WO2020108421A1 - Hexaarylbiimidazole hybrid photoinitiator and application - Google Patents
Hexaarylbiimidazole hybrid photoinitiator and application Download PDFInfo
- Publication number
- WO2020108421A1 WO2020108421A1 PCT/CN2019/120524 CN2019120524W WO2020108421A1 WO 2020108421 A1 WO2020108421 A1 WO 2020108421A1 CN 2019120524 W CN2019120524 W CN 2019120524W WO 2020108421 A1 WO2020108421 A1 WO 2020108421A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- photosensitive resin
- acrylate
- resin composition
- bis
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 239000011342 resin composition Substances 0.000 claims abstract description 56
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 90
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- 125000001424 substituent group Chemical group 0.000 claims description 13
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- 125000006617 triphenylamine group Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 125000002948 undecyl 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])[H] 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Images
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- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
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- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
Definitions
- the invention belongs to the technical field of photocuring, and specifically relates to a hexaarylbisimidazole mixed photoinitiator, a photosensitive resin composition containing the photoinitiator, and the application of the photosensitive resin composition.
- the manufacture of microelectronic circuits such as printed circuit boards, integrated circuits, thin film transistors, semiconductor packages, etc. generally includes the formation of resist patterns using photolithography.
- the photosensitive resin composition layer or laminate coated on the substrate is exposed in combination with a mask having a predetermined pattern, and then developed using a developer with different solubility in the exposed part and the non-exposed part to form a resist
- the pattern is etched, and then the substrate is plated and/or etched using the resist pattern as a mask to form a desired conductor pattern on the substrate.
- HABI Hexaarylbisimidazole compounds
- the current research also emphasizes that the photosensitive composition can be developed or processed in an aqueous phase. If the solubility of the components of the photosensitive resin composition in the developing solution is low, insoluble components that are poorly dispersible in the developing solution when the development process is repeated are remarkably increased, and aggregates (sludge) appear. When the development process is continued, the condensate will re-attach to the substrate, which may cause a short circuit and block the piping of the development tank.
- the purpose of the present invention is to provide A HABI type mixed photoinitiator.
- the hexaarylbisimidazole mixed photoinitiator of the present invention has the structure shown in the general formula (I), which contains four connection positions of 1'-2, 2-3', 1-2' and 2'-3 Of the biimidazole compound, and the total mass percentage of the four connected biimidazole compounds in the mixed photoinitiator is more than 92%,
- Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , and Ar 6 may be the same or different, and each independently represents a substituted or unsubstituted aryl group.
- the aryl group refers to any functional group or substituent derived from a simple aromatic ring, for example: phenyl, o-tolyl, 1-naphthyl (or ⁇ -naphthyl), 2-naphthyl and the like.
- the object of the present invention is also to provide a photosensitive resin composition containing the above-mentioned mixed photoinitiator, and the application of the composition in manufacturing printed circuit boards, protective patterns, conductor patterns, lead wires, semiconductor packages, and the like.
- the photosensitive resin composition containing the above-mentioned hexaarylbisimidazole-based mixed photoinitiator has good compatibility, excellent sensitivity, and a small amount of developing waste, and can be widely used as a dry film and a wet film.
- sludge and "developing waste” in this application refer to substances accumulated in the developing solution, which are insoluble in the developing solution and will be redeposited on the developed substrate, thereby reducing the efficiency of the developing solution.
- the hexaarylbisimidazole mixed photoinitiator of the present invention has the structure shown in the general formula (I), which contains four connection positions of 1'-2, 2-3', 1-2' and 2'-3 Of the biimidazole compound, and the total mass percentage of the four connected biimidazole compounds in the mixed photoinitiator is more than 92%,
- Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , and Ar 6 may be the same or different, and each independently represents a substituted or unsubstituted aryl group.
- biimidazole compounds satisfying the four connection positions 1'-2, 2-3', 1-2' and 2'-3 of the structure represented by the general formula (I) have the following structures:
- the substituted aryl group may be mono-substituted or poly-substituted.
- the substituent on the aryl group may be halogen, nitro, cyano, amine, hydroxy, C 1 -C 20 alkyl or alkenyl, C 1 -C 8 alkoxy, each of which is independent
- the methylene group in the variable ie, each substituent may be optionally substituted with oxygen, sulfur, and imine groups.
- the substituent on the aryl group may be fluorine, chlorine, bromine, nitro, cyano, amine, hydroxy, C 1 -C 10 alkyl or alkenyl, C 1 -C 5 alkoxy Group, wherein the methylene group in each independent variable may be optionally substituted by oxygen, sulfur, imine groups.
- At least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 is an aryl group containing a halogen substituent.
- the halogen substituent can improve the color change effect during the curing process to enhance the recognition ability of the electronic eye during development (Note: the photosensitive resin layer will change color after exposure, and form a color difference with the unexposed area, which is recognized by the electronic eye. The invention can make the color difference more obvious), thereby improving the quality of the applied products.
- the halogen substituent is chlorine.
- the HABI in this application means hexaaryldiimidazole, which is formed by coupling two triarylimidazoles (which may be the same or different, depending on the substituent on the aryl group). Due to the induction effect of the substituents on the aromatic ring, the ⁇ electron cloud density of the aromatic ring is reduced, and the induction effect causes the aromatic ring to twist. The conjugate center on the imidazole ring shifts, making the substituted aryl group and imidazole not in the same plane ( The triarylimidazole is in a curved state). When the two imidazoles are finally coupled, the connection of N and C shows different spatial configurations, which has a great impact on the performance of HABI.
- HABI photoinitiators also exist 1-4′, 1-5′, 3- 4', 3-5', 1-1', 1-3', 3-1', 3-3', 4-1', 4-3', 5-1', 5-3', etc. .
- the applicant's research found that HABI can only show the best performance when the four connection sites 1'-2, 2-3', 1-2', 2'-3 exist and the total content accounts for more than 92% of the total HABI. Excellent solubility and sensitivity.
- the solubility of a single substance at any kind of connection site is far less than the mixture of the present invention, and if the total content of these four kinds of connection sites is less than 92%, the sensitivity tends to become significantly lower.
- a biimidazole compound satisfying four connection positions of 1′-2, 2-3′, 1-2′ and 2′-3 of the structure represented by the general formula (I) is preferably The total mass percentage in the mixed photoinitiator is 95% or more, and it is particularly preferred that the four types of 1'-2, 2-3', 1-2' and 2'-3 satisfy the structure represented by the general formula (I)
- the connected position is composed of a biimidazole compound.
- CN1292892A mentions a HABI photoinitiator used in photoresist photopolymerization systems, namely 2,2',5-tris(o-chlorophenyl)-4-( 3,4-dimethoxyphenyl)-4',5'-diphenyl-1,2-diimidazole, commonly referred to as "TCDM-HABI", the document mentions that the use of at least one pro
- the HABI of water substituents (such as methoxy) can greatly reduce the amount of sludge in the used developer.
- HABI photoinitiators are a type of photoinitiator known in the photoresist field, and can be prepared by oxidative coupling of triphenylimidazoles or substituted triphenylimidazoles. Specific preparation processes can refer to, for example, US3784557, US4622286, and US4311783 Etc. in the prior art (the entire contents of which are hereby incorporated by reference). On the basis of the existing process, adding a solvent recrystallization process can easily obtain HABI mixed photoinitiators that meet the above composition requirements of the present invention.
- the solvent may be one or a combination of two or more of toluene, methanol, ethyl acetate, dichloromethane, and water.
- the photosensitive resin composition of the present invention generally includes, in addition to the HABI-based mixed photoinitiator, an alkali-soluble polymer; a compound having an ethylenically unsaturated double bond; other photoinitiators and/or sensitizers; And optional additives.
- the alkali-soluble polymer can impart a film-forming function to the photosensitive resin composition.
- As the alkali-soluble polymer as long as it has such characteristics, it can be applied without particular limitation.
- the applicable alkali-soluble polymer may be (meth)acrylic polymer, styrene polymer, epoxy polymer, aliphatic polyurethane (meth)acrylate polymer, aromatic polyurethane (method Group) acrylate polymer, amide resin, amide epoxy resin, alkyd resin, phenol resin, etc.
