KR101139055B1 - Novel Aromatic Enediyne Derivatives, and Organic Semiconductor and Electronic Device using the Same - Google Patents

Abstract

The present invention relates to novel aromatic enediyne derivatives, organic semiconductors and electronic devices using the same, and is capable of performing solution processes such as room temperature spin coating at the time of application of the device, as well as providing chemically and electrically stable and reliable semiconductor thin films Enediyne derivatives, organic semiconductors and electronic devices using the same. According to the present invention, it is possible to form a thin film having a large area by a solution process, thereby simplifying the process and reducing the cost, and providing an organic semiconductor that can be effectively applied to various fields such as organic thin film transistors, electroluminescence devices, can do.

An organic semiconductor, a solution process, a spin coating, a thin film transistor, an electroluminescent device, a solar cell, a memory

Description

TECHNICAL FIELD [0001] The present invention relates to novel aromatic enediyne derivatives, organic semiconductors and electronic devices using the same,

1 is a graph showing a differential scanning calorimetry of an aromatic enediyne derivative synthesized in Production Example 1 of the present invention,

2 is a graph showing differential scanning calorimetry of an aromatic enediyne derivative synthesized in Production Example 2 of the present invention,

3 is a graph showing differential scanning calorimetry of an aromatic enediyne derivative synthesized in Production Example 3 of the present invention,

4 is a graph of Differential Scanning Calorimetry of an aromatic enediyne derivative synthesized in Production Example 4 of the present invention,

5 is a thermogravimetry analysis graph of an aromatic enedione derivative synthesized in Production Example 1 of the present invention,

6 is a thermogravimetry analysis graph of the aromatic enedia derivative synthesized in Production Example 2 of the present invention,

7 is an infrared (IR) spectrum of the organic semiconductor thin film prepared in Example 1 of the present invention,

8 is a schematic cross-sectional view of an organic thin film transistor according to an embodiment of the present invention.

Description of the Related Art

1: substrate 2: gate electrode

3: gate insulating layer 4: source electrode

5: drain electrode 6: organic semiconductor layer

The present invention relates to a novel aromatic enedione derivative, an organic semiconductor and an electronic device using the same, and more particularly, to a novel aromatic enedione derivative, which is a novel aromatic enediyne derivative and which can be subjected to a solution process such as room temperature spin coating And an electronic device employing the same.

Flat panel display devices such as liquid crystal display devices and organic electroluminescence display devices are provided with various thin film transistors (TFT) for driving these devices. The thin film transistor includes a gate electrode, a source electrode and a drain electrode, and a semiconductor layer which is activated in response to driving of the gate electrode. The p-type or n- Acting as a conductive channel material.

Amorphous silicon (a-Si) and polycrystalline silicon (hereinafter, referred to as poly-Si) are mainly used as a semiconductor for use in a thin film transistor. However, due to recent trends of large- , Researches on semiconductors using an organic material in an inorganic material requiring a high-temperature vacuum process are being actively carried out.

Currently, studies on low molecular weight organic materials such as pentacene as an organic semiconductor material have been accelerated, and a low molecular organic material such as pentacene has a high charge mobility of 3.2 to 5.0 cm 2 / Vs or more and excellent current blink ratio However, expensive vacuum deposition equipment is required for forming a thin film, and it is difficult to form a fine pattern, which is unsuitable for cost and large area.

Also, as an oligomer organic semiconductor, IBM has reported a soluble pentacene precursor capable of annealing at about 120 to 200 DEG C with a charge mobility of about 0.1 cm2 / Vs (IBM, JACS 2002 , 124 , 8812.) The University of California reports an oligothiophene precursor material with charge mobility of about 0.03 to 0.05 cm2 / Vs and capable of annealing at 180 to 200 ° C (Univ. California, JACS 2004 , 126 , 1596). However, since the above-mentioned organic semiconductor is chemically unstable during the process for manufacturing a device, it is disadvantageous to apply it to an actual device manufacturing line, and when the current-electron sweeping is repeated with respect to the electrical stability, the voltage is delayed and the reliability is low .

