WO2020218600A1 - Composition pour former un composant optique - Google Patents

Composition pour former un composant optique Download PDF

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Publication number
WO2020218600A1
WO2020218600A1 PCT/JP2020/017901 JP2020017901W WO2020218600A1 WO 2020218600 A1 WO2020218600 A1 WO 2020218600A1 JP 2020017901 W JP2020017901 W JP 2020017901W WO 2020218600 A1 WO2020218600 A1 WO 2020218600A1
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group
carbon atoms
substituent
independently
compound
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PCT/JP2020/017901
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English (en)
Japanese (ja)
Inventor
佐藤　隆
越後　雅敏
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三菱瓦斯化学株式会社
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Priority to JP2021516320A priority Critical patent/JPWO2020218600A1/ja
Publication of WO2020218600A1 publication Critical patent/WO2020218600A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G85/00—General processes for preparing compounds provided for in this subclass
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/16—Condensation polymers of aldehydes or ketones with phenols only of ketones with phenols
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to a composition for forming an optical component.
  • a flattening film or a material used for forming a microlens that is, an optical component
  • good transparency and high refractive index may be required as optical properties, and such performance.
  • the development of materials is underway to improve.
  • Patent Document 1 describes an ionic liquid and a compound having a predetermined polyalkylene oxide structure and a (meth) acryloyl group.
  • An energy ray-curable resin composition for an optical lens sheet containing a predetermined (meth) acrylate monomer and a photopolymerization initiator is disclosed.
  • Patent Document 2 a resin composition containing a copolymer having a specific structural unit, a specific curing acceleration catalyst, and a solvent is suitably used for a microlens or a flattening film. Is described.
  • Patent Document 3 describes that a copolymer having a specific structural unit is suitably used for a microlens.
  • Patent Documents 1 to 3 still have room for improvement from the viewpoint of achieving both high refractive index and high transparency at a higher level as optical component forming materials.
  • the present invention has been made in view of the above-mentioned problems of the prior art, and an object of the present invention is to provide a composition for forming an optical component capable of achieving both high refractive index and high transparency.
  • a composition for forming an optical component which comprises a compound represented by the following formula (0).
  • X represents an oxygen atom, a sulfur atom or no crosslink.
  • R 0 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • R 0 is a hydroxyl group, crosslinkable group or dissociable group.
  • the alkyl group, the aryl group, the alkenyl group, the alkynyl group and the alkoxy group at R0 may contain an ether bond, a ketone bond or an ester bond.
  • Each of R 2 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • atom a nitro group, an amino group, a carboxyl group, a crosslinkable group, dissociative group, a thiol group or a hydroxyl group, wherein said at R 2 alkyl group, the aryl group, the alkenyl group, the alkynyl group and the alkoxy
  • the group may contain an ether bond, a ketone bond or an ester bond.
  • n 1 is an integer of 1 to 2 independently of each other.
  • n 0 is independently an integer from 0 to (4 + 2n 1 ), where at least one of n 0 is 1 to (4 + 2n 1 ).
  • n 4 is an integer of 0 to 1 independently of each other.
  • n 5 is an integer from 0 to (4 + 2n 4 ) independently of each other.
  • R is independently a hydrogen atom, a linear alkyl group having 1 to 30 carbon atoms which may have a substituent, a branched form having 3 to 30 carbon atoms which may have a substituent, or A cyclic alkyl group, an aryl group having 6 to 30 carbon atoms which may have a substituent, an alkenyl group which may have a substituent and may have 2 to 20 carbon atoms, and a carbon which may have a substituent.
  • the number 2 to 20 is an alkynyl group, a crosslinkable group or a dissociable group, wherein at least one of R is a hydrogen atom, a crosslinkable group or a dissociable group.
  • Each of R 1 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • n 2 is an integer from 1 to (4 + 2n 1 ) independently of each other.
  • n 3 is an integer from 0 to (4 + 2n 1 ⁇ n 2 ) independently of each other.
  • n 2 is an integer of 1 to 6 independently of each other.
  • n 3 is an integer from 0 to (6-n 2 ) independently of each other.
  • the composition for forming an optical component according to [2], wherein the compound represented by the formula (1) is represented by the following formula (3).
  • X, R 1 , R 2 , n 4 and n 5 have the same meaning as the above formula (1).
  • n 3 is an integer of 0 to 5 independently of each other.
  • a composition for forming an optical component which comprises a resin having a structural unit derived from a compound represented by the following formula (0).
  • X represents an oxygen atom, a sulfur atom or no crosslink.
  • R 0 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • R 0 is a hydroxyl group, crosslinkable group or dissociable group.
  • the alkyl group, the aryl group, the alkenyl group, the alkynyl group and the alkoxy group at R0 may contain an ether bond, a ketone bond or an ester bond.
  • Each of R 2 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • atom a nitro group, an amino group, a carboxyl group, a crosslinkable group, dissociative group, a thiol group or a hydroxyl group, wherein said at R 2 alkyl group, the aryl group, the alkenyl group, the alkynyl group and the alkoxy
  • the group may contain an ether bond, a ketone bond or an ester bond.
  • n 1 is an integer of 1 to 2 independently of each other.
  • n 0 is independently an integer from 0 to (4 + 2n 1 ), where at least one of n 0 is 1 to (4 + 2n 1 ).
  • n 4 is an integer of 0 to 1 independently of each other.
  • n 5 is an integer from 0 to (4 + 2n 4 ) independently of each other.
  • composition for forming an optical component according to any one of [1] to [9], which further contains a solvent [11] The composition for forming an optical component according to any one of [1] to [10], which further contains an acid generator. [12] The composition for forming an optical component according to any one of [1] to [11], which further contains a cross-linking agent.
  • composition for forming an optical component that can achieve both high refractive index and high transparency.
  • the present embodiment is an example for explaining the present invention, and the present invention is not limited to the present embodiment.
  • alkyl group may be a linear or branched alkyl group, or may be a cyclic alkyl group, even if not specified otherwise, and means to include these.
  • alkoxy group may be a linear or branched alkoxy group, or may be a cyclic alkoxy group, even if not specified, and is used in the sense of including these. To do.
  • composition for forming optical components contains a compound represented by the following formula (0).
  • X represents an oxygen atom, a sulfur atom or no crosslink.
  • R 0 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • the alkyl group, the aryl group, the alkenyl group, the alkynyl group and the alkoxy group at R0 may contain an ether bond, a ketone bond or an ester bond.
  • Each of R 2 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • n 1 is an integer of 1 to 2 independently of each other.
  • n 0 is independently an integer from 0 to (4 + 2n 1 ), where at least one of n 0 is 1 to (4 + 2n 1 ).
  • n 4 is an integer of 0 to 1 independently of each other.
  • n 5 is an integer from 0 to (4 + 2n 4 ) independently of each other.
  • the compound (0) is preferably a compound represented by the following formula (0') (hereinafter, also simply referred to as "compound (0')").
  • R 0 , R 2 , n 1 , n 0 , n 4 and n 5 are synonymous with the formula (0), and p1, p2, p3 and p4 are each fused ring. Indicates the condensation position within, and n1'is an integer from 0 to 1.
  • the condensation position in the fused ring (anthracene ring) is more preferably p1, p2 and / or p3, p4 in the above formula (0').
  • composition for forming an optical component of the present embodiment contains the compound (0), it is useful as an optical component forming material capable of achieving both high refractive index and high transparency. More specifically, the composition for forming an optical component of the present embodiment typically has the following characteristics (I) to (IV) (hereinafter, simply "predetermined characteristics" due to the structure of the compound (0). Also called.).
  • Compound (0) has excellent solubility in organic solvents (particularly safe solvents). Therefore, when compound (0) is used as an optical component forming material, an optical component can be formed by a wet process such as a spin coating method or screen printing.
