KR101081504B1 - High soluble polyacene derivative and organic electronic device using the same - Google Patents

Abstract

Disclosed are a polyacene derivative having excellent solubility characteristics as an organic semiconductor material and an organic electronic device using the same. The present invention provides a polyacene derivative having a novel structure and an organic electronic device using the same, which have high thermal mobility, excellent thermal stability, excellent solubility and oxidation resistance in general solvents, and which can be manufactured in a solution process.

Polyacene, organic electronic device, solution, derivative

Description

High soluble polyacene derivative and organic electronic device using the same

The present invention relates to a polyacene derivative having excellent solubility characteristics as an organic semiconductor material and an organic electronic device using the same.

Since it has been known since the late 1970s that proper doping of certain organics can bring the electrical conductivity close to copper, current organics are not only in terms of conductivity, but also from semiconductors, conductors (such as doped polyacetylene), from the best insulators (polystyrene, etc.). Not only that, but the superconductor (TMTSF) 2PF6, perchlorate, pentacen, etc., the best conductors, can be obtained in all parts of the material. Examples of semiconductors include p-type pentacene and n-type Alq ₃ , and dielectrics include ferroelectric PVDF and co-polymers based thereon.

In recent decades, the development of organic materials with semiconductor properties and various application studies using them have been actively conducted. The scope of application research using organic semiconductors such as electromagnetic shielding films, capacitors, organic electroluminescence (EL) displays, organic thin film transistors, solar cells, and memory devices using multiphoton absorption phenomena continues to expand. In particular, the organic EL field is partly commercialized and serves as a catalyst for activating applied research using organic materials in the electronic field.

Organic thin film transistors using organic materials are being studied for application to next-generation smart cards, starting with the use of active driving devices for organic EL. In addition, after the electrical oscillation characteristics using the organic semiconductor as an active layer were announced, research on the possibility of application as a laser diode and a research report on the high efficiency (2.4%) solar cell using the doped organic material (pentacene) were carried out. Active research is being conducted in the field of organic semiconductors, which are significantly lower in device fabrication cost.

In addition, since flexible electronic circuit boards are expected to be an important element technology for future industries, the development of organic thin film transistors capable of meeting these needs is emerging as an important research field. Organic thin film transistors cannot be used in high-speed devices that use silicon (Si) or germanium (Ge) due to their low charge mobility due to the characteristics of organic semiconductors. This is a useful aspect since it can be used and in particular a low cost process is possible. Recently, researchers at Philips have published a programmable code generator consisting of 326 transistors using substrates, electrodes, organic dielectrics (insulators), and organic semiconductors all using polymers.

The organic thin film transistor implemented on the plastic substrate can be applied to the driving of bendable liquid crystal display devices, electronic paper and organic light emitting devices. In particular, recently developed electronic paper is a display device that does not require high charge mobility and fast switching speed by voltage driving, and is a technology suitable for application to a large area that can be bent, and is highly applicable to an organic thin film transistor.

Research on organic thin film transistors began in the early 1980s and recently, full-scale research is being conducted worldwide. The transistor device includes a substrate, a gate electrode, an insulating film, a channel layer, a source / drain electrode, and a protective layer to prevent external moisture and oxygen transmission. Organic thin film transistors are fabricated using organic compounds or polymers that represent semiconducting properties that can replace the conventional silicon-based inorganic materials in the channel layer, which is the key part of charge transfer and most affects device characteristics. As the organic semiconductor material, polyacene compounds such as anthracene, tetracene, pentacene, and the like have been studied along with polyphenylenevinylene, polypyrrole, polythiophene and oligothiophene. Since it is strong, it has high crystallinity and thereby has high carrier mobility. Organic semiconductor materials are classified into n-type materials that move electrons and p-type materials that transport holes. At present, it is a low molecular organic semiconductor material such as pentacene that exhibits high charge mobility among p-type organic semiconductors.

