Diamine compounds, polyimide acids, polyimides, and methods for preparing same and uses thereof

Abstract

The present application provides a diamine compound, a polyimide acid, a polyimide, and a method for preparing and using the same. The diamine compound has a chemical structure represented by formula (I): [Formula 1] JPEG2025526974000068.jpg40131 (wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene).

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This disclosure claims priority to Chinese Patent Application No. 202211212701.2, filed on September 30, 2022, and entitled "Diamine Compounds, Polyimide Acids, Polyimides, and Preparation Methods Thereof, and Uses Thereof," which is incorporated herein by reference in its entirety.

[0002] Field TECHNICAL FIELD The present disclosure relates to the technical field of materials, in particular to diamine compounds, polyimide acids, polyimides, and methods for their preparation and uses. [Background technology]

[0003] With the continuous development of electronic devices, polyimide films, which offer various advantages, have become an important material attracting great interest from manufacturers. However, the current poor bonding strength between polyimides and metal components limits the use and development of polyimides. Therefore, there is a need to improve the performance of polyimides. Summary of the Invention

[0004] In view of this, the present disclosure provides a diamine compound, a polyimide acid, a polyimide, and methods for preparing and using the same. The diamine compound, the polyimide acid, and the polyimide have a 1,10-phenanthrolinyl group, which can coordinate to a metal atom to form a strong coordinate bond, thereby improving the bonding strength between the polyimide and a metal component and facilitating the use of the polyimide.

[0005] In a first aspect, the present disclosure provides a diamine compound having a chemical structure represented by formula (I): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene.

[0006] The diamine compound provided in the present disclosure has a 1,10-phenanthrolinyl group, and the diamine compound can be used as a raw material for preparing polyimide, so that the polyimide also has a 1,10-phenanthrolinyl group to ensure the bonding strength between the polyimide and the metal member.

[0007] In one embodiment of the present disclosure, the substituted or unsubstituted alkylene is a substituted or unsubstituted C1-C8 alkylene, The substituted or unsubstituted alkenylene is a substituted or unsubstituted C2-C8 alkenylene. The substituted or unsubstituted alkynylene is a substituted or unsubstituted C2-C8 alkynylene. The substituted or unsubstituted arylene is a substituted or unsubstituted C6-C 30 is an arylene, The substituted or unsubstituted arylene is a substituted or unsubstituted C7-C 40 arylene alkyl, The substituted or unsubstituted heteroarylene is a substituted or unsubstituted C-C 30 is heteroarylene, The substituted or unsubstituted arylene is a substituted or unsubstituted C3-C 40 heteroarylenealkyl, Substituted or unsubstituted alicylidene is a substituted or unsubstituted C3-C 30 It is alicylidene.

[0008] In one embodiment of the present disclosure, R1 and R2 are independently a single bond, a substituted or unsubstituted C6-C 30Arylene or substituted or unsubstituted C7-C 40 arylene alkyl.

[0009] In one embodiment of the present disclosure, the diamine compound is represented by the formulas (I-1) to (I-4): [ka] The compound includes one of the compounds represented by the formula:

[0010] In a second aspect, the present disclosure provides a method for preparing a diamine compound, the method comprising the steps of:

[0011] A first reactant is provided. The first reactant has a chemical structure represented by formula (II): [ka] wherein R3 and R4 are independently selected from a chlorine atom, a bromine atom, an iodine atom, or an astatine atom.

[0012] A second reactant is provided, the second reactant having a chemical structure represented by formula (III): H2N-R5(III) wherein R5 is selected from hydrogen, alkyl substituted with a boric acid or boric acid ester, alkenyl substituted with a boric acid or boric acid ester, alkynyl substituted with a boric acid or boric acid ester, aryl substituted with a boric acid or boric acid ester, aralkyl substituted with a boric acid or boric acid ester, heteroaryl substituted with a boric acid or boric acid ester, heteroarylalkyl substituted with a boric acid or boric acid ester, or alicylyl substituted with a boric acid or boric acid ester.

[0013] The first reactant and the second reactant are mixed under basic conditions to form a reaction solution, which is then reacted to obtain a diamine compound having a chemical structure represented by formula (I): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene.

[0014] The method for preparing the diamine compounds of the present disclosure is simple and convenient to operate, which allows large-scale production of the diamine compounds to be achieved, facilitating the production and use of polyimides.

[0015] In one embodiment of the present disclosure, the reaction solution further comprises a catalyst and a catalyst ligand.

[0016] The catalyst includes a copper-based catalyst and a palladium-based catalyst, the copper-based catalyst including cuprous oxide, and the palladium-based catalyst including at least one of bis(3,5,3',5'-dimethoxydibenzylideneacetone)palladium, bis(tri-tert-butyl)palladium, tris(dibenzylideneacetone)palladium, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium, and bis(tri-tert-butylphosphine)palladium.

[0017] The catalyst ligand includes at least one of N,N'-dimethylethylenediamine, triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, triphenylphosphine oxide, and tris(o-methylphenyl)phosphine.

[0018] The molar ratio of the first reactant, the second reactant, the catalyst, and the catalyst ligand is 1:(2-50):(0.005-0.2):(0.005-0.5).

[0019] The reaction solution further includes an alkaline substance, and the alkaline substance includes at least one of potassium carbonate, sodium carbonate, cesium fluoride, sodium hydroxide, potassium hydroxide, and barium hydroxide.

[0020] The molar ratio of the first reactant to the second reactant to the alkaline substance is 1:(2-50):(0.05-10).

[0021] The reaction temperature is 25°C to 180°C, and the reaction time is 2 hours to 72 hours.

[0022] In one embodiment of the present disclosure, the reaction solution further comprises a solvent, and the solvent comprises water, ethylene glycol, or 1,4-dioxane, and the volume ratio of 1,4-dioxane to water is 2-10.

[0023] In one embodiment of the present disclosure, the reaction is carried out under an inert atmosphere.

[0024] In a third aspect, the present disclosure provides a polyimide acid, the polyimide acid comprising a repeat unit represented by formula (IV): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; and R7 is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.

[0025] The polyimide acid provided in the present disclosure has a 1,10-phenanthrolinyl group, which can form a chemical bond with a metal member to improve adhesion to the metal member, thereby facilitating the preparation of the polyimide and improving the bonding strength between the polyimide and the metal member.

[0026] In one embodiment of the present disclosure, the polyimide acid has a chemical structure represented by formula (V): [ka] (wherein R8 is selected from substituted or unsubstituted alkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene; n is 5 to 2000; and m is 0 to 1000).

[0027] In a fourth aspect, the present disclosure provides a method for preparing a polyimide acid, the method comprising the steps of: mixing a first diamine compound with a dianhydride to form a mixed solution, and reacting the resulting mixture to obtain a polyimide acid. The first diamine compound is a diamine compound according to the first aspect or a diamine compound prepared by the preparation method according to the second aspect. The polyimide acid comprises a repeating unit represented by formula (IV): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; and R7 is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.

[0028] The method for preparing polyimide acid provided in the present disclosure is simple and easy to operate, which can achieve large-scale production of polyimide acid and facilitate the preparation of polyimide acid.

[0029] In one embodiment of the present disclosure, the molar ratio of the first diamine compound to the dianhydride is 0.9 to 1.1.

[0030] The dianhydride includes at least one of pyromellitic dianhydride, 2,3,3',4'-diphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 3,3',4,4'-diphenyl sulfone tetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl ether dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)benzophenone dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylmethane dianhydride, and 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride.

[0031] The mixed solution further includes a second diamine compound, and the second diamine compound includes at least one of 4,4'-diaminodiphenyl ether, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenyl sulfone, 1,3-diamino-2-methylpropane, N,N-bis(4-aminophenyl)-1,4-phenylenediamine, 9,9-bis(4-aminophenyl)fluorene, 1,2-diaminocyclohexane, and ethylenediamine.

