independently preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably a methyl group.

Examples of the ring formed by bonding ^{R 14} and R ¹⁵ to each other are the same as the ring formed by bonding ^{R 4} and R ^{5 to each other.}

Examples of the ring formed when ^{R 24} and R ²⁵ are bonded to each other are the same as the ring formed by bonding ^{R 4} and R ^{5 to each other.}

Examples of the ring formed by bonding ^{R 34} and R ³⁵ to each other are the same as the ring formed by bonding ^{R 4} and R ^{5 to each other.}

Examples of the ring formed by bonding ^{R 74} and R ⁷⁵ to each other are the same as the ring formed by bonding ^{R 4} and R ^{5 to each other.}

Examples of the ring formed by bonding ^{R 84} and R ⁸⁵ to each other are the same as the ring formed by bonding to ^{R 4} and R ^{5 .}

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² The heterocyclic group represented by , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ is the same as the heterocyclic group represented by ^{R 3 .} pyrrolidyl group, piperidyl group, tetrahydrofurfuryl group, tetrahydropyranyl group, tetrahydrothiopheno group, tetrahydrothiopyranyl group or pyridyl group is preferable.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are aliphatic hydrocarbon groups having 1 to 25 carbon atoms, represented by R ³ . The same thing as the C1-C25 aliphatic hydrocarbon group used is mentioned.

It is preferable that it is a C1-C15 alkyl group, and, as for the said C1-C25 aliphatic hydrocarbon group, it is more preferable that it is a C1-C12 alkyl group.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ may include a halogen atom or a hydroxyl group as a substituent which the aliphatic hydrocarbon group may have. , a nitro group, a cyano group, -SO ₃ H, and the like.

Also, R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , _{-CH 2} - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ^{112 is -NR 12A} -, -SO ₂ -, -CO-, -O-, -COO-, -OCO- , -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- may be substituted.

^{R 13, R 23, R 33} , R 43, R 53, R 63, R 73, R 83, R 93, -CH contained groups with a carbon number of 1 to 25 aliphatic hydrocarbon group represented by R ¹⁰³ and R ¹¹³ ₂ - or -CH= is, -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O- CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO -NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS -, -CS-S-, -S-CS-S-, -SO-, or -SO ₂ - may be substituted.

_{When -CH 2} - or -CH= included in the C1-C25 aliphatic hydrocarbon group is substituted, it is preferably substituted with -O-, -S-, -CO-O- or -SO _{2 -.}

_{When -CH 2} - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -O-, the aliphatic hydrocarbon group is -O-R'(R' is a carbon number 1 which may have a halogen atom) It is preferable that it is an alkoxy group represented by the alkyl group of -24). Moreover, polyalkyleneoxy groups, such as a polyethyleneoxy group and a polypropyleneoxy group, may be sufficient. Examples of the alkoxy group represented by -O-R' include a methoxy group, an ethoxy group, and a -OCF ₃ group.

_{When -CH 2} - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -S-, the aliphatic hydrocarbon group is -S-R'(R' is a carbon number 1 which may have a halogen atom) It is preferable that it is an alkylthio group represented by the alkyl group of -24). Moreover, polyalkylenethio groups, such as a polyethylenethio group and a polypropylenethio group, may be sufficient. Examples of the alkylthio group represented by -S-R' include a methylthio group, an ethylthio group, a -SCF ₃ group, a polyethylenethio group, and a polypropylenethio group.

_{When -CH 2} - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -COO-, the aliphatic hydrocarbon group is -COO-R'(R' may have a halogen atom; -24 alkyl group) is preferable.

_{When -CH 2} - or -CH= contained in the C1-C25 aliphatic hydrocarbon group _{is substituted with -SO 2} -, the aliphatic hydrocarbon group is -SO ₂ -R'(R' may have a halogen atom A group represented by a C1-C24 alkyl group) is preferable, and a -SO ₂ CHF ₂ group, a -SO ₂ CH ₂ F group or the like may be used.

An alkyl group having 1 to 6 carbon atoms represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A Examples of the group include the same as the alkyl group having 1 to 6 carbon atoms represented by ^{R 1A.}

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ as an aromatic hydrocarbon group having 6 to 18 carbon atoms, represented by R ³ The same thing as the aromatic hydrocarbon group represented by the C6-C18 used is mentioned, It is preferable that it is a C6-C18 aryl group, and it is more preferable that it is a phenyl group or a benzyl group.

Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms may have include a halogen atom; hydroxyl group; thiol group; amino group; nitro group; cyano group; -SO ₃ H group, and the like.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² _{-CH 2} - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by ^{is, -NR 12A} -, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, - CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- may be substituted.

^{R 13, R 23, R 33} , R 43, R 53, R 63, R 73, R 83, R 93, -CH contained groups aromatic hydrocarbon group of a carbon number of 6-18 represented by R ¹⁰³ and R ¹¹³ ₂ - or -CH= is, -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O- CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO -NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS -, -CS-S-, -S-CS-S-, -SO-, or -SO ₂ - may be substituted.

_{When -CH 2} - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted, it is preferably substituted with _{-O- or -SO 2 -.}

_{When -CH 2} - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -O-, the aromatic hydrocarbon group may include an aryloxy group having 6 to 17 carbon atoms such as a phenoxy group; It is preferable that they are an aryl alkoxy group of a phenoxyethyl group, a phenoxydiethylene glycol group, a phenoxy polyalkylene glycol group, etc.

_{When -CH 2} - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms _{is substituted with -SO 2} -, the aromatic hydrocarbon group is -SO ₂ -R"(R" is an aryl having 6 to 17 carbon atoms. group or an aralkyl group having 7 to 17 carbon atoms).

An alkyl group having 1 to 6 carbon atoms represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A As examples, the above-mentioned ones are mentioned.

R ² and R ³ may be linked to each other to form a ring. A component of a ring formed by connecting ^{R 2} and R ³ , and includes a double bond constituting the ^{ring W 1 .} That is, the ring formed by connecting ^{R 2} and R ^{3 and the ring W 1} form a condensed ring. Specific examples of the ring formed by connecting R ² and R ^{3 and the condensed ring formed by the ring W 1} include the ring structures described below.

The ^{ring formed by combining R 12} and R ¹³ with each other is a component of the ring formed by connecting ^{R 12} and R ¹³ , and includes a double bond constituting the ^{ring W 2 .} That is, ^{a ring formed by combining R 12} and R ¹³ with each other and a ring W ² form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

The ^{ring formed by combining R 42} and R ⁴³ with each other is a component of the ring formed by connecting ^{R 42} and R ⁴³ , and includes a double bond constituting the ^{ring W 5 .} That is, ^{the ring formed by combining R 42} and R ⁴³ with each other and the ring W ⁵ form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

And R ⁵² and R ⁵³ ring is formed are bonded to each other, comprising a double bond constituting the ring ⁶ W as a component of a ring formed by R ⁵² and R ⁵³ are connected. That is, ^{a ring formed by combining R 52} and R ⁵³ with each other and a ring W ⁶ form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

R ⁶² and R ⁶³ as a component of a ring formed by the ring formed by combining each other, R ⁶² and R ⁶³ are connected, and includes a double bond constituting the ring W ^7. That is, ^{a ring formed by combining R 62} and R ⁶³ with each other and a ring W ⁷ form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

R ⁷² and R ⁷³ combine with each other to form a ring that is, including a double bond constituting the ring W ⁸ as a component of a ring formed by R ⁷² and R ⁷³ are connected. That is, ^{a ring formed by combining R 72} and R ⁷³ with each other and a ring W ⁸ form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

R ⁸² and R ⁸³ combine with each other to form a ring that is, including a double bond constituting the ring W ⁹ as a component of a ring formed by R ⁸² and R ⁸³ are connected. That is, ^{a ring formed by combining R 82} and R ⁸³ with each other and a ring W ⁹ form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

R ⁹² and R ⁹³ as a component of a ring formed by the ring formed by combining each other, R ⁹² and R ⁹³ are connected, and includes a double bond constituting the ring W ^12. That is, ^{a ring formed by combining R 92} and R ⁹³ with each other and a ring W ¹² form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

R ¹⁰² and R ¹⁰³ as components of the ring formed by the ring formed by combining each other, R ¹⁰² and R ¹⁰³ is connected, includes a double bond constituting the ring W ^10. That is, ^{a ring formed by combining R 102} and R ¹⁰³ with each other and a ring W ¹⁰ form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

The ^{ring formed by combining R 112} and R ¹¹³ with each other is a component of the ring formed by connecting ^{R 112} and R ¹¹³ , and includes a double bond constituting the ^{ring W 11 .} That is, ^{a ring formed by combining R 112} and R ¹¹³ with each other and a ring W ¹¹ form a condensed ring. Specific examples include the same as the ring formed by connecting ^{R 2} and R ³ and the condensed ring formed by the ^{ring W 1 .}

R ¹ and R ² may be bonded to each other to form a ring. The ^{ring formed by combining R 1} and R ² with each other includes one nitrogen atom as a component of the ring. The ^{ring formed by combining R 1} and R ² with each other may be monocyclic or condensed, but is preferably monocyclic. The ^{ring formed by combining R 1} and R ² with each other may further contain a hetero atom (such as an oxygen atom, a sulfur atom, or a nitrogen atom) as a component of the ring. The ^{ring formed by combining R 1} and R ² with each other is preferably an aliphatic ring, and more preferably an aliphatic ring having no unsaturated bond.

The ^{ring formed by combining R 1} and R ² with each other is usually a 3 to 10 membered ring, preferably a 5 to 7 membered ring, and more preferably a 5 or 6 membered ring.

The ^{ring formed by combining R 1} and R ² with each other may have a substituent, for example, the same substituents as the substituents that the ^{ring W 2} to the ring W ^{12 may have are exemplified.}

Examples of the ring formed by bonding R ¹ and R ² to each other include the rings described below.

Examples of the ring formed by bonding ^{R 41} and R ⁴² to each other are the same as the ring formed by bonding ^{R 1} and R ^{2 to each other.}

Examples of the ring formed by bonding ^{R 51} and R ⁵² to each other are the same as the ring formed by bonding ^{R 1} and R ^{2 to each other.}

Examples of the ring formed by bonding ^{R 61} and R ⁶² to each other are the same as the ring formed by bonding ^{R 1} and R ^{2 to each other.}

^{Examples of} the ring formed by bonding R 91 and R ⁹² to each other are the same as the ring formed by bonding of ^{R 1} and R ^{2 to each other.}

Examples of the ring formed by bonding ^{R 101} and R ¹⁰² to each other are the same as the ring formed by bonding ^{R 1} and R ^{2 to each other.}

Examples of the ring formed by bonding ^{R 111} and R ¹¹² to each other are the same as the ring formed by bonding of ^{R 1} and R ^{2 to each other.}

The ^{divalent linking group represented by R 6} , R ⁷ and R ⁸ represents a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. _{-CH 2} - contained in the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group is -O-, -S-, -NR ^1B - (R ^1B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms); -CO-, -SO ₂ -, -SO-, -PO ₃ - may be substituted.

Moreover, as a substituent which the said divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxy group, an amino group, etc. are mentioned.

The ^{divalent linking group represented by R 6} , R ⁷ and R ⁸ is each independently preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and is preferably a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. It is more preferable that it is an aliphatic hydrocarbon group.

Specific examples of the divalent linking group represented by R ⁶ , R ⁷ and R ^{8 include the linking groups described below.} In the formula, * represents the number of bonds.

R ⁶ and R ⁷ are each independently preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a linking group represented by the following formula, and a divalent aliphatic group having 1 to 12 carbon atoms which may have a substituent. It is more preferable that it is a hydrocarbon group or a coupling group represented by the following formula.

It is preferable that R<^8> is a C1-C18 divalent aliphatic hydrocarbon group which may have a substituent, or a coupling group represented by the following formula.

Examples of the trivalent linking group represented by R ⁹ and R ¹⁰ include a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may each independently have a substituent or a trivalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. have. _{-CH 2} - included in the trivalent aliphatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO-, -NR ^11B - (R ^11B is a hydrogen atom or having 1 to 6 carbon atoms It may be substituted with an alkyl group.).

As a substituent which the said trivalent aliphatic hydrocarbon group and the said trivalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxy group, an amino group, etc. are mentioned.

R ⁹ and trivalent connecting group represented by R ¹⁰ are preferably each independently may have a substituent trivalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.

Specific examples of the trivalent linking group represented by R ⁹ and R ^{10 include the linking groups described below.}

Examples of the tetravalent linking group represented by R ¹¹ include a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. _{-CH 2} - contained in the tetravalent aliphatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO-, -NR ^11C - (R ^11C is a hydrogen atom or a C 1 to C 6 It may be substituted with an alkyl group.).

A halogen atom, a hydroxyl group, a carboxy group, an amino group, etc. are mentioned as a substituent which the said tetravalent aliphatic hydrocarbon group and the said tetravalent aromatic hydrocarbon group may have.

The ^{tetravalent linking group represented by R 11} is preferably a tetravalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may each independently have a substituent.

Specific examples of the tetravalent linking group represented by R ^{11 include the linking groups described below.}

R ¹ is preferably an alkyl group of 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

It is preferable that it is a C1-C15 alkyl group, and, as for R<^{2>, it is more preferable that it is a C1-C10 alkyl group.}

R ¹ and R ² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, a pyrrolidine ring or a piperidine ring structure It is particularly preferable to have

R ³ is a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group (preferably having 1 to 25 carbon atoms), a fluoroaryl group (preferably It is preferable that it is a C6-C18), -CO-OR ^111A, or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent a C1-C24 alkyl group.),

Cyano group, fluorine atom, chlorine atom, -OCF ₃ , -SCF ₃ , fluoroalkyl group, -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently may have a halogen atom An alkyl group having 1 to 24 carbon atoms is shown.), more preferably a cyano group or a fluorine atom, and particularly preferably a cyano group.

R ⁴ and R ⁵ are each independently a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group, a fluoroaryl group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.)

A nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom or carbon number which may have a substituent) It is more preferable that it is a C6-C18 aromatic hydrocarbon group which may have a 1-25 alkyl group or a substituent.),

A cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms. ) is more preferable, and it is particularly preferable that it is a cyano group.

It is preferable that at least one of R ⁴ and R ^{5 is a cyano group, R 4} is a cyano group, and R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom , an alkyl group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent) is more preferable.

R ⁴ and R ⁵ preferably has the same structure.

R ⁴ and R ⁵ is preferably a both a cyano group.

R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ and R ¹¹¹ are each independently preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ¹¹² are each independently preferably an alkyl group having 1 to 15 carbon atoms, and an alkyl group having 1 to 10 carbon atoms. more preferably.

R ⁴¹ and R ⁴² are preferably linked to each other to form a ring, more preferably form an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or It is preferred to have a piperidine ring structure.

R ⁵¹ and R ⁵² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or It is preferred to have a piperidine ring structure.

R ⁶¹ and R ⁶² are preferably linked to each other to form a ring, more preferably form an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or It is preferred to have a piperidine ring structure.

R ⁹¹ and R ⁹² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or It is preferred to have a piperidine ring structure.

R ¹⁰¹ and R ¹⁰² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or It is preferred to have a piperidine ring structure.

R ¹¹¹ and R ¹¹² are preferably linked to each other to form a ring, more preferably form an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or It is preferred to have a piperidine ring structure.

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a nitro group; cyano group; halogen atom; -OCF ₃ ; -SCF ₃ ; -SF ₅ ; -SF ₃ ; a fluoroalkyl group having 1 to 25 carbon atoms; a fluoroaryl group having 6 to 18 carbon atoms; -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.)

cyano group; fluorine atom; chlorine atom; -OCF ₃ ; -SCF ₃ ; a fluoroalkyl group having 1 to 12 carbon atoms; It is more preferable that -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.)

It is especially preferable that it is a cyano group.

R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ are each Independently a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -CO-OR ²²² , -SO ₂ -R ²²² (R ²²² may have a halogen atom represents an alkyl group having 1 to 25 carbon atoms), a fluoroalkyl group having 1 to 25 carbon atoms, or a fluoroaryl group having 6 to 18 carbon atoms.

A nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² represents 1 to C1-C which may have a halogen atom) It is more preferable that it represents the alkyl group of 25.),

It is more preferably a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² represents an alkyl group having 1 to 25 carbon atoms which may have a halogen atom.)

It is especially preferable that it is a cyano group.

It is preferable that R ¹⁴ and R ¹⁵ have the same structure.

It is preferable that R ²⁴ and R ²⁵ have the same structure.

It is preferable that R ³⁴ and R ³⁵ have the same structure.

It is preferable that R ⁷⁴ and R ⁷⁵ have the same structure.

It is preferable that R ⁸⁴ and R ⁸⁵ have the same structure.

The compound represented by the formula (I) is more preferably any of the compound represented by the formula (I-1A), the compound represented by the formula (I-2A), or the compound represented by the formula (I-3A). .

[wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above.

Rx ₁ , Rx ₂ , Rx ₃ , Rx ₄ , Rx ₅ , Rx ₆ , Rx ₇ and Rx ₈ each independently represent a hydrogen atom or a substituent.

m1 represents an integer from 0 to 4, m2 represents an integer from 0 to 5.]

Examples of the substituent represented by Rx _{1 to Rx 8} include the same substituents as the substituents that the ring W ¹ may have.

It is preferable that m1 and m2 are respectively independently 0 or 1.

It is preferable that the compound represented by Formula (II) is a compound represented by Formula (II-A).

[wherein, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ have the same meanings as above.

R _x9 , R _x10 , R _x11 and R _x12 each independently represent a hydrogen atom or a substituent.]

_Examples of the substituent represented by R _x9 to R x12 include the same substituents as the substituents that the ring W ¹ may have.

It is preferable that the compound represented by Formula (III) is a compound represented by Formula (III-A).

[Wherein, R ³ , R ⁴ , R ⁵ , R ²³ , R ²⁴ and R ²⁵ have the same meanings as above.

R _x13 , R _x14 , R _x15 and R _x16 each independently represent a hydrogen atom or a substituent.]

_Examples of the substituent represented by R _x13 to R x16 include the same substituents as the substituents that the ring W ¹ may have.

Examples of the compound represented by the formula (I) (hereinafter sometimes referred to as compound (I)) include the compounds described below.

Compound (I) is a formula (1-1) to formula (1-4), formula (1-7), formula (1-8), formula (1-10), formula (1-12), formula ( 1-20) to formula (1-25), formula (1-54) to formula (1-57), formula (1-59), formula (1-63) to formula (1-68), formula (1) -70) to formula (1-78), formula (1-80), formula (1-124) to formula (1-132), formula (1-135), formula (1-137) to formula (1- 142), a compound represented by a formula (1-158) to a formula (1-172), a formula (1-218) to a formula (1-229),

Formula (1-1), Formula (1-2), Formula (1-4), Formula (1-7), Formula (1-10), Formula (1-12), Formula (1-20), Formula (1-22), Formula (1-54) to Formula (1-56), Formula (1-59), Formula (1-63) to Formula (1-65), Formula (1-66), Formula ( 1-71), Formula (1-124), Formula (1-125), Formula (1-126), Formula (1-128), Formula (1-131), Formula (1-158), Formula (1) -160), a compound represented by a formula (1-164), a formula (1-169), a formula (1-218) - a formula (1-227) is more preferable,

Formulas (1-54) to (1-56), (1-59), (1-64), (1-125), (1-218) to (1-229) It is more preferable that it is a compound which becomes

Examples of the compound represented by the formula (II) (hereinafter sometimes referred to as compound (II)) include the compounds described below.

As compound (II), formula (2-1), formula (2-2), formula (2-5) - formula (2-12), formula (2-24) - formula (2-28), formula ( 2-32), formula (2-33), formula (2-38) - formula (2-44), formula (2-70), formula (2-71), formula (2-103) - formula (2) -106), it is preferable that it is a compound represented by Formula (2-1), Formula (2-2), Formula (2-5) - Formula (2-10), Formula (2-103) - Formula (2) -106) is more preferable.

Examples of the compound represented by the formula (III) (hereinafter sometimes referred to as compound (III)) include the compounds described below.

Examples of the compound represented by the formula (IV) (hereinafter sometimes referred to as compound (IV)) include the compounds described below.

Examples of the compound represented by the formula (V) (hereinafter, may be referred to as compound (V)) include compounds described below.

As compound (V), Formula (5-1) - Formula (5-3), Formula (5-6), Formula (5-7), Formula (5-9), Formula (5-15), Formula ( 5-21), a compound represented by a formula (5-23), a formula (5-25), a formula (5-26), a formula (5-32), a formula (5-36), a formula (5-38) It is preferable that it is, and it is more preferable that it is a compound represented by Formula (5-1) - Formula (5-3), Formula (5-21), Formula (5-25), Formula (5-36).

Examples of the compound represented by the formula (VI) (hereinafter sometimes referred to as compound (VI)) include the compounds described below.

As compound (VI), Formula (6-1), Formula (6-2), Formula (6-4), Formula (6-5), Formula (6-7), Formula (6-8), Formula (6-9), Formula (6-12), Formula (6-15), Formula (6-18), Formula (6-19), Formula (6-22), Formula (6-23), Formula ( 6-50), Formula (6-57), Formula (6-69), Formula (6-80), Formula (6-85), Formula (6-94) is preferably a compound represented by the formula ( 6-1), formula (6-2), formula (6-4), formula (6-8), formula (6-15), formula (6-22), a compound represented by formula (6-80) It is more preferable that

Examples of the compound represented by the formula (VII) (hereinafter sometimes referred to as compound (VII)) include the compounds described below.

As compound (VII), formula (7-1) - formula (7-9), formula (7-12), formula (7-14), formula (7-17), formula (7-42) - formula ( It is preferable that it is a compound represented by 7-44) and Formula (7-57), and it is more preferable that it is a compound represented by Formula (7-1) - Formula (7-8).

Examples of the compound represented by the formula (VIII) (hereinafter sometimes referred to as compound (VIII)) include the compounds described below.

As compound (VIII), Formula (8-1), Formula (8-2), Formula (8-4), Formula (8-5), Formula (8-11), Formula (8-13) - Formula ( 8-17), Formula (8-25), Formula (8-26), Formula (8-47), Formula (8-48) is preferably a compound represented by, Formula (8-1), Formula ( It is more preferable that it is a compound represented by 8-4), a formula (8-5), a formula (8-15), a formula (8-17), and a formula (8-25).

<Method for producing compound (I)>

Compound (I) is, for example, a compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) and a compound represented by formula (I-2) (hereinafter, compound ( It can be obtained by reacting I-2)).

[In the formula, the rings W ¹ and R ¹ to ^{R 5} have the same meanings as above.]

The reaction between compound (I-1) and compound (I-2) is usually carried out by mixing compound (I-1) and compound (I-2), and compound (I-1) is mixed with compound (I-1). -2) is preferably added.

In the reaction of compound (I-1) and compound (I-2), it is preferable to mix compound (I-1) and compound (I-2) in the presence of a base and a methylating agent,

It is preferable to mix compound (1-1), compound (I-2), a base and a methylating agent,

It is more preferable to mix compound (I-2) and a base with a mixture of compound (1-1) and a methylating agent,

It is more preferable to add a mixture of compound (I-2) and a base to the mixture of compound (1-1) and a methylating agent.

Examples of the base include metal hydroxides (preferably alkali metal hydroxides) such as sodium hydroxide, lithium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide, calcium hydroxide, barium hydroxide, and magnesium hydroxide; metal alkoxides (preferably alkali metal alkoxides) such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, sodium isopropoxide, sodium tert-butoxide and potassium tert-butoxide; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, lithium aluminum hydride, sodium borohydride, aluminum hydride, and sodium aluminum hydride; metal oxides such as calcium oxide and magnesium oxide; metal carbonates such as sodium hydrogencarbonate, sodium carbonate and potassium carbonate (preferably alkaline earth metal carbonates); organoalkyl metal compounds such as normal butyl lithium, tert-butyl lithium, methyl lithium, and Grignard reagent; Ammonia, triethylamine, diisopropylethylamine, ethanolamine, pyrrolidine, piperidine, diazabicycloundecene, diazabicyclononene, guanidine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyridine, aniline, amine compounds such as dimethoxyaniline, ammonium acetate and β-alanine (preferably tertiary amines such as triethylamine and diisopropylethylamine); metal amide compounds (preferably alkali metal amides) such as lithium diisopropylamide, sodium amide and potassium hexamethyldisilazide; sulfonium compounds such as trimethylsulfonium hydroxide; iodonium compounds such as diphenyliodonium hydroxide; and a phosphazene base.

The amount of the base used is usually 0.1 to 5 moles, preferably 0.5 to 2 moles, per 1 mole of compound (I-1).

Examples of the methylating agent include iodomethane, dimethyl sulfate, methyl methanesulfonate, methyl fluorosulfonate, methyl paratoluenesulfonate, methyl trifluoromethanesulfonate, and trimethyloxonium tetrafluoroborate.

The amount of the methylating agent to be used is usually 0.1 to 5 moles, preferably 0.5 to 2 moles, per 1 mole of compound (I-1).

The reaction between compound (I-1) and compound (I-2) may be carried out in the presence of a solvent. Examples of the solvent include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide. seed, N,N-dimethylacetamide, N,N-dimethylformamide, and water. Preferably they are acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether, More preferably, they are acetonitrile, tetrahydrofuran, chloroform, More preferably, they are acetonitrile.

Moreover, it is preferable that a solvent is a dehydration solvent.

The reaction time between compound (I-1) and compound (I-2) is usually 0.1 to 10 hours, preferably 0.2 to 3 hours.

The reaction temperature of compound (I-1) and compound (I-2) is usually -50 to 150°C, preferably -20 to 100°C.

The usage-amount of compound (I-2) is 0.1-10 mol normally with respect to 1 mol of compound (I-1), and it is preferable that it is 0.5-5 mol.

As compound (I-1), the compound etc. described below are mentioned, for example.

As the compound (I-2), a commercially available product may be used, and examples thereof include compounds described below.

Compound (I-1) is, for example, a compound represented by formula (I-3) (hereinafter sometimes referred to as compound (I-3)) and a compound represented by formula (I-4) (hereinafter, referred to as compound (I-3)). It can be obtained by reacting compound (I-4).

