WO2021049563A1 - 光塩基発生剤、化合物、光反応性組成物及び反応生成物 - Google Patents

光塩基発生剤、化合物、光反応性組成物及び反応生成物 Download PDF

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WO2021049563A1
WO2021049563A1 PCT/JP2020/034262 JP2020034262W WO2021049563A1 WO 2021049563 A1 WO2021049563 A1 WO 2021049563A1 JP 2020034262 W JP2020034262 W JP 2020034262W WO 2021049563 A1 WO2021049563 A1 WO 2021049563A1
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group
compound
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晃 有光
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Tokyo University of Science
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    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C07C59/11—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
    • C07D311/86—Oxygen atoms, e.g. xanthones
    • 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
    • C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F122/10—Esters
    • C08F122/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5046—Amines heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/66—Mercaptans
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • One may be bonded to each other to form a ring structure.
  • the structure represented by the general formula (1) -13 has a ring structure formed by bonding R 31 and R 33 to each other, the said structure.
  • the ring structure is not a ring structure showing aromaticity.
  • a first skeleton represented by the following general formula (a) and a second skeleton having a nitrogen atom which is bonded to the bond position of the first skeleton to form an amide group are provided.
  • a compound in which a base in which a hydrogen atom is bonded to the nitrogen atom of the second skeleton is generated by light irradiation, and the pKa of the conjugate acid of the base in water is 12 or more.
  • the nitrogen atom in the second skeleton which was bonded to the carbon and bonded to the carbonyl carbon, dissociates and bonds to the hydrogen atom.
  • the compound represented by the following general formula (1') and the amine compound represented by HX are generated.
  • the generated amine compound is a base, and the conjugate acid of this base has a pKa of 12 or more in water.
  • the decarboxylation reaction does not occur by light irradiation.
  • the decarboxylation reaction does not occur by light irradiation.
  • substituted alkyl group may be linear, branched or cyclic. When it is annular, it may be either monocyclic or polycyclic.
  • the substituted alkyl group preferably has 1 to 10 carbon atoms.
  • the linear or branched alkyl group preferably has 1 to 10 carbon atoms, and is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and the like.
  • R 1 to R 4 are independently each of a hydrogen atom, the substituted alkyl group, an alkoxy group, an aryloxy group, a dialkylamino group, a diarylamino group, an alkylarylamino group and an alkylcarbonyl.
  • the second skeleton preferably has a structure represented by the following general formula (1) -12, (1) -13 or (1) -14, and the following general formula (1) -13 or (1)-. It is more preferable that the structure is represented by 14.
  • the ring formed thereby may be either monocyclic or polycyclic.
  • the content of the photobase generator is preferably 4% by mass to 39% by mass, preferably 6% by mass to 36% by mass, based on the content of the base-reactive compound. It is more preferably%, and further preferably 8% by mass to 33% by mass.
  • the content of the photobase generator is 4% by mass or more, the reaction of the base-reactive compound proceeds more easily. Further, when the content of the photobase generator is 39% by mass or less, excessive use of the photobase generator is suppressed.
  • the photoreactive composition of the present disclosure may further contain other components in addition to the base-reactive compound and the photo-base generator.
  • the other components are not particularly limited as long as the effects of the present invention are not impaired, and can be arbitrarily selected depending on the intended purpose.
  • the other components contained in the photoreactive composition may be only one kind, may be two or more kinds, and when there are two or more kinds, the combination and ratio thereof can be arbitrarily set.
  • the thickness of the reaction product (thickness of the photoreactive composition layer after light irradiation) with respect to the thickness of the photoreactive composition layer (thickness of the photoreactive composition layer before light irradiation). ) ([Thickness of photoreactive composition layer after light irradiation] / [Thickness of photoreactive composition layer before light irradiation]), for example, 0.2 to 1.0.
  • compound (X) was reacted with thionyl chloride and 1,1,3,3-tetramethylguanidine in this order to produce compound (Y). That is, a mixed solution of compound (X) (2.1 g, 0.020 mol) and thionyl chloride (SOCl 2 , 10 mL) was stirred at room temperature for 7 hours, and then dried dichloromethane (20 mL) and 1 were added to this mixed solution. , 1,3,3-Tetramethylguanidine (2.3 g, 0.022 mol) and dry dichloromethane (15 mL) were added, respectively, and the mixture was stirred at 0 ° C. for 2 hours to carry out the reaction.
  • SOCl 2 thionyl chloride
  • Test Example 5 (Outgas confirmation test of compound (1) -1) A test resin composition was obtained by blending triglycidyl isocyanurate (0.041 g), compound (1) -1 (0.020 g), and methanol (0.097 g) and stirring at 25 ° C. for 1 minute. It was. Next, the test resin composition obtained above is applied onto a calcium fluoride plate, the calcium fluoride plate is placed on the obtained coating film, and the coating is applied with two calcium fluoride plates. A laminate was produced by sandwiching the film. An LED lamp was used to set the illuminance to 50 mW / cm 2 and irradiate the coating film of the laminate with light having a wavelength of 365 nm. At this time, the light irradiation amount (mJ / cm 2) for a 10,000 / cm 2. After the light irradiation, the appearance of the laminated body was confirmed, and it was confirmed whether outgas was generated.
  • Test Example 6 the film between the calcium fluoride plates turned yellow due to light irradiation, and bubbles were confirmed. Therefore, in Test Example 6, it is presumed that carbon dioxide is generated as outgas as shown in the following reaction formula. In addition, it is presumed that the reason why the film turned yellow in Test Example 6 was that nitroso groups derived from nitro groups were generated.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Materials For Photolithography (AREA)
PCT/JP2020/034262 2019-09-10 2020-09-10 光塩基発生剤、化合物、光反応性組成物及び反応生成物 Ceased WO2021049563A1 (ja)