[0032] The mixed solution further includes a solvent, and the solvent includes at least one of dimethyl sulfoxide, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, and m-cresol.

[0033] The reaction temperature is 0°C to 100°C, and the reaction time is 2 to 12 hours.

[0034] In a fifth aspect, the present disclosure provides a polyimide, the polyimide having a repeating unit represented by formula (VI): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; and R7 is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.

[0035] The polyimides provided in the present disclosure have 1,10-phenanthrolinyl groups, which can form chemical bonds with metal members to improve the adhesion of the polyimides to metal members and facilitate the use of the polyimides.

[0036] In one embodiment of the present disclosure, the polyimide has a chemical structure represented by formula (VII): [ka] (wherein R8 is selected from substituted or unsubstituted alkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene; n is 5 to 2000; and m is 0 to 1000).

[0037] In a sixth aspect, the present disclosure provides a method for preparing a polyimide, the method comprising the steps of: imidizing a polyimide acid according to the third aspect or a polyimide acid prepared by the preparation method according to the fourth aspect to obtain a polyimide, the polyimide having a repeating unit represented by formula (VI): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; and R7 is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.

[0038] The method for preparing polyimide provided in the present disclosure is simple and easy to operate, which allows large-scale production of polyimide to be achieved, and allows polyimide with high bonding strength with metal members to be prepared, thereby facilitating the use of polyimide.

[0039] In a seventh aspect, the present disclosure provides a battery assembly including a heat dissipation component, a polyimide film disposed on a surface of the heat dissipation component, and a battery core disposed on the surface of the polyimide film, wherein the polyimide film is made of a polyimide according to the fifth aspect or a polyimide prepared by the preparation method according to the sixth aspect.

[0040] In the battery assembly provided in the present disclosure, the heat dissipation component and the battery core are connected by a polyimide film, which improves the bonding strength to the heat dissipation component and has insulating properties, further ensuring the safety of the battery assembly.

[0041] In an eighth aspect, the present disclosure provides an electronic device including a battery assembly according to the seventh aspect.

[0042] The battery assembly for an electronic device provided in the present disclosure has high safety, thus facilitating the use of the electronic device.

[0043] In order to more clearly describe the technical solutions according to the embodiments of the present disclosure or in the prior art, the drawings required for use in the embodiments or the prior art are briefly described below. The specific embodiments described in this specification are merely used to explain the present disclosure, and the present disclosure is not limited thereto. [Brief explanation of the drawings]

[0044] [Figure 1] FIG. 2 is a schematic diagram illustrating the bonding of a polyimide to a metal atom provided in one embodiment of the present disclosure. [Figure 2] 1 is a schematic cross-sectional view of a battery assembly provided in one embodiment of the present disclosure. [Figure 3] 1A and 1B are schematic diagrams illustrating bonding of a polyimide film provided in one embodiment of the present disclosure to a heat-dissipating component. DETAILED DESCRIPTION OF THE INVENTION

[0045] The technical solutions according to the embodiments of the present disclosure are clearly and fully described below with reference to the accompanying drawings in the embodiments of the present disclosure. Obviously, the described embodiments are only a part, not all, of the embodiments of the present invention. All other embodiments obtained by those skilled in the art based on the embodiments of the present disclosure without creative efforts shall fall within the protection scope of the present invention.

[0046] The present disclosure provides a diamine compound having a chemical structure represented by formula (I): [ka] (wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene.) The diamine compounds provided in the present disclosure include those having a 1,10-phenanthrolinyl group (i.e., [ka] The diamine compound can be used as a raw material for preparing polyimide, and the prepared polyimide also has 1,10-phenanthrolinyl groups to ensure the bonding strength between the polyimide and the metal member.

[0047] In the present disclosure, R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene. R1 is selected from a single bond, alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene, substituted alkynylene, arylene, substituted arylene, arylene alkyl, substituted arylene alkyl, heteroarylene, substituted heteroarylene, heteroarylene alkyl, substituted heteroarylene alkyl, alicylidene, or substituted alicylidene. R2 is selected from a single bond, alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene, substituted alkynylene, arylene, substituted arylene, arylene alkyl, substituted arylene alkyl, heteroarylene, substituted heteroarylene, heteroarylene alkyl, substituted heteroarylene alkyl, alicylidene, or substituted alicylidene.

[0048] In the present disclosure, alkyl refers to a group obtained by removing one hydrogen atom from an alkane molecule and may include straight-chain alkyl and branched alkyl. In particular, alkyl may include, but is not limited to, at least one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 4-methylbutyl, 2,2-dimethylpropyl, n-hexyl, heptyl, 2-methylhexyl, 3-methylhexyl, 4-methylpentyl, 5-methylpentyl, 2-ethylbutyl, 3-ethylbutyl, heptyl, octyl, nonyl, and decyl. In one embodiment of the present disclosure, the substituted or unsubstituted alkyl may be a substituted or unsubstituted C1-C8 alkyl. That is, the alkyl has 1 to 8 carbon atoms. In particular, the alkyl may have, but is not limited to, 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms.

[0049] In the present disclosure, alkylene is a divalent saturated group formed by removing one hydrogen atom from an alkyl. In particular, alkylene may include, but is not limited to, at least one of -CH-, -CHCH-, -CHCHCH-, -CHCHCHCH-, -CHCHCHCHCH-, and -CHCHCHCHCHCHCHCH-. In one embodiment of the present disclosure, the substituted or unsubstituted alkylene is a substituted or unsubstituted C1-C8 alkylene. That is, the alkylene has 1 to 8 carbon atoms. In particular, the alkylene has, but is not limited to, 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms.

[0050] In the present disclosure, alkenyl refers to a divalent unsaturated hydrocarbon chain containing at least one double bond, and may include linear or branched alkenyl. In particular, alkenyl may include, but is not limited to, at least one of ethenyl, propenyl, isopropenyl, butenyl, butadienyl, pentenyl, pentadienyl, hexenyl, hexadienyl, heptenyl, octenyl, nonenyl, and decenyl. In one embodiment of the present disclosure, the substituted or unsubstituted alkenyl is a substituted or unsubstituted C2-C8 alkenyl. That is, the alkenyl has 2 to 8 carbon atoms. In particular, the alkenyl may have, but is not limited to, 2, 3, 4, 5, 6, 7, or 8 carbon atoms.

[0051] In the present disclosure, alkenylene is a divalent unsaturated group formed by removing one hydrogen atom from alkenyl. In particular, alkenylene may include, but is not limited to, at least one of -CH=CH-, -CH=CHCH2-, -CH2CH=CH-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2CH=CHCH2-, -CH=CH-CH=CH-, -CH=CHCH2CH2CH2-, -CH=CH-CH=CH-, -CH=CHCH2CH2CH2-, -CH=CH-CH=CH2CH2-, and -CH=CH2CH2CH=CH-. In one embodiment of the present disclosure, the substituted or unsubstituted alkenylene is a substituted or unsubstituted C2-C8 alkenylene. That is, the alkenylene has 2 to 8 carbon atoms. In particular, the alkenylene has, but is not limited to, 2, 3, 4, 5, 6, 7, or 8 carbon atoms.

[0052] In the present disclosure, alkynyl refers to a trivalent unsaturated hydrocarbon chain containing at least one triple bond, and may include straight-chain alkynyl or branched alkynyl. In particular, alkynyl may include, but is not limited to, at least one of ethynyl, propynyl, butynyl, pentynyl, and hexynyl. In one embodiment of the present disclosure, the substituted or unsubstituted alkynyl is a substituted or unsubstituted C2-C8 alkynyl. That is, the alkynyl has 2 to 8 carbon atoms. In particular, the alkynyl has, but is not limited to, 2, 3, 4, 5, 6, 7, or 8 carbon atoms.

