WO2016024425A1 - 素子、絶縁膜及びその製造方法、並びに感放射線性樹脂組成物 - Google Patents
素子、絶縁膜及びその製造方法、並びに感放射線性樹脂組成物 Download PDFInfo
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- WO2016024425A1 WO2016024425A1 PCT/JP2015/063901 JP2015063901W WO2016024425A1 WO 2016024425 A1 WO2016024425 A1 WO 2016024425A1 JP 2015063901 W JP2015063901 W JP 2015063901W WO 2016024425 A1 WO2016024425 A1 WO 2016024425A1
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- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910001120 nichrome Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229910002059 quaternary alloy Inorganic materials 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000001552 radio frequency sputter deposition Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000005394 sealing glass Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000005469 synchrotron radiation Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
-
- 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
-
- 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
- G03F7/075—Silicon-containing compounds
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/81—Anodes
- H10K50/818—Reflective anodes, e.g. ITO combined with thick metallic layers
Definitions
- the present invention relates to an element, an insulating film, a manufacturing method thereof, and a radiation-sensitive resin composition.
- a liquid crystal display which is a non-light emitting type is widespread.
- an electroluminescent display which is a self-luminous display is known.
- an organic electroluminescence (EL) element using electroluminescence by an organic compound is expected as a light emitting element provided in a next-generation lighting device in addition to a light emitting element provided in a display.
- an organic EL display or lighting device has an insulating film such as a flattening film and partition walls that partition pixels.
- an insulating film is generally formed using a radiation sensitive resin composition (see, for example, Patent Documents 1 and 2).
- Patent Document 3 proposes an example in which a polycrystalline thin film of an oxide made of In, Ga, Zn (hereinafter also abbreviated as “IGZO”) is used as a semiconductor layer of a TFT, and Patent Documents 3 and 4 describe an amorphous IGZO film.
- IGZO oxide made of In, Ga, Zn
- IGZO is known to suffer light degradation due to natural light, lighting, manufacturing processes, and the like. For this reason, when a TFT including a semiconductor layer made of a material having a large light deterioration such as IGZO is used as a driving element for a display or lighting device, particularly a driving element for an organic EL element, from the viewpoint of preventing light deterioration of IGZO, As a characteristic of the above-described insulating film, a light shielding property from ultraviolet to visible light is necessary. However, many insulating films currently used are transparent, for example, in the vicinity of the ultraviolet region.
- the radiation-sensitive resin composition needs to be able to form an insulating film with a small amount of outgas generation from the viewpoint of manufacturing a device having excellent light emission characteristics.
- the present invention provides a radiation-sensitive resin composition capable of forming an insulating film having a small amount of outgassing and having a light-shielding property in the vicinity of the ultraviolet region, an insulating film formed from the composition, a method for producing the same, and It is an object to provide an element having the insulating film.
- the present inventors have intensively studied to solve the above problems. As a result, the inventors have found that the above problems can be solved by adopting the following configuration, and have completed the present invention.
- the present invention relates to the following [1] to [15], for example.
- a display or lighting device element having an insulating film formed from a radiation-sensitive resin composition containing the above resin At least one selected from (B) a photosensitive agent, (C) a resin having a structural unit represented by formula (C1) described later, and a resin having a structure represented by formula (C2) described later.
- a in Formula (C1) is a divalent group represented by Formula (c1-1), Formula (c1-2), or Formula (c1-3) described later, [1] The element for a display or illumination device described in 1.
- Alkali-soluble resin (A) is polyimide (A1), polyimide precursor (A2), acrylic resin (A3), polysiloxane (A4), polybenzoxazole (A5), and precursor of polybenzoxazole.
- the photosensitive agent (B) according to any one of [1] to [7], wherein the photosensitive agent (B) is at least one selected from a photoacid generator, a photoradical polymerization initiator, and a photocationic polymerization initiator. Element for display or lighting device.
- the content of the resin (C) is 5 to 200 parts by mass with respect to 100 parts by mass of the resin (A).
- the display or lighting device element according to Item is
- At least one selected from (B) a photosensitive agent, (C) a resin having a structural unit represented by formula (C1) described later, and a resin having a structure represented by formula (C2) described later A radiation sensitive resin composition containing the resin.
- a step of forming a coating film on a substrate using the radiation-sensitive resin composition according to [11] or [12], a step of irradiating at least a part of the coating film, and the radiation The manufacturing method of an insulating film which has the process of developing the irradiated coating film, and the process of heating the developed said coating film.
- a radiation-sensitive resin composition capable of forming an insulating film having a small amount of outgassing and having a light-shielding property near the ultraviolet region, an insulating film formed from the composition, and a method for manufacturing the same
- an element having the insulating film can be provided.
- an organic EL element having, as a driving element, a thin film transistor including a semiconductor layer made of a material having a large light deterioration such as IGZO the light deterioration of the substance due to the use of the element can be suppressed. Therefore, an organic EL element with improved reliability and light emission characteristics can be obtained.
- FIG. 1 is a cross-sectional view schematically showing the structure of the main part of the organic EL device.
- the radiation-sensitive resin composition of the present invention the insulating film formed from the composition, the manufacturing method thereof, and the element having the insulating film will be described.
- the radiation-sensitive resin composition of the present invention includes a photosensitive agent (B), a resin having a structural unit represented by the formula (C1) described later, and a resin having a structure represented by the formula (C2) described later. Containing at least one selected resin (C). It is preferable that the composition further contains an alkali-soluble resin (A) described later.
- the composition contains the specific resin (C), it is possible to form an insulating film excellent in light shielding properties near the ultraviolet region, for example, light shielding properties at a wavelength of 400 nm. For this reason, in this invention, the optical deterioration of TFT, for example can be prevented. Moreover, since the said composition is excellent in patterning property and radiation sensitivity, it can respond to the request
- Resin (A) is an alkali-soluble resin excluding resin (C).
- the resin (A) examples include polyimide (A1), polyimide precursor (A2), acrylic resin (A3), polysiloxane (A4), polybenzoxazole (A5), and polybenzoxazole precursor ( And at least one selected from A6).
- the insulating film formed from the resin (A), particularly the insulating film formed from at least one selected from the polyimide (A1), the polyimide precursor (A2), and the polysiloxane (A4) is excellent in heat resistance.
- the polystyrene-equivalent weight average molecular weight (Mw) of the resin (A) is usually 2,000 to 500,000, preferably 3,000 to 100,000, as measured by gel permeation chromatography (GPC). 000, more preferably 4,000 to 50,000.
- Mw is not less than the lower limit of the above range, an insulating film having sufficient mechanical properties tends to be obtained.
- the Mw is not more than the upper limit of the above range, the solubility of the resin (A) in the solvent or developer tends to be excellent.
- alkali-soluble means that the resin (A) can swell or dissolve in an alkali solution, for example, an aqueous 2.38 mass% tetramethylammonium hydroxide solution.
- the content of the resin (A) is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and further preferably 30 to 75% by mass with respect to 100% by mass of the total solid content in the composition of the present invention. preferable.
- the polyimide (A1) preferably has a structural unit represented by the formula (A1).
- R 1 is a divalent group having a hydroxyl group
- X is a tetravalent organic group
- R 1 examples include a divalent group represented by the formula (a1).
- R 2 is a single bond, oxygen atom, sulfur atom, sulfonyl group, carbonyl group, methylene group, dimethylmethylene group or bis (trifluoromethyl) methylene group;
- R 3 is independently A hydrogen atom, a formyl group, an acyl group or an alkyl group; However, at least one of R 3 is a hydrogen atom.
- n1 and n2 are each independently an integer of 0 to 2. However, at least one of n1 and n2 is 1 or 2. When the total of n1 and n2 is 2 or more, the plurality of R 3 may be the same or different.
- examples of the acyl group include groups having 2 to 20 carbon atoms such as an acetyl group, a propionyl group, a butyryl group, and an isobutyryl group;
- examples of the alkyl group include a methyl group, an ethyl group, and n- Examples thereof include groups having 1 to 20 carbon atoms such as propyl group, isopropyl group, n-butyl group, n-pentyl group, n-hexyl group, n-octyl group, n-decyl group and n-dodecyl group.
- the divalent group represented by the formula (a1) is preferably a divalent group having 1 to 4 hydroxyl groups, and more preferably a divalent group having 2 hydroxyl groups.
- Examples of the divalent group having 1 to 4 hydroxyl groups represented by the formula (a1) include a divalent group represented by the following formula. In the following formula, * indicates a bond.
- Examples of the tetravalent organic group represented by X include a tetravalent aliphatic hydrocarbon group, a tetravalent aromatic hydrocarbon group, and a group represented by the following formula (1).
- X is preferably a tetravalent organic group derived from tetracarboxylic dianhydride. Among these, a group represented by the following formula (1) is preferable.
- Ar is each independently a trivalent aromatic hydrocarbon group
- A is a direct bond or a divalent group.
- the divalent group include an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, a methylene group, a dimethylmethylene group, and a bis (trifluoromethyl) methylene group.
- the carbon number of the tetravalent aliphatic hydrocarbon group is usually 4 to 30, preferably 8 to 24.
- the carbon number of the tetravalent aromatic hydrocarbon group and the trivalent aromatic hydrocarbon group in the above formula (1) is usually 6-30, preferably 6-24.
- Examples of the tetravalent aliphatic hydrocarbon group include a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aliphatic hydrocarbon group containing an aromatic ring in at least a part of the molecular structure.
- tetravalent chain hydrocarbon group examples include tetravalent groups derived from chain hydrocarbons such as n-butane, n-pentane, n-hexane, n-octane, n-decane, and n-dodecane. Can be mentioned.
- Examples of the tetravalent alicyclic hydrocarbon group include monocyclic hydrocarbons such as cyclobutane, cyclopentane, cyclopentene, methylcyclopentane, cyclohexane, cyclohexene, and cyclooctane; bicyclo [2.2.1] heptane, bicyclo Bicycles such as [3.1.1] heptane, bicyclo [3.1.1] hept-2-ene, bicyclo [2.2.2] octane, bicyclo [2.2.2] oct-5-ene formula hydrocarbons; tricyclo [5.2.1.0 2,6] decane, tricyclo [5.2.1.0 2, 6] deca-4-ene, adamantane, tetracyclo [6.2.1.1 3 , 6 . 0 2,7 ] tetravalent groups derived from tricyclic or higher hydrocarbons such as dodecane.
- monocyclic hydrocarbons such as cycl
- the number of benzene nuclei contained in the group is preferably 3 or less, and one is particularly preferable. More specifically, tetravalent groups derived from 1-ethyl-6-methyl-1,2,3,4-tetrahydronaphthalene, 1-ethyl-1,2,3,4-tetrahydronaphthalene and the like can be mentioned. .
- the tetravalent group derived from the above hydrocarbon is a tetravalent group formed by removing four hydrogen atoms from the above hydrocarbon.
- the excluded portion of the four hydrogen atoms is a portion where a tetracarboxylic dianhydride structure can be formed when the four hydrogen atoms are substituted with four carboxyl groups.
- the tetravalent aliphatic hydrocarbon group is preferably a tetravalent group represented by the following formula.
- * indicates a bond.
- Examples of the tetravalent aromatic hydrocarbon group and the group represented by the above formula (1) include a tetravalent group represented by the following formula.
- * indicates a bond.
- a polyimide (A1) can be obtained by imidation of the polyimide precursor (A2) demonstrated below.
- the imidization here may proceed completely or partially. In other words, the imidation ratio may not be 100%. Therefore, the polyimide (A1) further has at least one selected from the structural unit represented by the formula (A2-1) and the structural unit represented by the formula (A2-2), which will be described below. May be.
- the imidation ratio is preferably 5% or more, more preferably 7.5% or more, and further preferably 10% or more.
- the upper limit value of the imidization rate is preferably 50%, more preferably 30%. When the imidation ratio is in the above range, it is preferable from the viewpoint of heat resistance and solubility of the exposed portion in the developer.
- the imidization rate can be measured under the conditions described in the examples.
- the total content of the structural units represented by the formula (A1), formula (A2-1), and formula (A2-2) is usually 50% by mass or more, preferably 60% by mass or more. Preferably it is 70 mass% or more, Most preferably, it is 80 mass% or more.
- the polyimide precursor (A2) is a compound that can generate a polyimide (A1), preferably a polyimide (A1) having a structural unit represented by the formula (A1), by dehydration and cyclization (imidization).
- Examples of the polyimide precursor (A2) include polyamic acid and polyamic acid derivatives.
- the polyamic acid has a structural unit represented by the formula (A2-1).
- R 1 is a divalent group having a hydroxyl group
- X is a tetravalent organic group.
- Examples of the divalent group having a hydroxyl group represented by R 1 and the tetravalent organic group represented by X include the same groups as those exemplified as R 1 and X in the formula (A1).
- the content of the structural unit represented by the formula (A2-1) is usually 50% by mass or more, preferably 60% by mass or more, more preferably 70% by mass or more, and particularly preferably 80% by mass or more. is there.
- the polyamic acid derivative is a derivative synthesized by esterification of polyamic acid or the like.
- the polyamic acid derivative include a polymer in which the hydrogen atom of the carboxyl group in the structural unit represented by the formula (A2-1) of the polyamic acid is substituted with another group, and a polyamic acid ester is preferable.
- the polyamic acid ester is a polymer in which at least a part of the carboxyl group of the polyamic acid is esterified.
- Examples of the polyamic acid ester include a polymer having a structural unit represented by the formula (A2-2) capable of producing a polyimide (A1) having the structural unit represented by the formula (A1).
- R 1 is a divalent group having a hydroxyl group
- X is a tetravalent organic group
- R 4 is independently an alkyl group having 1 to 5 carbon atoms.
- Examples of the divalent group having a hydroxyl group represented by R 1 and the tetravalent organic group represented by X include the same groups as those exemplified as R 1 and X in the formula (A1).
- Examples of the alkyl group having 1 to 5 carbon atoms represented by R 4 include a methyl group, an ethyl group, and a propyl group.
- the content of the structural unit represented by the formula (A2-2) is usually 50% by mass or more, preferably 60% by mass or more, more preferably 70% by mass or more, and particularly preferably 80% by mass or more. It is.
- the polyamic acid which is a polyimide precursor (A2) can be obtained, for example, by polymerizing a tetracarboxylic dianhydride, a diamine having a hydroxyl group and, if necessary, another diamine in combination.
- the proportion of these used is, for example, 0.3 to 4 mol, preferably approximately equimolar, of the total diamine to 1 mol of the tetracarboxylic dianhydride.
- the mixed solution of the tetracarboxylic dianhydride and the total diamine is preferably heated at 50 ° C. to 200 ° C. for 1 hour to 24 hours.
- the polyamic acid derivative which is a polyimide precursor (A2) can be synthesized by esterifying the carboxyl group of the polyamic acid.
- a well-known method is applicable.
- the polyimide (A1) can be synthesized, for example, by synthesizing a polyamic acid by the above method and then dehydrating and cyclizing (imidizing) the polyamic acid; and a polyamic acid derivative is synthesized by the above method. Then, it can also synthesize
- the imidization reaction of the polyamic acid and the polyamic acid derivative a known method such as a heat imidization reaction or a chemical imidization reaction can be applied.
- the heating imidization reaction it is preferable to heat the solution containing the polyamic acid and / or the polyamic acid derivative at 120 ° C. to 210 ° C. for 1 hour to 16 hours.
- dicarboxylic acid such as maleic anhydride is used as an end-capping agent for sealing the end groups of polyimide, polyamic acid and polyamic acid derivatives.
- Anhydrides may be used.
