CN116003674A - Resin and preparation method of ArF wet photoresist containing resin - Google Patents
Resin and preparation method of ArF wet photoresist containing resin Download PDFInfo
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- CN116003674A CN116003674A CN202111231211.2A CN202111231211A CN116003674A CN 116003674 A CN116003674 A CN 116003674A CN 202111231211 A CN202111231211 A CN 202111231211A CN 116003674 A CN116003674 A CN 116003674A
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Abstract
The invention discloses a resin and a preparation method of ArF wet photoresist containing the same. The preparation method of the resin comprises the following steps: in a solvent, carrying out polymerization reaction on a monomer A, a monomer B, a monomer C and a monomer D to obtain the resin; wherein the weight portion of the monomer A is 40-47.5 portions; 1 to 7.5 parts by weight of monomer B; the said0.25-2.5 parts of monomer C; the monomer D is 0.25-2.5 parts by weight. The photoresist comprising the resin prepared by the preparation method of the invention has the advantages of excellent photosensitivity, good depth of focus (DOF) and good line width uniformity (CDU).
Description
Technical Field
The invention relates to a resin and a preparation method of ArF wet photoresist containing the same.
Background
The photolithography technique refers to a pattern micromachining technique for transferring a pattern designed on a mask plate onto a substrate through exposure, development, etching and other technological processes by utilizing chemical sensitivity of a photolithography material (particularly photoresist) under the actions of visible light, ultraviolet rays, electron beams and the like. Photolithography materials (particularly photoresists), also known as photoresists, are the most critical functional chemical materials involved in photolithography, the main components of which are resins, photoacid generators (Photo Acid Generator, PAG), and corresponding additives and solvents. The photoacid generator is a photosensitive compound which is decomposed under illumination to generate acid, and the generated acid can lead acid-sensitive resin to generate decomposition or crosslinking reaction, so that the dissolution contrast of an illumination part and a non-illumination part in a developing solution is increased, and the photoacid generator can be used in the technical field of pattern micromachining.
Three important parameters of photoresist include resolution, sensitivity, line width roughness, which determine the process window of the photoresist at the time of chip fabrication. With the continuous improvement of the performance of semiconductor chips, the integration level of integrated circuits increases exponentially, and the patterns in the integrated circuits continue to shrink. In order to make smaller sized patterns, the performance index of the above three photoresists must be improved. The use of a short wavelength light source in the photolithography process may increase the resolution of the photoresist according to the rayleigh equation. The light source wavelength of the photolithography process has evolved from 365nm (I-line) to 248nm (KrF), 193nm (ArF), 13nm (EUV). In order to improve the sensitivity of the photoresist, the currently mainstream KrF, arF, EUV photoresist adopts a chemically amplified photosensitive resin. Thus, photosensitizers (photoacid generators) compatible with chemically amplified photosensitive resins are widely used in high-end photoresists.
As photolithography processes evolve, to 193nm immersion processes, the complexity of the process increases, placing higher and higher demands on resists (i.e., photoresists). Developing photoresist capable of improving resolution, sensitivity and line width roughness becomes a problem to be solved urgently in industry.
Disclosure of Invention
The invention aims to overcome the defect of poor photoresist performance in the prior art, and provides a resin and a preparation method of ArF wet photoresist containing the resin, so as to improve the performances of photoresist in various aspects such as resolution, sensitivity, line width roughness and the like.
The invention solves the technical problems through the following technical proposal.
A method of preparing a resin comprising the steps of: in a solvent, carrying out polymerization reaction on a monomer A, a monomer B, a monomer C and a monomer D to obtain the resin;
the weight of the monomer A is 40-47.5 parts;
1 to 7.5 parts by weight of monomer B;
the monomer C is 0.25-2.5 parts by weight;
the monomer D is 0.25-2.5 parts by weight;
R 1 is C 1-10 An alkyl group;
R 2 is H or C 1-5 An alkyl group;
R 3 is C 1-10 An alkyl group;
R 4 is H or C 1-5 An alkyl group;
R 5 is C 2-5 Alkenyl groups;
R 6 is H or C 1-5 An alkyl group.
In some embodiments, the monomer A is present in an amount of 42.5 to 45 parts by weight.
In some embodiments, the monomer B is 2.5 to 4 parts by weight.
In some embodiments, the monomer C is present in an amount of 0.5 to 1.25 parts by weight.
In some embodiments, the monomer D is 0.5 to 1.25 parts by weight.
In some embodiments, R 1 In the above, the C 1-10 Alkyl is C 1-5 Alkyl is preferably methyl, ethyl, n-propyl or isopropyl.
In some embodiments, R 2 In the above, the C 1-5 Alkyl is methyl, ethyl, n-propyl or isopropyl.
In some embodiments, R 3 In the above, the C 1-10 Alkyl is C 1-5 Alkyl is preferably methyl, ethyl, n-propyl or isopropyl.
In some embodiments, R 4 In the above, the C 1-5 Alkyl is methyl, ethyl, n-propyl or isopropyl.