[0053] In the present disclosure, alkynylene is a divalent unsaturated group formed by removing one hydrogen atom from an alkynyl. In particular, alkynylene may include, but is not limited to, at least one of -C≡C-, -C≡CCH2-, -CH2C≡C-, -C≡CCH2CH2-, -CH2C≡CCH2-, -CH2CH2C≡C-, -C≡CC≡C-, -C≡CCH2CH2CH2-, -CH2C≡CCH2CH2-, -CH2CH2C≡CCH2-, -CH2C≡CC≡C-CH2-, -C≡CCH2CH2CH2CH2-, -CH2C≡CCH2CH2CH2-, -CH2CH2C≡CCH2CH2-, -CH2CH2CH2C≡CCH2-, and -CH2CH2CH2CH2C≡C-. In one embodiment of the present disclosure, the substituted or unsubstituted alkynylene is a substituted or unsubstituted C2-C8 alkynylene. That is, the alkynylene has 2 to 8 carbon atoms. In particular, the alkynylene has, but is not limited to, 2, 3, 4, 5, 6, 7, or 8 carbon atoms.

[0054] In the present disclosure, aryl is an aromatic group. In particular, aryl may include, but is not limited to, at least one of phenyl, naphthalenyl, anthracenyl, tetracenyl, pentacenyl, and tetrahydronaphthalenyl. In one embodiment of the present disclosure, substituted or unsubstituted aryl is a substituted or unsubstituted C6-C6 30It is an aryl. That is, the aryl has 6 to 30 carbon atoms. In particular, the aryl has, but is not limited to, 6, 10, 12, 14, 18, 22, 24, 26, or 30 carbon atoms.

[0055] In the present disclosure, arylene is a divalent aromatic group. In particular, arylene may include at least one of phenylene, naphthalenylene, anthracenylene, tetracenylene, pentacenylene, and tetrahydronaphthalenylene, but is not limited thereto. In one embodiment of the present disclosure, substituted or unsubstituted arylene is substituted or unsubstituted C6-C 30 It is an arylene. That is, the arylene has 6 to 30 carbon atoms. Particularly, the arylene has, but is not limited to, 6, 10, 12, 14, 18, 22, 24, 26, or 30 carbon atoms.

[0056] In the present disclosure, an arylene alkyl is a combination group formed by linking an arylene to an alkylene. In particular, an arylene alkyl is: [ka] and [ka] In one embodiment of the present disclosure, the substituted or unsubstituted arylene alkyl may include, but is not limited to, at least one of substituted or unsubstituted C7 to C8 40 It is an arylene alkyl. That is, the arylene alkyl has 7 to 40 carbon atoms. In particular, the arylene alkyl has, but is not limited to, 7, 8, 9, 10, 15, 18, 20, 25, 26, 30, 32, 37, or 40 carbon atoms.

[0057] In the present disclosure, heteroaryl is an aryl having at least one oxygen, sulfur, or nitrogen atom. In particular, heteroaryl may include, but is not limited to, at least one of pyridyl, furyl, thienyl, indolyl, quinolinyl, imidazolinyl, and thiazolyl. In one embodiment of the present disclosure, substituted or unsubstituted heteroaryl is a substituted or unsubstituted C2-C6 30 Heteroaryl. That is, heteroaryl has 2 to 30 carbon atoms. In particular, heteroaryl has, but is not limited to, 3, 5, 8, 12, 17, 20, 25, 28, or 30 carbon atoms.

[0058] In the present disclosure, heteroarylene is a divalent heteroaryl. In particular, heteroarylene may include, but is not limited to, at least one of pyridylene, furylene, thienylene, indolylene, quinolinylene, imidazolinylene, and thiazolylene. In one embodiment of the present disclosure, substituted or unsubstituted heteroarylene is a substituted or unsubstituted C2-C 30 Heteroarylene. That is, the heteroarylene has 2 to 30 carbon atoms. Particularly, the heteroarylene has, but is not limited to, 3, 5, 8, 12, 17, 20, 25, 28, or 30 carbon atoms.

[0059] In the present disclosure, heteroarylenealkyl is a combination group formed by linking a heteroarylene to an alkylene. In particular, heteroarylenealkyl is [ka] and [ka] In one embodiment of the present disclosure, the substituted or unsubstituted heteroarylene alkyl may include, but is not limited to, at least one of substituted or unsubstituted C3-C 40Heteroarylene alkyl. That is, heteroarylene alkyl has 2 to 40 carbon atoms. Particularly, heteroarylene alkyl has, but is not limited to, 5, 6, 10, 13, 18, 22, 27, 30, 33, or 39 carbon atoms.

[0060] In the present disclosure, alisilyl is a carbocyclic group that does not have a phenyl ring. In particular, alisilyl may include at least one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclopentenyl, but is not limited thereto. In one embodiment of the present disclosure, the substituted or unsubstituted alisilyl is a substituted or unsubstituted C3-C 30 It is an allicinyl. That is, the allicinyl has 3 to 30 carbon atoms. In particular, the allicinyl has, but is not limited to, 3, 5, 9, 10, 13, 15, 18, 23, 26, or 30 carbon atoms.

[0061] In the present disclosure, alicylidene is a divalent alicylyl. In particular, alicylidene may include, but is not limited to, at least one of cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, and cyclopentenylene. In one embodiment of the present disclosure, substituted or unsubstituted alicylidene is a substituted or unsubstituted C3-C 30 It is an alicylylene. That is, the alicylylene has 3 to 30 carbon atoms. In particular, the alicylylene has, but is not limited to, 3, 5, 9, 10, 13, 15, 18, 23, 26, or 30 carbon atoms.

[0062] In the present disclosure, substituted groups (e.g., alkyl, alkylene, alkenyl, alkenylene, alkynyl, alkynylene, aryl, arylene, arylene alkyl, heteroaryl, heteroarylene, heteroarylene alkyl, and arylcylidene) are groups substituted with a substituent. In one embodiment, the substituent includes at least one of halo, nitrogen atom, oxygen atom, sulfur atom, hydroxyl, nitro, amino, mercapto, methoxy, and cyano.

[0063] In the present disclosure, R1 and / or R2 may be a single bond, i.e., the amino group (-NH2) may be directly reacted with the phenanthrolinyl group. In one embodiment, R1 and R2 are both single bonds, and the diamine compound has the formula (I-1): [ka] It has the chemical structural formula:

[0064] The diamine compound represented by formula (I-1) has a simple structure and very stable performance, and facilitates the preparation of polyimides with stable performance.

[0065] In one embodiment of the present disclosure, R1 and R2 are independently a single bond, a substituted or unsubstituted C6-C 30 Arylene or substituted or unsubstituted C7-C 40 arylene alkyl. This further improves the structural stability of the diamine compound. In one embodiment, R1 and R2 are the same group. In another embodiment, R1 and R2 are different groups. In one embodiment of the present disclosure, the diamine compound is represented by the formulas (I-1) to (I-4): [ka] When R1 and R2 are both single bonds, the diamine compound has a chemical structural formula represented by formula (I-1), when R1 and R2 are both arylene, the diamine compound has a chemical structural formula represented by formula (I-2) or formula (I-3), and when R1 and R2 are both arylene alkyl, the diamine compound has a chemical structural formula represented by formula (I-4).

[0066] The present disclosure further provides a method for preparing a diamine compound, which may prepare a diamine compound according to any one of the above embodiments. The method includes the following steps:

[0067] A first reactant is provided. The first reactant has a chemical structure represented by formula (II): [ka] wherein R3 and R4 are independently selected from a chlorine atom, a bromine atom, an iodine atom, or an astatine atom.

[0068] A second reactant is provided, the second reactant having a chemical structure represented by formula (III): H2N-R5(III) wherein R5 is selected from hydrogen, alkyl substituted with a boric acid or boric acid ester, alkenyl substituted with a boric acid or boric acid ester, alkynyl substituted with a boric acid or boric acid ester, aryl substituted with a boric acid or boric acid ester, aralkyl substituted with a boric acid or boric acid ester, heteroaryl substituted with a boric acid or boric acid ester, heteroarylalkyl substituted with a boric acid or boric acid ester, or alisilyl substituted with a boric acid or boric acid ester.

