WO2017170182A1 - Photosensitive composition and novel compound - Google Patents
Photosensitive composition and novel compound Download PDFInfo
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- WO2017170182A1 WO2017170182A1 PCT/JP2017/011885 JP2017011885W WO2017170182A1 WO 2017170182 A1 WO2017170182 A1 WO 2017170182A1 JP 2017011885 W JP2017011885 W JP 2017011885W WO 2017170182 A1 WO2017170182 A1 WO 2017170182A1
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- group
- carbon atoms
- photosensitive composition
- substituent
- represented
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Chemical group C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- 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
- 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 photosensitive composition containing a compound having a specific structure, which is inactive at room temperature and is activated by heating to a predetermined temperature to exhibit a function, and a novel compound. Furthermore, the present invention relates to a colored photosensitive composition obtained by adding a colorant to the photosensitive composition, and a color filter using the colored photosensitive composition.
- Patent Documents 1 to 4 In order to improve the weather resistance and heat resistance of the photosensitive composition, a method of stabilizing by adding an ultraviolet absorber or an antioxidant is known (Patent Documents 1 to 4).
- Phenolic antioxidants and UV absorbers have the effect of trapping radicals that greatly affect the deterioration of the polymer, so adding them into the polymerization system generally acts as a so-called polymerization inhibitor and inhibits curing. Therefore, latent additives have been developed (Patent Document 5).
- a composition using a conventional latent additive has a large amount of outgas, so that there is a problem that the heating device is contaminated or the physical properties of the composition are lowered. There are problems of contamination of equipment and reduction of physical properties.
- the composition using the conventional latent additive has a problem that the cured product has low solvent resistance, and thus the cured product is eluted, and the luminance of the color filter is lowered, for example.
- Patent Document 6 discloses a triallylphenol compound useful as a curing agent, but does not suggest a photosensitive composition containing the triallylphenol compound.
- JP 2011-048382 A US Patent Application Publication No. 2016/016919 JP2015-108649A JP2015-132791A International Publication No. 2014/021023 Japanese Patent Laid-Open No. 3-232732
- an object of the present invention is to use a compound that is inactive at normal temperature and activated by heating to a predetermined temperature and that exhibits a function as an antioxidant or an ultraviolet absorber, and has a low outgas.
- the object is to provide a photosensitive composition having high solvent resistance.
- Another object of the present invention is to provide a colored photosensitive composition obtained by adding a colorant to the photosensitive composition, particularly a colored photosensitive composition suitable for a color filter.
- a photosensitive composition using a compound having a specific protecting group has less outgas, and the cured product has high solvent resistance. It was found that a colored photosensitive composition obtained by adding a colorant to a photosensitive composition is suitable for a color filter for an image display device such as a liquid crystal display panel without reducing the luminance of an optical filter (particularly a color filter).
- the present invention has been reached.
- the present invention has been made based on the above findings, and provides a photosensitive composition containing a compound having a substituent represented by the following general formula (1).
- R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl having 1 to 40 carbon atoms which may have a substituent
- An aryl group having 6 to 20 carbon atoms which may have a substituent, an arylalkyl group having 7 to 20 carbon atoms which may have a substituent, or a substituent In some cases represents a C2-C20 heterocyclic-containing group or a trialkylsilyl group
- the methylene group in the alkyl group or arylalkyl group represented by R 1 and R 2 is —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—.
- R' is a hydrogen atom or a carbon atom Represents an alkyl group of 1 to 8, j represents a number from 1 to 3, * Means that it is bonded to an adjacent group at the * part. )
- the photosensitive composition of the present invention contains a compound having a substituent represented by the above general formula (I).
- n represents an integer of 1 to 10
- X 1 represents an n-valent linking group
- R 1 , R 2 and j are the same as in the general formula (I).
- Examples of the halogen atom represented by R 1 and R 2 include fluorine, chlorine, bromine and iodine.
- Examples of the alkyl group having 1 to 20 carbon atoms represented by R 1 and R 2 include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl Tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl, adamantyl and the like,
- Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 1 and R 2 include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 9-anthracenylmethyl, 9-fluorenyl, 3 -Phenylpropyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl and the like,
- Examples of the heterocyclic group containing 2 to 20 carbon atoms represented by R 1 and R 2 include a pyridine ring, a pyrimidine ring, a pyridazine ring, a piperidine ring, a pyran ring, a pyrazoline ring, a triazine ring, a pyrroline ring, a quinoline ring, Isoquinoline ring, imidazoline ring, benzimi
- alkyl group having 1 to 8 carbon atoms represented by R ′ examples include those satisfying a predetermined number of carbon atoms among the above alkyl groups represented by R 1 . Containing an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic ring having 2 to 20 carbon atoms represented by R 1 and R 2 Substituents for substituting groups include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl and methacryloyl Acyl groups such as phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoro
- R 1 and R 2 a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an aryl group having 6 to 12 carbon atoms are preferable because of less outgassing. It is more preferable that R 1 and R 2 are either a hydrogen atom or a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, because outgas is small.
- X 1 represents an n-valent linking group. Specifically, for example, a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, the following (I -a) or (I-b), a group represented by, -CO -, - NH-CO -, - CO-NH -, - NR 3 -, - oR 3, -SR 3, -NR 3 R 4, Or an aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent having the same valence as n, and 6 to 35 carbon atoms which may have a substituent.
- R 3 and R 4 have a hydrogen atom or a substituent.
- n is 3
- X 1 is an oxygen atom or a sulfur atom, —CO— , —NH—CO—, —CO—NH— or —NR 3 —
- n is 2
- X 1 is a hydrogen atom, —OR 3 , —SR 3 or —NR 3 R 4 , n is 1 and X 1 may form a ring together with the benzene ring.
- the n groups are the same or different from each other.
- the value of n is 1 to 10, and preferably 2 to 6 from the viewpoint of low outgas.
- the aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent represented by X 1 in the general formula (IA) and having the same valence as n is n are monovalent, for example, methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3- Alkyl such as hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl
- Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, which may have a substituent having the same valence as n are those in which n is monovalent, such as benzyl, phenethyl, diphenylmethyl, Arylalkyl groups such as triphenylmethyl, styryl and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio; and these groups are substituted by substituents described later Group, etc.
- n is divalent, arylene groups such as phenylene and naphthylene; residues of bifunctional phenols such as catechol and bisphenol; 2,4,8,10-tetraoxaspiro [5,5] undecane and the like; A group in which the group is substituted by a substituent described later,
- Examples of the trivalent n include phenyl-1,3,5-trimethylene and groups in which these groups are substituted with a substituent described later.
- the heterocycle-containing group having 2 to 35 carbon atoms that may have a substituent having the same number of valences as n includes those in which n is monovalent, pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl , Pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyo
- Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 3 and R 4 include the aliphatic hydrocarbon group represented by X 1 and the aliphatic hydrocarbon group.
- Examples of the heterocyclic ring-containing group include an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms and a heterocyclic ring-containing group having 2 to 35 carbon atoms represented by the above X 1 and these groups and substituents described later.
- substituents include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl and phenylcarbonyl ( Benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl, etc .; acetyloxy, benzoyloxy, etc.
- X 1 when n is 2 to 6, X 1 can also be represented by the following general formulas (1) to (5), respectively.
- Y 1 represents a single bond, —CR 5 R 6 —, —NR 7 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, or 6 to 35 carbon atoms.
- the aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
- Z 1 and Z 2 are each independently a direct bond, —O—, —S—,> CO, —CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—,
- R 5 , R 6 and R 7 may each independently have a hydrogen atom, a substituent, or an aliphatic hydrocarbon group having 1 to 35 carbon atoms or a substituent.
- R 8 represents a hydrogen atom, a phenyl group which may have a substituent, or a cycloalkyl group having 3 to 10 carbon atoms
- R 9 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen atom
- the alkyl group, alkoxy group and alkenyl group are substituents.
- May have f is an integer from 0 to 5, * Means that it is bonded to an adjacent group at the * part.
- R 10 and R 11 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, or a carbon atom having 6 substituents which may have a substituent.
- the methylene group in the alkyl group and arylalkyl group may be replaced with an unsaturated bond, —O— or —S—, R 10 may form a ring with adjacent R 10 , p
- Y 11 represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 to 35 carbon atoms.
- Z 1 , Z 2 and Z 3 are each independently a direct bond, —O—, —S—, —CO—, —CO—O—, —O—CO—, —SO 2 —, —SS—
- R 12 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic carbon group having 6 to 35 carbon atoms which may have a substituent.
- the aliphatic hydrocarbon group includes a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—.
- the oxygen atom may be replaced by a linking group combining these without being adjacent to each other, * Means that it is bonded to an adjacent group at the * part.
- Y 12 represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or 2 carbon atoms. Represents ⁇ 35 heterocycle-containing groups,
- the aliphatic hydrocarbon group is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO.
- Z 1 to Z 4 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2), * Means that it is bonded to an adjacent group at the * part. )
- Y 13 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a complex having 2 to 20 carbon atoms. Represents a ring-containing group, The aliphatic hydrocarbon group is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO.
- Z 1 to Z 5 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2), * Means that it is bonded to an adjacent group at the * part. )
- Y 14 represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a complex having 2 to 35 carbon atoms. Represents a ring-containing group, The aliphatic hydrocarbon group is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO.
- Z 1 to Z 6 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2), * Means that it is bonded to an adjacent group at the * part. )
- the aliphatic hydrocarbon group having 1 to 35 carbon atoms, which may have a substituent, represented by R 5 , R 6 and R 7 includes the above general formula ( The monovalent aliphatic hydrocarbon group exemplified as the n-valent linking group represented by X 1 in IA), and the n valence represented by X 1 in the general formula (IA).
- Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent represented by R 5 , R 6 and R 7 include X 1 in the above general formula (IA).
- groups substituted by those exemplified as the substituents in the above those satisfying a predetermined number of carbon atoms, etc.
- the heterocyclic group having 2 to 35 carbon atoms which may have a substituent represented by R 5 , R 6 and R 7 is represented by X 1 in the above general formula (IA).
- monovalent heterocycle-containing groups exemplified as the n-valent linking group, and these groups are exemplified as substituents of the group representing the n-valent bond represented by X 1 in the general formula (IA).
- those substituted by the above those satisfying a predetermined number of carbon atoms can be mentioned.
- the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 1 in the general formula (1) is an n represented by X 1 in the general formula (IA).
- Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 1 include the divalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
- Examples of the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y 1 include the divalent aromatic compounds exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Of the ring-containing hydrocarbon groups and groups substituted by those exemplified as the substituents of the group representing the n-valent linking group represented by X 1 in the general formula (IA) And the like satisfying the number of carbon atoms.
- examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 8 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
- the alkyl group having 1 to 10 carbon atoms represented by R 9 satisfies the predetermined number of carbon atoms among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 1 and R 2. Groups, etc.
- Examples of the alkoxy group having 1 to 10 carbon atoms represented by R 9 include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy Hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, etc.
- the substituents of the phenyl group, cycloalkyl group, alkyl group, alkoxy group and alkenyl group are the same as those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). is there.
- the alkyl group having 1 to 10 carbon atoms, which may have a substituent, represented by R 10 and R 11 includes R 1 and R 2 Among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by the following: Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include an aryl group having 6 to 20 carbon atoms represented by R 1 and R 2 And the groups exemplified as Examples of the aryloxy group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy 4-methylphenyloxy, 4-vinylphenyldioxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hex
- arylthio group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 is an arylthio group having 6 to 20 carbon atoms which may have the above-mentioned substituent.
- the arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, represented by R 10 and R 11 , may have 6 to 20 carbon atoms which may have the above-mentioned substituent.
- Examples of the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 11 in the general formula (2) include an n-valent bond represented by X 1 in the general formula (IA).
- those satisfying the predetermined number of carbon atoms include trivalent groups substituted with Z 1 , Z 2 and Z 3 , etc.
- Examples of the trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by Y 11 in the general formula (2) include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2- Adamantyl, noradamantyl, 2-methyladamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydroanthracenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.
- Examples of the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 11 include the trivalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Of the aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). And those that satisfy the number of atoms.
- Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y 11 include the trivalent complex exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
- the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 12 in the general formula (3) is an n-valent aliphatic hydrocarbon group represented by X 1 in the general formula (IA).
- X 1 n-valent aliphatic hydrocarbon group represented by X 1 in the general formula (IA).
- Examples of the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 12 include the monovalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA). To a trivalent aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA).
- Examples of the tetravalent heterocyclic group having 2 to 35 carbon atoms represented by Y 12 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
- a valent heterocyclic ring-containing group and a tetravalent group derived from these groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA).
- those satisfying a predetermined number of carbon atoms can be mentioned.
- the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 13 in the general formula (4) is an n-valent bond represented by X 1 in the general formula (IA).
- the monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and these groups are substituted by those exemplified as the substituents of the n-valent linking group represented by X 1 in the general formula (IA).
- the pentavalent groups derived from these groups those satisfying a predetermined number of carbon atoms, etc.
- the pentavalent aromatic group-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 is a monovalent group exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
- Examples of the pentavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
- a valent heterocyclic ring-containing group and a pentavalent group derived from these groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA).
- the groups those satisfying a predetermined number of carbon atoms can be mentioned.
- the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 14 in the general formula (5) is an n-valent bond represented by X 1 in the general formula (IA).
- the monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and these groups are substituted by those exemplified as the substituents of the n-valent linking group represented by X 1 in the general formula (IA).
