JP2007183577A - Aqueous alkali photoresist cleaning composition and usage of the composition - Google Patents

Aqueous alkali photoresist cleaning composition and usage of the composition Download PDF

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JP2007183577A
JP2007183577A JP2006303565A JP2006303565A JP2007183577A JP 2007183577 A JP2007183577 A JP 2007183577A JP 2006303565 A JP2006303565 A JP 2006303565A JP 2006303565 A JP2006303565 A JP 2006303565A JP 2007183577 A JP2007183577 A JP 2007183577A
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Wang Hang Tsai
ハン ツァイ，ワン
Wen Cheng Liu
チェン リュウ，ウェン
Chen Chen Ching
チン チェン，チエン
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CMC Materials Taiwan Co Ltd
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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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/40—Monoamines or polyamines; Salts thereof
    • 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
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • 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
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
    • G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
    • 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
    • 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
    • C11D2111/22—

Abstract

<P>PROBLEM TO BE SOLVED: To provide an aqueous alkali photoresist cleaning composition having a simple composition, not containing an organic solvent harmful to a worker and the environment, and having excellent solvent power to photoresist used in a photo process of a semiconductor integrated circuit or a liquid crystal display or photoresist residue in a photoresist coating device and a developer piping system. <P>SOLUTION: The aqueous alkali photoresist cleaning composition contains 1-50 wt.% of at least one alkali compound, 0.1-20 wt.% of at least one diamine compound and 30-98.9 wt.% of water, based on the total weight of the composition and has a pH of >12. The photoresist scrubbing composition can be heated and/or diluted before use according to actual process conditions. Since the composition contains no organic solvent, it can safely be used in a regular work environment. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

本発明は、半導体集積回路又は液晶ディスプレイのフォトプロセスにおいてフォトレジストを除去するために使用でき、またフォトレジストコーティング装置及び現像液配管系統から残留フォトレジストを洗浄するために使用できる水性アルカリフォトレジスト洗浄組成物に関する。本発明の水性アルカリフォトレジスト洗浄組成物は特に、液晶ディスプレイのカラーフィルタープロセスに使用されるカラーフォトレジストの処理に好適である。   The present invention is an aqueous alkaline photoresist cleaning that can be used to remove photoresist in photo processing of semiconductor integrated circuits or liquid crystal displays and can be used to clean residual photoresist from photoresist coating equipment and developer piping systems. Relates to the composition. The aqueous alkaline photoresist cleaning composition of the present invention is particularly suitable for processing a color photoresist used in a color filter process of a liquid crystal display.

半導体及び光電気産業においては、とりわけフォトプロセスが最も重要な一工程である。フォトプロセスによって規定される線幅や積層モード、解像度は時代と共に進歩している。光電気産業の場合は通常、フォトプロセスにおいて最初にカラーフォトレジストがスピンコーティング又はこれと異なる方法でガラス基板上にコーティングされ、続いてソフトベーク、露光、現像が行われる。   In the semiconductor and optoelectronic industries, the photo process is one of the most important steps. The line width, stacking mode, and resolution defined by the photo process are improving with the times. In the optoelectronic industry, usually a color photoresist is first coated on a glass substrate by spin coating or a different method in a photo process, followed by soft baking, exposure and development.

これまで当産業におけるフォトプロセス用フォトレジスト洗浄液は主に次の２用途に使用されてきた。即ち、（１）フォトレジスト剥離；フォトレジストは、露光及び現像に際し架橋反応或いは酸性化処理に付された後、配線パターンが得られるように洗浄除去する必要がある；（２）エッチング残渣除去又はアッシング後の洗浄；フォトレジストは、プラズマによるエッチングに際し灰化し基板上に残存するので洗浄する必要がある。   Until now, the photoresist cleaning liquid for photo process in this industry has been mainly used for the following two applications. (1) Photoresist stripping; the photoresist needs to be washed and removed so as to obtain a wiring pattern after being subjected to a crosslinking reaction or acidification treatment in exposure and development; (2) Etching residue removal or Cleaning after ashing; the photoresist is ashed during plasma etching and remains on the substrate, so it must be cleaned.

