JP2022043063A - 芳香族下層 - Google Patents
芳香族下層 Download PDFInfo
- Publication number
- JP2022043063A JP2022043063A JP2021192554A JP2021192554A JP2022043063A JP 2022043063 A JP2022043063 A JP 2022043063A JP 2021192554 A JP2021192554 A JP 2021192554A JP 2021192554 A JP2021192554 A JP 2021192554A JP 2022043063 A JP2022043063 A JP 2022043063A
- Authority
- JP
- Japan
- Prior art keywords
- layer
- anthracene
- bis
- alkyl
- aromatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 127
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000001424 substituent group Chemical group 0.000 claims abstract description 24
- 239000010410 layer Substances 0.000 claims description 158
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 63
- 239000000758 substrate Substances 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 48
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 47
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 229920002120 photoresistant polymer Polymers 0.000 claims description 39
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 38
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 36
- 229910052710 silicon Inorganic materials 0.000 claims description 36
- 239000010703 silicon Substances 0.000 claims description 36
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 32
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- LHRCREOYAASXPZ-UHFFFAOYSA-N dibenz[a,h]anthracene Chemical compound C1=CC=C2C(C=C3C=CC=4C(C3=C3)=CC=CC=4)=C3C=CC2=C1 LHRCREOYAASXPZ-UHFFFAOYSA-N 0.000 claims description 24
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 24
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 24
- 125000005647 linker group Chemical group 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 22
- 239000008199 coating composition Substances 0.000 claims description 22
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 22
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 20
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 20
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 19
- 125000005580 triphenylene group Chemical group 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 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 7
- 239000011247 coating layer Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 238000000059 patterning Methods 0.000 claims description 4
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical group C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 claims description 4
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 claims 4
- 150000003573 thiols Chemical class 0.000 claims 2
- 239000004065 semiconductor Substances 0.000 abstract description 18
- 239000000463 material Substances 0.000 abstract description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 56
- 239000011541 reaction mixture Substances 0.000 description 56
- 239000000203 mixture Substances 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- -1 alkane radicals Chemical class 0.000 description 28
- 239000002904 solvent Substances 0.000 description 25
- 235000012431 wafers Nutrition 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 125000003396 thiol group Chemical class [H]S* 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 14
- 238000011049 filling Methods 0.000 description 14
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000005530 etching Methods 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 11
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 11
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 10
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 10
