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WO2019054707A1 - Nouveau dérivé de triazine et composition photosensible le comprenant - Google Patents

Nouveau dérivé de triazine et composition photosensible le comprenant Download PDF

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Publication number
WO2019054707A1
WO2019054707A1 PCT/KR2018/010549 KR2018010549W WO2019054707A1 WO 2019054707 A1 WO2019054707 A1 WO 2019054707A1 KR 2018010549 W KR2018010549 W KR 2018010549W WO 2019054707 A1 WO2019054707 A1 WO 2019054707A1
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Prior art keywords
compound
group
substituted
unsubstituted
formula
Prior art date
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PCT/KR2018/010549
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English (en)
Korean (ko)
Inventor
이규성
문봉석
진성민
강지승
하민수
진상준
박노길
이현우
변우근
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Treeel Co Ltd
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Treeel Co Ltd
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Priority claimed from KR1020180107042A external-priority patent/KR102145580B1/ko
Application filed by Treeel Co Ltd filed Critical Treeel Co Ltd
Priority to CN201880057939.8A priority Critical patent/CN111065628B/zh
Priority to US16/643,250 priority patent/US11427551B2/en
Priority to JP2020535948A priority patent/JP6965455B2/ja
Publication of WO2019054707A1 publication Critical patent/WO2019054707A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators

Definitions

  • the present invention relates to a novel triazine derivative and a photosensitive composition containing the same, and more particularly to a novel triazine derivative having a high refractive index after a photo-crosslinking process, excellent curability in a process of producing an optical material, A novel triazine derivative having excellent properties and a photosensitive composition containing the novel triazine derivative.
  • a liquid crystal display includes an optical sheet including an optical pattern formed on a base film and a base film, and a light guide plate is disposed under the optical sheet, or another optical sheet is provided between the optical sheet and the light guide plate .
  • optical sheets include a reflector sheet, a diffuser sheet, a prism sheet, These optical sheets are used for the purpose of improving the brightness of the backlight unit.
  • the optical sheet increases the brightness of light emitted in such a manner that light emitted from the light guide plate of the backlight is refracted and transmitted to the screen after passing through the liquid crystal.
  • the refractive index of the optical sheet such as prism and DBEF It should be high.
  • the conventional high-refraction monomers have a low refractive index and thus have limitations in realizing brightness enhancement effects. Further, even when the refractive index of the optical sheet is increased, yellowing occurs in the optical sheet.
  • Korean Patent Registration No. 10-1692343 2016.12.28
  • Korean Patent Laid-Open Publication No. 10-2017-0013674 2017.02.07 propose an acrylic monomer as a high refractive index monomer have.
  • a first technical object of the present invention is to provide a novel triazine derivative compound which has high transmittance, excellent light-crosslinking property and yellowing resistance, and which can be used as a monomer in a photosensitive composition having high refractive index .
  • a second technical object of the present invention is to provide a photosensitive composition comprising the triazine derivative compound and an optical article obtained by polymerizing the same.
  • the present invention provides a compound represented by any one of the following formulas (A) to (C).
  • Ra is any substituent selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 6 alkyl group,
  • L1 is a single bond, O, S, or -N (-R5) -,
  • L2 is a single bond, O, S, or -N (-R6) -,
  • X 1 to X 3 are the same or different and independently of each other are a single bond, O, S, -N (-R 7) - or -O ((CH 2 ) m O) n - n is an integer selected from 1 to 4, and at least two of X1 to X3 each represent -N (-R7) -, or two or more of X1 to X3 each independently represent - O ((CH 2) m O ) n - each -N (-R7) in the case of selecting - and -O ((CH 2) m O ) n - may be identical to or different from each other, and
  • R4 to R7 are the same or different, independently represent hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted C 6 -C 50 ring, each ring of A C 3 -C 30 cycloalkyl group, and a substituted or unsubstituted C 7 -C 24 arylalkyl group,
  • W1 is any one selected from an alkylene group of a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 1 -C 12 a,
  • W2 and W3 are the same or different and each independently represent a single bond, a substituted or unsubstituted C 1 a C 6 aryl group, a substituted or unsubstituted ring of -C 30 alkylene group, a substituted or unsubstituted -C 30 unsubstituted C 2 -C 30 of alkenylene group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkenyl group, the substituted or unsubstituted C 2 -C 50 hetero arylene group, and any one is selected from a substituted or unsubstituted heterocycloalkyl group of C 2 -C 30 a,
  • Y1 and Y2 are the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or non-substituted of unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 of each ring C, respectively of 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl of the group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkenyl group , A substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group, a
  • Rb and Rc are each the same or different, and independently are any one selected from the group consisting of hydrogen, deuterium, an alkyl group a substituted or unsubstituted C 1 -C 6 with each other,
  • Ar 1 is a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 2 -C 30 heteroarylene group, a substituted or unsubstituted C 1 -C 30 alkylene group, and the one which is C 2 -C 30 alkenylene group, selected from substituted or unsubstituted C 3 -C 30 cycloalkylene group, a substituted or unsubstituted C 5 -C 30 cycloalkenyl group of the,
  • L6 is any one selected from a single bond, O, S, -N (-R11) -,
  • L7 is any of a single bond, O, S, -N (-R12) -,
  • Rd is a substituent of any one selected from hydrogen, deuterium, an alkyl group a substituted or unsubstituted C 1 -C 6,
  • Each of L3 to L5 is the same or different and independently selected from a single bond, O, S, or -N (-R9) -,
  • each of -N (-R9) is the same or different
  • X4 to X7 are the same or different and each, independently of one another a single bond, O, S, -N (-R10 ) -, -O ((CH 2) m O) n - are optionally replaced with one selected from said m and n are the same or different and are each independently an integer selected from 1 to 4,
  • R8 to R12 are the same or different, independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or unsubstituted of C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 ring, each ring of the A C 3 -C 30 cycloalkyl group, and a substituted or unsubstituted C 7 -C 24 arylalkyl group,
  • W4 is any one selected from the group consisting of a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, and a substituted or unsubstituted C 1 -C 12 alkylene group,
