CN102279524A - Environment-friendly photoresist composition - Google Patents
Environment-friendly photoresist composition Download PDFInfo
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- CN102279524A CN102279524A CN 201110179507 CN201110179507A CN102279524A CN 102279524 A CN102279524 A CN 102279524A CN 201110179507 CN201110179507 CN 201110179507 CN 201110179507 A CN201110179507 A CN 201110179507A CN 102279524 A CN102279524 A CN 102279524A
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- environment
- photoetching compositions
- friendly type
- water
- type photoetching
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Abstract
The invention discloses an environment-friendly photoresist composition, which comprises a. an alkaline alkyl-contained bicyclic guanidine photo-alkali-generator formed when being exposed to radiation, of which the quantity is enough to initiate polymer crosslink; b. an ester group-contained water-soluble polymer; c. a hydroxyl group-contained water-soluble polymer; and d. a solvent. Preferentially, the mass ratio of the alkyl-contained bicyclic guanidine photo-alkali-generator, the ester group-contained water-soluble polymer and the hydroxyl group-contained water-soluble polymer is 1:5-20:5-20. According to the environment-friendly photoresist composition disclosed by the invention, the polymers with good water solubility are selected, the pollution of an organic solvent is avoided, and uniform membranes can be easily obtained; and the preparation method of the alkyl-contained bicyclic guanidine photo-alkali-generator is simple, the main raw materials are commercialized, the cost is low, the absorption spectrum is wide (190-280nm), and the optical excitation efficiency and the catalytic activity are high.
Description
Technical field
The present invention relates to a kind of photoetching compositions that alkyl bicyclo guanidine light alkali produces agent that contains.
Background technology
Modern civilization is that electronic chip drives, and electronic chip all is the product of photoetching process, and photoresist is the critical material of photoetching, claims photoresist again.Photoresist is widely used in processes such as the manufacturing of P.e.c. and integrated circuit and plate making.The microelectronics of China and dull and stereotyped display industry development have rapidly driven the foundation and the development of the relevant supporting enterprise in the industrial chains such as photoresist and high purity reagent supplier.Particularly 2009 LED (light emitting diode) fast development, more effectively promoted the development of photoresist industry.
But for a long time, there is following point in the photoresist industry: one. make and use the light acid producing agent, the organic acid corroding metal, the contaminated environment that produce in the use; Two. use costliness and with serious pollution organic solvent to make developer solution; Three. the polymkeric substance of hydroxyl and ester group, because the difference of polarity if there is not potent light-initiated catalyzer, is difficult to this two base polymer is cross-linked to form the even thing that is not separated, thereby limited its application at water-based system.Thereby the processing procedure of photoresist always relates to highly basic developer solution and high-purity organic solvent at present, and the deionized water of very economical environmental protection but seldom has its report as solvent or developer solution in the photoresist field.
Summary of the invention
The objective of the invention is to propose to contain alkyl bicyclo guanidine light alkali first and produce the research thinking that agent is applied to the water soluble polymer systems photoresist, manufactured experimently out environment-friendly type photoetching compositions with better patterning effect.
The invention provides a kind of environment-friendly type photoetching compositions, it comprises: a. forms alkali when being exposed to radiation the bicyclo guanidine light alkali that contains alkyl produces agent, and it is crosslinked that quantity is enough to the initiated polymerization thing; B. the water-soluble polymers that contains ester group; C. the water-soluble polymers that contains hydroxyl; D. solvent.The mass ratio that the bicyclo guanidine light alkali that contains alkyl produces agent, the water-soluble polymers that contains ester group, the water-soluble polymers that contains hydroxyl and solvent is preferably 1: 5～and 20: 5～20: 100～200.
The bicyclo guanidine light alkali that contains alkyl among a produces agent, and its structure is as follows:
R wherein
1-6Be selected from-H-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2, and R
1-6There are 5 to be-H simultaneously at the most; R
7-11Be selected from-H-CH
3,-CH
2CH
3,-OCH
3
Perhaps
R wherein
1-6Be selected from-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2, R
7-11Be selected from-H-CH
3,-CH
2CH
3,-OCH
3
The water-soluble polymers that described b contains ester group refers to 1-vinyl pyrrolidone and 1: 1 double focusing thing of 2-dimethylaminoethyl methacrylate mass ratio; The water-soluble polymers that contains hydroxyl among the c is the polymkeric substance that cellulose etc. contains a plurality of hydroxyls; Solvent is a deionized water among the d.
The preparation method that the described bicyclo guanidine light alkali that contains alkyl produces agent is: the bicyclo guanidine, tetraphenyl boron salt that will contain alkyl mixes in water (pH value of solution is higher than 4.0) with HCl with mass ratio 1: 1, filter then, at last at methyl alcohol and chloroform potpourri (v: v=4: crystallization 1).The described bicyclo guanidine that contains alkyl, its structure following (I) or (II) shown in:
R wherein
1-6Be selected from-H-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2, and R
1-6There are 5 to be-H simultaneously at the most;
Perhaps
R wherein
1-6Be selected from-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2
The preparation method of environment-friendly type photoetching compositions:
Described environment-friendly type photoetching compositions imaging method may further comprise the steps: (1). coating photoetching compositions film on microslide; (2). cure the dry solvent of removing; (3). with the UV-irradiation photoresist film; (4). the back baked photoresist; (5). with the deionized water is that the film that developer solution will shine develops.
