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JP-2026075072-A - Polymer, resist composition containing the same, and pattern formation method using the same

JP2026075072AJP 2026075072 AJP2026075072 AJP 2026075072AJP-2026075072-A

Abstract

[Problem] To provide a polymer, a resist composition containing the same, and a pattern formation method using the same. [Solution] A polymer containing a first repeating unit represented by the following chemical formula, a resist composition containing the same, and a pattern formation method using the same. In the formula, L 11 and L 12 are independently a single bond, O, S, C(=O), C(=O)O, etc., a11 and a12 are independently integers from 1 to 4, X 11 is a C6-C30 aryl group or a C1-C30 heteroaryl group, and X 12 is CN, C(=O)R 12 , C(=O)OR 12 , etc. [Selection Diagram] Figure 1

Inventors

  • 郭 允 鉉
  • 河 旻 永
  • 姜 哲
  • 金 旻 相
  • 金 範 錫
  • 金 惠 蘭
  • 朴 滸 潤
  • 李 在 俊
  • 林 圭 鉉
  • 崔 ヒョン 碩

Assignees

  • 三星電子株式会社

Dates

Publication Date
20260507
Application Date
20251017
Priority Date
20241021

Claims (20)

  1. A polymer containing a first repeating unit represented by the following chemical formula 1. In the aforementioned chemical formula 1, L11 and L12 are independently substituted or unsubstituted linear, branched or cyclic divalent hydrocarbon groups of C1- C30 that selectively contain a single bond, O, S, C(=O), C(=O)O, OC(=O), C(=O) NR11 , NR11C (=O), S(=O), S(=O) 2 , S(=O) 2O , OS(=O ) 2 , or heteroatoms. a11 and a12 are each independent integers between 1 and 4. X 11 is a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C1 - C30 heteroaryl group, X 12 is CN, C(=O)R 12 , C(=O)OR 12 , C(=O)SR 12 , or C(=O)NR 12R 13 , R11 to R13 are each independently substituted or unsubstituted C1 - C30 linear, branched, or cyclic monovalent hydrocarbon groups that selectively contain hydrogen, deuterium, or heteroatoms. * indicates a bonding site with an adjacent atom.
  2. L11 and L12 are independently single bonds, O, S, C(=O), C(=O)O, OC(=O), C(=O)NH, NHC(=O), S(=O), S(=O) ² , S(=O) ²O , OS(=O) ² , substituted or unsubstituted C1 - C30 alkylene groups, substituted or unsubstituted C3 - C30 cycloalkylene groups, substituted or unsubstituted C3 - C30 heterocycloalkylene groups, substituted or unsubstituted C2 - C30 alkenylene groups, substituted or unsubstituted C3- C30 cycloalkenylene groups, substituted or unsubstituted C3 - C30 heterocycloalkenylene groups, substituted or unsubstituted C6 - C30 arylene groups, or substituted or unsubstituted C1 -C The polymer according to claim 1, wherein the polymer has 30 heteroarylene groups.
  3. The polymer according to claim 1 , wherein X11 is selected from deuterium, halogen, cyano group, hydroxyl group, amino group, carboxylic acid group, thiol group, ester moisture, sulfonic acid ester moisture, carbonate moisture, carbamate moisture, lactone moisture, sultone moisture, carboxylic acid anhydride moisture, C1 - C20 alkyl group, C1 - C20 halogenated alkyl group, C1 - C20 alkoxy group, C3 - C20 cycloalkyl group, C3 - C20 cycloalkoxy group, C6 - C20 aryl group, or any combination thereof, substituted or unsubstituted, C6-C20 aryl group and C1 - C20 heteroaryl group.
  4. The polymer according to claim 1 , wherein X11 is selected from deuterium, halogen, cyano group, hydroxyl group, amino group, carboxylic acid group, thiol group, C1 - C20 alkyl group, C1 - C20 halogenated alkyl group, C1 - C20 alkoxy group, C3 - C20 cycloalkyl group, C3 - C20 cycloalkoxy group, C6- C20 aryl group, or any combination thereof, and is substituted or unsubstituted with C6 - C20 aryl groups and C1 - C20 heteroaryl groups.
  5. The polymer according to claim 1, wherein X12 is represented by any one of the following chemical formulas 4-1 to 4-4. In the aforementioned chemical formulas 4-1 to 4-4, R12 and R13 are defined as in the same way as in the above chemical formula 1. * indicates a bonding site with an adjacent atom.
