CN100595680C - Thinner composition for removing photosensitive resin - Google Patents
Thinner composition for removing photosensitive resin Download PDFInfo
- Publication number
- CN100595680C CN100595680C CN200410070223A CN200410070223A CN100595680C CN 100595680 C CN100595680 C CN 100595680C CN 200410070223 A CN200410070223 A CN 200410070223A CN 200410070223 A CN200410070223 A CN 200410070223A CN 100595680 C CN100595680 C CN 100595680C
- Authority
- CN
- China
- Prior art keywords
- ketone
- photosensitive resin
- substrate
- diluent composition
- composition
- 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.)
- Expired - Fee Related
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Classifications
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/044—Hydroxides or bases
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
Abstract
The present invention relates to a thinner composition for removing a photosensitive resin used for manufacturing a semiconductor device or a liquid crystal display, and more particularly to a thinner composition comprising a) an alkylamide and b) a ketone. The diluent composition may further comprise c) a perfluoroalkyl amine oxide. The thinner composition of the present invention is effective in removing unwanted color resists attached to the edges and back of a substrate, particularly a large-sized colored glass substrate used in the manufacture of liquid crystal displays. It also removes the remaining film and reduces the edge gap, thus effectively cleaning the substrate. Therefore, it is used for various processes with economic advantages, simplifying the manufacturing process and improving the yield.
Description
Technical field
The present invention relates in the manufacturing process of semiconductor devices or LCD, remove the diluent composition of resist, relate more specifically in the manufacturing process of LCD, effectively to remove the diluent composition of unwanted resist.
Background technology
When forming micro circuit pattern such as SIC (semiconductor integrated circuit) and TFT-LCD circuit by lithography, on substrate, form the film of oxide etc., resist is applied from the teeth outwards equably, resist is exposed and develops to form the resist pattern, as the film of mask selective etch below the resist pattern, remove all resists on the substrate with this pattern then fully.When making semiconductor devices or TFT-LCD by such lithography, must use thinning agent remove remaining unwanted resist on glass or the silicon wafer and before exposure and development at any unwanted film of the bottom of substrate formation.
What usually, can be used as thinning agent has ether and ether acetic acid ester such as cellosolve, cellosolve acetic acid esters, propylene glycol, propylene glycol acetic acid esters etc.; Ketone such as acetone, MEK, methyl isobutyl ketone, cyclohexanone etc.; With ester such as methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate etc.
For example, the open clear 4-49938 of No. of Jap.P. discloses propylene glycol monomethyl ether (PGMEA) and discloses the purposes of alkyl alkoxy propionic ester as thinning agent as purposes and the open clear 4-42523 of No. of Jap.P. of thinning agent.These methods use single solvents such as ethylene glycol monomethyl ether acetate (EGMEA), propylene glycol monomethyl ether (PGMEA), ethyl lactate (EL) etc.They have following limitation.
Although ethylene glycol monomethyl ether acetate has excellent solubleness, it has high volatile volatile and is inflammable, and particularly it can cause leukopenia, miscarriage etc.In the preparation technology of propylene glycol monomethyl ether, comprise β-type propylene glycol monomethyl ether inevitably, it can cause children's deformity and maternal toxicity.Because ethyl lactate has high viscosity and low solubility, use can not provide enough cleaning effects separately.Solvent such as acetone, MEK etc. have low-flash, make them be difficult to handle.
For addressing these problems, developed the method for mixing these conventional solvents.
The open clear 4-130715 of No. of Jap.P. discloses the purposes of the potpourri of pyruvate alkyl esters and MEK as thinning agent.The open clear 7-146562 of No. of Jap.P. discloses the diluent composition of the potpourri that comprises propylene glycol alkyl ether and alkyl-3-alkoxyl propionic ester.The open clear 7-128867 of No. of Jap.P. discloses the diluent composition that comprises propylene glycol alkyl ether, butyl acetate and ethyl lactate, or the diluent composition of the potpourri of butyl acetate, ethyl lactate and propylene glycol alkyl ether acetic acid ester.The open clear 7-160008 of No. of Jap.P. discloses the diluent composition of the potpourri of the potpourri that comprises propylene glycol alkyl ether propionic ester and MEK or propylene glycol alkyl ether propionic ester and butyl acetate.U.S. patent No.4,983,490 disclose the diluent composition and the U.S. patent No.4 of the potpourri that comprises propylene glycol alkyl ether acetic acid ester and propylene glycol alkyl ether, and 886,728 disclose the diluent composition of the potpourri that comprises ethyl lactate and MEK.
Yet,, thereby limited the application of these potpourris in these devices because semiconductor devices and LCD have higher integrated level and bigger size.
