WO2016121691A1 - 樹脂、感光性樹脂組成物およびそれらを用いた電子部品、表示装置 - Google Patents
樹脂、感光性樹脂組成物およびそれらを用いた電子部品、表示装置 Download PDFInfo
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- WO2016121691A1 WO2016121691A1 PCT/JP2016/052016 JP2016052016W WO2016121691A1 WO 2016121691 A1 WO2016121691 A1 WO 2016121691A1 JP 2016052016 W JP2016052016 W JP 2016052016W WO 2016121691 A1 WO2016121691 A1 WO 2016121691A1
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Images
Classifications
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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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/80—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two amino groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
- H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
- H01L2224/321—Disposition
- H01L2224/32135—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip
- H01L2224/32145—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip the bodies being stacked
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/484—Connecting portions
- H01L2224/48463—Connecting portions the connecting portion on the bonding area of the semiconductor or solid-state body being a ball bond
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- H01L2224/732—Location after the connecting process
- H01L2224/73201—Location after the connecting process on the same surface
- H01L2224/73203—Bump and layer connectors
- H01L2224/73204—Bump and layer connectors the bump connector being embedded into the layer connector
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
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- H01L2224/732—Location after the connecting process
- H01L2224/73251—Location after the connecting process on different surfaces
- H01L2224/73265—Layer and wire connectors
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/124—Insulating layers formed between TFT elements and OLED elements
Definitions
- the present invention relates to a resin containing a specific structure. More specifically, a surface protective film or an interlayer insulating film of an electronic component or a circuit board, a solder resist for a circuit board, an insulating layer of an organic electroluminescent element, a planarizing film of a driving thin film transistor substrate for a display device using the organic electroluminescent element
- the present invention relates to a resin suitable for applications such as an interlayer insulating film of a thin film transistor, an on-chip microlens of a solid-state image sensor, and a flattening film for various displays and solid-state image sensors, and a photosensitive resin composition using the same.
- the surface protection film and interlayer insulating film of electronic components or circuit boards, the insulating layer of organic electroluminescent elements, and the planarizing film of driving thin film transistor substrates for display devices using organic electroluminescent elements are organic materials with excellent insulating properties.
- a polymer resin is applied.
- polyimide resins and polybenzoxazole resins having excellent heat resistance, chemical resistance, mechanical properties, and the like have been widely used.
- the resin is also required to be imparted with characteristics that reduce the warpage of the substrate.
- Measures for reducing the warpage of the device substrate include reducing the difference in the coefficient of thermal expansion between the resin formed on the substrate and the substrate itself to reduce the stress generated by the difference in thermal expansion. Since the thermal linear expansion coefficient of a general resin is 10 ppm or more larger than the thermal linear expansion coefficient of the substrate, it is effective to reduce the thermal linear expansion coefficient of the resin in order to reduce the stress described above.
- polyimide resins having a rigid structure in the main chain and having a low coefficient of thermal linear expansion see, for example, Patent Documents 1 to 6
- polyimide-polybenzoxazole resins for example, see Patent Document 7
- the resin film formed using the above resin needs to form a pattern such as a through hole in the opening of the electrode portion.
- a pattern was formed by forming a positive photoresist or the like on a non-photosensitive resin film and etching it.
- a composition containing a polyamic acid ester containing a phenolic hydroxyl group and an o-quinonediazide compound see, for example, Patent Document 8
- a solvent-cyclized polyimide and naphthoquinonediazide for example, Patent Document 8
- a composition containing a compound for example, see Patent Document 9
- a composition containing a polybenzoxazole precursor and a naphthoquinonediazide compound for example, see Patent Document 10.
- the negative photosensitive resin composition As for the negative photosensitive resin composition, a polyimide precursor in which an acrylic compound is bonded to a side chain (for example, see Patent Document 11), and a mixture of an acrylic compound and polyimide (for example, see Patent Document 12) have been reported. Yes.
- the monomer of polyimide has mainly two types, a diamine monomer and a dianhydride monomer.
- a diamine monomer By changing the structures of the two types of monomers, the performance of each side of the polyimide, such as the coefficient of thermal expansion, light transmission, elastic modulus, etc., can be significantly improved.
- introduction of a hydroxyl group into a monomer can remarkably change the thermal expansion coefficient, light transmittance or elastic modulus of polyimide (see, for example, Non-Patent Document 1).
- dibromobiphenyl derivatives used in this are commonly used chemical raw materials, pharmaceutical intermediates, and electronic materials.
- the bromine group in the dibromobiphenyl compound can be further converted into a hydroxyl group, amino group, cyan group, alkoxy group, double bond, triple bond or organometallic compound, etc.
- a commonly used synthesis method for dibromobiphenyl derivatives is as follows. That is, using a biphenyl compound as a raw material, a dibromobiphenyl derivative can be obtained under the action of a brominating reagent.
- JP-A-2-283762 JP-A-8-48773 Japanese Patent Laid-Open No. 8-253854 JP-A-11-158279 JP 2002-363283 A JP 2003-212996 A JP 2007-177117 A JP-A-4-204945 Japanese Patent Laid-Open No. 3-209478 International Publication No. 10/092824 JP 2011-191749 A International Publication No. 04/109403 JP 2007-106859 A US Pat. No. 5,378,420 Chinese Patent Application Publication No. 2007800026866.6 Specification
- the above-mentioned resin having a small coefficient of thermal linear expansion has light absorption, especially i-line (light having a wavelength of 365 nm) which is widely used for patterning a photosensitive resin at present due to the rigid skeleton introduced into the main chain.
- i-line light having a wavelength of 365 nm
- the dibromobiphenyl derivative used in this method has a problem that the method disclosed in Patent Document 15 has a very low yield and is not suitable for mass production. Further, in the method disclosed in Non-Patent Document 2, there is a problem that the use of an acidic solvent and a salt causes relatively large corrosion on the equipment, making it difficult to recover the solvent, increasing the difficulty of post-treatment, and causing environmental pollution.
- the present invention has been made in view of the above-described problems of the prior art, and an object of the present invention is to provide a resin having a low coefficient of thermal expansion and low absorbance.
- the 5,5'-dihydroxyl-4,4'-diaminobiphenyl derivative used in these resins and the bromine atom are introduced with high selectivity at the 5,5 'position, and at the same time, the post-treatment process of the bromination reaction is simplified. It is an object of the present invention to provide a production method for converting a bromine atom into a hydroxyl group by a reaction of oxazole ring and ring opening after obtaining a 5,5′-dibromo-4,4′-diaminobiphenyl derivative. It is another object of the present invention to provide a method for synthesizing a dibromobiphenyl derivative that is used in the present invention and that is easy to achieve high yield, low cost, mass production, and has little environmental pollution.
- this invention is resin characterized by including the at least 1 structure chosen from the structure represented by following General formula (1), (2).
- R 1 and R 2 each independently represents a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 3 and R 4 are a hydroxyl group, a carboxyl group, and a carboxyl group.
- X 1 represents an organic group selected from a sulfonic acid group, X 1 represents a single bond, O, S, NH, SO- 2 , CO, a divalent organic group having 1 to 3 carbon atoms, or a combination of two or more thereof.
- N 1 is 0 or 1.
- n 1 0, a 1 is an integer of 1 to 3, b 1 is an integer of 1 to 3, and a 1 + b 1 Is an integer from 2 to 4.
- n 1 1
- a 1 is an integer from 1 to 4
- b 1 is an integer from 0 to 3
- a 2 is an integer from 0 to 4
- b 2 is an integer from 0 to 4.
- a 1 + b 1 is an integer of 1 to 4
- a 2 + b 2 is an integer of 0 to 4
- at least one of b 1 and b 2 is an integer of 1 or more.
- R 5 and R 6 each independently represent a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 7 and R 8 are An organic group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group, wherein X 2 is a single bond, O, S, NH, SO- 2 , CO, a divalent organic group having 1 to 3 carbon atoms, or 2 A divalent cross-linked structure formed by linking the above, a 3 , a 4 , b 3 , and b 4 are integers of 0 to 3, a 3 + b 3 is an integer of 0 to 3, and a 4 + b 4 is An integer of 0 to 3, at least one of a 3 and a 4 is an integer of 1 or more, and at least one of b 3 and b 4 is an integer of 1 or more, m 1 and m 2 are 0 or 1 An integer, m 1 and m 2 are 0 or 1 An integer, m
- a resin having a low coefficient of thermal linear expansion and low absorbance can be obtained.
- the present invention is a resin characterized by including at least one structure selected from structures represented by the following general formulas (1) and (2).
- R 1 and R 2 each independently represents a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 3 and R 4 are a hydroxyl group, a carboxyl group, and a carboxyl group.
- X 1 represents an organic group selected from a sulfonic acid group, X 1 represents a single bond, O, S, NH, SO- 2 , CO, a divalent organic group having 1 to 3 carbon atoms, or a combination of two or more thereof.
- N 1 is 0 or 1.
- n 1 0, a 1 is an integer of 1 to 3, b 1 is an integer of 1 to 3, and a 1 + b 1 Is an integer from 2 to 4.
- n 1 1
- a 1 is an integer from 1 to 4
- b 1 is an integer from 0 to 3
- a 2 is an integer from 0 to 4
- b 2 is an integer from 0 to 4.
- a 1 + b 1 is an integer of 1 to 4
- a 2 + b 2 is an integer of 0 to 4
- at least one of b 1 and b 2 is an integer of 1 or more.
- R 5 and R 6 each independently represent a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 7 and R 8 are An organic group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group, wherein X 2 is a single bond, O, S, NH, SO- 2 , CO, a divalent organic group having 1 to 3 carbon atoms, or 2 A divalent cross-linked structure formed by linking the above, a 3 , a 4 , b 3 , and b 4 are integers of 0 to 3, a 3 + b 3 is an integer of 0 to 3, and a 4 + b 4 is An integer of 0 to 3, at least one of a 3 and a 4 is an integer of 1 or more, and at least one of b 3 and b 4 is an integer of 1 or more, m 1 and m 2 are 0 or 1 (In the integer,
- preferred specific examples include methyl, methoxy, ethyl, ethoxy, fluoro, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, and pentafluoroethoxy groups.
- examples include, but are not limited to: From the viewpoint that the absorbance of the resulting resin can be reduced, a fluoro group, a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, and a pentafluoroethoxy group are more preferable, and a trifluoromethyl group and a pentafluoroethyl group are most preferable. .
- R ⁇ 1 >, R ⁇ 2 > exists in an ortho position with respect to a polymer chain from the point that the light absorbency of the resin obtained can be reduced. Furthermore, it is more preferable that R 1 and R 2 are bonded to positions 2 and 2 ′ from the viewpoint that the thermal linear expansion coefficient of the obtained resin can be reduced.
- R 3 and R 4 each represents an organic group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group. Preferably it is a hydroxyl group. Moreover, it is preferable that R ⁇ 3 >, R ⁇ 4 > exists in an ortho position with respect to a polymer chain from the point that the light absorbency of the resin obtained can be reduced.
- X 1 is a single bond, O, S, NH, SO 2 -2, CO, a divalent organic group having 1 to 3 carbon atoms, or a divalent crosslinked structure formed by linking two or more thereof. A single bond is preferable from the viewpoint that the thermal expansion coefficient of the obtained resin can be reduced.
- n 1 is 0 or 1.
- N 1 is preferably 1 in that the absorbance of the resulting resin can be reduced.
- a 1 is an integer of 1 to 3
- b 1 is an integer of 1 to 3
- a 1 + b 1 is an integer of 2 to 4.
- n 1 1, a 1 is an integer of 1 to 4, b 1 is an integer of 0 to 3, a 2 is an integer of 0 to 4, b 2 is an integer of 0 to 4, and a 1 + b 1 is An integer of 1 to 4, a 2 + b 2 is an integer of 0 to 4, and at least one of b 1 and b 2 is an integer of 1 or more.
- the aromatic ring having the structure represented by the general formula (1) is all bonded to the polymer main chain at the para position from the viewpoint that the coefficient of thermal expansion of the obtained resin can be reduced.
- preferred structures represented by the general formula (1) include the following structures, but are not limited thereto.
- R 5 and R 6 each independently represent a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- preferred specific examples include methyl, methoxy, ethyl, ethoxy, fluoro, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, and pentafluoroethoxy groups.
- methyl, methoxy, ethyl, ethoxy, fluoro, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, and pentafluoroethoxy groups For example, but not limited to.
- a fluoro group, a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, and a pentafluoroethoxy group are more preferable, and a trifluoromethyl group and a pentafluoroethyl group are most preferable.
- R ⁇ 5 >, R ⁇ 6 > exists in an ortho position with respect to a polymer chain from the point that the light absorbency of the resin obtained can be reduced. Furthermore, it is more preferable that R 5 and R 6 are bonded to the 2nd and 2 ′ positions from the viewpoint that the thermal linear expansion coefficient of the obtained resin can be reduced.
- R 7 and R 8 represent an organic group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group. Preferably it is a hydroxyl group.
- R ⁇ 7 >, R ⁇ 8 > exists in an ortho position with respect to a polymer chain from the point that the light absorbency of the resin obtained can be reduced.
- X 2 is a single bond, O, S, NH, SO 2 -2, CO, a divalent organic group having 1 to 3 carbon atoms, or a divalent crosslinked structure formed by linking two or more thereof.
- a single bond is preferable from the viewpoint that the thermal expansion coefficient of the obtained resin can be reduced.
- a 3 , a 4 , b 3 and b 4 are integers from 0 to 3, a 3 + b 3 is an integer from 0 to 3, a 4 + b 4 is an integer from 0 to 3, and a 3 and a 4 At least one is an integer of 1 or more, and at least one of b 3 and b 4 is an integer of 1 or more.
- m 1 and m 2 are integers of 0 or 1
- m 1 + m 2 is an integer of 1 or 2.
- examples of a preferable structure represented by the general formula (2) include the following structures.
- Examples of the resin containing at least one structure selected from the structures represented by the general formulas (1) and (2) include polyurethane, polyurea, polyester, polycarbonate, polyamine, polyazomethine, polyamide, polyamideimide, and polyamideimide precursor.
- Examples include, but are not limited to, ether ketone, polyether sulfone, or a random copolymer or block copolymer thereof.
- Such resins include, for example, dicarboxylic acid, tricarboxylic acid, tetracarboxylic acid or derivatives or anhydrides thereof, diamine, diisocyanate, or a compound in which these are substituted with a hydroxyl group or a carboxyl group, or a derivative thereof, It can be synthesized by reacting in the range of 30 ° C to 300 ° C.
- a polyimide precursor and a polyimide can be obtained by reacting a tetracarboxylic acid, a tetracarboxylic acid derivative or a tetracarboxylic dianhydride with a diamine.
- a polyamideimide precursor or polyamideimide can be obtained by reacting a tricarboxylic acid, a tricarboxylic acid derivative or a tricarboxylic acid anhydride with a diamine.
- a polybenzoxazole precursor or polybenzoxazole can be obtained by reacting bisaminophenol with a dicarboxylic acid or a dicarboxylic acid derivative such as a hydroxybenzotriazole ester or imidazolide compound thereof.
- the polymerization solvent is not particularly limited as long as the generated resin can be dissolved.
- polar aprotic solvents such as N-methyl-2-pyrrolidone, ⁇ -butyrolactone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide , Tetrahydrofuran, dioxane, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether and other glycol ethers, acetone, methyl ethyl ketone, diisobutyl ketone, diacetone ketone and other ketones, ethyl acetate , Butyl acetate, isobutyl acetate, propyl acetate, propylene glycol monomethyl ether a
- the polymerization solvent is preferably used in an amount of 100 to 1900 parts by weight, more preferably 150 to 950 parts by weight, based on 100 parts by weight of the resin obtained. By being in this range, the solution after polymerization becomes easy to handle.
- the specific structure of the resin in the present invention includes resins listed in the following general formulas (3) to (5).
- R 9 represents a divalent .R 10 of an organic group is trivalent or tetravalent organic group having 2 to 50 carbon atoms of 2 to 50 carbon atoms.
- R 9 Represents a structure selected from the general formula (1) or the following general formula (6), and / or R 10 represents a structure selected from the general formula (2) or the following general formula (7),
- R 11 represents hydrogen, Or an organic group having 1 to 10 carbon atoms, m 3 represents an integer of 1 or 2, and n 2 represents a range of 10 to 100,000.
- R 12 represents a trivalent or tetravalent organic group .R 13 number of 2 to 50 carbon atoms which represents a divalent organic group having 2 to 50 carbon atoms.
- R 12 Represents a structure selected from the general formula (1) or the following general formula (6)
- / or R 13 represents a structure selected from the general formula (2) or the following general formula (7)
- m 4 is 0 or 1 integer
- c 1 is an integer of 0 or 1
- the c 1 1
- R 14 and R 15 represent a tetravalent organic group having 2 to 50 carbon atoms, and R 14 and / or R 15 are represented by the general formula (1) or the following general formula (6). (Indicates the selected structure. N 4 is in the range of 10 to 100,000.)
- R 16 to R 19 each independently represents a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 20 and R 21 are a hydroxyl group, a carboxyl group, and a carboxyl group.
- X 3 represents an organic group selected from a sulfonic acid group, X 3 is a single bond, O, S, NH, SO— 2 , CO, a divalent organic group having 1 to 3 carbon atoms, or a combination of two or more thereof.
- X 4 and X 5 are structures selected from an amide bond and an azomethine bond, a 5 is an integer of 1 to 4, b 5 is an integer of 0 to 3, and a 6 is 0.
- b 6 is an integer from 0 to 4
- b 7 and b 8 are integers from 0 to 4
- a 5 + b 5 is an integer from 1 to 4
- a 6 + b 6 is an integer from 0 to 4
- B 5 , b 6 is an integer of 1 or more.
- R 22 to R 25 each independently represents a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 26 and R 27 are X 6 represents an organic group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group, and X 6 represents a single bond, O, S, NH, SO- 2 , CO, a divalent organic group having 1 to 3 carbon atoms, or 2 A divalent cross-linked structure formed by linking the above, wherein X 7 and X 8 are structures selected from an amide bond and an azomethine bond, a 7 is an integer of 1 to 4, b 9 is an integer of 0 to 3, 8 is an integer from 0 to 4, b 10 is an integer from 0 to 4, b 11 and b 12 are integers from 0 to 3, a 7 + b 9 is an integer from 1 to 4, and a 8 + b 10 is from 0 to 4
- an organic group having 5 to 40 carbon atoms containing an aromatic ring or a cyclic aliphatic group is preferable.