- the hexavalent groups derived from these groups those satisfying a predetermined number of carbon atoms, etc.
- the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 is a monovalent group exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
- X 1 n-valent linking group represented by X 1 in the general formula (IA)
- Examples of the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
- the groups those satisfying a predetermined number of carbon atoms can be mentioned.
- each of R 82 , R 83 and R 84 independently has a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or a substituent, which may have 1 carbon atom.
- R 92 and R 93 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms, which may have a substituent, Represents an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms, wherein R 1 and R 2 are the same as those in the above general formula (I) .)
- R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group,
- Y 1 , Z 1 and Z 2 are the same as those in the general formula (1).
- the aryl group the arylalkyl group having 7 to 20 carbon atoms, and the heterocycle-containing group having 2 to 20 carbon atoms, those exemplified in the description of R 1 and R 2 in the general formula (I) can be given. .
- Examples of the arylalkyl group having 7 to 20 carbon atoms and the heterocyclic ring-containing group having 2 to 20 carbon atoms include those exemplified in the description of R 1 and R 2 in the general formula (I).
- Examples of the alkyl group having 1 to 40 atoms, the aryl group having 6 to 20 carbon atoms, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic-containing group having 2 to 20 carbon atoms include those represented by the general formula (I).
- the thing illustrated by description of R ⁇ 1 > and R ⁇ 2 > in can be mentioned.
- R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, and R 2 is a hydrogen atom;
- R 82 , R 83 and R 84 are each independently a hydrogen atom,
- An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, a heterocyclic-containing group having 1 to 10 carbon atoms, particularly R 82 , R 83 and R 84 are preferably an alkyl group having 1 to 4 carbon atoms or a heterocyclic ring-containing group having 1 to 10 carbon atoms.
- R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, and R 2 is a hydrogen atom;
- R 92 and R 93 are each independently a hydrogen atom or carbon atom number
- An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, a heterocyclic-containing group having 1 to 10 carbon atoms, particularly R 92 or R 93 Is preferably an alkyl group having 1 to 4 carbon atoms or a heterocyclic-containing group having 1 to 10 carbon atoms.
- Y 10 is a sulfur atom, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, the number of carbon atoms 2 to 21 divalent heterocyclic ring-containing groups, divalent groups derived from 2,4,8,10-tetraoxaspiro [5,5] undecane, particularly alkylene groups having 1 to 15 carbon atoms, A divalent aromatic ring-containing hydrocarbon group having 6 to 15 carbon atoms and a divalent group derived from 2,4,8,10-tetraoxaspiro [5,5] undecane are preferred, Z 1 and Z 2 are a direct bond, —CO—O—, —O—CO—, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or 6 to 10 carbon atoms.
- an aromatic hydrocarbon group particularly an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent
- Y 11 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or a carbon atom
- Z 1 , Z 2 and Z 3 are preferably the same as Z 1 and Z 2
- Y 12 is preferably a tetravalent group corresponding to the group listed above as preferred Y 11 , Z 1 to Z 4 are preferably
- the production method of the compound having a substituent represented by the above general formula (I) is not particularly limited.
- JP-A-57-111375, JP-A-3-173843, JP-A-6-128195, JP-A-6-128195 It can be obtained by reacting a phenolic compound produced by the methods described in JP-A-7-206871, JP-A-7-252191 and JP-T-2004-501128 with an allyl halide compound.
- the compound having a substituent represented by the general formula (I) can be used as a latent additive in the photosensitive composition of the present invention.
- the latent additive is inactive in a pre-bake process at room temperature or 150 ° C. or less, for example 150 ° C. or less, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst. By heating, the protecting group is eliminated and becomes active.
- the content of the compound having a substituent represented by the general formula (I) as a latent additive is 0.001 to 20 in the solid content of the composition of the present invention. % By mass is preferable, and 0.005 to 5% by mass is more preferable.
- the photosensitive composition of the present invention is a composition whose properties are changed by light irradiation.
- a positive resist is one that is soluble in a chemical reaction
- a negative resist is one that is insoluble in a chemical reaction.
- the photosensitive composition of the present invention contains a compound having a substituent represented by the above general formula (I) as a latent antioxidant, a polymerizable compound having an ethylenically unsaturated bond having an acid value, and light.
- a radical polymerization initiator is contained as an essential component.
- Examples of the polymerizable compound having an ethylenically unsaturated bond having an acid value include (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, and isocrotonic acid.
- X 41 is a direct bond, an alkylene group having 1 to 4 carbon atoms which may have a substituent, or an alicyclic group having 3 to 20 carbon atoms which may have a substituent.
- Hydrocarbon group, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO— or a substitution represented by the above (1-1) to (1-3) Represents a group, R 41 , R 42 , R 43 and R 44 each independently have a hydrogen atom, a substituent or a C 1-5 alkyl group or a substituent.
- polymerizable compounds having an ethylenically unsaturated bond having an acid value can be used alone or in admixture of two or more, and are polymerizable having an ethylenically unsaturated bond having no acid value. It can be used in combination with a compound. When two or more kinds are mixed and used, they may be copolymerized in advance and used as a copolymer.
- the content of the polymerizable compound having an ethylenically unsaturated bond having an acid value is preferably 20 to 80% by mass in the solid content of the composition of the present invention. More preferred is 30 to 70% by mass.
- Examples of the polymerizable compound having an ethylenically unsaturated bond having no acid value include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, The following compound No. A1-No.
- A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (
- a monofunctional or polyfunctional epoxy compound can be used together with the polymerizable compound having an ethylenically unsaturated bond having the acid value.
- the polymerizable compound having an ethylenically unsaturated bond having an acid value preferably has a solid content acid value of 5 to 120 mgKOH / g, and the amount of the monofunctional or polyfunctional epoxy compound used is It is preferable to select so as to satisfy the value.
- Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
- the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a photosensitive composition with better characteristics can be obtained.
- the bisphenol type epoxy compound an epoxy compound represented by the above general formula (III) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used.
- glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
- novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; hetero
- the photo radical polymerization initiator may be any compound that can initiate radical polymerization upon receiving light irradiation.
- ketones such as acetophenone compounds, benzyl compounds, benzophenone compounds, thioxanthone compounds, etc.
- preferred compounds include oxime compounds and oxime compounds.
- acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, and 2-hydroxymethyl-2.
- benzylic compound examples include benzyl and anisyl.
- benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like.
- thioxanthone compound examples include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
- oxime compound a compound represented by the following general formula (IV) or (V) is particularly preferable from the viewpoint of sensitivity and heat resistance.
- R 51 and R 52 each independently have a hydrogen atom, a cyano group, a substituent, or an alkyl group having 1 to 20 carbon atoms or a substituent.
- a certain aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent or a complex having 2 to 20 carbon atoms which may have a substituent Represents a ring-containing group
- R 53 and R 54 are each independently a halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, R 55 , OR 56 , SR 57 , NR 58 R 59 , COR 60 , SOR 61 , SO 2 R 62 or CONR 63 R 64 , R 53 and R 54 may combine with each other to form a ring, R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62
- alkyl groups aryl groups having 6 to 30 carbon atoms which may have substituents
- arylalkyl groups having 7 to 30 carbon atoms which may have substituents or substituents
- X 3 represents an oxygen atom, a sulfur atom, a selenium atom, CR 75 R 76 , CO, NR 77 or PR 78
- X 4 represents a single bond or CO
- R 75 to R 78 represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and methylene in the alkyl group or arylalkyl group
- the group may be replaced by a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a heterocyclic group, or may be replaced
- R 101 and R 102 each independently represent R 111 , OR 111 , COR 111 , SR 111 , CONR 112 R 113 or CN;
- R 111 , R 112 and R 113 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom.
- R 111 , R 112 and R 113 Represents a heterocyclic-containing group of formula 2 to 20,
- the hydrogen atoms of the groups represented by R 111 , R 112 and R 113 are further R 121 , OR 121 , COR 121 , SR 121 , NR 122 R 123 , CONR 122 R 123 , —NR 122 —OR 123 , —NCOR 122.
- R 121 , R 122 and R 123 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom Represents a heterocyclic-containing group of formula 2 to 20,
- the hydrogen atom of the group represented by R 121 , R 122 and R 123 may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group,
- the alkyl part of the group represented by R 111 , R 112 , R 113 , R 121 , R 122 , R 123 and R 124 may have a branched side chain or a cyclic alkyl.
- R 103 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic ring-containing group having 2 to 20 carbon atoms.
- the alkyl part of the group represented by R 103 may have a branched side chain or may be a cyclic alkyl, and R 103 and R 107 , R 103 and R 108 , R 104 and R 105 , R 105 and R 106 and R 106 and R 107 may be combined to form a ring, Hydrogen atoms in the group represented by R 103 may further R 121, OR 121, COR 121 , SR 121, NR 122 R 123, CONR 122 R 123, -NR 122 -OR 123, -NCOR 122 -OCOR 123, NR 122 COR 121 , OCOR 121 , COOR 121 , SCOR 121 , OCSR 121 , COSR 121 , CSOR 121 , hydroxyl group, nitro group, CN, halogen atom, or COOR 121 may be substituted, R 104 , R 105 , R 106 and R
- radical photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pyr-1-yl)] titanium Etc.
- photo radical polymerization initiators can be used alone or in combination of two or more according to the desired performance.
- the content of the radical photopolymerization initiator as described above is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass, based on the solid content of the photosensitive composition of the present invention.
- the content of the photo radical polymerization initiator is less than 0.1% by mass, curing by exposure may be insufficient, and when it is greater than 30% by mass, the initiator is precipitated in the photosensitive composition. There is.
- the photosensitive composition of the present invention can be made into a colored photosensitive composition by further adding a colorant.
- the cured product of the colored photosensitive composition is suitably used as a color filter.
- the addition amount of the colorant is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass in the solid content of the colored photosensitive composition of the present invention. .
- the content of the colorant is less than 0.01% by mass, desired chromaticity may not be obtained.
- the colorant may be precipitated in the colored photosensitive composition. .
- the colorant examples include dyes and pigments.
- the dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm.
- inorganic pigments or organic pigments can be used.
- inorganic pigment or organic pigment commercially available pigments can also be used.
- a solvent can be further added to the photosensitive composition and the colored photosensitive composition of the present invention.
- the solvent is usually a solvent that can dissolve or disperse each of the above components as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, etc.
- Ketones such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate Ester solvents such as n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellosolv solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; methanol Alcohol solvents such as ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol, diacetone alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-a
- ketones, ether ester solvents, etc. particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because the compatibility of the resist and the radical photopolymerization initiator is good in the photosensitive composition.
- a solvent it is preferable from the viewpoint of handling and the like that the solid content of the photosensitive composition or colored photosensitive composition of the present invention is 25 to 35% by mass.
- the photosensitive composition and the colored photosensitive composition of the present invention can further contain an inorganic compound.
- the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Etc.
- a dispersant can be added.
- the dispersant is not particularly limited as long as it can disperse and stabilize colorants and inorganic compounds, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used and have a basic functional group.
- Polymer dispersing agent comprising polyester, polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / Those having g are preferably used.
- the photosensitive composition and the colored photosensitive composition of the present invention include, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, and phenothiazine; plasticizers; Agents; fillers; antifoaming agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; Conventional additives such as an agent, a catalyst, an effect promoter, a cross-linking agent, and a thickener can be added.
- thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, and phenothiazine
- plasticizers Agents
- Fillers such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants
- UV absorbers such as phenolic antioxidants, phos
- the characteristics of the cured product of the photosensitive composition of the present invention and the colored photosensitive composition are improved by using another organic polymer together with the polymerizable compound having an ethylenically unsaturated bond having the acid value.
- the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
- Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
- polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included. Masui.
- a chain transfer agent a sensitizer, a surfactant, a silane coupling agent, a melamine compound, and the like can be further used in combination.
- a sulfur atom-containing compound is generally used.
- Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
- the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
- fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
- anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
- silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, KBE-9007, KBM-502, KBE-403 and the like, silane cups having an isocyanate group, a methacryloyl group, and an epoxy group. A ring agent is preferably used.
- Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
- examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same or different.
- methylol groups that are not alkyl etherified may be self-condensed within one molecule or may be condensed between two molecules, resulting in the formation of an oligomer component.
- hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
- alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
- the photosensitive composition and colored photosensitive composition of the present invention are prepared by known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, and semiconductor substrate. It can be applied on a supporting substrate such as metal, paper, and plastic. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
- the active light source used for curing the photosensitive composition and the colored photosensitive composition of the present invention those capable of emitting light having a wavelength of 300 to 450 nm can be used.
- Mercury vapor arc, carbon arc, xenon arc, etc. can be used.
- the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
- the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
- the photosensitive composition and the colored photosensitive composition of the present invention can also be patterned through a double patterning process in which patterning is performed twice using two photosensitive compositions or colored photosensitive compositions.
- the method of curing the photosensitive composition or colored photosensitive composition of the present invention is a known method such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, It includes a step of forming a coating film on a supporting substrate such as quartz glass, semiconductor substrate, metal, paper, plastic, and the like, and a step of exposing the coating film to exposure and curing the active light.
- the photosensitive composition and the colored photosensitive composition (or cured product thereof) of the present invention are a photocurable paint or varnish, an adhesive such as a photocurable adhesive, a printed circuit board, a color television, a PC monitor, or portable information.