- 230000001681 protective effect Effects 0.000 description 9
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 8
- 239000003431 cross linking reagent Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 238000005229 chemical vapour deposition Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- FIUFMPJPALRVKV-UHFFFAOYSA-N (4-ethynylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C#C)C=C1 FIUFMPJPALRVKV-UHFFFAOYSA-N 0.000 description 5
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- MZKZVUSYFPNLRK-UHFFFAOYSA-N OC1=CC=C(C=C1)C#CC1=CC(=CC(=C1)C#CC1=CC=C(C=C1)O)C#CC1=CC=C(C=C1)O Chemical compound OC1=CC=C(C=C1)C#CC1=CC(=CC(=C1)C#CC1=CC=C(C=C1)O)C#CC1=CC=C(C=C1)O MZKZVUSYFPNLRK-UHFFFAOYSA-N 0.000 description 5
- 229910052581 Si3N4 Inorganic materials 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 5
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 5
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 5
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 239000002318 adhesion promoter Substances 0.000 description 4
- 229960002903 benzyl benzoate Drugs 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- QPXKBWDJNZJXOC-UHFFFAOYSA-N 1,3,5-tris[2-(4-fluorophenyl)ethynyl]benzene Chemical compound FC1=CC=C(C=C1)C#CC1=CC(=CC(=C1)C#CC1=CC=C(C=C1)F)C#CC1=CC=C(C=C1)F QPXKBWDJNZJXOC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DIHBEBXSUDAGON-UHFFFAOYSA-N 4-[2-[3,5-bis[2-(4-aminophenyl)ethynyl]phenyl]ethynyl]aniline Chemical compound C1=CC(N)=CC=C1C#CC1=CC(C#CC=2C=CC(N)=CC=2)=CC(C#CC=2C=CC(N)=CC=2)=C1 DIHBEBXSUDAGON-UHFFFAOYSA-N 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- MGILVODMVZTARP-UHFFFAOYSA-N [4-[2-[3,5-bis[2-(4-acetyloxyphenyl)ethynyl]phenyl]ethynyl]phenyl] acetate Chemical compound C(C)(=O)OC1=CC=C(C=C1)C#CC1=CC(=CC(=C1)C#CC1=CC=C(C=C1)OC(C)=O)C#CC1=CC=C(C=C1)OC(C)=O MGILVODMVZTARP-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000012876 topography Methods 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- FMEBJQQRPGHVOR-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)CCCC1 FMEBJQQRPGHVOR-UHFFFAOYSA-N 0.000 description 1
- JDTDWAGPXAYXCI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxymethanethioic s-acid Chemical class CC(C)(C)OC(S)=O JDTDWAGPXAYXCI-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- MXHYFISNECFQHA-UHFFFAOYSA-N (4-iodophenyl) acetate Chemical compound CC(=O)OC1=CC=C(I)C=C1 MXHYFISNECFQHA-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- ZDRMMTYSQSIGRY-UHFFFAOYSA-N 1,3,5-triethynylbenzene Chemical compound C#CC1=CC(C#C)=CC(C#C)=C1 ZDRMMTYSQSIGRY-UHFFFAOYSA-N 0.000 description 1
- HJQRITCAXSBOPC-UHFFFAOYSA-N 1,3,5-tris(4-bromophenyl)benzene Chemical compound C1=CC(Br)=CC=C1C1=CC(C=2C=CC(Br)=CC=2)=CC(C=2C=CC(Br)=CC=2)=C1 HJQRITCAXSBOPC-UHFFFAOYSA-N 0.000 description 1
- YWHGJGMJAYOZLI-UHFFFAOYSA-N 1,3,5-tris[2-(4-methoxyphenyl)ethynyl]benzene Chemical compound C1=CC(OC)=CC=C1C#CC1=CC(C#CC=2C=CC(OC)=CC=2)=CC(C#CC=2C=CC(OC)=CC=2)=C1 YWHGJGMJAYOZLI-UHFFFAOYSA-N 0.000 description 1
- HFIOZJQRZKNPKJ-UHFFFAOYSA-N 1,3-dibromo-5-(3,5-dibromophenoxy)benzene Chemical compound BrC1=CC(Br)=CC(OC=2C=C(Br)C=C(Br)C=2)=C1 HFIOZJQRZKNPKJ-UHFFFAOYSA-N 0.000 description 1