  • Compound (0) has a relatively high carbon concentration and a relatively low oxygen concentration. Further, when compound (0) has a phenolic hydroxyl group in the molecule, it is particularly useful for forming a cured product by reaction with a curing agent, but compound (0) alone also crosslinks the phenolic hydroxyl group at high temperature baking. By doing so, a cured product can be formed. Due to these, the compound (0) can exhibit particularly high heat resistance when it has a phenolic hydroxyl group, and when the compound (0) is used as an optical component forming material, the deterioration of the film at the time of high temperature baking is suppressed. , Coloring can be suppressed.
  • Compound (0) can exhibit high heat resistance and transparency as described above, and has excellent adhesion to a resist film and a resist intermediate layer film material. Therefore, when compound (0) is used as an optical component forming material, the optical component forming property is excellent.
  • optical component formability refers to a property in which large defects are unlikely to occur in the formed optical component and the optical properties such as light transmittance are excellent over a wide temperature range.
  • Compound (IV) compound (0) has a high refractive index due to its high aromatic ring density, is suppressed in coloring even after heat treatment, and is excellent in transparency.
  • the alkyl group is not particularly limited, but for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, neopentyl group, tert- Pentyl group, n-hexyl group, n-heptyl group, 2,2,4-trimethylpentyl group, n-octyl group, isooctyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group , N-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-n
  • N-Heptacosyl group, n-Nonacosyl group and other linear or branched alkyl groups having 1 to 30 carbon atoms can be mentioned, and carbon can be used from the viewpoint of making the predetermined characteristics of the present embodiment more effective. It is preferably a linear or branched alkyl group having 1 to 20 numbers, and more preferably a linear or branched alkyl group having 1 to 10 carbon atoms.
  • the cyclic alkyl group include a monocyclic group (monocyclic cycloalkyl group) and a polycyclic group (polycyclic cycloalkyl group).
  • the monocyclic group is not particularly limited, but for example, it has 3 to 30 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, and a cycloicosyl group.
  • the polycyclic group is not particularly limited, and examples thereof include a polycyclic group having 7 to 30 carbon atoms such as a dicyclopentyl group, a dicyclohexyl group, a norbornyl group, an adamantyl group, a tricyclodecyl group, and a tetracyclododecyl group. Be done.
  • the alkyl group may have a substituent.
  • the substituent is not particularly limited, but is, for example, a halogen atom (for example, a fluorine atom, a chlorine atom, and a bromine atom), a nitro group, an amino group which may have a substituent, a carboxyl group, a thiol group, and a hydroxyl group. Can be mentioned.
  • the number of substituents is not particularly limited and may be one or plural.
  • the aryl group is not particularly limited, but is, for example, a phenyl group, a naphthyl group (for example, 1-naphthyl group and 2-naphthyl group), an anthryl group (for example, 1-anthryl group), and a phenanthryl group (for example, 1-).
  • Aryl groups having 6 to 30 carbon atoms such as phenanthryl group) can be mentioned, and from the viewpoint of making the predetermined characteristics of the present embodiment more effective, aryl groups having 6 to 10 carbon atoms such as phenyl group and naphthyl group can be used. It is preferably present, and more preferably it is a phenyl group.
  • the aryl group may have a substituent.
  • the substituent is not particularly limited, and examples thereof include a substituent exemplified as a substituent of an alkyl group in the formula (0) and an alkyl group exemplified as an alkyl group in the formula (0).
  • the number of substituents is not particularly limited and may be one or plural.
  • the alkenyl group is not particularly limited, and examples thereof include an alkenyl group having 2 to 30 carbon atoms such as an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, and a hexenyl group.
  • the alkenyl group may have a substituent.
  • the substituent is not particularly limited, and examples thereof include a substituent exemplified as a substituent of an alkyl group in the formula (0) and an alkyl group exemplified as an alkyl group in the formula (0).
  • the number of substituents is not particularly limited and may be one or plural.
  • the alkynyl group is not particularly limited, and examples thereof include an alkynyl group having 2 to 30 carbon atoms such as an ethynyl group and a propagyl group.
  • the alkynyl group may have a substituent.
  • the substituent is not particularly limited, and examples thereof include a substituent exemplified as a substituent of an alkyl group in the formula (0) and an alkyl group exemplified as an alkyl group in the formula (0).
  • the number of substituents is not particularly limited and may be one or plural.
  • alkoxy group is not particularly limited, for example, group (wherein, R a, in formula (0), indicating the exemplified alkyl group as the alkyl group.) Represented by -O-R a, such as Alkoxy groups having 1 to 30 carbon atoms can be mentioned.
  • methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxo group, tert-butoxy group and the like It is preferably a linear or branched alkoxy group having 1 to 6 carbon atoms, more preferably a linear or branched alkoxy group having 1 to 3 carbon atoms, and is a methoxy group or an ethoxy group. Is even more preferable.
  • the alkoxy group may have a substituent.
  • the substituent is not particularly limited, and examples thereof include a substituent exemplified as a substituent of an alkyl group in the formula (0) and an alkyl group exemplified as an alkyl group in the formula (0).
  • the number of substituents is not particularly limited and may be one or plural.
  • the halogen atom is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, and an iodine atom.
  • R 0 is a hydroxyl group, a crosslinkable group or a dissociative group.
  • the compound of the present embodiment has a predetermined property by having such R 0 .
  • the density tends to be high, so that the number of atoms contained per unit thickness increases, and particularly a thin film. It tends to be advantageous for formation.
  • the condensation position in the fused ring is p1, p2, p3, p4 in the formula (0')
  • it tends to be more advantageous for thin film formation. ..
  • crosslinkable group in the present embodiment means a group that crosslinks in the presence of a catalyst or in the absence of a catalyst.
  • the crosslinkable group is not particularly limited, and has, for example, an alkoxy group having 1 to 20 carbon atoms, a group having an allyl group, a group having a (meth) acryloyl group, a group having an epoxy (meth) acryloyl group, and a hydroxyl group.
  • group containing these groups include -ORx (Rx is a group having an allyl group, a group having a (meth) acryloyl group, a group having an epoxy (meth) acryloyl group, a group having a hydroxyl group, and urethane (Rx).
  • Meta It has a group having an acryloyl group, a group having a glycidyl group, a group having a vinylphenylmethyl group, a group having various alkynyl groups, a group having a carbon-carbon double bond, and a carbon-carbon triple bond.
  • a group and an alkoxy group represented by (a group containing these groups) are preferable.
  • each of the above-mentioned functional groups (excluding the crosslinkable group) constitutes the compound of the present embodiment and there is an overlap with the crosslinkable group, it is based on the presence or absence of the crosslinkable property. Those without crosslinkability are treated as corresponding to each functional group, and those with crosslinkability are treated as corresponding to a crosslinkable group.
  • the group having an allyl group is not particularly limited, and examples thereof include a group represented by the following formula (X-1).
  • n X1 is an integer from 1 to 5.
  • the group having a (meth) acryloyl group is not particularly limited, and examples thereof include a group represented by the following formula (X-2).
  • n X2 is an integer of 1 to 5
  • RX is a hydrogen atom or a methyl group.
  • the group having an epoxy (meth) acryloyl group is not particularly limited, and examples thereof include a group represented by the following formula (X-3).
  • the epoxy (meth) acryloyl group refers to a group formed by the reaction of an epoxy (meth) acrylate with a hydroxyl group.
  • n x3 is an integer from 0 to 5, 0 are preferred, R X is hydrogen atom, or a methyl group, a methyl group is preferred.
  • the group having a urethane (meth) acryloyl group is not particularly limited, and examples thereof include a group represented by the following formula (X-4).
  • n x4 is an integer of 0 to 5, preferably 0, s is an integer of 0 to 3, preferably 0, and RX is a hydrogen atom or a methyl group. And a methyl group is preferable.
  • the group having a hydroxyl group is not particularly limited, and examples thereof include a group represented by the following formula (X-5).
  • n x 5 is an integer of 1 to 5, and 1 is preferable.
