Granted Patent B2

US 9,328,198 · App. 14/514,728 · Granted May 3, 2016

Abstract

Claims (44)

1. A dendrimer compound represented by the following formula (1):

Ar 1 (—Z 1 ) m1-k1 (-L 1 ′ p1 -L 1 -L 1 ′ p1 -A) k1   (1)

in which

Ar 1 is an aromatic skeleton selected from the group consisting of benzene skeleton, naphthalene skeleton and anthracene skeleton;

each Z 1 is hydrogen, a hydrocarbon group of 1 to 3 carbon atoms or a halogen provided that the plural Z 1 s may be the same or different from each other;

each L 1 is amide bond or ester bond provided that the plural L 1 s may be the same or different from each other;

each L 1 ′ is a divalent linking group selected from the group consisting of a hydrocarbon chain having 1 to 3 carbon atoms, an oxygen-containing hydrocarbon chain having 1 to 3 carbon atoms, and a sulfur-containing hydrocarbon chain having 1 to 3 carbon atoms, and may be a straight chain or a branched chain provided that the plural L 1 ′s may be the same or different from each other;

m1 is 6 if Ar 1 is benzene skeleton, 8 if Ar 1 is naphthalene skeleton or 10 if Ar 1 is anthracene skeleton;

k1 is a number of 2 or more but not more than m1;

each p1 is 0 or 1 provided that the plural p1s may be the same or different from each other; and

A is a group represented by the following formula (2):

—Ar 2 (—Z 2 ) m2-k2 (-L 2 ′ p2 -L 2 -L 2 ′ p2 -B) k2   (2)

in which

Ar 2 is an aromatic skeleton selected from the group consisting of benzene skeleton, naphthalene skeleton and anthracene skeleton;

each Z 2 is hydrogen, a hydrocarbon group of 1 to 3 carbon atoms or a halogen provided that the plural Z 2 s may be the same or different from each other;

each L 2 is amide bond or ester bond provided that the plural L 2 s may be the same or different from each other;

each L 2 ′ is a divalent linking group selected from the group consisting of a hydrocarbon chain having 1 to 4 carbon atoms, an oxygen-containing hydrocarbon chain having 1 to 4 carbon atoms, and a sulfur-containing hydrocarbon chain having 1 to 4 carbon atoms, and may be a straight chain or a branched chain provided that the plural L 2 ′s may be the same or different from each other;

m2 is 5 if Ar 2 is benzene skeleton, 7 if Ar 2 is naphthalene skeleton or 9 if Ar 2 is anthracene skeleton;

k2 is a number of 1 or more but not more than m2;

each p2 is 0 or 1 provided that the plural p2s may be the same or different from each other; and

B is a group represented by the above formula (2) or by the following formula (3A) or (3B):

—Ar 3 (—Z 3 ) m3   (3A)

—R 3   (3B)

in which

Ar 3 is an aromatic skeleton selected from the group consisting of benzene skeleton, naphthalene skeleton and anthracene skeleton;

each Z 3 is a group selected from the group consisting of hydrogen, a hydrocarbon group of 1 to 4 carbon atoms, a halogen, carboxyl group and ester group, provided that the plural Z 3 s may be the same or different from each other;

m3 is 5 if Ar 3 is benzene skeleton, 7 if Ar 3 is naphthalene skeleton or 9 if Ar 3 is anthracene skeleton; and

R 3 is a hydrocarbon group of 1 to 4 carbon atoms which may be substituted with a halogen;

and further wherein the dendrimer compound is further selected from the group consisting of a), b), c) d) e), f) and g;

a) the dendrimer compound, wherein all of said p1s are 0, the number of generation is 10 or less, said Ar 1 is benzene skeleton, K1 is 3 and the halogens in Z 3 and R 3 are selected from the group consisting of fluorine, chlorine, bromine, and iodine;

b) the dendrimer compound, wherein all of said p1s are 0, the number of generation is 10 or less, said Ar 1 is benzene skeleton, K1 is 3 and the halogens in Z 3 and R 3 are selected from the group consisting of fluorine and iodine;

c) the dendrimer compound wherein all of said p1s are 0, the number of generation is 10 or less, said Ar 1 is benzene skeleton, K1 is 3, Ar 2 is benzene skeleton, K2 is 3 or 2, Ar 3 is a benzene skeleton, and the halogens in Z 3 and R 3 are selected from the group consisting of fluorine, chlorine, bromine, and iodine;

d) the dendrimer compound wherein all of said p1s are 0, the number of generation is 10 or less, said Ar 1 is benzene skeleton, K1 is 3, Ar 2 is benzene skeleton, K2 is 3 or 2, Ar 3 is a benzene skeleton, and the halogens in Z 3 and R 3 are selected from the group consisting of fluorine and iodine;

e) the dendrimer compound wherein all of said p1s are 0, the number of generation is 6 or less, said Ar 1 is benzene skeleton, K1 is 3, Ar 2 is benzene skeleton, K2 is 3 or 2, Ar 3 is a benzene skeleton, and the halogens in Z 3 and R 3 are selected from the group consisting of fluorine and iodine;

f) the dendrimer compound wherein all of said p1s are 0, the number of generation is 10 or less, said Ar 1 is benzene skeleton, K1 is 3, Ar 2 is benzene skeleton, K2 is 3 or 2, and Z 2 is fluorine, chlorine, bromine, or iodine; and

g) the dendrimer compound wherein all of said p1s are 0, the number of generation is 10 or less, said Ar 1 is benzene skeleton, K1 is 3, Ar 2 is benzene skeleton, K2 is 3 or 2, and Z 2 is iodine or fluorine.

2. A composition for forming a resist underlayer film comprising the dendrimer compound according to claim 1 , a crosslinking agent, a thermal acid generating agent, and a solvent.

3. An underlayer film formed by coating on a substrate and then heating the composition for forming resist underlayer film according to claim 2 .

4. A pattern formation method comprising the steps of

coating on a semiconductor substrate and then baking the composition for forming resist underlayer film according to claim 2 , to form an underlayer film,

forming a photoresist layer on said underlayer film,

exposing to light said semiconductor substrate covered with said underlayer film and said photoresist layer, and

developing said exposed photoresist layer with a developer.

5. The pattern formation method according to claim 4 , wherein said exposing step is carried out by use of light in a wavelength range from the wavelength of electron beams to that of KrF excimer laser.

Assignments (6)