TW202132306A - Tetraazaporphyrin compound, ink composition, film, optical material, optical film, display surface film and display device - Google Patents

Abstract

A tetraazaporphyrin compound represented by the following general formula (1): (the symbols in the general formula (1) are as described in the Description.).

Description

Porphyrazine compound, ink composition, film, optical material, optical film, display surface film, and display device

The present invention relates to a porphyrazine compound and an ink composition, film, optical material, optical film, display surface film, and display device containing the porphyrazine compound.

In recent years, as the light source of lighting devices and display devices, white LEDs (Light Emitting Diodes) have been widely used. There are several types of white LED light sources, such as the following: a light source that combines three LEDs of R (red), G (green), and B (blue) with monochromatic light emission and mixed colors, and blue based on blue light-emitting LED A light source that is a combination of colored light and a yellow-emitting phosphor, and a light source that is based on a combination of a blue-emitting LED and a green and red-emitting phosphor.

Among them, when using a combination of blue light from a blue light emitting LED and a yellow light emitting phosphor, or a combination of a blue light emitting LED and a green and red light emitting phosphor to obtain white light, the following light is included , That is, in the spectrum of the obtained white light, the area near 590 nm shows orange and the area near 490 nm shows cyan light. It is known that if the luminous intensity of light in this area is higher, the color purity will decrease.

In order to improve the above problems, for example, Patent Document 1 discloses a color correction filter containing a porphyrazine compound having an absorption maximum in the wavelength region around 570 to 620 nm. [Prior Technical Literature] [Patent Literature]

Patent Document 1: Japanese Patent No. 5706097

[The problem to be solved by the invention]

The industry believes that in order to suppress light in the unwanted wavelength region caused by the reflection of light sources, optical components, or external light, it is effective to use a pigment compound that selectively absorbs light in the unwanted wavelength region. The porphyrazine compound described in Patent Document 1 has an absorption maximum in the vicinity of a wavelength of 570 to 620 nm, but has side absorption at a wavelength shorter than the maximum absorption wavelength, and therefore has color reproducibility (color purity). ) Or the problem of reduced brightness.

The present invention was completed in view of the above-mentioned actual situation, and its object is to provide a porphyrazine compound that reduces side absorption on the wavelength side (near 550 nm) shorter than the maximum absorption wavelength near the wavelength of 570 to 620 nm, and contains the tetraazaporphyrin compound. Ink composition, film, optical material, optical film, display surface film, and display device of azaporphyrin compound. [Technical means to solve the problem]

One embodiment of the present invention provides a porphyrazine compound represented by the following general formula (1).

[通式(1)中，R¹ 與R² 、R³ 與R⁴ 、R⁵ 與R⁶ 、及R⁷ 與R⁸ 之2個取代基中任一個取代基分別獨立地表示選自下述群組A中之基，另一個取代基分別獨立地表示選自下述群組B中之基，M表示二價之金屬原子或氧化金屬。 群組A：氫原子、及碳數1～12之脂肪族烴基 群組B：下述通式(2)所表示之一價基[化1]

[In the general formula (1), any one of the two substituents of ^{R 1} and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ^{8 is independently selected from the following} The group in group A and the other substituent each independently represent a group selected from the following group B, and M represents a divalent metal atom or metal oxide. Group A: Hydrogen atom and aliphatic hydrocarbon group with 1 to 12 carbons Group B: Monovalent group represented by the following general formula (2)

(通式(2)中，Ar表示(n＋1)價之芳香族烴基，X表示-O-、-S-、或-NH-，Y表示氫原子、丙烯醯基及甲基丙烯醯基中之至少1種。n為1～7之整數，*表示與四氮雜卟啉骨架之鍵結位置) 其中，於1分子中含有至少1個通式(2)所表示之一價基，該通式(2)所表示之一價基包含丙烯醯基及甲基丙烯醯基之至少1種作為Y]。[化2]

(In the general formula (2), Ar represents an aromatic hydrocarbon group of (n+1) valence, X represents -O-, -S-, or -NH-, and Y represents a hydrogen atom, one of an acrylic group and a methacrylic group At least one. n is an integer from 1 to 7, * represents the bonding position to the porphyrazine skeleton) wherein at least one monovalent group represented by the general formula (2) is contained in one molecule, the general The monovalent group represented by the formula (2) includes at least one of an acryloyl group and a methacryloyl group as Y].

One embodiment of the present invention provides an ink composition containing the porphyrazine compound according to one embodiment of the present invention and a binder component.

In one embodiment of the present invention, there is provided an ink composition, wherein the above-mentioned binder component contains a compound having an ethylenically unsaturated bond.

One embodiment of the present invention provides a film containing at least one of the ink composition and the cured product thereof according to one embodiment of the present invention.

An embodiment of the present invention provides an optical material containing the porphyrazine compound according to an embodiment of the present invention.

One embodiment of the present invention provides an optical film containing the porphyrazine compound according to one embodiment of the present invention.

One embodiment of the present invention provides a display device including the optical film of one embodiment of the present invention described above.

One embodiment of the present invention provides an ink composition for a display surface film, which contains the porphyrazine compound according to one embodiment of the present invention and a binder component.

In one embodiment of the present invention, there is provided an ink composition for a display surface film, wherein the adhesive component contains a compound having an ethylenically unsaturated bond.

One embodiment of the present invention provides a display surface film containing the porphyrazine compound according to one embodiment of the present invention.

One embodiment of the present invention provides a display device including the display surface film of one embodiment of the present invention. [Effects of Invention]

According to the embodiments of the present invention, there can be provided a porphyrazine compound that reduces side absorption on the wavelength side shorter than the maximum absorption wavelength near the wavelength of 570 to 620 nm, an ink composition containing the porphyrazine compound, Films, optical materials, optical films, display surface films and display devices.

Hereinafter, embodiments and examples of the present invention will be described with reference to the drawings and the like. However, the present invention can be implemented in many different aspects, and is not limited to the description of the embodiments and examples exemplified below. In addition, in order to explain more clearly, the drawings may schematically show the width, thickness, shape, etc. of each part compared with the actual state, but they are only an example and do not limit the interpretation of the present invention. In addition, in this specification and each drawing, the same reference numerals are attached to the same elements as those described in the already-shown drawings, and detailed descriptions may be omitted as appropriate. In addition, for the convenience of description, there are cases where the term "upper or lower" is used for description, but the up and down direction may be reversed. "In this specification, when a certain component or a certain area, etc., is located on the "upper (or below)" of other components or other areas, etc., as long as there is no special limitation, it does not only include that it is located directly above other components The case of (or directly below) also includes the case where it is located above (or below) other components, that is, the case where another component is contained in the space above (or below) other components.

In the present invention, (meth)acrylic acid means either acrylic acid or methacrylic acid, (meth)acrylate means either acrylate or methacrylate, and (meth)acryloyl means acryloyl or Each of the methacrylic acid groups. In addition, in this manual, the terms "plate", "sheet", and "membrane" are only different in terms of names, and are not distinguished from each other. "Film surface (plate surface, sheet surface)" refers to the overall and overall When observing the target film-shaped (plate-shaped, sheet-shaped) member, the surface that coincides with the plane direction of the target film-shaped member (plate-shaped member, sheet-shaped member) is observed. In addition, in this specification, "~" indicating a numerical range is used with the meaning that the numerical value described before and after it is included as the lower limit and the upper limit. Hereinafter, the porphyrazine compound, ink composition, film, optical material, optical film, display surface film, and display device of the present invention will be described in detail.

A. Porphyrazine compounds The porphyrazine compound of one embodiment of the present invention is a porphyrazine compound represented by the following general formula (1).

[通式(1)中，R¹ 與R² 、R³ 與R⁴ 、R⁵ 與R⁶ 、及R⁷ 與R⁸ 之2個取代基中任一個取代基分別獨立地表示選自下述群組A中之基，另一個取代基分別獨立地表示選自下述群組B中之基，M表示二價之金屬原子或氧化金屬。 群組A：氫原子、及碳數1～12之脂肪族烴基 群組B：下述通式(2)所表示之一價基[化3]

[In the general formula (1), any one of the two substituents of ^{R 1} and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ^{8 is independently selected from the following} The group in group A and the other substituent each independently represent a group selected from the following group B, and M represents a divalent metal atom or metal oxide. Group A: Hydrogen atom and aliphatic hydrocarbon group with 1 to 12 carbons Group B: Monovalent group represented by the following general formula (2)

(通式(2)中，Ar表示(n＋1)價之芳香族烴基，X表示-O-、-S-、或-NH-，Y表示氫原子、丙烯醯基及甲基丙烯醯基之至少1種；n為1～7之整數，*表示與四氮雜卟啉骨架之鍵結位置) 其中，於1分子中含有至少1個通式(2)所表示之一價基，該通式(2)所表示之一價基包含丙烯醯基及甲基丙烯醯基之至少1種作為Y]。[化4]

(In the general formula (2), Ar represents an aromatic hydrocarbon group with (n+1) valence, X represents -O-, -S-, or -NH-, and Y represents at least one of a hydrogen atom, an acrylic group and a methacrylic group One type; n is an integer from 1 to 7, * represents the bonding position to the porphyrazine skeleton) Wherein, at least one monovalent group represented by the general formula (2) is contained in one molecule, the general formula (2) The monovalent group represented includes at least one of an acrylic group and a methacrylic group as Y].