- Preferred examples include bis (3-amino-4-hydroxyphenyl) hexafluoropropane, bis (3-amino-4-hydroxyphenyl) sulfone, bis (3-amino-4-hydroxyphenyl) propane, bis (3 -Amino-4-hydroxyphenyl) methylene, bis (3-amino-4-hydroxyphenyl) ether, bis (3-amino-4-hydroxy) biphenyl, bis (3-amino-4-hydroxyphenyl) fluorene, 3, 5-diaminobenzoic acid, 3-carboxy-4,4′-diaminodiphenyl ether, 3-sulfonic acid-4,4′-diaminodiphenyl ether, dithiohydroxyphenylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-d
- R 10 and R 13 represent a residue of tetracarboxylic acid, tricarboxylic acid, tetracarboxylic dianhydride or tricarboxylic anhydride, and are trivalent having 2 to 50 carbon atoms or A tetravalent organic group is shown. Among them, an organic group having 5 to 40 carbon atoms containing an aromatic ring or a cyclic aliphatic group is preferable.
- Preferred specific examples include pyromellitic anhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, 2,3,3 ′, 4′-biphenyltetracarboxylic dianhydride, 2, 2 ', 3,3'-biphenyltetracarboxylic dianhydride, 3,3', 4,4'-benzophenone tetracarboxylic dianhydride, 2,2 ', 3,3'-benzophenone tetracarboxylic dianhydride 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1,1-bis (3,4- Dicarboxyphenyl) ethane dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydr
- R 10 and R 13 preferably contain a residue derived from pyromellitic anhydride from the viewpoint that the coefficient of thermal expansion of the obtained resin can be reduced. Further, the pyromellitic anhydride contained in the acid anhydride is more preferably 30 mol% to 80 mol% from the viewpoint that the absorbance can be reduced while reducing the thermal expansion coefficient.
- R 15 represents a residue derived from a dicarboxylic acid and represents a divalent organic group having 2 to 50 carbon atoms.
- dicarboxylic acids include terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, naphthalene dicarboxylic acid, bis (carboxyphenyl) propane, bis (carboxyphenyl) hexafluoropropane, biphenyldicarboxylic acid, benzophenone dicarboxylic acid, Aromatic dicarboxylic acid residues such as phenyldicarboxylic acid, aliphatic dicarboxylic acid residues such as cyclohexanedicarboxylic acid, adipic acid, sebacic acid, dodecanedioic acid, or these aromatic rings are substituted with alkyl groups or halogen atoms And the structure represented by the general formulas (1) and (6). These are used alone or in
- R 9 and R 12 represent a structure selected from the general formula (1) or (6)
- / or R 10 and R 13 represent the general formula (2) or (7 It is preferable to show a structure selected from:
- R 14 and R 15 has a structure selected from General Formula (1) or (6).
- R 9 , R 10 , R 12 , R 13 , and R 14 may be copolymerized with a siloxane structure within a range that does not decrease the heat resistance.
- R 9 , R 12 and R 14 include residues such as bis (3-aminopropyl) tetramethyldisiloxane and bis (p-amino-phenyl) octamethylpentasiloxane.
- R 10 and R 13 include residues such as dimethylsilanediphthalic dianhydride and 1,3-bis (phthalic acid) tetramethyldisiloxane dianhydride. These may be used alone or in combination of two or more, and are preferably copolymerized in an amount of 1 to 10 mol% of the entire R 10 and R 13 .
- R 9 , R 12 , and R 14 are within the range in which the heat resistance is not lowered in order to improve the adhesion between the heat-resistant film after the heat treatment and the metal substrate.
- An aliphatic structure having a polyalkylene oxide group may be copolymerized.
- Specific structures include Jeffermin (registered trademark) KH-511, Jeffermin ED-600, Jeffermin ED-900, Jeffermin ED-2003, Jeffermin EDR-148, Jeffermin EDR-176, Jeffermin D- 200, Jeffamine D-400, Jeffamine D-2000, Jeffamine D-4000 (trade name, manufactured by HUNTSMAN Co., Ltd.) and the like. These may be used singly or in combination of two or more, and are preferably copolymerized in an amount of 1 to 30 mol% of R 9 , R 12 and R 14 as a whole.
- R 11 represents hydrogen or an organic group having 1 to 10 carbon atoms.
- R 11 is preferably an organic group, but hydrogen is more preferable than the solubility of an alkaline aqueous solution.
- a hydrogen atom and an alkyl group can be mixed.
- R 11 contains at least one hydrocarbon group having 1 to 20 carbon atoms, and the others are hydrogen atoms.
- R 11 is a hydrocarbon group include a methyl group, an ethyl group, a propyl group, and a butyl group.
- m 3 represents an integer of 1 or 2. Preferably it is 2.
- m 4 is an integer of 0 or 1
- c 1 is an integer of 0 or 1
- Formula (6) is a divalent organic group, and R 16 to R 19 each independently represent a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 16 to R 19 each independently represent a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- preferred specific examples include methyl, methoxy, ethyl, ethoxy, fluoro, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, and pentafluoroethoxy groups.
- methyl, methoxy, ethyl, ethoxy, fluoro, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, and pentafluoroethoxy groups For example, but not limited to.
- R 16 to R 19 are preferably in the ortho position with respect to the polymer chain from the viewpoint that the absorbance of the resulting resin can be reduced. Furthermore, it is more preferable that R 16 to R 19 are bonded to positions 2 and 2 ′ from the viewpoint that the coefficient of thermal expansion of the obtained resin can be reduced.
- R 20 and R 21 represent an organic group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group. Preferably it is a hydroxyl group. Moreover, it is preferable that R ⁇ 20 >, R ⁇ 21 > exists in an ortho position with respect to a polymer chain from the point that the light absorbency of the resin obtained can be reduced.
- X 3 is a single bond, O, S, NH, SO 2 -2, CO, a divalent organic group having 1 to 3 carbon atoms, or a divalent crosslinked structure formed by linking two or more thereof.
- a single bond is preferable from the viewpoint that the thermal expansion coefficient of the obtained resin can be reduced.
- X 4 and X 5 each represent a structure selected from an amide bond and an azomethine bond. An amide bond is preferable because the absorbance of the resulting resin can be reduced.
- a 5 is an integer from 1 to 4
- b 5 is an integer from 0 to 3
- a 6 is an integer from 0 to 4
- b 6 is an integer from 0 to 4
- b 7 and b 8 are integers from 0 to 4
- a 5 + b 5 is an integer of 1 to 4
- a 6 + b 6 is an integer of 0 to 4
- at least one of b 5 and b 6 is an integer of 1 or more.
- preferred structures represented by the general formula (6) include the following structures, but are not limited thereto.
- Formula (7) is a trivalent or tetravalent organic group, and R 22 to R 25 each independently represent a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- R 22 to R 25 each independently represent a halogen atom or a monovalent organic group having 1 to 3 carbon atoms.
- preferred specific examples include methyl, methoxy, ethyl, ethoxy, fluoro, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, and pentafluoroethoxy groups. For example, but not limited to.
- a fluoro group, a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, and a pentafluoroethoxy group are more preferable, and a trifluoromethyl group and a pentafluoroethyl group are most preferable.
- R 22 to R 25 are preferably in the ortho position with respect to the polymer chain from the viewpoint that the absorbance of the obtained resin can be reduced. Furthermore, it is more preferable that R 22 to R 25 are bonded to positions 2 and 2 ′ from the viewpoint that the coefficient of thermal expansion of the obtained resin can be reduced.
- R 26 and R 27 represent an organic group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group. Preferably it is a hydroxyl group. From the viewpoint of reducing the absorbance of the resulting resin, it is preferred R 26, R 27 is in the ortho position with respect to the polymer chain.
- X 6 is a single bond, O, S, NH, SO 2 --2, CO, a divalent organic group having 1 to 3 carbon atoms, or a divalent crosslinked structure formed by linking two or more thereof. A single bond is preferable from the viewpoint that the thermal expansion coefficient of the obtained resin can be reduced.
- X 7 and X 8 each represents a structure selected from an amide bond and an azomethine bond. An amide bond is preferable because the absorbance of the resulting resin can be reduced.
- a 7 is an integer from 1 to 4
- b 9 is an integer from 0 to 3
- a 8 is an integer from 0 to 4
- b 10 is an integer from 0 to 4
- b 11 and b 12 are integers from 0 to 3
- a 7 + b 9 is an integer of 1 to 4
- a 8 + b 10 is an integer of 0 to 4
- at least one of b 9 and b 10 is an integer of 1 or more.
- m 5 and m 6 are integers of 0 or 1, and m 5 + m 6 is an integer of 1 or 2.
- preferable structures represented by the general formula (7) include the following structures, but are not limited thereto.
- X 9 each independently represents a structure represented by [Chemical Formula 5] to [Chemical Formula 7])
- n 2 , n 3 and n 4 are in the range of 10 to 100,000.
- At least one of both ends of the resin of the present invention may contain a phenol group and / or a thiophenol group.
- the introduction of the alkali-soluble group at the terminal can be performed by providing the terminal sealing agent with an alkali-soluble group.
- the end-capping agent monoamine, acid anhydride, monocarboxylic acid, monoacid chloride compound, monoactive ester compound and the like can be used.
- monoamines used as end-capping agents include 5-amino-8-hydroxyquinoline, 4-amino-8-hydroxyquinoline, 1-hydroxy-8-aminonaphthalene, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 1-hydroxy-3-aminonaphthalene, 1-hydroxy-2-aminonaphthalene, 1-amino-7 -Hydroxynaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 2-hydroxy-4-aminonaphthalene, 2-hydroxy-3-aminonaphthalene, 1 -Amino-2-hydroxynaphthalene, 1-ca Boxy-8-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy
- 5-amino-8-hydroxyquinoline 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2 -Hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5 Aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4- Amino salicylic acid, 5-amino salicylic acid, 6-amino salicy Acid, 2-aminobenzenesulfonic acid, 3-aminobenzo
- acid anhydrides examples include phthalic anhydride, maleic anhydride, nadic acid, cyclohexanedicarboxylic anhydride, 3-hydroxy Acid anhydrides such as phthalic anhydride, 2-carboxyphenol, 3-carboxyphenol, 4-carboxyphenol, 2-carboxythiophenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-8-carboxy Naphthalene, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-hydroxy-4-carboxynaphthalene, 1-hydroxy-3-carboxynaphthalene, 1-hydro Ci-2-carboxynaphthalene, 1-mercapto-8-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-
- phthalic anhydride maleic anhydride, nadic acid, cyclohexanedicarboxylic anhydride, acid anhydrides such as 3-hydroxyphthalic anhydride, 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene
- Monocarboxylic acids such as 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid and 4-carboxybenzenesulfonic acid, and monoacid chloride compounds and terephthalates in which these carboxyl groups are converted to acid chloride , Monocarboxylic groups of dicarboxylic acids such as phthalic acid, maleic acid, cyclohex
- the content of the end-capping agent such as monoamine, acid anhydride, acid chloride, monocarboxylic acid described above is preferably in the range of 0.1 to 70 mol% of the charged mole number of the acid component monomer or diamine component monomer. More preferred is ⁇ 50 mol%.
- the resin having an end-capping agent is terminated with a diamine or a tetracarboxylic dianhydride selectively in combination, or at the same time or a little later than these. It can be obtained by adding a sealant.
- the resin of the present invention is characterized by low absorbance.
- the absorbance at a wavelength of 365 nm per 1 ⁇ m thickness of the resin film formed of the resin of the present invention is preferably 0.005 or more and 0.3 or less, more preferably 0.008 or more and 0.2 or less. It is most preferable that it is 0.01 or more and 0.1 or less. In the case of 0.3 or less, energy loss can be reduced when used in a resin composition having photosensitivity by suppressing absorption of the resin itself, and in the case of 0.005 or more, it is caused by light reflection from the substrate. Pattern formation failure does not occur.
- the absorbance is set by selecting the structures of R 12 and R 13 and adjusting the copolymerization ratio. Resins having such characteristics can be preferably used in that the photosensitive performance, particularly the sensitivity, particularly when a photosensitive resin composition is obtained.
- the resin film preferably has a film thickness reduction rate of 10 nm / min or more and 30000 nm / min or less when immersed in a 2.38% tetramethylammonium hydroxide aqueous solution. More preferably, they are 50 nm / min or more and 20000 nm / min or less, Most preferably, they are 100 nm / min or more and 15000 nm / min or less. When it is 30000 nm / min or less, the developability of the resin is improved to the extent that pattern formation defects do not occur when used in a photosensitive resin composition, and when it is 10 nm / min or more, a relief pattern is obtained by development.
- the film thickness reduction rate is adjusted by selecting the structure of R 9 and R 10 and adjusting the copolymerization ratio, and adjusting the proportion of hydrogen in R 11.
- the molecular weight is adjusted by changing n 2 n 1 .
- Resins having such characteristics can be preferably used in that the photosensitive performance, particularly the sensitivity, particularly when a photosensitive resin composition is obtained.
- the resin film referred to here is a 120 ° C. hot plate (Dainippon Screen Mfg.
- the average coefficient of thermal expansion at 50 to 200 ° C. measured after the heat treatment of the resin of the present invention at 250 ° C. is ⁇ 10 to 40 ppm / ° C. More preferably, it is 0 to 30 ppm / ° C., further preferably 1 to 25 ppm / ° C., and most preferably 3 to 20 ppm / ° C. Even if it is larger or smaller than this range, the difference in thermal expansion coefficient from the substrate will increase, and the stress caused by the resin applied to the device will increase, which may adversely affect the yield during device manufacturing and product reliability. is there.
- the average thermal linear expansion coefficient is set by selecting the structures of R 12 and R 13 and adjusting the copolymerization ratio. Resins having such characteristics can be preferably used in that the warpage of the device can be reduced.
- the resin of the present invention is more preferably obtained by precipitating in a poor solvent for the resin such as methanol or water after completion of polymerization, followed by washing and drying.
- a poor solvent for the resin such as methanol or water
- the by-product by the esterifying agent, condensing agent and acid chloride used during the polymerization, and low molecular weight components of the resin precursor can be removed, so the mechanical properties of the resin composition after heat curing Has the advantage of greatly improving.
- the resin composition of the present invention may contain a solvent and, if necessary, an additive for functionalization in the resin of the present invention.
- the solvent preferably used in the resin composition of the present invention include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, Ethers such as ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propyl acetate, butyl acetate, isobutyl acetate, 3-methoxybutyl acetate, 3 -Methyl-3-me Acetates such as xylbutyl acetate, methyl lactate,
- the resin composition of the present invention may contain an alkali-soluble resin other than the resin of the present invention.
- acrylic polymers copolymerized with acrylic acid, phenol resins, siloxane resins, polyhydroxystyrene resins, and resins in which cross-linking groups such as methylol groups, alkoxymethyl groups, and epoxy groups are introduced, and their copolymerization Examples thereof include polymers.
- Preferable are phenol resins, polyhydroxystyrene resins, resins in which a crosslinking group such as a methylol group, an alkoxymethyl group or an epoxy group is introduced, and copolymers thereof.
- Such a resin is soluble in an aqueous alkali solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate.
- an aqueous alkali solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate.
- Preferred phenol resins include novolak resins and resol resins, which can be obtained by polycondensation of various phenols alone or a mixture of a plurality of them with aldehydes such as formalin.
- phenols constituting the novolak resin and the resol resin include phenol, p-cresol, m-cresol, o-cresol, 2, 3-dimethylphenol, 2, 4-dimethylphenol, 2, 5-dimethylphenol, 2 , 6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2,3,4-trimethylphenol, 2,3,5-trimethylphenol, 3,4,5-trimethylphenol, 2,4 , 5-trimethylphenol, methylene bisphenol, methylene bis p-cresol, resorcin, catechol, 2-methyl resorcin, 4-methyl resorcin, o-chlorophenol, m-chlorophenol, p-chlorophenol, 2,3-dichlorophenol, m-metoki Siphenol, p-methoxyphenol, p-butoxyphenol, o-ethylphenol, m-ethylphenol, p-ethylphenol, 2,3-diethylphenol,
- aldehydes include paraformaldehyde, acetaldehyde, benzaldehyde, hydroxybenzaldehyde, chloroacetaldehyde, and the like, and these can be used alone or as a mixture of a plurality of them.
- the phenol resin used in the present invention includes an alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group, an alkoxyl group, an ester group, a nitro group, a cyano group, and a fluorine atom. Or a structure substituted with 1 to 4 chlorine atoms.
- the preferred weight average molecular weight of the phenol resin used in the present invention is in the range of 2,000 to 50,000, preferably 3,000 to 30,000 in terms of polystyrene using gel permeation chromatography (GPC). Is preferred. When the molecular weight is 2,000 or more, the pattern shape, resolution, developability and heat resistance are excellent, and when the molecular weight is 50,000 or less, sufficient sensitivity can be maintained.
- Preferred polyhydroxystyrene resins include aromatics having a phenolic hydroxyl group such as p-hydroxystyrene, m-hydroxystyrene, o-hydroxystyrene, p-isopropenylphenol, m-isopropenylphenol, o-isopropenylphenol.
- Polymers or copolymers obtained by polymerizing aromatic vinyl compounds alone or in a known manner, and aromatics such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene A polymer or copolymer obtained by subjecting an alkoxy group to an addition reaction by a known method to a part of a polymer or copolymer obtained by polymerizing a vinyl compound alone or two or more types by a known method. A polymer is mentioned.
- aromatic vinyl compound having a phenolic hydroxyl group p-hydroxystyrene and / or m-hydroxystyrene is preferably used, and styrene is preferably used as the aromatic vinyl compound.
- some of the hydrogen atoms added to the aromatic ring are alkyl groups having 1 to 20 carbon atoms, fluoroalkyl groups, alkoxyl groups, ester groups, nitro groups, cyano groups, A structure in which 1 to 4 fluorine atoms or 1 to 4 chlorine atoms are substituted may be used.
- the preferred weight average molecular weight of the polyhydroxystyrene resin used in the present invention is preferably in the range of 3,000 to 60,000 in terms of polystyrene, using gel permeation chromatography (GPC), and 3,000 to 25 More preferably, it is in the range of 1,000.
- GPC gel permeation chromatography
- the content of these phenol resins and polyhydroxystyrene resins in the resin composition is 5 to 50 parts by weight, particularly 10 to 40 parts by weight, based on 100 parts by weight of the resin of the present invention.
- it is 40 parts by weight or less, the heat resistance and strength of the heat-resistant film after the heat treatment can be maintained, and when it is 10 parts by weight or more, the pattern formability of the resin film is improved.
- the resin composition of the present invention may contain a photoacid generator and can impart positive photosensitivity.
- the photoacid generator include a quinonediazide compound, a sulfonium salt compound, a phosphonium salt compound, a diazonium salt compound, an iodonium salt compound, and the like.
- a quinonediazide compound is preferable, and an o-quinonediazide compound is particularly preferable.
- quinonediazide compounds As quinonediazide compounds, quinonediazide sulfonic acid is bonded to a polyhydroxy compound with an ester, quinonediazide sulfonic acid is bonded to a polyamino compound with a sulfonamide bond, and a quinonediazide sulfonic acid is bonded to a polyhydroxypolyamino compound with an ester bond and / or sulfone. Examples include amide-bonded ones. Although all the functional groups of these polyhydroxy compounds and polyamino compounds may not be substituted with quinonediazide, it is preferable that 50 mol% or more of the entire functional groups are substituted with quinonediazide.
- quinonediazide By replacing 50 mol% or more with quinonediazide, there is an advantage that the solubility of the resin film in an alkaline developer is improved and a fine pattern having a high contrast with the unexposed portion can be obtained.
- a positive photosensitive resin composition sensitive to i-line (365 nm), h-line (405 nm), and g-line (436 nm) of a mercury lamp which is a general ultraviolet ray is obtained. be able to.
- Polyhydroxy compounds include Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, TrisP-SA, TrisOCR-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, BisOCP -IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, Methylenetris-FR-CR, BisRS-26X, DML-MBPC, DML-MBOC, DML-OCHP, DML-PCHP, DML-PC, DML-PTBP, DML-34X, DML-EP, DML-POP, dimethylol-BisOC-P, DML-PFP, DML-PSBP, DML-MTrisPC, TriML-P, TriML-35XL, TML-BP, TML-H , TML-pp-BPF, TML-BPA, TMOM-BP, HML-TPPHBA, HML-TPPHAP (
- Polyamino compounds include 1,4-phenylenediamine, 1,3-phenylenediamine, 4,4′-diaminodiphenyl ether, 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylsulfone, 4,4′-diaminodiphenyl Examples thereof include, but are not limited to, sulfhydrides.
- Examples of the polyhydroxypolyamino compound include 2,2-bis (3-amino-4- hydroxyphenyl) hexafluoropropane and 3,3′-dihydroxybenzidine, but are not limited thereto.
- quinonediazide is preferably a 5-naphthoquinonediazidesulfonyl group or a 4-naphthoquinonediazidesulfonyl group.
- the 4-naphthoquinonediazide sulfonyl ester compound has absorption in the i-line region of a mercury lamp and is suitable for i-line exposure.
- the 5-naphthoquinone diazide sulfonyl ester compound has absorption up to the g-line region of a mercury lamp and is suitable for g-line exposure.
- a naphthoquinone diazide sulfonyl ester compound can be obtained by using a 4-naphthoquinone diazide sulfonyl group and a 5-naphthoquinone diazide sulfonyl group in the same molecule, or a 4-naphthoquinone diazide sulfonyl ester compound and a 5-naphthoquinone diazide sulfonyl ester compound. Can also be used in combination.
- the molecular weight of the quinonediazide compound is preferably 300 or more, more preferably 350 or more. Moreover, 1500 or less is preferable and 1200 or less is more preferable. When the molecular weight is 300 or more, the exposure sensitivity is high, and when it is 1500 or less, there is an advantage that the mechanical properties of the heat-resistant film after the heat treatment are improved.
- the content of the photoacid generator is preferably 1 part by weight or more with respect to 100 parts by weight of the resin as a whole resin composition, and more preferably 3 parts by weight or more. Moreover, 50 weight part or less is preferable and 40 weight part or less is more preferable. In addition, the content in the case of the quinonediazide compound is preferably 1 part by weight or more and more preferably 3 parts by weight or more with respect to 100 parts by weight of the resin. Moreover, 50 weight part or less is preferable and 40 weight part or less is more preferable. Within this range, there is an advantage that the mechanical properties of the heat-resistant film after the heat treatment are good.
- the quinonediazide compound used in the present invention is synthesized from a specific phenol compound by the following method. For example, there is a method of reacting 5-naphthoquinonediazidesulfonyl chloride with a phenol compound in the presence of triethylamine. As a method for synthesizing a phenol compound, there is a method in which an ⁇ - (hydroxyphenyl) styrene derivative is reacted with a polyhydric phenol compound under an acid catalyst.
- sulfonium salts are preferably used among sulfonium salt compounds, phosphonium salt compounds, and diazonium salt compounds. Particularly preferred is a triarylsulfonium salt.
- the resin composition of the present invention has an ethyl methacrylate group, an ethyl acrylate group, a propyl methacrylate group, and a propyl acrylate group as R 11 in the general formula (3) in order to impart negative photosensitivity.
- a group having an ethylenically unsaturated double bond such as an ethyl methacrylamide group, a propyl methacrylamide group, an ethyl acrylamide group, or a propyl acrylamide group can be used.
- photopolymerizable compounds examples include 2-hydroxyethyl methacrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, propylene glycol dimethacrylate. , Methylene bismethacrylamide, methylene bisacrylamide and the like, but are not limited thereto.
- the photopolymerizable compound is preferably contained in the range of 1 to 30 parts by weight with respect to 100 parts by weight of the resin. Within this range, the sensitivity is high, and the film has a good mechanical property after thermosetting. These photopolymerizable compounds can be used alone or in combination of two or more.
- a photopolymerization initiator when imparting negative photosensitivity to the resin composition of the present invention, a photopolymerization initiator may be contained.
- the photopolymerization initiator suitable for the present invention include aromatic amines such as N-phenyldiethanolamine and N-phenylglycine, aromatic ketones such as Michler's ketone, and cyclic oximes represented by 3-phenyl-5-isoxazolone.
- Chain oxime compounds represented by 1-phenylpropanedione-2- (o-ethoxycarbonyl) oxime benzophenone, benzophenone derivatives such as methyl o-benzoylbenzoate, dibenzylketone, fluorenone, thioxanthone, 2-methyl
- thioxanthone derivatives such as thioxanthone and 2-isopropylthioxanthone.
- the content of the photopolymerization initiator is preferably 0.01 parts by weight or more and more preferably 0.1 parts by weight or more with respect to 100 parts by weight of the resin. Moreover, 30 weight part or less is preferable and 20 weight part or less is more preferable. Within this range, the sensitivity is high, and the film has a good mechanical property after thermosetting.
- These photopolymerization initiators can be used alone or in combination of two or more.
- Photosensitizers suitable for the present invention include aromatic monoazides such as azidoanthraquinone and azidobenzalacetophenone, aminocoumarins such as 7-diethylaminobenzoylcoumarin, 3,3′-carbonylbis (diethylaminocoumarin), and benzanthrone. And aromatic ketones such as phenanthrenequinone, which are generally used in photocurable resins.
- those used as a charge transfer agent for an electrophotographic photosensitive member can also be preferably used.
- the content of the photosensitizer is preferably 0.01 parts by weight with respect to 100 parts by weight of the resin, and more preferably 0.1 parts by weight or more. Moreover, 30 weight part or less is preferable and 20 weight part or less is more preferable. Within this range, the sensitivity is high, and the mechanical properties of the heat-resistant coating after heat treatment are also good. These photosensitizers can be used alone or in combination of two or more.
- the resin composition of the present invention can contain a compound having a phenolic hydroxyl group for the purpose of controlling the alkali developability of a resin film formed from the resin composition.
- a compound having a phenolic hydroxyl group that can be used in the present invention include Bis-Z, BisOC-Z, BisOPP-Z, BisP-CP, Bis26X-Z, BisOTBP-Z, BisOCHP-Z, and BisOCR-CP.
- preferred compounds having a phenolic hydroxyl group include, for example, Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP- IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, Methylenetris-FR-CR, BisRS-26X, BIP-PC, BIR-PC, BIR-PTBP, BIR-BIPC-F Etc.
- particularly preferred compounds having a phenolic hydroxyl group are Bis-Z, TekP-4HBPA, TrisP-HAP, TrisP-PA, BisRS-2P, BisRS-3P, BIR-PC, BIR-PTBP, BIR-BIPC- F.
- the resulting resin composition is easily dissolved in an alkali developer before exposure, becomes insoluble in an alkali developer upon exposure, and film loss due to development is reduced. Less development and easy development in a short time.
- the content of such a compound having a phenolic hydroxyl group is preferably 1 to 60 parts by weight, more preferably 3 to 50 parts by weight with respect to 100 parts by weight of the resin.
- the resin composition of the present invention may contain a thermal crosslinking agent.
- the thermal crosslinking agent include a methylol compound, a methoxymethylol compound, a urea compound, an epoxy compound, an oxetane compound, and any compound can be preferably used.
- Specific examples of the thermal cross-linking agent include, for example, ML-26X, ML-24X, ML-236TMP, 4-methylol 3M6C, ML-MC, ML-TBC (which are trade names as those having one thermal crosslinkable group). DM-BI25X-F, 46DMOC, 46DMOIPP, etc.
- thermally crosslinkable groups such as Honshu Chemical Industry Co., Ltd.), Pa-type benzoxazine (trade name, manufactured by Shikoku Kasei Kogyo Co., Ltd.), etc. 46DMOEP, TM-BIP-A (trade name, manufactured by Asahi Organic Materials Co., Ltd.), DML-MBPC, DML-MBOC, DML-OCHP, DML-PC, DML-PCHP, DML-PTBP, DML- 34X, DML-EP, DML-POP, DML-OC, dimethylol-Bis-C, dimethylol-BisOC-P, DML-BisOC Z, DML-BisOCHP-Z, DML-PFP, DML-PSBP, DML-MB25, DML-MTrisPC, DML-Bis25X-34XL, DML-Bis25X-PCHP, 2,6-dimethoxymethyl-4-t-butylphenol, 2 , 6-Dimeth
- a methoxymethylol compound is preferably used from the standpoint of standing stability after exposure.
- these thermal crosslinking agents By containing these thermal crosslinking agents, the shrinkage after curing is small and a film with high dimensional reproducibility is obtained.
- the composition when the composition is photosensitive, it hardly dissolves in an alkali developer before exposure, and easily dissolves in an alkali developer upon exposure. There are advantages you can do.
- the content of the thermal crosslinking agent is preferably 0.5 parts by weight or more, more preferably 3 parts by weight or more, and preferably 50 parts by weight or less, more preferably 40 parts by weight with respect to 100 parts by weight of the resin. It is as follows. Within this range, there is an advantage that the chemical resistance of the composition is improved.
- the resin composition of the present invention further improves the adhesion between the heat-resistant film after heat treatment and silicon-based substrates such as silicon, silicon nitride, silicon oxide, and phosphorous silicate glass, ITO substrates, various metal substrates, Contains silane coupling agents, titanium chelating agents, aluminum chelating agents, alkoxysilane-containing aromatic amine compounds, aromatic amide compounds, etc. as adhesion improvers to increase resistance to oxygen plasma and UV ozone treatment used for cleaning, etc.
- silicon-based substrates such as silicon, silicon nitride, silicon oxide, and phosphorous silicate glass, ITO substrates, various metal substrates, Contains silane coupling agents, titanium chelating agents, aluminum chelating agents, alkoxysilane-containing aromatic amine compounds, aromatic amide compounds, etc. as adhesion improvers to increase resistance to oxygen plasma and UV ozone treatment used for cleaning, etc.
- preferable silane coupling agents include N-phenylaminoethyltrimethoxysilane, N-phenylaminoethyltriethoxysilane, N-phenylaminopropyltrimethoxysilane, N-phenylaminopropyltriethoxysilane, and N-phenyl.
- a compound obtained by reacting an aromatic amine compound and an alkoxy group-containing silicon compound may be used.
- an aromatic amine compound and a group that reacts with an amino group such as an epoxy group or a chloromethyl group may be used.
- an amino group such as an epoxy group or a chloromethyl group.
- the compound etc. which are obtained by making the alkoxysilane compound which has it react are mentioned.
- the content of these adhesion improvers is preferably 0.01 to 15 parts by weight with respect to 100 parts by weight of the resin.
- the pretreatment method include the following methods. 0.5-20 wt.% Of the adhesion improver described above with respect to 100 wt. Parts of solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diethyl adipate. Surface treatment is performed on the partially dissolved solution by spin coating, dipping, spray coating, steam treatment, or the like.
- solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diethyl adipate.
- hexamethyldisilazane vapor may be directly sprayed for treatment. Thereafter, a vacuum drying treatment is performed as necessary, and the reaction between the surface of the silicon-based material and the adhesion improving agent is advanced by heating to 50 to 300 ° C.
- the resin composition of the present invention may contain a surfactant and can improve paintability with the substrate.
- Surfactants (trade name, manufactured by Sumitomo 3M Co., Ltd.), MegaFac (registered trademark) (trade name, manufactured by DIC Corporation), Sulfron (registered trademark) (trade name, manufactured by Asahi Glass Co., Ltd.) ), Etc., KP341 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), DBE (trade name, manufactured by Chisso Corporation), Granol (trade name, manufactured by Kyoeisha Chemical Co., Ltd.), BYK ( An organic siloxane surfactant such as BIC Chemie Co., Ltd., and an acrylic polymer surfactant such as Polyflow (trade name, manufactured by Kyoeisha Chemical Co., Ltd.).
- the resin composition of the present invention may contain a thermochromic compound.
- the thermochromic compound is a thermochromic compound that develops color by heat treatment and has an absorption maximum at 350 nm or more and 700 nm or less, more preferably a color that develops by heat treatment and has an absorption maximum at 350 nm or more and 500 nm or less.
- the thermochromic compound may be a general heat-sensitive dye or pressure-sensitive dye, or may be another compound. These thermochromic compounds are those that develop color by changing their chemical structure or charge state due to the action of acidic groups that coexist in the system during heat treatment, or cause thermal oxidation reaction due to the presence of oxygen in the air. And those that develop color.
- thermochromic compound examples include triarylmethane skeleton, diarylmethane skeleton, fluorane skeleton, bislactone skeleton, phthalide skeleton, xanthene skeleton, rhodamine lactam skeleton, fluorene skeleton, phenothiazine skeleton, phenoxazine skeleton, and spiropyran skeleton. It is done.
- a hydroxyl group-containing compound having a triarylmethane skeleton is preferred.
- hydroxyl group-containing compounds having a triarylmethane skeleton are particularly preferred because of their high thermochromic temperature and excellent heat resistance. These may be used alone or in admixture of two or more.
- a hydroxyl group-containing compound having a triarylmethane skeleton may be used as a quinonediazide compound by esterifying a sulfonic acid of naphthoquinonediazide to the compound.
- the content of the thermochromic compound in the resin composition of the present invention is preferably 5 to 80 parts by weight, more preferably 10 to 60 parts by weight, based on 100 parts by weight of the resin. If it is 5 weight part or more, the transmittance
- the resin composition of the present invention may contain a dye and / or an organic pigment.
- usage methods include a method using one kind of dye or an organic pigment, a method using a mixture of two or more dyes or an organic pigment, a method using a combination of one or more dyes and one or more organic pigments, etc.
- dyes and / or organic pigments having an absorption maximum at 436 to 750 nm are preferably selected.
- the dye used in the present invention is preferably one that is soluble in an organic solvent that dissolves the resin of the present invention and is compatible with the resin.
- a dye having high heat resistance and light resistance is preferred.
- preferable dyes include oil-soluble dyes, disperse dyes, reactive dyes, acid dyes, and direct dyes.
- the skeleton structure of the dye include anthraquinone series, azo series, phthalocyanine series, methine series, oxazine series, quinoline series, and triarylmethane series, and these dyes may be used alone or as a metal complex complex. .
- the organic pigment used in the present invention is preferably a pigment having high heat resistance and light resistance. Specific examples of the organic pigment used in the present invention are indicated by color index (CI) numbers. Examples of purple pigments include pigment violet 19, 23, 29, 32, 33, 36, 37, 38, and the like. Examples of blue pigments include Pigment Blue 15 (15: 3, 15: 4, 15: 6, etc.), 21, 22, 60, 64, and the like. Examples of green pigments include Pigment Green 7, 10, 36, 47, and the like. In addition, pigments other than these can also be used.
- CI color index
- the content of the organic pigment in the resin composition of the present invention is preferably 1 to 300 parts by weight, particularly preferably 10 to 200 parts by weight, based on 100 parts by weight of the resin.
- the amount used is 1 part by weight or more, light of a corresponding wavelength can be absorbed.
- the light of a corresponding wavelength can be absorbed, maintaining the adhesive strength of a resin film and a board
- the organic pigment used in the present invention may be subjected to surface treatment such as rosin treatment, acidic group treatment, basic group treatment, etc., if necessary. Moreover, it can be used with a dispersing agent depending on the case. Examples of the dispersant include cationic, anionic, nonionic, amphoteric, silicone, and fluorine surfactants.
- the resin composition of the present invention may contain inorganic particles, and the resin film and the heat-resistant film after the heat treatment can be made into a highly elastic and tough film.
- Preferred inorganic particles include, but are not limited to, silicon dioxide, titanium dioxide, alumina and the like.
- the resin composition of the present invention is a method of dissolving the above-described resin, if necessary, a solvent and other additives in a glass flask or stainless steel container, stirring and dissolving with a mechanical stirrer, etc., a method of dissolving with ultrasonic waves, It can be obtained by mixing by a method of stirring and dissolving with a planetary stirring deaerator.
- the conditions for stirring and mixing are not particularly limited.
- the viscosity of the resulting resin composition is preferably 1 to 10,000 mPa ⁇ s.
- the resin composition may be filtered through a filter having a pore size of 0.01 ⁇ m to 5 ⁇ m in order to remove foreign substances.
- the material for the filter examples include polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE), and polyethylene and nylon are preferable.
- PP polypropylene
- PE polyethylene
- NY nylon
- PTFE polytetrafluoroethylene
- polyethylene and nylon are preferable.
- a filtration filter having a pore size larger than these particle sizes.
- the resin composition of the present invention is applied on a support substrate to form a coating film, the coating film is dried to form a resin film, the resin film is exposed, and the exposed resin film is developed.
- a pattern can be formed through the process and the process of heat-processing the developed resin film.
- a resin composition is applied on a support substrate.
- the substrate may be a silicon wafer, ceramics, gallium arsenide, metal, glass, metal oxide insulating film, silicon nitride, ITO, IZO, amorphous silicon, microcrystal silicon, polysilicon, IGZO, or the like, but is not limited thereto.
- Application methods include spin coating using a spinner, spray coating, roll coating, slit die coating, inkjet coating, or a combination thereof.
- the coating film thickness varies depending on the coating method, the solid content concentration of the resin composition, the viscosity, etc., but it is generally applied so that the film thickness after drying is 0.1 to 150 ⁇ m.
- slit die coating or a method of rotating and coating after slit die coating is preferably used from the viewpoint of film thickness uniformity of the coating film.
- the substrate coated with the resin composition is dried to obtain a resin film. Drying is preferably performed using an oven, a hot plate, infrared rays, or the like in the range of 50 ° C. to 150 ° C. for 1 minute to several hours. If necessary, drying can be performed in two or more stages, such as 2 minutes at 80 ° C. and 2 minutes at 120 ° C.
- the pressure at the time of drying may be a normal pressure, but a step of drying at a reduced pressure first and then drying at a normal pressure from the viewpoint of film thickness uniformity of the resin film after drying is also preferably used.