また、フォトレジスト洗浄液はフォトプロセスに加え、フォトレジストコーティング装置や現像液配管系統からの残留フォトレジストの洗浄に使用されてきた。光電気産業においては、ガラス基板の大型化により現像液の消費量が増大しているが、現在、当産業で使用される現像液は現像後に再利用のため回収することができ、これにより現像液にかかる費用が低減される。しかしながら、カラーフォトレジストのコーティング中に、フォトレジストの一部がガラス基板から飛散してコーター内部に残存し、その結果、連続的な大量生産の後、フォトレジスト残渣の厚い層がコーターの壁に形成される。更にこれらのフォトレジスト残渣は、現像液回収システムを通って現像液配管系統やバレル型の浴に入り、その結果、乾燥したフォトレジストがコーティング装置と現像液配管系統の至る所に付着するという現象が生じる。このフォトレジスト残渣は剥落後に現像液配管系統に入ってフィルターコアの効率に影響を及ぼす。フォトレジスト残渣の剥落がフィルターコアの後部で生じると、現像液の出口側端部のノズルを更に閉塞させてしまい、現像プロセスに影響を及ぼしてプロセス中に異常な現象が生じる。   In addition to the photo process, the photoresist cleaning liquid has been used for cleaning residual photoresist from a photoresist coating apparatus and a developer piping system. In the optoelectronic industry, the consumption of the developer is increasing due to the increase in the size of the glass substrate. Currently, the developer used in this industry can be recovered for reuse after development. The cost of the liquid is reduced. However, during the color photoresist coating, some of the photoresist scatters from the glass substrate and remains inside the coater, resulting in a thick layer of photoresist residue on the coater wall after continuous mass production. It is formed. Furthermore, these photoresist residues pass through the developer recovery system and enter the developer piping system and barrel type bath, and as a result, the dried photoresist adheres throughout the coating apparatus and the developer piping system. Occurs. This photoresist residue enters the developer piping system after stripping and affects the efficiency of the filter core. If the photoresist residue is peeled off at the rear part of the filter core, the nozzle at the end of the outlet side of the developer is further blocked, which affects the developing process and causes an abnormal phenomenon during the process.

これまで当産業において使用されているフォトレジスト洗浄組成物のほとんどは、作業者や環境に有害な有機溶媒（例えば、プロピレングリコールモノメチルエーテルエステル（ＰＧＭＥＡ）やシクロヘキサノン、エチルラクテート、メチルイソブチルケトン（ＭＩＢＫ）、Ｎ−メチルピロリドン（ＮＭＰ）、γ−ブチロラクトン、又はそれらの組合せ）を含む。   Until now, most of the photoresist cleaning compositions used in the industry are organic solvents harmful to workers and the environment (for example, propylene glycol monomethyl ether ester (PGMEA), cyclohexanone, ethyl lactate, methyl isobutyl ketone (MIBK)). N-methylpyrrolidone (NMP), γ-butyrolactone, or combinations thereof).

例えば特許文献１は、水酸化テトラメチルアンモニウムと、水溶性アミンと、アルキルピロリドンと、糖又は糖アルコールとを含むフォトレジスト除去組成物を開示している。該組成物において、アルキルピロリドンとしてＮ−メチルピロリドン（ＮＭＰ）が１０〜９０重量％使用されている。   For example, Patent Document 1 discloses a photoresist removing composition containing tetramethylammonium hydroxide, a water-soluble amine, an alkylpyrrolidone, and a sugar or a sugar alcohol. In the composition, 10 to 90% by weight of N-methylpyrrolidone (NMP) is used as alkylpyrrolidone.

特許文献２は、アルコールアミンと、アミンを０．０１〜１００重量％、水溶性有機溶媒を５〜８０重量％、水を５〜６０重量％（実施例において、水の量はいずれも３０％未満）、防食剤を１〜３５重量％、含むフォトレジスト残渣洗浄剤を開示している。   Patent Document 2 describes alcohol amine, 0.01 to 100% by weight of amine, 5 to 80% by weight of water-soluble organic solvent, and 5 to 60% by weight of water (in the examples, the amount of water is 30% in all cases). Less), and a photoresist residue cleaning agent containing 1 to 35% by weight of an anticorrosive agent.

当産業の実務者は、作業者と環境に有害な有機溶媒を用いる必要のないフォトレジスト洗浄剤の研究開発に取組んでいる。   Practitioners in the industry are working on research and development of photoresist cleaners that do not require the use of organic solvents that are harmful to workers and the environment.