Polyacene compounds such as pentacene have a high π-π affinity resulting from aromatic molecules between neighboring molecules, and thus have high crystallinity and excellent charge mobility properties. Recent publications have reported high charge mobility of 3.2 to 5.0 cm ² / Vs using pentacene single crystals in Lucent Technologies or 3M (Mater. Res. Soc. Symp. Proc. Vol. 771, L6. 5.1 to L6.5.11 (2003). France's CNRS also uses oligothiophene derivatives to report relatively high charge mobility and current flicker ratios from 0.01 to 0.1 cm ² / Vs. However, the prior art has a disadvantage in that expensive vacuum equipment is required in order to manufacture a thin film required for device fabrication, and expensive process equipment is required and the process cost is high.

In order to solve this problem, researches are being developed to develop polyacene derivatives such as anthracene and pentacene, which can be solution-processed. The organic thin film transistor device exhibiting a charge mobility of 0.1 to 0.2 cm ² / Vs was reported as a method of implementing pentacene by treatment (PT Herwig and K. M, Adv . Mater . Vol. 11, p.480 (1999). )). Anthony (Anthony) researchers to impart solubility triisopropylsilyl ethynyl (triisopropylsilylethynyl) groups are pentamethyl to develop the derivative bonded to the sensor on both sides up to 1.5 cm ² / Vs enough charge movement in the solution process of the US University of Kentucky also An implementation of an organic thin film transistor device exhibiting characteristics has been reported (JE Anthony, et.al., J. Am . Chem . Soc ., Vol . 123, p . 9482 (2001); JE Anthony, et.al., Tech . Dig .- Int. Electron Devices Meet . , p. 113 (2006). In order to impart solubility, researchers at the University of Wurzburg (W) in Germany have developed a pentacene derivative in which trimethoxyphenylethynyl groups are introduced as substituents on both sides of pentacene to implement organic thin film transistor devices. (F. W, et . Al ., J. Mater . Chem . , Vol . 16, p . 3708 (2006)). However, these derivatives exhibited very low thermal and oxidative stability and low charge mobility.

In order to apply a polyacene-based organic semiconductor material such as pentacene to the solution process, it is generally necessary to increase the solubility by introducing a bulky or aliphatic alkyl substituent to pentacene, but at the same time, the thermal stability, oxidation stability, and high charge of the material Intermolecular affinity enhancement and crystallization techniques for mobility are also key requirements in the design and manufacture of organic semiconductor materials.

The present invention is to solve the problems of the prior art as described above, by introducing a substituent structure of benzylacetylene and thiophenylacetylene-based polyacene derivatives containing an anthracene structure to improve the solubility, crystallinity and stability of the compound To provide an organic semiconductor material and an organic electronic device comprising the same, which exhibits high hole mobility and excellent thermal stability, excellent solubility and oxidation resistance in general solvents for manufacturing organic electronic device in a solution process The purpose.

The present invention relates to a polyacene-based organic electronic device compound having excellent solubility characteristics, and is composed of a polyacene derivative including anthracene having excellent hole mobility characteristics, and is a functional group of saturated hydrocarbon (hexyl group) to increase solubility. consist of. It is designed to show the high hole mobility and the solution processing property in the same compound structure at the same time. Hexyl benzene group and hexyl thiophene group in the center of the anthracene, solubility is increased to enable the solution process. This is an example of effectively increasing the solubility characteristics of the organic semiconductor material that has been a problem in the past.

The present invention provides a compound for an organic electronic device represented by the following formula (1) in order to achieve the above object:

[Formula 1]

Wherein Ar ₁ is selected from the group consisting of naphthalene, anthracene, tetracene or pentacene,

Ar ₂ and Ar ₃ are each independently a 5- or 6-membered heterocycloalkyl including one or more selected from (C ₆ -C ₆₀ ) arylene, (C ₃ -C ₆₀ ) heteroarylene, N, O and S Ethylene, (C ₃ -C ₆₀ ) cycloalkylene, adamantylene, (C ₇ -C ₆₀ ) bicycloalkylene, (C ₂ -C ₆₀ ) alkenylene, (C ₂ -C ₆₀ ) alkynylene, ( C ₆ -C ₆₀ ) ar (C ₁ -C ₆₀ ) alkylene, (C ₁ -C ₆₀ ) alkylenethio, (C ₁ -C ₆₀ ) alkyleneoxy, (C ₆ -C ₆₀ ) aryleneoxy or (C ₆ -C ₆₀ ) arylenethio, and