[In formula (I-3), rings W ¹ , R ¹ , R ² and R ³ have the same meanings as described above. E ₁ represents a leaving group.]

Examples of the leaving group represented by E ₁ include a halogen atom, a p-toluenesulfonyl group, and a trifluoromethylsulfonyl group.

The reaction between compound (I-3) and compound (I-4) is carried out by mixing compound (I-3) and compound (I-4).

The usage-amount of compound (I-4) is 0.1-5 mol normally with respect to 1 mol of compound (I-3), and it is preferable that it is 0.5-2 mol.

The reaction between compound (I-3) and compound (I-4) may be carried out in the presence of a solvent. Examples of the solvent include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide. seed, N,N-dimethylacetamide, N,N-dimethylformamide, and water. Preferably, they are acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether, More preferably, they are acetonitrile, tetrahydrofuran, and chloroform, More preferably, they are methanol, ethanol, isopropanol, and acetonitrile.

The reaction time between compound (I-3) and compound (I-4) is usually 0.1 to 10 hours.

The reaction temperature between compound (I-3) and compound (I-4) is usually -50 to 150°C.

As compound (I-3), the compound described below is mentioned, for example.

As the compound (I-4), a commercially available product may be used. For example, chlorocyanide, bromocyanide, paratoluenesulfonylcyanide, trifluoromethanesulfonylcyanide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis (Tetrafluoroborate (also called Selectfluoro (registered trademark of Air Products and Chemicals)), benzoyl (phenyliodonio) (trifluoromethanesulfonyl) methanide, 2,8-difluoro-5 -(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate, N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinic imide and the like.

Compound (I-3) is a compound represented by formula (I-5) (hereinafter, sometimes referred to as compound (I-5)) and a compound represented by formula (I-6) (hereinafter, compound ( It can be obtained by reacting I-6)).

[Wherein, rings W ¹ , R ¹ and R ² have the same meanings as above.]

The reaction between compound (I-5) and compound (I-6) is carried out by mixing compound (I-5) and compound (I-6).

The usage-amount of compound (I-6) is 0.1-5 mol normally with respect to 1 mol of compound (I-5), and it is preferable that it is 0.5-2 mol.

The reaction between compound (I-5) and compound (I-6) may be carried out in the presence of a solvent. Acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, N-dimethylacetamide, N,N-dimethylformamide, water, etc. are mentioned. Preferably, they are benzene, toluene, ethanol, and acetonitrile.

The reaction time between compound (I-5) and compound (I-6) is usually 0.1 to 10 hours.

The reaction temperature between compound (I-5) and compound (I-6) is usually -50 to 150°C.

As compound (I-5), the compound etc. described below are mentioned, for example.

As compound (I-6), ammonia; primary amines such as methylamine, ethylamine, ethanolamine, and 4-hydroxybutylamine; and secondary amines such as dimethylamine, diethylamine, dibutylamine, pyrrolidine, piperidine, 3-hydroxypyrrolidine, 4-hydroxypiperidine and azetidine.

In addition, compound (I-1) is prepared by reacting compound (I-6) with a compound represented by formula (I-5-1) (hereinafter sometimes referred to as compound (I-5-1)). you may get

[In formula (I-5-1), rings W ¹ and R ³ have the same meanings as above.]

The reaction between compound (I-5-1) and compound (I-6) is carried out by mixing compound (I-5-1) and compound (I-6).

The usage-amount of compound (I-6) is 0.1-5 mol normally with respect to 1 mol of compound (I-5-1), and it is preferable that it is 0.5-2 mol.

The reaction between compound (I-5-1) and compound (I-6) may be carried out in the presence of a solvent. Acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, N-dimethylacetamide, N,N-dimethylformamide, water, etc. are mentioned. Preferably, they are benzene, toluene, ethanol, and acetonitrile.

The reaction time between compound (I-5-1) and compound (I-6) is usually 0.1 to 10 hours.

The reaction temperature between compound (I-5-1) and compound (I-6) is usually -50 to 150°C.

Examples of the compound represented by the formula (I-5-1) include the compounds described below.

Compound (I) can also be obtained by reacting compound (I-6) with a compound represented by formula (I-7) (hereinafter sometimes referred to as compound (I-7)).

[In formula (I-7), rings W ¹ , R ³ , R ⁴ and R ⁵ have the same meanings as above.]

The reaction of the compound (I-7) and the compound (I-6) is usually carried out by mixing the compound (I-7) and the compound (I-6), and the compound (I-7) is mixed with the compound (I-7). -6) is preferably added.

In addition, the reaction of compound (I-7) and compound (I-6) is preferably carried out by mixing compound (I-7) and compound (I-6) in the presence of a base and a methylating agent,

It is more preferable to mix compound (I-7), compound (I-6), a base and a methylating agent,

It is more preferable to mix compound (I-6) with a mixture of compound (I-7), a methylating agent, and a base.

Examples of the base include the same as the base used in the reaction between compound (I-1) and compound (I-2).

The amount of the base used is usually 0.1 to 5 moles, preferably 0.5 to 2 moles, per 1 mole of compound (I-7).

Examples of the methylating agent include the same as the methylating agent used in the reaction between compound (I-1) and compound (I-2).

As a usage-amount of a methylating agent, it is 0.1-5 mol normally with respect to 1 mol of compound (I-7), and it is preferable that it is 0.5-2 mol.

The usage-amount of compound (I-6) is 0.1-10 mol normally with respect to 1 mol of compound (I-7), and it is preferable that it is 0.5-5 mol.

The reaction between compound (I-7) and compound (I-6) may be carried out in the presence of a solvent. Examples of the solvent include the same solvent as the solvent used for the reaction between compound (I-1) and compound (I-2). Preferably, they are methanol, ethanol, isopropanol, toluene, and acetonitrile.

The reaction time between compound (I-7) and compound (I-6) is usually 0.1 to 10 hours.

The reaction temperature between compound (I-7) and compound (I-6) is usually -50 to 150°C.

As compound (I-7), the compound described below is mentioned, for example.

The compound (I-7) can also be obtained by reacting the compound represented by the formula (I-8) with the compound (I-4).

[In formula (I-8), rings W ¹ , R ⁴ and R ⁵ have the same meanings as above.]

The reaction between compound (I-8) and compound (I-4) can be carried out by mixing compound (I-8) and compound (I-4).

The reaction between compound (I-8) and compound (I-4) is preferably carried out in the presence of a base. Examples of the base include the same as the base used in the reaction between compound (I-1) and compound (I-2). Preferred are metal hydroxides (more preferably alkali metal hydroxides), metal alkoxides (more preferably alkali metal alkoxides), amine compounds, and metal amide compounds (more preferably alkali metal amides).

The amount of the base used is usually 0.1 to 10 moles, preferably 0.5 to 2 moles, per 1 mole of compound (I-8).

The reaction between compound (I-8) and compound (I-4) may be carried out in the presence of a solvent. As a solvent, the thing similar to the solvent used for the reaction of compound (I-1) and compound (I-2) is mentioned. Preferably, they are toluene, acetonitrile, methanol, ethanol, and isopropanol.

The reaction time between compound (I-8) and compound (I-4) is usually 0.1 to 10 hours.

The reaction temperature between compound (I-8) and compound (I-4) is usually -50 to 150°C.

The compound (I-8) includes, for example, the compounds described below.

Compound (I-8) can also be obtained by reacting compound (I-5) with compound (I-2). The reaction between compound (I-5) and compound (I-2) can be carried out by mixing compound (I-5) and compound (I-2).

The reaction between compound (I-5) and compound (I-2) is preferably performed in the presence of a base. Examples of the base include the same as the base used in the reaction between compound (I-1) and compound (I-2). The amount of the base used is usually 0.1 to 5 moles, preferably 0.5 to 2 moles, per 1 mole of compound (I-5).

The reaction between compound (I-5) and compound (I-2) may be carried out in the presence of a solvent. As a solvent, the thing similar to the solvent used for the reaction of compound (I-1) and compound (I-2) is mentioned. Preferably, they are methanol, ethanol, isopropanol, toluene, and acetonitrile.

The reaction time between compound (I-5) and compound (I-2) is usually 0.1 to 10 hours.

The reaction temperature between compound (I-5) and compound (I-2) is usually -50 to 150°C.

The usage-amount of compound (I-2) is 0.1-10 mol normally with respect to 1 mol of compound (I-5), and it is preferable that it is 0.5-2 mol.

Compound (I-7) can also be obtained by reacting compound (I-5-1) with compound (I-2).

The reaction between compound (I-5-1) and compound (I-2) is carried out by mixing compound (I-5-1) and compound (I-2).

The usage-amount of compound (I-2) is 0.1-5 mol normally with respect to 1 mol of compound (I-5-1), and it is preferable that it is 0.5-2 mol.

The reaction between compound (I-5-1) and compound (I-2) may be carried out in the presence of a solvent. Acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, N-dimethylacetamide, N,N-dimethylformamide, water, etc. are mentioned. Preferably, they are benzene, toluene, ethanol, and acetonitrile.

The reaction time between compound (I-5-1) and compound (I-2) is usually 0.1 to 10 hours.

The reaction temperature of compound (I-5-1) and compound (I-2) is usually -50 to 150°C.

<Method for producing compound (II) to compound (VIII)>

Compound (II) can be obtained, for example, by reacting 2 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (II-1).

[Wherein, R ² , R ¹² and R ⁶ have the same meanings as above.]

As a compound represented by Formula (II-1), the compound etc. which were described below are mentioned, for example.

Compound (III) can be obtained, for example, by reacting 2 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (III-1).

[Wherein, ring W ¹¹¹ has the same meaning as above.]

As a compound represented by Formula (III-1), the compound etc. which were described below are mentioned, for example.

Compound (IV) can be obtained, for example, by reacting 2 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (IV-1).

[Wherein, ring W ¹¹² , ring W ¹¹³ , and R ⁷ have the same meaning as above.]

As a compound represented by Formula (IV-1), the compound etc. which were described below are mentioned, for example.

Compound (V) can be obtained, for example, by reacting 2 molar equivalents of compound (I-1) with 1 molar equivalent of the compound represented by formula (V-1).

[Wherein, R ⁴ , R ⁸ and R ⁴⁴ have the same meaning as above.]

As a compound represented by Formula (V-1), the compound etc. which were described below are mentioned, for example.

Compound (VI) can be obtained, for example, by reacting 3 molar equivalents of compound (I-1) with 1 molar equivalent of the compound represented by formula (VI-1).

[Wherein, R ⁴ , R ⁸ , R ⁵⁴ and R ⁶⁴ have the same meaning as above.]

As a compound represented by Formula (VI-1), the compound etc. which were described below are mentioned, for example.

Compound (VII) can be obtained, for example, by reacting 3 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (VII-1).

[Wherein, R ² , R ¹⁰ , R ⁷² and R ⁸² have the same meaning as above.]

As a compound represented by Formula (VII-1), the compound etc. described below are mentioned, for example.

Compound (VIII) can be obtained, for example, by reacting 4 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (VIII-1).

[Wherein, R ⁴ , R ¹¹ , R ⁹⁴ , R ¹⁰⁴ and R ¹¹⁴ have the same meaning as above.]

As a compound represented by Formula (VIII-1), the compound etc. described below are mentioned, for example.

<Polarizer>

The polarizer is a film having a function of extracting linearly polarized light from incident natural light. The polarizer may be, for example, a stretched film to which a dichroic dye is adsorbed, or may be a cured product of a composition containing a horizontally aligned polymerizable liquid crystal compound and a horizontally aligned dichroic dye.

As a stretched film to which the dichroic dye was made to adsorb|suck, the polarizing film by which the adsorption orientation of dichroic dyes, such as an iodine and a dichroic organic dye, was carried out to the polyvinyl alcohol-type resin film is mentioned. Polyvinyl alcohol-type resin can be obtained by saponifying polyvinyl acetate-type resin. Examples of the polyvinyl acetate-based resin include polyvinyl acetate, which is a homopolymer of vinyl acetate, and a copolymer of a monomer copolymerizable with vinyl acetate and vinyl acetate. Examples of the monomer copolymerizable with vinyl acetate include unsaturated carboxylic acid, olefin, vinyl ether, unsaturated sulfonic acid, and acrylamide having an ammonium group.

The saponification degree of polyvinyl alcohol-type resin is 85 mol% - 100 mol% normally, Preferably it is 98 mol% or more. The polyvinyl alcohol-based resin may be modified, for example, polyvinyl formal or polyvinyl acetal modified with aldehyde may be used. The polymerization degree of the polyvinyl alcohol-based resin is usually 1,000 to 10,000, preferably 1,500 to 5,000.

What formed the polyvinyl alcohol-type resin into a film is normally used as a raw film of a polarizer. The polyvinyl alcohol-based resin can be formed by a known method. The film thickness of the said raw film is 1-150 micrometers normally, and when the easiness of extending|stretching etc. are considered, the film thickness becomes like this. Preferably it is 10 micrometers or more.

A polarizer, which is a stretched film to which a dichroic dye is adsorbed, is, for example, a step of uniaxially stretching a raw film, a step of dyeing the film with a dichroic dye to adsorb the dichroic dye, a step of treating the film with an aqueous boric acid solution, And, the process of washing the film with water is performed, and finally dried and manufactured. The film thickness of a polarizer is 1-30 micrometers normally. Moreover, the polarizer which is a stretched film to which the dichroic dye was made to adsorb|suck can be manufactured also with the manufacturing method of Unexamined-Japanese-Patent No. 10-186133, Unexamined-Japanese-Patent No. 2006-509250, etc.

When the optical layer of the present invention is a stretched film to which a dichroic dye is adsorbed, for example, the raw film is dyed with a solution containing the dichroic dye and the compound (X), and the dichroic dye and the compound (X) are applied to the raw film. It can obtain by making it adsorb|suck.

Although content in particular of compound (X) is not restrict|limited, From a viewpoint of the influence of the hue with respect to a polarizer, it is 0.01-50 mass parts normally with respect to 100 mass parts of raw resin films, Preferably it is 0.1-10 mass parts, more Preferably it is 0.2-7 mass parts, More preferably, it is 0.5-5 mass parts.

When the optical layer of the present invention is a polarizer that is a cured product of a composition comprising a horizontally aligned polymerizable liquid crystal compound and a horizontally aligned dichroic dye, a composition comprising a polymerizable liquid crystal compound, a dichroic dye, and compound (X) ( Hereinafter, it may be referred to as a composition (A).).

As a polymerizable liquid crystal compound, it is preferable that it is a thermotropic liquid crystal compound, and it is preferable that it is a thermotropic liquid crystal compound which shows a smectic liquid crystal phase. The polymerizable liquid crystal compound is a liquid crystal compound having at least one polymerizable group. The polymerizable group means a group capable of participating in a polymerization reaction by an active radical or acid generated from a polymerization initiator, for example, a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, An acryloyloxy group, a methacryloyloxy group, an oxiranyl group, oxetanyl group, etc. are mentioned.

As a polymeric liquid crystal compound, the polymeric liquid crystal compound of Unexamined-Japanese-Patent No. 2017-107232, and Unexamined-Japanese-Patent No. 4719156 is mentioned specifically,.

As a dichroic dye, it is preferable to have a maximum absorption wavelength in the range of 300-700 nm. For example, an acridine dye, an oxazine dye, a cyanine dye, a naphthalene dye, an azo dye, an anthraquinone dye, etc. are mentioned, It is preferable that it is an azo dye.

As a dichroic dye, the dichroic dye of Unexamined-Japanese-Patent No. 2017-107232 is mentioned, for example.

Content of the polymeric liquid crystal compound in a composition (A) is 70-99.9 mass % normally in 100 mass % of solid content of a composition (A), Preferably it is 90-99.9 mass %.

Content of compound (X) is 0.01-20 mass parts normally with respect to 100 mass parts of polymeric liquid crystal compounds, Preferably it is 0.1-10 mass parts, More preferably, it is 0.5-5 mass parts.

Content of a dichroic dye is 0.1-50 mass parts normally with respect to 100 mass parts of polymeric liquid crystal compounds, Preferably it is 0.1-20 mass parts, More preferably, it is 0.1-10 mass parts.

The composition (A) may further contain a polymerization initiator, a leveling agent, a photosensitizer, a solvent, etc. As a polymerization initiator and a leveling agent, the polymerization initiator and leveling agent of Unexamined-Japanese-Patent No. 2017-107232 are mentioned.

In the method of forming a polarizer with the composition (A), a coating film of the composition (A) is formed, the temperature of the coating film is raised, and the polymerizable liquid crystal compound is phase-transferred to a liquid crystal state (preferably a smectic liquid crystal state) to a liquid crystal state ( Preferably, while maintaining the smectic liquid crystal state), the method of polymerizing a polymerizable liquid crystal compound, etc. are mentioned.

Formation of the coating film of a composition (A) can be performed by apply|coating a composition (A) on a base material, for example. As a method of application|coating, well-known methods, such as the spin coating method, the bar coating method, the applicator method, are mentioned.

When a composition (A) contains a solvent, a dry coating film is formed by drying etc. removing a solvent on the conditions that a polymerizable liquid crystal compound does not superpose|polymerize. In addition, in order to phase transition the polymerizable liquid crystal compound, the temperature is raised to a temperature equal to or higher than the temperature at which the polymerizable liquid crystal compound undergoes phase transition to the liquid phase, and then the temperature is lowered to phase transition the polymerizable liquid crystal compound to a liquid crystal state (preferably a smectic liquid crystal state). Such phase transition may be performed after removal of the solvent in the coating film, or may be performed simultaneously with removal of the solvent. By polymerizing the polymerizable liquid crystal compound while maintaining the liquid crystal state of the polymerizable liquid crystal compound, a polarizer as a cured layer of the composition (A) is formed. The polymerization method is preferably a photopolymerization method.

The thickness of the polarizer formed from a composition (A) becomes like this. Preferably it is 0.5-10 micrometers, More preferably, it is 0.5-3 micrometers.

It is preferable that the polarizer formed from a composition (A) is formed on an alignment film. The said alignment film has the orientation regulating force which liquid-crystal-aligns a polymeric liquid crystal compound in a desired direction. Examples of the alignment film include an alignment film containing an oriented polymer, a photo-alignment film, a groove alignment film having a concave-convex pattern or a plurality of grooves on the surface, a stretched film stretched in the alignment direction, and the like, and a photo-alignment film is preferable.

As a specific example of an orientation film, the orientation film of Unexamined-Japanese-Patent No. 2017-107232 is mentioned, for example.

<Protection film>

A protective film is a film layer formed in order to protect other optical layers, such as a polarizer. As a protective film, the film formed from a transparent resin film is mentioned, When the optical layer of this invention is a protective film, it is formed from the composition containing a transparent resin film and a compound (X).

Examples of the transparent resin include cellulose resins, (meth)acrylic resins, polyester resins, polyolefin resins, polyamide resins, polyimide resins, polycarbonate resins, polyether ether ketone resins, and polysulfone resins. and the like.

<Transparent resin>

The cellulose-based resin is preferably a cellulose ester-based resin, that is, a resin in which at least a part of the hydroxyl groups in cellulose is acetic acid esterified, a part is acetic acid esterified, and a mixed ester in which a part is esterified with another acid. it's good too The cellulose ester-based resin is preferably an acetyl cellulose-based resin. Specific examples of the acetyl cellulose-based resin include triacetyl cellulose, diacetyl cellulose, cellulose acetate propionate, and cellulose acetate butyrate.

As the raw material for acetyl cellulose, cellulose raw materials such as wood pulp or cotton liter known from the Invention Association Publication Techniques 2001-1745 and the like can be used. In addition, acetyl cellulose can be synthesize|combined by the method described in wood chemistry pages 180-190 (Kyoritsu Publishing, Migita et al., 1968) etc.

Commercially available products of triacetyl cellulose include "UV-50", "UV-80", "SH-80", "TD-80U", "TD-TAC", "UZ-TAC" manufactured by FUJIFILM, etc. can be heard

As (meth)acrylic-type resin, the homopolymer of methacrylic acid alkylester or acrylic acid alkylester, the copolymer of methacrylic acid alkylester, and acrylic acid alkylester, etc. are mentioned. Specific examples of the alkyl methacrylate ester include methyl methacrylate, ethyl methacrylate, propyl methacrylate, and the acrylic acid alkyl ester, specifically methyl acrylate, ethyl acrylate, propyl acrylate, and the like. can be mentioned respectively. What is marketed as a general-purpose (meth)acrylic-type resin can be used for such (meth)acrylic-type resin. As the (meth)acrylic resin, what is called an impact-resistant (meth)acrylic resin may be used.

Moreover, "Acripet VH", "Acripet VRL20A", etc. of Mitsubishi Rayon Co., Ltd. are mentioned as a specific example of (meth)acrylic-type resin.

Polyester resin is a polymer resin which has the repeating unit of an ester bond in a principal chain, and is generally obtained by condensation polymerization of polyhydric carboxylic acid or its derivative(s), and polyhydric alcohol or its derivative(s).

As polyhydric carboxylic acid or its derivative(s) providing polyester, terephthalic acid, isophthalic acid, phthalic acid, 2,6-naphthalenedicarboxylic acid, diphenyldicarboxylic acid, diphenylsulfonedicarboxylic acid, diphenoxy Aromatic dicarboxylic acids such as ethanedicarboxylic acid and 5-sodium sulfonedicarboxylic acid; aliphatic dicarboxylic acids such as oxalic acid, succinic acid, adipic acid, sebacic acid, dimer acid, maleic acid, and fumaric acid; 1; Oxycarboxylic acids, such as alicyclic dicarboxylic acids, such as 4-cyclohexanedicarboxylic acid, and paraoxybenzoic acid, and these derivatives are mentioned. The dicarboxylic acid derivatives include, for example, dimethyl terephthalate, diethyl terephthalate, 2-hydroxyethylmethyl terephthalate, dimethyl 2,6-naphthalenedicarboxylic acid, dimethyl isophthalate, dimethyl adipate, diethyl maleate, dimer. and esterified products such as dimethyl acid. Among them, terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, and esters thereof are preferably used from the viewpoint of moldability and handleability.

Polyhydric alcohols or derivatives thereof imparting polyester include ethylene glycol, diethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5- Aliphatic dihydroxy compounds such as pentanediol, 1,6-hexanediol and neopentyl glycol, polyoxyalkylene glycol such as diethylene glycol, polyethylene glycol, polypropylene glycol and polytetramethylene glycol, 1,4-cyclohexane Alicyclic dihydroxy compounds, such as dimethanol and spiroglycol, aromatic dihydroxy compounds, such as bisphenol A and bisphenol S, and these derivatives are mentioned. Among them, ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, and 1,4-cyclohexanedimethanol are preferably used from the viewpoint of moldability and handleability.

Examples of the polyester-based resin include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polytrimethylene terephthalate, polytrimethylene naphthalate, polycyclohexanedimethyl terephthalate, polycyclohexanedimethyl Naphthalate etc. are mentioned. Among these, polyethylene terephthalate, polyethylene naphthalate, etc. are preferable.

Examples of the polyolefin-based resin include polyethylene-based resins, polypropylene-based resins, and cycloolefin-based resins, and cycloolefin-based resins are preferred.

The cycloolefin-based resin is, for example, a thermoplastic resin having a unit of a monomer composed of a cyclic olefin (cycloolefin) such as norbornene or a polycyclic norbornene-based monomer, and is also called a thermoplastic cycloolefin-based resin. The cycloolefin-based resin may be a hydrogenated product of the aforementioned ring-opened polymer of cycloolefin or a ring-opened copolymer using two or more types of cycloolefins, and may be a cycloolefin, a chain olefin, or an aromatic compound having a polymerizable double bond such as a vinyl group, etc. may be an addition polymer of A polar group may be introduce|transduced into the cycloolefin resin.

When a protective film is constituted by using a copolymer of a cycloolefin and an aromatic compound having a chain olefin and/or a vinyl group, examples of the chain olefin include ethylene and propylene, and as an aromatic compound having a vinyl group, , styrene, α-methylstyrene, nuclear alkyl-substituted styrene, and the like. In such a copolymer, 50 mol% or less may be sufficient as the unit of the monomer which consists of cycloolefin, Preferably, it is set to about 15-50 mol%. In particular, when a protective film is constituted by using a terpolymer of a cycloolefin, a chain olefin, and an aromatic compound having a vinyl group, the unit of the cycloolefin monomer can be made into a relatively small amount as described above. In such a terpolymer, the monomer unit composed of a chain olefin is usually 5 to 80 mol%, and the monomer unit composed of an aromatic compound having a vinyl group is usually 5 to 80 mol%.

As cycloolefin resin, an appropriate commercial item can be used. For example, "TOPAS" sold by Polyplastic Co., Ltd., "Aton" sold by JSR Co., Ltd., "ZEONOR" and "ZEONEX" sold by Nippon Zeon Co., Ltd., "Apel" sold by Mitsui Chemicals Co., Ltd. (above, all are brand names), etc. are mentioned.

The polyamide-based resin is a polymer resin containing an amide bond in a repeating unit as a main chain, for example, an aromatic polyamide (aramid) in which an aromatic ring skeleton is bonded by an amide bond or an aliphatic polyamide in which an aliphatic skeleton is bonded by an amide bond. and the like. In general, it can be obtained by, for example, a polymerization reaction between a polyhydric carboxylic acid or a derivative thereof and a polyvalent amine.

Examples of polyamide-giving polyamide carboxylic acids or derivatives thereof include terephthalic acid chloride, 2-chloro-terephthalic acid chloride, isophthalic acid dichloride, naphthalenedicarbonyl chloride, biphenyl dicarbonyl chloride, terphenyl dicarbonyl chloride, and the like. can be heard

Examples of the polyamide giving polyamide include 4,4'-diaminodiphenylether, 3,4'-diaminodiphenylether, 4,4'-diaminodiphenylsulfone, 3,3'-dia Minodiphenylsulfone, 2,2'-ditrifluoromethyl-4,4'-diaminobiphenyl, 9,9-bis(4-aminophenyl)fluorene, 9,9-bis(4-amino- 3-methylphenyl)fluorene, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]sulfone, 2,2-bis[4-(4-aminophenoxy) cy)phenyl]propane, 2,2-bis(4-aminophenyl)hexafluoropropane, etc. are preferred, but preferably 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenyl Sulfone, 2,2'-ditrifluoromethyl-4,4'-diaminobiphenyl, 9,9-bis(4-aminophenyl)fluorene, 9,9-bis(4-amino-3-methylphenyl ) fluorene, 1,4-cyclohexanediamine, and 1,4-norbornene diamine.

