Photoresist stripping liquid composition and method of making same

By using a photoresist stripping solution composition containing organic solvents, tetramethylammonium hydroxide, amine compounds, and antioxidants, the problems of insufficient stripping force and metal corrosion in the prior art are solved, achieving efficient photoresist removal and improved stability.

CN115598941BActive Publication Date: 2026-01-23ENF TECH CO LTD
View PDF 4 Cites 0 Cited by

Patent Information

Application Number
CN202210742158.0
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Priority Date
2021-06-28
Filing Date
2022-06-27
Publication Date
2026-01-23
Estimated Expiration
2042-06-27

AI Technical Summary

Technical Problem

Existing alkaline photoresist stripping solutions suffer from insufficient stripping force and corrosiveness to metals when removing photoresist. Furthermore, the stability of alkaline stripping solutions is easily affected by carbon dioxide fusion, leading to reduced stripping activity.

Method used

The composition comprises an organic solvent, tetramethylammonium hydroxide, an amine compound and an antioxidant, and is free of inorganic salts. The antioxidant, represented by chemical formula 1 or 2, enhances the stability of the stripping fluid and prevents metal corrosion.

Benefits of technology

It improves the photoresist removal power, prevents corrosion of the underlying film, enhances the stability of the composition over time, and reduces resistance-related issues in metal wiring.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN115598941B_ABST
    Figure CN115598941B_ABST
Patent Text Reader

Abstract

The present invention relates to a stripping solution composition for removing photoresist in a semiconductor device manufacturing process and a method for preparing the same. According to the present invention, it is possible to improve the stripping force of photoresist while preventing corrosion of a lower film and to improve the stability of the composition over time.
Need to check novelty before this filing date? Find Prior Art

Description

TECHNICAL FIELD

[0001] The present invention relates to a stripping solution composition for removing a photoresist in a semiconductor device manufacturing process and a preparation method thereof. BACKGROUND

[0002] The present invention relates to a stripping solution composition for removing a photoresist in a semiconductor device manufacturing process and a method of using the same. In more detail, the present invention relates to a stripping solution composition for a negative photoresist, i.e., a stripping solution composition for a negative photoresist suitable for a lithography process such as wiring, bump formation, etc. performed when manufacturing a circuit board and mounting a semiconductor or electronic component on the circuit board.

[0003] Generally, an alkaline stripping solution is used as a composition for removing a negative photoresist. As the alkaline stripping solution, there is a stripping solution composition consisting of a water-soluble organic amine and an organic solvent, but such an alkaline stripping solution does not have sufficient negative photoresist stripping power, and also has a problem of corrosion to a metal.

[0004] In addition, a tetramethylammonium hydroxide (TMAH) stripping solution used as a conventional photoresist stripping solution, when coming into contact with air and fusing with carbonic acid gas, consumes hydroxide ions constituting the above-mentioned alkaline stripping solution, forming bicarbonate or carbonate (hereinafter referred to as carbonate). Among the components of the alkaline stripping solution, the hydroxide ion forms a counter ion with the tetramethylammonium cation, and has stripping activity in a free state (a state of hydroxide). Therefore, by the generation of carbonate through the fusion with carbonic acid gas, there is a decrease in stripping activity.

[0005] In order to solve these problems, there is a need for a stripping solution having a stripping property of a level equivalent to the removal ability of a photoresist and the corrosion prevention ability of a metal wiring, and also a property of reducing the degeneration of an alkaline stripping solution. SUMMARY

[0006] Problems to be Solved by the Invention

[0007] The present invention aims to provide a stripping solution composition and a preparation method thereof, which improve the removal power of a photoresist while preventing corrosion of a metal and improving the stability of a stripping solution.

[0008] Means for Solving the Problems

[0009] In order to solve the above-mentioned problems, the present invention provides a photoresist stripping solution composition, which includes:

[0010] Organic solvents;

[0011] Tetramethylammonium hydroxide;

[0012] Amine compounds; and

[0013] Antioxidants

[0014] This composition does not contain inorganic salts.

[0015] The antioxidants mentioned above include compounds represented by chemical formula 1 or 2.

