Photoresist composition and preparation method thereof

By using compositions of alkali-soluble resins, photosensitizers, silicone leveling agents and organic solvents in photoresist, the problem of insufficient photosensitive properties of photoresist is solved, and a high photosensitive speed and high resolution photoresist is achieved Preparation, suitable for integrated circuits and semiconductor micromachining.

CN119200326APending Publication Date: 2024-12-27SU ZHOU LING XIN HUAN BAO KE JI YOU XIAN GONG SI
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Patent Information

Application Number
CN202310753099.1
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2023-06-26
Publication Date
2024-12-27

AI Technical Summary

Technical Problem

The existing photoresist is insufficient in photosensitiveness, making it difficult to meet the needs of high-precision and high-efficiency lithography in integrated circuits and semiconductor fine machining.

Method used

Using a photoresist composition, which includes an alkali-soluble resin, a photosensitizer, a silicone leveling agent and an organic solvent, is prepared by a specific stirring and heating process to form a photoresist with high photosensitive velocity and high resolution.

Benefits of technology

It realizes the high photosensitive speed and high resolution of photoresist, and the material surface is flat, which is suitable for high-precision photolithography processes.

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Abstract

The invention relates to a photoresist composition and a preparation method thereof, the photoresist composition comprises the following raw material components in parts by mass: 20-30 parts of alkali-soluble resin, 5-10 parts of a photosensitizer, 0.5-1 part of an organosilicon leveling agent and 50-60 parts of an organic solvent, and the raw material components are mixed to prepare a photoresist. The material disclosed by the invention is stable in photosensitive material and smooth in surface.
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Description

Technical Field

[0001] The invention relates to the field of photosensitive materials, and in particular to a photoresist composition and a preparation method thereof. Background Art

[0002] Photoresist is a type of etching-resistant thin film material whose solubility changes after being irradiated by energy such as light beams, electron beams, and ion beams. It is widely used in the micro-processing of integrated circuits and discrete semiconductor devices. By coating the photoresist on semiconductor, conductor, and insulator materials, the remaining part after exposure and development protects the bottom layer, and then etching with an etchant can transfer the required fine pattern from the mask to the substrate to be processed. Therefore, photoresist is a key material in micro-processing technology. According to the different photochemical reaction mechanisms, photoresists are divided into positive photoresists and negative photoresists: after exposure, the solubility of photoresists in the developer increases, and the pattern obtained is the same as the mask, which is called positive photoresist; after exposure, the solubility of photoresists in the developer decreases or even becomes insoluble, and the pattern obtained is the opposite of the mask, which is called negative photoresist. Both types of photoresists have their own different application fields. Generally speaking, positive photoresists are more commonly used, accounting for more than 80% of the total photoresists.

[0003] As the integration of integrated circuits increases and the width of processing lines decreases, photoresists corresponding to different exposure wavelengths are also developed. As the exposure wavelength changes, the composition and structure of the photoresist also change continuously, so that the comprehensive performance of the photoresist meets the requirements of the integrated process. However, its photosensitivity needs to be improved. Summary of the invention

[0004] In order to solve the above technical problems, the object of the present invention is to provide a photoresist composition and a preparation method thereof.

[0005] To achieve the above object, the present invention adopts the following technical solution:

[0006] A photoresist composition comprises the following raw material components in parts by weight: 20-30 parts of alkali-soluble resin, 5-10 parts of photosensitizer, 0.5-1 part of organic silicon leveling agent and 50-60 parts of organic solvent.

[0007] Preferably, in the photoresist composition, the alkali-soluble resin includes any one of acrylic resin, epoxy resin or bisphenol fluorene resin.

[0008] Preferably, in the photoresist composition, the organosilicon leveling agent is any one of polydimethylsiloxane or silicone oil.

[0009] Preferably, in the photoresist composition, the organic solvent is any one of ethyl lactate, ethyl acetate, n-butyl acetate, ethylene glycol monomethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol monomethyl ether or diethylene glycol monomethyl ether.

[0010] Preferably, in the photoresist composition, the photosensitizer is any one of an acyl oxime photoinitiator, an oxime ester photoinitiator, a ketone photoinitiator or a bisimidazole photoinitiator.