The polyimide-based resin is a polymer resin having an imide bond in a repeating unit as a main chain, and a condensed polyimide obtained by polycondensation using diamines and tetracarboxylic dianhydride as starting materials is common. As diamines, aromatic diamines, alicyclic diamines, aliphatic diamines, etc. can be used. As tetracarboxylic dianhydride, aromatic tetracarboxylic dianhydride, alicyclic tetracarboxylic dianhydride, acyclic aliphatic tetracarboxylic dianhydride, etc. can be used. Diamines and tetracarboxylic dianhydride may be used individually, respectively, and may be used in combination of 2 or more type. Instead of tetracarboxylic dianhydride, a tetracarboxylic acid compound selected from analogs of tetracarboxylic acid compounds such as acid chloride compounds may be used as a starting material.

From the viewpoint of transparency, mechanical strength, and moldability, the transparent resin is preferably a triacetyl cellulose-based resin, a cycloolefin-based resin, a (meth)acrylic-based resin, or a polyester-based resin.

The storage elastic modulus E' at 23 degreeC of a transparent resin is 100 MPa or more normally, Preferably it is 300 MPa or more, More preferably, it is 500 MPa or more, Especially preferably, it is 1000 MPa or more. Although the upper limit is not limited, it is usually 100000 MPa or less.

Content of compound (X) is 0.01-50 mass parts normally with respect to 100 mass parts of transparent resin, Preferably it is 0.1-20 mass parts, More preferably, it is 0.2-10 mass parts, Especially preferably, it is 0.5- 5 parts by mass.

When forming a protective film, the composition (henceforth a resin composition (1) may be mentioned.) containing at least compound (X) and a transparent resin can be formed by arbitrary suitable shaping|molding processing methods. Specific examples include a compression molding method, a transfer molding method, an injection molding method, an extrusion molding method, a blow molding method, a powder molding method, an FRP molding method, a cast coating method (eg, a casting method), a calender molding method, a hot press method, and the like. The extrusion molding method or the cast coating method is preferable at the point that the smoothness of the optical layer obtained can be improved and favorable optical uniformity can be obtained. Molding conditions can be appropriately set according to the composition or type of the resin used, characteristics required, and the like.

The protective film may further contain a plasticizer, an organic acid, a dye, an antistatic agent, a surfactant, a lubricant, a flame retardant, a filler, a rubber particle, a phase difference regulator, a ultraviolet absorber, a leveling agent, etc.

<Retardation film>

A retardation film is an optical film which shows optical anisotropy, and the retardation film which expressed the optical anisotropy by application|coating and orientation of the retardation film formed from a stretched film, or a liquid crystalline compound to a base material is mentioned.

Examples of the stretched film include polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, polystyrene, polysulfone, polyethersulfone, polyvinylidene fluoride/polymethylmethacrylate. , a stretched film obtained by stretching a polymer film made of acetylcellulose, saponified ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. to about 1.01 to 6 times. It is preferable that it is the polymer film which uniaxially or biaxially stretched the acetyl cellulose, polyester, a polycarbonate film, or a cycloolefin resin film among a stretched film.

When the optical layer of the present invention is a retardation film formed of a stretched film, it is formed of a resin composition comprising a resin and compound (X) forming the polymer film. For example, it can manufacture by extending|stretching the unstretched film obtained by melt-extruding or cast-molding the composition containing at least the resin which has arbitrary intrinsic birefringence, and compound (X). Uniaxial stretching may be sufficient as extending|stretching, and biaxial stretching may be sufficient as it. When extending|stretching, it is preferable to extend|stretch at the temperature higher than the glass transition temperature of resin. In addition, it is preferable to perform the process of thermally relaxing the residual stress of a film after extending|stretching. Moreover, the method of Unexamined-Japanese-Patent No. 2013-205500, etc. are mentioned.

In addition, in this specification, the retardation film includes a zero retardation film, and also includes a film called a uniaxial retardation film, a low photoelastic-modulus retardation film, a wide viewing angle retardation film, etc.

Zero retardation film is, the front retardation R _e and a retardation R _th all -15~15 nm in the thickness direction, refers to an optically isotropic film. Examples of the zero retardation film include a film formed of a resin film made of a cellulose-based resin, a polyolefin-based resin (chain polyolefin-based resin, polycycloolefin-based resin, etc.) or a polyethylene terephthalate-based resin. From the viewpoint of easy control, it is preferably formed of a cellulosic resin or a polyolefin-based resin.

A zero retardation film can be created by adjusting a draw ratio by the preparation method similar to the retardation film formed from the above-mentioned stretched film. Moreover, it can create also by extending|stretching the unstretched film which combined resin which has intrinsic birefringence with different positive and negative.

In the present invention, the retardation film is preferably a retardation film in which optical anisotropy is expressed by application and orientation of a liquid crystal compound.

The retardation film in which optical anisotropy was expressed by application and orientation of the liquid crystalline compound is formed from a composition (hereinafter, sometimes referred to as a composition (B)) containing the liquid crystalline compound and the compound (X). The composition (B) may further contain a photoinitiator.

As a liquid crystalline compound contained in the composition (B), "3.8.6 network (completely crosslinked type)" and "6.5 .1 liquid crystal material b. A compound having a polymerizable group among the compounds described in "polymerizable nematic liquid crystal material", and Japanese Patent Laid-Open Nos. 2010-31223, 2010-270108, and 2011-6360, Japanese Patent Application Laid-Open Nos. Polymeric liquid crystal described in Unexamined-Japanese-Patent No. 2011-207765, Unexamined-Japanese-Patent No. 2011-162678, Unexamined-Japanese-Patent No. 2016-81035, International Unexamined-Japanese-Patent No. 2017/043438, and Unexamined-Japanese-Patent No. 2011-207765. compounds, and the like.

Content of the liquid crystalline compound in composition (B) is 50-99 mass % normally in 100 mass % of solid content of composition (B), Preferably it is 75-90 mass %.

Content of compound (X) is 0.01-20 mass parts normally with respect to 100 mass parts of liquid crystalline compounds, Preferably it is 0.1-10 mass parts, More preferably, it is 0.5-5 mass parts.

As for the method of manufacturing a retardation film with a composition (B), the method of Unexamined-Japanese-Patent No. 2010-31223, etc. are mentioned, for example.

As a film to which optical anisotropy was expressed by application|coating and orientation of a liquid crystalline compound, the following 1st aspect - 5th aspect is mentioned.

First form: retardation film in which a rod-shaped liquid crystal compound is oriented in a horizontal direction with respect to a supporting substrate

Second form: retardation film in which the rod-shaped liquid crystal compound is oriented in a direction perpendicular to the supporting substrate

3rd form: retardation film in which the direction of orientation of the rod-shaped liquid crystal compound is changed spirally in the plane

4th form: retardation film in which disc-shaped liquid crystal compound is diagonally oriented

Fifth form: a biaxial retardation film in which a disk-shaped liquid crystal compound is oriented in a vertical direction with respect to a supporting substrate

For example, as an optical film used for an organic electroluminescent display, a 1st form, a 2nd form, and a 5th form are used suitably. Alternatively, a retardation film of this type may be laminated and used.

When the retardation film is a layer made of a polymer in an orientation state of the polymerizable liquid crystal compound (hereinafter, sometimes referred to as an "optically anisotropic layer"), the retardation film preferably has reverse wavelength dispersion. Reverse wavelength dispersion is an optical property in which the liquid crystal alignment in-plane retardation value at a short wavelength becomes smaller than the liquid crystal alignment in-plane retardation value at a long wavelength, and preferably, the retardation film satisfies the following formulas (7) and (8) will be. In addition, Re(λ) represents an in-plane retardation value with respect to light having a wavelength of λ nm.

Re(450)/Re(550)≤1 (7)

1≤Re(630)/Re(550) (8)

In the optical layer of the present invention, when the retardation film is the first form and has reverse wavelength dispersion, it is preferable because the coloration at the time of black display in the display device is reduced, and in the above formula (7), 0.82≤Re( 450)/Re(550) ? 0.93 is more preferable. 120≤Re(550)≤150 is more preferable.

In the case of the second aspect, the front retardation value Re (550) may be adjusted in the range of 0 to 10 nm, preferably in the range of 0 to 5 nm, and the retardation value R _th in the thickness direction is -10 to -300 nm In the range of, it is preferable to adjust in the range of -20 to -200 nm. _{The retardation value R th} in the thickness direction, which means refractive index anisotropy in the thickness direction, can be calculated from _{the retardation value R 50} and the in-plane retardation value R ₀ measured by tilting the in-plane fast axis by 50 degrees with the inclination axis. That is, the retardation value R _th in the thickness direction is from the in-plane retardation value R _{0 , the retardation value R 50} measured by tilting the fast axis by 50 degrees with the inclination axis, the thickness d of the retardation film, and the average refractive index n ₀ of the retardation film _{, n x} , n _y and n _z are obtained by the following equations (10) to (12), and can be calculated by substituting them into equation (9).

R _th =[(n _x +n _y )/2-n _z ]×d (9)

R ₀ =(n _x -n _y )×d (10)

R ₅₀ =(n _x -n _y ')×d/cos(φ) (11)

(n _x +n _y +n _z )/3=n ₀ (12)

here,

φ=sin ^-1 [sin(40°)/n ₀ ]

n _y '=n _y ×n _z /[n _y ² ×sin ² (φ)+n _z ² ×cos ² (φ)] ^1/2

The retardation film may be a multilayer film having two or more layers. For example, a protective film is laminated on one side or both sides of the retardation film, or two or more retardation films are laminated through an adhesive or an adhesive.

<Adhesive layer>

An adhesive layer has adhesiveness (pressure-sensitive adhesiveness), and is used in order to bond optical layers, an optical layer and another layer, or another layer, or to fix an optical layer to another object.

The pressure-sensitive adhesive layer is formed from, for example, a pressure-sensitive adhesive composition (hereinafter, sometimes referred to as pressure-sensitive adhesive composition (3)) containing a resin having a glass transition temperature of 30°C or less, a compound (X), and a crosslinking agent. As the resin having a glass transition temperature of 30 ° C. or less, rubber-based resins, (meth)acrylic resins, silicone-based resins, etc. can be used, but from the viewpoints of transparency, durability, ease of performance adjustment, and the like, (meth)acrylic resins are preferred.

((meth)acrylic resin)

It is preferable that the (meth)acrylic-type resin in an adhesive composition is a polymer which has the structural unit derived from (meth)acrylic acid ester as a main component (preferably 50 mass % or more is included.). The structural unit derived from (meth)acrylic acid ester may include a structural unit derived from a monomer other than one or more types of (meth)acrylic acid ester (eg, a structural unit derived from a monomer having a polar functional group).

As (meth)acrylic acid ester, the (meth)acrylic acid ester represented by a following formula (Y) is mentioned.

[In formula (Y), R ₁ represents a hydrogen atom or a methyl group, R ₂ represents an alkyl group having 1 to 14 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, and the hydrogen atom of the alkyl group or the aralkyl group is 1 It may be substituted with the alkoxy group of -10.]

R ₂ is preferably an alkyl group having 1 to 14 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.

As (meth)acrylic acid ester represented by Formula (Y),

(meth)methyl acrylate, (meth)ethyl acrylate, (meth)acrylic acid n-propyl, (meth)acrylic acid n-butyl, (meth)acrylic acid n-pentyl, (meth)acrylic acid n-hexyl, (meth)acrylic acid n- Heptyl, (meth)acrylic acid n-octyl, (meth)acrylic acid n-nonyl, (meth)acrylic acid n-decyl, (meth)acrylic acid n-dodecyl, (meth)acrylic acid lauryl, (meth)acrylic acid stearyl, etc. straight-chain alkyl esters of (meth)acrylic acid;

(meth)acrylic acid i-propyl, (meth)acrylic acid i-butyl, (meth)acrylic acid t-butyl, (meth)acrylic acid i-pentyl, (meth)acrylic acid i-hexyl, (meth)acrylic acid 2-ethylhexyl, ( Branched alkyl esters of (meth)acrylic acid, such as i-octyl meth)acrylic acid, i-nonyl (meth)acrylic acid, i-stearyl (meth)acrylic acid, and i-amyl (meth)acrylic acid;

(meth)acrylic acid cyclohexyl, (meth)acrylic acid isoboronyl, (meth)acrylic acid adamantyl, (meth)acrylic acid dicyclopentanyl, (meth)acrylic acid cyclododecyl, (meth)acrylic acid methylcyclohexyl, (meth) alicyclic skeleton-containing alkyl esters of (meth)acrylic acid such as trimethylcyclohexyl acrylate, tert-butylcyclohexyl (meth)acrylic acid, and cyclohexyl α-ethoxyacrylic acid;

Aromatic ring skeleton containing ester of (meth)acrylic acid, such as (meth)acrylic-acid phenyl;

and the like.

Moreover, the substituent-containing (meth)acrylic-acid alkylester in which the substituent was introduce|transduced into the alkyl group in (meth)acrylic-acid alkylester is also mentioned. The substituent of the substituent-containing (meth)acrylic acid alkyl ester is a group substituting a hydrogen atom in the alkyl group, and specific examples thereof include a phenyl group, an alkoxy group and a phenoxy group. As the substituent-containing (meth)acrylic acid alkylester, specifically, (meth)acrylic acid 2-methoxyethyl, (meth)acrylic acid ethoxymethyl, (meth)acrylic acid phenoxyethyl, (meth)acrylic acid 2-(2-phenoxy) ethoxy)ethyl, (meth)acrylic acid phenoxydiethylene glycol, (meth)acrylic acid phenoxypoly(ethylene glycol), etc. are mentioned.

These (meth)acrylic acid esters can be used independently, respectively, and may use a different several thing.

The (meth)acrylic resin contains a structural unit derived from an acrylic acid alkylester (a1) having a glass transition temperature Tg of less than 0°C of the homopolymer, and a structural unit derived from an acrylic acid alkylester (a2) having a homopolymer Tg of 0°C or higher It is preferable to do It is advantageous to contain the structural unit derived from an acrylic acid alkylester (a1) and the structural unit derived from an acrylic acid alkylester (a2) in improving the high temperature durability of an adhesive layer. As for Tg of the homopolymer of (meth)acrylic acid alkylester, literature values, such as POLYMER HANDBOOK (Wiley-Interscience), can be employ|adopted, for example.

Specific examples of the alkyl acrylate ester (a1) include ethyl acrylate, n- and i-propyl acrylate, n- and i-butyl acrylate, n-pentyl acrylate, n- and i-hexyl acrylate, n-heptyl acrylate, acrylic acid Acrylic acid alkyl esters having 2 to 12 carbon atoms in the alkyl group, such as n- and i-octyl, 2-ethylhexyl acrylate, n- and i-nonyl acrylate, n- and i-decyl acrylate, and n-dodecyl acrylate, etc. and n-butyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate, and the like are preferable.

Acrylic acid alkylester (a1) may use 2 or more types together.

The acrylic acid alkyl ester (a2) is an acrylic acid alkyl ester other than the acrylic acid alkyl ester (a1). Specific examples of the alkyl acrylate ester (a2) include methyl acrylate, cyclohexyl acrylate, isoboronyl acrylate, stearyl acrylate, and t-butyl acrylate, and methyl acrylate, cyclohexyl acrylate, isoboronyl acrylate, etc. It is preferable to contain, and it is more preferable to contain methyl acrylate.

Acrylic acid alkylester (a2) may use 12 or more types together.

The structural unit derived from the (meth)acrylic acid ester represented by the formula (Y) is preferably 50 mass% or more, preferably 60 to 95 mass%, among all the structural units contained in the (meth)acrylic resin; It is more preferable that it is 65-95 mass % or more.

As the structural unit derived from a monomer other than (meth)acrylic acid ester, a structural unit derived from a monomer having a polar functional group is preferable, and a structural unit derived from a (meth)acrylic acid ester having a polar functional group is more preferable. Examples of the polar functional group include a hydroxy group, a carboxyl group, a substituted or unsubstituted amino group, and a heterocyclic group such as an epoxy group.

As a monomer having a polar functional group,

(meth)acrylic acid 1-hydroxymethyl, (meth)acrylic acid 1-hydroxyethyl, (meth)acrylic acid 1-hydroxyheptyl, (meth)acrylic acid 1-hydroxybutyl, (meth)acrylic acid 1-hydroxypentyl; (meth)acrylic acid 2-hydroxyethyl, (meth)acrylic acid 2-hydroxypropyl, (meth)acrylic acid 2-hydroxybutyl, (meth)acrylic acid 2-hydroxypentyl, (meth)acrylic acid 2-hydroxyhexyl; (meth)acrylic acid 3-hydroxypropyl, (meth)acrylic acid 3-hydroxybutyl, (meth)acrylic acid 3-hydroxypentyl, (meth)acrylic acid 3-hydroxyhexyl, (meth)acrylic acid 3-hydroxyheptyl; (meth)acrylic acid 4-hydroxybutyl, (meth)acrylic acid 4-hydroxypentyl, (meth)acrylic acid 4-hydroxyhexyl, (meth)acrylic acid 4-hydroxyheptyl, (meth)acrylic acid 4-hydroxyoctyl; (meth)acrylic acid 2-chloro-2-hydroxypropyl, (meth)acrylic acid 3-chloro-2-hydroxypropyl, (meth)acrylic acid 2-hydroxy-3-phenoxypropyl, (meth)acrylic acid 5-hydroxy Roxypentyl, (meth)acrylic acid 5-hydroxyhexyl, (meth)acrylic acid 5-hydroxyheptyl, (meth)acrylic acid 5-hydroxyoctyl, (meth)acrylic acid 5-hydroxynonyl, (meth)acrylic acid 6-hydroxy Hydroxyhexyl, (meth)acrylic acid 6-hydroxyheptyl, (meth)acrylic acid 6-hydroxyoctyl, (meth)acrylic acid 6-hydroxynonyl, (meth)acrylic acid 6-hydroxydecyl, (meth)acrylic acid 7-hydroxy Hydroxyheptyl, (meth)acrylic acid 7-hydroxyoctyl, (meth)acrylic acid 7-hydroxynonyl, (meth)acrylic acid 7-hydroxydecyl, (meth)acrylic acid 7-hydroxyundecyl, (meth)acrylic acid 8- Hydroxyoctyl, (meth)acrylic acid 8-hydroxynonyl, (meth)acrylic acid 8-hydroxydecyl, (meth)acrylic acid 8-hydroxyundecyl, (meth)acrylic acid 8-hydroxydodecyl, (meth)acrylic acid 9-hydroxynonyl, (meth)acrylic acid 9-hydroxydecyl, (meth)acrylic acid 9-hydroxyundecyl, (meth)acrylic acid 9-hydroxydodecyl, (meth)acrylic acid 9-hydroxytridecyl, ( meth)acrylic acid 10-hydroxydecyl, (meth)acrylic acid 10-hydroxyundecyl, (meth)acrylic acid 10-hydroxydo Decyl, acrylic acid 10-hydroxytridecyl, (meth)acrylic acid 10-hydroxytetradecyl, (meth)acrylic acid 11-hydroxyundecyl, (meth)acrylic acid 11-hydroxydodecyl, (meth)acrylic acid 11-hydroxy Hydroxytridecyl, (meth)acrylic acid 11-hydroxytetradecyl, (meth)acrylic acid 11-hydroxypentadecyl, (meth)acrylic acid 12-hydroxydodecyl, (meth)acrylic acid 12-hydroxytridecyl, (meth)acrylic acid ) Acrylic acid 12-hydroxytetradecyl, (meth)acrylic acid 13-hydroxypentadecyl, (meth)acrylic acid 13-hydroxytetradecyl, (meth)acrylic acid 13-hydroxypentadecyl, (meth)acrylic acid 14-hydroxy Monomers having a hydroxyl group, such as tetradecyl, (meth)acrylic acid 14-hydroxypentadecyl, (meth)acrylic acid 15-hydroxypentadecyl, and (meth)acrylic acid 15-hydroxyheptadecyl;

Monomers having a carboxyl group such as (meth)acrylic acid, carboxyalkyl (meth)acrylate (eg, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate), maleic acid, maleic anhydride, fumaric acid, crotonic acid;

Acryloylmorpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, vinylpyridine, tetrahydrofurfuryl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, 3,4-epoxycyclohexyl monomers having a heterocyclic group such as methyl (meth)acrylate, glycidyl (meth)acrylate, and 2,5-dihydrofuran;

and monomers having a substituted or unsubstituted amino group, such as aminoethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, and dimethylaminopropyl (meth)acrylate.

Among them, from the viewpoint of reactivity between the (meth)acrylic acid ester polymer and the crosslinking agent, a monomer having a hydroxyl group or a monomer having a carboxyl group is preferable, and it is more preferable to include both a monomer having a hydroxyl group and a monomer having a carboxyl group.

As a monomer which has a hydroxyl group, 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, and 6-hydroxyhexyl acrylate are preferable. In particular, good durability can be obtained by using 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate and 5-hydroxypentyl acrylate.

It is preferable to use acrylic acid as a monomer which has a carboxyl group.

Moreover, it is preferable that (meth)acrylic-type resin does not contain the structural unit derived from the monomer which has an amino group substantially. Here, "not included" means that it is 0.1 mass part or less in 100 mass parts of all structural units which comprise (meth)acrylic-type resin.

The content of the structural unit derived from the monomer having a polar functional group is preferably 20 parts by mass relative to 100 parts by mass of all structural units of the (meth)acrylic resin from the viewpoint of the durability of the pressure-sensitive adhesive (peeling or cohesive failure at high temperature). parts, more preferably 0.5 parts by mass or more and 15 parts by mass or less, still more preferably 0.5 parts by mass or more and 10 parts by mass or less, particularly preferably 1 part by mass or more and 7 parts by mass or less. On the other hand, from the viewpoint of the bleed resistance of the compound (X) to be contained, with respect to 100 parts by mass of all structural units of the (meth)acrylic resin, preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, still more preferably is 5 parts by mass or more, particularly preferably 7.5 parts by mass or more. In order to achieve a balance between durability and bleed resistance, it is preferable to adjust the amount of polar functional groups according to the content of compound (X).

The content of the structural unit derived from the monomer having an aromatic group is preferably 20 parts by mass or less, more preferably 4 parts by mass or more and 20 parts by mass or less, with respect to 100 parts by mass of all the structural units of the (meth)acrylic resin. Preferably they are 4 mass parts or more and 16 mass parts or less.

Structural units derived from monomers other than (meth)acrylic acid esters include structural units derived from styrene-based monomers, structural units derived from vinyl-based monomers, and monomers having a plurality of (meth)acryloyl groups in the molecule. A structural unit, a structural unit derived from a (meth)acrylamide type monomer, etc. are mentioned.

Examples of the styrene-based monomer include styrene; alkyl styrenes such as methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene and octyl styrene; halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene; nitrostyrene; acetyl styrene; methoxystyrene; and divinylbenzene.

Examples of the vinyl-based monomer include fatty acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, and vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; vinylidene halides such as vinylidene chloride; nitrogen-containing heteroaromatic vinyls such as vinylpyridine, vinylpyrrolidone and vinylcarbazole; conjugated dienes such as butadiene, isoprene and chloroprene; and unsaturated nitriles such as acrylonitrile and methacrylonitrile.

Examples of the monomer having a plurality of (meth)acryloyl groups in the molecule include 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, and 1,9-nonanedioldi(meth)acrylate. ) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate in the molecule of two (meth) ) a monomer having an acryloyl group; The monomer which has three (meth)acryloyl groups in molecules, such as trimethylol propane tri(meth)acrylate, is mentioned.

Examples of the (meth)acrylamide-based monomer include N-methylol (meth)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, N-(4-hydroxybutyl)(meth)acrylamide, N-(5-hydroxypentyl)(meth)acrylamide, N-(6-hydroxyhexyl)(meth)acrylamide, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-(3-dimethylaminopropyl) (meth)acrylamide, N-(1,1- Dimethyl-3-oxobutyl)(meth)acrylamide, N-[2-(2-oxo-1-imidazolidinyl)ethyl](meth)acrylamide, 2-acryloylamino-2-methyl-1 -Propanesulfonic acid, N-(methoxymethyl)acrylamide, N-(ethoxymethyl)(meth)acrylamide, N-(propoxymethyl)(meth)acrylamide, N-(1-methylethoxymethyl) (meth)acrylamide, N-(1-methylpropoxymethyl)(meth)acrylamide, N-(2-methylpropoxymethyl)(meth)acrylamide, N-(butoxymethyl)(meth)acrylamide , N-(1,1-dimethylethoxymethyl)(meth)acrylamide, N-(2-methoxyethyl)(meth)acrylamide, N-(2-ethoxyethyl)(meth)acrylamide, N -(2-propoxyethyl)(meth)acrylamide, N-[2-(1-methylethoxy)ethyl](meth)acrylamide, N-[2-(1-methylpropoxy)ethyl](meth) ) acrylamide, N-[2-(2-methylpropoxy)ethyl](meth)acrylamide, N-(2-butoxyethyl)(meth)acrylamide, N-[2-(1,1-dimethyl) ethoxy)ethyl] (meth)acrylamide etc. are mentioned. Among them, N-(methoxymethyl)acrylamide, N-(ethoxymethyl)acrylamide, N-(propoxymethyl)acrylamide, N-(butoxymethyl)acrylamide, and N-(2-methylpropane) Foxymethyl)acrylamide is preferred.