[0016] [Chemical Formula 1]

[0017]

[0018] In the above formula,

[0019] X1 and X2 are either N or O independently of each other.

[0020] R 1 and R 2 H and C are independent of each other. 1-2 Alkyl, OH, or NH2, and not all of them H.

[0021] When R 1 Or R 2 When OH is present, X1 or X2 is O.

[0022] [Chemical Formula 2]

[0023]

[0024] In the above formula,

[0025] X3 and X4 are either N or O independently of each other.

[0026] R 3 and R 4 H and C are independent of each other. 1-2 Alkyl, COORa, OH or NH2, Ra is H or C 1-2 alkyl.

[0027] According to one embodiment of the present invention, the antioxidant may comprise a compound represented by chemical formula 1 or 2.

[0028] [Chemical Formula 1]

[0029]

[0030] In the above formula,

[0031] X1 and X2 are either N or O independently of each other.

[0032] R1 and R 2 H and C are independent of each other. 1-2 Alkyl, OH, or NH2, and not all of them H.

[0033] When R 1 Or R 2 When OH is present, X1 or X2 is O.

[0034] When R 1 Or R 2 When it is a C2 alkyl group, the other R 1 Or R 2 For H.

[0035] [Chemical Formula 2]

[0036]

[0037] In the above formula,

[0038] X3 and X4 are N.

[0039] R 3 and R 4 H and C are independent of each other. 1-2 Alkyl, COOH, or COOCH3.

[0040] Specifically, for example, the antioxidants mentioned above may include those selected from 3-methylpyrazole, 4-methylpyridazine, 4,5-dimethylpyridazin, 4-methylisoxazole, 4-methyl-5-isoxazole, 4-methyl-5-isoxazole, 4-methyl-5-isoxazolamine, 4-ethylpyridazine, and 4-ethyl-5-methylpyridazine. It is one or more of the following: pyridazine, 5-methyl-4-pyridazinamine, 4,5-dimethylisoxazole, methylpyridazine-4-carboxylate, 4-methylpyrazole, 4-ethylisoxazole, 3,4-dimethylisoxazole, and 4-methyl-5-isoxazolol.

[0041] According to one embodiment of the present invention, the organic solvent may include one or more selected from dimethyl sulfoxide, ethylpyrrolidone, methylpyrrolidone, methylformamide, ethylformamide, diethylformamide, dimethylformamide, dimethylacetamide, dipropylene glycol monomethyl ether, diethyl sulfoxide, dipropyl sulfoxide, sulfolane, pyrrolidone, dimethylpropionamide, and methylpropionamide.

[0042] According to one embodiment of the present invention, the molecular weight of the above-mentioned amine compound may be from 80 to 250 g / mol.

[0043] Specifically, for example, the aforementioned amine compound may include one or more selected from tetraethylenepentamine, aminoethoxyethanol, monoethanolamine, monoisopropanolamine, diethylenetriamine, diisopropylamine, and aminoethylethanolamine.

[0044] According to another embodiment of the present invention, the present invention provides a method for preparing a photoresist stripping solution composition, comprising the step of mixing 60 to 90 wt% of an organic solvent, 0.1 to 10 wt% of tetramethylammonium hydroxide, 0.1 to 10 wt% of an amine compound, 0.1 to 10 wt% of an antioxidant, and water to make the total weight of the composition 100 wt%.

[0045] No inorganic salts added.

[0046] The antioxidants mentioned above include compounds represented by chemical formula 1 or 2.

[0047] [Chemical Formula 1]

[0048]

[0049] In the above formula,

[0050] X1 and X2 are either N or O independently of each other.

[0051] R 1 and R 2 H and C are independent of each other. 1-2 Alkyl, OH, or NH2, and not all of them H, when R 1 Or R 2 When the OH group is present, either X1 or X2 is O.

[0052] [Chemical Formula 2]

[0053]

[0054] In the above formula,

[0055] X3 and X4 are either N or O independently of each other.

[0056] R 3 and R 4 H and C are independent of each other. 1-2 Alkyl, COORa, OH or NH2, Ra is H or C 1-2 alkyl.

[0057] Specific details of other embodiments of the present invention are included in the following detailed description.

