CN103197515A - Preparation method of photoetching developing liquid - Google Patents
Preparation method of photoetching developing liquid Download PDFInfo
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- CN103197515A CN103197515A CN2013101347541A CN201310134754A CN103197515A CN 103197515 A CN103197515 A CN 103197515A CN 2013101347541 A CN2013101347541 A CN 2013101347541A CN 201310134754 A CN201310134754 A CN 201310134754A CN 103197515 A CN103197515 A CN 103197515A
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Abstract
The invention discloses a preparation method of a photoetching developing liquid, and the preparation method is characterized in that tetramethyl-ammonium and triethyl-monomethyl-ammonium carbonate monomethyl ester mixture midbody are synthesized by mixing trimethylamine, triethylamine and methyl-carbonate according to a given ratio. The tetramethylammonium hydroxide and triethyl-monomethyl ammonium hydroxide mixed ammonium developing solution can be finally prepared through the procedures such as hydrolysis, purification and electrolysis. Meanwhile, alkyl ammonium hydroxide aqueous solution of the alkyl structure can be obtained by adding diethyl carbonate. The prepared alkyl ammonium hydroxide mixed ammonium developing solution of different chain length structures is low in production prices, simple in process, low in metal content and applicable to the developing requirement of a short wavelength light source technology with a fine precision narrow line.
Description
Technical field
The present invention relates to a kind of preparation method who is applied to the developer solution of the narrow linewidth photoresist developing technology in integrated circuit (IC) and the Thin Film Transistor-LCD (TFT-LCD), this developer solution can be used for occasions such as ultraviolet positive photoresist and chemical amplification type photoresist.
Background technology
Utilize photoresist coating, the light shield mask etching of developing then to obtain the photoresist etching technique of required pattern, be widely used in integrated circuit, field of microelectronic fabrication such as TFT-LCD.What be most widely used at present is organic base developer solution based on Tetramethylammonium hydroxide (TMAH), introduces metallic ion and causes problem of short-circuit to overcome inorganic base.Development with common ultraviolet positive photoresist is example, the mechanism of its development is: the photoresist emulsion of the area of the pattern by ultraviolet light on the light shield has partly generated indenes acid, destroy Novolak type phenolics simultaneously with main bridge linking effect based on hydrogen bond and nitrine coupling between the emulsion, thereby impelled photoresist to be dissolved in the alkali lye.Chemical amplification method photoresist then is to hang functional group's generation-O-C-O bond rupture under the situation of exposure light source irradiation by photo-acid generator catalytic polymer chain, produce more acidic-group, thereby make the polymer chain that originally is insoluble to alkali lye be dissolved in the purpose that reaches display pattern in the alkali lye.This acid catalysis effect makes the photoresist light sensitivity significantly strengthen, and the concentration of used alkali lye reduces, and more harsh to the requirement of developer solution etching speed and etching shape.
The industrialization of producing TMAH technology by the electrolysis tetramethyl ammonium successfully makes organic base possess the condition of large-scale application.Electron level TMAH has low price, and metal ion content is low, can be applicable to multiple novel positivity or the occasion of negativity photoresistance development, and advantage reliable for effect.The output of TMAH and consumption all surpass 60,000 tons in recent years, are mainly used in the TFT-LCD industry.
Yet the developing rate of the developer solution of single TMAH component is subject to the influence of Carbon Dioxide in Air, and the initial stage developing rate is very fast, because generating carbonate the development effect of developer solution is changed.The way that needs the NF molecule mwco membrane of application of expensive to remove TMAH carbonate and add TMAH is to overcome the influence that generates the developing performance deterioration that carbonate causes.Simultaneously, to widely used Array ultraviolet positive photoresist occasion in the TFT-LCD technology, the photoresistance of the non-exposed area of TMAH has significant dissolving power.In the use occasion of most of TMAH developer solution, the working concentration of TMAH developer solution is 0.26N(2.38%), to guarantee enough developing rate and product line production efficiency fast.This concentration can be to the swelling dissolving power significantly that has of the photoresistance of non-exposed area.In theory, the working concentration of TMAH should be less than 1%, far below 2.38% concentration value of common application from the maximum photoresistance dissolving (＜10%) that allows.Along with the further raising that the resolution sharpness of TFT-LCD requires, the live width of Array array is more and more littler, and the swelling dissolving of the non-exposed area of TMAH photoresistance can cause problems such as broken string.Thereby single TMAH solution not too is fit to be applied to the field to the further refinement requirement of live width.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of photoetch developer solution and preparation method thereof is provided.