- Color filters for color display liquid crystal display panels such as terminals and digital cameras, color filters for CCD image sensors, photo spacers, black column spacers, electrode materials for plasma display panels, touch panels, touch sensors, powder coatings, printing inks, printing To produce plates, dental compositions, stereolithography resins, gel coats, photoresists for electronics, electroplating resists, etching resists, both liquid and dry films, solder resists, and color filters for various display applications Or plasma display panel, electroluminescent display, and LC Resist for forming structures in the manufacturing process, composition for encapsulating electrical and electronic components, solder resist, magnetic recording materials, micromechanical components, waveguide, optical switch, plating mask, etching mask, color test Systems, glass fiber cable coatings, stencils
- the photosensitive composition of the present invention can be used as a transparent structure by curing.
- transparent structures include columnars called photo spacers (PS) and column spacers (CS); fine patterns of (nano) imprints; production of large advertising signs, color filters for liquid crystal displays, and alignment films
- PS photo spacers
- CS column spacers
- fine patterns of (nano) imprints production of large advertising signs, color filters for liquid crystal displays, and alignment films
- Examples thereof include an ink jet receiving layer used for manufacturing electronic devices such as printing.
- the transparent structure of the present invention is suitably used for display devices.
- the photosensitive composition of the present invention can be used for a transparent conductive film, a reflective film, a polarizing plate, a protective film, and the like, and each desired layer is sequentially applied to a transparent substrate and activated through a mask having a predetermined pattern shape. It can be used as a transparent laminate obtained by irradiating light, developing the exposed film with a developer, and heating the developed film. As a transparent laminated body, the thing etc. with which the transparent thin film layer and metal thin film layer which consist of a complex oxide of an indium oxide and a cerium oxide are alternated on the transparent base material are mentioned, for example.
- the photosensitive composition of the present invention containing a compound having a substituent represented by the general formula (I) as a latent additive may be used for each of the above-described layers, and the photosensitive composition may be used for any of the layers.
- a composition may be used.
- the transparent laminate is suitably used for a display device.
- the colored photosensitive composition of the present invention is used for the purpose of forming pixels of a color filter, and is particularly useful as a photosensitive composition for forming a color filter for a display device for an image display device such as a liquid crystal display panel. is there.
- the color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition of the present invention on a substrate, and (2) active light through a mask having a predetermined pattern shape on the coating film.
- the step of irradiating, (3) the step of developing the film after exposure with a developer, and (4) the step of heating the film after development are preferably formed.
- the colored photosensitive composition of the present invention is also useful as an inkjet-type colored photosensitive composition without a development step.
- a multi-tone mask such as a halftone mask or a gray scale mask can be used.
- novel compound of the present invention is represented by any of the following structures.
- the production method of the novel compound of the present invention is not particularly limited.
- a phenolic compound produced by the method described in each publication of JP-A-2004-501128 and an allyl halide compound can be obtained.
- novel compound of the present invention can be used as a latent antioxidant, a latent ultraviolet absorber, a dissolution regulator and the like.
- Example 1-1 Compound No. 1 Synthesis of Compound 1 Potassium carbonate (2 equivalents with respect to one phenol group) was added to a dimethylacetamide solution of 1 equivalent of 1 ′ phenol compound (3 times the theoretical yield), and the mixture was stirred at room temperature for 30 minutes. Allyl bromide (1.5 equivalent to one phenol group) was added, and the mixture was stirred at 60 ° C. for 5 hours. After adding ethyl acetate and washing with 1% hydrochloric acid solution, oil-water separation was performed, and after drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and crystallization was performed. The obtained solid was dried under reduced pressure at 60 ° C. for 3 hours to obtain the desired product. It was confirmed by 1 H-NMR and IR that the obtained solid was the desired product. The results are shown in [Table 1] to [Table 2].
- Example 1-1 Compound No. Synthesis of 2 to 6
- the following compound No. instead of the phenol compound of 1 ′, the following compound No.
- the target compound No. 2 was prepared in the same manner as in Example 1-1, except that 2 ′ to 6 ′ phenolic compounds were used. 2-6 were synthesized. It was confirmed by 1 H-NMR and IR that the obtained solid was the desired product. The results are shown in [Table 1] to [Table 2].
- Example 2-1 and Comparative Evaluation Examples 2-1 and 2-2 Solvent Resistance Evaluation
- the photosensitive composition No. obtained in Example 2-1 was used.
- Comparative photosensitive composition Nos. 1 and 2 obtained in Comparative Examples 2-1 and 2-3. 1 and no. 3 were each coated on a glass substrate under conditions of 410 rpm ⁇ 7 seconds and dried on a hot plate (90 ° C. ⁇ 90 seconds).
- the obtained coating film was exposed (40 mJ / cm 2 ) with an ultrahigh pressure mercury lamp.
- the exposed coating film was baked under conditions of 230 ° C. ⁇ 30 minutes.
- the film thickness of the obtained coating film After measuring the film thickness of the obtained coating film, it was immersed in PGMEA, cyclohexanone, N-methylpyrrolidone, and N-ethylpyrrolidone at room temperature for 30 minutes, and the film thickness after immersion was measured. It was evaluated that the solvent resistance was higher as the film thickness ratio before and after immersion (film thickness after immersion ⁇ 100 / film thickness before immersion) was closer to 100%.
- comparative photosensitive composition No. containing no antioxidant was used.
- a comparative photosensitive composition No. 1 containing a conventional phenolic antioxidant was used.
- the photosensitive composition No. 1 using the compound according to the present application as a latent additive was used. It is clear that No. 1 maintains the same solvent resistance as when no antioxidant is contained.
- the photosensitive composition using the compound of the present invention as a latent additive has less outgas and the cured product is excellent in solvent resistance.
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Abstract
Description
R1及びR2で表されるアルキル基又はアリールアルキル基中のメチレン基は、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR’-、-S-S-又は-SO2-から選ばれた基を酸素原子が隣り合わない条件で組み合わせた基で置き換えている場合もあり、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
jは、1~3の数を表し、
*は、*部分で、隣接する基と結合することを意味する。)
The methylene group in the alkyl group or arylalkyl group represented by R 1 and R 2 is —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—. O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—. , -NR '-, - S- S- or -SO 2 - from selected based on some cases where the oxygen atoms are replaced by a group composed of a combination under conditions which are not adjacent, R' is a hydrogen atom or a carbon atom Represents an alkyl group of 1 to 8,
j represents a number from 1 to 3,
* Means that it is bonded to an adjacent group at the * part. )
X1は、n価の結合基を表し、
R1、R2及びjは、上記一般式(I)と同じである。)
X 1 represents an n-valent linking group,
R 1 , R 2 and j are the same as in the general formula (I). )
R1及びR2で表される炭素原子数1~20のアルキル基としては、メチル、エチル、プロピル、iso-プロピル、ブチル、sec-ブチル、tert-ブチル、iso-ブチル、アミル、iso-アミル、tert-アミル、シクロペンチル、ヘキシル、2-ヘキシル、3-ヘキシル、シクロヘキシル、4-メチルシクロヘキシル、ヘプチル、2-ヘプチル、3-ヘプチル、iso-ヘプチル、tert-ヘプチル、1-オクチル、iso-オクチル、tert-オクチル、アダマンチル等が挙げられ、
R1及びR2で表される炭素原子数6~20のアリール基としては、フェニル、ナフチル、アントラセニル、フェナントリル、フルオレニル、インデニル、2-メチルフェニル、3-メチルフェニル、4-メチルフェニル、4-ビニルフェニル、3-iso-プロピルフェニル、4-iso-プロピルフェニル、4-ブチルフェニル、4-iso-ブチルフェニル、4-tert-ブチルフェニル、4-ヘキシルフェニル、4-シクロヘキシルフェニル、4-オクチルフェニル、4-(2-エチルヘキシル)フェニル、4-ステアリルフェニル、2,3-ジメチルフェニル、2,4-ジメチルフェニル、2,5-ジメチルフェニル、2,6-ジメチルフェニル、3,4-ジメチルフェニル、3,5-ジメチルフェニル、2,4-ジ-tert-ブチルフェニル、2,5-ジ-tert-ブチルフェニル、2,6-ジ-tert-ブチルフェニル、2,4-ジ-tert-ペンチルフェニル、2,5-ジ-tert-アミルフェニル、2,5-ジ-tert-オクチルフェニル、2,4-ジクミルフェニル、4-シクロヘキシルフェニル、(1,1’-ビフェニル)-4-イル、2,4,5-トリメチルフェニル、フェロセニル等が挙げられ、
R1及びR2で表される炭素原子数7~20のアリールアルキル基としては、ベンジル、1-メチル-1-フェニルエチル、1-ナフチルメチル、9-アントラセニルメチル、9-フルオレニル、3-フェニルプロピル、メチル-2-フェニルプロパン-2-イル、ジフェニルメチル、トリフェニルメチル、フェネチル、スチリル、シンナミル等が挙げられ、
R1及びR2で表される炭素原子数2~20の複素環含有基としては、ピリジン環、ピリミジン環、ピリダジン環、ピペリジン環、ピラン環、ピラゾリン環、トリアジン環、ピロリン環、キノリン環、イソキノリン環、イミダゾリン環、ベンゾイミダゾリン環、トリアゾリン環、フラン環、ベンゾフラン環、チアジアゾリン環、チアゾリン環、ベンゾチアゾリン環、チオフェン環、オキサゾリン環、ベンゾオキサゾリン環、イソチアゾリン環、イソオキサゾリン環、インドール環、ピロリジン環、ピペリドン環、ジオキサン環等の複素環とメチレン鎖を組み合わせた基が挙げられ、
R1及びR2で表されるトリアルキルシリル基としては、トリメチルシラン、トリエチルシラン、エチルジメチルシラン等の炭素原子数1~6のアルキル基(3つのアルキル基は同一かあるいは異なる)で置換されたシリル基が挙げられる。
R’で表される炭素原子数1~8のアルキル基としては、R1で表される上記アルキル基のうち、所定の炭素原子数を満たすものが挙げられる。
R1及びR2で表される炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を置換する置換基としては、ビニル、アリル、アクリル、メタクリル等のエチレン性不飽和基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;アセチル、2-クロロアセチル、プロピオニル、オクタノイル、アクリロイル、メタクリロイル、フェニルカルボニル(ベンゾイル)、フタロイル、4-トリフルオロメチルベンゾイル、ピバロイル、サリチロイル、オキザロイル、ステアロイル、メトキシカルボニル、エトキシカルボニル、t-ブトキシカルボニル、n-オクタデシルオキシカルボニル、カルバモイル等のアシル基;アセチルオキシ、ベンゾイルオキシ等のアシルオキシ基;アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2-エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N-メチル-アニリノ、ジフェニルアミノ,ナフチルアミノ、2-ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N-ジメチルアミノカルボニルアミノ、N,N-ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t-ブトキシカルボニルアミノ、n-オクタデシルオキシカルボニルアミノ、N-メチル-メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N-ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等の置換アミノ基;スルホンアミド基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、ニトロ基、メルカプト基、イミド基、カルバモイル基、スルホンアミド基、ホスホン酸基、リン酸基又はカルボキシル基、スルホ基、ホスホン酸基、リン酸基の塩等が挙げられる。
R1及びR2としては、水素原子、炭素原子数1~8のアルキル基、炭素原子数6~12のアリール基が、アウトガスが少ないため好ましい。R1及びR2が水素原子又は分岐を有する炭素原子数1~8のアルキル基、特にt-ブチル基の何れかであるものが、アウトガスが少ないためさらに好ましい。 Examples of the halogen atom represented by R 1 and R 2 include fluorine, chlorine, bromine and iodine.
Examples of the alkyl group having 1 to 20 carbon atoms represented by R 1 and R 2 include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl Tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl, adamantyl and the like,
Examples of the aryl group having 6 to 20 carbon atoms represented by R 1 and R 2 include phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4- Vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-ter -Butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2, 5-di-tert-octylphenyl, 2,4-dicumylphenyl, 4-cyclohexylphenyl, (1,1′-biphenyl) -4-yl, 2,4,5-trimethylphenyl, ferrocenyl, etc.
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 1 and R 2 include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 9-anthracenylmethyl, 9-fluorenyl, 3 -Phenylpropyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl and the like,
Examples of the heterocyclic group containing 2 to 20 carbon atoms represented by R 1 and R 2 include a pyridine ring, a pyrimidine ring, a pyridazine ring, a piperidine ring, a pyran ring, a pyrazoline ring, a triazine ring, a pyrroline ring, a quinoline ring, Isoquinoline ring, imidazoline ring, benzimidazoline ring, triazoline ring, furan ring, benzofuran ring, thiadiazoline ring, thiazoline ring, benzothiazoline ring, thiophene ring, oxazoline ring, benzoxazoline ring, isothiazoline ring, isoxazoline ring, indole ring, pyrrolidine Examples include groups combining heterocycles such as rings, piperidone rings, dioxane rings and methylene chains,
The trialkylsilyl group represented by R 1 and R 2 is substituted with an alkyl group having 1 to 6 carbon atoms (three alkyl groups are the same or different) such as trimethylsilane, triethylsilane, and ethyldimethylsilane. And silyl group.
Examples of the alkyl group having 1 to 8 carbon atoms represented by R ′ include those satisfying a predetermined number of carbon atoms among the above alkyl groups represented by R 1 .