The weight average molecular weight (Mw) of the (meth)acrylic resin is preferably 500,000 to 2.5 million, more preferably 600,000 to 1.8 million, still more preferably 700,000 to 1.7 million, particularly preferably 1 million to 160,000. Moreover, the molecular weight distribution (Mw/Mn) represented by ratio of a weight average molecular weight (Mw) and a number average molecular weight (Mn) is 2-10 normally, Preferably it is 3-8, More preferably, it is 3-6. A weight average molecular weight can be analyzed by gel permeation chromatography, and is a standard polystyrene conversion value.

When the (meth)acrylic acid resin is dissolved in ethyl acetate to obtain a solution having a concentration of 20% by mass, the viscosity at 25°C is preferably 20 Pa·s or less, more preferably 0.1 to 15 Pa·s. It is advantageous from a viewpoint of the coatability at the time of coating the adhesive composition (3) as it is a viscosity of the said range. In addition, a viscosity can be measured with a Brookfield viscometer.

The glass transition temperature (Tg) of the (meth)acrylic resin may be, for example, -60 to 20°C, preferably -50 to 15°C, more preferably -45 to 10°C, and particularly -40 to 0°C. In addition, a glass transition temperature can be measured with a differential scanning calorimeter (DSC).

(meth)acrylic resin can be manufactured by well-known methods, such as a solution polymerization method, the block polymerization method, the suspension polymerization method, and the emulsion polymerization method, for example, especially the solution polymerization method is preferable.

Content of (meth)acrylic-type resin is 60 mass % - 99.9 mass % normally in 100 mass % of adhesive composition (3), Preferably they are 70 mass % - 99.5 mass %, More preferably, they are 80 mass % - 99 mass %.

Content of compound (X) is 0.01-50 mass parts normally with respect to 100 mass parts of resin whose glass transition temperature is 30 degrees C or less, Preferably it is 0.1-20 mass parts, More preferably, it is 0.2-10 mass parts, Especially preferably, it is 0.5-5 mass parts.

The crosslinking agent reacts with a polar functional group (eg, a hydroxyl group, an amino group, a carboxyl group, a heterocyclic group, etc.) in the resin. The crosslinking agent forms a crosslinked structure with a resin or the like, and forms a crosslinked structure advantageous for durability.

Examples of the crosslinking agent include an isocyanate-based crosslinking agent, an epoxy-based crosslinking agent, an aziridine-based crosslinking agent, and a metal chelate-based crosslinking agent. It is preferable that it is a system crosslinking agent.

As the isocyanate-based compound, a compound having at least two isocyanate groups (-NCO) in the molecule is preferable, for example, an aliphatic isocyanate-based compound (such as hexamethylene diisocyanate), an alicyclic isocyanate-based compound (such as isophorone) diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate), aromatic isocyanate compounds (such as tolylene diisocyanate, xylylene diisocyanate diphenylmethane diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, etc.) can be heard Further, the crosslinking agent is an adduct (adduct) of the isocyanate compound with a polyhydric alcohol compound (eg, an adduct with glycerol, trimethylolpropane, etc.), isocyanurate, biuret-type compound, polyether polyol, polyester Derivatives, such as a urethane prepolymer type isocyanate compound, which were addition-reacted with polyol, acrylic polyol, polybutadiene polyol, polyisoprene polyol, etc. may be sufficient. A crosslinking agent can be used individually or in combination of 2 or more types. Among them, representatively, aromatic isocyanate compounds (eg tolylene diisocyanate, xylylene diisocyanate), aliphatic isocyanate compounds (eg hexamethylene diisocyanate) or polyhydric alcohol compounds thereof (eg glycerol, trimethylolpropane) are used. an adduct or an isocyanurate body. If the crosslinking agent is an aromatic isocyanate compound and/or an adduct of these polyhydric alcohol compounds, or an isocyanurate compound, this is because it is advantageous for formation of an optimal crosslinking density (or crosslinking structure), pressure-sensitive adhesive composition (3) It is possible to improve the durability of the optical layer formed of In particular, durability can be improved if it is a tolylene diisocyanate type compound and/or an adduct of these polyhydric alcohol compounds.

Content of a crosslinking agent is 0.01-15 mass parts normally with respect to 100 mass parts of resin (preferably (meth)acrylic-type resin) whose glass transition temperature is 30 degrees C or less, Preferably it is 0.05-10 mass parts, More preferably It is 0.1-5 mass parts.

The pressure-sensitive adhesive composition (3) may further contain a silane compound.

Examples of the silane compound include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxypropyltriethane. Toxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane , 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. are mentioned.

The silane compound may be a silicone oligomer. Specific examples of silicone oligomers are described in the form of a combination of monomers as follows.

3-mercaptopropyltrimethoxysilane-tetramethoxysilane oligomer, 3-mercaptopropyltrimethoxysilane-tetraethoxysilane oligomer, 3-mercaptopropyltriethoxysilane-tetramethoxysilane oligomer, 3- mercaptopropyl group-containing oligomers such as mercaptopropyltriethoxysilane-tetraethoxysilane oligomers; Mercaptomethyltrimethoxysilane-tetramethoxysilane oligomer, mercaptomethyltrimethoxysilane-tetraethoxysilane oligomer, mercaptomethyltriethoxysilane-tetramethoxysilane oligomer, mercaptomethyltriethoxysilane- mercaptomethyl group-containing oligomers such as tetraethoxysilane oligomers; 3-Glycidoxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane-tetraethoxysilane copolymer, 3-glycidoxypropyltriethoxysilane-tetramethoxy Silane copolymer, 3-glycidoxypropyltriethoxysilane-tetraethoxysilane copolymer, 3-glycidoxypropylmethyldimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropylmethyldimethoxysilane - 3-glycidoxy such as tetraethoxysilane copolymer, 3-glycidoxypropylmethyldiethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropylmethyldiethoxysilane-tetraethoxysilane copolymer propyl group-containing copolymer; 3-Methacryloyloxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane -Tetramethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-methacrylo Iloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropylmethyldiethoxysilane-tetraethoxysilane methacryloyloxypropyl group-containing oligomers such as oligomers; 3-Acryloyloxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropyltriethoxysilane-tetrame Toxysilane oligomer, 3-acryloyloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxy Acryloyloxypropyl such as silane-tetraethoxysilane oligomer, 3-acryloyloxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, and 3-acryloyloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer group-containing oligomers; Vinyltrimethoxysilane-tetramethoxysilane oligomer, vinyltrimethoxysilane-tetraethoxysilane oligomer, vinyltriethoxysilane-tetramethoxysilane oligomer, vinyltriethoxysilane-tetraethoxysilane oligomer, vinylmethyl Contains vinyl groups such as dimethoxysilane-tetramethoxysilane oligomer, vinylmethyldimethoxysilane-tetraethoxysilane oligomer, vinylmethyldiethoxysilane-tetramethoxysilane oligomer, and vinylmethyldiethoxysilane-tetraethoxysilane oligomer oligomers; 3-Aminopropyltrimethoxysilane-tetramethoxysilane copolymer, 3-aminopropyltrimethoxysilane-tetraethoxysilane copolymer, 3-aminopropyltriethoxysilane-tetramethoxysilane copolymer, 3- Aminopropyltriethoxysilane-tetraethoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetramethoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetraethoxysilane copolymer, 3-aminopropyl amino group-containing copolymers such as methyldiethoxysilane-tetramethoxysilane copolymer and 3-aminopropylmethyldiethoxysilane-tetraethoxysilane copolymer;

The silane compound may be a silane compound represented by the following formula (d1).

(Wherein, B represents an alkanediyl group having 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and -CH ₂ - constituting the alkanediyl group and the alicyclic hydrocarbon group is -O- or It may be substituted with -CO-, R ^d7 represents an alkyl group having 1 to 5 carbon atoms, and R ^d8 , R ^d9 , R ^d10 , R ^d11 and R ^d12 are each independently an alkyl group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms. represents an alkoxy group.)

In formula (d1), B is a C1-C20 alkanediyl group, such as a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a hexamethylene group, a heptamethylene group, and an octamethylene group; A cyclobutylene group (eg, a 1,2-cyclobutylene group), a cyclopentylene group (eg, a 1,2-cyclopentylene group), a cyclohexylene group (eg, a 1,2-cyclohexylene group), a cyclooctylene group (eg, 1 ,2-cyclooctylene group), a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or an alkanediyl group thereof and -CH ₂ -valent, constituting the alicyclic hydrocarbon group, is substituted with -O- or -CO- indicates a group that has been Preferred B is an alkanediyl group having 1 to 10 carbon atoms. R ^d7 represents an alkyl group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a s-butyl group, a t-butyl group, and a pentyl group, R ^d8 , R ^d9 , R ^d10 , R ^d11 and R ^d12 are each independently ^{an alkyl group having 1 to 5 carbon atoms as exemplified for R 3} above, or a methoxy group, ethoxy group, propoxy group, i-propoxy group, butoxy group, s-butoxy group, t-butoxy group A C1-C5 alkoxy group, such as Preferred R ^d8 , R ^d9 , R ^d10 , R ^d11 and R ^d12 are each independently an alkoxy group having 1 to 5 carbon atoms. These silane compounds (d) can be used individually or in combination of 2 or more types.

Examples of the silane compound represented by the formula (d1) include (trimethoxysilyl)methane, 1,2-bis(trimethoxysilyl)ethane, 1,2-bis(triethoxysilyl)ethane, 1, 3-bis(trimethoxysilyl)propane, 1,3-bis(triethoxysilyl)propane, 1,4-bis(trimethoxysilyl)butane, 1,4-bis(triethoxysilyl)butane, 1,5-bis(trimethoxysilyl)pentane, 1,5-bis(triethoxysilyl)pentane, 1,6-bis(trimethoxysilyl)hexane, 1,6-bis(triethoxysilyl) Hexane, 1,6-bis(tripropoxysilyl)hexane, 1,8-bis(trimethoxysilyl)octane, 1,8-bis(triethoxysilyl)octane, 1,8-bis(tripropoxy bis(tri C1-5 alkoxysilyl) C1-10 alkanes such as silyl)octane; bis(dimethoxymethylsilyl)methane, 1,2-bis(dimethoxymethylsilyl)ethane, 1,2-bis(dimethoxyethylsilyl)ethane, 1,4-bis(dimethoxymethylsilyl)butane, 1, 4-bis(dimethoxyethylsilyl)butane, 1,6-bis(dimethoxymethylsilyl)hexane, 1,6-bis(dimethoxyethylsilyl)hexane, 1,8-bis(dimethoxymethylsilyl)octane, bis(di C1-5 alkoxy C1-5 alkylsilyl) C1-10 alkanes such as 1,8-bis(dimethoxyethylsilyl)octane; Bis(mono C1-5 alkoxydi C1-5 alkylsilyl) C1-10 alkanes such as 1,6-bis(methoxydimethylsilyl)hexane and 1,8-bis(methoxydimethylsilyl)octane; and the like. . Among these, 1,2-bis(trimethoxysilyl)ethane, 1,3-bis(trimethoxysilyl)propane, 1,4-bis(trimethoxysilyl)butane, and 1,5-bis(trimethane) Bis(tri C1-3 alkoxysilyl) C1-10 alkanes, such as oxysilyl)pentane, 1,6-bis(trimethoxysilyl)hexane, and 1,8-bis(trimethoxysilyl)octane, are preferable, and especially , 1,6-bis(trimethoxysilyl)hexane and 1,8-bis(trimethoxysilyl)octane are preferred.

Content of a silane compound is 0.01-10 mass parts normally with respect to 100 mass parts of resin (preferably (meth)acrylic-type resin) whose glass transition temperature is 30 degrees C or less, Preferably it is 0.03-5 mass parts, More preferably is 0.05 to 2 parts by mass, more preferably 0.1 to 1 part by mass.

The pressure-sensitive adhesive composition (3) may further contain an antistatic agent.

As an antistatic agent, surfactant, a siloxane compound, a conductive polymer, an ionic compound, etc. are mentioned, It is preferable that it is an ionic compound. As an ionic compound, a conventional thing is mentioned. Examples of the cationic component constituting the ionic compound include organic cations and inorganic cations. Examples of the organic cation include pyridinium cation, pyrrolidinium cation, piperidinium cation, imidazolium cation, ammonium cation, sulfonium cation, phosphonium cation and the like. Examples of the inorganic cation include alkali metal cations such as lithium cation, potassium cation, sodium cation and cesium cation, and alkaline earth metal cations such as magnesium cation and calcium cation. In particular, a pyridinium cation, an imidazolium cation, a pyrrolidinium cation, a lithium cation, and a potassium cation are preferable from the viewpoint of compatibility with the (meth)acrylic resin. The anion component constituting the ionic compound may be either an inorganic anion or an organic anion, but an anion component containing a fluorine atom is preferable from the viewpoint of antistatic performance. Examples of the anion component containing a fluorine atom include hexafluorophosphate anion (PF ₆ ⁻ ), bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ⁻ ], bis(fluoro sulfonyl)imide anion [(FSO ₂ ) ₂ N ⁻ ], tetra(pentafluorophenyl) borate anion [(C ₆ F ₅ ) ₄ B ⁻ ], and the like. These ionic compounds can be used individually or in combination of 2 or more types. In particular, bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ^- ], bis(fluorosulfonyl)imide anion [(FSO ₂ ) ₂ N ^- ], tetra(pentafluoro The rophenyl)borate anion [(C ₆ F ₅ ) ₄ B ^- ] is preferred.

The ionic compound which is solid at room temperature from the point of the aging stability of the antistatic performance of the optical layer formed from the adhesive composition (3) is preferable.

Content of antistatic agent is 0.01-20 mass parts with respect to 100 mass parts of resin (preferably (meth)acrylic-type resin) whose glass transition temperature is 30 degrees C or less, for example, Preferably it is 0.1-10 mass parts, More preferably It is 1-7 mass parts.

The pressure-sensitive adhesive composition (3) may further contain one or more additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a pigment, a rust inhibitor, an inorganic filler, and light scattering fine particles.

As a method of forming the pressure-sensitive adhesive layer with the pressure-sensitive adhesive composition (3), it is dissolved or dispersed in a solvent to obtain a solvent-containing composition, and then applied to the surface of a substrate (such as a plastic film) or another optical layer and dried, etc. can be heard

The pressure-sensitive adhesive layer may be bonded to another layer after forming the pressure-sensitive adhesive layer on the release film, and after peeling the release film, the pressure-sensitive adhesive layer may be bonded to the surface of the pressure-sensitive adhesive layer from which the release film has been peeled and another layer. In addition, the pressure-sensitive adhesive layer may be bonded to another release film after forming the pressure-sensitive adhesive layer on the release film, stored in a state sandwiched between the release films, and may be bonded to the optical layer by peeling the release film during use.

<Adhesive layer>

An adhesive bond layer is used in order to bond optical layers, an optical layer and another layer, or another layer, or to fix an optical layer to another object. The adhesive layer can be formed by curing the adhesive composition, and a thermosetting adhesive in which the thermosetting component is cured by heat curing, or an active energy ray-curable adhesive in which the active energy ray composition is irradiated with an active energy ray to cure it can be used.

<Active energy ray-curable composition>

An active energy ray-curable composition is a composition which receives irradiation of an active energy ray and hardens|cures. As an active energy ray, an ultraviolet-ray, an electron beam, X-ray, visible light, etc. are mentioned, Preferably it is an ultraviolet-ray. As the ultraviolet light source, a light source having a light emission distribution at a wavelength of 400 nm or less is preferable, for example, a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultra-high pressure mercury lamp, a chemical lamp, a black light lamp, a microwave excited mercury lamp, a metal halide lamp, etc. can be heard

The active energy ray-curable composition (hereinafter, sometimes referred to as active energy ray-curable composition (2)) forming the optical layer of the present invention contains at least a photocurable component and compound (X), and further contains a photoinitiator. It is preferable to do

As a photocurable component, the compound or oligomer (radical polymerizable compound) hardened|cured by the radical polymerization reaction by irradiation of an active energy ray, and the compound hardened|cured by the cationic polymerization reaction by irradiation of an active energy ray (cationically polymerizable compound) , a compound hardened by an anionic polymerization reaction, and the like. The photocurable component may use together a radically polymerizable compound, a cationically polymerizable compound, and an anionically polymerizable compound.

<Radically polymerizable compound>

As a radically polymerizable compound, a radically polymerizable (meth)acrylic-type compound etc. are mentioned. In this specification, a "(meth)acrylic-type compound" means the compound which has one or more (meth)acryloyl groups in a molecule|numerator. The active energy ray-curable adhesive composition can contain 1 type(s) or 2 or more types of radically polymerizable (meth)acrylic-type compound.

As (meth)acrylic compounds, (meth)acrylate monomers having at least one (meth)acryloyloxy group in the molecule, (meth)acrylamide monomers, and (meth)acryloyl groups having at least two (meth)acryloyl groups in the molecule (meth)acryloyl group containing compounds, such as a meth)acryl oligomer, are mentioned. The (meth)acryl oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. A (meth)acrylic-type compound may be used individually by 1 type, and may use 2 or more types together.

As a (meth)acrylate monomer, the monofunctional (meth)acrylate monomer which has one (meth)acryloyloxy group in a molecule|numerator, and bifunctional (meth)acryl which has two (meth)acryloyloxy groups in a molecule|numerator and a polyfunctional (meth)acrylate monomer having 3 or more (meth)acryloyloxy groups in the molecule.

Examples of the monofunctional (meth)acrylate monomer include methyl (meth)acrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, t- alkyl (meth)acrylates such as butyl (meth)acrylate and 2-ethylhexyl (meth)acrylate; Aralkyl (meth)acrylates, such as benzyl (meth)acrylate; (meth)acrylates of terpene alcohols such as isobornyl (meth)acrylate; (meth)acrylates having a tetrahydrofurfuryl structure such as tetrahydrofurfuryl (meth)acrylate; A cycloalkyl group at the alkyl group moiety such as cyclohexyl (meth) acrylate, cyclohexylmethyl methacrylate, dicyclopentanyl acrylate, dicyclopentenyl (meth) acrylate, 1,4-cyclohexanedimethanol monoacrylate, etc. (meth)acrylate having; aminoalkyl (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate; 2-phenoxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, ethyl carbitol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate having an ether bond at the alkyl moiety (meth)acrylate etc. are mentioned.

Moreover, as a monofunctional (meth)acrylate monomer, the monofunctional (meth)acrylate which has a hydroxyl group in an alkyl part; and monofunctional (meth)acrylates having a carboxyl group in the alkyl moiety. Examples of the monofunctional (meth)acrylate having a hydroxyl group in the alkyl moiety include 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acryl. and 2-hydroxy-3-phenoxypropyl (meth)acrylate, trimethylolpropane mono(meth)acrylate, and pentaerythritol mono(meth)acrylate. Examples of the monofunctional (meth)acrylate having a carboxyl group in the alkyl moiety include 2-carboxyethyl (meth)acrylate, ω-carboxypolycaprolactone (n=2) mono(meth)acrylate, 1-[2-( Meth)acryloyloxyethyl]phthalic acid, 1-[2-(meth)acryloyloxyethyl]hexahydrophthalic acid, 1-[2-(meth)acryloyloxyethyl]succinic acid, 4-[2-( meth)acryloyloxyethyl] trimellitic acid, N-(meth)acryloyloxy-N',N'-dicarboxymethyl-p-phenylenediamine, etc. are mentioned.

Examples of the (meth)acrylamide monomer include N-methyl (meth)acrylamide, N-ethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, Nn-butyl (meth)acrylamide, Nt-butyl ( N-alkyl (meth)acrylamide, such as meth)acrylamide and N-hexyl (meth)acrylamide; N,N-dialkyl(meth)acrylamides such as N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide; hydroxyalkyl (meth)acrylamide, such as N-hydroxymethyl(meth)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, and N-(2-hydroxypropyl)(meth)acrylamide; N-acryloylpyrrolidine, 3-acryloyl-2-oxazolidinone, 4-acryloylmorpholine, N-acryloylpiperidine, N-methacryloylpiperidine, etc. are mentioned.

As a bifunctional (meth)acrylate monomer,

Ethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9- alkylene glycol di(meth)acrylates such as nonanediol di(meth)acrylate and neopentyl glycol di(meth)acrylate;

Diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, poly polyoxyalkylene glycol di(meth)acrylates such as propylene glycol di(meth)acrylate and polytetramethylene glycol di(meth)acrylate;

di(meth)acrylates of halogen-substituted alkylene glycols such as tetrafluoroethylene glycol di(meth)acrylate;

di(meth)acrylates of aliphatic polyols such as trimethylolpropane di(meth)acrylate, ditrimethylolpropane di(meth)acrylate, and pentaerythritol di(meth)acrylate;

hydrogenated dicyclopentadiene or di(meth)acrylate of tricyclodecanedialkanol such as hydrogenated dicyclopentadienyldi(meth)acrylate and tricyclodecanedimethanoldi(meth)acrylate;

di(meth)acrylates of dioxane glycol or dioxane dialkanol such as 1,3-dioxane-2,5-diyldi(meth)acrylate [alias: dioxane glycol di(meth)acrylate];

di(meth)acrylates of alkylene oxide adducts of bisphenol A or bisphenol F such as bisphenol A ethylene oxide adduct diacrylate and bisphenol F ethylene oxide adduct diacrylate;

Epoxydi(meth)acrylates of bisphenol A or bisphenol F, such as an acrylic acid adduct of bisphenol A diglycidyl ether and an acrylic acid adduct of bisphenol F diglycidyl ether; silicone di(meth)acrylate;

di(meth)acrylate of hydroxypivalic acid neopentyl glycol ester;

2,2-bis[4-(meth)acryloyloxyethoxyethoxyphenyl]propane; 2,2-bis[4-(meth)acryloyloxyethoxyethoxycyclohexyl]propane;

di(meth)acrylate of 2-(2-hydroxy-1,1-dimethylethyl)-5-ethyl-5-hydroxymethyl-1,3-dioxane];

tris(hydroxyethyl)isocyanurate di(meth)acrylate; and the like.

Examples of the trifunctional or higher polyfunctional (meth)acrylate monomer include glycerin tri(meth)acrylate, alkoxylated glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tri(meth) Acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta poly(meth)acrylates of trifunctional or higher aliphatic polyols such as (meth)acrylate and dipentaerythritol hexa(meth)acrylate; poly(meth)acrylates of trifunctional or more halogen-substituted polyols; tri(meth)acrylate of an alkylene oxide adduct of glycerin; tri(meth)acrylate of the alkylene oxide adduct of trimethylolpropane; 1,1,1-tris[(meth)acryloyloxyethoxyethoxy]propane; Tris (hydroxyethyl) isocyanurate tri (meth) acrylate etc. are mentioned.

As a (meth)acryl oligomer, a urethane (meth)acryl oligomer, a polyester (meth)acryl oligomer, an epoxy (meth)acryl oligomer, etc. are mentioned.

A urethane (meth)acryl oligomer is a compound which has a urethane bond (-NHCOO-) and at least two (meth)acryloyl groups in a molecule|numerator. Specifically, a urethanation reaction product of a hydroxyl group-containing (meth)acryl monomer and polyisocyanate each having at least one (meth)acryloyl group and at least one hydroxyl group in the molecule, or a terminal isoform obtained by reacting a polyol with a polyisocyanate. and a urethanation reaction product of a cyanato group-containing urethane compound and a (meth)acryl monomer each having at least one (meth)acryloyl group and at least one hydroxyl group in the molecule.

The hydroxyl group-containing (meth)acrylic monomer used in the urethanation reaction may be, for example, a hydroxyl group-containing (meth)acrylate monomer, and specific examples thereof include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, glycerin di(meth)acrylate, trimethylolpropane di(meth)acrylate , pentaerythritol tri (meth) acrylate, and dipentaerythritol penta (meth) acrylate. Specific examples other than the hydroxyl group-containing (meth)acrylate monomer include N-hydroxyalkyl (meth)acrylamide monomers such as N-hydroxyethyl (meth)acrylamide and N-methylol (meth)acrylamide. .

Examples of the polyisocyanate used for the urethanation reaction with the hydroxyl group-containing (meth)acrylic monomer include hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate, Among these diisocyanates, diisocyanates obtained by hydrogenating aromatic isocyanates (eg, hydrogenated tolylene diisocyanate, hydrogenated xylylene diisocyanate, etc.), triphenylmethane triisocyanate, di- or tri -isocyanate and the polyisocyanate obtained by making the said diisocyanate multimer, etc. are mentioned.

Moreover, as a polyol used in order to set it as the urethane compound containing a terminal isocyanato group by reaction with polyisocyanate, besides an aromatic, aliphatic or alicyclic polyol, polyester polyol, polyether polyol, etc. can be used. Examples of the aliphatic and alicyclic polyols include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethyl Allpropane, pentaerythritol, dipentaerythritol, dimethylolheptane, dimethylolpropionic acid, dimethylolbutanoic acid, glycerin, hydrogenated bisphenol A, etc. are mentioned.

A polyester polyol is obtained by the dehydration-condensation reaction of the said polyol, polybasic carboxylic acid, or its anhydride. Examples of polybasic carboxylic acids or their anhydrides are expressed by adding "(anhydrous)" to what may be anhydride, (anhydride) succinic acid, adipic acid, (anhydride) maleic acid, (anhydride) itaconic acid, (anhydride) trimellitic acid, (anhydrous) pyromellitic acid, (anhydrous) phthalic acid, isophthalic acid, terephthalic acid, hexahydro (anhydrous) phthalic acid, and the like.

The polyether polyol may be a polyoxyalkylene-modified polyol obtained by reaction of the polyol or dihydroxybenzenes with an alkylene oxide other than polyalkylene glycol.

A polyester (meth)acrylate oligomer means the oligomer which has an ester bond and at least two (meth)acryloyloxy groups in a molecule|numerator.

The polyester (meth)acrylate oligomer can be obtained by, for example, subjecting (meth)acrylic acid, a polybasic carboxylic acid or an anhydride thereof, and a polyol to a dehydration condensation reaction.

Examples of the polybasic carboxylic acid or anhydride thereof include succinic anhydride, adipic acid, maleic anhydride, itaconic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, phthalic acid, succinic acid, maleic acid, and itaconic acid. , trimellitic acid, pyromellitic acid, hexahydrophthalic acid, phthalic acid, isophthalic acid, terephthalic acid, and the like.