[0058] Invention Effects

[0059] The photoresist stripping solution composition and preparation method of the present invention can improve the stripping force of the photoresist while preventing corrosion of the underlying film and improving the stability of the composition over time. Attached Figure Description

[0060] Figure 1 This is a photograph showing the extent of damage to the copper surface as observed under a microscope. Detailed Implementation

[0061] This invention can be modified in various ways and has various embodiments, and therefore specific embodiments will be described in detail with reference to the accompanying drawings. However, this is not intended to limit the invention to the specific embodiments, and it should be understood that all modifications, equivalents, and substitutions are included within the spirit and technical scope of the invention. In describing the invention, detailed descriptions of relevant known technologies will be omitted if it is determined that such detailed descriptions may obscure the gist of the invention.

[0062] Unless otherwise specified in this specification, the expression "to" will be used to indicate that the corresponding numerical value is included. Specifically, for example, the expression "1 to 2" means not only that 1 and 2 are included, but also that all numerical values ​​between 1 and 2 are included.

[0063] The photoresist stripping solution composition and its preparation method according to embodiments of the present invention will now be described in more detail.

[0064] The composition of the present invention increases the density of the antioxidant molecular layer, thus preventing corrosion and damage to the underlying film while removing the photoresist. Furthermore, by minimizing the content changes caused by the decomposition of the alkali compounds, the antioxidant effect is improved, thereby enhancing the stability of the composition over time.

[0065] Specifically, the present invention provides a photoresist stripping solution composition, the composition comprising:

[0066] Organic solvents;

[0067] Tetramethylammonium hydroxide;

[0068] Amine compounds; and

[0069] Antioxidants

[0070] Contains no inorganic salts.

[0071] The antioxidants mentioned above include compounds represented by chemical formula 1 or 2.

[0072] [Chemical Formula 1]

[0073]

[0074] In the above formula, X1 and X2 are N or O independently of each other; for example, both can be N.

[0075] Furthermore, in the above formula, R 1 and R 2 H and C are independent of each other. 1-2 Alkyl, OH, or NH2, and not all of them simultaneously H, for example, each independently of H, methyl, ethyl, OH, or NH2.

[0076] When R 1 Or R 2 When R is OH, X1 or X2 is O. This does not mean that when R is OH, X1 or X2 is O. 1 Or R 2 If it is not OH, then X1 or X2 is not O.

[0077] Furthermore, in the above formula, when R 1 Or R 2 When it is a C2 alkyl group, the other R 1 Or R2 It can be H.

[0078] [Chemical Formula 2]

[0079]

[0080] In the above formula,

[0081] X3 and X4 are either N or O independently, for example, N.

[0082] R 3 and R 4 H and C are independent of each other. 1-2 Alkyl, COORa, OH or NH2, Ra is H or C 1-2 Alkyl groups, for example, that are independently H or C. 1-2 Alkyl, COOH, or COOCH3.

[0083] Specifically, for example, the aforementioned antioxidants may include those selected from 3-methylpyrazole, 4-methylpyridazine, 4,5-dimethylpyridazine, 4-methyl isoxazole, 4-methyl-5-isoxazole, 4-methyl-5-isoxazole, 4-methyl-5-isoxazol amine, 4-ethylpyridazine, 4-ethyl-5-methylpyridazine, 5-methyl-4-pyridazineamine, and 4,5-dimethylpyridazine. It contains one or more of the following: isoxazole, methylpyridazine-4-carboxylate, 4-methylpyrazole, 4-ethylisoxazole, 3,4-dimethylisoxazole, and 4-methyl-5-isoxazolol.

[0084] The antioxidant content can be from 0.1 to 10% by weight, for example, more than 0.1% by weight, more than 0.5% by weight, and for example, less than 10% by weight, less than 8% by weight, or less than 5% by weight. This invention prevents corrosion caused by the oxidation of copper (Cu) by containing antioxidants in the above-mentioned amounts, while also preventing the oxidation of tetramethylammonium hydroxide.