The objective of the invention is to be achieved through the following technical solutions: a kind of preparation method of photoetch developer solution comprises the following steps:
(1) the refining mixing: trimethylamine and triethylamine are absorbed with methyl alcohol rectified purified back respectively, add reactor, dimethyl carbonate adds reactor after rectified purified; The mol ratio of triethylamine and trimethylamine is 0.10-0.50:1; The mol ratio of trimethylamine and dimethyl carbonate is 0.7-1.4:1;
(2) synthetic: feed the nitrogen replacement air in the reactor, the control reacting system pressure is at 1.2MPa-3MPa, and temperature of reaction keeps the reaction time at 4-8 hour at 110-130 degree centigrade; Deliver to evaporator recovered under reduced pressure methanol solvate and unreacted trimethylamine and dimethyl carbonate after the reaction, obtain tetramethyl-ammonium carbonic acid mono-methyl and triethyl monomethyl ammonium carbonic acid mono-methyl potpourri intermediate;
(3) hydrolysis: the tetramethyl-ammonium carbonic acid mono-methyl that comes out from evaporator and triethyl monomethyl ammonium carbonic acid mono-methyl potpourri intermediate add excessive high purity water and are hydrolyzed, temperature control is at 68-72 ℃, hydrolysis time control obtained the mixture aqueous solution of tetramethyl ammonium hydrogen carbonate and triethyl monomethyl ammonium bicarbonate at 1 hour; Part water and methyl alcohol steam in the hydrolytic process, reclaim byproduct of reaction methyl alcohol after the condensation;
(4) refining: as the tetramethyl ammonium hydrogen carbonate of hydrolysis generation and the mixture aqueous solution of triethyl monomethyl ammonium bicarbonate to be made with extra care through stripping tower, and sent into exchange resin tower and further remove metallic ion;
(5) electrolysis: the tetramethyl ammonium hydrogen carbonate of purifying and the potpourri of triethyl monomethyl ammonium bicarbonate are imported the electrolyzer anode chamber that cation selective sees through the film isolation, control anode liquid level and internal circulating load, in catholyte, inject high purity water or low concentration TMAH, and the energising electrolysis; The rare tetramethyl ammonium hydrogen carbonate of separation and triethyl monomethyl bicarbonate ammonium salt enter the anolyte circulation groove in the anode chamber, separate electrolysis and produce gas; Obtain TMAH and triethyl monomethyl ammonium hydroxide mixing ammonium product at catholyte; Concentration range remains on 20-40%, and all metal ions concentration is less than 100ppb;
(6) dilution: being diluted to mass concentration is the photoetch developer solution of 0.5-25%.
The invention has the beneficial effects as follows, the present invention has used the organic alkali developer solution for mixing the ammonium developer solution, can overcome single Tetramethylammonium hydroxide unstable and under low concentration significant swelling dissolving unexposed area photoresist and the pattern that causes caves in and the shortcoming of photoresist layer attenuate, and manufacturing price is relatively cheap, easily preparation and industrial applications.The microfabrication demand of the short wavelength light source technology of the thinner accuracy requirement of suitable narrow linewidth.
Simultaneously owing to utilize process units and the process control method of existing electron level TMAH, can produce metallic ion is other developer solution of ppb level, thereby eliminated impurity metal ion for the transistorized adverse effect of TFT, adapted to the requirement that the high resolving power high image quality shows processing procedure.Also can satisfy the requirement of narrow linewidth IC manufacture craft.This be other systems of using additive formulations can't reach easily.