[0011] Preferably, in the photoresist composition, the weight average molecular weight of the alkali-soluble resin is 5000-12000, and the acid value of the alkali-soluble resin is 80-100 mgKOH / g.

[0012] A method for preparing a photoresist composition,

[0013] (1) uniformly stirring the alkali-soluble resin and the photosensitizer at a speed of 100 to 500 rpm;

[0014] (2) adding an organic silicon leveling agent to the uniformly stirred solution in (1);

[0015] (3) heating the mixed solution obtained in step (2) to 40° C. to 50° C., adding an organic solvent, and uniformly mixing at a constant temperature of 40° C. to 55° C.;

[0016] (4) The temperature is raised to 70° C. to 75° C. and stirred at 100 to 300 rpm for two to four hours, and then the solution is removed to obtain a photoresist composition.

[0017] Preferably, the method for preparing the photoresist composition comprises:

[0018] (1) 30 parts of acrylic resin and 10 parts of acyl oxime photoinitiator were uniformly stirred at a speed of 300 rpm;

[0019] (2) adding 0.5 parts of polydimethylsiloxane to the uniformly stirred solution of (1);

[0020] (3) heating the mixed solution obtained in step (2) to 40° C., adding 55 parts of ethyl lactate, and uniformly mixing at a constant temperature of 42° C.;

[0021] (4) The temperature was raised to 75° C. and stirred at 200 rpm for two and a half hours, and then the solution was removed to obtain a photoresist composition.

[0022] Preferably, the method for preparing the photoresist composition comprises: (1) mixing 20 parts of epoxy resin and 5 parts of oxime ester photoinitiator and uniformly stirring at a speed of 200 rpm;

[0023] (2) adding 1 part of polydimethylsiloxane to the uniformly stirred solution of (1);

[0024] (3) heating the mixed solution obtained in step (2) to 50° C., adding 60 parts of ethyl lactate, and uniformly mixing at a constant temperature of 55° C.;

[0025] (4) After the temperature was raised to 72° C. and stirred at 250 rpm for three hours, the solution was removed to obtain a photoresist composition.

[0026] Preferably, the method for preparing the photoresist composition comprises:

[0027] (1) 30 parts of epoxy resin and 10 parts of acyl oxime photoinitiator were uniformly stirred at a speed of 300 rpm;

[0028] (2) adding 0.8 parts of polydimethylsiloxane to the uniformly stirred solution of (1);

[0029] (3) heating the mixed solution obtained in step (2) to 45° C., adding 55 parts of ethyl lactate, and uniformly mixing at a constant temperature of 50° C.;

[0030] (4) The temperature was raised to 70° C. and stirred at 300 rpm for three and a half hours, and then the solution was removed to obtain a photoresist composition.

[0031] By means of the above scheme, the present invention has at least the following advantages:

[0032] The photoresist composition of the invention has the advantages of convenient preparation, good stability, fast photosensitivity, high resolution and smooth material surface during light irradiation imaging.

[0033] The above description is only an overview of the technical solution of the present invention. In order to more clearly understand the technical means of the present invention, it can be implemented according to the contents of the specification. DETAILED DESCRIPTION

[0034] In order to make the purpose, technical solution and advantages of the embodiments of the present application clearer, the technical solution in the embodiments of the present application will be clearly and completely described below in combination with the embodiments of the present application. Obviously, the described embodiments are part of the embodiments of the present application, not all of the embodiments.

[0035] Example

[0036] A photoresist composition comprises the following raw material components in parts by weight: 20-30 parts of alkali-soluble resin, 5-10 parts of photosensitizer, 0.5-1 part of organic silicon leveling agent and 50-60 parts of organic solvent.

[0037] The alkali-soluble resin in the present invention includes any one of acrylic resin, epoxy resin or bisphenol fluorene resin.

[0038] The organosilicon leveling agent in the present invention is any one of polydimethylsiloxane or silicone oil.