In some embodiments, R 5 In (C) 2-5 Alkenyl group is C 2-3 Alkenyl groups. The C is 2-3 Alkenyl is preferably isopropenyl or vinyl.
In some embodiments, R 6 In the above, the C 1-5 Alkyl is methyl, ethyl, n-propyl or isopropyl.
In some embodiments, R 2 Is C 1-5 An alkyl group.
In some embodiments, R 4 Is C 1-5 An alkyl group.
In some embodiments, R 6 Is C 1-5 An alkyl group.
In some embodiments, R 1 、R 2 、R 3 、R 4 And R is 6 Independently methyl.
In some embodiments, R 5 Is isopropenyl.
In some embodiments, the weight average molecular weight (Mw) of the resin is from 1,000 to 500,000.
In some embodiments, the resin has a weight average molecular weight (Mw) of 3,000 to 100,000, which may be 5000 to 10000, such as 6000, 7000, 8000 or 9000.
In some embodiments, the resin has a dispersity (Mw/Mn) of 1.0 to 2.0, preferably 1.5 to 2.0.
In some embodiments, the resin has a dispersity (Mw/Mn) of 1.1,1.2,1.4,1.8,1.9 or 2.
In some embodiments, the monomer a is 42.5 to 45 parts by weight;
2.5-4 parts by weight of monomer B;
the monomer C is 0.5-1.25 parts by weight;
the monomer D is 0.5-1.25 parts by weight.
In some embodiments, R 1 、R 2 、R 3 、R 4 And R is 6 Is methyl, R 5 Is isopropenyl.
In some embodiments, the monomer a is
The weight portion is 42.5-47.5 portions.
In some embodiments, the monomer B is
The weight portion is 1-7.5 portions.
In some embodiments, the monomer C is
The weight portion is 0.25-1.75 portions.
In some embodiments, the monomer D is
The weight portion is 0.5-1.75 portions.
In some embodiments, the resin is selected from any one of the following resins 1-8:
resin 1:42.5 parts of
5 parts->
1.25 parts of
And 1.25 parts of->
Resin 2:45 parts of
4 parts->
0.5 part->
And 0.5 part of->
Resin 3:45 parts of
4 parts->
0.25 part of
And 0.75 part->
Resin 4:45 parts of
2.5 parts->
1.25 parts of
And 1.25 parts of->
Resin 5:42.5 parts of
4 parts->
1.75 parts of
And 1.75 parts->
Resin 6:47.5 parts of
1 part->
0.75 part->
And 0.75 part->
Resin 7:40 parts of
7.5 parts->
1.5 parts of
And 1 part->
Resin 8:46 parts of
2.5 parts->
0.75 part
And 0.75 part->
In some embodiments, the solvent is one or more of toluene, benzene, tetrahydrofuran (THF), diethyl ether, dioxane, methyl Ethyl Ketone (MEK), propylene Glycol Monomethyl Ether Acetate (PGMEA), and gamma-butyrolactone, preferably PGMEA.
In some embodiments, the polymerization is carried out by heating and/or adding a free radical initiator thereto.
In some embodiments, when the polymerization reaction is carried out by heating, the heating temperature is 50 to 150 ℃, preferably 60 to 100 ℃, more preferably 70 ℃.
In some embodiments, when the polymerization is performed by adding a free radical initiator thereto, the free radical initiator is one or more of 2,2 '-Azobisisobutyronitrile (AIBN), 2' -azobis (2, 4-dimethylvaleronitrile), methyl 2, 2-azobis (2-methylpropionate), benzoyl peroxide, and lauroyl peroxide.
In some embodiments, the preparation process may further comprise adding any known chain transfer agent thereto, preferably dodecyl mercaptan or 2-mercaptoethanol thereto.
In some embodiments, the amount of chain transfer agent is preferably from 0.01 to 10 mole percent, based on the total moles of monomer to be polymerized.
In some embodiments, the reaction time of the preparation process is 2 to 24 hours, e.g., 3 hours.
In some embodiments, the method of preparing the resin comprises the steps of: (1) Dissolving the monomers A, B, C and D in a solvent to form a solution; (2) Adding the solution in the step (1) to the same solvent in the step (1);
preferably, the mass ratio of the solvent in step (1) to the solvent in step (2) is from 5:1 to 1:1, for example 7:3; in the step (2), the adding mode is dripping; the time of addition is 1-8 hours, for example 5 hours.
In some embodiments, the method of preparation further comprises a post-treatment step, such as one or more of cooling, precipitation, and drying.
The solvent used in the precipitation may be an alcohol solvent such as methanol.
Wherein the drying may be vacuum drying (e.g., vacuum drying at 40 ℃ for 24 hours).
The invention also provides the resin prepared by the preparation method of the resin.
The invention also provides a preparation method of the photoresist composition, which comprises the following steps: the resin, the solvent, the photoacid generator, the quencher and the surfactant which are prepared by the preparation method of the resin are uniformly mixed.