On the other hand, U.S. Patent No. 6,683,782 discloses an organic compound containing an acetylene group and a method for producing the thin film by a vacuum deposition polymerization method. However, since the thin film is produced by a vacuum deposition method, it is not suitable in terms of price and large area as in the case of pentacene.

It is an object of the present invention to solve the problems of the prior art described above, and it is an object of the present invention to provide a method of manufacturing a semiconductor device capable of performing a solution process such as room temperature spin coating at the time of application of a device and also capable of manufacturing a chemically and electrically stable and reliable organic semiconductor Enediyne < / RTI > derivative of formula (I).

It is another object of the present invention to provide an organic semiconductor comprising an aromatic naphthoindene derivative and an electronic device including the same as a carrier transport layer.

According to an aspect of the present invention,

The present invention relates to an aromatic enediyne derivative represented by any of the following formulas (1) to (3).

[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,

X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted C3-C30 arylene group; And a substituted or unsubstituted C2-C30 heteroarylene group,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are each independently hydrogen; A halogen element; A nitro group; An amino group; Cyano; -SiR ¹ R ² R ³ wherein R ¹ , R ² , and R ³ are each independently hydrogen or a C 1 -C 10 alkyl group; A substituted or unsubstituted C1-C20 alkyl group; A substituted or unsubstituted C2-C20 alkenyl group; A substituted or unsubstituted C2-C20 alkynyl group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6-C20 arylalkyl group; A substituted or unsubstituted C6-C30 aryloxy group; A substituted or unsubstituted C2-C30 heteroaryloxy group; A substituted or unsubstituted C1-C20 heteroalkyl group; And a substituted or unsubstituted C2-C30 heteroarylalkyl group, provided that in Formula 1, R ₁ , R ₂ , R ₃ , and R ₄ are not simultaneously hydrogen, R ₅ and R ₆ are hydrogen at the same time, except that R ₃ and R ₄ in the above formula (3) are simultaneously hydrogen,

a, b, c, d, e and f are each independently an integer of 0 to 10, and a + b + c? 0 and c + d + f?

Another aspect of the present invention for achieving the above object is an organic semiconductor formed using the aromatic enedia derivative and an electronic device including the same as a carrier transport layer.

Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

The aromatic enediyne derivatives according to the present invention are represented by any one of the following formulas (1) to (3).

[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,

X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted C3-C30 arylene group; And a substituted or unsubstituted C2-C30 heteroarylene group,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are each independently hydrogen; A halogen element; A nitro group; An amino group; Cyano; -SiR ¹ R ² R ³ wherein R ¹ , R ² , and R ³ are each independently hydrogen or a C 1 -C 10 alkyl group; A substituted or unsubstituted C1-C20 alkyl group; A substituted or unsubstituted C2-C20 alkenyl group; A substituted or unsubstituted C2-C20 alkynyl group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6-C20 arylalkyl group; A substituted or unsubstituted C6-C30 aryloxy group; A substituted or unsubstituted C2-C30 heteroaryloxy group; A substituted or unsubstituted C1-C20 heteroalkyl group; And a substituted or unsubstituted C2-C30 heteroarylalkyl group, provided that in Formula 1, R ₁ , R ₂ , R ₃ , and R ₄ are not simultaneously hydrogen, and in Formula 2, R ₅ and R ₆ are hydrogen at the same time, except that R ₃ and R ₄ in the above formula (3) are simultaneously hydrogen,

a, b, c, d, e and f are each independently an integer of 0 to 10, and a + b + c? 0 and c + d + f?

In the case of using a plastic substrate in the production of a flexible display, since it can not withstand a heat curing temperature of 150 ° C or more, problems may arise in weight reduction and softening, while in the present invention, a low molecular substance having linear conjugated chains It is possible to manufacture an organic semiconductor thin film which can simultaneously perform a solution process at a low temperature by producing an organic semiconductor thin film using an aromatic enediyne derivative as a semiconductor material and simultaneously have a regularity of the molecular arrangement of the low molecular semiconductor and an electrical stability of the polymer have. The aromatic enediyne derivative used in the present invention is structurally composed of two acetylene groups bonded to a double bond of an aromatic substituent to form an unsaturated core and has a high reactivity due to its unique chemical structure and active mechanism, The radical benzene ring can be easily polymerized through intermolecular bonding by forming a chemical formula.