[0039] The organic solvent in the present invention is any one of ethyl lactate, ethyl acetate, n-butyl acetate, ethylene glycol monomethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol monomethyl ether or diethylene glycol monomethyl ether.

[0040] The photosensitizer in the present invention is any one of acyl oxime photoinitiator, oxime ester photoinitiator, ketone photoinitiator or bisimidazole photoinitiator.

[0041] The weight average molecular weight of the alkali-soluble resin in the present invention is 5000-12000, and the acid value of the alkali-soluble resin is 80-100 mgKOH / g.

[0042] A method for preparing a photoresist composition,

[0043] (1) uniformly stirring the alkali-soluble resin and the photosensitizer at a speed of 100 to 500 rpm;

[0044] (2) adding an organic silicon leveling agent to the uniformly stirred solution in (1);

[0045] (3) heating the mixed solution obtained in step (2) to 40° C. to 50° C., adding an organic solvent, and uniformly mixing at a constant temperature of 40° C. to 55° C.;

[0046] (4) The temperature is raised to 70° C. to 75° C. and stirred at 100 to 300 rpm for two to four hours, and then the solution is removed to obtain a photoresist composition.

[0047] Embodiment 1

[0048] A method for preparing a photoresist composition,

[0049] (1) 30 parts of acrylic resin and 10 parts of acyl oxime photoinitiator were uniformly stirred at a speed of 300 rpm;

[0050] (2) adding 0.5 parts of polydimethylsiloxane to the uniformly stirred solution of (1);

[0051] (3) heating the mixed solution obtained in step (2) to 40° C., adding 55 parts of ethyl lactate, and uniformly mixing at a constant temperature of 42° C.;

[0052] (4) The temperature was raised to 75° C. and stirred at 200 rpm for two and a half hours, and then the solution was removed to obtain a photoresist composition.

[0053] Embodiment 2

[0054] A method for preparing a photoresist composition,

[0055] (1) 20 parts of epoxy resin and 5 parts of oxime ester photoinitiator were uniformly stirred at a speed of 200 rpm;

[0056] (2) adding 1 part of polydimethylsiloxane to the uniformly stirred solution of (1);

[0057] (3) heating the mixed solution obtained in step (2) to 50° C., adding 60 parts of ethyl lactate, and uniformly mixing at a constant temperature of 55° C.;

[0058] (4) After the temperature was raised to 72° C. and stirred at 250 rpm for three hours, the solution was removed to obtain a photoresist composition.

[0059] Embodiment 3

[0060] A method for preparing a photoresist composition,

[0061] (1) 30 parts of epoxy resin and 10 parts of acyl oxime photoinitiator were uniformly stirred at a speed of 300 rpm;

[0062] (2) adding 0.8 parts of polydimethylsiloxane to the uniformly stirred solution of (1);

[0063] (3) heating the mixed solution obtained in step (2) to 45° C., adding 55 parts of ethyl lactate, and uniformly mixing at a constant temperature of 50° C.;

[0064] (4) The temperature was raised to 70° C. and stirred at 300 rpm for three and a half hours, and then the solution was removed to obtain a photoresist composition.

[0065] Comparative Example

[0066] (1) dissolving 2 parts of naphthoquinone diazonium sulfonate in 30 parts of ethyl acetate, 20 parts of propylene glycol methyl ether acetate and 0.5 parts of dimethylacetamide, and stirring the mixture to obtain a solution;

[0067] (2) Add 0.5 parts of citric acid to the solution;

[0068] (3) heating the mixed solution obtained in step (2) to 40° C., adding 4 parts of 2-hydroxyethyl methyl acrylate, 2 parts of trimethylolpropane trimethacrylate and 4 parts of n-butyl methacrylate, and mixing at a constant temperature;

[0069] (4) Raise the temperature to 60° C. and stir at the constant temperature for 1 hour to remove the solvent to obtain a photoresist composition.

[0070] The photosensitivity of the photoresists of Examples 1 to 3 and the comparative example was measured immediately after preparation, and the results are shown in Table 1:

[0071] Table 1

[0072] <![CDATA[Photosensitivity speed mj / cm 2 > Surface flatness Embodiment 1 10.3 smooth Embodiment 2 10.5 smooth Embodiment 3 10.7 smooth Comparative Example 6.2 There are bulges

[0073] It can be seen from Table 1 that the photoresists prepared in Examples 1 to 3 of the present invention have a higher photosensitivity and the surface flatness of the materials is also relatively flat.

