KR20190013429A - Organic compound and organic thin film and electronic device - Google Patents

Abstract

The present invention relates to: a compound represented by chemical formula 1A; a compound represented by chemical formula 1B; an organic compound selected from combinations thereof; an organic thin film comprising the organic compound; an organic thin film transistor; and an electronic device. The organic compound has liquid crystal properties by having an asymmetric substituent, and in case of heat treating the organic compound in a liquid crystal section, the organic compound exhibits an ordered liquid crystal phase, thereby being able to further increase charge mobility.

Description

ORGANIC COMPOUND AND ORGANIC THIN FILM AND ELECTRONIC DEVICE BACKGROUND OF THE INVENTION 1. Field of the Invention [0001]

Organic compounds, organic thin films and electronic devices.

2. Description of the Related Art A flat panel display device such as a liquid crystal display (LCD), an organic light emitting diode (OLED) display, and an electrophoretic display includes a plurality of pairs of electric field generating electrodes And an electro-optic active layer contained therein. In the case of a liquid crystal display device, a liquid crystal layer is included as an electro-optical active layer, and an organic light emitting layer is included as an electro-optical active layer in an organic light emitting display device.

One of the pair of electric field generating electrodes is usually connected to the switching element to receive an electric signal, and the electro-optic active layer converts the electric signal into an optical signal to display an image.

In a flat panel display device, a thin film transistor (TFT), which is a three terminal device, is used as a switching device, and a gate line for transmitting a scan signal for controlling the thin film transistor and a signal to be applied to the pixel electrode A data line to be transmitted is provided in the flat panel display.

Among these thin film transistors, organic thin film transistors (OTFTs) including organic semiconductors such as low-molecular or high-polymer materials are being actively studied instead of inorganic semiconductors such as silicon (Si).

Organic thin film transistors have attracted attention as a key element of flexible display devices because they can be made in the form of fibers or films due to the nature of organic materials. Also, since the organic thin film transistor can be manufactured by a solution process such as inkjet printing, the organic thin film transistor can be easily applied to a large area flat panel display device which is limited only by a deposition process.

One embodiment provides organic compounds that can be applied to electronic devices such as organic thin film transistors.

Another embodiment provides an organic thin film comprising the organic compound.

Another embodiment provides an electronic device comprising the organic thin film.

According to one embodiment, there is provided an organic compound selected from a compound represented by the formula (1A), a compound represented by the formula (1B), and combinations thereof.

≪ EMI ID =

≪ RTI ID = 0.0 &

In the above formulas 1A and 1B,

Ar ¹ and Ar ² are each independently benzene, naphthalene or anthracene,

X ¹ to X ⁴ each independently represent O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom or a combination thereof,

n1, n2 and n3 are each independently 0 or 1,

R ¹ to R ⁴ are each independently hydrogen, a halogen atom, a substituted or unsubstituted straight or branched chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain or branched C2 to C30 alkenyl group, a substituted or unsubstituted straight- A substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, C30 alkylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, or a combination thereof,

R ¹ and R ² are groups having different structures, or R ³ and R ⁴ are groups having different structures.

When n1 = 0, n2 = n3 = 0 or n2 = n3 = 1, and when n1 = 1, n2 = n3 = 0 can be satisfied.

Any one of R ¹ and R ² is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,

The other of R ¹ and R ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,

R ³ and R ⁴ are each independently hydrogen or a halogen atom; or

Either of R ³ and R ⁴ is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,

The other of R ³ and R ⁴ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 A substituted or unsubstituted C7 to C30 arylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 A heterocycloalkyl group, or a combination thereof,

R ¹ and R ² may each independently be hydrogen or a halogen atom.

Also, any one of R ¹ and R ² is a substituted or unsubstituted branched C3-C30 alkyl group, a substituted or unsubstituted branched C4-C30 alkenyl group, a substituted or unsubstituted branched C4-C30 alkynyl group, Lt; / RTI >

The other of R ¹ and R ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,

R ³ and R ⁴ are each independently hydrogen or a halogen atom; or

Any one of R ³ and R ⁴ is a substituted or unsubstituted branched C3-C30 alkyl group, a substituted or unsubstituted branched C4-C30 alkenyl group, a substituted or unsubstituted branched C4-C30 alkynyl group, Lt; / RTI &

The other of R ³ and R ⁴ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,

R ¹ and R ² may each independently be hydrogen or a halogen atom.

In the above formula (1A) or (1B), X ⁴ is S, R ² is a fluorine-substituted C 6 to C 30 aryl group, a fluorine-substituted C 2 to C 30 heteroaryl group, a fluorine-substituted C 7 to C 30 alkylaryl group, fluoro A substituted C2 to C30 alkylheteroaryl group, a fluoro substituted C5 to C30 cycloalkyl group, a fluoro substituted C2 to C30 heterocycloalkyl group, or a combination thereof.

In the above formula (1A) or (1B), R ² may be a substituted or unsubstituted pentagonal ring, a substituted or unsubstituted hexagonal ring, or a combination thereof.

In the above formula (1A) or (1B), R ² may be a heterocyclic group represented by the following formula (2A) or (2B), a substituted or unsubstituted alkylaryl group represented by the following formula (2C), or a combination thereof.

(2A)

(2B)

[Chemical Formula 2C]

In the above formulas (2A), (2B) and (2C)

X ⁵ is O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom, or a combination thereof,

X < ⁶ > is N,

R ⁵ R ⁶ and R ⁷ are each independently selected from the group consisting of a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,

a is an integer of 0 to 3,

b is an integer of 0 to 4,

c is an integer of 0 to 4,

R ^a and R ^b are each independently hydrogen or a C 1 to C 6 alkyl group and m is 0 to 20, and when m is 2 or more, - (CR ^a R ^b ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,

R ^c and R ^d are each independently hydrogen or a C 1 to C 6 alkyl group and n is 0 to 20, and when n is 2 or more, - (CR ^c R ^d ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,

R ^e and R ^f are each independently hydrogen or a C 1 to C 6 alkyl group and r is 0 to 20, and when r is 2 or more, - (CR ^e R ^f ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,

* Is the connection point.

And either one of R ¹ and R ² is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group, ,

And the other of R ¹ and R ² is a substituted or unsubstituted branched C3-C30 alkyl group, a substituted or unsubstituted branched C4-C30 alkenyl group, a substituted or unsubstituted branched C4-C30 alkynyl group, Lt; / RTI &

R ³ and R ⁴ are each independently hydrogen or a halogen atom; or

Either of R ³ and R ⁴ is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,

The other of R ³ and R ⁴ is a substituted or unsubstituted branched C3 to C30 alkyl group, a substituted or unsubstituted branched C4 to C30 alkenyl group, a substituted or unsubstituted branched C4 to C30 alkynyl group, Lt; / RTI &

R ¹ and R ² may each independently be hydrogen or a halogen atom.

If n1 = ¹ Ar 1 and Ar ² may be a benzene.

The organic compound may have a molecular weight of 300 to 5,000.

R ¹ and R ² are from each other when caused by having a different structure, R ³ and R ⁴ are each independently hydrogen or halogen atom, R ³ and R ⁴ are each case caused with the other structures, R ¹ and R ² are independently Hydrogen or a halogen atom.

The compound may exhibit a smectic phase at a temperature of 300 ° C or higher in the temperature raising process of differential scanning calorimetry (DSC) analysis.

According to another embodiment, there is provided an electronic device including the organic thin film transistor.

The electronic device may be selected from a liquid crystal display device, an organic light emitting device, an electrophoresis device, an organic photoelectric device, and an organic sensor.

According to another embodiment, there is provided an electronic device comprising the organic thin film.

An organic compound which improves charge mobility and solubility is provided. The organic compound has a liquid crystal property by having an asymmetric substituent, and when subjected to heat treatment in a liquid crystal section, the ordered liquid crystal phase is exhibited, so that the charge mobility can be enhanced.

1 is a cross-sectional view illustrating an organic thin film transistor according to one embodiment,
2 is a graph of thermal gravimetric analysis (TGA) of the compound obtained according to Comparative Synthesis Example 1,
3 is a TGA graph of the compound obtained according to Comparative Synthesis Example 2,
4 is a TGA graph of the compound obtained according to Synthesis Example 1,
5 is a graph of differential scanning calorimetry (DSC) of a compound obtained according to Comparative Synthesis Example 1,
6 is a DSC graph of the compound obtained according to Comparative Synthesis Example 2,
7 is a DSC graph of the compound obtained according to Comparative Synthesis Example 3,
8 is a DSC graph of the compound obtained according to Synthesis Example 1,
9 is a DSC graph of the compound obtained according to Synthesis Example 2,
10 is a DSC graph of the compound obtained according to Synthesis Example 3,
11 is a DSC graph of the compound obtained according to Synthesis Example 4,
12 is a DSC graph of the compound obtained according to Synthesis Example 5. Fig.