  • the W5 to W7 are the same or different and each independently represent a single bond, a substituted or unsubstituted C 1 -C 30 an alkyl group, an arylene group, a substituted or unsubstituted substituted or unsubstituted C 6 -C 30 unsubstituted C 2 -C 30 of alkenylene group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkenyl group, the substituted or unsubstituted C 2 -C 50 hetero arylene group, and any one is selected from a substituted or unsubstituted heterocycloalkyl group of C 2 -C 30 a,
  • the Y3 to Y5 are the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted aryl group, a substituted or non-substituted of unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 of each ring C, respectively of 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl of the group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 cycloalkenyl group , A substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 -C 30 alkylsilyl group, a
  • Rb and Rc are each the same or different, and independently are any one selected from the group consisting of hydrogen, deuterium, an alkyl group a substituted or unsubstituted C 1 -C 6 with each other,
  • the present invention also provides a photosensitive composition
  • a photosensitive composition comprising a compound represented by any one of the above-mentioned formulas (A) to (C) and an optical material or an optical article obtained by polymerizing the same.
  • novel triazine derivative compounds represented by any one of the formulas (A) to (C) according to the present invention can be used in a photosensitive composition to provide a property of high refractive index after the photo-crosslinking step.
  • a photosensitive composition having a high transmittance and an excellent yellowing resistance characteristic, and has a limit in realizing a luminance improvement effect due to a low refractive index according to the prior art, and can solve the problem of color change of the optical sheet due to yellowing (DBEF) film, a coating material for an organic light emitting device (OLED), an optical lens, and a multifocal lens, which can be applied to a prism sheet, a microlens, a coating material for an LCD, a DBEF (Dual Brightness Enhancement Film)
  • DBEF Yellowing
  • the compound represented by any one of the above-mentioned formulas (A) to (C) according to the present invention contains 1 to 3 triazine structures and may contain N, O, S or a single bond to each carbon atom of the triazine A first connecting portion; A second connecting portion comprising a single bond, an alkylene group or an arylene group; And a third connecting portion having N, O, S, alkylene oxide, or a single bond, and having a double bond such as at least one acrylic acid derivative at the terminal, wherein, among three carbon atoms of triazine,
  • a technical feature is that a nitrogen atom is bonded to at least one carbon atom and a terminal thereof has a double bond such as an acrylic acid derivative.
  • the carbon numbers of the C 1 -C 20 alkyl group and the C 6 -C 50 aryl group are each an alkyl moiety or an aryl moiety constituting the alkyl moiety or the aryl moiety when considered to be unsubstituted, Means the number of carbon atoms.
  • a phenyl group substituted with a butyl group at the para position should be considered to correspond to a C 6 aryl group substituted with a C 4 butyl group.
  • the aryl group which is a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to form a ring.
  • the heteroaryl group which is a substituent used in the compound of the present invention is a heteroaryl group having 1, 2 or 3 hetero atoms selected from N, O, P, Si, S, Ge, Se and Te in the aryl group, Means a C 2 -C 24 ring aromatic system, which rings can be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.
  • alkyl group as a substituent used in the present invention examples include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl and hexyl.
  • the hydrogen atoms of the above hydrogen atoms can be substituted with the same substituents as those in the aryl group.
  • alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.
  • alkylaryl group used as the substituent in the compound of the present invention include methylphenyl, dimethylphenyl, n -propylphenyl, t -butylphenyl, methylnaphthyl and the like, May be substituted with the same substituents as those in the aryl group.
  • the above hydrogen atoms may be substituted with substituents similar to those in the aryl group.
  • silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , And dimethylpurylsilyl.
  • At least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.
  • R6 is preferably the same or different, and independently represent hydrogen, deuterium, substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C of each other, respectively And an aryl group having 6 to 20 carbon atoms, and Ra, Rb and Rc are preferably the same or different, and independently of each other may be any substituent selected from hydrogen and a deuterated methyl group.
  • At least one of Y1 and Y2 in formula (A) may be a structural formula (1) or a structural formula (2).
  • L 1 in the formula (A) may be -N (-R 5) - or S
  • L 2 may be -N (-R 6) - or S, more preferably L 1 is -N (-R 5)
  • L2 is a -N (-R6) -
  • R5 and R6 are either same or different and are each, independently represent hydrogen, deuterium, aryl selected from the group of C 1 -C 10 alkyl, C 6 -C 20 of Lt; / RTI >
  • L 1 and L 2 may each contain a nitrogen atom or a sulfur atom, and when they contain a nitrogen atom or a sulfur atom, they are more preferable since they have a high transparency and a high refractive index.