- JEIHSRORUWXJGF-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]propan-2-yl acetate Chemical compound CC(=O)OC(C)COC(C)(C)C JEIHSRORUWXJGF-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- QXSWHQGIEKUBAS-UHFFFAOYSA-N 1-ethynyl-4-fluorobenzene Chemical group FC1=CC=C(C#C)C=C1 QXSWHQGIEKUBAS-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- XWOYCQCJZYOINY-UHFFFAOYSA-N 2-(oxan-2-ylsulfanyl)oxane Chemical compound O1CCCCC1SC1OCCCC1 XWOYCQCJZYOINY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LNMBCRKRCIMQLW-UHFFFAOYSA-N 2-tert-butylsulfanyl-2-methylpropane Chemical compound CC(C)(C)SC(C)(C)C LNMBCRKRCIMQLW-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- KNYIBRCMYLCPIG-UHFFFAOYSA-N 4-[2-[3-[3,5-bis[2-(4-hydroxyphenyl)ethynyl]phenoxy]-5-[2-(4-hydroxyphenyl)ethynyl]phenyl]ethynyl]phenol Chemical compound O(C=1C=C(C=C(C=1)C#CC1=CC=C(C=C1)O)C#CC1=CC=C(C=C1)O)C=1C=C(C=C(C=1)C#CC1=CC=C(C=C1)O)C#CC1=CC=C(C=C1)O KNYIBRCMYLCPIG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G03F7/004—Photosensitive materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/225—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
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- G03F7/025—Non-macromolecular photopolymerisable compounds having carbon-to-carbon triple bonds, e.g. acetylenic compounds
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- 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
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- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- 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
- G03F7/20—Exposure; Apparatus therefor
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2014—Contact or film exposure of light sensitive plates such as lithographic plates or circuit boards, e.g. in a vacuum frame
- G03F7/2016—Contact mask being integral part of the photosensitive element and subject to destructive removal during post-exposure processing
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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- Paints Or Removers (AREA)
Abstract
Description
の3個以上の置換基を含む電子デバイスが本発明によって提供される。
の化合物を更に提供する。
の3個以上の置換基を含む1種以上の硬化性化合物を含む。ZはOR1、保護ヒドロキシル、カルボキシル(C(=O)OH)、保護カルボキシル、SH、フッ素、及びNHR2から独立して選択されることが好ましい。より好ましくは、それぞれのZは、ヒドロキシル(OH)、保護ヒドロキシル、OCH2C≡CH、C(=O)OH、保護カルボキシル、及びNHR2から、その上より好ましくはOH、保護ヒドロキシル、OCH2C≡CH、カルボキシル、及び保護カルボキシルから、更により好ましくはOH及び保護ヒドロキシルから独立して選択される。それぞれのR1は、H、C1~10アルキル、C2~10不飽和ヒドロカルビル、及びC5~30アリールから、より好ましくはH、C1~10アルキル、C2~10アルケニル、C2~10アルキニル、及びC5~30アリールから独立して選択される。好ましい一実施形態において、R1はHである。好ましくは、R2は、H、C1~10アルキル、C2~10不飽和ヒドロカルビル、及びC5~30アリールから、より好ましくはH、C1~10アルキル、C2~10アルケニル及びC2~10アルキニルから選択される。本明細書で用いるところでは、用語「芳香族コア」は、式(1)の少なくとも2個の部分がそれに結合している単芳香環又は縮合芳香環系を意味する。芳香族コアは、任意選択的に、C1~20脂肪族又は脂環式部分及びC5~30アリール部分から選択される1個以上の置換基で置換されていてもよい。好ましくは、芳香族コアは、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、カルバゾール、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから、より好ましくはベンゼン、ナフタレン、カルバゾール、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから、更により好ましくはベンゼン、ナフタレン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、及びフェナレンから選択される。式(1)において、それぞれのAr1は、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから、より好ましくはベンゼン、ナフタレン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから、更により好ましくはベンゼン、ナフタレン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、及びフェナレンから独立して選択されることが好ましい。x=1又は2である、より好ましくはx=1であることが好ましい。本硬化性化合物は、式(I)の少なくとも3個の部分を有し、ここで、式(1)の少なくとも2個の置換基が芳香族コアに直接結合している。本硬化性化合物は、3~10個、好ましくは3~8個、より好ましくは3~6個、更により好ましくは3又は4個などの任意の好適な数の式(1)の部分を有し得る。本硬化性化合物は芳香族コアに直接結合した2~4個の式(1)の部分を有することが更に好ましい。