Examples of the polyol include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaeryth and ritol, dipentaerythritol, dimethylolheptane, dimethylolpropionic acid, dimethylolbutanoic acid, glycerin, and hydrogenated bisphenol A.

The epoxy (meth)acryl oligomer can be obtained by addition reaction of polyglycidyl ether and (meth)acrylic acid. The epoxy (meth)acryl oligomer has at least two (meth)acryloyloxy groups in the molecule.

As polyglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, bisphenol A diglycidyl dil ether etc. are mentioned.

<Cation polymerizable compound>

A cationically polymerizable compound is a compound or oligomer which a cationic polymerization reaction advances and hardens|cures by irradiation or heating of active energy rays, such as an ultraviolet-ray, visible light, an electron beam, and X-ray. As a cationically polymerizable compound, an epoxy compound, an oxetane compound, a vinyl compound, etc. are mentioned. A cationically polymerizable compound may be used independently and may use several types together.

The cationically polymerizable compound is preferably an epoxy compound. An epoxy compound is a compound which has 1 or more (preferably 2 or more) epoxy groups in a molecule|numerator.

As an epoxy compound, an alicyclic epoxy compound, an aromatic epoxy compound, a hydrogenated epoxy compound, an aliphatic epoxy compound, etc. are mentioned.

An alicyclic epoxy compound is a compound which has one or more epoxy groups couple|bonded with the alicyclic ring in a molecule|numerator. As an epoxy group couple|bonded with the alicyclic ring, an epoxycyclopentane structure, an epoxycyclohexane structure, etc. are mentioned, for example. Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate; 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexanecarboxylate; ethylenebis(3,4-epoxycyclohexanecarboxylate); bis(3,4-epoxycyclohexylmethyl)adipate; bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; diethylene glycol bis (3,4-epoxycyclohexylmethyl ether); ethylene glycol bis (3,4-epoxycyclohexylmethyl ether); 2,3,14,15-diepoxy-7,11,18,21-tetraoxatrispiro[5.2.2.5.2.2]henicoic acid; 3-(3,4-epoxycyclohexyl)-8,9-epoxy-1,5-dioxaspiro[5.5]undecane; 4-vinylcyclohexene dioxide; limonene dioxide; bis(2,3-epoxycyclopentyl)ether; Dicyclopentadiene dioxide etc. are mentioned.

An aromatic epoxy compound is a compound which has an aromatic ring and an epoxy group in a molecule|numerator. As an aromatic epoxy compound, Bisphenol-type epoxy compounds, such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, and diglycidyl ether of bisphenol S, or its oligomer; novolak-type epoxy resins such as phenol novolac epoxy resins, cresol novolac epoxy resins, and hydroxybenzaldehyde phenol novolac epoxy resins; Polyfunctional epoxy compounds such as glycidyl ether of 2,2',4,4'-tetrahydroxydiphenylmethane and glycidyl ether of 2,2',4,4'-tetrahydroxybenzophenone ; and polyfunctional epoxy resins such as epoxidized polyvinyl phenol.

The hydrogenated epoxy compound is a glycidyl ether of a polyol having an alicyclic ring, and a nuclear hydrogenated polyhydroxy compound obtained by selectively hydrogenating an aromatic polyol to an aromatic ring under pressure in the presence of a catalyst is glycidyl It may be etherified. Specific examples of the aromatic polyol include, for example, bisphenol-type compounds such as bisphenol A, bisphenol F, and bisphenol S; novolak-type resins such as phenol novolak resin, cresol novolak resin, and hydroxybenzaldehyde phenol novolak resin; and polyfunctional compounds such as tetrahydroxydiphenylmethane, tetrahydroxybenzophenone and polyvinylphenol. It can be set as glycidyl ether by making epichlorohydrin react with the alicyclic polyol obtained by performing a hydrogenation reaction on the aromatic ring of an aromatic polyol. As a preferable thing among hydrogenated epoxy compounds, the diglycidyl ether of hydrogenated bisphenol A is mentioned.

An aliphatic epoxy compound is a compound which has at least 1 oxylan ring (3-membered cyclic ether) couple|bonded with an aliphatic carbon atom in a molecule|numerator. For example, monofunctional epoxy compounds, such as butyl glycidyl ether and 2-ethylhexyl glycidyl ether; bifunctional epoxy compounds such as 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, and neopentyl glycol diglycidyl ether; trifunctional or more trifunctional epoxy compounds such as trimethylolpropane triglycidyl ether and pentaerythritol tetraglycidyl ether; and an epoxy compound having one epoxy group directly bonded to an alicyclic ring, such as 4-vinylcyclohexene dioxide and limonene dioxide, and an oxylan ring bonded to an aliphatic carbon atom.

An oxetane compound is a compound containing one or more oxetane rings (oxetanyl group) in a molecule|numerator. Examples of the oxetane compound include 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, 1,4-bis[{(3-ethyloxetan-3-yl)methoxy}methyl]benzene; 3-ethyl-3[{(3-ethyloxetan-3-yl)methoxy}methyl]oxetane, 3-ethyl-3-(phenoxymethyl)oxetane, 3-(cyclohexyloxy)methyl- 3-ethyloxetane etc. are mentioned.

As a vinyl compound, an aliphatic or alicyclic vinyl ether compound is mentioned. Examples of the vinyl compound include n-amyl vinyl ether, i-amyl vinyl ether, n-hexyl vinyl ether, n-octyl vinyl ether, 2-ethylhexyl vinyl ether, n-dodecyl vinyl ether, stearyl vinyl ether, oleyl. vinyl ethers of alkyl or alkenyl alcohols having 5 to 20 carbon atoms such as vinyl ether; hydroxyl group-containing vinyl ethers such as 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, and 4-hydroxybutyl vinyl ether; vinyl ethers of monoalcohols having an aliphatic ring or an aromatic ring, such as cyclohexyl vinyl ether, 2-methylcyclohexyl vinyl ether, cyclohexylmethyl vinyl ether, and benzyl vinyl ether; Glycerol monovinyl ether, 1,4-butanediol monovinyl ether, 1,4-butanediol divinyl ether, 1,6-hexanediol divinyl ether, neopentyl glycol divinyl ether, pentaerythritol divinyl ether, pentaerythritol Tetravinyl ether, trimethylol propane divinyl ether, trimethylol propane trivinyl ether, 1,4-dihydroxycyclohexane monovinyl ether, 1,4-dihydroxycyclohexane divinyl ether, 1,4-dihydro mono-polyvinyl ethers of polyhydric alcohols such as hydroxymethylcyclohexane monovinyl ether and 1,4-dihydroxymethylcyclohexanedivinyl ether; polyalkylene glycol mono to divinyl ethers such as diethylene glycol divinyl ether, triethylene glycol divinyl ether, and diethylene glycol monobutyl monovinyl ether; Glycidyl vinyl ether, ethylene glycol vinyl ether methacrylate, etc. are mentioned.

Content of a photocurable component is 50-99.5 mass % normally with respect to 100 mass % of solid content of active energy ray-curable composition (2), Preferably it is 70-97 mass %.

Content of compound (X) is 0.01-50 mass parts normally with respect to 100 mass parts of photocurable components, Preferably it is 0.1-20 mass parts, More preferably, it is 0.5-10 mass parts, More preferably, it is 0.5 -5 parts by mass.

<Photoinitiator>

(Photoradical polymerization initiator)

When the photocurable component is a radical polymerization compound, the photopolymerization initiator contains a photoradical polymerization initiator. Moreover, you may contain the thermal radical polymerization initiator further. A photoradical polymerization initiator initiates the polymerization reaction of a radically curable compound by irradiation of active energy rays like visible light, an ultraviolet-ray, an X-ray, or an electron beam.

As the photo-radical polymerization initiator and the thermal-radical polymerization initiator, conventionally known ones can be used. Examples of the photo-radical polymerization initiator include acetophenone, 3-methylacetophenone, benzyl dimethyl ketal, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 2-methyl-1- acetophenone-based initiators such as [4-(methylthio)phenyl-2-morpholinopropan-1-one and 2-hydroxy-2-methyl-1-phenylpropan-1-one; benzophenone-based initiators such as benzophenone, 4-chlorobenzophenone, and 4,4'-diaminobenzophenone; benzoin ether initiators such as benzoin propyl ether and benzoin methyl ether benzoin ethyl ether; thioxanthone-based initiators such as 4-isopropylthioxanthone; xanthone, fluorenone, camphorquinone, benzaldehyde, anthraquinone and the like; 1-[4-(phenylthio)phenyl]-, 2-(o-benzoyloxime)-1,2-octanedione, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole- Oxime ester system initiators, such as 3-yl]- and 1-(o-acetyl oxime)-ethanone, etc. are mentioned.

A photoradical polymerization initiator may use 2 or more types together.

Content of a photoradical polymerization initiator is 0.01-20 mass parts normally with respect to 100 mass parts of radically polymerizable compounds, Preferably it is 0.1-10 mass parts, More preferably, it is 0.5-5 mass parts. By containing 0.5 mass parts or more of a radical polymerization initiator, a radically polymerizable compound can fully be hardened|cured.

(photocationic polymerization initiator)

When a photocurable component is a cationically polymerizable compound, a photoinitiator is a photocationic polymerization initiator. A photocationic polymerization initiator generates a cationic species or a Lewis acid by irradiation of an active energy ray like a visible light, an ultraviolet-ray, X-ray, or an electron beam, and initiates the polymerization reaction of a cation-curable compound. As a compound which generates a cationic species or a Lewis acid by irradiation of an active energy ray, For example, Onium salts, such as an aromatic iodonium salt and an aromatic sulfonium salt; aromatic diazonium salts; An iron-arene complex etc. are mentioned.

The aromatic iodonium salt is a compound having a diaryliodonium cation, and examples of the cation include typically a diphenyliodonium cation. The aromatic sulfonium salt is a compound having a triarylsulfonium cation, and examples of the cation include a triphenylsulfonium cation and a 4,4'-bis(diphenylsulfonio)diphenylsulfide cation. have. An aromatic diazonium salt is a compound which has a diazonium cation, and a benzenediazonium cation is mentioned typically as said cation. In addition, the iron-arene complex is typically a cyclopentadienyl iron(II) arene cation complex salt.

The cation shown above is paired with an anion (anion) and comprises a photocationic polymerization initiator. Examples of anions constituting the photocationic polymerization initiator include a special phosphorus anion [(Rf) _n PF _6-n ] ^- , hexafluorophosphate anion PF ₆ ^- , hexafluoroantimonate anion SbF ₆ ^- , pentafluoro rhohydroxyantimonate anion SbF ₅ (OH) ^- , hexafluoroacetate anion AsF ₆ ^- , tetrafluoroborate anion BF ₄ ^- , tetrakis(pentafluorophenyl)borate anion B(C ₆ F ₅ ) ₄ ^- and so on. Among them, from the viewpoint of the curability of the cationically polymerizable compound and the safety of the resulting optical layer, a special phosphorus anion [(Rf) _n PF _6-n ] ^- , hexafluorophosphate anion PF ₆ ^- , tetrakis (pentafluorophenyl) ) borate anion B(C ₆ F ₅ ) ₄ ^- is preferred.

A photocationic polymerization initiator may use 2 or more types together. Among them, aromatic sulfonium salts are preferable in that they have ultraviolet absorption characteristics even in a wavelength region of around 300 nm, are excellent in curability, and can provide a cured product having good mechanical strength and adhesive strength.

Content of a photocationic polymerization initiator is 0.01-20 mass parts normally with respect to 100 mass parts of cationically polymerizable compounds, Preferably it is 0.1-10 mass parts, More preferably, it is 0.5-5 mass parts. By mix|blending 0.5 mass parts or more of a photocationic polymerization initiator, a cationically polymerizable compound can fully be hardened|cured.

From the viewpoint of curability of the adhesive composition and control of the effect of coloring upon curing, the adhesive composition preferably contains a radically polymerizable curing component, and preferably contains a radically polymerizable (meth)acrylic component. Moreover, it is preferable to contain an oxime ester type photoradical polymerization initiator from a sclerosis|hardenable viewpoint. Moreover, it is preferable that it is a solvent-free type|system|group.

As the thermosetting adhesive, a thermosetting compound having a functional group capable of reacting with heat can be used. The thermosetting compound may be any of a monomer, an oligomer, or a polymer. Examples of functional groups that can be reacted with heat include an epoxy group, a hydroxyl group, a carboxyl group, an amino group, a thiol group, an isocyanate group, a silanol group, an alkoxysilyl group, a cyanate group, an amide group, an acid anhydride group, an aldehyde group, an acetoacetyl group, a diketone group and the like.

Although the thermosetting component may use only a single functional group, since it hardens efficiently at a lower temperature, it is preferable to combine several functional group. Moreover, you may use a crosslinking agent together separately.

The adhesive composition may contain additives as needed. Examples of the additive include an ion trapping agent, a chain transfer agent, a polymerization accelerator, a sensitizer, a sensitizer auxiliary, a filler, a flow regulator, a plasticizer, an antifoaming agent, a leveling agent, a light-transmitting fine particle, an organic solvent, etc., a thermal polymerization initiator, a blocking agent, an antifouling agent , a surfactant, a curing agent, a viscosity modifier, an antifouling agent, a slip agent, a refractive index modifier, and a dispersant.

<Hard coat layer>

The hard coat layer is a layer having a function of preventing the optical layer or other layers from being damaged or dented, and most of them are laminated on a protective film or the like.

The hard coat layer can be formed from the same components as the adhesive composition described above. It is preferable that the composition which forms a hard-coat layer is an active-energy-ray-curable composition (2).

It is preferable to contain a photo-radically polymerizable component from the point of being easy to adjust the performance of the abrasion resistance, hardness, and softness|flexibility of a hard-coat layer, More preferably, it is preferable to contain a (meth)acrylic-type component. Moreover, it is preferable to contain the polyfunctional (meth)acrylate of trifunctional or more from the point which it is easy to fully raise abrasion resistance and hardness. In addition, in order to provide flexibility, it is preferable to include a urethane acryl oligomer. It is also preferable to include a photoradical initiator. From the viewpoint of curability, the photoradical initiator is preferably an oxime ester-based initiator. Moreover, it is preferable to contain a leveling agent from a viewpoint of the leveling property of the liquid surface at the time of base material coating.

As a leveling agent, well-known things, such as a fluorine-type leveling agent, a silicone-type leveling agent, and an acryl-type leveling agent, are mentioned, for example. When it contains a leveling agent, it is preferable that it is 0.01-1 mass part with respect to 100 mass parts of photocurable components.

Any of an organic solvent, water, and nonsolvent may be sufficient as the composition which forms a hard-coat layer. It is preferable to include an organic solvent from the point of the point which control of a viscosity is easy, the point rich in the kind of hardening component which can be melt|dissolved, and a leveling property.

Examples of the organic solvent include aliphatic hydrocarbons such as hexane, cyclohexane and octane; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, 1-propanol, isopropanol, n-butanol, s-butanol, t-butanol, benzyl alcohol, ethylene glycol and cyclohexanol; ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, heptanone, diisobutyl ketone, and diethyl ketone; esters such as ethyl acetate, butyl acetate, and isobutyl acetate; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether; esterified glycol ethers such as ethylene glycol monomethyl ether acetate and propylene glycol monomethyl ether acetate; cellosolves such as 2-methoxyethanol, 2-ethoxyethanol, and 2-butoxyethanol; carbitols such as 2-(2-methoxyethoxy)ethanol, 2-(2-ethoxyethoxy)ethanol, and 2-(2-butoxyethoxy)ethanol; aliphatic hydrocarbons such as hexane and cyclohexane; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; aromatic hydrocarbons such as benzene, toluene, and xylene; amides such as dimethylformamide, dimethylacetamide, and n-methylpyrrolidone; ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ether alcohols, such as 1-methoxy-2- propanol, etc. are mentioned.

You may use these organic solvents in mixture of several types as needed. When the active energy ray-curable composition 2 contains an organic solvent, it is necessary to evaporate the organic solvent after coating. Therefore, it is preferable that an organic solvent has a boiling point in the range of 60 degreeC - 160 degreeC. Moreover, it is preferable that the saturated vapor pressure at 20 degreeC exists in the range of 0.1 kPa - 20 kPa.

The optical layer of the present invention can be formed by coating the active energy ray-curable composition (2) on a substrate (plastic film, etc.) or other optical layer to form a coating film, and drying the coating film after drying if necessary. . That is, the hardened|cured material of the active-energy-ray-curable composition (2) is the optical layer of this invention.

As a method of applying the active energy ray-curable composition (2) to form a coating film, for example, a spin coat method, a dip method, a spray method, a die coat method, a bar coat method, a roll coater method, a meniscus coater method, a flexographic printing method Well-known various methods, such as the method, the screen printing method, and the bead coater method, are mentioned.

It does not specifically limit as a method of drying. The drying temperature is usually 30 to 120°C, and the drying time is preferably 3 to 300 seconds.

After apply|coating the active energy ray-curable composition 2 to a base material etc., a coating film can be hardened by irradiating an active energy ray to a coating film. Although the active energy ray irradiation intensity is determined by the mixing|blending of the active energy ray-curable composition (2), it is preferable to make it so that the light irradiation intensity of the wavelength region effective for activation of a photoinitiator may become 0.1-2000 mW/cm<2>. In addition, although the light irradiation time with respect to the coating film of the active energy ray-curable composition (2) is also determined by the compounding of the active energy ray-curable composition (2), the accumulated light amount expressed as the product of the light irradiation intensity and the light irradiation time is 10 It is preferable to set it so that it may become -5000 mJ/cm<2>.

When the optical layer formed of the active energy ray-curable composition (2) is a hard coat layer, the thickness of the hard coat layer is preferably 0.5 to 20 µm, more preferably 1 to 10 µm, still more preferably 2 -7 mu m, particularly preferably 3-5 mu m.

Moreover, when the optical layer formed from the active energy ray-curable composition (2) is a hard-coat layer, content of compound (X) is 0.01-50 mass parts normally with respect to 100 mass parts of photocurable components, Preferably it is 0.1 It is -20 mass parts, More preferably, it is 0.5-10 mass parts, More preferably, it is 0.5-5 mass parts.

<Optical laminate>

This invention also includes the optical laminated body containing the optical layer of this invention and another layer. As another layer, the above-mentioned arbitrary optical layer may be sufficient. Any one layer may be sufficient as the optical layer containing compound (X) among the several optical layer laminated|stacked, and multiple layers may be sufficient as it.

When the optical layer is laminated, it is preferably laminated through an adhesive layer or a pressure-sensitive adhesive layer. When passing through an adhesive layer, for example, a laminate can be formed by applying an adhesive composition to either optical layer, bonding the other optical layer, and then curing it by heating or irradiation with an active energy ray. In the case of using a solvent-based or water-based adhesive composition, the adhesive composition may be applied to the optical layer and dried to remove the solvent, and then bonded to the optical layer, or the solvent may be dried and removed after bonding.

When laminating through an adhesive layer, similarly to the adhesive layer, the adhesive composition may be applied and bonded to one optical layer, but the adhesive layer is first formed on the release film, transferred to the optical layer, and then the release film is peeled off By doing so, you may bond to an optical layer.

Moreover, the adhesive bond layer formed from a well-known adhesive composition may be sufficient as an adhesive bond layer and an adhesive layer, the adhesive layer formed from a well-known adhesive composition may be sufficient, and the optical layer of this invention may be sufficient as it.

The cross-sectional schematic diagrams of the laminated constitution of the optical laminated body of this invention are shown in FIGS.

The optical laminated body 10 described in FIG. 1 is a laminated body containing the optical film 40, the optical layer 3, and the light emitting element 30. As shown in FIG. Here, the optical layer 3 is preferably an optical layer formed of the pressure-sensitive adhesive composition (3). The optical layer 3 may be a pressure-sensitive adhesive layer having an adhesive function.

10A of optical laminated body described in FIG. 2 is a laminated body containing the optical layer 1 of this invention, the adhesive bond layer 4, the polarizer 5, the adhesive agent layer 6, and the protective film 7 . Here, it is preferable that the optical layer (1) of this invention is an optical layer formed of the resin composition (1). The optical layer 1 functions as a protective film of a polarizer. Moreover, the optical layer of this invention may be sufficient as the protective film 7, and a well-known protective film may be sufficient as it. In addition, if the adhesive bond layer 4 is a well-known adhesive bond layer, it will not specifically limit, A well-known water-system adhesive agent may be sufficient, and a well-known active energy ray hardening-type adhesive agent may be sufficient as it.

The optical laminated body 10B of FIG. 3 is the optical laminated body containing the protective film 7, the adhesive bond layer 4, the polarizer 5, the optical layer 2 of this invention, and the protective film 8. . Here, the optical layer 2 is preferably an optical layer formed of the active energy ray-curable composition 2, and the optical layer may be an adhesive layer having an adhesive function.

The optical laminate 10C described in FIG. 4 is a laminate including an optical layer 2 , a protective film 7 , an adhesive layer 4 , a polarizer 5 , an adhesive layer 6 , and a protective film 8 . it's a chain Here, the optical layer (2) is preferably an optical layer formed of the active energy ray-curable composition (2), and the optical layer may be a surface treatment layer.

The optical laminated body 10D of FIG. 5 and the optical laminated body 10E of FIG. 6 are the surface treatment layer 20, the protective film 7, the adhesive bond layer 4, the polarizer 5, and the adhesive agent layer. (6), it is an optical laminated body containing the optical film 40, the adhesive layer 6a, and the light emitting element 30 (liquid crystal cell, organic electroluminescent cell).

The optical laminated body described in FIG.5 and FIG.6 is an example of the laminated body containing a multilayer retardation film. For example, the laminate shown in FIG. 5 includes a quarter-wave retardation layer 50 that imparts a phase difference of 1/4 wavelength to transmitted light and a half-wave retardation layer that imparts a phase difference of 1/2 wavelength to transmitted light. 70 includes a retardation film 110 laminated through an adhesive layer or an adhesive layer 60 . In addition, the laminate shown in FIG. 6 is a configuration diagram including an optical film 40 in which a quarter-wave retardation layer 50a and a positive C layer 80 are laminated through an adhesive layer 60 can

In FIG. 5 , the quarter-wave retardation layer 50 imparting a phase difference of 1/4 wavelength, and the half-wave retardation layer 70 imparting a phase difference of 1/2 wavelength to transmitted light are the first The retardation film of the form may be sufficient, and the retardation film of the 5th form may be sufficient. In the case of the structure of FIG. 4, it is more preferable that at least one is a 5th aspect.

It is preferable that it is an optical film of the said 1st form, and, as for the 1/4 wavelength retardation layer 50a in FIG. 6, it is more preferable to satisfy Formula (7) and Formula (8).

5 and 6, any of the surface treatment layer 20, the protective film 7, the adhesive layer 4, the pressure-sensitive adhesive layer 6, and the pressure-sensitive adhesive layer 6a may be the optical layer of the present invention. . The surface treatment layer 20 may be an optical layer formed of the active energy ray-curable composition 2 described above, or may be a known surface treatment layer. Moreover, as for the surface treatment layer 20, a hard-coat layer etc. are mentioned, for example. The adhesive layer 4 may be an optical layer formed from the active energy ray-curable composition 2 mentioned above, and the adhesive agent formed from a well-known adhesive composition may be sufficient as it. An adhesive bond layer may be sufficient as the adhesive agent layer 6, and an adhesive layer may be sufficient as it. When the adhesive layer 6 is an adhesive bond layer, the optical layer formed from the above-mentioned active energy ray-curable composition may be sufficient, and the adhesive agent formed from a well-known adhesive composition may be sufficient. When the adhesive layer 6 is an adhesive layer, the adhesive layer formed from the above-mentioned adhesive composition may be sufficient, and the adhesive layer formed from a well-known adhesive composition may be sufficient. The optical layer formed from the resin composition 1 mentioned above may be sufficient as the protective film 7, and a well-known protective film may be sufficient as it. An optical layer formed from the above-mentioned adhesive composition 3 may be sufficient as the adhesive layer 6a, and the adhesive layer formed from a well-known adhesive composition may be sufficient as it. 5 or 6, in the case of an optical laminate, the surface treatment layer 20 or the pressure-sensitive adhesive layer 6 is preferably the optical layer of the present invention, the pressure-sensitive adhesive layer 6 is the above-described pressure-sensitive adhesive composition (3) It is more preferable that it is an adhesive layer formed with

<Image display device>

The optical layer of this invention and the optical laminated body containing the said optical layer are laminated|stacked on display elements, such as an organic electroluminescent element and a liquid crystal cell, and image display apparatuses (FPD: flat panel display), such as an organic electroluminescent display device and a liquid crystal display device. ) is available for

When the optical layer of the present invention is used as an optical laminate or an image display device, the order in which the optical layer and other optical layers in the laminate are laminated is not particularly limited, but from the viewpoint of suppressing light deterioration of a liquid crystal retardation film or an organic EL light emitting element. In, the optical layer containing the compound (X) is preferably disposed on the viewing side than the liquid crystal retardation film or the organic EL light emitting device.

Example

Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated more concretely, this invention is not limited by these examples. In the examples, % and parts indicating the content or the amount used are based on mass unless otherwise specified.

(Synthesis Example 1) Synthesis of the compound represented by the formula (UVA-1)

The inside of a 300 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer was made into a nitrogen atmosphere, 5 parts of 2-methyl 1,3-cyclohexanedione, 3.7 parts of piperidine, and 50 parts of toluene were put, and it refluxed and stirred for 5 hours. . The solvent was distilled off from the obtained mixture, refinement|purification was performed, and 6.8 parts of compounds represented by Formula (M-1) were obtained.

In a nitrogen atmosphere, the obtained compound represented by the formula (M-1), 1.3 parts of dimethyl sulfuric acid, and 4 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. 0.75 parts of malononitrile, 1.2 parts of triethylamine, and 4 parts of isopropanol were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.3 parts of the compound represented by the formula (UVA-1).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-1) was produced.