[0069] The first reactant and the second reactant are mixed under basic conditions to form a reaction solution, which is then reacted to obtain a diamine compound having a chemical structure represented by formula (I): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene.

[0070] The method for preparing the diamine compounds of the present disclosure is simple and convenient to operate, which allows large-scale production of the diamine compounds to be achieved, facilitating the production and use of polyimides.

[0071] In the present disclosure, R3 and R4 in the first reactant may be the same group or different groups. In one embodiment, R3 and R4 are the same group to facilitate the reaction. In particular, the first reactant is [ka] and [ka] In the present disclosure, R5 in the second reactant may be selected from hydrogen, alkyl substituted with a boric acid or boric acid ester, alkenyl substituted with a boric acid or boric acid ester, alkynyl substituted with a boric acid or boric acid ester, aryl substituted with a boric acid or boric acid ester, aralkyl substituted with a boric acid or boric acid ester, heteroaryl substituted with a boric acid or boric acid ester, heteroarylalkyl substituted with a boric acid or boric acid ester, or alicyclic substituted with a boric acid or boric acid ester. In particular, R5 is selected from NH3, [ka] , [ka] , and [ka] In the present disclosure, the first reactant and the second reactant are subjected to Suzuki coupling to prepare a diamine compound.

[0072] In one embodiment of the present disclosure, the reaction solution further comprises a catalyst and a catalytic ligand. The addition of the catalyst and catalytic ligand promotes the progress of the reaction. In one embodiment of the present disclosure, the catalyst comprises a copper-based catalyst and a palladium-based catalyst. The copper-based catalyst comprises cuprous oxide, and the palladium (Pb)-based catalyst comprises at least one of bis(3,5,3',5'-dimethoxydibenzylideneacetone)palladium, bis(tri-tert-butyl)palladium, tris(dibenzylideneacetone)palladium, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium, and bis(tri-tert-butylphosphine)palladium. In one embodiment of the present disclosure, the catalyst ligand includes at least one of N,N'-dimethylethylenediamine, triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, triphenylphosphine oxide, and tris(o-methylphenyl)phosphine. The catalyst and catalyst ligand can effectively promote the progress of the Suzuki coupling. In one embodiment of the present disclosure, the molar ratio of the first reactant to the second reactant to the catalyst and catalyst ligand is 1:(2-50):(0.005-0.2):(0.005-0.5). This facilitates the progress of the Suzuki coupling and improves the preparation efficiency of the diamine compound. In one embodiment, the molar ratio of the first reactant to the second reactant to the catalyst to the catalyst ligand is 1:(3-45):(0.01-0.18):(0.01-0.45). In another embodiment, the molar ratio of the first reactant to the second reactant to the catalyst to the catalyst ligand is 1:(8-37):(0.05-0.16):(0.1-0.4). In another embodiment, the molar ratio of the first reactant to the second reactant to the catalyst to the catalyst ligand is 1:(10-25):(0.05-0.1):(0.1-0.3). In another embodiment, the molar ratio of the first reactant to the second reactant to the catalyst to the catalyst ligand is 1:(30-50):(0.1-0.2):(0.3-0.5).

[0073] In one embodiment of the present disclosure, the reaction solution further contains an alkaline substance to facilitate the reaction under basic conditions. In one embodiment of the present disclosure, the alkaline substance includes at least one of potassium carbonate, sodium carbonate, cesium fluoride, sodium hydroxide, potassium hydroxide, and barium hydroxide. In one embodiment of the present disclosure, the molar ratio of the first reactant, the second reactant, and the alkaline substance is 1:(2-50):(0.05-10). This facilitates the Suzuki coupling and improves the efficiency of preparing the diamine compound. In one embodiment, the molar ratio of the first reactant, the second reactant, and the alkaline substance is 1:(3-45):(0.1-9). In another embodiment, the molar ratio of the first reactant, the second reactant, and the alkaline substance is 1:(8-37):(2-8). In another embodiment, the molar ratio of the first reactant, the second reactant, and the alkaline substance is 1:(10-25):(1-4). In another embodiment, the molar ratio of the first reactant to the second reactant to the alkaline substance is 1:(30-50):(5-8).

[0074] In one embodiment of the present disclosure, the reaction solution further comprises a solvent, which is used to dissolve and disperse components in the reaction solution. In the present disclosure, the solvent may be, but is not limited to, water, ethylene glycol, or 1,4-dioxane. In one embodiment, the solvent may be a mixture of water and 1,4-dioxane. In particular, the volume ratio of 1,4-dioxane to water may be, but is not limited to, 2 to 10.

[0075] In one embodiment of the present disclosure, the reaction temperature is 25°C to 180°C, and the reaction time is 2 hours to 72 hours. This can ensure the progress of the reaction, improve the preparation efficiency of the diamine compound, and prevent the occurrence of side reactions. In particular, the reaction temperature in the preparation of the diamine compound may be, but is not limited to, 25°C, 30°C, 40°C, 45°C, 60°C, 80°C, 100°C, 115°C, 130°C, 145°C, or 180°C, and the reaction time may be, but is not limited to, 2 hours, 8 hours, 10 hours, 20 hours, 35 hours, 40 hours, 55 hours, 65 hours, or 70 hours. In one embodiment, the reaction temperature is 45°C to 90°C, and the reaction time is 35 hours to 72 hours. In another embodiment, the reaction temperature is 100°C to 180°C, and the reaction time is 2 hours to 30 hours. In one embodiment of the present disclosure, the reaction may be carried out under an inert gas atmosphere to prevent the occurrence of side reactions. In particular, the inert gas may be, but is not limited to, argon, nitrogen, etc. In particular, after the reaction, the diamine compound may be obtained by separation and purification.

[0076] In one embodiment of the present disclosure, the first reactant is reacted with NH to prepare a diamine compound represented by formula (I-1). [ka] is mixed with aqueous ammonia and reacted to prepare a compound represented by formula (I-1). In particular, a catalyst, a catalyst ligand, an alkaline substance, and the like may also be added. In a specific embodiment, brominated 1,10-phenanthroline, 28% concentrated aqueous ammonia, a copper-based catalyst (cuprous oxide), N,N'-dimethylethylenediamine, and potassium carbonate are dissolved in ethylene glycol under a nitrogen atmosphere and stirred at 45°C to 180°C for 2 to 72 hours to obtain a diamine compound represented by formula (I-1). In particular, the molar ratio of brominated 1,10-phenanthroline, 28% concentrated aqueous ammonia, copper-based catalyst (cuprous oxide), N,N'-dimethylethylenediamine, and potassium carbonate may be, but is not limited to, 1:(10-50):(0.01-0.1):(0.05-0.5):(0.05-0.5). The reaction scheme of the above reaction is shown below. [ka]

[0077] In one embodiment of the present disclosure, [ka] but [ka] and react to prepare a compound represented by formula (I-2). In particular, a catalyst, a catalyst ligand, an alkaline substance, etc. may also be added. In a specific embodiment, under a nitrogen atmosphere, [ka] , [ka] The palladium catalyst, the catalyst ligand, and the alkaline substance were dissolved in a solvent and stirred at 45°C to 120°C for 2 to 72 hours to obtain the diamine compound of formula (I-2). [ka] and, [ka] The molar ratio of the palladium catalyst, the catalyst ligand, and the alkaline substance may be, but is not limited to, 1:(2-4):(0.01-0.1):(0.01-0.5):(2-10). The reaction scheme of the above reaction is shown below. [ka]

