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US 11,066,553 B2Granted
Imidazoyl urea polymers and their use in metal or metal alloy plating bath compositions
AssigneeAtotech Deutschland GmbH
InventorsHeiko Brunner, Lars Kohlmann, Agnieszka Witczak, Olivier Mann
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Abstract
The present invention relates to imidazoyl urea polymers and their use in aqueous acidic plating baths for metal or metal alloy deposition such as electrolytic deposition of copper or alloys thereof in the manufacture of printed circuit boards, IC substrates, semiconducting and glass devices for electronic applications. The plating bath according to the present invention comprises at least one source of metal ions and an imidazoyl urea polymer. The plating bath is particularly useful for filling recessed structures and build-up of pillar bump structures.
Claims21
An imidazoyl urea polymer comprising a polymeric building block according to formula (I)
- wherein A represents a unit of one or both of the following formulae (A1) and (A2)
- wherein
- X is a divalent residue selected from the group consisting of
- wherein Z is selected from —CH2—, O, S;
- z and z′ are integers independently ranging from 1 to 6, R and R′ are monovalent residues each selected independently from the group consisting of hydrogen, alkyl, aryl, aralkyl and —CH2—CH2—(OCH2CH2)y—OH wherein y is an integer from 1 to 4;
- R1 and R2 are divalent residues each selected independently from the group consisting of —(CH2)b— and —(CH2)b—[CH(R4)—CH2O]d—(CH2)e— wherein b is an integer ranging from 2 to 12;
- wherein c is an integer ranging from 0 to 3;
- d is an integer ranging from 1 to 100;
- e is an integer ranging from 1 to 3;
- each R4 is independently from each other selected from the group consisting of alkyl, aryl and hydrogen;
- R3 is a divalent residue which is selected from the group consisting of alkylene, arylene and —(CH2)f[CH(R5)—CH2—O]g—(CH2)h—, wherein f is an integer ranging from 0 to 3;
- g is an integer ranging from 1 to 100;
- h is an integer ranging from 1 to 3;
- each R5 is independently from each other selected from the group consisting of alkyl, aryl and hydrogen;
- a is an integer and ranges from 1 to 40;
- and
- D is a divalent residue and is selected from the group consisting of —CH2—CH(OH)—CH2—, —CH2—CH(SH)—CH2—, —(CH2)i—[CH(R6)—CH2—O]j—(CH2)k— and —CH2—CH(OH)—(CH2)l—[CH(R7)—CH2—O]m—(CH2)n—CH(OH)—CH2—
- wherein i is an integer ranging from 0 to 3;
- j is an integer ranging from 1 to 100;
- k is an integer ranging from 1 to 3;
- each R6 is independently from each other selected from the group consisting of alkyl, aryl and hydrogen;
- l is an integer ranging from 1 to 3;
- m is an integer ranging from 1 to 100;
- n is an integer ranging from 1 to 3;
- each R7 is independently from each other selected from the group consisting of alkyl, aryl and hydrogen;
- wherein the individual units A may be the same or different, and
- wherein the individual units D may be the same or different.
24 more elements
A process for forming an imidazoyl urea polymer, comprising reacting a monomer urea compound of the following formulae (A1′) and (A2′)
- wherein
- X′ is a monovalent residue selected from the group consisting of
- wherein Z′ is selected from —CH2—, O, S;
- z″ and z′″ are integers independently ranging from 1 to 6;
- R″ and R′″ are monovalent residues each selected independently from the group consisting of hydrogen, alkyl, aryl, aralkyl and —CH2—CH2—(OCH2CH2)y—OH, wherein y′ is an integer from 1 to 4;
- R1′ and R2′ are divalent residues each selected independently from the group consisting of
- —CH2)b′—, wherein b′ is an integer from 2 to 12, and
- —CH2)c′—[CH(R4)—CH2—O]d′—(CH2)e′—, wherein c′ is an integer ranging from 0 to 3;
- d′ is an integer ranging from 1 to 100;
- e′ is an integer ranging from 1 to 3;
- each R4′ is independently from each other selected from the group consisting of alkyl, aryl and hydrogen;
- R3′ is a divalent residue which is selected from the group consisting of alkylene, arylene and —(CH2)f′—[CH(R9)—CH2—O]g′, —(CH2)h′, wherein f′ is an integer ranging from 0 to 3;
- g′ is an integer ranging from 1 to 100;
- h′ is an integer ranging from 1 to 3;
- each R5′ is independently from each other selected from the group consisting of alkyl, aryl and hydrogen,
- with one or more monomers B selected from the group consisting of (B1), (B2), (B3) or (B4), each of which are represented by the following formulae
- E-G1-E (B1),
- E-G2-R9 (B2),
- wherein
- G1 and G2 are divalent residues represented by the following formula —(CH2)r—[CH(R10)—CH2—O]s—(CH2)t— wherein r is an integer ranging from 0 to 3, s is an integer ranging from 1 to 100, t is an integer ranging from 1 to 3;
- each R10 is independently from each other selected from the group consisting of alkyl, aryl and hydrogen;
- E each represents a leaving group individually selected from triflate, nonaflate, alkylsulphonates, arylsulphonates and halogenides;
- and
- R9 is a monovalent residue selected from the group consisting of C1- to C8-alkyl, C1- to C8-alkenyl, aralkyl, and aryl,
- wherein the reacting is carried out in one or more polar protic solvent at a temperature ranging from 50° C. to 100° C. until the one or more monomers B is completely consumed.
22 more elements
Dependencies are inferred from the claim text.