特許文献３は、フォトレジストやポリイミド、ポリアミック酸等のポリマー残渣を除去するための水性洗浄液を開示している。該洗浄液は、アルカリ金属水酸化物又は水酸化テトラアルキルアンモニウムと、アルコールアミンと、非イオン性界面活性剤又は両性界面活性剤と、多塩基有機酸又は多塩基有機酸の塩とを含む。   Patent document 3 is disclosing the aqueous cleaning liquid for removing polymer residues, such as a photoresist, a polyimide, a polyamic acid. The cleaning liquid contains an alkali metal hydroxide or a tetraalkylammonium hydroxide, an alcohol amine, a nonionic surfactant or an amphoteric surfactant, and a polybasic organic acid or a salt of a polybasic organic acid.

特許文献４は、ｐＨ２〜６の酸性フォトレジスト洗浄組成物を用いてフォトレジスト残渣を除去する洗浄方法を開示している。該組成物は、水と、アミン又は水酸化テトラアルキルアンモニウムと、酸性ヒドロキシルアミンとを含む。このフォトレジスト洗浄組成物は、オゾン水発生器（ozone water machine）と共に使用する必要がある。   Patent Document 4 discloses a cleaning method for removing a photoresist residue using an acidic photoresist cleaning composition having a pH of 2 to 6. The composition comprises water, an amine or tetraalkylammonium hydroxide, and acidic hydroxylamine. This photoresist cleaning composition needs to be used with an ozone water machine.

特許文献５及び６は、プリント配線板（ＰＷＢ）からフォトレジスト粒子を除去するための洗浄方法及び洗浄装置を開示している。該方法に使用されるフォトレジスト洗浄組成物は主に、一般式（ＲkＮ）nＣqＲmで表されるオルガノアミンと、一般式［ＮyＲ’w］+［Ａ］-で表されるイオン性窒素化合物と、アルカリ金属又はアルカリ土類金属の水酸化物とを含む。これら明細書の開示内容によれば、前記オルガノアミンはアルコールアミン化合物であることが好ましい。
米国特許第６４４０３２６号明細書 米国特許第６６３８６９４号明細書 米国特許第６６３５１１８号明細書 米国特許第６２４５１５５号明細書 米国特許第５５９９４４４号明細書 米国特許第５５３１８８９号明細書 Patent Documents 5 and 6 disclose a cleaning method and a cleaning apparatus for removing photoresist particles from a printed wiring board (PWB). The photoresist cleaning composition used in the method is mainly composed of an organoamine represented by the general formula (R k N) n C q R m and a general formula [N y R ′ w ] + [A] − . And an ionic nitrogen compound represented by alkali metal or alkaline earth metal hydroxide. According to the disclosure of these specifications, the organoamine is preferably an alcohol amine compound.
US Pat. No. 6,440,326 US Pat. No. 6,638,694 US Pat. No. 6,635,118 US Pat. No. 6,245,155 US Pat. No. 5,599,444 US Pat. No. 5,531,889

当産業においては、組成が単純で、作業者及び環境に有害な有機溶媒を含有せず、且つ、半導体集積回路又は液晶ディスプレイのフォトプロセスに使用されるフォトレジスト、或いはフォトレジストコーティング装置及び現像液配管系統のフォトレジスト残渣に対して優れた溶解能を有する水性フォトレジスト洗浄組成物が依然として必要とされている。   In this industry, the composition is simple, does not contain an organic solvent harmful to workers and the environment, and is used in a photo process of a semiconductor integrated circuit or a liquid crystal display, or a photoresist coating apparatus and a developer. There remains a need for aqueous photoresist cleaning compositions that have excellent solubility in piping system photoresist residues.

本発明の主たる目的は、水性アルカリフォトレジスト洗浄組成物であって、該組成物の総重量に対して、少なくとも一種のアルカリ化合物を１〜５０重量％、少なくとも一種のジアミン化合物を０．１〜２０重量％、水を３０〜９８．９重量％含み、ｐＨが１２超である組成物を提供することである。   The main object of the present invention is an aqueous alkaline photoresist cleaning composition, comprising at least one alkali compound in an amount of 1 to 50% by weight and at least one diamine compound in an amount of 0.1 to 0.1% based on the total weight of the composition. It is to provide a composition containing 20% by weight, 30-98.9% by weight of water and having a pH of more than 12.

