Methods for producing a dielectric, dielectric having self-generating pores, monomer for porous dielectrics, process for preparing poly-o-hydroxyamides, process for preparing ploybenzoxazoles, and processes for producing an electronic component
AssigneeInfineon Technologies AG
InventorsRecai Sezi, Andreas Walter, Klaus Lowack, Anna Maltenberger, Robert Banfic
Life of this patent
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Abstract
Poly-o-hydroxyamides include binaphthyl substituents as repeating units. The poly-o-hydroxyamides can be cyclized to give the polybenzoxazole by heating. Pore formation occurs, so that a dielectric having a very low dielectric constant k of less than 2.5 is obtained.
Claims14
A method for producing a dielectric, which comprises:
- using a poly-o-hydroxyamides of Formula I
- where
- E1 and E2, in each case independently, are substituents selected from the group consisting of hydrogen, a hydroxyl group, a saturated monovalent hydrocarbon, and an unsaturated monovalent hydrocarbon;
- Y1 and Y2, in each case independently for each position, are a divalent hydrocarbon;
- Z1, in each case independently for each position, is a structural unit having a formula selected from the group consisting of Formula IIa and IIb
- the bond (-*) and the substituent -GR5 being disposed in the ortho position relative to one another,
- Z2, in each case independently for each position, is a tetravalent hydrocarbon composed of groups linked to one another and selected from the group consisting of alkyl and aryl groups;
- R1, R2, R3, and R4, in each case independently, are substituents selected from the group consisting of H, —C6H5, —(CH2)n—CH3, -G-(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, -G-CH(CH3)2, —C(CH3)3, -G-C(CH3)3, —(CF2)n—CF3, -G-(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —N(CH3)2, —N(CF3)2,
- R5, in each case independently, is a substituent selected from the group consisting of H, —CO(CH2)n—CH3, —COO—(CH2)n—CH3, —(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, —C(CH3)3, —(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —(CH2)n—C6H5, —COO—(CH2)n—C6H5;
- G is a heteroatom selected from the group consisting of oxygen and sulfur;
- a is an integer from 0 to 1;
- b has a value from 1 to 200;
- c has a value from 0 to 200;
- d is an integer from 0 to 1;
- n is an integer from 0 to 5;
- R6 is a divalent substituent selected from the group consisting of:
- R7 is a substituent selected from the group consisting of an alkyl group having from 1 to 10 carbon atoms and an aryl group having from 5 to 22 carbon atoms;
- and
- e is an integer from 1 to 10.
A monomer for the preparation of a poly-o-hydroxyamide usable in dielectrics, comprising a backbone having a formula selected from the group consisting of Formula IVa and IV
- where
- R1, R2, R3, and R4, in each case independently, are selected from the group of substituents selected from the group consisting of H, —C6H5, —(CH2)n—CH3, -G-(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, -G-CH(CH3)2, —C(CH3)3, -G-C(CH3)3, —(CF2)n—CF3, -G-(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —N(CH3)2, —N(CF3)2,
- R5, in each case independently, is a substituent selected from the group consisting of H, —CO(CH2)n—CH3, —COO—(CH2)n—CH3, —(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, —C(CH3)3, —(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —(CH2)n—C6H5, —COO—(CH2)n—C6H5;
- and
- G is a heteroatom selected from the group consisting of oxygen and sulfur.