X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , Ar ₁ and Ar ₂ in the aromatic enediyl derivatives represented by the above Formulas 1 to 3 may be independently selected from the group represented by the following formula And more preferably a thiophene group or a phenyl group is preferable in terms of improving the mobility of the semiconductor.

[Chemical Formula 4]

을 제외하고 선택된다.)(Provided that Ar < 1 > and Ar &_lt; _{2 &}

. ≪ / RTI >

More specifically, the aromatic enediyne derivative may be represented by the following formula (5).

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 5 to 6, R represents a halogen element; A nitro group; An amino group; Cyano; -SiR ¹ R ² R ³ wherein R ¹ , R ² , and R ³ are each independently hydrogen or a C 1 -C 10 alkyl group; A substituted or unsubstituted C1-C20 alkyl group; A substituted or unsubstituted C2-C20 alkenyl group; A substituted or unsubstituted C2-C20 alkynyl group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6-C20 arylalkyl group; A substituted or unsubstituted C6-C30 aryloxy group; A substituted or unsubstituted C2-C30 heteroaryloxy group; A substituted or unsubstituted C1-C20 heteroalkyl group; And a substituted or unsubstituted C2-C30 heteroarylalkyl group,

m and n are each an integer of 1 to 10;

More specific examples of the aromatic enediyne derivative include compounds represented by the following formulas (6) to (9).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

The aromatic enediyne derivatives of the present invention can be synthesized using conventional methods and are not particularly limited.

Such an aromatic enedione derivative is used as a new organic semiconductor material composing an active layer and can be effectively applied to the manufacture of various electronic devices such as a thin film transistor, an electroluminescent device, a solar cell, or a memory.

Another aspect of the invention pertains to organic semiconductors formed using derivatives of these aromatic enediyes.

The organic semiconductor according to the present invention is coated on a substrate using a precursor solution containing an aromatic ene derivative and an organic solvent to form a coating film, followed by crosslinking the coating film by heat treatment to form a polymer.

The precursor solution may contain two or more different kinds of aromatic diene derivatives represented by the general formulas (1) to (3), and the aromatic diene derivative is preferably 0.01 to 30% by weight in the precursor solution .

Examples of the organic solvent used in the production of the organic semiconductor of the present invention include aliphatic hydrocarbon solvents such as hexane and heptane; Aromatic hydrocarbon solvents such as toluene, pyridine, quinoline, anisol, mesitylene and xylene; aromatic hydrocarbon solvents such as toluene, pyridine, quinoline, anisole, mesitylene and xylene; Ketone-based solvents such as methyl isobutyl ketone, 1-methyl-2-pyrrolidinone, cyclohexanone, and acetone, ); Ether-based solvents such as tetrahydrofuran and isopropyl ether; Acetate-based solvents such as ethyl acetate, butyl acetate, and propylene glycol methyl ether acetate; Alcohol-based solvents such as isopropyl alcohol and butyl alcohol; Amide solvents such as dimethylacetamide and dimethylformamide; Silicon-based solvent; And a mixture of the above-mentioned solvents.

When the precursor solution containing the aromatic enediyne derivative and the organic solvent is prepared, the precursor solution is coated on the substrate to form a coating film.

The substrate on which the organic semiconductor is formed is not particularly limited as long as it does not impair the object of the present invention. Examples of the substrate include a glass substrate, a silicon wafer, an ITO glass, a quartz, a silica coated substrate, A substrate or the like can be selected and used depending on the application.