¹ H-NMR (heavy dimethyl sulfoxide (hereinafter sometimes referred to as heavy DMSO) δ: 1.68-1.75 (m, 8H), 2.16 (s, 3H), 2.50-2.62 (dt, 4H) 3.40-3.43 (t, 4H)

LC-MS; [M+H] ⁺ =242.5

<Measurement of maximum absorption wavelength and gram extinction coefficient ε>

A 2-butanone solution (0.006 g/L) of the compound represented by the obtained formula (UVA-1) was placed in a 1 cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), The absorbance in the wavelength range of 300 to 800 nm was measured for every 1 nm step by the double beam method. The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound represented by the formula (UVA-1) in the solution, and the optical path length of the quartz cell.

ε(λ)=A(λ)/CL

[wherein ε(λ) represents the gram extinction coefficient (L/(g·cm)) of the compound represented by the formula (UVA-1) at the wavelength of λ nm, and A(λ) is the gram extinction coefficient (L/(g·cm)) at the wavelength of λ nm. Absorbance is shown, C is concentration (g/L), and L is optical path length (cm) of the quartz cell.]

The maximum absorption wavelength of the compound represented by the obtained formula (UVA-1) was 412.9 nm. ε(λmax) of the compound represented by the obtained formula (UVA-1) is 1.946 L/(g·cm), ε(λmax+30 nm) is 0.138 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 14.1.

(Synthesis Example 2) Synthesis of the compound represented by the formula (UVA-2)

The inside of a 300 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer was made into a nitrogen atmosphere, 5 parts of 2-methyl 1, 3- cyclopentanedione, 4.2 parts of piperidine, and 50 parts of toluene were put, and it was refluxed and stirred for 5 hours. . The solvent was distilled off from the obtained mixture, refinement|purification was performed, and 4 parts of compounds represented by Formula (M-2) were obtained.

In a nitrogen atmosphere, the compound represented by the obtained formula (M-2), 1.7 parts of dimethyl sulfuric acid, and 4.5 parts of acetonitrile were mixed, and the mixture was stirred at 20 to 30°C for 3 hours. To the resulting mixture were added 2.4 parts of (2-ethylbutyl)cyanoacetate, 1.4 parts of triethylamine and 4.5 parts of isopropanol, followed by stirring at 20 to 30°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.5 parts of the compound represented by the formula (UVA-2).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-2) was produced.

¹ H-NMR (heavy DMSO) δ: 0.89-0.93 (t, 6H), 1.36-1.48 (m, 4H), 1.52-1.62 (m, 2H) 1.69-1.71 (m, 6H), 2.22 (s, 3H) ), 2.57-2.60 (t, 2H), 3.15-3.18 (t, 2H), 3.53-3.55 (t, 4H), 4.05-4.06 (d, 2H)

LC-MS; [M+H] ⁺ =331.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-2) was 382.6 nm. ε(λmax) of the compound represented by the obtained formula (UVA-2) is 1.9 L/(g·cm), ε(λmax+30 nm) is 0.057 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 33.3.

(Synthesis Example 3) Synthesis of the compound represented by the formula (UVA-3)

In a nitrogen atmosphere, 2 parts of the compound represented by the formula (M-2), 1.5 parts of dimethyl sulfuric acid, and 4 parts of acetonitrile were mixed, and the mixture was stirred at 20 to 30°C for 3 hours. To the resulting mixture were added 0.8 parts of malononitrile, 1.2 parts of triethylamine and 4 parts of isopropanol, followed by stirring at 20 to 30°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.7 parts of the compound represented by the formula (UVA-3).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (UVA-3) was produced.

¹ H-NMR (heavy DMSO) δ: 1.69-1.74 (m, 6H), 2.19 (s, 3H), 2.65-2.81 (dt, 4H) 3.57-3.59 (t, 4H)

LC-MS; [M+H] ⁺ =228.5(+H)

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-3) was 376.8 nm. ε(λmax) of the compound represented by the obtained formula (UVA-3) is 2.81 L/(g·cm), ε(λmax+30 nm) is 0.058 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 48.4.

(Synthesis Example 4) Synthesis of the compound represented by the formula (UVA-4)

In a nitrogen atmosphere, 1.5 parts of 1,7-dimethyl-1-2,3,4,6,7,8-hexahydroquinolin-5(1H)-one, 1.1 parts of dimethyl sulfuric acid, and 9 parts of acetonitrile are added, and 20 to It stirred at 30 degreeC for 3 hours. 0.6 parts of malononitrile, 0.9 parts of triethylamine, and 9 parts of isopropanol were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.2 parts of the compound represented by the formula (UVA-4).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-4) was produced.

¹ H-NMR (heavy DMSO) δ: 1.08-1.09 (d, 3H), 1.76-2.13 (m, 5H), 2.55-2.59 (dd, 1H), 2.66-2.74 (m, 1H), 2.81-2.93 ( m, 2H), 3.12 (s, 3H), 3.28-3.37 (m, 2H)

LC-MS; [M+H] ⁺ =228.2

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-4) was 401.8 nm. ε(λmax) of the compound represented by the obtained formula (UVA-4) is 2.76 L/(g·cm), ε(λmax+30 nm) is 0.055 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 50.1.

(Synthesis Example 5) Synthesis of the compound represented by the formula (UVA-5)

In a nitrogen atmosphere, 1.5 parts of 1,7-dimethyl-1-2,3,4,6,7,8-hexahydroquinolin-5(1H)-one, 1.1 parts of dimethyl sulfuric acid and 9 parts of acetonitrile are mixed, 20 The mixture was stirred at -30°C for 3 hours. To the resulting mixture were added 1.6 parts of (2-ethylbutyl)cyanoacetate, 0.9 parts of triethylamine and 9 parts of isopropanol, followed by stirring at 20 to 30°C for 3 hours. The solvent was distilled off from the obtained mixture, and refinement|purification was performed, and 1 part of the compound represented by Formula (UVA-5) was obtained.

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-5) was produced.

¹ H-NMR (heavy DMSO) δ: 0.89-0.93 (t, 6H), 1.07-1.08 (d, 3H), 1.36-1.48 (m, 4H), 1.57-1.62 (m, 3H), 1.82-2.04 ( m, 4H), 2.04-2.21 (dd, 1H), 2.52-2.57 (dd, 1H), 2.73 (m, 1H), 3.09 (s, 3H), 3.30-3.33 (t, 2H), 4.04-4.06 ( dd, 2H)

LC-MS; [M+H] ⁺ =: 331.2

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-5) was 412.7 nm. ε(λmax) of the compound represented by the obtained formula (UVA-5) is 1.36 L/(g cm), ε(λmax+30 nm) is 0.202 L/(g cm), ε(λmax)/ε( λmax+30 nm) was 6.74.

(Synthesis Example 6) Synthesis of the compound represented by the formula (UVA-6)

The inside of a 500 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer was made into nitrogen atmosphere, 20 parts of dimedone, 11.2 parts of pyrrolidine, and 200 parts of toluene were put, and it refluxed and stirred for 5 hours. The solvent was distilled off from the obtained mixture, refinement|purification was performed, and 27.4 parts of compounds represented by Formula (M-3) were obtained.

In a nitrogen atmosphere, 1.0 part of the compound represented by the obtained formula (M-3), 2.8 parts of para-toluenesulfonylcyanide, and 10 parts of acetonitrile were mixed. The resulting mixture was stirred at 0-5 DEG C for 5 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.6 parts of the compound represented by the formula (M-4).

In a nitrogen atmosphere, 4.8 parts of the compound represented by the formula (M-4), 4.6 parts of methyl triflate and 24 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. 1.9 parts of malononitrile, 3 parts of triethylamine, and 24 parts of acetonitrile were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 2.9 parts of the compound represented by the formula (UVA-6).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-6) was produced.

¹ H-NMR (CDCl ₃ ) δ: 0.99 (s, 6H), 1.90-1.96 (m, 4H), 2.48-2.51 (m, 4H), 3.70-3.88 (dt, 4H)

LC-MS; [M+H] ⁺ =284.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-6) was 380 nm. ε(λmax) of the compound represented by the obtained formula (UVA-6) is 1.75 L/(g cm), ε(λmax+30 nm) is 0.032 L/(g cm), ε(λmax)/ε( λmax+30 nm) was 54.53.

(Synthesis Example 7) Synthesis of the compound represented by the formula (UVA-7)

In a nitrogen atmosphere, 1 part of the compound represented by the formula (M-4), 0.6 parts of methyl triflate, and 10 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. 5.2 parts of ethyl cyanoacetate, 4.6 parts of triethylamine, and 10 parts of acetonitrile were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.5 parts of the compound represented by the formula (UVA-7).

LC-MS measurement and ¹ H-NMR analysis were performed as described above, and it was confirmed that the compound represented by the formula (UVA-7) was produced.

¹ H-NMR (heavy DMSO) δ: 0.960-0.994 (d, 6H), 1.20-1.26 (m, 3H), 1.93 (m, 4H), 2.53-2.91 (m, 4H), 3.77-3.81 (m, 4H), 4.10-4.19 (m, 2H)

LC-MS; [M+H] ⁺ =314.5(+H)

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-7) was 382.7 nm. ε(λmax) of the compound represented by the obtained formula (UVA-7) is 1.08 L/(g·cm), ε(λmax+30 nm) is 0.153 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 7.04.

(Synthesis Example 8) Synthesis of the compound represented by the formula (UVA-8)

In a nitrogen atmosphere, 0.5 parts of the compound represented by the formula (M-4), 0.5 parts of dimethyl sulfuric acid, and 5 parts of acetonitrile were mixed, and the mixture was stirred and reacted at 20 to 30°C for 3 hours. 0.4 parts of pivaloylacetonitrile, 0.5 parts of triethylamine, and 5.0 parts of acetonitrile were added, followed by stirring at 20 to 30°C for 3 hours. After completion of the reaction, the solvent was distilled off and purification was performed to obtain 0.07 parts of the compound represented by the formula (UVA-8).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-8) was produced.

¹ H-NMR (heavy DMSO) δ: 0.92 (s, 6H), 1.26 (s, 9H), 1.90 (s, 4H), 2.55 (m, 4H), 3.64-3.71 (m, 4H)

LC-MS; [M+H] ⁺ =326.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-8) was 377.4 nm. ε(λmax) of the compound represented by the obtained formula (UVA-8) is 0.66 L/(g·cm), ε(λmax+30 nm) is 0.395 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 1.68.

(Synthesis Example 9) Synthesis of the compound represented by the formula (UVA-9)

The inside of a 300 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer was made into nitrogen atmosphere, and 70.0 parts of dimedone, 10.4 parts of malononitrile, 40.6 parts of diisopropylethylamine, and 100.0 parts of ethanol were put, and it heated and refluxed and stirred for 3 hours. did it After completion of the reaction, the solvent was distilled off and purification was performed to obtain 15.1 parts of the compound represented by the formula (M-5).

In a nitrogen atmosphere, 5 parts of the compound represented by the formula (M-5), 5.8 parts of paratoluenesulfonylcyanide, 3 parts of potassium tert-butoxide, and 50 parts of ethanol were mixed. The resulting mixture was stirred at 0 to 5°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 3.3 parts of the compound represented by the formula (M-6).

In a nitrogen atmosphere, 1 part of the compound represented by the formula (M-6), 1 part of methyl triflate, 0.8 parts of diisopropylethylamine, and 20 parts of acetonitrile were mixed, and the mixture was stirred at 20 to 30°C for 3 hours. To the resulting mixture, 1.4 parts of piperidine and 20 parts of acetonitrile were added, followed by stirring at 20 to 30°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.5 parts of the compound represented by the formula (UVA-9).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (UVA-9) was produced.

¹ H-NMR (heavy DMSO) δ: 0.99 (s, 6H), 1.60 (m, 6H), 2.71 (s, 2H), 3.80 (m, 4H)

LC-MS; [M+H] ⁺ =281.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-9) was 385.6 nm. ε(λmax) of the compound represented by the obtained formula (UVA-9) is 1.65 L/(g·cm), ε(λmax+30 nm) is 0.088 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 18.8.

(Synthesis Example 10) Synthesis of the compound represented by the formula (UVA-A1)

10 parts of the compound represented by Formula (M-7) synthesized with reference to Japanese Patent Application Laid-Open No. 2014-194508, acetic anhydride in a 200 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer in a nitrogen atmosphere 3.6 parts, (2-butyloctyl)cyanoacetate 6.9 parts and acetonitrile 60 parts were added and stirred at 20-30°C. 4.5 parts of diisopropylethylamine was dripped at the obtained mixture over 1 hour, and it stirred for 2 hours. The solvent was distilled off and purified from the obtained mixture to obtain 4.6 parts of the compound represented by the formula (UVA-A1).

(Synthesis Example 11) Synthesis of the compound represented by the formula (UVA-A2)

In a 100 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer, a nitrogen atmosphere was made, 6 parts of the compound represented by the formula (M-8), 14.2 parts of dibutylamine, and 31.3 parts of isopropanol were mixed and heated to reflux, Stirred for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 4.6 parts of the compound represented by the formula (UVA-A2).

(Synthesis Example 12) Synthesis of the compound represented by the formula (UVA-A3)

The inside of a 300 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer was made into a nitrogen atmosphere, and 30 parts of malonaldehyde dianilide hydrochloride, 18.4 parts of Meldrum acid, 12.9 parts of triethylamine, and 90 parts of methanol were put, and 20-30 ° C. The reaction was stirred for 3 hours. After completion of the reaction, the solvent was distilled off and purification was performed to obtain 24.4 parts of the compound represented by the formula (M-8).

6 parts of the compound represented by the formula (M-8), 21.7 parts of dibenzylamine, and 31.3 parts of isopropanol were mixed and heated to reflux, followed by stirring and reaction for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 3.5 parts of the compound represented by the formula (UVA-A3).

(Synthesis Example 13) Synthesis of the compound represented by the formula (UVA-A4)

The inside of a 100 mL-four-necked flask equipped with a Dimroth cooling tube and a thermometer was made into a nitrogen atmosphere, 2-phenyl-1-methylindole-3-carboxyaldehyde 5 parts, piperidine 1.8 parts, malononitrile 1.5 parts, and ethanol 20 parts were mixed, heated to reflux, and stirred for 18 hours. The obtained mixture was heated to 80 degreeC, and it heat-retained at 80 degreeC for 18 hours. The solvent was distilled off from the obtained mixture, and refinement|purification was performed, and 4.9 parts of compounds represented by a formula (UVA-A4) were obtained.

(Example 1) Preparation of light-selective absorption composition (1)

Each component was mixed in the following ratios, and the photoselective absorption composition (active energy ray-curable resin composition) (1) was prepared.

Polyfunctional acrylate ("A-DPH-12E": manufactured by Shin-Nakamura Chemical Industry Co., Ltd.)

70 copies

Urethane acrylate ("UV-7650B": manufactured by Nippon Chemical Industry Co., Ltd.) 30 copies

Photoinitiator ("NCI-730": manufactured by ADEKA Co., Ltd.) Part 3

A compound represented by the formula (UVA-1) synthesized in Synthesis Example 1 part 2

methyl ethyl ketone part 34

(Example 2) Preparation of photoselective absorption composition (2)

A light-selective absorption composition (2) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-2).

(Example 3) Preparation of photoselective absorption composition (3)

A light-selective absorption composition (3) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-3).

(Example 4) Preparation of photoselective absorption composition (4)

A light-selective absorption composition (4) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-4).

(Example 5) Preparation of light-selective absorption composition (5)

A light-selective absorption composition (5) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-5).

(Example 6) Preparation of light-selective absorption composition (6)

A light-selective absorption composition (6) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-6).

(Example 7) Preparation of light-selective absorption composition (7)

A light-selective absorption composition (7) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-7).

(Example 8) Preparation of light-selective absorption composition (8)

A light-selective absorption composition (8) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-8).

(Example 9) Preparation of photoselective absorption composition (9)

A light-selective absorption composition (9) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-9).

(Preparation Example 1) Preparation of light-selective absorption composition (A1)

A photoselective absorption composition (A1) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-A1).

(Preparation Example 2) Preparation of light-selective absorption composition (A2)

A light-selective absorption composition (A2) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-A2).

(Preparation Example 3) Preparation of light-selective absorption composition (A3)

A photoselective absorption composition (A3) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-A4).

(Example 10) Preparation of a film with a cured layer (1)

Corona discharge treatment is performed on the surface of a resin film [trade name "ZEONOR", manufactured by Nippon Zeon Co., Ltd.] made of a cyclic polyolefin resin having a thickness of 23 µm, and the corona discharge treatment surface is subjected to a photoselective absorption composition (6) was coated using a bar coater. The coated film was put into a drying oven and dried at 100° C. for 2 minutes. After putting the coating film after drying into a nitrogen substitution box and sealing nitrogen in the box for 1 minute, the film with a hardened layer (6) was obtained by irradiating with ultraviolet rays from the coating surface side. Moreover, the film thickness of the hardened layer was about 6.0 micrometers.

As the ultraviolet irradiation apparatus, an ultraviolet irradiation apparatus with a belt conveyor (the lamp was "H valve" manufactured by Fusion UV Systems) was used, and ultraviolet rays were irradiated so that the accumulated light amount was 400 mJ/cm 2 (UVB).

(Comparative Example 1) Preparation of a film with a cured layer (A1)

Except having changed the light selective absorption composition (6) into the light selective absorption composition (A1), it carried out similarly to Example 10, and obtained the film with a cured layer (A1).

(Comparative Example 2) Preparation of a film with a cured layer (A2)

Except having changed the light selective absorption composition (6) into the light selective absorption composition (A2), it carried out similarly to Example 10, and obtained the film with a cured layer (A2).

(Comparative example 3) Preparation of a film with a cured layer (A3)

Except having changed the light selective absorption composition (6) into the light selective absorption composition (A3), it carried out similarly to Example 10, and obtained the film with a cured layer (A3).

<Measurement of absorbance of film with cured layer>

The film (1) with a cured layer obtained in Example 10 was cut to a size of 30 mm x 30 mm to obtain a sample (1). The obtained sample (1) and alkali-free glass [trade name "EAGLE XG" manufactured by Corning Corporation] were bonded through an acrylic adhesive to obtain a sample (2). The absorbance of the prepared sample (2) in the wavelength range of 300 to 800 nm was 1 nm Each step was measured using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation).The absorbance at a wavelength of 395 nm and a wavelength of 430 nm was measured at a wavelength of 395 nm and a wavelength of 430 nm of the film with a cured layer (1). The results are shown in Table 1. In addition, the absorbance at a wavelength of 395 nm and a wavelength of 430 nm of the alkali-free glass is almost 0, and that of the resin film made of a cyclic polyolefin resin has a wavelength of 395 nm and a wavelength of 430 The absorbance at nm is almost zero, and the absorbance at a wavelength of 395 nm and a wavelength of 430 nm of the acrylic pressure-sensitive adhesive is almost zero.

<Measurement of Absorbance Retention of Film with Cured Layer>

The sample (2) after absorbance measurement was put into a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd.) under conditions of a temperature of 63°C and a relative humidity of 50% RH for 48 hours to perform a weather resistance test. The absorbance of the sample (2) after the weather resistance test was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample (2) at a wavelength of 395 nm was determined based on the following formula. A result is shown in Table 1. A value close to 100 for the absorbance retention indicates that the photoselective absorption function is not deteriorated and has good weather resistance. A (395) represents the absorbance at a wavelength of 395 nm.

Absorbance retention (%) = (A (395) after endurance test / A (395) before endurance test) x 100

Instead of the film with a cured layer (1), using a film with a cured layer (A1), a film with a cured layer (A2), and a film with a cured layer (A3), respectively, the evaluation was performed in the same manner as for the film with a cured layer (1). did. A result is shown in Table 1.

(Example 11) Preparation of optical film (1)

A rubber having a particle diameter of 250 nm consisting of 70 parts of polymethyl methacrylate resin (Sumitomo Chemical Co., Ltd.: Sumipex MH) and a core-shell structure of polymethyl methacrylate resin (PMMA)/polybutyl acrylate resin (PBA). 30 parts of particles, 2 parts of the compound represented by the formula (UVA-6), and a resin solution (solid concentration: 25 mass%) consisting of 2-butanone were put into a mixing tank and stirred to dissolve each component.

The obtained melt was uniformly cast on a glass support using an applicator, dried in an oven at 40°C for 10 minutes, and then dried in an oven at 80°C for further 10 minutes. After drying, the optical film (1) was peeled off from the glass support body, and the optical film (1) which has light-selective absorption ability was obtained. The film thickness of the optical film 1 after drying was 30 micrometers.

(Example 12) Preparation of optical film (2)

A resin solution (solid content concentration) consisting of 100 parts of cellulose triacetate (acetyl substitution degree: 2.87), 2 parts of the compound represented by the formula (UVA-6), and a mixed solution of chloroform and ethanol (mass ratio, chloroform: ethanol = 90: 10) : 7% by mass) was put into a mixing tank and stirred to dissolve each component.

The obtained melt was uniformly cast on a glass support using an applicator, dried in an oven at 40°C for 10 minutes, and then further dried in an oven at 80°C for 10 minutes. After drying, the optical film (2) was peeled off from the glass support body, and the optical film (2) which has light-selective absorption ability was obtained. The film thickness of the optical film 2 after drying was 30 micrometers.

(Example 13) Preparation of optical film 3

A resin solution consisting of 100 parts of a cycloolefin polymer resin (manufactured by JSR: ARTON F4520), 2 parts of the compound represented by the formula (UVA-6), and a mixed solution of dichloromethane and toluene (mass ratio, dichloromethane:toluene=50:50) (solid content concentration: 20 mass %) was thrown into the mixing tank, and it stirred to melt|dissolve each component.

The obtained melt was uniformly cast on a glass support using an applicator, dried in an oven at 40°C for 10 minutes, and then further dried in an oven at 80°C for 10 minutes. After drying, the optical film (3) was peeled off from the glass support body, and the optical film (3) which has light-selective absorption ability was obtained. The film thickness of the optical film 3 after drying was 30 micrometers.

(Comparative Example 4) Preparation of the optical film (4)

An optical film (4) was produced in the same manner as in Example 11 except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-A1).

(Comparative Example 5) Preparation of the optical film 5

An optical film (5) was produced in the same manner as in Example 12 except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-A1).

(Comparative Example 6) Preparation of the optical film 6

An optical film (6) was produced in the same manner as in Example 11 except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-A4).

(Comparative Example 7) Preparation of the optical film 7

An optical film 7 was produced in the same manner as in Example 12 except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-A4).

<Measurement of absorbance of optical film>

After corona discharge treatment was performed on one side of the optical film 1 obtained in Example 11, the acrylic adhesive was bonded with a laminator, and cured for 7 days under the conditions of a temperature of 23 ° C. and a relative humidity of 65% RH, and an optical film with an adhesive (1) was obtained. Next, the optical film 1 with an adhesive was cut out to the size of 30 mm x 30 mm, it was bonded to alkali-free glass [the Corning company brand name "EAGLE XG"], and the sample 3 was produced. The created sample (3) ), the absorbance in the wavelength range of 300 to 800 nm is measured at every 1 nm step by using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation).The absorbance at the measured wavelength of 395 nm and wavelength 430 nm is measured using an optical film ( It was set as the absorbance at wavelength 395 nm and wavelength 430 nm of 1) The result is shown in Table 2. In addition, the absorbance at wavelength 395 nm and wavelength 430 nm of alkali free glass is almost 0, and the wavelength 395 nm of acrylic adhesive and absorbance at a wavelength of 430 nm is almost zero.

The sample (3) after the absorbance measurement was put into a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd.) under the conditions of a temperature of 63°C and a relative humidity of 50% RH, and a weather resistance test was performed for 200 hours. The absorbance of the sample (3) after the weather resistance test was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 395 nm was determined based on the following formula. A result is shown in Table 2. A value close to 100 for the absorbance retention indicates that the photoselective absorption function is not deteriorated and has good weather resistance.

Absorbance retention (%) = (A (395) after endurance test / A (395) before endurance test) x 100

Instead of the optical film (1), the optical film (2) - the optical film (7) were respectively used, and evaluation was performed similarly to the optical film (1). A result is shown in Table 2.

(Example 14) Preparation of the pressure-sensitive adhesive composition (1)

<Preparation of acrylic resin (A)>

In a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer, 81.8 parts of ethyl acetate as a solvent, 70.4 parts of butyl acrylate as a monomer, 20.0 parts of methyl acrylate, and 8.0 parts of 2-phenoxyethyl acrylate, 2-hydroxyethyl acrylate A mixed solution of 1.0 parts of ethyl and 0.6 parts of acrylic acid was added, and the air in the reaction vessel was substituted with nitrogen gas, and the internal temperature was raised to 55°C while not containing oxygen. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 1.42 million, and Mw/Mn was 5.2. Let this be an acrylic resin (A).

<Preparation of adhesive composition (1)>

To 100 parts of the solid content of the ethyl acetate solution (1) (resin concentration: 20%) of the acrylic resin (A) synthesized above, an ethyl acetate solution of the trimethylpropane adduct of tolylene diisocyanate (solid content concentration 75%) ), manufactured by Tosoh Corporation, trade name "Colonate L") 0.5 part, silane compound (3-glycidoxypropyl trimethoxysilane, Shin-Etsu Chemical Co., Ltd. product name "KBM403") 0.5 part, formula (UVA-1) 2.0 parts of the compound represented by was mixed, and ethyl acetate was further added so that solid content concentration might become 14%, and the adhesive composition (1) was obtained. In addition, the compounding quantity of the said crosslinking agent is a mass part as an active ingredient.

(Example 15) Preparation of the pressure-sensitive adhesive composition (2)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-2), it carried out similarly to Example 14, and obtained the adhesive composition (2).

(Example 16) Preparation of the pressure-sensitive adhesive composition (3)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-3), it carried out similarly to Example 14, and obtained the adhesive composition (3).

(Example 17) Preparation of the pressure-sensitive adhesive composition (4)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-4), it carried out similarly to Example 14, and obtained the adhesive composition (4).

(Example 18) Preparation of the pressure-sensitive adhesive composition (5)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-5), it carried out similarly to Example 14, and obtained the adhesive composition (5).

(Example 19) Preparation of the pressure-sensitive adhesive composition (6)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-6), it carried out similarly to Example 14, and obtained the adhesive composition (6).