  • At least one of the formula (A) in W1 to W3 in the present invention is substituted or unsubstituted C 6 arylene group may be the date -C 30 ring, preferably, W1 to two are a substituted or unsubstituted C of W3 6 or an aryl group of 30 or -C W1 to W3 can all arylene date of substituted or unsubstituted C 6 -C 30.
  • the plate structure is formed due to the aromatic plane structure of the C 6 -C 30 arylene group and the plane structure of the triazine, and thus high high-refraction characteristics can be obtained.
  • At least one of the formula (A) in W1 to W3 is a substituted or Examples of the unsubstituted aryl group of C 6 -C 30, wherein the formula (A) in W1 is a substituted or unsubstituted phenylene group ring, wherein W2 and W3 May be the same or different and independently of each other, a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 1 -C 12 alkylene group.
  • W 1 is a substituted or unsubstituted phenylene group
  • W 2 and W 3 are the same At least one of them is a substituted or unsubstituted C 6 -C 30 arylene group
  • W 1 to W 3 are the same or different, and at least two of them are a substituted or unsubstituted phenylene group
  • W1 to W3 are the same or different and each is a substituted or unsubstituted phenylene group.
  • the above-mentioned [Chemical Formula B] and [Chemical Formula C] within substituents R8 to R12 are preferably identical or different and, independently from each other hydrogen, deuterium, an alkyl group a substituted or unsubstituted C 1 -C 20 respectively according to the present invention , substituted or unsubstituted and which is selected from aryl groups unsubstituted C 6 -C 20 a, Ra, Rb and Rc is preferably any of the substituents, the same or different and independently selected from hydrogen, deuterium, a methyl group from each other, respectively Lt; / RTI >
  • At least one of Y 3 and Y 5 in the above formulas (B) and (C) may be a structural formula 1 or a structural formula 2. By having such a structure, both ends of the monomer have a double bond, Can be adjusted.
  • L 3 to L 7 are the same or different and independently of each other, a single bond, -N (-R 9) - or S, and two or more of L 3 to L 7 are each -N ) each in the case of selecting -N (-R9) - are either the same or different, independently represent hydrogen, deuterium, aryl selected from the group of C 1 -C 10 alkyl, C 6 -C 20 of Lt; / RTI >
  • L3 to L5 are the same or different and independently of each other, a single bond, -N (-R9) - or S, and two or more of L3 to L5 are each -N ) each in the case of selecting -N (-R9) - are either the same or different, independently represent hydrogen, deuterium, aryl selected from the group of C 1 -C 10 alkyl, C 6 -C 20 of Lt; / RTI >
  • L3 to L7 in the above formulas (B) and (C) may contain a nitrogen atom or a sulfur atom, and when they contain a nitrogen atom or a sulfur atom, they have a high transparency and a high refractive index, Do.
  • the one selected from Formula B] and [Chemical Formula C] within R9, R11 to R12 are the same or different and each independently represent hydrogen, deuterium, aryl group of C 1 -C 10 alkyl, C 6 -C 20 of each other It can be one.
  • the plate structure is formed due to the aromatic plane structure of the C 6 -C 30 arylene group and the plane structure of the triazine, and thus high high-refraction characteristics can be obtained.
  • the W4 to the remaining one or two phenylene groups, not of W7 are the same or different and independently of each other a single bond, an arylene group, a substituted or unsubstituted substituted or unsubstituted C 6 -C 30 ring And may be a C 1 -C 12 alkylene group.
  • W4 to W7 in the above formulas (B) and (C) are substituted or unsubstituted C 6 -C 30 arylene groups, And all or four of them may be a substituted or unsubstituted phenylene group.
  • the W4 through W7 3 dogs substituted or unsubstituted on the remaining unsubstituted phenylene group is not phenylene group one is a single bond, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C of Or an alkylene group of 1 to 12 carbon atoms.
  • the present invention provides a photosensitive composition
  • a photosensitive composition comprising a compound represented by any one of the above-mentioned formulas (A) to (C).
  • the compound represented by any one of the above-mentioned formulas (A) to (C) according to the present invention may be contained in the photoreactive composition as a photocrosslinkable monomer to form a thin film or a prism by light such as UV,
  • the composition When the composition is used in a composition for a display or an electronic material, it has an excellent compatibility with a solvent or an acrylic monomer.
  • the compounds represented by any one of the above-mentioned formulas (A) to (C) are excellent in refractive index, transmittance and yellowing resistance and can improve brightness and performance when used as a high refractive index monomer for TFT-LCD and OLED.
  • the photosensitive composition may further include a photoinitiator or a photopolymerizable monomer, and may include, but not limited to, a substance used in other known photosensitive compositions.
  • the present invention also provides an optical article obtained by polymerizing the photosensitive composition.
  • the photosensitive composition of the present invention 1 to 95 parts by weight of a compound represented by any one of the above formulas (A) to (C), 0 to 90 parts by weight of a photopolymerizable compound and 0.1 to 20 parts by weight of a photoinitiator.
  • the photopolymerizable compound means a compound containing one or two or more acryl groups, methacrylic groups or vinyl groups
  • the photoinitiator according to the present invention is a compound which is formed by radicals generated by UV and crosslinked by the generated radicals.
