Photoresist composition and method of manufacturing a semiconductor device

1 . A photoresist composition, comprising:

a photoactive compound;

a polymer; and

a crosslinker,

wherein the polymer has a structure

wherein A 1 is a substituted or unsubstituted C1-C30 alkyl group, C1-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C1-C30 heterocyclic group, or C1-C30 chain,

wherein A2 is a substituted or unsubstituted C6-C30 aryl group, C1-C30 alkyl group, C1-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C1-C30 heterocyclic group, or C1-C30 chain,

wherein A 3 is a substituted or unsubstituted C1-C30 alkyl group, C1-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C1-C30 heterocyclic group, or C1-C30 chain,

wherein R 1 is a substituted or unsubstituted C4-C15 chain, cyclic, or 3-D structure alkyl group, C4-C15 cycloalkyl group, C4-C15 hydroxylalkyl group, C4-C15 alkoxy group, or C4-C15 alkoxyl alkyl group,

wherein a proportion of x, y, and z in the polymer is 0<x/(x+y+z)<1, 0<y/(x+y+z)<1, and 0<z/(x+y+z)<1,

the crosslinker is a monomer, oligomer, or polymer including one or more structures selected from

wherein B1, B2, B3, B4, and D are each independently a substituted or unsubstituted C6-C30 aryl group, C1-C30 alkyl group, C3-C30 cycloalkyl group, C2-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C3-C30 hydrocarbon ring, saturated or unsaturated C1-C30 heterocyclic group, or a C1-C30 chain, ring, or 3-D structure, and

wherein R and Ra are each independently a substituted or unsubstituted C4-C15 chain, cyclic, or 3-D structure alkyl group, C4-C15 cycloalkyl group, C4-C15 hydroxylalkyl group, C4-C15 alkoxy group, or C4-C15 alkoxyl alkyl group.

2 . The photoresist composition of claim 1 , wherein R 1 is an acid labile group selected from one or more of

3 . The photoresist composition of claim 1 , wherein the photoactive compound is a photoacid generator.

4 . The photoresist composition of claim 1 , further comprising a solvent.

5 . The photoresist composition of claim 1 , further comprising metal oxide nanoparticles and one or more organic ligands.

6 . The photoresist composition of claim 1 , wherein the crosslinker includes one or more epoxy groups.

7 . The photoresist composition of claim 1 , wherein R 1 is an adamantyl group or a norbornenyl group.

8 . The photoresist composition of claim 1 , wherein B1, B2, B3, B4, D, R, and Ra are substituted with one or more fluoro, chloro, bromo, or iodo groups.

9 . A photoresist composition, comprising:

a photoacid generator;

a polymer;

metal nanoparticles complexed with one or more organic ligands; and

a crosslinker,

wherein the polymer has a structure

wherein A 1 is a substituted or unsubstituted C1-C30 alkyl group, C3-C30 cycloalkyl group, C1-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, C2-C30-acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C1-C30 heterocyclic group, or C1-C30 chain,

wherein A 2 and A 3 are independently a substituted or unsubstituted C6-C30 aryl group, C1-C30 alkyl group, C3-C30 cycloalkyl group, C1-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C3-C30 hydrocarbon ring, saturated or unsaturated C1-C30 heterocyclic group, or C1-C30 chain, ring, or 3-D structure,

wherein R 1 is a substituted or unsubstituted C4-C15 chain, cyclic, or 3-D structure alkyl group, C4-C15 cycloalkyl group, C4-C15 hydroxylalkyl group, C4-C15 alkoxy group, or C4-C15 alkoxyl alkyl group,

wherein a proportion of x, y, and z in the polymer is 0<x/(x+y+z)<1, 0<y/(x+y+z)<1, and 0<z/(x+y+z)<1,

the crosslinker is a monomer, oligomer, or polymer including one or more structures selected from

wherein B1, B2, B3, B4, and D are each independently a substituted or unsubstituted C6-C30 aryl group, C1-C30 alkyl group, C3-C30 cycloalkyl group, C2-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C3-C30 hydrocarbon ring, saturated or unsaturated C1-C30 heterocyclic group, or a C1-C30 chain, ring, or 3-D structure, and

wherein R and Ra are each independently a substituted or unsubstituted C4-C15 chain, cyclic, or 3-D structure alkyl group, C4-C15 cycloalkyl group, C4-C15 hydroxylalkyl group, C4-C15 alkoxy group, or C4-C15 alkoxyl alkyl group.

10 . The photoresist composition of claim 9 , wherein the metal nanoparticles include one or more selected from the group consisting of Ba, La, Ce, In, Sn, Ag, Sb, and oxides thereof.