These organic ammonium potpourri developer solution products with different chain length structure can keep molar equivalent hydroxy consistent with single Tetramethylammonium hydroxide when using, i.e. 0.26N (2.38%).Improve when correspondingly, the massfraction of mixing ammonium is than single Tetramethylammonium hydroxide.Because the increase of alkyl chain length, sterically hindered increase mixes ammonium to the rate of dissolution reduction of exposed photoresist, and the ability of dissolving exposed photoresist increases.But the diffusivity that enters unexposed photoresist is reduced, thereby minimizing is to the dissolving of the photoresistance of unexposed area.On the other hand, mix ammonium to the receptivity reduction of carbon dioxide, developer solution stability increases, and can reduce pattern defect rate and stain rate.
Description of drawings
Fig. 1 is the process chart of the organic mixing ammonium of preparation electron level photoetch developer solution.
Embodiment
The organic ammonium mixed liquor of the different chain structures that photoetch developer solution of the present invention is electron level, be mainly used in narrow linewidth, high-resolution integrated circuit (IC) and high resolving power Thin Film Transistor-LCD (TFT-LCD) field, pattern when being developer solution with TMAH separately to solve narrow linewidth technology easily caves in, dissolubility to the non-exposed area is good excessively, process window is young, and the development quality is subject to problems such as carbon dioxide influence.
Photoetch developer solution of the present invention is organic mixing ammonium, and key component is Tetramethylammonium hydroxide.Simultaneously, according to the needs of developing process, by the amount of control synthesis phase adding triethylamine, can produce the triethyl monomethyl ammonium hydroxide of different content and the mixed liquor of Tetramethylammonium hydroxide.By introducing certain backbone tetra-allkylammonium, can effectively adjust developing rate, alleviate the risk that pattern caves in.Can change simultaneously the wetting state to the non-exposed area, thereby improve the development quality.On the other hand, the organic ammonium mixed liquor can significantly improve the stability of developer solution, improves the process window applicability, and prolongs developer solution serviceable life, improves the developer solution service efficiency.
The compound developer solution of photoetch of the present invention is the organic ammonium mixed liquor of electron level, can avoid under the narrow linewidth application conditions introducing a large amount of impurity metal ions when adding other adjuvant, be reduced in the case because of the exceed standard risk of the line short that causes of metallic ion.
The preparation method of photoetch developer solution of the present invention comprises the following steps:
The first step, the refining mixing: refining trimethylamine and triethylamine are absorbed with the methyl alcohol polar solvent, and add reactor according to preset proportion.The addition of trimethylamine and triethylamine can be in following ratio: mole dosage is than triethylamine: trimethylamine=0.10-0.50:1.Preferred mole dosage is than triethylamine: trimethylamine=0.10-0.20:1.Dimethyl carbonate adds reactor after rectified purified.The addition of dimethyl carbonate is: mole dosage is than trimethylamine: dimethyl carbonate=0.7-1.4:1.Preferred mole dosage is than trimethylamine: dimethyl carbonate=0.9-1.3:1.
Second step, synthetic: that above-mentioned solution is fully mixed in autoclave.Use the nitrogen replacement air, system pressure is confirmed in pressurization, and the control reacting system pressure is at 1.2MPa-3MPa.With steam temperature of charge slowly is increased to about 90 degrees centigrade.After confirming system pressure, continue to heat up, keep temperature of reaction at 110-130 degree centigrade.Keep the reaction time at 4-8 hour.Reaction back recovered under reduced pressure methanol solvate and a small amount of unreacted trimethylamine and dimethyl carbonate return system's use after refining.Determine reaction conversion ratio with the gas chromatography determination DMC addition.
In this step, can make the potpourri intermediate of tetramethyl-ammonium carbonic acid mono-methyl and triethyl monomethyl ammonium carbonic acid mono-methyl.
In this step, the intermediate synthesis reaction vessel is batch reactor or continuous high pressure reactor.
In the 3rd step, hydrolysis: the intermediate that comes out from evaporator adds excessive high purity water and is hydrolyzed, and temperature is controlled about 70 degrees centigrade (68-72 ℃), and hydrolysis time was controlled about 1 hour.Part water and methyl alcohol steam in the hydrolytic process, start the Methanol Recovery device, reclaim byproduct of reaction methyl alcohol after the condensation.