- the alkali-soluble polymer can be obtained by radical polymerization of a polymerizable monomer.
- the polymerizable monomer include styrene, vinyl toluene, ⁇ -methylstyrene, p-methylstyrene, p-ethylstyrene, p-chlorostyrene, etc.
- Maleic acid monoester fumaric acid, cinnamic acid, ⁇ -cyanocinnamic acid, itaconic acid, crotonic acid, propanoic acid, N-vinyl caprolactam; N-vinyl pyrrolidone, etc.
- These polymerizable monomers may be used alone or in combination of two or more.
- the alkali-soluble polymer having a carboxyl group may be an acrylic resin containing (meth)acrylic acid as a monomer unit, which is introduced into the carboxyl group by using (meth)acrylic acid as a monomer unit; it may further contain (meth)acrylic acid in addition ( A copolymer of alkyl methacrylate as a monomer unit; it may also contain a polymerizable monomer other than (meth)acrylic acid and alkyl (meth)acrylate in addition to (meth)acrylic acid (such as A copolymer having an ethylenically unsaturated group as a monomer component.
- the carboxyl group-containing alkali-soluble polymer can be obtained by radical polymerization of a polymerizable monomer having a carboxyl group and other polymerizable monomers, especially from (meth)acrylate, ethylenically unsaturated carboxylic acid and other (Meth) acrylate polymer made by copolymerization of comonomers.
- the (meth)acrylate may be methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate , Hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, (meth)acrylic acid Decyl ester, undecyl (meth)acrylate, dodecyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, diethyl (meth)acrylate Aminoethyl, (meth)acrylate dimethylaminoethyl, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, furfuryl (meth)acrylate
- the ethylenically unsaturated carboxylic acid may be acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, with acrylic acid and methacrylic acid being particularly preferred. These ethylenically unsaturated carboxylic acids may be used alone or in combination of two or more.
- the other copolymerizable monomers may be (meth)acrylamide, n-butyl (meth)acrylate, styrene, vinyl naphthalene, (meth)acrylonitrile, vinyl acetate, vinyl cyclohexane Wait. These other copolymerizable monomers may be used alone or in combination of two or more.
- the alkali-soluble polymer may be used alone or in combination of two or more.
- Examples of the alkali-soluble polymers used in combination of two or more include two or more types of alkali-soluble polymers composed of different copolymerization components, two or more types of alkali-soluble polymers with different weight average molecular weights, and two types with different degrees of dispersion. The above alkali-soluble polymers, etc.
- the weight-average molecular weight of the alkali-soluble polymer is not particularly limited, but in terms of mechanical strength and alkali developability, the weight-average molecular weight is preferably 15,000 to 200,000, and more preferably 30,000 to 150,000, particularly preferably 30000-120000.
- the weight average molecular weight is greater than 15,000, the developer resistance after exposure tends to be further improved, and when the weight average molecular weight is less than 200,000, the development time tends to become shorter, and can maintain other components such as photoinitiator Of compatibility.
- the weight-average molecular weight of the alkali-soluble polymer is measured by gel permeation chromatography (GPC), and is obtained by conversion using a standard polystyrene standard curve.
- the acid value of the alkali-soluble polymer is preferably 50-300 mgKOH/g, more preferably 50-250 mgKOH/g, still more preferably 70-250 mgKOH/g, and particularly preferably 100- 250mgKOH/g.
- the acid value of the alkali-soluble resin is less than 50 mgKOH/g, it is difficult to ensure a sufficient development speed.
- it exceeds 300 mgKOH/g the adhesion is reduced, pattern short-circuiting is likely to occur, and the storage stability and viscosity of the composition are prone to occur. The problem of rising.
- the molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the alkali-soluble resin is preferably 1.5 to 6.0, and particularly preferably 1.8 to 3.7. When the molecular weight distribution is within the above range, the developability is excellent.
- the content of the alkali-soluble polymer in the composition is preferably 20 to 70 parts by mass, more preferably 30 to 60 parts by mass based on 100 parts by mass of the total photosensitive resin composition.
- the content of the alkali-soluble polymer is 20 parts by mass or more, the durability of the photosensitive resin composition to plating treatment, etching treatment, etc. can be improved, and when the content is 70 parts by mass or less, it is beneficial to improve the photosensitive resin composition Sensitivity.
- the compound having an ethylenically unsaturated double bond can promote the film formation of the photosensitive resin composition.
- the compound having an ethylenically unsaturated double bond is not particularly limited, and a photopolymerizable compound having at least one ethylenically unsaturated bond in the molecule can be used.
- Illustrative examples include: compounds obtained by reacting ⁇ , ⁇ -unsaturated carboxylic acids with polyols, bisphenol A (meth)acrylate compounds, ⁇ , ⁇ -unsaturated carboxylic acids and glycidyl groups The compound obtained by the reaction of the compound, a urethane monomer such as a (meth)acrylate compound having a urethane bond in the molecule, nonylphenoxypolyvinyloxyacrylate, ⁇ -chloro- ⁇ -hydroxypropyl - ⁇ '-(meth)acryloyloxyethyl-phthalate, ⁇ -hydroxyethyl- ⁇ '-(meth)acryloyloxyethyl-phthalate, ⁇ -hydroxypropyl- ⁇ '-(meth)
- Examples of the compound obtained by reacting the above-mentioned ⁇ , ⁇ -unsaturated carboxylic acid with a polyhydric alcohol include polyethylene glycol di(meth)acrylate having an ethyleneoxy number of 2-14, and the number of propyleneoxy groups being Polypropylene glycol di(meth)acrylate of 2-14, polyethyleneoxy ⁇ polypropyleneoxydiol di(methyl) with an ethyleneoxy number of 2-14 and a propyleneoxy number of 2-14 Acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, EO modified trimethylolpropane tri(meth)acrylate, PO modified trihydroxy Methylpropane tri(meth)acrylate, EO, PO modified trimethylolpropane tri(meth)acrylate, tetramethylolmethane tri(meth)acrylate, tetramethylolmethane tetra(meth)acrylate Base)
- EO means ethylene oxide
- PO means propylene oxide
- the compound modified with PO means a compound having a block structure of an oxypropylene group.
- Examples of the bisphenol A-based (meth)acrylate compound include 2,2-bis(4-((meth)acryloyloxypolyethoxy)phenyl)propane, 2,2- Bis(4-((meth)acryloyloxypolypropoxy)phenyl)propane, 2,2-bis(4-((meth)acryloyloxypolybutoxy)phenyl)propane, 2,2-bis(4-((meth)acryloyloxypolyethoxypolypropoxy)phenyl)propane, etc.
- 2,2-bis(4-((meth)acryloyloxypolyethoxy)phenyl)propane examples include 2,2-bis(4-((meth)acryloyloxy Diethoxy)phenyl)propane, 2,2-bis(4-((meth)acryloyloxytriethoxy)phenyl)propane, 2,2-bis(4-((methyl ) Acryloyloxytetraethoxy)phenyl)propane, 2,2-bis(4-((meth)acryloyloxypentethoxy)phenyl)propane, 2,2-bis(4- ((Meth)acryloyloxyhexaethoxy)phenyl)propane, 2,2-bis(4-((meth)acryloyloxyheptethoxy)phenyl)propane, 2,2- Bis(4-((meth)acryloyloxyoctaethoxy)phenyl)propane, 2,2-bis(4-((meth)acryl
- the number of oxyethylene groups per molecule of the 2,2-bis(4-((meth)acryloyloxypolyethoxy)phenyl)propane is preferably 4-20, and more preferably 8-15. These compounds may be used alone or in combination of two or more.
- the (meth)acrylate compound having a urethane bond in the molecule a (meth)acrylic monomer having an OH group at the ⁇ position and a diisocyanate compound (isophorone diisocyanate, 2 , 6-toluene diisocyanate, 2,4-toluene diisocyanate, 1,6-hexamethylene diisocyanate, etc.) addition reaction product, tri((meth)acryloyloxytetraethylene glycol isocyanate ) Hexamethylene isocyanurate, EO modified urethane di(meth)acrylate, PO modified urethane di(meth)acrylate, EO, PO modified urethane di(meth)acrylic acid Ester etc. These compounds may be used alone or in combination of two or more.