[0085] Specifically, tetramethylammonium hydroxide reacts with carbon dioxide (CO2) in the air to form the carbonate form of tetramethylammonium (TMA). The converted substance is a neutral salt and has no removal power for photoresist. The antioxidant of this invention can inhibit bicarbonate (HCO3) - The generation of ) is used to prevent the oxidation of tetramethylammonium hydroxide, ultimately increasing the number of substrates processed.

[0086] According to one embodiment of the present invention, tetramethylammonium hydroxide is used to dissolve photoresist. Its content can be from 0.1 to 10% by weight, for example, more than 0.1% by weight, more than 0.5% by weight, and for example, less than 10% by weight, less than 8% by weight, and less than 6% by weight.

[0087] According to one embodiment of the present invention, the above-mentioned organic solvent may be an aprotic polar solvent. Specifically, for example, it may include one or more selected from dimethyl sulfoxide (DMSO), ethylpyrrolidone (NEP), methylpyrrolidone (NMP), methylformamide (NMF), ethylformamide (NEF), diethylformamide (DEF), dimethylformamide (DMF), dimethylacetamide (DMAc), dipropylene glycol monomethyl ether (DPM), diethyl sulfoxide, dipropyl sulfoxide, sulfolane, pyrrolidone, dimethyl propionamide (DMPA), and methyl propioamide (NMPA).

[0088] The content of organic solvent can be 60 to 90% by weight, for example, more than 60% by weight, more than 70% by weight, more than 80% by weight, and for example, less than 90% by weight, less than 85% by weight.

[0089] According to one embodiment of the present invention, the molecular weight of the amine compound can be from 80 to 250 g / mol, for example, from 100 to 200 g / mol. If the molecular weight is too low, it may cause metal corrosion.

[0090] Specifically, for example, the aforementioned amine compound may include one or more selected from tetraethylenepentamine (TEPA), amino ethoxyethanol (AEE), monoethanolamine (MEA), monoisopropanolamine (MIPA), diethylenetriamine (DETA), diisopropylamine (DIPA), and amino ethylethanolamine (AEEA).

[0091] The content of amine compounds can be from 0.1% to 10% by weight, for example, more than 0.1% by weight, more than 0.5% by weight, and for example, less than 10% by weight, less than 7% by weight, and less than 5% by weight.

[0092] Because this invention does not contain inorganic salts, it minimizes problems related to wiring resistance. For example, in semiconductor processes, residual cations from inorganic salts such as potassium hydroxide (KOH) can affect wiring resistance, leading to defects.

[0093] According to one embodiment of the present invention, the present invention may include water in a balance of 100% by weight of the total composition. The water used is not particularly limited, but deionized water may be used, preferably deionized water with a resistivity of 18 MΩ / cm or higher, indicating the degree of ion removal from the water.

[0094] According to one embodiment of the present invention, in order to improve performance, the composition of the present invention may further contain any additives commonly used in compositions in the art. For example, it may further contain one or more additives selected from stabilizers, surfactants, chelating agents, corrosion inhibitors, antioxidants, and mixtures thereof.

[0095] The stabilizer may be an etching stabilizer, which is included to suppress side effects or byproducts that may occur with the composition or the object being treated.

[0096] To improve the wettability of the composition, enhance the foaming properties of the additives, and increase the solubility of other organic additives, a surfactant may be further added. The surfactant may be one or more selected from nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants. Its content relative to the total weight of the composition may be 0.0005 to 5% by weight, preferably 0.001 to 2% by weight. When the content of the surfactant is less than 0.0005% by weight, the desired effect cannot be achieved; when the content of the surfactant is greater than 5% by weight, solubility problems may occur, or excessive foaming may cause process problems.

[0097] To further increase the solubility of the composition for metallic impurities or to form a uniform etched surface, a chelating agent may be added. The chelating agent may be one or more organic acids containing carboxyl groups, and its content may be 0.1 to 5% by weight relative to the total weight of the composition. Preferably, it may be an organic acid containing both carboxyl and hydroxyl groups.

[0098] For the purpose of protecting the metal or metal compound used as a semiconductor device material, corrosion inhibitors and antioxidants may be included. The corrosion inhibitors and antioxidants mentioned above, as long as they are commonly used in the art, may be added without limitation; for example, they may include, but are not limited to, azole compounds, and their content may be from 0.01 to 10% by weight relative to the total weight of the composition.

