WO2010150518A1 - Résine soluble en milieu alcalin, composition de résine photosensible positive, film durci, film protecteur, film isolant, et dispositif semi-conducteur et dispositif d'affichage les contenant - Google Patents

Résine soluble en milieu alcalin, composition de résine photosensible positive, film durci, film protecteur, film isolant, et dispositif semi-conducteur et dispositif d'affichage les contenant Download PDF

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Publication number
WO2010150518A1
WO2010150518A1 PCT/JP2010/004136 JP2010004136W WO2010150518A1 WO 2010150518 A1 WO2010150518 A1 WO 2010150518A1 JP 2010004136 W JP2010004136 W JP 2010004136W WO 2010150518 A1 WO2010150518 A1 WO 2010150518A1
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group
alkali
soluble resin
resin composition
aminophenol
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PCT/JP2010/004136
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English (en)
Japanese (ja)
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寺山美樹
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住友ベークライト株式会社
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Priority to JP2011519591A priority Critical patent/JPWO2010150518A1/ja
Publication of WO2010150518A1 publication Critical patent/WO2010150518A1/fr

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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
    • C08G73/22—Polybenzoxazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • 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

Definitions

  • the present invention relates to an alkali-soluble resin, a positive photosensitive resin composition, a cured film, a protective film, an insulating film, a semiconductor device using the same, and a display device.
  • protective films and insulating films for semiconductor elements are polyimide resins having excellent heat resistance and excellent electrical and mechanical properties, polybenzoxazole resins that are considered to have good moisture resistance reliability in addition to the above properties, etc. was used.
  • polyimide resin, polybenzoxazole resin, and their precursor resins themselves are given photosensitivity so that part of the relief pattern creation process can be simplified, while having high sensitivity and fine processability, and high heat resistance.
  • a photosensitive resin composition has been developed that has high performance, excellent electrical and mechanical properties, and is effective in shortening the process and improving yield (productivity). It also has potential as a composition.
  • Patent Document 1 discloses a positive photosensitive resin composition composed of a polybenzoxazole precursor as an alkali-soluble resin and a diazoquinone compound as a photosensitizer.
  • the development mechanism of this positive photosensitive resin composition is as follows. When a positive photosensitive resin composition applied on a substrate is irradiated with actinic radiation through a mask on which a desired pattern is drawn, the exposed portion (exposed portion) of the diazoquinone compound undergoes a chemical change, resulting in an alkaline aqueous solution. So that the alkali-soluble resin is dissolved.
  • the unexposed portion (unexposed portion) of the diazoquinone compound is insoluble in the aqueous alkali solution and becomes resistant to the interaction with the alkali-soluble resin.
  • Resin polybenzoxazole resin.
  • the glass transition temperature (Tg) of the cured film has a Tg equal to or higher than the reflow temperature assuming the use of lead-free solder even when the curing temperature is low.
  • the positive photosensitive resin composition is 250 ° C. It is desired that the Tg of the cured film after being cured at a low temperature is 260 ° C. or higher.
  • An object of the present invention is to provide an alkali-soluble resin having excellent heat resistance and reliability even when cured at a low temperature when used as a positive photosensitive resin composition.
  • Another object of the present invention is to provide a positive photosensitive resin composition, a cured film, a protective film, an insulating film, and a semiconductor device using the same, which are highly sensitive and have excellent heat resistance and reliability even when cured at a low temperature. It is to provide a body device.
  • the above bis (aminophenol) has a phenolic hydroxyl group at an adjacent site of both amino groups and a substituent at an adjacent site on the opposite side of the amino group.
  • the alkali-soluble resin according to (2), wherein the bis (aminophenol) is represented by the following formula (1).
  • R 1 is an organic group.
  • R 2 is an alkyl group, an alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different.
  • R 3 is a hydrogen atom, an alkyl group, Any one of an alkoxy group, an acyloxy group, and a cycloalkyl group, which may be the same or different.
  • An alkali-soluble resin comprising a polybenzoxazole precursor structure composed of bis (aminophenol) and a structure derived from dicarboxylic acid,
  • the dihedral angle AB—R 4 —D of the bis (aminophenol) represented by the following formula (2) is rotated by 5 degrees in the range of ⁇ 180 degrees to 180 degrees, and the heat of formation in each conformation
  • An alkali-soluble resin wherein the difference between the highest heat of formation and the lowest heat of formation when determined by a molecular orbital method is 3 [kcal / mol] or more.
  • R 4 is an organic group.
  • R 5 is an alkyl group, an alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different.
  • R 6 is a hydrogen atom, an alkyl group, Any one of an alkoxy group, an acyloxy group, and a cycloalkyl group, which may be the same or different.
  • a positive photosensitive resin composition comprising the alkali-soluble resin according to any one of (1) to (4) above and a photosensitive agent.
  • Composition (7) The positive photosensitive resin composition according to the above (5) or (6), wherein the glass transition temperature is 260 ° C. or higher.
  • a cured film comprising a cured product of the positive photosensitive resin composition according to any one of (5) to (9) above.
  • a protective film comprising the cured film as described in (10) above.
  • An insulating film comprising the cured film as described in (10) above.
  • a semiconductor device comprising the cured film according to (10).
  • a display device having the cured film according to (10).
  • the present invention when used as a positive photosensitive resin composition, it is possible to provide an alkali-soluble resin that is highly sensitive and excellent in heat resistance and reliability even when cured at a low temperature. Further, according to the present invention, a positive photosensitive resin composition, a cured film, a protective film, an insulating film, and a semiconductor device using the same, which are highly sensitive and have excellent heat resistance and reliability even when cured at a low temperature A body device can be provided.
  • the alkali-soluble resin used in the present invention includes a polybenzoxazole precursor structure composed of bis (aminophenol) and a structure derived from dicarboxylic acid, and the bis (aminophenol) is included therein.
  • the energy barrier in dihedral angle rotation calculated by computational chemistry is 3 [kcal / mol] or more.
  • the positive photosensitive resin composition contains the alkali-soluble resin and the photosensitive agent.
  • the protective film and the insulating film of the present invention are characterized in that they are composed of a cured film that is a cured product of the positive photosensitive resin composition.
  • the semiconductor device and the display device of the present invention are characterized by having the cured film.
  • the alkali-soluble resin of the present invention contains a polybenzoxazole precursor structure composed of bis (aminophenol) and a structure derived from dicarboxylic acid, and includes two aromatic rings contained in the bis (aminophenol).
  • the energy barrier in rotation of the dihedral angle calculated by computational chemistry is 3 [kcal / mol] or more.
  • the energy barrier for rotation of the dihedral angle of bis (aminophenol) can be calculated by using, for example, the PM5 method of MOPAC 2006 with a Scigress Explorer manufactured by Fujitsu Limited. Specifically, the structure of bis (aminophenol) represented by the formula (2) is drawn, and the dihedral angle ABCR 4 -D is rotated by 5 degrees in the range of ⁇ 180 degrees to 180 degrees, and the heat of formation is reduced. The value of the energy barrier can be obtained by calculation.
  • R 4 is an organic group.
  • R 5 is an alkyl group, an alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different.
  • R 6 is a hydrogen atom, an alkyl group, Any one of an alkoxy group, an acyloxy group, and a cycloalkyl group, which may be the same or different.
  • an alkali-soluble resin in which the cured film of the positive photosensitive resin composition exhibits a high Tg is required, but Tg decreases as the curing temperature decreases. Therefore, conventionally, there has been no alkali-soluble resin having a polybenzoxazole precursor structure having a high Tg and excellent heat resistance even when cured at a low temperature.
  • techniques for increasing the Tg of a polymer include improvement of rigidity of the main chain, improvement of symmetry, use of intermolecular interactions such as introduction of polar groups, and the like.
  • numerator and obtaining high Tg by requiring a high thermal energy for glass transition was examined. Therefore, the difficulty of the rotational movement of the molecule is regarded as an energy barrier in the rotation of the molecule, and the difference between the maximum value and the minimum value of the generated heat in the rotation of the dihedral angle is calculated by computational chemistry.
  • kcal / mol] or higher a positive photosensitive resin composition having a Tg of 260 ° C. or higher and excellent heat resistance even when cured at a low temperature of 250 ° C. is obtained. I found out.
  • the difference between the heat of formation of the most stable structure and the heat of formation of the most unstable structure is more preferably 4 [kcal / mol] or more, and particularly preferably 5 [kcal / mol] or more. When the difference is within the above range, the heat resistance is particularly excellent.
  • an upper limit it is preferable that it is 30 [kcal / mol] or less. If it is larger than the above upper limit, it is necessary to introduce a very large substituent on the aromatic ring. Therefore, the synthesis of such aminophenol is very difficult due to steric hindrance, and Since the yield becomes very low, it is not preferable.
  • bis (aminophenol) has a structure in which rotational motion is difficult to occur, for example, R 1 shown in Formula (1) is bulky, or an amide bond And a method of introducing a substituent on two aromatic rings.
  • the difference in heat of formation can be remarkably increased by introducing a substituent on two aromatic rings, particularly by introducing a substituent at an ortho position adjacent to the amino group.
  • bis (aminophenol) satisfying that the difference in heat of generation is 3 [kcal / mol] or more include bis (aminophenol) represented by the formula (3).
  • bis (aminophenol) represented by the formula (3) it is considered that the rotation of the two aromatic rings is more difficult to rotate by the substituent (R 8 ) in the ortho position of the amino group, and is higher until the glass transition occurs. It is thought that heat energy will be required.
  • R 7 is an organic group.
  • R 8 is an alkyl group, an alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different.
  • R 9 is a hydrogen atom or an alkyl group. , An alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different.
  • organic group represented by R 7 examples include alkylene, substituted alkylene, —O—, —S—, —SO 2 —, —Si (CH 3 ) 2 —, —C 6 H 4 —, —CO—, —NHCO—, —COO—, —C (CF 3 ) 2 — and the like.
  • R 10 is an organic group selected from alkylene, substituted alkylene, —O—, —S—, —SO 2 —, —CO—, —C (CF 3 ) 2 —.
  • R 11 is alkyl
  • R 12 is any one of a hydrogen atom, an alkyl group, an alkoxy group, an acyloxy group, and a cycloalkyl group, and may be the same or different. May be different.
  • R 13 is an alkylene, substituted alkylene, -O -, - S -, - SO 2 -, - CO -, - C (CF 3) 2 -, an organic group selected from .
  • R 14 is R 15 is any one of an alkyl group, an alkoxy group, an acyloxy group, and a cycloalkyl group, and may be the same or different. May be.
  • R 1 in formula ( 1 ), R 7 in formula (3), R 10 in formula (4), and R 13 in formula (5) and substituted alkylene include, for example, —CH 2 — , —CH (CH 3 ) —, —C (CH 3 ) 2 —, —CH (CH 2 CH 3 ) —, —C (CH 3 ) (CH 2 CH 3 ) —, —C (CH 2 CH 3 ) (CH 2 CH 3 ) —, —CH (CH 2 CH 2 CH 3 ) —, —C (CH 3 ) (CH 2 CH 2 CH 3 ) —, —CH (CH (CH 3 ) 2 ) —, —C (CH 3 ) (CH (CH 3 ) 2 ) —, —CH (CH 2 CH 2 CH 3 ) —, —C (CH 3 ) (CH (CH 3 ) 2 ) —, —CH (CH 2 CH 2 CH 2 CH 3 ) —, —C (CH 3 )
  • R 2 and R 3 in formula (1), R 8 and R 9 in formula (3), R 11 and R 12 in formula (4), and R 14 and R 15 in formula (5) are alkyl groups or alkoxy It is preferable to use the group bis (aminophenol), thereby maintaining a higher Tg even when cured at a low temperature, and having a sufficient solubility in an aqueous alkali solution and a better balance.
  • An alkali-soluble resin is obtained.
  • Specific examples of the alkyl group include, for example, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH (CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2.
  • CH (CH 3 ) 2 —CH (CH 3 ) (CH 2 CH 3 ), —C (CH 3 ) 3 , —CH 2 CH 2 CH 2 CH 2 CH 3 , —CH 2 CH 2 CH (CH 3 ) 2 , —CH 2 CH (CH 3 ) (CH 2 CH 3 ), —CH (CH 2 CH 3 ) (CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 2 CH 3 ), —CH (CH 3 ) (CH (CH 3 ) 2 ), —CH 2 CH 2 CH 2 CH 2 CH 3 , —CH (CH 3 ) (CH 2 CH 2 CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 2 CH 2 CH 3 ), —CH (CH 3 ) ( CH 2 CH (CH 3) 2 ), - CH 2 CH 2 CH CH 2 CH 2 CH 3 , etc.
  • alkoxy group examples include, for example, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH (CH 3 ) 2 , —OCH 2 CH 2 CH 2 CH 3 , —OCH 2 CH (CH 3 ) 2 , —OCH (CH 3 ) (CH 2 CH 3 ), —OC (CH 3 ) 3 and the like can be mentioned.
  • the alkali-soluble resin used in the present invention has a polybenzoxazole precursor structure, but is not limited thereto and may have another structure.
  • examples of other structures include a structure having at least one of a polybenzoxazole structure and a polyimide structure, and having a hydroxyl group, a carboxyl group, an ether group or an ester group in the main chain or side chain, a polyimide precursor structure, a polyamide It is an acid ester structure.
  • a polyamide resin having a structure represented by formula (6-1) is preferable from the viewpoint of heat resistance and reliability after final heating. More preferred is a polybenzoxazole precursor resin represented by the formula (6-2).
  • X and Y are organic groups.
  • R 19 and R 24 are a hydroxyl group or —O—R 25 , which may be the same or different, and R 20 is a hydroxyl group, a carboxyl group, —O—R 25 , —COO—. Any one of R 25 , which may be the same or different, m is an integer of 0 to 2, n is an integer of 0 to 4, p is an integer of 0 to 2.
  • R 25 is an integer of 1 to 15 carbon atoms
  • R 19 when R 19 has no hydroxyl group, at least one R 20 must be a carboxyl group, and when R 20 does not have a carboxyl group, R 19 must be at least one must be a hydroxyl group .
  • R 1 , R 21 is alkylene, substituted alkylene, -O -, - S -, - SO 2 -, - CO -, - NHCO -, - C (CF 3) 2 - from an organic group selected .
  • R 17, R 22 is an alkyl group, an alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different, and R 18 and R 23 are any of a hydrogen atom, an alkyl group, an alkoxy group, an acyloxy group, and a cycloalkyl group. And may be the same or different.
  • alkylene and substituted alkylene of R 16 and R 21 in the formula (6) include —CH 2 —, —CH (CH 3 ) —, —C (CH 3 ) 2 —, —CH (CH 2 CH 3 ) —, —C (CH 3 ) (CH 2 CH 3 ) —, —C (CH 2 CH 3 ) (CH 2 CH 3 ) —, —CH (CH 2 CH 2 CH 3 ) —, —C ( CH 3 ) (CH 2 CH 2 CH 3 ) —, —C—CH (CH (CH 3 ) 2 ) —, —C (CH 3 ) (CH (CH 3 ) 2 ) —, —C (CH 3 ) (CH (CH 3 ) 2 ) —, —CH (CH 2 CH 2 CH 2 CH 3 ) —, —C (CH 3 ) (CH 2 CH 2 CH 3 ) —, —CH (CH 2 CH 2 CH 3 ) —, —C (CH
  • alkyl group of R 17 , R 18 , R 22 and R 23 in the formula (6) include —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH (CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH (CH 3 ) 2 , —CH (CH 3 ) (CH 2 CH 3 ), —C (CH 3 ) 3 , —CH 2 CH 2 CH 2 CH 3, -CH 2 CH 2 CH (CH 3) 2, -CH 2 CH (CH 3) (CH 2 CH 3), - CH (CH 2 CH 3) (CH 2 CH 3), - CH (CH 3 ) (CH 2 CH 2 CH 3 ), —CH (CH 3 ) (CH (CH 3 ) 2 ), —CH 2 CH 2 CH 2 CH 3 , —CH (CH 3 ) (CH (CH 3 ) 2 ), —CH 2 CH 2 CH 2 CH 2 CH 3 , —CH (CH 3 ) (CH (CH 3
  • alkoxy group examples include —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH (CH 3 ) 2 , —OCH 2 CH 2 CH 2 CH 3 , —OCH 2 CH (CH 3) 2, -OCH ( CH 3) (CH 2 CH 3), - OC (CH 3) 3 and the like.
  • the light transmittance at a wavelength of 365 nm per film thickness of 5 ⁇ m formed after applying and drying the alkali-soluble resin is 30% or more.
  • the transmittance of the film is high, the sensitivity is improved because more actinic rays reach the inner part of the film.
  • the exposure time is shortened to improve productivity. More preferably, the light transmittance is 50% or more.
  • an alkali-soluble resin having a high light transmittance of a film with respect to actinic radiation having a wavelength of 365 nm, which is often used as an exposure light source for forming a relief pattern can be obtained.
  • the reason for this is that the aromatic structure via R 1 is bent due to the steric hindrance between the substituents represented by R 2 in the formula (1), making it difficult to obtain a planar structure and charge transfer is less likely to occur. Conceivable.
  • the polyamide resin having the structure represented by the formula (6-1) is, for example, a bis (aminophenol) represented by the formula (4) and a diamine or bis (aminophenol) containing 2, if necessary, 2,4-diamino.
  • the polybenzoxazole precursor resin represented by the formula (6-2) includes, for example, a bis (aminophenol) represented by the formula (4) and, if necessary, bis (aminophenol), 2,4-diaminophenol And a compound selected from a dicarboxylic acid containing Y, a dicarboxylic acid dichloride, a dicarboxylic acid derivative, or the like.
  • a dicarboxylic acid an active ester dicarboxylic acid derivative obtained by reacting 1-hydroxy-1,2,3-benzotriazole or the like in advance may be used in order to increase the reaction yield and the like.
  • an alkali-soluble resin having a cured film Tg of 260 ° C. or higher can be obtained even when cured at a low temperature of 250 ° C.
  • —O—R 25 as a substituent of X, —O—R 25 and —COO—R 25 as a substituent of Y are an aqueous alkali solution of a hydroxyl group and a carboxyl group Is a group protected with R 25 , which is an organic group having 1 to 15 carbon atoms, and a hydroxyl group or a carboxyl group may be protected if necessary.
  • R 25 examples include formyl group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, tertiary butoxycarbonyl group, phenyl group, benzyl group, tetrahydrofuranyl group, tetrahydropyranyl group and the like. It is done.
  • this alkali-soluble resin When this alkali-soluble resin is heated at a low temperature of 150 ° C. or higher and lower than 280 ° C., when heated at a high temperature of 280 ° C. or higher and 380 ° C. or lower, it undergoes dehydration and ring closure, resulting in polybenzoxazole resin or polybenzoxazole resin and polyimide resin A heat-resistant resin is obtained in the form of copolymerization with. Heat treatment at a low temperature is effective in improving yield even in a semiconductor element having low heat resistance.
  • X in the formula (6) is an organic group, and examples thereof include aromatic compounds such as benzene ring and naphthalene ring, heterocyclic compounds such as bisphenols, pyrroles and furans, and siloxane compounds.
  • Preferred examples include those represented by the following formula (7). These may be used singly or in combination of two or more if necessary so as not to affect Tg when cured at low temperature.
  • R 26 represents one selected from an alkyl group, an alkyl ester group, an alkyl ether group, and a halogen atom, and each is the same or different.
  • R 27 represents one selected from a hydrogen atom, an alkyl group, an alkyl ester group, and a halogen atom, R is an integer of 0 to 2, and R 28 to R 31 are organic groups.
  • alkyl group represented by R 26 and R 27 in the formula (7) include —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH (CH 3 ) 2 , —CH 2. CH 2 CH 2 CH 3 , —CH 2 CH (CH 3 ) 2 , —CH (CH 3 ) (CH 2 CH 3 ), —C (CH 3 ) 3 , —CH 2 CH 2 CH 2 CH 2 CH 3 , —CH 2 CH 2 CH (CH 3 ) 2 , —CH 2 CH (CH 3 ) (CH 2 CH 3 ), —CH (CH 2 CH 3 ) (CH 2 CH 3 ), —CH (CH 2 CH 3 ) (CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 2 CH 3 ), —CH (CH 3 ) (CH (CH 3 ) 2 ), —CH 2 CH 2 CH 2 CH 3 , —CH (CH 3 ) (CH (CH 3 ) 2 ), —CH 2 CH 2
  • R 19 or R 24 are bonded to X. (In the formula (7), R 19 and R 24 are omitted).
  • b and d which are mole percentages of repeating units including X, may be zero.
  • Y in the formula (6) is an organic group, and examples thereof include those similar to X.
  • aromatic compounds such as benzene ring and naphthalene ring
  • complex compounds such as bisphenols, pyrroles, pyridines and furans.
  • a cyclic compound, a siloxane compound, etc. are mentioned, More specifically, what is shown by following formula (8) can be mentioned preferably. These may be used alone or in combination of two or more.
  • R 32 represents one selected from an alkyl group, an alkyl ester group, an alkyl ether group, and a halogen atom, and may be the same or different.
  • R 34 to R 37 are organic groups. .)
  • alkyl group represented by R 32 and R 33 in Formula (8) include —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH (CH 3 ) 2 , —CH 2. CH 2 CH 2 CH 3 , —CH 2 CH (CH 3 ) 2 , —CH (CH 3 ) (CH 2 CH 3 ), —C (CH 3 ) 3 , —CH 2 CH 2 CH 2 CH 2 CH 3 , —CH 2 CH 2 CH (CH 3 ) 2 , —CH 2 CH (CH 3 ) (CH 2 CH 3 ), —CH (CH 2 CH 3 ) (CH 2 CH 3 ), —CH (CH 2 CH 3 ) (CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 2 CH 3), —CH (CH 3 ) (CH 2 CH 2 CH 3), - CH (CH 3) (CH (CH 3) 2), - CH 2 CH 2 CH 2 CH 2 CH 3, -CH (CH 3) (CH 2 CH 2 CH
  • a compound represented by the following formula (9) is particularly preferable.
  • the position where both C ⁇ O groups are bonded is in the meta position, and both are in the para position.
  • a structure including each of the para positions may be used.
  • R 38 represents one selected from an alkyl group, an alkyl ester group, an alkyl ether group, a benzyl ether group, and a halogen atom
  • X and Y in the formula (6) are preferably cyclic compounds, particularly aromatic. Group compounds are preferred.
  • the alkali-soluble resin represented by the above formula (6) is an acid anhydride containing an amino group at the terminal of the alkali-soluble resin, an aliphatic group having at least one alkenyl group or alkynyl group, or a cyclic compound group.
  • the product is capped as an amide.
  • preservability can be improved.
  • Examples of such a group derived from an acid anhydride containing an aliphatic group or cyclic compound group having at least one alkenyl group or alkynyl group after reacting with an amino group include formula (10) and formula (11). ) And the like. These may be used alone or in combination of two or more.
  • a group selected from the formula (12) is particularly preferable. Thereby, especially storability can be improved.
  • the terminal carboxylic acid contained in the alkali-soluble resin is an amide using an amine derivative containing an aliphatic group or cyclic compound group having at least one alkenyl group or alkynyl group. Can also be capped.
  • the positive photosensitive resin composition contains the alkali-soluble resin and the photosensitive agent.
  • a photosensitizer capable of positive patterning can be used.
  • a compound that generates an acid by light such as a photosensitive diazoquinone compound or an onium salt, or a dihydropyridine compound is used.
  • the photosensitive diazoquinone compound include esters of a phenol compound and 1,2-naphthoquinone-2-diazide-5-sulfonic acid or 1,2-naphthoquinone-2-diazide-4-sulfonic acid.
  • Specific examples include ester compounds represented by formula (13) to formula (16). These may be used alone or in combination of two or more.
  • Q is selected from a hydrogen atom, formula (17), and formula (18).
  • at least one of Q of each compound is represented by formula (17) or formula (18).
  • the positive-type photosensitive resin composition of the present invention uses an alkali-soluble resin having a polybenzoxazole precursor structure composed of bis (aminophenol) of the present invention represented by formulas (3), (4), and (5).
  • a polybenzoxazole precursor structure composed of bis (aminophenol) of the present invention represented by formulas (3), (4), and (5).
  • the cyclization rate is improved when cured at a low temperature. This is considered to be due to the amide bond in the polybenzoxazole precursor structure being pushed out to the hydroxyl group side by steric hindrance with the substituent at the ortho position of the amino group.
  • Examples of a method for obtaining an alkali-soluble resin that achieves a value equal to or higher than the ratio described above include, for example, reducing the weight-average molecular weight of the alkali-soluble resin to 10,000 or less, or forming a siloxane bond, an aliphatic hydrocarbon bond, etc. Among them, a method using bis (aminophenol) represented by the following formulas (3), (4) and (5) is preferable.
  • bis (aminophenol) has a phenolic hydroxyl group at the site adjacent to both amino groups, and further has a substituent at the site adjacent to the opposite side of the amino group.
  • examples of the bis (aminophenol) include a compound represented by the formula (3).
  • the amide bond in the alkali-soluble resin is pushed out to the hydroxyl group side by steric hindrance with the substituent (R 8 ) at the ortho position of the amino group of formula (3), and the carbonyl carbon of the amide bond and the oxygen atom of the hydroxyl group
  • the oxygen atom of the hydroxyl group derived from bis (aminophenol) in the cyclization reaction is easily nucleophilic attacked to the carbon atom of the carbonyl group in the amide bond and cured at a low temperature of 250 ° C. Since the cyclization rate is 80% or more, since the high cyclization rate is exhibited by curing in a wide temperature range, the above-described effect of increasing the Tg is also synergistic, and more excellent reliability can be given.
  • R 7 is an organic group.
  • R 8 is an alkyl group, an alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different.
  • R 9 is a hydrogen atom or an alkyl group. , An alkoxy group, an acyloxy group, or a cycloalkyl group, which may be the same or different.
  • organic group for R 7 examples include alkylene, substituted alkylene, —O—, —S—, —SO 2 —, —Si (CH 3 ) 2 —, —C 6 H 4 —, —CO—. , —NHCO—, —COO—, —C (CF 3 ) 2 — and the like.
  • the bis (aminophenol) is more preferably a bis (aminophenol) represented by the formula (4).
  • R 10 is an organic group selected from alkylene, substituted alkylene, —O—, —S—, —SO 2 —, —CO—, —C (CF 3 ) 2 —.
  • R 11 is alkyl
  • R 12 is any one of a hydrogen atom, an alkyl group, an alkoxy group, an acyloxy group, and a cycloalkyl group, and may be the same or different. May be different.
  • bis (aminophenol) represented by the formula (5). This is because when a bis (aminophenol) having a substituent at the ortho position (R 15 ) of the phenolic hydroxyl group is used, the phenolic hydroxyl group is pushed out to the amide bond side due to steric hindrance with the substituent as described above. It is because it is thought that it approaches.
  • R 13 is an organic group selected from alkylene, substituted alkylene, —O—, —S—, —SO 2 —, —CO—, —C (CF 3 ) 2 —.
  • R 14 is alkyl
  • R 15 is an alkyl group, an alkoxy group, an acyloxy group or a cycloalkyl group, which may be the same or different. Good.
  • R 7 in formula (3), R 10 in formula (4), and R 13 alkylene in formula (5) and substituted alkylene include, for example, —CH 2 — and —CH (CH 3 ) —. , -C (CH 3 ) 2- , -CH (CH 2 CH 3 )-, -C (CH 3 ) (CH 2 CH 3 )-, -C (CH 2 CH 3 ) (CH 2 CH 3 )-, —CH (CH 2 CH 2 CH 3 ) —, —C (CH 3 ) (CH 2 CH 2 CH 3 ) —, —CH (CH (CH 3 ) 2 ) —, —C (CH 3 ) (CH (CH 3) 2) -, - CH (CH 2 CH 2 CH 2 CH 3) -, - C (CH 3) (CH 2 CH 2 CH 2 CH 3) -, - CH (CH 2 CH (CH 3) 2) -, - C (CH 3) (CH 2 CH (CH 3) 2) -, -
  • R 8 and R 9 of formula (3), R 14 and R 15 is an alkyl group of the formula R 11 and R 12 and wherein the (4) (5) or the use of bis (aminophenol) is an alkoxy group,
  • the alkyl group include, for example, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH (CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2.
  • CH (CH 3 ) 2 —CH (CH 3 ) (CH 2 CH 3 ), —C (CH 3 ) 3 , —CH 2 CH 2 CH 2 CH 2 CH 3 , —CH 2 CH 2 CH (CH 3 ) 2 , —CH 2 CH (CH 3 ) (CH 2 CH 3 ), —CH (CH 2 CH 3 ) (CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 2 CH 3 ), —CH (CH 3 ) (CH (CH 3 ) 2 ), —CH 2 CH 2 CH 2 CH 2 CH 3 , —CH (CH 3 ) (CH 2 CH 2 CH 2 CH 3 ), —CH (CH 3 ) (CH 2 CH 2 CH 2 CH 3 ), —CH (CH 3 ) ( CH 2 CH (CH 3) 2 ), - CH 2 CH 2 CH CH 2 CH 2 CH 3 , etc.
  • alkoxy group examples include, for example, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH (CH 3 ) 2 , —OCH 2 CH 2 CH 2 CH 3 , —OCH 2 CH (CH 3 ) 2 , —OCH (CH 3 ) (CH 2 CH 3 ), —OC (CH 3 ) 3 and the like can be mentioned.
  • a phenolic compound can be added so that patterning can be performed with high sensitivity and without resin residue (scum) after development.
  • the resin composition and the photosensitive resin composition in the present invention may contain additives such as a leveling agent and a silane coupling agent as necessary.
  • Solvents include N-methyl-2-pyrrolidone, ⁇ -butyrolactone, N, N-dimethylacetamide, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, propylene glycol Monomethyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3-butylene glycol acetate, 1,3-butylene glycol-3-monomethyl ether, methyl pyruvate, ethyl pyruvate, methyl-3-methoxypropio And the like, and may be used alone or in combination.
  • the composition is applied to a suitable support, for example, a silicon wafer, a ceramic substrate, an aluminum substrate or the like.
  • a suitable support for example, a silicon wafer, a ceramic substrate, an aluminum substrate or the like.
  • the application amount is such that the final film thickness after curing is 0.1 to 30 ⁇ m. If the film thickness is lower than the lower limit, it may be difficult to fully function as a protective film or insulating film for the semiconductor element, and if the upper limit is exceeded, it is difficult to obtain a fine relief pattern. In addition, processing may take time and throughput may decrease.
  • the coating method include spin coating using a spinner, spray coating using a spray coater, dipping, printing, roll coating, and the like.
  • actinic radiation is applied to the desired pattern shape.
  • actinic radiation X-rays, electron beams, ultraviolet rays, visible rays and the like can be used, but those having a wavelength of 200 to 500 nm are preferable.
  • a relief pattern is obtained by dissolving and removing the irradiated portion with a developer.
  • the developer include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and aqueous ammonia, primary amines such as ethylamine and n-propylamine, diethylamine, di-n Secondary amines such as propylamine, tertiary amines such as triethylamine and methyldiethylamine, alcohol amines such as dimethylethanolamine and triethanolamine, quaternary ammonium such as tetramethylammonium hydroxide and tetraethylammonium hydroxide
  • An aqueous solution of an alkali such as a salt and an aqueous solution to which an appropriate amount of a water-soluble organic solvent such as methanol or ethanol or a surfactant is added can be preferably used.
  • methods such as sodium hydro
  • the relief pattern formed by development is rinsed. Distilled water is used as the rinse liquid.
  • heat treatment (curing) is performed to form an oxazole ring, or an oxazole ring and an imide ring, and a cured product having high heat resistance is obtained.
  • the heat treatment can be performed at high temperature or low temperature, and the heat treatment temperature at high temperature is preferably 280 ° C. to 380 ° C., more preferably 290 ° C. to 350 ° C.
  • the heat treatment temperature at a low temperature is preferably 150 ° C. to 280 ° C., more preferably 180 ° C. to 260 ° C.
  • the cured film which is a cured product of the photosensitive resin composition, is used not only for semiconductor devices such as semiconductor elements, but also for display device devices such as TFT-type liquid crystals and organic EL, interlayer insulation films for multilayer circuits, and flexible copper-clad plates. It is also useful as a cover coat, solder resist film or liquid crystal alignment film.
  • Examples of semiconductor device applications include a passivation film formed by forming a cured film of the above-described photosensitive resin composition on a semiconductor element, and a buffer formed by forming a cured film of the above-described photosensitive resin composition on the passivation film.
  • a protective film such as a coating film, an insulating film such as an interlayer insulating film formed by forming a cured film of the above-described photosensitive resin composition on a circuit formed on a semiconductor element, an ⁇ -ray blocking film, a flat surface
  • Examples thereof include a chemical film, a protrusion (resin post), and a partition wall.
  • Examples of display device applications include a protective film formed by forming a cured film of the above-described photosensitive resin composition on a display element, an insulating film or a planarizing film for TFT elements and color filters, MVA type liquid crystal, etc. Examples thereof include protrusions for display devices, partition walls for organic EL element cathodes, and the like.