本発明の更なる目的は、液晶ディスプレイのカラーフィルターの製造方法であって、本発明の水性アルカリフォトレジスト洗浄組成物をカラーフォトレジストフィルムに接触させることにより、カラーフォトレジストフィルムをガラス基板から除去する段階を含む方法を提供することである。   A further object of the present invention is a method for producing a color filter for a liquid crystal display, wherein the color photoresist film is removed from the glass substrate by bringing the aqueous alkaline photoresist cleaning composition of the present invention into contact with the color photoresist film. Providing a method comprising the steps of:

本発明の更なる目的は、カラーフォトレジストコーティング装置及び現像液配管系統からカラーフォトレジスト残渣を洗浄する方法であって、本発明の水性アルカリフォトレジスト洗浄組成物をカラーフォトレジストコーティング装置及び現像液配管系統に接触させることにより、カラーフォトレジストコーティング装置及び現像液配管系統からカラーフォトレジスト残渣を除去する段階を含む方法を提供することである。   A further object of the present invention is a method for cleaning a color photoresist residue from a color photoresist coating apparatus and a developer piping system, the aqueous alkaline photoresist cleaning composition of the present invention being used as a color photoresist coating apparatus and a developer. It is to provide a method comprising removing color photoresist residue from a color photoresist coating apparatus and developer piping system by contacting the piping system.

本発明の水性アルカリフォトレジスト洗浄組成物は、組成物総重量に対して、少なくとも一種のアルカリ化合物を１〜５０重量％、少なくとも一種のジアミン化合物を０．１〜２０重量％、水を３０〜９８．９重量％含み、ｐＨが１２超、好ましくは１３超である。   The aqueous alkaline photoresist cleaning composition of the present invention comprises 1 to 50% by weight of at least one alkali compound, 0.1 to 20% by weight of at least one diamine compound, and 30 to 30% of water based on the total weight of the composition. It contains 98.9% by weight and the pH is more than 12, preferably more than 13.

本発明に用いられるアルカリ化合物は無機塩基又は有機塩基である。無機塩基は、好ましくは例えば、水酸化ナトリウムや水酸化カリウム、それらの混合物等の水酸化アルカリ金属化合物から選択され、また、有機塩基は、好ましくは次式で表される水酸化四級アンモニウム化合物から選択される。   The alkali compound used in the present invention is an inorganic base or an organic base. The inorganic base is preferably selected from alkali metal hydroxide compounds such as sodium hydroxide, potassium hydroxide and mixtures thereof, and the organic base is preferably a quaternary ammonium hydroxide compound represented by the following formula: Selected from.

Figure 2007183577
Figure 2007183577

（式中、Ｒ1、Ｒ2、Ｒ3及びＲ4は同一でも異なってもよく、それぞれ独立に１〜６個の炭素原子を有するアルキル又はヒドロキシアルキルを表す）。
より好ましくは、前記有機塩基は水酸化テトラメチルアンモニウムである。 (Wherein R 1 , R 2 , R 3 and R 4 may be the same or different and each independently represents alkyl or hydroxyalkyl having 1 to 6 carbon atoms).
More preferably, the organic base is tetramethylammonium hydroxide.

本発明におけるアルカリ化合物の使用量は、組成物総重量に対して１〜５０重量％の範囲であり、好ましくは１０〜５０重量％、より好ましくは２０〜５０重量％である。   The usage-amount of the alkali compound in this invention is the range of 1-50 weight% with respect to the composition total weight, Preferably it is 10-50 weight%, More preferably, it is 20-50 weight%.

本発明に用いるジアミン化合物は、好ましくはエチレンジアミン、プロピレンジアミン、テトラメチレンジアミン、ペンタメチレンジアミン、ヘキサメチレンジアミン、フェニレンジアミン、ジエチレンジアミン、トリエチレンジアミン、テトラエチレンジアミン及びそれらの混合物から成る群から選択され、なかでもエチレンジアミン、ジエチレンジアミン及びそれらの混合物がより好ましい。
本発明におけるジアミン化合物の使用量は、組成物総重量に対して０．１〜２０重量％の範囲であり、好ましくは１〜１０重量％、より好ましくは１〜５重量％である。 The diamine compound used in the present invention is preferably selected from the group consisting of ethylenediamine, propylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, phenylenediamine, diethylenediamine, triethylenediamine, tetraethylenediamine and mixtures thereof. However, ethylenediamine, diethylenediamine and mixtures thereof are more preferred.
The usage-amount of the diamine compound in this invention is the range of 0.1-20 weight% with respect to a composition total weight, Preferably it is 1-10 weight%, More preferably, it is 1-5 weight%.