R ₁ and R ₂ each independently include one or more selected from hydrogen, deuterium, halogen, (C ₁ -C ₆₀ ) alkyl, (C ₆ -C ₆₀ ) aryl, N, O and S (C ₃ -C ₆₀₎ heteroaryl, morpholino, tea Omo poly furnace, N, O, and 5-ring or 6-ring heterocycloalkyl containing one or more selected from S, (C ₃ -C ₆₀₎ cycloalkyl, tri (C ₁ - C ₆₀ ) alkylsilyl, di (C ₁ -C ₆₀ ) alkyl (C ₆ -C ₆₀ ) arylsilyl, tri (C ₆ -C ₆₀ ) arylsilyl, adamantyl, (C ₇ -C ₆₀ ) bicycloalkyl , (C ₂ -C ₆₀ ) alkenyl, (C ₂ -C ₆₀ ) alkynyl, (C ₁ -C ₆₀ ) alkoxy, cyano, (C ₆ -C ₆₀ ) ar (C ₁ -C ₆₀ ) alkyl, (C ₁ -C ₆₀ ) alkyloxy, (C ₁ -C ₆₀ ) alkylthio, (C ₆ -C ₆₀ ) aryloxy, (C ₆ -C ₆₀ ) arylthio, (C ₁ -C ₆₀ ) alkoxycarbonyl , (C ₁ -C ₆₀ ) alkylcarbonyl, (C ₆ -C ₆₀ ) arylcarbonyl, (C ₆ -C ₆₀ ) aryloxycarbonyl, (C ₁ -C ₆₀ ) alkoxycarbonyloxy, (C ₁ -C ₆₀ ) alkylcarbonyloxy, (C ₆ -C ₆₀ ) arylcarbonyloxy, (C ₆ -C ₆₀ ) aryl Oxycarbonyloxy, (C ₁ -C ₆₀ ) alkylcarbonyloxy, (C ₆ -C ₆₀ ) arylcarbonyloxy, carboxyl, nitro or hydroxy, wherein adjacent substituents are bonded to each other Saturated or unsaturated fused rings can be formed.

Ar ₁ may be exemplified as a polyacene selected from the following structures, but is not limited thereto.

In addition, Ar ₂ and Ar ₃ may be selected from the following structures independently from each other, but is not limited thereto.

Wherein R ₃ to R ₁₁ are each independently selected from hydrogen, deuterium, (C ₁ -C ₆₀ ) alkyl, (C ₃ -C ₆₀ ) cycloalkyl, (C ₆ -C ₆₀ ) aryl or N, O and S It is selected from the group consisting of (C ₃ -C ₆₀ ) heteroaryl containing one or more.

R ₁ and R ₂ may be independently selected from the following structures, but are not limited thereto.

R ₂₁ to R ₃₁ are each independently hydrogen, deuterium, (C ₁ -C ₆₀ ) alkyl, (C ₃ -C ₆₀ ) cycloalkyl, (C ₆ -C ₆₀ ) aryl or one selected from N, O and S It may be selected from the group consisting of (C ₃ -C ₆₀ ) heteroaryl containing the above.

The polyacene derivatives of the present invention can be synthesized using conventional methods, and are not particularly limited. Synthesis process of the polyacene derivative, wherein Ar ₁ is an anthracene in Formula 1 is illustrated in Scheme 1 below, and the following preparation method does not limit the method of preparing the polyacene derivative of Formula 1 according to the present invention. Modifications of the preparation method will be apparent to those skilled in the art, and unless otherwise stated, the definitions of the substituents in the following schemes are the same as those in the general formula (1).

[Scheme 1]

Intermediate Compound A was synthesized by reacting 1-bromo-4-hexylbenzene and trimethyl silyl acetylene at 50 to 70 ° C. for 12-24 hours, and reacting Compound A with potassium carbonate at room temperature for 3-10 hours to obtain trimethyl silyl. The removed intermediate compound B can be synthesized. Intermediate C can be synthesized by reacting 2,6-diaminoanthracene-9,10-dione with tert-butyl nitrite and cooperbromide at 65 ° C. for 6-12 hours. Intermediate D may be synthesized by sequentially treating normal butyllithium, hydrochloric acid, and tin chromide to react the intermediate compound B with the intermediate compound C. The intermediate compound D and tributyl (5-hexylthiophen-2-yl) stannein may be reacted at 90 ° C. for 12-24 hours to synthesize the final compound HB-ant-HT.