Baking temperature in the step (2) is 50 ℃～90 ℃, and the thickness of dry film is 0.5～1.5 micron; Step (3) medium ultraviolet optical wavelength is 150～300nm, and intensity is 5～15mW/cm
2Stoving temperature is 130 ℃～170 ℃ in the step (4), and the time is 10～30 minutes.
Advantage of the present invention:
1. it is simple that the bicyclo guanidine light alkali that contains alkyl produces the agent preparation method, and primary raw material is commercialization, and cost is low, the absorbing light spectrum width (190～280nm), optical excitation efficient height, the catalytic activity height.
2. adopt the polymkeric substance of good water solubility, avoid the pollution of organic solvent, and the homogeneous film that is easy to get, photoetching compositions film development effect is good, generates the character and the photomask Perfect Matchings of the reverse figure of parallel sections of pattern displaying.
3. deionized water substitutes traditional expensive high-purity organic solvent or contains the inorganic of highly basic and the organic solvent developer solution, avoids polluting, reducing cost.
Embodiment:
Below the specific embodiment of the present invention is elaborated.But, the invention is not restricted to following embodiment, can in the scope of main points, carry out various distortion and implement.
Embodiment 1 environment-friendly type photoetching compositions and imaging method thereof: coating photoetching compositions film on microslide, comprise α, α '-tetramethyl-1,5, double focusing thing, 2-hydroxyethyl cellulose, the deionized water solvent of 7-three azabicyclos [4.4.0] last of the ten Heavenly stems-5-alkene tetraphenylboron salt, 1-vinyl pyrrolidone and 2-dimethylaminoethyl methacrylate, four mass ratioes 1: 5: 5: 20.Cure the dry solvent of removing under 80 ℃, dry film thickness is 1.0 microns.Use wavelength 220nm then, intensity 10mW/cm
2The UV-irradiation photoresist film.Again at 160 ℃ of following back baked photoresist composition 20min.The last film that with the deionized water is developer solution will shine develops.
Embodiment 2 environment-friendly type photoetching compositions and imaging method thereof: coating photoetching compositions film on microslide, comprise α, α '-tetraethyl-1,5, double focusing thing, 2-hydroxyethyl cellulose, the deionized water solvent of 7-three azabicyclos [4.4.0] last of the ten Heavenly stems-5-alkene tetraphenylboron salt, 1-vinyl pyrrolidone and 2-dimethylaminoethyl methacrylate, four mass ratioes 1: 5: 10: 25.Cure the dry solvent of removing under 80 ℃, dry film thickness is 1.0 microns.Use wavelength 220nm then, intensity 10mW/cm
2The UV-irradiation photoresist film.Again at 160 ℃ of following back baked photoresist composition 20min.The last film that with the deionized water is developer solution will shine develops.
Embodiment 3 environment-friendly type photoetching compositions and imaging method thereof: coating photoetching compositions film on microslide, comprise β, β '-tetraethyl-1,5, double focusing thing, 2-hydroxyethyl cellulose, the deionized water solvent of 7-three azabicyclos [4.4.0] last of the ten Heavenly stems-5-alkene tetraphenylboron salt, 1-vinyl pyrrolidone and 2-dimethylaminoethyl methacrylate, four mass ratioes 1: 10: 5: 15.Cure the dry solvent of removing under 60 ℃, dry film thickness is 1.0 microns.Use wavelength 220nm then, intensity 10mW/cm
2The UV-irradiation photoresist film.Again at 170 ℃ of following back baked photoresist composition 20min.The last film that with the deionized water is developer solution will shine develops.
Embodiment 4 environment-friendly type photoetching compositions and imaging method thereof: coating photoetching compositions film on microslide, comprise α, α '-tetraethyl-1,5, the double focusing thing of 7-three azabicyclos [4.4.0] last of the ten Heavenly stems-5-alkene durene boron salt, 1-vinyl pyrrolidone and 2-dimethylaminoethyl methacrylate and 2-hydroxyethyl cellulose, deionized water solvent, four mass ratioes 1: 15: 10: 20.Cure the dry solvent of removing under 80 ℃, dry film thickness is 1.0 microns.Use wavelength 220nm then, intensity 10mW/cm
2The UV-irradiation photoresist film.Again at 140 ℃ of following back baked photoresist composition 20min.The last film that with the deionized water is developer solution will shine develops.
