Resist underlayer film-forming composition
A resist underlayer and composition technology, which is applied in the field of resist underlayer film forming compositions for photolithography, can solve problems such as inability to form resist patterns, and achieve the effect of suppressing bending
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[0045] The weight-average molecular weights and polydispersities shown in Synthesis Examples 1 to 3, Comparative Synthesis Example 1, and Comparative Synthesis Example 2 below are based on measurements obtained by gel permeation chromatography (hereinafter, abbreviated as GPC in this specification). result. For the measurement, a GPC system manufactured by Tosoh Corporation was used, and the measurement conditions are as follows.
[0046] GPC column: TSKgel SuperMultipore [registered trademark] Hz-N (Tosoh Corporation)
[0047] Column temperature: 40°C
[0048] Solvent: Tetrahydrofuran (THF)
[0049] Flow: 0.35ml / min
[0050] Standard sample: Polystyrene (Tosoh Corporation)
Synthetic example 1
[0052] 3,3',5,5'-tetramethoxymethyl-4,4'-dihydroxybiphenyl (hereinafter, abbreviated as TMOM-BP in this specification.) (23.83g, 0.066mol, produced by Honshu Chemical Industry Co., Ltd.), pyrene (27.00g, 0.134mol, produced by Tokyo Chemical Industry Co., Ltd.), p-toluenesulfonic acid monohydrate (0.53g, 0.003mol, produced by Tokyo Chemical Industry Co., Ltd. ), further loaded into 1,4-two Alkane (119.84 g, manufactured by Kanto Chemical Co., Ltd.) was stirred, and the temperature was raised until reflux was confirmed to dissolve and start polymerization. After standing to cool to 60 degreeC after 6 hours, it reprecipitated in methanol (1000g, the Kanto Chemical Co., Ltd. product). The obtained precipitate was filtered and dried at 60° C. for 12 hours with a vacuum drier to obtain a target polymer having a structural unit represented by the following formula (3) (hereinafter, abbreviated as TMOM-Py in this specification.) 28.6g. The obtained TMOM-Py had a weight average mol...
Synthetic example 2
[0055] TMOM-BP (2.21 g, 0.006 mol, manufactured by Honshu Chemical Industry Co., Ltd.), carbazole (5.00 g, 0.030 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 1-pyrene formaldehyde (5.76 g, 0.025mol, manufactured by Sigma Aldrich), p-toluenesulfonic acid monohydrate (0.89g, 0.006mol, manufactured by Tokyo Chemical Industry Co., Ltd.), and further charged with 1,4-di Alkane (25.75 g, manufactured by Kanto Chemical Co., Ltd.) was stirred, and the temperature was raised until reflux was confirmed to dissolve it, and polymerization was started. After standing to cool to 60 degreeC after 7 hours, it reprecipitated in methanol (1000g, the Kanto Chemical Co., Ltd. product). The precipitate obtained was filtered, and dried at 60° C. for 12 hours with a decompression dryer to obtain the target polymer (hereinafter referred to as TMOM-Cz for short in this specification) with two structural units represented by the following formula (4). -PCA.) 6.3 g. The obtained TMOM-Cz-PC...
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