WO2019156363A1 - Composition de solution de nettoyage de masque - Google Patents
Composition de solution de nettoyage de masque Download PDFInfo
- Publication number
- WO2019156363A1 WO2019156363A1 PCT/KR2019/000230 KR2019000230W WO2019156363A1 WO 2019156363 A1 WO2019156363 A1 WO 2019156363A1 KR 2019000230 W KR2019000230 W KR 2019000230W WO 2019156363 A1 WO2019156363 A1 WO 2019156363A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- minutes
- cleaning liquid
- liquid composition
- mask cleaning
- mask
- 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.)
- Ceased
Links
Classifications
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
-
- 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
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
-
- 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
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
Definitions
- the present invention relates to a mask cleaning liquid composition, specifically, a mask cleaning liquid composition for removing various organic substances on a mask used in a deposition process.
- FPDs Flat panel displays
- OLEDs organic light emitting diodes
- the liquid crystal display device that is most used as a display has advantages such as light weight, small volume, and low power, compared to a conventional CRT (Cathode ray tube).
- CRT Cathode ray tube
- the backlight should be used, and the viewing angle is limited by using liquid crystal.
- OLED devices have advantages such as low voltage driving, high luminous efficiency, wide viewing angle, and fast response speed, and above all, they do not need back light because they are self-luminous.
- the OLED device emits light by recombining electrons and holes supplied from a cathode and an anode using a light emitting organic material that emits light.
- a semiconductor device or a flat panel display such as an OLED may perform deposition of an organic material using a mask to form organic material layers such as various light emitting layers, hole injection layers, hole transport layers, electron transport layers, electron injection layers, and the like during the manufacturing process.
- organic material layers such as various light emitting layers, hole injection layers, hole transport layers, electron transport layers, electron injection layers, and the like during the manufacturing process.
- the organic material is attached to the surface of the mask, the shape of the pattern formed by the mask may be deformed due to the organic material attached. This causes a decrease in the efficiency of the deposition process and may affect the performance of the semiconductor device or flat panel display to be manufactured, so it is necessary to remove the organic matter deposited on the mask.
- Republic of Korea Patent Publication No. 2011-0095814 relates to a deposition material cleaning liquid composition and a cleaning method using the same, N-methyl-2-pyrrolidone (N-Methyl-2-pyrrolidone); And 1,3-dimethyl-2-imidazolidinone (1,3-Dimethyl-2-imidazolidinone).
- Korean Patent No. 1388283 relates to a mask cleaning apparatus, comprising: an ultrasonic cleaner for generating ultrasonic waves to clean a mask immersed in a cleaning liquid;
- the ultrasonic cleaning unit includes a cleaning solution circulation unit for discharging and supplying the cleaning solution, and the ultrasonic wave in the ultrasonic cleaning unit has a frequency of 75 KHz or more and 90 KHz or less, the intensity is 800 W or more and 1100 W or less, and the cleaning solution is NMP (N-Methyl Pyrrolidinone).
- N-methylpyrrolidinone N-methylpyrrolidinone
- NMP N-methyl-2-pyrrolidone
- the mask cleaning process should not degrade performance after long-term storage in the standby state because the operating time is determined according to the manufacturing process conditions. In particular, due to exposure to the atmosphere, there should be no degradation in water absorption.
- Patent Document 1 Republic of Korea Patent Publication No. 2011-0095814 (2011.08.25.)
- Patent Document 2 Republic of Korea Patent No. 1388283 (2014.04.16.)
- An object of the present invention is to provide a cleaning liquid composition that exhibits good cleaning power without including an environmental regulatory substance.
- the present invention provides a mask cleaning liquid composition
- a mask cleaning liquid composition comprising a glyme-based compound represented by the following formula (1) and containing no nonpolar solvent.
- R1 and R2 are each independently C1 to C10 straight chain or C3 to C10 branched alkyl group
- R3 is C1 to C10 straight chain or C3 to C10 branched alkylene group
- n is an integer of 1-4.
- the mask cleaning liquid composition according to the present invention can exhibit a good cleaning power without including an environmental regulatory material such as NMP, there is an advantage in the easy operation of the process.