The porphyrazine compound represented by the general formula (1) has four isomers. Any one of the two substituents of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ each independently represents a group selected from the above group A, and the other Substituents each independently represent a group selected from the above-mentioned group B. Therefore, if the group selected from the above-mentioned group A is represented as G _A , and the group selected from the above-mentioned group B is represented as G _B , then There are 4 types of isomers represented by the following formula (1)-a to formula (1)-d. The above general formula (1) means ^{all four isomers including R 1} and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ in which the positional relationship of the two substituents is different. The porphyrazine compound of an embodiment of the present invention may contain only one of these isomers, or may contain two or more kinds in the form of a mixture.

Furthermore, in the porphyrazine compounds represented by the general formula (1) and the following formulas (1)-a to (1)-d, the groups selected from the group A may be the same as each other They may be different, and the groups selected from the above group B may be the same or different.

(通式(1)-a～式(1)-d中，G_A 表示選自上述群組A中之基，G_B 表示選自上述群組B中之基，M表示二價之金屬原子或氧化金屬)。[化5]

(In general formulas (1)-a to (1)-d, G _A represents a group selected from the above group A, G _B represents a group selected from the above group B, and M represents a divalent metal atom Or oxidized metal).

The group selected from the above group A is selected from hydrogen atoms and aliphatic hydrocarbon groups having 1 to 12 carbon atoms. As the aliphatic hydrocarbon group having 1 to 12 carbons, a linear, branched or cyclic saturated or unsaturated aliphatic hydrocarbon group having 1 to 12 carbons may be mentioned, and it may also be a linear or branched aliphatic hydrocarbon group and A combination of cyclic aliphatic hydrocarbon groups. Examples of the aliphatic hydrocarbon group having 1 to 12 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, tertiary butyl, and n-pentyl. Base, isopentyl, neopentyl, tertiary pentyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, 1-methylpentyl, 2 -Methylpentyl, 4-methylpentyl, 4-methyl-2-pentyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl Butyl, 1-ethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, 3-methylhexyl, 5-methylhexyl, 2,4-dimethylpentyl, ring Hexylmethyl, n-octyl, tertiary octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, 2,5-dimethylhexyl, 2,5,5-trimethyl Hexyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, 4-ethyloctyl Group, n-undecyl, 1-methyldecyl, n-dodecyl, 1,3,5,7-tetramethyloctyl, cyclopentyl, 2-methylcyclopentyl, cyclohexyl, 4-methylcyclohexyl, 2,6-dimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, nor-alkyl, adamantyl and other linear, branched or cyclic Shape of the alkyl group. Examples of unsaturated aliphatic hydrocarbon groups include ethylene, propylene, butylene, hexenyl, octenyl, dodecenyl, cyclohexenyl, ethynyl, and tertiary butylacetylene. Base and so on. As the group selected from the above group A, in terms of the thermal stability of the compound, an aliphatic hydrocarbon group having 1 to 10 carbon atoms is preferred, and an aliphatic hydrocarbon group having 3 to 10 carbon atoms is more preferred, More preferably, it is a tertiary butyl group or a cyclohexyl group.

The group selected from the above group B is selected from monovalent groups represented by the following general formula (2).

(通式(2)中，Ar表示(n＋1)價之芳香族烴基，X表示-O-、-S-、或-NH-，Y表示氫原子、丙烯醯基及甲基丙烯醯基之至少1種；n為1～7之整數，**表示與四氮雜卟啉骨架之鍵結位置。 其中，於1分子中含有至少1個通式(2)所表示之一價基，該通式(2)所表示之一價基包含丙烯醯基及甲基丙烯醯基之至少1種作為Y)。[化6]

(In the general formula (2), Ar represents an aromatic hydrocarbon group of (n+1) valence, X represents -O-, -S-, or -NH-, and Y represents at least one of a hydrogen atom, an acrylic group and a methacrylic group One type; n is an integer from 1 to 7, ** represents the bonding position with the porphyrazine skeleton. Among them, at least one monovalent group represented by the general formula (2) is contained in one molecule, and the general The monovalent group represented by the formula (2) includes at least one of an acryloyl group and a methacryloyl group as Y).

In the general formula (2), Ar represents an aromatic hydrocarbon group of (n+1) valence. Examples of the aromatic hydrocarbon include benzene, naphthalene, and biphenyl. In terms of solubility, benzene is preferred. n is an integer of 1-7, and among them, in terms of the stability of the compound, it is preferably an integer of 1-4, and more preferably an integer of 1-2. X represents -O-, -S-, or -NH-, and when n is 2 or more, X in the general formula (2) may be the same or different. Among them, in order to form a hydrogen bond, X is preferably -O- or -NH-, and more preferably -O-.

In the general formula (2), Y represents at least one of a hydrogen atom, an acrylic group, and a methacrylic group, and when n is 2 or more, Y in the general formula (2) may be the same or different. Among them, the porphyrazine compound represented by the general formula (1) contains at least one monovalent group represented by the general formula (2) in one molecule, and the monovalent group represented by the general formula (2) contains propylene At least one of an acyl group and a methacrylic group is referred to as Y. In order to form a crosslink with the binder component, the porphyrazine compound represented by the general formula (1) preferably contains two or more monovalent groups represented by the general formula (2) in one molecule, more preferably In order to contain 3 or more, and more preferably 4, the monovalent group represented by the above general formula (2) includes at least one of an acryloyl group and a methacryloyl group as Y.

In the aromatic hydrocarbon group of the general formula (2), the position where -X-Y is bonded is not particularly limited. As the monovalent group represented by the above general formula (2), for example, 2-(meth)acryloyloxyphenyl, 3-(meth)acryloyloxyphenyl, 4-(methyl) ) Allyloxyphenyl, 2,4-bis(meth)acryloxyphenyl, 2,5-bis(meth)acryloxyphenyl, 2,6-bis(meth)propylene Glyoxyphenyl, 3,5-bis(meth)acryloxyphenyl, 3,4,5-tris(meth)acryloxyphenyl, 2,3,5,6-tetra( (Methyl)acryloyloxyphenyl, 2-(meth)acryloylphenylsulfanyl, 3-(meth)acryloylphenylsulfanyl, 4-(meth)acryloylphenylsulfanyl, 2 ,4-Di(meth)acryloylphenylthio, 2,6-bis(meth)acryloylphenylthio, 3,5-bis(meth)acryloylphenylthio, 2-( Meth)acrylamidophenyl, 3-(meth)acrylamidophenyl, 4-(meth)acrylamidophenyl, 2,4-bis(meth)acrylamido Aminophenyl, 2,6-Di(meth)acrylamidophenyl, 3,5-Di(meth)acrylamidophenyl, 2-(meth)acryloxy -1-naphthyl, 2-(meth)propenyloxy-2-naphthyl, 2-(meth)propenylthio-1-naphthyl, 2-(meth)propenylthio -2-naphthyl, 2-(meth)acrylamido-1-naphthyl, 2-(meth)acrylamido-2-naphthyl, 2,3-bis(meth)propene Acetyloxy-1-naphthyl, 2-(meth)propenyloxybiphenyl, 2-(meth)propenylthiobiphenyl, 2-(meth)propenylamino biphenyl Phenyl and so on.

In the aromatic hydrocarbon group of the general formula (2), the position where -XY is bonded is not particularly limited. Among them, the aromatic hydrocarbon group of the general formula (2) is preferred in terms of easy reduction of side absorption. Among them, -XY is bonded at a remote position opposite to the position of the carbon atom bonded to the porphyrazine skeleton. Specifically, when the aromatic hydrocarbon of the aromatic hydrocarbon group of the general formula (2) is benzene, when the position of the carbon atom bonded to the porphyrazine skeleton is taken as the 1-position, it is preferably 4 The position is at least bonded with -XY. When the aromatic hydrocarbon is naphthalene, when the position of the carbon atom bonded to the porphyrazine skeleton is taken as the 1-position, it is preferably at least bonded to the 4-position or 5-position When -XY is bonded, and the position of the carbon atom bonded to the porphyrazine skeleton is taken as the 2-position, it is preferable that at least -XY is bonded to the 6-position. In this case, it is also possible to bond -XY to the adjacent carbon atom of the carbon atom bonded to the porphyrazine skeleton, and to bond with the carbon atom to the porphyrazine skeleton When the position is set as 1 position, -XY may be bonded to a position far away such as 3 positions.

M represents a divalent metal atom or an oxide metal. As M, Cu, Zn, Fe, Co, Ni, Ru, Rh, Pd, Pt, Mn, Mg, Ti, Be, Ca, Ba, Cd, Hg, Pb, Sn, etc. may be mentioned, for example. As the oxide metal represented by M, for example, VO, MnO, TiO, etc. may be mentioned. In the general formula (1), in terms of the stability of the compound, M is more preferably selected from the group consisting of Cu, Zn, Fe, Co, Ni, Pd, Mn, Mg, VO, and TiO At least one, more preferably at least one selected from the group consisting of Cu, Ni, Pd, and VO, and particularly preferably Cu or VO.

As the porphyrazine compound represented by the above general formula (1), for example, the following can be exemplified: Among the porphyrazine compounds represented by the above formula (1)-a to (1)-d, The group G _A selected from the aforementioned group A and the G _B selected from the aforementioned group B are the following combinations, but are not limited to them. Furthermore, in the following compounds (C1) to (C27), M in general formula (1)-a to formula (1)-d represents selected from Cu, Zn, Fe, Co, Ni, Pd, Mn, One of the group consisting of Mg, VO, and TiO, preferably the same as the above.

