KR20180113422A - Diamine compound, polyamic acid prepared therefrom, polyimide prepared therefrom, and polyimide film including polyimde - Google Patents

Abstract

Provided is a diamine compound represented by chemical formula 1, Ar_1-X_1-Ar_2. Moreover, provided are a polyamic acid produced therefrom, polyimide, and polyimide film. In the chemical formula, X, Ar_1, and Ar2 are the same as defined in the present specification. According to the present invention, the polyimide film containing the polyimide ensures excellent transparency and durability while having low permittivity.

Description

A diamine compound, a polyimide film formed from the polyamic acid and a polyimide, and a polyimide film containing the polyimide and a polyimide. (Diamine compound, polyamic acid prepared therefrom, polyimide prepared therefrom, and polyimide film including polyimide)

A novel diamine compound, a polyamic acid formed from the same, a polyimide, and a polyimide film containing the polyimide.

The polyimide is a polymer having an imide bond in the main chain and has heat resistance and chemical resistance derived from the chemical stability of the imide. In particular, aromatic polyimides among polyimides are used for high-strength and high-temperature applications such as automobile materials and aerospace materials, as well as daily living products, due to their superior mechanical properties and electrical insulating properties due to their rigid backbone structures. It is widely applied in the field. However, in spite of such excellent properties, the polyimide has a high aromatic ring density formed on the benzene ring, causing a coloring phenomenon, which causes a decrease in light transmittance, making application to optical materials difficult.

In addition, aromatic polyimides are widely used for insulating films for semiconductors such as interlayer materials of semiconductors and metal wirings due to their excellent heat resistance, but they are expected to have low dielectric properties as device integration increases. In order to overcome this problem, studies have been carried out to lower the dielectric constant of polyimide using various inorganic particles. However, such a composite material has low chemical stability and low light transmittance.

Accordingly, conventional techniques fail to provide a polyimide film that is high enough to be applied to an advanced integrated device, and it is difficult to provide a polyimide film that is superior to the conventional polyimide film in terms of mechanical durability, heat resistance and easiness in the manufacturing process, It is urgently required to develop a polyimide film which can be used for semiconductor substrate materials and the like.

According to one aspect, there is provided a novel diamine compound.

According to another aspect, there is provided a polyimide obtained from a polyamic acid and a polyamic acid formed from the above-mentioned diamine compound.

Another object of the present invention is to provide a polyimide film containing the polyimide described above and having excellent light transmittance and heat resistance and low dielectric constant characteristics.

According to one aspect, there is provided a diamine compound represented by the following formula (1).

[Chemical Formula 1]

X ₁ is selected from the group consisting of oxygen (O), sulfur (S), sulfur monoxide (SO), sulfur dioxide (SO ₂ ) and selenium (Se)

Ar ₁ is selected from the group consisting of the following formulas (1-1) to (1-3)

[Formula 1-1] [Formula 1-2] [Formula 1-3]

In Formulas 1-1 to 1-3, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen or an alkyl group having 1 to 30 carbon atoms, * indicates a binding site,

Ar ₂ is selected from the group consisting of the following formulas 1-4 - 1-7,

[Formula 1-4] [Formula 1-5]

[Chemical Formula 1-6] [Chemical Formula 1-7]

In formulas (1-4) and (1-5), R and R 'are each independently a fluorinated C1-C10 alkyl group substituted with fluorine and * indicates a binding site.

According to other aspects There is provided a polyamic acid which is a polymerization product of the above-mentioned diamine compound and an acid dianhydride.

According to another aspect, there is provided a polyimide which is an imidation reaction product of the above-mentioned polyamic acid.

According to another aspect, there is provided a polyimide film comprising the polyimide described above.

The polyamic acid formed from the diamine compound according to one embodiment and the polyimide film containing the polyamic acid obtained therefrom have a low dielectric constant while being excellent in transparency and heat resistance.

FIG. 1 shows a nuclear magnetic resonance (NMR) spectrum of a diamine compound of Formula 6 prepared according to Example 1. FIG.
2 shows the NMR analysis spectrum of the diamine compound represented by the formula (7) prepared according to Example 2.