- the mask cleaning liquid composition according to the present invention has the advantage that the performance degradation due to moisture absorption is suppressed.
- a member when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.
- One aspect of the present invention relates to a mask cleaning liquid composition containing a glyme-based compound represented by the following formula (1) and containing no nonpolar solvent.
- R1 and R2 are each independently C1 to C10 straight chain or C3 to C10 branched alkyl group
- R3 is C1 to C10 straight chain or C3 to C10 branched alkylene group
- n is an integer of 1-4.
- the linear or branched alkyl group is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl , n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n -Heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1-e
- alkyl group may be applied except that the alkylene group is divalent.
- the mask cleaning liquid composition according to the present invention may be in a neat state of the glame-based compound represented by Chemical Formula 1.
- the mask cleaning liquid composition according to the present invention may be formed of a glymeic compound represented by Chemical Formula 1.
- the glyme compound represented by the formula (1) is ethylene glycol dimethyl ether (DMG), diethylene glycol dimethyl ether (DMDG), triethylene glycol dimethyl ether (DMTG), diethylene glycol diethyl Ether (DEDG), diethylene glycol methyl ethyl ether (MEDG), diethylene glycol methyl butyl ether (MBDG), triethylene glycol methyl butyl ether (MBTG), propylene glycol dimethyl ether (PDM), dipropylene glycol dimethyl ether (DPDM )
- ethylene glycol diethyl ether (DEG) may be one or more selected from, for example, the glyme-based compound may be used alone or in combination of two or more thereof.
- the glyme-based compound represented by Formula 1 has a ⁇ P of 4.5 to 6.5 MPa 1/2 , ⁇ H
- The may be one having a Hansen solubility constant (Hansen Solubility Parameter) value of 4.0 to 6.0 MPa 1/2.
- the glyme-based compound represented by Formula 1 has a Hansen Parameter value that satisfies the above range, since the polar solubility parameter and the hydrogen bonding solubility parameter have low values at the same time, It is preferable to have an advantage of obtaining a mask cleaning liquid having high solubility and excellent cleaning / removing ability with respect to an organic material including a polymer material.
- Glidden critical compound of the formula (1) is the ⁇ P is 4.5 to 6.5 MPa 1/2, ⁇ H Of 4.0 to 6.0 and MPa 1/2, ⁇ D is 15.0 to 16.0 MPa 1/2, ⁇ T is 16 to 25 MPa 1/2, specifically, ⁇ T is 16.5 to 18.0 MPa 1/2 the Hansen solubility constant It can be used, and in this case it is preferable because the above-described advantages can be maximized.
- the ⁇ T is ( ⁇ P 2 + ⁇ H 2 + ⁇ D 2 ) Can be calculated as 1/2 .
- the mask cleaning liquid composition according to the present invention includes the glyme-based compound represented by Chemical Formula 1, the mask cleaning liquid composition has excellent mask cleaning power, and does not cause damage to materials such as SUS and Invar forming a mask, for example, NMP. Because it can be used instead of environmentally harmful substances such as environmentally friendly and has an easy advantage in terms of process. Specifically, the mask cleaning liquid composition according to the present invention does not cause damage such as corrosion, such as a mask of Invar material used to form the organic light emitting device and a stainless steel (SUS 304, 316, 420, etc.) supporting the mask. There is this.
- the mask cleaning liquid composition according to the present invention does not contain nonpolar solvents, and thus has an advantage of excellent cleaning power.
- the nonpolar solvent is not limited thereto, for example, hexane, heptane, carbon tetrachloride, benzene, toluene, xylene, N-methylpyrrolidone, tetrahydrofuran, nitrobenzene, N, N-dimethylformamide, dimethyl sulfoxide (dimethylsulfoxide) diethylcarbonate, benzyl acetate, dimethyl glutarate, dimethyl acetate, ethylacetoacetate, isobutyl isobutanoate, isobutyl acetate ), Meta-cresol or a mixture of two or more thereof, but is not limited thereto.
- the mask cleaning liquid composition according to the present invention does not contain the non-polar solvent, thereby having an advantage of preventing the problem.
- the mask cleaning liquid composition according to the present invention is excellent in cleaning power for various organic substances adhered to the mask.