本発明に用いる水は脱イオン水が好ましく、その量は組成物の総重量に対して３０〜９８．９重量％の範囲であり、好ましくは４０〜８９重量％、より好ましくは４５〜７９重量％である。   The water used in the present invention is preferably deionized water, and the amount thereof is in the range of 30 to 98.9% by weight, preferably 40 to 89% by weight, more preferably 45 to 79% by weight based on the total weight of the composition. %.

本発明の洗浄組成物には、洗浄組成物の表面張力を４０ｍＮ／ｍ未満とすることができる少なくとも一種の界面活性剤を、組成物総重量に対して０．０１〜３重量％任意に含有させることができる。界面活性剤を添加することによって、前記洗浄組成物の湿潤特性を向上させることができると共に表面張力を小さくすることができ、フォトレジストの剥離作用が向上する。本発明の好適な界面活性剤は、特に限定されないが、アニオン性、カチオン性、或いは非イオン性の界面活性剤である。   The cleaning composition of the present invention optionally contains 0.01 to 3% by weight of at least one surfactant capable of making the surface tension of the cleaning composition less than 40 mN / m with respect to the total weight of the composition. Can be made. By adding a surfactant, the wet characteristics of the cleaning composition can be improved, the surface tension can be reduced, and the photoresist peeling action is improved. A suitable surfactant of the present invention is not particularly limited, but is an anionic, cationic or nonionic surfactant.

本発明の水性アルカリフォトレジスト洗浄組成物は、半導体集積回路又は液晶ディスプレイのフォトプロセスにおいて用いられるフォトレジスト、或いはフォトレジストコーティング装置及び現像液配管系統のフォトレジスト残渣に対して優れた溶解能を有する。従って本発明の組成物は、フォトレジストを除去するためにフォトプロセスで用いることができ、またフォトレジストコーティング装置及び現像液配管系統からフォトレジスト残渣を洗浄するために用いることができる。   The aqueous alkaline photoresist cleaning composition of the present invention has an excellent dissolving ability for a photoresist used in a photo process of a semiconductor integrated circuit or a liquid crystal display, or a photoresist residue of a photoresist coating apparatus and a developer piping system. . Thus, the compositions of the present invention can be used in photoprocesses to remove photoresist and can be used to clean photoresist residues from photoresist coating equipment and developer piping systems.

好ましい実施形態においては、本発明の水性アルカリフォトレジスト洗浄組成物は、特に、液晶ディスプレイのカラーフィルターとして使用されるカラーフォトレジストの処理に適している。   In a preferred embodiment, the aqueous alkaline photoresist cleaning composition of the present invention is particularly suitable for the processing of color photoresists used as color filters for liquid crystal displays.

従って本発明は更に、液晶ディスプレイのカラーフィルターの製造方法であって、本発明の水性アルカリフォトレジスト洗浄組成物をカラーフォトレジストフィルムに接触させることにより、カラーフォトレジストフィルムをガラス基板から除去する段階を含む方法を提供する。   Accordingly, the present invention further provides a method for producing a color filter for a liquid crystal display, the step of removing the color photoresist film from the glass substrate by bringing the aqueous alkaline photoresist cleaning composition of the present invention into contact with the color photoresist film. A method comprising:

また本発明は、カラーフォトレジストコーティング装置及び現像液配管系統からカラーフォトレジスト残渣を洗浄する方法であって、本発明の水性アルカリフォトレジスト洗浄組成物をカラーフォトレジストコーティング装置及び現像液配管系統に接触させることにより、カラーフォトレジストコーティング装置及び現像液配管系統からカラーフォトレジスト残渣を除去する段階を含む方法を提供する。   The present invention is also a method for cleaning a color photoresist residue from a color photoresist coating apparatus and a developer piping system, and the aqueous alkaline photoresist cleaning composition of the present invention is applied to a color photoresist coating apparatus and a developer piping system. A method is provided that includes removing color photoresist residues from the color photoresist coating apparatus and developer piping system by contacting.