Hereinafter, exemplary embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

In the drawings, the thickness is enlarged to clearly represent the layers and regions.

Whenever a portion of a layer, film, region, plate, or the like is referred to as being "on" another portion, it includes not only the case where it is "directly on" another portion, but also the case where there is another portion in between. Conversely, when a part is "directly over" another part, it means that there is no other part in the middle.

As used herein, the term " combination thereof " means a mixture, a laminate, a mutual substitution, or the like of the composition.

As used herein, " hetero " means one to four heteroatoms selected from N, O, S, Se, Si and P in the compound. The total number of members constituting the ring may be from 3 to 10. If multiple rings are present, each ring can be an aromatic ring, a saturated or partially saturated ring or a multiple ring (fused ring, pendant ring, spiacyclic ring or a combination thereof). The heterocycloalkyl group may be at least one non-aromatic ring containing a heteroatom, and the heteroaryl group may be at least one aromatic ring containing a heteroatom. Non-aromatic and / or carbocyclic rings may be present in the heteroaryl group if the at least one ring is an aromatic ring containing a heteroatom.

Unless otherwise defined herein, the term " ring group " is a concept including both a case in which a hetero atom is not contained in a ring and a case in which a hetero atom is contained in a ring.

Unless otherwise defined hereinafter, the term "alkyl group" includes straight chain or branched chain, saturated, monovalent hydrocarbon groups (for example, methyl, ethyl, propyl, isobutyl, sec-butyl, T-butyl, iso-amyl, hexyl, etc.).

&Quot; Alkenyl group " means a straight or branched, saturated, monovalent hydrocarbon group (e. G., An ethynyl group) having at least one carbon-carbon double bond.

&Quot; Alkynyl " means a straight or branched, saturated, monovalent hydrocarbon group (e.g., an ethynyl group) having at least one carbon-carbon triple bond.

&Quot; Alkoxy group " means an alkyl group connected through oxygen, for example, methoxy, ethoxy, and sec-butyloxy groups.

&Quot; Aryl group " means a monovalent functional group formed by the removal of a hydrogen atom present in at least one ring of arene, for example, phenyl or naphthyl. The arene is a hydrocarbon group having an aromatic ring and includes a single ring and multiple ring hydrocarbon groups, and the additional ring of the multiple ring hydrocarbon group may be an aromatic ring or a non-aromatic ring.

&Quot; Alkylaryl " means that some of the hydrogen atoms in the alkyl group are replaced by aryl groups.

&Quot; Aryloxy group " means an aryl group connected through oxygen, and the aryl group is as described above.

"Arylalkyl" means that some of the hydrogen atoms in the aryl group are replaced by lower alkylenes such as methylene, ethylene, propylene, and the like. For example, a benzyl group and a phenylethyl group.

&Quot; Cycloalkyl group " means a monovalent functional group (e.g., a "cyclopentyl group and a cyclohexyl group") having one or more saturated rings in which all members are carbon.

&Quot; Heteroalkyl group " means a group in which the methylene (- (CH) ₂ -) of the alkyl group defined above is replaced by -O-, -S-, -S (= O) _2- , -Se- or -NR- Independently, hydrogen or a C1 to C10 alkyl group).

The term " arylheteroalkyl group " means that at least one of the hydrogen atoms of the above-defined heteroalkyl group is substituted with an aryl group.

&Quot; Heteroarylalkyl " means that at least one of the hydrogen atoms of an alkyl group as defined above is replaced by a heteroaryl group.

The term " alkylheteroaryl group " means that at least one of the hydrogen atoms of the heteroaryl group as defined above is substituted with an alkyl group.

As used herein, unless otherwise defined, the term "aromatic ring" refers to a functional group in which all elements of the functional group in the form of a ring have a p-orbital, and these p-orbital forms a conjugation. For example, the aromatic ring may be a C6 to C20 aryl group.

&Quot; Substitution " as used herein refers to the substitution of a halogen (-F, -Cl, -Br or -I) group, a C1 to C30 linear or branched alkyl group Such as straight or branched chain alkyl groups of C1 to C10, straight or branched alkenyl groups of C2 to C30 such as straight or branched alkenyl groups of C2 to C10, straight or branched alkynyl groups of C2 to C30, For example, a C2 to C10 linear or branched alkynyl group, a C6 to C30 aryl group such as a C6 to C12 aryl group, a C2 to C30 heteroaryl group such as a C2 to C12 heteroaryl group, A C1 to C20 perfluoroalkyl group (C _n F _{2n + 1} ), a C1 to C30 linear or branched alkoxy group, a C3 to C30 cycloalkoxy group, a C3 to C30 cycloalkyl group, a C1 to C20 fluoroalkyl group, , C2 to C30 linear or branched alkoxyalkyl groups, C4 Of C30 cycloalkoxy group, a cyano group, an amino group (-NRR ', wherein R and R' are independently an alkyl group of one another hydrogen or a C1 to C10), amidino group _{(-C (= NH) NH 2} ), nitro group (-NO _2), amide group (-C (= O) NHR, where R is an alkyl group of hydrogen or C1 to C10), aldehyde group (-C (= O) H) , hydroxyl group (-OH), sulfonyl (-S (═O) ₂ R, wherein R is independently of each other hydrogen or a C1 to C10 alkyl group) and a carbamate group (-NHC (═O) OR, wherein R is a C1 to C10 alkyl group ). ≪ / RTI >

The organic compounds according to one embodiment will be described below.

The organic compound according to one embodiment may be selected from a compound represented by the following formula (1A), a compound represented by the formula (1B), and combinations thereof.

≪ EMI ID =

≪ RTI ID = 0.0 &

In the above formulas 1A and 1B,

Ar ¹ and Ar ² are each independently benzene, naphthalene or anthracene,

X ¹ to X ⁴ each independently represent O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom or a combination thereof,

n1, n2 and n3 are each independently 0 or 1,

R ¹ to R ⁴ are each independently hydrogen, a halogen atom, a substituted or unsubstituted straight or branched chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain or branched C2 to C30 alkenyl group, a substituted or unsubstituted straight- A substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, C30 alkylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, or a combination thereof,

R ¹ and R ² are groups having different structures, or R ³ and R ⁴ are groups having different structures.

The organic compound is a low molecular compound having two substituents (R ¹ and R ² , or R ³ and R ⁴ ) positioned asymmetrically on both sides of a condensed polycyclic group in which at least six rings are fused.

Refers to the case of "R ¹ and R ² are each a group having a different structure" in the present specification that "R ¹ and R ² are asymmetric with one another", "R ³ and R group ⁴ has a different structure Quot; is referred to as " R ³ and R ⁴ are asymmetrically positioned with respect to each other ".

The organic compound improves the planarity of the compound by appropriately controlling the number of fused rings, thereby enhancing the packing and stacking between the molecules, and has a compact planar molecular structure, When applied, the oxidation potential can be uniform and stable.

By locating a single fused benzene ring between the heterocycles in the above formula (1A) or (1B), it is possible to increase intermolecular interactions by enlarging the conjugated structure, thereby improving the charge mobility and thermal stability.

In addition, the presence of the heterocycle between the benzene rings can improve the solubility of the condensed polycyclic heteroaromatic compound in the organic solvent.

The organic compound has a structure in which a heteroaromatic ring is located in the outermost ring to increase intermolecular interactions, which is advantageous for molecular alignment, thereby improving charge mobility.

For example, in the above formula (1A) or (1B), n2 = n3 = 0 or n2 = n3 = 1 when n1 = 0 and n2 = n3 = 0 when n1 = 1 can be satisfied. , in the case of n1 = ¹ Ar 1 and Ar ² may be, for example, benzene. As described above, the organic compound can control physical properties by appropriately adjusting the number of rings to be fused in the core.

The core of the organic compound may be a polycyclic ring group in which at least six pentagonal or hexagonal rings are fused and may have better thermal stability characteristics as compared with an organic compound containing less than 6 rings of cores, It is applicable to both solution processes.

The compound may exhibit a smectic phase at a temperature of 300 ° C or higher in the temperature raising process of differential scanning calorimetry (DSC) analysis.

Hereinafter, R ¹ to R ⁴ in the above formulas 1A and 1B will be described.

As described above, the organic compound has two substituents (R ¹ and R ² , or R ³ and R ⁴ ) positioned asymmetrically on both sides of the condensed polycyclic group described above, wherein the term "asymmetrically located" R ¹ and R ² are groups having different structures, or R ³ and R ⁴ have groups having different structures.

Here, the term " a group having a different structure " includes, for example, the following cases (i) to (iv), but the present invention is not limited thereto. ":

(i) when either of them contains a linear or branched hydrocarbon moiety, the other is a cyclic group;

(ii) when either of them contains a branching hydrocarbon moiety and the other is a ring group;

(iii) when either of them contains a branching hydrocarbon moiety and the other comprises a linear chain of hydrocarbons; or

(iv) when either one is hydrogen, a halogen atom, or a combination thereof, and the other is an aliphatic group, an aromatic group, or a combination thereof.

For example, in Formula 1A or 1B, any one of R ¹ and R ² may be a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight- A C2 to C30 alkynyl group, or a combination thereof,

The other of R ¹ and R ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,

R ³ and R ⁴ may each independently be hydrogen or a halogen atom.

For example, any one of R ¹ and R ² may be, for example, a substituted or unsubstituted branched C3 to C30 alkyl group, a substituted or unsubstituted branched C4 to C30 alkenyl group, a substituted or unsubstituted branched C4 to C30 alkynyl group Or a combination thereof,

The other of R ¹ and R ² is, for example, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, A substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group,

R ³ and R ⁴ may each independently be hydrogen or a halogen atom.

For example, when either one of R ¹ and R ² is a substituted or unsubstituted straight chain C1 to C30 alkyl group, a substituted or unsubstituted straight chain C2 to C30 alkenyl group, a substituted or unsubstituted straight chain C2 to C30 alkynyl group, In the combination thereof, the other of R ¹ and R ² is a substituted or unsubstituted branched C1 to C30 alkyl group, a substituted or unsubstituted branched C2 to C30 alkenyl group, a substituted or unsubstituted branched C2 to C30 An alkynyl group, or a combination thereof.

For example, when either one of R ¹ and R ² is a hydrogen atom or a halogen atom, the other of R ¹ and R ² is a substituted or unsubstituted straight or branched C 1 to C 30 alkyl group , A substituted or unsubstituted straight or branched C2 to C30 alkenyl group, a substituted or unsubstituted straight or branched C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 Substituted or unsubstituted C7 to C30 alkylaryl groups, substituted or unsubstituted C2 to C30 alkylheteroaryl groups, substituted or unsubstituted C7 to C30 arylheteroaryl groups, substituted or unsubstituted C5 to C30 cycloalkyl groups, Alkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, or a combination thereof.

Although R ¹ and R ² are asymmetrically positioned as described above, it is to be understood that the above examples can be applied to cases where R ³ and R ⁴ are asymmetrically located with respect to each other.

For example, when R ¹ and R ² are groups having different structures (that is, when R ¹ and R ² are positioned asymmetrically with respect to each other), R ³ and R ⁴ are each independently hydrogen or a halogen atom However, the present invention is not limited thereto. Similarly, when R ³ and R ⁴ are groups having different structures (that is, when R ³ and R ⁴ are asymmetrically positioned with respect to each other), R ¹ and R ² each independently may be hydrogen or a halogen atom, But is not limited thereto.

For example, in the above formula (1A) or (1B), R ¹ is a substituted or unsubstituted linear or branched C1 to C30 alkyl group, R ² is a substituted or unsubstituted C6 to C30 aryl group, and R ³ and R ⁴ are May independently be hydrogen or a halogen atom, but is not limited thereto.

For example, in Formula 1A or 1B, R ³ is a substituted or unsubstituted linear or branched C1 to C30 alkyl group, R ⁴ is a substituted or unsubstituted C6 to C30 aryl group, and R ¹ and R ² are May independently be hydrogen or a halogen atom, but is not limited thereto.

For example, the organic compound can increase the solubility by including, for example, the above-mentioned aliphatic chain group on one side of the condensed polycyclic group and include the above-mentioned ring group on the other side to improve the heat resistance property.

For example, when R ¹ and R ² are asymmetrically located in the organic compound represented by Formula 1A or 1B, X ⁴ is S, R ² is a fluorine-substituted C 6 to C 30 aryl group, A C 2 to C 3 0 heteroaryl group, a fluorinated C 7 to C 30 alkylaryl group, a fluoro substituted C 2 to C 30 alkylheteroaryl group, a fluoro substituted C 5 to C 30 cycloalkyl group, a fluoro substituted C 2 to C 30 heterocyclo Alkyl group, or a combination thereof. In this case, the interaction between S located at the thiophene portion of the core and F located at the substituent can be further strengthened.

For example, when R ¹ and R ² are asymmetric in the organic compound represented by Formula 1A or 1B, R ² is, for example, a substituted or unsubstituted pentagonal ring, a substituted or unsubstituted hexagonal ring, Specifically, R ² may be, for example, a heterocyclic group represented by the following formula (2A) or (2B), a substituted or unsubstituted alkylaryl group represented by the following formula (2C), or a combination thereof, but is not limited thereto. Here, " combination " is a concept including that two or more ring groups are fused together.

(2A)

(2B)

[Chemical Formula 2C]

In the above formulas (2A), (2B) and (2C)

X ⁵ is O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom, or a combination thereof,

X < ⁶ > is N,

R ⁵ R ⁶ and R ⁷ are each independently selected from the group consisting of a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,

a is an integer of 0 to 3,

b is an integer of 0 to 4,

c is an integer of 0 to 4,

R ^a and R ^b are each independently hydrogen or a C 1 to C 6 alkyl group and m is 0 to 20; and when m is 2 or more, optionally - (CR ^a R ^b ) - is -O-, -C (= O) -, -OC (= O) O- or -C (= O) O-,

R ^c and R ^d are each independently hydrogen or a C 1 to C 6 alkyl group and n is 0 to 20, and when n is 2 or more, - (CR ^c R ^d ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,

R ^e and R ^f are each independently hydrogen or a C 1 to C 6 alkyl group and r is 0 to 20, and when r is 2 or more, - (CR ^e R ^f ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,

* Is the connection point.

R ¹ to R ⁴ may be specifically selected from the following Group 1 or Group 2.

[Group 1]

[Group 2]

The condensed polycyclic heteroaromatic compounds according to one embodiment have an average molecular weight of from about 300 to about 5,000, from about 300 to about 4,000, or from about 300 to about 3,000. When having an average molecular weight in the above range, handling is easy.

The above-mentioned organic compound can have the liquid crystal property at a predetermined temperature range by locating the above-mentioned aliphatic chain group and the ring group 'asymmetric' on both sides of the core. When the organic compound is subjected to heat treatment at a predetermined temperature, the organic compound exhibits smectic liquid crystal properties and thus has increased molecular alignment. When the organic compound is annealed by applying, for example, a solution process to a thin film transistor, The mobility can be further increased. Here, the annealing can be performed at about 200 ° C to 250 ° C.

Specific examples of the organic compounds include, but are not limited to, the compounds listed in Group 3 below.

[Group 3]

The organic compound may be implemented as an organic thin film through a deposition or solution process. The organic thin film may be applied to various devices including organic semiconductors. For example, the organic compound may be applied to an organic thin film transistor, and may be applied as a charge transport layer and / or an active layer in an electronic device such as a solar cell, an organic light emitting diode display, and an organic sensor.

Hereinafter, an organic thin film transistor including the organic compound will be described with reference to the drawings.

In the drawings, the thickness is enlarged to clearly represent the layers and regions. Like parts are designated with like reference numerals throughout the specification. Whenever a portion of a layer, film, region, plate, or the like is referred to as being "on" another portion, it includes not only the case where it is "directly on" another portion, but also the case where there is another portion in between. Conversely, when a part is "directly over" another part, it means that there is no other part in the middle.

1 is a cross-sectional view illustrating an organic thin film transistor according to one embodiment.

A gate electrode 124 is formed on a substrate 110 made of transparent glass, silicon, or plastic. The gate electrode 124 is connected to a gate line (not shown) for transmitting a gate signal. The gate electrode 124 may be formed of a metal such as Au, Cu, Ni, Al, Mo, Cr, Ta, Ti, Or a combination thereof.

