Polyhydroxystyrene, method for preparing same polyhydroxystyrene, and photoresist composition comprising same

Abstract

The present invention relates to high-purity polyhydroxystyrene, a method for preparing polyhydroxystyrene, and a photoresist composition comprising same, wherein the high-purity polyhydroxystyrene has a purity of 95 % or more and, in a 13C-NMR analysis graph, does not exhibit a peak at 140-150 ppm caused by residual styrene and a peak at 10-25 ppm caused by an aliphatic alkyl group. In the present invention, the manufacture of high-purity polyhydroxystyrene could be achieved by changing the structure of an initiator instead of using a conventional initiator. As such, the high-purity polyhydroxystyrene of the present invention is included in a photoresist composition and can be widely applied to electronic materials for various uses.

Description

Poly-hydroxy styrene, method for producing poly-hydroxy styrene thereof, and photoresist composition comprising the same

[0001] The present invention relates to poly-hydroxy styrene, a method for producing the poly-hydroxy styrene, and a photoresist composition comprising the same, and more particularly, to high-purity poly-hydroxy styrene with a low impurity content, a method for producing the same, and a photoresist composition comprising the same.

[0002] Polyhydroxystyrene (hereinafter referred to as 'PHS') is manufactured by adding an initiator to hydroxystyrene and reacting it through living radical polymerization or anionic polymerization.

[0003] In addition, the hydroxyl group at the terminal of the PHS homopolymer thus manufactured is blocked and used for various purposes, or it is manufactured as a copolymer with a styrene monomer and the hydroxyl group at the terminal of the PHS is blocked and used. Its uses include the manufacture of electronic materials, resins, elastomers, adhesives, coatings, automotive finishes, and inks, or it can be used as an additive in elastomer and resin formulations.

[0004] These PHS polymers are manufactured by living radical polymerization or anionic polymerization. However, impurities resulting from the styrene-based initiators used in living radical polymerization or the organic alkali metal initiators used in anionic polymerization reduce the purity of the final PHS polymer, posing a problem for its intended use.

[0005] Therefore, there is an urgent need for a method to manufacture high-purity polyhydroxy-styrene, which is used in various electronic materials.

[0006] For reference, U.S. Patent No. 5,925,718 discloses a method for producing polyhydroxystyrene derivatives, and U.S. Patent No. 4,316,995 discloses a method for producing vinyl phenol.

[0007] Accordingly, the purpose of the present invention is to provide high-purity poly-hydroxy styrene by optimizing the structure of a polymerization initiator used so as to minimize the production of impurities.

[0008] In addition, another object of the present invention is to provide a method for producing the high-purity poly-hydroxy styrene.

[0009] Additionally, the present invention aims to provide a photoresist composition usable for various materials, including the high-purity poly-hydroxy styrene.

[0010] According to one embodiment of the present invention, a high-purity poly-hydroxy styrene has a purity of 95% or more, 13 It is characterized by not showing a peak at 140 to 150 ppm due to residual styrene and a peak at 10 to 25 ppm due to an aliphatic alkyl group in the C-NMR analysis graph.

[0011] The poly-hydroxy styrene according to the present invention may have a weight average molecular weight in the range of 2,000 to 30,000.

[0012] According to one embodiment of the present invention, a high-purity poly-hydroxy styrene may be manufactured using a compound represented by the following chemical formula 1 as a polymerization initiator.

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] R1 is a C1~C9 substituted or unsubstituted alkoxy or acetoxy group,

[0017] R2 to R5 are the same or different, each of which is hydrogen; or a C1~C9 substituted or unsubstituted alkyl group,

[0018] R4 and R5 can be linked to each other to form a hydrocarbon ring,

[0019] m is an integer from 0 to 4.

[0020]

[0021] In addition, the method for producing high-purity poly-hydroxy styrene of the present invention may include a step of synthesizing a poly-hydroxy styrene intermediate in the presence of a hydroxyl-protected styrene monomer, a polymerization initiator, and a solvent, and a step of hydrolyzing the poly-hydroxy styrene intermediate to polymerize a poly-hydroxy styrene polymer.

[0022] According to one embodiment of the present invention, the hydroxyl group of the hydroxyl-protected styrene monomer is substituted with a C1 to C9 substituted or unsubstituted alkoxy or acetoxy group, and has the characteristic of substantially not containing a hydroxyl group.