In some embodiments, the photoacid generator has an X-ray structure + Y - And/or photoacid generator 1 of the structure of (2), wherein X + The structure of (1) is that
(X 1 )、/>
(X 2 )、/>
(X 3 )、/>
(X 4 ) Or->
(X 5 )；Y - The structure of (2) is->
(Y 1 )、/>
(Y 2 )、/>
(Y 3 )、/>
(Y 4 )、/>
(Y 5 )、/>
(Y 6 )、/>
(Y 7 ) Or->
(Y 8 )；
The photoacid generator 1 is a compound capable of generating an acid upon exposure to high temperature radiation.
In some embodiments, the photoacid generator is
(X 1 Y 1 )、
(X 1 Y 3 )、/>
(X 2 Y 5 )、/>
(X 3 Y 6 )、/>
(X 4 Y 4 )、/>
(X 5 Y 8 )、/>
(X 1 Y 8 ) Or (b)
(X 2 Y 7 )。
In some embodiments, the photoacid generator 1 is preferably one or more of sulfonium salts, iodonium salts, sulfonyldiazomethane, N-sulfonyloxy imides, and oxime-O-sulfonate acid generators.
In some embodiments, the solvent is one or more of ketone solvents, alcohol solvents, ether solvents, and ester solvents, preferably one or more of ketone solvents, ether solvents, and ester solvents.
In some embodiments, the ketone solvent is cyclohexanone or methyl-2-n-amyl ketone.
In some embodiments, the alcoholic solvent is one or more of 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, and diacetone alcohol.
In some embodiments, the ether solvent is one or more of propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, and diethylene glycol dimethyl ether.
In some embodiments, the ester solvent is one or more of Propylene Glycol Monomethyl Ether Acetate (PGMEA), propylene glycol monoethyl ether acetate, methyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, t-butyl acetate, t-butyl propionate, propylene glycol mono-t-butyl ether acetate, and gamma-butyrolactone.
In some embodiments, the photoresist composition is prepared by a process wherein the solvent is one or more of cyclohexanone, ethylene glycol monoethyl ether, and gamma-butyrolactone.
In some embodiments, the quencher is an amine compound, sulfonate or carboxylate, preferably sulfonate, in a process for preparing a photoresist composition.
In some embodiments, the amine compound is a primary, secondary or tertiary amine compound, preferably an amine compound having a hydroxyl, ether, ester, lactone, cyano or sulfonate group.
In some embodiments, the quencher is
(Q1) or->
(Q2)。
In some embodiments, the photoresist composition is prepared by a process wherein the surfactant is insoluble or substantially insoluble in water and soluble in an alkaline developer, and/or insoluble or substantially insoluble in both water and alkaline developer, preferably one or more of FC-4430 (3M), S-381 (AGC SeimiChemical), E1004 (Air Products), KH-20 and KH-30 (Asahi Glass), more preferably KH-20 and/or KH-30.
In the preparation method of the photoresist composition, the contents of the components are conventional in the photoresist in the field, and the following contents are preferred.
In some embodiments, the resin may be present in the photoresist composition in an amount of 75 to 95 parts by weight (e.g., 75, 85, 90, 95).
In some embodiments, the photoresist composition may include 1 to 10 parts by weight (e.g., 1,3, 5,7, 10) of the photoacid generator.
In some embodiments, the photoresist composition can include 1000 to 2000 parts by weight (e.g., 1000, 1200, 1500, 1600, 2000) of the solvent.
In some embodiments, the weight fraction of the quencher in the photoresist composition may be 0.5 to 3 parts (e.g., 0.5, 0.8, 1.5, 2, 3) by weight.
In some embodiments, the weight fraction of the surfactant in the photoresist composition may be 0.1 to 2 parts, for example 0.15 parts, by weight.
In some embodiments, the photoresist composition can be prepared by a process comprising: the resin as described above (including the kind and the part of the resin), the photoacid generator as described above (including the kind and the part of the photoacid generator), the solvent as described above (including the kind and the part of the solvent), the quencher as described above (including the kind and the part of the quencher), and the surfactant as described above (including the kind and the part of the surfactant).
In some embodiments, the photoresist composition is any photoresist composition prepared from the following resins, photoacid generators, solvents, quenchers, and surfactants:
photoresist composition 1:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 2:75 parts of resin 1,1 part of photoacid generator X 1 Y 1 1000 parts of solvent cyclohexanone, 0.5 part of quencher Q1 and surfactant KH-30;
photoresist composition 3:80 parts of resin 1,3 parts of photoacid generator X 1 Y 1 1200 parts of solvent cyclohexanone, 0.8 part of quencher Q1 and surfactant KH-30;
photoresist composition 4:90 parts of1,5 parts of photoacid generator X 1 Y 1 1600 parts of solvent cyclohexanone, 1.5 parts of quenching agent Q1 and surfactant KH-30;
photoresist composition 5:95 parts of resin 1 and 10 parts of photoacid generator X 1 Y 1 2000 parts of solvent cyclohexanone, 3 parts of quencher Q1 and surfactant KH-30;
photoresist composition 6:85 parts of resin 1,7 parts of photoacid generator X 1 Y 3 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 7:85 parts of resin 1,7 parts of photoacid generator X 2 Y 5 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 8:85 parts of resin 1,7 parts of photoacid generator X 3 Y 6 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 9:85 parts of resin 1,7 parts of photoacid generator X 4 Y 4 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 10:85 parts of resin 1,7 parts of photoacid generator X 5 Y 8 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 11:85 parts of resin 1,7 parts of photoacid generator X 1 Y 8 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 12:85 parts of resin 1,7 parts of photoacid generator X 2 Y 7 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 13:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent ethylene glycol monoethyl ether, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 14:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of2 parts of solvent gamma-butyrolactone, a quencher Q1 and a surfactant KH-30;
photoresist composition 15:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quenching agent Q2 and surfactant KH-30;
photoresist composition 16:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-20;
photoresist composition 17:85 parts of resin 2,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 18:85 parts of resin 3,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 19:85 parts of resin 4,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 20:85 parts of resin 5,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 21:85 parts of resin 6,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 22:85 parts of resin 7,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 23:85 parts of resin 8,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30.