A process for preparing polybenzoxazoles having a Formula III
- where
- Z1 has a formula selected from the group consisting of
- E1 and E2, in each case independently, are substituents selected from the group consisting of hydrogen, a hydroxyl group, a saturated monovalent hydrocarbon, and an unsaturated monovalent hydrocarbon;
- Y1 and Y2, in each case independently for each position, are a divalent hydrocarbon;
- Z2, in each case independently for each position, is a tetravalent hydrocarbon composed of groups linked to one another and selected from the group consisting of alkyl and aryl groups;
- R1, R2, R3, and R4, in each case independently, are substituents selected from the group consisting of H, —C6H5, —(CH2)n—CH3, -G-(CH2)n—CH3, —CH((CH2)nCH3)2, —CH (CH3)2, -G-CH(CH3)2, —C(CH3)3, -G-C(CH3)3, —(CF2)n—CF3, -G-(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —N(CH3)2, —N(CF3)2,
- R5, in each case independently, is a substituent selected from the group consisting of H, —CO(CH2)n—CH3, —COO—(CH2)n—CH3, —(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, —C(CH3)3, —(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —(CH2)n—C6H5, —COO—(CH2)n—C6H5;
- G is a heteroatom selected from the group consisting of oxygen and sulfur;
- a is an integer from 0 to 1;
- b has a value from 1 to 200;
- c has a value from 0 to 200;
- and
- d is an integer from 0 to 1;
- the method which comprises:
- heating poly-o-hydroxyamides having a Formula I
- where
- E1 and E2, in each case independently, are substituents selected from the group consisting of hydrogen, a hydroxyl group, a saturated monovalent hydrocarbon, and an unsaturated monovalent hydrocarbon;
- Y1 and Y2, in each case independently for each position, are a divalent hydrocarbon;
- Z1, in each case independently for each position, is a structural unit having a formula selected from the group consisting of Formula IIa and IIb
- in which the bond (-*) and the substituent -GR5 are disposed in the ortho position relative to one another,
- Z2, in each case independently for each position, is a tetravalent hydrocarbon composed of groups linked to one another and selected from the group consisting of alkyl and aryl groups;
- R1, R2, R3, and R4, in each case independently, are substituents selected from the group consisting of H, —C6H5, —(CH2)n—CH3, -G-(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, -G-CH(CH3)2, —C(CH3)3, -G-C(CH3)3, —(CF2)n—CF3, -G-(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —N(CH3)2, —N(CF3)2,
- R5, in each case independently, is a substituent selected from the group consisting of H, —CO (CH2)n—CH3, —COO—(CH2)n—CH3, —(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, —C(CH3)3, —(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —(CH2)n—C6H5, —COO—(CH2)n—C6H5;
- G is a heteroatom selected from the group consisting of oxygen and sulfur;
- a is an integer from 0 to 1;
- b has a value from 1 to 200;
- c has a value from 0 to 200;
- d is an integer from 0 to 1;
- n is an integer from 0 to 5;
- R6 is a divalent substituent selected from the group consisting of:
- R7 is a substituent selected from the group consisting of an alkyl group having from 1 to 10 carbon atoms and an aryl group having from 5 to 22 carbon atoms;
- and p1 e is an integer from 1 to 10.
A process for producing an electronic component, which comprises:
- preparing a solution of a poly-o-hydroxyamide having a Formula I in a solvent
- where
- E1 and E2, in each case independently, are substituents selected from the group consisting of hydrogen, a hydroxyl group, a saturated monovalent hydrocarbon, and an unsaturated monovalent hydrocarbon;
- Y1 and Y2, in each case independently for each position, are a divalent hydrocarbon;
- Z1, in each case independently for each position, is a structural unit having a formula selected from the group consisting of Formula IIa and IIb
- in which the bond (-*) and the substituent -GR5 are disposed in the ortho position relative to one another,
- Z2, in each case independently for each position, is a tetravalent hydrocarbon composed of groups linked to one another and selected from the group consisting of alkyl and aryl groups;
- R1, R2, R3, and R4, in each case independently, are substituents selected from the group consisting of H, —C6H5, —(CH2)n—CH3, -G-(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, -G-CH(CH3)2, —C(CH3)3, -G-C(CH3)3, —(CF2)n—CF3, -G-(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —N(CH3)2, —N(CF3)2,
- R5, in each case independently, is a substituent selected from the group consisting of H, —CO(CH2)n—CH3, —COO—(CH2)n—CH3, —(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, —C(CH3)3, —(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —(CH2)n—C6H5, —COO—(CH2)n—C6H5;