[0023] The polymerization initiator of the present invention may be represented by the chemical formula 1.

[0024] According to one embodiment of the present invention, the production of the poly-hydroxy styrene intermediate may be performed at a temperature of 20°C to 250°C for 1 hour to 100 hours.

[0025] In addition, the poly-hydroxy styrene intermediate manufactured according to the present invention has the characteristic of not containing a hydroxyl group at its terminal.

[0026] According to one embodiment of the present invention, the hydrolysis of the poly-hydroxy styrene intermediate is carried out in the presence of an acid or base catalyst, and is characterized in that a hydroxyl group is generated during this process.

[0027] The poly-hydroxy styrene according to the present invention may be produced by living radical polymerization or anionic polymerization.

[0028] Additionally, the present invention can provide a photoresist composition comprising the high-purity poly-hydroxy styrene.

[0029] In the present invention, the purity is 95% or more, 13 High-purity poly-hydroxy styrene was produced, which did not exhibit a peak at 140 to 150 ppm due to residual styrene and a peak at 10 to 25 ppm due to aliphatic alkyl groups in the C-NMR analysis graph.

[0030] In the present invention, the structure of a styrene-based initiator used in conventional living radical polymerization was changed to enable the production of high-purity poly-hydroxy styrene.

[0031]

[0032] Figures 1 and 3 are each a polyhydroxy-styrene polymer manufactured according to Example 1. 13 This is the result of C-NMR analysis and its enlarged image (140-160 ppm).

[0033] Figures 2 and 4 are each a polyhydroxy-styrene polymer manufactured according to Comparative Example 1. 13 This is the result of C-NMR analysis and its enlarged image (140-160 ppm).

[0034] Figure 5 is a diagram of a polyhydroxy-styrene polymer manufactured according to Comparative Example 2. 13 This is the result of C-NMR analysis.

[0035] The present invention is described in more detail below.

[0036] The terminology used herein is for the purpose of describing particular embodiments and is not intended to limit the invention.

[0037] As used herein, the singular forms include the plural forms unless the context clearly dictates otherwise. Furthermore, as used herein, the words "comprise" and / or "comprising" specify the presence of stated features, numbers, steps, operations, elements, components and / or groups thereof, but do not preclude the presence or addition of one or more other features, numbers, operations, elements, components and / or groups thereof.

[0038]

[0039] The present invention relates to high-purity poly-hydroxy styrene, a method for producing the poly-hydroxy styrene, and a photoresist composition comprising the same.

[0040] The high-purity poly-hydroxy styrene according to the present invention may have a purity of 95% or more, preferably 98% or more, and more preferably 99% or more. Since a higher purity corresponds to the effects of the present invention, the upper limit is not limited, but may be 100% or less. Specifically, it includes a purity of 95% or more as measured by gel permeation chromatography (GPC).

[0041] In addition, the high purity poly-hydroxy styrene according to the present invention 13 It is characterized by not showing a peak at 140 to 150 ppm due to residual styrene and a peak at 10 to 25 ppm due to an aliphatic alkyl group in the C-NMR analysis graph.

[0042] Above 13 The peaks found in the C-NMR analysis graph are predicted to be mainly caused by residues of compounds used as polymerization initiators.

[0043] For example, when poly-hydroxy styrene is prepared together with hydroxy styrene monomer by adding TEMPO (2,2',6,6'-tetramethylpiperidine N-oxide 2, R¼), ethylbenzene, and t-BuOOH, a copper halide, the styrene monomer remains in the final prepared poly-hydroxy styrene polymer, which causes 13 In the C-NMR measurement graph, a peak at 140-160 ppm is found, which acts as an impurity.

[0044] In addition, in the production of poly-hydroxystyrene by anionic polymerization, organic alkali metals, specifically, alkyl lithiums such as n-butyl lithium and sec-butyl lithium, were used as conventional polymerization initiators. However, in this case, due to the use of the organic alkali metals, a peak at 10 to 25 ppm due to alkyl groups (aliphatic alkyls) in the final PHS polymer, etc. 13 It is found in the C-NMR results and is soon considered to be an impurity in the final manufactured polymer.

[0045]

[0046] In order to solve the problems arising from the use of such initiators, the structure of the initiator is changed in the present invention so that such residues do not remain as impurities, thereby enabling the production of high-purity poly-hydroxy styrene.