  6. The polymer according to claim 1, wherein R11 to R13 are each independently selected from hydrogen; deuterium; and deuterium, halogen, cyano group, hydroxyl group, amino group, carboxylic acid group, thiol group, ester moisture, sulfonic acid ester moisture, carbonate moisture, carbamate moisture, lactone moisture, sultone moisture, carboxylic acid anhydride moisture, C1 - C20 alkyl group, C1 - C20 halogenated alkyl group, C1 - C20 alkoxy group, C3 - C20 cycloalkyl group, C3 - C20 cycloalkoxy group, C6-C20 aryl group , or any combination thereof, substituted or unsubstituted C1 - C20 alkyl group, C3-C20 cycloalkyl group, and C6 - C20 aryl group.
  7. The polymer according to claim 1, wherein the first repeating unit is selected from the following group I. In group I, * represents a bonding site with an adjacent atom.
  8. The polymer according to claim 1, further comprising a second repeating unit represented by the following chemical formula 2. In the aforementioned chemical formula 2, L21 and L22 are independently substituted or unsubstituted linear, branched or cyclic divalent hydrocarbon groups of C1- C30 that selectively contain a single bond, O, S, C(=O), C(=O)O, OC(=O), C(=O) NR21 , NR21C (=O), S(=O), S(=O) 2 , S(=O) 2O , OS(=O ) 2 , or heteroatoms. a21 and a22 are each independent integers between 1 and 4. X21 is an electron-withdrawing group, X 22 is CN, C(=O)R 22 , C(=O)OR 22 , C(=O)SR 22 , or C(=O)NR 22R 23 , R21 to R23 are each independently substituted or unsubstituted C1 - C30 linear, branched, or cyclic monovalent hydrocarbon groups that selectively contain hydrogen, deuterium, or heteroatoms. * indicates a bonding site with an adjacent atom.
  9. X21 is selected from halogens; cyano groups; C1 -C30 alkyl groups, C3- C30 cycloalkyl groups, C2 - C30 alkenyl groups, C3 - C30 cycloalkenyl groups, C2 - C30 alkynyl groups, C6 - C30 aryl groups, and C7 - C30 arylalkyl groups, substituted with halogens , cyano groups, C1 - C20 halogenated alkyl groups, or any combination thereof ; and OSO2Rx . The polymer according to claim 8, wherein R x is a substituted or unsubstituted C1 - C10 alkyl group or a substituted or unsubstituted C6 - C10 aryl group.
  10. X21 is selected from halogens; cyano groups; C1 - C20 alkyl groups and C6 - C20 aryl groups substituted with halogens, cyano groups, C1 - C20 halogenated alkyl groups, or any combination thereof; and OSO2Rx . The polymer according to claim 8, wherein R x is a substituted or unsubstituted C1 - C10 alkyl group or a substituted or unsubstituted C6 - C10 aryl group.
  11. The polymer according to claim 8, wherein X22 is represented by any one of the following chemical formulas 5-1 to 5-4. In the aforementioned chemical formulas 5-1 to 5-4, R22 and R23 are defined as in the same way as in the above chemical formula 2. * indicates a bonding site with an adjacent atom.
  12. The polymer according to claim 8, wherein the second repeating unit is selected from the following group II. In Group II, OMs are OSO₂CH₃ , OTf is OSO₂CF₃ , OTs are OSO₂C₆H₄ ( CH₃ ), and * indicates a bonding site with an adjacent atom.
  13. A resist composition comprising the polymer and solvent described in any one of claims 1 to 12.
  14. The resist composition according to claim 13, wherein the resist composition does not contain any compounds with a molecular weight of 1,000 or more other than the polymer.
  15. The resist composition according to claim 13, wherein the resist composition substantially does not contain a photoacid generator.
  16. The resist composition according to claim 13, wherein the resist composition does not contain an organometallic compound.
  17. The steps include: applying the resist composition according to claim 13 onto a substrate to form a resist film; A step of exposing at least a portion of the resist film with a high-energy beam, A pattern formation method comprising the step of developing an exposed resist film using a developer.
  18. The pattern forming method according to claim 17, wherein the exposure step is performed by irradiating with ultraviolet light, far ultraviolet light (DUV), extreme ultraviolet light (EUV), X-rays, gamma rays, electron beams (EB), and/or alpha rays.
  19. The pattern-forming method according to claim 17, wherein the main chain of the polymer is decomposed by the exposure.
  20. The exposed resist film includes an exposed portion and an unexposed portion. The pattern forming method according to claim 17, wherein the exposed portion is removed during the developing step.