In some embodiments, the method for preparing the photoresist composition may further comprise a filtering step after the mixing. The filtration may be carried out in a manner conventional in the art, preferably by filtration using a filter. The pore size of the filter membrane of the filter is preferably 0.2 μm.
The invention also provides a method for forming the photoetching pattern, which comprises the following steps:
(1) Coating the photoresist composition on a substrate, and pre-baking to obtain a photoresist film;
(2) Exposing the photoresist film obtained in the step (1);
(3) Baking the photoresist film obtained in the step (2) on a hot plate;
(4) Developing the photoresist film obtained in the step (3).
In some embodiments, in step (1), the substrate may be a substrate for integrated circuit fabrication (e.g., si, siO 2 One or more of SiN, siON, tiN, WSi, BPSG, SOG and organic anti-reflective film) or a substrate for mask circuit fabrication (e.g., cr, crO, crON, moSi 2 And SiO 2 One or more of the following).
In some embodiments, in step (1), the coating may be performed in a conventional manner known in the art for forming photolithographic patterns, such as spin coating.
In some embodiments, in step (1), the pre-bake temperature is 60 to 150 ℃, preferably 80 to 250 ℃, more preferably 200 ℃.
In some embodiments, in step (1), the pre-bake time is from 1 to 10 minutes, preferably from 1 to 5 minutes, more preferably 1 minute.
In some embodiments, in step (1), the photoresist film is typically 0.05 to 2 μm thick, e.g., 100nm.
In some embodiments, in step (2), the exposure is performed under conventional procedures used in the art to form lithographic patterns, such as high energy radiation (e.g., krF excimer laser, arF excimer laser, or EUV), where the exposure dose may be 1-200mJ/cm 2 (e.g., 10-100 mJ/cm) 2 ) The method comprises the steps of carrying out a first treatment on the surface of the For example, electron beam exposure is used, wherein the exposure dose may be 0.1-100. Mu.C/cm 2 (e.g., 0.5-50. Mu.C/cm) 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Also e.g. byImmersion lithography methods that provide a liquid (e.g., water) having a refractive index of at least 1.0 between the projection lens and the photoresist layer accomplish the exposure. In the case of immersion lithography, a water-insoluble protective film may be formed on the photoresist layer.
Among them, when a water-insoluble protective film for immersion lithography is used to prevent any component from leaching out of a resist film and improve water slidability (water slip page) at the film surface, the protective film is generally classified into two types. The first type is an organic solvent peelable protective film, which must be peeled off with an organic solvent in which the resist film is insoluble before alkaline development. The second type is an alkali-soluble protective film which is soluble in an alkali developer so that it can be removed simultaneously with the removal of the dissolved region of the resist film. The second type of protective film preferably comprises a polymer having 1, 3-hexafluoro-2-propanol residues, which is insoluble in water and soluble in an alkaline developer, as a base material in an alcohol solvent of at least 4 carbon atoms, an ether solvent of 8 to 12 carbon atoms, or a mixture thereof. Alternatively, the aforementioned surfactant, which is insoluble in water and soluble in an alkaline developer, may be dissolved in an alcohol solvent of at least 4 carbon atoms, an ether solvent of 8 to 12 carbon atoms, or a mixture thereof to form a material from which the second type of protective film is formed.
In some embodiments, in step (3), the baking temperature is 60 to 150 ℃, preferably 80 to 140 ℃, more preferably 95 ℃.
In some embodiments, in step (3), the baking time is from 1 to 5 minutes, preferably from 1 to 3 minutes, more preferably 1 minute.
In some aspects, in step (4), the means of development may be conventional in the art for forming lithographic patterns, such as one or more of immersion, spin-on immersion and spraying.
In some embodiments, in step (4), the developed developer may be a conventional developer used in the art to form lithographic patterns, such as an aqueous alkaline solution and/or an organic solvent.
Wherein the alkaline aqueous solution is 0.1 to 5wt% of tetramethyl ammonium hydroxide aqueous solution, preferably 2 to 3 wt% of tetramethyl ammonium hydroxide aqueous solution.