- the organic material may be, for example, a material forming an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), or the like that emits red, green, and / or blue light.
- the emission layer may emit red, green, and / or blue, and may be formed of a phosphor or a fluorescent material.
- the light emitting host material may be CBP ((carbazole-9-yl) biphenyl), BSBF (2- (9,9-Spirobifluoren-2-yl) -9,9-spirobifluorene), TPBi (1,3,5- Tris (1-phenyl-1Hbenzimidazol-2-yl) benzene) or mCP (1,3-bis (carbazol-9-yl) -benzene) may be used, but is not limited thereto.
- CBP ((carbazole-9-yl) biphenyl)
- BSBF (9,9-Spirobifluoren-2-yl) -9,9-spirobifluorene
- TPBi 1,3,5- Tris (1-phenyl-1Hbenzimidazol-2-yl) benzene
- mCP 1,3-bis (carbazol-9-yl) -benzene
- Red luminescent dopants include PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonato iridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonato iridium), PQIr (tris (1-phenylquinoline) iridium), PtOEP (octaethylporphyrin platinum) Phosphors such as), fluorescent materials such as tris- (8-hydroxyquinoline) aluminum), and the like may be used.
- a phosphor such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or a fluorescent material such as Alq3 (tris- (8-hydroxyquinoline) aluminum) may be used, but is not limited thereto. no.
- blue light emitting dopants include phosphors such as (4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, ditylbenzene (DSB), distriarylene (DSA), PFO-based polymers, and PPV.
- Fluorescent materials such as polymers may be used, but are not limited thereto.
- the hole transport layer is NPD (N, N'-Di (1-naphthyl) -N, N ''-diphenyl- (1,1'-biphenyl) -4,4'-diamine), TPD (N, N'-bis -(3-methylphenyl) -N, N'-bis- (phenyl) -benzidine), s-TAD and MTDATA (4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenyl-amino)- triphenylamine), but is not limited thereto, such as triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkaine derivatives, pyrazoline derivatives and pyrazolone derivatives, for example, as a hole transport layer material.
- Phenylenediamine derivatives Phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane-based, aniline-based aerials Copolymers, conductive polymer oligomers (particularly thiophene oligomers) and the like.
- oxadiazole derivatives triazole derivatives, phenanthroline derivatives, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), aluminum complexes and the like contained in the hole blocking layer may be used.
- the material for the hole injection layer at least one selected from the group consisting of copper phthalocyanine (PuPc), poly (3,4) -ethylenedioxythiophene (PEDOT), polyaniline (PANI), and NPD may be used.
- the mask cleaning liquid composition may further comprise a water-soluble polar solvent.
- the water-soluble polar solvent may include one or more selected from the group consisting of a proton polar solvent and an aprotic polar solvent.
- the water-soluble polar solvent according to the present invention may include a proton polar solvent and an aprotic polar solvent, and these may be used alone or in combination.
- the proton polar solvent is, for example, ethylene glycol monomethyl ether (MG), ethylene glycol monoethyl ether (EC), ethylene glycol monoisopropyl ether (iPG), ethylene glycol monobutyl ether (BC), diethylene glycol monomethyl ether (MDG), diethylene glycol monoethyl ether (EDG), diethylene glycol monoisopropyl ether (iBDG), diethylene glycol monobutyl ether (BDG), triethylene glycol monomethyl ether (MTG), triethylene glycol monoethyl Ether (ETG), triethylene glycol monoisopropyl ether (iBTG), triethylene glycol monobutyl ether (BTG), polyethylene glycol monomethyl ether (MPG), polyethylene glycol monobutyl ether (BPG), propylene glycol monomethyl ether ( Alkylene glycol monoalkyl ethers such as MFG), dipropylene glycol monomethyl ether (MFDG), and tripropylene glyco
- the aprotic polar solvent is, for example, N, N-dimethylpropionamide (DMPA), N, N, -dimethylacetamide (DMAC), N, N-dimethylisobutylamide (DMIB), N, N-dimethylacrylamide ( DMAR), N, N-dimethylmethacrylamide, N, N-dimethyldecanamide (DMDA), N, N-diethylformamide (DEF), N, N-diethylacetamide (DEAC), N, N -Diethylpropionamide (DEPA), N, N-diethylisobutylamide (DEIB), N, N-diethylacrylamide (DEA), N, N-diethylmethacrylamide, 3-methoxy-N Dialkylamides such as N-dimethylpropionamide (MDMP) and 3-butoxy-N, N-dimethylpropionamide, N, N-diethylformamide (DEF) and N, N-dimethylform
- an amide compound such as a dialkylamide compound or a monoamide compound, and more preferably a dialkylamide compound is preferable in view of washability.