Containing an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic ring having 2 to 20 carbon atoms represented by R 1 and R 2 Substituents for substituting groups include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl and methacryloyl Acyl groups such as phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl; Benzoylo Acyloxy group such as amino; amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino , Methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarboni Substituted amino groups such as ruamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N, N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino; sulfonamide group, sulfonyl Group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, carbamoyl group, sulfonamide group, phosphonic acid group, phosphoric acid group or carboxyl group, sulfo group, phosphonic acid group, phosphoric acid group And the like.
As R 1 and R 2 , a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an aryl group having 6 to 12 carbon atoms are preferable because of less outgassing. It is more preferable that R 1 and R 2 are either a hydrogen atom or a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, because outgas is small.
但し、X1が窒素原子、リン原子又は下記(I-a)若しくは(I-b)で表される結合基の場合、nは3であり、X1が酸素原子又は硫黄原子、-CO-、-NH-CO-、-CO-NH-又は-NR3-の場合、nは2であり、X1が水素原子、-OR3、-SR3又は-NR3R4の場合、nは1であり、X1は、ベンゼン環と一緒になって環を形成している場合もある。 In the general formula (IA), X 1 represents an n-valent linking group. Specifically, for example, a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, the following (I -a) or (I-b), a group represented by, -CO -, - NH-CO -, - CO-NH -, - NR 3 -, - oR 3, -SR 3, -NR 3 R 4, Or an aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent having the same valence as n, and 6 to 35 carbon atoms which may have a substituent. Represents an aromatic ring-containing hydrocarbon group or a heterocyclic group having 2 to 35 carbon atoms, which may have a substituent, and R 3 and R 4 have a hydrogen atom or a substituent. In some cases, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, or an aromatic hydrocarbon group having 6 to 35 carbon atoms that may have a substituent. Represents a ring-containing hydrocarbon group or a heterocyclic group having 2 to 35 carbon atoms, which may have a substituent, and the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocyclic ring-containing group are carbon -Carbon double bond, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —O—CO—NH—, —NR′—, — In some cases, the group is replaced with a group selected from S—S—, —SO 2 — or a nitrogen atom.
However, when X 1 is a nitrogen atom, a phosphorus atom, or a linking group represented by the following (Ia) or (Ib), n is 3, X 1 is an oxygen atom or a sulfur atom, —CO— , —NH—CO—, —CO—NH— or —NR 3 —, n is 2, and when X 1 is a hydrogen atom, —OR 3 , —SR 3 or —NR 3 R 4 , n is 1 and X 1 may form a ring together with the benzene ring.
nが2価のものとして、メチレン、エチレン、プロピレン、ブチレン、ブチルジイル等のアルキレン;前記アルキレンのメチレン鎖が-O-、-S-、-CO-O-、-O-CO-で置き換えられたもの;エタンジオール、プロパンジオール、ブタンジオール、ペンタンジオール、ヘキサンジオール等のジオールの残基;エタンジチオール、プロパンジチオール、ブタンジチオール、ペンタンジチオール、ヘキサンジチオール等のジチオールの残基;及びこれらの基が後述する置換基により置換された基等が挙げられ、
nが3価のものとして、例えば、プロピリジン、1,1,3-ブチリジン等のアルキリジン;及びこれらの基が後述する置換基により置換された基が挙げられる。
nと同数の価数を有する、置換基を有している場合もある炭素原子数6~35の芳香環含有炭化水素基としては、nが1価のものとして、ベンジル、フェネチル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル等のアリールアルキル基;フェニル、ナフチル等のアリール基;フェノキシ、ナフチルオキシ等のアリールオキシ基;フェニルチオ、ナフチルチオ等のアリールチオ基;及びこれらの基が後述する置換基により置換された基等が挙げられ、
nが2価のものとして、フェニレン、ナフチレン等のアリーレン基;カテコール、ビスフェノール等の二官能フェノールの残基;2,4,8,10-テトラオキサスピロ[5,5]ウンデカン等;及びこれらの基が後述する置換基により置換された基が挙げられ、
nが3価のものとして、フェニル-1,3,5-トリメチレン及びこれらの基が後述する置換基により置換された基が挙げられる。
nと同数の価数を有する、置換基を有している場合もある炭素原子数2~35の複素環含有基としては、nが1価のものとして、ピリジル、ピリミジル、ピリダジル、ピペリジル、ピラニル、ピラゾリル、トリアジル、ピロリル、キノリル、イソキノリル、イミダゾリル、ベンゾイミダゾリル、トリアゾリル、フリル、フラニル、ベンゾフラニル、チエニル、チオフェニル、ベンゾチオフェニル、チアジアゾリル、チアゾリル、ベンゾチアゾリル、オキサゾリル、ベンゾオキサゾリル、イソチアゾリル、イソオキサゾリル、インドリル、2-ピロリジノン-1-イル、2-ピペリドン-1-イル、2,4-ジオキシイミダゾリジン-3-イル、2,4-ジオキシオキサゾリジン-3-イル、ベンゾトリアゾイル等;及びこれらの基が後述する置換基により置換された基等が挙げられ、
nが2価のものとして、ピリジン環、ピリミジン環、ピペリジン環、ピペラジン環、トリアジン環、フラン環、チオフェン環、インドール環等を有する基;及びこれらの基が後述する置換基により置換された基が挙げられ、
nが3価のものとしては、イソシアヌル環を有する基、トリアジン環を有する基;及びこれらの基が後述する置換基により置換された基が挙げられる。
R3及びR4で表される、置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基としては、上記X1で表される脂肪族炭化水素基及び該脂肪族炭化水素基と上記置換基との組み合わせのうち、所定の炭素原子数を満たすものが挙げられ、
R3及びR4で表される、置換基を有している場合もある炭素原子数6~35の芳香環含有炭化水素基及び置換基を有している場合もある炭素原子数2~35の複素環含有基としては、上記X1で表される炭素原子数6~35の芳香環含有炭化水素基及び炭素原子数2~35の複素環含有基並びにこれらの基と後述する置換基とを組み合わせた基のうち、所定の炭素原子数を満たすものが挙げられる。
置換基としては、ビニル、アリル、アクリル、メタクリル等のエチレン性不飽和基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;アセチル、2-クロロアセチル、プロピオニル、オクタノイル、アクリロイル、メタクリロイル、フェニルカルボニル(ベンゾイル)、フタロイル、4-トリフルオロメチルベンゾイル、ピバロイル、サリチロイル、オキザロイル、ステアロイル、メトキシカルボニル、エトキシカルボニル、t-ブトキシカルボニル、n-オクタデシルオキシカルボニル、カルバモイル等のアシル基;アセチルオキシ、ベンゾイルオキシ等のアシルオキシ基;アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2-エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N-メチル-アニリノ、ジフェニルアミノ、ナフチルアミノ、2-ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N-ジメチルアミノカルボニルアミノ、N,N-ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t-ブトキシカルボニルアミノ、n-オクタデシルオキシカルボニルアミノ、N-メチル-メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N-ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等の置換アミノ基;スルホンアミド基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、ニトロ基、メルカプト基、イミド基、カルバモイル基、スルホンアミド基、ホスホン酸基、リン酸基又はカルボキシル基、スルホ基、ホスホン酸基、リン酸基の塩等が挙げられ、これらの基は更に置換されている場合もある。また、カルボキシル基及びスルホ基は塩を形成している場合もある。 The aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent represented by X 1 in the general formula (IA) and having the same valence as n is n Are monovalent, for example, methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3- Alkyl such as hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl, decyl Groups: methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, 2-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tert-heptyloxy, n-octyloxy, isooctyloxy, tert-octyloxy Alkoxy groups such as 2-ethylhexyloxy, nonyloxy, decyloxy; methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio, isobutylthio, amylthio, isoamylthio, tert-amylthio, hexylthio, cyclohexylthio, Alkylthio groups such as heptylthio, isoheptylthio, tertiary heptylthio, n-octylthio, isooctylthio, tertiary octylthio, 2-ethylhexylthio; Vinyl, 1-methylethenyl, 2-methylethenyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, bicyclohexenyl, Alkenyl groups such as heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, tricosenyl; and groups in which these groups are substituted with substituents described later, and the like,
n is divalent, alkylene such as methylene, ethylene, propylene, butylene, butyldiyl; the methylene chain of the alkylene is replaced by —O—, —S—, —CO—O—, —O—CO— Residues of diols such as ethanediol, propanediol, butanediol, pentanediol, hexanediol; residues of dithiols such as ethanedithiol, propanedithiol, butanedithiol, pentanedithiol, hexanedithiol; and these groups are described later Groups substituted by substituents to
Examples of those in which n is trivalent include alkylidines such as propyridine and 1,1,3-butyridine; and groups in which these groups are substituted with substituents described later.
Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, which may have a substituent having the same valence as n, are those in which n is monovalent, such as benzyl, phenethyl, diphenylmethyl, Arylalkyl groups such as triphenylmethyl, styryl and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio; and these groups are substituted by substituents described later Group, etc.
n is divalent, arylene groups such as phenylene and naphthylene; residues of bifunctional phenols such as catechol and bisphenol; 2,4,8,10-tetraoxaspiro [5,5] undecane and the like; A group in which the group is substituted by a substituent described later,
Examples of the trivalent n include phenyl-1,3,5-trimethylene and groups in which these groups are substituted with a substituent described later.
The heterocycle-containing group having 2 to 35 carbon atoms that may have a substituent having the same number of valences as n includes those in which n is monovalent, pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl , Pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyoxazolidine-3-yl, benzotriazoyl, etc .; and these groups Will be described later Groups substituted by substituent can be mentioned,
a group having a pyridine ring, a pyrimidine ring, a piperidine ring, a piperazine ring, a triazine ring, a furan ring, a thiophene ring, an indole ring or the like, and a group in which these groups are substituted by a substituent described later, Are mentioned,
Examples of the group in which n is trivalent include a group having an isocyanuric ring, a group having a triazine ring; and a group in which these groups are substituted with a substituent described later.
Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 3 and R 4 include the aliphatic hydrocarbon group represented by X 1 and the aliphatic hydrocarbon group. Among the combinations of group hydrocarbon groups and the above substituents, those satisfying a predetermined number of carbon atoms can be mentioned,
The aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent represented by R 3 and R 4 and 2 to 35 carbon atoms which may have a substituent Examples of the heterocyclic ring-containing group include an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms and a heterocyclic ring-containing group having 2 to 35 carbon atoms represented by the above X 1 and these groups and substituents described later. Among the groups in which are combined, those satisfying a predetermined number of carbon atoms can be mentioned.
Examples of the substituent include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl and phenylcarbonyl ( Benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl, etc .; acetyloxy, benzoyloxy, etc. Acyloxy group; amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chloro Enylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino, N, N -Dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino Sulfamoylamino, N, N-dimethylaminosulfonylamino, methylsulfonylamino, butyls Substituted amino groups such as phonylamino, phenylsulfonylamino, etc .; sulfonamide groups, sulfonyl groups, carboxyl groups, cyano groups, sulfo groups, hydroxyl groups, nitro groups, mercapto groups, imide groups, carbamoyl groups, sulfonamide groups, phosphonic acid groups, phosphorus Examples thereof include salts of acid groups or carboxyl groups, sulfo groups, phosphonic acid groups, and phosphoric acid groups, and these groups may be further substituted. In addition, the carboxyl group and the sulfo group may form a salt.
(1)~(5)のように表すこともできる。 In the above general formula (IA), when n is 2 to 6, X 1 can also be represented by the following general formulas (1) to (5), respectively.