Hereinafter, the diamine compound according to one embodiment, the polyamic acid formed therefrom, the polyimide obtained from the polyamic acid, and the polyimide film containing the polyimide will be described in more detail.

There is provided a diamine compound represented by the following formula (1).

[Chemical Formula 1]

Wherein X ₁ is selected from the group consisting of oxygen (O), sulfur (S), sulfur monoxide (SO), sulfur dioxide (SO ₂ ) and selenium (Se)

Ar ₁ is independently selected from the group consisting of the following formulas (1-1) to (1-3)

[Formula 1-1] [Formula 1-2] [Formula 1-3]

In Formulas 1-1 to 1-3, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen or an alkyl group having 1 to 30 carbon atoms, * indicates a binding site,

Ar ₂ is selected from the group consisting of Formulas 1-4 to 1-7,

[Formula 1-4] [Formula 1-5]

[Chemical Formula 1-6] [Chemical Formula 1-7]

In formulas (1-4) and (1-5), R and R 'are each independently a fluorinated C1-C10 alkyl group substituted with fluorine and * indicates a binding site.

The fluorinated C 1 -C 10 alkyl group substituted with fluorine is a perfluorinated alkyl group having 1 to 10 carbon atoms which is partially or completely fluorinated. The fluorine-substituted alkyl group having 1 to 10 carbon atoms includes, for example, -CF ₃ , or -CF ₂ CF ₃ . The alkyl group having 1 to 10 carbon atoms substituted with fluorine has a lower dielectric constant and better optical characteristics than an alkyl group partially substituted with fluorine when it is a completely fluorinated alkyl group.

In general, as the benzene ring present in the main chain of the compound is included, the transition of the pi electrons of the benzene ring can easily occur. This may result in the absorption of light in the visible light region, which may result in browning of the color of the compound, which may degrade the light transmission.

Diamine compound in accordance with one embodiment, the oxygen (O) in the benzene ring, a sulfur (S), monoxide, sulfur (SO), sulfur dioxide (SO _2), selenium (Se), fluorine (F), methyl (CF _{3-trifluoromethyl} ), And the like, and they can reduce the movement of? Electrons in the molecule, so that absorption of light in the visible light region can be reduced. In addition, the trifluormethyl structure of the diamine compound has a fluorine atom with a large molecular radius, thereby minimizing the interaction between the polymer main chains, thereby lowering the high aromatic ring density. Accordingly, a polymer produced using the polymer as a monomer, for example, a polyamic acid and a polyimide, and a polyimide film containing the polyimide are colorless and transparent and can exhibit excellent light transmittance.

The diamine compound according to an embodiment includes a carbon-fluorine bond having a high binding energy, so that it is structurally very stable and has a very high chemical stability. Accordingly, the polymer and / or the polyimide film produced using this as a monomer can exhibit excellent heat resistance and chemical / mechanical durability. In addition, since the diamine compound contains a large number of fluorine atoms which lower the refractive index and the dielectric constant, polymers and polyimide films produced using the same as monomers can also exhibit low refractive index and dielectric constant. The diamine compound according to an embodiment has a structure in which aromatics are linked to a 16-cycle flexible element in the molecule, and therefore, the polymers and the polyimide film produced using the same have a reduced crystallinity and an intramolecular anisotropy, The temperature can be high and the birefringence can also be kept low.

The compound of Formula 1 has a structure in which Ar ₁ and Ar ₂ are asymmetrically arranged around X ₁ . R ₁ to R ₄ in Ar ₁ are selected from unfluorinated alkyl groups, and Ar 2 has a group in which R and R 'are fluorinated as shown in the above formulas 1-4 to 1-7. The fluorinated group includes, for example, a trifluoromethyl group, and this group has a fluorine atom with a large molecular radius, and has an effect of minimizing the interaction between the polymer main chains, so that a high aromatic ring density can be lowered.

As a result of the above-described structural features, the crystallinity of the polymer is lowered compared with a compound having a structure in which Ar ₁ and Ar 2 are symmetrically arranged around X ₁ , the transmittance of the polyimide film obtained by using the compound is improved, The dielectric constant is reduced.