  • the group having a glycidyl group is not particularly limited, and examples thereof include a group represented by the following formula (X-6).
  • n x6 is an integer from 1 to 5.
  • the group having a vinyl-containing phenylmethyl group is not particularly limited, and examples thereof include a group represented by the following formula (X-7).
  • n x7 is an integer of 1 to 5, and 1 is preferable.
  • the group having various alkynyl groups is not particularly limited, and examples thereof include a group represented by the following formula (X-8).
  • n x 8 is an integer from 1 to 5.
  • Examples of the carbon-carbon double bond-containing group include a (meth) acryloyl group, a substituted or unsubstituted vinylphenyl group, and a group represented by the following formula (X-9-1).
  • Examples of the carbon-carbon triple bond-containing group include a substituted or unsubstituted ethynyl group and a substituted or unsubstituted propargyl group represented by the following formulas (X-9-2) and (X-9-3). The group to be used is mentioned.
  • RX9A , RX9B and RX9C are independently hydrogen atoms or monovalent hydrocarbon groups having 1 to 20 carbon atoms.
  • RX9D , RX9E and RX9F are independently hydrogen atoms or monovalent hydrocarbons having 1 to 20 carbon atoms. It is the basis.
  • the "dissociative group” in the present embodiment means a group that dissociates in the presence or absence of a catalyst.
  • the acid dissociative group refers to a group that cleaves in the presence of an acid to change the alkali-soluble group or the like.
  • the alkali-soluble group is not particularly limited, and examples thereof include a phenolic hydroxyl group, a carboxyl group, a sulfonic acid group, a hexafluoroisopropanol group, and the like. Among them, from the viewpoint of easy availability of the introduction reagent, the phenolic hydroxyl group and the carboxyl group can be mentioned. Groups are preferred, phenolic hydroxyl groups are more preferred.
  • the acid dissociative group preferably has the property of causing a chain cleavage reaction in the presence of an acid in order to enable highly sensitive and high resolution pattern formation.
  • the acid dissociable group is not particularly limited, but is appropriately selected from those proposed in, for example, hydroxystyrene resins used in chemically amplified resist compositions for KrF and ArF, (meth) acrylic acid resins, and the like. Can be used. Specific examples of the acid dissociative group include those described in International Publication No. 2016/158168.
  • Examples of the acid dissociable group include a 1-substituted ethyl group, a 1-substituted-n-propyl group, a 1-branched alkyl group, a silyl group, an acyl group, a 1-substituted alkoxymethyl group, and a cyclic group having the property of dissociating with an acid.
  • an alkoxycarbonyl group eg, -C (O) OC (CH 3 ) 3, etc.
  • each of the above-mentioned functional groups constitutes the compound of the present embodiment and there is an overlap with the dissociative group, it is based on the presence or absence of dissociation.
  • Non-dissociative ones are treated as corresponding to each functional group, and dissociative ones are treated as corresponding to dissociative groups.
  • the substituent to be substituted with the dissociable group is not particularly limited, but for example, a halogen atom, an alkyl group, an aryl group, an aralkyl group, an alkenyl group, an acyl group, an alkoxycarbonyl group, an alkyloxy group, an aryloyloxy group, and the like. Examples thereof include a cyano group, a nitro group, and a hetero atom.
  • the halogen atom is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, and an iodine atom.
  • the alkyl group may be linear, branched or cyclic.
  • the alkyl group is not particularly limited, and examples thereof include an alkyl group having 1 to 10 carbon atoms such as a methyl group, a tert-butyl group, a cyclohexyl group, and an adamantyl group.
  • the aryl group is not particularly limited, and examples thereof include an aryl group having 6 to 20 carbon atoms such as a phenyl group, a tolyl group, and a naphthyl group.
  • the aryl group may further have a substituent such as a halogen atom or an alkyl group having 1 to 5 carbon atoms.
  • the aralkyl group is not particularly limited, and examples thereof include a benzyl group and a phenethyl group.
  • the aralkyl group may further have a substituent such as a halogen atom or an alkyl group having 1 to 5 carbon atoms.
  • the alkynyl group is not particularly limited, and examples thereof include an ethynyl group and a propagyl group.
  • the acyl group is not particularly limited, and examples thereof include an aliphatic acyl group having 1 to 6 carbon atoms such as a formyl group and an acetyl group, and an aromatic acyl group such as a benzoyl group.
  • the alkoxycarbonyl group is not particularly limited, and examples thereof include an alkoxycarbonyl group having 2 to 5 carbon atoms such as a methoxycarbonyl group.
  • the alkyloxy group is not particularly limited, and examples thereof include an acetoxy group.
  • the allylloyloxy group is not particularly limited, and examples thereof include a benzoyloxy group.
  • the hetero atom is not particularly limited, and examples thereof include an oxygen atom, a sulfur atom, a selenium atom, a nitrogen atom, and a phosphorus atom. Heteroatoms may be substituted with the carbon atoms of each group.
  • the carbon number of each group described in the present specification is the total carbon number including the substituent when the above-mentioned substituent is included.
  • X in compound (0) represents an oxygen atom, a sulfur atom or no crosslink.
  • X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • N 1 in compound (0) is an integer of 1 to 2 independently, and is preferably 1.
  • n 0 is independently an integer from 0 to (4 + 2n1), where at least one of n 0 is an integer from 1 to (4 + 2n 1 ), preferably 1 to 2.
  • n 4 is an integer of 0 to 1, preferably 0.
  • n 5 is an integer from 0 to (4 + 2n 4 ), preferably 0 to 2.
  • the compound (0) of the present embodiment preferably has a cardo structure from the viewpoint of making a predetermined property more effective.
  • Compound (0) has a relatively low molecular weight, but has high heat resistance due to the rigidity of its structure, so that it can be used even under high-temperature baking conditions.
  • the composition for forming an optical component of the present embodiment containing the compound (0) may be used. It has excellent flatness and optical component formability.
  • the organic solvent include the organic solvents described in [Solvent] described later.
  • Compound (0) has a high refractive index due to its high aromatic ring density, and its coloring is suppressed even by a wide range of heat treatment from low temperature to high temperature, so that it is useful for forming various optical components described later.
  • the composition for forming an optical component of the present embodiment is preferably used for forming an optical component.
  • the optical component is not particularly limited, but for example, a film-shaped component, a sheet-shaped component, a prism lens, a lenticular lens, a microlens, a frennel lens, a viewing angle control lens, a plastic lens such as a contrast improving lens, a retardation film, and the like.
  • the compound (0) is an embedded film and a flattening film on a photodiode, which is a member of a solid-state image sensor for which a particularly high refractive index is required, a flattening film before and after a color filter, a microlens, and a flattening on a microlens. It is particularly preferably used as a material for forming a film and a conformal film.
  • the compound (0) is preferably a compound represented by the following formula (1) (hereinafter, also simply referred to as “compound (1)”) from the viewpoint of easy cross-linking and solubility in an organic solvent. ..
  • R is independently a hydrogen atom, a linear alkyl group having 1 to 30 carbon atoms which may have a substituent, a branched form having 3 to 30 carbon atoms which may have a substituent, or A cyclic alkyl group, an aryl group having 6 to 30 carbon atoms which may have a substituent, an alkenyl group which may have a substituent and may have 2 to 20 carbon atoms, and a carbon which may have a substituent.
  • the number 2 to 20 is an alkynyl group, a crosslinkable group or a dissociable group, wherein at least one of R is a hydrogen atom, a crosslinkable group or a dissociable group.
  • Each of R 1 independently has an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, and a substituent.
  • n 2 is an integer from 1 to (4 + 2n 1 ) independently of each other.
  • n 3 is an integer from 0 to (4 + 2n 1 ⁇ n 2 ) independently of each other.
  • an alkyl group, an aryl group, an alkenyl group, an alkoxy group, a halogen atom, a crosslinkable group, a dissociable group, and a substituent substituted for each group are not particularly limited, but for example, the formula (0) is used.
