TWI247968B - Improved anti-reflective coating compositions comprising polymerized aminoplasts - Google Patents
Improved anti-reflective coating compositions comprising polymerized aminoplasts Download PDFInfo
- Publication number
- TWI247968B TWI247968B TW089118827A TW89118827A TWI247968B TW I247968 B TWI247968 B TW I247968B TW 089118827 A TW089118827 A TW 089118827A TW 89118827 A TW89118827 A TW 89118827A TW I247968 B TWI247968 B TW I247968B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- polymer
- composition
- acid
- dispersion
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 239000006117 anti-reflective coating Substances 0.000 title claims abstract description 27
- 229920003180 amino resin Polymers 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- -1 alkoxy alkyl melamines Chemical class 0.000 claims abstract description 20
- 230000003667 anti-reflective effect Effects 0.000 claims abstract description 18
- 239000000758 substrate Substances 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 31
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 24
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 24
- 239000006185 dispersion Substances 0.000 claims description 20
- 239000002689 soil Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 229940116333 ethyl lactate Drugs 0.000 claims description 12
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 12
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000005647 linker group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 239000002270 dispersing agent Substances 0.000 claims description 7
- 229920002301 cellulose acetate Polymers 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000001856 Ethyl cellulose Substances 0.000 claims description 5
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 5
- 229920001249 ethyl cellulose Polymers 0.000 claims description 5
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 238000004448 titration Methods 0.000 claims description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 238000005530 etching Methods 0.000 claims description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229930003658 monoterpene Natural products 0.000 claims description 2
- 150000002773 monoterpene derivatives Chemical class 0.000 claims description 2
- 235000002577 monoterpenes Nutrition 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- NXNZDVKCENYFQF-UHFFFAOYSA-N 2-ethyl-4-methylpentanedioic acid Chemical compound CCC(C(O)=O)CC(C)C(O)=O NXNZDVKCENYFQF-UHFFFAOYSA-N 0.000 claims 3
- 229920002125 Sokalan® Polymers 0.000 claims 3
- 239000004584 polyacrylic acid Substances 0.000 claims 3
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- JFBYGMUJXBUWEO-UHFFFAOYSA-N 3-methylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C)=CC2=C1 JFBYGMUJXBUWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052704 radon Inorganic materials 0.000 claims 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 23
- 239000010410 layer Substances 0.000 description 12
- 229920003270 Cymel® Polymers 0.000 description 11
- 229920002120 photoresistant polymer Polymers 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000011229 interlayer Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002079 cooperative effect Effects 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 238000000572 ellipsometry Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 description 2