- the polymerization solvent used for the synthesis of the resin (A) such as the polyimide (A1) and the polyimide precursor (A2) is preferably a raw material for synthesis or a solvent capable of dissolving the resin (A).
- a polymerization solvent the solvent similar to the solvent illustrated as the solvent (E) mentioned later can be used. The same applies to the synthesis of other resins (A3) to (A6) described later.
- the polyimide (A1) and the polyimide precursor (A2) preferably have the above specific structure having a hydroxyl group, and thereby have excellent solubility in the solvent (E) described later.
- the acrylic resin (A3) is, for example, a resin obtained by polymerizing at least a radical polymerizable monomer having a carboxyl group.
- a radical polymerizable monomer having a carboxyl group for example, a radically polymerizable monomer (a3-1) having a crosslinkable group, a radically polymerizable monomer (a3-2) having a carboxyl group, and other radically polymerizable monomers (a3- Examples thereof include resins obtained by polymerizing 3).
- the monomers (a3-1) to (a3-3) are also referred to as “components (a3-1) to (a3-3)”, respectively.
- the components (a3-1) and (a3-2) used here ) And component (a3-3) will be sequentially described.
- the crosslinkable group in component (a3-1) is a crosslinkable group other than a carboxyl group, and examples thereof include an epoxy group and an oxetanyl group.
- Examples of the component (a3-1) include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, 3-methyl-3- (meth) acryloxymethyloxetane, 3-ethyl-3- (meth) acryloxymethyl oxetane, 3-methyl-3- (meth) acryloxyethyl oxetane, 3-ethyl-3- (meth) acryloxyethyl oxetane, 3-ethyl p-vinylbenzoate Mention may be made of oxetane-3-ylmethyl ester and p-vinylphenyl-3-ethyloxeta-3-ylmethyl ether.
- the acrylic resin (A3) obtained by using the component (a3-1) is used, a small pattern can be formed with high heat resistance and chemical resistance.
- Component (a3-1) can be used alone or in combination of two or more.
- the component (a3-1) is preferably used in an amount of 1 to 70% by mass based on the total mass of all monomers. Such a range is preferable because the size of the pattern obtained from the composition of the present invention is close to the mask dimension and the chemical resistance of the coating film is increased.
- the range of the component (a3-1) is from 10 to 65% by mass, the heat resistance becomes higher, which is more preferable. It is more preferable that the range of the component (a3-1) is 15 to 50% by mass because the developability becomes better.
- Component (a3-2) examples include (meth) acrylic acid, crotonic acid, ⁇ -chloroacrylic acid, cinnamic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, and ⁇ -carboxypolycaprolactone.
- (meth) acrylic acid and mono (2-methacryloyloxyethyl) succinate are preferable.
- (meth) acrylic acid is used, the pattern size of the composition is close to the mask dimension, and transparency Is high, there are few development residues, and the composition excellent in storage stability is obtained.
- Component (a3-2) can be used alone or in combination of two or more.
- the component (a3-2) is preferably used in an amount of 5 to 50% by mass based on the total mass of all monomers. Within such a range, the developability of the composition of the present invention with an alkaline aqueous solution is improved, which is preferable. It is more preferable that the range of the component (a3-2) is 6 to 40% by mass because the pattern size becomes close to the mask dimension. It is more preferable that the range of the component (a3-2) is 7 to 32% by mass because the composition has high sensitivity.
- the component (a3-3) is not particularly limited as long as it is a radical polymerizable monomer copolymerizable with the components (a3-1) and (a3-2).
- the composition of the present invention is applied, exposed and developed. Furthermore, the pattern size is close to the mask dimension, and a desired pattern can be obtained with a low exposure amount, which is preferable. Considering the balance between development time and adhesion, the range of the component (a3-3) is preferably 20 to 78% by mass.
- the acrylic resin (A3) can be obtained, for example, by polymerizing a mixture of radically polymerizable monomers containing the component (a3-1), the component (a3-2) and the component (a3-3).
- the method for polymerizing the monomer is not particularly limited, but radical polymerization in a solution using a solvent is preferable.
- the polymerization temperature is not particularly limited as long as radicals are sufficiently generated from the polymerization initiator to be used, but is usually in the range of 50 ° C to 150 ° C.
- the polymerization time is not particularly limited, but is usually in the range of 3 to 24 hours.
- the polymerization can be performed under any pressure of pressure, reduced pressure, or atmospheric pressure.
- Examples of the polymerization initiator used for synthesizing the acrylic resin (A3) include compounds that generate radicals by heat, and examples thereof include azobisisobutyronitrile, dimethyl-2,2′-azobis (2-methylpropyl).
- An azo initiator such as Pionate
- a peroxide initiator such as benzoyl peroxide can be used.
- a suitable amount of a chain transfer agent such as thioglycolic acid may be added.
- Polysiloxane (A4) examples include polysiloxane obtained by reacting an organosilane represented by the formula (a4).
- R 1 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group-containing group having 6 to 15 carbon atoms, or an epoxy ring having 2 to 15 carbon atoms group, or the alkyl group formed by substituting a substituent one or more hydrogen atoms contained in the group (substituents) may be the same or different each when R 1 is more;
- R 2 is A hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 15 carbon atoms, and when there are a plurality of R 2 s , they may be the same or different;
- n Is an integer from 0 to 3.
- substituents include at least one selected from a halogen atom, an amino group, a hydroxyl group, a mercapto group, and a (meth) acryloyloxy group.
- alkyl group in R 1 and R 2 and its substituent examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, n-hexyl group, and n-decyl group.
- Trifluoromethyl group, 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 3-aminopropyl group, 3-mercaptopropyl group, 3- (meth) acryloyloxypropyl group Can be mentioned.
- Examples of the alkenyl group for R 1 include a vinyl group.
- Examples of the aryl group-containing group in R 1 include an aryl group such as a phenyl group, a tolyl group, and a naphthyl group; a hydroxyaryl group such as a p-hydroxyphenyl group; an aralkyl group such as a benzyl group and a phenethyl group; 1- (p Examples thereof include hydroxyaralkyl groups such as -hydroxyphenyl) ethyl group and 2- (p-hydroxyphenyl) ethyl group; 4-hydroxy-5- (p-hydroxyphenylcarbonyloxy) pentyl group.
- Examples of the epoxy ring-containing group in R 1 include a 3-glycidoxypropyl group and a 2- (3,4-epoxycyclohexyl) ethyl group.
- Examples of the acyl group for R 2 include an acetyl group.
- Examples of the aryl group for R 2 include a phenyl group.
- N in the formula (a4) is an integer of 0 to 3.
- organosilane examples include tetrafunctional silanes such as tetramethoxysilane and tetraphenoxysilane; methyltrimethoxysilane, vinyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, phenyl Trimethoxysilane, phenyltriethoxysilane, p-hydroxyphenyltrimethoxysilane, 1- (p-hydroxyphenyl) ethyltrimethoxysilane, 2- (p-hydroxyphenyl) ethyltrimethoxysilane, 3-glycidoxypropyltri Trifunctional silanes such as methoxysilane, 3-glycidoxypropyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane; dimethyldimethoxysilane, diphenyldime
- organosilane examples include compounds described in JP 2013-210558 A, JP 2014-106250 A, JP 2014-149330 A, and the like.
- Organosilane may be used alone or in combination of two or more.
- the content of the phenyl group contained in the polysiloxane (A4) is preferably 20 to 70 mol, more preferably 35 to 55 moles.
- the phenyl group content is less than or equal to the above upper limit value, an insulating film having a high hardness tends to be obtained, and when the phenyl group content is greater than or equal to the lower limit value, an insulating film having a high crack resistance tends to be obtained. It is in.
- the content of the phenyl group is determined, for example, by measuring the 29 Si-nuclear magnetic resonance spectrum of polysiloxane (A4), and the peak area of Si to which the phenyl group is bonded and the peak area of Si to which the phenyl group is not bonded. It can be obtained from the ratio.
- Polysiloxane (A4) can be obtained, for example, by hydrolyzing and partially condensing the organosilane described above.
- a general method can be used for hydrolysis and partial condensation. For example, a solvent, water and, if necessary, a catalyst are added to organosilane, and the mixture is heated and stirred. During the stirring, hydrolysis by-products such as alcohol and condensation by-products such as water may be distilled off as necessary.
- the reaction temperature is not particularly limited, but is usually in the range of 0 ° C to 200 ° C.
- the reaction time is not particularly limited, but is usually in the range of 1 to 48 hours.
- the amount of the solvent added is preferably 10 to 1000 parts by mass with respect to 100 parts by mass of the organosilane.
- the amount of water used for the hydrolysis reaction is preferably 0.5 to 2 mol with respect to 1 mol of the hydrolyzable group.
- Examples of the catalyst include an acid catalyst and a base catalyst.
- Examples of the acid catalyst include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, acetic acid, trifluoroacetic acid, formic acid, polyvalent carboxylic acid, and anhydrides thereof.
- Examples of the base catalyst include triethylamine, tripropylamine, trioctylamine, diethylamine, triethanolamine, diethanolamine, sodium hydroxide, potassium hydroxide, and alkoxysilane having an amino group.
- the addition amount of the catalyst is preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the organosilane.
- the polybenzoxazole (A5) preferably has a structural unit represented by the formula (A5).
- X 1 is a tetravalent group containing at least one aromatic ring
- Y 1 is a divalent group containing at least one ring selected from an alicyclic hydrocarbon ring and an aromatic hydrocarbon ring. It is the basis of. N and O bonded to X 1 are bonded to adjacent carbon atoms on the same aromatic ring in X 1 to form a benzoxazole ring.
- X 1 may be a group containing at least one aromatic ring, and is not particularly limited, but a group having a linear structure is preferably used, and 1 to 4 aromatic rings A group having an aromatic ring is preferred, and a group having two aromatic rings is more preferred. Thereby, polybenzoxazole (A5) can be made excellent in rigidity.
- the aromatic ring contained in X 1 may be either a substituted or unsubstituted ring.
- Examples of the structure of X 1 include a group represented by the following formula.
- * indicates a bond.
- X 1 is preferably a group composed of an aromatic hydrocarbon ring composed of a carbon atom and a hydrogen atom.
- the plurality of aromatic rings may have either a linked polycyclic system or a condensed polycyclic structure, but have a linked polycyclic structure. It is preferable. Thereby, polybenzoxazole (A5) can be made excellent in both light-shielding property and rigidity.
- the total number of carbon atoms in X 1 is preferably 6 to 24, more preferably 6 to 18, and still more preferably 6 to 14. Thereby, the said effect can be exhibited more notably.
- X 1 is particularly preferably a biphenylene group or a derivative thereof. Thereby, it can be set as polybenzoxazole (A5) excellent in especially rigidity.
- Y 1 may be a group containing at least one ring selected from an alicyclic hydrocarbon ring and an aromatic hydrocarbon ring, and is not particularly limited. A group having a hydrogen ring is preferable, and a group having one alicyclic hydrocarbon ring is more preferable. Thereby, polybenzoxazole (A5) can be made excellent in rigidity and light resistance.
- the alicyclic hydrocarbon ring and aromatic hydrocarbon ring contained in Y 1 may be either substituted or unsubstituted rings.
- Examples of the structure of Y 1 include a group represented by the following formula.
- * indicates a bond.
- the total number of carbon atoms of Y 1 is preferably 4 to 24, more preferably 4 to 15, and still more preferably 6 to 9. Thereby, the said effect can be exhibited more notably.
- Y 1 is particularly preferably a cyclohexylene group or a derivative thereof.
- the cyclohexylene group preferably has a chair-type trans configuration.
- the elastic modulus can be improved when polybenzoxazole (A5) is used.
- Polybenzoxazole (A5) can be obtained by a cyclization reaction of a polybenzoxazole precursor (A6) described below.
- the cyclization reaction here may proceed completely or partially. That is, the cyclization rate may not be 100%.
- polybenzoxazole (A5) may further have a structural unit represented by the formula (A6) described below.
- the cyclization rate is preferably 5% or more, more preferably 7.5% or more, and further preferably 10% or more.
- the upper limit of the cyclization rate is preferably 50%, more preferably 30%.
- the cyclization rate can be measured in the same manner as the imidation rate described in the Examples. However, in the case of polybenzoxazole (A5), around 1557cm -1 from benzoxazole ring, an absorption peak around 1574 -1 can be measured cyclization ratio based.
- polybenzoxazole (A5) the total content of the structural units represented by formula (A5) and formula (A6) is usually 50% by mass or more, preferably 60% by mass or more, more preferably 70% by mass or more, Especially preferably, it is 80 mass% or more.
- the polybenzoxazole precursor (A6) is a compound capable of generating polybenzoxazole (A5), preferably polybenzoxazole (A5) having a structural unit represented by the formula (A5) by dehydration and cyclization. It is.
- the precursor (A6) has, for example, a structural unit represented by the formula (A6).
- X 1 is a tetravalent group containing at least one aromatic ring
- Y 1 is a divalent group containing at least one alicyclic hydrocarbon ring.
- N and OH bonded to X 1 are bonded to adjacent carbons on the same aromatic ring.
- Examples of the divalent group represented by tetravalent group and Y 1 represented by X 1, include those similar to the groups exemplified as X 1 and Y 1 in each formula (A5).
- the content of the structural unit represented by the formula (A6) is usually 50% by mass or more, preferably 60% by mass or more, more preferably 70% by mass or more, and particularly preferably 80% by mass. It is at least mass%.
- the polybenzoxazole precursor (A6) includes, for example, at least one alicyclic hydrocarbon ring, at least one selected from dicarboxylic acids, diesters thereof, and dihalides thereof, and at least one aromatic ring. It can be obtained by polymerizing a diamine having two hydroxyl groups. The ratio of these is, for example, 0.5 to 4 mol, preferably 1 to 2 mol of the diamine with respect to 1 mol of the total of the dicarboxylic acid, diester and dihalide. In the polymerization, the mixed solution is preferably heated at 50 ° C. to 200 ° C. for 1 hour to 72 hours.
- Polybenzoxazole (A5) can be synthesized, for example, by synthesizing a polybenzoxazole precursor (A6) by the above method and then dehydrating and cyclizing the polybenzoxazole precursor (A6).
- the cyclization reaction of the polybenzoxazole precursor (A6) a known method can be applied.
- the solution containing the polybenzoxazole precursor (A6) is preferably heated at 150 to 400 ° C. for 1 to 16 hours. If necessary, it may be carried out while removing water in the system using an azeotropic solvent such as toluene, xylene, mesitylene and the like.
- the photosensitive agent (B) is a compound that generates an acid, a compound that generates a radical, or a compound that generates a cation by a treatment including irradiation of radiation.
- radiation include visible light, ultraviolet light, far ultraviolet light, X-rays, and charged particle beams.
- the radiation-sensitive resin composition can exhibit radiation-sensitive characteristics and can have good radiation sensitivity.
- a photoacid generator is preferred.
- the content of the photosensitive agent (B) in the composition of the present invention is usually 1 to 80 parts by weight, preferably 5 to 60 parts by weight with respect to a total of 100 parts by weight of the resin (C) and the resin (A). More preferably, it is 10 to 55 parts by mass.
- the content of the photosensitive agent (B) in the composition of the present invention is usually 5 to 100 parts by weight, preferably 10 to 60 parts by weight, more preferably 15 to 55 parts by weight with respect to 100 parts by weight of the resin (A). Part by mass.
- the content of the photosensitive agent (B) in the above range, the difference in solubility between the irradiated portion and the unirradiated portion with respect to an alkaline aqueous solution or the like serving as a developer can be increased, and the patterning performance can be improved.
