CN1157426A - Organic base catalytic non-developing gas-phase photoresist - Google Patents
Organic base catalytic non-developing gas-phase photoresist Download PDFInfo
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- CN1157426A CN1157426A CN 96114150 CN96114150A CN1157426A CN 1157426 A CN1157426 A CN 1157426A CN 96114150 CN96114150 CN 96114150 CN 96114150 A CN96114150 A CN 96114150A CN 1157426 A CN1157426 A CN 1157426A
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- photosensitivity
- photosensitizer
- solvent
- development
- less gas
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Links
- 229920002120 photoresistant polymer Polymers 0.000 title abstract description 14
- 230000003197 catalytic effect Effects 0.000 title description 3
- 150000007530 organic bases Chemical class 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 11
- CUARLQDWYSRQDF-UHFFFAOYSA-N 5-Nitroacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] CUARLQDWYSRQDF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 206010034972 Photosensitivity reaction Diseases 0.000 claims abstract description 10
- 230000036211 photosensitivity Effects 0.000 claims abstract description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 6
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims abstract description 5
- -1 2-benzyl-2-dimethylamino-1-morpholinophenyl Chemical group 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 244000028419 Styrax benzoin Species 0.000 claims abstract description 3
- 235000000126 Styrax benzoin Nutrition 0.000 claims abstract description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940114081 cinnamate Drugs 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 238000001259 photo etching Methods 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- 238000005530 etching Methods 0.000 claims description 14
- 239000003292 glue Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 235000015511 Liquidambar orientalis Nutrition 0.000 claims description 2
- 239000004870 Styrax Substances 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 238000001459 lithography Methods 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 abstract 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004925 Acrylic resin Substances 0.000 abstract 1
- 229920000178 Acrylic resin Polymers 0.000 abstract 1
- 235000008411 Sumatra benzointree Nutrition 0.000 abstract 1
- 229960002130 benzoin Drugs 0.000 abstract 1
- RJUVPCYAOBNZAX-UHFFFAOYSA-N ethyl 3-(dimethylamino)-2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=CN(C)C RJUVPCYAOBNZAX-UHFFFAOYSA-N 0.000 abstract 1
- 235000019382 gum benzoic Nutrition 0.000 abstract 1
- JKEMAHLSSQQCDX-UHFFFAOYSA-N n,n-bis(methylamino)formamide Chemical compound CNN(NC)C=O JKEMAHLSSQQCDX-UHFFFAOYSA-N 0.000 abstract 1
- 150000003512 tertiary amines Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- YWFJEGOSKAAABP-UHFFFAOYSA-N ethane-1,2-diol;propanedioic acid Chemical compound OCCO.OC(=O)CC(O)=O YWFJEGOSKAAABP-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000004026 adhesive bonding Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
A non-developing gas-phase photoresist belongs to the field of lithography technology. The invented photoresist is composed of film-forming agent, photosensitizer, etch-accelerating agent with photosensitivity and solvent. Its film-forming agent is made up by using uv-curable photosensitive resins, such as cinnamate resin and acrylic resin, and its photosensitizer can use 5-nitroacenaphthene, benzoin dimethyl ether and diphenyl ketone, and the like. The photosensitive etch-accelerating agent can use photosensitive compounds with tertiary amine group, such as ethyl N,N-dimethylaminomethacrylate, 2-methyl-1-(p-methylthiophenyl)-2-morpholinoacetone and 2-benzyl-2-dimethylamino-1-morpholinophenyl) butanone-1. The above-mentioned solvent can use organic solvents, such as cyclohexanone, N,N-dimethylaminoformamide and glycol ethyl ether acetate, which can dissolve the compouned mentioned above. Their mixing ratio is 8-9:0.7-1.0:0.3-1.0:90, and its etch-out depth can be up to 1600nm, and the exposure volume can be reduced to 400 mJ/cm2.
Description
The present invention relates to photoresist, belong to the technical field of lithography that semiconductor devices is made with organic base catalytic gas phase fluorination hydrogen and silicon dioxde reaction.