  • the photopolymerizable compound may be an alkyl acrylate such as hexyl (meth) acrylate, cyclohexyl (meth) acrylate, tetradecyl (meth) acrylate and hexadecyl (meth) acrylate; (Meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, (Meth) acrylate, trimethylol propane di (meth) acrylate, trimethylol propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, acrylic acid, methacrylic acid, glycidyl acrylate, .
  • alkyl acrylate such as hexyl (meth) acrylate, cyclohexyl (
  • photoinitiator examples include ketones, ketoacetals, thioguanthones, phosphine oxides, anthraquinones, trichloromethyl triazine, and oxime esters.
  • photo initiators include phenylbiphenyl ketone, 1-benzyl-1-dimethylamino-1- (4-morpholino-benzoyl) propane, 1-hydroxy-1-benzoylcyclopentane, Benzoyl-4-methylphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoyl propane, 2-methyl- Butylbenzoyl trichloromethane, 4-phenoxybenzoyl dichloromethane, diphenyl-2,4,6-trimethylbenzoylphosphine oxide, methyl benzoylformate, methyl benzoate, (Trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) Na
  • Such a photoinitiator is more preferably used in an amount of 0.1 to 20 parts by weight, preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive composition, in order to control exposure sensitivity and pattern characteristics.
  • an organic solvent may optionally be used to dissolve the photosensitive composition, Is used for improving the coating property, and it is preferable to use an organic solvent as such solvent.
  • organic solvent preferably ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethyl ethyl ether, methyl methoxy propionate, ethyl ethoxypropionate (EEP), ethyl lactate, propylene glycol Methyl ether acetate (PGMEA), propylene glycol methyl ether, propylene glycol propyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol methyl acetate, diethylene glycol ethyl acetate, acetone, methyl isobutyl ketone, (NMP), gamma -butyrolactone, diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol dimethyl ether
  • the reaction conditions are as follows: Diglyme, tetrahydrofuran (THF), methanol,
  • the photosensitive composition according to the present invention can be used for producing any one selected from a prism sheet, a microlens, a coating material for LCD, a DBEF film, a coating material for an organic light emitting diode (OLED) have.
  • the reaction scheme 1 shows a synthetic mechanism for a part of the compounds having an acryl group and may be appropriately substituted with a substituent such that the substituent is appropriately substituted with a substituent selected from the group consisting of a variety of acrylic groups represented by any one of the formulas (A), (B) Compounds can be synthesized.
  • reaction vessel 150 mL of THF is added to a 500 mL reactor, and 15.0 g (81.3 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 ° C, 5.0 g (81.3 mmol) of 2-aminoethanol and 12.7 g (162.6 mmol) of 2-mercaptoethanol were slowly added in succession for 30 min each time with stirring, and 20.0 g (243.9 mmol) . The reaction vessel is heated to 80 ° C and stirred for 15 hours. After the completion of the reaction, distilled water and ethyl acetate are added and removed.
  • a 250 ml reactor was charged with 100 ml of THF, 20 ml of triethylamine and 10.0 g of 2,2 '- ((6 - ((2-hydroxyethyl) thio) -1,3,5-triazine-2,4-diyl) bis (methylazanediyl) 32.9 mmol) were successively added thereto, followed by cooling to 0 ° C under nitrogen. 10.3 g (98.8 mmol) of methacryloyl chloride was slowly added to the above reaction vessel for 30 minutes and then stirred at room temperature for 10 hours.
  • Diacetyl) diphenol 23.0 g of 3,3 '- ((6 - ((2-hydroxyethyl) amino) -1,3,5-triazine- (Yield: 73%).
  • Example 1 and Example 2 the high-refraction monomers were prepared by using the following R1 (((9H-fluorene-9,9-diyl) bis (4,1- phenylene)) bis (Ethane-2, 1 -dine) diacrylate.
  • the synthesized high-refractive-index acrylic monomer was dissolved in the same weight ratio to 2 - ([1,1'-biphenyl] -2-yloxy) ethyl acrylate and then measured by ABBE refractometer at 25 ° C.
  • the high-refractive-index acrylic monomers thus synthesized were dissolved in the same weight ratio to 2 - ([1,1'-biphenyl] -2-yloxy) ethyl acrylate, and the viscosity was measured with a Brookfield viscometer at 25 ° C.
  • a crosslinked prism sheet specimen was prepared by UV irradiation at 500 mJ / cm 2 on an optical PET substrate.
  • the crosslinked prism sheet was measured for UV transmittance at 400 nm using a UV-vis.
  • the crosslinked prism sheet was subjected to a UVA lamp 1J for 8 hours at 95 ° C for 8 hours at 60 ° C using a reliability evaluation system (QUV tester) for 120 hours and then the value of change ⁇ YI Respectively.
  • QUV tester a reliability evaluation system
  • the photosensitive compositions of Examples 1 to 16 of the present invention exhibited remarkably high refractive index and similar viscosities to those of the compositions of Comparative Examples 1 and 2.
  • the light transmittance was excellent as compared with the compositions of Comparative Examples 1 and 2, and it was confirmed that the yellowing property after the reliability evaluation was excellent.
  • the triazine derivative compound according to the present invention is used in a photosensitive composition and exhibits a high refractive index after the photo-crosslinking process, and solves the problem of color change of the optical sheet due to yellowing phenomenon according to the prior art, (DBEF) film, a coating material for an organic light emitting device (OLED), an optical lens, a multifocal lens, and the like can be provided. It is possible to apply it as a material for industrial application.