本発明の水性アルカリフォトレジスト洗浄組成物は、通常の温度でそのまま用いることができ、また実際のプロセスに必要な条件に応じて超純水にて希釈した後に用いることもできる。更に本発明の水性アルカリフォトレジスト洗浄組成物は、作業者及び環境に有害な有機溶媒を含有しないため、通常の作業環境で安全に利用することができる。プロセスの必要条件により、溶解作用を向上させるために昇温する必要がある場合でも、作業者は加熱によって起こり得る有毒物に注意を払う必要がない。更に、製造プロセスで生じる廃水は、ｐＨを中性にして通常使用される廃水処理により簡単に処理することができ、有機溶媒のための追加的な廃水処理を行う必要がない。   The aqueous alkaline photoresist cleaning composition of the present invention can be used as it is at a normal temperature, or can be used after being diluted with ultrapure water according to the conditions required for an actual process. Furthermore, since the aqueous alkaline photoresist cleaning composition of the present invention does not contain an organic solvent harmful to workers and the environment, it can be safely used in a normal working environment. Even if the process requirements require that the temperature be raised to improve dissolution, the operator need not pay attention to the toxic substances that can be caused by heating. Furthermore, the wastewater generated in the manufacturing process can be easily treated by a commonly used wastewater treatment with a neutral pH, and no additional wastewater treatment for the organic solvent is required.

以下、実施例を挙げて本発明を更に説明するが、これら実施例は本発明の範囲を限定することを意図するものではない。当業者によって容易に達成される変更や改変はいずれも本発明の範囲内にあるものとする。   EXAMPLES Hereinafter, although an Example is given and this invention is further demonstrated, these Examples do not intend limiting the scope of the present invention. Any changes or modifications readily achieved by those skilled in the art are intended to be within the scope of the present invention.

実施例１
操作方法
次表に示す組成の洗浄液組成物を各５０ｍＬとフォトレジストポリマー０．０６ｇを室温にて攪拌した。フォトレジストポリマーを１ｍｍ2未満までに溶解するのに要する時間を測定した。 Example 1
Method of Operation 50 mL of the cleaning liquid composition having the composition shown in the following table and 0.06 g of the photoresist polymer were stirred at room temperature. The time required to dissolve the photoresist polymer to less than 1 mm 2 was measured.

観察結果
表１の結果からアルカリ化合物のみを添加した場合には、カラーフォトレジストポリマーを短時間で１ｍｍ2未満までに効果的に溶解することができなかったことが分かる。 Observation Results From the results in Table 1, it can be seen that when only an alkali compound was added, the color photoresist polymer could not be effectively dissolved in less than 1 mm 2 in a short time.

Figure 2007183577
Figure 2007183577

表２の結果から、アルカリ化合物の他に界面活性剤（ＢＹＫ−Ｃｈｅｍｉｅ ＧｍｂＨ、ドイツ；ＢＹＫ−３８０Ｎ）を添加したことにより、カラーフォトレジストポリマーの溶解時間を更に短縮することができるが、フォトレジストの溶解に要する時間は依然として極めて長いことが分かる。これは界面活性剤の添加は、溶解効率を向上させることを目的としているのではなく、表面張力を小さくすると共に湿潤性を向上させることによって配管系統の壁部からのフォトレジストの剥離効率を向上させることを目的としているからである。表２と表３を比較すると分かるように、更にジアミン化合物を組成物に添加する場合に限って、カラーフォトレジストの溶解時間を大幅に短縮できる。   From the results shown in Table 2, the addition of a surfactant (BYK-Chemie GmbH, Germany; BYK-380N) in addition to the alkali compound can further shorten the dissolution time of the color photoresist polymer. It can be seen that the time required for dissolution of is still very long. This is because the addition of a surfactant is not intended to improve the dissolution efficiency, but to improve the stripping efficiency of the photoresist from the wall of the piping system by reducing the surface tension and improving the wettability. It is because it aims to make it. As can be seen by comparing Table 2 and Table 3, the dissolution time of the color photoresist can be greatly shortened only when a diamine compound is further added to the composition.

Figure 2007183577
Figure 2007183577

Figure 2007183577
Figure 2007183577

実施例２
操作方法
次表に示す組成の洗浄液組成物を、脱イオン水を用いて各倍率に希釈した。各希釈倍率の洗浄液組成物５０ｍＬとフォトレジストポリマー０．０６ｇを３５℃で攪拌した。フォトレジストポリマーを１ｍｍ2未満にまで溶解するのに要する時間を測定した。 Example 2
Operation method The cleaning liquid composition having the composition shown in the following table was diluted to each magnification with deionized water. 50 mL of the cleaning liquid composition at each dilution ratio and 0.06 g of the photoresist polymer were stirred at 35 ° C. The time required to dissolve the photoresist polymer to less than 1 mm 2 was measured.

