Partially carboxymethylated novolaks for photoresist systems: New photoresists for development under mildly alkaline conditions

Westerwelle, Ulrich; Bahr, Gunnar von; Grützner, Gabi; Reuther, F.

doi:10.1016/s0167-9317(98)00079-3

Cited by 4 publications

(3 citation statements)

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“…A polymer with the desired pendant functional group can be synthesized in two ways: 1) by the incorporation of the functional group as a pendant unit of the monomer itself and polymerizing the same by any one of the chain‐growth mechanisms; 2) by chemical modification of the nonfunctionalized polymer. It is well known that the introduction of carboxyl groups in a polymer chain improves solubility and resolution of the photoresist,19 and that would afford the aqueous‐based development of the uncrossed linked/nonexposed polymeric regions through a neutralization reaction. The introduction of a pendant aliphatic group on the polymer backbone would provide the necessary photoactivated imaging functionality via an acid‐catalyzed crosslinking reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of poly(N‐isopropylacrylamide) with a low molecular weight and a low polydispersity index by single‐electron transfer living radical polymerization

Turan

Zengi̇n

Çaykara

2011

J. Polym. Sci. A Polym. Chem.

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The single‐electron transfer living radical polymerization (SET‐LRP) method in the presence of chain transfer agent was used to synthesize poly(N‐isopropylacrylamide) [poly(NIPAM)] with a low molecular weight and a low polydispersity index. This was achieved using Cu(I)/2,2′‐bipyridine as the catalyst, 2‐bromopropionyl bromide as the initiator, 2‐mercaptoethanol as the chain transfer agent (TH), and N,N‐dimethylformamide (DMF) as the solvent at 90 °C. The copper nanoparticles with diameters of 16 ± 3 nm were obtained in situ by the disproportionation of Cu(I) to Cu(0) and Cu(II) species in DMF at 22 °C for 24 h. The molecular weights of poly(NIPAM) produced were significantly higher than the theoretical values, and the polydispersities were less than 1.18. The chain transfer constant (Ctr) was found to be 0.051. Although the kinetic analysis of SET‐LRP in the presence of TH corroborated the characteristics of controlled/living polymerization with pseudo‐first‐order kinetic behavior, the polymerization also exhibited a retardation period (k papp > ktr). The influence of molecular weight on lower critical solution temperature (LCST) was investigated by refractometry. Our experimental results explicitly elucidate that the LCST values increase slightly with decreasing molecular weight. Reversibility of solubility and collapse in response to temperature well correlated with increased molecular weight of poly(NIPAM). © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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Section: Introductionmentioning

confidence: 99%

Synthesis of poly(N‐isopropylacrylamide) with a low molecular weight and a low polydispersity index by single‐electron transfer living radical polymerization

Turan

Zengi̇n

Çaykara

2011

J. Polym. Sci. A Polym. Chem.

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“…Cationic photopolymerization of vinyl and heterocyclic monomers and photocrosslinking of polymers containing oxirane and thirane rings initiated by an acid generated via photolysis of onium salts are well known [9,10]. A radiation sensitive mixture which contains an acidforming compound and a polymeric compound having recurrent orthocarboxylic acid ester groupings for the production of positive and negative relief images have been reported [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Novel Crosslinking Method for Negative Tone Photoresist having Pendant Carboxyl Moieties

Liu

Shih

2001

High Performance Polymers

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We have developed a novel photo-crosslinking method for the negative tone photoresist comprising binder resins with pendant carboxyl groups. A series of copolymers have been synthesized deriving from methacrylic acid, methyl methacrylate, n-butyl methacrylate, and α-methacryloxy-γ -butyrolactone with various feed molar ratios. The existence of lactonic methacrylate units in copolymers was found to increase the sensitivity of the photoresist. Increasing photosensitivity was investigated by using a model compound of α-acetoxy-γbutyrolactone (ACBL). Heat treatment of ACBL compounds in the presence of acid was found to cause the formation of dimers. The following were also investigated: thermogravimetric properties of binder resins, the exposure characteristic curves, and the lithographic evaluation of the negative tone photoresist of copolymers. The existence of alicyclic γ -butyrolactone groups was found to increase the etching resistance of the resists.

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“…A polymer with the desired pendant functional group can be synthesized in two ways: 1) by the incorporation of the functional group as a pendant unit of the monomer itself and polymerizing the same by any one of the chain-growth mechanisms; 2) by chemical modification of the nonfunctionalized polymer. It is well known that the introduction of carboxyl groups in a polymer chain improves solubility and resolution of the photoresist, 19 and that would afford the aqueous-based development of the uncrossed linked/nonexposed polymeric regions through a neutralization reaction. The introduction of a pendant aliphatic group on the polymer backbone would provide the necessary photoactivated imaging functionality via an acidcatalyzed crosslinking reaction.…”

mentioning

confidence: 99%

Synthesis of succinylated poly(4‐hydroxystyrene) and its application for negative‐tone photoresist

Cho

Kim

Patil

et al. 2006

J of Applied Polymer Sci

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Atom transfer radical polymerization (ATRP) was used to prepare poly(acetoxystyrene) (PAS) with a controlled molecular weight and narrow polydispersity. Using 1-phenylethylbromide (PEBr)/CuBr/Cu(0)/2,2 0 -bipyridine as an initiating system, the heterogeneous ATRP of 4-acetoxystyrene was carried out to form PAS as a precursor polymer. The reaction follows the first-order kinetics with respect to the conversion of monomer. A linear molecular weight (polydispersities Mw/Mn ¼ 1.07-1.27) indicates the ''living''/controlled nature of polymerization. The obtained PAS was chemically modified to obtain succinylated poly(hydroxystyrene) (Succ-PHS). The formulation of Succ-PHS, crosslinker (benzoguanamine-formaldehyde), and triphenylsulfonium triflate (TPST) as a photo acid generator (PAG) was carried out by UV irradiation using an i-line tool. The performance of the resultant polymer as the negative resist pattern photoresist for photolithography was studied with instrumental techniques.

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Partially carboxymethylated novolaks for photoresist systems: New photoresists for development under mildly alkaline conditions

Cited by 4 publications

References 0 publications

Synthesis of poly(N‐isopropylacrylamide) with a low molecular weight and a low polydispersity index by single‐electron transfer living radical polymerization

Synthesis of poly(N‐isopropylacrylamide) with a low molecular weight and a low polydispersity index by single‐electron transfer living radical polymerization

Novel Crosslinking Method for Negative Tone Photoresist having Pendant Carboxyl Moieties

Synthesis of succinylated poly(4‐hydroxystyrene) and its application for negative‐tone photoresist

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