- WSWCOQWTEOXDQX-UHFFFAOYSA-N 2,4-Hexadienoic acid Chemical compound CC=CC=CC(O)=O WSWCOQWTEOXDQX-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- AMXMODDEDUGKDR-UHFFFAOYSA-N 3-hydroxy-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(O)=C(C(=O)O)NC2=C1 AMXMODDEDUGKDR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 102100021899 Cyclin-L2 Human genes 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 101000897452 Homo sapiens Cyclin-L2 Proteins 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 238000001792 White test Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- LZKPUVULVAMJGR-UHFFFAOYSA-N acetic acid;benzene-1,4-diol Chemical compound CC(O)=O.OC1=CC=C(O)C=C1 LZKPUVULVAMJGR-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 description 1
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
- G02B1/111—Anti-reflection coatings using layers comprising organic materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31667—Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31859—Next to an aldehyde or ketone condensation product
- Y10T428/31862—Melamine-aldehyde
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Paints Or Removers (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/552,236 US6323310B1 (en) | 2000-04-19 | 2000-04-19 | Anti-reflective coating compositions comprising polymerized aminoplasts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI247968B true TWI247968B (en) | 2006-01-21 |
Family
ID=24204467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089118827A TWI247968B (en) | 2000-04-19 | 2000-09-14 | Improved anti-reflective coating compositions comprising polymerized aminoplasts |
Country Status (8)
| Country | Link |
|---|---|
| US (7) | US6323310B1 (https=) |
| EP (1) | EP1284829A4 (https=) |
| JP (1) | JP4886146B2 (https=) |
| CN (1) | CN1248787C (https=) |
| AU (1) | AU2000273568A1 (https=) |
| MY (1) | MY133726A (https=) |
| TW (1) | TWI247968B (https=) |
| WO (1) | WO2001081010A1 (https=) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW556047B (en) | 2000-07-31 | 2003-10-01 | Shipley Co Llc | Coated substrate, method for forming photoresist relief image, and antireflective composition |
| JP4117871B2 (ja) * | 2000-11-09 | 2008-07-16 | 東京応化工業株式会社 | 反射防止膜形成用組成物 |
| TW576859B (en) | 2001-05-11 | 2004-02-21 | Shipley Co Llc | Antireflective coating compositions |
| US6893684B2 (en) * | 2001-06-05 | 2005-05-17 | Brewer Science Inc. | Anti-reflective coating compositions for use with low k dielectric materials |
| TW591341B (en) * | 2001-09-26 | 2004-06-11 | Shipley Co Llc | Coating compositions for use with an overcoated photoresist |
| US7070914B2 (en) * | 2002-01-09 | 2006-07-04 | Az Electronic Materials Usa Corp. | Process for producing an image using a first minimum bottom antireflective coating composition |
| US20030215736A1 (en) * | 2002-01-09 | 2003-11-20 | Oberlander Joseph E. | Negative-working photoimageable bottom antireflective coating |
| US8012670B2 (en) | 2002-04-11 | 2011-09-06 | Rohm And Haas Electronic Materials Llc | Photoresist systems |
| US20040067437A1 (en) * | 2002-10-06 | 2004-04-08 | Shipley Company, L.L.C. | Coating compositions for use with an overcoated photoresist |
| EP1560070B1 (en) * | 2002-10-09 | 2009-12-30 | Nissan Chemical Industries, Ltd. | Composition for forming antireflection film for lithography |
| US7038328B2 (en) * | 2002-10-15 | 2006-05-02 | Brewer Science Inc. | Anti-reflective compositions comprising triazine compounds |
| KR20040044368A (ko) * | 2002-11-20 | 2004-05-28 | 쉬플리 캄파니, 엘.엘.씨. | 다층 포토레지스트 시스템 |
| EP1422565A3 (en) * | 2002-11-20 | 2005-01-05 | Shipley Company LLC | Multilayer photoresist systems |