  • the use method is based on forming the photosensitive resin composition layer patterned on the substrate on which the display element and the color filter are formed according to the semiconductor device application by the above method. High transparency is required for display device applications, especially for insulating films and flattening films. By introducing a post-exposure step before curing of the photosensitive resin composition layer, excellent transparency is achieved. A resin layer can be obtained, which is more preferable in practical use.
  • Alkali-soluble resin (A-1) is a mixture of 60% aminophenol and 40% 4,4'-methylenebis (2-amino-3,6-dimethylphenol) and 40% 4,4'-methylenebis (2-aminophenol).
  • the difference in heat of formation is 4,4′-methylenebis (2-amino-3,6-dimethylphenol) 4.7 times [kcal / mol] multiplied by 0.6 and 4,4
  • the value obtained by adding 1.0 [kcal / mol] of '-methylenebis (2-aminophenol) to 0.4 times was 3.2 [kcal / mol].
  • the difference between the heat generated during the re-stable structure of the amine and the heat generated during the re-stable structure was defined as the energy barrier [kcal / mol] for dihedral angle rotation.
  • Transmittance evaluation A resin in which 4.0 g of alkali-soluble resin (A-1) is dissolved in 8.0 g of ⁇ -butyrolactone is applied to a quartz plate using a spin coater, and then dried on a hot plate at 120 ° C. for 4 minutes to obtain a film thickness of 5 ⁇ m. Coating film was obtained. The transmittance of this coating film was measured with an ultraviolet-visible spectrophotometer (manufactured by Shimadzu Corporation). The transmittance at a wavelength of 365 nm was 31%.
  • Cyclization rate evaluation (alkali-soluble resin): The alkali-soluble resin was applied onto three silicon wafers using a spin coater, and then prebaked on a hot plate at 120 ° C. for 4 minutes to obtain a coating film having a thickness of about 5 ⁇ m. Next, one film-coated silicon wafer was immersed in 2% hydrofluoric acid to obtain a film. The film was measured using a Fourier transform infrared spectrophotometer PARAGON1000 (Perkin Elmer) was calculated ratio of the peak (a) with the wholly aromatic amide group and 1490cm -1 of 1650 cm -1.
  • PARAGON1000 Perkin Elmer
  • the cyclization rate [A] at 250 ° C. was obtained by multiplying (1 ⁇ (b) / (a)) by 100. The cyclization rate thus determined was 89%.
  • the cyclization rate [B] at 320 ° C. was obtained by multiplying (1 ⁇ (c) / (a)) by 100. The cyclization rate thus determined was 100%.
  • [A] / [B] was 0.89, and an alkali-soluble resin with little variation in cyclization rate was obtained even in a wide temperature range.
  • Phenol formula (B-1) 13.53 g (0.0214 mol) and triethylamine 7.62 g (0.0737 mol), 4 ports equipped with thermometer, stirrer, raw material inlet, and dry nitrogen gas inlet pipe Were added and dissolved in 108.65 g of tetrahydrofuran. After cooling the reaction solution to 10 ° C. or lower, 19.80 g (0.0737 mol) of 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride was gradually added dropwise with 100 g of tetrahydrofuran so as not to exceed 10 ° C. . Thereafter, the mixture was stirred at 10 ° C.
  • Sensitivity evaluation This photosensitive resin composition was applied onto a silicon wafer using a spin coater and then prebaked at 120 ° C. for 4 minutes on a hot plate to obtain a coating film having a thickness of about 8.0 ⁇ m.
  • An i-line stepper (Nikon Co., Ltd., 4425i) is passed through this coating film through a mask made by Toppan Printing Co., Ltd. (test chart No. 1: remaining pattern and blank pattern with a width of 0.88-50 ⁇ m are drawn). Used to irradiate with varying exposure.
  • paddle development was performed by adjusting the development time so that the film thickness difference between the pre-baked and the unexposed areas after development was 1 ⁇ m. Then, it rinsed with the pure water for 10 seconds. As a result, it was confirmed that a pattern was formed from the portion irradiated with an exposure amount of 210 mJ / cm 2 . (Sensitivity is 210 mJ / cm 2 ). The resolution was as high as 5 ⁇ m.
  • Glass transition temperature (Tg) evaluation The photosensitive resin composition was applied onto a 6-inch silicon wafer using a spin coater and then prebaked at 120 ° C. for 4 minutes on a hot plate to obtain a coating film having a thickness of about 10 ⁇ m. Next, the silicon wafer with a coating film was heated at 250 ° C./90 minutes using an oven. Next, the obtained cured film was immersed in 2% hydrogen fluoride water, and the film was peeled off from the silicon wafer. The obtained film was sufficiently washed with pure water and dried in an oven. The dried film was cut to a width of 5 mm to produce a sample piece, and the glass transition temperature was measured using a thermomechanical analyzer (TMA) SS6000 manufactured by Seiko Instruments Inc. As a result, it was 270 ° C.
  • TMA thermomechanical analyzer
  • An alkali-soluble resin (A-2) comprising the above compound was synthesized. Others produced the photosensitive resin composition like Example 1, and performed evaluation similar to Example 1. FIG. The energy barrier for rotation of the dihedral angle was 3.6 [kcal / mol].
  • Dicarboxylic acid derivative (activity) obtained by reacting 0.45 mol of isophthalic acid, 0.45 mol of diphenyl ether-4,4′-dicarboxylic acid and 1.8 mol of 1-hydroxy-1,2,3-benzotriazole Esters) 401.76 g (0.9 mol) and 4,4′-methylenebis (2-amino-3,6-dimethylphenol) 286.37 g (1 mol) were thermometer, stirrer, raw material inlet, Into a four-necked separable flask equipped with a dry nitrogen gas inlet tube, 3441 g of N-methyl-2-pyrrolidone was added and dissolved. Thereafter, the mixture was reacted at 75 ° C.