In order to increase the purity of the intermediate compound and final compound in each synthesis step, the compound is purified by recrystallization, pressure distillation, column chromatography, and the like. Purity and structure confirmation of the compound can be performed using a nuclear magnetic resonance spectrometer, gas chromatography, melting point measurement.

Polyacene-based compound having an anthracene structure of formula (1) according to the present invention is preferably for an organic thin film transistor, can be implemented as an organic thin film transistor interposed between the first electrode and the second electrode, in particular, substrate, source-drain In an organic thin film transistor including an electrode, an organic semiconductor thin film, an insulating film, and a gate electrode, the organic semiconductor thin film may be formed of at least one polyacene compound including an anthracene structure of Formula 1 according to the present invention. The organic thin film transistor device according to the present invention may be manufactured according to a general device structure, and may take a bottom gate method in which a substrate, a gate electrode, an insulating film, an organic base film, a source, and a drain electrode are sequentially manufactured, or a substrate / source-drain. A top gate method of an electrode / derived conductor thin film / insulating film / gate electrode can be taken.

In this case, the polyacene-based compound including an anthracene structure, which is an organic semiconductor material of the present invention, may be dissolved in an organic solvent to form a thin film by spin coating, drop casting, or inkjet coating, and applied to a device. The organic solvent may be dichlorobenzene, trichloroethane, N-methylpyrrolidone, toluene and the like, but is not limited thereto. In addition, the polyacene-based compound including the anthracene structure is mixed with at least one organic polymer compound selected from polyalphamethylstyrene, amorphous polycarbonate, or polycarbazole, dissolved in an organic solvent to form a thin film by the coating method. Can be formed.

As the gate insulating film of the organic thin film transistor of the present invention, SiO ₂ formed on a silicon substrate can be used, or a polymer insulating film such as Cytop (Japan Asahi Glass Co., Ltd.) or polyvinylphenol can be used.

The polyacene derivative compound according to the present invention is excellent in thermal stability while implementing high hole mobility, and excellent in solubility and oxidation resistance in general solvents, thus enabling device fabrication by a solution process.

Hereinafter, a method for synthesizing a polyacene derivative and a method for manufacturing an organic electronic device using the same will be described in more detail.

Example 1 Synthesis of 2,6-Dibromo-9,10-bis ((4-hexylphenyl) ethynyl) anthracene (3.HB-ant-Br)

In a 250 mL magnetic stirred round bottom flask dried in an oven, 1-ethynyl-4-hexylbenzene (0.720 g, 3.86 mmol) was dissolved in just distilled tetrahydrofuran (30 mL). The solution was then cooled to −78 ° C. and then n -butyllithium ( n- BuLi (1.57 mL, 3.92 mmol, 2.5 M sol'n. In hexane)) was added dropwise over 15 minutes. The solution was stirred for 30 minutes and 2,6-dibromoanthracene-9,10-dione (2,6-dibromoanthracene-9,10-dione, 0.574 g, 1.57 mmol) was added at -78 ° C. The solution was stirred at room temperature for 3 hours, and then water, tin chloride and hydrochloric acid were added to terminate the reaction. After completion of the reaction, the solution was poured into methanol to collect a precipitate. At this time, the yield was 0.740 g, the yield was 67%. ¹ H NMR and HRMS data of the obtained material are as follows.

¹ H-NMR (400 MHz, CDCl ₃ ): (ppm) 8.77 (s, 2H), 8.49 (d, J = 9.4 Hz, 2H), 7.64-7.68 (m, 6H), 7.28 (d, J = 7.8 Hz, 4H), 2.68 (t, 4H), 1.62-1.70 (m, 4H), 1.30-1.39 (m, 12H), 0.90 (t, 6H).