  • the formula (0) is used.
  • n 2 is an integer of 1 to (4 + 2n 1 ) independently of each other, and is preferably 1 to 2.
  • n 3 is an integer of 0 to (4 + 2n 1 ⁇ n 2 ) independently of each other, and is preferably 0 to 2.
  • the compound (1) is preferably a compound represented by the following formula (2) (hereinafter, also simply referred to as “compound (2)”) from the viewpoint of raw material supply.
  • n 2 is an integer of 1 to 6 independently of each other.
  • n 3 is an integer from 0 to (6-n 2 ) independently of each other.
  • the compound (2) is preferably a compound represented by the following formula (3) (hereinafter, also simply referred to as “compound (3)”).
  • R 1 , R 2 , n 4 and n 5 have the same meaning as the above formula (1).
  • n 3 is an integer of 0 to 5 independently of each other.
  • the compound (1) is preferably a compound represented by the following formula (4) (hereinafter, also simply referred to as “compound (4)”).
  • n 5 is an integer of 0 to 4 independently.
  • the compound (1) is preferably a compound represented by the following formula (5) (hereinafter, also simply referred to as “compound (5)”).
  • n 3 are independently integers from 0 to 5 and n 5 is an integer of 0 to 4 independently.
  • the method for producing the compound (0) is not particularly limited, and examples thereof include the following methods. That is, under normal pressure, a compound represented by the following formula (0-x) (hereinafter, compound (0-x)) and a compound represented by the following formula (0-y) (hereinafter, compound (0-y)). ) And the compound represented by the following formula (0-z) (hereinafter, compound (0-z)) are subjected to a polycondensation reaction under an acid catalyst or a base catalyst to obtain compound (0). Be done. In the polycondensation reaction, compounds (0-x), compounds (0-y) and precursors of compound (0-y) can also be used. The above reaction may be carried out under pressure, if necessary.
  • R 0 , n 0 , n 1 and n 5 are as defined in equation (0), respectively.
  • R 0 , n 0 , n 1 and n 5 are as defined in equation (0), respectively.
  • R 2 , n 4 and n 5 are as defined in each formula (0).
  • the compound (0-x) and the compound (0-y) may be the same.
  • compound (0) is obtained by polycondensation reaction under a base catalyst.
  • the compound (0-x) and the compound (0-y) are not particularly limited, and for example, 2,7-dihydroxynaphthalene, 2,7-dihydroxy-3-bromonaphthalene, 2-naphthol, 2,6-dihydroxy. Anthracene and the like can be mentioned. These compounds may be used alone or in combination of two or more. Among these compounds, 2,7-dihydroxynaphthalene is preferable.
  • the compound (0-z) is not particularly limited, but for example, 9-fluorenone, 11H-benzo [b] fluorene-11-one, 11H-benzo [a] fluorene-11-one, 3,6-dibromo-.
  • examples thereof include 9H-fluorene-9-one, 2-bromo-9-fluorenone, 2,7-dihydroxy-9H-fluorene-9-one, 2-hydroxy-9-fluorenone and the like. These compounds may be used alone or in combination of two or more. Among these compounds, 9-fluorenone is preferable.
  • the acid catalyst used in the above reaction is not particularly limited, but is, for example, an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid, or hydrofluoric acid, oxalic acid, malonic acid, succinic acid, adipic acid, and sebacic acid.
  • an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid, or hydrofluoric acid, oxalic acid, malonic acid, succinic acid, adipic acid, and sebacic acid.
  • Citric acid fumaric acid, maleic acid, formic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, naphthalenesulfonic acid, naphthalenedisulfonic acid, etc.
  • organic acids such as zinc chloride, aluminum chloride, iron chloride and boron trifluoride
  • solid acids such as silicate tung acid, phosphotung acid, silicate molybdic acid and phosphomolybdic acid.
  • organic acids and solid acids are preferable from the viewpoint of production, and hydrochloric acid or sulfuric acid is preferably used from the viewpoint of production such as easy availability and handling.
  • the amount of the acid catalyst used can be appropriately set according to the raw material used, the type of catalyst used, the reaction conditions, and the like, and is not particularly limited, but is 0.01 to 100 parts by mass with respect to 100 parts by mass of the reaction raw material. Is preferable.
  • the base catalyst used in the above reaction is not particularly limited, but is, for example, metal alcoxide (alkali metal such as sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, or alkaline earth metal alcoxide), metal hydroxide.
  • metal alcoxide alkali metal such as sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, or alkaline earth metal alcoxide
  • metal hydroxide metal hydroxide
  • alkali metals such as sodium hydroxide and potassium hydroxide or alkaline earth metal hydroxides, etc.
  • alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate or alkaline earth hydrogen carbonates
  • amines for example, third Carous acid metal salts (sodium acetate, etc.) such as secondary amines (trialkylamines such as triethylamine, aromatic tertiary amines such as N, N-dimethylaniline, heterocyclic tertiary amines such as 1-methylimidazole), etc.
  • Organic bases such as alkali metals acetate such as calcium acetate or alkaline earth metal salts) can be mentioned.
  • base catalysts are used alone or in combination of two or more. From the above viewpoint, metal alcoxides, metal hydroxides and amines are preferable, and sodium hydroxide is preferably used from the viewpoint of manufacturing such as easy availability and handling.
  • the amount of the base catalyst used is the amount to be used. It can be appropriately set according to the type of raw material to be used, the type of catalyst used, reaction conditions, etc., and is not particularly limited, but is preferably 0.01 to 100 parts by mass with respect to 100 parts by mass of the reaction raw material.
  • a reaction solvent may be used in the above reaction.
  • the reaction solvent is not particularly limited, and examples thereof include water, methanol, ethanol, propanol, butanol, tetrahydrofuran, dioxane, 1-methoxy-2-propanol, ethylene glycol dimethyl ether, ethylene glycol diethyl ether and the like. These solvents may be used alone or in combination of two or more.
  • the amount of the solvent used can be appropriately set according to the raw material used, the type of catalyst used, the reaction conditions, and the like, and is not particularly limited, but is in the range of 0 to 2000 parts by mass with respect to 100 parts by mass of the reaction raw material. Is preferable.
  • the reaction temperature in the above reaction can be appropriately selected depending on the reactivity of the reaction raw material, and is not particularly limited, but is usually in the range of 10 to 200 ° C.
  • the reaction temperature is preferably high, specifically in the range of 60 to 200 ° C.
  • the reaction method is not particularly limited, and for example, there are a method of charging the raw material (reactant) and the catalyst in a batch, and a method of sequentially dropping the raw material (reactant) in the presence of the catalyst.
  • isolation of the obtained compound can be carried out according to a conventional method and is not particularly limited.
  • a general method such as raising the temperature of the reaction kettle to 130 to 230 ° C. and removing volatile substances at about 1 to 50 mmHg is adopted. Thereby, the target compound can be obtained.
  • Preferred reaction conditions include a compound represented by the above formula (0-x) and a compound represented by the above formula (0-y) with respect to 1 mol of the ketones represented by the above formula (0-z). Examples thereof include conditions in which 1.0 mol to an excess amount is used, 0.001 to 1 mol of an acid catalyst is used, and the reaction is carried out at 50 to 150 ° C. for about 20 minutes to 100 hours at normal pressure.
  • the target product can be isolated by a known method.
  • the reaction solution is concentrated, pure water is added to precipitate the reaction product, the reaction product is cooled to room temperature, filtered to separate the reaction product, and the obtained solid product is filtered and dried, and then column chromatography is performed.
  • the compound (0), which is the target product can be obtained by separating and purifying from the by-product, distilling off the solvent, filtering, and drying.
  • the resin in this embodiment contains a structural unit derived from the compound represented by the above formula (0). That is, the resin in the present embodiment contains the compound represented by the above formula (0) as a monomer component.
  • a resin having a structure represented by the following formula (6) (hereinafter, also simply referred to as “resin (6)”) is preferable.
  • L is a divalent group having 1 to 60 carbon atoms
  • M is a unit structure derived from a compound represented by any of the formulas (0) to (5).
  • linking group examples include residues derived from a compound having a cross-linking reaction described later.
  • L a divalent hydrocarbon group having 1 to 30 carbon atoms is preferably used.
  • the divalent hydrocarbon group is not particularly limited, and examples thereof include a linear or branched hydrocarbon group such as an alkylene group or a cyclic hydrocarbon group.
  • the resin (6) is obtained by reacting the compound (0) with a compound having a cross-linking reactivity.
  • the compound having a cross-linking reactivity may be any compound capable of oligomerizing or polymerizing compound (0), for example, aldehydes, ketones, carboxylic acids, carboxylic acid halides, halogen-containing compounds, amino compounds, iminos. Examples thereof include compounds, isocyanate compounds, and unsaturated hydrocarbon group-containing compounds.
  • the resin (6) is not particularly limited, and examples thereof include a novolakized resin obtained by a condensation reaction between the compound (0) and aldehydes or ketones which are compounds having a cross-linking reaction.
  • the aldehydes used for novolacizing the compound (0) are not particularly limited, but for example, formaldehyde, trioxane, paraformaldehyde, benzaldehyde, acetaldehyde, propylaldehyde, phenylacetaldehyde, phenylpropionaldehyde, hydroxybenzaldehyde, and the like.
  • aldehydes may be used alone or in combination of two or more. Further, in addition to these aldehydes, one or more kinds of ketones can be used in combination.
  • benzaldehyde hydroxybenzaldehyde, chlorobenzaldehyde, nitrobenzaldehyde, methylbenzaldehyde
  • ethylbenzaldehyde butylbenzaldehyde, cyclohexylbenzaldehyde, biphenylaldehyde, naphthaldehyde, anthracenecarbaldehyde, phenanthrencarbaldehyde, pyrenecarbaldehyde, and furfural
  • formaldehyde preferable.
  • the amount of the aldehydes used is not particularly limited, but is preferably
  • the ketones used for novolacizing the compound (0) are not particularly limited, but for example, acetone, methyl ethyl ketone, cyclobutanone, cyclopentanone, cyclohexanone, norbornanone, cyclohexanedione, cyclohexanetrione, cyclodecantrion, adamantanone, Fluolenone, benzofluorenone, dibenzofluorenone, acenaphthenquinone, acenaphthenone, anthraquinone, acetophenone, diacetylbenzene, triacetylbenzene, acetonaphthone, acetylmethylbenzene, acetyldimethylbenzene, acetyltrimethylbenzene, acetylethylbenzene, acetylpropylbenzene, acetylbutylbenzene,
  • ketones may be used alone or in combination of two or more.
  • a catalyst can also be used in the condensation reaction between compound (0) and aldehydes or ketones.
  • the acid catalyst or base catalyst used here can be appropriately selected from known ones and is not particularly limited.
  • the acid catalyst and the base catalyst are the same as those given in the method for producing the compound (0).
  • These catalysts may be used alone or in combination of two or more.
  • organic acids and solid acids are preferable from the viewpoint of production, and hydrochloric acid or sulfuric acid is preferable from the viewpoint of production such as easy availability and handling.
  • the amount of the acid catalyst used can be appropriately set according to the raw material used, the type of catalyst used, the reaction conditions, and the like, and is not particularly limited, but is 0.01 to 100 parts by mass with respect to 100 parts by mass of the reaction raw material. Is preferable.
  • indene hydroxyindene, benzofuran, hydroxyanthracene, acenaphthylene, biphenyl, bisphenol, trisphenol, dicyclopentadiene, tetrahydroindene, 4-vinylcyclohexene, norbornadiene, 5-vinylnorborna-2-ene, ⁇ -pinene, ⁇ -pinene.
  • a copolymerization reaction with a compound having a non-conjugated double bond such as limonene
  • aldehydes or ketones are not always necessary.
  • a reaction solvent can also be used in the condensation reaction between the compound (0) and aldehydes or ketones.
  • the reaction solvent in this polycondensation can be appropriately selected from known ones and used, and is not particularly limited, but for example, water, methanol, ethanol, propanol, butanol, 1-methoxy-2-propanol, tetrahydrofuran, etc. Dioxane or a mixed solvent thereof can be mentioned. These solvents may be used alone or in combination of two or more.
  • the amount of the solvent used can be appropriately set according to the raw material used, the type of catalyst used, the reaction conditions, and the like, and is not particularly limited, but is in the range of 0 to 2000 parts by mass with respect to 100 parts by mass of the reaction raw material. Is preferable.
  • the reaction temperature can be appropriately selected depending on the reactivity of the reaction raw material, and is not particularly limited, but is usually in the range of 10 to 200 ° C.
  • the reaction method the above compound (0), aldehydes and / or ketones and a catalyst are collectively charged, and the above compound (0), aldehydes and / or ketones are sequentially added in the presence of a catalyst. There is a method of dropping the compound into the water.
  • the obtained resin can be isolated according to a conventional method and is not particularly limited.
  • a general method such as raising the temperature of the reaction kettle to 130 to 230 ° C. and removing volatile substances at about 1 to 50 mmHg is adopted.
  • the target product for example, a novolakized resin
  • the resin (6) may be obtained together with the synthetic reaction of the compound (0). That is, the resin (6) may be a polymer of aldehydes or ketones derived from the raw materials used in the synthesis of the compound (0) and the compound (0).
  • the resin (6) may be a homopolymer of the compound (0), or may be a copolymer with other phenols or the like.
  • the phenols that can be copolymerized here are not particularly limited, but are, for example, phenol, cresol, dimethylphenol, trimethylphenol, butylphenol, phenylphenol, diphenylphenol, naphthylphenol, resorcinol, methylresorcinol, catechol, butylcatechol, methoxy. Examples thereof include phenol, methoxyphenol, propylphenol, pyrogallol, timol and the like.
  • the resin (6) may be copolymerized with a polymerizable monomer in addition to the other phenols described above.
  • the copolymerization monomer is not particularly limited, but for example, naphthol, methylnaphthol, methoxynaphthol, dihydroxynaphthalene, indene, hydroxyindene, benzofuran, hydroxyanthracene, acenaphthylene, biphenyl, bisphenol, trisphenol, dicyclopentadiene, tetrahydroindene, etc. 4-Vinylcyclohexene, norbornadiene, vinylnorbornaen, pinen, limonene and the like can be mentioned.
  • the resin (6) is a copolymer of the compound (0) and the above-mentioned phenols in a binary or more (for example, 2 to 4 elements) copolymer
  • the compound (0) and the above-mentioned copolymerized monomer are used.
  • the compound (1), the above-mentioned phenols, and the above-mentioned copolymerized monomer are three or more elements (for example, 3 to 4). It may be a (primary) copolymer.
  • the weight average molecular weight (Mw) of the resin (6) is not particularly limited, but is preferably 300 to 100,000, more preferably 500 to 30,000, in terms of polystyrene as measured by GPC. It is more preferably 750 to 20,000. Further, from the viewpoint of increasing the crosslinking efficiency and suppressing the volatile components in the bake, the resin (6) preferably has a dispersity (weight average molecular weight Mw / number average molecular weight Mn) in the range of 1 to 7.
  • the above-mentioned compound (0) and / or resin (6) are preferably highly soluble in a solvent from the viewpoint of facilitating the application of a wet process. More specifically, these compounds (0) and / or the resin (6) are also referred to as propylene glycol monomethyl ether (hereinafter, also referred to as “PGME”) and / or propylene glycol monomethyl ether acetate (hereinafter, also referred to as “PGMEA”). ) Is used as a solvent, the solubility in the solvent is preferably 10% by mass or more.