- actinic radiation is irradiated on the resin film through a mask having a desired pattern.
- actinic rays used for exposure include ultraviolet rays, visible rays, electron beams, and X-rays.
- i rays (365 nm), h rays (405 nm), and g rays (436 nm) of a mercury lamp are used. preferable.
- photoresist film When photosensitivity is not imparted to the resin composition, it is necessary to form another layer of a photoresist film on the resin film.
- a photoresist a general novolak resist such as OFPR-800 (manufactured by Tokyo Ohka Co., Ltd.) is preferably used.
- the formation of the photoresist film is performed by the same method as the formation of the resin composition.
- a process of baking before development may be incorporated.
- This temperature is preferably in the range of 50 to 180 ° C, more preferably in the range of 60 to 150 ° C.
- the time is preferably 10 seconds to several hours. Within this range, there are advantages that the reaction proceeds satisfactorily and the development time can be shortened.
- development processing is performed. When the resin composition has negative photosensitivity, the relief pattern can be obtained by removing the unexposed portion with a developer, and when the resin composition has positive photosensitivity, the exposed portion is removed with the developer.
- An appropriate developer can be selected according to the structure of the resin composition, but ammonia, tetramethylammonium, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine
- An aqueous solution of an alkaline compound such as methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, and hexamethylenediamine can be preferably used.
- polar aqueous solutions such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, isopropanol are used in these alkaline aqueous solutions.
- alcohols such as ethyl lactate, esters such as propylene glycol monomethyl ether acetate, ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, and methyl isobutyl ketone may be added.
- N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, hexaxene which are good solvents for the resin composition of the present invention are used.
- a mixed solution of -3-methoxypropionate, ethyl-3-ethoxypropionate, 2-heptanone, cyclopentanone, cyclohexanone, ethyl acetate and the like alone or in combination of several kinds can be preferably used.
- the development can be performed by a method such as irradiating the developer on the coating film surface of the resin composition as it is or mist-like, immersing in the developer, or applying ultrasonic waves while immersing.
- the rinsing treatment may be performed with a liquid obtained by adding an ester such as ethanol, isopropyl alcohol or propylene glycol monomethyl ether acetate, an acid such as carbon dioxide, hydrochloric acid or acetic acid to water.
- an ester such as ethanol, isopropyl alcohol or propylene glycol monomethyl ether acetate, an acid such as carbon dioxide, hydrochloric acid or acetic acid
- the photoresist film formed on the resin film must be removed after development. This removal is often performed by dry etching or wet etching with a stripping solvent.
- a stripping solvent organic solvents such as acetone, butyl acetate, ethyl lactate, propylene glycol monomethyl ether acetate, methyl-3-methoxypropionate, ethyl-3-ethoxypropionate, 2-heptanone, ethyl acetate, An aqueous solution of sodium hydroxide or potassium hydroxide is used, but not limited thereto.
- the resin composition When a resin that forms a cyclic structure by heating or a catalyst, such as a polyimide precursor or a polybenzimidazole precursor, is used as the resin composition, the resin composition is converted to a heat-resistant resin having a cyclic structure. Is converted to a heat resistant coating.
- This heat treatment is preferably carried out for 5 minutes to 5 hours by selecting the temperature and raising the temperature stepwise, or selecting a certain temperature range and continuously raising the temperature.
- a method of performing heat treatment at 130 ° C., 200 ° C., and 350 ° C. for 30 minutes each, a method of linearly raising the temperature from room temperature to 320 ° C. over 2 hours, and the like can be mentioned.
- the heat treatment is preferably performed at 250 ° C. or lower because there is a fear that the electrical characteristics of the element may change due to high-temperature heating or repetition thereof, and the warpage of the substrate may increase.
- polyimide or polyamideimide is preferably used as the resin contained in the resin composition, and more preferably a resin including a structure represented by the general formula (4).
- the polyimide resin represented by the general formula (4) is most preferable. Since the polyimide resin represented by the general formula (4) already has a cyclic structure, it is not necessary to perform dehydration and ring closure by increasing the heat treatment temperature, so that the low temperature treatment of 250 ° C. or less is possible. Is an advantage.
- the residual stress resulting from the resin forming the heat resistant film of the substrate with the heat resistant film obtained by the above-described manufacturing method is 30 MPa or less. More preferably, it is 25 MPa or less, and most preferably 15 MPa or less. If the residual stress due to the resin is large, there is a possibility that the yield deteriorates during the manufacturing process of the device including the substrate with the heat-resistant coating and the reliability of the product is poor.
- the heat-resistant film formed from the resin composition of the present invention can be used for electronic parts such as semiconductor devices and multilayer wiring boards.
- a semiconductor passivation film, a surface protection film of a semiconductor element, an interlayer insulating film, an interlayer insulating film of a multilayer wiring for high-density mounting, an insulating layer of an organic electroluminescence element, a planarization film of a thin film transistor substrate, and an interlayer insulating film transistor Although used suitably for uses, such as a film, it is not restricted to this but can take various structures.
- a resin composition contains a conductive filler, it can also be used as a wiring material.
- FIG. 1 is an enlarged cross-sectional view of a pad portion of a semiconductor device having a bump according to the present invention.
- a passivation film 3 is formed on an input / output Al pad 2 in the silicon wafer 1, and a via hole is formed in the passivation film 3.
- a pattern (insulating film) 4 made of the resin composition of the present invention is formed thereon, and a metal (Cr, Ti, Ni, TiW, etc.) film 5 and a metal (Cu, Au, etc.) wiring 6 are further formed.
- a second insulating film 7 is formed on the Al pad 2 so as to be sequentially connected.
- the insulating film 7 is opened around the solder bump 10 and insulates the pads. Barrier metal 8 and solder bumps 10 are formed on the insulated pads.
- the resin composition of the present invention since the warpage of the wafer is small, exposure and transportation of the wafer can be performed with high accuracy.
- the resin of the present invention is excellent in mechanical characteristics, stress from the sealing resin can be relieved even during mounting, so that damage to the low-k layer can be prevented and a highly reliable semiconductor device can be provided.
- FIG. 2 shows a detailed method for producing a semiconductor device having bumps.
- the resin composition of the present invention is applied, and the insulating film 4 is formed through a photolithography process.
- the metal film 5 is formed by the sputtering method in 2b, and the metal wiring 6 is formed by the plating method in 2c.
- the resin composition of the present invention is applied again in 2d, and an insulating film 7 as shown in 2e is formed through a photolithography process.
- each layer can be formed by repeating the above steps.
- barrier metal 8 and solder bump 10 are formed. Finally, dicing is performed along the scribe line 9 to separate each chip. It is very preferable that the stress caused by the resin is low in this series of manufacturing processes because the warpage of the substrate can be reduced and the yield and reliability of the semiconductor device can be improved.
- FIG. 3B are enlarged sectional views of electrode portions of the chip stacked semiconductor device of the present invention.
- a passivation film 13 is formed on the input / output Al pad 12 in the silicon wafer 11, and a via hole is formed in the passivation film 13.
- a pattern (insulating film) 14 of the resin composition of the present invention is formed thereon, and these chips are laminated in multiple layers via an adhesive film 15 such as a die attach film, and wires (Cu, Au or the like) 16 is connected to the external terminal.
- an adhesive film 15 such as a die attach film
- wires (Cu, Au or the like) 16 is connected to the external terminal.
- a passivation film 24 is formed on the through electrode 22 and input / output pads (Al, Cu, etc.) 23 at both ends thereof in the silicon wafer 21, and a via hole is formed in the passivation film 24.
- a pattern (insulating film) 25 made of the resin composition of the present invention is formed thereon, and a barrier metal 26 and a solder bump 27 are sequentially formed. These chips are stacked vertically via an adhesive film 28 such as a die attach film.
- an adhesive film 28 such as a die attach film.
- the resin composition of the present invention is applied to a padded device substrate, and a pattern (insulating film 14) as shown in 5b is formed through a photolithography process.
- the substrate is ground and thinned as necessary, and is diced along the scribe line 9 in 5c and cut into chips.
- the chips cut in 5d are stacked via the adhesive film 15 so that the pads are exposed.
- the electrode exposed in 5e is connected to the outside with a wire. It is very preferable that the stress caused by the resin is low in this series of manufacturing processes because the warpage of the substrate can be reduced and the yield and reliability of the semiconductor device can be improved.
- the resin composition of the present invention is applied to the through electrode and the padded device substrate, and a pattern (insulating film 25) as shown in 6b is formed through a photolithography process.
- a pattern as shown in 6c, the wafer is diced along the scribe line 29 and cut into chips.
- a barrier metal 26 and a solder bump 27 are formed.
- the chips cut as shown in 6e are laminated through the adhesive film 28 so that the through electrodes are arranged vertically. It is very preferable that the stress caused by the resin is low in this series of manufacturing processes because the warpage of the substrate can be reduced and the yield and reliability of the semiconductor device can be improved.
- the heat resistant coating obtained from the resin composition of the present invention is suitably used as a planarizing film of a display device having a substrate on which a TFT (thin film transistor) is formed, a planarizing film, and a display element in this order.
- a display device include a liquid crystal display device and an organic EL display device.
- An active matrix type display device has a flattening film on a substrate such as glass or various plastics, which has a TFT and a wiring located on a side portion of the TFT and connected to the TFT, covering the unevenness thereon.
- a display element is provided over the planarization film. The display element and the wiring are connected through a contact hole formed in the planarization film.
- FIG. 7 shows a cross-sectional view of the TFT substrate.
- bottom gate type or top gate type TFTs 31 are provided in a matrix, and an insulating film 33 is formed so as to cover the TFTs 31.
- a wiring 32 connected to the TFT 31 is provided on the insulating film 33.
- a planarizing film 34 is provided on the insulating film 33 so as to bury the wiring 32.
- a contact hole 37 reaching the wiring 32 is provided in the planarizing film 34.
- An ITO (transparent electrode) 35 is formed on the planarizing film 34 while being connected to the wiring 32 through the contact hole 37.
- the ITO 35 serves as an electrode of a display element (for example, an organic EL element).
- the organic EL element may be a top emission type that emits emitted light from the side opposite to the substrate 36 or a bottom emission type that extracts light from the substrate 36 side, but is preferably a top emission type.
- an active matrix type organic EL display device in which the TFT 31 for driving the organic EL element is connected to each organic EL element is obtained.
- R 28 and R 33 are the same, and are independently substituted or unsubstituted C 1 -C 6 alkyl groups, substituted or unsubstituted C 1 -C 6 alkoxyl groups, hydroxyl groups , Halogenated alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C 30 heterocyclic aryl It is selected from one of group, ester group and nitro group.
- R 29 and R 32 are the same, R 30 and R 31 are the same, hydrogen, halogen, a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 alkoxyl group, Hydroxyl group, halogenated alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C 30 complex
- a ring aryl group, an ester group or a nitro group is selected, and the substituents may be the same or different, and may be halogen, trifluoromethyl, trimethylsilyl, a C 1 -C 6 alkoxyl group, C 1 One of a C 6 alkyl group, an arylalkoxyl group, a C 6 C 30 aryl group, or a C 4 C 30 hetero
- the substituted or unsubstituted C 1 to C 6 alkyl group is a C 1 to C 6 linear alkyl group, a C 1 to C 6 side chain alkyl group, or C 1 to C 6.
- 6 cycloalkyl groups are preferred, methyl, trifluoromethyl, ethyl, trifluoroethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl or Cyclohexyl and the like are more preferable.
- the substituted or unsubstituted C 1 -C 6 alkoxyl group is a C 1 -C 6 straight chain alkyl group, a C 1 -C 6 side chain alkyl group or a C 1 -C 6 cyclo group bonded by an ether group.
- An alkyl group is preferred, and methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, t-butoxy, n-pentyloxy, n-hexyloxy or cyclohexyloxy is more preferred.
- the halogenated alkyl group is preferably trifluoromethyl, trifluoroethyl, trichloromethyl, trichloroethyl, tribromomethyl, tribromoethyl or triiodomethyl, and more preferably trifluoromethyl or trifluoroethyl.
- the substituted or unsubstituted amino group is preferably a primary amino group, a secondary amino group or a tertiary amino group, and the amino group can be substituted by one or two groups, and the substituents are the same or different.
- a C 1 -C 6 alkyl group, a C 6 -C 30 aryl group, or a C 6 -C 30 heteroaryl group is preferred, and an amino group, methylamino, ethylamino, dimethylamino, phenylamino, More preferred is benzylamino, pyridineamino or furanylamino.
- the substituted or unsubstituted amide group is preferably an alkylamide group, an arylamide group, or an alkoxyamide group, and the substituent may be linked to a carbonyl group or an amino group.
- the substituted or unsubstituted C 6 -C 30 aryl group is a substituted or unsubstituted aromatic hydrocarbon group such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a biphenyl group, or a terphenyl group. preferable.
- the substituted or unsubstituted C 4 -C 30 heterocyclic aryl group is preferably a furanyl group or a pyridine group, and the ester group is an alkoxy carbonate group, of which the alkoxyl group is not particularly limited, and is a methoxy carbonate ester Ethoxy carbonate, propoxy carbonate, butoxy carbonate, t-butoxy carbonate, benzyloxy carbonate, fluorenyl methoxy carbonate and the like are preferable.
- the halogen is preferably fluoro, chloro or iodine, and the substituted or unsubstituted C 1 -C 6 alkyl group, the substituted or unsubstituted C 1 ⁇ alkoxy group C 6, the halogenated alkyl group, the substituted or unsubstituted amino group, the substituted or unsubstituted amide group, the substituted or unsubstituted C 6 ⁇ C 30 aryl group, the substituted or unsubstituted
- the substituted C 4 -C 30 heterocyclic aryl group and the ester group are all the same as described above.
- the halogen is preferably fluoro, chloro or iodine.
- the C 1 -C 6 alkoxy group is preferably a C 1 -C 6 linear alkyl group, a C 1 -C 6 side chain alkyl group or a C 1 -C 6 cycloalkyl group bonded by an ether group, More preferred are methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, t-butoxy, n-pentyloxy, n-hexyloxy or cyclohexyloxy.
- the C 1 -C 6 alkyl group is preferably a C 1 -C 6 straight chain alkyl group, a C 1 -C 6 side chain alkyl group or a C 1 -C 6 cycloalkyl group, such as methyl, trifluoromethyl, More preferred are ethyl, trifluoroethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, cyclohexyl and the like.
- the arylalkoxy group includes benzyloxy, naphthylmethoxy, anthracenylmethoxy, fluorenylmethoxy, 3,5-di-t-butylphenyl-1-isopropoxy, phenylethoxy, naphthylethoxy, benzidine-3-methoxy, etc. Are preferred, and benzyloxy or fluorenylmethoxy is more preferred.
- the C 6 -C 30 aryl group is preferably a substitutable aromatic hydrocarbon group such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a biphenyl group, or a terphenyl group, and the C 4 -C
- the 30 heteroaryl group is preferably a pyridine group, a carbazoyl group, an imidazole group, a furanyl group, a thiophene group, an oxazole group, an indolyl group, a benzofuranyl group, or a benzothiophene group.
- R 29, R 30, R 31 and R 32 in the described it is preferred that R 29, R 30, R 31 and R 32 are hydrogen.
- the present invention further describes a method for producing a 5,5'-dihydroxyl-4,4'-diaminobiphenyl derivative.
- a 5,4′-dibromo-4,4′-diaminobiphenyl derivative represented by the general formula (12) is obtained by bromination reaction of the 4,4′-diaminobiphenyl derivative represented by the general formula (11).
- R 34 and R 39 are the same, and each independently represents a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 alkoxyl group, a hydroxyl group Group, halogenated alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C 30 heterocycle It is selected from one of an aryl group, an ester group and a nitro group.
- R 35 and R 38 are the same, R 36 and R 37 are the same, and each independently represents hydrogen, halogen, a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 Alkoxyl group, hydroxyl group, alkyl halide group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C It is selected from one of 30 heterocyclic aryl groups, ester groups or nitro groups.
- R 40 and R 45 are the same and each independently represents a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 alkoxyl group, hydroxyl Group, halogenated alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C 30 heterocycle It is selected from one of an aryl group, an ester group and a nitro group.
- R 41 and R 44 are the same, R 42 and R 43 are the same, and each independently represents hydrogen, halogen, a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 Alkoxyl group, hydroxyl group, alkyl halide group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C It is selected from one of 30 heterocyclic aryl groups, ester groups or nitro groups.
- the substituents may be the same or different, and are each independently halogen, trifluoromethyl, trimethylsilyl, C 1 -C 6 alkoxyl group, C 1 -C 6 alkyl group, aryl alkoxyl group, C 6 -C 30 aryl Or a C 4 to C 30 heterocyclic group, wherein R 34 and R 39 , R 40 and R 45 are substituted or unsubstituted C 1 to C 6 .
- the C 30 aryl group, the substituted or unsubstituted C 4 -C 30 heterocyclic aryl group, and the ester group are all the same as described above.
- the halogen is preferably fluoro, chloro or iodine.
- the substituted or unsubstituted C 1 -C 6 alkyl group, the substituted or unsubstituted C 1 -C 6 alkoxy group, the halogenated alkyl group, the substituted or unsubstituted amino group, the substituted or unsubstituted The amide group, the substituted or unsubstituted C 6 -C 30 aryl group, the substituted or unsubstituted C 4 -C 30 heterocyclic aryl group, and the ester group are all the same as described above.
- the 30 aryl groups and the C 4 -C 30 heterocyclic group are all the same as described above.
- R 35 , R 36 , R 37 and R 38 are hydrogen
- R 41 , R 42 , R 43 and R 44 are hydrogen.
- the reaction solvent used in the bromination reaction is preferably an aprotic organic solvent, and is selected from methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethylene glycol dimethyl ether, tetrahydrofuran, 1,4-dioxane or a mixed solvent of the above solvents. 1 type or multiple types of is more preferable.
- the brominated solvent used in the bromination reaction is preferably liquid bromine or NBS.
- the reaction temperature is preferably between -30 ° C and 60 ° C, more preferably between -20 ° C and 60 ° C.
- the reaction time is preferably 1 h to 48 h, and more preferably 1 h to 12 h from the viewpoint of reaction rate and industrialization cost.
- the 5,5′-dibromo-4,4′-diaminobiphenyl derivative represented by the general formula (12) obtained by the above production method is further subjected to an amidation reaction using an acid anhydride or acyl chloride.
- a 5,5′-dibromo-4,4′-diamidobiphenyl derivative represented by the formula (13) is obtained.
- R 46 and R 51 are the same and each independently represents a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 alkoxyl group, hydroxyl Group, halogenated alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C 30 heterocycle It is selected from one of an aryl group, an ester group and a nitro group.