該脂肪族炭化水素基は、-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-若しくは-NHCO-、又は酸素原子が隣り合うことなしにこれらを組み合わせた結合基で置き換えられている場合もあり、
Z1及びZ2は、それぞれ独立に、直接結合、-O-、-S-、>CO、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、-NR7-又は-PR7-を表し、
R5、R6及びR7は、それぞれ独立に、水素原子、置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合もある炭素原子数6~35の芳香族炭化水素基又は置換基を有している場合もある炭素原子数2~35の複素環含有基を表し、
*は、*部分で、隣接する基と結合することを意味する。)
The aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom. In some cases, it is replaced with a combination of these without combining,
Z 1 and Z 2 are each independently a direct bond, —O—, —S—,> CO, —CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—, Represents —NR 7 — or —PR 7 —,
R 5 , R 6 and R 7 may each independently have a hydrogen atom, a substituent, or an aliphatic hydrocarbon group having 1 to 35 carbon atoms or a substituent. Represents an aromatic hydrocarbon group having 6 to 35 carbon atoms or a heterocyclic group having 2 to 35 carbon atoms which may have a substituent,
* Means that it is bonded to an adjacent group at the * part. )
R9は炭素原子数1~10のアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数2~10のアルケニル基又はハロゲン原子を表し、上記アルキル基、アルコキシ基及びアルケニル基は置換基を有している場合もあり、
fは0~5の整数であり、
*は、*部分で、隣接する基と結合することを意味する。)
R 9 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen atom, and the alkyl group, alkoxy group and alkenyl group are substituents. May have
f is an integer from 0 to 5,
* Means that it is bonded to an adjacent group at the * part. )
該アルキル基及びアリールアルキル基中のメチレン基は、不飽和結合、-O-又は-S-で置き換えられている場合もあり、
R10は、隣接するR10同士で環を形成している場合もあり、
pは0~4の数を表し、
qは0~8の数を表し、
gは0~4の数を表し、
hは0~4の数を表し、
gとhの数の合計は2~4であり、
*は、*部分で、隣接する基と結合することを意味する。)
The methylene group in the alkyl group and arylalkyl group may be replaced with an unsaturated bond, —O— or —S—,
R 10 may form a ring with adjacent R 10 ,
p represents a number from 0 to 4,
q represents a number from 0 to 8,
g represents a number from 0 to 4,
h represents a number from 0 to 4,
The total number of g and h is 2-4,
* Means that it is bonded to an adjacent group at the * part. )
Z1、Z2及びZ3は、それぞれ独立に、直接結合、-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、-NR12-又は-PR12-を表し、
R12は、水素原子、置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合もある炭素原子数6~35の芳香族炭化水素基又は置換基を有している場合もある炭素原子数2~35の複素環含有基を表し、
脂肪族炭化水素基は、炭素-炭素二重結合、-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-若しくは-NHCO-、又は酸素原子が隣り合うことなしにこれらを組み合わせた結合基で置き換えられている場合もあり、
*は、*部分で、隣接する基と結合することを意味する。)
Z 1 , Z 2 and Z 3 are each independently a direct bond, —O—, —S—, —CO—, —CO—O—, —O—CO—, —SO 2 —, —SS—, Represents —SO—, —NR 12 — or —PR 12 —,
R 12 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic carbon group having 6 to 35 carbon atoms which may have a substituent. Represents a hydrogen-containing group or a substituent containing 2 to 35 carbon atoms which may have a substituent,
The aliphatic hydrocarbon group includes a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—. Or the oxygen atom may be replaced by a linking group combining these without being adjacent to each other,
* Means that it is bonded to an adjacent group at the * part. )
該脂肪族炭化水素基は、炭素-炭素二重結合、-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-若しくは-NHCO-、又は酸素原子が隣り合うことなしにこれらを組み合わせた結合基で置き換えられている場合もあり、
Z1~Z4は、それぞれ独立に、上記一般式(2)におけるZ1~Z3で表される基と同じ範囲の基であり、
*は、*部分で、隣接する基と結合することを意味する。)
The aliphatic hydrocarbon group is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO. -, Or in some cases, oxygen atoms are replaced by linking groups combining them without being adjacent,
Z 1 to Z 4 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2),
* Means that it is bonded to an adjacent group at the * part. )
該脂肪族炭化水素基は、炭素-炭素二重結合、-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-若しくは-NHCO-、又は酸素原子が隣り合うことなしにこれらを組み合わせた結合基で置き換えられている場合もあり、
Z1~Z5は、それぞれ独立に、上記一般式(2)におけるZ1~Z3で表される基と同じ範囲の基であり、
*は、*部分で、隣接する基と結合することを意味する。)
The aliphatic hydrocarbon group is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO. -, Or in some cases, oxygen atoms are replaced by linking groups combining them without being adjacent,
Z 1 to Z 5 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2),
* Means that it is bonded to an adjacent group at the * part. )
該脂肪族炭化水素基は、炭素-炭素二重結合、-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-若しくは-NHCO-、又は酸素原子が隣り合うことなしにこれらを組み合わせた結合基で置き換えられている場合もあり、
Z1~Z6は、それぞれ独立に、上記一般式(2)におけるZ1~Z3で表される基と同じ範囲の基であり、
*は、*部分で、隣接する基と結合することを意味する。)
The aliphatic hydrocarbon group is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO. -, Or in some cases, oxygen atoms are replaced by linking groups combining them without being adjacent,
Z 1 to Z 6 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2),
* Means that it is bonded to an adjacent group at the * part. )
R5、R6及びR7で表される、置換基を有している場合もある炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価の芳香環含有炭化水素基、及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基を表す基の置換基として例示したものにより置換された基のうち、所定の炭素原子数を満たすもの等が挙げられ、
R5、R6及びR7で表される、置換基を有している場合もある炭素原子数2~35の複素環含有基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価の複素環含有基、及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合を表す基の置換基として例示したものにより置換された基のうち、所定の炭素原子数を満たすもの等が挙げられる。
また、上記一般式(1)においてY1で表される、2価の炭素原子数1~35の脂肪族炭化水素基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した2価の脂肪族炭化水素基、及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基を表す基の置換基として例示したものにより置換された基のうち、所定の炭素原子数を満たすもの等が挙げられ、
Y1で表される2価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した2価の芳香環含有炭化水素基、及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基を表す基の置換基として例示したものにより置換された基のうち、所定の炭素原子数を満たすもの等が挙げられ、
Y1で表される2価の炭素原子数2~35の複素環含有基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した2価の芳香環含有炭化水素基、及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基を表す基の置換基として例示したものにより置換された基のうち、所定の炭素原子数を満たすもの等が挙げられる。 In the general formula (1), the aliphatic hydrocarbon group having 1 to 35 carbon atoms, which may have a substituent, represented by R 5 , R 6 and R 7 includes the above general formula ( The monovalent aliphatic hydrocarbon group exemplified as the n-valent linking group represented by X 1 in IA), and the n valence represented by X 1 in the general formula (IA). Among the groups substituted by those exemplified as the substituent of the group representing the bonding group, those satisfying the predetermined number of carbon atoms, and the like can be mentioned,
Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent represented by R 5 , R 6 and R 7 include X 1 in the above general formula (IA). A monovalent aromatic ring-containing hydrocarbon group exemplified as an n-valent linking group represented by formula (I), and a group in which these groups represent an n-valent linking group represented by X 1 in formula (IA). Among the groups substituted by those exemplified as the substituents in the above, those satisfying a predetermined number of carbon atoms, etc.
The heterocyclic group having 2 to 35 carbon atoms which may have a substituent represented by R 5 , R 6 and R 7 is represented by X 1 in the above general formula (IA). And monovalent heterocycle-containing groups exemplified as the n-valent linking group, and these groups are exemplified as substituents of the group representing the n-valent bond represented by X 1 in the general formula (IA). Among those substituted by the above, those satisfying a predetermined number of carbon atoms can be mentioned.
In addition, the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 1 in the general formula (1) is an n represented by X 1 in the general formula (IA). Examples of the divalent aliphatic hydrocarbon group exemplified as the valent linking group, and substituents of the group representing the n-valent linking group represented by X 1 in the general formula (IA). Among the groups substituted by ones, those satisfying a predetermined number of carbon atoms, etc. are mentioned,
Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 1 include the divalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Of these aromatic ring-containing hydrocarbon groups and groups substituted by those exemplified as the substituents of the group representing the n-valent linking group represented by X 1 in the general formula (IA). And those satisfying a predetermined number of carbon atoms.
Examples of the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y 1 include the divalent aromatic compounds exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Of the ring-containing hydrocarbon groups and groups substituted by those exemplified as the substituents of the group representing the n-valent linking group represented by X 1 in the general formula (IA) And the like satisfying the number of carbon atoms.
R9で表される炭素原子数1~10のアルキル基としては、R1及びR2で表される炭素原子数1~40のアルキル基として例示した基のうち、所定の炭素原子数を満たす基等が挙げられ、
R9で表される炭素原子数1~10のアルコキシ基としては、メチルオキシ、エチルオキシ、プロピルオキシ、イソプロピルオキシ、ブチルオキシ、第二ブチルオキシ、第三ブチルオキシ、イソブチルオキシ、アミルオキシ、イソアミルオキシ、第三アミルオキシ、ヘキシルオキシ、シクロヘキシルオキシ、ヘプチルオキシ、イソヘプチルオキシ、第三ヘプチルオキシ、n-オクチルオキシ、イソオクチルオキシ、第三オクチルオキシ、2-エチルヘキシルオキシ、ノニルオキシ、デシルオキシ等が挙げられ、
フェニル基、シクロアルキル基、アルキル基、アルコキシ基及びアルケニル基の置換基は、上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものと同様である。 In the substituent represented by (1-1) above, examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 8 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like. ,
The alkyl group having 1 to 10 carbon atoms represented by R 9 satisfies the predetermined number of carbon atoms among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 1 and R 2. Groups, etc.
Examples of the alkoxy group having 1 to 10 carbon atoms represented by R 9 include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy Hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, etc.
The substituents of the phenyl group, cycloalkyl group, alkyl group, alkoxy group and alkenyl group are the same as those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). is there.
R10及びR11で表される、置換基を有している場合もある炭素原子数6~20のアリール基としては、R1及びR2で表される炭素原子数6~20のアリール基として例示した基等が挙げられ、
R10及びR11で表される、置換基を有している場合もある炭素原子数6~20のアリールオキシ基としては、フェニルオキシ、ナフチルオキシ、2-メチルフェニルオキシ、3-メチルフェニルオキシ、4-メチルフェニルオキシ、4-ビニルフェニル二オキシ、3-iso-プロピルフェニルオキシ、4-iso-プロピルフェニルオキシ、4-ブチルフェニルオキシ、4-tert-ブチルフェニルオキシ、4-へキシルフェニルオキシ、4-シクロヘキシルフェニルオキシ、4-オクチルフェニルオキシ、4-(2-エチルヘキシル)フェニルオキシ、2,3-ジメチルフェニルオキシ、2,4-ジメチルフェニルオキシ、2,5-ジメチルフェニルオキシ、2.6-ジメチルフェニルオキシ、3.4-ジメチルフェニルオキシ、3.5-ジメチルフェニルオキシ、2,4-ジーtert-ブチルフェニルオキシ、2,5-ジーtert-ブチルフェニルオキシ、2,6-ジーtert-ブチルフェニルオキシ、2.4-ジーtert-ペンチルフェニルオキシ、2,5-tert-アミルフェニルオキシ、4-シクロへキシルフェニルオキシ、2,4,5-トリメチルフェニルオキシ、フェロセニルオキシ等の基が奉げられ、
R10及びR11で表される、置換基を有している場合もある炭素原子数6~20のアリールチオ基としては、上記置換基を有している場合もある炭素原子数6~20のアリールオキシ基の酸素原子を硫黄原子に置換した基等が奉げられ、
R10及びR11で表される、置換基を有している場合もある炭素原子数8~20のアリールアルケニル基としては、上記置換基を有している場合もある炭素原子数6~20のアリールオキシ基の酸素原子をビニル、アリル、1-プロペニル、イソプロペニル、2-ブテニル、1,3-ブタジエニル、2-ペンテニル、2-オクテニル等のアルケニル基で置換した基等が挙げられ、
R10及びR11で表される、置換基を有している場合もある炭素原子数7~20のアリールアルキル基としては、R1及びR2で表される炭素原子数7~20のアリールアルキル基として例示した基等が挙げられ、
R10及びR11で表される、置換基を有している場合もある炭素原子数2~20の複素環含有基としては、R1及びR2で表される炭素原子数2~20の複素環含有基として例示した基等が挙げられる。 In the group represented by (1-3) above, the alkyl group having 1 to 10 carbon atoms, which may have a substituent, represented by R 10 and R 11 includes R 1 and R 2 Among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by the following:
Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include an aryl group having 6 to 20 carbon atoms represented by R 1 and R 2 And the groups exemplified as
Examples of the aryloxy group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy 4-methylphenyloxy, 4-vinylphenyldioxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hexylphenyloxy 4-cyclohexylphenyloxy, 4-octylphenyloxy, 4- (2-ethylhexyl) phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2.6 -Dimethylphenyloxy, 3.4-dimethylphenyloxy, 3. -Dimethylphenyloxy, 2,4-di-tert-butylphenyloxy, 2,5-di-tert-butylphenyloxy, 2,6-di-tert-butylphenyloxy, 2.4-di-tert-pentylphenyloxy, 2 , 5-tert-amylphenyloxy, 4-cyclohexylphenyloxy, 2,4,5-trimethylphenyloxy, ferrocenyloxy, etc.
The arylthio group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 is an arylthio group having 6 to 20 carbon atoms which may have the above-mentioned substituent. A group in which the oxygen atom of the aryloxy group is replaced with a sulfur atom, etc.
The arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, represented by R 10 and R 11 , may have 6 to 20 carbon atoms which may have the above-mentioned substituent. Groups in which the oxygen atom of the aryloxy group is substituted with an alkenyl group such as vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, and the like,
Examples of the arylalkyl group having 7 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include aryl having 7 to 20 carbon atoms represented by R 1 and R 2 Examples include the groups exemplified as the alkyl group,
Examples of the heterocyclic group having 2 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include those having 2 to 20 carbon atoms represented by R 1 and R 2 . The group etc. which were illustrated as a heterocyclic containing group are mentioned.