  • the solubility in PGME and / or PGMEA is "mass of compound (0) and / or resin (6) ⁇ (mass of compound (0) and / or resin (6) + mass of solvent) x 100 (mass). %) ”Is defined.
  • 10 g of the compound (0) and / or the resin (6) is evaluated to have high solubility in 90 g of PGMEA because the solubility of the compound (0) and / or the resin (6) in PGMEA is "10 mass by mass”. % Or more, and it is evaluated that the solubility is not high when the solubility is "less than 10% by mass”.
  • composition for forming an optical component of the present embodiment contains a compound (0) and / or a resin (6). Therefore, a wet process can be applied, and it is excellent in heat resistance and flattening characteristics. Further, since the composition for forming an optical component of the present embodiment contains the compound (0) and / or the resin (6), the aromatic ring density is high, so that the refractive index is high and the range from low temperature to high temperature is wide. Coloring is also suppressed by the heat treatment of. Therefore, the composition for forming an optical component of the present embodiment is suitable for forming an optical component.
  • a solvent a cross-linking agent, a cross-linking accelerator, an acid generator, a basic compound, and other components may be contained, if necessary.
  • these optional components will be described.
  • the composition for forming an optical component of the present embodiment may contain a solvent.
  • the solvent is not particularly limited as long as it is a solvent capable of dissolving the compound (0) and / or the resin (6).
  • the compound (0) and / or the resin (6) are excellent in solubility in an organic solvent, and therefore various organic solvents are preferably used.
  • the solvent is not particularly limited, but for example, a ketone solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; a cellosolve solvent such as PGME and PGMEA; ethyl lactate, methyl acetate, ethyl acetate, butyl acetate and isoamyl acetate, Ester solvents such as ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate; alcohol solvents such as methanol, ethanol, isopropanol and 1-ethoxy-2-propanol; aromatic hydrocarbons such as toluene, xylene and anisole. Can be mentioned. These solvents may be used alone or in combination of two or more.
  • the amount of the solid component is not particularly limited, but is preferably 1 to 80% by mass with respect to 100% by mass of the total mass of the solid component and the solvent. It is more preferably 50% by mass, further preferably 2 to 40% by mass, still more preferably 2 to 10% by mass and 90 to 98% by mass of the solvent.
  • the amount of the solvent is not particularly limited, but is preferably 20 to 99% by mass, preferably 50 to 99% by mass, based on 100% by mass of the total mass of the solid component and the solvent. It is more preferably by mass, more preferably 60 to 98% by mass, and even more preferably 90 to 98% by mass.
  • a "solid component" means a component other than a solvent.
  • the content of the solvent is not particularly limited, but may be 100 to 10,000 parts by mass with respect to 100 parts by mass of the compound (0) and / or the resin (6) from the viewpoint of solubility and film formation. It is preferably 200 to 5,000 parts by mass, and even more preferably 200 to 1,000 parts by mass.
  • the composition for forming an optical component of the present embodiment may contain a cross-linking agent from the viewpoint of improving the solvent resistance after forming the optical component.
  • the cross-linking agent is not particularly limited, and for example, those described in International Publication No. 2013/024779 and International Publication No. 2018/016614 can be used.
  • the cross-linking agent is not particularly limited, but for example, a phenol compound, an epoxy compound, a cyanate compound, an amino compound, a benzoxazine compound, an acrylate compound, a melamine compound, a guanamine compound, a glycoluril compound, a urea compound, an isocyanate compound, an azide compound and the like. Can be mentioned.
  • These cross-linking agents may be used alone or in combination of two or more. Among these, one or more selected from the group consisting of benzoxazine compounds, epoxy compounds and cyanate compounds is preferable, and benzoxazine compounds are more preferable from the viewpoint of improving etching resistance.
  • the content of the cross-linking agent is not particularly limited, but is preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of the compound (0) and / or the resin (6). It is more preferably 50 parts by mass, and even more preferably 10 to 40 parts by mass.
  • the content of the cross-linking agent is within the above range, the solvent resistance after forming the optical component tends to be improved, and the film-forming property after cross-linking tends to be improved.
  • the composition for forming an optical component of the present embodiment may contain a cross-linking accelerator in order to promote a cross-linking reaction (curing reaction), if necessary.
  • a cross-linking accelerator include a radical polymerization initiator.
  • the radical polymerization initiator may be a photopolymerization initiator that initiates radical polymerization by light, or a thermal polymerization initiator that initiates radical polymerization by heat.
  • the radical polymerization initiator is not particularly limited, and examples thereof include a ketone-based photopolymerization initiator, an organic peroxide-based polymerization initiator, and an azo-based polymerization initiator.
  • the radical polymerization initiator is not particularly limited, but for example, the one described in International Publication No. 2018/016614 can be used.
  • radical polymerization initiators are used alone or in combination of two or more.
  • the content of the radical polymerization initiator in the present embodiment is not particularly limited, but is preferably 0.05 to 25 parts by mass when the compound (0) or the resin (6) is 100 parts by mass, and is 0. .1 to 10 parts by mass is more preferable.
  • the content of the radical polymerization initiator is 0.05 parts by mass or more, it tends to be possible to prevent insufficient curing, while the content of the radical polymerization initiator is 25 parts by mass or less. In this case, it tends to be possible to prevent the long-term storage stability at room temperature from being impaired.
  • the composition for forming an optical component of the present embodiment may contain an acid generator from the viewpoint of further promoting the cross-linking reaction by heat.
  • an acid generator those that generate acid by thermal decomposition, those that generate acid by light irradiation, and the like are known, and any of them can be used.
  • the acid generator is not particularly limited, but for example, the acid generator described in International Publication No. 2013/024779 can be used.
  • the content of the acid generator in the composition for forming an optical component is not particularly limited, but may be 0.1 to 50 parts by mass with respect to 100 parts by mass of the compound (0) and / or the resin (6). It is preferably 0.5 to 40 parts by mass, more preferably 0.5 to 40 parts by mass. When the content of the acid generator is within the above range, the cross-linking reaction tends to be enhanced, and the solvent resistance after forming the optical component tends to be improved.
  • the composition for forming an optical component of the present embodiment may contain a basic mixture from the viewpoint of improving storage stability and the like.
  • the basic compound plays a role of preventing the acid generated in a small amount from the acid generator from advancing the cross-linking reaction, that is, a role of quenching against the acid.
  • Such basic compounds are not particularly limited, and examples thereof include those described in International Publication No. 2013/024779.
  • the content of the basic compound in the composition for forming an optical component of the present embodiment is not particularly limited, but is 0.001 to 2 parts by mass with respect to 100 parts by mass of the compound (0) and / or the resin (6). It is preferable that the amount is 0.01 to 1 part by mass.
  • the content of the basic compound is within the above range, the storage stability tends to be enhanced without excessively impairing the cross-linking reaction.
  • the composition for forming an optical component of the present embodiment may contain other resins and / or compounds for the purpose of imparting curability by heat or light and controlling the absorbance.
  • Such other resins and / or compounds are not particularly limited, and for example, naphthalene resin, xylene resin, naphthalene-modified resin, phenol-modified resin of naphthalene resin; polyhydroxystyrene, dicyclopentadiene resin, (meth) acrylate, and the like.
  • Non-resin examples thereof include resins or compounds containing an alicyclic structure such as rosin-based resins, cyclodextrines, adamantan (poly) all, tricyclodecane (poly) all and derivatives thereof.
  • the lithographic film-forming composition of the present embodiment may contain known additives other than those described above.
  • additives include, but are not limited to, heat and / or photocurable catalysts, polymerization inhibitors, flame retardants, fillers, coupling agents, thermosetting resins, photocurable resins, dyes, pigments. , Thickeners, lubricants, defoaming agents, leveling agents, ultraviolet absorbers, surfactants, colorants, nonionic surfactants and the like.