(EA analysis) C ₄₂ H ₄₀ Br ₂ : C, 71.60 H, 5.72, found: C, 71.62; H, 5. 64.

Example 2 Synthesis of 2,6-Dibromo-9,10-bis (phenylethynyl) anthracene (4.B-ant-Br)

The manufacturing method is the same as in Example 1. Ethinylbenzene was used instead of 1-ethynyl-4-hexylbenzene of Example 1. After completion of the reaction, the solution was poured into methanol to collect a precipitate. The yield was 1.85 g and the yield was 63%. ¹ H NMR and HRMS data of the obtained material are as follows.

¹ H-NMR (400 MHz, CDCl ₃ ): (ppm) 8.77 (s, 2H), 8.48 (d, J = 9.0 Hz, 2H), 7.75 (d, J = 7.4 Hz, 4H), 7.66 (d, J = 4.5 Hz, 2H), 7.42-7.48 (m, 6H).

(EA analysis) C ₃₀ H ₁₆ Br ₂ : C, 67.19 H, 3.01, Pound: C, 67.22; H, 3.01.

Example 3 5,5 ′-(9,10-bis ((4-hexylphenyl) ethynyl) anthracene-2,6-diyl) bis (2-hexylthiophene) (7.HB-ant-HT )

In a 100 mL round bottom flask for magnetic stirring, dried in an oven, the solution of [Example 1] (0.650 g, 0.923 mmol) and tributyl (5-hexylcysyl) in just distilled N, N-dimethylformamide (30 mL) Offen-2-yl) stannene (1.69 g, 3.70 mmol) was added together. The reaction was stirred for 0.5 h and then tetrakis (triphenylphosphine) palladium (0) (0,213 g, 0.185 mmol) was added. The mixture was stirred at 90 ° C. for 12 h. After the reaction was completed, the solution was poured into ethanol to collect a precipitate. Yield was 0.705 g, 87%. ¹ H NMR and HRMS data of the obtained material are as follows.

¹ H-NMR (400 MHz, CDCl ₃ ): (ppm) 8.80 (s, 2H), 8.61 (d, J = 9.0 Hz, 2H), 7.85 (d, J = 9.0 Hz, 2H), 7.73 (d, J = 8.2Hz, 4H), 7.38 (d, J = 3.5Hz, 2H), 7.30 (d, J = 8.2Hz, 4H), 6.84 (d, J = 3.5Hz, 2H), 2.89 (t, 4H) , 2.69 (t, 4H), 1.72-1.80 (m, 4H), 1.64-1.72 (m, 4H), 1.33-1.46 (m, 24H), 0.89-0.93 (m, 12H).

(EA analysis) C ₆₂ H ₇₀ S ₂ : C, 84.68 H, 8.02 S, 7.29, Pound: C, 84.71; H, 7.98; S, 7.14.

Example 4 5 ', 5'-(9,10-bis ((4-hexylphenyl) ethynyl) anthracene-2,6-diyl) bis (5-hexyl-2,2'bithiophene) ( 8.HB-ant-HBT)

The synthesis method is the same as in [Example 3] . Tributyl (5'-hexyl-2,2'-bithiophen-5-yl) stannein is substituted for the tributyl (5-hexylthiophen-2-yl) stannein of Example 3 Was used. After completion of the reaction, the solution was poured into ethanol to collect a precipitate. Yield was 1.38 g, 71%. ¹ H NMR and HRMS data of the obtained material are as follows.

¹ H-NMR (400 MHz, CDCl ₃ ): (ppm) 8.86 (s, 2H), 8.66 (d, J = 8.6 Hz, 2H), 7.90 (d, J = 8.6 Hz, 2H), 7.78 (d, J = 8.2Hz, 4H), 7.49 (d, J = 3.9Hz, 2H), 7.35 (d, J = 8.2Hz, 4H), 7.20 (d, J = 3.5, 2H), 7.13 (d, J = 3.5 , 2H), 6.78 (d, J = 3.5, 2H), 2.88 (t, 4H), 2.75 (t, 4H), 1.71-1.80 (m, 8H), 1.39-1.48 (m, 24H), 0.97 (t , 12H). (EA analysis) C ₇₀ H ₇₄ S ₄ : C, 80.56 H, 7.15 S, 12.29, Pound: C, 80.58; H, 7. 20; S, 12.07.