| US7018779B2 (en) * | 2003-01-07 | 2006-03-28 | International Business Machines Corporation | Apparatus and method to improve resist line roughness in semiconductor wafer processing |
| US7291293B2 (en) * | 2003-02-28 | 2007-11-06 | Northwestern University | Vapor deposited electro-optic films self-assembled through hydrogen bonding |
| US8461234B2 (en) * | 2003-03-14 | 2013-06-11 | Eastman Chemical Company | Refinish coating compositions comprising low molecular weight cellulose mixed esters |
| US8039531B2 (en) * | 2003-03-14 | 2011-10-18 | Eastman Chemical Company | Low molecular weight cellulose mixed esters and their use as low viscosity binders and modifiers in coating compositions |
| US7893138B2 (en) * | 2003-03-14 | 2011-02-22 | Eastman Chemical Company | Low molecular weight carboxyalkylcellulose esters and their use as low viscosity binders and modifiers in coating compositions |
| US8124676B2 (en) * | 2003-03-14 | 2012-02-28 | Eastman Chemical Company | Basecoat coating compositions comprising low molecular weight cellulose mixed esters |
| US20050074688A1 (en) * | 2003-10-03 | 2005-04-07 | Toukhy Medhat A. | Bottom antireflective coatings |
| US7795369B2 (en) * | 2004-10-12 | 2010-09-14 | Nissan Chemical Industries, Ltd. | Sulfur atom-containing anti-reflective coating forming composition for lithography |
| KR101248826B1 (ko) * | 2004-11-01 | 2013-03-29 | 닛산 가가쿠 고교 가부시키 가이샤 | 시클로덱스트린 화합물을 함유하는 리소그라피용 하층막 형성 조성물 |
| US8137895B2 (en) * | 2005-08-09 | 2012-03-20 | Taiwan Semiconductor Manufacturing Company, Ltd. | Structure and method for improving photoresist pattern adhesion |
| US20080085953A1 (en) * | 2006-06-05 | 2008-04-10 | Deepanjan Bhattacharya | Coating compositions comprising low molecular weight cellulose mixed esters and their use to improve anti-sag, leveling, and 20 degree gloss |
| US20070282038A1 (en) * | 2006-06-05 | 2007-12-06 | Deepanjan Bhattacharya | Methods for improving the anti-sag, leveling, and gloss of coating compositions comprising low molecular weight cellulose mixed esters |
| WO2008026468A1 (fr) * | 2006-08-28 | 2008-03-06 | Nissan Chemical Industries, Ltd. | Composition servant à créer une sous-couche de réserve et contenant un additif liquide |
| US20090042133A1 (en) * | 2007-08-10 | 2009-02-12 | Zhong Xiang | Antireflective Coating Composition |
| US8361695B2 (en) | 2007-12-13 | 2013-01-29 | Nissan Chemical Industries, Ltd. | Resist underlayer film forming composition and method for forming resist pattern |
| US8221965B2 (en) * | 2008-07-08 | 2012-07-17 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
| US8329387B2 (en) | 2008-07-08 | 2012-12-11 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
| US20100092894A1 (en) * | 2008-10-14 | 2010-04-15 | Weihong Liu | Bottom Antireflective Coating Compositions |
| CN102203951A (zh) | 2008-10-31 | 2011-09-28 | 日产化学工业株式会社 | 形成光电转换装置用波长转换膜的组合物、光电转换装置用波长转换膜以及光电转换装置 |
| WO2010150748A1 (ja) | 2009-06-23 | 2010-12-29 | 日産化学工業株式会社 | 光配向性を有する熱硬化膜形成組成物 |
| CN102471629B (zh) * | 2009-07-21 | 2015-09-09 | 日产化学工业株式会社 | 形成具有光取向性的热固化膜的组合物 |
| US8507192B2 (en) * | 2010-02-18 | 2013-08-13 | Az Electronic Materials Usa Corp. | Antireflective compositions and methods of using same |
| EP2557119B1 (en) | 2010-04-08 | 2015-12-09 | Nissan Chemical Industries, Ltd. | Composition forming heat-cured film having photo-alignment properties |
| CN103261273B (zh) * | 2010-11-01 | 2015-09-16 | 日产化学工业株式会社 | 含三嗪环的聚合物和含有该聚合物的成膜用组合物 |
| EP2753662B1 (en) | 2011-09-07 | 2020-06-24 | MicroChem Corp. | Epoxy formulations and processes for fabrication of relief patterns on low surface energy substrates |