[0078] In one embodiment of the present disclosure, [ka] but [ka] and react to prepare a compound represented by formula (I-3). In particular, a catalyst, a catalyst ligand, an alkaline substance, etc. may also be added. In a specific embodiment, under a nitrogen atmosphere, [ka] , [ka] The palladium catalyst, the catalyst ligand, and the alkaline substance were dissolved in a solvent and stirred at 45°C to 120°C for 2 to 72 hours to obtain the diamine compound of formula (I-3). [ka] and, [ka] The molar ratio of the palladium catalyst, the catalyst ligand, and the alkaline substance may be, but is not limited to, 1:(2-4):(0.01-0.1):(0.01-0.5):(2-10). The reaction scheme of the above reaction is shown below. [ka]

[0079] In one embodiment of the present disclosure, [ka] but [ka] and react to prepare a compound represented by formula (I-4). In particular, a catalyst, a catalyst ligand, an alkaline substance, etc. may also be added. In a specific embodiment, under a nitrogen atmosphere, [ka] , [ka] The palladium catalyst, the catalyst ligand, and the alkaline substance were dissolved in a solvent and stirred at 45°C to 120°C for 2 to 72 hours to obtain the diamine compound of formula (I-4). [ka] and, [ka] The molar ratio of the palladium catalyst, the catalyst ligand, and the alkaline substance may be, but is not limited to, 1:(2-4):(0.01-0.1):(0.01-0.5):(2-10). The reaction scheme of the above reaction is shown below. [ka]

[0080] The present disclosure provides a method for preparing a polyimide acid, the method comprising the steps of: mixing a first diamine compound according to any of the above embodiments with a dianhydride to form a mixed solution and reacting to obtain a polyimide acid, the polyimide acid comprising a repeat unit represented by formula (IV): [ka] wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; and R7 is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.

[0081] The method for preparing polyimide acid provided in the present disclosure is simple and easy to operate, thereby enabling large-scale production of polyimide acid. The prepared polyimide acid has a 1,10-phenanthrolinyl group, which can form a chemical bond with a metal member to improve adhesion to the metal member, thereby facilitating the preparation of polyimide and improving the bonding strength between the polyimide and the metal member. It can be understood that R1 and R2 in the diamine compound represented by formula (I) are the same as the repeating unit in the polyimide acid represented by formula (IV).

[0082] In the present disclosure, R7 is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene, and the R7 group shares two carbon atoms with the groups on either side of the R7 group. For example, when R7 is phenyl, the repeat unit represented by formula (IV) is: [ka] In one embodiment of the present disclosure, the number of repeating units represented by formula (IV) in the polyimide acid may be, but is not limited to, 5 to 2000. In one embodiment, the number of repeating units represented by formula (IV) in the polyimide acid may be 20 to 2000. In another embodiment, the number of repeating units represented by formula (IV) in the polyimide acid may be 100 to 1800. In another embodiment, the number of repeating units represented by formula (IV) in the polyimide acid may be 300 to 1500.

[0083] In one embodiment of the present disclosure, the dianhydride includes at least one of pyromellitic dianhydride, 2,3,3',4'-diphenylethertetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 3,3',4,4'-diphenylsulfonetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylether dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)benzophenone dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylmethane dianhydride, and 4,4'-bis(3,4-dicarboxyphenoxy)diphenylsulfone dianhydride. The choice of dianhydride determines the R7 group.

[0084] In one embodiment of the present disclosure, the molar ratio of the first diamine compound to the dianhydride is 0.9 to 1.1, which facilitates the rapid preparation of polyimide acid. In particular, the molar ratio of the first diamine compound to the dianhydride may be, but is not limited to, 0.9, 0.95, 1, 1.05, or 1.1.

[0085] In one embodiment of the present disclosure, the mixed solution further includes a solvent. The components in the mixed solution are mixed and dispersed in the solvent. In one embodiment of the present disclosure, the solvent may include at least one of dimethyl sulfoxide, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, and m-cresol.

[0086] In one embodiment of the present disclosure, the reaction temperature is 0°C to 100°C, and the reaction time is 2 to 12 hours. In particular, the reaction temperature in the preparation of polyimide acid may be, but is not limited to, 0°C, 5°C, 10°C, 15°C, 20°C, 25°C, 30°C, 40°C, 45°C, 50°C, 60°C, 70°C, 80°C, 90°C, or 100°C, and the reaction time may be, but is not limited to, 2 hours, 3 hours, 5 hours, 6 hours, 8 hours, 9 hours, or 12 hours. In one embodiment, the reaction temperature is 45°C to 60°C, and the reaction time is 7 to 12 hours. In another embodiment, the reaction temperature is 60°C to 100°C, and the reaction time is 2 to 7 hours. In another embodiment, the reaction temperature is 0°C to 50°C, and the reaction time is 3 to 7 hours.

[0087] In one embodiment of the present disclosure, the mixed solution further includes a second diamine compound. Addition of the second diamine compound improves the film-forming properties of the polyimide acid and polyimide. In one embodiment of the present disclosure, the second diamine compound includes at least one of 4,4'-diaminodiphenyl ether, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenyl sulfone, 1,3-diamino-2-methylpropane, N,N-bis(4-aminophenyl)-1,4-phenylenediamine, 9,9-bis(4-aminophenyl)fluorene, 1,2-diaminocyclohexane, and ethylenediamine. The second diamine compound has rotational properties, such as sp3 hybridized oxygen, to improve the film-forming properties of the polyimide acid. In one embodiment, the content of the second diamine compound in the mixed solution is less than the content of the first diamine compound. In a specific embodiment, the mixed solution includes a second diamine compound, which can ensure the film-forming properties of the polyimide film in the subsequent preparation of the polyimide film.

[0088] In one embodiment of the present disclosure, when the mixed solution contains a second diamine compound, the polyimide acid has a chemical structural formula represented by formula (V): [ka] wherein R8 is selected from substituted or unsubstituted alkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene. The choice of the second diamine compound determines the R8 group.

[0089] In one embodiment of the present disclosure, n may be 5 to 2000. In one embodiment, n is 20 to 2000. In another embodiment, n is 20 to 2000. In another embodiment, n is 100 to 1800. In another embodiment, n is 300 to 1500. In another embodiment, n is 500 to 1000. In another embodiment, n is 1000 to 1500.

[0090] In one embodiment of the present disclosure, m is 1000 or less. In one embodiment, m is 0 to 1000. That is, the mixed solution does not contain a second diamine compound, and m is 0. In another embodiment, m is 10 to 900. In another embodiment, m is 100 to 850. In another embodiment, m is 200 to 700. In another embodiment, m is 200 to 500. In another embodiment, m is 500 to 800.

[0091] The present disclosure provides a polyimide acid, which comprises a repeating unit represented by formula (IV): [ka] (wherein R1 and R2 are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; and R7 is selected from a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene.) The polyimide acid provided in the present disclosure has a 1,10-phenanthrolinyl group, which can form a chemical bond with a metal member to improve adhesion to the metal member, thereby facilitating the preparation of the polyimide and improving the bonding strength between the polyimide and the metal member. In the present disclosure, the polyimide acid may be prepared according to any embodiment of the method for preparing a polyimide acid.

[0092] The present disclosure provides a method for preparing a polyimide, the method comprising the steps of: imidizing a polyimide acid according to any one of the above embodiments to obtain a polyimide, the polyimide comprising a repeating unit represented by formula (VI): [ka] (wherein R1, R2 and R7 are the same as in polyimide acid).

[0093] The method for preparing polyimides provided in the present disclosure is simple and easy to operate, which allows for large-scale production of polyimides. The prepared polyimides have 1,10-phenanthrolinyl groups, which can form chemical bonds with metal members to improve the adhesion of polyimides to metal members, thereby facilitating the use of polyimides.

[0094] In the present disclosure, the imidization may be, but is not limited to, a heat treatment. After the heat treatment, the polyimide acid is converted into a polyimide. In one embodiment of the present disclosure, when a second diamine compound is used in the preparation process of the polyimide acid, the polyimide has a chemical structure represented by formula (VII): [ka] (wherein R8 is the same as in polyimide acid).