A gate insulating film 140 is formed on the gate electrode 124. The gate insulating layer 140 may be formed of an organic material or an inorganic material. Examples of the organic material include a polyvinyl alcohol-based compound, a polyimide-based compound, a polyacryl-based compound, a polystyrene- polystyrene-based compounds, benzocyclobutane (BCB), and the like. Examples of inorganic substances include silicon nitride (SiN _x ) and silicon oxide (SiO ₂ ).

A source electrode 173 and a drain electrode 175 are formed on the gate insulating layer 140. The source electrode 173 and the drain electrode 175 face the gate electrode 124 as a center. The source electrode 173 is connected to a data line (not shown) for transmitting a data signal. The source electrode 173 and the drain electrode 175 may be formed of a metal such as Au, Cu, Ni, Al, Mo, Cr, Ta, ), An alloy thereof, or a combination thereof.

An organic semiconductor 154 is formed on the source electrode 173 and the drain electrode 175. The organic semiconductor 154 may be made of the above-described organic compound. The organic semiconductor 154 may be prepared by preparing a solution of the above-mentioned organic compound in a solution process such as spin coating, slit coating, or inkjet printing. However, the organic compound described above may be formed by a dry process such as vapor deposition.

Although an organic thin film transistor having a bottom gate structure has been described herein as an example of an organic thin film transistor, the present invention is not limited thereto and can be applied to organic thin film transistors having all structures such as a top gate organic transistor.

The organic thin film transistor may be applied to various electronic devices as a switching device or a driving device, and the electronic device may include, for example, a liquid crystal display device, an organic light emitting display device, an electrophoretic display device, an organic photoelectric device and an organic sensor.

Hereinafter, embodiments of the present invention will be described in detail with reference to examples. The following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

Synthesis of organic compounds

Synthetic example  One

[Reaction Scheme 1]

(1) ((5- ((3-bromo-5-decylthiophen-2-yl) methyl) thieno [3,2- b] thiophene 2-yl) methyl) thieno [3,2-b] pyridin-2-yl) ] thiophen-2-yl) (3-bromo-5-phenylthiophen-2-yl) methanol)

4-Bromo-2-phenylthiophene (6 g, 25.1 mmol) was dissolved in dry ether (300 mL) in dry tetrahydrofuran (THF) and cooled to -78 ° C. After dropwise addition of LDA (2M solution) (15.1 ml, 30 mmol), compound 1 (12.1 g, 25.1 mmol) is added. The temperature is gradually raised and stirred at room temperature for 12 hours. Add 100 mL of saturated ammonium chloride solution, extract with ethyl acetate, and wash several times with water. After drying with magnesium sulfate and filtration, the ethyl acetate solvent is removed and the residue is purified by silica column chromatography to obtain the desired compound 2. (Yield 67%)

^{1 H NMR (500 MHz, CDCl} 3): δ ppm 7.53 (d, 2H), 7.43 (m, 2H), 7.31 (d, 1H), 7.17 (s, 1H), 7.13 (s, 1H), 7.01 ( 2H), 1.58 (m, 2H), 1.27 (m, 14H), 0.87 (t, 2H) , 3H)

(2) 2 - ((3- Bromo -5- Decylthiophene -2 days) methyl ) -5- ((3-bromo-5-phenylthiophen-2-yl) methyl) 3-bromo-5-phenylthiophen-2-yl) methyl) thieno [3,2-b] thiophene [3,2-b] thiophene (Compound 3 of  synthesis)

The compound (10 g, 13.84 mmol) was dissolved in 700 mL of dichloromethane, and ZnI ₂ A (7.07 g, 23.5 mmol) and _{NaCNBH 3 (6.09 g, 96.86 mmol} ) is added slowly. The mixture is stirred at room temperature for 24 hours, and then passed through a celite pad. The filtrate was washed with saturated ammonium chloride solution and water, respectively, and then dried with MgSO ₄ and concentrated under reduced pressure to obtain a yellow oil. The obtained material is purified by silica column chromatography to obtain the desired compound 3. [ (Yield: 92%)

^{1 H NMR (500 MHz, CDCl} 3): δ ppm 7.50 (d, 2H), 7.35 (m, 2H), 7.28 (m, 1H), 7.13 (s, 1H), 7.03 (s, 1H), 7.0 ( 2H), 1.55 (m, 2H), 1.27 (m, 2H), 6.76 (s, , 14H), 0.87 (t, 3H)

(3) Synthesis of 2 - ((5 - ((3-cyano-5-decylthiophen-2-yl) methyl) thieno [3,2- b] thiophen- 3-cyano-5-decylthiophen-2-yl) methyl) thieno [3,2-b] thiophen-2-yl) phenylthiophene-3-carbonitrile (Synthesis of Compound 4)

The compound (9 g, 12.73 mmol) was dissolved in 135 ml of N-methylpyrrolidone, and then 3.42 g (38.2 mmol) of cupricanide (CuCN) React for 2 hours. After completion of the reaction, it is poured into 1N HCl solution and stirred for 30 minutes. The solid is filtered, extracted with chloroform (CHCl ₃ ) and washed with water. After drying with magnesium sulfate and filtration, the chloroform solvent is removed and purified by silica column chromatography to obtain the desired compound 4. [ (Yield 60%)

^{1 H NMR (500 MHz, CDCl} 3): δ ppm 7.49 (d, 2H), 7.38 (m, 2H), 7.34 (d, 1H), 7.29 (s, 1H), 7.11 (s, 1H), 7.06 ( 2H), 1.50 (m, 2H), 1.27 (m, 14H), 0.86 (t, , 3H)

(4) 5-Decyl-2 - ((5- ((3-formyl-5-phenylthiophen-2-yl) methyl) thieno [3,2- b] thiophene 3-formyl-5-phenylthiophen-2-yl) methyl) thieno [3,2-b] pyridin- thiophen-2-yl) methyl) thiophene-3-carbaldehyde) (Synthesis of Compound 5)

The above compound (4.56 g, 7.61 mmol) is dissolved in 600 mL of dichloromethane, and then the temperature is lowered to 0 캜. Diisobutylaluminium hydride (DIBALH, 1.0 M solution in cyclohexane) (18.27 ml, 18.27 mmol) was added thereto and stirred for 2 hours. The reaction is terminated by pouring 5% citric acid, then extracted with chloroform (CHCl ₃ ) and washed with water and brine. Thereafter, the organic layer is dried over MgSO ₄ and concentrated under reduced pressure, and the material is then purified by silica chromatography to obtain the desired compound 5. (Yield 67%)

^{1 H NMR (500 MHz, CDCl} 3): δ ppm 10.1 (s, 1H), 9.99 (s, 1H), 7.59 (s, 1H), 7.55 (d, 2H), 7.37 (m, 2H), 7.31 ( 2H), 1.62 (m, 2H), 1.28 (m, 2H), 7.06 (s, m, 14H), 0.87 (t, 3H)

(5) Synthesis of Compound 6

Compound 5 (3.1 g, 5.12 mmol) was dissolved in 300 mL benzene, Amberlyst 15 (3.1 g) was added thereto, and the mixture was stirred under reflux using a Dean-Stark trap To remove water. After about 24 hours, a pale yellow solid precipitates. The temperature is lowered to room temperature and Amberlyst 15 is precipitated, the supernatant is filtered off and the desired compound 6 is obtained as a yellow solid. (Yield 50%)

MS (MALDI-TOF-MS, m / z) 568.194 (M +)

Synthetic example  2

[Reaction Scheme 2]

(1) (3-브로모-5-데실티오펜-2-일)티에노 [3,2-b]티오펜-2-일)메탄올 (3-bromo-5-decylthiophen-2-yl)(thieno[3,2-b]thiophen-2-yl)methanol (화합물 1의 합성)

(1) (3-bromo-5-de silti 2-yl) thieno [3,2-b] thiophen-2-yl) methanol to (3-bromo-5-decylthiophen -2-yl) ( thieno [3,2-b] thiophen-2-yl) methanol (Synthesis of Compound 1)

Thieno [3,2-b] thiophen (7.5 g, 53.5 mmol) is dissolved in diethylether and cooled to 0 ° C. n-BuLi (25.7 mL, 64.2 mmol) is slowly added dropwise followed by the addition of 3-bromo-5-decyl-2-thiophencarboxyaldehyde (23.04 g, 69.5 mmol). The temperature is gradually raised and stirred at room temperature for 12 hours. Add 200 mL of saturated ammonium chloride solution, extract with ethyl acetate, and wash several times with water. After drying with magnesium sulfate and filtration, the ethyl acetate solvent is removed, and the residue is purified by silica column chromatography to obtain the desired compound 1. (Yield: 90%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 7.34 (d, 1H), 7.22 (d, 1H), 7.21 (s, 1H), 6.64 (s, 1H), 6.38 (d, 1H), 2.74 ( (m, 2H), 1.27 (m, 14H), 0.88 (t, 3H)