  • the composition for forming an optical component of the present embodiment is used for forming an optical component. That is, the optical component of the present embodiment includes the composition for forming an optical component of the present embodiment.
  • the optical component is not particularly limited, but for example, a film-shaped component, a sheet-shaped component, a prism lens, a lenticular lens, a micro lens, a frennel lens, a viewing angle control lens, a plastic lens such as a contrast improving lens, a retardation film, and the like.
  • the compound (0) is an embedded film and a flattening film on a photodiode, which is a member of a solid-state image sensor for which a particularly high refractive index is required, a flattening film before and after a color filter, a microlens, and a flattening on a microlens. It is suitably used as a material for forming a film and a conformal film.
  • the optical component is used as a film-like or sheet-like component, and after forming a desired optical component pattern on a layer formed from an optical component-forming composition formed on the film, if necessary. It may be an optical component formed by reflowing the pattern by heating.
  • optical component of this embodiment when applied to devices are microlens materials, sealing materials such as LEDs and PDs, and thin display-related materials such as thin film transistor protective films, liquid crystal color filter protective films, and black matrices. , Spacers and the like.
  • the optical component containing the composition for forming an optical component of the present embodiment tends to have an extremely excellent advantage that it is excellent in heat resistance and moisture resistance and is less contaminated by sublimation components.
  • the material tends to be a material having high sensitivity, high heat resistance, and moisture absorption reliability with little deterioration of image quality due to important contamination.
  • the composition for forming an optical component of the present embodiment may contain various kinds of curing agents and, if necessary, other resins, surfactants and dyes, fillers, cross-linking agents, dissolution accelerators and the like. It may be prepared by adding an additive and dissolving it in an organic solvent.
  • the composition for forming an optical component of the present embodiment can be prepared by blending each of the above components and mixing them using a stirrer or the like.
  • a disperser such as a dissolver, a homogenizer, or a three-roll mill.
  • the method for purifying the compound (0) and / or the resin (6) is a solution containing an organic solvent that is arbitrarily immiscible with water and the compound (0) and / or the resin (6) (hereinafter, simply, “solution (hereinafter, simply” solution (hereinafter, “solution”). It is preferable to include an extraction step of contacting A) with an acidic aqueous solution for extraction.
  • the compound (0) and / or the resin (6) is dissolved in an organic solvent that is not arbitrarily mixed with water, and the solution is brought into contact with an acidic aqueous solution to perform an extraction treatment. It is preferable that the metal component contained in the solution (A) is transferred to the aqueous phase, and then the organic phase and the aqueous phase are separated and purified.
  • the purification method of the present embodiment can significantly reduce the content of various metals in the compound or resin of the present embodiment.
  • the "organic solvent immiscible with water” means that the solubility in water at 20 ° C. is less than 50% by mass, and from the viewpoint of productivity, it is preferably less than 25% by mass. ..
  • the organic solvent that is not arbitrarily miscible with water is not particularly limited, but an organic solvent that can be safely applied to the semiconductor manufacturing process is preferable.
  • the amount of the organic solvent used is usually about 1 to 100 times by mass with respect to the compound (0) and / or the resin (6).
  • organic solvent examples are not particularly limited, but examples thereof include those described in International Publication WO2015 / 080240. These solvents may be used alone or in combination of two or more. Among these, toluene, 2-heptanone, cyclohexanone, cyclopentanone, methyl isobutyl ketone, PGMEA, ethyl acetate and the like are preferable, and cyclohexanone and PGMEA are more preferable.
  • the acidic aqueous solution to be used is appropriately selected from generally known organic compounds or aqueous solutions in which an inorganic compound is dissolved in water.
  • these acidic aqueous solutions may be used alone or in combination of two or more.
  • aqueous solutions of sulfuric acid, nitric acid, and carboxylic acids such as acetic acid, oxalic acid, tartaric acid, and citric acid are preferable
  • aqueous solutions of sulfuric acid, oxalic acid, tartaric acid, and citric acid are more preferable
  • aqueous solutions of oxalic acid are even more preferable.
  • polyvalent carboxylic acids such as oxalic acid, tartaric acid, and citric acid can remove more metals because they coordinate with metal ions and produce a chelating effect.
  • water having a low metal content for example, ion-exchanged water or the like is preferably used according to the purpose of the present embodiment.
  • the pH of the acidic aqueous solution used in the present embodiment is not particularly limited, but usually, the pH range is preferably about 0 to 5, and more preferably about 0 to 3.
  • the amount of the acidic aqueous solution used in the present embodiment is not particularly limited, but if the amount is too small, it is necessary to increase the number of extractions for removing the metal, and conversely, if the amount of the aqueous solution is too large, the whole The amount of liquid may increase, causing operational problems.
  • the amount of the acidic aqueous solution used is usually preferably 10 to 200% by mass, preferably 20 to 100% by mass, based on the solution (A).
  • the metal component is extracted by bringing the above acidic aqueous solution into contact with the solution (A).
  • the temperature at which the extraction process is performed is usually preferably 20 to 90 ° C, more preferably 30 to 80 ° C.
  • the extraction operation is performed by, for example, stirring well and then allowing the mixture to stand. As a result, the metal content contained in the solution (A) shifts to the aqueous phase. Further, by this operation, the acidity of the solution is lowered, and the alteration of the compound (0) and / or the resin (6) can be suppressed.
  • the compound (0) and / or the resin (6) and the organic solvent are separated by decantation or the like. Recover the containing organic phase.
  • the standing time is not particularly limited, but for example, it is preferably 1 minute or longer, more preferably 10 minutes or longer, and even more preferably 30 minutes or longer. Further, although the extraction process may be performed only once, it is also effective to repeat the operations of mixing, standing, and separating a plurality of times.
  • the compound (0) and / or the resin (6) extracted and recovered from the acidic aqueous solution after the treatment and an organic solvent are contained.
  • the organic phase is preferably further extracted with water.
  • the extraction treatment is carried out by mixing the organic phase and water well by stirring or the like, and then allowing the mixture to stand. Then, the obtained solution is separated into a solution phase containing the compound (0) and / or the resin (6) and an organic solvent and an aqueous phase, so that the compound (0) and / or the resin (6) and the organic solvent are separated by decantation or the like. Recover the containing solution phase.
  • the water used here is preferably one having a low metal content, for example, ion-exchanged water, etc., in line with the purpose of the present embodiment.
  • the extraction process may be performed only once, but it is also effective to repeat the operations of mixing, standing, and separating a plurality of times.
  • the conditions such as the ratio of use of both in the extraction treatment, temperature, and time are not particularly limited, but the same as in the case of the contact treatment with the acidic aqueous solution may be used.
  • the water mixed in the solution containing the compound (0) and / or the resin (6) and the organic solvent thus obtained can be easily removed by performing an operation such as vacuum distillation. Further, if necessary, an organic solvent can be added to adjust the concentration of the compound (0) and / or the resin (6) to an arbitrary concentration.
  • the method for obtaining only the compound (0) and / or the resin (6) from the obtained solution containing the compound (0) and / or the resin (6) and the organic solvent is as follows: removal under reduced pressure, separation by reprecipitation, and a combination thereof. Etc., it can be carried out by a known method. If necessary, known treatments such as concentration operation, filtration operation, centrifugation operation, and drying operation can be performed.
  • the method for evaluating the amount of impurities in the compound (0) and / or the resin (6) compound (0) and / or the resin (6) after the purification method of the present embodiment, that is, after purification, is not particularly limited. , The amount of various metals measured by ICP-MS described in Examples described later can be evaluated.
  • LC-MS analysis measurement of molecular weight
  • Mn, Mw and Mw / Mn were determined by gel permeation chromatography (GPC) analysis in terms of polystyrene under the following measurement conditions.
  • Flow velocity 1 mL / min
  • Temperature 40 ° C
  • ICP-MS Measurement was performed using an inductively coupled plasma mass spectrometer (hereinafter, also referred to as “ICP-MS”) “ELAN DRCII” (product name, manufactured by PerkinElmer).