The 4th step, refining: as the tetramethyl ammonium hydrogen carbonate of hydrolysis generation and the mixture aqueous solution of triethyl monomethyl ammonium bicarbonate to be made with extra care through stripping tower, and sent into exchange resin tower and further remove metallic ion.
The 5th step, electrolysis: the tetramethyl ammonium hydrogen carbonate of purifying and the potpourri of triethyl monomethyl ammonium bicarbonate (concentration about 60%) are imported the cation selective of a film two Room through the electrolyzer anode chamber of film isolation, control anode liquid level and internal circulating load, in catholyte, inject high purity water or low concentration TMAH, and the energising electrolysis.The rare tetramethyl ammonium hydrogen carbonate of separation and triethyl monomethyl bicarbonate ammonium salt enter the anolyte circulation groove in the anode chamber, separate electrolysis and produce gas.Obtain TMAH and triethyl monomethyl ammonium hydroxide mixing ammonium product at catholyte, the mass concentration scope remains on 20-40%, all metal ions concentration is less than 100ppb, control less than 10ppb. wherein, cationic membrane can adopt the Nafion of E.I.Du Pont Company series, the Aciplex-F series of company of Asahi Chemical Industry, and the 8-series of Japan AGC.Electrode anode can adopt stainless steel electrode or titanium base to cover metal oxide such as ruthenic oxide, titanium dioxide etc.; Be negative electrode with stainless steel electrode or nickel.The high-purity plastics of cell lining are to reach the electronic grade product production requirement.The operating conditions of electrolytic tank is: current density is 100-10000A/m
2, preferred 500-5000A/m
2Electrolysis temperature is controlled at 20-80 ° of C, preferred 30-70 ° of C.
The 6th step, dilution: be diluted to the 0.5-25% product according to final user's needs.
Photoetch developer solution of the present invention also comprises uses above-mentioned flow process, use the trimethylamine of different proportion, dimethyl carbonate, and diethyl carbonate is reaction raw materials, making with TMAH is principal ingredient, comprises the mixing ammonium developer solution of trimethyl list ethyl ammonium hydroxide.
Photoetch developer solution of the present invention also comprises uses above-mentioned flow process, use the trimethylamine of different proportion, triethylamine, dimethyl carbonate, diethyl carbonate is reaction raw materials, making with TMAH is principal ingredient, comprises trimethyl list ethyl ammonium hydroxide, the mixing ammonium developer solution of triethyl monomethyl ammonium hydroxide.
Certainly, photoetch developer solution of the present invention also comprises uses above-mentioned technology, according to practical application developing process needs, by regulating different ratios of raw materials, prepared TMAH and the variety classes that contains different proportion, the developer solution of the organic ammonium of different chain length structure.
Developer solution of the present invention can be by the process units production of industrialized electron level TMAH, can effectively control tenor, thereby it is low to have a metal ion content, cost is low, the soup long service life, to advantage such as a little less than the swelling dissolving power of non-exposed area, be applicable to the IC technology of high-resolution TFT-LCD processing procedure and narrow linewidth.
With embodiment the present invention is described in further detail with reference to the accompanying drawings below, it is more obvious that purpose of the present invention and effect will become.
Embodiment 1
The trimethylamine of 0.5 mole triethylamine and 1 mole is refining respectively, and be dissolved in 2.8 moles of refining methyl alcohol, add autoclave, again 1 mole dimethyl carbonate is added autoclave, use nitrogen replacement, at 110 ° of C, pressure is to react 8 hours under the 1.2MPa.Reaction conversion ratio counts 98% with dimethyl carbonate.The intermediate that reaction obtains is removed most of methyl alcohol after decompression distillation, add excessive high purity water then and be hydrolyzed under 68 degrees centigrade, and part water and methyl alcohol are steamed in the hydrolysis, make with extra care back the methyl alcohol storage tank after condensation.Salt is sent into electrowinning process after the hydrolysis after refining.The electrolytic tank electrolysis temperature is 70 degrees centigrade, current density 500A/m
2, electrolysis products obtained therefrom concentration is 20%, is recorded by the standard salt acidimetry.Obtaining can be used for producing volumetric molar concentration on the line through dilution is that the product of 0.26N is A.