Examples of the method of applying the precursor solution on a substrate include spin coating, dip coating, roll coating, screen coating, spray coating, spin casting a spin coating method, a flow coating method, a screen printing method, an ink jet method or a drop casting method may be used. The most preferred coating method in terms of convenience and uniformity is spin coating. In the case of spin coating, the spin rate is in the range of 100 to 10,000 rpm Lt; / RTI >

Then, the formed coating film is formed into a semiconductor thin film by cross-linking and polymerizing by a heat treatment furnace. It is preferable that the heat treatment is performed at a temperature of 100 to 250 DEG C, and the heating may be performed at an appropriate temperature in the temperature range for 1 minute to 100 minutes or sequentially.

An example of the mechanism of the cross-linking reaction of the above-mentioned aromatic enediyne derivative is shown in the following Reaction Scheme 2.

[Reaction Scheme 2]

As shown in Reaction Scheme 2, the acetylene group bonded at both ends of the aromatic double bond in the aromatic enediyne derivative forms a radical benzene ring when the reaction temperature reaches a certain temperature due to the high reactivity of the enediyne active agent. Thereby finally forming a polymer network.

In the case of forming a semiconductor thin film by using the existing precursor solution, unlike the case where cracks are generated in the thin film due to the ejection of gas generated in the solvent or intermolecular bonding in the heat treatment process, the organic semiconductor thin film according to the present invention has an endothermic Due to the high reactivity of the mechanism, it is polymerized through the radical reaction, which not only prevents the cracking problem of the thin film which can be generated by the gas generation during the continuous process but also acts as an impurity, It is possible to prevent counter-productive effects.

Organic semiconductors thus formed not only maintain excellent transistor characteristics due to the regular arrangement of monomolecular aromatic endian derivatives and intermolecular packing due to the formation of an intermolecular cross network but are also formed as a polymer type thin film, And reliability can be ensured. When applied to an electronic device as a carrier transporting layer, excellent physical properties can be provided, and a cost saving effect by a room temperature solution process can be maximized.

Examples of the electronic device include an organic thin film transistor, an electroluminescent device, a solar cell, and a memory. The aromatic enedium derivative of the present invention can be applied to the device by a conventional process known in the art .

Hereinafter, the present invention will be described in more detail by way of examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.

Manufacturing example  One : Aromatic Nendaiin  Synthesis of derivative A

A solution of 2,3-dibromothiophene (2 mL, 18.0 mmol) and 1-heptyne (3.5 mL, 27.0 mmol) in tetrahydrofuran / diisopropylamine (1: Palladium dichlorodiphosphine (0.23 g, 0.36 mmol) and copper iodide (70 mg, 0.36 mmol) and triphenylphosphine (0.1 g, 0.36 mmol) were added in this order. The solution was heated at 70 [deg.] C for 8 hours. Washed with an aqueous ammonium chloride solution, and the obtained organic layer was dried over magnesium sulfate, dried under reduced pressure and purified by silica gel column chromatography to obtain 4.6 g of 2-heptynyl 3-bromothiophene. 3.3 g (23.2 mmol) of trimethylsilylacetylene was added to the obtained compound, and 2.7 g (9.84 mmol) of 2-heptynyl-3-trimethylsilylethynylthiophene was obtained by the above- ). To this was added 12.8 mL (12.8 mmol) of lithium diisopropylamine (1M) at -70 [deg.] C. After stirring at the same temperature for 30 minutes, 2.4 mL (11.8 mmol) of dioxaborolane was added and the reaction was allowed to proceed to room temperature in the bath. Poured into 1N HCl aqueous solution, the organic layer was taken up with chloroform, dried over magnesium sulfate, and distilled under reduced pressure to obtain 4.1 g of an oil-like 1a . ^{1 H NMR (300 MHz, CDCl} 3), δ (ppm) 0.24 (s, 9H), 0.92 (t, 3H, J = 7.2 Hz), 1.24-1.64 (m, 18H), 2.49 (t, 2H, J = 7.0 Hz), 7.47 (s, 1 H)