- the water-soluble polar solvent serves to dissolve the organic material remaining in the mask with the glyme-based compound represented by the formula (1), and also to facilitate the removal of the cleaning solution by water in the rinse process of deionized water after cleaning Minimize the resorption / reattachment of the organic material or can play a role that can be implemented to improve the removal of the specific organic material.
- the water-soluble polar solvent may be selected according to the performance required in the subsequent cleaning process, it is preferable that the water-soluble polar solvent does not have a low boiling point for proper cleaning power and stable operation of the process. For example, it is preferable to have a boiling point of 150-290 degreeC. When using a water-soluble polar solvent having a boiling point within the above range it may be preferable in terms of environmental and process.
- the boiling point of the water-soluble solvent is low, it is preferable to use a water-soluble polar solvent having a boiling point within the above range because it may be volatilized in the cleaning process and the process usage may increase and adversely affect the working environment.
- the water-soluble polar solvent may be included in an amount of 0 to 90 parts by weight, preferably 0 to 80 parts by weight, based on 100 parts by weight of the cleaning liquid composition.
- the water-soluble polar solvent is included in the above range, it is preferable because it has an excellent cleaning power, it is possible to prepare a cleaning liquid composition that is easy to remove the cleaning liquid by water in the rinse process of deionized water after cleaning.
- water may be included in an amount of 7 parts by weight or less based on 100 parts by weight in total.
- the mask cleaning liquid composition may contain 5 parts by weight or less based on 100 parts by weight of the total.
- the mask cleaning liquid composition may include 3 parts by weight or less of the water based on 100 parts by weight of the total.
- the water may be deionized water (DIW) or ultrapure water in which impurities are reduced as much as possible, but are not limited thereto.
- DIW deionized water
- ultrapure water in which impurities are reduced as much as possible, but are not limited thereto.
- the water may be included by absorbing moisture over time, it is preferable that the cleaning liquid composition according to the present invention does not contain water.
- the cleaning liquid composition according to the present invention has excellent cleaning power including the glyme-based compound represented by Chemical Formula 1, ultrasonic cleaning and electrolytic cleaning are unnecessary.
- the mask cleaning liquid composition may be a mask cleaning liquid composition for cleaning a mask used in an organic material vacuum deposition process.
- the mask cleaning liquid composition according to the present invention has an advantage of excellent cleaning power without including environmental regulatory substances such as NMP, NEP, DMF, and the like.
- the organic material was separated from the mask, made into a powder form using a mortar, and then separated into a 224 ⁇ m sieve.
- the solubility (melting rate, measurement in minutes) was dissolved by dissolving the organic material powder in the mask cleaning liquid composition at room temperature to satisfy 0.1% by weight with respect to 100% by weight of the total mask cleaning liquid composition prepared according to the Examples and Comparative Examples using a 50 ml beaker. The evaluation is shown in Table 2 below.
- Comparative Example 1 which includes an environmental regulatory substance, one or more masks showed 30 minutes or more, indicating that the dissolving ability was reduced.
- the organic material was separated from the mask, and then made into a powder form using a mortar and then separated into a 224 ⁇ m sieve.
- a glass 50 ml glass bottle was aliquoted and then room temperature. After leaving for 24 hours in the evaluation of the stability (turbidity increase and precipitate) of the mask cleaning liquid composition (chemical solution) according to Examples and Comparative Examples are shown in Table 3 below.