11 . The photoresist composition of claim 9 , wherein the metal nanoparticles have an average particle size between 1 nm and 20 nm.

12 . The photoresist composition of claim 9 , wherein the organic ligands include C1-C7 alkyl groups or C1-C7 fluoroalkyl groups.

13 . The photoresist composition of claim 12 , wherein the C1-C7 alkyl groups or C1-C7 fluoroalkyl groups include one or more substituents selected from the group consisting of —CF 3 , —SH, —OH, ═O, —S—, —P—, —PO 2 , —C(═O)SH, —C(═O)OH, —C(═O)O—, —O—, —N—, —C(═O)NH, —SO 2 OH, —SO 2 SH, —SOH, and —SO 2 —.

14 . A photoresist composition, comprising:

a photoactive compound;

a polymer;

metal nanoparticles; and

a crosslinker,

wherein the polymer has a structure

wherein A 1 and A 2 are each independently a substituted or unsubstituted C1-C30 alkyl group, C3-C30 cycloalkyl group, C1-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C3-C30 hydrocarbon ring, saturated or unsaturated C1-C30 heterocyclic group, or C1-C30 chain, ring, or 3-D structure,

wherein A 3 is a substituted or unsubstituted C1-C30 alkyl group, C3-C30 cycloalkyl group, C1-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C1-C30 heterocyclic group, or C1-C30 chain or 3-D structure,

wherein R 1 is an acid labile group selected from one or more of

wherein a proportion of x, y, and z in the polymer is 0<x/(x+y+z)<1, 0<y/(x+y+z)<1, and 0<z/(x+y+z)<1,

the crosslinker is a monomer, oligomer, or polymer including one or more structures selected from

wherein B1, B2, B3, B4, and D are each independently a substituted or unsubstituted C6-C30 aryl group, C1-C30 alkyl group, C3-C30 cycloalkyl group, C2-C30 hydroxylalkyl group, C2-C30 alkoxy group, C3-C30 alkoxyl alkyl group, acetyl group, C3-C30 acetylalkyl group, C1-C30 carboxyl group, C2-C30 alkyl carboxyl group, C4-C30 cycloalkyl carboxyl group, saturated or unsaturated C3-C30 hydrocarbon ring, saturated or unsaturated C1-C30 heterocyclic group, or a C1-C30 chain, ring, or 3-D structure, and

wherein R and Ra are each independently a substituted or unsubstituted C4-C15 chain, cyclic, or 3-D structure alkyl group, C4-C15 cycloalkyl group, C4-C15 hydroxylalkyl group, C4-C15 alkoxy group, or C4-C15 alkoxyl alkyl group.

15 . The photoresist composition of claim 14 , wherein one of A 1 and A 2 includes a carboxyl group.

16 . The photoresist composition of claim 14 , further comprising a quencher selected from the group consisting of trimethylamine, diethylamine, triethylamine, di-n-propylamine, tri-n-propylamine, tripentylamine, diethanolamine, and triethanolamine.

17 . The photoresist composition of claim 14 , further comprising a quencher selected from the group consisting of malonic acid, citric acid, malic acid, succinic acid, benzoic acid, salicylic acid, phosphoric acid, phosphoric acid di-n-butyl ester, phosphoric acid diphenyl ester, phosphonic acid, phosphonic acid dimethyl ester, phosphonic acid di-n-butyl ester, phenylphosphonic acid, phosphonic acid diphenyl ester, phosphonic acid dibenzyl ester, phosphinic acid, and phenylphosphinic acid.

18 . The photoresist composition of claim 14 , further comprising ligands selected from the group consisting of C1-C7 alkyl groups or C1-C7 fluoroalkyl groups, wherein the C1-C7 alkyl groups and C1-C7 fluoroalkyl groups include one or more substituents selected from the group consisting of —CF 3 , —SH, —OH, ═O, —S—, —P—, —PO 2 , —C(═O)SH, —C(═O)OH, —C(═O)O—, —O—, —N—, —C(═O)NH, —SO 2 OH, —SO 2 SH, —SOH, and —SO 2 —.

19 . The photoresist composition of claim 5 , wherein the metal oxide nanoparticles include an oxide of at least one of Ti, Zn, Zr, Ni, Co, Mn, Cu, Fe, Sr, W, V, Cr, Sn, Hf, In, Cd, Mo, Ta, Nb, Al, Cs, Ba), La, Ce, Ag, or Sb.

20 . The photoresist composition of claim 5 , wherein the metal oxide nanoparticles have an average particle size ranging from 2 nm to 5 nm.