[Table 1] Table 1. Compound G _A G _B (C1) Tertiary butyl 2-(meth)acryloyloxyphenyl (C2) Tertiary butyl 3-(meth)acryloyloxyphenyl (C3) Tertiary butyl 4-(meth)acryloyloxyphenyl (C4) Tertiary butyl 2,4-bis(meth)acryloyloxyphenyl (C5) Tertiary butyl 2,5-bis(meth)acryloyloxyphenyl (C6) Tertiary butyl 2,6-Di(meth)acryloyloxyphenyl (C7) Tertiary butyl 4-(meth)acryloyloxyphenyl: 2,4-bis(meth)acryloyloxyphenyl=2:2 (C8) Tertiary butyl 4-(meth)acryloyloxyphenyl: 2,4-bis(meth)acryloyloxyphenyl=3:1 (C9) Tertiary butyl 4-(meth)acryloyloxyphenyl: 2,4-bis(meth)acryloyloxyphenyl=1:3 (C10) Isopropyl 2-(meth)acryloyloxyphenyl (C11) Isopropyl 3-(meth)acryloyloxyphenyl (C12) Isopropyl 4-(meth)acryloyloxyphenyl (C13) Isopropyl 2,4-bis(meth)acryloyloxyphenyl (C14) Isopropyl 2,5-bis(meth)acryloyloxyphenyl (C15) Isopropyl 2,6-Di(meth)acryloyloxyphenyl (C16) Third pentyl 2-(meth)acryloyloxyphenyl (C17) Third pentyl 3-(meth)acryloyloxyphenyl (C18) Third pentyl 4-(meth)acryloyloxyphenyl (C19) Third pentyl 2,4-bis(meth)acryloyloxyphenyl (C20) Third pentyl 2,5-bis(meth)acryloyloxyphenyl (C21) Third pentyl 2,6-Di(meth)acryloyloxyphenyl (C22) Cyclohexyl 2-(meth)acryloyloxyphenyl (C23) Cyclohexyl 3-(meth)acryloyloxyphenyl (C24) Cyclohexyl 4-(meth)acryloyloxyphenyl (C25) Cyclohexyl 2,4-bis(meth)acryloyloxyphenyl (C26) Cyclohexyl 2,5-bis(meth)acryloyloxyphenyl (C27) Cyclohexyl 2,6-Di(meth)acryloyloxyphenyl In Table 1, for example, the compound (C7) represents the following situation, that is, in the porphyrazine compound represented by the above formula (1)-a to formula (1)-d, there are 4 G _{A in one molecule} It is a tertiary butyl group, two G _Bs in one molecule are 4-(meth)acryloyloxy phenyl groups, and two G _Bs in one molecule are 2,4-bis(meth)acryloyloxy phenyl groups. Phenyl.

The porphyrazine compound represented by the above general formula (1) can be produced by referring to a known method. As a known manufacturing method, for example, Japanese Patent Laid-Open No. 11-11015, Japanese Patent Laid-Open No. 11-43619, Japanese Patent Laid-Open No. 11-100520, and Japanese Patent Laid-Open No. 11-116574 , Japanese Patent Laid-Open No. 11-130971, Japanese Patent Laid-Open No. 2002-129052, Japanese Patent Laid-Open No. 2006-321925, etc. The porphyrazine compound represented by the above general formula (1) can be carried out, for example, by combining a compound represented by the following general formula (3a) to general formula (3d) with a metal or metal salt in the presence of a base as required Reaction to manufacture. As said metal or metal salt, a metal halide, a metal carboxylate, etc. are mentioned, for example. In addition, as the above-mentioned base, for example, ammonium molybdate, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,5-diazabicyclo[4.3.0]- 5-nonene, trialkylamine, ammonia, etc.

(通式(3a)～通式(3d)中，R¹ ～R⁸ 表示與通式(1)相同之含義)。[化7]

(In general formula (3a) to general formula (3d), R ¹ to R ^{8 have the} same meaning as in general formula (1)).

The porphyrazine compound represented by the general formula (1) obtained by the cyclization reaction of the compound represented by the general formula (3a) to the general formula (3d) is usually R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ are a mixture of isomers in which the positional relationship of the two substituents is different.

Regarding the porphyrazine compound represented by the above general formula (1), in order to improve the color purity of the display device in the visible light range, the maximum absorption wavelength (λmax) in the wavelength range of 380 nm to 750 nm in the absorption spectrum , That is, the minimum transmission wavelength in the range of 380 nm to 750 nm in the transmission spectrum is preferably 570 nm to 620 nm, more preferably 580 nm to 610 nm, and even more preferably 585 nm to 605 nm. The maximum absorption wavelength or minimum transmission wavelength of the porphyrazine compound in the wavelength range of 380 nm to 750 nm can be appropriately changed by changing the central metal or substituent of the porphyrazine compound. Moreover, in order to cut off only the unnecessary light of the display device, the half-value width of the maximum absorption wavelength or the minimum transmission wavelength within the wavelength range of 380 nm to 750 nm is preferably 60 nm to 20 nm, and more preferably 50 nm to 50 nm. 20 nm.

In addition, the porphyrazine compound represented by the general formula (1) preferably has a reduced side absorption in 530 nm to 570 nm on the short-wavelength side, which is higher than the wavelength of 380 nm in the absorption spectrum. The maximum absorption wavelength (λmax) in the range from nm to 750 nm, that is, the shortest side of the minimum transmission wavelength in the range of 380 nm to 750 nm in the transmission spectrum, that is, at the minimum transmission wavelength of 540 nm to 560 nm The transmittance is preferably 78% or more, more preferably 80% or more.

Furthermore, the porphyrazine compound represented by the general formula (1) has a minimum transmission wavelength in the range of 380 nm to 750 nm in the transmission spectrum, and a minimum transmission wavelength in the range of 530 nm to 570 nm The transmittance can be measured in the following way. Specifically, first, with respect to 1 part by mass of the porphyrazine compound represented by the above-mentioned general formula (1), 79 parts by mass of pentaerythritol triacrylate (for example, trade name M305, manufactured by Toagosei Co., Ltd.), 1- 3 parts by mass of hydroxycyclohexyl phenyl ketone (for example, brand name Irgacure 184, manufactured by BASF) and 296 parts by mass of methyl ethyl ketone as a solvent were used to prepare a composition for spectrometry. Then, the composition for spectroscopic measurement was coated on a glass substrate (manufactured by Nippon Electric Glass Co., Ltd., "OA-10G") with a thickness of 0.7 mm using a spin coater. Thereafter, it was heated and dried on a hot plate at 80°C for 3 minutes to obtain a coating film. ^{The coating film was irradiated with ultraviolet rays of 500 mJ/cm 2} in terms of 254 nm using an ultra-high pressure mercury lamp, thereby obtaining a cured film. Furthermore, the film thickness is adjusted so that the transmittance of the minimum transmission wavelength in the range of 380 nm to 750 nm in the transmission spectrum becomes 40%. The transmission spectroscopic spectrum of the cured film was measured using the "microscopic spectrophotometer OSPSP200" manufactured by Olympus.

Regarding the porphyrazine compound represented by the general formula (1) of the present invention, any of the substituents of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ are respectively Independently represents a group selected from hydrogen atoms and aliphatic hydrocarbon groups having 1 to 12 carbon atoms, and the other substituent independently represents a monovalent group represented by the above general formula (2), therefore, at wavelengths of 570 to 620 There is a maximum absorption wavelength near nm, and the side absorption on the wavelength side shorter than the maximum absorption wavelength is reduced. Therefore, the porphyrazine compound represented by the general formula (1) of the present invention further selectively absorbs light in the desired wavelength region, that is, a pigment compound with a narrower absorption wavelength region and higher wavelength selectivity. If the porphyrazine compound represented by the general formula (1) of the present invention is used, the decrease in color purity or lightness caused by the aforementioned side absorption is suppressed, and the color purity or lightness is improved. It is speculated that the side absorption on the wavelength side shorter than the maximum absorption wavelength near the wavelength of 570 to 620 nm is caused by the association of porphyrazine compounds with each other. In view of this, it is presumed that the porphyrazine compound represented by the general formula (1) of the present invention includes an aromatic hydrocarbon group having a polar group as R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and one of R ⁷ and R ⁸ have 4 substituents, which inhibit self-association due to their polarity and bulkiness, and are compatible with heteroatom-containing adhesives commonly used to form coatings The performance is improved, and the compound is more uniformly dispersed, thereby reducing the side absorption near 550 nm on the wavelength side of the shorter wavelength side than the maximum absorption wavelength near the wavelength of 570 to 620 nm.

In addition, if in the aromatic hydrocarbon group of the above general formula (2), there is a bond at a position far away from the position of the carbon atom bonded to the porphyrazine skeleton, for example, the para position of the benzene ring- XY, the side absorption tends to decrease easily. It is presumed that the reason is that if the aromatic hydrocarbon group of the above general formula (2) is at a position far away from the position of the carbon atom bonded to the porphyrazine skeleton, for example, the bond is at the para position of the benzene ring With -XY, the kinetic energy of the porphyrazine skeleton can be inactivated in the horizontal direction, and the formation of vibration energy levels that cause side absorption can be inhibited (Figure 3).

