CN110441997B - Improved environment-friendly aqueous photoresist stripping liquid - Google Patents
Improved environment-friendly aqueous photoresist stripping liquid Download PDFInfo
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- CN110441997B CN110441997B CN201910764972.0A CN201910764972A CN110441997B CN 110441997 B CN110441997 B CN 110441997B CN 201910764972 A CN201910764972 A CN 201910764972A CN 110441997 B CN110441997 B CN 110441997B
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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
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Abstract
The invention discloses an improved environment-friendly water-based photoresist stripping liquid, which mainly comprises the following components: the organic amine, water-soluble organic solvent, water and water-soluble organic phosphoric acid, wherein the molecular structure of the water-soluble organic phosphoric acid has an amino group; the content of the water-soluble organic phosphoric acid is 0.01 to 3 percent by weight. The improved environment-friendly water-based photoresist stripping liquid takes water-soluble organic phosphoric acid with amino as a copper corrosion inhibitor, takes amino and phosphoric acid groups in the organic phosphoric acid as coordination groups to react with copper, and compared with benzotriazole corrosion inhibitors in the prior art, the improved environment-friendly water-based photoresist stripping liquid has weaker coordination capacity, weakens the protection capacity of a corrosion inhibition system on copper wiring, and realizes the selective etching of the copper wiring; the water-soluble organic phosphoric acid can adjust the pH value of a stripping system, and the organic phosphoric acid attached to the surface of copper and molybdenum adjusts the potential difference of the copper and molybdenum interface while alkanolamine attacks photoresist, so that the undercut phenomenon is prevented.
Description
Technical Field
The invention relates to the technical field of semiconductor production, in particular to an improved environment-friendly aqueous photoresist stripping solution.
Background
In order to reduce the wiring line width in the advanced panel to save space, the copper wiring with better resistivity is adopted to replace the aluminum wiring, but the adhesion between the copper wiring and the glass substrate is poor, and the lower layer needs to be assisted by one material selected from molybdenum, molybdenum alloy, titanium and titanium alloy, wherein the titanium and the titanium alloy are expensive, and the performance price ratio of the molybdenum and the molybdenum alloy is higher.
The production process of the substrate comprises the following steps: the wiring material layer formed on the substrate is coated with a photoresist, exposed to light and developed to form a resist pattern, the conductive metal layer, the insulating film, and the like are etched using the patterned resist as a mask to form fine wiring, and then the unnecessary photoresist layer is removed with a stripper. As the photoresist stripper composition, a single solvent such as an organic base, an inorganic base, an organic acid, an inorganic acid, a polar solvent, or a mixed solution thereof is used. It is also known to use a mixed solution of an amine and water in order to improve the photoresist stripping property.
The substrate peeling process comprising a copper wiring layer and a molybdenum/molybdenum alloy layer has the following technical drawbacks: first, copper is easily oxidized into copper oxide in the air due to its chemical properties, resulting in poor conductivity and increased impedance. The copper protective agent benzotriazole and the like in the prior art have strong corrosion inhibition performance, so that components in the stripping liquid cannot selectively etch copper through a protective layer formed by the corrosion inhibitor to remove a surface oxide layer; secondly, a potential difference exists between copper and molybdenum, and when the copper and molybdenum are treated by the alkaline stripping solution, molybdenum is preferentially corroded to generate an undercut phenomenon, so that the line width of the pattern is distorted.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide an improved environment-friendly water-based photoresist stripping solution, which improves undercut and selectively etches copper by adjusting the potential difference of a copper-molybdenum interface.
In order to realize the technical effects, the technical scheme of the invention is as follows: an improved environment-friendly water-based photoresist stripping solution is characterized by comprising the following main components: the organic amine, a water-soluble organic solvent, water and water-soluble organic phosphoric acid, wherein the molecular structure of the water-soluble organic phosphoric acid has an amino group; the content of the water-soluble organic phosphoric acid is 0.01-3% by weight, and the pH value of the environment-friendly water-based photoresist stripping liquid is more than 8.
The preferable technical scheme is that amino in the water-soluble organic phosphoric acid is a primary amine group or a secondary amine group.
The preferable technical scheme is that the environment-friendly water-based photoresist stripping solution comprises the following components in percentage by weight: 3 to 30 percent of primary alkanolamine and/or tertiary alkanolamine, 50 to 80 percent of water-soluble organic solvent, 0.05 to 1 percent of water-soluble organic phosphoric acid and 10 to 30 percent of water.
Preferably, the water-soluble organic phosphoric acid having an amino group is one or a combination of two or more selected from the group consisting of aminobis (methylenephosphoric acid), (1-amino-2-methylbutyl) phosphoric acid, (1-aminobutyl) phosphoric acid, (1-aminopropyl) phosphoric acid, (1-amino-2, 2-dimethylpropyl) phosphoric acid, (1-amino-2-methylpropyl) phosphoric acid, and 1-amino-1, 1-ethylidenediphosphonic acid.
The preferable technical proposal is that the water-soluble organic phosphoric acid is one or the combination of more than two of aminodi (methylene phosphate), (1-amino-2, 2-dimethylpropyl) phosphoric acid and 1-amino-1, 1-ethylidene diphosphonic acid.
The preferable technical scheme is that the water-soluble organic solvent is one or the combination of more than two of diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether and propylene glycol methyl ether.
The preferable technical scheme is that the organic amine is one or the combination of more than two of diethanolamine, triethanolamine and N-methyldiethanolamine.
The preferable technical proposal is that the water-soluble organic phosphoric acid is formed by combining amino di (methylene phosphoric acid) and 1-amino-1, 1-ethylidene diphosphonic acid, and the weight percentage of the amino di (methylene phosphoric acid) in the water-soluble organic phosphoric acid is 23 to 45 percent.
Another object of the present invention is to provide a method for stripping a photoresist, which comprises wet-treating a substrate having a wiring layer made of copper or a copper alloy, an auxiliary connection layer made of molybdenum or a molybdenum alloy, and a base material layer with the use of the environmentally friendly aqueous photoresist stripping solution.
The invention has the advantages and beneficial effects that:
the improved environment-friendly water-based photoresist stripping liquid takes water-soluble organic phosphoric acid with amino as a copper corrosion inhibitor, takes amino and phosphate groups in the organic phosphoric acid as coordination groups to react with copper, and has weaker coordination capability compared with benzotriazole corrosion inhibitors in the prior art, so that the protection capability of a corrosion inhibition system on copper wiring is weakened, and the selective etching of the copper wiring is realized;
the water-soluble organic phosphoric acid can adjust the pH value of a stripping system, and the organic phosphoric acid attached to the surface of copper and molybdenum adjusts the potential difference of a copper and molybdenum interface while alkanolamine attacks photoresistance, so that the undercut phenomenon is prevented;
in a further aspect of the present invention,the decay rate of the copper film is controlled by adjusting the concentration of the water-soluble organic phosphoric acid and preferably the molecular structure of the water-soluble organic phosphoric acid
Detailed Description
The following further describes embodiments of the present invention with reference to examples. The following examples are only for illustrating the technical solutions of the present invention more clearly, and the protection scope of the present invention is not limited thereby.
Water soluble organic phosphoric acid
The water-soluble organic phosphoric acid is classified into primary amine, secondary amine and tertiary amine according to the substitution of the amino group by a hydrocarbon group, and tertiary amine such as amino trimethylene phosphonic acid contains three phosphoric acid groups and one tertiary amine group in its molecule, and has a strong coordination ability, which is not favorable for corrosion of copper wiring by a stripping solution, and oxide remains on the surface of copper wiring of a substrate after treatment, compared with primary amine and secondary amine. Therefore, the amino group in the preferred water-soluble organic phosphoric acid is a primary amine group or a secondary amine group.
Further, the range of choice for organic phosphoric acids having primary and secondary amine groups includes: aminodi (methylenephosphoric acid), (1-amino-2-methylbutyl) phosphoric acid, (1-aminobutyl) phosphoric acid, (1-aminopropyl) phosphoric acid, (1-amino-2, 2-dimethylpropyl) phosphoric acid, (1-amino-2-methylpropyl) phosphoric acid, 1-amino-1, 1-ethylidenediphosphonic acid. Among the organic phosphoric acids, aminodi (methylenephosphonic acid) and 1-amino-1, 1-ethylidenediphosphonic acid.
In the water-soluble organic phosphoric acid, the molecular structures of aminodi (methylene phosphonic acid) and 1-amino-1, 1-ethylidene diphosphonic acid have two phosphate groups, the coordination probability with copper is high, in addition, the secondary amine group in the molecular structure of aminodi (methylene phosphonic acid) has small steric hindrance, the electron cloud density of secondary amine N is high, the alkalinity is strong, and the coordination capability is stronger than that of 1-amino-1, 1-ethylidene diphosphonic acid; the tertiary butyl in the molecular structures of the (1-amino-2, 2-dimethylpropyl) phosphoric acid and the 1-amino-1, 1-ethylidene diphosphonic acid has large steric hindrance, reduces the coordination reaction speed and is convenient for leading the small-molecular alkanolamine to corrode the surface layer of the copper wiring.
Furthermore, the corrosion inhibitor composed of amino di (methylene phosphate) and 1-amino-1, 1-ethylidene diphosphonic acid has proper copper corrosion prevention effect and alkalinity, and achieves the technical effects of controlling the copper corrosion rate and adjusting the potential difference of a copper-molybdenum interface.
Water soluble organic solvent
In the prior art, the common organic solvent is strong polar solvent such as N-methyl pyrrolidone, dimethyl sulfoxide and the like, but in consideration of the odor in the using process, safety factors such as user health and the like, the improved organic solvent is alcohol ether organic solvent, such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether and propylene glycol methyl ether.
Organic amine
The organic amine has the function of promoting the cracking of the photoresist skeleton polymer. Including but not limited to cycloaliphatic alcohol amines, alkanol amines, quaternary ammonium hydroxides. Small organic amines such as diethanolamine, triethanolamine and N-methyldiethanolamine are preferred.
The aqueous resist stripping solution of the present invention may contain, in addition to the above components, an auxiliary agent such as a surfactant and an antifoaming agent, and the amount of the auxiliary agent is specifically determined in accordance with the stripping effect, and usually, the weight percentage of the surfactant and the antifoaming agent in the aqueous resist stripping solution is not more than 5%, and further, not more than 1%.
Examples 1 to 3 and comparative example 1
The compositions (in weight percent) of the improved environmental protection water-based photoresist stripper in examples (abbreviated as S, the same below) 1-11 are shown in the following table:
in examples 1 to 3 and comparative example 1, the organic amine was triethanolamine, the water-soluble organic solvent was diethylene glycol dimethyl ether, and the water-soluble organic phosphoric acid was (1-aminobutyl) phosphoric acid having one primary amine group and one phosphoric acid group in the molecular structure.
Example 4 is based on example 3 with the difference that the organic amine is diethanolamine and the water-soluble organic solvent is diethylene glycol monomethyl ether.
Examples 5-9 are based on example 4, with the difference that:
example 5 the water-soluble organic phosphoric acid is aminodi (methylene phosphate) having one secondary amine group and two phosphoric acid groups in the molecular structure.
Example 6 a water-soluble organophosphonic acid is 1-amino-1, 1-ethylidene diphosphonic acid having one primary amine group and two phosphate groups in the molecular structure.
Example 7 the water-soluble organic phosphoric acid is (1-amino-2, 2-dimethylpropyl) phosphoric acid having a primary amine group, a tertiary butyl group and a phosphoric acid group in the molecular structure.
Example 8 a water-soluble organic phosphoric acid was prepared by combining aminodi (methylenephosphoric acid), (1-amino-2, 2-dimethylpropyl) phosphoric acid in a weight ratio of 1.
Example 9A water-soluble organic phosphoric acid was prepared by combining a water-soluble organic phosphoric acid comprising aminodi (methylene phosphate) and 1-amino-1, 1-ethylidene diphosphonic acid, wherein the weight percentage of aminodi (methylene phosphate) in the water-soluble organic phosphoric acid was 70%.
Examples 10-11 the weight percentages of aminodi (methylene phosphate) in the water-soluble organic phosphoric acid based on example 9 were 10% and 35%, respectively.
Examples and comparative examples evaluation tests:
1. sputtering a copper film with the thickness of 50nm on a glass substrate, then soaking the substrate in an environment-friendly water-based photoresist stripping liquid with the temperature of 50 ℃, treating for 30min, drying, observing the corrosion condition of the copper film according to the soaking time of 2min/5 min/15 min/30min, and calculating the attenuation rate of the copper film within 30 min;
2. a molybdenum-niobium alloy and copper were formed on glass by sputtering in this order, and then a photoresist merck AZ-p100 was applied thereon to form a film, and the photoresist was patterned by UV exposure, development, and the like, and then copper and molybdenum were etched together with a hydrogen peroxide-containing copper etchant under conditions of 40 ℃/50 seconds, and the obtained substrate was used as an evaluation target. The substrate was immersed in a photoresist remover composition adjusted to 50 ℃, subjected to a 10-minute stripping and immersion treatment, dried, and observed for undercut and photoresist stripping.
Undercut evaluation criteria: no undercutting,. Circa very little undercutting, (below unacceptable) \9679withsevere undercutting;
evaluation criteria for photoresist stripping: no peeling residue, (below defective) verygood residual photoresist coverage area of 5% or less and 96795% or more, residual photoresist coverage area of more than 5%.
The copper decay rates, undercutting and photoresist stripping results for the examples and comparative examples are shown in the following table:
the comparison of the types of the corrosion inhibitors is formed in the embodiment 3 and the comparative example 1, the 1% benzotriazole copper corrosion inhibitor in the comparative example 1 has the content of the conventional corrosion inhibitor, and the attenuation rate of the copper film is known, so that the organic phosphoric acid containing amino is beneficial to the corrosion of the surface of the copper film or the copper wiring, and the requirement of stripping liquid on the trace corrosion of the copper surface layer is met;
in example 1, the content of organic phosphoric acid is low, which means that the copper decay rate is low, the copper film decay is concentrated in the first 10min of the soaking treatment, and the photoresist on the surface of the substrate subjected to the stripping treatment in example 1 has a small amount of residue;
the alkalinity of amino in the molecular structure of the organic phosphoric acid directly influences the pH value of a wet stripping system and the adjustment result of the potential difference of a copper-molybdenum interface, and the preferred embodiments 7 to 11 almost have no undercut phenomenon;
the steric hindrance of the phosphate group, the amino group and the coordination group in the molecular structure of the organic phosphoric acid directly influences the copper film attenuation rate, and generally, the copper film attenuation rate needs to be controlled within 30min
Copper film decay rates of examples 3 to 11The ratio can be controlled within the above numerical range. Furthermore, the water-soluble organic phosphoric acid which is formed by combining aminodi (methylene phosphoric acid) and 1-amino-1, 1-ethylidene diphosphonic acid is adopted, the attenuation rate of the copper film can be further controlled within the numerical value range, the ineffective copper film corrosion is reduced, and the conductivity of the copper wiring is improved.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the technical principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. An improved environment-friendly water-based photoresist stripping liquid is characterized by comprising the following main components: the organic amine, a water-soluble organic solvent, water and water-soluble organic phosphoric acid, wherein the molecular structure of the water-soluble organic phosphoric acid has an amino group; the content of the water-soluble organic phosphoric acid is 0.01 to 3 percent by weight; the organic amine is a primary alkanolamine and/or a tertiary alkanolamine;
the water-soluble organic phosphoric acid with amino is one or the combination of more than two of aminodi (methylene phosphoric acid), (1-amino-2-methylbutyl) phosphoric acid, (1-aminobutyl) phosphoric acid, (1-aminopropyl) phosphoric acid, (1-amino-2, 2-dimethylpropyl) phosphoric acid, (1-amino-2-methylpropyl) phosphoric acid and 1-amino-1, 1-ethylidene diphosphonic acid;
the environment-friendly water system photoresist stripping liquid comprises the following components in percentage by weight: 3 to 30 percent of primary alkanolamine and/or tertiary alkanolamine, 50 to 80 percent of water-soluble organic solvent, 0.05 to 1 percent of water-soluble organic phosphoric acid and 10 to 30 percent of water.
2. The improved eco-friendly aqueous photoresist stripper according to claim 1, wherein the water-soluble organic phosphoric acid is one or a combination of two or more selected from aminodi (methylene phosphoric acid), (1-amino-2, 2-dimethylpropyl) phosphoric acid, and 1-amino-1, 1-ethylidene diphosphonic acid.
3. The improved eco-friendly aqueous photoresist stripper according to claim 1, wherein the water-soluble organic solvent is one or a combination of two or more selected from the group consisting of diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, and propylene glycol methyl ether.
4. The improved environmental protection water system photoresist stripping solution as defined in claim 1, wherein the organic amine is one or a combination of two or more selected from diethanolamine, triethanolamine and N-methyldiethanolamine.
5. The improved eco-friendly aqueous photoresist stripper as claimed in claim 2, wherein the water soluble organic phosphoric acid is composed of aminodi (methylene phosphonic acid) and 1-amino-1, 1-ethylidene diphosphonic acid, and the weight percentage of aminodi (methylene phosphonic acid) in the water soluble organic phosphoric acid is 23-45%.
6. A method for stripping a resist, comprising wet-treating a substrate with the aqueous environmental-friendly resist stripping solution according to any one of claims 1 to 5, the substrate having a wiring layer, an auxiliary connection layer and a base material layer, wherein the wiring layer is made of copper or a copper alloy, and the auxiliary connection layer is made of molybdenum or a molybdenum alloy.
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| US5472830A (en) * | 1994-04-18 | 1995-12-05 | Ocg Microelectronic Materials, Inc. | Non-corrosion photoresist stripping composition |
| CN102227687A (en) * | 2008-12-25 | 2011-10-26 | 长瀬化成株式会社 | Photoresist remover composition, method for removing photoresist of multilayer metal circuit board, and method for producing multilayer metal circuit board |
| CN103424999A (en) * | 2012-05-24 | 2013-12-04 | 东友Fine-Chem股份有限公司 | Resist stripper composition and method for manufacturing TFT array substrate using the same |
| CN104614954A (en) * | 2015-01-09 | 2015-05-13 | 苏州瑞红电子化学品有限公司 | Photoresist-removing water-based stripping liquid composition |
| CN105527804A (en) * | 2016-03-09 | 2016-04-27 | 长沙晟辉新材料有限公司 | Low-temperature aqueous positive photo-resistant stripping liquid |
| CN109143800B (en) * | 2018-11-02 | 2022-01-28 | 江阴江化微电子材料股份有限公司 | Universal photoresist stripping liquid and application thereof |
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