The compound represented by the formula (1) is selected from the compounds represented by the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In formulas (2) to (5), R ₂ and R ₃ are alkyl groups having 1 to 10 carbon atoms and R 'is an alkyl group having 1 to 10 carbon atoms substituted with fluorine.

The compound represented by the formula (1) is selected from the compounds represented by the following formulas (6) to (11).

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

The compounds represented by the above-described formulas (6) to (11) have a methyl group at an ortho position of an amino group with an asymmetric structure, and thus the CN imide bond is distorted during imide polymerization and the packing between the polymers is inhibited It has an effect of lowering the dielectric constant and the refractive index, and it is possible to improve the glass transition temperature of the polymer by firmly holding the polymer chain. The compounds represented by the formulas (6) to (11) have the formula CF ₃ and CF ₂ CH ₃ groups, and when used, have the effect of lowering the dielectric constant and the refractive index.

According to another aspect there is provided a polyamic acid which is a polymerization product of the above-mentioned diamine compound and an acid dianhydride.

The acid dianhydride is not particularly limited, and any acid dianhydride that is commonly used in the art can be used. The acid dihydrate may be, for example, a compound represented by the following formula (12).

[Chemical Formula 12]

In the formula (12), R ₅ is a group selected from the group represented by the formula (12-1).

이다.R < ₅ > in formula (12) is, for example,

to be.

In an exemplary embodiment, the polyamic acid may be a polymer represented by the following formula (13).

[Chemical Formula 13]

X ₁ is selected from the group consisting of oxygen (O), sulfur (S), sulfur monoxide (SO), sulfur dioxide (SO ₂ ) and selenium (Se)

Ar ₃ is independently selected from the group represented by the following formula (1-8)

[Chemical Formula 1-8]

In Formula 1-8, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen or an alkyl group having 1 to 30 carbon atoms, * represents a binding site,

Ar < ₄ > is selected from the group represented by the following formula (1-9)

[Chemical Formula 1-9]

In Formula 1-9, R and R 'are each independently a fluorinated C1-C10 alkyl group substituted with fluorine, * indicates a binding site,

R < ₅ > is a group selected from the group consisting of the formula (12-1)

[Formula 12-1]

and n is an integer of 10 to 1,000.

The polyamic acid represented by the formula (13) may be, for example, a polymer represented by the following formula (13a) or a polymer represented by the formula (13b).

[Chemical Formula 13a]

In the formula (13a), n is an integer of 10 to 1,000, for example, an integer of 10 to 100,

[Chemical Formula 13b]

In formula (13b), n is an integer of 10 to 1,000, for example, an integer of 10 to 100

The polyamic acid according to one embodiment has a number average molecular weight of 10,000 to 500,000 g / mol. When such a number average molecular weight is obtained, the dielectric constant and optical characteristics of the polyamic acid are excellent.

According to another aspect, there is provided a polyimide obtained by imidizing the above-mentioned polyamic acid.

In an exemplary embodiment, the polyimide may be a compound represented by the following formula (14).

[Chemical Formula 14]

In formula (14), Ar ₃ is independently selected from the group consisting of the following formulas (1-8)

[Chemical Formula 1-8]

In Formula 1-8, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen or an alkyl group having 1 to 30 carbon atoms,

Ar < ₄ > is selected from the group represented by the following formula (1-9)

[Chemical Formula 1-9]

In Formula 1-9, R and R 'are each independently a fluorinated C1-C10 alkyl group substituted with fluorine, * indicates a binding site,

R < ₅ > is a group selected from the group consisting of the formula (12-1)

[Formula 12-1]

and n is an integer of 10 to 1,000.

The polyimide represented by the formula (14) is, for example, a polymer represented by the following formula (17) or a polymer represented by the following formula (18).

[Chemical Formula 17]

In Formula 17, n is an integer of 10 to 1,000, for example, an integer of 10 to 100,

[Chemical Formula 18]

In the general formula (18), n is an integer of 10 to 1,000, for example, an integer of 10 to 100.

The polyamic acid of the present invention and the method for producing the polyimide using the polyamic acid will now be described.

The polyamic acid is obtained by mixing a diamine compound of the formula (1) and an acid dianhydride with a solvent, and then conducting a polymerization reaction in an inert gas atmosphere to prepare a polyamic acid. As the solvent, for example, N-methylpyrrolidone, tetrahydrofuran and the like are used.