Example 5 5,5 '-(9,10-bis (phenylethynyl) anthracene-2,6-diyl) bis

(2-hexylthiophene) (9.B-ant-HT)

In a 100 mL round bottom flask for magnetic stirring, dried in an oven, the solution of [Example 2] (1.00 g, 1.86 mmol) and tributyl (5-hexyl) in just distilled N, N-dimethylformamide (50 mL) Thiophen-2-yl) stannene (3.419 g, 7.46 mmol) was added. The reaction was stirred for 0.5 h and then tetrakis (triphenylphosphine) palladium (0) (0.430 g, 0.372 mmol) was added. The mixture was stirred at 90 for 12 hours. After completion of the reaction, the solution was poured into ethanol to collect a precipitate. Yield was 1.10 g, 83%. ¹ H NMR and HRMS data of the obtained material are as follows. ¹ H-NMR (400 MHz, CDCl ₃ ): (ppm) 8.76 (s, 2H), 8.58 (d, J = 8.6 Hz, 2H), 7.84 (d, J = 9.0 Hz, 2H), 7.76-7.82 ( m, 4H), 7.44-7.51 (m, 6H), 7.37 (d, J = 3.5 Hz, 4H), 6.84 (d, J = 3.5, 2H), 2.88 (t, 4H), 1.72-1.79 (m, 4H), 1.32-1.46 (m, 12H), 0.91 (t, 6H). (EA analysis) C ₅₀ H ₄₆ S ₂ : C, 84.46 H, 6.52 S, 9.02, Pound: C, 84.46; H, 6. 59; S, 9.22.

Example 6 5 ', 5'-(9,10-bis (phenylethynyl) anthracene-2,6-diyl) bis (5-hexyl-2,2'bithiophene) (10.B-ant -HBT)

The synthesis method is the same as in [Example 5] . Tributyl (5'-hexyl-2,2'-bithiophen-5-yl) stannein is substituted for the tributyl (5-hexylthiophen-2-yl) stannein of Example 5 Was used. After completion of the reaction, the solution was poured into ethanol to collect a precipitate. Yield was 0.983 g, 57%. ¹ H NMR and HRMS data of the obtained material are as follows.

¹ H-NMR (400 MHz, CDCl ₃ ): (ppm) 8.89 (s, 2H), 8.69 (d, J = 9.0 Hz, 2H), 7.94 (d, J = 9.0 Hz, 2H), 7.88 (d, J = 7.8Hz, 4H), 7.50 ~ 7.56 (m, 6H), 7.27 (d, J = 7.8Hz, 2H), 7.21 (d, J = 3.9, 2H), 7.13 (d, J = 3.5, 2H) , 6.79 (d, J = 3.5, 2H), 2.88 (t, 4H), 1.74-1.81 (m, 4H), 1.39-1.48 (m, 12H), 0.97 (t, 6H).

(EA analysis) C ₅₈ H ₅₀ S ₄ : C, 79.59 H, 5.76 S, 14.65, found: C, 79.52; H, 5.87; S, 14.69.

Example 7 UV-Visible Absorbance Irradiation Before and After Annealing of HB-ant-HT

Solution state (solvent: chloroform, concentration: 1x10 mole / L, solid line), spin-coated (as-spun, dotted line) and thin film state after annealing as measured by UV-Vis spectrometer (HP8453, Photodiode array type) Ultraviolet-visible light spectrum for (annealed film, dashed line) is shown in FIG. Annealing was carried out at 170 to 30 minutes. The as-coated thin film before the heat treatment of FIG. 2 shows a spectrum almost similar to the heat treatment. This means that even if the compound according to the present invention is formed into a thin film and further subjected to heat treatment, the orderness of the molecular arrangement is already fully developed in the thin film formation step before the heat treatment, so that there is no further significant change.