B. Ink composition The ink composition of the present invention contains at least the above-mentioned porphyrazine compound of the present invention and a binder component. The ink composition of the present invention, by combining the porphyrazine compound of the present invention and the binder component, can form the side absorption of the shorter wavelength side than the maximum absorption wavelength near the wavelength of 570-620 nm. A film or molded article with improved color purity or brightness. The ink composition of the present invention contains at least the above-mentioned porphyrazine compound of the present invention and a binder component, and may also contain other components as necessary. Hereinafter, each component of the ink composition of the present invention will be described in detail in turn.

(Porphyrazine compound of the present invention) The above-mentioned porphyrazine compound of the present invention contained in the ink composition of the present invention may be the same as described above, and therefore, the description here is omitted. The porphyrazine compound of the present invention may be used alone in the ink composition of the present invention, or two or more of them may be used in combination. In addition, the porphyrazine compound of the present invention may be one compound or a mixture composed of two or more positional isomers. These positional isomers usually do not differ greatly in the absorption peak positions of each other, so even if it is a mixture, the peaks are relatively steep. If necessary, separate each positional isomer from the mixture of positional isomers, and use one compound of the positional isomers.

(Adhesive ingredients) The ink composition of the present invention contains a binder component in order to impart film-forming properties, moldability, and adhesion to the coated surface. The binder component preferably contains at least a resin. The resin may be any one of an adhesive, a thermoplastic resin, a thermosetting resin, and a photocuring resin. The resin here is not limited to a high-molecular compound or polymer, and may be a low-molecular compound or monomer. In addition, it may be particles of synthetic resin such as a resin emulsion. The binder component is preferably light-transmitting. When only the binder component is used to form a film with a thickness of 3 μm, the transmittance in the visible light region is preferably 80% or more, and more preferably 84% or more. Furthermore, the above-mentioned transmittance can be measured according to JISK7361-1 (Test Method for Total Light Transmittance of Plastic-Transparent Materials).

Examples of adhesives include acrylic adhesives, silicone adhesives, urethane adhesives, polyvinyl butyral adhesives, ethylene-vinyl acetate adhesives, poly Adhesives such as vinyl ether, saturated amorphous polyester, and melamine resin. In addition, as the thermoplastic resin, for example, acrylic resins such as poly(meth)acrylic acid, poly(meth)acrylate, polyacrylonitrile, polyacrylamide, etc.; polystyrene resins; nitrocellulose, ethylene Cellulose resins such as base cellulose and triacetyl cellulose; Polyester resins such as polyethylene terephthalate; Polycarbonate resins; Thermoplastic urethane resins; Chlorinated polyethylene, chlorine Polypropylene and other modified olefin resins; vinyl acetate resins, vinyl chloride-vinyl acetate copolymers, butyraldehyde resins and other vinyl resins, polyamide resins; polyimide resins; cyclic polyolefins, Olefin resins such as polyolefins, etc.

In order to impart sufficient hardness to the coating film, it is preferable to contain a curable binder component containing a thermosetting resin or a photocurable resin. The curable adhesive component is not particularly limited, and conventionally known curable adhesive components can be suitably used. As the curable adhesive component, for example, a photocurable adhesive component or a thermosetting adhesive component can be used. The photocurable adhesive component includes light that can be polymerized and cured by visible rays, ultraviolet rays, electron beams, etc. The curable resin, the thermosetting adhesive component includes a thermosetting resin that can be polymerized and hardened by heating.

As the thermosetting adhesive, a combination of a compound having two or more thermosetting functional groups in one molecule and a curing agent is usually used, and a catalyst that can promote the thermosetting reaction may be further added. As a thermosetting functional group, an epoxy group, an oxetanyl group, an isocyanate group, an ethylenically unsaturated bond, etc. are mentioned. As the thermosetting functional group, an epoxy group can be preferably used. As a specific example of the thermosetting adhesive component, for example, the one described in International Publication No. 2012/144521 can be mentioned.

On the other hand, as a photocurable adhesive, a combination of a compound having one or more photocurable functional groups in one molecule and a photoinitiator is generally used. These compounds and photoinitiators can be appropriately selected and used previously known. Examples of the photocurable functional group include radically polymerizable ethylenically unsaturated bond-containing groups, cationic polymerizable epoxy groups, and oxetanyl groups. As the photocurable functional group, an ethylenically unsaturated bond-containing group can be preferably used. Specifically, a vinyl group, a (meth)acryloyl group, and the like can be mentioned. The porphyrazine compound of the present invention has at least one (meth)acryloyl group in one molecule, and therefore can react with a compound having an ethylenically unsaturated bond. Therefore, in order to improve the dispersion stability of the porphyrazine compound of the present invention in the binder component, and inhibit the association of the porphyrazine compound with each other to obtain a steeper absorption characteristic, the binder component is preferably Contains compounds with ethylenically unsaturated bonds. In order to increase the hardness, the number of photocurable functional groups contained in one molecule of the photocurable compound is preferably 2 or more, and more preferably 3 or more. In order to increase the hardness, the number of ethylenically unsaturated bond-containing groups in a molecule of the compound having an ethylenically unsaturated bond is preferably 2 or more, and more preferably 3 or more. As the above-mentioned radically polymerizable compound, in order to have high reactivity, a compound having a (meth)acryloyl group is preferred, and a compound having two or more (meth)acryloyl groups per molecule is preferably used. Compounds such as multifunctional (meth)acrylate monomers; and (meth)acrylate urethane, polyester (meth)acrylate, epoxy (meth)acrylate, melamine (meth)acrylate Ester, polyfluoroalkyl (meth)acrylate, polysiloxane (meth)acrylate and other oligomers with more than two (meth)acrylic acid groups in the molecule and molecular weights ranging from hundreds to thousands, and It is also preferable to use a polyfunctional (meth)acrylate polymer having two or more (meth)acrylic acid groups on the side chain of the acrylate polymer. Among them, in order to increase the hardness, a multifunctional (meth)acrylate monomer having two or more (meth)acrylic groups in one molecule can be preferably used.

Moreover, as a resin emulsion, an acrylic emulsion, a styrene-acrylic emulsion, a vinyl acetate emulsion, an ethylene-vinyl acetate emulsion, etc. are mentioned.

In addition, when the film has a pattern and a photolithography step is used when forming the film, it is suitable to use a photosensitive adhesive component having alkali developability. As the photosensitive binder component, a positive photosensitive binder component and a negative photosensitive binder component can be mentioned. As the positive photosensitive adhesive component, for example, a system containing an o-quinonediazide group-containing compound as an alkali-soluble resin and a photosensitive imparting component can be mentioned. As the alkali-soluble resin, for example, a polyimide precursor can be mentioned. Wait.

As a negative photosensitive adhesive component, a system containing at least an alkali-soluble resin, a polyfunctional monomer, and a photoinitiator is suitably used. As specific examples of alkali-soluble resins, polyfunctional monomers, and photoinitiators, for example, those described in International Publication No. 2012/144521 may be mentioned.

The porphyrazine compound of the present invention includes an aromatic hydrocarbon group having a polar group as 4 of one of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ It can be used in combination with adhesive components containing heteroatoms such as oxygen atoms, sulfur atoms, and nitrogen atoms to improve compatibility with adhesive components containing heteroatoms. Since at least one of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ⁸ of the porphyrazine compound of the present invention has a (meth)acryloyl group, , Can react with compounds having ethylenic unsaturated bonds, and can be suitably used in combination with adhesive components containing compounds having ethylenic unsaturated bonds. In addition, the porphyrazine compound of the present invention described above contains an aromatic hydrocarbon group having a polar group containing a (meth)acryloyl group as four substituents, whereby even if there are two or more (methyl) groups in one molecule ) The radical polymerizable compound combination of acrylic group suppresses the side absorption around 550 nm. Therefore, a radical polymerizable compound having two or more (meth)acrylic acid groups in a molecule can be suitably used as a bonding agent.剂 Ingredients. Among them, in the following ink composition for display surface film, in order to increase the hardness of the display surface, it is preferable to contain a radical polymerizable compound having two or more (meth)acrylic groups in one molecule as a binder component .

(Solvent) The ink composition of the present invention may further contain a solvent. As the solvent used in the ink composition of the present invention, a solvent capable of dissolving or dispersing the porphyrazine compound of the present invention, the binder component, and other components added as necessary can be appropriately selected and used. As the solvent used in the ink composition of the present invention, for example, ethyl acetate, butyl acetate, methyl methoxypropionate, ethyl ethoxypropionate, ethyl lactate, methoxy acetate Ethyl acetate, propylene glycol monomethyl ether acetate, 3-methoxy-3-methyl-1-butyl acetate, 3-methoxybutyl acetate, methoxybutyl acetate, ethoxyethyl acetate , Ethyl acetate cellosolve and other ester solvents; methanol, ethanol and other alcohol solvents; methoxyethoxyethanol, ethoxyethoxyethanol and other carbitol solvents; acetone, methyl ethyl ketone, Ketone-based solvents such as methyl isobutyl ketone, cyclohexanone, and 2-heptanone, etc., but are not limited to them.

化合物、吡咯亞甲基化合物等。 本發明之墨水組合物還可進而包含例如於490 nm附近之波長區域具有吸收極大值之化合物。(Optional Additives) The ink composition of the present invention may also contain other light-absorbing compounds and various additives as needed within the scope not to impair the purpose of the present invention. As other light-absorbing compounds, for example, compounds having desired absorption in the visible light region, squaraine compounds, anthraquinone compounds, phthalocyanine compounds, methine compounds, methine azo compounds, 㗁𠯤 compounds, Azo compounds, styrene compounds, coumarin compounds, porphyrin compounds, dibenzofuranone compounds, diketopyrrolopyrrole compounds, rhodamine compounds, 𠮿

Compounds, pyrromethene compounds, etc. The ink composition of the present invention may further include, for example, a compound having an absorption maximum in a wavelength region near 490 nm.