The inert gas atmosphere is formed using argon, nitrogen, or the like.

The above-mentioned polymerization reaction may vary depending on the type of diamine compound and acid dihydrate to be used and reaction conditions such as temperature. For example, the polymerization reaction may be carried out, for example, at a temperature in the range of from 25 ° C to 150 ° C.

Imidization reaction of the polyamic acid is carried out to obtain the desired polyimide.

The imidization reaction includes a dehydrating cyclization by heating and a dehydration cyclization using a dehydrating agent.

The dehydrating cyclization by heating is carried out, for example, at a high temperature of 300 to 400 캜 to carry out imidization.

The method of dehydrating cyclization using a dehydrating agent is carried out at a temperature of 200 ° C or lower to carry out imidation. It is also possible to use a catalyst such as an acid or base together with a dehydrating agent. For example, an organic acid such as p-hydroxyphenylacetic acid is used as the acid catalyst and isoquinoline, triethylamine, pyridine, 1,4-diazabicyclo [2.2.2] octane or the like is used as the base catalyst .

The polyimide according to one embodiment has a number average molecular weight of 10,000 to 500,000 g / mol.

In an exemplary embodiment, the polyimide may be used to produce a polyimide film.

The diamine compound according to one embodiment contains a large number of carbon-fluorine bonds having a high binding energy, so that it is structurally very stable and highly stable in chemical stability. Accordingly, polymers and / or polyimide films prepared using the same as monomers can exhibit excellent heat resistance and chemical / mechanical durability.

In an exemplary embodiment, the polyimide film produced using the diamine compound has a total weight of the polyimide film reduced to 90% at a temperature between about 553 and 554 relative to the total weight of the polyimide film at room temperature can do.

Also, since the diamine compound containing trifluoromethyl contains a large number of fluorine atoms which lower the refractive index and the dielectric constant, the polymers and polyimide films prepared using the same as monomers can also exhibit low refractive index and dielectric constant.

In an exemplary embodiment, the polyimide film may exhibit a refractive index of 1.5 to 1.6, e.g., a refractive index of about 1.547. And in an exemplary embodiment, the polyimide film may exhibit a dielectric constant of 2.3 to 2.4, for example, a dielectric constant of about 2.39. And is very useful as an optical film when the polyimide film has the above-described refractive index and permittivity characteristics.

The 10% weight reduction temperature of the polyimide film according to one embodiment is 550 to 560 占 폚. As used herein, the term "10% weight loss temperature" refers to the temperature at which the total weight of the film or compound decreases to 90% of the total weight of the film or compound at room temperature. That is, the temperature at which the weight decreases by 10% with respect to the total weight at room temperature.

The glass transition temperature of the polyimide is 300 to 320 ° C. The glass transition temperature of the polyimide is excellent in the thermal stability in the above range.

The amine-based compound according to the present invention and the polymer as a curing reaction product of the curable monomer can be applied to a glass fiber composite film, a spectacle lens, a light diffusion film, an encapsulating material, and the like.

The polyimide film according to one embodiment can be used for an optical film, and such an optical film is useful as a film and a coating material in manufacturing a microlens, a functional optical coating, and a high-light LED (Light Emitting Diode).

The polyimide film is useful as an LED encapsulant or a substrate.

Hereinafter, the present invention will be described with reference to the following examples, but it should be understood that the present invention is not limited to the following examples.

Example  1: Diamine  Preparation of compounds

In a 250 ml round bottom flask, 150 ml of DMF, 10 g of 4-amino-3,5-xylenol (A), 10.77 ml of 5-chloro-2-nitrobenzotrifluoride (B) 15 g of potassium was added and the mixture was refluxed for 1 day. Then, reduction reaction was carried out with ethanol as a solvent using hydrazine and palladium catalyst to obtain 5.6 g of the final product of the formula (6).