| US9244199B2 (en) | 2011-10-11 | 2016-01-26 | Nissan Chemical Industries, Ltd. | Cured film formation composition, orientation material, and retardation material |
| US9962430B2 (en) | 2012-02-15 | 2018-05-08 | Chirhoclin, Inc. | Methods for treating pain associated with chronic pancreatitis |
| US11635688B2 (en) | 2012-03-08 | 2023-04-25 | Kayaku Advanced Materials, Inc. | Photoimageable compositions and processes for fabrication of relief patterns on low surface energy substrates |
| US11406718B2 (en) | 2012-05-29 | 2022-08-09 | Chirhoclin, Inc. | Methods of detecting pancreobiliary ductal leaks |
| KR102641678B1 (ko) * | 2016-02-09 | 2024-02-28 | 닛산 가가쿠 가부시키가이샤 | 트라이아진환 함유 중합체 및 그것을 포함하는 조성물 |
| US11744878B2 (en) | 2020-08-19 | 2023-09-05 | Chirhoclin, Inc. | Methods for treatment of COVID-19 syndrome |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197392A (en) * | 1978-08-21 | 1980-04-08 | General Electric Company | Melamine coatings |
| CA1264880A (en) | 1984-07-06 | 1990-01-23 | John Brooke Gardiner | Viscosity index improver - dispersant additive useful in oil compositions |
| JPH0713127B2 (ja) * | 1986-01-22 | 1995-02-15 | 大日精化工業株式会社 | 紫外線反射材料 |
| US5094765A (en) | 1990-04-30 | 1992-03-10 | Texaco Inc. | Lubricating oil composition |
| US5536835A (en) * | 1993-11-26 | 1996-07-16 | Ppg Industries, Inc. | Etherified alkyl or arylcarbamylmethylated aminotriazines and curable compositions containing the same |
| US5731385A (en) * | 1993-12-16 | 1998-03-24 | International Business Machines Corporation | Polymeric dyes for antireflective coatings |
| JP2953562B2 (ja) * | 1994-07-18 | 1999-09-27 | 東京応化工業株式会社 | リソグラフィー用下地材及びそれを用いた多層レジスト材料 |
| US5693691A (en) | 1995-08-21 | 1997-12-02 | Brewer Science, Inc. | Thermosetting anti-reflective coatings compositions |
| JP3436843B2 (ja) | 1996-04-25 | 2003-08-18 | 東京応化工業株式会社 | リソグラフィー用下地材及びそれを用いたリソグラフィー用レジスト材料 |
| TW406215B (en) * | 1996-08-07 | 2000-09-21 | Fuji Photo Film Co Ltd | Composition for anti-reflective coating material in lithographic process, and process for forming resist pattern |
| JPH1090908A (ja) * | 1996-09-17 | 1998-04-10 | Fuji Photo Film Co Ltd | 反射防止膜材料用組成物 |
| JPH10120940A (ja) * | 1996-10-18 | 1998-05-12 | Fuji Photo Film Co Ltd | 反射防止膜用組成物 |
| JP3506357B2 (ja) * | 1996-12-13 | 2004-03-15 | 東京応化工業株式会社 | リソグラフィー用下地材 |
| US5948847A (en) * | 1996-12-13 | 1999-09-07 | Tokyo Ohka Kogyo Co., Ltd. | Undercoating composition for photolithographic patterning |
| JP3851414B2 (ja) * | 1997-06-04 | 2006-11-29 | 富士写真フイルム株式会社 | 反射防止膜材料組成物及びこれを用いたレジストパターン形成方法 |
| JPH1165125A (ja) | 1997-08-21 | 1999-03-05 | Tokyo Ohka Kogyo Co Ltd | パターン形成方法 |
| US6156479A (en) * | 1997-09-30 | 2000-12-05 | Brewer Science, Inc. | Thermosetting anti-refective coatings |
| US5919599A (en) | 1997-09-30 | 1999-07-06 | Brewer Science, Inc. | Thermosetting anti-reflective coatings at deep ultraviolet |
| US5935760A (en) * | 1997-10-20 | 1999-08-10 | Brewer Science Inc. | Thermosetting polyester anti-reflective coatings for multilayer photoresist processes |
| KR20010042973A (ko) | 1998-04-29 | 2001-05-25 | 테리 브레우어 | 셀룰로식 결합제로부터 유도된 급속 에칭, 열경화성 반사방지 코팅 |
| TW476865B (en) | 1999-01-28 | 2002-02-21 | Tokyo Ohka Kogyo Co Ltd | Undercoating composition for photolithographic resist |
| JP3456937B2 (ja) * | 1999-01-28 | 2003-10-14 | 東京応化工業株式会社 | リソグラフィー用下地材組成物 |
| JP4117871B2 (ja) * | 2000-11-09 | 2008-07-16 | 東京応化工業株式会社 | 反射防止膜形成用組成物 |
-
2000
- 2000-04-19 US US09/552,236 patent/US6323310B1/en not_active Expired - Lifetime