- nonylphenoxypolyvinyloxy acrylate examples include nonylphenoxytetravinyloxy acrylate, nonylphenoxypentavinyloxy acrylate, and nonylphenoxyhexaethylene.
- phthalic acid compounds examples include ⁇ -chloro- ⁇ -hydroxypropyl- ⁇ '-(meth)acryloyloxyethyl phthalate and ⁇ -hydroxyalkyl- ⁇ '-(Meth)acryloyloxyalkyl phthalate, etc. These compounds may be used alone or in combination of two or more.
- alkyl (meth)acrylate examples include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, N-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, phenyl (meth)acrylate, (meth) ) Isobornyl acrylate, hydroxymethyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, (meth)acrylic acid 2-hydroxypropyl ester, benzyl (meth)acrylate, amyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isooctyl (
- methyl (meth)acrylate preferred are methyl (meth)acrylate, ethyl (meth)acrylate, trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, Pentaerythritol tri(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexaacrylate. These compounds may be used alone or in combination of two or more.
- the compound having an ethylenically unsaturated double bond is preferably a bisphenol A-based (meth)acrylate compound and a compound having a urethane bond in the molecule ( Meth)acrylate compound. From the viewpoint of improving sensitivity and resolution, a bisphenol A (meth)acrylate compound is preferred.
- 2,2-bis(4-((meth)acryloyloxypolyethoxy)phenyl)propane such as Shin Nakamura Chemical Industry Co., Ltd., BPE-200
- polyethoxybisphenol A methacrylate such as Shin Nakamura Chemical Industry Co., Ltd., BPE-5000; Hitachi Chemical Co., Ltd., FA-321M
- 2-bis(4-((meth)acryloyloxypolybutoxy)phenyl)propane such as Shin Nakamura Chemical Industry Co., Ltd., BPE-1300
- the content of the compound having an ethylenically unsaturated double bond is preferably 20-50 parts by mass, and more preferably 25-45 parts by mass.
- the sensitivity and resolution of the photosensitive resin composition will be further improved; when the content is less than 50 parts by mass, the photosensitive resin composition is easier It is thinned and the durability against etching is further improved.
- the HABI hybrid photoinitiator of the present invention has the structure shown in the general formula (I), which contains four connections of 1'-2, 2-3', 1-2' and 2'-3 Bis-imidazole compound, and the total mass percentage of the four-linked bis-imidazole compound in the mixed photoinitiator is 92% or more, preferably 95% or more, and particularly preferably 100%,
- Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , and Ar 6 may be the same or different, and each independently represents a substituted or unsubstituted aryl group.
- the HABI-based hybrid photoinitiator of the present invention may be selected from or include:
- compounds such as compound A1 and compound A2 may exist alone, or two or more kinds may be used in combination.
- the hexaarylbisimidazole-based mixed photoinitiator of the present invention is preferably 1 to 10 parts by mass. Within this content range, the composition can exhibit good system compatibility and excellent curing performance.
- the photosensitive resin composition of the present invention may further contain other photoinitiators and/or sensitizers to increase the compatibility, sensitivity, and resolution of the photosensitive resin system through a common/synergistic effect.
- the other photoinitiators and/or sensitizers may include (but are not limited to): diimidazoles, pyrazolines, aromatic ketones, anthraquinones, benzoin and benzoin alkyl ethers, Oxime esters, triazines, triphenylamines, coumarins, thioxanthones, acridines and other photoinitiators known to those skilled in the art. These photoinitiators can be used alone or in combination of two or more.
- the bisimidazole compounds include: 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-diimidazole, 2,2',5-tri(o Chlorophenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl-1,1'-diimidazole, 2,2',5-tri(2-fluoro Phenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl-diimidazole, 2,2'-bis(2,4-dichlorophenyl)-4 ,4',5,5'-tetraphenyl-diimidazole, 2,2'-bis(2-fluorophenyl)-4-(o-chlorophenyl)-5-(3,4-dimethoxy Phenyl)-4',5'-diphenyl-diimidazole, 2,2'-bis(
- the pyrazoline compounds include: 1-phenyl-3-(4-tert-butylstyryl)-5-(4-tert-butylphenyl)pyrazoline, 1-phenyl-3 -Biphenyl-5-(4-tert-butylphenyl) pyrazoline, ethoxylated (9) trimethylol pyrazoline ester, ethoxylated (10) bisphenol A pyrazoline ester And the like. These pyrazoline compounds may be used alone or in combination of two or more.
- the aromatic ketone compounds include: acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1 ,1-dichloroacetophenone, benzophenone, 4-benzoyldiphenyl sulfide, 4-benzoyl-4'-methyldiphenyl sulfide, 4-benzoyl-4'-ethyl Diphenyl sulfide, 4-benzoyl-4'-propyl diphenyl sulfide, 4,4'-bis(diethylamino) benzophenone, 4-p-toluene mercaptobenzophenone, 2 ,4,6-trimethylbenzophenone, 4-methylbenzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(methyl, ethyl (Amino) benzophenone, acetophenone dimethyl ketal, benzyl dimethyl
- the anthraquinone compounds include: 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 2,3-dimethylanthraquinone, 2-ethylanthracene-9,10-diethyl, 1,2,3-trimethylanthracene-9,10-dioctyl fat, 2-ethylanthracene-9,10-bis(4-chlorobutyric acid Methyl ester), 2-(3-((3-ethyloxetan-3-yl)methoxy)-3-oxopropyl)anthracene-9,10-diethyl ester, 9,10 -Dibutoxyanthracene, 9,10-diethoxy-2-ethylanthracene, 9,10-bis(3-chloropropoxy)anthracene, 9,10-bis(2-hydroxye
- benzoin and benzoin alkyl ether compounds include: benzoin methyl ether, benzoin ethyl ether, benzoin phenyl ether and the like. These benzoin and benzoin alkyl ether compounds may be used alone or in combination of two or more.
- the oxime ester compounds include: 1-(4-phenylthiophenyl)-n-octane-1,2-dione-2-benzoic acid oxime ester, 1-(6-(2-methyl Benzoyl)-9-ethylcarbazol-3-yl)-ethane-1-one-oxime acetate, 1-(6-(2-methylbenzoyl)-9-ethylcarbazole- 3-yl)-butane-1-one-oxime acetate, 1-(6-(2-methylbenzoyl)-9-ethylcarbazol-3-yl)-propane-1-one-acetic acid Oxime ester, 1-(6-(2-methylbenzoyl)-9-ethylcarbazol-3-yl)-1-cyclohexyl-methane-1-one-oxime acetate, 1-(6- (2-methylbenzoyl)-9-ethylcarbazol-3-yl)-3-cyclopenty
- triazine compounds include: 2-(4-ethylbiphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(3,4- Methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 3- ⁇ 4-[2,4-bis(trichloromethyl)-s-triazine -6-yl]phenylthio ⁇ propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl-3- ⁇ 4-[2,4-bis(trichloromethyl)-s- Triazin-6-yl]phenylthio ⁇ propionate, ethyl-2- ⁇ 4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio ⁇ ethyl Ester, 2-ethoxyethyl-2- ⁇ 4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]
- the triphenylamine compounds include: N,N-bis-[4-(2-styryl-1-yl)-phenyl]-N,N-bis(2-ethyl-6methylbenzene Group)-1,1-bisphenyl-4,4-diamine, N,N-bis-[4-(2-styryl-1-yl)-4′-methylphenyl]-N, N-bis(2-ethyl-6methylphenyl)-1,1-bisphenyl-4,4-diamine and the like. These triphenylamine compounds may be used alone or in combination of two or more.
- the coumarin compounds include: 3,3'-carbonylbis(7-diethylamine coumarin), 3-benzoyl-7-diethylamine coumarin, 3,3'-carbonyl Bis(7-methoxycoumarin), 7-(diethylamino)-4-methylcoumarin, 3-(2-benzothiazole)-7-(diethylamino)coumarin , 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one (7-(diethylamino)-4-methylcoumarin), 3-benzoyl- 7-Methoxycoumarin and its analogues.
- These coumarin compounds may be used alone or in combination of two or more.