観察結果
（１）表４の結果から希釈後においても本発明に係る洗浄組成物は、赤色フォトレジストポリマーに対する優れた溶解作用を有することが分かる。 Observation Result (1) From the results in Table 4, it can be seen that the cleaning composition according to the present invention has an excellent dissolving action on the red photoresist polymer even after dilution.

Figure 2007183577
Figure 2007183577

（２）表５の結果から、希釈後においても本発明に係る洗浄組成物は、緑色フォトレジストポリマーに対する優れた溶解作用を有することが分かる。 (2) From the results in Table 5, it can be seen that the cleaning composition according to the present invention has an excellent dissolving action on the green photoresist polymer even after dilution.

Figure 2007183577
Figure 2007183577

（３）表６の結果から、希釈後においても本発明に係る洗浄組成物は、青色フォトレジストポリマーに対する優れた溶解作用を有することが分かる。 (3) From the results in Table 6, it can be seen that the cleaning composition according to the present invention has an excellent dissolving action on the blue photoresist polymer even after dilution.

Figure 2007183577
Figure 2007183577

実施例３
操作方法
次表に示す組成の洗浄液組成物を１．３倍に希釈した。希釈洗浄液組成物を各５０ｍＬとフォトレジストポリマー０．０６ｇを、温度を変えて攪拌した。フォトレジストポリマーを１ｍｍ2未満までに溶解するのに要する時間を測定した。 Example 3
Operation method The cleaning liquid composition having the composition shown in the following table was diluted 1.3 times. 50 mL each of the diluted cleaning solution composition and 0.06 g of the photoresist polymer were stirred at different temperatures. The time required to dissolve the photoresist polymer to less than 1 mm 2 was measured.

観察結果
表７の結果から分かるように、操作温度を上げることで本発明洗浄組成物のフォトレジスト溶解能を著しく向上させることができる。 Observation Results As can be seen from the results in Table 7, the ability to dissolve the photoresist of the cleaning composition of the present invention can be significantly improved by raising the operating temperature.

Figure 2007183577
Figure 2007183577

実施例４
操作方法
次表に示す組成の洗浄液組成物を各５０ｍＬとフォトレジストポリマー０．０６ｇを室温にて攪拌した。フォトレジストポリマーを１ｍｍ2未満までに溶解するのに要する時間を測定した。 Example 4
Method of Operation 50 mL of the cleaning liquid composition having the composition shown in the following table and 0.06 g of the photoresist polymer were stirred at room temperature. The time required to dissolve the photoresist polymer to less than 1 mm 2 was measured.

観察結果
表８の結果から分かるように、先行技術に開示のアルコールアミン化合物（即ち、エタノールアミン又はジエタノールアミン）に代えてジアミン化合物（ジエチレンジアミン）を用いることにより、洗浄組成物のフォトレジスト溶解能を著しく向上させることができる。 Observation results As can be seen from the results in Table 8, the use of a diamine compound (diethylenediamine) in place of the alcoholamine compound (ie, ethanolamine or diethanolamine) disclosed in the prior art improves the photoresist dissolving ability of the cleaning composition. It can be significantly improved.

Figure 2007183577
Figure 2007183577

Claims (13)