(2) 2- (3-bromo-5-de silti-2-yl) methyl-thieno [3,2-b] thiophene (2- (3-bromo- 5- decylthiophen-2-yl) methylthieno [3,2-b] thiophene) (Synthesis of Compound 2)

Compound 1 (22.6 g, 47.9 mmol) was dissolved in 1 L of dichloromethane, then ZnI ₂ A (24.5 g, 76.7 mmol) and _{NaCNBH 3 (21.1 g, 335.5 mmol} ) is added slowly. The mixture was stirred at room temperature for 24 hours, and then 200 mL of a saturated ammonium chloride solution was added to terminate the reaction. Extract with dichloromethane and wash several times with water. Drying and concentration under reduced pressure with MgSO ₄ to give a yellow oil. This material is purified by silica column chromatography to give the desired compound 3. < Desc / (Yield: 89%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 7.29 (d, 1H), 7.17 (d, 1H), 7.06 (s, 1H), 6.62 (s, 1H), 4.29 (s, 2H), 2.70 ( t, 2H), 1.64 (m, 2H), 1.25 (m, 14H), 0.88 (t,

(3) (5- ((3-bromo-5-decylthiophen-2-yl) methyl) thieno [3,2- b] thiophene Yl) (3- Bromo (3-bromo-5-decylthiophen-2-yl) methyl) thieno [3,2-b] thiophen-2-yl) bromo-5-isopropylthiophen-2-yl) methanol) (Synthesis of Compound 3)

Compound 2 (11.7 g, 25.6 mmol) is dissolved in 300 mL of dry tetrahydrofuran (THF) and cooled to -78 < 0 > C. 3-bromo-5-isopropyl-2-thiophencarboxyaldehyde (6.6 g, 28.3 mmol) is added dropwise slowly to a solution of LDA (2M solution) (16.7 ml, 33.4 mmol). The temperature is gradually raised and stirred at room temperature for 12 hours. Add 100 mL of saturated ammonium chloride solution, extract with dichloromethane, and wash several times with water. After drying with magnesium sulfate, purification is carried out by silica column chromatography to obtain the desired compound 2. (Yield: 49%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 7.12 (s, 1H), 7.01 (s, 1H), 6.65 (s, 1H), 6.61 (s, 1H), 6.35 (d, 1H), 4.27 ( (m, 2H), 3.07 (m, 1H), 2.70 (t, 2H), 2.65

(4) 2 - ((3- Bromo -5- Decylthiophene -2 days) methyl ) -5- ((3-Bromo-5-isopropylthiophen-2-yl) 3-bromo-5-isopropylthiophen-2-yl) methyl) thieno [3,2-b] thiophene ) thieno [3,2-b] thiophene (Compound 4 of  synthesis)

Compound 3 (8.2 g, 11.95 mmol) was dissolved in 1 L of dichloromethane and ZnI ₂ A (6.1 g, 19.1 mmol) and _{NaCNBH 3 (5.3 g, 83.7 mmol} ) is added slowly. The mixture was stirred at room temperature for 24 hours, washed with saturated ammonium chloride solution and water, and then dried over MgSO ₄ and concentrated under reduced pressure to obtain a yellow oil. This material is purified by silica column chromatography to give the desired compound 4. < Desc / (Yield: 98%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 6.97 (s, 2H), 6.61 (d, 2H), 4.27 (s, 4H), 3.09 (m, 1H), 2.68 (t, 2H), 1.60 ( m, 2H), 1.27 (m, 20H), 0.88 (t, 3H)

(5) Synthesis of 2 - ((5 - ((3-cyano-5-decylthiophen-2-yl) methyl) thieno [3,2- b] thiophen- 2-yl) methyl) thieno [3,2-b] thiophen-2-yl) methyl) 5-isopropylphenylthiophene-3-carbonitrile (Synthesis of Compound 5)

 Compound 4 (8.2 g, 12.2 mmol) was dissolved in 120 ml of N-methylpyrrolidone, and then cupricanide (CuCN) (4.2 g, 48.9 mmol) was added thereto. The mixture was heated in a microwave reactor at 50 W and 180 ° C. React for 2 hours. After completion of the reaction, it is poured into 1N HCl solution and stirred for 30 minutes. The solid is filtered off, extracted with dichloromethane and washed with water. After drying with magnesium sulfate, short-path column using celite and silica to obtain desired compound 5. (Yield: 81%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 7.05 (s, 2H), 6.80 (d, 2H), 4.46 (s, 4H), 3.09 (m, 1H), 2.69 (t, 2H), 1.60 ( m, 2H), 1.27 (m, 20H), 0.88 (t, 3H)

(6) 5-Decyl-2 - ((5- ((3-formyl-5-isopropylthiophen-2-yl) methyl) thieno [3,2-b] thi Yl) methyl) thiophene-3-carbaldehyde

(5- decyl 2-yl) methyl) thiophene-3-carbaldehyde) (Synthesis of Compound (6) )

Compound 5 (5.4 g, 9.6 mmol) is dissolved in 800 mL of dichloromethane and then cooled to 0 < 0 > C. Diisobutylaluminium hydride (DIBALH, 1.0M solution in cyclohexane) (27.9 ml, 27.9 mmol) was added thereto and stirred for 5 minutes. The reaction solution of methanol and water mixture (Methanol: water = 2: 1 ) a termination of the pour reaction in the following dichloromethane (dichloromethane) by extraction, washed with water and Dublin (brine), MgSO and the organic layer ₄ Dried and concentrated under reduced pressure, and then the material is purified by silica chromatography to obtain the desired compound 6. (Yield: 91%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 10.0 (s, 2H), 7.09 (s, 1H), 7.06 (s, 1H) 7.00 (s, 2H), 4.68 (s, 4H), 3.07 (m (M, 2H), 1.28 (m, 20H), 0.88 (t, 3H)

(7) Synthesis of Compound 7

Compound 6 (5.0 g, 8.8 mmol) was dissolved in 300 mL benzene and Amberlyst 15 (4.0 g) was added thereto. The mixture was stirred under reflux using a Dean-Stark trap To remove water. The temperature of the pale yellow liquid produced after 24 hours is lowered to room temperature to form a white precipitate. The precipitated suspension was recovered by filtration with a filter, and then recrystallized in a mixture of nucleic acid and chloroform to obtain Compound 7 as a white solid. (Yield: 72%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 8.27 (s, 2H), 8.12 (s, 2H) 7.12 (s, 1H), 7.10 (s, 1H), 3.28 (m, 1H), 2.93 (t , 2H), 1.78 (m, 2H), 1.44 (d, 6H), 1.27 (m,

MS (MALDI-TOF-MS, m / z) 534.249 (M +)

Synthetic example  3

[Reaction Scheme 3]

(1) (3- 브로모 -5- 데실티오펜 -2-일)(6-((3- 브로모 -5- 페닐티오펜 -2-일)(히드록시)메틸)벤조[1,2-b:4,5-b']디티오펜-2-일)메탄올((3-bromo-5-decylthiophen-2-yl)(6-((3-bromo-5-phenylthiophen-2-yl)(hydroxy)methyl)benzo[1,2-b:4,5-b']dithiophen-2-yl)methanol) (화합물 2의 합성)

(1) (3-bromo-5-de silti-2-yl) (6 - ((3-bromo-5-phenyl-thiophen-2-yl) (hydroxy) methyl) benzo [1,2 5-decylthiophen-2-yl) (6 - ((3-bromo-5-phenylthiophen-2-yl) hydroxy) methyl) benzo [1,2-b: 4,5-b '] dithiophen-2-yl)

4-Bromo-2-phenylthiophene (6 g, 25.1 mmol) was dissolved in dry ether (300 mL) in dry tetrahydrofuran (THF) and cooled to -78 ° C. After dropwise addition of LDA (2M solution) (15.1 ml, 30 mmol), compound 1 (19.8 g, 25.1 mmol) is added. The temperature is gradually raised and stirred at room temperature for 12 hours. Add 100 mL of saturated ammonium chloride solution, extract with ethyl acetate, and wash several times with water. After drying with magnesium sulfate and filtration, the ethyl acetate solvent is removed and purified by silica column chromatography to obtain the desired compound 2. [ (Yield: 65%)