- the thioxanthone compounds include: thioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2 -Chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone and the like. These thioxanthone compounds may be used alone or in combination of two or more.
- acridine compounds include: 9-phenyl acridine, 9-p-methylphenyl acridine, 9-m-methylphenyl acridine, 9-o-chlorophenyl acridine, 9-o-fluorine [4-(9-acridinyl)phenoxy]acetate of phenylacridine, 2-ethyl-2-(hydroxymethyl)-1,3-propanediol ether cyclohexane ether (ie PAD107, Produced by Changzhou Qiangli Electronic New Materials Co., Ltd.), 1,7-bis(9-acridinyl)heptane, 9-ethylacridine, 9-(4-bromophenyl)acridine, 9-(3 -Chlorophenyl) acridine, 1,7-bis(9-acridine) heptane, 1,5-bis(9-acridinepentane), 1,3
- the content of the other photoinitiator and/or sensitizer is not more than 8 parts by mass.
- the photosensitive resin composition of the present invention may optionally contain an appropriate amount of other auxiliary agents as needed.
- the auxiliary agent may be dyes such as malachite green, tribromophenyl sulfone, colorless crystal violet and other light color developers, pigments, fillers, plasticizers, stabilizers, coating aids, peeling accelerators, etc. .
- dyes, pigments, and photochromic agents exemplarily, tris(4-dimethylaminophenyl)methane, tris(4-dimethylamino-2methylphenyl)methane, fluorane Phthalocyanines such as dyes, toluenesulfonic acid monohydrate, basic magenta, phthalocyanine green and phthalocyanine blue, auramine, by-product magenta, crystal violet, methyl orange, Nile blue 2B, Victoria blue, peacock Green, Diamond Green, Basic Blue 20, Brilliant Green, Eosin, Ethyl Violet, Erythrosine Sodium B, Methyl Green, Phenolphthalein, Alizarin Red S, Thymol Phenolphthalein, Methyl Violet 2B, Quinadine Red, Rose Bengal Agar, Mitaniel Yellow, Thymol Sulfophthalein, Xylenol Blue, Methyl Orange, Orange IV, Diphenyl Fluorane Phthalocyanines
- tris(4-dimethylaminophenyl)methane ie, leuco crystal violet, LCV.
- These dyes, pigments and photochromic agents may be used alone or in combination of two or more.
- fillers such as silica, alumina, talc, calcium carbonate, and barium sulfate (excluding the above-mentioned inorganic pigments) may be used.
- the filler may be used alone or in combination of two or more.
- plasticizer for example, it may be: phthalate such as dibutyl phthalate, diheptyl phthalate, dioctyl phthalate, diallyl phthalate, etc.
- Glycol esters such as acid esters, triethylene glycol diacetate, tetraethylene glycol diacetate, sulfonamides such as p-toluenesulfonamide, benzenesulfonamide, n-butylbenzenesulfonamide, triphenyl phosphate, Trimethyl phosphate, triethyl phosphate, triphenyl phosphate, tricresyl phosphate, tricresyl phosphate, tolyl diphenyl phosphate, tricresyl phosphate, 2-naphthyl Diphenyl phosphate, tolyl bis 2,6-xylyl phosphate, aromatic condensed phosphate, tri(chloropropy
- the above stabilizer exemplarily, it may be: hydroquinone, 1,4,4-trimethyl-diazobicyclo(3.2.2)-non-2-ene-2,3-dioxide, 1 -Phenyl-3-pyrazolidone, p-methoxyphenol, alkyl and aryl substituted hydroquinones and quinones, tert-butylcatechol, 1,2,3-pyrogallol, copper resinate, naphthalene Amine, ⁇ -naphthol, cuprous chloride, 2,6-di-tert-butyl-p-cresol, phenothiazine, pyridine, nitrobenzene, dinitrobenzene, p-toluoquinone and chloroquinone.
- the stabilizer may be used alone or in combination of two or more.
- the coating aid from the viewpoint of safety and versatility, it may be: acetone, methanol, methyl alcohol, ethyl alcohol, isopropyl alcohol, methyl ethyl ketone, propylene glycol monomethyl ether acetate , Ethyl lactate, cyclohexanone, ⁇ -butyrolactone, dichloromethane, etc.
- the coating aid may be used alone or in combination of two or more.
- peeling accelerator examples include benzenesulfonic acid, toluenesulfonic acid, xylenesulfonic acid, phenolsulfonic acid, methyl, propyl, heptyl, octyl, decyl, and dodecane Alkylbenzene sulfonic acid, etc.
- the peeling accelerator may be used alone or in combination of two or more.
- the content of the auxiliary agent is not more than 10 parts by mass.
- the photosensitive resin composition of the present invention can be prepared as a dry film, that is, a photosensitive resin laminate, and is used in the manufacture of printed circuit boards, protective patterns, conductor patterns, lead wires, and semiconductor packages through different processes in different The desired pattern is formed on the substrate.
- the photosensitive resin composition of the present invention can also be applied to the corresponding substrate in each corresponding manufacturing step by a wet film coating machine, that is, used as a wet film for printed circuit boards, protective patterns, conductor patterns, frame wires, In the manufacture of semiconductor packages, different patterns are formed on different substrates through different processes.
- the photosensitive resin laminate which is a dry film of the present invention includes a photosensitive resin layer formed of a photosensitive resin composition and a support that supports the photosensitive resin layer.
- the production of a dry film includes: coating a photosensitive resin composition on a support and drying to form a photosensitive resin layer; optionally, attaching a cover film (protective layer) as needed.
- the drying conditions are at 60-100°C for 0.5-15 min.
- the thickness of the photosensitive resin layer is preferably 5-95 ⁇ m, more preferably 10-50 ⁇ m, and more preferably 15-30 ⁇ m. If the thickness of the photosensitive resin layer is less than 5 ⁇ m, the insulation is not good, and if the thickness of the photosensitive resin layer exceeds 95 ⁇ m, the resolution may be poor.
- plastic films such as polyethylene terephthalate, polyethylene naphthalate, polypropylene, polyethylene, cellulose acetate, polyalkylmethacrylate Ester, methacrylate copolymer, polyvinyl chloride, polyvinyl alcohol, polycarbonate, polystyrene, cellophane, vinyl chloride copolymer, polyamide, polyimide, ethylene chloride-vinyl acetate copolymer, polytetramethylene Vinyl fluoride, polytrifluoroethylene and the like.
- composite materials composed of two or more materials can also be used.
- polyethylene terephthalate having excellent light penetration is used.
- the thickness of the support is preferably 5-150 ⁇ m, and more preferably 10-50 ⁇ m.
- the coating of the photosensitive resin composition is not particularly limited, and for example, a spray coating method, a drum coating method, a spin coating method, a slit coating method, a compression coating method, a curtain coating method, and a dye coating can be used Conventional methods such as cloth method, line coating method, blade coating method, roll coating method, blade coating method, spray coating method, dip coating method, etc.
- the present invention provides the application of the above dry film in the manufacture of printed circuit boards, including:
- Lamination step Laminating a photosensitive resin laminate on a copper-clad laminate or flexible substrate;
- Exposure step Expose the photosensitive resin layer in the photosensitive resin laminate, and irradiate active light in the form of an image to photocur the exposed portion;
- Conductor pattern forming process etching or plating the part of the surface of the copper-clad laminate or flexible substrate that is not covered by the protection pattern;
- Peeling step peeling the protective pattern from the copper-clad laminate or flexible substrate.
- the present invention provides the application of the above dry film in manufacturing a protective pattern, including the above-mentioned lamination step, exposure step and development step, the difference is that in the lamination step, the photosensitive resin laminate can be laminated on various materials On the substrate.
- the present invention provides the application of the above dry film in manufacturing a conductor pattern, including the above-mentioned lamination step, exposure step, development step, and conductor pattern formation step, except that in the lamination step, the photosensitive resin laminate is laminated on the metal Board or metal-coated insulating board.
- the present invention provides the application of the above dry film in manufacturing a frame wire, including the above-mentioned lamination step, exposure step, development step, and conductor pattern forming step, except that the photosensitive resin laminate is laminated in the lamination step On the metal plate, the part not covered by the protection pattern is etched in the conductor pattern forming process.