[0047] The poly-hydroxy styrene of the present invention preferably has a weight average molecular weight of 2,000 to 30,000 in terms of solubility, adhesiveness, session edge roughness, development rate, etching resistance, etc.

[0048]

[0049] In addition, the high-purity poly-hydroxy styrene of the present invention can be manufactured by including a step of synthesizing a poly-hydroxy styrene intermediate in the presence of a hydroxyl-protected styrene monomer, a polymerization initiator, and a solvent, and a step of hydrolyzing the poly-hydroxy styrene intermediate to polymerize a poly-hydroxy styrene polymer.

[0050] Step 1 involves synthesizing a poly-hydroxy styrene intermediate using a hydroxyl-protected styrene monomer, a polymerization initiator, and a solvent.

[0051] In order to manufacture poly-hydroxy styrene, a hydroxy styrene monomer is required, but a styrene monomer containing a hydroxy group has a high molecular weight and PDI due to the hydroxy group at the terminal, and the problem of poor polymerization reproducibility is solved by using a hydroxy group-protected styrene monomer in which the hydroxy group is protected by another substituent.

[0052] Here, the term 'hydroxyl-protected styrene monomer' refers to a styrene monomer that substantially does not contain a hydroxyl group by replacing the hydroxyl group of a hydroxyl-protected styrene monomer with another functional group.

[0053] Specifically, the hydroxyl group of the hydroxyl-protected styrene monomer according to the present invention is substituted with a C1 to C9 substituted or unsubstituted alkoxy or acetoxy group, and has a structure that substantially does not contain a hydroxyl group.

[0054] As a result, the final manufactured poly-hydroxy styrene is 13 It has the effect that the peak at 140-150 ppm due to residual styrene is not found in the C-NMR analysis graph.

[0055]

[0056] In addition, the poly-hydroxy styrene finally manufactured by using a compound represented by the following chemical formula 1 as a polymerization initiator instead of using lithium alkali metal 13 It has the effect that the peak at 10 to 25 ppm due to the aliphatic alkyl group is not found in the C-NMR analysis graph.

[0057] Therefore, a preferred polymerization initiator of the present invention may be a compound represented by the following chemical formula 1.

[0058] [Chemical Formula 1]

[0059]

[0060] In chemical formula 1,

[0061] R1 is a C1~C9 substituted or unsubstituted alkoxy or acetoxy group,

[0062] R2 to R5 are the same or different, each of which is hydrogen; or a C1~C9 substituted or unsubstituted alkyl group,

[0063] R4 and R5 can be linked to each other to form a hydrocarbon ring,

[0064] m is an integer from 0 to 4.

[0065] The organic solvent used in the production of the above poly-hydroxy styrene intermediate may be propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), cyclohexanone (CH), ethyl lactate (EL), gamma-butyrolactone (GBL), etc., which may be used alone or in combination, and among these, propylene glycol monomethyl ether acetate (PGMEA) is preferred.

[0066] The above poly-hydroxy styrene intermediate can be obtained by introducing a hydroxyl-protected styrene monomer, a polymerization initiator, a solvent, a reaction catalyst, etc. into a jacket reactor under a nitrogen atmosphere and stirring well to sufficiently dissolve the monomer. Then, the residual gas inside the reactor is removed and polymerization is performed for 1 to 100 hours while maintaining the internal temperature at 20 to 250°C.

[0067] The polymer obtained above can be obtained as a yellow solid powder through a normal cooling process, decompression process, vacuum drying process, etc.

[0068] The poly-hydroxy styrene intermediate of the present invention thus obtained has the characteristic of not containing a hydroxyl group at its terminal.

[0069]

[0070] In the present invention, the poly-hydroxy styrene intermediate is introduced into a reactor, completely dissolved in a solvent, and then reacted in the presence of an acid or base catalyst. In this process, the hydroxyl-protected functional groups are hydrolyzed to generate hydroxyl groups, thereby polymerizing the final poly-hydroxy styrene polymer.

[0071] The solvent used at this time may be tetrahydrofuran, methanol, acetone, etc., and the acid or base catalyst required for the hydrolysis reaction may be any known one, and its type is not particularly limited.

[0072] In addition, by cooling the obtained polymer to room temperature and going through neutralization, decompression, vacuum drying, etc., a white solid powder can be obtained.