上記一般式(2)におけるY11で表される3価の炭素原子数3~35の脂環族炭化水素基としては、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、シクロデカニル、1-アダマンチル、2-アダマンチル、ノルアダマンチル、2-メチルアダマンチル、ノルボルニル、イソノルボルニル、パーヒドロナフチル、パーヒドロアントラセニル、ビシクロ[1.1.0]ブチル、ビシクロ[1.1.1]ペンチル、ビシクロ[2.1.0]ペンチル、ビシクロ[3.1.0]ヘキシル、ビシクロ[2.1.1]ヘキシル、ビシクロ[2.2.0]ヘキシル、ビシクロ[4.1.0]ヘプチル、ビシクロ[3.2.0]ヘプチル、ビシクロ[3.1.1]ヘプチル、ビシクロ[2.2.1]ヘプチル、ビシクロ[5.1.0]オクチル、ビシクロ[4.2.0]オクチル、ビシクロ[4.1.1]オクチル、ビシクロ[3.3.0]オクチル、ビシクロ[3.2.1]オクチル、ビシクロ[2.2.2]オクチル、スピロ〔4,4〕ノナニル、スピロ〔4,5〕デカニル、デカリン、トリシクロデカニル、テトラシクロドデカニル、セドロール、シクロドデカニル等の基から誘導される3価の基等が挙げられ、
Y11で表される3価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した3価の芳香環含有炭化水素基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基のうち、所定の炭素原子数を満たすもの等が挙げられ、
Y11で表される3価の炭素原子数2~35の複素環含有基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した3価の複素環含有基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基のうち、所定の炭素原子数を満たすもの等が挙げられる。
また、R12で表される、置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合もある炭素原子数6~35の芳香族炭化水素基及び置換基を有している場合もある炭素原子数2~35の複素環含有基としては、それぞれ、上記一般式(1)におけるR5、R6及びR7の説明で例示した脂肪族炭化水素基、芳香環含有炭化水素基、複素環含有基が挙げられる。 Examples of the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 11 in the general formula (2) include an n-valent bond represented by X 1 in the general formula (IA). Of the trivalent aliphatic hydrocarbon group exemplified as the group and groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). Among them, those satisfying the predetermined number of carbon atoms include trivalent groups substituted with Z 1 , Z 2 and Z 3 , etc.
Examples of the trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by Y 11 in the general formula (2) include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2- Adamantyl, noradamantyl, 2-methyladamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydroanthracenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1. 0] pentyl, bicyclo [3.1.0] hexyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.0] hexyl, bicyclo [4.1.0] heptyl, bicyclo [3.2. 0] heptyl, bicyclo [3.1.1] heptyl, bicyclo [2.2.1] heptyl, bicyclo [5.1.0] Octyl, bicyclo [4.2.0] octyl, bicyclo [4.1.1] octyl, bicyclo [3.3.0] octyl, bicyclo [3.2.1] octyl, bicyclo [2.2.2] And trivalent groups derived from groups such as octyl, spiro [4,4] nonanyl, spiro [4,5] decanyl, decalin, tricyclodecanyl, tetracyclododecanyl, cedrol, cyclododecanyl, etc. ,
Examples of the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 11 include the trivalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Of the aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). And those that satisfy the number of atoms.
Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y 11 include the trivalent complex exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Among the ring-containing groups and groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the above general formula (IA), the predetermined number of carbon atoms is satisfied. And the like.
In addition, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 12 , and an aromatic group having 6 to 35 carbon atoms which may have a substituent. Examples of the heterocyclic group having 2 to 35 carbon atoms which may have a hydrocarbon group and a substituent may be exemplified in the description of R 5 , R 6 and R 7 in the general formula (1). And aliphatic hydrocarbon groups, aromatic ring-containing hydrocarbon groups, and heterocyclic ring-containing groups.
Y12で表される4価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価~3価の芳香環含有炭化水素基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基から誘導される4価の基のうち、所定の炭素原子数を満たすもの等が挙げられ、
Y12で表される4価の炭素原子数2~35の複素環含有基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価~3価の複素環含有基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基から誘導される4価の基のうち、所定の炭素原子数を満たすもの等が挙げられる。 The tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 12 in the general formula (3) is an n-valent aliphatic hydrocarbon group represented by X 1 in the general formula (IA). Monovalent to trivalent aliphatic hydrocarbon groups exemplified as the linking group and these groups substituted by those exemplified as the substituents of the n-valent linking group represented by X 1 in the general formula (IA). Among the tetravalent groups derived from the generated groups, those satisfying a predetermined number of carbon atoms, and the like can be mentioned,
Examples of the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 12 include the monovalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA). To a trivalent aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). Among the tetravalent groups that satisfy the predetermined number of carbon atoms, and the like,
Examples of the tetravalent heterocyclic group having 2 to 35 carbon atoms represented by Y 12 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA). A valent heterocyclic ring-containing group and a tetravalent group derived from these groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). Among the groups, those satisfying a predetermined number of carbon atoms can be mentioned.
Y14で表される5価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価~3価の芳香環含有炭化水素基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基から誘導される5価の基のうち、所定の炭素原子数を満たすもの等が挙げられ、
Y14で表される5価の炭素原子数2~35の複素環含有基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価~3価の複素環含有基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基から誘導される5価の基のうち、所定の炭素原子数を満たすもの等が挙げられる。 The pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 13 in the general formula (4) is an n-valent bond represented by X 1 in the general formula (IA). The monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and these groups are substituted by those exemplified as the substituents of the n-valent linking group represented by X 1 in the general formula (IA). Among the pentavalent groups derived from these groups, those satisfying a predetermined number of carbon atoms, etc.
The pentavalent aromatic group-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 is a monovalent group exemplified as the n-valent linking group represented by X 1 in the general formula (IA). To a trivalent aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). Among the pentavalent groups that satisfy the predetermined number of carbon atoms, and the like,
Examples of the pentavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA). A valent heterocyclic ring-containing group and a pentavalent group derived from these groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). Among the groups, those satisfying a predetermined number of carbon atoms can be mentioned.
Y14で表される6価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価~3価の芳香環含有炭化水素基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基から誘導される6価の基のうち、所定の炭素原子数を満たすもの等が挙げられ、
Y14で表される6価の炭素原子数2~35の複素環含有基としては、上記一般式(I-A)におけるX1で表されるn価の結合基として例示した1価~3価の複素環含有基及びこれらの基が上記一般式(I-A)におけるX1で表されるn価の結合基の置換基として例示したものにより置換された基から誘導される6価の基のうち、所定の炭素原子数を満たすもの等が挙げられる。 The hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 14 in the general formula (5) is an n-valent bond represented by X 1 in the general formula (IA). The monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and these groups are substituted by those exemplified as the substituents of the n-valent linking group represented by X 1 in the general formula (IA). Among the hexavalent groups derived from these groups, those satisfying a predetermined number of carbon atoms, etc.
The hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 is a monovalent group exemplified as the n-valent linking group represented by X 1 in the general formula (IA). To a trivalent aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). Among the hexavalent groups that satisfy the predetermined number of carbon atoms, and the like,
Examples of the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA). A hexavalent divalent ring-containing group and a hexavalent group derived from the group substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). Among the groups, those satisfying a predetermined number of carbon atoms can be mentioned.
上記一般式(II-2)におけるR92及びR93で表されるハロゲン原子、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基としては、上記一般式(I)におけるR1及びR2の説明で例示したものが挙げられる。
上記一般式(II-3)におけるR201、R202、R203、R204、R205、R206、R207、R208で表されるハロゲン原子、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基としては、上記一般式(I)におけるR1及びR2の説明で例示したものが挙げられる。 The halogen atom represented by R 82 , R 83 and R 84 in the general formula (II-1), an alkyl group having 1 to 40 carbon atoms which may have a substituent, and 6 to 20 carbon atoms As the aryl group, the arylalkyl group having 7 to 20 carbon atoms, and the heterocycle-containing group having 2 to 20 carbon atoms, those exemplified in the description of R 1 and R 2 in the general formula (I) can be given. .
The halogen atom represented by R 92 and R 93 in the general formula (II-2), an alkyl group having 1 to 40 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms Examples of the arylalkyl group having 7 to 20 carbon atoms and the heterocyclic ring-containing group having 2 to 20 carbon atoms include those exemplified in the description of R 1 and R 2 in the general formula (I).
Carbons that may have a halogen atom or a substituent represented by R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 in the general formula (II-3) Examples of the alkyl group having 1 to 40 atoms, the aryl group having 6 to 20 carbon atoms, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic-containing group having 2 to 20 carbon atoms include those represented by the general formula (I). The thing illustrated by description of R < 1 > and R < 2 > in can be mentioned.
R1が分岐を有する炭素原子数1~8のアルキル基、特にt-ブチル基であり、R2が水素原子であるもの;R82、R83及びR84が、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~10のアリール基、炭素原子数7~12のアリールアルキル基、炭素原子数1~10の複素環含有基であるもの、特に、R82、R83及びR84の何れか1つが炭素原子数1~4のアルキル基又は炭素原子数1~10の複素環含有基であるものが好ましい。 Among the compounds represented by the general formula (II-1),
R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, and R 2 is a hydrogen atom; R 82 , R 83 and R 84 are each independently a hydrogen atom, An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, a heterocyclic-containing group having 1 to 10 carbon atoms, particularly R 82 , R 83 and R 84 are preferably an alkyl group having 1 to 4 carbon atoms or a heterocyclic ring-containing group having 1 to 10 carbon atoms.
R1が分岐を有する炭素原子数1~8のアルキル基、特にt-ブチル基であり、R2が水素原子であるもの;R92及びR93が、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~10のアリール基、炭素原子数7~12のアリールアルキル基、炭素原子数1~10の複素環含有基であるもの、特に、R92又はR93が炭素原子数1~4のアルキル基又は炭素原子数1~10の複素環含有基であるものが好ましい。
X2が上記一般式(1)となる場合、Y10が、硫黄原子、炭素原子数1~20のアルキレン基、炭素原子数6~25の2価の芳香環含有炭化水素基、炭素原子数2~21の2価の複素環含有基、2,4,8,10-テトラオキサスピロ[5,5]ウンデカンから誘導される2価の基、特に、炭素原子数1~15のアルキレン基、炭素原子数6~15の2価の芳香環含有炭化水素基、2,4,8,10-テトラオキサスピロ[5,5]ウンデカンから誘導される2価の基であるものが好ましく、
Z1及びZ2が直接結合、-CO-O-、-O-CO-、又は置換基を有していても良い炭素原子数1~20の脂肪族炭化水素基、炭素原子数6~10の芳香族炭化水素基、特に置換基を有していても良い炭素原子数1~8の脂肪族炭化水素基であるものが好ましい。
X2が上記一般式(2)となる場合、Y11が、炭素原子数1~20のアルキル基、炭素原子数6~10のアリール基、炭素原子数7~12のアリールアルキル基又は炭素原子数1~10の複素環含有基から誘導される3価の基、特に、炭素原子数1~8のアルキル基、炭素原子数6~9のアリール基又は炭素原子数1~6の複素環含有基から誘導される3価の基であるものが好ましく、
Z1、Z2及びZ3は、Z1及びZ2と同様のものが好ましく、
X2が上記一般式(3)となる場合、Y12は、好ましいY11として上に挙げた基に対応する4価の基が好ましく、
Z1~Z4は、Z1及びZ2と同様であるものが好ましく、
X2が上記一般式(4)となる場合、Y13は、好ましいY11として上に挙げた基に対応する5価の基が好ましく、
Z1~Z5はZ1及びZ2と同様であるものが好ましく、
X2が上記一般式(5)となる場合、Y14は、好ましいY11として上に挙げた基に対応する6価の基が好ましく、
Z1~Z6は、Z1及びZ2と同様であるものが好ましい。 Among the compounds represented by the general formula (II-2),
R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, and R 2 is a hydrogen atom; R 92 and R 93 are each independently a hydrogen atom or carbon atom number An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, a heterocyclic-containing group having 1 to 10 carbon atoms, particularly R 92 or R 93 Is preferably an alkyl group having 1 to 4 carbon atoms or a heterocyclic-containing group having 1 to 10 carbon atoms.
When X 2 is the above general formula (1), Y 10 is a sulfur atom, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, the number of carbon atoms 2 to 21 divalent heterocyclic ring-containing groups, divalent groups derived from 2,4,8,10-tetraoxaspiro [5,5] undecane, particularly alkylene groups having 1 to 15 carbon atoms, A divalent aromatic ring-containing hydrocarbon group having 6 to 15 carbon atoms and a divalent group derived from 2,4,8,10-tetraoxaspiro [5,5] undecane are preferred,
Z 1 and Z 2 are a direct bond, —CO—O—, —O—CO—, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or 6 to 10 carbon atoms. Of these, an aromatic hydrocarbon group, particularly an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, is preferred.
When X 2 is the above general formula (2), Y 11 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or a carbon atom A trivalent group derived from a heterocyclic group having 1 to 10 carbon atoms, particularly an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 9 carbon atoms, or a heterocyclic ring having 1 to 6 carbon atoms Those which are trivalent groups derived from a group are preferred,
Z 1 , Z 2 and Z 3 are preferably the same as Z 1 and Z 2 ,
When X 2 is the above general formula (3), Y 12 is preferably a tetravalent group corresponding to the group listed above as preferred Y 11 ,
Z 1 to Z 4 are preferably the same as Z 1 and Z 2 ,
When X 2 is the above general formula (4), Y 13 is preferably a pentavalent group corresponding to the group listed above as preferred Y 11 ,
Z 1 to Z 5 are preferably the same as Z 1 and Z 2 ,
When X 2 is represented by the general formula (5), Y 14 is preferably a hexavalent group corresponding to the group listed above as preferred Y 11 ,
Z 1 to Z 6 are preferably the same as Z 1 and Z 2 .
上記潜在性添加剤とは、常温、あるいは150℃以下、例えば150℃以下のプリベーク工程では不活性であり、100~250℃で加熱するか、あるいは酸/塩基触媒存在下で80~200℃で加熱することにより、保護基が脱離して活性となるものである。 The compound having a substituent represented by the general formula (I) can be used as a latent additive in the photosensitive composition of the present invention.
The latent additive is inactive in a pre-bake process at room temperature or 150 ° C. or less, for example 150 ° C. or less, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst. By heating, the protecting group is eliminated and becomes active.