- the present invention provides the application of the above dry film in the manufacture of semiconductor packages, including the above-mentioned lamination step, exposure step, development step, and conductor pattern forming step, the difference is that in the lamination step, the photosensitive resin laminate is laminated on On a wafer with a large-scale integrated circuit, the part not covered by the protection pattern is plated in the conductor pattern forming process.
- the photosensitive resin composition of the present invention can be directly applied on a substrate by a wet film method, and is used for the manufacture of printed circuit boards, protective patterns, conductor patterns, lead wires, semiconductor packages, and the like.
- the photosensitive resin composition can be applied on the substrate by conventional methods such as roll coating, blade coating, spray coating, and dip coating, and dried to form the photosensitive resin layer.
- the exposure may include a mask exposure method (a method in which a negative or positive mask pattern of a wiring pattern irradiates active light in the form of an image), a projection exposure method, or a direct imaging exposure method using laser, digital optics
- a mask exposure method a method in which a negative or positive mask pattern of a wiring pattern irradiates active light in the form of an image
- a projection exposure method or a direct imaging exposure method using laser, digital optics
- the method of direct drawing exposure such as the processing exposure method, irradiates the active light in the form of an image.
- a well-known light source such as a carbon arc lamp, a mercury vapor arc lamp, an ultra-high pressure indicator lamp, a high-pressure indicator lamp, a gas laser such as a xenon lamp, an argon laser, a solid laser such as a YAG laser, a semiconductor laser, and gallium nitride can be used It is a blue-violet laser and other light sources that effectively emit ultraviolet light.
- a light source that efficiently emits visible light such as a floodlight for photography or a fluorescent lamp can also be used.
- the photosensitive resin composition of the present invention is not particularly limited to the type of light source of active light, and the exposure amount is preferably 10-1000 mJ/cm 2 .
- the unexposed portion of the photosensitive resin layer is removed with a developer.
- the support When the support is present on the photosensitive resin layer, the support can be removed by an automatic peeler, etc., and then the unexposed portion can be removed using a developer such as an alkaline aqueous solution, an aqueous developer, or an organic solvent.
- a developer such as an alkaline aqueous solution, an aqueous developer, or an organic solvent.
- the alkaline aqueous solution may be 0.1-5 mass% sodium carbonate solution, 0.1-5 mass% potassium carbonate solution, 0.1-5 mass% sodium hydroxide solution, etc.
- the pH value is preferably 9-11.
- Surfactants, defoamers, organic solvents, etc. can also be added to the alkaline aqueous solution.
- the development method may be conventional methods such as dipping, spraying, and brushing.
- the conductor layer of the uncovered circuit-forming substrate is etched away to form a conductor pattern.
- the etching method can be selected according to the conductor layer to be removed.
- examples of the etching solution include copper oxide solution, iron oxide solution, alkali etching solution, hydrogen peroxide-based etching solution, and the like.
- the plating process using the resist pattern formed on the substrate as a mask, copper, solder, or the like is plated on the insulating plate of the uncovered circuit-forming substrate. After the plating process, the resist pattern is removed to form a conductor pattern.
- a method of the plating treatment either electroplating treatment or electroless plating treatment may be used, and electroless plating treatment is preferable.
- Examples of the electroless plating treatment include copper plating such as copper sulfate plating and copper pyrophosphate plating, high-throw solder plating and other solder plating, and watt bath (nickel sulfate-chloride) Nickel) plating and nickel sulfamate plating and other nickel plating, hard gold plating and soft gold plating and other gold plating.
- copper plating such as copper sulfate plating and copper pyrophosphate plating, high-throw solder plating and other solder plating, and watt bath (nickel sulfate-chloride) Nickel) plating and nickel sulfamate plating and other nickel plating, hard gold plating and soft gold plating and other gold plating.
- the resist pattern can be removed by an aqueous solution that is more alkaline than the alkaline aqueous solution used in the development step.
- an aqueous solution that is more alkaline than the alkaline aqueous solution used in the development step.
- a strong alkaline aqueous solution for example, a 1-10% by mass sodium hydroxide aqueous solution can be used.
- Figure 1 is a high performance liquid chromatogram of compound a1.
- Figure 2 is the structure spectrum of T1 obtained by single crystal diffraction
- Figure 3 is a comparison of the sensitivity test results of compounds a1, a2, a3, a8, a9, a10
- the product was analyzed using high performance liquid chromatography.
- Figure 1 is a high performance liquid chromatogram of product a1.
- the analysis result shows that the total content of the product peaks of the four connection sites of 1'-2, 2-3', 1-2' and 2'-3 is 92.5%.
- the product a1 is a mixture obtained from two different monoimidazoles (ie, M1, M2) by pair-wise coupling and mutual coupling, including T1, T2, and T3.
- M1, M2 monoimidazoles
- T1, T2, and T3 the components a1-1, a1-2 and a1-3 were verified and analyzed.
- T1 has only one peak in the liquid phase, but two peak shapes are obtained by single crystal diffraction, see Figure 2. According to the structural characteristics, it can be determined that the main product of the coupling of two monoimidazoles is a mixture of N containing hydrogen on one imidazole and C on the 2-position of the other imidazole, thus indicating that the structure of T1 is The 1-2' and 2'-3 connection positions mentioned above.
- the imidazole used to synthesize T1 is M1, which belongs to symmetric imidazole, so the 1-2' and 2'-3 obtained by coupling are of similar polarity, and the liquid phase is difficult to separate. And because of the structural symmetry of M1, the structure of the product obtained by its own coupling is 1-2' and 1'-2, and 2'-3 and 3-2' are the same, so the main structure of T1 is 1-
- the products of the two connecting positions of 2'and 3-2' have the structural formulas as shown below, respectively T1-1: 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl -1,2'-diimidazole and T1-2: 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-2',3-diimidazole;
- the monoimidazole M2 synthesized by T2 belongs to asymmetric monoimidazole. There are two configurations of M2, M2-1 and M2-2, as shown below:
- T2 is synthesized by asymmetric monoimidazole coupling.
- there are eight main structures connected by 1-2 and 2-3 connecting sites but for the self-coupled monoimidazole, the structure of 1-2' is the same as 1'-2.
- the structure of 2'-3 and 3-2' is also the same, so for T2, there are actually four main structures connected by 1-2 and 2-3 connection sites, and their compositions are:
- T2-1 2,2',5,5'-tetra(o-chlorophenyl)-4,4'-bis(3,4-dimethoxyphenyl)-2',3-diimidazole
- T2 -2 2,2',4,5'-tetra(o-chlorophenyl)-4',5-bis(3,4-dimethoxyphenyl)-1,2'-diimidazole
- T2- 3 2,2',5,5'-tetra(o-chlorophenyl)-4,4'-bis(3,4-dimethoxyphenyl)-1,2'-diimidazole
- T2-4 2,2',4,5'-tetra(o-chlorophenyl)-4',5-bis(3,4-dimethoxyphenyl)-2',3-diimidazole, the structure is shown below :
- T3 is formed by coupling M1 and M2 two by two.
- the main structure of the pure T3 separated in the liquid phase is the product with four kinds of connection positions.
- the structure of the products with four kinds of connection positions is confirmed by LCMS.
- Mass spectrometry analysis obtained molecular fragment peaks of 755 and 756 with the software attached to the instrument.
- the molecular weight of the product was 754, which was consistent with T+1 and T+2, proving that these four products have similar structures and the same molecular weight.
- T3 is formed by connecting symmetrical imidazole M1 and asymmetrical imidazole M2 two by two. There are four main structures connected by 1-2 and 2-3 connection sites, which are composed of:
- T3-1 2,2',5-tris(o-chlorophenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl-1,2'-di Imidazole
- T3-2 2,2',5-tris(o-chlorophenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl-2',3 -Diimidazole
- T3-3 2,2',5-tris(o-chlorophenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl-2, 3'-diimidazole
- T3-4 2,2',5-tris(o-chlorophenyl)-4-(3,4-dimethoxyphenyl)-4',5'-diphenyl- 1',2-Diimidazole, the structural formula is as follows:
- the product a1 is composed of T1 (T1-1, T1-2), T2 (T2-1, T2-2, T2-3, T2-4) and T3 (T3-1, T3-2, T3-3, T3-4) combined, in which the content of the biimidazole compound composed of four connecting positions 1'-2, 2-3', 1-2' and 2'-3 in a1 is 92.5% .