- G is a heteroatom selected from the group consisting of oxygen and sulfur;
- a is an integer from 0 to 1;
- b has a value from 1 to 200;
- c has a value from 0 to 200;
- d is an integer from 0 to 1;
- n is an integer from 0 to 5;
- R6 is a divalent substituent selected from the group consisting of:
- R7 is a substituent selected from the group consisting of an alkyl group having from 1 to 10 carbon atoms and an aryl group having from 5 to 22 carbon atoms;
- and
- e is an integer from 1 to 10;
- applying the solution to a substrate;
- evaporating the solvent to obtain a film;
- heating the film to cyclize the poly-o-hydroxyamide having the Formula I to yield a polybenzoxazole having a Formula III
- where
- Z1 has a formula selected from the group consisting of
- E1 and E2, in each case independently, are substituents selected from the group consisting of hydrogen, a hydroxyl group, a saturated monovalent hydrocarbon, and an unsaturated monovalent hydrocarbon;
- Y1 and Y2, in each case independently for each position, are a divalent hydrocarbon;
- Z2, in each case independently for each position, is a tetravalent hydrocarbon composed of groups linked to one another and selected from the group consisting of alkyl and aryl groups;
- R1, R2, R3, and R4, in each case independently, are substituents selected from the group consisting of H, —C6H5, —(CH2)n—CH3, -G-(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, -G-CH(CH3)2, —C(CH3)3, -G-C(CH3)3, —(CF2)n—CF3, -G-(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —N(CH3)2, —N(CF3)2,
- R5, in each case independently, is a substituent selected from the group consisting of H, —CO (CH2)n—CH3, —COO—(CH2)n—CH3, —(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)2, —C(CH3)3, —(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —(CH2)n—C6H5, —COO—(CH2)n—C6H5;
- G is a heteroatom selected from the group consisting of oxygen and sulfur;
- a is an integer from 0 to 1;
- b has a value from 1 to 200;
- c has a value from 0 to 200;
- and
- d is an integer from 0 to 1;
- structuring the film to obtain a resist structure having trenches;
- depositing a conductive material on the resist structure so that the trenches are filled with a conductive material;
- and
- removing excess of the conductive material.
A process for producing an electronic component, which comprises:
- preparing a solution of a poly-o-hydroxyamide in a solvent, the poly-o-hyroxyamide having a Formula I
- where
- E1 and E2, in each case independently, are substituents selected from the group consisting of hydrogen, a hydroxyl group, a saturated monovalent hydrocarbon, and an unsaturated monovalent hydrocarbon;
- Y1 and Y2, in each case independently for each position, are a divalent hydrocarbon;
- Z1, in each case independently for each position, is a structural unit having a formula selected from the group consisting of Formula IIa and IIb
- in which the bond (-*) and the substituent -GR5 are disposed in the ortho position relative to one another,
- Z2, in each case independently for each position, is a tetravalent hydrocarbon composed of groups linked to one another and selected from the group consisting of alkyl and aryl groups;
- R1, R2, R3, and R4, in each case independently, are substituents selected from the group consisting of H, —C6H5, —(CH2)n—CH3, -G-(CH2)n—CH3, —CH((CH2)nCH3)2, —CH (CH3)2, -G-CH(CH3)2, —C(CH3)3, -G-C(CH3)3, —(CF2)n—CF3, -G-(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —N(CH3)2, —N(CF3)2,
- R5, in each case independently, is a substituent selected from the group consisting of H, —CO(CH2)n—CH3, —COO—(CH2)n—CH3, —(CH2)n—CH3, —CH((CH2)nCH3)2, —CH(CH3)3)2, —C(CH3)3, —(CF2)n—CF3, —CF((CF2)nCF3)2, —CF(CF3)2, —C(CF3)3, —(CH2)n—C6H5, —COO—(CH2)n—C6H5;
- G is a heteroatom selected from the group consisting of oxygen and sulfur;
- a is an integer from 0 to 1;
- b has a value from 1 to 200;
- c has a value from 0 to 200;
- d is an integer from 0 to 1;
- n is an integer from 0 to 5;
- R6 is a divalent substituent selected from the group consisting of:
- R7 is a substituent selected from the group consisting of an alkyl group having from 1 to 10 carbon atoms and an aryl group having from 5 to 22 carbon atoms;
- and
- e is an integer from 1 to 10;
- applying the solution to a substrate having a surface with metallic structures and trenches formed between the metallic structures;
- evaporating the solvent to fill the trenches with the poly-o-hydroxyamide of the Formula I;
- and
- heating the substrate to cyclize the poly-o-hydroxyamide of the formula I to yield the polybenzoxazole having a Formula III.
Dependencies are inferred from the claim text.