Examples of additives include: polymerization terminator, chain transfer agent, leveling agent, plasticizer, surfactant, defoamer, silane coupling agent, ultraviolet absorber, adhesion promoter, antistatic agent, filler, etc. . As additives, inorganic or organic fine particles for adjusting hardness and refractive index, anti-glare agents, antifouling agents, flame retardants, antioxidants, light stabilizers, surface modifiers, etc. may be further included.

(The blending ratio of each component in the composition) In the ink composition of the present invention, the content of the porphyrazine compound of the present invention is not particularly limited, as long as it is appropriately selected according to the purpose. In order to improve the color purity of the display device by sufficiently cutting off unnecessary light and allowing the required light to pass through, the content of the porphyrazine compound of the present invention relative to the total solid content of the composition is preferably 0.5 -5% by mass, more preferably in the range of 0.8-3% by mass. If the porphyrazine compound is too small, it may be difficult to obtain the desired absorbance for light in an unnecessary wavelength region. In addition, if there are too many porphyrazine compounds, the composition is applied to the support and dried, and the adhesiveness with the support when it is cured, the surface roughness of the film, the hardness of the coating film, etc. It may become insufficient. Furthermore, in the present invention, the solid components are all components except the above-mentioned solvents, and also include polyfunctional monomers that are liquid at 25°C. The total content of the binder components is not particularly limited, as long as it is appropriately selected depending on any added components. The total content of the binder components relative to the total solid content of the composition is preferably 80% by mass or more, more preferably 85% by mass or more, 95% by mass or more, or 97% by mass or more. On the other hand, the upper limit is preferably 99.5% by mass or less, and more preferably 99.2% by mass or less. In addition, when a solvent is contained in the composition, the content of the porphyrazine compound may be appropriately adjusted in terms of dispersibility of the porphyrazine compound and coating properties of the composition. The solvent is usually preferably in the range of 65 to 95% by mass, and more preferably in the range of 75 to 88% by mass, relative to the total amount of the composition containing the solvent. Moreover, when an additive is contained in a composition, the content is not specifically limited, What is necessary is just to select suitably according to the objective. When other light-absorbing compounds are contained in the composition, the content thereof is not particularly limited, as long as it is appropriately selected according to the purpose. Regarding the content in the case of containing other light-absorbing compounds, for example, it may be in the range of 0.5 to 5% by mass, and further 0.8 to 3% by mass, relative to the total solid content of the composition.

(Manufacture of composition) The manufacturing method of the composition is not particularly limited. When an adhesive or a thermoplastic resin is used as an adhesive component, the above-mentioned porphyrazine compound of the present invention can also be added to the adhesive or thermoplastic resin and mixed and put into use. Alternatively, a method or the like may be exemplified by adding a binder component and various additional components as necessary to a solvent and mixing them, and then adding the porphyrazine compound of the present invention to the solvent and mixing them.

C. Membrane The film of one embodiment of the present invention contains at least one of the ink composition of one embodiment of the present invention and its cured product. The film of one embodiment of the present invention, by containing at least one of the ink composition of one embodiment of the present invention and its hardened substance, can selectively absorb wavelengths around 570-620 nm, and is more absorbing than this. The side absorption on the shorter wavelength side is reduced, and the color purity or brightness is improved. The film of the present invention may have a pattern, or may be a film without a pattern (flat film). In addition, the film of the present invention can be used in a state where it is laminated on a support, or it can be used after peeling off the film from the support.

The film of the present invention may also be called a sheet or a plate, and the film thickness can be appropriately adjusted according to the purpose. The film thickness may be 200 μm or less, and further may be 150 μm or less. Among them, in order to ensure the total light transmittance, the film of the present invention is preferably 100 μm or less, more preferably 80 μm or less, and still more preferably 50 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and still more preferably 0.3 μm or more.

The film of the present invention contains the porphyrazine compound of the present invention, so when the film thickness is 3 μm, the transmittance at a wavelength of 590 nm is preferably 40% or less, more preferably 30% or less, and more preferably Less than 20%. Furthermore, with regard to the transmittance of different thicknesses, a conversion value can be obtained using the Lambeau-Beer law based on the measured value of the transmittance at a certain thickness, and the obtained conversion value can be used as the transmittance of different thicknesses. Specifically, according to the Ramber-Beer law, the transmittance T is _{expressed by Log 10} (1/T)=kcb (k=constant inherent to a substance, c=concentration, b=optical path length). In the case of the transmittance of the film, if it is assumed that the density is constant even if the film thickness changes, then c is also a constant, so the above formula can be expressed as Log ₁₀ (1/T)=fb (f=kc) using the constant f . Here, if the transmittance at a certain film thickness is known, the intrinsic constant f of each substance can be obtained. Therefore, if the mathematical expression T=1/10 ^{f · b is used} , and the intrinsic constant is substituted into f, and the target film thickness is substituted into b, the transmittance at the required film thickness can be obtained.

In addition, the film of the present invention contains the above-mentioned porphyrazine compound of the present invention, thereby reducing the side absorption on the wavelength side (near 550 nm) which is shorter than the maximum absorption wavelength near the wavelength of 570 to 620 nm. Specifically, for example, the ratio (T ₂ /T _{1 ) of the transmittance T 2} (%) to the transmittance T ₁ (%) is preferably 1.95 or more, more preferably 2.00 or more, and the above-mentioned transmittance T ₂ (% ) Is the transmittance at the smallest transmission wavelength in the range of 530 nm to 570 nm. The above-mentioned transmittance T ₁ (%) is the transmittance at the smallest transmission wavelength in the range of 380 nm to 750 nm in the transmission spectrum.

As a method of manufacturing a film of one embodiment of the present invention, for example, a method including the steps of: using the ink composition of one embodiment of the present invention to form a composition layer on a support; and further using The above composition layer hardens.

The support is not particularly limited, except that it contains glass, silicon, polycarbonate, polyester, polyacrylic acid, aromatic polyamide, polyamide imide, polyimide, cycloolefin polymer, and In addition to the support made of cellulose and other materials, it can also be other optical components used in display devices.

As a method of applying the ink composition to the support, a known method can be appropriately selected and used. For example, gravure coating method, reverse coating method, blade coating method, dip coating method, spray coating method, air knife coating method, spin coating method, roll coating method, printing method, dipping and pulling method can be mentioned. , Curtain coating method, die nozzle coating method, casting method, bar coating method, extrusion coating method, E-type coating method and other coating methods, inkjet, nozzle jet and other spray system printing, soft Various printing methods such as plate printing, screen printing, gravure printing, reverse offset printing, metal mask printing method, transfer method using molds, etc., nano imprinting method, etc.

The composition layer applied on the support can be formed into a film by properly removing (drying) the solvent as needed.

As the step of hardening the above-mentioned composition layer, depending on the curability of the adhesive component contained in the composition, a well-known method such as applying at least one of heating and light irradiation can be appropriately selected to harden the adhesive component. . In addition, the support can also be removed after the membrane is manufactured.

As a manufacturing method when the film has a pattern in one embodiment of the present invention, a method including the following steps can be further exemplified: forming a pattern on the composition layer by a photolithography method or a dry etching method. Regarding the photolithography method or the dry etching method, there is no particular limitation, and a known method can be appropriately selected and applied depending on the binder component contained in the composition.

As another manufacturing method of the film of one embodiment of the present invention, for example, a method of using and molding the ink composition of one embodiment of the present invention described above can be exemplified. As a molding method, a known method can be appropriately selected and applied depending on the binder component contained in the ink composition.

The film of one embodiment of the present invention can be used for solid-state imaging devices such as CCD (Charge Coupled Device) and CMOS (complementary metal oxide semiconductor) in addition to image display devices. Various devices. In addition, the film of one embodiment of the present invention is suitable for use in optical films for the purpose of transmitting or reflecting and absorbing light to impart various effects, and can also be used for recording media that use selective wavelengths of heat absorption. Since the film of one embodiment of the present invention can selectively absorb wavelengths around 570-620 nm, and the side absorption on the shorter wavelength side than the maximum absorption wavelength around 570-620 nm is reduced, the color purity or brightness is improved. Therefore, it is particularly suitable for the following display surface film.

D. Optical materials, optical films, optical filters and display surface films The optical material of one embodiment of the present invention contains the above-mentioned porphyrazine compound of the present invention. In addition, the optical film of one embodiment of the present invention contains the above-mentioned porphyrazine compound of the present invention. In addition, the optical filter of one embodiment of the present invention contains the above-mentioned porphyrazine compound of the present invention. In addition, a display surface film of one embodiment of the present invention contains the porphyrazine compound of the present invention.

The optical material of one embodiment of the present invention is a material for the purpose of transmitting or reflecting and absorbing light to impart various effects. As the optical material of the present invention, for example, a lens or the like may be mentioned. The lens may, for example, be a plastic spectacle lens, sunglasses lens, goggles, and the like. Moreover, as the optical material of the present invention, for example, an optical film can be exemplified, which is a film for the purpose of transmitting or reflecting and absorbing light to impart various effects. As an optical film, specifically, an anti-reflection film, an alignment film, etc. are mentioned, for example. In addition, the optical film includes, for example, an optical filter that transmits only light having a predetermined property (for example, light in a specific wavelength range) among incident light, and does not transmit other light. As the optical filter, for example, a specific wavelength absorption filter that selectively absorbs light in an unnecessary wavelength range, a color correction filter that adjusts the color tone, an ultraviolet cut filter, and an infrared cut filter can be mentioned. Pieces and so on. As an optical filter, for example, it is applied to display devices, lighting devices, window materials, and the like.