[0095] When the second diamine compound is not used in the preparation process of the polyimide acid, m is 0 in the chemical structure of the polyimide represented by formula (VII).

[0096] The present disclosure provides a polyimide, the polyimide comprising a repeating unit represented by formula (VI): [ka] (wherein R1 and R2 are independently selected from a single bond, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, a substituted or unsubstituted arylene alkyl, a substituted or unsubstituted heteroarylene, a substituted or unsubstituted heteroarylene alkyl, or a substituted or unsubstituted alicylidene; and R7 is selected from a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene.) The polyimides provided in the present disclosure have a 1,10-phenanthrolinyl group, which can form a chemical bond with a metal member to improve the adhesion of the polyimide to the metal member, thereby facilitating the use of the polyimide. In the present disclosure, the polyimides may be prepared according to any embodiment of the polyimide preparation method. The polyimides provided in the present disclosure have good thermal stability and can still maintain a rigid structure at high temperatures, which is beneficial for their use. In one embodiment, the polyimides can still maintain good stability at 500°C or higher.

[0097] Figure 1 shows a schematic diagram of the bonding of a polyimide to a metal atom according to one embodiment of the present disclosure, where m represents the metal element and the dotted line represents the coordinate bond formed between the polyimide and the metal. The polyimides according to the present disclosure can form a coordination compound having a five-membered ring with the metal element, thereby increasing the bonding strength between the polyimide film and the metal surface when the polyimide is used. In particular, the metal element may be, but is not limited to, aluminum, copper, iron, zinc, titanium, etc.

[0098] The present disclosure further provides a method for preparing a polyimide film, comprising the following steps: A polyimide acid is coated and then imidized to obtain a polyimide film. In one embodiment, the imidization comprises a heat treatment at 80°C to 400°C for 1 hour to 10 hours. Specifically, the imidization temperature may be, but is not limited to, 120°C, 150°C, 180°C, 200°C, 230°C, 250°C, 290°C, 310°C, or 370°C. The imidization time may be, but is not limited to, 1 hour, 3 hours, 7 hours, 9 hours, or 10 hours. In another embodiment, the imidization comprises a heat treatment at 80°C to 200°C for 1 hour to 6 hours, followed by heating to 200°C to 400°C and a heat treatment for 1 hour to 4 hours. The heat treatment at a high temperature can improve the efficiency of the imidization. Furthermore, the heating rate may be 1°C / min to 7°C / min. In particular, the heating rate may be, but is not limited to, 2°C / min, 3°C / min, 4°C / min, 5°C / min, or 6°C / min. In one particular embodiment, the imidization comprises a heat treatment at 120°C for 1 hour, followed by heating to 250°C and heat treatment for 1 hour, and heating to 350°C and heat treatment for 1 hour, with a heating rate of 2°C / min. In another particular embodiment, the imidization comprises a heat treatment at 80°C for 2 hours, followed by heating to 120°C and heat treatment for 1 hour, heating to 160°C and heat treatment for 1 hour, heating to 180°C and heat treatment for 1 hour, heating to 240°C and heat treatment for 1 hour, heating to 280°C and heat treatment for 1 hour, and heating to 350°C and heat treatment for 1 hour, with a heating rate of 2°C / min.

[0099] In this disclosure, the inventors have found through research that when R1 and R2 in Formula (I) are independently selected from a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, or substituted or unsubstituted alicylidene, the film-forming properties of the polyimide acid and polyimide are reduced unless a second diamine compound is added during the preparation of the polyimide acid and polyimide. Therefore, when R1 and R2 are independently selected from a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, or substituted or unsubstituted alicylidene, the film-forming properties of the polyimide acid and polyimide can be increased by adding a second diamine compound. In one embodiment, when a polyimide acid or polyimide is prepared using one of the compounds represented by Formulas (I-1) to (I-4), a second diamine compound may be added to improve the film-forming properties of the polyimide acid or polyimide.

[0100] The present disclosure provides a battery assembly including a polyimide film, wherein the polyimide film is made of a polyimide according to any one of the above-described embodiments. FIG. 2 is a schematic cross-sectional view of a battery assembly provided in one embodiment of the present disclosure. The battery assembly 10 includes a heat dissipation component 13, a polyimide film 12 disposed on the surface of the heat dissipation component 13, and a battery core 11 disposed on the surface of the polyimide film 12. In the related art, the battery core 11 generates heat during use, so the heat dissipation component 13 must be disposed to transfer the heat generated by the battery core 11, thereby reducing the temperature of the battery core 11 and ensuring the life and safety of the battery core 11 during use. When the heat dissipation component 13 is disposed on the surface of the battery core 11, it is necessary to connect the heat dissipation component 13 and the battery core 11 to ensure a strong bond between them and to prevent relative movement during use. If a connecting structure is used, the weight of the battery assembly 10 will be excessively increased, and the connecting structure may damage the surface of the heat dissipation component 13, thereby reducing safety during use. In the battery assembly 10 provided in the present disclosure, the battery core 11 and the heat dissipation component 13 are connected by the polyimide film 12. Because the polyimide used in the polyimide film 12 has a 1,10-phenanthrolinyl group, the bonding strength between the polyimide film 12 and the heat dissipation component 13 is increased so that the polyimide film 12 used for insulation does not fall off during use, thereby improving the safety and lifespan of the battery assembly 10. Furthermore, in related art, as the energy density of the battery core 11 increases, insulation treatment between the battery core 11 and the heat dissipation component 13 is required to ensure the safety of the battery assembly 10. With the application and development of cell-to-body (CTB) technology for the battery core 11, the battery assembly 10 must be placed under the vehicle seat and support the weight of the passenger, raising higher requirements for the safety of the battery assembly 10. The polyimide film 12 made from the polyimides provided in the present disclosure is insulating, further improving the safety of the battery assembly 10 during use.

[0101] In one embodiment of the present disclosure, the surface of the heat dissipation component 13 is made of a metallic material. This facilitates the formation of a chemical bond between the polyimide film 12 and the surface of the heat dissipation component 13, improving the bonding strength. In particular, the metallic material may be, but is not limited to, at least one of aluminum, copper, an aluminum alloy, and a copper alloy, or stainless steel. In the present disclosure, the heat dissipation component 13 may be, but is not limited to, a liquid-cooled plate. FIG. 3 is a schematic diagram illustrating the bonding of the polyimide film 12 to the heat dissipation component 13 provided in one embodiment of the present disclosure. In the figure, the surface of the heat dissipation component 13 is made of a metallic material, M is a metal element, and the dotted line represents a coordinate bond formed between the polyimide of the polyimide film 12 and the metal element of the heat dissipation component 13. In one embodiment of the present disclosure, the surface of the battery core 11 is made of a metallic material. A chemical bond is formed between the polyimide film 12 and the surface of the battery core 11, improving the bonding strength. In particular, the metallic material may be, but is not limited to, at least one of aluminum, copper, an aluminum alloy, and a copper alloy, or stainless steel.

[0102] The present disclosure provides an electronic device including a battery assembly 10 according to any one of the above embodiments. The electronic device may be, but is not limited to, a vehicle, a mobile phone, a server, a computer, etc. The battery assembly 10 of the electronic device provided in the present disclosure has high safety, thus facilitating the use of the electronic device.

[0103] The technical solutions of the present disclosure are further illustrated by specific examples and comparative examples. [Example]

[0104] The diamine compound was prepared by the following method.

[0105] Under a nitrogen atmosphere, cuprous oxide (catalyst), brominated 1,10-phenanthroline, 28% concentrated aqueous ammonia, potassium carbonate (alkaline substance), and N,N'-dimethylethylenediamine (catalyst ligand) (molar ratio 0.1:1:50:0.5:0.5) were dissolved in ethylene glycol and stirred at 180°C for 72 hours. After the reaction, the solution was cooled to room temperature, extracted with ethyl acetate, and purified by column chromatography to obtain the diamine compound of formula (I-1). [Example]

[0106] The diamine compound was prepared by the following method.