[0099] The embodiments of the present invention will now be described in detail to enable those skilled in the art to readily implement them. However, the present invention can be implemented in various different forms and is not limited to the embodiments described herein.

[0100] Example

[0101] Each photoresist stripping solution composition was prepared according to the composition described in Table 1 below. Content is expressed in weight %.

[0102] Table 1

[0103]

[0104]

[0105] TMAH: Tetramethyl ammonium hydroxide

[0106] AEE: Diethylene glycolamine (2-(2-Aminoethoxy)ethanol) (Molecular weight: 105.1 g / mol)

[0107] DETA: Diethylene triamine (molecular weight: 103.2 g / mol)

[0108] DIPA: Diisopropylamine (molecular weight: 101.2 g / mol)

[0109] TEPA: Tetraethylene pentamine (molecular weight: 189.3 g / mol)

[0110] AEEA: Amino ethyl ethanol amine (molecular weight: 104.2 g / mol)

[0111] DMSO: Dimethyl sulfoxide

[0112] NEP: N-ethyl pyrrolidone

[0113] NMP: N-methyl pyrrolidone

[0114] NMF: N-methyl formamide

[0115] NEF: N-ethyl formamide

[0116] DEF: N,N-diethyl formamide

[0117] DMF: N,N-dimethylformamide

[0118] Comparative example

[0119] Each photoresist stripping solution composition was prepared according to the compositions described in Table 2 below. Content is expressed in weight percent.

[0120] Table 2

[0121]

[0122] TMAH: Tetramethyl ammonium hydroxide

[0123] KOH: Potassium hydroxide

[0124] DETA: Diethylene triamine (molecular weight: 103.2 g / mol)

[0125] MEA: Monoethanolamine (Molecular weight: 61.1 g / mol)

[0126] MIPA: Monoisopropanol amine (molecular weight: 75.1 g / mol)

[0127] TEPA: Tetraethylene pentamine (molecular weight: 189.3 g / mol)

[0128] DMSO: Dimethyl sulfoxide

[0129] NMP: N-methyl pyrrolidone

[0130] NMF: N-methyl formamide

[0131] BTA: Benzotriazole

[0132] TT: Tolyltriazole

[0133] Experimental Example 1: Evaluation of Photoresist Peel-off Force

[0134] For each stripper composition, to evaluate the photoresist stripping performance, a photoresist film with a thickness of approximately 50 to 60 μm was formed on a copper-plated wafer. The wafer was then cut into 2 cm × 1.5 cm pieces to prepare evaluation samples. These samples were immersed in each stripper composition at 60°C for 7 minutes to remove the photoresist. The photoresist-removed samples were then washed with ultrapure water and dried with nitrogen.

[0135] Subsequently, the removal of photoresist was confirmed under a microscope. The evaluation was conducted according to the following evaluation criteria, and the evaluation results are shown in Tables 3 and 4 below.

[0136] ◎: 100% complete removal of photoresist, with no residue.

[0137] ○: More than 80% but less than 100% of the photoresist has been removed, leaving almost no residue.

[0138] △: More than 50% but less than 80% of the photoresist was removed, leaving a slightly larger amount of residue.

[0139] ×: Less than 50% of the photoresist was removed, leaving a considerable amount of residue.

[0140] Experimental Example 2: Evaluation of the Corrosion Resistance of the Lower Membrane

[0141] For each stripping solution composition, a copper film with a thickness of approximately 1000 nm was formed on a silicon wafer to evaluate its resistance to copper film corrosion. The wafers were then cut into 3 cm × 2.5 cm pieces to prepare evaluation samples. After measuring the sheet resistance of the samples, they were immersed in each stripping solution composition and soaked in 60°C for 10 minutes. The samples were then washed with ultrapure water and dried with nitrogen.

[0142] Then, the sheet resistance of the dried sample (1000 mm thick) was measured using a 4-point probe (CMT-SR1000N, automatic contact system). The measurement method was described as 1-2 Mohm / sq, and the specific resistivity was calculated using the initial thickness value. Following this, the sheet resistance was measured again after evaluation, and the thickness was determined.