[0074] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. It should be pointed out that a person skilled in the art can make several improvements and modifications without departing from the technical principles of the present invention, and these improvements and modifications should also be regarded as within the scope of protection of the present invention.

Claims

1. A photoresist composition, characterized in that The invention comprises the following raw material components in parts by weight: 20 to 30 parts of alkali-soluble resin, 5 to 10 parts of photosensitizer, 0.5 to 1 part of organic silicon leveling agent and 50 to 60 parts of organic solvent.

2. A photoresist composition according to claim 1, characterized in that: The alkali-soluble resin includes any one of acrylic resin, epoxy resin or bisphenol fluorene resin.

3. A photoresist composition according to claim 1, characterized in that: The organic silicon leveling agent is any one of polydimethylsiloxane or silicone oil.

4. A photoresist composition according to claim 1, characterized in that: The organic solvent is any one of ethyl lactate, ethyl acetate, n-butyl acetate, ethylene glycol monomethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol monomethyl ether or diethylene glycol monomethyl ether.

5. A photoresist composition according to claim 1, characterized in that: The photosensitizer is any one of an acyl oxime photoinitiator, an oxime ester photoinitiator, a ketone photoinitiator or a bisimidazole photoinitiator.

6. A photoresist composition according to claim 1, characterized in that: The weight average molecular weight of the alkali-soluble resin is 5000-12000, and the acid value of the alkali-soluble resin is 80-100 mgKOH / g.

7. A method for preparing a photoresist composition according to claims 1 to 6, characterized in that: (1) uniformly stirring the alkali-soluble resin and the photosensitizer at a speed of 100 to 500 rpm; (2) adding an organic silicon leveling agent to the uniformly stirred solution in (1); (3) heating the mixed solution obtained in step (2) to 40° C. to 50° C., adding an organic solvent, and uniformly mixing at a constant temperature of 40° C. to 55° C.; (4) The temperature is raised to 70° C. to 75° C. and stirred at 100 to 300 rpm for two to four hours, and then the solution is removed to obtain a photoresist composition.

8. The method for preparing a photoresist composition according to claim 7, characterized in that: (1) 30 parts of acrylic resin and 10 parts of acyl oxime photoinitiator were uniformly stirred at a speed of 300 rpm; (2) adding 0.5 parts of polydimethylsiloxane to the uniformly stirred solution of (1); (3) heating the mixed solution obtained in step (2) to 40° C., adding 55 parts of ethyl lactate, and uniformly mixing at a constant temperature of 42° C.; (4) The temperature was raised to 75° C. and stirred at 200 rpm for two and a half hours, and then the solution was removed to obtain a photoresist composition.

9. The method for preparing a photoresist composition according to claim 7, characterized in that: (1) 20 parts of epoxy resin and 5 parts of oxime ester photoinitiator were uniformly stirred at a speed of 200 rpm; (2) adding 1 part of polydimethylsiloxane to the uniformly stirred solution of (1); (3) heating the mixed solution obtained in step (2) to 50° C., adding 60 parts of ethyl lactate, and uniformly mixing at a constant temperature of 55° C.; (4) After the temperature was raised to 72° C. and stirred at 250 rpm for three hours, the solution was removed to obtain a photoresist composition.

10. The method for preparing a photoresist composition according to claim 7, characterized in that: (1) 30 parts of epoxy resin and 10 parts of acyl oxime photoinitiator were uniformly stirred at a speed of 300 rpm; (2) adding 0.8 parts of polydimethylsiloxane to the uniformly stirred solution of (1); (3) heating the mixed solution obtained in step (2) to 45° C., adding 55 parts of ethyl lactate, and uniformly mixing at a constant temperature of 50° C.; (4) The temperature was raised to 70° C. and stirred at 300 rpm for three and a half hours, and then the solution was removed to obtain a photoresist composition.