該酸価を有するエチレン性不飽和結合を有する重合性化合物としては、(メタ)アクリル酸、α-クロルアクリル酸、イタコン酸、マレイン酸、シトラコン酸、フマル酸、ハイミック酸、クロトン酸、イソクロトン酸、ビニル酢酸、アリル酢酸、桂皮酸、ソルビン酸、メサコン酸、コハク酸モノ[2-(メタ)アクリロイロキシエチル]、フタル酸モノ[2-(メタ)アクリロイロキシエチル]、ω-カルボキシポリカプロラクトンモノ(メタ)アクリレート等の両末端にカルボキシ基と水酸基とを有するポリマーのモノ(メタ)アクリレート、ヒドロキシエチル(メタ)アクリレート・マレート、ヒドロキシプロピル(メタ)アクリレート・マレート、ジシクロペンタジエン・マレート或いは1個のカルボキシル基と2個以上の(メタ)アクリロイル基とを有する多官能(メタ)アクリレート等の不飽和多塩基酸;フェノール及び/又はクレゾールノボラックエポキシ樹脂、ビフェニル骨格、ナフタレン骨格を有するノボラックエポキシ樹脂、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物、多官能エポキシ基を有するポリフェニルメタン型エポキシ樹脂、下記一般式(III)で表されるエポキシ化合物等のエポキシ樹脂のエポキシ基に不飽和一塩基酸を作用させた樹脂、エポキシ樹脂のエポキシ基に不飽和一塩基酸を作用させ、更に多塩基酸無水物を作用させて得られた樹脂、ペンタエリスリトールトリアクリレート、ジペンタエリスリトールペンタアクリレート等の水酸基含有多官能アクリレートと無水コハク酸、無水フタル酸、テトラヒドロ無水フタル酸等の二塩基酸無水物の反応物である酸価を有する多官能アクリレート等が挙げられる。 The photosensitive composition of the present invention is a composition whose properties are changed by light irradiation. A positive resist is one that is soluble in a chemical reaction, and a negative resist is one that is insoluble in a chemical reaction. . The photosensitive composition of the present invention contains a compound having a substituent represented by the above general formula (I) as a latent antioxidant, a polymerizable compound having an ethylenically unsaturated bond having an acid value, and light. A radical polymerization initiator is contained as an essential component.
Examples of the polymerizable compound having an ethylenically unsaturated bond having an acid value include (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, and isocrotonic acid. Vinyl acetate, allyl acetate, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ω-carboxypoly Mono (meth) acrylate, hydroxyethyl (meth) acrylate / malate, hydroxypropyl (meth) acrylate / malate, dicyclopentadiene / malate, which has a carboxy group and a hydroxyl group at both ends, such as caprolactone mono (meth) acrylate 1 carboxyl group and 2 or more (meth) acryloyl Unsaturated polybasic acids such as polyfunctional (meth) acrylates having a group; phenol and / or cresol novolac epoxy resin, biphenyl skeleton, novolac epoxy resin having naphthalene skeleton, bisphenol A novolac epoxy compound, dicyclopentadiene novolac type An unsaturated monobasic acid is allowed to act on the epoxy group of an epoxy resin such as an epoxy compound such as an epoxy compound, a polyphenylmethane type epoxy resin having a polyfunctional epoxy group, and an epoxy compound represented by the following general formula (III) Resin obtained by allowing unsaturated monobasic acid to act on the epoxy group of epoxy resin, epoxy resin, and polybasic acid anhydride, polyfunctional acrylate containing hydroxyl group such as pentaerythritol triacrylate, dipentaerythritol pentaacrylate When Water succinic acid, phthalic acid anhydride, a polyfunctional acrylate having an acid value which is a reaction product of a dibasic acid anhydride such as tetrahydrophthalic anhydride.
R41、R42、R43及びR44は、それぞれ独立に、水素原子、置換基を有している場合もある炭素原子数1~5のアルキル基、置換基を有している場合もある炭素原子数1~8のアルコキシ基、置換基を有している場合もある炭素原子数2~5のアルケニル基又はハロゲン原子を表し、
mは0~10の整数である。)
R 41 , R 42 , R 43 and R 44 each independently have a hydrogen atom, a substituent or a C 1-5 alkyl group or a substituent. An alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms which may have a substituent, or a halogen atom;
m is an integer of 0 to 10. )
本発明の感光性組成物において、酸価を有するエチレン性不飽和結合を有する重合性化合物の含有量は、本発明の組成物の固形分中、20~80質量%が好ましく、固形分中の30~70質量%がさらに好ましい。 These polymerizable compounds having an ethylenically unsaturated bond having an acid value can be used alone or in admixture of two or more, and are polymerizable having an ethylenically unsaturated bond having no acid value. It can be used in combination with a compound. When two or more kinds are mixed and used, they may be copolymerized in advance and used as a copolymer.
In the photosensitive composition of the present invention, the content of the polymerizable compound having an ethylenically unsaturated bond having an acid value is preferably 20 to 80% by mass in the solid content of the composition of the present invention. More preferred is 30 to 70% by mass.
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4-エポキシ-6-メチルシクロヘキシルメチル-3,4-エポキシ-6-メチルシクロヘキサンカルボキシレート、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、1-エポキシエチル-3,4-エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジル-p-アミノフェノール、N,N-ジグリシジルアニリン等のグリシジルアミン類;1,3-ジグリシジル-5,5-ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物、トリフェニルメタン型エポキシ化合物、ジシクロペンタジエン型エポキシ化合物等を用いることもできる。 As the polyfunctional epoxy compound, it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a photosensitive composition with better characteristics can be obtained. As the bisphenol type epoxy compound, an epoxy compound represented by the above general formula (III) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used. Examples of the glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (glycidyloxymethyl) methane, 1,1,1,1- tetra (glycidyloxymethyl) include methane.
Other novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy compounds such as 1,3-diglycidyl-5,5-dimethylhydantoin and triglycidyl isocyanurate; Dioxide compounds such as cyclopentadiene dioxide; naphthalene type epoxy compounds, triphenylmethane type epoxy compounds, dicyclopentadiene type epoxy compounds and the like can also be used.
R53及びR54は、それぞれ独立に、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R55、OR56、SR57、NR58R59、COR60、SOR61、SO2R62又はCONR63R64を表し、R53及びR54は、互いに結合して環を形成している場合もあり、
R55、R56、R57、R58、R59、R60、R61、R62、R63及びR64は、それぞれ独立に、置換基を有している場合もある炭素原子数1~20のアルキル基、置換基を有している場合もある炭素原子数6~30のアリール基、置換基を有している場合もある炭素原子数7~30のアリールアルキル基又は置換基を有している場合もある炭素原子数2~20の複素環含有基を表し、
X3は、酸素原子、硫黄原子、セレン原子、CR75R76、CO、NR77又はPR78を表し、
X4は、単結合又はCOを表し、
R75~R78は、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基又は炭素原子数7~30のアリールアルキル基を表し、該アルキル基又はアリールアルキル基中のメチレン基は、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基又は複素環含有基で置き換えられている場合もあり、-O-で置き換えられている場合もあり、
R53及びR54は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成している場合もあり、
aは、0~4の整数を表し、
bは、0~5の整数を表す。)
R 53 and R 54 are each independently a halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, R 55 , OR 56 , SR 57 , NR 58 R 59 , COR 60 , SOR 61 , SO 2 R 62 or CONR 63 R 64 , R 53 and R 54 may combine with each other to form a ring,
R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62 , R 63 and R 64 each independently have 1 to 1 carbon atoms which may have a substituent. 20 alkyl groups, aryl groups having 6 to 30 carbon atoms which may have substituents, arylalkyl groups having 7 to 30 carbon atoms which may have substituents or substituents Represents a heterocyclic group containing 2 to 20 carbon atoms, which may be
X 3 represents an oxygen atom, a sulfur atom, a selenium atom, CR 75 R 76 , CO, NR 77 or PR 78 ,
X 4 represents a single bond or CO,
R 75 to R 78 represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and methylene in the alkyl group or arylalkyl group The group may be replaced by a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a heterocyclic group, or may be replaced by -O-
R 53 and R 54 may each independently form a ring together with one of the adjacent benzene rings,
a represents an integer of 0 to 4,
b represents an integer of 0 to 5. )
R111、R112及びR113は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R111、R112及びR113で表わされる基の水素原子は、更にR121、OR121、COR121、SR121、NR122R123、CONR122R123、-NR122-OR123、-NCOR122-OCOR123、NR122COR121、OCOR121、COOR121、SCOR121、OCSR121、COSR121、CSOR121、水酸基、ニトロ基、CN又はハロゲン原子で置き換えられている場合もあり、
R121、R122及びR123は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R121、R122及びR123で表される基の水素原子は、更に水酸基、ニトロ基、CN、ハロゲン原子、水酸基又はカルボキシル基で置換されている場合もあり、
R111、R112、R113、R121、R122及びR123で表される基のアルキレン部分は、-O-、-S-、-COO-、-OCO-、-NR124-、-NR124COO-、-OCONR124-、-SCO-、-COS-、-OCS-又は-CSO-により酸素原子が隣り合わない条件で1~5回置き換えられている場合もあり、
R124は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R111、R112、R113、R121、R122、R123及びR124で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、
R103は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、R103で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、また、R103とR107、R103とR108、R104とR105、R105とR106及びR106とR107はそれぞれ一緒になって環を形成している場合もあり、
R103で表わされる基の水素原子は、更にR121、OR121、COR121、SR121、NR122R123、CONR122R123、-NR122-OR123、-NCOR122-OCOR123、NR122COR121、OCOR121、COOR121、SCOR121、OCSR121、COSR121、CSOR121、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR121で置換されている場合もあり、
R104、R105、R106及びR107は、それぞれ独立に、R111、OR111、SR111、COR114、CONR151R116、NR112COR111、OCOR111、COOR114、SCOR111、OCSR111、COSR114、CSOR111、水酸基、CN又はハロゲン原子を表し、R104とR105、R105とR106及びR106とR107はそれぞれ一緒になって環を形成している場合もあり、
R114、R115及びR116は、水素原子又は炭素原子数1~20のアルキル基を表し、
R108は、R111、OR111、SR111、COR111、CONR112R113、NR112COR111、OCOR111、COOR111、SCOR111、OCSR111、COSR111、CSOR111、水酸基、CN又はハロゲン原子を表し、
wは、0又は1を表す。)
R 111 , R 112 and R 113 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom. Represents a heterocyclic-containing group of formula 2 to 20,
The hydrogen atoms of the groups represented by R 111 , R 112 and R 113 are further R 121 , OR 121 , COR 121 , SR 121 , NR 122 R 123 , CONR 122 R 123 , —NR 122 —OR 123 , —NCOR 122. -OCOR 123 , NR 122 COR 121 , OCOR 121 , COOR 121 , SCOR 121 , OCSR 121 , COSR 121 , CSOR 121 , hydroxyl group, nitro group, CN or halogen atom may be substituted,
R 121 , R 122 and R 123 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom Represents a heterocyclic-containing group of formula 2 to 20,
The hydrogen atom of the group represented by R 121 , R 122 and R 123 may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group,
The alkylene part of the group represented by R 111 , R 112 , R 113 , R 121 , R 122 and R 123 is —O—, —S—, —COO—, —OCO—, —NR 124 —, —NR 124 COO—, —OCONR 124 —, —SCO—, —COS—, —OCS— or —CSO— may be substituted 1 to 5 times under the condition that the oxygen atoms are not adjacent to each other,
R 124 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic ring-containing group having 2 to 20 carbon atoms. Represent,
The alkyl part of the group represented by R 111 , R 112 , R 113 , R 121 , R 122 , R 123 and R 124 may have a branched side chain or a cyclic alkyl.
R 103 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic ring-containing group having 2 to 20 carbon atoms. The alkyl part of the group represented by R 103 may have a branched side chain or may be a cyclic alkyl, and R 103 and R 107 , R 103 and R 108 , R 104 and R 105 , R 105 and R 106 and R 106 and R 107 may be combined to form a ring,
Hydrogen atoms in the group represented by R 103 may further R 121, OR 121, COR 121 , SR 121, NR 122 R 123, CONR 122 R 123, -NR 122 -OR 123, -NCOR 122 -OCOR 123, NR 122 COR 121 , OCOR 121 , COOR 121 , SCOR 121 , OCSR 121 , COSR 121 , CSOR 121 , hydroxyl group, nitro group, CN, halogen atom, or COOR 121 may be substituted,
R 104 , R 105 , R 106 and R 107 are each independently R 111 , OR 111 , SR 111 , COR 114 , CONR 151 R 116 , NR 112 COR 111 , OCOR 111 , COOR 114 , SCOR 111 , OCSR 111 , COSR 114 , CSOR 111 , a hydroxyl group, CN or a halogen atom, R 104 and R 105 , R 105 and R 106, and R 106 and R 107 may be combined to form a ring,
R 114 , R 115 and R 116 each represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;
R 108 is R 111 , OR 111 , SR 111 , COR 111 , CONR 112 R 113 , NR 112 COR 111 , OCOR 111 , COOR 111 , SCOR 111 , OCSR 111 , COSR 111 , CSOR 111 , hydroxyl group, CN or halogen atom Represents
w represents 0 or 1. )
本発明の着色感光性組成物において、着色剤の添加量は、本発明の着色感光性組成物の固形分中、0.01~50質量%が好ましく、0.1~30質量%がより好ましい。上記着色剤の含有量が0.01質量%より小さいと、所望の色度が得られない場合があり、50質量%より大きいと、着色感光性組成物中に着色剤が析出する場合がある。 The photosensitive composition of the present invention can be made into a colored photosensitive composition by further adding a colorant. The cured product of the colored photosensitive composition is suitably used as a color filter.