[0073] The poly-hydroxy styrene of the present invention may be produced by living radical polymerization or anionic polymerization.

[0074] The present invention can also provide a photoresist composition comprising the poly-hydroxy styrene. In one embodiment of the present invention, the photoresist composition may, of course, include conventional additives included in conventional photoresist compositions, such as a photoacid generator, an acid diffusion control agent, a corrosion inhibitor, and a solvent.

[0075] In the present invention, a photoresist composition containing high-purity poly-hydroxy styrene with minimized impurity content is used in a photoresist process that uses a photo process such as a semiconductor or display, and is particularly used in a CAR (Chemically amplified resist) of a KrF light source, and can have the effect of ensuring transparency while also having excellent thermal properties and etching resistance.

[0076] Preferred embodiments of the present invention will be described in detail below. The following examples are intended solely to illustrate the present invention and should not be construed as limiting the scope of the present invention. Furthermore, while specific compounds are used in the examples below, it will be apparent to those skilled in the art that equivalent compounds of these compounds can also produce similar or equivalent effects.

[0077]

[0078] <Example>

[0079] Under a nitrogen atmosphere, 150 g (0.92 mol) of an acetoxy-protected styrene monomer, 4.34 g (0.013 mol) of an initiator having a structure in which R1 in the chemical formula 1 is an acetoxy group, R2 and R3 are hydrogen, m is 0, and R4 and R5 are connected to each other to form a hydrocarbon ring, the terminal of which is substituted with an OH group, 2.91 g (0.03 mol) of acetic acid, and 112.5 g of the solvent PGMEA were charged into a jacket reactor and stirred for 30 minutes to completely dissolve the acetoxy-protected styrene monomer. Thereafter, any residual gas inside was removed using nitrogen bubbling for 30 minutes.

[0080] Next, the reactor was heated to maintain the internal temperature at 130°C and reacted for 24 hours to polymerize a polyhydroxystyrene intermediate. The obtained intermediate was filtered under reduced pressure to obtain a wet polymer. This was vacuum-dried at 60°C for 12 hours to obtain 128 g of yellow polymer powder. (Mw: 10898, PDI 1.30)

[0081] 122 g of the poly-hydroxy styrene intermediate obtained above, 183.0 g of THF, and 366.0 g of methanol were charged into a reactor, stirred for 1 hour to completely dissolve, and then 116.0 g (0.83 mol) of NH4OH was charged and heated to reach an internal temperature of 50°C, and then reacted for 12 hours under a nitrogen atmosphere to mature, thereby obtaining a poly-hydroxy styrene polymer.

[0082] Next, 149.1 g (2.48 mol) of acetic acid was added dropwise to the solution cooled to room temperature to neutralize it, and this was added dropwise to 3904 g of ultrapure water and filtered under reduced pressure to obtain a wet polymer. This was dried at 60°C for 48 hours to obtain 97.6 g of white polymer powder. (Mw 10735, PDI 1.21)

[0083]

[0084] Comparative Example 1

[0085] In Comparative Example 1, poly-hydroxy styrene was prepared by adding ethylbenzene, t-BuOOH, CuBr2 catalyst, and hydroxy-styrene monomer using an initiator represented by the following chemical formula 2.

[0086] Specifically, under a nitrogen atmosphere, 150 g (0.92 mol) of an acetoxy-protected styrene monomer, 3.38 g (0.013 mol) of an initiator represented by the above chemical formula 2, 2.91 g (0.03 mol) of acetic acid, and 112.5 g of the solvent PGMEA were charged into a jacket reactor and stirred for 30 minutes to completely dissolve the acetoxy-protected styrene monomer. Thereafter, any residual gas within was removed using nitrogen bubbling for 30 minutes.

[0087] Next, the reactor was heated to maintain the internal temperature at 130°C and reacted for 24 hours to polymerize a polyhydroxystyrene intermediate. The obtained intermediate was filtered under reduced pressure to obtain a wet polymer. This was vacuum-dried at 60°C for 12 hours to obtain 122 g of yellow polymer powder. (Mw: 9616, PDI 1.21)

[0088] 122 g of the poly-hydroxy styrene intermediate obtained above, 183.0 g of THF, and 366.0 g of methanol were charged into a reactor, stirred for 1 hour to completely dissolve, and then 116.0 g (0.83 mol) of NH4OH was charged and heated to reach an internal temperature of 50°C, followed by reaction for 12 hours under a nitrogen atmosphere to mature, thereby obtaining a poly-hydroxy styrene polymer.