The optical material of one embodiment of the present invention can be manufactured by, for example, molding the ink composition of one embodiment of the present invention described above, or it can be manufactured in the same manner as the film of one embodiment of the present invention described above. Furthermore, the optical film of one embodiment of the present invention including the optical filter of one embodiment of the present invention preferably includes the film of one embodiment of the present invention described above.

The optical film of one embodiment of the present invention may be the same as the film of one embodiment of the present invention described above, may include a support, and may further laminate an adhesive layer and a peelable release film. As the support, the adhesive layer, and the peelable release film, a previously known structure can be appropriately selected and applied. As specific examples of the adhesive layer and the peelable release film, for example, those described in Japanese Patent Laid-Open No. 2009-251511 can be cited.

The optical film of one embodiment of the present invention may further have other functional layers. As other functional layers, for example, a polarizing element, a protective film, an anti-reflection layer, an anti-glare layer, an antifouling layer, an antistatic layer, a hard coat layer, an adhesive layer, an adhesive layer, etc. may be mentioned. As the polarizing element, protective film, anti-reflection layer, anti-glare layer, anti-fouling layer, anti-static layer, hard coat layer, adhesive layer, and adhesive layer, previously known constitutions can be adopted respectively.

In addition, in the optical film of one embodiment of the present invention, the film containing the porphyrazine compound of the present invention may further impart other functions in addition to the function of selectively absorbing wavelengths around 570 to 620 nm. As other functions, for example, one or more layers selected from the group consisting of a protective film, an anti-reflection layer, an anti-glare layer, an anti-fouling layer, an antistatic layer, a hard coat layer, an adhesive layer, and an adhesive layer can be mentioned. The functions it has.

The optical film of one embodiment of the present invention may also contain the above-mentioned porphyrazine compound of the present invention in the structure of a previously known optical film. For example, an optical film in which the above-mentioned at least one functional layer contains the above-mentioned porphyrazine compound according to an embodiment of the present invention can be exemplified.

The optical film of one embodiment of the present invention may also be a display surface film provided on the observer side surface of a display panel in a display device. The display surface film of one embodiment of the present invention contains the above-mentioned porphyrazine compound of the present invention, and can usually have the required surface functional layer on the surface of the display, and then on the support of the surface functional layer and the surface of the support The functional layer has an adhesive layer or an adhesive layer on the opposite side. As the surface functional layer, for example, at least one layer of a hard coat layer, an anti-reflection layer, an anti-glare layer, an antifouling layer, and an antistatic layer may be mentioned. As the surface functional layer, in order to increase the surface hardness of the display surface film and form a coating film by a solution process, it is preferably a layer with the function of a hard coat layer, and more preferably has at least a hard coat layer and an anti-reflection layer Functional layer.

The hard coat layer is usually a layer having a hardness higher than that of the protective film and at least imparting scratch resistance. The hard coat layer preferably exhibits a hardness of "H" or higher in the pencil hardness test (4.9 N load) specified in JIS K5600-5-4 (1999). The hard coat layer preferably has an anti-reflection function and an anti-glare function to improve visibility, and may further have an anti-fouling function and an anti-static function. The hard coat layer can be appropriately selected and used in the optical filter or the hard coat layer used in the optical film of the previously known display device. As the hard coat layer, for example, the hard coat layer described in International Publication No. 2012/018087, International Publication No. 2011/065531, Japanese Patent Laid-Open No. 2018-51918, etc. can be referred to, although this content is incorporated in this specification , But not limited to them.

As the structure of the anti-reflective layer, anti-glare layer, anti-fouling layer, and anti-static layer used as the surface functional layer, a previously known structure can also be appropriately selected. For example, refer to Japanese Patent No. 6070195 and Japanese Patent No. 6040936 , Japanese Patent Publication No. 2017-21293, Japanese Patent Publication No. 2013-142817, Japanese Patent Publication No. 2011-90301, etc.

Fig. 1 is a schematic cross-sectional view showing an example of the display surface film of the present invention. As shown in FIG. 1, the display surface film 40 may be a laminate having a surface functional layer 30 on one side of the support 1 and an adhesive layer or an adhesive layer 2 on the other side of the support 1. The display surface film of the present invention may also only include a film equivalent to the surface functional layer 30. However, the above-mentioned surface functional layer 30 may be one layer, or a laminate including two or more layers. As the structure when the surface functional layer 30 is a laminate, for example, a structure in which a hard coat layer and an anti-reflection layer including a low refractive index layer and a high refractive index layer are sequentially laminated can be exemplified.

The display surface film of the present invention may contain the porphyrazine compound of the present invention in any one of the surface functional layer 30, the support 1, and the adhesive layer or the adhesive layer 2, and may also contain the porphyrazine compound of the present invention in two or more layers. Porphyrazine compounds. The surface functional layer 30, the support 1, and the adhesive layer or the adhesive layer 2 containing the porphyrazine compound of the present invention can be appropriately selected with adhesive components and other components as required to be compatible with the production of the above-mentioned present invention. The film of one embodiment is manufactured in the same way. The material of the support 1 is preferably appropriately selected from the thermoplastic resin in the binder component of the ink composition of one embodiment of the present invention, and it can be combined with the support of the film of one embodiment of the present invention. same. As the support 1, among them, in terms of optical characteristics, a triacetyl cellulose film (TAC film), a cycloolefin polymer film, and the like are suitably used. In addition, as the material of the adhesive layer or the adhesive layer 2, it is necessary to appropriately select and use from the adhesive or curable adhesive component in the adhesive component of the ink composition of one embodiment of the present invention. Transmittance in the visible light region A higher binder composition is sufficient.

As far as the existing manufacturing steps of the display device can be used, the porphyrazine compound of the present invention is preferably included in the surface functional layer 30. Even if the porphyrazine compound of the present invention is combined with a radically polymerizable compound having two or more (meth)acryloyl groups in one molecule, it can suppress side absorption near 550 nm and is suitably used. Therefore, the display surface film of the present invention may include a layer or film containing the porphyrazine compound of the present invention and a cured product of a radical polymerizable compound having two or more (meth)acryloyl groups in one molecule, It can selectively absorb the wavelengths around 570-620 nm, and can reduce the side absorption on the shorter wavelength side than the maximum absorption wavelength around 570-620 nm, and increase the hardness of the display surface, thereby improving the scratch resistance.

In the display surface film of the present invention, the total thickness of the surface functional layer may be appropriately selected. For example, it may be 10 to 150 μm, but it is usually 20 to 100 μm. In the display surface film of the present invention, the thickness of the support when it has a support may be appropriately selected, for example, 10 to 150 μm, but usually 20 to 100 μm. In the display surface film of the present invention, the thickness of the adhesive layer or the adhesive layer when the adhesive layer or the adhesive layer is provided may be appropriately selected, for example, 10 to 150 μm, but usually 20 to 100 μm.

Regarding the display surface film of the present invention, the transmittance in the visible light region (380 nm to 750 nm) measured in accordance with JISK7361-1 is preferably 80% or more, more preferably 90% or more.

E. Display device A display device according to one embodiment of the present invention is a display device provided with the optical film according to one embodiment of the present invention. The above-mentioned optical film of the present invention may be used as long as it is assembled into a display device, and the method of assembling is not particularly limited. As a display device, it can be applied without particular limitation. Examples of the display elements constituting the display device include: liquid crystal display elements, EL (inorganic EL, organic EL) display elements, plasma display elements, electronic paper display elements, LED display elements (micro LEDs, etc.), light emission using quantum dots Display components of the diode (QLED), etc. That is, as a display device, for example, a liquid crystal display device, an EL (inorganic EL, organic EL) display device, a plasma display device, an electronic paper display device, an LED display device (micro LED, etc.), a light emitting diode using quantum dots Display devices such as QLED. Furthermore, in the case of a liquid crystal display device, it is necessary to arrange a backlight on the side opposite to the molded body of the display element. Among them, in order to have high color purity of the displayed color, the display device of one embodiment of the present invention preferably includes a display surface film containing the porphyrazine compound of the present invention.

An example of a display device according to an embodiment of the present invention will be described with reference to the drawings. As shown in FIG. 2, the image display device 100 mainly includes a display panel 10 for displaying images, and a backlight device 20 arranged on the back side of the display panel 10. In this embodiment, the display panel 10 is a liquid crystal display panel. Therefore, the image display device 100 includes the backlight device 20. However, depending on the type of the display panel (display element), the backlight device 20 may not be provided.

(Display panel) As shown in FIG. 2, the display panel 10 has a protective film 11, a polarizing element 12, a protective film 13, a translucent adhesive layer 14, a display element 15, and a translucent adhesive layer laminated in this order from the backlight device 20 side to the viewer side. 16. The structure of the protective film 17, the polarizing element 18, the translucent adhesive layer 16', the protective film 19, and the surface functional layer 30. In FIG. 2, the laminated body of the translucent adhesive layer 16 ′, the protective film 19, and the surface functional layer 30 corresponds to the display surface film 40. In addition, the display panel 10 only needs to include the display element 15 and does not need to include the protective film 11 and the like.

