Underlayer compositions and patterning methods

Abstract

An underlayer composition, comprising a polymer comprising a repeating unit of formula (1):wherein Ar is a monocyclic or polycyclic C5-60 aromatic group, wherein the aromatic group comprises one or more aromatic ring heteroatoms, a substituent group comprising a heteroatom, or a combination thereof; X is C or O; R1, R2; Ra and Rb are as provided herein; optionally, R1 and R2 can be taken together form a 5- to 7-membered ring; optionally, one of R11 to R13 can be taken together with R1 to form a 5- to 7-membered ring; wherein Ra and Rb optionally may be taken together to form a 5- to 7-membered ring; wherein one of Ra or Rb optionally may be taken together with R2 to form a 5- to 7-membered ring; and when X is O, Ra and Rb are absent.

1 . An underlayer composition, comprising a polymer comprising a repeating unit of formula (1): 
       
         
           
           
               
               
           
         
       
       wherein,
 Ar is a monocyclic or polycyclic C 5-60  aromatic group, wherein the aromatic group comprises one or more aromatic ring heteroatoms, a substituent group comprising a heteroatom, or a combination thereof; 
 X is C or O; 
 R 1  is hydrogen, substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  heteroalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 2-30  alkenyl, substituted or unsubstituted C 2-30  alkynyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 7-30  alkylaryl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl; 
 R 2  is substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  heteroalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 2-30  alkenyl, substituted or unsubstituted C 2-30  alkynyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 7-30  alkylaryl, substituted or unsubstituted C 3-30  heteroaryl, substituted or unsubstituted C 4-30  heteroarylalkyl, or —NR 11 R 12 , wherein R 11  to R 12  are each independently hydrogen, substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl; 
 optionally, R 1  and R 2  can be taken together form a 5- to 7-membered ring; 
 optionally, one of R 11  to R 12  can be taken together with R 1  to form a 5- to 7-membered ring; 
 when X is C, R a  and R b  are each independently hydrogen, substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  heteroalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 2-30  alkenyl, substituted or unsubstituted C 2-30  alkynyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7 _30 arylalkyl, substituted or unsubstituted C 7-30  alkylaryl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl; 
 wherein R a  and R b  optionally may be taken together to form a 5- to 7-membered ring; 
 wherein one of R a  or R b  optionally may be taken together with R 2  to form a 5- to 7-membered ring; and 
 when X is O, R a  and R b  are absent. 
 
     
     
         2 . The underlayer composition of  claim 1 , wherein Ar is a monocyclic or polycyclic C 5-60  heteroarylene group or a monocyclic or polycyclic C 6-60  arylene group, optionally substituted with at least one of substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  haloalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 1-30  heterocycloalkyl, substituted or unsubstituted C 2-30  alkenyl, substituted or unsubstituted C 2-30  alkynyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 7-30  alkylaryl, substituted or unsubstituted C 3-30  heteroaryl, substituted or unsubstituted C 4-30  heteroarylalkyl, halogen, —OR 21 , —SR 22 , or —NR 23 R 24  wherein R 21  to R 24  are each independently hydrogen, substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl,
 provided that the monocyclic or polycyclic C 6-60  arylene group is substituted with at least one substituent group comprising a heteroatom. 
 
     
     
         3 . The underlayer composition of  claim 1 , wherein Ar comprises a group of formula (2): 
       
         
           
           
               
               
           
         
       
       wherein,
 A1, A2, and A3 each may be present or absent, and each independently represents 1 to 3 fused aromatic rings; 
 R 3  and R 4  are each independently substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  heteroalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 2-30  alkenyl, substituted or unsubstituted C 2-30  alkynyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 7-30  alkylaryl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl, halogen, —OR 31 , —SR 32 , or —NR 33 R 34 ; 
 provided that at least one of R 3  or R 4  is —OR 31 , —SR 32 , or —NR 33 R 34 ; 
 R 31  to R 34  are each independently hydrogen, substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl; 
 m is an integer 0 to 4; 
 n is an integer 0 to 4; and 
 provided that the sum of m and n is an integer greater than 0. 
 
     
     
         4 . The underlayer composition of  claim 1 , wherein Ar comprises a group of formula (3a), (3b), or (3c): 
       
         
           
           
               
               
           
         
       
       wherein,
 A4 may be present or absent, and represents 1 to 3 fused aromatic rings; 
 Z 1  and Z 2  are each independently C or N; 
 each R 5  is independently substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  heteroalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 2-30  alkenyl, substituted or unsubstituted C 2-30  alkynyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 7-30  alkylaryl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl; and 
 p is an integer of 0 to 4, 
 wherein A4 comprises at least one heteroaryl ring, at least one of Z 1  and Z 2  is N, or a combination thereof. 
 
     
     
         5 . The underlayer composition of  claim 1 , wherein Ar comprises a group of formula (4): 
       
         
           
           
               
               
           
         
       
       wherein,
 L 1  is a single bond, —O—, —S—, —S(O)—, —SO 2 —, —C(O)—, —CR 51 R 52 —, —NR 53 —, or —PR 54 —; 
 L 2  is absent, a single bond, —O—, —S—, —S(O)—, —SO 2 —, —C(O)—, substituted or unsubstituted C 1-2  alkylene, substituted or unsubstituted C 6-30  arylene, or substituted or unsubstituted C 5-30  heteroarylene; 
 R 8  and R 9  are each independently substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  heteroalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 2-30  alkenyl, substituted or unsubstituted C 2-30  alkynyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 7-30  alkylaryl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl, halogen, —OR 55 , —SR 56 , or —NR 57 R 58 ; 
 R 51  to R 58  are each independently hydrogen, substituted or unsubstituted C 1-30  alkyl, substituted or unsubstituted C 1-30  heteroalkyl, substituted or unsubstituted C 3-30  cycloalkyl, substituted or unsubstituted C 2-30  heterocycloalkyl, substituted or unsubstituted C 6-30  aryl, substituted or unsubstituted C 7-30  arylalkyl, substituted or unsubstituted C 3-30  heteroaryl, or substituted or unsubstituted C 4-30  heteroarylalkyl; 
 a is an integer of 0 to 4; and 
 b is an integer of 0 to 4. 
 
     
     
         6 . The photoresist underlayer composition of  claim 1 , wherein the monocyclic or polycyclic C 5-60  aromatic group is a monocyclic or polycyclic C 6-60  arylene group substituted with hydroxyl. 
     
     
         7 . The underlayer composition of  claim 1 , wherein the polymer comprises a repeating unit of any one or more of formulae (6) to (12): 
       
         
           
           
               
               
           
         
         wherein Ar is as defined in any one of  claims 1  to  6 . 
       
     
     
         8 . The underlayer composition of  claim 1 , wherein X is C. 
     
     
         9 . The underlayer composition of  claim 1 , further comprising one or more of a curing agent, a crosslinking agent, and a surfactant. 
     
     
         10 . A method of forming a pattern, the method comprising: (a) applying a layer of the underlayer composition of  claim 1  on a substrate; (b) curing the applied underlayer composition to form an underlayer; and (c) forming a photoresist layer over the underlayer. 
     
     
         11 . The method of  claim 10 , further comprising forming a silicon-containing layer, an organic antireflective coating layer, or a combination thereof, above the underlayer prior to forming the photoresist layer. 
     
     
         12 . The method of  claim 10 , further comprising patterning the photoresist layer and transferring a pattern from the patterned photoresist layer to the underlayer to a layer below the underlayer.