- the acid-generating compound examples include a photoacid generator, such as a quinonediazide compound, an oxime sulfonate compound, an onium salt, an N-sulfonyloxyimide compound, a halogen-containing compound, a diazomethane compound, a sulfone compound, a sulfonic acid ester compound, Examples thereof include carboxylic acid ester compounds.
- a photoacid generator such as a quinonediazide compound, an oxime sulfonate compound, an onium salt, an N-sulfonyloxyimide compound, a halogen-containing compound, a diazomethane compound, a sulfone compound, a sulfonic acid ester compound, Examples thereof include carboxylic acid ester compounds.
- a quinonediazide compound, an oxime sulfonate compound, an onium salt, and a sulfonate compound are preferable, a quinonediazide compound and an oximesulfonate compound are more preferable, and a quinonediazide compound is particularly preferable.
- the quinonediazide compound generates carboxylic acid by processing including irradiation with radiation and development using an aqueous alkali solution.
- Examples of the quinonediazide compound include a condensate of a phenolic compound or an alcoholic compound and 1,2-naphthoquinonediazidesulfonic acid halide.
- Examples of the quinonediazide compound include compounds described in JP2014-111723, JP2014-149330, JP2014-170080, JP2015-4000, and the like.
- Examples of commercially available quinonediazide compounds include trade names “MG-300”, “NT-200”, “NT-300P”, and “TS-200” (all manufactured by Toyo Gosei Co., Ltd.). it can.
- oxime sulfonate compound examples include compounds described in JP 2011-227106 A, JP 2012-234148 A, JP 2013-054125 A, and the like.
- onium salt examples include, for example, Japanese Patent No. 5208573, Japanese Patent No. 5397152, Japanese Patent No. 5413124, Japanese Patent Application Laid-Open No. 2004-210525, Japanese Patent Application Laid-Open No. 2008-129623, Japanese Patent Application Laid-Open No. 2010-215616, and Japanese Patent Application No. 2013-2013. And compounds described in publications such as No. 228526.
- Examples of the compound that generates radicals include photo radical polymerization initiators, and examples thereof include alkylphenone compounds, acylphosphine oxide compounds, oxime ester compounds, benzoin compounds, benzophenone compounds, anthraquinones, and thioxanthones.
- photo radical polymerization initiators include alkylphenone compounds, acylphosphine oxide compounds, oxime ester compounds, benzoin compounds, benzophenone compounds, anthraquinones, and thioxanthones.
- Examples of the compound include JP-A-11-060995, JP-A-2005-202387, JP-A-2006-285226, JP-A-2007-102070, JP-A-2010-049262, JP-A-2010-083970, Examples thereof include compounds described in JP 2012-241127 A, JP 2014-186342 A, JP 2015-050269 A, and the like.
- photo radical polymerization initiators examples include “IRACURE 127”, “IRACURE 651”, “IRACURE 369”, “IRACURE 379EG”, “IRACURE OXE01”, “IRACURE OXE02” (all of which are BASF Japan). Manufactured).
- Examples of the compound that generates a cation include a photocation polymerization initiator, and examples thereof include a sulfonium salt, an iodonium salt, and a diazonium salt.
- a photocation polymerization initiator By using a cationic photopolymerization initiator, a composition exhibiting negative radiation sensitive characteristics can be obtained.
- Examples of the sulfonium salt-based, iodonium salt-based, or diazonium salt-based photocationic polymerization initiator include, for example, JP-A-11-060995, JP-A-2008-088253, JP-A-2010-074250, and JP-A-2011-238307. Examples thereof include compounds described in JP 2012-157996 A and JP-A No. 2015-001667.
- photocationic polymerization initiators examples include sulfonium salt cationic polymerization initiators such as trade names “UVACURE1590” (manufactured by Daicel Cytec Co., Ltd.), “CPI-110P” (manufactured by San Apro Co., Ltd.), Iodonium salt cationic polymerization initiators such as “IRGACURE250” (BASF Japan Ltd.), “WPI-113” (Wako Pure Chemical Industries, Ltd.), “Rp-2074” (Rhodia Japan Ltd.) Is mentioned.
- UVACURE1590 manufactured by Daicel Cytec Co., Ltd.
- CPI-110P manufactured by San Apro Co., Ltd.
- Iodonium salt cationic polymerization initiators such as “IRGACURE250” (BASF Japan Ltd.), “WPI-113” (Wako Pure Chemical Industries, Ltd.), “Rp-2074” (Rhodia Japan Ltd.) Is mentioned.
- the photosensitive agent (B) may be used alone or in combination of two or more.
- the resin (C) is at least one resin selected from a resin having a structural unit represented by the formula (C1) and a resin having a structure represented by the formula (C2).
- the resin having the structural unit represented by the formula (C1) is also referred to as “resin (C1)”
- the resin having the structure represented by the formula (C2) is also referred to as “resin (C2)”.
- A is a divalent aromatic group having a phenolic hydroxyl group
- L is represented by formula (c2-1), formula (c2-2), or formula (c2-3) described later. It is a monovalent group.
- a ′ is a k + m + n-valent aromatic group having a phenolic hydroxyl group
- L is represented by formula (c2-1), formula (c2-2) or formula (c2-3) described later.
- a plurality of L may be the same or different. * Is a bond with another A ′.
- k is an integer from 0 to 9
- m is an integer from 0 to 9
- n is an integer from 0 to 9.
- k + m + n is an integer of 1 to 9, preferably an integer of 2 to 9, and more preferably an integer of 2 to 5.
- the resin (C2) is, for example, a condensate of a resole resin.
- A is a divalent aromatic group having a phenolic hydroxyl group, and is preferably a divalent group represented by formula (c1-1), formula (c1-2), or formula (c1-3). .
- A1 is an integer from 1 to 4.
- b1 is an integer of 0 to 3.
- a2 to a5 and b2 to b5 are each independently an integer of 0 to 4.
- a6 and b6 are integers of 0-2.
- a2 + a3 is an integer from 1 to 6
- b2 + b3 is an integer from 0 to 5
- a2 + a3 + b2 + b3 is an integer from 1 to 6
- a4 + a5 + a6 is an integer from 1 to 8
- b4 + b5 + b6 is 0 or more It is an integer of 7 or less
- a4 + a5 + a6 + b4 + b5 + b6 is an integer of 1 or more and 8 or less.
- A1, a2 + a3, a4 + a5 + a6 are each preferably an integer of 1 to 3.
- R is a hydrocarbon group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, and when there are a plurality of R, they may be the same or different.
- the hydrocarbon group include alkyl groups such as a methyl group, a propyl group, an isopropyl group, and a t-butyl group.
- the alkoxy group include a methoxy group.
- the bonding positions of —OH and —R are not particularly limited, and the bonding positions of two —CH (L) — are not particularly limited.
- two —CH (L) — may be bonded to different benzene nuclei (for example, (1) below), or may be bonded to the same benzene nuclei (for example, (2) below).
- * is a bond.
- the following formulas (1) and (2) are specific examples of the formula (c1-2), but the same applies to the formula (c1-3). For convenience, substituents on the benzene nucleus are omitted.
- the bonding position to —CH (L) — is preferably, for example, the o-position and / or the p-position with respect to the hydroxyl group contained in A.
- the above A is preferably a group represented by the formula (c1-2) or the formula (c1-3) from the viewpoint of imparting light shielding properties and heat resistance and alkali developability, and represented by the formula (c1-2). Are more preferred.
- a ′ is a k + m + n-valent aromatic group having a phenolic hydroxyl group.
- a divalent group represented by the formula (c1-1), the formula (c1-2) or the formula (c1-3) The group changed into k + m + n valent group is mentioned.
- —CH (L) OCH (L) —, —CH (L) —, and —CH (L) OH are bonded to an aromatic ring.
- a1 to a6 and b1 to b6 in the formulas (c1-1) to (c1-3) are as follows.
- a1 is an integer of 1 or more and “6 ⁇ (k + m + n)” or less.
- b1 is an integer of 0 to “5- (k + m + n)”.
- a2 to a5 and b2 to b5 are each independently an integer of 0 to 4.
- a6 and b6 are integers of 0-2.
- a2 + a3 is an integer of 1 to “8 ⁇ (k + m + n)”
- b2 + b3 is an integer of 0 to “7 ⁇ (m + n)”
- a2 + a3 + b2 + b3 is an integer of 1 to “8 ⁇ (k + m + n)”.
- A4 + a5 + a6 is an integer from 1 to “10 ⁇ (k + m + n)”, b4 + b5 + b6 is an integer from 0 to “9 ⁇ (k + m + n)”, and a4 + a5 + a6 + b4 + b5 + b6 is from 1 to “10 ⁇ (k + m + n)” It is an integer. Further, 1 ⁇ a1 + b1 ⁇ “6 ⁇ (k + m + n)”, a2 + b2 ⁇ 4, a3 + b3 ⁇ 4, a4 + b4 ⁇ 4, a5 + b5 ⁇ 4, and a6 + b6 ⁇ 2.
- L is a monovalent group represented by formula (c2-1), formula (c2-2), or formula (c2-3).
- X is an oxygen atom, a sulfur atom, —CH 2 — or —NH—, preferably an oxygen atom or a sulfur atom.
- R 1 is a monovalent group selected from a halogen atom, —OH, —SH, —NO 2 , —NH 2 , a hydrocarbon group, and a heteroatom-containing group having 1 or more carbon atoms.
- R 1 When a plurality of R 1 are present, they may be the same or different, and R 1 bonded to adjacent ring carbons may be bonded to each other to form a ring, for example, a benzene ring.
- Y represents a nitrogen atom, C—H or C—R 2 .
- R 2 has the same meaning as R 1 in formula (c2-1).
- R 3 and R 4 are each independently a hydrogen atom or a hydrocarbon group.
- n is an integer of 0 to 4, preferably an integer of 0 to 3, and d is 0 or 1.
- R 2 When a plurality of R 2 are present, they may be the same or different, and R 2 bonded to adjacent ring carbons may be bonded to each other to form a ring.
- Examples of the ring formed by bonding R 2 to each other include a condensed carbocyclic ring and a condensed heterocyclic ring when shown together with a benzene nucleus or a pyridine nucleus to which R 2 is bonded. Is mentioned. These rings may further have the groups listed for R 1 . * In the formula is a bond. From the viewpoint of light shielding properties of the insulating film, L preferably has a condensed carbocyclic ring such as a naphthalene ring or an anthracene ring.
- R 5 has the same meaning as R 1 in formula (c2-1).
- Each l is independently an integer of 0 to 5, preferably 0.
- R 5 bonded to adjacent ring carbons may be bonded to each other to form a ring, for example, a benzene ring.
- Examples of the hydrocarbon group in R 1 to R 5 include aryl groups having 1 to 18 carbon atoms such as methyl group, ethyl group, isopropyl group, isobutyl group and pentyl group, and aryl groups having 6 to 24 carbon atoms such as phenyl group. Groups.
- hetero atom-containing group having 1 or more carbon atoms in R 1 to R 2 and R 5 examples include halogenated hydrocarbon groups such as a halogenated alkyl group having 1 to 18 carbon atoms such as a carboxyl group and a trifluoromethyl group, C1-C18 hydroxyalkyl group such as hydroxymethyl group, C1-C18 alkoxy group such as methoxy group and hetoxy group, phenoxy group, aryloxy group having 6-30 carbon atoms such as tolyloxy group, methylthio group C1-C18 thioalkoxy group such as benzyloxy group, C7-C30 aralkyloxy group such as benzyloxy group, C2-C20 acyloxyalkyl group such as acetoxymethyl group, dimethylamino group, diphenylamino group, etc.
- halogenated hydrocarbon groups such as a halogenated alkyl group having 1 to 18 carbon atoms such as a carb
- Substituted amino group, furanyl group, thienyl group, pyrrolyl group, imidazolyl group, pyridinyl group, pyrimidinyl group, pyra Heterocycles such as a dinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, and a morpholinyl group are exemplified.
- R 1 is preferably an alkyl group, an aryl group, a hydroxyalkyl group, an acyloxyalkyl group, or —NO 2 .
- R 2 is preferably a halogen atom, a halogenated alkyl group, a carboxyl group, an alkoxy group, a thioalkoxy group, an aralkyloxy group, a substituted amino group, or a heterocyclic ring. Also preferred is an embodiment in which two R 2 bonded to adjacent ring carbons are bonded to each other to form a ring.
- Resin (C) is a substance that develops color when heated.
- the coating film formed from the composition containing the resin (C) before exposure does not have a light shielding property near the ultraviolet region, for example, a light shielding property at a wavelength of 400 nm.
- the resin (C) is ketoized by heating after exposure and development, and the obtained insulating film is presumed to have a light-shielding property at the wavelength.
- the light shielding property is not imparted at a heating temperature of about 60 to 130 ° C. during pre-baking, and the light shielding property can be imparted at a temperature of about 300 ° C. or less exceeding the heating temperature of 130 ° C. during post-baking. .
- a novolak resin having a repeating structural unit represented by the formula (C1) is preferable because it has good alkali solubility (developability).
- developerability alkali solubility
- Resin (C1) can be obtained, for example, by condensing phenols and aldehydes in the presence of an acid catalyst and distilling off unreacted components as necessary. As reaction conditions, phenols and aldehydes are usually reacted at 60 to 200 ° C. for about 1 to 20 hours in a solvent. For example, it can be synthesized by the method described in Japanese Patent Publication Nos. 47-15111 and 63-238129.
- m + n is an integer of 1 or more).
- the resol resin can be obtained, for example, by condensing phenols and aldehydes in the presence of a base catalyst and distilling off unreacted components as necessary. As reaction conditions, phenols and aldehydes are usually reacted at 40 to 120 ° C. for about 1 to 20 hours in a solvent. In this way, for example, a resole resin in which —CH (L) OH is bonded to an aromatic ring contained in phenols can be obtained.
- the condensate of the resole resin can be obtained by advancing the dehydration condensation reaction by adding heat or acid to the resole resin. This reaction proceeds by dehydration condensation of —CH (L) OH contained in the resole resin.
- the resol resin or a solution thereof is usually reacted at 60 to 200 ° C. for about 1 to 20 hours.
- the resol resin or a solution thereof is usually reacted at 60 to 200 ° C. for about 1 to 20 hours.
- it can be synthesized by the method described in Japanese Patent No. 3889274, Japanese Patent No. 4013111, Japanese Patent Application Laid-Open No. 2010-111013, and the like.
- phenols include: Compounds having 1 to 4 hydroxyl groups, preferably 1 to 3 and having 1 benzene nucleus, specifically phenol, orthocresol, metacresol, paracresol, 2,3-dimethylphenol, 2, 5-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2,4-dimethylphenol, 2,6-dimethylphenol, 2,3,5-trimethylphenol, 2,3,6-trimethylphenol 2-t-butylphenol, 3-t-butylphenol, 4-t-butylphenol, 2-methylresorcinol, 4-methylresorcinol, 5-methylresorcinol, 4-t-butylcatechol, 2-methoxyphenol, 3-methoxyphenol 2-propylphenol, 3-propylphenol, 4 Propyl phenol, 2-isopropyl phenol, 2-methoxy-5-methylphenol, 2-t-butyl-5-methylphenol, 2-isopropyl-5-methylphenol, 5-isopropyl-2-methylphenol; Compounds having 1
- aldehydes examples include compounds represented by L—C ( ⁇ O) —H (L in the formula has the same meaning as L in the formula (C1)). The compound of this is mentioned.
- the amount of aldehyde used is usually 0.3 mol or more, preferably 0.4 to 3 mol, more preferably 0.5 to 2 mol, relative to 1 mol of phenols. It is.
- Examples of the acid catalyst in the synthesis of the novolak resin include hydrochloric acid, paratoluenesulfonic acid, and trifluoromethanesulfonic acid.
