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Aromatic resins for primer

A bottom layer and substrate technology, materials used in semiconductor manufacturing, the field of manufacturing electronic devices, can solve problems such as undesired degassing or sublimation

Inactive Publication Date: 2020-01-21
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such relatively low molecular weight crosslinking additives are prone to unwanted outgassing or sublimation during the curing process

Method used

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  • Aromatic resins for primer
  • Aromatic resins for primer
  • Aromatic resins for primer

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0058] Example 1: Synthesis of Polymer-B1. Polymer-B1 was prepared by the reaction sequence shown in Scheme 3.

[0059] Process 3

[0060]

[0061] A 1-L 3-neck round bottom flask equipped with a Dean-Stark trap, condenser, and nitrogen inlet was placed in a silicone oil bath. 4,4'-Dichlorobenzophenol (16.6g, 66.10mmol, Aldrich), 9,9-bis(4-hydroxyphenyl)fluorene (25g, 71.34mmol, Aldrich), Potassium carbonate (21.9 g, 158.47 mmol), anhydrous N,N-dimethylacetamide (150 mL) and toluene (25 mL) were added to the flask and heated to 175 °C (oil bath temperature) while volatile toluene components Collect and remove. After heating at 175° C. with continuous stirring for 16 hr., the reaction mixture was filtered to remove insoluble salts, and the resulting solution was added to methanol (2.5 L) to precipitate Polymer-A1, which was isolated by filtration and washed with water (2 L ) and then washed the wet cake with methanol (2 L). The yield of vacuum drying Polymer-A1 was 3...

example 2

[0063] Example 2: Synthesis of Polymer-B2. Polymer-B2 was prepared by the reaction sequence shown in Scheme 4.

[0064] Process 4

[0065]

[0066] Polymer-A2 was obtained according to the general procedure of Example 1 with 4,4'-dichlorobenzophenol (5.16 g, 20.55 mmol, Aldrich) and 6,6'-(9H-fluorene-9, Starting from 9-diyl)-bis-naphthalen-2-ol (10.0 g, 22.20 mmol) yielded 12.2 g of Polymer-A2. Subsequent reduction of 5.0 g of Polymer-A2 with sodium borohydride yielded 4.8 g of Polymer-B2. GPC analysis of polymer-B2 shows that, according to standard polystyrene, the molecular weight M of the polymer w is 11950 and the polydispersity M w / M n It is 2.45.

example 3

[0067] Example 3: Synthesis of Polymer-B3. Polymer-B3 was prepared by the reaction sequence shown in Scheme 5.

[0068] Process 5

[0069]

[0070] General procedure according to Example 1 starting with 4,4'-dichlorobenzophenol (14.2 g, 65.0 mmol, Aldrich) and 1,1'-di-2-naphthol (18.8 g, 65.60 mmol) Polymer-A3 (18.5 g) was obtained at a reaction temperature of 165° C. and a reaction time of 5 hr. GPC analysis shows, according to standard polystyrene, the molecular weight M of Polymer-A3 w is 2540 and the polydispersity M w / M n It is 1.60. Subsequent reduction of 15.0 g of Polymer-A3 with sodium borohydride yielded 12.5 g of Polymer-B3. GPC analysis of polymer-B3 shows that, according to standard polystyrene, the molecular weight M of the polymer w is 2910 and the polydispersity M w / M n It is 1.6.

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Abstract

The present invention relates to aromatic resin polymers and compositions containing the same, which are useful as primers in semiconductor manufacturing processes.

Description

technical field [0001] The present invention relates generally to the field of manufacturing electronic devices, and more particularly to the field of materials used in semiconductor manufacturing. Background technique [0002] It is well known in the photolithography process that if the resist pattern is too tall (high aspect ratio), the resist pattern may collapse due to surface tension from the developer used. Multi-layer resist processes (such as three-layer and four-layer processes) have been designed that can solve this pattern collapse problem when high aspect ratios are required. Such multilayer processes use a resist top layer, one or more intermediate layers, and a bottom layer (or underlayer). In such multilayer resist processes, the top photoresist layer is imaged and developed in a typical manner to provide a resist pattern. The pattern is then transferred to one or more intermediate layers, typically by etching. Each intermediate layer is chosen such that a ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03F7/004G03F7/00
CPCC09D171/00C08G65/4012G03F7/091G03F7/094G03F7/40C08G65/48C08G2650/40H01L21/02118
Inventor E·阿卡德M·李S·山田S·W·赵
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC