Photosensitive resin composition, method for producing hardened relief pattern, semiconductor device and display device
A technology of photosensitive resin and resin mixture, which is applied in the field of photosensitive resin composition, and can solve problems such as poor heat resistance and increased thermosetting
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[0409] Hereinafter, the present invention will be specifically described with reference to synthesis examples, examples, and comparative examples, but the present invention is not limited thereto.
[0410] In addition, the measurement conditions in an Example are as follows.
[0411]
[0412] By GPC, it calculated based on standard polystyrene (Showa Denko Co., Ltd. organic solvent system standard sample STANDARDSM-105). The GPC apparatus and measurement conditions used are as follows.
[0413] Pump: JASCO PU-980
[0414] Detector: JASCO RI-930
[0415] Column oven: JASCO CO-965 40°C
[0416] Column: Shodex KD-806M 2 in series
[0417] Mobile phase: 0.1 mol / l LiBr / N-methylpyrrolidone
[0418] Flow rate: 1.0ml / min
[0419]
[0420] The resin was dissolved in γ-butyrolactone at a solid content concentration of 37% by mass, and this was spin-coated on a silicon wafer, and the silicon wafer and the spin-coated film were prebaked on a heating plate at 120° C. In 180 seco...
Synthetic example 1
[0491]
[0492] 76.4 g (0.36 mol) of propyl gallate, 4,4'-bis(methoxy 67.9 g (0.28 mol) of methyl) biphenyl, 2.2 g (0.014 mol) of diethyl sulfate, 100 g of diglyme (hereinafter also referred to as "DMDG"), and dissolve the solid matter.
[0493] The mixed solution was heated to 140° C. in an oil bath, and it was confirmed that methanol was generated from the reaction liquid. The reaction solution was stirred directly at 140° C. for 5 hours.
[0494] Next, the reaction container was cooled in the air, and 150 g of tetrahydrofuran was added thereto and stirred. The above reaction diluent was added dropwise to 5L of water under high-speed stirring to disperse and precipitate the resin, which was recovered, washed with water, dehydrated, and vacuum-dried to obtain the resin (P1-1) with a yield of 76%. The weight average molecular weight by GPC of the resin (P1-1) synthesize|combined in this way was 10900 in terms of polystyrene. Dissolve P1-1 in a deuterated dimethyl sulfoxid...
Synthetic example 2
[0496]
[0497] Using 70.6 g (0.42 mol) of methyl 3,5-dihydroxybenzoate instead of propyl gallate in Synthesis Example 1, it synthesized similarly to Synthesis Example 1, and obtained resin (P1-2) in 78% yield. The weight average molecular weight by GPC of the synthesize|combined resin (P1-2) was 14600 in polystyrene conversion. In the same manner as the synthesis example, the obtained P1-2 was measured 1 H NMR spectrum as figure 2 shown.
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