- 2000-08-29 MY MYPI20003965 patent/MY133726A/en unknown
- 2000-09-06 CN CNB008194416A patent/CN1248787C/zh not_active Expired - Lifetime
- 2000-09-06 EP EP00961646A patent/EP1284829A4/en not_active Withdrawn
- 2000-09-06 AU AU2000273568A patent/AU2000273568A1/en not_active Abandoned
- 2000-09-06 JP JP2001578095A patent/JP4886146B2/ja not_active Expired - Lifetime
- 2000-09-06 WO PCT/US2000/024595 patent/WO2001081010A1/en not_active Ceased
- 2000-09-14 TW TW089118827A patent/TWI247968B/zh not_active IP Right Cessation
- 2000-10-18 US US09/691,780 patent/US6432611B1/en not_active Expired - Lifetime
- 2000-10-18 US US09/691,771 patent/US6403152B1/en not_active Expired - Lifetime
- 2000-10-18 US US09/691,774 patent/US6399686B1/en not_active Expired - Lifetime
-
2001
- 2001-05-30 US US09/870,171 patent/US20020007038A1/en not_active Abandoned
- 2001-10-10 US US09/975,837 patent/US6524708B2/en not_active Expired - Lifetime
-
2002
- 2002-04-12 US US10/122,069 patent/US6512084B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20020007038A1 (en) | 2002-01-17 |
| AU2000273568A1 (en) | 2001-11-07 |
| US6403152B1 (en) | 2002-06-11 |
| CN1452521A (zh) | 2003-10-29 |
| US20020061408A1 (en) | 2002-05-23 |
| MY133726A (en) | 2007-11-30 |
| US6399686B1 (en) | 2002-06-04 |
| JP2003531252A (ja) | 2003-10-21 |
| JP4886146B2 (ja) | 2012-02-29 |
| US20020161175A1 (en) | 2002-10-31 |
| CN1248787C (zh) | 2006-04-05 |
| US6524708B2 (en) | 2003-02-25 |
| WO2001081010A1 (en) | 2001-11-01 |
| EP1284829A1 (en) | 2003-02-26 |
| US6323310B1 (en) | 2001-11-27 |
| EP1284829A4 (en) | 2003-07-02 |
| US6512084B2 (en) | 2003-01-28 |
| US6432611B1 (en) | 2002-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI247968B (en) | Improved anti-reflective coating compositions comprising polymerized aminoplasts | |
| TWI223128B (en) | Antireflective composition for a deep ultraviolet photoresist | |
| TW576859B (en) | Antireflective coating compositions | |
| TWI224239B (en) | Composition for forming gap-filling material for lithography | |
| TW483917B (en) | Improved thermosetting coatings for inhibiting the reflection of light at deep ultraviolet wavelengths | |
| TWI308671B (https=) | ||
| JP4471123B2 (ja) | 多孔質下層膜及び多孔質下層膜を形成するための下層膜形成組成物 | |
| JP2001521187A (ja) | 多層ホトレジストプロセスのための熱硬化性ポリエステル抗反射コーティング | |
| TWI272455B (en) | Composition for antireflection film formation | |
| WO2005064403A1 (ja) | ハードマスク用塗布型窒化膜形成組成物 | |
| TW201011078A (en) | An antireflective coating composition | |
| TW200413839A (en) | Anti-reflective compositions comprising triazine compounds | |
| TW200916543A (en) | Antireflective coating compositions | |
| TW201239047A (en) | Underlayer coating composition and process thereof | |
| KR20180134863A (ko) | 막밀도가 향상된 레지스트 하층막을 형성하기 위한 조성물 | |
| TW201841961A (zh) | 含有醯胺溶劑之阻劑下層膜形成組成物 | |
| US6653411B2 (en) | Anti-reflective coating compositions comprising polymerized aminoplasts | |
| TW200809416A (en) | Antireflective coating compositions | |
| TW200421038A (en) | Composition containing acrylic polymer for forming gap-filling material for lithography | |
| KR20180123155A (ko) | 글리콜우릴 골격을 갖는 화합물을 첨가제로서 포함하는 레지스트 하층막 형성 조성물 | |
| CN109564388A (zh) | 下层抗反射膜形成用组合物 | |
| TW200903579A (en) | Electronic device manufacture | |
| TW201204795A (en) | Antireflective coating composition and process thereof | |
| TW574234B (en) | Thermally cured underlayer for lithographic application | |
| KR101259001B1 (ko) | 유기 반사방지막 형성용 조성물 및 이를 포함하는 유기 반사방지막 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiration of patent term of an invention patent |