For example, comprise that the potpourri of pyruvate alkyl esters solvent and MEK has for 1, the solubleness that 2-naphtho-quinone diazide photosensitizer reduces, and this photosensitizer is a kind of key component of light-sensitive surface.When using the potpourri of height volatile solvent such as propylene glycol alkyl ether propionic ester and butyl acetate, bigger variation can take place in the thickness of substrate cooling back light-sensitive surface.When using the potpourri of the less solvent of volatility such as ethyl lactate and MEK, the cleaning of edges of substrate may be not exclusively.Especially, known some solvent such as methyl pyruvate, ethyl pyruvate etc. can corrode the metal parts of container.
Same when these potpourris are used to make the large scale stained glass substrate of LCD, may not remove unwanted resist fully.Remaining resist can form band after developing.
Summary of the invention
One aspect of the present invention provides a kind of diluent composition of removing photosensitive resin, said composition can be removed the unwanted colored resist that adheres at edges of substrate and the back side effectively at short notice, especially for the large scale stained glass substrate of making LCD.
Another aspect of the present invention provides a kind of diluent composition of removing photosensitive resin, and said composition is effective clean substrate by the gap that reduces the edge.
Embodiment
For reaching two aspects as above, the invention provides a kind of diluent composition of removing photosensitive resin, said composition comprises: a) alkylamide; And b) ketone.
This diluent composition can further comprise c) perfluoroalkyl amine oxide (perfluoroalkyl amineoxide).
Preferably, the diluent composition of removing photosensitive resin of the present invention comprises: a) alkylamide of 10～90 weight portions; B) ketone of 10～90 weight portions; And c) the perfluoroalkyl amine oxide of 0.001～1 weight portion.
Below, more detailed description the present invention.
The invention is characterized in the diluent composition of removing photosensitive resin by a kind of, effectively remove the unwanted colored resist that adheres at large scale stained glass edges of substrate and the back side at short notice, and therefore be used for producing the semiconductor devices or LCD.
In diluent composition of the present invention, a) alkylamide; B) ketone and c) each of perfluoroalkyl amine oxide is selected from ultrapure level semiconductor (ultrapure semiconductor level).In VLSI (very large scale integrated circuit) (VLSI) level, use the level that is filled into 0.1 μ m.
Alkylamide is used to improve the solubleness of composition.The alkyl of alkylamide contains at least one carbon atom, preferred 2～5 carbon atoms.Particularly, the preferred alkyl acid amides is to be selected from least a in the following compound: N-methylacetamide, dimethyl formamide and dimethyl acetamide.Consider the factor of solubleness, be more preferably dimethyl acetamide.
Preferably, the alkylamide that in per 100 weight portion compositions, comprises 10～90 weight portions.If the content of alkylamide less than 10 weight portions, to the solubleness of colored resist, makes residue still be retained in the substrate end.In addition, if it surpasses 90 weight portions, volatility reduces, and makes the EBR line become inhomogeneous, under serious situation, may be penetrated in the interface of colored resist.
Operable ketone is to be selected from least a in the following compound: cyclic ketones and by general formula R
1COR
2(R wherein
1And R
2Each be to contain at least one carbon atom, the alkyl of preferred 1～5 carbon atom) expression compound.Particularly, preferred ketone is to be selected from least a in the following compound: acetone, methyl isopropyl Ketone, methyl n-pro-pyl ketone, MEK, methyl isobutyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone and cycloheptanone.
Preferably, the ketone that in per 100 weight portion compositions, comprises 10～90 weight portions.If the content of ketone is less than 10 weight portions, volatility reduces, and makes the EBR line become inhomogeneous.On the other hand, if it surpasses 90 weight portions, the ability of the removing reduction to colored resist makes residue still be retained in the edge of glass substrate.
Diluent composition of the present invention can further comprise the perfluoroalkyl amine oxide.The perfluoroalkyl amine oxide has the good solubility to water and all kinds of solvents.Preferably, the alkyl in the perfluoroalkyl amine oxide contains 5～30 carbon atoms.
The example of commercially available perfluoroalkyl amine oxide is the S-141 of Ashahi Glass.
In per 100 parts by weight diluent compositions, preferably include the perfluoroalkyl amine oxide of 0.001～1 weight portion.If the content of perfluoroalkyl amine oxide is less than 0.001 weight portion, cleaning effect descends.On the other hand, if it surpasses 1 weight portion, the ability of removing reduces.
Diluent composition of the present invention can be used for removing photoresist.That is, by dripping or spraying diluent composition to remove unwanted photoresist at the edges of substrate and the back side.Can be according to the dropping and the sprinkling amount of light-sensitive surface kind and film thickness control thinning agent.Preferably, consumption is selected from the scope of 5～100ml/min.After spraying diluent composition, can form micro circuit pattern by lithography.
Below, by the present invention of embodiment more detailed description.Yet following embodiment only is used for understanding of the present invention, rather than limitation of the present invention.
