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US 2019/0169436 A1Published application
Silsesquioxane resin and silyl-anhydride composition
OwnerDavid Altergott, Peng-Fei Fu +1inventors
InventorsDavid Altergott, Peng-Fei Fu, Wonbum Jang
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Abstract
A silsesquioxane-containing composition comprising a silsesquioxane resin and a silyl-anhydride of formula (II) (see description), products prepared therefrom, photoresist compositions comprising the silsesquioxane-containing composition and a photoacid generator, products prepared therefrom, methods of making and using same, and manufactured articles and semiconductor devices containing same.
Claims14
A silsesquioxane-containing composition comprising (A) a silsesquioxane resin and (B) a silyl-anhydride, wherein:
- the (A) silsesquioxane resin is of formula (I):
- [HSiO3/2]t1[Z-L-SiO3/2]t2[H(R1O)SiO2/2]d[(R1O)xSiO(4-x)/2]y[R2SiO3/2]t3 (I),
- wherein:
- subscript t1 is a mole fraction of from 0.4 to 0.9;
- subscript t2 is a mole fraction of from 0.1 to 0.6;
- subscript d is a mole fraction from 0 to 0.45;
- subscript x is an integer of 1, 2, or 3;
- subscript y is a mole fraction from 0 to 0.25;
- subscript t3 is a mole fraction from 0 to 0.15;
- the sum of t1+t2=from ≥0.9 to ≤1 and the sum of t1+t2+d+y+t3=1;
- each R1 is independently H or (C1-C6)alkyl;
- each R2 is independently HO-L- or HOOC-L-;
- each L is independently a divalent (C1-C20)hydrocarbon group that is unsubstituted or substituted with at least 1 substituent independently selected from (C1-C3)alkyl, —OH, and a fluorine atom up to and including perfluoro-substitution;
- and
- each Z is —OH, —COOH, —O-THP, —OCH(R3a)2, —OC(R3b)3, —COOCH(R3a)2, —COOC(R3b)3, —OCOOCH(R3a)2, or —OCOOC(R3b)3,
- wherein THP is tetrahydropyran-2-yl;
- wherein each R3a is independently a (C1-C6)alkyl, (C3-C12)cycloalkyl, (C6-C10)aralkyl, ((C1-C6)alkyl)3SiCH2CH2-, or 2 R3a together with the carbon atom to which they are both bonded are a (C3-C12)cycloalkyl or a (C6-C12)bicycloalkyl;
- and
- wherein each R3b is independently a (C1-C6)alkyl, (C3-C12)cycloalkyl, (C6-C10)aralkyl, ((C1-C6)alkyl)3SiCH2CH2-;
- or 2 R3b together with the carbon atom to which they are both bonded are a (C3-C12)cycloalkyl or a (C6-C12)bicycloalkyl and the remaining R3b is independently a (C1-C6)alkyl, (C3-C12)cycloalkyl, (C6-C10)aralkyl, or ((C1-C6)alkyl)3SiCH2CH2-;
- or all 3 R3b together with the carbon atom to which they are all bonded are a (C7-C12)bicycloalkyl;
- and
- the (B) silyl-anhydride is of formula (II):
- (R4O)3Si-(L1)m-C(R5)2—C(═O)—O—C(═O)—R6 (II), wherein:
- each R5 is independently H, a (C1-C6)alkyl, or a monovalent group of formula -(L2)n-Si(OR4)3;
- or both R5 are taken together to form a (C2-C5)alkane-diyl;
- or one R5 is taken together with R6 to form a bond or (C1-C4)alkane-diyl, and the remaining R5 is independently H, a (C1-C6)alkyl, or a monovalent group of formula -(L2)n-Si(OR4)3;
- or both R5 are taken together with R6 to form ═CH—;
- R6 is taken together with R5 as described above or R6 is a (C1-C8)hydrocarbyl or a monovalent group of formula —C(R7)2-(L2)n-Si(OR4)3;
- subscript m is an integer of 0 or 1;
- each subscript n is independently an integer of 0 or 1;
- each R4 is independently an unsubstituted (C1-C6)alkyl;
- each L1 and L2 is independently a (C1-C8)hydrocarbon-diyl;
- and
- each R7 is independently H or a (C1-C6)alkyl;
- or both R7 are taken together to form a (C2-C5)alkane-diyl.
33 more elements
Dependencies are inferred from the claim text.