Wherein the organic solvent is one or more of 2-octanone, 2-nonanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-hexanone, 3-hexanone, diisobutyl ketone, methylcyclohexanone, acetophenone, methylacetophenone, propyl acetate, butyl acetate, isobutyl acetate, amyl acetate, isoamyl acetate, butenyl acetate, phenyl acetate, propyl formate, butyl formate, isobutyl formate, pentyl formate, isopentyl formate, methyl valerate, methyl pentenoate, methyl crotonate, ethyl crotonate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, isobutyl lactate, pentyl lactate, isopentyl lactate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, methyl benzoate, ethyl benzoate, benzyl acetate, methyl phenylacetate, benzyl formate, phenyl ethyl formate, methyl 3-phenylpropionate, benzyl propionate, ethyl phenylacetate or 2-phenylethyl acetate.
In some embodiments, in step (4), the development time of the development is from 0.1 to 3 minutes, preferably from 0.5 to 2 minutes.
In some aspects, the patterning method may further include:
after forming the photoresist film, a step of rinsing with pure water (post-soaking) may be introduced to extract an acid generator or the like from the film surface or wash out particles;
after exposure, a rinse (after saturation) step may be introduced to remove any water remaining on the film after exposure.
The above preferred conditions can be arbitrarily combined on the basis of not deviating from the common knowledge in the art, and thus, each preferred embodiment of the present invention can be obtained.
The reagents and part of raw materials used in the invention are commercially available, and part of raw materials are self-made.
The invention has the positive progress effects that: the photoresist comprising the resin prepared by the preparation method of the invention has the advantages of excellent photosensitivity, good depth of focus (DOF) and good line width uniformity (CDU).
Detailed Description
The invention is further illustrated by means of the following examples, which are not intended to limit the scope of the invention. The experimental methods, in which specific conditions are not noted in the following examples, were selected according to conventional methods and conditions, or according to the commercial specifications.
(R of monomer in the following examples and comparative examples) 1 -R 4 Are all methyl, R 5 Is isopropenyl, R 6 Methyl group)
Example 1 preparation of resin
A solution was prepared by dissolving 42.5 parts by weight of (g) monomer A, 5 parts by weight of (g) monomer B, 1.25 parts by weight of (g) monomer C, and 1.25 parts by weight of (g) monomer D in 70g of PGMEA under a nitrogen atmosphere. The solution was added dropwise to 30g of PGMEA over 5 hours under nitrogen atmosphere while stirring at 70 ℃. After the completion of the dropwise addition, stirring was continued at 70℃for 3 hours. The reaction solution was cooled to room temperature and added dropwise to 1000g of methanol. The solid thus precipitated was collected by filtration and dried under vacuum at 40 ℃ for 24 hours to obtain resin 1 as a powder solid. Weight average molecular weight (M) of resin 1 W ) 6200, a molecular weight distribution or dispersity (Mw/Mn) of 1.4.
Examples 2 to 8 and comparative examples 1 to 8
Preparation of the resins of examples 2-8 and comparative examples 1-8 reference example 1. Parts by weight (g) of monomers used, weight average molecular weight (M) of the resulting resin W ) The molecular weight distribution or dispersity is shown in the following table.
TABLE 1
| Monomer A | Monomer B | Monomer C | Monomer D | Mw | Mw/Mn | |
| Preparation example 2 | 45 | 4 | 0.5 | 0.5 | 6800 | 1.7 |
| Preparation example 3 | 45 | 4 | 0.25 | 0.75 | 9600 | 1.9 |
| Preparation example 4 | 45 | 2.5 | 1.25 | 1.25 | 9900 | 1 |
| Preparation example 5 | 42.5 | 4 | 1.75 | 1.75 | 9800 | 1.2 |
| Preparation example 6 | 47.5 | 1 | 0.75 | 0.75 | 9500 | 1.4 |
| Preparation example 7 | 40 | 7.5 | 1.5 | 1 | 9700 | 1.7 |
| Preparation example 8 | 46 | 2.5 | 0.75 | 0.75 | 6400 | 1.8 |
| Comparative example 1 | 45 | 4 | 1 | 0 | 8300 | 1.1 |
| Comparative example 2 | 47.5 | 2 | 0 | 0.5 | 6800 | 2 |
| Comparative example 3 | 47.5 | 0 | 1.25 | 1.25 | 5800 | 2 |
| Comparative example 4 | 39 | 7.5 | 2 | 1.5 | 6700 | 2 |
| Comparative example 5 | 39 | 7.5 | 2.5 | 1 | 6800 | 1.6 |
| Comparative example 6 | 50 | 0 | 0 | 0 | 9800 | 1.7 |
| Comparative example 7 | 49.25 | 0.25 | 0.25 | 0.25 | 7200 | 1.1 |
| Comparative example 8 | 45 | 0.5 | 2 | 2.5 | 9000 | 1.1 |
EXAMPLE 9 preparation of Photoresist composition
85 parts by weight (pbw) of the resin 1 obtained in example 1,7 parts by weight (pbw) of the photoacid generator X1Y1, 2 parts by weight (pbw) of the quencher Q1 were dissolved in 1500 parts by weight (pbw) of cyclohexanone containing 0.01% by weight of the surfactant KH-30, and the resulting solution was filtered through a filter having a pore size of 0.2. Mu.m, to prepare a photoresist composition 1.