(2) 2 - ((3- Bromo -5- Decylthiophene -2 days) methyl ) -6- ((3-bromo-5-phenylthiophen-2-yl) methyl) 5-decylthiophen-2-yl) methyl) -6 - ((3-bromo-5-phenylthiophen-2- -yl) methyl) benzo [1,2-b: 4,5-b '] dithiophene) (Synthesis of Compound 3)

The above compound (10 g, 12.68 mmol) was dissolved in 700 mL of dichloromethane, and ZnI ₂ A (6.88 g, 21.56 mmol) and _{NaCNBH 3 (5.58 g, 88.76 mmol} ) is added slowly. The mixture is stirred at room temperature for 24 hours, and then passed through a celite pad. The filtrate was washed with saturated ammonium chloride solution and water, respectively, and then dried with MgSO ₄ and concentrated under reduced pressure to obtain a yellow oil. The material is purified by silica column chromatography to give the desired compound 3. (Yield: 90%)

(3) 2 - ((6- ((3-cyano-5-decylthiophen-2-yl) methyl) benzo [1,2- b: 4,5- b '] dithiophene Yl) methyl) -5-phenylthiophene-3-carbonitrile (2 - ((6 - ((3-cyano-5-decylthiophen- , 5-b '] dithiophen-2-yl) methyl) -5-phenylthiophene-3-carbonitrile)

The compound (9 g, 11.89 mmol) was dissolved in 135 ml of N-methylpyrrolidone and then 3.13 g of CuCN (3.9 g, 35.68 mmol) was added thereto. React for 2 hours. After completion of the reaction, it is poured into 1N HCl solution and stirred for 30 minutes. The solid is filtered, then extracted with chloroform (CHCl ₃ ) and washed with water. After drying with magnesium sulfate and filtration, the chloroform solvent is removed and purified by silica column chromatography to obtain the desired compound 4. [ (Yield: 65%)

(4) 5-Decyl-2 - ((6- ((3-formyl-5-phenylthiophen-2-yl) methyl) benzo [1,2- b: 4 , 5-b '] Dithiophene 2-yl) methyl) benzo [1,2-b: 3-formyl-5-phenylthiophen- 4,5-b '] dithiophen-2-yl) methyl) thiophene-3-carbaldehyde (Synthesis of Compound 5)

The above compound (5 g, 7.70 mmol) is dissolved in dichloromethane (600 mL) and the temperature is lowered to 0 ° C. Diisobutylaluminium hydride (DIBALH, 1.0 M solution in cyclohexane) (18.48 ml, 18.48 mmol) was added thereto and stirred for 2 hours. After the reaction was terminated by pouring 5% citric acid, the reaction mixture was extracted with chloroform (CHCl ₃ ) and washed with water and brine. The organic layer was dried over MgSO ₄ and concentrated under reduced pressure. Purification by silica chromatography affords the desired compound 5. (Yield: 65%)

(5) Synthesis of Compound 6

Compound 5 (3.5 g, 5.34 mmol) was dissolved in 300 mL of benzene and Amberlyst 15 (3.1 g) was added thereto. The mixture was stirred under reflux using a Dean-Stark trap To remove water. After about 24 hours, a pale yellow solid precipitated. The temperature is lowered to room temperature and Amberlyst 15 is precipitated and the supernatant is filtered off to give the desired compound 6 as a yellow solid. (Yield 50%)

Synthetic example  4

[Reaction Scheme 4]

1. 5,5'- Dibromo -2,2'- Batiotopen  (5,5'- dibromo -2,2'- bithiophene ) (Synthesis of Compound 1)

2,2'-bithiophene (11.7 g, 70.1 mmol) was dissolved in 500 mL of N, N-dimethylmethanamide and N-bromosuccinimide (N- bromo succinimide (31 g, 175.2 mmol) is added dropwise and brominated. Thereafter, reflux for 2 hours, water (1 L) is added, and the resulting precipitate is collected by a filter. The recovered powder was dissolved in chloroform (700 mL), washed with water, dried over magnesium sulfate, and then evaporated. Washed with normal nucleic acid, and dried to obtain desired compound 1 (yield: 93%).

1H-NMR (300 MHz, CDCl 3): δ 6.96 (d, J = 3.6 Hz, 1H), 6.85 (d, J = 3.6 Hz, 1H)

2. (5'- Bromo - [2,2'- Batiotopen ]-5 days)( Tursley -Butyl) Dimethylsilane  ((5'-bromo- [2,2'-bithiophen] -5-yl) (tert-butyl) dimethylsilane 2) of  synthesis

2,5-dibromo-bithiophene (20.3 g, 62.6 mmol) was added to 1.7 L of tetrahydrofuran to prepare a cooled solution (-78 ° C). To this solution was added n-butyl Lithium (2.5 M in hexane, 30 mL, 1.2 eq.) Is added and the reaction mixture stirred vigorously for 30 min. T-Butyldimethylsilyl chloride (10.3 g, 68.9 mmol, 1.1 eq.) Was then added thereto. The reaction mixture was then stirred at -78 ° C overnight, diluted with dichloromethane, washed with water and brine The organic layer was dried over magnesium sulfate and evaporated, and the resulting yellow liquid was purified by silica column chromatography to obtain 16.9 g of a white solid (yield: 75.3%).

1H-NMR (300 MHz, CDCl 3): δ 7.17 (d, J = 3.3 Hz, 1H), 7.12 (d, J = 3.3 Hz, 1H), 6.96 (d, J = 3.9 Hz, 1H), 6.85 ( d, J = 3.9 Hz, 1 H) 0.94 (s, 9H), 0.29 (s, 6H)

3. Preparation of (4-bromo-5 '- (tert-butyldimethylsilyl) - [2,2'-bithiophen] Yl) methyl) thieno [3,2-b] thiophen-2-yl) methanol yl) methyl) (Synthesis of Compound 4) Synthesis of Compound 5 (5-methyl-5-decylthiophen-

(8.9 g, 24.9 mmol) was added to 1.3 L of dry tetrahydrofuran to prepare a cooled solution (-78 ° C). Lithium diisopropylamide (2.0 M in THF / heptane / ethylbenzene, 18.7 mL, 37.2 mmol) and the reaction mixture is vigorously stirred at -78 < 0 > C for 2 hours. Then, Compound 3 (12.0 g, 24.9 mmol) is added thereto, slowly warmed to room temperature, stirred for 20 minutes, and then saturated ammonium chloride solution is added. The solution is then diluted with dichloromethane and washed several times with water, then the organic layer is dried over magnesium sulfate and evaporated to give a brown liquid. The desired compound 4 was obtained by purification by silica column chromatography. (Yield: 59%)

^{1 H-NMR (300 MHz,} CDCl 3): δ 7.21 (d, J = 3.6 Hz, 1H), 7.17 (s, 1H), 7.12 (d, J = 3.6 Hz, 1H), 7.02 (s, 1H) J = 7.2 Hz, 2H), 2.66 (d, 2H), 7.02 (s, 1H) J = 3.6 Hz, 1H), 1.62 (m, 2H), 1.25 (m, 14H), 0.92 (s, 9H), 0.87

(4-Bromo-5 '- ((5 - ((3-bromo-5-decylthiophen-2- yl) methyl) thieno [3,2- b] thiophen- 5 '- ((3-bromo-5-decylthiophen-2-yl) methyl) - [2,2'-bithiophen] yl) (tert-butyl) dimethylsilane (Synthesis of Compound (5)) [0142] < EMI ID =

Compound 4 (13.6 g, 16.1 mmol) was dissolved in 1 L of dichloromethane, then ZnI ₂ A (8.2 g, 25.8 mmol) and _{NaCNBH 3 (7.1 g, 112.9 mmol} ) was added slowly. The mixture was stirred at room temperature for 6 hours, and 200 mL of a saturated ammonium chloride solution was added thereto to terminate the reaction. Extracted with dichloromethane and washed several times with water. Drying and concentration under reduced pressure with MgSO ₄ to yield a yellow oil. This material was purified by silica column chromatography to obtain the desired compound 3. < 1 > (Yield: 94%)

¹ H NMR (300 MHz, CDCl ₃ ):? Ppm 7.15 (d, 1H), 7.10 (d, 1H), 7.02 (s, (s, 2H), 4.26 (s, 2H), 2.70 (t, 2H), 1.67 (m, 2H), 1.25 , 6H)