[0089] Next, 149.1 g (2.48 mol) of acetic acid was added dropwise to the solution cooled to room temperature to neutralize it, and this was added dropwise to 3904 g of ultrapure water and filtered under reduced pressure to obtain a wet polymer. This was dried at 60°C for 48 hours to obtain 97.6 g of white polymer powder. (Mw 9776, PDI 1.22)

[0090] [Chemical Formula 2]

[0091]

[0092]

[0093] Comparative Example 2: PHS polymerization using anionic polymerization

[0094] Under a nitrogen atmosphere, 150 g (0.92 mol) of a butoxy-protected styrene monomer and 930 g of THF solvent were charged into a jacket reactor, stirred for 30 minutes, and then the reactor was cooled to maintain the internal temperature at -78°C. 10.61 g (0.0270 mol) of normal butyllithium was added dropwise over 1 hour, reacted for 2 hours, and 22.39 g of methanol was added to terminate the reaction. The intermediate thus obtained was charged into 3375 g of methanol, filtered, and white crystals were obtained, which were vacuum-dried at 60°C for 12 hours to obtain 146 g of the product. (Mw: 8286, PDI 1.2)

[0095] 146 g of the poly-hydroxy styrene intermediate obtained above and 438.0 g of acetone were charged into a reactor, stirred for 30 minutes, and completely dissolved. Then, 105.0 g (1.02 mol l) of a 35% HCL aqueous solution was added, aged for 12 hours, and then precipitated in 6890 g of ultrapure water and filtered to obtain a white poly-hydroxy styrene polymer. (Mw: 8468, PDI 1.2)

[0096]

[0097] <Experimental Example 1: Conversion Rate Measurement>

[0098] In the above examples and comparative examples, the conversion rate was measured 24 hours after the start of the reaction during PHS production, and the results are shown in Table 1 below.

[0099] Classification Implementation Preliminary Comparison Example 1 Comparison Example 2 Conversion Rate 92.9% 85.4% 98.28%

[0100] From the above results, it was confirmed that the conversion rate of poly-hydroxy styrene (Example) manufactured using the present invention and an initiator having a structure different from that of a conventional polymerization initiator was equivalent to that of conventionally used initiators or higher than that of Comparative Example 1. Therefore, even when using the initiator of the present invention having a modified structure, PHS can be manufactured with high efficiency.

[0101]

[0102] <Experimental Example 2: Molecular Weight Measurement>

[0103] The poly-hydroxy styrene manufactured in the above example was synthesized three times, and the molecular weight, purity, and molecular weight distribution of the synthesized polymer were measured by GPC, and the results are shown in Table 2 below.

[0104] Classification GPC Measurement Results MwPDIPurity 1 time 2 4 hours 84301.3084.92 Final 85411.1999.74 2 times 2 4 hours 90711.2685.40 Final 91581.2199.38 3 times 2 4 hours 101461.3692.90 Final 99861.2199.84

[0105] Referring to the results in Table 2 above, it can be confirmed that although the molecular weight varies somewhat depending on the number of synthesis steps, the PDI and purity of the final polymer have similar values. In addition, the color and precipitation patterns of the manufactured intermediate and final polymer showed similar results to those of polymers manufactured using conventional methods.

[0106] In addition, it was confirmed that the molecular weight of the present invention can be easily controlled by adjusting the amount of polymerization initiator. In addition, compared to existing initiators, the initiation temperature was slightly higher (the reaction initiation temperature was confirmed through TGA measurement to be 157.06°C for the present invention and 123.51°C for Comparative Example 1), so the initial initiation speed was slow, and the molecular weight was confirmed to be higher than that of the Comparative Example.

[0107]

[0108] <Experimental Example 3: 13 Identification of impurities through C-NMR analysis>

[0109] Each poly-hydroxy styrene polymer manufactured in the above examples and comparative examples 13 The ratio of non-substituted hydroxyl groups was calculated using C-NMR analysis and expressed as impurity content (%), and the results are shown in Table 3 and Figures 1 to 5.