Examples 10 to 31 and comparative examples 9 to 31
Preparation of the photoresist compositions of examples 10-31 and comparative examples 9-31 reference example 9. The resins used and parts by weight (pbw), photoacid generator used and parts by weight (pbw), solvent used and parts by weight (pbw), quencher used and parts by weight (pbw), surfactant used are given in the table below.
TABLE 2
TABLE 3 Table 3
Remarks: s1 in tables 2 and 3 is cyclohexanone, S2 is ethylene glycol monoethyl ether, and S3 is γ -butyrolactone).
Application and Effect examples ArF immersion lithography patterning test (hole Pattern test)
1. Hole pattern formation:
on a substrate (silicon wafer), a spin-on carbon film ODL-70 (carbon content: 65wt%, shin-Etsu Chemical Co., ltd.) was deposited to a thickness of 200nm and a spin-on hard mask SHB-A940 (silicon content: 43 wt%; shin-Etsu Chemical Co., ltd.) containing silicon was deposited thereon to a thickness of 35 nm. Then, a photoresist composition was spin-coated thereon, and then baked at 200 ℃ for 60 seconds on a hot plate to form a 100nm thick photoresist film.
Using an ArF excimer laser immersion scanner NSR-S610C (Nikon corp., NA1.30, σ0.9/0.72, 35 ° cross-polar opening, azimuthal polarized illumination), the photoresist film was exposed through a 6% halftone phase shift mask using immersion lithography at varying doses. The photoresist film was baked (PEB) at a temperature of 95 ℃ for 60 seconds. After PEB, developer was injected from the development nozzle while the wafer was rotated at 30rpm for 3 seconds, followed by static suspension immersion development for 27 seconds. A hole pattern with a pitch of 100nm was formed.
2. Evaluating photosensitivity:
the hole pattern formed above was observed under a TD-SEM (CG-4000,Hitachi High-Technologies Corp.). The optimum dose (Eop) is an exposure dose (mJ/cm 2) that provides a hole diameter of 50nm at a pitch of 100nm, and is used as an index of photosensitivity.
3. Depth of focus (DOF) limit was evaluated:
pore size at the optimum dose was measured under TD-SEM (CG-4000) from which the DOF margin providing a size of 50 nm.+ -. 5nm was determined. The larger value indicates that the smaller the change in pattern size with DOF change and thus the better DOF margin.
4. Evaluation of CDU:
the hole pattern formed above was observed under TD-SEM (CG-4000) and the diameters of 125 holes were measured. From which a triple value (3σ) of the standard deviation (σ) was calculated and recorded as CDU. Smaller 3 sigma values indicate smaller deviations of the holes.
5. Evaluation of PPD:
immediately after PEB (no delay, ppd=0h) the wafer was developed in a cantilever immersion for 30 seconds to form a hole pattern with a diameter of 50nm and a pitch of 100nm. In another run, the wafer was held 6 hours after PEB (ppd=6h) and then developed as such to form a pattern.
The pore pattern at ppd=0h and 6h was observed under TD-SEM (CG-4000) and the diameter of 125 pores was measured. The average value thereof was taken as a pore size (CD), and the CDU was calculated by the same method as above. The difference between the CD at PPD 0h and the CD at PPD6h was taken as the CD shrinkage due to PPD (ΔPPDCD).
TABLE 4 Table 4
As can be seen from the above table, the photoresist composition within the scope of the present invention shows DOF and CDU improvement and a reduction in CD shrinkage (small CD change) due to PPD as compared to the photoresist composition of the comparative example.
Claims (10)
1. A method of preparing a resin comprising the steps of: in a solvent, carrying out polymerization reaction on a monomer A, a monomer B, a monomer C and a monomer D to obtain the resin;
wherein the weight portion of the monomer A is 40-47.5 portions;
1 to 7.5 parts by weight of monomer B;
the monomer C is 0.25-2.5 parts by weight;
the monomer D is 0.25-2.5 parts by weight;
R 1 is C 1-10 An alkyl group;
R 2 is H or C 1-5 An alkyl group;
R 3 is C 1-10 An alkyl group;
R 4 is H or C 1-5 An alkyl group;
R 5 is C 2-5 Alkenyl groups;
R 6 is H or C 1-5 An alkyl group.
2. The method for producing a resin according to claim 1, wherein,
the weight of the monomer A is 42.5-45 parts;
and/or the monomer B is 2.5-4 parts by weight;
and/or the monomer C is 0.5-1.25 parts by weight;
and/or the monomer D is 0.5-1.25 parts by weight;
and/or R 1 In the above, the C 1-10 Alkyl is C 1-5 Alkyl, preferably methyl, ethyl, n-propyl or isopropyl;
and/or R 2 In the above, the C 1-5 Alkyl is methyl, ethyl, n-propyl or isopropyl;
and/or R 3 In the above, the C 1-10 Alkyl isC 1-5 Alkyl, preferably methyl, ethyl, n-propyl or isopropyl;
and/or R 4 In the above, the C 1-5 Alkyl is methyl, ethyl, n-propyl or isopropyl;
and/or R 5 In (C) 2-5 Alkenyl group is C 2-3 Alkenyl, said C 2-3 Alkenyl is preferably isopropenyl or vinyl;
and/or R 6 In the above, the C 1-5 Alkyl is methyl, ethyl, n-propyl or isopropyl.