Embodiment 2
The trimethylamine potpourri of 0.1 mole triethylamine and 1 mole is refining, be dissolved in 2.8 moles of refining methyl alcohol, add autoclave.Again 0.8 mole dimethyl carbonate and 0.2 mole diethyl carbonate are added autoclave, use nitrogen replacement, at 130 ° of C, pressure is to react 4 hours under the 3MPa.Reaction conversion ratio in dimethyl carbonate 99.11%.The intermediate that reaction obtains is removed most of methyl alcohol after decompression distillation, add excessive high purity water then and be hydrolyzed (72 degrees centigrade of temperature), and part water and methyl alcohol are steamed in the hydrolysis, make with extra care back the methyl alcohol storage tank after condensation.Salt is sent into electrowinning process after the hydrolysis after refining.The electrolytic tank electrolysis temperature is 65 degrees centigrade, current density 5000A/m
2, electrolysis products obtained therefrom concentration is 40%, is recorded by the standard salt acidimetry.Obtaining can be used for producing volumetric molar concentration on the line through dilution is that the product of 0.26N is B.
Embodiment 3
With the cut-back product A in above-described embodiment, B, and 2.38%TMAH, 3.88% tetraethyl ammonium hydroxide solution was placed in the air, measured pH value every 24 hours, absorbed the influence of Carbon Dioxide in Air under the simulated field applicable cases.Result such as table 1 mix organic ammonium and can reduce Carbon Dioxide in Air significantly to the influence of pH value.
Table 1: mix the aerial stability of organic ammonium developer solution
| pH | 2.38%TMAH | Product A | Product B | 3.88%TEAH |
| 0 | 13.22 | 13.25 | 13.29 | 13.2 |
| 1 day | 13.11 | 13.24 | 13.27 | 13.22 |
| 2 days | 12.95 | 13.1 | 13.21 | 12.97 |
| 3 days | 12.61 | 13.05 | 13.12 | 12.68 |
| 4 days | 10.61 | 11.61 | 11.95 | 10.69 |
| 5 days | 10.6 | 11.01 | 11.38 | 10.67 |
Embodiment 4
With the fresh developer solution sample among the embodiment 3, and the sample of the above-mentioned concentration after displaying 6 days dissolves the ultraviolet positive photoresist AZ1400K after the excessive exposure respectively.Filter the back and detect absorbance at the 290nm place with ultraviolet spectrophotometer.Result such as table 2, mixing organic ammonium can increase the amount of dissolving photoresist significantly than single TMAH, thereby improves the developer solution service efficiency.
Table 2: the dissolving photoresistance ability of mixing the organic ammonium developer solution
| The sample situation | Sample type | pH | The 290nm absorbance |
| Fresh | 2.38%TMAH | 13.22 | 69 |
| Fresh | Product A | 13.04 | 116.5 |
| Fresh | Product B | 13.10 | 121.1 |
| Fresh | 3.88%TEAH | 13.13 | 131.4 |
| After 6 days | 2.38%TMAH | 10.62 | 1.479 |
| After 6 days | Product A | 10.72 | 1.78 |
| After 6 days | Product B | 10.92 | 2.34 |
| After 6 days | 3.88%TEAH | 10.58 | 1.294 |
Certainly, the present invention still has multiple concrete embodiment, and all employings are equal to replacement or equivalent transformation and all technical schemes of forming, all drop within the scope of protection of present invention.