- A2-a10 were prepared separately, and the conditions of each product are shown in Table 1 below.
- solubility of pure HABI (a6 and a7) with a single structure is very poor, and even if it is mixed with other HABI (a4 and a5), the solubility cannot be improved.
- the initiator must have the structure of the same substituent and there are four kinds of linking sites simultaneously to achieve the optimal solubility shown in the present invention.
- the photosensitive resin compositions of Comparative Examples 1-6 were prepared for sensitivity test, and the unit of dosage of each substance in the table was g.
- TMPTA was purchased from Tianjin Beilian Fine Chemical Development Co., Ltd.
- NPG was purchased from Shenzhen Pengshunxing Technology Co., Ltd.
- PGMEA was purchased from Jinan Huifengda Chemical Co., Ltd.
- the peak value represents the maximum heat dissipation, mw/mg, the greater the heat dissipation, the higher the sensitivity.
- the slope represents the curing rate, the smaller the slope, the higher the sensitivity.
- the results are shown in Figure 3.
- the sensitivity test results are: a10 (76.1%) ⁇ a9 (83.0%) ⁇ a8 (88.5%) ⁇ a1 (92.5%) ⁇ a2 (95.6%) ⁇ a3 (98.3).
- This further confirms that the total mass of the biimidazole compound composed of four connection sites of 1'-2, 2-3', 1-2' and 2'-3 in the mixed photoinitiator has a certain effect on the sensitivity, when When the content is higher than 92%, the sensitivity is improved.
- the analysis result shows that the total content of the product peaks of the four connection sites of 1'-2, 2-3', 1-2' and 2'-3 is 92.5%.
- the product a11 is a mixture obtained from two different monoimidazoles (ie, M2 and M3) by pairwise coupling and mutual coupling, including T2, T4 and T5.
- T2, T4 and T5 were analyzed and verified.
- T2, T4 and T5 were obtained respectively, and the structure was confirmed separately.
- T2 has the same structure as compound a1.
- T4 is formed by the coupling of asymmetric monoimidazole M3 itself, there are four main structures connected by 1-2 and 2-3 connection sites, and their composition is:
- T4-1 2,2'-bis(4-chlorophenyl)-5,5'-bis(o-chlorophenyl)-4,4'-bis(3,4-dimethoxyphenyl)- 2,3'-Diimidazole
- T4-2 2,2'-bis(4-chlorophenyl)-4,5'-bis(o-chlorophenyl)-4',5-bis(3,4- Dimethoxyphenyl)-1,2'-diimidazole
- T4-3 2,2'-bis(4-chlorophenyl)-5,5'-bis(o-chlorophenyl)-4,4 '-Bis(3,4-dimethoxyphenyl)-1,2'-diimidazole
- T4-4 2,2'-bis(4-chlorophenyl)-4',5-bis(o Chlorophenyl)-4,5'-bis(3,4-dimethoxyphenyl)-2,3'-diimi
- T5 is formed by the coupling of asymmetric M2 and asymmetric M3, and there are four main structures connected by 1-2 and 2-3 connection sites.
- Their composition is:
- T5-1 2-(4-chlorophenyl)-2', 5,5'-tri(o-chlorophenyl)-4,4'-bis(3,4-dimethoxyphenyl)-2 ,3'-diimidazole
- T5-2 2'-(4-chlorophenyl)-2,5,5'-tri(o-chlorophenyl)-4,4'-bis(3,4-dimethyl Oxyphenyl)-1,2'-diimidazole
- T5-3 2-(4-chlorophenyl)-2',5,5'-tris(o-chlorophenyl)-4,4'-bis (3,4-dimethoxyphenyl)-2',3-diimidazole
- T5-4 2'-(4-chlorophenyl)-2,5,5'-tri(o-chlorophenyl) -4,4'-bis(3,4-dimethoxyphenyl)-1',2-diimidazole
- the product a11 is composed of T2 (T2-1, T2-2, T2-3, T2-4), T4 (T4-1, T4-2, T4-3, T4-4) and T5 ( T5-1, T5-2, T5-3, T5-4), which consists of biimidazole compounds composed of four connecting positions 1'-2, 2-3', 1-2' and 2'-3
- T2 T2-1, T2-2, T2-3, T2-4
- T4 T4-1, T4-2, T4-3, T4-4
- T5 T5-1, T5-2, T5-3, T5-4
- A12-a20 were prepared separately, and the conditions of each product are shown in Table 3 below.
- solubility data in the table above further shows that the solubility of pure HABI (a16 and a17) with a single structure is very poor, and even if it is mixed with other HABI (a14 and a15), the solubility cannot be improved. It is necessary for the structure of the same substituent to have four kinds of connection sites at the same time in order to achieve the optimal solubility shown in the present invention.
- the analysis result showed that the total content of the product peaks of the four connection sites of 1'-2, 2-3', 1-2' and 2'-3 was 92.1%.
- the product a21 is a mixture obtained from two different symmetrical monoimidazoles (ie, M1, M4) by pairwise self-coupling and mutual coupling, including T1, T6, and T7. In order to accurately verify the structure of the product, the components T1, T6 and T7 were verified and analyzed.
- T1, T6 and T7 were obtained respectively, and the structure was confirmed separately.
- T1 has the same structure as compound a1.
- T6 has two structures, but there is only one peak in the liquid phase, and its structural composition is similar to that of T1.
- T6 is obtained by self-coupling of symmetric imidazole, so the polarities of 1-2' and 2'-3 obtained by coupling are similar ,
- the liquid phase is difficult to separate, the structural formula is as follows, respectively T6-1: 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1 , 2'-diimidazole and T6-2: 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-2',3-diimidazole;
- the separated T6 was analyzed, and the structure was confirmed by LCMS. Mass spectrometry analysis obtained 729 and 730 molecular fragment peaks with the software attached to the instrument. The molecular weight of the product was 728, which was in agreement with T+1 and T+2, proving that these two products have similar peak structures and the same molecular weight.
- T7 is formed by coupling symmetrical M1 and symmetrical M4 two by two. There are four main structures connected by 1-2 and 2-3 connection sites, whose composition are:
- T7-1 2-(2,4-dichlorophenyl)-2'-(o-chlorophenyl)-4,4',5,5'-tetraphenyl-2,3'-diimidazole
- T7 -2 2-(2,4-dichlorophenyl)-2'-(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1',2-diimidazole
- T7- 3 2-(2,4-dichlorophenyl)-2'-(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-diimidazole
- T7-4 2-(2,4-dichlorophenyl)-2'-(o-chlorophenyl)-4,4',5,5'-tetraphenyl-2',3-diimidazole, the structural formula is shown below :
- the product a21 is composed of T1 (T1-1, T1-2), T6 (T6-1, T6-2) and T7 (T7-1, T7-2, T7-3, T7-4) It is a combination, in which the content of the biimidazole compound composed of four connecting positions of 1'-2, 2-3', 1-2' and 2'-3 in a21 is 92.1%.
- A22-a30 were prepared separately, and the conditions of each product are shown in Table 4 below.
- the solubility data in the table above further shows that the solubility of pure HABI (a26 and a27) with a single structure is very poor, and even if it is mixed with other HABI (a24 and a25), the solubility cannot be improved.
- the HABI-type mixed photoinitiators described in the present invention It is necessary for the structure of the same substituent to have four kinds of connection sites at the same time in order to achieve the optimal solubility shown in the present invention.
- the analysis result shows that the total content of the product peaks of the four connection sites of 1'-2, 2-3', 1-2' and 2'-3 is 92.7%.
- the product a31 is a mixture obtained from two different symmetrical monoimidazoles (ie, M1, M5) through pairwise self-coupling and mutual coupling, including T1, T8, and T9. In order to accurately verify the structure of the product, the components T1, T8 and T9 were verified and analyzed.
- T1, T8 and T9 were obtained respectively, and the structure was confirmed separately.
- T1 has the same structure as compound a1.
- T8 has two structures, but there is only one peak in the liquid phase, and its structural composition is similar to that of T1.
- T8 is obtained by self-coupling of symmetric imidazole (M5), so the 1-2' and 2'-3 obtained by coupling The polarities are similar, and the liquid phase is difficult to separate.
- the structural formulas are as follows: T8-1: 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetra(2-naphthyl )-1,2'-diimidazole and T8-2: 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetrakis(2-naphthyl)-2',3- Diimidazole
- the separated T8 was analyzed, and the structure was confirmed by LCMS. Mass spectrometry analysis obtained the molecular fragment peaks of 860 and 861 with the software attached to the instrument. The molecular weight of the product was 859, which was in agreement with T+1 and T+2, proving that the two products had similar peak structures and the same molecular weight.
- T9 is formed by coupling symmetrical M1 and symmetrical M5 two by two. There are four main structures connected by 1-2 and 2-3 connection sites, and their composition is:
- T9-1 2,2'-bis(o-chlorophenyl)-4,5-bis(2-naphthyl)-4'5'-diphenyl-1,2'-diimidazole
- T9-2 2,2'-bis(o-chlorophenyl)-4,5-bis(2-naphthyl)-4'5'-diphenyl-2',3-diimidazole
- T9-3 2,2' -Bis(o-chlorophenyl)-4,5-bis(2-naphthyl)-4'5'-diphenyl-1',2-diimidazole
- T9-4 2,2'-bis(o Chlorophenyl)-4,5-bis(2-naphthyl)-4'5'-diphenyl-2,3'-diimidazole, the structural formula is as follows:
- the separated T9 was analyzed, and the structure was confirmed by LCMS.
- the mass spectrometry analysis obtained the molecular fragment peaks of 760 and 761 with the software attached to the instrument.
- the molecular weight of the product was 759, which was consistent with T+1 and T+2, which proved that the four products had similar peak structures and the same molecular weight.
- the product a31 is composed of T1 (T1-1, T1-2), T8 (T8-1, T8-2) and T9 (T9-1, T9-2, T9-3, T9-4) It is a combination, in which the content of the biimidazole compound composed of four connecting positions of 1'-2, 2-3', 1-2' and 2'-3 in a21 is 92.7%.
- A32-a40 were prepared separately, and the conditions of each product are shown in Table 5 below.
- the solubility data in the above table further shows that the solubility of pure HABI (a36 and a37) with a single structure is very poor, and even if it is mixed with other HABI (a34 and a35), the solubility cannot be improved.
- the HABI-type mixed photoinitiators described in the present invention It is necessary for the structure of the same substituent to have four kinds of connection sites at the same time in order to achieve the optimal solubility shown in the present invention.
- the photosensitive resin composition was sufficiently stirred, and it was evenly coated on the surface of a 25 ⁇ m thick polyethylene terephthalate film as a support using a bar coater, and dried in a dryer at 95° C. for 5 minutes. A photosensitive resin layer with a thickness of 40 ⁇ m was formed, and then a 15 ⁇ m-thick polyethylene film as a protective layer was laminated on the surface of the photosensitive resin layer where no polyethylene terephthalate film was laminated to obtain a dry film.
- a 1.2-mm-thick copper-clad laminate laminated with a 35- ⁇ m-thick rolled copper foil was used, and the surface was subjected to wet polishing roll grinding (Scotch-Brite (registered trademark) HD#600 manufactured by 3M Corporation, and passed twice ).
- the polyethylene film protective layer was peeled off from the dry film, and then using a hot roll laminator (AL-70 manufactured by Asahi Kasei Co., Ltd.), it was laminated on a copper clad preheated to 60°C at a roll temperature of 105°C. Laminate.
- the gas pressure is 0.35 MPa, and the lamination speed is 1.5 m/min.
- the mask was placed on a polyethylene terephthalate film as a support, and exposed by an ultra-high pressure mercury lamp (HMW-201KB manufactured by ORCMANUFACTURINGCO., LTD.).
- HMW-201KB manufactured by ORCMANUFACTURINGCO., LTD.
- the polyethylene terephthalate film was peeled off, and a 1% by mass Na 2 CO 3 aqueous solution at 30° C. was sprayed on the photosensitive resin layer using an alkali developing machine (developer for dry film manufactured by FujiKiko Co., Ltd.) Above, the unexposed portion of the photosensitive resin layer is dissolved and removed in a time twice as long as the minimum development time.
- the minimum development time is the shortest time required to completely dissolve the photosensitive resin layer of the unexposed portion.
- the photosensitive resin composition was sufficiently stirred, and the composition was uniformly coated on the surface of a 25 ⁇ m-thick polyethylene terephthalate film as a support using a bar coater. Dry in a dryer at 95°C for 5 min to form a photosensitive resin layer. Then the surface of the photosensitive resin layer was visually inspected and graded as follows:
- the photosensitive resin layer was exposed for 15 minutes using a 21-stage stepped exposure meter manufactured by Stouffer with a 21-stage brightness change from transparent to black to evaluate its sensitivity. After the exposure, development is carried out at twice the minimum development time, and according to the exposure amount of the stepped exposure table with the resist film completely remaining being 8, the following classification is performed:
- the exposure is 20mJ/cm 2 or less
- the exposure is 20mJ/cm 2 -50mJ/cm 2 , excluding the end value;
- the exposure is 50mJ/cm 2 or more.
- the resolution of the dry film was measured.
- the resolution is the minimum value of the pattern after the unexposed portion is cleaned out of the resist pattern formed by development after exposure.
- the resolution value is 30 ⁇ m-50 ⁇ m, excluding the end value
- ⁇ The resolution value is above 50 ⁇ m.
- the hydrophilicity was evaluated by the amount of precipitation after the photosensitive resin layer was dissolved.
- the photosensitive resin composition was sufficiently stirred, and applied uniformly on the surface of a 25 ⁇ m-thick polyethylene terephthalate film as a support using a bar coater. Dry in a dryer at 95°C for 4 minutes to form a photosensitive resin layer with a layer thickness of approximately 30.5 ⁇ m and a layer weight of approximately 3.2 g.
- 0 precipitation amount is less than 0.005g
- 5 Medium amount of light yellow substance (usually fine), the amount of precipitation is between 0.05-0.08g;
- the developability is evaluated according to the following criteria:
- the HABI mixed photoinitiator of the present invention has excellent compatibility when applied to a photosensitive resin composition.
- the composition has high sensitivity, good resolution and developability, and has excellent hydrophilicity, making the developer It can be reused, and there will be no clogging of the filter by developing garbage.
- the comprehensive application performance advantage of the present invention is remarkable.
Abstract
Description
Claims (20)
- 一种六芳基双咪唑类混合光引发剂,具有如通式(I)所示结构,其中含有1’-2、2-3’、1-2’和2’-3四种连接位的双咪唑化合物,且由这四种连接位组成的双咪唑化合物在六芳基双咪唑混合光引发剂中的总质量百分含量为92%以上,A hexaarylbisimidazole mixed photoinitiator with a structure as shown in the general formula (I), which contains four connection positions of 1'-2, 2-3', 1-2' and 2'-3 A double imidazole compound, and the total mass percentage of the double imidazole compound composed of these four connection positions in the hexaarylbisimidazole mixed photoinitiator is more than 92%,通式(I)中,Ar 1、Ar 2、Ar 3、Ar 4、Ar 5、Ar 6可以相同也可以不同,各自独立地表示取代或未取代的芳基。 In the general formula (I), Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , and Ar 6 may be the same or different, and each independently represents a substituted or unsubstituted aryl group.