(Example 20) Preparation of the pressure-sensitive adhesive composition (7)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-7), it carried out similarly to Example 14, and obtained the adhesive composition (7).

(Example 21) Preparation of the pressure-sensitive adhesive composition (8)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-8), it carried out similarly to Example 14, and obtained the adhesive composition (8).

(Example 22) Preparation of the pressure-sensitive adhesive composition (9)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-9), it carried out similarly to Example 14, and obtained the adhesive composition (9).

(Comparative Example 8) Preparation of the pressure-sensitive adhesive composition (10)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-A1), it carried out similarly to Example 14, and obtained the adhesive composition (10).

(Example 23) Preparation of the pressure-sensitive adhesive layer (1) and the pressure-sensitive adhesive sheet (1)

The obtained pressure-sensitive adhesive composition (6) was applied using an applicator to the release-treated surface of a separate film made of a polyethylene terephthalate film subjected to a release treatment [trade name "PLR-382190" obtained from Lintech Co., Ltd.], and 1 at 100 ° C. It was dried for minutes, and the adhesive layer (1) was produced. The thickness of the obtained adhesive layer was 15 micrometers.

After bonding the obtained pressure-sensitive adhesive layer (1) to a 23 µm ultraviolet absorber-containing cycloolefin film [trade name "ZEONOR" obtained from Nippon Zeon Co., Ltd.] with a laminator, the temperature was 23°C and the relative humidity was 65% for 7 days. It was cured to obtain an adhesive sheet (1).

(Example 24) Preparation of the pressure-sensitive adhesive layer (2) and the pressure-sensitive adhesive sheet (2)

Except having changed the adhesive composition (6) into the adhesive composition (7), it carried out similarly to Example 23, and produced the adhesive layer (2) and the adhesive sheet (2).

(Comparative Example 9) Preparation of the pressure-sensitive adhesive layer (3) and the pressure-sensitive adhesive sheet (3)

Except having changed the adhesive composition (6) into the adhesive composition (10), it carried out similarly to Example 23, and produced the adhesive layer (3) and the adhesive sheet (3).

<Measurement of absorbance of adhesive sheet>

The obtained pressure-sensitive adhesive sheet (1) was cut to a size of 30 mm × 30 mm, the separate film was peeled off, the pressure-sensitive adhesive layer (1) and alkali-free glass [trade name "EAGLE XG" manufactured by Corning Corporation] were bonded together, and this was sampled ( 4).The absorbance in the wavelength range of 300 to 800 nm of the prepared sample (4) was measured every 1 nm step by using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation).Measured wavelength of 395 nm and wavelength The absorbance at 430 nm was defined as the absorbance at a wavelength of 395 nm and a wavelength of 430 nm of the pressure-sensitive adhesive sheet 1. The results are shown in Table 3. In addition, both the single cycloolefin film and the alkali-free glass have a wavelength of 395 nm and The absorbance at a wavelength of 430 nm is zero.

<Measurement of absorbance retention of adhesive sheet>

The sample (4) after absorbance measurement was put into a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd.) under conditions of a temperature of 63°C and a relative humidity of 50% RH for 200 hours, and a weather resistance test was performed. The absorbance of the taken out sample (4) was measured in the same manner as above. From the measured absorbance, the absorbance retention rate of the sample at 395 nm was calculated|required based on the following formula. A result is shown in Table 3. A value close to 100 for the absorbance retention indicates that the photoselective absorption function is not deteriorated and has good weather resistance.

Absorbance retention (%) = (A (395) after endurance test / A (395) before endurance test) x 100

Instead of the pressure-sensitive adhesive sheet 1, the pressure-sensitive adhesive sheet 2 and the pressure-sensitive adhesive sheet 3 were used, respectively, and evaluation was performed in the same manner as the pressure-sensitive adhesive sheet 1 . A result is shown in Table 3.

(Synthesis Example 14) Synthesis of the compound represented by the formula (UVA-10)

In a nitrogen atmosphere, 2.5 parts of the compound represented by the formula (M-9), 15.1 parts of benzoyl(phenyliodonio)(trifluoromethanesulfonyl)methanide, 0.4 parts of copper(I) chloride, and 100 parts of dioxane are mixed did. The resulting mixture was stirred at 30°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.7 parts of the compound represented by the formula (M-10).

In a nitrogen atmosphere, 1.5 parts of the compound represented by the formula (M-10), 1.4 parts of methyl triflate and 10 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. 1.3 parts of diisopropylethylamine and 0.7 parts of malononitrile were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.0 part of the compound represented by the formula (UVA-10).

LC-MS measurement and ¹ H-NMR analysis were performed as described above, and it was confirmed that the compound represented by the formula (UVA-10) was produced.

¹ H-NMR (medium DMSO) δ: 1.00 (s, 3H), 1.15 (s, 3H), 1.86 (m, 2H), 2.18 (m, 2H), 2.32 to 2.91 (m, 4H), 3.50 to 4.20 (m, 4H)

LC-MS; [M+H] ⁺ =343.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-10) was 384.2 nm. ε(λmax) of the compound represented by the obtained formula (UVA-10) is 1.29 L/(g·cm), ε(λmax+30 nm) is 0.075 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 17.2.

(Synthesis Example 15) Synthesis of the compound represented by the formula (UVA-11)

In a nitrogen atmosphere, 5 parts of the compound represented by the formula (M-6), 4.9 parts of methyl triflate, 3.8 parts of diisopropylethylamine, and 10 parts of acetonitrile were mixed, followed by stirring at 20 to 30°C for 3 hours. 5 parts of dimethylamine was added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 3.1 parts of the compound represented by the formula (UVA-11).

LC-MS measurement and ¹ H-NMR analysis were performed as described above, and it was confirmed that the compound represented by the formula (UVA-11) was produced.

¹ H-NMR (heavy DMSO) δ: 1.08 (s, 6H), 2.42 (s, 2H), 2.55 (s, 2H), 3.40 (m, 6H)

LC-MS; [M+H] ⁺ =241.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-11) was 379.4 nm. ε(λmax) of the compound represented by the obtained formula (UVA-11) is 1.93 L/(g cm), ε(λmax+30 nm) is 0.063 L/(g cm), ε(λmax)/ε( λmax+30 nm) was 30.6.

(Synthesis Example 16) Synthesis of the compound represented by the formula (UVA-12)

In a nitrogen atmosphere, 5 parts of the compound represented by the formula (M-6), 4.9 parts of methyl triflate, 3.8 parts of diisopropylethylamine, and 10 parts of acetonitrile were mixed, followed by stirring at 20 to 30°C for 3 hours. 8.4 parts of diethylamine was added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 2.9 parts of the compound represented by the formula (UVA-12).

LC-MS measurement and ¹ H-NMR analysis were performed as described above, and it was confirmed that the compound represented by the formula (UVA-12) was produced.

¹ H-NMR (heavy DMSO) δ: 1.08 (s, 6H), 1.39 (t, 6H), 2.44 (s, 2H), 2.58 (s, 2H), 3.74 (m, 4H)

LC-MS; [M+H] ⁺ =269.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-12) was 380.5 nm. ε(λmax) of the obtained compound represented by the formula (UVA-12) is 1.75 L/(g·cm), ε(λmax+30 nm) is 0.098 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 17.6.

(Synthesis Example 17) Synthesis of the compound represented by the formula (UVA-13)

In a nitrogen atmosphere, 5 parts of the compound represented by the formula (M-6), 4.9 parts of methyl triflate, 3.8 parts of diisopropylethylamine, and 10 parts of acetonitrile were mixed, followed by stirring at 20 to 30°C for 3 hours. 14.8 parts of dibutylamine was added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 2.5 parts of the compound represented by the formula (UVA-13).

LC-MS measurement and ¹ H-NMR analysis were performed as described above, and it was confirmed that the compound represented by the formula (UVA-13) was produced.

¹ H-NMR (medium DMSO) δ: 0.99 (t, 6H), 1.07 (s, 6H), 1.32 to 1.46 (m, 4H), 1.70 (m, 4H), 2.40 (s, 2H), 2.57 (s) , 2H), 3.32 to 3.85 (m, 4H).

LC-MS; [M+H] ⁺ =325.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-13) was 382.8 nm. ε(λmax) of the compound represented by the obtained formula (UVA-13) is 1.42 L/(g·cm), ε(λmax+30 nm) is 0.095 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 14.9.

(Synthesis Example 18) Synthesis of the compound represented by the formula (UVA-14)

In a nitrogen atmosphere, 5 parts of the compound represented by the formula (M-6), 3.6 parts of potassium carbonate, 7.7 parts of methyl triflate and 40 parts of methyl ethyl ketone were mixed, followed by stirring at 0 to 5°C for 4 hours. To the resulting mixture, 2 parts of azetidine was added and stirred at 0 to 5°C for 10 minutes. The solvent was distilled off and purified from the obtained mixture to obtain 2.6 parts of the compound represented by the formula (UVA-14).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (UVA-14) was produced.

¹ H-NMR (heavy DMSO) δ: 1.05 (s, 6H), 2.14 (s, 2H), 2.45 to 2.53 (m, 4H), 4.36 (t, 2H), 4.91 (t, 2H)

LC-MS; [M+H] ⁺ =253.3

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-14) was 377.2 nm. ε(λmax) of the compound represented by the obtained formula (UVA-14) is 1.93 L/(g cm), ε(λmax+30 nm) is 0.028 L/(g cm), ε(λmax)/ε( λmax+30 nm) was 68.9.

(Synthesis Example 19) Synthesis of the compound represented by the formula (UVA-15)

In a nitrogen atmosphere, 4.0 parts of the compound represented by the formula (M-6), 3.7 parts of methyl triflate, and 40 parts of acetonitrile were mixed, followed by stirring at 20 to 30°C for 3 hours. To the resulting mixture were added 2.9 parts of diisopropylethylamine and 40 parts of a solution obtained by dissolving methylamine in tetrahydrofuran (methylamine concentration; 7% by mass), followed by stirring at 20 to 30°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.9 parts of the compound represented by the formula (UVA-15).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-15) was produced.

¹ H-NMR (heavy DMSO) δ: 0.98 (s, 6H), 2.48 to 2.58 (m, 4H), 3.03 (s, 3H), 9.15 (s, 1H)

LC-MS; [M+H] ⁺ =226.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-15) was 364.8 nm. ε(λmax) of the compound represented by the obtained formula (UVA-15) is 1.86 L/(g·cm), ε(λmax+30 nm) is 0.066 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 28.2.

(Synthesis Example 20) Synthesis of the compound represented by the formula (UVA-16)

In a nitrogen atmosphere, 4.0 parts of the compound represented by the formula (M-6), 3.7 parts of methyl triflate, and 40 parts of acetonitrile were mixed, followed by stirring at 20 to 30°C for 3 hours. To the resulting mixture were added 2.9 parts of diisopropylethylamine and 40 parts of a solution obtained by dissolving ethylamine in tetrahydrofuran (ethylamine concentration; 10% by mass), followed by stirring at 20 to 30°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.5 parts of the compound represented by the formula (UVA-16).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-16) was produced.

¹ H-NMR (heavy DMSO) δ: 0.98 (s, 6H), 2.48 to 2.58 (m, 4H), 3.03 (t, 3H), 4.21 (m, 2H), 9.15 (s, 1H)

LC-MS; [M+H] ⁺ =240.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-16) was 364.8 nm. ε(λmax) of the compound represented by the obtained formula (UVA-16) is 1.80 L/(g·cm), ε(λmax+30 nm) is 0.074 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 24.4.

(Synthesis Example 21) Synthesis of the compound represented by the formula (UVA-17)

In a nitrogen atmosphere, 1.7 parts of the compound represented by the formula (M-6), 1.6 parts of methyl triflate, and 17 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. To the obtained mixture, 1.2 parts of diisopropylethylamine and 100 parts of a solution of ammonia dissolved in tetrahydrofuran (ammonia molar concentration; 0.4 mol%) were added, and the mixture was stirred at 20 to 30°C for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.7 parts of the compound represented by the formula (UVA-17).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-17) was produced.

¹ H-NMR (heavy DMSO) δ: 0.98 (s, 6H), 2.48 to 2.58 (m, 4H), 9.15 (m, 2H)

LC-MS; [M+H] ⁺ =213.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-17) was 352.6 nm. ε(λmax) of the compound represented by the obtained formula (UVA-17) is 1.75 L/(g·cm), ε(λmax+30 nm) is 0.11 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 15.9.

(Synthesis Example 22) Synthesis of the compound represented by the formula (UVA-18)

In a nitrogen atmosphere, 3.5 parts of the compound represented by the formula (M-6), 3.2 parts of methyl triflate and 35 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. 2.2 parts of potassium carbonate and 0.8 parts of N,N'-dimethylethylenediamine were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.4 parts of a compound represented by the formula (UVA-18).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-18) was produced.

¹ H-NMR (heavy DMSO) δ: 0.98 (s, 12H), 2.67 (m, 4H), 3.44 (m, 8H), 4.05 (m, 6H)

LC-MS; [M+H] ⁺ =479.7

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-18) was 391.4 nm. ε(λmax) of the compound represented by the obtained formula (UVA-18) is 1.52 L/(g·cm), ε(λmax+30 nm) is 0.036 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 42.2.

(Synthesis Example 23) Synthesis of the compound represented by the formula (UVA-19)

In a nitrogen atmosphere, 3.5 parts of the compound represented by the formula (M-6), 3.2 parts of methyl triflate and 35 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. 2.2 parts of potassium carbonate and 1.0 part of N,N'- dimethyltrimethylenediamine were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.2 parts of a compound represented by the formula (UVA-19).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-19) was produced.

¹ H-NMR (medium DMSO) δ: 0.99 (s, 12H), 2.50 (m, 8H), 2.66 (m, 6H), 3.32 (m, 6H)

LC-MS; [M+H] ⁺ =493.7

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-19) was 384.9 nm. ε(λmax) of the compound represented by the obtained formula (UVA-19) is 1.63 L/(g·cm), ε(λmax+30 nm) is 0.036 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 45.3.

(Example 25) Preparation of photoselective absorption composition (10)

A light-selective absorption composition (10) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-10).

(Example 26) Preparation of photoselective absorption composition (11)

A light-selective absorption composition (11) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-11).

(Example 27) Preparation of photoselective absorption composition (12)

A light-selective absorption composition (12) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-12).

(Example 28) Preparation of light-selective absorption composition (13)

A light-selective absorption composition (13) was prepared in the same manner as in Example 1 except that the compound represented by the formula (UVA-1) was used as the compound represented by the formula (UVA-13).

(Example 29) Preparation of the film with a cured layer (2)

A film with a cured layer (2) was obtained in the same manner as in Example 10 except that the light selective absorption composition (1) was replaced with the light selective absorption composition (11).

(Example 30) Preparation of the film 3 with a cured layer

A film with a cured layer (3) was obtained in the same manner as in Example 10 except that the light selective absorption composition (1) was replaced with the light selective absorption composition (12).

<Measurement of absorbance of film with cured layer and measurement of absorbance retention>

Absorbance was measured in the same manner as in <Measurement of absorbance of film with cured layer>, except that the film with a cured layer (2) and the film with a cured layer (3) were used instead of the film with a cured layer (1).

The cured film (1) and Comparative Example 3 obtained in Example 10 in the same manner as in the above <Measurement of Absorbance Retention of Film with Cured Layer> except that the input time to the sunshine weather meter was 75 hours. The absorbance retention of the film with a cured layer (A3) obtained in was measured.

In addition, instead of the film with a cured layer (1), the film with a cured layer (2) and a film with a cured layer (3) were used, and except that the input time to the sunshine weather meter was 75 hours, the <cured layer The absorbance retention was measured in the same manner as in >Measurement of the absorbance retention of the attached film.

These results are shown in Table 4. In Table 4, the value of the absorbance of the film with a cured layer obtained in Example 10 (1) and the film with a cured layer (A3) obtained in the comparative example 3 is also shown.

(Example 31) Preparation of the pressure-sensitive adhesive composition (11)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-10), it carried out similarly to Example 14, and obtained the adhesive composition (11).

(Example 32) Preparation of the pressure-sensitive adhesive composition (12)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-11), it carried out similarly to Example 14, and obtained the adhesive composition (12).

(Example 33) Preparation of the pressure-sensitive adhesive composition (13)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-12), it carried out similarly to Example 14, and obtained the adhesive composition (13).

(Example 34) Preparation of the pressure-sensitive adhesive composition (14)

Except having changed the compound represented by a formula (UVA-1) into the compound represented by a formula (UVA-13), it carried out similarly to Example 14, and obtained the adhesive composition (14).

(Example 35) Preparation of the pressure-sensitive adhesive layer 4 and the pressure-sensitive adhesive sheet 4

Except having changed the adhesive composition (6) into the adhesive composition (9), it carried out similarly to Example 23, and produced the adhesive layer (4) and the adhesive sheet (4).

(Example 36) Preparation of the pressure-sensitive adhesive layer (5) and the pressure-sensitive adhesive sheet (5)

Except having changed the adhesive composition (6) into the adhesive composition (11), it carried out similarly to Example 23, and produced the adhesive layer (5) and the adhesive sheet (5).

(Example 37) Preparation of the pressure-sensitive adhesive layer 6 and the pressure-sensitive adhesive sheet 6

Except having changed the adhesive composition (6) into the adhesive composition (12), it carried out similarly to Example 23, and produced the adhesive layer (6) and the adhesive sheet (6).

(Example 38) Preparation of the pressure-sensitive adhesive layer 7 and the pressure-sensitive adhesive sheet 7

Except having changed the adhesive composition (6) into the adhesive composition (13), it carried out similarly to Example 23, and produced the adhesive layer (7) and the adhesive sheet (7).

(Example 39) Preparation of the pressure-sensitive adhesive layer (8) and the pressure-sensitive adhesive sheet (8)

Except having changed the adhesive composition (6) into the adhesive composition (14), it carried out similarly to Example 23, and produced the adhesive layer (8) and the adhesive sheet (8).

(Example 40) Preparation of the pressure-sensitive adhesive composition (15)

In the same manner as in Example 14, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-18), and the content was 1.0 parts by mass with respect to 100 parts by mass of the acrylic resin (A). Thus, the pressure-sensitive adhesive composition (15) was obtained.

(Example 41) Preparation of the pressure-sensitive adhesive layer 9 and the pressure-sensitive adhesive sheet 9

Except having changed the adhesive composition (6) into the adhesive composition (15), it carried out similarly to Example 23, and produced the adhesive layer (9) and the adhesive sheet (9).

<Measurement of absorbance of adhesive sheet and measurement of absorbance retention>

Absorbance and absorbance retention in the same manner as in <Measurement of absorbance of the pressure-sensitive adhesive sheet> and <Measurement of absorbance retention of the pressure-sensitive adhesive sheet> except that the pressure-sensitive adhesive sheet 4 to the pressure-sensitive adhesive sheet 9 were used instead of the pressure-sensitive adhesive sheet 1 was measured. The results are shown in Table 5.

(Synthesis Example 24) Synthesis of the compound represented by the formula (UVA-20)

In a nitrogen atmosphere, 17 parts of the compound represented by the formula (M-3), 12.2 parts of potassium carbonate, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2.]octane bis(tetra 15.9 parts of fluoroborate) (Selectfluoro, a registered trademark of Air Products and Chemicals) and 85 parts of methyl ethyl ketone were mixed and stirred in an ice bath for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 3.7 parts of the compound represented by the formula (M-11).

In a nitrogen atmosphere, 18 parts of the compound represented by the formula (M-11), 28 parts of methyl triflate, and 90 parts of methyl ethyl ketone were mixed and stirred at 20 to 30°C for 3 hours. 13.0 parts of potassium carbonate and 8.4 parts of malononitrile were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 5.8 parts of the compound represented by the formula (UVA-20).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-20) was produced.

¹ H-NMR (heavy DMSO) δ: 1.08 (s, 6H), 1.97 (m, 4H), 2.40 (d, 2H), 2.50 (d, 2H), 3.53 (m, 2H), 3.86 (m, 2H) )

LC-MS; [M+H] ⁺ =260.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-20) was 407.5 nm. ε(λmax) of the compound represented by the obtained formula (UVA-20) is 2.30 L/(g·cm), ε(λmax+30 nm) is 0.041 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 56.0.

(Synthesis Example 25) Synthesis of the compound represented by the formula (UVA-21)

In a nitrogen atmosphere, 5 parts of 3-hydroxypiperidine, 13.6 parts of tert-butyldiphenylsilyl chloride, 6.7 parts of imidazole and 40 parts of dichloromethane were mixed, followed by stirring at 20 to 30°C for 4 hours. The solvent was distilled off and purified from the obtained mixture to obtain 10.5 parts of the compound represented by the formula (M-12).

In a nitrogen atmosphere, 4.0 parts of the compound represented by the formula (M-6), 3.2 parts of diisopropylethylamine, 4.0 parts of methyl triflate and 80 parts of acetonitrile were mixed, and the mixture was stirred at 20 to 30°C for 4 hours. 8.3 parts of the compound represented by Formula (M-12) was added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off and purified from the obtained mixture to obtain 6.5 parts of the compound represented by the formula (UVA-21).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (UVA-21) was produced.

¹ H-NMR (medium DMSO) δ: 0.97 (s, 6H), 1.04 (s, 9H), 1.70 (m, 2H), 1.85 (m, 2H), 2.48 (s, 2H), 2.65 (s, 2H) ), 3.72 (m, 2H), 3.94 (m, 2H), 4.13 (m, 1H), 7.42 to 7.52 (m, 6H), 7.61 to 7.64 (m, 4H)

LC-MS; [M+H] ⁺ =535.9

(Synthesis Example 26) Synthesis of the compound represented by the formula (UVA-22)

In a nitrogen atmosphere, 4.2 parts of the compound represented by the formula (UVA-21) and 50 parts of a 1M solution of tetrabutylammonium fluoride/tetrahydrofuran were mixed, followed by stirring at 20 to 30°C for 40 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.8 parts of the compound represented by the formula (UVA-22).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-22) was produced.

¹ H-NMR (heavy DMSO) δ: 0.98 (s, 6H), 1.59 (m, 2H), 1.92 (m, 2H), 2.67 (s, 2H), 3.68 to 3.95 (m, 4H), 4.97 (m) , 1H)

LC-MS; [M+H] ⁺ =297.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-22) was 384.6 nm. ε(λmax) of the compound represented by the obtained formula (UVA-22) is 1.43 L/(g cm), ε(λmax+30 nm) is 0.085 L/(g cm), ε(λmax)/ε( λmax+30 nm) was 16.8.

(Synthesis Example 27) Synthesis of the compound represented by the formula (UVA-23)

In nitrogen atmosphere, 5.0 parts of the compound represented by Formula (M-6), 3.6 parts of potassium carbonate, 7.7 parts of methyl triflate, and 40 parts of acetonitrile were mixed, and it stirred at 20-30 degreeC for 4 hours. 2.0 parts of azetidine was added to the obtained mixture, and it stirred at 20-30 degreeC for 4 hours. The solvent was distilled off and purified from the obtained mixture to obtain 2.3 parts of the compound represented by the formula (UVA-23).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-23) was produced.

¹ H-NMR (heavy DMSO) δ: 1.05 (s, 6H), 2.14 (s, 2H), 2.44 to 2.53 (m, 4H), 4.36 (t, 2H), 4.91 (t, 2H)

LC-MS; [M+H] ⁺ =253.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-23) was 377.2 nm. ε(λmax) of the compound represented by the obtained formula (UVA-23) is 1.93 L/(g cm), ε(λmax+30 nm) is 0.028 L/(g cm), ε(λmax)/ε( λmax+30 nm) was 68.9.

(Synthesis Example 28) Synthesis of the compound represented by the formula (UVA-24)

In a nitrogen atmosphere, 2.5 parts of the compound represented by the formula (M-6), 1.6 parts of potassium carbonate, 2.3 parts of methyl triflate, and 25 parts of acetonitrile were mixed, followed by stirring at 20 to 30°C for 4 hours. To the resulting mixture, 0.6 parts of piperazine was added and stirred at 20 to 30°C for 4 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.0 part of the compound represented by the formula (UVA-24).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (UVA-24) was produced.

¹ H-NMR (medium DMSO) δ: 0.93 (s, 2H), 1.01 (s, 12H), 1.24 (s, 2H), 2.65 (s, 4H), 4.09 (m, 8H)

LC-MS; [M+H] ⁺ =477.5

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-24) was 390.5 nm. ε(λmax) of the compound represented by the obtained formula (UVA-24) is 1.92 L/(g·cm), ε(λmax+30 nm) is 0.033 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 58.2.

(Synthesis Example 29) Synthesis of the compound represented by the formula (UVA-25)

In a nitrogen atmosphere, 2.5 parts of the compound represented by the formula (M-6), 1.6 parts of potassium carbonate, 2.3 parts of methyl triflate, and 25 parts of methyl ethyl ketone were mixed, followed by stirring at 20 to 30°C for 4 hours. 1.0 part of 1,4-bisaminomethylcyclohexane was added to the obtained mixture, and it stirred at 20-30 degreeC for 4 hours. The solvent was distilled off and purified from the obtained mixture to obtain 1.0 part of the compound represented by the formula (UVA-25).

LC-MS measurement and ¹ H-NMR analysis were performed, and it was confirmed that the compound represented by the formula (UVA-25) was produced.

¹ H-NMR (medium DMSO) δ: 0.98 (m, 12H), 1.38 to 1.78 (m, 10 H), 2.67 (m, 6H), 3.40 (m, 2H), 9.15 (m, 2H)

LC-MS; [M+H] ⁺ =533.6

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-25) was 372.7 nm. ε(λmax) of the compound represented by the obtained formula (UVA-25) is 1.59 L/(g·cm), ε(λmax+30 nm) is 0.036 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 44.1.

(Synthesis Example 30) Synthesis of the compound represented by the formula (UVA-26)

In a nitrogen atmosphere, 2.5 parts of the compound represented by the formula (M-6), 1.6 parts of potassium carbonate, 2.3 parts of methyl triflate, and 25 parts of methyl ethyl ketone were mixed, followed by stirring at 20 to 30°C for 4 hours. 0.8 part of 1,2-bis(ethylamino)ethane was added to the obtained mixture, and it stirred at 20-30 degreeC for 4 hours. The solvent was distilled off and purified from the obtained mixture to obtain 0.9 parts of the compound represented by the formula (UVA-26).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound represented by the formula (UVA-26) was produced.