Embodiment
Substrate sample is prepared as follows
Using diameter is the silicon oxide substrate of 5 inches (127mm).Substrate is cleaned in two baths that contain hydrogen peroxide and sulfuric acid respectively, (immerse each bathe in 5 minutes), and adopt the ultrapure water washing.Use the clean facilities of special preparation to carry out this process.Then, use rotary drier (the SRD 1800-6 of VERTEQ) Rotary drying substrate.The light-sensitive surface of coating predetermined thickness on substrate.Adopt spin coated device (the EBR TRACK of Korea Semiconductor System) coating light-sensitive surface.
Spin coated technology is as follows.Keeping static substrate center to drip 10ml light-sensitive surface composition.Then, use the spin coated device under 300rpm, to disperse light-sensitive surface 3 seconds.Substrate under about 500rpm rotated to obtain required photographic film thickness thereafter.Rotational time is about 25 seconds.
Embodiment 1～4 and Comparative Examples 1～5
Composition and content that every kind of diluent composition according to the form below 1 provides are prepared (unit: weight portion).
Table 1
Remarks)
1.DMAc=dimethyl acetamide
2.CXN=cyclohexanone
3.PGME=propylene glycol monomethyl ether
4.PGMEA=propylene glycol monomethyl ether
5.nBA=butyl acetate (butyl ethanoate)
6.S=perfluoroalkyl amine oxide (S-141 ' of Ashahi Glass)
Remove unwanted light-sensitive surface
Coating light-sensitive surface composition on 5 inches (127mm) silicon oxide substrate.Every kind of diluent composition of use embodiment 1～4 and Comparative Examples 1～5 is removed the unwanted light-sensitive surface (edge pearl residue is removed (edge bead removing) test: hereinafter referred to as the EBR test) at edges of substrate.In the EBR test, use identical spin coated device to be used on substrate, applying light-sensitive surface.
On substrate, spray every kind of diluent composition in the table 1 by the EBR nozzle, wherein on this substrate, applied the photosensitive resin composition in the following table 2.Remove the spherical photosensitive material at edge under the condition that in following table 3, provides.Add every kind of diluent composition with being equipped with manometric pressurized tank.Pressure is set in 1.0kgf, will be from the diluent composition flow set of EBR nozzle ejection at 10～20ml/min.
In following table 4, provide the EBR test result of every kind of photosensitive resin composition.
The kind of photosensitive resin composition and film thickness
Table 2
The EBR test condition
Table 3
The EBR test result of every kind of photosensitive resin composition
Table 4
In table 4, the JSR developing solution 100 by rotary spraying on substrate dilution continues to develop in 60 seconds, and this substrate is by resist coating, the process of spraying thinning agent and prebaking.
Remarks)
The edge of ◎=clearly
Zero=linear edge (80% or more than)
The edge of △=be out of shape by the dissolving of thinning agent
*=trail at edge generation film
As seeing at table 4, all diluent compositions of the present invention (embodiment 1～4) show for the excellent EBR ability (clearly edge) of all light-sensitive surfaces and fully remove all bands that form after developing.Having sprayed on the substrate of diluent composition does not have film to stay.Especially, comprise that the diluent composition (embodiment 2 and 4) of perfluoroalkyl amine oxide is better than the diluent composition of embodiment 1 and 3.This shows that the perfluoroalkyl amine oxide can improve the ability that photoresist removes.
Equally, diluent composition of the present invention excellent xsect of maintenance under the EBR rpm condition that changes.This means that diluent composition of the present invention provides excellent ability under various conditions, this proves that it is more stable than conventional diluent composition.
As mentioned above, the diluent composition of removing photosensitive resin of the present invention can effectively be removed the unwanted colored resist that adheres at edges of substrate and the back side, especially for the large scale stained glass substrate of making LCD.It is also removed the residue film and reduces the level difference at edge, thus clean substrate effectively.Therefore, it is used for various technologies with its economic advantage, and simplified manufacturing technique also provides productive rate.
Although describe the present invention in detail with reference to embodiment preferred, those skilled in the art understand and can carry out various improvement and replacement and do not deviate from the spirit and scope of the invention that provides in claims it.
Claims (5)
1, a kind of diluent composition that is used to remove photosensitive resin comprises:
A) alkylamide; With
B) ketone,
Wherein alkylamide is to be selected from least a in the following compound: N-methylacetamide, dimethyl formamide and dimethyl acetamide,
Wherein ketone is to be selected from least a in the following compound: acetone, methyl isopropyl Ketone, methyl n-pro-pyl ketone, MEK, methyl isobutyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone and cycloheptanone.
2, the diluent composition that is used to remove photosensitive resin of claim 1 comprises:
A) alkylamide of 10～90 weight portions; With
B) ketone of 10～90 weight portions.