- Example 1 ⁇ ⁇ ⁇ Example 2 ⁇ ⁇ ⁇ Example 3 ⁇ ⁇ ⁇ Example 4 ⁇ ⁇ ⁇ Example 5 ⁇ ⁇ ⁇ Example 6 ⁇ ⁇ ⁇ Example 7 ⁇ ⁇ ⁇ Example 8 ⁇ ⁇ ⁇ Example 9 ⁇ ⁇ ⁇ Example 10 ⁇ ⁇ ⁇ Example 11 ⁇ ⁇ ⁇ Example 12 ⁇ ⁇ ⁇ Example 13 ⁇ ⁇ ⁇ Example 14 ⁇ ⁇ ⁇ Example 15 ⁇ ⁇ ⁇ Example 16 ⁇ ⁇ ⁇ Example 17 ⁇ ⁇ ⁇ Example 18 ⁇ ⁇ ⁇ Example 19 ⁇ ⁇ ⁇ Example 20 ⁇ ⁇ ⁇ Example 21 ⁇ ⁇ ⁇ Example 22 ⁇ ⁇ ⁇ Example 23 ⁇ ⁇ ⁇ Example 24 ⁇ ⁇ ⁇ Example 25 ⁇ ⁇ ⁇ Comparative Example 1 ⁇ ⁇ ⁇ Comparative Example 2 ⁇ ⁇ ⁇ Comparative Example 3 ⁇ ⁇ ⁇ Comparative Example 4 ⁇
- Comparative Examples except for Comparative Example 1 containing an environmental regulatory substance it may be confirmed that one or more chemical solutions are opaque and the dissolution stability is lowered.
- the comparative example containing a nonpolar solvent it can confirm that melt
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- Organic Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
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Abstract
La présente invention concerne une composition de solution de nettoyage de masque, comprenant un composé à base de glyme représenté par la formule chimique 1, mais ne contenant pas de solvant non polaire. Selon la présente invention, la composition de solution de nettoyage de masque démontre une puissance de nettoyage satisfaisante même sans comprendre de matériaux soumis à une réglementation environnementale.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2018-0014367 | 2018-02-06 | ||
| KR20180014367 | 2018-02-06 | ||
| KR1020180157353A KR102640138B1 (ko) | 2018-02-06 | 2018-12-07 | 마스크 세정액 조성물 |
| KR10-2018-0157353 | 2018-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2019156363A1 true WO2019156363A1 (fr) | 2019-08-15 |
Family
ID=67549732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2019/000230 Ceased WO2019156363A1 (fr) | 2018-02-06 | 2019-01-08 | Composition de solution de nettoyage de masque |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2019156363A1 (fr) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003129089A (ja) * | 2001-10-24 | 2003-05-08 | Daikin Ind Ltd | 洗浄用組成物 |
| KR20050037511A (ko) * | 2002-06-06 | 2005-04-22 | 이케이씨 테크놀로지, 인코포레이티드 | 반도체 공정상의 잔류물 제거 조성물 및 방법 |
| KR20080016930A (ko) * | 2005-07-19 | 2008-02-22 | 쇼와 덴코 가부시키가이샤 | 감광성 조성물용 제거액 |
| KR20080099413A (ko) * | 2007-05-09 | 2008-11-13 | 동우 화인켐 주식회사 | 감광성 수지 제거용 씬너 조성물 |
| KR20120039255A (ko) * | 2010-10-15 | 2012-04-25 | 동우 화인켐 주식회사 | 감광성 수지 제거용 세정액 조성물 |
-
2019
- 2019-01-08 WO PCT/KR2019/000230 patent/WO2019156363A1/fr not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003129089A (ja) * | 2001-10-24 | 2003-05-08 | Daikin Ind Ltd | 洗浄用組成物 |
| KR20050037511A (ko) * | 2002-06-06 | 2005-04-22 | 이케이씨 테크놀로지, 인코포레이티드 | 반도체 공정상의 잔류물 제거 조성물 및 방법 |
| KR20080016930A (ko) * | 2005-07-19 | 2008-02-22 | 쇼와 덴코 가부시키가이샤 | 감광성 조성물용 제거액 |
| KR20080099413A (ko) * | 2007-05-09 | 2008-11-13 | 동우 화인켐 주식회사 | 감광성 수지 제거용 씬너 조성물 |
| KR20120039255A (ko) * | 2010-10-15 | 2012-04-25 | 동우 화인켐 주식회사 | 감광성 수지 제거용 세정액 조성물 |
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