Thieno [2,3-b] thiophen-2-yl) methyl ) - [2, 3-cyano-5-decylthiophen-2-yl) methyl) thieno [3,2-b] thiophen-2-yl) methyl] ) - [2,2'-bithiophene] -4-carbonitrile) (Synthesis of Compound 6)

   Compound solvent 5 was dissolved in 120 ml of N-methylpyrrolidone (11.6 g, 14.0 mmol) and cupricyanide (CuCN) (4.9 g, 56.1 mmol) was added thereto. And reacted at 50 W and 180 ° C for 2 hours in a microwave reactor, respectively. After completion of the reaction, the mixture was poured into 1N HCl solution and stirred for 30 minutes. The solid was filtered, extracted with dichloromethane, and washed with water. The organic layer was dried over magnesium sulfate and evaporated to give a brown liquid. The desired compound 6 was obtained by purification by silica column chromatography. (Yield: 54%)

^{1 H NMR (300 MHz, CDCl} 3): δ ppm 7.27 (d, 1H), 7.15 (s, 1H), 7.14 (d, 1H), 7.10 (s, 1H), 7.06 (s, 1H), 7.01 ( 2H), 1.63 (s, 3H), 1.86 (m, 2H), 1.45 (m, , 3H)

6. 5 - ((5- ((5-decyl-3-formylthiophen-2-yl) methyl) thieno [3,2- b] thiophene Yl) methyl) - [2,2'-bithiophene] -4-carbaldehyde (5 - ((5 - (5-decyl-3-formylthiophen- , 2-b] thiophen-2-yl) methyl) - [2,2'-bithiophene] -4-carbaldehyde)

Compound 6 (4.6 g, 7.6 mmol) was dissolved in 800 mL of dichloromethane and then cooled to 0 ° C. Diisobutylaluminium hydride (DIBALH, 1.0 M solution in cyclohexane) (22.8 ml, 22.8 mmol) was added thereto and stirred for 5 minutes. The reaction solution of methanol and water mixture (Methanol: water = 2: 1 ) a termination of the pour reaction in the following dichloromethane (dichloromethane) by extraction, washed with water and Dublin (brine), MgSO and the organic layer ₄ And concentrated under reduced pressure. This material was then purified by silica chromatography to obtain the desired compound 6. < 1 > (Yield: 56%)

¹ H NMR (300 MHz, CDCl ₃ ):? 10.04 (s, IH), 9.99 (s, IH), 7.43 (s, 2H), 2.71 (t, 2H), 1.62 (m, 1H), 7.07 (s, 2H), 1.25 (m, 14H), 0.87 (t, 3H)

7. Synthesis of Compound 8

Compound 7 (2.5 g, 4.1 mmol) was dissolved in 350 mL of benzene and Amberlyst 15 (5.2 g) was added thereto. The mixture was stirred under reflux using a Dean-Stark trap To remove water. After 24 hours, the temperature of the pale yellow liquid produced was lowered to room temperature to form a precipitate. The precipitated suspension was collected by filtration through a filter, washed with benzene, MC, EA, THF, and MC to obtain Compound 7. (Yield: 61%)

MS (MALDI-TOF-MS, m / z) 574.224 (M +)

Synthetic example  5

[Reaction Scheme 5]

1. (3- Bromo -5- (4- Octylphenyl ) Thiophen-2-yl) ( Tieno [3,2-b] -thiophen-2-yl) methanol

((3- bromo -5- (4- octylphenyl ) thiophen -2- yl ) ( thieno [3,2-b] thiophen -2-yl) methanol) (Synthesis of Compound 1)

 After dissolving 4-bromo-2- (4-octylphenyl) thiophene (7.04 g, 20.0 mmol) in dry tetrahydrofuran (THF) Lt; / RTI > After dropwise addition of LDA (2M solution, 12.02 ml, 24 mmol), thieno [3,2-b] thiophene-2 -carbaldehyde) (3.07 g, 20.0 mmol). The temperature was gradually raised and stirred at room temperature for 12 hours. To this was added 100 mL of a saturated ammonium chloride solution, extracted with ethyl acetate, and washed several times with water. After drying with magnesium sulfate, after removing the ethyl acetate solvent after filtration, the desired compound 1 was obtained by purification by silica column chromatography. (Yield: 89%)

2. 2- (3- Bromo -5- (4- Octylphenyl ) Thiophen-2-yl) methyl ) Thieno [3,2-b] thiophene  (Synthesis of Compound 2) A solution of 2-bromo-5- (4-octylphenyl) thiophen-2-yl) methyl thieno [3,2-b] thiophene

Compound 1 (9.26 g, 17.8 mmol) was dissolved in 1 L of dichloromethane and ZnI ₂ A (9.10 g, 28.5 mmol) and _{NaCNBH 3 (7.84 g, 124.8 mmol} ) was added slowly. The mixture was stirred at room temperature for 24 hours, and then 200 mL of a saturated ammonium chloride solution was added thereto to terminate the reaction. Extracted with dichloromethane and washed several times with water. Drying and concentration under reduced pressure with MgSO ₄ to yield a yellow oil. This material was purified by silica column chromatography to obtain the desired compound 3. < 1 > (Yield: 89%)

3. ((3- Bromo -5- (4- Octylphenyl ) Thiophen-2-yl) (5- ((3-bromothiophen-2-yl) methyl) thieno (3-bromothiophen-2-yl) methyl) thieno [3,2-b] thiophen-2-yl) [3,2-b] thiophen-2-yl) methanol) (Synthesis of Compound 3)

Compound 2 (8.63 g, 17.1 mmol) was dissolved in 300 mL of dry tetrahydrofuran (THF) and cooled to -78 < 0 > C. 3-bromothiophene-2-carbaldehyde (3.6 g, 18.9 mmol) was added after slowly dropwise addition of LDA (2M solution) (10.3 ml, 20.6 mmol). The temperature was gradually raised and stirred at room temperature for 12 hours. To this was added 100 mL of a saturated ammonium chloride solution, extracted with dichloromethane, and washed several times with water. After drying with magnesium sulfate, it was purified by silica column chromatography to obtain desired compound 2. (Yield: 49%)

4. 2 - ((3- Bromo -5- (4- Octylphenyl ) Thiophen-2-yl) methyl ) -5- ((3-bromothiophen-2-yl) methyl) thieno (3-bromothiophen-2-yl) methyl) thieno [2, 3 -bromo-5- 3,2-b] thiophene) (Synthesis of Compound 4)

Compound 3 (5.2 g, 7.4 mmol) was dissolved in 1 L of dichloromethane and then ZnI ₂ A (3.8 g, 11.9 mmol) and _{NaCNBH 3 (3.3 g, 52.1 mmol} ) was added slowly. The mixture was stirred at room temperature for 24 hours, washed with saturated ammonium chloride solution and water, and then dried over MgSO ₄ and concentrated under reduced pressure to obtain a yellow oil. This material was purified by silica column chromatography to give the desired compound 4. (Yield: 98%)

Thieno [2,3-b] thiophen-2-yl) methyl) -5- (4-methoxyphenyl) 3-cyanothiophen-2-yl) methyl) thieno [3,2-b] thiophen-2-yl) methyl) -5- (4-octylphenyl) thiophene-3-carbonitrile) (Synthesis of Compound 5)

The compound 4 (0.3 g, 0.44 mmol) was dissolved in 6 ml of N-methylpyrrolidone, and then cupricanide (CuCN) (0.16 g, 1.8 mmol) Lt; / RTI > After completion of the reaction, the mixture was poured into 1N HCl solution and stirred for 30 minutes. The solid was filtered, extracted with dichloromethane, and washed with water. After drying with magnesium sulfate, the desired compound 5 was obtained by short path column using celite and silica. (Yield: 81%)

6. (2 - ((5-decyl- ((3-formylthiophen-2-yl) methyl) thieno [3,2-b] thiophen-2-yl) methyl 2-yl) methyl) thieno [3,2-b] thiophen-2-yl) methyl) thiophene-3-carbaldehyde ) -5- (4-octylphenyl) thiophene-3-carbaldehyde) (Synthesis of Compound 6)

Compound 5 (1.6 g, 4.2 mmol) was dissolved in dichloromethane (200 mL) and the temperature was lowered to 0 캜. Diisobutylaluminium hydride (DIBALH, 1.0 M solution in cyclohexane) (10.1 ml, 10.1 mmol) was added thereto, followed by stirring for 4 hours. The reaction solution of methanol and water mixture (Methanol: water = 2: 1 ) After completion of the reaction is poured in, and then extracted with dichloromethane (dichloromethane), washed with water and Dublin (brine), the organic layer with MgSO ₄ After drying and concentration under reduced pressure, the material was purified by silica chromatography to obtain the desired compound 6. (Yield: 91%)