¹ H-NMR (heavy DMSO) δ: 1.00 (s, 12H), 1.29 (t, 6H), 2.56 (s, 4H), 2.70 (s, 4H), 3.85 (m, 4H), 4.05 (m, 4H) )

LC-MS; [M+H] ⁺ =507.7

In addition, the maximum absorption wavelength and the gram extinction coefficient were measured as described above. The maximum absorption wavelength of the compound represented by the obtained formula (UVA-26) was 390.7 nm. ε(λmax) of the compound represented by the obtained formula (UVA-26) is 1.30 L/(g·cm), ε(λmax+30 nm) is 0.048 L/(g·cm), ε(λmax)/ε( λmax+30 nm) was 27.1.

(Example 42) Preparation of the pressure-sensitive adhesive composition (16)

In the same manner as in Example 14, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-23), and the content was 0.5 parts with respect to 100 parts of the acrylic resin (A), An adhesive composition (16) was obtained.

(Example 43) Preparation of the pressure-sensitive adhesive composition (17)

In the same manner as in Example 14, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-26), and the content was 0.2 parts with respect to 100 parts of the acrylic resin (A), An adhesive composition (17) was obtained.

(Example 44) Preparation of the pressure-sensitive adhesive layer (10) and the pressure-sensitive adhesive sheet (10)

Except having changed the adhesive composition (6) into the adhesive composition (16), it carried out similarly to Example 23, and produced the adhesive layer (10) and the adhesive sheet (10).

(Example 45) Preparation of the pressure-sensitive adhesive layer 11 and the pressure-sensitive adhesive sheet 11

Except having changed the adhesive composition (6) into the adhesive composition (17), it carried out similarly to Example 23, and produced the adhesive layer (11) and the adhesive sheet (11).

<Measurement of absorbance of adhesive sheet and measurement of absorbance retention>

Absorbance and absorbance retention in the same manner as in <Measurement of absorbance of the pressure-sensitive adhesive sheet> and <Measurement of absorbance retention of the pressure-sensitive adhesive sheet> except that the pressure-sensitive adhesive sheet 10 and the pressure-sensitive adhesive sheet 11 were used instead of the pressure-sensitive adhesive sheet 1 was measured. The results are shown in Table 6.

(Example 46) Preparation of the pressure-sensitive adhesive composition (18)

<Preparation of acrylic resin (A-2)>

In a reaction vessel equipped with a cooling tube, nitrogen inlet tube, thermometer and stirrer, a mixed solution of 81.8 parts of ethyl acetate as a solvent, 96 parts of butyl acrylate as a monomer, 3 parts of 2-hydroxyethyl acrylate, and 1 part of acrylic acid was placed thereinto, followed by nitrogen gas. The internal temperature was raised to 55 degreeC while replacing the air in the reaction vessel to make it oxygen-free. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 1.4 million. Mw/Mn was 4.8. Let this be an acrylic resin (A-2).

<Preparation of the adhesive composition (18)>

With respect to 100 parts of solid content of the ethyl acetate solution (resin concentration: 20%) of the acrylic resin (A-2) synthesized above, ethyl acetate solution (solid content concentration: 75%) of a crosslinking agent (trimethylpropane adduct of tolylene diisocyanate) , Tosoh Corporation make, trade name "Colonate L") 0.5 part, silane compound (1,6-bis(trimethoxysilyl)hexane, Shin-Etsu Chemical Co., Ltd. make, trade name "KBM3066") 0.3 part, formula (UVA-6) 3 parts of the compound represented by ) was mixed, and ethyl acetate was further added so that solid content concentration might become 14%, and the adhesive composition (18) was obtained. In addition, the compounding quantity of the said crosslinking agent is a mass part as an active ingredient.

(Example 47) Preparation of the pressure-sensitive adhesive composition (19)

<Preparation of acrylic resin (A-3)>

In a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer, 81.8 parts of ethyl acetate as a solvent, 60 parts of methyl acrylate as a monomer, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 20 parts of 2-phenoxyethyl acrylate The negative mixed solution was added, and the internal temperature was raised to 55°C while replacing the air in the reaction vessel with nitrogen gas so as to not contain oxygen. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 920,000. Mw/Mn=7.8. Let this be an acrylic resin (A-3).

<Preparation of the pressure-sensitive adhesive composition (19)>

Instead of the acrylic resin (A-2), except having used the acrylic resin (A-3) synthesize|combined above, it carried out similarly to Example 46, and obtained the adhesive composition (19).

(Example 48) Preparation of the pressure-sensitive adhesive composition (20)

<Preparation of acrylic resin (A-4)>

In a reaction vessel equipped with a cooling tube, nitrogen introduction tube, thermometer and stirrer, 81.8 parts of ethyl acetate as a solvent, 10 parts of butyl acrylate as a monomer, 60 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 2 parts of acrylic acid - A mixed solution of 10 parts of phenoxyethyl was added, and the air in the reaction vessel was substituted with nitrogen gas, and the internal temperature was raised to 55°C while not containing oxygen. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 940,000. Mw/Mn = 8.5. Let this be an acrylic resin (A-4).

<Preparation of the pressure-sensitive adhesive composition (20)>

Instead of the acrylic resin (A-2), except having used the acrylic resin (A-4) synthesize|combined above, it carried out similarly to Example 46, and obtained the adhesive composition (20).

(Example 49) Preparation of the pressure-sensitive adhesive composition (21)

<Preparation of acrylic resin (A-5)>

In a reaction vessel equipped with a cooling tube, nitrogen inlet tube, thermometer and stirrer, 81.8 parts of ethyl acetate as a solvent, 20 parts of butyl acrylate as a monomer, 50 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 2 parts of acrylic acid - A mixed solution of 10 parts of phenoxyethyl was added, and the air in the reaction vessel was substituted with nitrogen gas, and the internal temperature was raised to 55°C while not containing oxygen. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 910,000. Let this be an acrylic resin (A-5).

<Preparation of the pressure-sensitive adhesive composition (21)>

Instead of the acrylic resin (A-2), except having used the acrylic resin (A-5) synthesize|combined above, it carried out similarly to Example 46, and obtained the adhesive composition (21).

(Example 50) Preparation of the pressure-sensitive adhesive composition (22)

<Preparation of acrylic resin (A-6)>

In a reaction vessel equipped with a cooling tube, nitrogen inlet tube, thermometer and stirrer, 81.8 parts of ethyl acetate as a solvent, 50 parts of butyl acrylate as a monomer, 10 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 2 parts of acrylic acid - A mixed solution of 20 parts of phenoxyethyl was added, and the air in the reaction vessel was substituted with nitrogen gas, and the internal temperature was raised to 55°C while not containing oxygen. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 1.2 million. Let this be an acrylic resin (A-6).

<Preparation of the pressure-sensitive adhesive composition (22)>

Instead of the acrylic resin (A-2), except having used the acrylic resin (A-6) synthesize|combined above, it carried out similarly to Example 46, and obtained the adhesive composition (22).

(Example 51) Preparation of the pressure-sensitive adhesive composition (23)

<Preparation of acrylic resin (A-7)>

In a reaction vessel equipped with a cooling tube, nitrogen introduction tube, thermometer and stirrer, 81.8 parts of ethyl acetate as a solvent, 60 parts of butyl acrylate as a monomer, 10 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 2 parts of acrylic acid - A mixed solution of 10 parts of phenoxyethyl was added, and the air in the reaction vessel was substituted with nitrogen gas, and the internal temperature was raised to 55°C while not containing oxygen. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 1.18 million. Let this be an acrylic resin (A-7).

<Preparation of the pressure-sensitive adhesive composition (23)>

Instead of the acrylic resin (A-2), except having used the acrylic resin (A-7) synthesize|combined above, it carried out similarly to Example 46, and obtained the adhesive composition (23).

(Example 52) Preparation of the pressure-sensitive adhesive composition (24)

<Preparation of acrylic resin (A-8)>

In a reaction vessel equipped with a cooling tube, nitrogen introduction tube, thermometer and stirrer, 81.8 parts of ethyl acetate as a solvent, 70 parts of butyl acrylate as a monomer, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 10 parts of 2-phenoxyethyl acrylate The negative mixed solution was added, and the internal temperature was raised to 55°C while replacing the air in the reaction vessel with nitrogen gas so as to not contain oxygen. Then, the whole amount of the solution which melt|dissolved 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, the temperature was maintained at this temperature for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, when the concentration of the acrylic resin reached 35% , the addition of ethyl acetate was stopped, and the temperature was further maintained at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight Mw of polystyrene conversion by GPC was 1.1 million. Let this be an acrylic resin (A-8).

<Preparation of the pressure-sensitive adhesive composition (24)>

Instead of the acrylic resin (A-2), except having used the acrylic resin (A-8) synthesize|combined above, it carried out similarly to Example 46, and obtained the adhesive composition (23).

<Evaluation of crystal precipitation (bleed resistance) of the pressure-sensitive adhesive layer>

The pressure-sensitive adhesive composition 18 is applied to the release-treated surface of a release-treated polyethylene terephthalate film made of a polyethylene terephthalate film [trade name “PLR-382190” obtained from Lintech Co., Ltd.] using an applicator, and applied at 100° C. for 1 minute It was dried to prepare a pressure-sensitive adhesive layer. A separate film was further laminated|stacked on the other side of this adhesive layer, and the adhesive layer with a double-sided separate film was obtained. The thickness of the obtained adhesive layer was 15 micrometers.

The obtained pressure-sensitive adhesive layer with a double-sided separate film was cured under conditions of a temperature of 23°C and a relative humidity of 65% for 7 days. The presence or absence of crystal precipitation of the compound in the surface was confirmed for the adhesive layer with a double-sided separate film after curing using the microscope. A case without crystal precipitation was evaluated as a, and a case with crystal precipitation was evaluated as b. The evaluation result is shown in the column of "After curing" of Table 7.

Moreover, the obtained adhesive layer with a double-sided separate film was stored in the air of the temperature of 40 degreeC for 1 month. The presence or absence of crystallization of the compound in the surface was confirmed for the adhesive layer with a double-sided separate film after storage using the microscope. A case without crystal precipitation was evaluated as a, and a case with crystal precipitation was evaluated as b. An evaluation result is shown in the column of "40 degreeC 1M" of Table 7.

Except having changed the adhesive composition (18) into the adhesive composition (19) - the adhesive composition (24), it carried out similarly, and the presence or absence of crystal precipitation was confirmed. A result is shown in Table 7.

(Example 53) Preparation of the pressure-sensitive adhesive layer 12 and the pressure-sensitive adhesive sheet 12

The obtained pressure-sensitive adhesive composition (18) was applied using an applicator to the release-treated surface of a separate film made of a polyethylene terephthalate film subjected to a release treatment [trade name "PLR-382190" obtained from Lintech Co., Ltd.], and 1 at 100 ° C. It was dried for a minute, and the adhesive layer 12 was produced. The thickness of the obtained adhesive layer was 15 micrometers.

After bonding the obtained pressure-sensitive adhesive layer 12 to a cycloolefin film that does not contain a 23 μm ultraviolet absorber with a laminator, it is cured for 7 days under conditions of a temperature of 23° C. and a relative humidity of 65%, and the pressure-sensitive adhesive sheet 12 is obtained. got it

(Example 54) Preparation of the pressure-sensitive adhesive layer 13 and the pressure-sensitive adhesive sheet 13

Except having changed the adhesive composition 18 into the adhesive composition 19, it carried out similarly to Example 53, and produced the adhesive layer 13 and the adhesive sheet 13.

(Example 55) Preparation of the pressure-sensitive adhesive layer 14 and the pressure-sensitive adhesive sheet 14

Except having changed the adhesive composition 18 into the adhesive composition 20, it carried out similarly to Example 53, and produced the adhesive layer 14 and the adhesive sheet 14.

(Example 56) Preparation of the pressure-sensitive adhesive layer 15 and the pressure-sensitive adhesive sheet 15

Except having changed the adhesive composition 18 into the adhesive composition 21, it carried out similarly to Example 53, and produced the adhesive layer 15 and the adhesive sheet 15.

(Example 57) Preparation of the pressure-sensitive adhesive layer 16 and the pressure-sensitive adhesive sheet 16

Except having changed the adhesive composition 18 into the adhesive composition 22, it carried out similarly to Example 53, and produced the adhesive layer 16 and the adhesive sheet 16.

(Example 58) Preparation of the pressure-sensitive adhesive layer 17 and the pressure-sensitive adhesive sheet 17

Except having changed the adhesive composition 18 into the adhesive composition 23, it carried out similarly to Example 53, and produced the adhesive layer 17 and the adhesive sheet 17.

(Example 59) Preparation of the pressure-sensitive adhesive layer 18 and the pressure-sensitive adhesive sheet 18

Except having changed the adhesive composition 18 into the adhesive composition 24, it carried out similarly to Example 53, and produced the adhesive layer 18 and the adhesive sheet 18.

<Measurement of absorbance retention of adhesive sheet>

The obtained pressure-sensitive adhesive sheet 12 was cut to a size of 30 mm x 30 mm, the separate film was peeled off, the pressure-sensitive adhesive layer 12 and alkali-free glass (trade name "EAGLE XG" manufactured by Corning Corporation) were bonded together, and this was sampled ( 5).The absorbance in the wavelength range of 300 to 800 nm of the prepared sample 5 was measured at every 1 nm step by using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation). The absorbance was defined as the absorbance at a wavelength of 400 nm of the pressure-sensitive adhesive sheet 12. The results are shown in Table 8. In addition, the absorbance at a wavelength of 400 nm is 0 for both the cycloolefin film alone and the alkali-free glass alone.

The sample (5) after absorbance measurement was put into a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd.) under conditions of a temperature of 63°C and a relative humidity of 50% RH for 150 hours to perform a weather resistance test. The absorbance of the extracted sample (5) was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 400 nm was determined based on the following formula. A result is shown in Table 8. A value close to 100 for the absorbance retention indicates that the photoselective absorption function is not deteriorated and has good weather resistance.

Moreover, the absorbance retention at the time of injecting|throwing-in the sample (5) into a sunshine weather meter (made by Suga Testing Instruments Co., Ltd.) for 225 hours under the conditions of a temperature of 63 degreeC and a relative humidity of 50%RH was also calculated|required.

Absorbance retention (%) = (A(400) after endurance test / A(400) before endurance test) x 100

The absorbance retention was measured similarly except having changed the adhesive sheet 12 into the adhesive sheet 13 - the adhesive sheet 18. A result is shown in Table 8.

(Example 60) Preparation of the pressure-sensitive adhesive sheet 19

A pressure-sensitive adhesive sheet 19 was produced in the same manner as in Example 53 except that the 23 µm cycloolefin film not containing the ultraviolet absorber was changed to the 23 µm ultraviolet absorber-containing cycloolefin film.

(Example 61) Preparation of the pressure-sensitive adhesive sheet 20

A pressure-sensitive adhesive sheet 20 was produced in the same manner as in Example 54 except that the 23 µm cycloolefin film not containing the ultraviolet absorber was changed to the 23 µm ultraviolet absorber-containing cycloolefin film.

(Example 62) Preparation of the pressure-sensitive adhesive sheet 21

The pressure-sensitive adhesive sheet 21 was produced in the same manner as in Example 55 except that the 23 µm cycloolefin film not containing the ultraviolet absorber was changed to the 23 µm ultraviolet absorber-containing cycloolefin film.

(Example 63) Preparation of the pressure-sensitive adhesive sheet 22

The pressure-sensitive adhesive sheet 22 was produced in the same manner as in Example 56 except that the 23 µm cycloolefin film not containing the ultraviolet absorber was changed to the 23 µm ultraviolet absorber-containing cycloolefin film.

(Example 64) Preparation of the pressure-sensitive adhesive sheet 23

The pressure-sensitive adhesive sheet 23 was produced in the same manner as in Example 57 except that the 23 µm cycloolefin film not containing the ultraviolet absorber was changed to the 23 µm ultraviolet absorber-containing cycloolefin film.

(Example 65) Preparation of the pressure-sensitive adhesive sheet 24

A pressure-sensitive adhesive sheet 24 was produced in the same manner as in Example 58 except that the 23 µm cycloolefin film not containing the ultraviolet absorber was changed to the 23 µm ultraviolet absorber-containing cycloolefin film.

(Example 66) Preparation of the pressure-sensitive adhesive sheet 25

The pressure-sensitive adhesive sheet 25 was produced in the same manner as in Example 59 except that the 23 µm cycloolefin film not containing the ultraviolet absorber was changed to the 23 µm ultraviolet absorber-containing cycloolefin film.

<Measurement of absorbance retention of adhesive sheet>

The obtained pressure-sensitive adhesive sheet 19 was cut to a size of 30 mm x 30 mm, the separate film was peeled off, the pressure-sensitive adhesive layer 19 and alkali-free glass (trade name "EAGLE XG" manufactured by Corning Corporation) were bonded together, and this was sampled ( 6).The absorbance in the wavelength range of 300 to 800 nm of the prepared sample 5 was measured at every 1 nm step by using a spectrophotometer (UV-2450: manufactured by Shimadzu Corporation). The absorbance was defined as the absorbance of the pressure-sensitive adhesive sheet 19 at a wavelength of 405 nm.

The sample (6) after absorbance measurement was put into a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd.) for 150 hours under conditions of a temperature of 63°C and a relative humidity of 50% RH, and a weather resistance test was performed. The absorbance of the extracted sample (5) was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 405 nm was determined based on the following formula. A result is shown in Table 9. A value close to 100 for the absorbance retention indicates that the photoselective absorption function is not deteriorated and has good weather resistance.

Moreover, the absorbance retention at the time of injecting|throwing-in the sample 6 into the sunshine weather meter (made by Suga Testing Instruments Co., Ltd.) for 225 hours under the conditions of a temperature of 63 degreeC, and a relative humidity of 50%RH was also calculated|required.

Absorbance retention (%) = (A (405) after endurance test / A (405) before endurance test) x 100

Except having changed the adhesive sheet 19 into the adhesive sheet 20 - the adhesive sheet 25, it carried out similarly, and the absorbance retention was measured. A result is shown in Table 9.

The optical layer of the present invention has a good light absorption function at a wavelength of 380 to 400 nm even after a weather resistance test, and has good weather resistance (durability). Therefore, the optical film of this invention can maintain the function which suppresses deterioration of the retardation film or organic electroluminescent element by short wavelength visible light.

The optical film of this invention is used suitably for image display apparatuses, such as a liquid crystal panel and a liquid crystal display device.

1: Optical layer of the present invention
2: Optical layer of the present invention
3: Optical layer of the present invention
4: adhesive layer
5: Polarizer
6: adhesive layer
6a: adhesive layer
7: protective film
8: protective film
20: surface treatment layer
30: light emitting element
40: optical film
50, 50a: 1/4 wavelength retardation layer
60: adhesive layer
70: 1/2 wavelength retardation layer
80: positive C layer
100: polarizer
10A, 10B, 10C, 10D, 10E: laminate.

Claims (26)

An optical layer formed from a composition containing a compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X).

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.
R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.] The optical layer according to claim 1, wherein the compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X) is any of the compound represented by the formula (I) to the compound represented by the formula (VIII). .

[In formulas (I) to (VIII),
Rings W ¹ and R ³ have the same meanings as described above.
Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently It represents a ring structure having at least one double bond as a component.
Ring W ¹¹¹ represents a ring having at least two nitrogen atoms as a component.
Ring W ¹¹² and ring W ¹¹³ each independently represent a ring having at least one nitrogen atom as a constituent element.
R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ^{112 .} are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, which may have a substituent represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= ^{contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -NR 12A} -, - SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- it may be good
R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a heterocyclic group, a halogen atom, a nitro group, a cyano group, or a hydroxyl group , thiol group, carboxyl group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon having 6 to 18 carbon atoms which may have a substituent _{group and -CH 2} - or -CH= contained in this aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO -, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A are each independently a hydrogen atom or carbon number An alkyl group of 1-6 is represented.
R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ each independently represents an electron withdrawing group.
R ¹ and R ² may be bonded to each other to form a ring.
R ⁴¹ and R ⁴² may be bonded to each other to form a ring.
R ⁵¹ and R ⁵² may be bonded to each other to form a ring.
R ⁶¹ and R ⁶² may be bonded to each other to form a ring.
R ⁹¹ and R ⁹² may be bonded to each other to form a ring.
R ¹⁰¹ and R ¹⁰² may be bonded to each other to form a ring.
R ¹¹¹ and R ¹¹² may be bonded to each other to form a ring.
R ² and R ³ may be bonded to each other to form a ring.
R ¹² and R ¹³ may be bonded to each other to form a ring.
R ⁴² and R ⁴³ may be bonded to each other to form a ring.
R ⁵² and R ⁵³ may be bonded to each other to form a ring.
R ⁶² and R ⁶³ may be bonded to each other to form a ring.
R ⁷² and R ⁷³ may combine with each other to form a ring.
R ⁸² and R ⁸³ may be bonded to each other to form a ring.
R ⁹² and R ⁹³ may be bonded to each other to form a ring.
R ¹⁰² and R ¹⁰³ may be bonded to each other to form a ring.
R ¹¹² and R ¹¹³ may be bonded to each other to form a ring.
R ⁴ and R ⁵ may be bonded to each other to form a ring.
R ¹⁴ and R ¹⁵ may be bonded to each other to form a ring.
R ²⁴ and R ²⁵ may be bonded to each other to form a ring.
R ³⁴ and R ³⁵ may be bonded to each other to form a ring.
R ⁷⁴ and R ⁷⁵ may be bonded to each other to form a ring.
R ⁸⁴ and R ⁸⁵ may be bonded to each other to form a ring.
R ⁶ and R ⁸ each independently represent a divalent linking group.
R ⁷ represents a single bond or a divalent linking group.
R ⁹ and R ¹⁰ each independently represent a trivalent linking group.
R ¹¹ represents a tetravalent linking group.] The ^{at least one selected from R 4} and R ⁵ is a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group, or a fluoroaryl group. group, -CO-OR ²²² , -SO ₂ -R ²²² or -CO-R ²²² (R ²²² is a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or optionally a substituent having 6 to 18 carbon atoms represents an aromatic hydrocarbon group). ^{The at least one selected from R 4} and R ⁵ is a nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR according to claim 2 or 3 ²²² or -SO ₂ -R ²²² (R ²²² represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.); ^{The at least one selected from R 4} and R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom, a substituent according to any one of claims 2 to 4) represents an alkyl group having 1 to 25 carbon atoms which may have or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent). The optical layer according to any one of claims 2 to 5, wherein at least one selected from ^{R 4} and R ^{5 is a cyano group.} 7. The method according to any one of claims 2 to 6, wherein R ⁴ is a cyano group,
R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic group having 6 to 18 carbon atoms represents a hydrocarbon group). 8. The optical layer according to any one of claims 2 to 7, wherein R ⁴ and R ⁵ are both cyano groups. The optical layer according to any one of claims 2 to 8, wherein R ¹ and R ² are each independently an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent. The optical layer according to any one of claims 2 to 8, wherein R ¹ and R ² are connected to each other to form a ring. The optical layer according to claim 10, wherein ^{a ring formed by connecting R 1} and R ² to each other is an aliphatic ring. 12. The ring according to any one of claims 2 to 11, wherein the ring W ² , the ring W ³ , the ring W ⁴ , the ring W ⁵ , the ring W ⁶ , the ring W ⁷ , the ring W ⁸ , the ring W ⁹ , the ring W ¹⁰ , Ring W ¹¹ and ring W ¹² are each independently a ring having no aromaticity. 13. The method according to any one of claims 1 to 12, wherein R ³ is a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group, a fluoroaryl group , -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). 14. The method according to any one of claims 1 to 13, wherein R ³ is a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.). 15. The optical layer according to any one of claims 1 to 14, wherein R ³ is a cyano group. The optical layer according to any one of claims 1 to 15, which satisfies the following formula (a).
A(395)≥0.5 (a)
[A (395) represents the absorbance at a wavelength of 395 nm of the optical layer.] The optical layer according to any one of claims 1 to 16, which satisfies the following formula (b).
A(395)/A(430)≥10 (b)
[A(395) represents the absorbance at a wavelength of 395 nm of the optical layer, and A(430) represents the absorbance at a wavelength of 430 nm of the optical layer.] 18. The optical layer according to any one of claims 1 to 17, wherein the film thickness is from 1 to 500 mu m. The compound according to any one of claims 1 to 18, wherein the compound has a molecular weight of 3000 or less and has a partial structure represented by formula (X);
A resin having a glass transition temperature of 30° C. or less, and
An optical layer formed of a composition comprising a crosslinking agent. The compound according to any one of claims 1 to 18, wherein the compound has a molecular weight of 3000 or less and has a partial structure represented by formula (X);
a photocurable component,
An optical layer formed of a composition comprising a photoinitiator. The composition according to any one of claims 1 to 18, comprising a compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X), and at least one resin selected from the following group A. The optical layer formed.
Group A: Cellulose-based resins, (meth)acrylic-based resins, polyester-based resins, polyamide-based resins, polyimide-based resins and cycloolefin-based resins The optical laminated body containing the optical layer in any one of Claims 1-21, and a polarizer. An image display device comprising the optical laminate according to claim 22. A compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X);
A resin having a glass transition temperature of 30° C. or less, and
A composition comprising a crosslinking agent.

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.
R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.] A compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X);
a photocurable component,
A composition comprising a photoinitiator.

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.
R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.] A composition comprising a compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X), and at least one resin selected from the following group A.
Group A: Cellulose-based resins, (meth)acrylic-based resins, polyester-based resins, polyamide-based resins, polyimide-based resins and cycloolefin-based resins

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a constituent of the ring and not having aromaticity.
R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms. represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -O-CO-NR ^3A -, -NR ^4A -CO-, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, - CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S- , -SO- or -SO ₂ - may be substituted.
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A and R ^11A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

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