[0143] Specific resistivity (ohm·cm) = ohm / sq × thickness (cm)

[0144] The degree of corrosion on the copper film surface was determined by comparing the etching thickness values ​​before and after the stripping step. The evaluation was conducted according to the following criteria, and the results are shown in Tables 3 and 4 below. Figure 1 .

[0145] Figure 1 The left side shows Comparative Example 2, and the right side shows the evaluation results based on Example 1.

[0146] No corrosion occurred: ≤50

[0147] Mild corrosion occurs: greater than 50 to less than or equal to 100

[0148] Corrosion occurs: greater than 100 to less than or equal to 500

[0149] Severe corrosion occurs: greater than 500 to less than or equal to 1000

[0150] As shown in the comparative example photograph, damage was confirmed on the surface of the copper substrate treated with the composition containing tetramethylammonium hydroxide.

[0151] Conversely, it was confirmed that the copper substrate surface treated with the composition of the examples was completely undamaged.

[0152] Experimental Example 3: Evaluation of Time-Related Stability

[0153] The stability of each stripping solution composition over time was evaluated. The examples and comparative examples were subjected to harsh conditions of heating at 60°C for 48 hours to induce changes over time. The concentration of tetramethylammonium hydroxide was confirmed by acid titration analysis. The evaluation was conducted according to the following evaluation criteria, and the results are shown in Tables 3 and 4 below.

[0154] ◎: TMAH concentration change rate is less than 10%

[0155] ○: The rate of change in TMAH concentration is greater than 10% and less than or equal to 30%.

[0156] △: The rate of change in TMAH concentration is greater than 30% and less than or equal to 50%.

[0157] ×: The TMAH concentration change rate is greater than 50% and less than or equal to 100%.

[0158] Table 3

[0159] Distinguishing Peeling force Anticorrosive power Stability against change over time Example 1 ◎ 24 ◎ Example 2 ◎ 64 ◎ Example 3 ◎ 31 ◎ Example 4 ◎ 10 ◎ Example 5 ◎ 51 ◎ Example 6 ◎ 71 ◎ Example 7 ○ 11 ◎ Example 8 ◎ 15 ◎ Example 9 ◎ 66 ◎ Example 10 ◎ 42 ○ Example 11 ◎ 34 ◎ Example 12 ◎ 12 ◎ Example 13 ◎ 31 ◎ Example 14 ◎ 53 ○ Example 15 ◎ 68 ○

[0160] Table 4

[0161] Distinguishing Peeling force Anticorrosive power Stability against change over time Comparative Example 1 × 3 - Comparative Example 2 ◎ 998 × Comparative Example 3 × 990 × Comparative Example 4 ◎ 748 × Comparative Example 5 ◎ 998 × Comparative Example 6 ◎ 893 × Comparative Example 7 ○ 990 ×

[0162] As shown in Tables 3 and 4 above, it can be confirmed that the compositions of the examples showed almost no corrosion, and exhibited excellent peel strength and stability over time. In particular, it was also confirmed that the composition of Example 4 not only had excellent peel strength and stability over time, but also the best corrosion resistance.

[0163] In contrast, most of the compositions in the comparative examples were severely corroded. Although Comparative Example 1 was not corroded, its peel strength decreased and a large amount of photoresist remained, thus it was determined to be unsuitable as a photoresist stripping solution composition.

[0164] As described above, the photoresist stripping solution composition of the present invention can improve stripping performance and stability over time, while also inhibiting corrosion of the underlying metal film.

[0165] The specific details of the present invention have been described above. For those skilled in the art, these specific techniques are merely preferred embodiments and are not intended to limit the scope of the invention. Those skilled in the art can make various applications and modifications within the scope of the invention based on the above description. Therefore, the essential scope of the invention is defined by the appended claims and their equivalents.