水性アルカリフォトレジスト洗浄組成物であって、該組成物の総重量に対し、
（ａ）少なくとも１種のアルカリ化合物を１〜５０重量％；
（ｂ）少なくとも１種のジアミン化合物を０．１〜２０重量％；及び
（ｃ）水を３０〜９８．９重量％含み、
ｐＨが１２超である組成物。 An aqueous alkaline photoresist cleaning composition, relative to the total weight of the composition,
(A) 1 to 50% by weight of at least one alkali compound;
(B) 0.1-20 wt% of at least one diamine compound; and (c) 30-98.9 wt% of water,
A composition having a pH greater than 12. アルカリ化合物は無機塩基又は有機塩基である、請求項１に記載の組成物。   The composition according to claim 1, wherein the alkali compound is an inorganic base or an organic base. 無機塩基は水酸化アルカリ金属化合物であり、有機塩基は次式：
Figure 2007183577
 （式中、Ｒ1、Ｒ2、Ｒ3及びＲ4は同一でも異なってもよく、それぞれ独立に１〜６個の炭素原子を有するアルキル又はヒドロキシアルキルを表す）で表される水酸化四級アンモニウム化合物である、請求項２に記載の組成物。 The inorganic base is an alkali metal hydroxide compound, and the organic base has the following formula:
Figure 2007183577
 (Wherein R 1 , R 2 , R 3 and R 4 may be the same or different and each independently represents alkyl or hydroxyalkyl having 1 to 6 carbon atoms). The composition of claim 2 which is an ammonium compound. 水酸化アルカリ金属化合物は水酸化ナトリウム又は水酸化カリウムであり、水酸化四級アンモニウム化合物は水酸化テトラメチルアンモニウムである、請求項３に記載の組成物。   The composition according to claim 3, wherein the alkali metal hydroxide compound is sodium hydroxide or potassium hydroxide, and the quaternary ammonium hydroxide compound is tetramethylammonium hydroxide. ジアミン化合物は、エチレンジアミン、プロピレンジアミン、テトラメチレンジアミン、ペンタメチレンジアミン、ヘキサメチレンジアミン、フェニレンジアミン、ジエチレンジアミン、トリエチレンジアミン及びテトラエチレンジアミンから成る群から選択される、請求項１に記載の組成物。   The composition of claim 1, wherein the diamine compound is selected from the group consisting of ethylenediamine, propylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, phenylenediamine, diethylenediamine, triethylenediamine, and tetraethylenediamine. アルカリ化合物の量は１０〜５０重量％の範囲であり、ジアミン化合物の量は１〜１０重量％の範囲であり、水の量は４０〜８９重量％の範囲である、請求項１に記載の組成物。   The amount of alkali compound is in the range of 10 to 50 wt%, the amount of diamine compound is in the range of 1 to 10 wt%, and the amount of water is in the range of 40 to 89 wt%. Composition. アルカリ化合物の量は２０〜５０重量％の範囲であり、ジアミン化合物の量は１〜５重量％の範囲であり、水の量は４５〜７９重量％の範囲である、請求項６に記載の組成物。   The amount of alkali compound is in the range of 20-50% by weight, the amount of diamine compound is in the range of 1-5% by weight, and the amount of water is in the range of 45-79% by weight. Composition. 洗浄組成物の表面張力を４０ｍＮ／ｍ未満とすることができる少なくとも一種の界面活性剤を組成物の総重量に対して０．０１〜３重量％の量において更に含む、請求項１に記載の組成物。   2. The surfactant according to claim 1, further comprising at least one surfactant capable of bringing the surface tension of the cleaning composition to less than 40 mN / m in an amount of 0.01 to 3% by weight relative to the total weight of the composition. Composition. 界面活性剤はアニオン性、カチオン性又は非イオン性の界面活性剤である、請求項８に記載の組成物。   9. A composition according to claim 8, wherein the surfactant is an anionic, cationic or nonionic surfactant. 前記組成物のｐＨは１３超である、請求項１に記載の組成物。   The composition of claim 1, wherein the pH of the composition is greater than 13. フォトレジストは液晶ディスプレイのカラーフィルターとして使用されるカラーフォトレジストである、請求項１に記載の組成物。   The composition according to claim 1, wherein the photoresist is a color photoresist used as a color filter of a liquid crystal display. カラーフォトレジストフィルムを請求項１に記載の水性アルカリフォトレジスト洗浄組成物と接触させることにより、ガラス基板上の前記カラーフォトレジストフィルムを除去する段階を含む、液晶ディスプレイのカラーフィルターの製造方法。   A method for producing a color filter for a liquid crystal display, comprising the step of removing the color photoresist film on a glass substrate by bringing the color photoresist film into contact with the aqueous alkaline photoresist cleaning composition according to claim 1. カラーフォトレジストコーティング装置及び現像液配管系統を請求項１に記載の水性アルカリフォトレジスト洗浄組成物と接触させることにより、前記カラーフォトレジストコーティング装置及び現像液配管系統からカラーフォトレジスト残渣を除去する段階を含む、カラーフォトレジストコーティング装置及び現像液配管系統からカラーフォトレジスト残渣を洗浄するための方法。   Removing a color photoresist residue from the color photoresist coating apparatus and developer piping system by contacting the color photoresist coating apparatus and developer piping system with the aqueous alkaline photoresist cleaning composition of claim 1. A method for cleaning color photoresist residues from a color photoresist coating apparatus and developer piping system.
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