.alpha.-diazoacetoacetates and photosensitive resin compositions containing the same

• US 5,158,855 A
• Filed: 09/22/1988
• Issued: 10/27/1992
• Est. Priority Date: 09/24/1987
• Status: Expired due to Term

• Current Assignee: Hitachi, Ltd.
• Original Assignee: Hitachi, Ltd.
• Inventors: Ebata, Keisuke, Mizushima, Akiko, Nate, Kazuo, Sugiyama, Hisashi
• Primary Examiner(s): Bowers, Jr., Charles L.
• Assistant Examiner(s): CHU, JOHN S Y
• Application Number:
  US07/247,882
• Time in Patent Office: 1,496 Days
• Field of Search: 430/193, 430/189, 430/192, 430/191, 430/270, 430/326, 430/313, 430/323, 430/272, 534/556
• US Class Current: 430/192
• CPC Class Codes: G03F 7/0163 Non ionic diazonium compounds, e.g. diazosulphonates; Precursors thereof, e.g. triazenes

Abstract

An α-diazoacetoacetic acid ester derived from cholic acid, deoxycholic acid, lithocholic acid or a derivative thereof is effective as a sensitizer in a photosensitive resin composition containing an alkali-soluble resin to form a resist for lithography using KrF excimer laser.

Claims

1. An α

-diazoacetoacetic acid ester of the formula;

##STR101## wherein R₁ is --CO₂ R₉ or ##STR102## R₂, R₃ and R₄ are independently hydrogen, --OH or ##STR103## R₉ is an alkyl group having 1 to 10 carbon atoms;

provided that at least one of R₁ through R₄ contains a moiety of the formula;

##STR104##

2. An α

-diazoacetoacetic acid ester according to claim 1, which is represented by the formula;

##STR105## wherein R₁ is --CO₂ R₉ or ##STR106## R₉ is an alkyl group having 1 to 10 carbon atoms; and

R₁₀ is hydrogen or ##STR107## provided that at least one of R₁ and R₁₀ should contain the moiety of the formula;

##STR108##

3. An α

-diazoacetoacetic acid ester according to claim 1, which is represented by the formula;

##STR109## wherein R₁ is --CO₂ R₉ or ##STR110## R₉ is an alkyl group having 1 to 10 carbon atoms; and

R₁₀ is hydrogen or ##STR111## provided that at least one of R₁ and R₁₀ should contain the moiety of the formula;

##STR112##

4. An α

-diazoacetoacetic acid ester according to claim 1, which is represented by the formula;

##STR113## wherein R₁ is --CO₂ R₉ or ##STR114## R₉ is an alkyl group having 1 to 10 carbon atoms; and

R₁₀ is hydrogen or ##STR115## provided that at least one of R₁ and R₁₀ should contain the moiety of the formula;

##STR116##

5. A photosensitive resin composition comprising an alkali-soluble resin and the α

-diazoacetoacetic acid ester of claim 1 as a sensitizer.

6. A photosensitive resin composition according to claim 5, wherein the alkali-soluble resin is at least one member selected from those containing aromatic rings therein and represented by the formulae:

##STR117## wherein n is an integer of 4 or more.

7. A photosensitive resin composition according to claim 5, wherein the alkali-soluble resin is at least one member selected from alkali-soluble organosilicon resins represented by the formulae:

##STR118## wherein R₁₁, R₁₂, R₁₄, R₁₅, R₁₆ and R₁₈ are independently an alkyl group having 1 to 6 carbon atoms;

R₁₃, R₁₇ and R₁₉ are independently a trialkylsilyl group;

d and k are independently 1 or 2;

a, e and h are independently an integer of 1 or more; and

b, c, f, g, i and j are independently zero or an integer of 1 or more, provided that a/(a+b+c), e/(e+f+g) and h/(h+i+j) are 0.4 or more.

8. A photosensitive resin composition according to claim 5, wherein the photosensitive resin composition comprises 50 to 95 parts by weight of a resin represented by the formula:

##STR119## wherein n is an integer of 4 or more, and 50 to 5 parts by weight of a sensitizer represented by the formula;

##STR120## wherein R₁ is --CO₂ R₉ or ##STR121## R₉ is an alkyl group having 1 to 10 carbon atoms;

R₁₀ is hydrogen or ##STR122## provided that at least one of R₁ and R₁₀ should contain the moiety of the formula;

##STR123##

9. A photosensitive resin composition according to claim 7, wherein the photosensitive resin composition comprises 50 to 95 parts by weight of a resin represented by the formula:

##STR124## wherein n is an integer of 4 or more, and 50 to 5 parts by weight of a sensitizer represented by the formula;

##STR125## wherein R₁ is --CO₂ R₉ or ##STR126## R₉ is an alkyl group having 1 to 10 carbon atoms;

R₁₀ is hydrogen or ##STR127## provided that at least one of R₁ and R₁₀ should contain the moiety of the formula;

##STR128##

10. A photosensitive resin composition according to claim 5, wherein the photosensitive resin composition comprises 60 to 95 parts by weight of a silicone resin represented by the formula:

##STR129## wherein R₁₈ is an alkyl group having 1 to 6 carbon atoms;

R₁₉ is a trialkylsilyl group;

k is 1 or 2;

h is an integer of 1 or more;

i and j are independently zero or an integer of 1 or more, provided that h/(h+i+j) is 0.4 or more, and 40 to 5 parts by weight of a sensitizer represented by the formula;

##STR130## wherein R₁ is --CO₂ R₉ or ##STR131## R₉ is an alkyl group having 1 to 10 carbon atoms;

R₁₀ is hydrogen or ##STR132## provided that at least one of R₁ and R₁₀ should contain the moiety of the formula;

##STR133##

11. A photosensitive resin composition according to claim 5, wherein the photosensitive resin composition comprises 60 to 95 parts by weight of a silicone resin represented by the formula:

##STR134## wherein R₁₈ is an alkyl group having 1 to 6 carbon atoms;

R₁₉ is a trialkylsilyl group;

k is 1 or 2;

h is an integer of 1 or more;

i and j are independently zero or an integer of 1 or more, provided that h/(h+i+j) is 0.4 or more, and 40 to 5 parts by weight of a sensitizer represented by the formula;

##STR135## where R₁ is --CO₂ R₉ or ##STR136## R₉ is an alkyl group having 1 to 10 carbon atoms; and

R₁₀ is hydrogen or ##STR137## provided that at least one of R₁ and R₁₀ should contain the moiety of the formula;

##STR138##

12. An α

-diazoacetoacetic acid ester according to claim 1, wherein R₁, R₂, R₃, and R₄ in the formula ##STR139##