[Chemical Formula 6]

[Reaction Scheme 1]

Example  2: Diamine  Preparation of compounds

As shown in Reaction Scheme 2, 150 ml of DMF, 10 g of 4-amino-3,5-xylenol, 10.77 ml of 2-chloro-5-nitrobenzotrifluoride and 15 g of potassium carbonate were added to a 250 ml round- And the mixture was refluxed for 1 day, followed by reduction using ethanol as a solvent with a palladium catalyst and hydrogen gas to obtain 3.2 g of a diamine compound represented by the formula (7).

 (7)

[Reaction Scheme 2]

Example  3: Preparation of polyimide represented by general formula (17)

In a 50 ml round-bottom flask, 1.0 g of the diamine compound of Formula 6 prepared in Example 1, 1.51 g of 4,4'-hexafluoroisopropylidene diphthalic anhydride (6FDA) After adding 9.77 ml of water, the solution was reacted at room temperature for 24 hours under a nitrogen atmosphere to prepare a polyamic acid solution having a solid content of 20 wt%. About 5 drops of isoquinoline were added for chemical imidization, The resulting mixture is stirred for about 12 hours while removing water. Thereafter, the precipitate was precipitated in methanol to prepare a polyimide precipitate represented by the general formula (17). The number average molecular weight of the solidified polyimide was about 50,000 (measuring conditions: 80, gel permeation chromatography, GPC).

[Chemical Formula 17]

In formula (17), n is 70 in terms of degree of polymerization.

Example  4: Preparation of polyimide represented by the general formula (18)

In a 50 ml round-bottom flask, 1.0 g of the diamine of the formula (7) prepared in accordance with Example 2, 1.51 g of 4,4'-hexafluoroisopropylidene diphthalic anhydride (6FDA) After adding 9.77 ml of the solution, the solution was reacted at room temperature for 24 hours under a nitrogen atmosphere to prepare a polyamic acid solution having a solid content of 20 wt%. About 5 drops of isoquinoline were added for chemical imidization, The mixture is stirred for about 12 hours while removing water. Thereafter, the precipitate was precipitated in methanol to prepare a polyimide precipitate represented by the general formula (18). The number average molecular weight of the solidified polyimide was measured at about 50,000 (measuring conditions: 80, gel permeation chromatography, GPC).

6FDA

[Chemical Formula 18]

In the formula (18), n is 70 as the degree of polymerization.

Example  5: Preparation of polyimide film

The solidified polyimide represented by the formula (17) prepared in Example 3 was dissolved in triethylene glycol dimethyl ether (triglyme) at a solid content of 15 wt% to prepare a polyimide solution. Thereafter, the film was cast on each of a glass plate, a silicon substrate, and a quartz plate, and then dried in a vacuum oven at 150 for 5 hours to remove the solvent, thereby producing a polyimide film having a thickness of about 10 mm.

Example  6: Preparation of polyimide film

A polyimide film was produced in the same manner as in Example 5, except that the polyimide represented by the formula (18) prepared in accordance with the example 4 was used instead of the polyimide represented by the formula (17) .

<Comparative Example>

Comparative Example  1: Preparation of polyimide and polyimide film

A polyimide was produced in the same manner as in Example 1 except that a diamine compound represented by the following formula (14) was used in the production of the polyimide. A polyimide was prepared in the same manner as in Example 5 except that the polyimide thus obtained was used.

[Chemical Formula 14]

The diamine compound represented by the above formula (14) was obtained in the same manner as in Preparation Example 1 except that the following compound was used instead of the compound (B) in Production Example 1.

  (D)

Comparative Example  2: Preparation of polyimide film

A polyimide was produced in the same manner as in Example 1 except that a diamine compound represented by the following formula (15) was used in the production of the polyimide. A polyimide was produced in the same manner as in Example 5 except that this polyimide was used.

[Chemical Formula 15]

The diamine compound represented by the formula (15) was obtained according to the synthesis method using 2-chloro-5-nitrobenzotrifluoride (Y. Maki and K. Inukai, Nippon Kagaku Kaishi J: 675-7 (1972) ).

Comparative Example  3: Preparation of polyimide film

A polyimide was produced in the same manner as in Example 1 except that the diamine compound represented by the following formula (16) was used in the production of the polyimide. A polyimide was produced in the same manner as in Example 5 except that this polyimide was used.