[0107] Under a nitrogen atmosphere, palladium acetate (catalyst), triphenylphosphine (catalyst ligand), brominated 1,10-phenanthroline, aminophenylboronic acid hydrochloride, and sodium hydroxide (alkaline substance) (molar ratio 0.02:0.05:1:2.1:8) were dissolved in 1,4-dioxane and stirred at 100°C for 18 hours. After the reaction, the solution was cooled to room temperature, filtered, and purified by column chromatography to obtain the diamine compound of formula (I-2). [Example]

[0108] The diamine compound was prepared by the following method.

[0109] Under a nitrogen atmosphere, bis(3,5,3',5'-dimethoxydibenzylideneacetone)palladium (catalyst), triphenylphosphine (catalyst ligand), brominated 1,10-phenanthroline, aminophenylboronic acid hydrochloride, and potassium carbonate (alkaline substance) (molar ratio 0.01:0.02:1:2.1:8) were dissolved in 1,4-dioxane and water (volume ratio 5:1) and stirred at 100°C for 18 hours. After the reaction, the solution was cooled to room temperature, filtered, and purified by column chromatography to obtain the diamine compound of formula (I-3). [Example]

[0110] The diamine compound was prepared by the following method.

[0111] Under a nitrogen atmosphere, palladium acetate (catalyst), triphenylphosphine (catalyst ligand), brominated 1,10-phenanthroline, 4-(aminomethyl)phenylboronic acid, and potassium carbonate (alkaline substance) (molar ratio 0.01:0.02:1:2.1:8) were dissolved in 1,4-dioxane and stirred at 100°C for 12 hours. After the reaction, the solution was cooled to room temperature, filtered, and purified by column chromatography to obtain the diamine compound of formula (I-4). [Example]

[0112] The polyimide acid was prepared by the following method.

[0113] 10.5 g of the diamine compound prepared in Example 1, 10 g of 4,4'-diaminodiphenyl ether, and 160 g of N,N-dimethylformamide were sequentially added to a reactor, stirred, and adjusted to a temperature of 60°C. 21.8 g of pyromellitic anhydride was slowly added to the reactor, stirred for 6 hours, and then cooled to room temperature to obtain polyimide acid. [Example]

[0114] The polyimide acid was prepared by the following method.

[0115] 18.1 g of the diamine compound prepared in Example 2, 10 g of 4,4'-diaminodiphenyl ether, and 180 g of N,N-dimethylformamide were sequentially added to a reactor, stirred, and the temperature was adjusted to 60°C. 21.8 g of pyromellitic anhydride was slowly added to the reactor, stirred for 12 hours, and then cooled to room temperature to obtain polyimide acid. [Example]

[0116] The polyimide acid was prepared by the following method.

[0117] 18.1 g of the diamine compound prepared in Example 3, 10 g of 4,4'-diaminodiphenyl ether, and 160 g of N,N-dimethylformamide were sequentially added to a reactor, stirred, and the temperature was adjusted to 45°C. 21.8 g of pyromellitic anhydride was slowly added to the reactor, stirred for 4 hours, and then cooled to room temperature to obtain polyimide acid. [Example]

[0118] The polyimide acid was prepared by the following method.

[0119] 39 g of the diamine compound prepared in Example 4 and 160 g of N,N-dimethylformamide were sequentially added to a reactor, stirred, and the temperature was adjusted to 0° C. 21.8 g of pyromellitic anhydride was slowly added to the reactor, stirred for 6 hours, and then cooled to room temperature to obtain polyimide acid.

[0120] (Comparative Example 1) The polyimide acid was prepared by the following method.

[0121] 20 g of 4,4'-diaminodiphenyl ether and 160 g of N,N-dimethylformamide were added to the reactor in order, stirred, and adjusted to a temperature of 45° C. 21.8 g of pyromellitic anhydride was slowly added to the reactor, stirred for 4 hours, and then cooled to room temperature to obtain polyimide acid.

[0122] Performance Test The structures of the diamine compounds obtained in Examples 1 to 4 were characterized by nuclear magnetic resonance spectroscopy. The results of 1H NMR are as follows:

[0123] Formula (I-1): 1H NMR (500MHz, chloroform-d) δ 8.44 (d, 1H), 7.49 (m, 2H), 4.51 (d, 1H), 4.40 (d, 1H); Formula (I-2): 1H NMR (500 MHz, クロロホルム-d) δ 8.88 (d, 2H), 8.38 (m, 2H), 7.87 (t, 2H), 7.63-7.57 (m, 2H), 6.67-6.1 (m, 2H), 4.20 (d, 1H), 4.13 (d, 1H); Formula (I-3): 1H NMR (500 MHz, クロロホルム-d) δ 8.89 (d, 2H), 8.46 (m, 21H), 7.87 (t, 2H), 7.29 (m, 2H), 7.28 (m, 2H), 6.98 (t, 2H), 6.68-6.62 (m, 2H), 4.38 (d, 2H), 4.29 (d, 2H); および Formula (I-4): 1H NMR (500 MHz, chromohol-d) δ 8.95 (d, J = 2.0 Hz, 1H), 8.61 (q, J = 1.4 Hz, 1H), 7.87 (t, J = 1.3 Hz, 1H), 7.68-7.63 (m, 2H), 7.30 (dt, J = 8.0, 1.1 Hz, 2H), 4.05 (tt, J = 6.2, 1.0 Hz, 2H), 2.52 (dt, J = 7.1, 6.2 Hz, 1H), 2.36 (dt, J = 7.0, 6.2 Hz, 1H).

[0124] The polyimide acids prepared in Examples 5-8 and Comparative Example 1 were coated and cast onto the surface of aluminum plates to form wet films of the corresponding solutions. The wet films were then transferred to an oven and imidized by heating according to the following procedure: 80°C for 2 hours, 120°C for 1 hour, 160°C for 1 hour, 180°C for 1 hour, 240°C for 1 hour, 280°C for 1 hour, and 350°C for 1 hour, with a heating rate of 2°C / min. Polyimide films were formed on the surfaces of the aluminum plates. The bonding strength between the polyimide films and the aluminum plates was tested according to ASTM D3359 Method B, Cross-Cut Tape Test, and the results are shown in Table 1. Furthermore, the decomposition temperature of the formed polyimide films (5% weight loss) was determined according to GB / T 13464-2008. The results are shown in Table 1. The polyimide acids prepared in Examples 5 to 8 and Comparative Example 1 were coated and cast onto the surface of glass plates to prepare wet films of the corresponding solutions. The wet films were then transferred to an oven and imidized according to the same heating procedure as above. Polyimide films were formed on the surface of the glass plates. After the glass plates were cooled to room temperature, they were immersed in deionized water, and the polyimide films were peeled off to obtain the corresponding free-standing polyimide films. Film-forming performance was specifically evaluated as follows: If a film formed on the glass as a single piece of film material and the film surface remained intact and unbroken after peeling, the film-forming performance was considered very good. If a film formed on the glass as a single piece of film material and the film surface remained intact but unbroken after peeling, the film-forming performance was considered normal. If the film broke into pieces on the glass, the film-forming performance was considered poor. It can be seen from Table 1 that the decomposition temperature at 5% weight loss of the polyimide film provided in the present disclosure is higher than that of Comparative Example 1, indicating excellent thermal stability.Compared with Example 7, the amino groups in the diamine compound used in Example 6 and the prepared polyimide are located on the rotation axis of the phenyl ring, which improves linearity and thermal stability. The 1,10-phenanthrolinyl group in the polyimide film can form coordinate bonds with aluminum, which increases the bonding strength between the polyimide film and the aluminum plate, thus facilitating the use of polyimide. [Table 1]

[0125] The diamine compounds, polyimide acids, and polyimides provided in the present disclosure have 1,10-phenanthrolinyl groups, which can form chemical bonds with metal components to improve the bonding strength with the metal components, thereby facilitating their use in electronic devices.