のものである。Arcは、5~25個の炭素原子、より好ましくは5~20個の炭素原子を有する芳香族コアであることが好ましい。Arcについての好適な芳香族コアには、限定なしに、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、カルバゾール、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレン、好ましくはベンゼン、ナフタレン、カルバゾール、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレン、より好ましくはベンゼン、ナフタレン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、及びフェナレンが含まれる。Ar1は、ベンゼン、ピリジン、ナフタレン、キノリン、イソキノリン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから選択されることが好ましい。より好ましくは、Ar1、Ar2、及びAr3のそれぞれは、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから、より好ましくはベンゼン、ナフタレン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから、その上より好ましくはベンゼン、ナフタレン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、及びフェナレンから独立して選択される。Arcは、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから選択され、Ar1、Ar2、及びAr3のそれぞれは、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから独立して選択されることが更に好ましい。それぞれのZ1及びZ2は、OR1、保護ヒドロキシル、カルボキシル(C(=O)OH)、保護カルボキシル、SH、フッ素、NHR2から、より好ましくはヒドロキシル(OH)、保護ヒドロキシル、OCH2C≡CH、C(=O)OH、保護カルボキシル、及びNHR2から、その上より好ましくはOH、保護ヒドロキシル、OCH2C≡CH、カルボキシル、及び保護カルボキシルから、更により好ましくはOH及び保護ヒドロキシルから独立して選択されることが好ましい。それぞれのR1は、H、C1~10アルキル、C2~10不飽和ヒドロカルビル、及びC5~30アリールから、より好ましくはH、C1~10アルキル、C2~10アルケニル、C2~10アルキニル、及びC5~30アリールから独立して選択される。好ましい一実施形態において、R1はHである。好ましくは、R2は、H、C1~10アルキル、C2~10不飽和ヒドロカルビル、及びC5~30アリールから、より好ましくはH、C1~10アルキル、C2~10アルケニル及びC2~10アルキニルから選択される。それぞれのZ1は同じものであることが好ましい。それぞれのZ2は同じものであることがまた好ましい。Z1=Z2であることが更に好ましい。x1及びx2のそれぞれは、1~3から独立して選択され、より好ましくは独立して1又は2、その上より好ましくはそれぞれ1であることが好ましい。好ましくは、各y2=0~2である。y1+各y2は3~8、より好ましくは3~6、その上より好ましくは3又は4であることが好ましい。好ましくは、w=0~1である。好ましい一実施形態において、Arc及びそれぞれのAr1は、w=0である場合フェニルではない。好ましい一実施形態において、Yは一重共有結合である。別の好ましい実施形態において、Yは、二価又は三価連結基である。Yのための例示的な連結基には、O、S、N(R3)r、S(=O)2、CR4R5、ビス-イミド部分、ビス-エーテルイミド部分、ビス-ケトイミド部分、ビス-ベンゾオキサゾール部分、ビス-ベンズイミダゾール部分、及びビス-ベンゾチアゾール部分(ここで、r=0又は1である)が含まれるが、それらに限定されず、好ましくはYのための連結基は、O、N(R3)w、及びCR4R5である。R3は、**-C(=O)-C5~30アリール又は**-S(=O)2-C5~30アリール(ここで、**は、Nへの結合点である)である。R4及びR5は、H、C1~10アルキル及びC5~10アリールから独立して選択され、R4及びR5は、それらが結合している炭素と一緒になって、1個以上の芳香環に縮合していてもよい5又は6員環を形成してもよい。Y=CR4R5である場合の1つの好適な連結基は、次式(A)
のフルオレニル部分である。Yについての好適なビス-イミド部分連結基は、式(B)及び式(C)(式中、Y1は、一重共有結合又はC5~30アリーレンであり、*は、Arc及びAr2への結合点を示す)によって示される。好適なビス-エーテルイミド及びビス-ケトイミド部分は、式(C)(式中、Y1は、それぞれ、O又は-C(=O)-であり、*は、Arc及びAr2への結合点を示す)のものである。好適なビス-ベンゾオキサゾール、ビス-ベンズイミダゾール、及びビス-ベンゾチアゾール部分は、式(D)(式中、Gは、それぞれ、O、NH、及びSであり、Y2は、一重共有結合又はC5~30アリーレンであり、*は、Arc及びAr2への結合点を示す)のものである。
反応スキーム1
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反応スキーム5
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反応スキーム7
反応スキーム8
反応スキーム9
反応スキーム10
。本反応は、次の反応スキームに示される。
反応スキーム10
Claims (12)
- 式(2)
の化合物。 - Z1及びZ2のそれぞれが、OR1、保護ヒドロキシル、カルボキシル、保護カルボキシル、SH、フッ素及びNHR2から独立して選択される請求項1に記載の化合物。
- Arcの芳香族コアが、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、カルバゾール、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから選択される請求項1に記載の化合物。
- Ar1、Ar2及びAr3のそれぞれが、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから独立して選択される請求項1に記載の化合物。
- (a)電子デバイス基板を提供する工程と;
(b)式(2)
(c)前記硬化性化合物の前記層を硬化させて下層を形成する工程と;
(d)フォトレジストの層を前記下層上にコートする工程と;
(e)マスクを通して前記フォトレジスト層を化学線に露光する工程と;
(f)前記露光フォトレジスト層を現像してレジストパターンを形成する工程と;
(g)前記パターンを前記下層に転写して前記電子デバイス基板の複数部分を露出させる工程とを含む方法。 - 前記基板をパターン化する工程と;次に前記パターン化された下層を取り除く工程とを更に含む請求項5に記載の方法。
- 工程(d)の前にシリコン含有層、有機反射防止コーティング層及びそれらの組み合わせの1つ以上を前記下層一面にコートする工程を更に含む請求項5に記載の方法。
- 工程(f)の後及び工程(g)の前に前記シリコン含有層、前記有機反射防止コーティング層及び前記それらの組み合わせの1つ以上に前記パターンを転写する工程を更に含む請求項6に記載の方法。
- Z1及びZ2のそれぞれが、OR1、保護ヒドロキシル、カルボキシル、保護カルボキシル、SH、フッ素及びNHR2から独立して選択される請求項5に記載の方法。
- Arcの芳香族コアが、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、カルバゾール、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから選択される請求項5に記載の方法。
- Ar1、Ar2及びAr3のそれぞれが、ピリジン、ベンゼン、ナフタレン、キノリン、イソキノリン、アントラセン、フェナントレン、ピレン、コロネン、トリフェニレン、クリセン、フェナレン、ベンズ[a]アントラセン、ジベンズ[a,h]アントラセン、及びベンゾ[a]ピレンから独立して選択される請求項5に記載の方法。
- 前記コーティング組成物が、有機溶媒、硬化剤、及び表面均展剤の1つ以上を更に含む請求項5に記載の方法。
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US20220197143A1 (en) * | 2020-12-18 | 2022-06-23 | Rohm And Haas Electronic Materials Llc | Adhesion promoting photoresist underlayer composition |
US20230057401A1 (en) * | 2021-07-06 | 2023-02-23 | Rohm And Haas Electronic Materials Llc | Coated underlayer for overcoated photoresist |
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