  • Table 1 shows the results obtained for the above Examples and Comparative Examples.
  • Examples 1 to 4 had high sensitivity and high Tg even when cured at a low temperature of 250 ° C., and were excellent in heat resistance and reliability. It was also found that there was little variation in the cyclization rate even when cured in a wide temperature range, and that the cyclization rate was high even when cured at a low temperature.
  • a positive photosensitive resin composition when used as a positive photosensitive resin composition, it is possible to provide an alkali-soluble resin that is highly sensitive and excellent in heat resistance and reliability even when cured at a low temperature.
  • a positive photosensitive resin composition, a cured film, a protective film, an insulating film, and a semiconductor device and a display device using the same which are highly sensitive and have excellent heat resistance and reliability even when cured at a low temperature. Can be provided.

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Abstract

La présente invention concerne une résine soluble en milieu alcalin comprenant une structure de précurseur de polybenzoxazole composée à la fois d'un bis(aminophénol) et d'une structure dérivée d'un acide dicarboxylique, la barrière énergétique à la rotation pour l'angle dièdre, telle qu'obtenue par un calcul basé sur la chimie par modélisation numérique, lorsque les deux cycles aromatiques du bis(aminophénol) sont pivotés, étant de 3 kcal/mol ou plus.
PCT/JP2010/004136 2009-06-26 2010-06-22 Résine soluble en milieu alcalin, composition de résine photosensible positive, film durci, film protecteur, film isolant, et dispositif semi-conducteur et dispositif d'affichage les contenant WO2010150518A1 (fr)

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Citations (10)

* Cited by examiner, † Cited by third party
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JPH0497138A (ja) * 1990-08-09 1992-03-30 Naoya Ogata 高分子薄膜非線形光学材料およびその製造方法
JP2000143804A (ja) * 1998-11-17 2000-05-26 Sumitomo Bakelite Co Ltd ポリベンゾオキサゾール前駆体及び樹脂
JP2001281858A (ja) * 2000-03-31 2001-10-10 Hitachi Chemical Dupont Microsystems Ltd 感光性樹脂組成物、パターン製造法及び半導体装置
JP2002105202A (ja) * 2000-10-03 2002-04-10 Daikin Ind Ltd ビス（３−アミノ−５−アリール−４−ヒドロキシアリール）フルオロアルカン誘導体
JP2007246440A (ja) * 2006-03-16 2007-09-27 Toray Ind Inc ジアミン化合物およびそれを用いたアルカリ可溶性樹脂、感光性樹脂組成物
WO2008050886A1 (fr) * 2006-10-24 2008-05-02 Sumitomo Bakelite Company Limited Dérivé de bis(aminophénol), procédé de production de celui-ci, résine de polyamide, compositions de résine photosensible positive, film protecteur, diélectrique intercouches, dispositif semi-conducteur et élément d'affichage
JP2008156614A (ja) * 2006-11-30 2008-07-10 Sumitomo Bakelite Co Ltd ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置。
WO2008102890A1 (fr) * 2007-02-19 2008-08-28 Sumitomo Bakelite Co., Ltd. Composition de résine photosensible, film durci, film protecteur, film isolant et dispositif semi-conducteur utilisant le film isolant, et dispositif d'affichage
JP2009155481A (ja) * 2007-12-27 2009-07-16 Sumitomo Bakelite Co Ltd アルカリ可溶性樹脂、ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置
WO2010010842A1 (fr) * 2008-07-22 2010-01-28 住友ベークライト株式会社 Composition de résine photosensible de type positif, film durci, film de protection, film isolant et dispositif à semi-conducteur et dispositif d’affichage, chacun comprenant le film durci

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0497138A (ja) * 1990-08-09 1992-03-30 Naoya Ogata 高分子薄膜非線形光学材料およびその製造方法
JP2000143804A (ja) * 1998-11-17 2000-05-26 Sumitomo Bakelite Co Ltd ポリベンゾオキサゾール前駆体及び樹脂
JP2001281858A (ja) * 2000-03-31 2001-10-10 Hitachi Chemical Dupont Microsystems Ltd 感光性樹脂組成物、パターン製造法及び半導体装置
JP2002105202A (ja) * 2000-10-03 2002-04-10 Daikin Ind Ltd ビス（３−アミノ−５−アリール−４−ヒドロキシアリール）フルオロアルカン誘導体
JP2007246440A (ja) * 2006-03-16 2007-09-27 Toray Ind Inc ジアミン化合物およびそれを用いたアルカリ可溶性樹脂、感光性樹脂組成物
WO2008050886A1 (fr) * 2006-10-24 2008-05-02 Sumitomo Bakelite Company Limited Dérivé de bis(aminophénol), procédé de production de celui-ci, résine de polyamide, compositions de résine photosensible positive, film protecteur, diélectrique intercouches, dispositif semi-conducteur et élément d'affichage
JP2008156614A (ja) * 2006-11-30 2008-07-10 Sumitomo Bakelite Co Ltd ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置。
WO2008102890A1 (fr) * 2007-02-19 2008-08-28 Sumitomo Bakelite Co., Ltd. Composition de résine photosensible, film durci, film protecteur, film isolant et dispositif semi-conducteur utilisant le film isolant, et dispositif d'affichage
JP2009155481A (ja) * 2007-12-27 2009-07-16 Sumitomo Bakelite Co Ltd アルカリ可溶性樹脂、ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置
WO2010010842A1 (fr) * 2008-07-22 2010-01-28 住友ベークライト株式会社 Composition de résine photosensible de type positif, film durci, film de protection, film isolant et dispositif à semi-conducteur et dispositif d’affichage, chacun comprenant le film durci

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