[0126] The above embodiments are merely some implementations of the present application and are described in detail, but they should not be construed as limiting the scope of the present disclosure. It should be understood by those skilled in the art that some modifications and improvements can be made by those skilled in the art without departing from the concept of the present disclosure, and all of these are contemplated within the scope of protection of the present disclosure. Therefore, the scope of protection of the present disclosure should be defined by the appended claims. [Explanation of symbols]

[0127] 10 Battery Assembly 11 Battery Core 12 Polyimide film 13 Heat dissipation components

Claims

1. A diamine compound having a chemical structural formula represented by formula (I): 【Chemical 1】 (In the formula, R １ and R ２ are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene.

2. The substituted or unsubstituted alkylene is a substituted or unsubstituted C １ ~C ８ is alkylene, The substituted or unsubstituted alkenylene is a substituted or unsubstituted C ２ ~C ８ is alkenylene, The substituted or unsubstituted alkynylene is a substituted or unsubstituted C ２ ~C ８ is alkynylene, The substituted or unsubstituted arylene is a substituted or unsubstituted C ６ ~C ３０ is an arylene, The substituted or unsubstituted arylene is a substituted or unsubstituted C ７ ~C ４０ arylene alkyl, The substituted or unsubstituted heteroarylene is a substituted or unsubstituted C ２ ~C ３０ is heteroarylene, The substituted or unsubstituted arylene is a substituted or unsubstituted C ３ ~C ４０ heteroarylenealkyl, The substituted or unsubstituted alicylidene is a substituted or unsubstituted C ３ ~C ３０ The diamine compound of claim 1 which is an allylicylidene.

3. R １ and R ２ are independently a single bond, a substituted or unsubstituted C ６ ~C ３０ Arylene, or substituted or unsubstituted C ７ ~C ４０ The diamine compound of claim 1 selected from arylene alkyls.

4. Formulas (I-1) to (I-4): 【Chemistry 2】 4. The diamine compound of claim 3, comprising one of the compounds represented by:

5. 1. A method for preparing a diamine compound, comprising: providing a first reactant having a chemical structure represented by formula (II): 【Chemistry 3】 (In the formula, R ３ and R ４ are independently selected from a chlorine atom, a bromine atom, an iodine atom, or an astatine atom), providing a second reactant having a chemical structure represented by formula (III): H ２ !! ５ (_=) (In the formula, R ５ is selected from hydrogen, alkyl substituted with a borate or borate ester, alkenyl substituted with a borate or borate ester, alkynyl substituted with a borate or borate ester, aryl substituted with a borate or borate ester, aralkyl substituted with a borate or borate ester, heteroaryl substituted with a borate or borate ester, heteroarylalkyl substituted with a borate or borate ester, or alisilyl substituted with a borate or borate ester); The first reactant and the second reactant are mixed under basic conditions to form a reaction solution, and then reacted to obtain a diamine compound having a chemical structure represented by formula (I). 【Chemistry 4】 (In the formula, R １ and R ２ are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene. A method for providing

6. the reaction solution further comprises a catalyst and a catalyst ligand; the catalyst comprises a copper-based catalyst and a palladium-based catalyst, the copper-based catalyst comprising cuprous oxide, and the palladium-based catalyst comprising at least one of bis(3,5,3',5'-dimethoxydibenzylideneacetone)palladium, bis(tri-tert-butyl)palladium, tris(dibenzylideneacetone)palladium, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium, and bis(tri-tert-butylphosphine)palladium; the catalyst ligand comprises at least one of N,N'-dimethylethylenediamine, triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, triphenylphosphine oxide, and tris(o-methylphenyl)phosphine; the molar ratio of the first reactant to the second reactant to the catalyst to the catalyst ligand is 1:(2-50):(0.005-0.2):(0.005-0.5); the reaction solution further comprises an alkaline substance, the alkaline substance comprising at least one of potassium carbonate, sodium carbonate, cesium fluoride, sodium hydroxide, potassium hydroxide, and barium hydroxide; the molar ratio of the first reactant to the second reactant to the alkaline substance is 1:(2-50):(0.05-10); The reaction temperature is 25°C to 180°C, and the reaction time is 2 hours to 72 hours. The preparation method according to claim 5.

7. 7. The preparation method according to claim 5 or 6, wherein the reaction solution further comprises a solvent, the solvent comprising water, ethylene glycol, and 1,4-dioxane, and the volume ratio of 1,4-dioxane to water is 2-10.

8. 8. The process according to any one of claims 5 to 7, wherein the reaction is carried out under an inert atmosphere.

9. Polyimide acid having a repeating unit represented by formula (IV): 【Chemistry 5】 (In the formula, R １ and R ２ are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; R ７ is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene).

10. The polyimide acid according to claim 9, having a chemical structure represented by formula (V): 【Chemistry 6】 (In the formula, R ８ is selected from substituted or unsubstituted alkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene; n is 5 to 2000; and m is 0 to 1000.

11. A method for preparing a polyimide acid, comprising mixing a first diamine compound and a dianhydride to form a mixed solution and reacting them to obtain a polyimide acid, wherein the first diamine compound is the diamine compound according to any one of claims 1 to 4 or the diamine compound prepared by the preparation method according to any one of claims 5 and 6, and comprises a repeating unit represented by formula (IV). 【Chemistry 7】 (In the formula, R １ and R ２ are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; R ７ is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene).

12. a molar ratio of the first diamine compound to the dianhydride of 0.9 to 1.1; the dianhydride comprises at least one of pyromellitic dianhydride, 2,3,3',4'-diphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 3,3',4,4'-diphenyl sulfone tetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl ether dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)benzophenone dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylmethane dianhydride, and 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride; the mixed solution further comprises a second diamine compound, the second diamine compound comprising at least one of 4,4'-diaminodiphenyl ether, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenyl sulfone, 1,3-diamino-2-methylpropane, N,N-bis(4-aminophenyl)-1,4-phenylenediamine, 9,9-bis(4-aminophenyl)fluorene, 1,2-diaminocyclohexane, and ethylenediamine; the mixed solution further comprises a solvent, the solvent comprising at least one of dimethyl sulfoxide, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, and m-cresol; The preparation method according to claim 11, wherein the reaction temperature is 0°C to 100°C and the reaction time is 2 hours to 12 hours.

13. A polyimide having a repeating unit represented by formula (VI): 【Chemistry 8】 (In the formula, R １ and R ２ are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; R ７ is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene).

14. The polyimide according to claim 13, having a chemical structure represented by formula (VII): 【Chemistry 9】 (In the formula, R ８ is selected from substituted or unsubstituted alkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene; n is 5 to 2000; and m is 0 to 1000.

15. A method for preparing a polyimide, comprising imidizing the polyimide acid according to any one of claims 9 and 10 or the polyimide acid prepared by the preparation method according to any one of claims 11 and 12 to obtain a polyimide, wherein the polyimide comprises a repeat unit represented by formula (VI): 【Chemistry 10】 (In the formula, R １ and R ２ are independently selected from a single bond, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted arylene, substituted or unsubstituted arylene alkyl, substituted or unsubstituted heteroarylene, substituted or unsubstituted heteroarylene alkyl, or substituted or unsubstituted alicylidene; R ７ is selected from substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene).

16. 16. A battery assembly (10) comprising a heat-dissipating component (13), a polyimide film (12) disposed on a surface of the heat-dissipating component (13), and a battery core (11) disposed on the surface of the polyimide film (12), wherein the polyimide film (12) is made of the polyimide according to any one of claims 13 and 14 or a polyimide prepared by the preparation method according to claim 15.

17. 17. The battery assembly (10) of claim 16, wherein the surface of the heat-dissipating component (13) is made of a metallic material and the surface of the battery core (11) is made of a metallic material.

18. An electronic device comprising a battery assembly (10) according to claim 16 or 17.

Images