3. The method for producing a resin according to claim 1, wherein,
R 2 is C 1-5 An alkyl group;
and/or R 4 Is C 1-5 An alkyl group;
and/or R 6 Is C 1-5 An alkyl group;
and/or the weight average molecular weight of the resin is 3,000 to 100,000, may be 5000 to 10000, such as 6000, 7000, 8000 or 9000;
and/or the dispersity of the resin is 1.0 to 2.0, preferably 1.5 to 2.0.
4. The method of producing a resin according to claim 1, wherein the resin is selected from any one of the following resins 1 to 8:
resin 1:42.5 parts of
5 parts->
1.25 parts->
And 1.25 parts of->
Resin 2:45 parts of
4 parts->
0.5 part->
And 0.5 part of monomer->
Resin 3:45 parts of
4 parts->
0.25 part->
And 0.75 part of monomer->
Resin 4:45 parts of
2.5 parts->
1.25 parts->
And 1.25 parts of monomer->
/>
Resin 5:42.5 parts of
4 parts->
1.75 parts->
And 1.75 parts of monomer->
Resin 6:47.5 parts of
1 part->
0.75 part->
And 0.75 part of monomer->
Resin 7:40 parts of
7.5 parts->
1.5 parts->
And 1 part of monomer->
Resin 8:46 parts of
2.5 parts->
0.75 part->
And 0.75 part->
5. The method for producing a resin according to any one of claim 1 to 4,
the solvent is one or more of toluene, benzene, tetrahydrofuran, diethyl ether, dioxane, methyl ethyl ketone, propylene glycol monomethyl ether acetate and gamma-butyrolactone, preferably propylene glycol monomethyl ether acetate;
and/or, said polymerization is carried out by heating and/or adding a free radical initiator thereto; when the polymerization is carried out by heating, the heating temperature is 50 to 150 ℃, preferably 60 to 100 ℃, more preferably 70 ℃; when the polymerization is performed by adding thereto a radical initiator, the radical initiator is one or more of 2,2 '-Azobisisobutyronitrile (AIBN), 2' -azobis (2, 4-dimethylvaleronitrile), 2-azobis (methyl 2-methylpropionate), benzoyl peroxide and lauroyl peroxide;
and/or the preparation method further comprises adding thereto any known chain transfer agent, preferably dodecyl mercaptan or 2-mercaptoethanol; the amount of the chain transfer agent is preferably 0.01 to 10mol% based on the total mole number of the monomers to be polymerized;
and/or the reaction time of the preparation method is 2 to 24 hours, for example 3 hours;
and/or the preparation method further comprises a post-treatment step, such as one or more of cooling, precipitation and drying; the solvent used in the precipitation may be an alcoholic solvent, such as methanol; the drying may be vacuum drying, for example, vacuum drying at 40 ℃ for 24 hours;
and/or, the preparation method comprises the following steps: (1) Dissolving the monomers A, B, C and D in a solvent to form a solution; (2) Adding the solution in the step (1) to the same solvent in the step (1);
preferably, the mass ratio of the solvent in step (1) to the solvent in step (2) is from 5:1 to 1:1, for example 7:3; in the step (2), the adding mode is dripping; the time of addition is 1-8 hours, for example 5 hours.
6. A method of preparing a photoresist composition comprising the steps of: the resin obtained by the method for producing a resin according to any one of claims 1 to 5, wherein the resin, the solvent, the photoacid generator, the quencher and the surfactant are uniformly mixed.
7. The method of preparing a photoresist composition according to claim 6,
in the preparation method of the photoresist composition, the photoacid generator has X + Y - And/or photoacid generator 1 of the structure of (2), wherein X + The structure of (1) is that
Y - The structure of (1) is that
/>
The photoacid generator 1 is a compound capable of generating acid when exposed to high-temperature radiation;
and/or, in the preparation method of the photoresist composition, the solvent is one or more of ketone solvents, alcohol solvents, ether solvents and ester solvents, preferably one or more of ketone solvents, ether solvents and ester solvents;
and/or, in the preparation method of the photoresist composition, the quencher is an amine compound, sulfonate or carboxylate, preferably sulfonate, more preferably sulfonate
And/or, in the preparation method of the photoresist composition, the surfactant is insoluble or basically insoluble in water and soluble in an alkaline developer, and/or insoluble or basically insoluble in water and the surfactant in the alkaline developer;
and/or, in the preparation method of the photoresist composition, the weight part of the resin may be 75 to 95 parts, for example, 75, 85, 90 or 95 parts;
and/or, in the preparation method of the photoresist composition, the weight part of the photoacid generator may be 1 to 10 parts, for example, 1,3, 5,7 or 10 parts;
and/or, in the preparation method of the photoresist composition, the solvent may be 1000 to 2000 parts by weight, for example 1000, 1200, 1500, 1600 or 2000 parts by weight;
and/or, in the preparation method of the photoresist composition, the quencher may be 0.5 to 3 parts by weight, for example, 0.5, 0.8, 1.5, 2 or 3 parts by weight;
and/or, in the preparation method of the photoresist composition, the weight part of the surfactant may be 0.1 to 2 parts, for example, 0.15 parts, in terms of weight part.
