Search

KR-20260063488-A - Polyimide compound containing side chain and method for producing same

KR20260063488AKR 20260063488 AKR20260063488 AKR 20260063488AKR-20260063488-A

Abstract

According to the present disclosure, a polyimide-based compound is provided, said polyimide-based compound comprises: a main chain having a monomer comprising an imide functional group; and one or more side chains of Formula 1 bonded to said main chain. Here, R is an alkyl group having 1 to 30 carbon atoms, and X represents O, S, or NH. The above-mentioned polyimide-based compound has the advantage of excellent dielectric properties and excellent solubility in organic solvents.

Inventors

  • 양현승
  • 박성대
  • 조수빈

Assignees

  • 한국전자기술연구원

Dates

Publication Date
20260507
Application Date
20241030

Claims (11)

  1. As a polyimide compound: A main chain having a monomer containing an imide functional group; and A polyimide compound comprising one or more side chains of Formula 1 bonded to the main chain. Here, R is an alkyl group having 1 to 30 carbon atoms, and X represents O, S, or NH.
  2. In claim 1, The above main chain is a polyimide compound comprising a monomer of Chemical Formula 2.
  3. In claim 1, The above polyimide-based compound is a polyimide-based compound comprising 1 to 50 side chains.
  4. In claim 1, The above polyimide-based compound is a polyimide-based compound having a weight average molecular weight (M w ) of 10,000 to 20,000.
  5. As a method for manufacturing a polyimide-based compound: Step of providing polyamic acid; A step of converting polyamic acid into polyimide; and A method for manufacturing a polyimide-based compound, comprising the step of reacting a polyimide with an isocyanate compound to bond the isocyanate compound to the polyimide.
  6. In claim 5, A method for preparing a polyimide-based compound, wherein the step of bonding an isocyanate compound to a polyimide is performed at a temperature of 50 to 200 ℃ without a catalyst.
  7. In claim 5, A method for preparing a polyimide-based compound, wherein the isocyanate compound comprises an alkyl group having 1 to 30 carbon atoms.
  8. In claim 5, A method for preparing a polyimide-based compound, wherein the step of bonding an isocyanate compound to a polyimide is performed for 20 to 60 minutes.
  9. In claim 5, A method for preparing a polyimide-based compound, wherein the molar ratio of the isocyanate compound reacted to the polyimide in the step of bonding the isocyanate compound to the polyimide is 1 to 50.
  10. As a polyimide film: The polyimide compound of claim 1; Reactive diluent; and A polyimide film containing a photoinitiator.
  11. In claim 10, The above polyimide film is a photocured and heat-cured polyimide film.

Description

Polyimide compound containing side chain and method for producing same The present disclosure relates to a polyimide-based compound containing a side chain and a method for manufacturing the same. Recently, active research and development have been underway regarding substrate materials applicable to ultra-high-speed communication electronic components in the high-frequency range. To achieve high-speed signal processing while minimizing communication signal delay, substrate materials with low dielectric constants, excellent low dielectric loss characteristics, and superior heat resistance are required. Substrate materials are primarily fabricated using compositions containing thermosetting polymers; among various polymer materials, polyimide is attracting attention as a substrate material for ultra-high-speed communication and for the construction of redistribution layers (RDLs) due to its excellent dielectric properties and heat resistance. It is known that the dielectric constant of a polymer matrix decreases as the free volume between polymer chains increases. To lower the dielectric constant of polyimide, a technique has been proposed to increase the free volume by introducing a bulky chemical structure into the internal chemical structure of polyimide. FIG. 1 is a schematic diagram of the steps for manufacturing polyamic acid according to one embodiment. FIG. 2 is a schematic diagram of the conversion step of polyamic acid to polyimide (PI) according to one embodiment. FIG. 3 is a schematic diagram of the bonding step of an isocyanate compound to a polyimide according to one embodiment. Figures 4 to 6 are nuclear magnetic resonance (H-NMR) peak data for a polyimide-based compound according to one embodiment. Hereinafter, the present disclosure will be described in detail with reference to the attached drawings. However, this is merely illustrative and the present disclosure is not limited to the specific embodiments described illustratively. Polyimide compounds A polyimide compound according to the first aspect of the present disclosure comprises: a main chain having a monomer comprising an imide functional group; and one or more side chains of Formula 1 bonded to the main chain. Here, R is an alkyl group having 1 to 30 carbon atoms, and X represents O, S, or NH. A main chain having a monomer containing an imide functional group refers to a long chain formed by the polymerization of a monomer containing an imide functional group. The main chain is a polyimide that imparts dielectric properties and heat resistance to polyimide-based compounds. The main chain may be a saturated hydrocarbon polyimide or an unsaturated hydrocarbon polyimide. A saturated hydrocarbon polyimide refers to a polyamide in which unsaturated hydrocarbons are not present in the monomer, and an unsaturated hydrocarbon polyimide refers to a polyimide in which unsaturated hydrocarbons are present in the monomer. In particular, when the main chain is an aromatic polyimide among unsaturated hydrocarbon polyimides, a carboxylic acid anhydride group present in the polyimide functional group may act as an electron acceptor, and an amine group bonded to an aromatic ring may act as an electron donor to form a charge transfer complex (CTC). This can contribute to the optical stability of the main chain. In one embodiment, the main chain may include a monomer of Formula 2. The main chain formed by the polymerization of the above monomer corresponds to an aromatic polyimide. The above monomer facilitates the bonding of a side chain at a corresponding position by having the oxygen atom of the phenyl group bonded to the nitrogen of the imide functional group act as an electron donor, thereby improving the heat resistance of the polyimide-based compound containing it. The side chain of Chemical Formula 1 bonded to the main chain is formed by bonding a carbon portion of an isocyanate group with a chemical structure like Chemical Formula 3 to a part of the main chain. Specifically, the side chain is formed when a carbon atom forming double bonds with the nitrogen and oxygen of Chemical Formula 3 receives electrons from an electron pair donor present in the main chain to form a bond. The side chain provides a steric effect to the polyimide compound. The steric effect refers to an increase in free volume due to the gap between each polyimide chain caused by the protrusion of the side chain when multiple polyimide chains are stacked. As the free volume increases, the dielectric constant of the polyimide resin containing it is lowered, and consequently, the insulation properties of the polyimide resin can be improved. Additionally, the side chain exhibits polarity, which can provide the advantage of strong adhesion to the substrate when the polyimide compound is deposited on a metal substrate. In one embodiment, the polyimide-based compound may include 1 to 50 side chains. If the polyimide-based compound includes fewer than 1 side chain, the aforementio