Photoetching technique is to make an important process of semiconductor devices.From early sixties, semiconductor devices and integrated circuit are developed rapidly, are inseparable with the application of photoetching technique.The conventional lithography process flow process as shown in Figure 1.Gluing promptly is in growth gluing on the silicon chip of silicon dioxide film to be arranged.After baking, put the special mask plate of lastblock, expose then, after the exposure, because photochemical effect, the photoresist on the exposure region changes to the solubleness of solvent, utilizes the dissolution with solvents soluble fraction, obtain the figure of a photoresist film, this step is called development.The photoresist that stays has effect against corrosion to hydrofluorite, can protect the SiO under the glued membrane
2Be not corroded, exposed silicon dioxide is then fallen by the hydrofluorite corrosion dissolution, is exactly corrosion process.Remove photoresist at last.Semiconductor devices is exactly to utilize such method graphical window that etching need be mixed and be contacted with electrode on deielectric-coating such as silicon dioxide with integrated circuit, and by mixing, technology such as wiring are produced again.In producing semiconductor devices and integrated circuit, a slice, thin piece often needs to carry out the several photoetching.Therefore the quality of photoetching quality directly influences the performance and the yield rate of product.
Because above-mentioned conventional lithography process is subjected to diffraction of light, the swelling set of photoresist film, each homogeny of chemical corrosion reaction, and the influence of problems such as the step of silicon chip surface and inhomogeneity, the resolution of photoetching is very limited, it is generally acknowledged that 2-3 μ m is its limiting resolution, therefore be difficult to use in the preparation of VLSI (very large scale integrated circuit).In order to overcome above-mentioned defective, especially the swelling set of photoresist film in the wet development, so developed DFVP technology, the technological process of DFVP technology as shown in Figure 2, DFVP technology is to utilize the photosensitizer in the photoresist can promote HF and SiO
2Corrosive attack, need not develop and just carry out corrosion process, at present the development-less gas-phase photoetching glue that adopts is by film forming matter, photosensitizer and solvent composition.Film forming matter is generally the cinnamic acid photosensitive resin, and photosensitizer is generally 5-nitro acenaphthene.Solvent is for dissolving the organic solvent of above-mentioned substance.After the exposure, cinnamic acid produces cross-linking reaction, and its glass temperature (Tg) is raise, so can prevent the volatilization of the 5-nitro acenaphthene in the photoresist, but not the exposure district then cinnamic acid do not take place crosslinked, so 5-nitro acenaphthene volatilizees easily, content reduces, thereby forms the SiO of exposure region
2Easily corroded the SiO of non-exposed area by HF
2Can not be corroded, so just can develop and just carry out photoetching corrosion.But with the very high exposure (5.4J/cm of this arts demand
2), so throughput rate is low, and the 5-nitro acenaphthene of exposure region also can volatilization loss in etching process, thus can not be very dark with this technology photoetching degree of depth, generally can only reach 800nm.Therefore limited the application prospect of DFVP technology greatly.
It is dark to the purpose of this invention is to provide a kind of photoetching degree of depth, and short development-less gas-phase photoetching glue of time shutter.
Development-less gas-phase photoetching glue of the present invention is by film forming matter, photosensitizer, etching promoter and solvent composition with photosensitivity.Film forming matter photosensitive resin such as cinnamate resinoid, the acrylic acid resinoid etc. of uV curable; Photosensitizer can be used 5-nitro acenaphthene, styrax dimethyl ether, benzophenone; Photosensitivity etching promoter is light-sensitive compound such as the N that has tertiary amine groups, silomate ylmethyl acrylic acid ethyl ester, 2-methyl isophthalic acid-(to the first sulfur phenenyl)-2-morpholine acetone, 2-benzyl-2-dimethylamino-1-(to morpholinyl phenyl) butanone-1 etc.Solvent is for dissolving the organic solvent such as the cyclohexanone of above-mentioned substance, N, N dimethylamine base formamide, ethylene glycol ether, above-mentioned the ratio of each component is: film forming matter: photosensitizer: photosensitivity etching promoter: solvent is (8-9): (0.7-1.0): (0.3-1.0): 90.
Illustrate that embodiment is as follows:
Embodiment one,
1, the preparation of development-less gas-phase photoetching glue
Get poly-cinnamic acid fork ethylene glycol malonate 1g.N, N dimethylamine ylmethyl ethyl acrylate 0.5ml, 5-nitro acenaphthene 0.1g.Put into brown reagent bottle, add ethylene glycol ether 10ml again, treat that polymkeric substance dissolves fully after, filtration can be used.
2, DFVP technology
The photoresist of coating above-mentioned preparation on the silicon chip of thin layer of silicon dioxide is arranged in growth, thickness 500-800nm, 70 ℃ down baking can expose after 10 minutes, generally expose and under the 125W high-pressure sodium lamp, exposed 35 seconds.Be placed on then and carry out etching in the etching apparatus, at first open nitrogen cylinder, about control nitrogen flow 0.3ml/min, temperature of reaction is between 110-130 ℃, allows the reaction chamber internal pressure remain on and is higher than more than the external atmosphere pressure 4cm water column.React half an hour, can the thick silicon dioxide layer of the saturating 1600nm of etching.Take out silicon chip then, with cleaning fluid (ammoniacal liquor: hydrogen peroxide: deionized water=1: 2: 4) remove photoresist, promptly obtain the positivity litho pattern.
Embodiment two,
The preparation of development-less gas-phase photoetching glue
Get poly-cinnamic acid fork ethylene glycol malonate 1g.2-methyl isophthalic acid-(to the first sulfur phenenyl)-2-morpholine acetone 0.6g, 5-nitro acenaphthene 0.1g.Put into brown reagent bottle, add ethylene glycol ether 10ml again, treat that polymkeric substance dissolves fully after, filtration can be used.
Photoetching process is the same.
Embodiment three,
The preparation of development-less gas-phase photoetching glue
Get poly-cinnamic acid fork ethylene glycol malonate 1g.2-benzyl-2-dimethylamino-1-(to morpholinyl phenyl) butanone-10.7g, 5-nitro acenaphthene 0.1g.Put into brown reagent bottle, add ethylene glycol ether 10ml again, treat that polymkeric substance dissolves fully after, filtration can be used.
Photoetching process is the same.
Adopt development-less gas-phase photoetching glue of the present invention that the photoetching degree of depth is reached more than the 1600nm, exposure can be reduced to 400mJ/cm
2
Claims (4)
1, a kind of development-less gas-phase photoetching glue that contains film forming matter, photosensitizer, solvent is characterized in that also containing that the etching promoter of photosensitivity, said film forming matter are the photosensitive resin of uV curable such as cinnamate resinoid, acrylic acid resinoid; Said photosensitizer can be used 5-nitro acenaphthene, styrax dimethyl ether, benzophenone; Said photosensitivity etching promoter is the light-sensitive compound that has tertiary amine groups, said solvent is for dissolving the organic solvent such as the cyclohexanone of above-mentioned substance, N, N dimethylamine base formamide, ethylene glycol ether, above-mentioned the ratio of each component is: film forming matter: photosensitizer: photosensitivity etching promoter: solvent is (8-9): (0.7-1.0): (0.3-1.0): 90.
2,, it is characterized in that said photosensitivity etching promoter is N, silomate ylmethyl acrylic acid second fat according to the said development-less gas-phase photoetching glue of claim 1.
3,, it is characterized in that said photosensitivity etching promoter is 2-methyl isophthalic acid-(to the first sulfur phenenyl)-2-morpholine acetone according to the said development-less gas-phase photoetching glue of claim 1
4,, it is characterized in that said photosensitivity etching promoter is 2-benzyl-2-dimethylamino-1-(to morpholinyl phenyl) butanone-1 according to the said development-less gas-phase photoetching glue of claim 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 96114150 CN1065971C (en) | 1996-12-27 | 1996-12-27 | Organic base catalytic non-developing gas-phase photoresist |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 96114150 CN1065971C (en) | 1996-12-27 | 1996-12-27 | Organic base catalytic non-developing gas-phase photoresist |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1157426A true CN1157426A (en) | 1997-08-20 |
| CN1065971C CN1065971C (en) | 2001-05-16 |
Family
ID=5121965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 96114150 Expired - Fee Related CN1065971C (en) | 1996-12-27 | 1996-12-27 | Organic base catalytic non-developing gas-phase photoresist |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1065971C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1313883C (en) * | 1999-05-06 | 2007-05-02 | 太阳油墨制造株式会社 | Solder resist ink composition |
| CN100422854C (en) * | 2004-09-08 | 2008-10-01 | 上海宏力半导体制造有限公司 | Method for reducing lead wire figure by T-shaped photoresist pattern |
-
1996
- 1996-12-27 CN CN 96114150 patent/CN1065971C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1313883C (en) * | 1999-05-06 | 2007-05-02 | 太阳油墨制造株式会社 | Solder resist ink composition |
| CN100422854C (en) * | 2004-09-08 | 2008-10-01 | 上海宏力半导体制造有限公司 | Method for reducing lead wire figure by T-shaped photoresist pattern |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1065971C (en) | 2001-05-16 |
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