Embodiment 5 environment-friendly type photoetching compositions and imaging method thereof: coating photoetching compositions film on microslide, comprise β, β '-tetraethyl-1,5, the double focusing thing of 7-three azabicyclos [4.4.0] last of the ten Heavenly stems-5-alkene durene boron salt, 1-vinyl pyrrolidone and 2-dimethylaminoethyl methacrylate and 2-hydroxyethyl cellulose, deionized water solvent, four mass ratioes 1: 5: 10: 30.Cure the dry solvent of removing under 90 ℃, dry film thickness is 1.0 microns.Use wavelength 220nm then, intensity 10mW/cm
2The UV-irradiation photoresist film.Again at 160 ℃ of following back baked photoresist composition 20min.The last film that with the deionized water is developer solution will shine develops.
Claims (9)
1. the environment-friendly type photoetching compositions is characterized in that, comprising: a. forms alkali when being exposed to radiation the bicyclo guanidine light alkali that contains alkyl produces agent; B. the water-soluble polymers that contains ester group; C. the water-soluble polymers that contains hydroxyl; D. solvent.
2. environment-friendly type photoetching compositions according to claim 1, it is characterized in that the mass ratio that contains the bicyclo guanidine light alkali generation agent of alkyl, the water-soluble polymers that contains ester group, the water-soluble polymers that contains hydroxyl and solvent is 1: 5～20: 5～20: 100～200.
3. environment-friendly type photoetching compositions according to claim 1 and 2 is characterized in that, the described water-soluble polymers that contains ester group refers to 1-vinyl pyrrolidone and 1: 1 double focusing thing of 2-dimethylaminoethyl methacrylate mass ratio.
4. environment-friendly type photoetching compositions according to claim 1 and 2 is characterized in that, the described water-soluble polymers that contains hydroxyl is cellulose and derivant thereof.
5. environment-friendly type photoetching compositions according to claim 1 and 2 is characterized in that, the described bicyclo guanidine light alkali that contains alkyl produces agent, and its structure is as follows:
R wherein
1-6Be selected from-H-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2, and R
1-6There are 5 to be-H simultaneously at the most; R
7-11Be selected from-H-CH
3,-CH
2CH
3,-OCH
3
Perhaps
R wherein
1-6Be selected from-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2, R
7-11Be selected from-H-CH
3,-CH
2CH
3,-OCH
3
6. the described environment-friendly type photoetching compositions of claim 1 imaging method is characterized in that, may further comprise the steps: (1) is coated with the photoetching compositions film on microslide; (2) cure the dry solvent of removing; (3) with the UV-irradiation photoresist film; (4) back baked photoresist; (5) be that the film that developer solution will shine develops with the deionized water.
7. environment-friendly type photoetching compositions imaging method according to claim 6 is characterized in that, the baking temperature in the step (2) is 50 ℃～90 ℃, and the thickness of dry film is 0.5～1.5 micron.
8. environment-friendly type photoetching compositions imaging method according to claim 6 is characterized in that, step (3) medium ultraviolet optical wavelength is 150～300nm, and intensity is 5～15mW/cm
2
9. environment-friendly type photoetching compositions imaging method according to claim 6 is characterized in that, stoving temperature is 130 ℃～170 ℃ in the step (4), and the time is 10～30 minutes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110179507 CN102279524A (en) | 2011-06-29 | 2011-06-29 | Environment-friendly photoresist composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110179507 CN102279524A (en) | 2011-06-29 | 2011-06-29 | Environment-friendly photoresist composition |
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| Publication Number | Publication Date |
|---|---|
| CN102279524A true CN102279524A (en) | 2011-12-14 |
Family
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Family Applications (1)
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|---|---|---|---|
| CN 201110179507 Pending CN102279524A (en) | 2011-06-29 | 2011-06-29 | Environment-friendly photoresist composition |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100136477A1 (en) * | 2008-12-01 | 2010-06-03 | Ng Edward W | Photosensitive Composition |
| CN102093348A (en) * | 2010-12-29 | 2011-06-15 | 山东大学 | Unsaturated alkyl bicyclic guanidine as well as preparation method and application of unsaturated alkyl bicyclic guanidine |
-
2011
- 2011-06-29 CN CN 201110179507 patent/CN102279524A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100136477A1 (en) * | 2008-12-01 | 2010-06-03 | Ng Edward W | Photosensitive Composition |
| CN102093348A (en) * | 2010-12-29 | 2011-06-15 | 山东大学 | Unsaturated alkyl bicyclic guanidine as well as preparation method and application of unsaturated alkyl bicyclic guanidine |
Non-Patent Citations (2)
| Title |
|---|
| 《Journal of the American Chemical Society》 20081231 Xun Sun, Jian Ping Gao, and Zhi Yuan Wang Bicyclic Guanidinium Tetraphenylborate A Photobase Generator and A Photocatalyst for Living Anionic Ring-Opening Polymerization and Cross-Linking of Polymeric Materials Containing Ester and Hydroxy Groups 第8130-8131页 第130卷, * |
| 《Polymer》 20100707 Cheng Bo Cao, Chen Zhou, Xun Sun, Jian Ping Gao, Zhi Yuan Wang Photo-induced crosslinking of water-soluble polymers with a new photobase generator 第4058-4062页 第51卷, * |
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Application publication date: 20111214 |