[Chemical Formula 16]

The diamine compound represented by the formula (16) was prepared by the same method as that of the compound represented by the formula (15) of Comparative Example 2 except that the composition of the corresponding starting material was changed so as to obtain the target compound.

Evaluation example  1: Nuclear magnetic resonance analysis (NMR)

NMR analysis of the diamine compound of the formula (6) of Example 1 and the diamine compound of the formula (7) prepared according to the Example 2 was carried out, and the analysis results thereof are shown in FIG. 1 and FIG. 2, respectively.

NMR analysis was performed on 600 MHz NMR spectrometer manufacturers (Agilent Technologies, Inc. and Bruker BioSpin Corp.).

Referring to FIG. 1, the peaks from a to g appear at chemical shifts of 7.07, 6.94, 6.69, 6.61 and 2.16 ppm, respectively, and the hydrogen peaks of amines at chemical shifts of 3.95 and 3.46 ppm, respectively, appear in e and f. The structure of the diamine compound of Formula 6 was confirmed by confirming the peaks of each hydrogen.

Referring to FIG. 2, the peaks from a to g appear in chemical shifts of 6.87, 6.73, 6.67, 6.46 and 2.04 ppm, respectively, and the hydrogen peaks of amines with chemical shifts of 5.18 and 4.28 ppm, respectively, appear in e and f. The structure of the diamine compound of Formula 7 was confirmed by confirming the peaks of each hydrogen.

Evaluation example  2: Experiment to confirm the refractive index, dielectric constant and heat resistance of the polyimide film

The refractive indexes of the polyimide films prepared using polyimide according to Examples 3 and 4 and the polyimide films prepared according to Comparative Examples 1-3 were analyzed with a prism coupler. The permittivity was calculated from the refractive index according to Maxwell's equations (ε = 1.1n _av ² ). Further, heat resistance was measured by TGA and DSC analysis, and the results are shown in Table 1.

Polyimide Diamine Acid dianhydride Refractive index
at 637 nm permittivity
at 471 THz 10% weight reduction temperature (캜) Glass transition temperature (캜) Example 3 Example 1 6FDA 1.5475 2.395 554 314 Example 4 Example 2 6FDA 1.5470 2.393 553 313 Comparative Example 2 Formula 15 6FDA - 2.76 524 295

Referring to Table 1, the polyimide films prepared using the polyimide polymers according to Examples 3 and 4 all exhibit a refractive index of 1.6 or less, indicating excellent refractive index. Also, the dielectric constant of the polyimide film was also measured to be as low as 2.3. In addition, the polyimide films prepared using the polyimide polymers according to Examples 3 and 4 all showed a weight reduction of 10% at a temperature of 550 or higher, a glass transition temperature of 300 or higher, And it was confirmed that it is excellent.

On the other hand, the dielectric constant of the polyimide film of Comparative Example 2 was 2.76 as shown in Table 1, which was about 15.24% higher than that of the polyimide film of Example 3, and compared with the dielectric constant of the polyimide film of Example 4 Which is about 15.33%. And the 10% weight reduction temperature of Comparative Example 2 was 524 and the glass transition temperature was 295, which indicated that the thermal properties were degraded as compared with the polyimide films of Examples 3 and 4.

The dielectric constant and thermal properties of the polyimide films of Comparative Examples 1 and 3 were analyzed. As a result, the polyimide films of Comparative Example 2 and Comparative Example 3 exhibited the same or similar properties as those of the polyimide film of Comparative Example 2. As described above, it was found that the polyimide films of Examples 3 and 4 had higher refractive index, lower dielectric constant, and improved thermal characteristics than the polyimide films of Comparative Examples 1 to 3.

The embodiments of the present invention described above should not be construed as limiting the technical idea of the present invention. The scope of protection of the present invention is limited only by the matters described in the claims, and those skilled in the art will be able to modify the technical idea of the present invention in various forms. Accordingly, such improvements and modifications will fall within the scope of protection of the present invention as long as it is obvious to those skilled in the art.