  • the reaction mixture is cooled, extracted twice with 1 L of ethyl acetate, concentrated, separated by column chromatography, and recrystallized with isopropyl alcohol three times.
  • the target compound represented by the following formula (XBisN-F1) (XBisN-F1) 1.3 g of XBisN-F1) was obtained.
  • the molecular weight of the obtained compound (XBisN-F1) was measured by the above-mentioned "LC-MS analysis" method and found to be 464.
  • the obtained resin (R1-XBisN-1) was Mn: 3650, Mw: 6950, and Mw / Mn: 1.90.
  • the mixture is cooled to 50 ° C., the reaction solution is dropped in pure water, the precipitated solid is filtered, dried, and then separated and purified by a column chromatograph.
  • the target compound (XBisN-F1) represented by the following formula is obtained.
  • -Ea) was obtained in an amount of 1.4 g.
  • the mixture is cooled to 50 ° C., the reaction solution is dropped in pure water, the precipitated solid is filtered, dried, and then separated and purified by column chromatography.
  • the target compound (XBisN-F1-) represented by the following formula is obtained.
  • Ua) was obtained in an amount of 1.5 g.
  • the mixture was neutralized and washed with water, and ethylbenzene and unreacted 1,5-dimethylnaphthalene were distilled off under reduced pressure to obtain 1.25 kg of a light brown solid dimethylnaphthalene formaldehyde resin.
  • the molecular weight of the obtained dimethylnaphthalene formaldehyde resin was number average molecular weight (Mn): 562, weight average molecular weight (Mw): 1168, and dispersity (Mw / Mn): 2.08.
  • a four-necked flask having an internal volume of 0.5 L equipped with a Dimroth condenser, a thermometer and a stirring blade was prepared.
  • 100 g (0.51 mol) of the dimethylnaphthalene formaldehyde resin obtained as described above and 0.05 g of p-toluenesulfonic acid were charged under a nitrogen stream, and the temperature was raised to 190 ° C. After heating for 2 hours, the mixture was stirred. After that, 52.0 g (0.36 mol) of 1-naphthol was further added, the temperature was further raised to 220 ° C., and the reaction was carried out for 2 hours.
  • the obtained resin (C-1) was Mn: 885, Mw: 2220, and Mw / Mn: 2.51.
  • Acid generator Ditert-butyldiphenyliodonium nonafluoromethanesulfonate (hereinafter, also referred to as "DTDPI”) (manufactured by Midori Chemical Co., Ltd.)
  • Crosslinking agent "Nicarax MX270” (hereinafter, also referred to as “MX270”) (Product name, manufactured by Sanwa Chemical Co., Ltd.)
  • Organic solvent Propylene glycol monomethyl ether (PGME)
  • composition for forming an optical component and the storage stability of the composition for forming an optical component containing a thin film forming compound are maintained at 23 ° C. for 3 days after the composition for forming an optical component is prepared.
  • the presence or absence of precipitation was evaluated by visually observing.
  • the composition for forming an optical component was rotationally coated on a clean silicon wafer and then baked (PB) before exposure on a hot plate at 110 ° C. to form a resist film having a thickness of 50 nm.
  • the prepared composition for forming optical components was evaluated as ⁇ when it was a uniform solution and the thin film formation was good, ⁇ when it was a uniform solution but the thin film had defects, and ⁇ when there was precipitation.
  • Refractive index and transparency test [Refractive index and transparency test]
  • the composition for forming an optical component was applied onto a SiO 2 substrate having a film thickness of 300 nm and baked at 260 ° C. for 300 seconds to form a film for an optical component having a film thickness of 100 nm.
  • the refractive index and transparency of the film for optical components were evaluated by the following methods. That is, using a vacuum ultraviolet multi-incident angle spectroscopic ellipsometer (product name "M-2000DI-YK", manufactured by JA Woolam Japan Co., Ltd.), a refractive index and transparency test at a wavelength of 633 nm were performed. The refractive index and transparency were evaluated according to the following criteria.
  • the compound (0) and the resin (6) have no problems in solubility in an organic solvent, storage stability, and film formation as optical component forming materials, and have a high refractive index and transparency. It can be said that they are compatible with each other. That is, the optical component forming composition of the present embodiment is useful as an optical component film forming material.
  • composition for forming an optical component containing the compound and / or resin of the present invention can be widely and effectively used in the application for forming an optical component. Therefore, according to the present invention, for example, a film-shaped or sheet-shaped component, a prism lens, a lenticular lens, a microlens, a Fresnel lens, a viewing angle control lens, a plastic lens such as a contrast improving lens, a retardation film, an electromagnetic wave shielding film, Prism, optical fiber, solder resist for flexible printed wiring, plating resist, interlayer insulating film for multilayer printed wiring board, photosensitive optical waveguide, liquid crystal display, organic electroluminescence (EL) display, optical semiconductor (LED) element, solid-state imaging element, Examples include organic thin film transistors, dye-sensitized solar cells, and organic thin film transistors (TFTs).
  • TFTs organic thin film transistors, dye-sensitized solar cells, and organic thin film transistors (TFTs).
  • the compound (1) is an embedded film and a flattening film on a photodiode, which is a member of a solid-state image sensor for which a particularly high refractive index is required, a flattening film before and after a color filter, a microlens, and a flattening on a microlens. It can be widely and effectively used in films and materials for forming conformal films.

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  • Chemical & Material Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Materials For Photolithography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition permettant de former des composants optiques qui contient un composé représenté par la formule (0). (Dans la formule (0), X représente un atome d'oxygène ou de soufre ou représente un état non ponté, les fractions R0 sont chacune indépendamment un groupe alkyle éventuellement substitué contenant 1 à 30 atomes de carbone, un groupe aryle éventuellement substitué contenant 6 à 30 atomes de carbone, un groupe alcényle éventuellement substitué contenant 2 à 30 atomes de carbone, un groupe alcynyle éventuellement substitué contenant 2 à 30 atomes de carbone, un groupe alcoxy éventuellement substitué contenant 1 à 30 atomes de carbone, un atome d'halogène, un groupe nitro, un groupe amino, un groupe carboxyle, un groupe réticulable, un groupe dissociable, un groupe thiol ou un groupe hydroxyle, au moins l'une des fractions R0 est un groupe hydroxyle, un groupe réticulable ou un groupe dissociable, et les groupes alkyle, aryle, alcényle, alcynyle et alcoxy en tant que fractions R0 peuvent chacun contenir une liaison éther, une liaison cétone ou une liaison ester, les fractions R2 sont chacune indépendamment un groupe alkyle éventuellement substitué contenant 1 à 30 atomes de carbone, un groupe aryle éventuellement substitué contenant 6 à 30 atomes de carbone, un groupe alcényle éventuellement substitué contenant 2 à 30 atomes de carbone, un groupe alcynyle éventuellement substitué contenant 2 à 30 atomes de carbone, un groupe alcoxy éventuellement substitué contenant 1 à 30 atomes de carbone, un atome d'halogène, un groupe nitro, un groupe amino, un groupe carboxyle, un groupe réticulable, un groupe dissociable, un groupe thiol ou un groupe hydroxyle et les groupes alkyle, aryle, alcényle, alcynyle et alcoxy en tant que fractions R2 peuvent chacun contenir une liaison éther, une liaison cétone, ou une liaison ester, chaque symbole n1 est indépendamment un nombre entier de 1 ou 2, chaque symbole n0 est indépendamment un nombre entier compris entre 0 et (4+2n1) (au moins un n0 compris entre 1 et (4+2n1)), chaque symbole n4 est indépendamment un nombre entier de 0 ou 1, et chaque symbole n5 est indépendamment un nombre entier compris entre 0 et (4+2n4).)
PCT/JP2020/017901 2019-04-26 2020-04-27 Composition pour former un composant optique WO2020218600A1 (fr)

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