The display element 15 in FIG. 2 is a liquid crystal display element. However, the display element 15 is not limited to a liquid crystal display element, and may be, for example, a display element as described above. In the liquid crystal display element, a liquid crystal layer, an alignment film, an electrode layer, a color filter, etc. are arranged between two glass substrates. The protective film, the polarizing element, and the light-transmitting adhesive layer can be appropriately selected and used previously known. As a protective film, a triacetyl cellulose film (TAC film), a cycloolefin polymer film, etc. are mentioned suitably. As the light-transmitting adhesive layer, for example, an adhesive sheet such as OCA (Optical Clear Adhesive) is suitable, or a liquid containing a polymerizable compound such as OCR (Optically Clear Resin). Cured products of the composition for curable adhesive layer.

The surface functional layer 30 in FIG. 2 is a layer that is located on the surface of the display panel in the display device and imparts various functions, and may be one layer or two or more layers. The surface functional layer 30 is a layer having at least one function of a hard coating layer, an anti-reflection layer, an anti-glare layer, an anti-fouling layer, and an antistatic layer. The surface functional layer 30 may be the same as the surface functional layer described in the display surface film of one embodiment of the present invention.

(Backlight device) The backlight device 20 illuminates the display panel 10 from the back side of the display panel 10. As the backlight device 20, a well-known backlight device can be used, and the backlight device 20 can be either an edge-lit type or a direct type backlight device. In addition, as the light source of the backlight, an LED, CCFL (Cold Cathode Fluorescent Lamp, cold cathode fluorescent tube), etc. can be exemplified. The backlight using quantum dots as the light source can easily improve the color reproducibility.

The display device of one embodiment of the present invention includes an optical film containing the porphyrazine compound of the present invention, and therefore, it is suitable for use in a display device using a white LED as a light source. Among them, if the optical film containing the porphyrazine compound of the present invention is used, it is necessary to appropriately remove the orange light near 590 nm and correct the chromaticity of white light to a better one, preferably a white LED A display device with a light source in the following manner, that is, a method of obtaining white light by the combination of blue light of a blue light emitting LED and a yellow light emitting phosphor, or a method of obtaining white light by a blue light emitting LED and a green and red light emitting phosphor The combination of light bodies to obtain white light.

The display device of one embodiment of the present invention includes an optical film containing the porphyrazine compound of the present invention, and the optical film may not be the display surface film of one embodiment of the present invention. The installation position of the optical film is not particularly limited, as long as it is arranged between the backlight light source and the observer of the display device. Regarding the display device of one embodiment of the present invention, for example, in FIG. 2, the translucent adhesive layer 16 and the protective film 17 existing between the display element 15 and the polarizing element 12 can be made of the tetraazaporin of the present invention. The optical film of the phyrin compound, the protective film 11, the protective film 13, or the translucent adhesive layer 14 may also be an optical film containing the porphyrazine compound of the present invention.

The display device according to an embodiment of the present invention is not limited to the above-mentioned examples, as long as it appropriately selects and adopts a previously known configuration. The display device according to one embodiment of the present invention may be provided with a touch panel, for example, on the side of the observer closer to the observer side than the display panel 10 of FIG. 2 via, for example, a light-transmitting adhesive layer. Example

Hereinafter, examples will be shown to specifically describe the present invention. The embodiments of the present invention are not limited by these descriptions.

(Synthesis Example 1: Synthesis of Compound 1) (1) Synthesis of Intermediate 1 Combine 2,7,12,17-tetra-tert-butyl-5,10,15,20-copper porphyrazine 40 g, N-bromosuccinimide (NBS) 49.8 g, and dimethyl 400 g of dimethanamide (DMF) was heated in 400 ml of toluene at 75-80°C for 4 hours. The obtained reaction solution was concentrated, and 300 ml of methanol was added to the concentrated reaction solution to precipitate the precipitate. The precipitate was filtered and dried to obtain 57 g of the following intermediate 1 as a blue powder. According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 915(M+) ・Elemental analysis value: CHN measured value (42.01%, 3.80%, 12.00%) ; Theoretical value (41.97%, 3.96%, 12.24%)

[化8] Intermediate 1

(2) Synthesis of Intermediate 2 The above-obtained intermediate 17.25 g, 2-methoxyphenylboronic acid 4.93 g, sodium carbonate 3.44 g, and tetrakis (triphenylphosphine) palladium 0.92 g were dispersed in 70 ml of toluene, 40 ml of water, and ethanol. In 20 ml of mixed solvent, react at 80～85℃ for 30 hours. After the reaction, the reaction solution was cooled to room temperature, 200 ml of toluene and 200 ml of water were added, and the reaction product was extracted in toluene. The residue was obtained by concentrating the toluene solution under reduced pressure. The residue was dispersed with methanol, filtered, and dried to obtain 7.3 g of the following intermediate 2 as a blue powder. According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 1024(M+H), ・Elemental analysis value: CHN measured value (70.10%, 6.33%, 11.00%) ; Theoretical value (70.32%, 6.30%, 10.93%)

[化9] Intermediate 2

(3) Synthesis of intermediate 3 Disperse 2 6.5 g of the intermediate obtained above in 65 ml of dichloromethane, add dropwise 41.1 g of dichloromethane solution (1 mol/L) of boron tribromide at 5°C, and then stir at 5°C for 1 After hours, it was stirred at room temperature (25°C) for 3 hours. The precipitate was filtered, washed with 20 ml of dichloromethane and 200 ml of water, and dried to obtain 4.9 g of the following intermediate 3 as a blue powder. According to the following analysis results, the obtained compound was confirmed to be the target compound. MS(ESI)(m/z): 968(M+) ・Elemental analysis value: CHN measured value (69.30%, 5.75%, 11.50%) ; Theoretical value (69.44%, 5.83%, 11.57%)

[化10] Intermediate 3

(4) Synthesis of compound 1 3.5 g of the intermediate 3, 4.4 g of triethylamine, and 4.0 g of propylene chloride obtained above were dispersed in 50 ml of tetrahydrofuran, and reacted at 40°C for 4 hours. After the reaction, the reaction solution was concentrated under reduced pressure to obtain a residue. The residue was dispersed with methanol, filtered, and dried to obtain 3.0 g of the following compound 1 as a blue powder. According to the following analysis results, the obtained compound was confirmed to be the target compound. · MS(ESI)(m/z): 1184(M+H), ・Elemental analysis value: CHN measured value (68.90%, 5.33%, 9.30%) ; Theoretical value (68.93%, 5.44%, 9.46%)

[化11] Compound 1

(Synthesis Example 2: Synthesis of Compound 2) (1) Synthesis of intermediate 4 In the synthesis of Intermediate 2 of Synthesis Example 1, 4.93 g of 3-methoxyphenylboronic acid was used instead of 4.93 g of 2-methoxyphenylboronic acid. Otherwise, the synthesis with Intermediate 2 of Synthesis Example 1 In the same way, 8.0 g of the following intermediate 4 as a blue powder was obtained. According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 1024(M+H) ・Elemental analysis value: CHN measured value (70.30%, 6.20%, 10.70%) ; Theoretical value (70.32%, 6.30%, 10.93%)

[化12] Intermediate 4

(2) Synthesis of intermediate 5 In Synthesis Example 1 above, 6.5 g of Intermediate 4 was used instead of 6.5 g of Intermediate 2. In the same manner as in Synthesis Example 1, 5.5 g of the following Intermediate 5 was obtained as a blue powder. According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 968(M+), ・Elemental analysis value: CHN measured value (69.48%, 5.80%, 11.61%) ; Theoretical value (69.44%, 5.83%, 11.57%)

[化13] Intermediate 5

(3) Synthesis of compound 2 In Synthesis Example 1, 3.5 g of Intermediate 5 was used instead of 3.5 g of Intermediate 3. In the same manner as in Synthesis Example 1, 3.3 g of the following compound 2 was obtained as a blue powder. According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 1184(M+H), ・Elemental analysis value: CHN measured value (68.85%, 5.43%, 9.50%) ; Theoretical value (68.93%, 5.44%, 9.46%)

[Chemical Formula 14] Compound 2

(Synthesis Example 3: Synthesis of Compound 3) (1) Synthesis of Intermediate 6 In the synthesis of Intermediate 2 of Synthesis Example 1, 4.93 g of 4-methoxyphenylboronic acid was used instead of 4.93 g of 2-methoxyphenylboronic acid. Otherwise, the synthesis with Intermediate 2 of Synthesis Example 1 In the same way, 7.1 g of the following intermediate 6 as a blue powder was obtained. According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 1024(M+H), ・Elemental analysis value: CHN measured value (70.29%, 6.35%, 10.80%) ; Theoretical value (70.32%, 6.30%, 10.93%)

[化15] Intermediate 6

(2) Synthesis of Intermediate 7 In Synthesis Example 1 described above, 6.5 g of Intermediate 6 was used instead of 6.5 g of Intermediate 2. In the same manner as in Synthesis Example 1 described above, 5.0 g of the following Intermediate 7 as a blue powder was obtained. According to the following analysis results, the obtained compound was confirmed to be the target compound. · MS(ESI)(m/z): 968(M+), ・Elemental analysis value: CHN measured value (69.38%, 5.86%, 11.62%) ; Theoretical value (69.44%, 5.83%, 11.57%)