Description

This invention relates to a polymer, a resist composition containing the same, and a pattern-forming method using the same. During semiconductor manufacturing, resists that change their properties in response to light are used to form fine patterns. Among these, chemically amplified resists have been widely used. Chemically amplified resists enable patterning by reacting light with a photoacid generator to form an acid, which then reacts again with the base resin, changing the solubility of the base resin in the developer. In particular, when using high-energy rays with relatively very high energies, such as EUV, there is a problem in that the number of photons is significantly lower even when irradiated with light of the same energy. This creates a demand for resist compositions that can function effectively even with smaller quantities, providing improved sensitivity, improved resolution, and/or reduced defects. This is a flowchart showing a pattern formation method according to one embodiment of the present invention.This is a side cross-sectional view showing a pattern formation method according to one embodiment of the present invention.This is a side cross-sectional view showing a pattern formation method according to one embodiment of the present invention.This is a side cross-sectional view showing a pattern formation method according to one embodiment of the present invention.This is a side cross-sectional view showing a method for forming a patterned structure according to one embodiment of the present invention.This is a side cross-sectional view showing a method for forming a patterned structure according to one embodiment of the present invention.This is a side cross-sectional view showing a method for forming a patterned structure according to one embodiment of the present invention.This is a side cross-sectional view showing a method for forming a patterned structure according to one embodiment of the present invention.This is a side cross-sectional view showing a method for forming a patterned structure according to one embodiment of the present invention.This is a side cross-sectional view showing a method for forming a semiconductor device according to an embodiment.This is a side cross-sectional view showing a method for forming a semiconductor device according to an embodiment.This is a side cross-sectional view showing a method for forming a semiconductor device according to an embodiment.This is a side cross-sectional view showing a method for forming a semiconductor device according to an embodiment.This is a side cross-sectional view showing a method for forming a semiconductor device according to an embodiment.This graph shows the thin film thickness after development using the dose of Example 1-1.This graph shows the thin film thickness after development using the doses of Examples 2-1 and 2-2.This is a pattern image of Example 3-1.This is a pattern image of Example 3-2.This is a pattern image of Example 3-3. This invention can be subjected to various transformations and has many different embodiments. Specific embodiments are illustrated in the drawings and described in detail in the detailed description. However, this is not intended to limit the invention to specific embodiments; rather, it should be understood that the invention includes all transformations, equivalents, or substitutes that fall within the spirit and technical scope of the invention. If a specific description of related prior art in explaining this invention is deemed to obscure the gist of the invention, such detailed description will be omitted. Terms such as "first," "second," and "third" are used to describe various components, but they are used solely to distinguish one component from others and do not limit the order or type of the components. In this specification, when a part such as a layer, film, region, or plate is described as being "above" or "on top of" another part, this includes not only parts that are immediately above, below, left, or right in contact, but also parts that are above, below, left, or right in non-contact. Unless explicitly stated otherwise in the context, singular expressions include plural expressions. Terms such as "includes" or "possesses," unless otherwise stated, indicate the presence of the features, numbers, stages, operations, components, parts, ingredients, materials, or combinations thereof described in the specification, and should not be understood to preemptively exclude the possibility of the presence or addition of one or more other features, numbers, stages, operations, components, parts, ingredients, materials, or combinations thereof. Each time a range of values is listed, that range includes all values that fall within that range as explicitly recorded, and further includes the range boundaries. Therefore, the range "X to Y" includes all values between X and Y, and also includes X and Y themselves. In this specification, "C x - C y " means that the substituent