- a base catalyst in the synthesis combination of a resole resin, ammonia water and a tertiary amine are mentioned, for example.
- the weight average molecular weight (Mw) in terms of polystyrene of the resin (C) is usually 100 to 50,000, preferably 150 to 10,000, more preferably as measured by gel permeation chromatography (GPC). Is 500 to 6,000. Resin (C) having Mw in the above range is preferable in terms of resolution.
- Resin (C) may be used alone or in combination of two or more.
- the content of the resin (C) is preferably 5 to 85% by mass, more preferably 10 to 75% by mass, and further preferably 10 to 70% by mass with respect to 100% by mass of the total solid content in the composition of the present invention. preferable.
- the content of the resin (C) is usually 5 to 200 parts by weight, preferably 10 to 100 parts by weight, more preferably 15 to 90 parts by weight with respect to 100 parts by weight of the resin (A). Part by mass, particularly preferably 18 to 80 parts by mass.
- the content of the resin (C) is not less than the lower limit of the above range, the effect of imparting light-shielding properties and developability based on the resin (C) is easily exhibited.
- the content of the resin (C) is not more than the upper limit of the above range, there is little possibility that deterioration of the low water absorption of the insulating film, increase in the outgas amount, and decrease in heat resistance will occur.
- the crosslinking agent (D) is a compound having a crosslinkable functional group.
- a crosslinking agent (D) the compound which has a 2 or more crosslinkable functional group in 1 molecule is mentioned, for example.
- the compound corresponding to both acrylic resin (A3) and a crosslinking agent (D) is classified into acrylic resin (A3), and the compound applicable to both resin (C) and crosslinking agent (D) is And classified into resin (C).
- the organic EL device When the insulating film made of the composition of the present invention is used as a constituent element of an organic EL device, the organic EL device deteriorates when the organic light emitting layer comes into contact with moisture. It is preferable to reduce the property.
- crosslinkable functional groups include isocyanate groups and blocked isocyanate groups, oxetanyl groups, glycidyl ether groups, glycidyl ester groups, glycidyl amino groups, methoxymethyl groups, ethoxymethyl groups, benzyloxymethyl groups, acetoxymethyl groups, benzoic groups.
- Roxymethyl group formyl group, acetyl group, dimethylaminomethyl group, diethylaminomethyl group, dimethylolaminomethyl group, diethylolaminomethyl group, morpholinomethyl group; ethylenic group such as vinyl group, vinylidene group, (meth) acryloyl group Examples thereof include a group having an unsaturated bond.
- the crosslinking agent (D) may be used alone or in combination of two or more.
- the content of the crosslinking agent (D) is usually 1 to 210 parts by mass, preferably 10 to 150 parts by mass, with respect to 100 parts by mass in total of the resin (C) and the resin (A). Part, more preferably 15 to 100 parts by weight.
- the content of the crosslinking agent (D) is not less than the lower limit of the above range, the low water absorption of the insulating film tends to be improved.
- the content of the crosslinking agent (D) is not more than the upper limit of the above range, the heat resistance of the insulating film tends to be improved.
- crosslinking agent (D) for example, a compound having two or more glycidyl groups in one molecule, a compound having two or more oxetanyl groups in one molecule, and two or more ethylenic unsaturations in one molecule
- Compound having a bond methoxymethyl group-containing phenol compound, methylol group-containing melamine compound, methylol group-containing benzoguanamine compound, methylol group-containing urea compound, methylol group-containing phenol compound, alkoxyalkyl group-containing melamine compound, alkoxyalkyl group-containing benzoguanamine compound, Alkoxyalkyl group-containing urea compounds, alkoxyalkyl group-containing phenolic compounds, carboxymethyl group-containing melamine resins, carboxymethyl group-containing benzoguanamine resins, carboxymethyl group-containing urea resins, carboxymethyl group-containing phenols Resins, carboxymethyl group-containing melamine compounds,
- Examples of the compound having two or more glycidyl groups in one molecule include ethylene glycol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, and trimethylolpropane triglycidyl ether.
- Examples of the compound having two or more glycidyl groups in one molecule include, for example, JP-A No. 2014-170949, JP-A No. 2014-189616, JP-A No. 2014-205838, JP-A No. 2014-229596, JP-A No. 2015-2015. And compounds described in publications such as 27665.
- Examples of the compound having two or more oxetanyl groups in one molecule include 4,4-bis [(3-ethyl-3-oxetanyl) methyl] biphenyl, 3,7-bis (3-oxetanyl) -5 Oxanonane, 3,3 ′-[1,3- (2-methylenyl) propanediylbis (oxymethylene)] bis (3-ethyloxetane), ethylene glycol bis [(3-ethyl-3-oxetanyl) methyl] ether, Examples include dicyclopentenyl bis [(3-ethyl-3-oxetanyl) methyl] ether and triethylene glycol bis [(3-ethyl-3-oxetanyl) methyl] ether.
- Examples of the compound having two or more oxetanyl groups in one molecule include JP2013-234230, JP2014-149330, JP2014-186300, JP2015-38182, and JP2015. And compounds described in publications such as No. 42713.
- Examples of the compound having two or more ethylenically unsaturated bonds in one molecule include polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, trimethylolethane tri (meth) acrylate, trimethylolpropane tri (Meth) acrylate, trimethylolpropane di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipenta Examples include polyfunctional (meth) acrylates such as erythritol penta (meth) acrylate.
- Examples of the compound having two or more ethylenically unsaturated bonds in one molecule include, for example, JP 2001-104878, JP 2013-029780, JP 2013-41225, JP 2013-57755, And compounds described in publications such as No. 4400936.
- crosslinking agent (D) examples include a compound having a group in which an isocyanate group is blocked by a protective group.
- the said compound is also called "block isocyanate compound.”
- a group in which an isocyanate group is blocked with a protective group is also referred to as a “blocked isocyanate group”.
- Examples of the blocked isocyanate compound include JP2013-225031, JP51332096, JP5071686, JP2013223238, JP51999752, JP200341185, JP4879557, And compounds described in Japanese Laid-Open Patent Publication No. 2006-119441.
- solvent (E) A solvent (E) can be used in order to make a radiation sensitive resin composition liquid.
- solvent (E) examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, ethyl-3-ethoxypropionate, propylene glycol monomethyl ether, propylene glycol monoethyl ether.
- Methoxypropyl acetate diethylene glycol ethyl methyl ether, diethyl ketone, methyl butyl ketone, dipropyl ketone, methyl ethyl ketone, dioxane, acetone, cyclohexanone, cyclopentanone, n-pentanol, diacetone alcohol, and ⁇ -butyrolactone.
- Examples of the solvent (E) include the solvents described in JP 2012-12472 A, JP 2013-54376 A, JP 2014-115438 A, JP 2014-197171 A, JP 2014-189561 A, and the like. Also mentioned.
- Examples of the solvent (E) can further include amide solvents, and examples thereof include compounds described in Japanese Patent Nos. 4618632 and 5613851.
- Examples of the solvent (E) include propylene glycol monomethyl ether acetate (hereinafter also referred to as “PGMEA”), propylene glycol monomethyl ether (hereinafter also referred to as “PGME”), diethylene glycol ethyl methyl ether (hereinafter also referred to as “EDM”), diacetone alcohol. (Hereinafter also referred to as “DAA”) is particularly preferable.
- PGMEA propylene glycol monomethyl ether acetate
- PGME propylene glycol monomethyl ether
- EDM diethylene glycol ethyl methyl ether
- DAA diacetone alcohol
- ⁇ -butyrolactone (hereinafter also referred to as “BL”) is preferably used as the solvent (E), and a mixed solvent containing BL is preferable.
- the BL content is preferably 70% by mass or less, more preferably 20 to 60% by mass, based on 100% by mass of the total amount of the solvent (E).
- BL is preferably used in combination with at least one selected from PGMEA, PGME and EDM. It exists in the tendency which can maintain suitably the melt
- solvent (E) in addition to the solvents exemplified above, alcohol solvents such as propanol and butanol; aromatic hydrocarbon solvents such as toluene and xylene can be used in combination as necessary.
- Solvent (E) may be used alone or in combination of two or more.
- the content of the solvent (E) is such that the solid content concentration of the composition is usually 5 to 60% by mass, preferably 10 to 55% by mass, more preferably 15 to 50% by mass. It is.
- solid content means all components other than a solvent (E).
- the radiation-sensitive resin composition is within a range that does not impair the effects of the present invention, and other additives such as an adhesion assistant (F), a surfactant (G), and a dye (H) as necessary.
- An optional component may be contained.
- Other optional components may be used alone or in combination of two or more.
- the adhesion aid (F) is a component that improves the adhesion between a film forming object such as a substrate and the insulating film.
- the adhesion assistant (F) is particularly useful for improving the adhesion between the inorganic substrate and the insulating film.
- the inorganic substance include silicon compounds such as silicon, silicon oxide, and silicon nitride; and metals such as gold, copper, and aluminum.
- a functional silane coupling agent is preferable.
- functional silane coupling agents include silane coupling agents having reactive substituents such as carboxyl groups, halogen atoms, vinyl groups, methacryloyl groups, isocyanate groups, epoxy groups, oxetanyl groups, amino groups, and thiol groups. Can be mentioned.
- Examples of the functional silane coupling agent include N-phenyl-3-aminopropyltrimethoxysilane, trimethoxysilylbenzoic acid, ⁇ -methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, ⁇ - Isocyanatopropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylalkyldialkoxysilane, ⁇ -chloropropyltrialkoxysilane, ⁇ -mercaptopropyltrialkoxysilane, ⁇ - (3,4- (Epoxycyclohexyl) ethyltrimethoxysilane.
- N-phenyl-3-aminopropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylalkyldialkoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxy Silane and ⁇ -methacryloxypropyltrimethoxysilane are preferred.
- the content of the adhesion assistant (F) in the composition of the present invention is 100% by mass of the total solid content in the composition of the present invention, preferably 20% by mass or less, more preferably 0.01 to 15% by mass. is there.
- Surfactant (G) is a component which improves the film-forming property of a radiation sensitive resin composition.
- the radiation-sensitive resin composition can improve the surface smoothness of the coating film, and as a result, the film thickness uniformity of the insulating film can be further improved.
- the surfactant (G) include a fluorine-based surfactant and a silicone-based surfactant.
- surfactant (G) examples include specific examples described in JP-A Nos. 2003-015278 and 2013-231869.
- the content of the surfactant (G) in the composition of the present invention is preferably 100% by mass or less, more preferably 20% by mass or less, more preferably 0.01 to 15% by mass in the total solid content in the composition of the present invention. More preferably, it is 0.05 to 10% by mass.
- the dye (H) is a component that enhances the light shielding property of the insulating film. By using the dye (H), it is possible to obtain a display or lighting device that is more reliable.
- the dye (H) may be any component that absorbs light in the wavelength range of 400 nm to 1000 nm, and examples thereof include anthraquinone-based, methine-based, indigoid-based, and azo-based organic compound pigments.
- Examples of the dye (H) include JP-A No. 2003-246840, JP-A No. 2007-177088, JP-A No. 2008-255241, JP-A No. 2012-321818, JP-A No. 2013-509988, and JP-A No. 2015-30753. And compounds described in JP-A-2015-32660 and JP-A-2015-43378.
- H examples include trade names “OilBlue 5511”, “PlastBlueDB-463”, “SDO-11”, “SDO-12”, “SDO-14”, “SDO-C8”, “SDO-C8”.
- -C12 "," SDO-C33 "(Arimoto Chemical Co., Ltd.),” NEOSUPERBLACK C-832 "(Chuo Synthetic Chemical Co., Ltd.),” Aizen Spiron Red BEH Special “(Hodogaya Chemical Co., Ltd.) ).
- the content of the dye (H) is preferably 1 to 50% by mass, more preferably 3 to 50% by mass, further preferably 100% by mass of the total solid content in the composition of the present invention. Is 5 to 50% by mass.
- Dye (H) may be used alone or in combination of two or more.
- the radiation-sensitive resin composition can be prepared, for example, by mixing the solvent (E) with essential components such as the photosensitizer (B) and the resin (C) and other components as necessary. Moreover, in order to remove dust, after mixing each component uniformly, you may filter the obtained mixture with a filter.
- the method for forming an insulating film of the present invention includes a step 1 for forming a coating film on a substrate using the above-described radiation-sensitive resin composition, a step 2 for irradiating at least a part of the coating film, and the radiation It has the process 3 which develops the irradiated coating film, and the process 4 which heats the said developed coating film.
- an insulating film having excellent light shielding properties and a small outgas amount it is possible to form an insulating film having excellent light shielding properties and a small outgas amount. Moreover, since the above-mentioned radiation sensitive resin composition is excellent in radiation sensitivity, an insulating film having a fine and elaborate pattern can be easily formed by forming a pattern by exposure, development, and heating utilizing the characteristics. can do.
- step 1 the radiation-sensitive resin composition is applied to the substrate surface, and preferably the pre-baking is performed to remove the solvent (E) to form a coating film.
- the film thickness of the coating film can be usually 0.3 to 25 ⁇ m, preferably 0.5 to 20 ⁇ m after pre-baking.
- the substrate examples include a resin substrate, a glass substrate, and a silicon wafer.
- the substrate further includes, for example, a TFT substrate on which TFTs and wirings thereof are formed in an organic EL element being manufactured.
- Examples of the coating method of the radiation sensitive resin composition include a spray method, a roll coating method, a spin coating method, a slit die coating method, a bar coating method, and an ink jet method. Among these coating methods, spin coating and slit die coating are preferable.
- the pre-baking conditions vary depending on the composition of the radiation-sensitive resin composition, but for example, the heating temperature is 60 to 130 ° C. and the heating time is about 30 seconds to 15 minutes.
- the pre-bake is preferably performed at a temperature at which the light shielding property based on the resin (C) is not imparted to the coating film.
- step 2 the coating film formed in step 1 is irradiated with radiation through a mask having a predetermined pattern.
- the radiation used at this time include visible light, ultraviolet light, far ultraviolet light, X-rays, and charged particle beams.
- visible light include g-line (wavelength 436 nm) and h-line (wavelength 405 nm).
- ultraviolet rays include i-line (wavelength 365 nm).
- Examples of the far ultraviolet light include laser light from a KrF excimer laser.
- X-rays include, for example, synchrotron radiation.
- Examples of the charged particle beam include an electron beam.
- the exposure dose is preferably 6000 mJ / cm 2 or less, and preferably 20 to 2000 mJ / cm 2 .
- the amount of exposure can be measured by measuring the intensity of radiation at a wavelength of 365 nm with an illuminometer (“OAI model 356” from OAI Optical Associates).
- step 3 the coating film irradiated with radiation in step 2 is developed.
- a portion irradiated with radiation is removed, and when a negative composition is used, a non-irradiated portion is removed to form a desired pattern.
- an alkaline aqueous solution is preferable.
- alkaline compound contained in the alkaline aqueous solution examples include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, diethylaminoethanol, di-n-propyl.
- the concentration of the alkaline compound in the alkaline aqueous solution is preferably from 0.1% by mass to 5% by mass from the viewpoint of obtaining appropriate developability.
- the organic solvent in the latter aqueous solution the same solvent as the solvent (E) for obtaining the resin (A) or the radiation sensitive resin composition can be used.
- Examples of the developing method include a liquid piling method, a dipping method, a rocking dipping method, and a shower method.
- the development time varies depending on the composition of the radiation sensitive resin composition, but is usually about 10 seconds to 180 seconds. Following such development processing, for example, washing with running water is performed for 30 seconds to 90 seconds, and then a desired pattern can be formed by, for example, air drying with compressed air or compressed nitrogen.