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JP2021545584A JP7626457B2 (ja) 2019-09-10 2020-09-10 光塩基発生剤、化合物、光反応性組成物及び反応生成物
US17/641,574 US11873354B2 (en) 2019-09-10 2020-09-10 Photobase generator, compound, photoreactive composition, and reaction product

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JP2019164946 2019-09-10
JP2019-164946 2019-09-10

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Publication number Priority date Publication date Assignee Title
EP4067453B1 (en) * 2019-12-26 2026-03-25 Tokyo University of Science Foundation Photobase generator, compound, photoreactive composition, and reaction product
CN120936613A (zh) * 2023-02-28 2025-11-11 维也纳科技大学 光碱

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IN177137B (https=) * 1992-12-11 1996-11-16 Hoechst India
JP2009080452A (ja) * 2007-09-03 2009-04-16 Tokyo Univ Of Science 感光性樹脂組成物
JP2012113256A (ja) * 2010-11-26 2012-06-14 Wako Pure Chem Ind Ltd 感光性樹脂組成物
JP2012211276A (ja) * 2011-03-31 2012-11-01 Dainippon Printing Co Ltd 塩基発生剤、感光性樹脂組成物、当該感光性樹脂組成物からなるパターン形成用材料、当該感光性樹脂組成物を用いたレリーフパターンの製造方法並びに物品
JP2013087149A (ja) * 2011-10-14 2013-05-13 Dainippon Printing Co Ltd 感光性樹脂組成物及び粘接着シート
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JP2012211276A (ja) * 2011-03-31 2012-11-01 Dainippon Printing Co Ltd 塩基発生剤、感光性樹脂組成物、当該感光性樹脂組成物からなるパターン形成用材料、当該感光性樹脂組成物を用いたレリーフパターンの製造方法並びに物品
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WO2019216321A1 (ja) * 2018-05-07 2019-11-14 学校法人東京理科大学 光反応性組成物、反応生成物及び反応生成物の製造方法
WO2019216322A1 (ja) * 2018-05-07 2019-11-14 学校法人東京理科大学 硬化性組成物、化合物、塩基変換増殖剤及び硬化物

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Title
AKIYAMA, TAKAFUMI ET AL: "Synthesis of photobase generators that generate strong bases by intramolecular photocyclization reaction and application to photoreactive materials", POLYMER PREPRINTS, vol. 67, no. 2, 29 August 2018 (2018-08-29), Japan *

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