Claims (14)

A diamine compound represented by the following formula (1):
[Chemical Formula 1]

X ₁ is selected from the group consisting of oxygen (O), sulfur (S), sulfur monoxide (SO), sulfur dioxide (SO ₂ ) and selenium (Se)
Ar ₁ is selected from the group consisting of the following formulas (1-1) to (1-3)
[Formula 1-1] [Formula 1-2] [Formula 1-3]

In Formulas 1-1 to 1-3, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen or an alkyl group having 1 to 30 carbon atoms, * indicates a binding site,
Ar ₂ is selected from the group consisting of the following formulas 1-4 - 1-7,
[Formula 1-4] [Formula 1-5]

[Chemical Formula 1-6] [Chemical Formula 1-7]

In formulas (1-4) and (1-5), R and R 'are each independently a fluorinated C1-C10 alkyl group substituted with fluorine and * indicates a binding site. The method according to claim 1,
Wherein the compound represented by Formula 1 is at least one selected from the group consisting of compounds represented by the following Formulas 2 to 4:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In formulas (2) to (5), R ₂ and R ₃ are alkyl groups having 1 to 10 carbon atoms and R 'is an alkyl group having 1 to 10 carbon atoms substituted with fluorine. The method according to claim 1,
Wherein the compound represented by the formula (1) is one selected from the compounds represented by the following formulas (6) to (11):
[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

A polyamic acid which is a polymerization reaction product of an acid dianhydride with a diamine compound of any one of claims 1 to 3. 5. The method of claim 4,
Wherein the acid dianhydride is a polyamic acid:
[Chemical Formula 12]

In the formula (12), R ₅ is a group selected from the group represented by the formula (12-1).

5. The method of claim 4,
Wherein the polyamic acid is a compound represented by the following formula (13): &lt; EMI ID =
[Chemical Formula 13]

X ₁ is selected from the group consisting of oxygen (O), sulfur (S), sulfur monoxide (SO), sulfur dioxide (SO ₂ ) and selenium (Se)
Ar ₃ is independently selected from the group represented by the following formula (1-8)
[Chemical Formula 1-8]

In Formula 1-8, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen or an alkyl group having 1 to 30 carbon atoms, * represents a binding site,
Ar &lt; ₄ &gt; is selected from the group represented by the following formula (1-9)
[Chemical Formula 1-9]

In Formula 1-9, R and R 'are each independently a fluorinated C1-C10 alkyl group substituted with fluorine, * indicates a binding site,
R &lt; ₅ &gt; is a group selected from the group consisting of the formula (12-1)
[Formula 12-1]

and n is an integer of 10 to 1,000. 5. The method of claim 4,
Wherein the polyamic acid is a polymer represented by the following formula (13a) or a polyamic acid represented by the formula (14):
[Chemical Formula 13a]

In formula (13a), n is an integer of 10 to 1,000,
[Chemical Formula 13b]

In formula (13b), n is an integer of 10 to 1,000 A polyimide which is an imidation reaction product of the polyamic acid according to claim 4. 9. The method of claim 8,
Wherein the polyimide is a polyimide represented by the following formula (14):
[Chemical Formula 14]

In formula (14), Ar ₃ is independently selected from the group consisting of the following formulas (1-8)
[Chemical Formula 1-8]

In Formula 1-8, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen or an alkyl group having 1 to 30 carbon atoms, * represents a binding site,
Ar &lt; ₄ &gt; is selected from the group represented by the following formula (1-9)
[Chemical Formula 1-9]

In Formula 1-9, R and R 'are each independently a fluorinated C1-C10 alkyl group substituted with fluorine, * indicates a binding site,
R &lt; ₅ &gt; is a group selected from the group consisting of the formula (12-1)
[Formula 12-1]

and n is an integer of 10 to 1,000. 9. The method of claim 8,
Wherein the polyimide is a polymer represented by the following formula (17) or a polymer represented by the following formula (18):
[Chemical Formula 17]

In the general formula (17), n is an integer of 10 to 1,000,
[Chemical Formula 18]

In Formula 18, n is an integer of 10 to 1,000. 9. A polyimide film comprising the polyimide of claim 8. 12. The method of claim 11,
Wherein the polyimide film has a refractive index of 1.5 to 1.6. 12. The method of claim 11,
Wherein the polyimide film has a dielectric constant of 2.3 to 2.4. 12. The method of claim 11,
Wherein the polyimide film has a 10% weight reduction temperature of from 550 to 560.

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