- step 4 After step 3, using a heating device such as a hot plate or an oven, the coating film is cured by a heat treatment (post-bake treatment) on the coating film to obtain an insulating film.
- the heating temperature in this heat treatment is, for example, more than 130 ° C. and not more than 300 ° C., and the heating time varies depending on the type of heating equipment, but for example, 5 minutes to 30 minutes when performing the heat treatment on a hot plate. When the heat treatment is performed in an oven for 30 minutes, it is 30 minutes to 90 minutes. At this time, a step baking method or the like in which a heating process is performed twice or more can also be used.
- the heat treatment in the above temperature range gives the insulating film a light shielding property such that the total light transmittance at a wavelength of 400 nm is, for example, 15% or less, preferably 12% or less, more preferably 5% or less. In this manner, an insulating film having a target pattern can be formed on the substrate.
- the patterned coating film may be rinsed or decomposed.
- the rinse treatment it is preferable to wash the coating film using the solvent mentioned as the solvent (E).
- the photosensitive agent (B) such as a quinonediazide compound remaining in the coating film can be decomposed by irradiating the entire surface with radiation (post-exposure) from a high-pressure mercury lamp or the like.
- the amount of exposure in this post-exposure is preferably about 1000 to 5000 mJ / cm 2 .
- the composition of the present invention exhibits good characteristics in patterning property and radiation sensitivity, and the insulating film thus obtained has a light shielding property with respect to light in the ultraviolet region, for example, at a wavelength of 400 nm. Further, the insulating film generates a small amount of outgas and exhibits good characteristics in heat resistance and low water absorption. For this reason, the said insulating film can be used suitably as an insulating film as a protective film or a planarization film
- the thickness of the insulating film of the present invention is usually from 0.3 to 25 ⁇ m, preferably from 0.5 to 20 ⁇ m, from the viewpoint of light shielding properties.
- the insulating film of the present invention has a total light transmittance at a wavelength of 400 nm of preferably 0 to 15%, more preferably 0 to 12%, and further preferably 0 to 5%. Further, the insulating film of the present invention has a total light transmittance at a wavelength of 600 nm of preferably 30% or less, more preferably 10% or less.
- the total light transmittance can be measured using, for example, a spectrophotometer (“150-20 type double beam” manufactured by Hitachi, Ltd.).
- Examples of the display device having the element of the present invention include a liquid crystal display (LCD), an electrochromic display (ECD), an electroluminescent display (ELD), and particularly an organic EL display.
- LCD liquid crystal display
- ECD electrochromic display
- ELD electroluminescent display
- organic EL lighting is mentioned, for example.
- the display or lighting device is generically called “device”.
- One embodiment of the element of the present invention includes a first electrode provided on a TFT substrate and connected to the TFT, and the first electrode formed on the first electrode so as to partially expose the first electrode. It has an insulating film and a second electrode provided to face the first electrode.
- An embodiment of the device having the element of the present invention includes a TFT substrate, a first electrode provided on the TFT substrate and connected to the TFT, and a first electrode so as to partially expose the first electrode.
- the insulating film of the present invention formed above and a second electrode provided to face the first electrode.
- the insulating film is formed so as to cover at least a part of the first electrode and partially expose the first electrode.
- the insulating film is preferably formed so as to cover the edge portion of the first electrode.
- the film thickness of the insulating film is not particularly limited, but is preferably 0.3 to 25 ⁇ m, more preferably 0.5 to 20 ⁇ m, considering the ease of film formation and patterning.
- the insulating film is formed so as to straddle adjacent first electrodes, for example. For this reason, the insulating film is required to have good electrical insulation.
- the volume resistivity of the insulating film is preferably 10 10 ⁇ ⁇ cm or more, more preferably 10 12 ⁇ ⁇ cm or more.
- the insulating film is, for example, a partition that partitions the surface of the TFT substrate into a plurality of regions.
- the insulating film (partition wall) is preferably formed on the TFT substrate so as to be disposed at least above the semiconductor layer, from the viewpoint of light shielding with respect to the semiconductor layer included in the TFT.
- “upward” is a direction from the TFT substrate toward the second electrode.
- the insulating film exposing the first electrode has a light shielding property near the ultraviolet region, for example, at a wavelength of 400 nm as described above.
- the insulating film functions as a light-shielding film. Photodegradation of the semiconductor layer due to use or the like can be suppressed.
- the semiconductor layer constituting the TFT may be a layer containing an oxide semiconductor containing one or more elements selected from In, Ga, Sn, Ti, Nb, Sb and Zn.
- oxide semiconductor containing one or more elements selected from In, Ga, Sn, Ti, Nb, Sb and Zn.
- the oxide in this case include a single crystal oxide, a polycrystalline oxide, an amorphous oxide, and a mixture thereof.
- an oxide semiconductor containing one or more elements selected from In, Ga, Sn, Ti, Nb, Sb, and Zn for example, a quaternary system such as an In—Sn—Ga—Zn—O-based oxide semiconductor Metal oxide: In-Ga-Zn-O-based oxide semiconductor, In-Sn-Zn-O-based oxide semiconductor, In-Al-Zn-O-based oxide semiconductor, Sn-Ga-Zn-O-based oxide Ternary metal oxides such as semiconductors, Al—Ga—Zn—O-based oxide semiconductors, Sn—Al—Zn—O-based oxide semiconductors; In—Zn—O-based oxide semiconductors, Sn—Zn—O-based semiconductors Oxide semiconductors, Al—Zn—O-based oxide semiconductors, Zn—Mg—O-based oxide semiconductors, Sn—Mg—O-based oxide semiconductors, In—Mg—O-based oxide semiconductors, In—Ga—O Binary metal oxides such as In-based materials;
- the semiconductor layer constituting the TFT is the above oxide semiconductor layer, particularly when the semiconductor layer is an oxide semiconductor layer made of an In—Ga—Zn—O-based oxide semiconductor (IGZO semiconductor). Photodegradation can be prevented.
- IGZO semiconductor In—Ga—Zn—O-based oxide semiconductor
- the apparatus of the present invention includes a first electrode provided on the TFT substrate and connected to the TFT, an organic light emitting layer formed on the first electrode in a region partitioned by the partition, and an organic light emitting layer
- An organic EL device having an organic EL element including the second electrode provided on the top is preferable.
- the TFT substrate includes, for example, a support substrate, a TFT provided on the support substrate corresponding to the organic EL element, and a planarization layer covering the TFT.
- the first electrode is formed on the planarization layer, and is connected to the TFT through a through hole penetrating the planarization layer.
- the insulating film (partition wall) having a light shielding property is preferably formed on the first electrode and the planarization layer so as to partially expose the first electrode.
- FIG. 1 is a cross-sectional view schematically showing the structure of the main part of an organic EL display or illumination device (hereinafter also simply referred to as “organic EL device”) according to the present invention.
- the organic EL device 1 in FIG. 1 is an active matrix organic EL device having a plurality of pixels formed in a matrix.
- the organic EL device 1 may be either a top emission type or a bottom emission type.
- the property of the material constituting each member, such as transparency, is appropriately selected according to the top emission type and the bottom emission type.
- the organic EL device 1 includes a support substrate 2, a thin film transistor (hereinafter also referred to as “TFT”) 3, a first insulating film 4, an anode 5 as a first electrode, a through hole 6, a second insulating film 7, and an organic light emitting layer. 8.
- a cathode 9 as a second electrode, a passivation film 10 and a sealing substrate 11 are provided.
- the second insulating film 7 the insulating film of the present invention is used.
- the support substrate 2 is made of an insulating material.
- the insulating material for example, transparent resins such as highly transparent polyethylene terephthalate, polyethylene naphthalate, and polyimide, and glass materials such as alkali-free glass are preferable.
- any insulator can be used as the insulating material, and the above-described transparent resin and glass material can be used.
- the TFT 3 is an active element of each pixel portion and is formed on the support substrate 2.
- the TFT 3 includes a gate electrode, a gate insulating film, a semiconductor layer, a source electrode, and a drain electrode.
- the present invention is not limited to the bottom gate type in which the gate insulating film and the semiconductor layer are sequentially provided on the gate electrode, and may be the top gate type in which the gate insulating film and the gate electrode are sequentially provided on the semiconductor layer.
- the semiconductor layer can be formed using the above-described oxide semiconductor containing one or more elements selected from In, Ga, Sn, Ti, Nb, Sb, and Zn.
- the first insulating film 4 is a flattening film that plays a role of flattening surface irregularities due to the TFT 3.
- the first insulating film 4 is formed so as to cover the entire TFT 3.
- the 1st insulating film 4 may be formed using the radiation sensitive resin composition mentioned above, and may be formed using a conventionally well-known radiation sensitive resin composition.
- the first insulating film 4 can be formed by the method described in the above-described insulating film forming method.
- the anode 5 forms a pixel electrode.
- the anode 5 is formed on the first insulating layer 4 with a conductive material.
- the organic EL device 1 is a bottom emission type, the anode 5 is required to be transparent. Therefore, as the material of the anode 5, highly transparent ITO (Indium Tin Oxide), IZO (Indium Zinc Oxide), and tin oxide are preferable.
- the organic EL device 1 is a top emission type, the anode 5 is required to have light reflectivity.
- Al aluminum
- APC alloy silica, palladium, copper alloy
- ARA silica, rubidium, gold alloy
- MoCr molybdenum and chromium alloy having high light reflectivity
- NiCr nickel and chromium alloy
- a laminated film of these metals and a highly transparent electrode eg, ITO
- the through hole 6 is formed to connect the anode 5 and the drain electrode of the TFT 3.
- the second insulating film 7 serves as a partition (bank) having a recess 70 that defines the arrangement region of the organic light emitting layer 8.
- the second insulating film 7 is formed so as to cover a part of the anode 5 and to expose a part of the anode 5.
- the 2nd insulating film 7 can be formed by the method etc. which were demonstrated in the formation method of an insulating film using the radiation sensitive resin composition mentioned above.
- the thickness of the second insulating film 7 (distance between the uppermost surface of the second insulating film 7 and the lowermost surface of the organic light emitting layer 8) is preferably 0.3 ⁇ m or more and 25 ⁇ m or less, and preferably 0.5 ⁇ m or more and 20 ⁇ m or less. More preferred.
- Organic light emitting layer 8 emits light when an electric field is applied.
- the organic light emitting layer 8 is a layer containing an organic light emitting material that emits electroluminescence.
- the organic light emitting layer 8 is formed on the anode 5 in a region defined by the second insulating film 7, that is, a recess 70. In this way, by forming the organic light emitting layer 8 in the recess 70, the periphery of the organic light emitting layer 8 is surrounded by the second insulating film 7, and adjacent pixels can be partitioned.
- a hole injection layer and / or a hole transport layer may be disposed between the anode 5 and the organic light emitting layer 8, and an electron transport layer and / or an electron between the organic light emitting layer 8 and the cathode 9.
- An injection layer may be disposed.
- the cathode 9 is formed so as to cover a plurality of pixels in common, and serves as a common electrode of the organic EL device 1.
- the cathode 9 is made of a conductive member.
- the cathode 9 is preferably a visible light transmissive electrode, and examples thereof include an ITO electrode and an IZO electrode.
- the cathode 9 does not need to be a visible light transmissive electrode.
- examples of the constituent material of the cathode 9 include barium (Ba), barium oxide (BaO), aluminum (Al), and an alloy containing Al.
- the passivation film 10 suppresses intrusion of moisture and oxygen into the organic EL element.
- the passivation film 10 is provided on the cathode 9.
- the sealing substrate 11 seals the main surface on which the organic light emitting layer 8 is disposed (the surface opposite to the support substrate 2 in the TFT substrate).
- the sealing substrate 11 include glass substrates such as non-alkali glass substrates.
- the main surface on which the organic light emitting layer 8 is disposed is preferably sealed with the sealing substrate 11 through the sealing layer 12 using a sealing agent applied in the vicinity of the outer peripheral edge of the TFT substrate.
- the sealing layer 12 can be, for example, a layer of an inert gas such as dried nitrogen gas or a layer of a filling material such as an adhesive.
- the second insulating film 7 has a light shielding property with respect to light having a wavelength of 400 nm, it is possible to suppress the photodegradation of the semiconductor layer associated with the use of the device, Further, since the outgas amount from the second insulating film 7 is small, the light emission characteristics are excellent.
- the first insulating film 4 and the second insulating film 7 can be formed using a radiation-sensitive resin composition having low water absorption, and in the process of forming these insulating films 4 and 7, Processing such as cleaning using a low water-absorbing material is possible.
- part means “part by mass” unless otherwise specified.
- “NICOLET6700FT-IR” manufactured by Thermo Electron
- the flask was immersed in an oil bath at 70 ° C. and stirred for 1 hour, and then the temperature of the oil bath was raised to 115 ° C. over 30 minutes. One hour after the start of temperature increase, the internal temperature of the solution reached 100 ° C., and was then heated and stirred for 2 hours (internal temperature was 100 to 110 ° C.). During the reaction, a total of 115 g of methanol and water as by-products were distilled out. Diacetone alcohol was added to the obtained resin (A-4) in diacetone alcohol so that the resin (A-4) concentration was 40% by mass, and the resin (A-4) in diacetone alcohol was added. Obtained. The obtained resin (A-4) had a weight average molecular weight (Mw) of 5000 and a phenyl group content of 35 mol with respect to 100 mol of Si atoms.
- Mw weight average molecular weight
- novolak resin (C-1) had a weight average molecular weight (Mw) of 4,500.
- Synthesis Examples C2 to C8 were performed in the same manner as Synthesis Example C1 except that the aldehydes shown in Table 1 were used, and novolak resins (C-2) to (C-6) and other novolak resins (C-7) To (C-8) was obtained. The results are shown in Table 1.
- Resin (A) used for the preparation of the radiation sensitive resin composition is Resin (A-1) to (A-4) of Synthesis Examples A1 to A4, and Resin (C) is the novolak resin of Synthesis Examples C1 to C6.
- B-1 Naphthoquinonediazide sulfonic acid ester (NT-300P, manufactured by Toyo Gosei Co., Ltd.)
- B-2 1,2-octanedione-1- [4- (phenylthio) -2- (O-benzoyloxime)] (“IRACURE OXE01” manufactured by BASF Japan Ltd.)
- D-1 4,4-bis [(3-ethyl-3-oxetanyl) methyl] biphenyl (“OXBP” manufactured by Ube Industries, Ltd.)
- D-2 Dipentaerythritol hexaacrylate (“M-402” manufactured by Toagosei Co., Ltd.)
- PGMEA propylene glycol monomethyl ether acetate
- PGME propylene glycol monomethyl ether
- DAA diacetone alcohol
- Solvent Red83 ("Aizen Spiron Red BEH Special” manufactured by Hodogaya Chemical Co., Ltd.) [Example 1] In a resin solution containing resin (A-1) of Synthesis Example A1 (amount corresponding to 40 parts (solid content) of resin (A-1)), 16 parts of (B-1), 25 parts of (C-1), (D-1) 15 parts, (F-1) 3 parts, (G-1) 1 part, and a solvent are mixed and filtered through a membrane filter having a diameter of 0.2 ⁇ m to have the composition shown in Table 2. Radiation sensitive resin composition 1 was prepared. In addition, the solid content concentration of the said composition was 30 mass%.
- Example 2 to 27 and Comparative Examples 1 to 3 radiation-sensitive resin compositions 2 to 30 were prepared in the same manner as in Example 1 except that the components of the types and blending amounts shown in Table 2 were used. .
- an insulating film and an organic EL element were produced by the method described below.
- the patterning property and radiation sensitivity of the composition, the light-shielding property (transmittance), water absorption, heat resistance, and outgas amount of the obtained insulating film, and the device characteristics of the obtained organic EL device, were as follows. evaluated.
- the “composition” means a radiation-sensitive resin composition obtained in Examples and Comparative Examples.
- the composition was applied onto a silicon substrate using a spinner and then pre-baked on a hot plate at 120 ° C. for 2 minutes to form a coating film.
- This coating film was exposed with an exposure amount of 100 mJ / cm 2 at a wavelength of 365 nm through a pattern mask having a predetermined pattern using an exposure machine (“MPA-6000” manufactured by Canon Inc.).
- the exposure amount was measured with an illuminometer (“OAI model 356” manufactured by OAI Optical Associates). After that, development was performed by using a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 25 ° C.
- ⁇ Radiation sensitivity> The composition was applied onto a silicon substrate using a spinner and then pre-baked on a hot plate at 120 ° C. for 2 minutes to form a coating film having a thickness of 3.0 ⁇ m.
- the coating film was exposed using an exposure machine (Canon “MPA-6000”) while changing the exposure amount through a pattern mask having a predetermined pattern. After that, development was performed by using a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 25 ° C. for 80 seconds, washed with ultrapure water for 1 minute, dried, and dried on a silicon substrate. A coating film having a plurality of through holes of 20.0 ⁇ m was formed.
- the exposure amount required for the coating film to completely dissolve in accordance with the shape of the mask pattern having a diameter of 20.0 ⁇ m was measured, and the exposure amount at this time was defined as radiation sensitivity (exposure sensitivity).
- the radiation sensitivity was “good” when the exposure dose at a wavelength of 365 nm was 100 mJ / cm 2 or less, and “bad” when the exposure amount exceeded 100 mJ / cm 2 .
- the exposure amount was measured with an illuminometer (“OAI model 356” manufactured by OAI Optical Associates).
- the total light transmittance was measured in the wavelength range of 300 nm to 780 nm using a spectrophotometer (“150-20 type double beam” manufactured by Hitachi, Ltd.). The total light transmittance was determined. This transmittance is “excellent” when the total light transmittance at a wavelength of 400 nm is 5% or less, “good” when it exceeds 5% and 15% or less, and “bad” when it exceeds 15%. did. Moreover, the total light transmittance in wavelength 600nm was calculated
- thermogravimetric apparatus manufactured by TA Instruments.
- a 5% weight loss temperature was determined by performing TGA measurement at 10 ° C. (in air, at a rate of temperature increase of 10 ° C./min). The heat resistance was “excellent” when the 5% weight loss temperature exceeded 350 ° C., and “good” when the temperature was 350 to 330 ° C.
- the TFT substrate was formed by the following procedure. First, a molybdenum film was formed on a glass substrate by sputtering, and a gate electrode was formed by photolithography using a resist and etching. Next, a silicon oxide film was formed by sputtering on the entire surface of the glass substrate and on the upper layer of the gate electrode to form a gate insulating film. An InGaZnO-based amorphous oxide film (InGaZnO 4 ) was formed on the gate insulating film by sputtering, and a semiconductor layer was formed by photolithography and etching using a resist.
- InGaZnO-based amorphous oxide film InGaZnO 4
- a molybdenum film was formed on the semiconductor layer by sputtering, and a source electrode and a drain electrode were formed by photolithography and etching using a resist. Finally, a silicon oxide film was formed by sputtering on the entire surface of the substrate and on the upper layer of the source electrode and drain electrode to obtain a passivation film, thereby obtaining a TFT substrate.
- the device characteristics were evaluated as switching response characteristics.
- the switching response characteristic was evaluated by measuring the ON / OFF ratio.
- the ON / OFF ratio was calculated by measuring the current flowing between the source electrode and the drain electrode with a voltage applied to the gate electrode using a prober and a semiconductor parameter analyzer. Specifically, the drain electrode is set to plus 10 V under the condition that the semiconductor layer is irradiated with white light (illuminance 30000 lux) centered on a wavelength of 450 nm or 500 nm from above the insulating film formed from the above composition.
- the ratio of the current value when the voltage applied to the gate electrode is plus 10 V and minus 10 V when the source electrode is 0 V is defined as the ON / OFF ratio.
- the switching response characteristic that is, the element characteristic, was “good” when the ON / OFF ratio was 1.0 ⁇ 10 5 or more, and “bad” when it was less than 1.0 ⁇ 10 5 .
- TFT reliability refers to changes in Id-Vg characteristics (amount of change in threshold voltage Vth) when an electrical stress is applied between the gate electrode and the source electrode, when the evaluation element is irradiated with light and when light is not irradiated. It was evaluated by comparing with.
- the electrical stress is applied by keeping the potential of the source electrode of the evaluation element at 0 V, the potential of the drain electrode at +10 V, and applying the voltage between the source electrode and the drain electrode, and the potential Vg of the gate electrode at ⁇ 20 V. To + 20V.
- the potential Vg of the gate electrode is changed, the current Id flowing between the drain electrode and the source electrode is plotted to obtain the Id-Vg characteristic.
- the voltage at which the current value is ON is set to the threshold voltage Vth.
- the TFT reliability is assumed to be “excellent”.
- the TFT reliability is determined to be “good” when it is suppressed to 5 to 2 times, and the TFT reliability is determined to be “bad” when it exceeds 2 times.
- ⁇ EL emission characteristic evaluation> Using a glass substrate (Corning “Corning 7059”), an ITO transparent electrode was sputtered on this glass substrate, and then a photosensitive resist (“NN700”, manufactured by JSR Corporation) was applied by spin coating. It dried and exposed through the predetermined pattern mask. After exposure, development and heat curing were performed to form a predetermined resist pattern. Subsequently, the ITO film was etched using an etching solution to form a predetermined ITO film pattern, and then the resist pattern was removed with a stripping solution.
- a photosensitive resist (“NN700”, manufactured by JSR Corporation) was applied by spin coating. It dried and exposed through the predetermined pattern mask. After exposure, development and heat curing were performed to form a predetermined resist pattern. Subsequently, the ITO film was etched using an etching solution to form a predetermined ITO film pattern, and then the resist pattern was removed with a stripping solution.
- a photosensitive resist (“NN700”, manufactured by JSR Corporation) to a film thickness of 5 ⁇ m by spin coating on the glass substrate on which ITO transparent electrodes are formed in an array as described above
- a coating film was formed by pre-baking on a hot plate at 80 ° C. for 3 minutes. Subsequently, this coating film was exposed through a predetermined pattern mask. After exposure, the film was developed and post-baked at 200 ° C. for 5 minutes in a clean oven. In this way, a planarization layer having a contact hole in which only a part of the ITO transparent electrode was exposed was formed on the glass substrate.
- the thickness of the planarization layer after post-baking was 3 ⁇ m.
- a plurality of glass substrates on which a planarizing layer was formed as described above were prepared and used in the following steps.
- An Al film having a thickness of 100 nm was formed on a glass substrate on which a planarizing layer was formed by DC sputtering using an Al target.
- a photosensitive resist (“NN700”, manufactured by JSR Corporation) was applied by a spin coat method, dried, and exposed through a predetermined pattern mask. After exposure, development and heat curing were performed to form a predetermined resist pattern.
- the Al film was etched using a mixed acid etching solution to form a predetermined Al film pattern, and then the resist pattern was removed with a stripping solution.
- the glass substrate was transferred to a sputtering apparatus, and an ITO film having a thickness of 20 nm was formed on the Al pattern by a DC magnetron reactive sputtering method using an ITO target.
- a photosensitive resist (“NN700”, manufactured by JSR Corporation) was applied by a spin coat method, dried, and exposed through a predetermined pattern mask. After exposure, development and heat curing were performed to form a predetermined resist pattern.
- the ITO film was etched using an etching solution to form an ITO film pattern similar to the Al film on the Al film, and then the resist pattern was removed with a stripping solution. In this way, an anode composed of an Al film and an ITO film was formed.
- An organic EL element was formed on the anode substrate on which the partition walls were formed by a vacuum deposition method.
- the organic EL element was prepared by the following procedure.
- the anode substrate on which the partition walls were formed was subjected to ultrasonic cleaning, and then the substrate was transferred into an N 2 atmosphere and dried at 200 ° C. for 3 hours. Further, the substrate was transferred to an oxygen plasma processing apparatus, evacuated, and 50 W RF power was applied to a ring electrode provided in the vicinity of the substrate to perform an oxygen plasma cleaning process.
- the oxygen pressure was 0.6 Pa and the treatment time was 40 seconds.
- molybdenum oxide (MoOx) having a hole injection property is deposited on the substrate using a vapor deposition mask having a predetermined pattern.
- a film was formed by resistance heating vapor deposition at a film formation rate of 0.004 to 0.005 nm / sec to form a hole injection layer having a thickness of 1 nm.
- tris (8-quinolinolato) aluminum (Alq 3 ), which is an alkylate complex, is used as a green light-emitting material by a resistance heating vapor deposition method in the same manner as the hole transport layer using a vapor deposition mask having a predetermined pattern.
- a light emitting layer having a film thickness of 35 nm was formed. The film formation rate was 0.5 nm / sec or less.
- lithium fluoride was deposited by resistance heating vapor deposition under the same exhaust conditions as the hole injection layer to form an electron injection layer having a thickness of 0.8 nm.
- the film formation rate was 0.004 nm / sec or less.
- the substrate was transferred to another film formation chamber (sputter chamber), and a cathode having a thickness of 130 nm was formed on the electron injection layer by an RF sputtering method using an ITO target.
- sputter chamber film formation chamber
- the substrate is transferred to the glove box, N 2 leaks, and the sealing glass with the hygroscopic material attached to the element surface side is bonded to the substrate using a UV curing acrylic adhesive. And sealed.
- the organic EL element for evaluation was stored in a constant temperature and humidity chamber having a temperature of 85 ° C. and a humidity of 85% for 500 hours, and then the organic EL element was started at room temperature and a dark spot (non-light emitting portion) was observed. The case where the area of the dark spot was less than 10% with respect to the whole was determined as “good”, and the case where it was 10% or more or quenched was determined as “bad”.
- the insulating films formed in Examples 1 to 27 were excellent in light shielding properties and had a small outgas amount. Further, the compositions and insulating films of Examples 1 to 27 were excellent in patternability, radiation sensitivity, low water absorption and heat resistance. An element using this insulating film and a semiconductor layer that is easily deteriorated in light was excellent in switching response characteristics and TFT reliability even in a light irradiation environment. Moreover, the obtained organic EL element was excellent in EL light emission characteristics.
- the formed insulating film was inferior in light shielding properties and inferior in device characteristics.
- the novolak resin is not a resin having a structural unit represented by the formula (C1) (corresponding to the alkali-soluble resin (A)).
- the insulating films formed from the compositions of Comparative Examples 1 and 2 have a large amount of outgas and are inferior in EL emission characteristics, and the compositions of Comparative Examples 1 and 2 are inferior in patternability and radiation sensitivity. It was.
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Abstract
Description
本発明の感放射線性樹脂組成物は、感光剤(B)と、後述する式(C1)で表される構造単位を有する樹脂、および後述する式(C2)で表される構造を有する樹脂から選ばれる少なくとも1種の樹脂(C)とを含有する。上記組成物は、さらに後述するアルカリ可溶性樹脂(A)を含有することが好ましい。
樹脂(A)は、樹脂(C)を除く、アルカリ可溶性樹脂である。
ポリイミド(A1)は、式(A1)で表される構造単位を有することが好ましい。
ポリイミド前駆体(A2)は、脱水・環化(イミド化)によって、ポリイミド(A1)、好ましくは式(A1)で表される構造単位を有するポリイミド(A1)を生成することができる化合物である。ポリイミド前駆体(A2)としては、例えば、ポリアミック酸およびポリアミック酸誘導体が挙げられる。
ポリアミック酸は、式(A2-1)で表される構造単位を有する。
ポリアミック酸誘導体は、ポリアミック酸のエステル化等により合成される誘導体である。ポリアミック酸誘導体としては、例えば、ポリアミック酸が有する式(A2-1)で表される構造単位中のカルボキシル基の水素原子を他の基に置換した重合体が挙げられ、ポリアミック酸エステルが好ましい。
ポリイミド前駆体(A2)であるポリアミック酸は、例えば、テトラカルボン酸二無水物と、水酸基を有するジアミン及び必要に応じて他のジアミンとを組み合わせて重合させることにより、得ることができる。これらの使用割合は、例えば前記テトラカルボン酸二無水物1モルに対して前記の全ジアミンを0.3~4モル、好ましくは略等モルである。前記重合において、前記テトラカルボン酸二無水物および前記の全ジアミンの混合溶液を50℃~200℃、1時間~24時間加熱することが好ましい。
アクリル樹脂(A3)としては、例えば、カルボキシル基を有するラジカル重合性モノマーを少なくとも重合させて得られる樹脂である。例えば、架橋性基を有するラジカル重合性モノマー(a3-1)、カルボキシル基を有するラジカル重合性モノマー(a3-2)、および前記重合性モノマーと共重合可能なその他のラジカル重合性モノマー(a3-3)を重合させて得られる樹脂が挙げられる。
成分(a3-1)における架橋性基は、カルボキシル基以外の架橋性基であり、例えばエポキシ基、オキセタニル基が挙げられる。
成分(a3-2)としては、例えば、(メタ)アクリル酸、クロトン酸、α-クロルアクリル酸、けい皮酸、マレイン酸、フマル酸、イタコン酸、シトラコン酸、メサコン酸、ω-カルボキシポリカプロラクトンモノ(メタ)アクリレート、コハク酸モノ[2-(メタ)アクリロイロキシエチル]、マレイン酸モノ[2-(メタ)アクリロイロキシエチル]、シクロヘキセン-3,4-ジカルボン酸モノ[2-(メタ)アクリロイロキシエチル]である。これらの中でも、(メタ)アクリル酸、コハク酸モノ(2-メタクリロイロキシエチル)が好ましく、特に(メタ)アクリル酸を用いると、組成物のパターンサイズがマスク寸法に近くなり、また、透明性が高く、現像残渣が少なく、保存安定性に優れた組成物が得られる。
成分(a3-3)は、成分(a3-1)および(a3-2)と共重合可能なラジカル重合性モノマーであれば、特に限定されるものではない。例えば、スチレン、メチルスチレン、ビニルトルエン、クロルメチルスチレン、(メタ)アクリルアミド、トリシクロ[5.2.1.02,6]デカニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、ベンジル(メタ)アクリレート、イソボルニル(メタ)アクリレート、メチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、ブチル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、フェニル(メタ)アクリレート、グリセロールモノ(メタ)アクリレート、N-フェニルマレイミド、N-アクリロイルモルホリン、インデンが挙げられ、また、5-テトラヒドロフルフリルオキシカルボニルペンチルアクリレート等の、テトラヒドロフルフリルアルコールをε-カプロラクトンで変性して得られる化合物の(メタ)アクリル酸エステルが挙げられる。
アクリル樹脂(A3)は、例えば、成分(a3-1)、成分(a3-2)および成分(a3-3)を含有するラジカル重合性モノマーの混合物を重合させて得ることができる。前記モノマーの重合方法は特に制限されないが、溶媒を用いた溶液中でのラジカル重合が好ましい。重合温度は使用する重合開始剤からラジカルが十分発生する温度であれば特に限定されないが、通常50℃~150℃の範囲である。重合時間も特に限定されないが、通常3~24時間の範囲である。また、当該重合は、加圧、減圧または大気圧のいずれの圧力下でも行うことができる。
ポリシロキサン(A4)としては、例えば、式(a4)で表されるオルガノシランを反応させて得られるポリシロキサンが挙げられる。
ポリベンゾオキサゾール(A5)は、式(A5)で表される構造単位を有することが好ましい。
ポリベンゾオキサゾール前駆体(A6)は、脱水・環化によって、ポリベンゾオキサゾール(A5)、好ましくは式(A5)で表される構造単位を有するポリベンゾオキサゾール(A5)を生成することができる化合物である。前駆体(A6)は、例えば、式(A6)で表される構造単位を有する。
ポリベンゾオキサゾール前駆体(A6)は、例えば、脂環式炭化水素環を少なくとも1つ含む、ジカルボン酸、そのジエステル体およびそのジハライド体から選ばれる少なくとも1種と、芳香族環を少なくとも1つ含み、水酸基を2つ有するジアミンとを重合させることにより、得ることができる。これらの使用割合は、例えば前記ジカルボン酸とジエステル体とジハライド体との合計1モルに対して前記ジアミンを0.5~4モル、好ましくは1~2モルである。前記重合において、前記混合溶液を50℃~200℃、1時間~72時間加熱することが好ましい。
感光剤(B)は、放射線の照射を含む処理によって、酸を発生する化合物、ラジカルを発生する化合物、カチオンを発生する化合物である。放射線としては、例えば、可視光線、紫外線、遠紫外線、X線、荷電粒子線が挙げられる。感放射線性樹脂組成物は、感光剤(B)を含有することで、感放射線特性を発揮することができ、かつ良好な放射線感度を有することができる。感光剤(B)としては、光酸発生剤が好ましい。
酸を発生する化合物としては、光酸発生剤が挙げられ、例えば、キノンジアジド化合物、オキシムスルホネート化合物、オニウム塩、N-スルホニルオキシイミド化合物、ハロゲン含有化合物、ジアゾメタン化合物、スルホン化合物、スルホン酸エステル化合物、カルボン酸エステル化合物が挙げられる。光酸発生剤を用いることで、ポジ型の感放射線特性を発揮する組成物を得ることができる。
キノンジアジド化合物は、放射線の照射およびアルカリ水溶液を用いた現像を含む処理によってカルボン酸を発生する。キノンジアジド化合物としては、例えば、フェノール性化合物またはアルコール性化合物と、1,2-ナフトキノンジアジドスルホン酸ハライドとの縮合物が挙げられる。
オキシムスルホネート化合物の具体例としては、例えば、特開2011-227106号、特開2012-234148号、特開2013-054125号等の公報に記載された化合物が挙げられる。オニウム塩の具体例としては、例えば、特許第5208573号、特許第5397152号、特許第5413124号、特開2004-2110525号、特開2008-129423号、特開2010-215616号および特開2013-228526号等の公報に記載された化合物が挙げられる。
ラジカルを発生する化合物としては、光ラジカル重合開始剤が挙げられ、例えば、アルキルフェノン化合物、アシルホスフィンオキサイド化合物、オキシムエステル化合物、ベンゾイン化合物、ベンゾフェノン化合物、アントラキノン類、チオキサントン類が挙げられる。光ラジカル重合開始剤を用いることで、ネガ型の感放射線特性を発揮する組成物を得ることができる。
カチオンを発生する化合物としては、光カチオン重合開始剤が挙げられ、例えば、スルホニウム塩、ヨードニウム塩、ジアゾニウム塩が挙げられる。光カチオン重合開始剤を用いることで、ネガ型の感放射線特性を発揮する組成物を得ることができる。
樹脂(C)は、式(C1)で表される構造単位を有する樹脂と、式(C2)で表される構造を有する樹脂とから選ばれる少なくとも1種の樹脂である。以下、前記式(C1)で表される構造単位を有する樹脂を「樹脂(C1)」ともいい、前記式(C2)で表される構造を有する樹脂を「樹脂(C2)」ともいう。
Aは、フェノール性水酸基を有する2価の芳香族基であり、式(c1-1)、式(c1-2)または式(c1-3)で表される2価の基であることが好ましい。
A’は、フェノール性水酸基を有するk+m+n価の芳香族基であり、例えば、式(c1-1)、式(c1-2)または式(c1-3)で表される2価の基を、k+m+n価の基に変更した基が挙げられる。ただし、-CH(L)OCH(L)-、-CH(L)-および-CH(L)OHは、芳香環に結合するものとする。
Lは、式(c2-1)、式(c2-2)または式(c2-3)で表される1価の基である。
水酸基数が1~4であり、好ましくは1~3であり、かつベンゼン核数が1の化合物、具体的にはフェノール、オルトクレゾール、メタクレゾール、パラクレゾール、2,3-ジメチルフェノール、2,5-ジメチルフェノール、3,4-ジメチルフェノール、3,5-ジメチルフェノール、2,4-ジメチルフェノール、2,6-ジメチルフェノール、2,3,5-トリメチルフェノール、2,3,6-トリメチルフェノール、2-t-ブチルフェノール、3-t-ブチルフェノール、4-t-ブチルフェノール、2-メチルレゾルシノール、4-メチルレゾルシノール、5-メチルレゾルシノール、4-t-ブチルカテコール、2-メトキシフェノール、3-メトキシフェノール、2-プロピルフェノール、3-プロピルフェノール、4-プロピルフェノール、2-イソプロピルフェノール、2-メトキシ-5-メチルフェノール、2-t-ブチル-5-メチルフェノール、2-イソプロピル-5-メチルフェノール、5-イソプロピル-2-メチルフェノール;
水酸基数が1~6であり、好ましくは1~3であり、かつベンゼン核数が2の化合物(ナフタレン型化合物)、具体的には1-ナフトール、2-ナフトール等のモノヒドロキシナフタレン、1,2-ジヒドロキシナフタレン、1,3-ジヒドロキシナフタレン、1,4-ジヒドロキシナフタレン、1,5-ジヒドロキシナフタレン、1,6-ジヒドロキシナフタレン、1,7-ジヒドロキシナフタレン、1,8-ジヒドロキシナフタレン、2,3-ジヒドロキシナフタレン、2,6-ジヒドロキシナフタレン、2,7-ジヒドロキシナフタレン等のジヒドロキシナフタレン;
水酸基数が1~8であり、好ましくは1~3であり、かつベンゼン核数が3の化合物(アントラセン型化合物)、具体的には1-ヒドロキシアントラセン、2-ヒドロキシアントラセン、9-ヒドロキシアントラセン等のモノヒドロキシアントラセン、1,4-ジヒドロキシアントラセン、9,10-ジヒドロキシアントラセン等のジヒドロキシアントラセン、1,2,10-トリヒドロキシアントラセン、1,8,9-トリヒドロキシアントラセン、1,2,7-トリヒドロキシアントラセン等のトリヒドロキシアントラセン;
が挙げられる。
架橋剤(D)は、架橋性官能基を有する化合物である。架橋剤(D)としては、例えば、1分子中に2個以上の架橋性官能基を有する化合物が挙げられる。
溶剤(E)は、感放射線性樹脂組成物を液状とするために使用することができる。
感放射線性樹脂組成物は、上記必須成分に加え、本発明の効果を損なわない範囲で、必要に応じて密着助剤(F)、界面活性剤(G)、染料(H)等のその他の任意成分を含有してもよい。その他の任意成分は、単独で使用しても2種以上を併用してもよい。
密着助剤(F)は、基板等の膜形成対象物と絶縁膜との接着性を向上させる成分である。密着助剤(F)は、特に無機物の基板と絶縁膜との接着性を向上させるために有用である。無機物としては、例えば、シリコン、酸化シリコン、窒化シリコン等のシリコン化合物;金、銅、アルミニウム等の金属が挙げられる。
界面活性剤(G)は、感放射線性樹脂組成物の塗膜形成性を高める成分である。感放射線性樹脂組成物は、界面活性剤(G)を含有することで、塗膜の表面平滑性を向上でき、その結果、絶縁膜の膜厚均一性をより向上できる。界面活性剤(G)としては、例えば、フッ素系界面活性剤、シリコーン系界面活性剤が挙げられる。
染料(H)は、絶縁膜の遮光性を高める成分である。染料(H)を用いることで、信頼性により優れた表示又は照明装置用を得ることができる。染料(H)は、400nm~1000nmの波長域での光線を吸収する成分であればよく、例えば、アントラキノン系、メチン系、インジゴイド系、アゾ系の有機化合物の色素が挙げられる。
感放射線性樹脂組成物は、例えば溶剤(E)に、感光剤(B)、樹脂(C)等の必須成分と、必要に応じて他の成分とを混合することによって調製することができる。また、ゴミを取り除くために、各成分を均一に混合した後、得られた混合物をフィルター等で濾過してもよい。
本発明の絶縁膜の形成方法は、上述した感放射線性樹脂組成物を用いて基板上に塗膜を形成する工程1、前記塗膜の少なくとも一部に放射線を照射する工程2、前記放射線が照射された塗膜を現像する工程3、および前記現像された塗膜を加熱する工程4を有する。
工程1では、感放射線性樹脂組成物を基板表面に塗布し、好ましくはプレベークを行うことにより溶剤(E)を除去することで、塗膜を形成する。前記塗膜の膜厚としては、プレベーク後の値として、通常0.3~25μm、好ましくは0.5~20μmとすることができる。