- R 47 and R 50 are the same, R 48 and R 49 are the same, and each independently represents hydrogen, halogen, a substituted or unsubstituted C 1 to C 6 alkyl group, a substituted or unsubstituted C 1 to C 6 Alkoxyl group, hydroxyl group, alkyl halide group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C It is selected from one of 30 heterocyclic aryl groups, ester groups or nitro groups.
- substituents may be the same or different, and are each independently halogen, trifluoromethyl, trimethylsilyl, C 1 -C 6 alkoxyl group, C 1 -C 6 alkyl group, aryl alkoxyl group, C 6 -C 30 Or a C 4 -C 30 heterocyclic group, wherein R 52 is a substituted or unsubstituted C 1 -C 6 alkyl group or a substituted or unsubstituted aryl group. Selected from one of them.
- the substituent in R 52 is one or more of a methyl group, a sulfo group, a fluorine atom, an amino group, and a methoxy group.
- the substituted or unsubstituted C 1 -C 6 alkyl group, the substituted or unsubstituted C 1 -C 6 alkoxy group, the halogenated alkyl group, the substituted or unsubstituted A substituted amino group, the substituted or unsubstituted amide group, the substituted or unsubstituted C 6 -C 30 aryl group, the substituted or unsubstituted C 4 -C 30 heterocyclic aryl group, and the ester group Are all the same as described above.
- the halogen is preferably fluoro, chloro or iodine, the substituted or unsubstituted C 1 -C 6 alkyl group, the substituted or unsubstituted C 1 ⁇ alkoxy group C 6, the halogenated alkyl group, the substituted or unsubstituted amino group, the substituted or unsubstituted amide group, the substituted or unsubstituted C 6 ⁇ C 30 aryl group, the substituted or unsubstituted
- the substituted C 4 -C 30 heterocyclic aryl group and the ester group are all the same as described above.
- the halogen, the C 1 -C 6 alkoxy group, the C 1 -C 6 alkyl group, the aryl alkoxy group, the C 6 -C 30 aryl group, the C 4 -C All 30 heterocyclic groups are the same as described above.
- the substituted or unsubstituted C 1 -C 6 alkyl group is a substituted or unsubstituted C 1 -C 6 linear alkyl group, a C 1 -C 6 side chain alkyl group or C C 1 -C 6 cycloalkyl groups are preferred, methyl, trifluoromethyl, ethyl, trifluoroethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n -Hexyl or cyclohexyl is more preferred, and the substituent of R 52 is more preferably one or more of a methyl group, a sulfo group, a fluorine atom, an amino group, and a methoxy group.
- the substituted or unsubstituted aryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted biphenyl group is preferred.
- a phenyl group, p-methylphenyl, o-methylphenyl, m-methylphenyl, sulfophenyl, p-methoxyphenyl, p-fluorophenyl and the like are preferable, and the substituent of R 52 is a methyl group, a sulfo group, a fluorine atom, One or more of amino groups and methoxy groups are preferred.
- R 47, R 48, R 49 and R 50 of the described it is preferred that R 47, R 48, R 49 and R 50 is hydrogen.
- the acid anhydride has the general formula (R 52 CO) 2 O, and from the viewpoint of industrialization cost, the acid anhydride is preferably acetic anhydride, benzoic anhydride, or trifluoroacetic anhydride.
- the acyl chloride has the general formula R 52 COCl, and the R 25 is the same as described above. From the viewpoint of industrialization cost, the acyl chloride is acetyl chloride, propionic acid chloride, hexanenoyl chloride, benzoyl chloride, or pivaloyl chloride. Is preferred.
- the temperature of the amidation reaction is preferably 0 ° C. to 80 ° C., more preferably 10 ° C. to 40 ° C.
- the amide reaction solvent used is an aprotic solvent, more preferably tetrahydrofuran or dichloromethane.
- the reaction time is preferably 1 h to 48 h, and more preferably 1 h to 12 h from the viewpoint of reaction rate and industrialization cost.
- the 5,5′-dibromo-4,4′-diamidebiphenyl derivative represented by the general formula (13) obtained by the above production method is further reacted under the action of a catalyst and an inorganic alkali.
- a 6,6′-dibenzoxazole derivative represented by the formula (14) is obtained.
- R 54 and R 59 are the same and each independently represents a substituted or unsubstituted C 1 -C 6 alkyl group, a substituted or unsubstituted C 1 -C 6 alkoxyl group, hydroxyl Group, halogenated alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C 30 heterocycle It is selected from one of an aryl group, an ester group and a nitro group.
- R 55 and R 58 are the same, R 56 and R 57 are the same, and each independently represents hydrogen, halogen, a substituted or unsubstituted C 1 to C 6 alkyl group, a substituted or unsubstituted C 1 to C 6 Alkoxyl group, hydroxyl group, alkyl halide group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted C 6 -C 30 aryl group, substituted or unsubstituted C 4 -C It is selected from one of 30 heterocyclic aryl groups, ester groups or nitro groups.
- the substituents may be the same or different, and are each independently halogen, trifluoromethyl, trimethylsilyl, C 1 -C 6 alkoxyl group, C 1 -C 6 alkyl group, aryl alkoxyl group, C 6 -C 30 Or a C 4 -C 30 heterocyclic group, and one of a C 1 -C 6 alkyl group or a substitutable aryl group in which R 60 can be substituted.
- the substituent in R 60 is one or more of a methyl group, a sulfo group, a fluorine atom, an amino group, and a methoxy group.
- the substituted or unsubstituted C 1 -C 6 alkyl group, the substituted or unsubstituted C 1 -C 6 alkoxy group, the halogenated alkyl group, the substituted or unsubstituted A substituted amino group, the substituted or unsubstituted amide group, the substituted or unsubstituted C 6 -C 30 aryl group, the substituted or unsubstituted C 4 -C 30 heterocyclic aryl group, and the ester group Are all the same as described above.
- the halogen is preferably fluoro, chloro or iodine, the substituted or unsubstituted C 1 to C 6 alkyl group, the substituted or unsubstituted C 1 ⁇ alkoxy group C 6, the halogenated alkyl group, the substituted or unsubstituted amino group, the substituted or unsubstituted amide group, the substituted or unsubstituted C 6 ⁇ C 30 aryl group, the substituted or unsubstituted
- the substituted C 4 -C 30 heterocyclic aryl group and the ester group are all the same as described above.
- the halogen, the C 1 -C 6 alkoxy group, the C 1 -C 6 alkyl group, the aryl alkoxy group, the C 6 -C 30 aryl group, the C 4 -C All 30 heterocyclic groups are the same as described above.
- the substituted or unsubstituted C 1 -C 6 alkyl group is a substituted or unsubstituted C 1 -C 6 linear alkyl group, a C 1 -C 6 side chain alkyl group, or C C 1 -C 6 cycloalkyl groups are preferred, methyl, trifluoromethyl, ethyl, trifluoroethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n -Hexyl or cyclohexyl is more preferred.
- the substituent for R 60 is more preferably one or more of a methyl group, a sulfo group, a fluorine atom, an amino group, and a methoxy group.
- the substituted or unsubstituted aryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted biphenyl group is preferred.
- a phenyl group, p-methylphenyl, o-methylphenyl, m-methylphenyl, sulfophenyl, p-methoxyphenyl, p-fluorophenyl and the like are preferable, and the substituent of R 60 is a methyl group, a sulfo group, a fluorine atom, One or more of amino groups and methoxy groups are preferred.
- R 55 , R 56 , R 57 and R 58 described above R 55 , R 56 , R 57 and R 58 are preferably hydrogen.
- the catalyst contains at least a copper catalyst and may or may not contain a ligand.
- the copper catalyst may be copper iodide (I), copper oxide (I), copper acetate (I ) Or copper (I) cyanide, more preferably copper (I) iodide or copper (I) oxide, of which the ligand is N, N'-dimethylethylenediamine, ethylenediamine, ethylene glycol or 1,10- Orthophenanthroline is preferred, N, N′-dimethylethylenediamine is more preferred, and the inorganic alkali in the catalytic reaction process is preferably one or more of potassium carbonate or potassium phosphate, and the reaction temperature is 100 ° C. to 140 ° C. preferable.
- the solvent used is preferably a high boiling point organic solvent, more preferably toluene or xylene.
- the present invention further provides the 5,5′-dihydroxyl-4,4′-diaminobiphenyl derivative by subjecting the 6,6′-dibenzoxazole derivative obtained by the above production method to a ring-opening reaction under acidic conditions. .
- the acidic condition is preferably an inorganic strong acid
- the inorganic strong acid is preferably hydrochloric acid, sulfuric acid, acetic acid, phosphoric acid, nitric acid or formic acid, and hydrochloric acid or sulfuric acid is more preferable from the viewpoint of industrialization cost.
- the solvent used for the ring-opening reaction is a protic solvent, preferably ethanol, methanol, isopropanol or water, and more preferably ethanol or water from the viewpoint of industrialization cost.
- the present invention relates to a class of 5,5′-dihydroxyl-4,4′-diaminobiphenyl derivatives and industrialized production methods thereof.
- the production method has a high reaction yield and simple post-treatment. Production cost is low.
- the 5,5′-dihydroxyl-4,4′-diaminobiphenyl derivative produced according to the present invention is used in the field of electronic materials such as polyimide resins, thin films, liquid crystal materials, semiconductors, flat panel displays, or drug intermediates. Can be done.
- the reaction is performed using a biphenyl compound having the structure described in the general formula (15) as a raw material, without using any other reactant (such as a catalyst), and an aprotic solvent and a bromination reagent.
- the dibromobiphenyl derivatives having the structure described in the general formula (16) can be obtained under the reaction conditions of This method has a high reaction yield, simple post-treatment, good solvent recovery, low environmental pollution, and easy mass production.
- R 61 and R 62 may be the same or different. Hydrogen, halogen, C 1 -C 6 alkyl group, C 1 -C 6 alkoxyl group, hydroxyl group, halogenated alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted Selected from one of C 6 -C 30 aryl groups, ester groups and nitro groups.
- R 3 and R 4 may be the same or different.
- C 1 -C 6 alkyl group C 1 -C 6 alkoxyl group, hydroxyl group, substituted or unsubstituted aryl group, substituted or unsubstituted amino group, substituted or unsubstituted amide group, substituted or unsubstituted It is selected from one of an imide group, a substituted or unsubstituted sulfamine group, a substituted or unsubstituted sulfinamide group, or a substituted or unsubstituted aromatic heterocyclic group.
- the substituents may be the same or different, and are trifluoromethyl, trimethylsilyl, C 1 -C 6 alkoxyl group, C 1 -C 6 alkyl group, aryl alkoxyl group, C 6 -C 30 aryl group Or one or more of the heterocyclic groups.
- the halogen is preferably fluoro, chloro or bromo, more preferably fluoro or chloro.
- the C 1 -C 6 alkyl group is preferably a C 1 -C 6 straight chain alkyl group, a C 1 -C 6 side chain alkyl group or a C 1 -C 6 cycloalkyl group, such as methyl, ethyl, n- More preferred are C 1 -C 6 saturated aliphatic hydrocarbon groups such as propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, or cyclohexyl.
- the C 1 -C 6 alkoxyl group is preferably a C 1 -C 6 linear alkoxyl group, a C 1 -C 6 side chain alkoxyl group or a C 1 -C 6 cycloalkoxyl group.
- Methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, cyclopentyloxy, cyclohexyloxy and the like are more preferable.
- the halogenated alkyl group is preferably trifluoromethyl, trifluoroethyl, chloromethyl, dichloromethyl, trichloromethyl, dichloroethyl, tetrachloroethyl, bromomethyl, or bromoethyl, more preferably trifluoromethyl or trifluoroethyl, More preferred is fluoromethyl.
- the substituted or unsubstituted amino group is preferably a primary amino group, a secondary amino group, or a tertiary amino group, and the amino group can be substituted by one or two groups, and the substituent in the amino group is It may be the same or different.
- the substituent is preferably a linear alkyl group, a side chain alkyl group, a cycloalkyl group, a halogenated alkyl group, an arylalkoxyl group, an aryl group, a heteroaryl group or a heterocyclic group.
- Amino group methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, isopropylamino, t-butylamino, cyclopentylamino, cyclohexylamino, dimethylamino, trifluoromethylamino, phenylamino, naphthylamino, anthracene Amino, phenanthrylamino, pyrenylamino, benzylamino, pyridineamino, furanylamino, pyronylamino, carbazoylamino, thiophenamino, quinolineamino, and the like are more preferable, and an amino group is more preferable.
- the substituted or unsubstituted amide group is preferably an alkylamide group, a halogenated alkylamide group, an arylalkoxyamide group, a heterocyclic group amide group, an arylamide group, or an alkoxyamide group.
- the substituent may be linked to a carbonyl group or may be linked to an amino group, acetamide, propionamide, butyrylamino, pentanamide, hexaneamide, trifluoromethylamide, tertiary butoxide amide, benzamide, More preferred are naphthamide, bibenzamide, benzyloxyamide, pyridineformamide, furanylformamide, thiopheneformamide, acetopropylamine, or acetanilide. Acetamide, tertiary butoxide amide, benzyloxyamide and the like are more preferable.
- the substituted or unsubstituted aryl group is not particularly limited, but is preferably an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a biphenyl group, or a terphenyl group.
- the ester group is preferably a substituted or unsubstituted alkoxy carbonate group, methoxy carbonate, ethoxy carbonate, propoxy carbonate, butoxy carbonate, tertiary butoxide carbonate, benzyloxy carbonate, or fluorenylmethoxy. Carbonic acid esters and the like are more preferable.
- R 63 and R 64 the C 1 -C 6 alkyl group, the C 1 -C 6 alkoxyl group, the substituted or unsubstituted aryl group, the substituted or unsubstituted amino group, the substituted or unsubstituted
- the explanation of the substituted amide group and the substituent is as described above.
- the substituted or unsubstituted imide group includes a C 1 to C 6 alkylimide group, a C 1 to C 6 halogenated alkylimide group, a C 1 to C 6 alkoxyimide group, and a C 6 to C 30 arylimide group.
- a arylalkoxyimide group or a multi-ring imide group is preferred, and phthalimide, succinimide, ditertiary butoxide dicarboximide, or dibenzyloxydicarboximide is more preferred.
- the substituted or unsubstituted sulfamine group is preferably a C 1 -C 6 alkylsulfamine group, a C 1 -C 6 halogenated alkylsulfamine group, a C 1 -C 6 arylsulfamine group, or a multi-ring sulfamine group.
- Methanesulfonamide, trifluoromethylsulfamine, benzenesulfonamide, p-toluenesulfonamide, and the like are more preferable.
- the substituted or unsubstituted sulfinamide group is a C 1 -C 6 alkylsulfinamide group, a C 1 -C 6 halogenated alkylsulfinamide group, a C 1 -C 6 arylsulfinamide group, or a multi-ring sulfinamide group.
- Amide groups and the like are preferable, and methylsulfinamide, trifluoromethylsulfinamide, phenylsulfinamide, p-toluenesulfinamide, t-butylsulfinamide and the like are more preferable.
- the substituted or unsubstituted aromatic heterocyclic group is preferably a cyclic aromatic group having a heteroatom other than carbon in one or more rings, and may be substituted or unsubstituted.
- an aromatic heterocyclic group having 2 to 30 carbon atoms is preferable, and a pyrrole group, a pyridine group, a pyrimidinyl group, a quinoline group, a pyrazine group, a carbazoyl group, an indolyl group.
- a nitrogen-containing aromatic heterocyclic group such as a phthalimide group is preferred, and a phthalimide group is more preferred.
- the C 1 -C 6 alkoxyl group is preferably a C 1 -C 6 linear alkoxyl group, a C 1 -C 6 side chain alkoxyl group or a C 1 -C 6 cycloalkoxyl group, More preferred are ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, or cyclohexyloxy.
- the C 1 -C 6 alkyl group is preferably a C 1 -C 6 straight chain alkyl group, a C 1 -C 6 side chain alkyl group or a C 1 -C 6 cycloalkyl group, such as methyl, ethyl, n- More preferred are C 1 -C 6 saturated aliphatic hydrocarbon groups such as propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, or cyclohexyl.
- the arylalkoxyl group is a benzyloxy group, a naphthylmethoxy group, an anthracenylmethoxy group, a fluorenylmethoxy group, a 3,5-di-t-butylphenyl-1-isopropoxy group, a phenylethoxy group, a naphthylethoxy group, or A benzidine-3-methoxy group or the like is preferable, and a benzyloxy group or a fluorenylmethoxy group is more preferable.
- the C 6 -C 30 aryl group is preferably an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a biphenyl group, or a terphenyl group.
- the heterocyclic group is pyridine group, carbazoyl group, imidazole group, furanyl group, thiophene group, oxazoyl group, indolyl group, benzofuranyl group, benzothiophene group, thiazinyl group, pyrimidine group, quinolyl group, isoquinolyl group, pyrazo group, imidazole group A thiazoyl group, a pyranyl group, a biperazine group, a phenazine group, a phenothiazine group, a pyridazinyl, a tetrahydrofuran group, a dioxane group, a phthalimide group, or a succinimide group, and a phthalimide group or a succinimide group is more preferable.
- R 61 and R 62 may be the same or different, and are each halogen, C 1 -C 6 alkyl group, C 1 -C 6 alkoxyl group, halogenated alkane, ester It is preferably selected from one of a group or a nitro group.
- the halogenated alkane is preferably trifluoromethyl or one of trifluoroethyl
- the C 1 -C 6 alkyl group is more preferably methyl
- the C 1 -C 6 alkoxyl group is methoxy. More preferred.
- R 63 and R 64 may be the same or different from each other, and are substituted or unsubstituted amino groups, substituted or unsubstituted amide groups, substituted or unsubstituted. It is preferably selected from one of a substituted imide group, a substituted or unsubstituted sulfamine group, a substituted or unsubstituted sulfinamide group, or a substituted or unsubstituted aromatic heterocyclic group.
- each of amino group, acetamide group, tertiary butoxide amide group, benzyloxyamide group, ditertiary butoxide dicarboximide group, dibenzyloxydicarboximide group, or phthalimide group independently.
- One type is more preferable.
- the aprotic solvent used in the present invention is an alkane solvent (eg, cyclohexane, normal hexane, normal pentane, etc.), an arene solvent (eg, benzene, toluene, xylene, etc.), a haloalkane solvent (eg, dichloromethane, trichloromethane, tetrachloride).
- alkane solvent eg, cyclohexane, normal hexane, normal pentane, etc.
- an arene solvent eg, benzene, toluene, xylene, etc.
- a haloalkane solvent eg, dichloromethane, trichloromethane, tetrachloride
- ester solvents eg, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, propylene glycol methyl ether
- ether solvents eg, ethyl ether, tetrahydrofuran, 1,4-dioxane, etc.
- Ketones acetone, butanone, methyl ethyl ketone, etc.
- aprotic solvents eg, N, N-dimethylformamide, N-methylpyrrolidone, acetonitrile, dimethyl sulfoxide, etc.