[化16] Intermediate 7

(3) Synthesis of compound 3 In Synthesis Example 1, 3.5 g of Intermediate 7 was used instead of 3.5 g of Intermediate 3. In the same manner as in Synthesis Example 1, 3.5 g of the following compound 3 was obtained as a blue powder. According to the following analysis results, the obtained compound was confirmed to be the target compound. · MS(ESI)(m/z): 1184(M+H), ・Elemental analysis value: CHN measured value (68.70%, 5.50%, 9.30%) ; Theoretical value (68.93%, 5.44%, 9.46%)

[化17] Compound 3

(Comparative Synthesis Example 1: Synthesis of Comparative Compound 1) Under a nitrogen atmosphere, add 1.34 g of 2-tert-butyl-2-maleonitrile and 0.33 g of cuprous chloride to 30 ml of n-pentanol. After heating to 90°C, add 1,8-diazepine Heterobicyclo[5.4.0]-7-undecene (DBU) 1.52 g was added dropwise to the mixture over 30 minutes. After the dropwise addition, the mixture was stirred at 125°C for 8 hours. After the reaction mixture was cooled to room temperature, 100 ml of methanol was added, and then, 50 ml of water was further added dropwise. The precipitated solid was separated by filtration. After dissolving the solid in toluene, it was purified by silica gel column chromatography [developing solution: toluene/n-hexane (volume ratio: 2/1)] to obtain 0.82 g of the following comparative compound 1 as a blue solid . According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 599(M+), ・Elemental analysis value: CHN measured value (64.06%, 6.71%, 18.67%) ; Theoretical value (64.03%, 6.72%, 18.69%)

[Chemical Formula 18] Comparative Compound 1

(Comparative Synthesis Example 2: Synthesis of Comparative Compound 2) 1.57 g of vanadium trichloride was added to 50 g of 1-pentanol, and 1.02 g of ammonia gas was introduced into the reaction solution at 20°C for 1 hour. After stirring for 1 hour at 20-30°C, 5.38 g of 2-tert-butyl-2-maleonitrile was charged, and stirring was continued at 125°C for 6 hours. Then, about 40 g of 1-pentanol was removed from the reaction mixture by distillation, and methanol-water (weight ratio of methanol to water 1:1) was charged and stirred. The precipitate was collected by filtration, washed with methanol, and dried to obtain 5.46 g of the following comparative compound 2 as a blue solid. According to the following analysis results, the obtained compound was confirmed to be the target compound. ・MS(ESI)(m/z): 603(M+), ・Elemental analysis value: CHN measured value (63.70%, 6.71%, 18.55%) ; Theoretical value (63.67%, 6.60%, 18.56%)

[Chemical Formula 19] Comparative Compound 2

(Example 1) (1) Preparation of ink composition With respect to 1 part by mass of Compound 1 of Synthesis Example 1, 79 parts by mass of pentaerythritol triacrylate (trade name M305, manufactured by Toagosei Co., Ltd.) and 3 parts by mass of 1-hydroxycyclohexyl phenyl ketone (trade name Irgacure 184, manufactured by BASF) were mixed Part and 296 parts by mass of methyl ethyl ketone as a solvent were filtered under pressure to obtain the ink composition 1 of Example 1.

(2) Film production The ink composition obtained in (1) was coated on a glass substrate (manufactured by Nippon Electric Glass Co., Ltd., "OA-10G") with a thickness of 0.7 mm using a spin coater. Thereafter, it was heated and dried on a hot plate at 80°C for 3 minutes to obtain a coating film. ^{The coating film was irradiated with ultraviolet rays of 500 mJ/cm 2} in terms of 254 nm using an ultra-high pressure mercury lamp to obtain a cured film, and the film 1 of Example 1 was produced. Furthermore, the thickness of the cured film is adjusted so that the transmittance of the minimum transmission wavelength of the following cured film in the range of the wavelength range of 380 nm to 750 nm in the transmission spectrum becomes 40%.

(Examples 2～3) (1) Preparation of ink composition In (1) of Example 1, Compound 1 was changed to Compounds 2 to 3. Except for this, the ink compositions 2 to 3 of Examples 2 to 3 were obtained in the same manner as in (1) of Example 1 respectively. .

(2) Manufacture of film In (2) of Example 1, the ink composition 1 was changed to ink compositions 2 to 3, respectively, except that the film 2 of Examples 2 to 3 was obtained in the same manner as in (2) of Example 1 ~3.

(Comparative Examples 1～2) (1) Preparation of comparative ink composition In (1) of Example 1, Compound 1 was changed to Comparative Compounds 1 to 2. Except for this, the Comparative Ink Composition 1 of Comparative Examples 1 to 2 was obtained in the same manner as in (1) of Example 1 respectively. ~2.

(2) Manufacture of film In (2) of Example 1, the Ink Composition 1 was changed to Comparative Ink Compositions 1-2, respectively. Except for this, the comparison of Comparative Examples 1-2 was obtained in the same manner as in (2) of Example 1 Membrane 1～2.

[Evaluation] <Measurement of transmission spectrum of cured film> The transmission spectra of the films obtained in the examples and comparative examples were measured using the "microscopic light measuring device OSP-SP200" manufactured by Olympus. In the measured transmission spectrum, find the transmittance difference between the transmittance of the minimum transmittance wavelength (the wavelength when the transmittance takes the minimum value) and the transmittance of the reference line within the wavelength range of 380 nm to 750 nm: ΔT (%), calculate the transmittance T _1/2 (%) when the ΔT (%) becomes 1/2. In the valley of the minimum transmission wavelength that gives the transmission spectrum, calculate the half-value width based on the difference between the maximum wavelength and the minimum wavelength (the width of the valley) _{from the reference line to satisfying T 1/2 (%).} Furthermore, the minimum transmission wavelength in the transmission spectrum corresponds to the maximum absorption wavelength in the absorption spectrum.

[Table 2] Table 2. Porphyrazine compounds Half width (nm) Side absorption (550 nm) Transmittance (%) Example 1 Compound 1 30 82 Example 2 Compound 2 30 81 Example 3 Compound 3 30 83 Comparative example 1 Comparative compound 1 30 76 Comparative example 2 Comparative compound 2 28 77

(Result summary) It is clear that the films containing the porphyrazine compound of the present invention of Examples 1 to 3 have a higher transmission rate of side absorption (550 nm) than the films containing the porphyrazine compound of Comparative Examples 1 and 2 , The side absorption is suppressed. It is believed that the reason is that, in the film containing the porphyrazine compound of the present invention of Examples 1 to 3, the self-association of the porphyrazine compound of the present invention is suppressed and side absorption is reduced. The reason for this is considered to be that the porphyrazine compound of the present invention is not easy to self-associate due to the specific substituents, and the compatibility with the light-curing binder component is improved, and the pigment molecules can be more uniformly dispersed. In addition, in Examples 1 to 3, the film of Example 3 containing the porphyrazine compound having an acryloyl group at the para position of the benzene ring has a higher transmittance at 550 nm, and the side absorption is reduced. It is thought that this means that when the acryloyl group of the benzene ring bonded to the porphyrazine skeleton is located at the para position, it functions most effectively as a compatible group and a group directly bonded to the binder. In addition, it is speculated that the acryloyl group at the para position deactivates the kinetic energy of the porphyrazine skeleton in the horizontal direction, thereby suppressing the formation of vibrational energy levels that cause side absorption (Figure 3).

1: Support 2: Adhesive layer or adhesive layer 10: Display panel 11, 13, 17, 19: protective film 12, 18: Polarizing element 14,16,16': light-transmitting adhesive layer 15: Display components 20: Backlight device 30: Surface functional layer 40: display surface film 100: Image display device

FIG. 1 is a schematic cross-sectional view of an example of a display surface film according to an embodiment of the present invention. 2 is a schematic cross-sectional view of an example of a display device according to an embodiment of the present invention. Fig. 3 is a diagram illustrating an example of the porphyrazine compound of the present invention.

1: Support

2: Adhesive layer or adhesive layer

30: Surface functional layer

40: display surface film

Claims (11)

A porphyrazine compound represented by the following general formula (1), [化1]

[In the general formula (1), any one of the two substituents of ^{R 1} and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , and R ⁷ and R ^{8 is independently selected from the following} The group in group A, and the other substituent each independently represents a group selected from the following group B, M represents a divalent metal atom or an oxide metal, group A: hydrogen atom, and carbon number 1-12 The aliphatic hydrocarbon group B: the monovalent group represented by the following general formula (2) [化2]

(In the general formula (2), Ar represents an aromatic hydrocarbon group of (n+1) valence, X represents -O-, -S-, or -NH-, and Y represents at least one of a hydrogen atom, an acrylic group and a methacrylic group One type, n is an integer from 1 to 7, * represents the bonding position to the porphyrazine skeleton) Among them, at least one monovalent group represented by the general formula (2) is contained in one molecule, the general formula (2) The monovalent group represented includes at least one of an acrylic group and a methacrylic group as Y]. An ink composition containing the porphyrazine compound of claim 1 and a binder component. The ink composition according to claim 2, wherein the above-mentioned binder component contains a compound having an ethylenically unsaturated bond. A film containing at least one of the ink composition of claim 2 or 3 and its hardened substance. An optical material containing the porphyrazine compound of claim 1. An optical film containing the porphyrazine compound of claim 1. A display device provided with the optical film as claimed in claim 6. An ink composition for a surface film of a display, which contains the porphyrazine compound of claim 1 and a binder component. The ink composition for a display surface film of claim 8, wherein the binder component contains a compound having an ethylenically unsaturated bond. A surface film for a display, which contains the porphyrazine compound of claim 1. A display device provided with the display surface film of claim 10.

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