工程2では、工程1で形成された塗膜に、所定のパターンを有するマスクを介して、放射線を照射する。このときに用いられる放射線としては、例えば、可視光線、紫外線、遠紫外線、X線、荷電粒子線が挙げられる。可視光線としては、例えば、g線(波長436nm)、h線(波長405nm)が挙げられる。紫外線としては、例えば、i線(波長365nm)が挙げられる。遠紫外線としては、例えば、KrFエキシマレーザによるレーザ光が挙げられる。X線としては、例えば、シンクロトロン放射線が挙げられる。荷電粒子線としては、例えば、電子線が挙げられる。
工程3では、工程2で放射線を照射した塗膜の現像を行う。これにより、例えばポジ型の組成物を用いた場合は放射線の照射部分を除去し、ネガ型の組成物を用いた場合は放射線の非照射部分を除去し、所望のパターンを形成することができる。現像処理に用いられる現像液としては、アルカリ水溶液が好ましい。
工程4では、工程3の後に、ホットプレート、オーブン等の加熱装置を用いて、塗膜に対する加熱処理(ポストベーク処理)により塗膜の硬化処理を行うことで絶縁膜を得る。この加熱処理における加熱温度は、例えば、130℃を超えて300℃以下であり、加熱時間は、加熱機器の種類により異なるが、例えば、ホットプレート上で加熱処理を行う場合には5分間~30分間、オーブン中で加熱処理を行う場合には30分間~90分間である。この際に、2回以上の加熱工程を行うステップベーク法等を用いることもできる。
以下、本発明の絶縁膜を有する表示又は照明装置用素子について説明する。
樹脂(A)および樹脂(C)の重量平均分子量(Mw)および分子量分布(Mw/Mn)は、ゲルパーミエーションクロマトグラフィー(GPC)法により、以下の条件で測定した。
・標準物質:ポリスチレン
・装置 :東ソー(株)製、商品名:HLC-8020
・カラム :東ソー(株)製ガードカラムHXL-H、TSK gel G7000HXL、TSK gel GMHXL 2本、TSK gel G2000HXLを順次連結したもの
・溶媒 :テトラヒドロフラン(ただし、ポリイミドの場合はN,N-ジメチルホルムアミド)
・サンプル濃度:0.7質量%
・注入量 :70μL
・流速 :1mL/min
[NMR分析]
樹脂(A)の化学シフトは、核磁気共鳴(NMR)法により、以下の条件で測定した。
・装置:日本電子(株)製、商品名:JNM-ECX400
・溶媒:CDCL3
[ポリイミドのイミド化率]
まず、ポリイミドの赤外吸収スペクトルを測定し、ポリイミドに起因するイミド構造の吸収ピーク(1780cm-1付近、1377cm-1付近)の存在を確認した。次に、そのポリイミドについて、350℃で1時間熱処理した後、再度、赤外吸収スペクトルを測定した。熱処理前と熱処理後の1377cm-1付近のピーク強度を比較した。熱処理後のポリイミドのイミド化率を100%として、熱処理前のポリイミドのイミド化率={熱処理前の1377cm-1付近のピーク強度/熱処理後の1377cm-1付近のピーク強度}×100(%)を求めた。赤外吸収スペクトルの測定には、「NICOLET6700FT-IR」(サーモエレクトロン社製)を用いた。
[合成例A1]樹脂(A-1)の合成
3口フラスコに重合溶剤としてのγ-ブチロラクトン(BL)340gを加えた後、プロピレングリコールモノメチルエーテルアセテート(PGMEA)50gを加え、重合溶剤の合計390gに対してジアミン化合物としての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120gを重合溶剤中に加えた。ジアミン化合物を重合溶剤に溶解させた後、酸二無水物としての4,4’-オキシジフタル酸二無水物71gを加えた。その後、60℃で1時間反応させた後、末端封止剤としての無水マレイン酸19gを加え、60℃で更に1時間反応させた後、昇温して140℃で4時間反応させた。反応の際はN2フロー条件でディーンスターク管を用い、低沸点溶剤のPGMEAを溜去した。これにより、樹脂(A-1)を含む溶液を約550g得た。得られた樹脂(A-1)のMwは7500であった。得られた樹脂(A-1)のイミド化率は10%であった。
攪拌器付3口フラスコに、成分(a3-1)として3,4-エポキシシクロヘキシルメチルメタクリレート20部、成分(a3-2)としてメタクリル酸10部、成分(a3-3)としてベンジルメタクリレート65部、溶剤としてプロピレングリコールモノメチルエーテルアセテート150部、重合開始剤としてジメチル-2,2’-アゾビス(2-メチルプロピオネート)3部、および連鎖移動剤としてチオグリコール酸2部を仕込み、65℃で6時間加熱し、樹脂(A-2)を含む溶液を得た。得られた樹脂(A-2)の重量平均分子量(Mw)は10000であった。
攪拌器付3口フラスコに、成分(a3-1)として3,4-エポキシシクロヘキシルメチルメタクリレート40部、成分(a3-2)としてコハク酸モノ(2-メタクリロイロキシエチル)30部、成分(a3-3)としてベンジルメタクリレート25部、溶剤としてプロピレングリコールモノメチルエーテルアセテート150部、重合開始剤としてジメチル-2,2’-アゾビス(2-メチルプロピオネート)3部、および連鎖移動剤としてチオグリコール酸2部を仕込み、65℃で6時間加熱し、樹脂(A-3)を含む溶液を得た。得られた樹脂(A-3)の重量平均分子量(Mw)は15000であった。
500mLの三口フラスコに、メチルトリメトキシシランを63.39g(0.55mol)、フェニルトリメトキシシランを69.41g(0.35mol)、2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシランを24.64g(0.1mol)、ジアセトンアルコールを150.36g仕込み、室温で攪拌しながら、水55.8gにリン酸0.338g(仕込みモノマーに対して0.2質量%)を溶かしたリン酸水溶液を10分かけて添加した。その後、フラスコを70℃のオイルバスに浸けて1時間攪拌した後、オイルバスを30分かけて115℃まで昇温した。昇温開始1時間後に溶液の内温が100℃に到達し、そこから2時間加熱攪拌した(内温は100~110℃)。反応中に副生成物であるメタノールおよび水が合計115g留出した。得られた樹脂(A-4)のジアセトンアルコール溶液に、樹脂(A-4)濃度が40質量%となるようにジアセトンアルコールを加えて、樹脂(A-4)のジアセトンアルコール溶液を得た。得られた樹脂(A-4)の重量平均分子量(Mw)は5000であり、Si原子100モルに対するフェニル基含有量は35モルであった。
[合成例C1]ノボラック樹脂(C-1)の合成
温度計、冷却管、分留管、撹拌器を取り付けたフラスコに、1-ナフトール144.2g(1.0モル)、メチルイソブチルケトン400g、α-メチルシンナムアルデヒド102.3g(0.7モル)を仕込んだ。続いて、攪拌しながら、30質量%濃度のパラトルエンスルホン酸のメタノール溶液3.4gを加えた。その後、100℃で8時間反応させた。反応終了後に純水200gを加え、系内の溶液を分液ロートに移して、水層を有機層から分離除去した。次いで、洗浄水が中性を示すまで有機層を水洗した後、有機層から溶媒を加熱減圧下に除去し、ノボラック樹脂(C-1)を157g得た。得られたノボラック樹脂(C-1)の重量平均分子量(Mw)は4500であった。
合成例C2~C8では、表1に記載したアルデヒドを用いたこと以外は合成例C1と同様に行い、ノボラック樹脂(C-2)~(C-6)および他のノボラック樹脂(C-7)~(C-8)を得た。結果を表1に示す。
感放射線性樹脂組成物の調製に用いた樹脂(A)は合成例A1~A4の樹脂(A-1)~(A-4)であり、樹脂(C)は合成例C1~C6のノボラック樹脂(C-1)~(C-6)であり、他の樹脂(C’)は合成例C7~C8の他のノボラック樹脂(C-7)~(C-8)であり、感光剤(B)、架橋剤(D)、溶剤(E)、密着助剤(F)、界面活性剤(G)および染料(H)は、下記の通りである。
・感光剤(B)
B-1:ナフトキノンジアジドスルホン酸エステル
(NT-300P、東洋合成工業(株)製)
B-2:1,2-オクタンジオン-1-[4-(フェニルチオ)-2-(O-ベンゾイルオキシム)](BASFジャパン(株)製の「IRACURE OXE01」)
・架橋剤(D)
D-1:4,4-ビス[(3-エチル-3-オキセタニル)メチル]ビフェニル(宇部興産(株)製の「OXBP」)
D-2:ジペンタエリスリトールヘキサアクリレート
(東亞合成(株)製の「M-402」)
・溶剤(E)
BL:γ-ブチロラクトン
PGMEA:プロピレングリコールモノメチルエーテルアセテート
PGME:プロピレングリコールモノメチルエーテル
DAA:ジアセトンアルコール
・密着助剤(F)
F-1:N-フェニル-3-アミノプロピルトリメトキシシラン
(信越化学工業(株)製の「KBM-573」)
・界面活性剤(G)
G-1:シリコーン系界面活性剤(東レダウコーニング社製の「SH8400」)
・染料(H)
H-1:C.I.Solvent Blue70
(有本化学製の「OilBlue5511」)
H-2:C.I.Solvent Blue45
(有本化学製の「PlastBlueDB-463」)
H-3:C.I.Solvent Black27
(中央合成化学製の「NEOSUPERBLACK C-832」)
H-4:C.I.Solvent Red83(保土ヶ谷化学工業社製の「Aizen Spilon Red BEH Special」)
[実施例1]
合成例A1の樹脂(A-1)を含む樹脂溶液(樹脂(A-1)40部(固形分)に相当する量)に、(B-1)16部、(C-1)25部、(D-1)15部、(F-1)3部、(G-1)1部、および溶剤を混合し、口径0.2μmのメンブランフィルタで濾過して、表2に記載の組成を有する感放射線性樹脂組成物1を調製した。なお、前記組成物の固形分濃度は30質量%であった。
実施例2~27および比較例1~3では、表2に示す種類および配合量の各成分を用いたこと以外は実施例1と同様にして、感放射線性樹脂組成物2~30を調製した。
実施例・比較例で得られた感放射線性樹脂組成物を用いて、以下に説明する方法により絶縁膜および有機EL素子を作製した。前記組成物のパターニング性および放射線感度を、得られた絶縁膜の遮光性(透過率)、吸水性、耐熱性およびアウトガス量を、また得られた有機EL素子の素子特性を、それぞれ下記方法で評価した。なお、以下の評価において、「上記組成物」とは、実施例・比較例で得られた感放射線性樹脂組成物を意味する。
スピンナーを用いて、シリコン基板上に上記組成物を塗布した後、ホットプレート上で120℃にて2分間プレベークして、塗膜を形成した。この塗膜に対して、露光機(キヤノン社の「MPA-6000」)を用い、所定のパターンを有するパターンマスクを介して波長365nmにおける露光量100mJ/cm2で露光した。露光量は、照度計(OAI Optical Associates社の「OAI model356」)により測定した。その後、2.38質量%テトラメチルアンモニウムヒドロキシド水溶液を用いて25℃にて80秒間液盛り法で現像し、超純水で1分間流水洗浄を行い、乾燥させて、シリコン基板上に直径が5μmの複数のスルーホールが列状に並ぶパターンを有する塗膜を形成した。この塗膜をクリーンオーブン中で250℃にて45分間ポストベークして、膜厚3.0μmの絶縁膜を得た。
スピンナーを用いて、シリコン基板上に上記組成物を塗布した後、ホットプレート上で120℃にて2分間プレベークして、膜厚3.0μmの塗膜を形成した。この塗膜に対して、露光機(キヤノン社の「MPA-6000」)を用い、所定のパターンを有するパターンマスクを介して露光量を変化させて露光した。その後、2.38質量%テトラメチルアンモニウムヒドロキシド水溶液を用いて25℃にて80秒間液盛り法で現像し、超純水で1分間流水洗浄を行い、乾燥させて、シリコン基板上に直径が20.0μmの複数のスルーホールを有する塗膜を形成した。
スピンナーを用いて、ガラス基板(コーニング社の「コーニング7059」)上に上記組成物を塗布した後、ホットプレート上で120℃にて2分間プレベーク後、クリーンオーブン中で250℃にて45分間ポストベークして、膜厚3.0μmを有する絶縁膜を形成した。
スピンナーを用いて、シリコン基板上に上記組成物を塗布した後、ホットプレート上で120℃にて2分間プレベーク後、クリーンオーブン中で250℃にて45分間ポストベークして、膜厚3.0μmを有する絶縁膜を形成した。
<吸水性>の評価と同様にして上記組成物を用いて絶縁膜を形成し、この絶縁膜について、熱重量測定装置(TAインスツルメント社の「TGA2950」)を用いて、100℃から500℃においてTGA測定(空気下、昇温速度10℃/分)を行うことで5%重量減少温度を求めた。耐熱性は、5%重量減少温度が350℃を超える場合に「優良」、350~330℃の場合に「良好」とした。
<吸水性>の評価と同様にして上記組成物を用いて絶縁膜を形成し、絶縁膜付きシリコン基板を1cm×5cm片に切断し、切断したシリコン基板4枚について、シリコンウエハーアナライザー装置(商品名「加熱脱着装置JTD-505」日本分析工業(株)製、「ガスクロマトグラフ質量分析計GCMS-QP2010Plus」島津製作所(株)製)を用いて、230℃、15分保持(昇温速度10℃/分)した際のアウトガス量μg/cm3を求めた。
ガラス基板(コーニング社の「コーニング7059」)を用い、このガラス基板上にTFTを形成したTFT基板を作製した後に、このTFT基板上に絶縁膜を形成して評価用素子を作製した。この評価用素子について、素子特性の評価を行った。
素子特性はスイッチング応答特性として評価した。スイッチング応答特性は、ON/OFF比を測定することで評価した。ON/OFF比は、プローバおよび半導体パラメーターアナライザーを用いて、ゲート電極に電圧を印可した状態でソース電極-ドレイン電極間に流れる電流を測定することで算出した。具体的には、半導体層に対して上記組成物から形成された絶縁膜の上方から波長450nmまたは500nmを中心とした白色光(照度30000ルックス)を照射した条件下において、ドレイン電極をプラス10V、ソース電極を0Vとした場合にゲート電極に印可された電圧がプラス10Vとマイナス10Vの時の電流値の比をON/OFF比とした。スイッチング応答特性、すなわち素子特性は、ON/OFF比が1.0×105以上の場合に「良好」、1.0×105未満の場合に「不良」とした。
TFT信頼性は、ゲート電極-ソース電極間に電気的なストレスを印可した際のId-Vg特性の変化(閾値電圧Vthの変化量)を、評価用素子に対する光照射時と光非照射時とで比較することによって評価した。
電気的なストレスの印可は、評価用素子のソース電極の電位を0V、ドレイン電極の電位を+10Vに保ち、ソース電極-ドレイン電極間に電圧を印可した状態で、ゲート電極の電位Vgを-20Vから+20Vまで変化させることで行った。このようにゲート電極の電位Vgを変化させた際、ドレイン電極-ソース電極間に流れる電流Idをプロットすることで、Id-Vg特性を得た。このId-Vg特性においては、電流値がONとなる電圧を閾値電圧Vthに設定した。
電気的なストレスは、ゲート電極-ソース電極間に、+20Vの正電圧及び-20Vの負電圧をそれぞれ12時間ずつ印加することで与えた。このような電気的なストレスは、評価用素子の半導体膜に対して上方から光を照射した条件下、および半導体膜に対して光を照射しない条件下のそれぞれについて行った。閾値電圧Vthの変化量は、光照射条件および光非照射条件のそれぞれについて、Id-Vg特性から算出した。そして、光照射時の閾値電圧Vthの変化量が、光非照射時の閾値電圧Vthの変化量の1.5倍未満に抑えられている場合にTFT信頼性が「優良」であるとし、1.5倍~2倍に抑えられている場合にTFT信頼性が「良好」であるとし、2倍を超えている場合にTFT信頼性が「不良」であるとした。
ガラス基板(コーニング社の「コーニング7059」)を用い、このガラス基板上にITO透明電極をスパッタし、続いて感光性レジスト(「NN700」、JSR(株)製)をスピンコート法で塗布して乾燥し、所定のパターンマスクを介して露光した。露光後、現像し、加熱硬化して、所定のレジストパターンを形成した。続いてエッチング液を用いて、ITO膜をエッチングして、所定のITO膜のパターンを形成した後、レジストパターンを剥離液で除去した。
Claims (15)
- (B)感光剤と、
(C)式(C1)で表される構造単位を有する樹脂、および
式(C2)で表される構造を有する樹脂
から選ばれる少なくとも1種の樹脂と
を含有する感放射線性樹脂組成物から形成された絶縁膜
を有する表示又は照明装置用素子。
式(c2-2)中、Yは窒素原子、C-HまたはC-R2であり、R2は式(c2-1)中のR1と同義であり、R3およびR4はそれぞれ独立に水素原子または炭化水素基であり、nは0~4の整数であり、dは0または1であり、ただし、式(C1)の場合では、n=d=0のときはYはC-Hではなく、またn=d=0且つYがC-R2であるとき、またはn=1、d=0且つYがC-HであるときはR2は-NO2、-OHではなく、R2が複数存在する場合、各々同一であっても異なってもよく、また隣接する環炭素に結合したR2は相互に結合して環を形成していてもよく;
式(c2-3)中、R5は式(c2-1)中のR1と同義であり、lはそれぞれ独立に0~5の整数であり、R5が複数存在する場合、各々同一であっても異なってもよく、また隣接する環炭素に結合したR5は相互に結合して環を形成していてもよい。] - 式(C1)中のAが、式(c1-1)、式(c1-2)または式(c1-3)で表される2価の基である、請求項1に記載の表示又は照明装置用素子。
- 前記感放射線性樹脂組成物が、
(A)前記樹脂(C)を除くアルカリ可溶性樹脂
を更に含有する、請求項1または2に記載の表示又は照明装置用素子。 - アルカリ可溶性樹脂(A)が、ポリイミド(A1)、前記ポリイミドの前駆体(A2)、アクリル樹脂(A3)、ポリシロキサン(A4)、ポリベンゾオキサゾール(A5)および前記ポリベンゾオキサゾールの前駆体(A6)から選択される少なくとも1種である、請求項3に記載の表示又は照明装置用素子。
- アクリル樹脂(A3)が、カルボキシル基を有するラジカル重合性モノマーを少なくとも重合させて得られる樹脂である請求項4に記載の表示又は照明装置用素子。
- ポリシロキサン(A4)が、式(a4)で表されるオルガノシランを反応させて得られるポリシロキサンである請求項4に記載の表示又は照明装置用素子。
- 感光剤(B)が、光酸発生剤、光ラジカル重合開始剤および光カチオン重合開始剤から選ばれる少なくとも1種である請求項1~7のいずれか1項に記載の表示又は照明装置用素子。
- 前記感放射線性樹脂組成物において、樹脂(C)の含有量が、樹脂(A)100質量部に対して5~200質量部である請求項3~7のいずれか1項に記載の表示又は照明装置用素子。
- 有機エレクトロルミネセンス素子である、請求項1~9のいずれか1項に記載の表示又は照明装置用素子。
- (B)感光剤と、
(C)式(C1)で表される構造単位を有する樹脂、および
式(C2)で表される構造を有する樹脂
から選ばれる少なくとも1種の樹脂と
を含有する感放射線性樹脂組成物。
式(c2-2)中、Yは窒素原子、C-HまたはC-R2であり、R2は式(c2-1)中のR1と同義であり、R3およびR4はそれぞれ独立に水素原子または炭化水素基であり、nは0~4の整数であり、dは0または1であり、ただし、式(C1)の場合では、n=d=0のときはYはC-Hではなく、またn=d=0且つYがC-R2であるとき、またはn=1、d=0且つYがC-HであるときはR2は-NO2、-OHではなく、R2が複数存在する場合、各々同一であっても異なってもよく、また隣接する環炭素に結合したR2は相互に結合して環を形成していてもよく;
式(c2-3)中、R5は式(c2-1)中のR1と同義であり、lはそれぞれ独立に0~5の整数であり、R5が複数存在する場合、各々同一であっても異なってもよく、また隣接する環炭素に結合したR5は相互に結合して環を形成していてもよい。] - (A)前記樹脂(C)を除くアルカリ可溶性樹脂
を更に含有する、請求項11に記載の感放射線性樹脂組成物。 - (B)感光剤と、
(C)式(C1)で表される構造単位を有する樹脂、および
式(C2)で表される構造を有する樹脂
から選ばれる少なくとも1種の樹脂と
を含有する感放射線性樹脂組成物から形成された絶縁膜。
式(c2-2)中、Yは窒素原子、C-HまたはC-R2であり、R2は式(c2-1)中のR1と同義であり、R3およびR4はそれぞれ独立に水素原子または炭化水素基であり、nは0~4の整数であり、dは0または1であり、ただし、式(C1)の場合では、n=d=0のときはYはC-Hではなく、またn=d=0且つYがC-R2であるとき、またはn=1、d=0且つYがC-HであるときはR2は-NO2、-OHではなく、R2が複数存在する場合、各々同一であっても異なってもよく、また隣接する環炭素に結合したR2は相互に結合して環を形成していてもよく;
式(c2-3)中、R5は式(c2-1)中のR1と同義であり、lはそれぞれ独立に0~5の整数であり、R5が複数存在する場合、各々同一であっても異なってもよく、また隣接する環炭素に結合したR5は相互に結合して環を形成していてもよい。] - 前記感放射線性樹脂組成物が、
(A)前記樹脂(C)を除くアルカリ可溶性樹脂
を更に含有する、請求項13に記載の絶縁膜。 - 請求項11または12に記載の感放射線性樹脂組成物を用いて基板上に塗膜を形成する工程、前記塗膜の少なくとも一部に放射線を照射する工程、前記放射線が照射された塗膜を現像する工程、および前記現像された塗膜を加熱する工程を有する、絶縁膜の製造方法。
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