- an asterisol solvent, an ether solvent or a mixture thereof is more preferable.
- methyl acetate, ethyl acetate, propyl acetate, acetic acid Butyl, propylene glycol methyl ether, glycol dimethyl ether, tetrahydrofuran, 1,4-dioxane and the like, or one or more of the above mixed solvents are more preferable.
- the bromination solvent used in the present invention is selected from one or more of the following reagents.
- the molar ratio of the raw material biphenyl compound to the brominating reagent is 1: 2 to 1: 6, and from the comprehensive viewpoint of the raw material price, yield, and post-treatment difficulty, the raw material biphenyl compound and bromine
- the molar ratio with the chlorinating reagent is preferably 1: 2 to 1: 3.
- the molar concentration of the raw material biphenyl compound in the present invention is preferably 0.05 mol / L to 5 mol / L. From the viewpoint of solubility and solvent cost, the molar concentration of the raw material biphenyl compound is 0.2 mol / L to 2 mol / L. Is more preferable.
- the reaction temperature in the present invention is preferably -30 ° C to 60 ° C, and more preferably -20 ° C to 60 ° C from the viewpoint of mass production cost.
- the reaction time in the present invention is preferably 1 h to 48 h, and more preferably 1 h to 12 h from the viewpoint of reaction rate and mass production cost.
- the alkali used is preferably an inorganic alkali.
- sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate, potassium bicarbonate, Sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide or the like is preferable.
- the solvent used is petroleum ether, ethyl acetate, butyl acetate, toluene, xylene, dichloromethane, 1,2-dichloroethane, acetonitrile, ethanol, from the viewpoint of solvent cost and solubility.
- solvents such as methanol, isopropanol, propylene glycol methyl ether acetate, glycol dimethyl ether, ethyl ether, tetrahydrofuran, or 1,4-dioxane are preferable.
- the resin film was heated to 250 ° C. at an oxygen concentration of 20 ppm or less at 5 ° C./min, and heat-treated at 250 ° C. for 1 hour. Then, it was cooled to 50 ° C. at 5 ° C./min. Subsequently, it was immersed in hydrofluoric acid for 1 to 4 minutes to peel the film from the substrate and air-dried to obtain a heat-treated film. The number of rotations during spin coating was adjusted so that the resin film thickness after the heat treatment was 10 ⁇ m.
- the film after the heat treatment was measured under a nitrogen stream using a thermomechanical analyzer (EXSTAR6000 TMA / SS6000 manufactured by SII Nanotechnology Co., Ltd.).
- the temperature raising method was performed under the following conditions. In the first stage, the temperature was raised to 200 ° C. at a temperature rising rate of 5 ° C./min to remove adsorbed water from the sample, and in the second stage, air cooling was performed to a room temperature at a temperature lowering rate of 5 ° C./min. In the third stage, the main measurement was performed at a temperature elevation rate of 5 ° C./min, and the average value of the thermal linear expansion coefficient from 50 ° C. to 200 ° C. was obtained.
- the resin solution was spin-coated on a glass substrate (AN-100 manufactured by Asahi Glass Co., Ltd.) having a thickness of 50 mm ⁇ 50 mm ⁇ 0.7 mm using a spin coater MS-A200 manufactured by Mikasa Co., Ltd. Subsequently, it was baked for 3 minutes on a 120 ° C. hot plate (using a hot plate D-SPIN manufactured by Dainippon Screen Co., Ltd.) to obtain a resin film. The number of rotations during spin coating was adjusted so that the resin film thickness was 10 ⁇ m.
- the obtained resin film was measured for absorbance at 365 nm using an ultraviolet-visible spectrophotometer (MultiSpec 1500, manufactured by Shimadzu Corporation). The obtained absorbance was divided by the resin film thickness to obtain the absorbance per 1 ⁇ m.
- the resin film was developed with a 2.38 wt% tetramethylammonium (TMAH) aqueous solution (ELM-D, manufactured by Mitsubishi Gas Chemical Co., Ltd.) for 60 seconds, and then rinsed with pure water. The film thickness after rinsing was measured, and the decrease in film thickness per minute was calculated.
- TMAH tetramethylammonium
- Residual stress measurement method The resin solution was spin-coated on an 8-inch silicon wafer, and then baked for 3 minutes on a 120 ° C. hot plate (using a coating and developing apparatus Act-8 manufactured by Tokyo Electron Ltd.). A resin film was obtained.
- the resin film was heated to 250 ° C. at an oxygen concentration of 20 ppm or less at 5 ° C./min, and heat-treated at 250 ° C. for 1 hour. Then, it was cooled to 50 ° C. at 5 ° C./min. Subsequently, it was immersed in hydrofluoric acid for 1 to 4 minutes to peel the film from the substrate and air-dried to obtain a heat-treated film. The number of rotations during spin coating was adjusted so that the resin film thickness after the heat treatment was 10 ⁇ m.
- the residual stress was measured in a 23 degreeC, 45% RH, air atmosphere using the thin film stress measuring apparatus (made by KLA Tencor Co., Ltd.), and the blank applied the resin solution.
- the silicon wafer before being used was used.
- Photosensitivity evaluation method A resin solution is spin-coated on an 8-inch silicon wafer, and then baked for 3 minutes on a 120 ° C. hot plate (using a coating and developing apparatus Act-8 manufactured by Tokyo Electron Co., Ltd.). A 6 ⁇ m pre-baked film was prepared. This film was exposed using an i-line stepper (NIKON NSR i9) at an exposure dose of 0 to 1000 mJ / cm 2 in 10 mJ / cm 2 steps. After the exposure, the resist film was developed for 90 seconds with a 2.38% by weight tetramethylammonium (TMAH) aqueous solution (ELM-D, manufactured by Mitsubishi Gas Chemical Co., Ltd.), and then rinsed with pure water.
- TMAH tetramethylammonium
- the exposure amount (hereinafter referred to as the minimum exposure amount Eth) at which the exposed portion was not completely eluted after exposure and development was defined as sensitivity. If Eth is 700 mJ / cm 2 or less, it can be determined that the sensitivity is high. 500 mJ / cm 2 or less is more preferable.
- BAHF 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane
- HFHA 2,2-bis [3- (3-aminobenzamido) -4-hydroxyphenyl] hexafluoropropane
- DAE 4,4 '-Diaminodiphenyl ether.
- Synthesis Example 2 Synthesis of Hydroxyl Group-Containing Diamine Compound (b) 2,2′-bis (trifluoromethyl) -5,5′-dihydroxybenzidine (17.6 g, 0.05 mol) was added to 2,2′-dimethyl-5 , 5′-dihydroxybenzidine A hydroxyl group-containing diamine compound (b) represented by the following formula was obtained in the same manner as in Synthesis Example 1 except that the amount was changed to 17.6 g (0.05 mol). The obtained solid was used for the reaction as it was.
- Synthesis Example 3 Synthesis of Hydroxyl Group-Containing Diamine Compound (c) Synthesis Example 1 except that 20.4 g (0.11 mol) of 3-nitrobenzoyl chloride was changed to 20.4 g (0.11 mol) of 4-nitrobenzoyl chloride In the same manner as above, a hydroxyl group-containing diamine compound (c) represented by the following formula was obtained. The obtained solid was used for the reaction as it was.
- Synthesis Example 5 Synthesis of quinonediazide compound (e) In a dry nitrogen stream, TrisP-PA (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) 21.22 g (0.05 mol) and 5-naphthoquinonediazidesulfonyl acid chloride 26.86 g (0.10 mol) and 13.43 g (0.05 mol) of 4-naphthoquinonediazide sulfonyl chloride were dissolved in 50 g of 1,4-dioxane and brought to room temperature. To this, 15.18 g of triethylamine mixed with 50 g of 1,4-dioxane was added dropwise so that the temperature inside the system would not exceed 35 ° C.
- TrisP-PA trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- Synthesis example 80 The same method as Synthesis Example 58, except that 15.8 g (0.045 mol) of 2,2′-bis (trifluoromethyl) -3,3′-dihydroxybenzidine was changed to 9.73 g (0.045 mol) of HAB. However, the polymer was precipitated during cooling of the liquid after the reaction at 200 ° C., and an insoluble resin was obtained.
- Synthesis Examples 82 to 84 Resins (D2) to (D4) were obtained in the same manner as in Synthesis Example 81 using the combination of the amine component, acid component, and terminal blocking agent shown in Table 4.
- Synthesis example 85 Under a dry nitrogen stream, 17.6 g (0.05 mol) of 2,2′-bis (trifluoromethyl) -3,3′-dihydroxybenzidine was dissolved in 100 g of NMP. Diphenyl ether dicarboxylic acid diimidazolide 14.32g (0.04mol) was added here with NMP10g, and it stirred at 85 degreeC for 4 hours. Thereafter, 3.28 g (0.02 mol) of NA was added, and the mixture was further stirred at 85 ° C. for 2 hours. After completion of the reaction, 30 g of acetic acid was slowly added while keeping the solution temperature at 30 ° C. or lower. The solution after stirring for 30 minutes at 30 ° C.
- Example 64 17.5 g of the resin (B1), 2.3 g of the quinonediazide compound (b) obtained in Synthesis Example 5 and 0.5 g of KBM-403 were added to 45 g of GBL to obtain a photosensitive resin composition. Photosensitivity evaluation was performed as mentioned above using the obtained photosensitive resin composition. The evaluation results are shown in Table 6.
- Examples 65 to 106, Comparative Examples 17 to 26 A photosensitive resin composition was obtained in the same manner as in Example 64 for resins (B2) to (B26), resins (C1) to (C22), and resins (D1) to (D5). Photosensitivity evaluation was performed as mentioned above using the obtained photosensitive resin composition. The evaluation results are shown in Table 6.
- reaction yield is in mole percent.
- Both the solvent and catalyst used in the examples are purchased from a reagent supplier such as National Drug, Aldrich, TCI or Alfa, and are used directly in the reaction without post-treatment.
- the structure of the reaction product was confirmed by a nuclear magnetic resonance spectrum, and the nuclear magnetic resonance apparatus used was JEOL (400 MHz).
- the purity of the reaction product was measured using high performance liquid chromatography.
- the high performance liquid chromatography used was SHIMADZU Prominence, and the chromatographic column was YMC Pack Ph.
- Example 107 To a Erlenmeyer flask, 2,2,2′-ditrifluoromethyl-4,4′-diaminobiphenyl (80.0 g, 0.25 mol) and ethyl acetate (800 mL) were added, and the reaction flask was replaced with nitrogen gas three times. Was placed in an ice bath ( ⁇ 20 ° C.) and stirred, and then liquid bromine (26.2 mL, 0.51 mol) was added dropwise to the reaction flask, and liquid bromine was added dropwise while controlling the reaction temperature to 20 ° C. or lower. did. The reaction was followed by high performance liquid chromatography.
- Example 109 To the Erlenmeyer flask was added 2,2′-ditrifluoromethyl-5,5′-dibromo-4,4′-diaminobiphenyl (95.6 g, 0.2 mol) and dichloromethane (500 mL) obtained by the above production method, and triethylamine was added. (71.8 ml, 0.514 mol) and pivaloyl chloride (63.0 ml, 0.514 mol) were added, the reaction flask was placed in a 40 ° C constant temperature oil bath and stirred overnight, and the reaction was monitored by high performance liquid chromatography.
- the raw material biphenyl compound having the general formula (13) structure is dissolved in an aprotic solvent, and a bromination reagent is added to the reaction flask under the conditions of ⁇ 30 ° C. to 60 ° C. until the raw material is almost exhausted.
- a bromination reagent is added to the reaction flask under the conditions of ⁇ 30 ° C. to 60 ° C. until the raw material is almost exhausted.
- the reaction yield is in mole percent.
- Example 110 Add 2,2'-ditrifluoromethyl-4,4'-diaminebiphenyl (80.0 g, 0.25 mol) and ethyl acetate (800 mL) to the Erlenmeyer flask, and replace with nitrogen gas three times.
- the liquid bromine (26.2 mL, 0.51 mol) was added dropwise to the reaction flask, and the liquid bromine was added dropwise, followed by stirring, and the reaction was measured by high performance liquid chromatography.
- Example 113 Add 2,2'-ditrifluoromethyl-4,4'-di (phthalimido) biphenyl (145.0 g, 0.25 mol) and propylene glycol methyl ether acetate (500 mL) to the Erlenmeyer flask and replace with nitrogen gas three times. Stirring was performed at room temperature, and then liquid bromine (26.2 mL, 0.51 mol) was added dropwise to the reaction flask. After liquid bromine was added dropwise, stirring was continued.
- the reaction was followed by high performance liquid chromatography, and when the content of the raw material was less than 3%, the stirring was stopped, a saturated sodium carbonate solution was gradually added to the reaction flask, the pH value was adjusted to neutral, and the organic phase was The organic phase was washed with water (300 mL each time, washed twice), dried over anhydrous sodium sulfate, filtered, and then the organic solvent was removed to obtain a crude product yellow solid.
- the reaction was monitored by high performance liquid chromatography. When the content of the raw material was less than 3%, the stirring was stopped, a saturated sodium carbonate solution was gradually added to the reaction flask, and the pH value was adjusted to neutral. Separation, the organic phase was washed with water (500 mL each time, washed twice), dried over anhydrous sodium sulfate and filtered. After filtration, the organic solvent was removed to obtain a crude product yellow solid.
- N-bromosuccinimide 17.8 g, 0.10 mmol
- sodium hydroxide was added to the reaction flask.
- the organic phase is separated, the organic phase is washed with water (200 mL each time, washed twice), dried over anhydrous sodium sulfate, filtered, and filtered with an organic solvent. Was removed to give a crude reddish orange solid.
- NBS 8.9 g, 0.05 mol
- NBS 8.9 g, 0.05 mol
- the stirring was stopped when the content of the raw material was less than 3%, and the sodium hydroxide solution was gradually added to the reaction flask.
- ethyl acetate 300 mL was added to separate the organic phase
- the organic phase was washed with saturated brine (200 mL, washed twice), washed with water (200 mL), Anhydrous sodium sulfate was added and dried, and after filtration, the organic solvent was removed to obtain a crude product reddish orange solid.