3, the diluent composition that is used to remove photosensitive resin of claim 1 further comprises: c) perfluoroalkyl amine oxide.
4, the diluent composition that is used to remove photosensitive resin of claim 3 comprises:
A) alkylamide of 10～90 weight portions;
B) ketone of 10～90 weight portions; With
C) the perfluoroalkyl amine oxide of 0.001～1 weight portion.
5, claim 3 or 4 the diluent composition that is used to remove photosensitive resin, wherein in the perfluoroalkyl amine oxide alkyl contain 5～30 carbon atoms.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020030053380A KR101016724B1 (en) | 2003-08-01 | 2003-08-01 | Thinner composition for removing photosensitive resin |
| KR1020030053380 | 2003-08-01 | ||
| KR10-2003-0053380 | 2003-08-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1580959A CN1580959A (en) | 2005-02-16 |
| CN100595680C true CN100595680C (en) | 2010-03-24 |
Family
ID=34374110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200410070223A Expired - Fee Related CN100595680C (en) | 2003-08-01 | 2004-07-30 | Thinner composition for removing photosensitive resin |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4494897B2 (en) |
| KR (1) | KR101016724B1 (en) |
| CN (1) | CN100595680C (en) |
| TW (1) | TWI306184B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4753641B2 (en) * | 2005-07-01 | 2011-08-24 | 株式会社Ｓｏｋｕｄｏ | Substrate processing system |
| US7766565B2 (en) | 2005-07-01 | 2010-08-03 | Sokudo Co., Ltd. | Substrate drying apparatus, substrate cleaning apparatus and substrate processing system |
| KR101328097B1 (en) * | 2006-01-11 | 2013-11-13 | 주식회사 동진쎄미켐 | A color resist remover composition for tft-lcd preparation |
| WO2023092278A1 (en) * | 2021-11-23 | 2023-06-01 | 才将科技股份有限公司 | Composition for cleaning bonding layer and application thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52100235A (en) * | 1976-02-19 | 1977-08-23 | Sony Corp | Stripping solution of photosolubilizable light sensitive resin |
| JPS61172147A (en) * | 1985-01-25 | 1986-08-02 | Konishiroku Photo Ind Co Ltd | Correcting agent for lithographic printing plate |
| JPH02981A (en) * | 1988-02-25 | 1990-01-05 | Hoya Corp | Stripping liquid for photosensitive resin and method of stripping photosensitive resin by using this liquid |
| JPH05181289A (en) * | 1992-01-06 | 1993-07-23 | Fuji Xerox Co Ltd | Removing method for organic film of organic photosensitive body, and regenerated base body for organic photosensitive body |
| US6326130B1 (en) * | 1993-10-07 | 2001-12-04 | Mallinckrodt Baker, Inc. | Photoresist strippers containing reducing agents to reduce metal corrosion |
| JP3386264B2 (en) * | 1994-12-15 | 2003-03-17 | 昭和電工株式会社 | Back rinse solution for cleaning polyimide precursor |
| JPH08286394A (en) * | 1995-04-11 | 1996-11-01 | Toray Eng Co Ltd | Removal method for photosensitive coating film |
| JPH10183191A (en) * | 1996-02-16 | 1998-07-14 | Nitto Chem Ind Co Ltd | Cleaning of remains attached on industrial apparatus |
| JP3978255B2 (en) * | 1997-06-24 | 2007-09-19 | Ａｚエレクトロニックマテリアルズ株式会社 | Lithographic cleaning agent |
| JPH11218933A (en) * | 1998-01-30 | 1999-08-10 | Fuji Film Olin Kk | Solvent for cleaning and removing resist and manufacture of device for forming electronic parts |
| KR100335011B1 (en) * | 1999-08-19 | 2002-05-02 | 주식회사 동진쎄미켐 | Resist removing composition |
| KR100378552B1 (en) | 2000-01-14 | 2003-03-29 | 주식회사 동진쎄미켐 | Resist remover composition |
| JP2001244258A (en) * | 2000-02-29 | 2001-09-07 | Sumitomo Bakelite Co Ltd | Method of forming organic insulating film for semiconductor |
-
2003
- 2003-08-01 KR KR1020030053380A patent/KR101016724B1/en active IP Right Grant
-
2004
- 2004-06-29 TW TW093119118A patent/TWI306184B/en not_active IP Right Cessation
- 2004-07-22 JP JP2004213791A patent/JP4494897B2/en active Active
- 2004-07-30 CN CN200410070223A patent/CN100595680C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101016724B1 (en) | 2011-02-25 |
| TW200506551A (en) | 2005-02-16 |
| KR20050014955A (en) | 2005-02-21 |
| TWI306184B (en) | 2009-02-11 |
| JP2005055886A (en) | 2005-03-03 |
| JP4494897B2 (en) | 2010-06-30 |
| CN1580959A (en) | 2005-02-16 |
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