1.6 g (4.00 mmol) of borolane 1a was added to 0.5 g (1.54 mmol) of 2,2'-dibromo-5,5'-bithiophene, (PPh ₃ ) ₄ [tetrakis (triphenylphosphine) palladium (0) (Aldrich)] catalyst and potassium carbonate (Pd) were added to toluene and water, ), The reaction was carried out at 110 ° C for 8 hours, and the organic layer was washed with 1N HCl aqueous solution. The organic layer was dried and purified by silica gel column chromatography to obtain 0.64 g (58%) of 2a . ^{1 H NMR (300 MHz, CDCl} 3), δ (ppm) 0.26 (s, 18H), 0.93 (t, 6H, J = 7.2 Hz), 1.24-1.67 (m, 12H), 2.50 (t, 4H, J = 7.0 Hz), 7.05 (d, 4H, J = 2.8 Hz), 7.34 (s, 2H)

0.54 g of 2a was dissolved in chloroform / methyl alcohol (1/3), 1 g of NaOH was added, and the mixture was stirred for 10 minutes. After washing with an aqueous 1N HCl solution, the organic layer was dried and purified by silica gel column chromatography to obtain 0.3 g of the derivative A. ^{1 H NMR (300 MHz, CDCl} 3), δ (ppm) 0.93 (t, 6H, J = 7.1 Hz), 1.35-1.67 (m, 12H), 2.51 (t, 4H, J = 7.0 Hz), 3.26 ( s, 2H), 7.05-7.07 (m, 6H)

Manufacturing example  2 : Aromatic Nendaiin  Synthesis of derivative B

0.25 g (1 mmol) of terthiophene was added to chloroform and 0.35 g (2.0 mmol) of N-bromosuccinimide was added to obtain dibromide 1b. The derivative B was synthesized by Suzuki coupling and desilylation under the same conditions as the synthesis of the derivative A. ^{1 H NMR (300 MHz, CDCl} 3), δ (ppm) 0.93 (t, 6H, J = 7.2 Hz), 1.24-1.67 (m, 12H), 2.51 (t, 4H, J = 7.0 Hz), 3.26 ( s, 2H), 7.05-7.08 (m, 8H)

Manufacturing example  3 : Aromatic Nendaiin  Synthesis of derivative C

Coupling of 2,2'-Dibromobithiophene with 2-bromothiophene was performed by Suzuki coupling, and N-bromosuccinimide was added to the obtained product to obtain dibromotetradiophene 1c. The derivative C was synthesized by Suzuki coupling and desilylation under the same conditions as the synthesis of the derivative A. ^{1 H NMR (300 MHz, CDCl} 3), δ (ppm) 0.93 (t, 6H, J = 7.2 Hz), 1.24-1.67 (m, 12H), 2.51 (t, 4H, J = 7.0 Hz), 3.27 ( s, 2H), 7.05-7.09 (m, 10H)

Manufacturing example  4 : Aromatic Nendaiin  Synthesis of derivative D

(4.2 mmol) of 1,4-dibromobenzene was coupled with 2-bromothiophene and Suzuki coupling, and 0.72 g (3.0 mmol) of the product was added to chloroform. 1.1 g (6.2 mmol) of N-bromosuccinimide 0.6 g of dibromide 1d was obtained. Derivative D was synthesized via Suzuki coupling and decylation under the same conditions as the synthesis of the derivative A. ^{1 H NMR (300 MHz, CDCl} 3), δ (ppm) 0.93 (t, 6H, J = 7.2 Hz), 1.24-1.67 (m, 12H), 2.51 (t, 4H, J = 7.0 Hz), 3.27 ( s, 2H), 7.01 (s , 2H), 7.13 (d, 2H, J = 3.8 Hz), 7.25 (d, 2H, J = 3.8 Hz), 7.60 (s, 4H)

Example  One : Fabrication of Organic Semiconductor Thin Films

First, an aluminum / niobium (Al / Nb) alloy used as a gate electrode was deposited on a cleaned plastic substrate by sputtering to a thickness of 1000 Å. SiO ₂ , which is used as a gate insulating film used as a gate insulating film, was deposited to a thickness of 1000Å by CVD.