Example 8 Investigation of XRD Pattern of HB-ant-HT

XRD experiments were performed under temperature conditions using Synchrotron Radiation (1.542 Å Pohang Synchrotron Laboratory). The pattern that the thin film of spincoated HB-ant-HT shows during the heating and cooling cycles is shown in FIG. 3. The thin film was formed via drop-casting on a silicon wafer and dried to 70 in vacuo (solvent: chloroform, concentration: 10 mg / ml). The diffraction pattern at each temperature is the result of the thin film produced for 5 minutes at each temperature. Optimized molecular alignment analysis was performed by measuring the length of the molecules via the DFT method (Spartan'06).

Example 9 AFM Image Irradiation of HB-ant-HT Thin Film

AFM (Digital Instrument Multimode, including nanoscope IIIa controller) observed the surface of the sample using a silicon cantilever in tapping mode. Thin film samples were applied onto silicon wafers by spin coating (1500 rpm), followed by annealing and dried in vacuo to 170 (solvent: chloroform, concentration: 10 mg / ml). 4 shows that the thin film structure of the present invention prepared at room temperature already exists in a form of organic packing between molecules before heat treatment, and the organic packing between molecules is further after heat treatment. It is showing an increase.

Example 10 Fabrication of Organic Thin Film Transistor (OTFT)

To verify its function as a thin film transistor, HB-ant-HT was spin-coated to 40-50 nm thick using chloroform as a solvent on a strongly n-doped Si / SiO 2 substrate. The surface was treated with octyltrichlorosilane (OTS) to create a hydrophobic dielectric surface. Source and drain electrodes were deposited (100 nm) through shadow masks having channels of width and length of 1500 um and 150 um, respectively. All field effect mobility is calculated by μ _sat = (2I _DS L) / (WC (V _g -V _th ) ² ) , where I _DS saturation drain current, C is capacitance of oxide dielectric , V _g denotes a gate bias, and V _th denotes a threshold voltage. The performance of the manufactured equipment was measured with a Keithley 237 high voltage source meter at room temperature. 5 shows that the organic thin film according to the present invention exhibits high field-effect mobility of 0.01 cm ² / Vs.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the invention as defined in the appended claims. It will be understood that the invention may be varied and varied without departing from the scope of the invention. Many embodiments other than the above-described embodiments are within the scope of the claims of the present invention.

1 is a cross-sectional view of a transistor device including an organic semiconductor layer made of a polyacene derivative compound including an anthracene structure according to an embodiment of the present invention.

Figure 2 shows the ultraviolet-visible absorption spectrum of the compound in the solution state and the film state according to Example 3 of the present invention.

Figure 3 shows the XRD spectrum which can confirm the crystallinity of the compound in the film state according to Example 3 of the present invention.

Figure 4 shows the AFM image which can confirm the crystallinity of the compound in the film state according to Example 3 of the present invention.

Figure 5 shows the current density according to each hole movement made of a polyacene derivative compound containing an anthracene structure according to Example 3 of the present invention.

Claims (8)

Anthracene-based derivatives represented by Formula 1 below: [Formula 1]

Wherein Ar ₁ is an anthracene; Ar ₂ and Ar ₃ are each independently (C ₆ -C ₆₀ ) arylene or (C ₃ -C ₆₀ ) heteroarylene; R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, (C ₁ -C ₆₀ ) alkyl and (C ₃ -C ₆₀ ) heteroaryl, and adjacent substituents are bonded to each other to form a saturated or unsaturated fused ring can do. Here, relative to the anthracene molecules to the substitution site of Ar ₂ and Ar ₃ expression to indicate the symmetry in vertical and horizontal directions, and Ar ₂ is (2,6), and Ar ₃ is (9, 10). [Formula 2]

delete delete delete An organic electronic device comprising an organic semiconductor thin film formed using one or more of the compounds according to claim 1. The organic electronic device of claim 5, further comprising an organic semiconductor thin film formed by dissolving the compound in an organic solvent using spin coating, drop casting, or ink jet coating. The organic electronic device of claim 5, wherein the organic semiconductor thin film further comprises one or more organic polymer compounds selected from polyalphamethylstyrene, amorphous polycarbonate, or polycarbazole. The organic electronic device of claim 6, wherein the organic solvent is selected from the group consisting of dichlorobenzene, trichloroethane, N-methylpyrrolidone, and toluene.

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