Claims

1. A photoresist stripping solution composition, wherein, The composition comprises: Organic solvents; Tetramethylammonium hydroxide; Amine compounds; and Antioxidants Furthermore, the composition does not contain inorganic salts. The antioxidant comprises compounds represented by chemical formula 1 or 2. The content of the organic solvent is 60 to 90% by weight. [Chemical Formula 1] In the above formula, X1 and X2 are either N or O independently of each other. R 1 and R 2 H and C are independent of each other. 1-2 Alkyl, OH, or NH2, and not all of them H. When R 1 Or R 2 When the OH group is present, either X1 or X2 is O. [Chemical Formula 2] In the above formula, X3 and X4 are either N or O independently of each other. R 3 and R 4 H and C are independent of each other. 1-2 Alkyl, COORa, OH or NH2, Ra is H or C 1-2 alkyl.

2. The photoresist stripping solution composition according to claim 1, wherein, The antioxidant comprises a compound represented by chemical formula 1 or 2: [Chemical Formula 1] In the above formula, X1 and X2 are either N or O independently of each other. R 1 and R 2 H and C are independent of each other. 1-2 Alkyl, OH, or NH2, and not all of them H. When R 1 Or R 2 When OH is present, X1 or X2 is O. R 1 Or R 2 When it is a C2 alkyl group, the other R 1 Or R 2 For H; [Chemical Formula 2] In the above formula, X3 and X4 are N. R 3 and R 4 H and C are independent of each other. 1-2 Alkyl, COOH, or COOCH3.

3. The photoresist stripping solution composition according to claim 1, wherein, The antioxidant comprises one or more selected from 3-methylpyrazole, 4-methylpyridazine, 4,5-dimethylpyridazine, 4-methylisoxazole, 4-methyl-5-isoxazole, 4-methyl-5-isoxazoleamine, 4-ethylpyridazine, 4-ethyl-5-methylpyridazine, 5-methyl-4-pyridazineamine, 4,5-dimethylisoxazole, methyl pyridazine-4-carboxylate, 4-methylpyrazole, 4-ethylisoxazole, 3,4-dimethylisoxazole, and 4-methyl-5-isoxazole alcohol.

4. The photoresist stripping solution composition according to claim 1, wherein, The organic solvent includes one or more selected from dimethyl sulfoxide, ethylpyrrolidone, methylpyrrolidone, methylformamide, ethylformamide, diethylformamide, dimethylformamide, dimethylacetamide, dipropylene glycol monomethyl ether, diethylene sulfoxide, dipropylene sulfoxide, sulfolane, pyrrolidone, dimethylpropionamide, and methylpropionamide.

5. The photoresist stripping solution composition according to claim 1, wherein, The molecular weight of the amine compound is 80 to 250 g / mol.

6. The photoresist stripping solution composition according to claim 1, wherein, The amine compound includes one or more selected from tetraethylenepentamine, diethylene glycolamine, monoethanolamine, monoisopropanolamine, diethylenetriamine, diisopropylamine, and hydroxyethylethylenediamine.

7. A method for preparing a photoresist stripping solution composition, wherein, The preparation method includes the step of mixing 60 to 90 wt% of an organic solvent, 0.1 to 10 wt% of tetramethylammonium hydroxide, 0.1 to 10 wt% of an amine compound, 0.1 to 10 wt% of an antioxidant, and water to make the total weight of the composition 100 wt%. No inorganic salts are added in the preparation method described above. Furthermore, the antioxidant comprises a compound represented by chemical formula 1 or 2; [Chemical Formula 1] In the above formula, X1 and X2 are either N or O independently of each other. R 1 and R 2 H and C are independent of each other. 1-2 Alkyl, OH, or NH2, and not all of them H. When R 1 Or R 2 When the OH group is present, either X1 or X2 is O. [Chemical Formula 2] In the above formula, X3 and X4 are either N or O independently of each other. R 3 and R 4 H and C are independent of each other. 1-2 Alkyl, COORa, OH or NH2, Ra is H or C 1-2 alkyl.

Citation Information

Patent Citations

  • Peeling liquid for cured film of photopolymerizable composition

    JP2001343759A

  • Method for removing photoresist

    JP2002062668A

  • Stripper composition for thick negative photoresist

    JP2014048667A

  • Compositions and methods for the removal of photoresist for a wafer rework application

    US20100056410A1