In the colored photosensitive composition of the present invention, the addition amount of the colorant is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass in the solid content of the colored photosensitive composition of the present invention. . When the content of the colorant is less than 0.01% by mass, desired chromaticity may not be obtained. When the content is greater than 50% by mass, the colorant may be precipitated in the colored photosensitive composition. .
染料としては、380~1200nmに吸収を有する化合物であれば特に限定されないが、例えば、アゾ化合物、アントラキノン化合物、インジゴイド化合物、トリアリールメタン化合物、キサンテン化合物、アリザリン化合物、アクリジン化合物、スチルベン化合物、チアゾール化合物、ナフトール化合物、キノリン化合物、ニトロ化合物、インダミン化合物、オキサジン化合物、フタロシアニン化合物、シアニン化合物、ジインモニウム化合物、シアノエテニル化合物、ジシアノスチレン化合物、ローダミン化合物、ペリレン化合物、ポリエンナフトラクタム化合物、クマリン化合物、スクアリリウム化合物、クロコニウム化合物、スピロピラン化合物、スピロオキサジン化合物、メロシアニン化合物、オキソノール化合物、スチリル化合物、ピリリウム化合物、ローダニン化合物、オキサゾロン化合物、フタルイミド化合物、シンノリン化合物、ナフトキノン化合物、アザアントラキノン化合物、ポルフィリン化合物、アザポルフィリン化合物、ピロメテン化合物、キナクリドン化合物、ジケトピロロピロール化合物、インジゴ化合物、アクリジン化合物、アジン化合物、アゾメチン化合物、アニリン化合物、キナクリドン化合物、キノフタロン化合物、キノンイミン化合物、イリジウム錯体化合物、ユーロピウム錯体化合物等の染料等が挙げられ、これらは複数を混合して用いてもよい。 Examples of the colorant include dyes and pigments.
The dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm. For example, azo compound, anthraquinone compound, indigoid compound, triarylmethane compound, xanthene compound, alizarin compound, acridine compound, stilbene compound, thiazole compound , Naphthol compound, quinoline compound, nitro compound, indamine compound, oxazine compound, phthalocyanine compound, cyanine compound, diimmonium compound, cyanoethenyl compound, dicyanostyrene compound, rhodamine compound, perylene compound, polyenenaphtholactam compound, coumarin compound, squarylium compound, croconium Compound, spiropyran compound, spirooxazine compound, merocyanine compound, oxonol compound, styrylation Product, pyrylium compound, rhodanine compound, oxazolone compound, phthalimide compound, cinnoline compound, naphthoquinone compound, azaanthraquinone compound, porphyrin compound, azaporphyrin compound, pyromethene compound, quinacridone compound, diketopyrrolopyrrole compound, indigo compound, acridine compound, azine Examples thereof include dyes such as compounds, azomethine compounds, aniline compounds, quinacridone compounds, quinophthalone compounds, quinoneimine compounds, iridium complex compounds, and europium complex compounds, and these may be used in combination.
上記マスクとしては、ハーフトーンマスク又はグレースケールマスク等の多階調マスクを用いることもできる。 The color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition of the present invention on a substrate, and (2) active light through a mask having a predetermined pattern shape on the coating film. Preferably, the step of irradiating, (3) the step of developing the film after exposure with a developer, and (4) the step of heating the film after development are preferably formed. In addition, the colored photosensitive composition of the present invention is also useful as an inkjet-type colored photosensitive composition without a development step.
As the mask, a multi-tone mask such as a halftone mask or a gray scale mask can be used.
下記化合物No.1’のフェノール化合物1当量のジメチルアセトアミド溶液(理論収量の3倍量)に炭酸カリウム(1つのフェノール基に対して2当量)を加え、室温で30分撹拌した。アリルブロマイド(1つのフェノール基に対して1.5当量)を加え、60℃で5時間撹拌した。酢酸エチルを加えて1%塩酸溶液で洗浄した後油水分離を行い、有機層を無水硫酸ナトリウムで乾燥後、溶媒を留去し、晶析を行った。得られた固体を60℃で3時間減圧乾燥させ、目的物を得た。得られた固体が目的物であることは1H-NMR、IRにて確認した。結果を[表1]~[表2]に示す。 [Example 1-1] Compound No. 1 Synthesis of Compound 1 Potassium carbonate (2 equivalents with respect to one phenol group) was added to a dimethylacetamide solution of 1 equivalent of 1 ′ phenol compound (3 times the theoretical yield), and the mixture was stirred at room temperature for 30 minutes. Allyl bromide (1.5 equivalent to one phenol group) was added, and the mixture was stirred at 60 ° C. for 5 hours. After adding ethyl acetate and washing with 1% hydrochloric acid solution, oil-water separation was performed, and after drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and crystallization was performed. The obtained solid was dried under reduced pressure at 60 ° C. for 3 hours to obtain the desired product. It was confirmed by 1 H-NMR and IR that the obtained solid was the desired product. The results are shown in [Table 1] to [Table 2].
実施例1-1において、下記化合物No.1’のフェノール化合物に代えて、下記化合物No.2’~6’のフェノール化合物を用いた以外は実施例1-1と同様にして、目的物である化合物No.2~6を合成した。得られた固体が目的物であることは1H-NMR、IRにて確認した。結果を[表1]~[表2]に示す。 [Examples 1-2 to 1-6] Compound No. Synthesis of 2 to 6 In Example 1-1, the following compound No. Instead of the phenol compound of 1 ′, the following compound No. The target compound No. 2 was prepared in the same manner as in Example 1-1, except that 2 ′ to 6 ′ phenolic compounds were used. 2-6 were synthesized. It was confirmed by 1 H-NMR and IR that the obtained solid was the desired product. The results are shown in [Table 1] to [Table 2].
SPC-1000(昭和電工社製、固形分29%のPGMEA溶液)50.0g、アロニックスM-450(東亜合成社製)11.6g、NCI-930(ADEKA社製)0.3g、PGMEA34.7g、FZ2122(東レ・ダウコーニング社製、固形分1%のPGMEA溶液)2.9g及び[表3]記載の化合物0.81gを混合し、不溶物が無くなるまで撹拌し、感光性組成物No.1~No.2及び比較感光性組成物No.1~No.3を得た。 [Examples 2-1 to 2-2 and Comparative Examples 2-1 to 2-3] Photosensitive composition Nos. 1-No. 2 and comparative photosensitive composition no. 1-No. Preparation of 3 SPC-1000 (manufactured by Showa Denko KK, PGMEA solution with a solid content of 29%) 50.0 g, Aronix M-450 (manufactured by Toagosei), 11.6 g, NCI-930 (manufactured by ADEKA) 0.3 g, 34.7 g of PGMEA, 2.9 g of FZ2122 (manufactured by Toray Dow Corning Co., Ltd., PGMEA solution with a solid content of 1%) and 0.81 g of the compound described in [Table 3] are mixed, and stirred until insoluble matter is eliminated, and photosensitive composition Item No. 1-No. 2 and comparative photosensitive composition no. 1-No. 3 was obtained.
化合物No.1、化合物No.2並びに比較化合物No.2をそれぞれ5mg測り取り、熱質量測定装置にて室温から230℃まで昇温(20℃/min.)した後、230℃で30分間保持した時点での重量減少率を測定して、感光性組成物No.1~No.2及び比較感光性組成物No.2のアウトガス評価とした。重量減少が小さいほど、アウトガスが少ないことを示す。結果を[表4]に示す。 [Evaluation Example 1-1 and Comparative Evaluation Example 1-1] Outgas Evaluation 1, compound no. 2 and comparative compound no. 5 mg of each 2 was measured, and the temperature was increased from room temperature to 230 ° C. (20 ° C./min.) With a thermal mass measuring device, and then the weight reduction rate at the time of holding at 230 ° C. for 30 minutes was measured. Composition No. 1-No. 2 and comparative photosensitive composition no. An outgas rating of 2 was assigned. A smaller weight loss indicates less outgas. The results are shown in [Table 4].
上記実施例2-1で得られた感光性組成物No.1及び比較例2-1及び2-3で得られた比較感光性組成物No.1及びNo.3を、それぞれガラス基板に410rpm×7秒の条件で塗工し、ホットプレートで乾燥(90℃×90秒)させた。得られた塗膜に超高圧水銀ランプで露光(40mJ/cm2)した。露光後の塗膜を、230℃×30分の条件で焼成した。得られた塗膜の膜厚を測定した後、室温で30分間、PGMEA、シクロヘキサノン、N-メチルピロリドン、N-エチルピロリドンに浸漬させ、浸漬後の膜厚を測定した。浸漬前後での膜厚比(浸漬後の膜厚×100/浸漬前の膜厚)が100%に近いほど、耐溶剤性は高いと評価した。 [Evaluation Example 2-1 and Comparative Evaluation Examples 2-1 and 2-2] Solvent Resistance Evaluation The photosensitive composition No. obtained in Example 2-1 was used. Comparative photosensitive composition Nos. 1 and 2 obtained in Comparative Examples 2-1 and 2-3. 1 and no. 3 were each coated on a glass substrate under conditions of 410 rpm × 7 seconds and dried on a hot plate (90 ° C. × 90 seconds). The obtained coating film was exposed (40 mJ / cm 2 ) with an ultrahigh pressure mercury lamp. The exposed coating film was baked under conditions of 230 ° C. × 30 minutes. After measuring the film thickness of the obtained coating film, it was immersed in PGMEA, cyclohexanone, N-methylpyrrolidone, and N-ethylpyrrolidone at room temperature for 30 minutes, and the film thickness after immersion was measured. It was evaluated that the solvent resistance was higher as the film thickness ratio before and after immersion (film thickness after immersion × 100 / film thickness before immersion) was closer to 100%.
According to the present invention, there is little outgassing and a solvent resistance of a cured product using a compound that is inactive at room temperature and activated by heating to a predetermined temperature and exhibits a function as an antioxidant or an ultraviolet absorber. Highly sensitive photosensitive composition can be provided.
Claims (9)
- 下記一般式(I)で表される置換基を有する化合物を含有する感光性組成物。
R1及びR2で表されるアルキル基又はアリールアルキル基中のメチレン基は、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR’-、-S-S-又は-SO2-から選ばれた基を酸素原子が隣り合わない条件で組み合わせた基で置き換えている場合もあり、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
jは、1~3の数を表し、
*は、*部分で、隣接する基と結合することを意味する。) The photosensitive composition containing the compound which has a substituent represented with the following general formula (I).
The methylene group in the alkyl group or arylalkyl group represented by R 1 and R 2 is —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—. O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—. , -NR '-, - S- S- or -SO 2 - from selected based on some cases where the oxygen atoms are replaced by a group composed of a combination under conditions which are not adjacent, R' is a hydrogen atom or a carbon atom Represents an alkyl group of 1 to 8,
j represents a number from 1 to 3,
* Means that it is bonded to an adjacent group at the * part. ) - 上記一般式(I)で表される置換基を有する化合物が、下記一般式(I-A)で表される化合物である請求項1に記載の感光性組成物。
X1は、n価の結合基を表し、
R1、R2及びjは、上記一般式(I)と同じである。) The photosensitive composition according to claim 1, wherein the compound having a substituent represented by the general formula (I) is a compound represented by the following general formula (IA).
X 1 represents an n-valent linking group,
R 1 , R 2 and j are the same as in the general formula (I). ) - 請求項1又は2に記載の感光性組成物の硬化物。 Hardened | cured material of the photosensitive composition of Claim 1 or 2.
- 請求項3に記載の硬化物を用いて形成される透明積層体又は透明構造体を少なくとも一部に具備してなる表示デバイス。 A display device comprising at least a part of a transparent laminate or a transparent structure formed using the cured product according to claim 3.
- 請求項1又は2に記載の感光性組成物にさらに着色剤を含有させてなる着色感光性組成物。 A colored photosensitive composition obtained by further adding a colorant to the photosensitive composition according to claim 1.
- 請求項5に記載の着色感光性組成物の硬化物。 A cured product of the colored photosensitive composition according to claim 5.
- 請求項6に記載の硬化物を用いて形成されるカラーフィルタ。 A color filter formed using the cured product according to claim 6.
- 請求項1若しくは2に記載の感光性組成物又は請求項5に記載の着色感光性組成物を支持基体上に塗布して塗膜を形成する工程、及び該塗膜に活性光を露光して硬化させる工程を含む、請求項1若しくは2に記載の感光性組成物又は請求項5に記載の着色感光性組成物を硬化させる方法。 A step of coating the photosensitive composition according to claim 1 or 2 or the colored photosensitive composition according to claim 5 on a supporting substrate to form a coating film, and exposing the coating film to active light The method to harden the photosensitive composition of Claim 1 or 2 or the colored photosensitive composition of Claim 5 including the process to harden | cure.
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TW201806918A (en) | 2018-03-01 |
KR102316645B1 (en) | 2021-10-25 |
TWI771294B (en) | 2022-07-21 |
KR20180132599A (en) | 2018-12-12 |
JP6889151B2 (en) | 2021-06-18 |
JPWO2017170182A1 (en) | 2019-02-07 |
CN108473609A (en) | 2018-08-31 |
CN108473609B (en) | 2022-08-30 |
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