- 根据权利要求1所述的六芳基双咪唑类混合光引发剂,其特征在于,满足通式(I)所示结构的1’-2、2-3’、1-2’和2’-3四种连接位的双咪唑化合物具有下列结构:The hexaarylbisimidazole-based mixed photoinitiator according to claim 1, characterized in that it satisfies 1'-2, 2-3', 1-2' and 2'- of the structure represented by the general formula (I) 3 Four kinds of biimidazole compounds at the linking position have the following structure:
- 根据权利要求1或2所述的六芳基双咪唑类混合光引发剂,其特征在于:芳基上的取代基为卤素、硝基、氰基、胺基、羟基、C 1-C 20的烷基或链烯基、C 1-C 8的烷氧基,其中各独立变量中的亚甲基可以任选地被氧、硫、亚胺基所取代。 The hexaarylbisimidazole mixed photoinitiator according to claim 1 or 2, wherein the substituents on the aryl group are halogen, nitro, cyano, amine, hydroxyl, C 1 -C 20 Alkyl or alkenyl, C 1 -C 8 alkoxy, wherein the methylene in each independent variable may be optionally substituted with oxygen, sulfur, imino.
- 根据权利要求1-3中任一项所述的六芳基双咪唑类混合光引发剂,其特征在于:芳基上的取代基为氟、氯、溴、硝基、氰基、胺基、羟基、C 1-C 10的烷基或链烯基、C 1-C 5的烷氧基,其中各独立变量中的亚甲基可以任选地被氧、硫、亚胺基所取代。 The hexaarylbisimidazole mixed photoinitiator according to any one of claims 1-3, wherein the substituents on the aryl group are fluorine, chlorine, bromine, nitro, cyano, amine, Hydroxyl group, C 1 -C 10 alkyl group or alkenyl group, C 1 -C 5 alkoxy group, wherein the methylene group in each independent variable may be optionally substituted by oxygen, sulfur, imine group.
- 根据权利要求1-4中任一项所述的六芳基双咪唑类混合光引发剂,其特征在于:Ar 1、Ar 2、Ar 3、Ar 4、Ar 5、Ar 6中至少一个是含有卤素取代基的芳基。 The hexaarylbisimidazole mixed photoinitiator according to any one of claims 1 to 4 , wherein at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 contains The aryl group of the halogen substituent.
- 根据权利要求5所述的六芳基双咪唑类混合光引发剂,其特征在于:所述的卤素取代基为氯。The hexaarylbisimidazole mixed photoinitiator according to claim 5, wherein the halogen substituent is chlorine.
- 根据权利要求1-6中任一项所述的六芳基双咪唑类混合光引发剂,其特征在于:满足通式(I)所示结构的1’-2、2-3’、1-2’和2’-3四种连接位的双咪唑化合物在混合光引发剂中的总质量百分含量为95%以上。The hexaarylbisimidazole mixed photoinitiator according to any one of claims 1-6, characterized in that it satisfies 1'-2, 2-3', 1- that satisfy the structure represented by the general formula (I) The total mass percentage content of the 4′ and 2′-3 biimidazole compounds in the mixed photoinitiator is more than 95%.
- 根据权利要求1-7中任一项所述的六芳基双咪唑类混合光引发剂,其特征在于:由满足通式(I)所示结构的1’-2、2-3’、1-2’和2’-3四种连接位的双咪唑化合物组成。The hexaarylbisimidazole-based mixed photoinitiator according to any one of claims 1 to 7, characterized in that: 1'-2, 2-3', 1 satisfying the structure represented by the general formula (I) -2'and 2'-3 four imidazole compounds connected position.
- 感光性树脂组合物,含有权利要求1-9中任一项所述的六芳基双咪唑类混合光引发剂。A photosensitive resin composition containing the hexaarylbisimidazole mixed photoinitiator according to any one of claims 1-9.
- 根据权利要求9所述的感光性树脂组合物,还包含:碱可溶性聚合 物,具有烯属不饱和双键的化合物,其它光引发剂和/或增感剂,以及任选的助剂。The photosensitive resin composition according to claim 9, further comprising: an alkali-soluble polymer, a compound having an ethylenically unsaturated double bond, other photoinitiators and/or sensitizers, and optional auxiliary agents.
- 根据权利要求10所述的感光性树脂组合物,其特征在于:所述的碱可溶性聚合物选自(甲基)丙烯酸系聚合物、苯乙烯系聚合物、环氧系聚合物、脂肪族聚氨酯(甲基)丙烯酸酯聚合物、芳香族聚氨酯(甲基)丙烯酸酯聚合物、酰胺系树脂、酰胺环氧系树脂、醇酸系树脂、以及酚醛系树脂。The photosensitive resin composition according to claim 10, wherein the alkali-soluble polymer is selected from (meth)acrylic polymer, styrene polymer, epoxy polymer, and aliphatic polyurethane (Meth)acrylate polymer, aromatic urethane (meth)acrylate polymer, amide resin, amide epoxy resin, alkyd resin, and phenol resin.
- 根据权利要求10或11所述的感光性树脂组合物,其特征在于:所述碱可溶性聚合物是含羧基的碱可溶性聚合物。The photosensitive resin composition according to claim 10 or 11, wherein the alkali-soluble polymer is an alkali-soluble polymer containing a carboxyl group.
- 根据权利要求12所述的感光性树脂组合物,其特征在于:所述含羧基的碱可溶性聚合物是由(甲基)丙烯酸酯、乙烯性不饱和羧酸和其它可共聚单体共聚而成的(甲基)丙烯酸酯系聚合物。The photosensitive resin composition according to claim 12, wherein the carboxyl group-containing alkali-soluble polymer is formed by copolymerizing (meth)acrylate, ethylenically unsaturated carboxylic acid, and other copolymerizable monomers (Meth)acrylate polymer.
- 根据权利要求10所述的感光性树脂组合物,其特征在于:所述具有烯属不饱和双键的化合物是在分子内具有至少一个乙烯性不饱和键的光聚合性化合物。The photosensitive resin composition according to claim 10, wherein the compound having an ethylenically unsaturated double bond is a photopolymerizable compound having at least one ethylenically unsaturated bond in the molecule.
- 根据权利要求10或14所述的感光性树脂组合物,其特征在于:所述具有烯属不饱和双键的化合物选自双酚A类(甲基)丙烯酸酯化合物和分子内具有氨酯键的(甲基)丙烯酸酯化合物。The photosensitive resin composition according to claim 10 or 14, wherein the compound having an ethylenically unsaturated double bond is selected from bisphenol A (meth)acrylate compounds and has a urethane bond in the molecule (Meth)acrylate compound.
- 根据权利要求10所述的感光性树脂组合物,其特征在于:所述其它光引发剂和/或增感剂选自双咪唑类、吡唑啉类、芳香族酮类、蒽醌类、苯偶姻和苯偶姻烷基醚类、肟酯类、三嗪类、三苯胺类、香豆素类、噻吨酮类、吖啶类光引发剂中的至少一种。The photosensitive resin composition according to claim 10, wherein the other photoinitiator and/or sensitizer is selected from the group consisting of diimidazoles, pyrazolines, aromatic ketones, anthraquinones, and benzene At least one of benzoin and benzoin alkyl ethers, oxime esters, triazines, triphenylamines, coumarins, thioxanthones, and acridine photoinitiators.
- 根据权利要求10所述的感光性树脂组合物,其特征在于:所述助剂选自染料、光显色剂、颜料、填充剂、增塑剂、稳定剂、涂布助剂、剥 离促进剂中的至少一种。The photosensitive resin composition according to claim 10, wherein the auxiliary agent is selected from the group consisting of dyes, photochromic agents, pigments, fillers, plasticizers, stabilizers, coating aids, and peeling accelerators At least one of them.
- 感光性树脂层叠体,包含:权利要求9-17中任一项所述的感光性树脂组合物形成的感光性树脂层,以及支撑该感光性树脂层的支撑体。A photosensitive resin laminate comprising: the photosensitive resin layer formed of the photosensitive resin composition according to any one of claims 9-17; and a support for supporting the photosensitive resin layer.
- 权利要求18所述的感光性树脂层叠体在制造印刷电路板、保护图案、导体图案、引框线、半导体封装中的应用。Use of the photosensitive resin laminate according to claim 18 in the manufacture of printed circuit boards, protective patterns, conductor patterns, lead wires, and semiconductor packages.
- 权利要求9-17中任一项所述的感光性树脂组合物在制造印刷电路板、保护图案、导体图案、引框线、半导体封装中的应用。Use of the photosensitive resin composition according to any one of claims 9 to 17 in the manufacture of printed circuit boards, protective patterns, conductor patterns, lead wires, and semiconductor packages.
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