8. The method of preparing a photoresist composition according to claim 7,
the photoacid generator 1 is one or more of sulfonium salt, iodonium salt, sulfonyl diazomethane, N-sulfonyl oxy imide and oxime-O-sulfonate acid generator;
and/or the photoacid generator is
/>
And/or, the ketone solvent is cyclohexanone or methyl-2-n-amyl ketone;
and/or the alcohol solvent is one or more of 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol and diacetone alcohol;
and/or the ether solvent is one or more of propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether and diethylene glycol dimethyl ether;
and/or the ester solvent is one or more of propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, methyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, tert-butyl acetate, tert-butyl propionate, propylene glycol mono-tert-butyl ether acetate and gamma-butyrolactone;
and/or the amine compound is a primary, secondary or tertiary amine compound, preferably an amine compound having a hydroxyl, ether, ester, lactone, cyano or sulfonate group;
and/or the surfactant is one or more of FC-4430, S-381, E1004, KH-20 and KH-30, preferably KH-20 and/or KH-30.
9. The method of claim 6, further comprising a step of filtering after said mixing, wherein said filtering is performed by a filter having a membrane size of preferably 0.2 μm.
10. The method of claim 6, wherein the photoresist composition is any one of the following resins, photoacid generator, solvent, quencher and surfactant:
photoresist composition 1:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 2:75 parts of resin 1,1 part of photoacid generator X 1 Y 1 1000 parts of solvent cyclohexanone, 0.5 part of quencher Q1 and surfactant KH-30;
photoresist composition 3:80 parts of resin 1,3 parts of photoacid generator X 1 Y 1 1200 parts of solvent cyclohexanone, 0.8 part of quencher Q1 and surfactant KH-30;
photoresist composition 4:90 parts of resin 1,5 parts of photoacid generator X 1 Y 1 1600 parts of solvent cyclohexanone, 1.5 parts of quenching agent Q1 and surfactant KH-30;
photoresist composition 5:95 parts of resin 1 and 10 parts of photoacid generator X 1 Y 1 2000 parts of solvent cyclohexanone, 3 parts of quencher Q1 and surfactant KH-30;
photoresist composition 6:85 parts of resin 1,7 parts of photoacid generator X 1 Y 3 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 7:85 parts of resin 1,7 parts of photoacid generator X 2 Y 5 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 8:85 parts of resin 1,7 parts of photoacid generator X 3 Y 6 1500 parts of solvent cyclohexaneKetone, 2 parts of a quenching agent Q1 and a surfactant KH-30;
photoresist composition 9:85 parts of resin 1,7 parts of photoacid generator X 4 Y 4 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 10:85 parts of resin 1,7 parts of photoacid generator X 5 Y 8 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 11:85 parts of resin 1,7 parts of photoacid generator X 1 Y 8 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 12:85 parts of resin 1,7 parts of photoacid generator X 2 Y 7 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 13:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent ethylene glycol monoethyl ether, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 14:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent gamma-butyrolactone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 15:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quenching agent Q2 and surfactant KH-30;
photoresist composition 16:85 parts of resin 1,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-20;
photoresist composition 17:85 parts of resin 2,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 18:85 parts of resin 3,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 19:85 parts of resin 4,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 20:85 parts of resin 5,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 21:85 parts of resin 6,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 22:85 parts of resin 7,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30;
photoresist composition 23:85 parts of resin 8,7 parts of photoacid generator X 1 Y 1 1500 parts of solvent cyclohexanone, 2 parts of quencher Q1 and surfactant KH-30.
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| US20030186161A1 (en) * | 2001-07-05 | 2003-10-02 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition |
| US20050074690A1 (en) * | 2003-10-01 | 2005-04-07 | Shenggao Liu | Photoresist compositions comprising diamondoid derivatives |
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| US20200218154A1 (en) * | 2019-01-08 | 2020-07-09 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
| US20200249571A1 (en) * | 2019-02-05 | 2020-08-06 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
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2021
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| US20030186161A1 (en) * | 2001-07-05 | 2003-10-02 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition |
| US20050074690A1 (en) * | 2003-10-01 | 2005-04-07 | Shenggao Liu | Photoresist compositions comprising diamondoid derivatives |
| CN105924373A (en) * | 2016-05-09 | 2016-09-07 | 武汉大学 | Methacrylate monomer containing disulfide bond and adamantine and preparation method of methacrylate monomer |
| US20200218154A1 (en) * | 2019-01-08 | 2020-07-09 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
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