[0110] Preliminary comparative example of classification 1 Impurity content (%) Not detected 1.15%

[0111] Referring to the results in Table 3 above, it can be confirmed that the poly-hydroxy styrene polymer according to the present invention has no impurities detected at 140 to 150 ppm, while in the comparative example, 1.15% of impurities are detected. This 13 As can be confirmed from the C-NMR measurement results shown in FIGS. 1 to 4, in the poly-hydroxy styrene polymer according to Comparative Example 1, impurities were detected due to a peak at 140 to 150 ppm caused by residual styrene because the terminal of the initiator used contained a styrene structure (see FIG. 2 and its enlarged version, FIG. 4).

[0112] However, in the poly-hydroxy styrene polymer according to the present invention, the structure of the initiator is changed to protect the styrene structure at the terminal, so unlike the conventional method, no impurities are detected due to the peak at 140-150 ppm caused by residual styrene. (See Fig. 1 and its enlarged version, Fig. 3.)

[0113]

[0114] In addition, even when the alkyl lithium initiator of Comparative Example 2 is used and polyhydroxy-styrene is produced by anionic polymerization, it can be confirmed that a peak due to the n-butyl group at 10 to 25 ppm is found, as shown in FIG. 5 below.

[0115] However, it can be confirmed that in the poly-hydroxy styrene polymer of the present invention, no peak due to an aliphatic alkyl group is found even at 10 to 25 ppm. (See Fig. 1)

[0116]

[0117] While specific aspects of the present invention have been described in detail above, it will be apparent to those skilled in the art that these specific descriptions merely represent preferred embodiments and are not intended to limit the scope of the present invention. Accordingly, the substantial scope of the present invention is defined by the appended claims and their equivalents.

[0118]

[0119] The high-purity poly-hydroxy styrene of the present invention can be included in a photoresist composition and widely applied to electronic materials for various purposes.

Claims

1. The purity is 95% or higher, 13 High-purity poly-hydroxy styrene characterized by not showing a peak at 140 to 150 ppm due to residual styrene and a peak at 10 to 25 ppm due to aliphatic alkyl groups in the C-NMR analysis graph.

2. In paragraph 1, The above poly-hydroxy styrene is a high-purity poly-hydroxy styrene having a weight average molecular weight in the range of 2,000 to 30,000.

3. In paragraph 1, The above high-purity poly-hydroxy styrene is a high-purity poly-hydroxy styrene manufactured using a compound represented by the following chemical formula 1 as a polymerization initiator: [Chemical Formula 1] In chemical formula 1, R1 is a C1~C9 substituted or unsubstituted alkoxy or acetoxy group, R2 to R5 are the same or different, each of which is hydrogen; or a C1~C9 substituted or unsubstituted alkyl group, R4 and R5 can be linked to each other to form a hydrocarbon ring, m is an integer from 0 to 4.

4. A step of synthesizing a poly-hydroxy styrene intermediate in the presence of a hydroxyl-protected styrene monomer, a polymerization initiator, and a solvent, and A method for producing high-purity poly-hydroxy styrene according to claim 1, comprising a step of hydrolyzing the poly-hydroxy styrene intermediate to polymerize a poly-hydroxy styrene polymer.

5. In paragraph 4, A method for producing high-purity poly-hydroxy styrene, wherein the hydroxyl group of the above-mentioned hydroxyl-protected styrene monomer is substituted with a C1-C9 substituted or unsubstituted alkoxy or acetoxy group and substantially does not contain a hydroxyl group.

6. In paragraph 4, A method for producing high-purity poly-hydroxy styrene, wherein the polymerization initiator is represented by the chemical formula 1 according to claim 3.

7. In paragraph 4, A method for producing poly-hydroxy styrene, wherein the production of the above poly-hydroxy styrene intermediate is performed at a temperature of 20°C to 250°C for 1 to 100 hours.

8. In paragraph 4, A method for producing poly-hydroxy styrene, wherein the poly-hydroxy styrene intermediate produced above does not contain a hydroxy group at its terminal.

9. In paragraph 4, A method for producing poly-hydroxy styrene, wherein hydrolysis of the above poly-hydroxy styrene intermediate is carried out under an acid or base catalyst, and a hydroxyl group is generated in the process.

10. In paragraph 4, The above poly-hydroxy styrene is a method for producing poly-hydroxy styrene using living radical polymerization or anionic polymerization.

11. A photoresist composition comprising poly-hydroxy styrene according to claim 1.

Images