And Au, which is used as a source-drain electrode, was deposited thereon to a thickness of 1200Å by sputtering. The substrate was washed with isopropyl alcohol for 10 minutes before the organic semiconductor material was deposited, dried and used. The sample was immersed in octadecyltrichlorosilane diluted to a concentration of 10 mM in hexane for 30 seconds, washed with acetone, and dried. Then, the endian derivative A obtained in Preparation Example 1 was added to the xylene solvent at a concentration of 0.1 wt% , Spin-coated on the substrate, and baked at 150 ° C for 30 minutes in an argon atmosphere to produce a bottom-contact type organic thin film transistor device shown in FIG.

Example  2-4 : Fabrication of Organic Thin Film Transistor

The organic thin film transistor device was fabricated in the same manner as in Example 1, except that the aromatic enantiomers B, C and D prepared in Preparation Examples 2 to 4 were used as the organic active layer forming material, respectively .

Differential scanning calorimetry was measured for the aromatic enediyne derivatives obtained in Production Examples 1 to 4, and the results are shown in Figs. 1 to 4. Fig.

Referring to FIGS. 1 to 4, it can be seen that the aromatic enediyne derivative according to the present invention starts to undergo crosslinking reaction at about 120 ° C., and the reaction proceeds actively at 200 ° C. or lower. As can be seen from the above results, it can be seen that the aromatic enenidine derivative according to the present invention can be formed into a semiconductor thin film through a low-temperature wet process.

A thermogravimetry analysis graph of the aromatic enediyne derivative obtained in Preparation Example 1-2 was measured, and the results are shown in FIGS. 5-6.

Referring to FIGS. 5-6, it can be seen that weight loss does not occur up to about 300 ° C. The absence of weight loss, even though the aromatic enediyne derivative of the present invention far exceeds the reaction temperature of 120-160 ° C, means that no more gas evolution occurs in the polymer formed. Therefore, it can be seen that the problem of cracking of the thin film due to the generation of gas can be prevented when the semiconductor thin film is formed using the aromatic enedia derivative of the present invention.

IR was measured to observe the structural change of the organic semiconductor thin film according to the temperature in the organic semiconductor thin film produced according to Example 1. The result is shown in FIG. Referring to FIG. 7, it can be seen that as the annealing temperature increases, the peaks of the triple bond (C≡C) and the hydrogen bond (? C-H) bonded thereto decrease. This means that the higher the temperature, the higher the enantiomer of the benzene ring.

In order to measure the electrical characteristics of the organic thin film transistor device manufactured according to Examples 1 to 4, current transfer characteristics were measured using Semiconductor Characterization System (4200-SCS) manufactured by KEITHLEY. The calculated values of charge mobility and blocking leakage current are shown in Table 1 below.

The charge mobility was obtained from the slope by obtaining a graph using the current transfer curve and using the current equation of the following saturation region as a variable, (I _SD ) ^1/2 and V _G :

Wherein, I _SD is the source-and-drain current, μ or μ _FET is also the charge transfer, C0 is oxide capacitance, W is the channel width, and L is channel length, V _G is the gate voltage, V _T Is the threshold voltage.

In addition, the blocking leakage current (I _off ) is a current flowing when the off state is obtained, and a minimum current is obtained from the off state at the current ratio.

 [Table 1]

The organic semiconductor layer Charge mobility (㎠ / Vs) Breaking leakage current (A) Example 1 7 x 10 ^-5 10 ^-11 Example 2 5 × 10 ^-4 10 ^-10 Example 3 8 × 10 ^-3 5 × 10 ^-11 Example 4 5 × 10 ^-4 10 ^-11

As can be seen from the above Table 1, the aromatic enediyne derivative of the present invention maintains the performance of the transistor and has a very low blocking leakage current of 10 < ^-10 > A or less and is suitable for thin film transistors, electroluminescent elements, It is possible to provide an organic semiconductor thin film excellent in electrical characteristics when applied to various electronic devices such as a semiconductor device.