Claims (4)
1. the preparation method of a photoetch developer solution is characterized in that, comprises the following steps:
(1) the refining mixing: trimethylamine and triethylamine are absorbed with methyl alcohol rectified purified back respectively, add reactor, dimethyl carbonate adds reactor after rectified purified; The mol ratio of triethylamine and trimethylamine is 0.10-0.50:1; The mol ratio of trimethylamine and dimethyl carbonate is 0.7-1.4:1;
(2) synthetic: feed the nitrogen replacement air in the reactor, the control reacting system pressure is at 1.2MPa-3MPa, and temperature of reaction keeps the reaction time at 4-8 hour at 110-130 degree centigrade; Deliver to evaporator recovered under reduced pressure methanol solvate and unreacted trimethylamine and dimethyl carbonate after the reaction, obtain tetramethyl-ammonium carbonic acid mono-methyl and triethyl monomethyl ammonium carbonic acid mono-methyl potpourri intermediate;
(3) hydrolysis: the tetramethyl-ammonium carbonic acid mono-methyl that comes out from evaporator and triethyl monomethyl ammonium carbonic acid mono-methyl potpourri intermediate add excessive high purity water and are hydrolyzed, temperature control is at 68-72 ℃, hydrolysis time control obtained the mixture aqueous solution of tetramethyl ammonium hydrogen carbonate and triethyl monomethyl ammonium bicarbonate at 1 hour; Part water and methyl alcohol steam in the hydrolytic process, reclaim byproduct of reaction methyl alcohol after the condensation;
(4) refining: as the tetramethyl ammonium hydrogen carbonate of hydrolysis generation and the mixture aqueous solution of triethyl monomethyl ammonium bicarbonate to be made with extra care through stripping tower, and sent into exchange resin tower and further remove metallic ion;
(5) electrolysis: the tetramethyl ammonium hydrogen carbonate of purifying and the potpourri of triethyl monomethyl ammonium bicarbonate are imported the electrolyzer anode chamber that cation selective sees through the film isolation, control anode liquid level and internal circulating load, in catholyte, inject high purity water or low concentration TMAH, and the energising electrolysis; The rare tetramethyl ammonium hydrogen carbonate of separation and triethyl monomethyl bicarbonate ammonium salt enter the anolyte circulation groove in the anode chamber, separate electrolysis and produce gas; Obtain TMAH and triethyl monomethyl ammonium hydroxide mixing ammonium product at catholyte; Concentration range remains on 20-40%, and all metal ions concentration is less than 100ppb;
(6) dilution: being diluted to mass concentration is the photoetch developer solution of 0.5-25%.
2. according to the preparation method of the described photoetch developer solution of claim 1, it is characterized in that in the described step 1, preferably, the mol ratio of triethylamine and trimethylamine is 0.10-0.20:1; The mol ratio of trimethylamine and dimethyl carbonate is 0.9-1.3:1.
3. according to the preparation method of the described photoetch developer solution of claim 1, it is characterized in that in the described step 1, described reactor can be batch reactor or continuous high pressure reactor.
4. according to the preparation method of the described photoetch developer solution of claim 1, it is characterized in that in the described step 4, the operating conditions of described electrolytic tank is: current density is 100-10000A/m
2, preferred 500-5000A/m
2Electrolysis temperature is controlled at 20-80 ℃, preferred 30-70 ℃.
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| CN108440306A (en) * | 2018-05-24 | 2018-08-24 | 梁小朝 | A kind of device and method of the green production of tetramethyl ammonium carbonate |
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| CN114570307A (en) * | 2022-03-18 | 2022-06-03 | 西安吉利电子新材料股份有限公司 | Preparation system and method for directly producing electronic-grade tetramethylammonium hydroxide from dimethyl carbonate |
| TWI821542B (en) * | 2019-03-28 | 2023-11-11 | 日商Ｈｏｙａ股份有限公司 | Photomask, method of manufacturing a photomask, and method of manufacturing a display device |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111065966A (en) * | 2017-09-21 | 2020-04-24 | 霍尼韦尔国际公司 | Improved fill material for reducing pattern collapse |
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| TWI821542B (en) * | 2019-03-28 | 2023-11-11 | 日商Ｈｏｙａ股份有限公司 | Photomask, method of manufacturing a photomask, and method of manufacturing a display device |
| CN114570307A (en) * | 2022-03-18 | 2022-06-03 | 西安吉利电子新材料股份有限公司 | Preparation system and method for directly producing electronic-grade tetramethylammonium hydroxide from dimethyl carbonate |
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Application publication date: 20130710 |