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Abstract

La présente invention concerne un composé représenté par l'une quelconque des formules suivantes A à C, et une composition photosensible comprenant celui-ci, la structure du composé représenté par l'une quelconque des formules A à C étant telle que décrite dans la description détaillée de l'invention.
PCT/KR2018/010549 2017-09-13 2018-09-10 Nouveau dérivé de triazine et composition photosensible le comprenant Ceased WO2019054707A1 (fr)

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CN201880057939.8A CN111065628B (zh) 2017-09-13 2018-09-10 新型三嗪衍生物以及包含该三嗪衍生物的光敏组合物
US16/643,250 US11427551B2 (en) 2017-09-13 2018-09-10 Triazine derivative and photosensitive composition comprising same
JP2020535948A JP6965455B2 (ja) 2017-09-13 2018-09-10 新規なトリアジン誘導体及びこれを含む感光性組成物

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KR1020180107042A KR102145580B1 (ko) 2017-09-13 2018-09-07 신규한 트리아진 유도체 및 이를 포함하는 감광성 조성물

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2021230002A1 (fr) * 2020-05-15 2021-11-18

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03256048A (ja) * 1990-03-07 1991-11-14 Nippon Soda Co Ltd めっきレジスト剥離防止剤
US5597485A (en) * 1988-05-13 1997-01-28 Vilmax S.A. Process for separating proteins
KR101569344B1 (ko) * 2014-05-19 2015-11-16 한국화학연구원 광경화성 코팅조성물

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5597485A (en) * 1988-05-13 1997-01-28 Vilmax S.A. Process for separating proteins
JPH03256048A (ja) * 1990-03-07 1991-11-14 Nippon Soda Co Ltd めっきレジスト剥離防止剤
KR101569344B1 (ko) * 2014-05-19 2015-11-16 한국화학연구원 광경화성 코팅조성물

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BU, J. ET AL.: "Preparation and Expansion Properties of a Novel UV-curable Intumescent Flame-retardant Coating", JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, vol. 122, 2015, pages 329 - 338, XP035547092, DOI: doi:10.1007/s10973-015-4733-7 *
GRABCHEV, I. ET AL.: "Photoisomerization of Triazine-stilbene Fluorescent Brighteners in Solution and in Their Copolymers with Styrene", ZEITSCHRIFT FUR NATURFORSCHUNG, vol. 55, 2000, pages 833 - 836, XP055584993 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2021230002A1 (fr) * 2020-05-15 2021-11-18
WO2021230002A1 (fr) * 2020-05-15 2021-11-18 富士フイルム株式会社 Composition durcissable, matériau thermoconducteur, feuille thermoconductrice, dispositif à couche thermoconductrice, et composé
JP7440626B2 (ja) 2020-05-15 2024-02-28 富士フイルム株式会社 硬化性組成物、熱伝導材料、熱伝導シート、熱伝導層付きデバイス、化合物

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