As described above, the aromatic enedione derivative of the present invention can be applied to a semiconductor process requiring a large-area process because it can be coated by a room temperature wet process as a low-molecular organic semiconductor material of a new structure, and is stable not only chemically and electronically, It is possible to provide a reliable semiconductor thin film whose arrangement is regular and free from cracks. The organic semiconductor according to the present invention can be utilized in various fields such as an organic thin film transistor, an electroluminescence device, a solar cell, and a memory.

Claims (13)

An aromatic enediyne derivative represented by any one of the following formulas (1) to (3): [Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3, X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , Ar ₁ and Ar ₂ are each independently selected from the group represented by the following formula (4) R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are each independently hydrogen; A substituted or unsubstituted C1-C20 alkyl group (provided that R ₁ , R ₂ , R ₃ , and R ₄ are not simultaneously hydrogen, and R ₅ , when the R ₆ are hydrogen at the same time is excluded, and, if in the above general formula (3) is R _3, R ₄ are hydrogen at the same time is excluded), a, b, c, d, e and f are each independently an integer of 0 to 10, and a + b + c? 0 and c + d + f? [Chemical Formula 4]

(Provided that Ar < 1 > and Ar &_lt; _{2 &}

. ≪ / RTI > delete 2. The aromatic enediyne derivative according to claim 1, wherein the enediyne derivative comprises at least two thiophene rings in X ₁ , X ₂ , X ₃ , Ar ₁ and Ar ₂ of the formula (1) . The aromatic enediyne derivative according to claim 1, wherein the enediyne derivative is a compound represented by the following formula (5) or (6): [Chemical Formula 5]

[Chemical Formula 6]

In the above formulas (5) and (6) R is selected from the group consisting of a substituted or unsubstituted C1-C20 alkyl group, m and n are each an integer of 1 to 5; A precursor solution for the production of an organic semiconductor comprising an aromatic enediyne derivative according to any one of claims 1 to 3 and an organic solvent. [Claim 6] The precursor solution for organic semiconductor according to claim 5, wherein the precursor solution comprises two or more different aromatic dendrimers represented by the general formulas (1) to (3). 6. The precursor solution for the production of an organic semiconductor according to claim 5, wherein the aromatic enediyde derivative is 0.01 to 30% by weight in the precursor solution. 6. The method of claim 5, wherein the organic solvent is selected from the group consisting of an aliphatic hydrocarbon solvent such as hexane, heptane and the like; Aromatic hydrocarbon solvents such as toluene, pyridine, quinoline, anisol, mesitylene and xylene; aromatic hydrocarbon solvents such as toluene, pyridine, quinoline, anisole, mesitylene and xylene; Ketone-based solvents such as methyl isobutyl ketone, 1-methyl-2-pyrrolidinone, cyclohexanone, and acetone, ); Ether-based solvents such as tetrahydrofuran and isopropyl ether; Acetate-based solvents such as ethyl acetate, butyl acetate and propylene glycol methyl ether acetate; Alcohol-based solvents such as isopropyl alcohol and butyl alcohol; Amide solvents such as dimethylacetamide and dimethylformamide; Silicon-based solvent; And a mixture of the above-mentioned solvents. The precursor solution for the production of an organic semiconductor according to claim 1, The organic semiconductor according to claim 5, wherein the precursor solution is coated on a substrate to form a coating film, and the coating film is polymerized by crosslinking by heat treatment. The method of claim 9, wherein the precursor solution is selected from the group consisting of spin coating, dip coating, roll coating, screen coating, spray coating, spin casting, Wherein the organic semiconducting material is applied using a flow coating, a screen printing, an ink jet or a drop casting. The organic semiconductor according to claim 9, wherein the coating film is subjected to heat treatment crosslinking at 100 to 250 ° C. An electronic device comprising the organic semiconductor according to claim 9 as a carrier transporting layer. The electronic device according to claim 12, wherein the electronic device is a thin film transistor, an electroluminescent device, a solar cell, or a memory.

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