Compound, ion-conducting polymer produced using the same, and separation membrane produced using the same

Abstract

To provide a compound for producing an ion-conducting polymer having improved electrochemical properties, and an ion-conducting polymer and a separation membrane produced from the compound. [Solution] This disclosure relates to a compound represented by the following chemical formula 1, comprising an organic group, an ether group, and a multi-aromatic ring in which at least one hydrogen atom is substituted with a halogen atom. [Formula 1] JPEG2026096914000064.jpg26170 In chemical formula 1, m and n are each independent integers from 1 to 6, R 1 Each is an organic group with 1 to 10 carbon atoms, R 2 Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or arylene group; X is a halogen atom; and Ars is a polyaromatic ring having 10 to 50 carbon atoms.

Claims

[Claim 1] A compound represented by the following chemical formula 1. 【Chemistry 1】 (In chemical formula 1, m and n are each independent integers from 1 to 6, R １ Each is an organic group with 1 to 10 carbon atoms, R ２ (Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or arylene group; X is a halogen atom; and Ars is a polyaromatic ring having 10 to 50 carbon atoms.) [Claim 2] The compound according to claim 1, wherein the compound represented by chemical formula 1 comprises at least one of the compounds represented by the following chemical formulas 2 to 4. 【Chemistry 2】 (In chemical formula 2, R ４ and R ５ Each is an organic group with 1 to 10 carbon atoms, R ６ and R ７ Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or arylene group, X ａ and X ｂ (It is a halogen atom.) 【Transformation 3】 (In Chemical Formula 3, R ９ and R １０ are each independently an organic group having 1 to 10 carbon atoms, R １１ and R １２ are each independently an organic group having 1 to 20 carbon atoms containing at least one of an alkylene group or an arylene group, X ｃ and X ｄ are halogen atoms.) 【Chemistry 4】 (In chemical formula 4, R １４ and R １５ Each is an organic group with 1 to 10 carbon atoms, R １６ and R １７ Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or arylene group, X ｅ and X ｆ (It is a halogen atom.) [Claim 3] The compound according to claim 2, wherein the compounds represented by chemical formulas 2 to 4 include, respectively, compounds represented by the following chemical formulas 2-1 to 4-1. 【Transformation 5】 【Transformation 6】 【Transformation 7】 [Claim 4] The compound according to claim 1, wherein the compound is a monomer for polymerization. [Claim 5] A precursor polymer having repeating units represented by the following chemical formula 1a. 【Transformation 8】 (In chemical formula 1a, m and n are each independent integers from 1 to 6, R １ Each is an organic group with 1 to 10 carbon atoms, R ２ Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or an arylene group, R ３ (wherein H is an organic group having 1 to 15 carbon atoms, X is a halogen atom, and Ars is a polyaromatic ring having 10 to 50 carbon atoms.) [Claim 6] An ionic conductive polymer having repeating units represented by the following chemical formula 5. 【Chemistry 9】 (In chemical formula 5, A ＋ is a quaternary ammonium, B － R is an anion, m and n are integers from 1 to 6, and R is an integer. １ Each is an organic group with 1 to 10 carbon atoms, R ２ Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or an arylene group, R ３ (wherein H is an organic group with 1 to 15 carbon atoms, and Ars is a polyaromatic ring with 10 to 50 carbon atoms.) [Claim 7] The ion-conducting polymer according to claim 6, wherein the repeating unit represented by chemical formula 5 has at least one of the repeating units represented by chemical formulas 6 to 8 below. 【Chemistry 10】 (In chemical formula 6, A １ ＋ and A ２ ＋ is a quaternary ammonium, B １ － and B ２ － R is an anion. ４ and R ５ Each is an organic group with 1 to 10 carbon atoms, R ６ and R ７ Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or an arylene group, R ８ (This refers to H or an organic group having 1 to 15 carbon atoms.) 【Chemistry 11】 (In chemical formula 7, A ３ ＋ and A ４ ＋ is a quaternary ammonium, B ３ － and B ４ － R is an anion. ９ and R １０ Each is an organic group with 1 to 10 carbon atoms, R １１ and R １２ Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or an arylene group, R １３ (This refers to H or an organic group having 1 to 15 carbon atoms.) 【Chemistry 12】 (In chemical formula 8, A ５ ＋ and A ６ ＋ is a quaternary ammonium, B ５ － and B ６ － R is an anion. １４ and R １５ Each is an organic group with 1 to 10 carbon atoms, R １６ and R １７ Each of these is an organic group having 1 to 20 carbon atoms, each independently containing at least one alkylene group or an arylene group, R １８ (This refers to H or an organic group having 1 to 15 carbon atoms.) [Claim 8] The ion-conducting polymer according to claim 7, wherein the repeating units represented by chemical formulas 6 to 8 have repeating units represented by the following chemical formulas 6-1 to 8-1. 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 [Claim 9] The OH of the ionic conductive polymer at 25°C － The ion-conducting polymer according to claim 6, wherein the ion conductivity is 40 mS / cm to 80 mS / cm. [Claim 10] A separation membrane comprising the ion-conducting polymer described in claim 6. [Claim 11] Positive electrode and, A negative electrode opposite the positive electrode, An apparatus comprising the separation membrane described in claim 10. [Claim 12] The aforementioned apparatus includes a water electrolysis device and a CO2 electrolysis device. ２ The apparatus according to claim 11, comprising an electrolytic device, a fuel cell, an electrolytic battery, and a vanadium flow battery.

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