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Abstract
Description
すなわち、本発明は、下記一般式(1)、(2)で表される構造から選ばれる少なくとも1つの構造を含むことを特徴とする樹脂である。
一般式(1)は2価の有機基であり、R1、R2は各々独立にハロゲン原子または炭素数1~3の1価の有機基を示す。得られる樹脂の耐熱性という点から、メチル基、メトキシ基、エチル基、エトキシ基、フルオロ基、トリフルオロメチル基、ペンタフルオロエチル基、トリフルオロメトキシ基、ペンタフルオロエトキシ基などが好ましい具体例として挙げられるがこれらに限定されない。得られる樹脂の吸光度を低減できるという点から、フルオロ基、トリフルオロメチル基、ペンタフルオロエチル基、トリフルオロメトキシ基、ペンタフルオロエトキシ基がさらに好ましく、トリフルオロメチル基、ペンタフルオロエチル基が最も好ましい。また、得られる樹脂の吸光度を低減できるという点から、R1、R2はポリマー鎖に対してオルソ位にあることが好ましい。さらに、得られる樹脂の熱線膨張係数を低減できるという点からR1、R2は2位、2’位の位置に結合していることがより好ましい。
一般式(3)、(4)、(5)中、R9、R12、R14はジアミン、シリル化ジアミン、またはジイソシアネートの残基を表し、炭素数2~50の2価の有機基を示す。中でも芳香族環又は環状脂肪族基を含有する炭素原子数5~40の有機基が好ましい。好ましい具体例としては、ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン、ビス(3-アミノ-4-ヒドロキシフェニル)スルホン、ビス(3-アミノ-4-ヒドロキシフェニル)プロパン、ビス(3-アミノ-4-ヒドロキシフェニル)メチレン、ビス(3-アミノ-4-ヒドロキシフェニル)エーテル、ビス(3-アミノ-4-ヒドロキシ)ビフェニル、ビス(3-アミノ-4-ヒドロキシフェニル)フルオレン、3,5-ジアミノ安息香酸、3-カルボキシ-4,4’-ジアミノジフェニルエーテル、3-スルホン酸-4,4’-ジアミノジフェニルエーテル、ジチオヒドロキシフェニレンジアミン、3,4’-ジアミノジフェニルエーテル、4,4’-ジアミノジフェニルエーテル、3,4’-ジアミノジフェニルメタン、4,4’-ジアミノジフェニルメタン、3,4’-ジアミノジフェニルスルホン、4,4’-ジアミノジフェニルスルホン、3,4’-ジアミノジフェニルスルフィド、4,4’-ジアミノジフェニルスルフィド、1,4-ビス(4-アミノフェノキシ)ベンゼン、1,3-ビス(4-アミノフェノキシ)ベンゼン、ベンジジン、m-フェニレンジアミン、p-フェニレンジアミン、1,5-ナフタレンジアミン、2,6-ナフタレンジアミン、ビス(4-アミノフェノキシフェニル)スルホン、ビス(3-アミノフェノキシフェニル)スルホン、ビス(4-アミノフェノキシ)ビフェニル、ビス{4-(4-アミノフェノキシ)フェニル}エーテル、2,2’-ジメチル-4,4’-ジアミノビフェニル、2,2’-ジエチル-4,4’-ジアミノビフェニル、3,3’-ジメチル-4,4’-ジアミノビフェニル、3,3’-ジエチル-4,4’-ジアミノビフェニル、2,2’,3,3’-テトラメチル-4,4’-ジアミノビフェニル、3,3’,4,4’-テトラメチル-4,4’-ジアミノビフェニル、2,2’-ジ(トリフルオロメチル)-4,4’-ジアミノビフェニル、9,9-ビス(4-アミノフェニル)フルオレンの残基、これらの化合物の芳香族環にアルキル基やハロゲン原子で置換した化合物の残基、これらの化合物の水添化物の残基、及び一般式(1)、(6)で表される構造などが挙げられる。これらは単独で又は2種以上を組み合わせて使用される。
一般式(7)は3価または4価の有機基であり、R22~R25は各々独立にハロゲン原子または炭素数1~3の1価の有機基を示す。得られる樹脂の耐熱性という点から、メチル基、メトキシ基、エチル基、エトキシ基、フルオロ基、トリフルオロメチル基、ペンタフルオロエチル基、トリフルオロメトキシ基、ペンタフルオロエトキシ基などが好ましい具体例として挙げられるが、これらに限定されない。得られる樹脂の吸光度を低減できるという点から、フルオロ基、トリフルオロメチル基、ペンタフルオロエチル基、トリフルオロメトキシ基、ペンタフルオロエトキシ基がさらに好ましく、トリフルオロメチル基、ペンタフルオロエチル基が最も好ましい。また、得られる樹脂の吸光度を低減できるという点から、R22~R25はポリマー鎖に対してオルソ位にあることが好ましい。さらに、得られる樹脂の熱線膨張係数を低減できるという点からR22~R25は2位、2’位の位置に結合していることがより好ましい。
一般式(3)、(4)、(5)においてn2、n3、n4は10~100,000の範囲を示す。
ポリイミド、ポリアミドイミドが好ましく用いられる、さらに好ましくは一般式(4)で表される構造を含む樹脂である。耐熱性の点で、最も好ましくは一般式(4)であらわされるポリイミド樹脂である。一般式(4)で表されるポリイミド樹脂は既に環状構造を有しているため、加熱処理温度を高温にして脱水閉環する必要がないので250℃以下の低温処理が可能となることが最大の利点である。
前記記載のR34とR39 、R40とR45において、前記置換もしくは無置換のC1~C6のアルキル基、前記置換もしくは無置換のC1~C6のアルコキシ基、前記ハロゲン化アルキル基、前記置換もしくは無置換のアミノ基、前記置換もしくは無置換のアミド基、前記置換もしくは無置換のC6~C30のアリール基、前記置換もしくは無置換のC4~C30の複素環アリール基、及び前記エステル基が全て前記と同じである。
前記製造方法において、前記R35、R36、R37及びR38が水素で、前記R41、R42、R43及びR44が水素であることが好ましい。
本発明はさらに、前記製造方法で得た 6,6’-ジベンゾオキサゾール誘導体を、酸性条件下で開環反応することで前記5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体が得る。
ジブロモビフェニル誘導体の合成方法に関し、前記反応は一般式(15)に記載の構造を有するビフェニル類化合物を原料とし、他の反応剤(触媒など)を使用せず、非プロトン性溶媒及び臭素化試薬のみの反応条件下で一般式(16)に記載の構造を有するジブロモビフェニル類誘導体が得られる。この方法は、反応収率が高く、後処理が簡便で、溶媒回収利用がよく、環境に対する汚染が小さく、量産化実現しやすい。
前記C1~C6のアルキル基はC1~C6の直鎖アルキル基、C1~C6の側鎖アルキル基またはC1~C6のシクロアルキル基が好ましく、メチル、エチル、n-プロピル、イソプロピル、n-ブチル、sec-ブチル、t -ブチル、n-ペンチル、イソペンチル、ネオペンチル、シクロペンチル、n-ヘキシル、またはシクロヘキシル等のC1~C6の飽和脂肪族炭化水素基がより好ましい。前記C1~C6のアルコキシル基はC1~C6の直鎖アルコキシル基、C1~C6の側鎖アルコキシル基またはC1~C6のシクロアルコキシル基が好ましい。メトキシ、エトキシ、プロポキシ、イソプロポキシ、n-ブトキシ、イソブトキシ、t-ブトキシ、n-ペンチルオキシ、イソペンチルオキシ、ネオペンチルオキシ、n-ヘキシルオキシ、シクロペンチルオキシ、またはシクロヘキシルオキシ等がより好ましい。
本発明における反応温度は-30℃~60℃が好ましく、量産コストの観点から、-20℃~60℃がより好ましい。本発明における反応時間は1h~48hが好ましく、反応速度及び量産のコストの観点から、1h~12hがより好ましい。
本発明の粗生成物を精製する時に、溶媒のコスト及び溶解性の観点から、使用する溶媒は石油エーテル、酢酸エチル、酢酸ブチル、トルエン、キシレン、ジクロロメタン、1,2-ジクロロエタン、アセトニトリル、エタノール、メタノール、イソプロパノール、酢酸プロピレングリコールメチルエーテル、グリコールジメチルエーテル、エチルエーテル、テトラヒドロフラン、または1,4-ジオキサン等の溶媒のうちの1種または複数種が好ましい。
実施例中の樹脂および樹脂組成物の評価は以下の方法により行った。
大日本スクリーン製造(株)製ラムダエースSTM-602を使用し、樹脂膜、加熱硬化後の被膜とも、屈折率を1.629として測定した。
樹脂溶液を8インチのシリコンウエハー上に回転塗布し、次いで、120℃のホットプレート(東京エレクトロン(株)製の塗布現像装置Act-8使用)で3分間ベークし、樹脂膜を得た。
樹脂溶液を50mm×50mm×0.7mm厚のガラス基板(旭硝子(株)製AN-100)に、ミカサ(株)製のスピンコーターMS-A200を用いて回転塗布し、次いで、120℃のホットプレート(大日本スクリーン(株)製ホットプレートD-SPIN使用)で3分間ベークし、樹脂膜を得た。回転塗布時の回転数は樹脂膜厚が10μmなるように調整した。
樹脂溶液を8インチのシリコンウエハー上に回転塗布し、次いで、120℃のホットプレート(東京エレクトロン(株)製の塗布現像装置Act-8使用)で4分間ベークし、樹脂膜を得た。回転塗布時の回転数は樹脂膜厚が10μmになるよう調整した。
樹脂溶液を8インチのシリコンウエハー上に回転塗布し、次いで、120℃のホットプレート(東京エレクトロン(株)製の塗布現像装置Act-8使用)で3分間ベークし、樹脂膜を得た。
8インチシリコンウエハー上に樹脂溶液を回転塗布し、次いで、120℃のホットプレート(東京エレクトロン(株)製の塗布現像装置Act-8使用)で3分間ベークし、厚さ6μmのプリベーク膜を作製した。この膜を、i線ステッパー(NIKON NSR i9)を用いて0~1000mJ/cm2の露光量にて10mJ/cm2ステップで露光した。露光後、2.38重量%のテトラメチルアンモニウム(TMAH)水溶液(三菱ガス化学(株)製、ELM-D)で90秒間現像し、ついで純水でリンスした。このとき、露光および現像後、露光部分が完全に溶出してなくなった露光量(最小露光量Ethという)を感度とした。Ethが700mJ/cm2以下であれば高感度であると判断できる。500mJ/cm2以下がより好ましい。
PMDA:無水ピロメリット酸
ODPA:3,3’,4,4’-ジフェニルエーテルテトラカルボン酸二無水物
SiDA:1,1,3,3-テトラメチル-1,3-ビス(3-アミノプロピル)ジシロキサン
NMP:N-メチル-2-ピロリドン
GBL:ガンマーブチロラクトン
3-Aph:m-アミノフェノール
PMDA-H:1S,2S,4R,5R-シクロへキサンテトラカルボン酸二無水物
NA:5-ノルボルネン-2.3-ジカルボン酸無水物
TFMB:2,2’‐ビス(トリフルオロメチル)ベンジジン
HAB:3,3’-ジヒドロキシベンジジン
BPDA:3,3’,4,4’-ビフェニルテトラカルボン酸二無水物
KBM-403:3-グリシドキシプロピルトリメトキシシラン。
BAHF: 2,2-ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン
HFHA:2,2-ビス[3-(3-アミノベンズアミド)-4-ヒドロキシフェニル]ヘキサフルオロプロパン
DAE:4,4’-ジアミノジフェニルエーテル。
2,2’-ビス(トリフルオロメチル)-5,5’-ジヒドロキシベンジジン17.6g(0.05モル)をアセトン100mL、プロピレンオキシド17.4g(0.3モル)に溶解させ、-15℃に冷却した。ここに3-ニトロベンゾイルクロリド20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、-15℃で4時間反応させ、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
2,2’-ビス(トリフルオロメチル)-5,5’-ジヒドロキシベンジジン17.6g(0.05モル)を2,2’-ジメチル-5,5’-ジヒドロキシベンジジン17.6g(0.05モル)に変えた以外は合成例1と同様にして下記式で表されるヒドロキシル基含有ジアミン化合物(b)を得た。得られた固体をそのまま反応に使用した。
3-ニトロベンゾイルクロリド20.4g(0.11モル)を4-ニトロベンゾイルクロリド20.4g(0.11モル)に変えた以外は合成例1と同様にして下記式で表されるヒドロキシル基含有ジアミン化合物(c)を得た。得られた固体をそのまま反応に使用した。
乾燥窒素気流下、2,2’-ビス(トリフルオロメチル)-5,5’-ジヒドロキシベンジジン17.6g(0.05モル)とアリルグリシジルエーテル34.2g(0.3モル)を酢酸エチル100gに溶解させ、-15℃に冷却した。ここに酢酸エチル50gに溶解させた無水トリメリット酸クロリド22.1g(0.11モル)を反応液の温度が0℃を越えないように滴下した。滴下終了後、0℃で4時間攪拌した。
乾燥窒素気流下、TrisP-PA(商品名、本州化学工業(株)製)21.22g(0.05モル)と5-ナフトキノンジアジドスルホニル酸クロリド26.86g(0.10モル)、4-ナフトキノンジアジドスルホニル酸クロリド13.43g(0.05モル)を1,4-ジオキサン50gに溶解させ、室温にした。ここに、1,4-ジオキサン50gと混合したトリエチルアミン15.18gを、系内が35℃以上にならないように滴下した。滴下後30℃で2時間撹拌した。トリエチルアミン塩を濾過し、ろ液を水に投入した。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、下記式で表されるキノンジアジド化合物(e)を得た。
乾燥窒素気流下、アミン成分として2,2’-ビス(トリフルオロメチル)-3,3’-ジヒドロキシベンジジン15.8g(0.045モル)、SiDA0.62g(0.0025モル)をGBL 100gに溶解させた。ここに酸成分としてPMDA10.91g(0.05モル)をGBL10gとともに加えて、60℃で2時間反応させ、次いで末端封止剤として3-Aph0.545g(0.005モル)をNMPGBL10gとともに加えて、さらに60℃で2時間撹拌し樹脂溶液(A1)を得た。
表1に示したアミン成分、酸成分、末端封止剤の組み合わせを用いて合成例6と同様の方法で樹脂溶液(A2)~(A26)を得た。
乾燥窒素気流下、アミン成分として2,2’-ビス(トリフルオロメチル)-3,3’-ジヒドロキシベンジジン15.8g(0.045モル)、SiDA0.62g(0.0025モル)をNMP100gに溶解させた。ここに酸成分としてPMDA10.91g(0.05モル)をNMP10gとともに加えて、40℃で1時間反応させ、次いで末端封止剤として3-Aph0.545g(0.005モル)をNMP10gとともに加えて、さらに40℃で2時間撹拌した。その後、N,N-ジメチルホルムアミドジメチルアセタール15.19g(0.127モル)をNMP4gで希釈した溶液を10分かけて滴下した。滴下後、40℃で2時間撹拌した。反応終了後、溶液の液温を30℃以下に保ちながら酢酸を30gゆっくりと投入した。30℃以下で30分撹拌後の溶液を水2Lに投入して、ポリマー粉体の沈殿をろ過で集めた。この沈殿をろ過で集めて、水で3回洗浄した後、ポリマー粉体を50℃の真空乾燥機で72時間乾燥し樹脂(B1)の粉末を得た。
表2に示したアミン成分、酸成分、末端封止剤の組み合わせを用いて合成例32と同様の方法で樹脂溶液(B2)~(B26)を得た。
乾燥窒素気流下、アミン成分として2,2’-ビス(トリフルオロメチル)-3,3’-ジヒドロキシベンジジン15.8g(0.045モル)、SiDA0.62g(0.0025モル)をNMP 100gに溶解させた。ここに酸成分としてPMDA10.91g(0.05モル)をNMP10gとともに加えて、60℃で1時間反応させ、次いで末端封止剤として3-Aph0.545g(0.005モル)をNMP10gとともに加えて、さらに60℃で1時間、200℃で4時間撹拌した。撹拌終了後、溶液を水2Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し樹脂(C1)の粉末を得た。
表3に示したアミン成分、酸成分、末端封止剤の組み合わせを用いて合成例58と同様の方法で樹脂(C2)~(C22)の粉末を得た。
2,2’-ビス(トリフルオロメチル)-3,3’-ジヒドロキシベンジジン15.8g(0.045モル)をHAB9.73g(0.045モル)に変更した以外は合成例58と同様の方法で実施したが、200℃反応後の液を冷却中にポリマーが析出してしまい、不溶の樹脂を得た。
乾燥窒素気流下、2,2’-ビス(トリフルオロメチル)-3,3’-ジヒドロキシベンジジン17.6g(0.05モル)をNMP50g、グリシジルメチルエーテル26.4g(0.3モル)に溶解させ、溶液の温度を-15℃まで冷却した。ここにイソフタル酸クロリド8.12g(0.04モル)をGBL25gに溶解させた溶液を、内部の温度が0℃を越えないように滴下した。滴下終了後、6時間-15℃で撹拌を続けた。その後、NA3.28g(0.02モル)を投入して、常温で4時間撹拌した。反応終了後、溶液をメタノールを10重量%含んだ水3Lに投入して白色の沈殿を析出させた。この沈殿をろ過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し、樹脂(D1)の粉末を得た。
表4に示したアミン成分、酸成分、末端封止剤の組み合わせを用いて合成例81と同様の方法で樹脂(D2)~(D4)の粉末を得た。
乾燥窒素気流下、2,2’-ビス(トリフルオロメチル)-3,3’-ジヒドロキシベンジジン17.6g(0.05モル)をNMP100gに溶解させた。ここにジフェニルエーテルジカルボン酸ジイミダゾリド14.32g(0.04モル)をNMP10gとともに加えて、85℃で4時間撹拌した。その後、NA3.28g(0.02モル)を投入して、85℃でさらに2時間撹拌した。反応終了後、溶液の液温を30℃以下に保ちながら酢酸を30gゆっくりと投入した。30℃以下で30分攪拌後の溶液を水2Lに投入して、ポリマー粉体の沈殿をろ過で集めた。この沈殿をろ過で集めて、水で3回洗浄した後、ポリマー粉体を50℃の真空乾燥機で72時間乾燥し樹脂(D5)の粉末を得た。
樹脂(A1)~(A26)は溶液のまま、樹脂(B1)~(B26)、樹脂(C1)~(C22)、および樹脂(D1)~(D5)はGBLに溶解し、濃度40%の溶液を作製した。得られた溶液を用いて前記のように熱線膨張係数、吸光度、アルカリ現像速度、残留応力を測定した結果を表5-1、表5-2に示す。
樹脂(B1)17.5g、合成例5で得られたキノンジアジド化合物(b)2.3g、KBM-403 0.5gをGBL 45gに加えて感光性樹脂組成物を得た。得られた感光性樹脂組成物を用いて前記のように、感光性評価を行った。評価結果を表6に示す。
樹脂(B2)~(B26)、樹脂(C1)~(C22)、樹脂(D1)~(D5)について、実施例64と同様の方法で、感光性樹脂組成物を得た。得られた感光性樹脂組成物を用いて前記のように、感光性評価を行った。評価結果を表6に示す。
反応収率はモル百分数である。実施例に使用される溶媒、触媒は共に国薬、Aldrich、TCIまたはAlfa等の試薬供給先から購入され、後処理せず反応に直接使用する。反応生成物の構造は核磁気共鳴スペクトルによって確認され、使用された核磁気共鳴装置がJEOL(400MHz)である。反応生成物の純度は高速液体クロマトグラフィーを用いて測定、使用した高速液体クロマトグラフィーがSHIMADZU Prominenceで、クロマトグラフカラムがYMC Pack Phである。
実施例108
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジアミノビフェニル(32.0g,0.10mol)及びジオキサン(300mL)を加え、窒素ガスで3回置換し、反応フラスコを氷浴に入れて撹拌を行い、その後反応フラスコに対して回数分けてN-ブロモスクシンイミド(NBS)(35.6g,0.20mol)を加えた後温度を60℃まで上げて撹拌を行い、高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より小さい時に撹拌を停止した。反応フラスコに対して飽和炭酸ナトリウム溶液を徐々に加え、pH値を中性まで調節し、有機相を分離、有機相を水洗浄(200mL×2)、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を除去して粗生成物赤橙色固体を得た。引き続き粗生成物に石油エーテル/酢酸エチル(60ml/2ml)を加えて室温で30Min撹拌し、ろ過を行い、白色固体2,2’-ジトリフルオロメチル-5,5’ -ジブロモ-4,4’-ジアミノビフェニル37.5g(収率78%、純度95%)を得た。
三角フラスコに前記製造方法で得た2,2’-ジトリフルオロメチル-5,5’ -ジブロモ-4,4’-ジアミノビフェニル(95.6g,0.2mol)及びジクロロメタン(500mL)を加え、トリエチルアミン(71.8ml,0.514mol)とピバロイルクロリド(63.0ml, 0.514mol)を加え、反応フラスコを40℃恒温のオイルバスに入れて撹拌して一夜置き、高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より小さい時に撹拌を停止し、飽和炭酸ナトリウム水溶液(200ml)を入れ、一時間撹拌した。有機層を水、飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下で濃縮した。石油エーテル(200ml)と酢酸エチル(10ml)混合溶媒洗浄、濾過し、真空乾燥機に入れて乾燥を行い、白色固体2,2’-ジトリフルオロメチル-5,5’-ジブロモ-4,4’-ジブチルアミドビフェニル130.2g(収率94.9%,純度97%)を得た。
<ジブロモビフェニル誘導体>
反応過程測定:高速液体クロマトグラフィーで測定を行い、型番がSHIMADZU LC-20ADで、クロマトグラフカラムがYMC-Pack Ph(250×4.6mml.D)である。
純度:高速液体クロマトグラフィーで測定を行い、型番がSHIMADZU LC-20ADで、クロマトグラフカラムがYMC-Pack Ph(250×4.6mml.D)である。
構造同定:核磁気共鳴装置、JEOL(400MHz)、溶媒が重水素化クロロホルムまたはジメチルスルホキシド-d6である。
収率:モル収率、秤量して算出し得る。
2,2’-ジトリフルオロメチル-4,4’-ジアミン基ビフェニル:J&K Chemicalより購入;
液体臭素:国薬集団から購入;
N-ブロモスクシンイミド:国薬集団から購入;
溶媒:国薬集団から購入。
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジアミンビフェニル(80.0g,0.25mol)及び酢酸エチル(800mL)を加え、窒素ガスで3回置換し、反応フラスコを氷浴に入れて撹拌を行い、その後反応フラスコに対して液体臭素(26.2mL,0.51mol)を滴下し、液体臭素を滴下した後続けて撹拌を行い、高速液体クロマトグラフィーで反応を測定し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに対して飽和炭酸ナトリウム溶液を徐々に加え、pH値を中性まで調節し、有機相を分離、有機相を水洗浄(毎回500mL、2回洗浄)、無水硫酸ナトリウムを加えて乾燥、ろ過後、有機溶媒を除去して粗生成物黄色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(150ml/5ml)を加えて室温で30Min撹拌、ろ過を行い白色固体2,2’-ジトリフルオロメチル-4,4’-ジアミン-5,5’-ジブロモビフェニル106.5g(収率90%、純度96%)を得た。
実施例111
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジアミンビフェニル(32.0g,0.10mol)及び1,4-ジオキサン(300mL)を加え、窒素ガスで3回置換し、反応フラスコを氷浴に入れて撹拌を行い、その後反応フラスコに対してN-ブロモスクシンイミド(NBS)(35.6g,0.20mol)を数回分けて添加した後続けて撹拌を行った。高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに対して水酸化ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、酢酸エチル(300mL)を加えて有機相を分離、有機相を飽和食塩水洗浄(毎回200mL、2回洗浄)、水洗浄(200mL)、無水硫酸ナトリウムを加えて乾燥、ろ過後、有機溶媒を除去して粗生成物赤橙色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(60ml/2ml)を加えて室温で30Min撹拌、ろ過を行い白色固体2,2’-ジトリフルオロメチル-4,4’-ジアミン-5,5’-ジブロモビフェニル33.5g(収率70%、純度95%)を得た。
実施例112
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジアセトアミドビフェニル(101.0g,0.25mol)及びテトラヒドロフラン(500mL)を加え、窒素ガスで3回置換し、反応フラスコを-20℃の低温反応槽に入れて撹拌を行い、その後反応フラスコに対して液体臭素(26.2mL,0.51mol)を滴下後続けて撹拌を行った。高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに対して飽和炭酸ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、、酢酸エチル(500mL)を加えて有機相を分離、有機相を飽和食塩水洗浄(毎回500mL、2回洗浄)、水洗浄(200mL)、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を留去して粗生成物黄色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(150ml/5ml)を加えて室温で30Min撹拌し、ろ過を行い白色固体2,2’-ジトリフルオロメチル-4,4’-ジアセトアミド-5,5’-ジブロモビフェニル119.6g(収率85%、純度96%)を得た。
実施例113
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジ(フタルイミド)ビフェニル(145.0g,0.25mol)及び酢酸プロピレングリコールメチルエーテル(500mL)を加え、窒素ガスで3回置換し、室温で撹拌を行い、その後反応フラスコに対して液体臭素(26.2mL,0.51mol)を滴下し、液体臭素を滴下した後続けて撹拌を行った。、高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに飽和炭酸ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、有機相を分離、有機相を水洗浄(毎回300mL、2回洗浄)、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を除去して粗生成物黄色固体を得た。引き続き粗生成物に石油エーテル/酢酸エチル(150ml/5ml)を加えて室温で30Min撹拌し、ろ過を行い、白色固体2,2’-ジトリフルオロメチル-4,4’-ジ(フタルイミド)-5,5’-ジブロモビフェニル166.0g(収率90%、純度95%)を得た。
実施例114
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジ(ジターシャリーブトオキサイドジカルボキシイミド)ビフェニル(180.0g,0.25mol)及び酢酸ブチル(500mL)を加え、窒素ガスで3回置換し、-30℃の低温反応溝に入れて撹拌を行い、その後反応フラスコに対して液体臭素(26.2mL,0.51mol)を滴下した後続けて撹拌を行った。高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに飽和炭酸ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、、有機相を分離、有機相を水洗浄(毎回500mL、2回洗浄)、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を除去して粗生成物黄色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(150ml/5ml)を加えて室温で30Min撹拌し、ろ過を行い、白色固体2,2’-ジトリフルオロメチル-4,4’-ジ(ジターシャリーブトオキサイドジカルボキシイミド)-5,5’-ジブロモビフェニル177.6g(収率81%、純度95%)を得た。
実施例115
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジ(ターシャリーブトオキサイドカルバミド)ビフェニル(130.0g,0.25mol)及び酢酸ブチル(500mL)を加え、窒素ガスで3回置換し、-30℃の低温反応槽に入れて撹拌を行い、その後反応フラスコに対して液体臭素(26.2mL,0.51mol)を滴下した後続けて撹拌を行った。高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに飽和炭酸ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、有機相を分離、有機相を水洗浄(毎回500mL、2回洗浄)、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を除去して粗生成物黄色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(150ml/5ml)を加えて室温で30Min撹拌し、ろ過を行い、白色固体2,2’-ジトリフルオロメチル-4,4’-ジ(ターシャリーブトオキサイドカルバミド)-5,5’-ジブロモビフェニル141.1g(収率83%、純度95%)を得た。
実施例116
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジアミンビフェニル(32.0g,0.10mol)及びジクロロメタン(300mL)を加え、窒素ガスで3回置換し、反応フラスコを氷浴に入れて撹拌を行い、その後反応フラスコに対してN-ブロモスクシンイミド(NBS)(35.6g,0.20mol)を数回分けて添加した後、続けて撹拌を行った。高速液体クロマトグラフィーで反応を追跡しながら、N-ブロモスクシンイミド(17.8g,0.10mmol)を補充添加し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに水酸化ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、有機相を分離、有機相を水洗浄(毎回200mL、2回洗浄)し、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を除去して粗生成物赤橙色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(60ml/2ml)を加えて室温で30Min撹拌し、ろ過を行い白色固体2,2’-ジトリフルオロメチル-4,4’-ジアミン-5,5’-ジブロモビフェニル23.8g(収率50%、純度95%)を得た。
実施例117
三角フラスコに2,2’-ジトリフルオロメチル-4,4’-ジアミンビフェニル(32.0g,0.10mol)及びアセトニトリル(300mL)を加え、窒素ガスで3回置換し、反応フラスコを氷浴に入れて撹拌を行い、その後反応フラスコに対してN-ブロモスクシンイミド(NBS)(35.6g,0.20mol)を数回分けて添加した後、続けて撹拌を行った。高速液体クロマトグラフィーで反応を追跡しながら、NBS(8.9g,0.05mol)を補充添加し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに水酸化ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、酢酸エチル(300mL)を加えて有機相を分離、有機相を飽和食塩水洗浄(毎回200mL、2回洗浄)し、水洗浄(200mL)し、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を除去して粗生成物赤橙色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(60ml/2ml)を加えて室温で30Min撹拌し、ろ過を行い浅黄色固体2,2’-ジトリフルオロメチル-4,4’-ジアミン-5,5’-ジブロモビフェニル15.7g(収率33%、純度95%)を得た。
実施例118
三角フラスコに2,2’-ジメトキシ-4,4’-ジメチルビフェニル(60.5g,0.25mol)及び酢酸エチル(500mL)を加え、窒素ガスで3回置換し、反応フラスコを室温で撹拌し、その後反応フラスコに対して液体臭素(26.2mL,0.51mol)を滴下した後続けて撹拌を行った。高速液体クロマトグラフィーで反応を追跡し、原料の含有量が3%より少ない時に撹拌を停止し、反応フラスコに飽和炭酸ナトリウム溶液を徐々に加え、pH値を中性まで調節した後、有機相を分離、有機相を水洗浄(毎回500mL、2回洗浄)、無水硫酸ナトリウムを加えて乾燥し、ろ過後、有機溶媒を除去して粗生成物黄色固体を得た。引き続き、粗生成物に石油エーテル/酢酸エチル(150ml/5ml)を加えて室温で30Min撹拌し、ろ過を行い白色固体2,2’-ジメトキシ-4,4’-ジメチル-5,5’-ジブロモビフェニル94.3g(収率94%、純度95%)を得た。
比較例27
三角フラスコに酢酸(50mL)、酢酸ナトリウム(1.3g)及び原料1(1.46g, 3.78mmol)を加え、窒素ガスで3回置換し、室温で撹拌し、その後反応フラスコに対して液体臭素Br2(0.4mL, 7.76mmol)及び酢酸(5mL)の混合溶液を滴下した後室温で続けて48h反応した。薄層クロマトグラフィー(TLC)で反応を追跡し(展開溶媒:石油エーテル/酢酸エチル、10mL/1mL)、液体臭素(0.4mL)及び酢酸(5mL)を補充添加し、続けて24h撹拌し、反応液に飽和亜硫酸ナトリウム(5mL)を加え、ジクロロメタン(毎回70mL、5回抽出)を加えて抽出し、有機相を合わせ、水洗浄、無水硫酸マグネシウムを加えて乾燥し、ろ過後、有機溶媒を除去して油状物を得た。油状物をジクロロメタンを用いて再結晶し、製品2、1.64g(収率80%)を得た。
比較例28
三角フラスコに100mLエタノール、20.0g(62.5mmol)2,2’-ジトリフルオロメチルベンジジンを加え、窒素ガスで3回置換し、反応フラスコを氷浴に入れて撹拌し、その後反応フラスコに対して21.0g(131.2mmol)臭素を滴下し、その後室温で1h撹拌した後、トルエンを加え、有機相を3回水洗浄、その後飽和炭酸水素ナトリウム水及び水でそれぞれ2回洗浄し、有機相を乾燥、ろ過後、有機溶媒を除去した後ノルマルヘキサン/トルエンで再結晶を行い、2,2’-ジトリフルオロメチル-4,4’-ジアミン-5,5’-ジブロモビフェニル11.5g(収率38.5%)を得た。
2 Alパッド
3 パッシベーション膜
4 絶縁膜
5 金属(Cr、Ti、Ni、TiW等)膜
6 金属(Al、Cu、Au等)配線
7 絶縁膜
8 バリアメタル
9 スクライブライン
10 ハンダバンプ
11 シリコンウエハー
12 Alパッド
13 パッシベーション膜
14 絶縁膜
15 接着フィルム
16 ワイヤー(Cu、Au等)
21 シリコンウエハー
22 貫通電極(Cu等)
23 パッド(Al、Cu等)
24 パッシベーション膜
25 絶縁膜
26 バリアメタル
27 ハンダバンプ
28 接着フィルム
29 スクライブライン
31 TFT
32 配線
33 絶縁膜
34 平坦化膜
35 ITO
36 基板
37 コンタクトホール
Claims (36)
- 下記一般式(1)、(2)で表される構造から選ばれる少なくとも1つの構造を含むことを特徴とする樹脂。
- 前記樹脂が、ポリイミド、ポリアミドイミド、ポリベンゾオキサゾール、ポリイミド前駆体、ポリベンゾオキサゾール前駆体、またはそれらの共重合体から選ばれる少なくとも1つを含むことを特徴とする請求項1記載の樹脂。
- 前記樹脂が、下記一般式(3)~(5)で表される構造またはそれらの共重合体から選ばれる少なくとも1つを含むことを特徴とする請求項1または2に記載の樹脂。
- 前記樹脂が、1μm厚当たりの波長365nmにおける吸光度が0.005以上0.3以下の樹脂膜を形成する樹脂であることを特徴とする請求項1~3のいずれかに記載の樹脂。
- 前記樹脂が、前記樹脂を250℃で加熱処理した後測定した50~200℃の平均熱線膨張係数が-10~40ppm/℃であることを特徴とする請求項1~4のいずれかに記載の樹脂。
- 前記樹脂が、2.38%テトラメチルアンモニウムヒドロキシド水溶液に浸漬した際の膜厚減少速度が10nm/分以上、30000nm/分以下である樹脂膜を形成することを特徴とする請求項1~5のいずれかに記載の樹脂。
- 請求項1~6のいずれかに記載の樹脂を含有する樹脂組成物。
- 光酸発生剤または光重合開始剤を含むことを特徴とする請求項7記載の樹脂組成物。
- 請求項7または8に記載の樹脂組成物を、支持基板上に塗布し、塗布膜を形成する工程、該塗布膜を乾燥し樹脂膜を形成する工程、該樹脂膜を露光する工程、露光した樹脂膜を現像する工程、および現像した樹脂膜を加熱処理する工程を含む耐熱性被膜の製造方法。
- 請求項7または8に記載の樹脂組成物を、スリットノズルを用いて支持基板上に塗布し、塗布膜を形成する工程、該塗布膜を減圧乾燥し樹脂膜を形成する工程、該樹脂膜を露光する工程、露光した樹脂膜を現像する工程、および現像した樹脂膜を加熱処理する工程を含む耐熱性被膜の製造方法。
- 樹脂膜を加熱処理する工程が250℃以下で行なわれることを特徴とする請求項9または10に記載の耐熱性被膜の製造方法。
- 前記耐熱性被膜の製造方法によって得られた耐熱性被膜付基板の、耐熱性被膜を形成する樹脂の残留応力が30MPa以下であることを特徴とする請求項9~11のいずれかに記載の耐熱性被膜の製造方法。
- 基板と、基板の片面、または両面に形成された被膜とを含む構造が、1層または複数積層された状態で装着されている電子部品であって、前記被膜が請求項9~12のいずれかに記載の製造方法により得られる耐熱性被膜であることを特徴とする電子部品。
- 基板と、基板上に交互に形成された被膜層と配線層からなる再配線構造、または多層配線構造とを含む電子部品であって、前記被膜層が請求項9~12のいずれかに記載の製造方法により得られる耐熱性被膜であることを特徴とする電子部品。
- 基板上に形成された第一電極と第一電極を部分的に露光せしめるように第一電極上に形成された絶縁層と、第一電極に対向して設けられた第二電極とを含む表示装置であって、前記絶縁層が請求項9~12のいずれかに記載の製造方法により得られる耐熱性被膜であることを特徴とする表示素子。
- 薄膜トランジスタ(TFT)が形成された基板上の凹凸を覆う状態で設けられた平坦化膜と、平坦化膜上に設けられた表示素子とを備えてなる表示素子であって、前記平坦化膜が請求項9~12のいずれかに記載の製造方法により得られる耐熱性被膜であることを特徴とする表示素子。
- 下記一般式(8)で表される5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体。
- 前記R29、R30、R31及びR32がそれぞれ水素であることを特徴とする請求項17記載の5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体。
- 一般式(9)記載の4,4’-ジアミノビフェニルを臭素化反応することで一般式(10)に記載の5,5’-ジブロモ-4,4’-ジアミノビフェニル誘導体を得る製造方法を含むことを特徴とする5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 前記R35、R36、R37及びR38が水素で、前記R41、R42、R43及びR44が水素であることを特徴とする請求項19記載の5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 臭素化反応における反応温度が-30℃~60℃で、臭素化反応における反応溶媒が酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、エチレングリコールジメチルエーテル、テトラヒドロフラン、1,4-ジオキサンまたは前記溶媒の混合溶媒のうちの1種または複数種であり、臭素化反応に使用される臭素化試薬が液体臭素またはN-ブロモスクシンイミドであることを特徴とする請求項19記載の5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 5,5’-ジブロモ-4,4’-ジアミノビフェニル誘導体を酸無水物または塩化アシルを用いて、アミド化反応することで一般式(11)に示す5,5’-ジブロモ-4,4’-ジアミドビフェニル誘導体を得る製造方法を含むことを特徴とする5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 一般式(11)におけるR47、R48、R49及びR50が水素であることを特徴とする請求項22に記載の5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 5,5’-ジブロモ-4,4’-ジアミドビフェニル誘導体を、触媒及び無機アルカリの作用下で反応することで、一般式(12)に示す6,6’-ジベンゾオキサゾール誘導体を得る製造方法を含むことを特徴とする5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 一般式(12)におけるR55、R56、R57及びR58が水素であることを特徴とする請求項24記載の5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 前記触媒には少なくとも銅触媒を含み、使用される無機アルカリが炭酸カリウムまたはリン酸カリウムのうちの1種または複数種で、その反応温度が100℃~140℃で、反応溶媒が高沸点溶媒であることを特徴とする請求項24記載の5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 6,6’-ジベンゾオキサゾール誘導体を、無機強酸下で開環反応して得ることを特徴とする5,5’-ジヒドロキシル-4,4’-ジアミノビフェニル誘導体の製造方法。
- 5,5’-ジブロモビフェニル誘導体の製造方法において、一般式(13)に記載の構造を有するビフェニル類化合物を原料とし、非プロトン性溶媒及び臭素化試薬の作用下で、一般式(14)に記載の構造を有する5,5’-ジブロモビフェニル誘導体を得ることを特徴とする5,5’-ジブロモビフェニル誘導体の製造方法。
- 前記非プロトン性溶媒がエステル類溶媒、エーテル類溶媒、アレーン類溶媒または上記溶媒の混合溶媒のうちの1種または複数種から選ばれることを特徴とする請求項28記載の5,5’-ジブロモビフェニル誘導体の製造方法。
- 前記非プロトン性溶媒が酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、プロピレングリコールモノメチルエーテルアセテート、エチレングリコールジメチルエーテル、テトラヒドロフラン、1,4-ジオキサンまたは上記溶媒の混合溶媒のうちの1種または複数種から選ばれることを特徴とする請求項29記載の5,5’-ジブロモビフェニル誘導体の製造方法。
- 一般式(13)及び(14)において、R61及びR62がそれぞれ同じでも異なっていてもよく、ハロゲン、C1~C6のアルキル基、C1~C6のアルコキシル基、ハロゲン化アルキル基、エステル基またはニトロ基のうちの1種から選ばれることを特徴とする請求項28記載の5,5’-ジブロモビフェニル誘導体の製造方法。
- 前記ハロゲン化アルキル基がトリフルオロメチル、またはトリフルオロエチルのうちの1種から選ばれることを特徴とする請求項31記載の5,5’-ジブロモビフェニル誘導体の製造方法。
- 前記C1~C6のアルキル基がメチル基であることを特徴とする請求項31記載の5,5’-ジブロモビフェニル誘導体の製造方法。
- 前記C1~C6のアルコキシル基がメトキシ基であることを特徴とする請求項31記載の5,5’-ジブロモビフェニル誘導体の製造方法。
- 一般式(13)及び(14)において、R63及びR64がそれぞれ同じでも異なっていてもよく、置換もしくは無置換のアミノ基、置換もしくは無置換のアミド基、置換もしくは無置換のイミド基、置換もしくは無置換のスルファミン基、置換もしくは無置換のスルフィンアミド基、または置換もしくは無置換の芳香族複素環基のうちの1種から選ばれることを特徴とする請求項28記載の5,5’-ジブロモビフェニル誘導体の製造方法。
- 一般式(13)及び(14)において、R63及びR64がそれぞれ同じでも異なっていてもよく、アミノ基、アセトアミド基、ターシャリーブトオキサイドアミド基、ベンジルオキシアミド基、ジターシャリーブトオキサイドジカルボキシイミド基、ジベンジルオキシジカルボキシイミド基、またはフタルイミド基うちの1種から選ばれることを特徴とする請求項28記載の5,5’-ジブロモビフェニル誘導体の製造方法。
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Also Published As
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SG11201706068QA (en) | 2017-08-30 |
TW201723024A (zh) | 2017-07-01 |
US20180011402A1 (en) | 2018-01-11 |
US11333976B2 (en) | 2022-05-17 |
CN107406590A (zh) | 2017-11-28 |
JP6750499B2 (ja) | 2020-09-02 |
KR102386553B1 (ko) | 2022-04-14 |
KR20170108949A (ko) | 2017-09-27 |
CN107406590B (zh) | 2020-08-04 |
JPWO2016121691A1 (ja) | 2017-11-02 |
TWI686425B (zh) | 2020-03-01 |
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