7. Synthesis of Compound 7

The compound 6 (1.1 g, 1.9 mmol) was dissolved in 100 mL of benzene, Amberlyst 15 (1.1.0 g) was added thereto, and the mixture was stirred under reflux in a Dean-Stark trap. To remove water. After 24 hours, the temperature of the pale yellow liquid was lowered to room temperature to form a white precipitate. The precipitated suspension was collected by filtration with a filter, and then recrystallized in a mixture of nucleic acid and chloroform to obtain Compound 7 as a white solid. (Yield: 72%)

MS (MALDI-TOF-MS, m / z) 540.11 (M +)

Comparative Synthetic Example  One

[Reaction Scheme 1A]

(1) Synthesis of Compound 2

Thienothiophene (1) is synthesized by the method developed by Iddon et al . (See Lance S. Fuller, Brian Iddon, Kevin A. Smith J. Chem . Soc ., Perkin Trans. 3470). Thienothiophene (3.35 g, 24 mmol) was dissolved in 50 mL of dry ether and added dropwise to 100 mL of dry ether solution containing butyllithium (21 mL of 2.5 M in hexane solution) cooled to 0, And the mixture was stirred at room temperature for 2 hours. Dimethylformamide (DMF; 4.6 mL) is slowly added dropwise to the cloudy solution and stirred overnight. To this is added 50 mL of saturated ammonium chloride solution, and the precipitated material is filtered off and washed several times with water and ether to obtain the desired compound 2 (yield: 75%).

_{^{1 NMR (CDCl 3) d 10.1}} (s, 2H), 8.05 (s, 2H).

(2) Synthesis of Compound 3

Dissolve 2,3-dibromothiophene (2.42 g, 10 mmole) in 100 mL of a 5: 1 solution of ether and THF and cool to -78 ° C. To this was slowly added butyllithium (11 mmole) dropwise and stirred for 30 minutes. The solution was slowly added dropwise to a solution (0.99 g, 5 mmole) in THF (100 mL) (-78 ° C), and the temperature was gradually raised to room temperature with stirring. 100 ml of a saturated ammonium chloride solution was added to terminate the reaction, 200 ml of ether was added, and the organic layer was separated. The separated organic layer was washed with Dublin (brine), dried to obtain a yellow oil and concentrated by MgSO _4. This material is purified by silica chromatography (hexane: ethyl acetate = 5: 1) to obtain the desired diol compound.

_{^{1 NMR (CDCl 3) d 7.32}} (d, 2H), 7.18 (s, 2H), 6.97 (dd, 2H), 6.42 (d, 2H), 2.76 (d, 2H).

The diol compound (1.4 g, 2.7 mmole) was dissolved in 150 mL of dichloromethane. Then, ZnI ₂ (2.75 g, 8.6 mmole) and NaCNBH ₃ (2.4 g, 37.66 mmole) were slowly added thereto. The mixture is stirred at room temperature for 24 hours, and then passed through a Celite pad. The filtrate is washed with a saturated ammonium chloride solution and water, respectively, and then dried over MgSO ₄ and concentrated under reduced pressure to give a yellow oil. This material is purified by silica chromatography to obtain the desired compound 3 (yield: 80%).

_{^{1 NMR (CDCl 3) d 7.17}} (d, 2H), 6.98 (s, 2H), 6.94 (d, 2H), 4.34 (s, 4H)

(3) Synthesis of Compound 4

THF (5 mL) solution of Compound 3 (385 mg, 0.79 mmole) dissolved in THF (10 mL) cooled to -78 ° C in which butyllithium (1.73 mmole) is dissolved is slowly added dropwise. After stirring at -78 [deg.] C for about 20 minutes, DMF (150 mL, 1.97 mmole) is added and stirred for another 2 hours. After pouring water to terminate the reaction, 30 mL of ether is added, washed with water and brine, then the organic layer is dried over MgSO ₄ and concentrated under reduced pressure to give a colorless oil. This material is purified by silica chromatography to give the desired compound 4 (yield: 70%).

_{NMR (CDCl 3) d 10.1 (} s, 2H), 7.43 (d, 2H), 7.20 (d, 2H), 7.02 (s, 2H), 4.76 (s, 4H).

(4) Synthesis of Compound 5

Compound 4 (200 mg) was dissolved in 1 mL of toluene, Amberlyst 15 (300 mg) was added, and the mixture was stirred and refluxed to remove water using a Dean-Stark trap. After about 24 hours, a beige solid precipitates. The temperature is lowered to room temperature to precipitate amberlist 15, and the supernatant is filtered off to obtain the desired compound 5 as a pale yellow solid (yielding 60% of a blue fluorescent substance). The compound 5 is purified by sublimation under high vacuum (<10 ^-4 torr) (mp 423).

Comparative Synthetic Example  2

(X)

Referring to paragraphs [0061] to [0091] of U.S. Patent No. 7,816,673 (US 7,816,673 B2, Oct. 19, 2010), the compound represented by Formula X is obtained.

Comparative Synthetic Example  3

[Formula Y]

The compound represented by Formula Y is obtained by referring to [0113] to [0148] of Korean Patent Laid-Open No. 10-2013-0136938 (Dec. 13, 2013).

Organic compound Thermal stability

In order to evaluate the thermal stability of the compounds obtained in Synthesis Example 1 and Comparative Synthesis Examples 1 and 2, the pyrolysis temperature was measured and evaluated. The thermal degradation temperature (T _d ) is the temperature at which the compound begins to decompose and is the temperature at which the compound is deformed without maintaining its original molecular structure. Generally, above the pyrolysis temperature, the intramolecular atoms constituting the compound volatilize and disappear into the atmosphere or vacuum, so that the pyrolysis temperature can be evaluated as the temperature at which the initial weight of the compound begins to decrease by heat. Here, thermal gravimetric analysis (TGA) is used.

FIG. 2 is a graph of thermal gravimetric analysis (TGA) of the compound obtained according to Comparative Synthesis Example 1, FIG. 3 is a graph of thermal gravimetric analysis (TGA) of the compound obtained according to Comparative Synthesis Example 2, 4 is a graph of thermal gravimetric analysis (TGA) of the compound obtained according to Synthesis Example 1. Fig.

2 to 4, the decomposition temperature at which 1 wt% of the compound according to Comparative Synthesis Example 1 disappears is about 336 DEG C, the decomposition temperature at which 1 wt% of the compound according to Comparative Synthesis Example 2 disappears is about 350 DEG C, The decomposition temperature at which 1 wt% of the compound according to Synthesis Example 1 disappears is about 386 ° C. From this, it can be confirmed that the compound of Synthesis Example 1 is superior to the compounds of Comparative Synthesis Examples 1 and 2 in thermal stability.

Liquid Crystalline Properties of Organic Compounds

In order to confirm the liquid crystal properties of the compounds obtained in Synthesis Example 1 and Comparative Synthesis Examples 1 to 3, differential scanning calorimetry (DSC) was used.

5 to 7 are differential scanning calorimetry (DSC) graphs of the compounds obtained according to Comparative Synthesis Examples 1 to 3, respectively. Figs. 8 to 12 are graphs showing the differential scanning calorimetry Differential scanning calorimetry (DSC) graph.

5 to 12, the compounds according to Comparative Synthesis Example 1 showed no liquid crystallinity, the compounds according to Comparative Synthesis Examples 2 and 3 showed nematic liquid crystallinity, and the compounds according to Synthesis Examples 1 to 5 exhibited nematic It can be seen that not only liquid crystallinity but also smectic liquid crystallinity is confirmed (2D structure).

Example  1: Organic Thin Film Transistor ( OTFT ) Production

First, chromium used as a gate electrode is deposited on the cleaned glass substrate by sputtering to a thickness of 1000 Å, followed by deposition of SiO ₂ which is used as an insulating layer by CVD to a thickness of 3000 Å. Au, which is used thereon, is deposited to a thickness of 700Å by sputtering to form a source electrode and a drain electrode. Before the organic compound is applied to the glass substrate Wash with isopropyl alcohol for 10 minutes and dry. Also, UV / O ₃ is treated for 30 minutes before modifying the surface of SiO ₂ used as an insulating layer. Subsequently, the substrate was immersed in an octyl trichlorosilane solution diluted with n-hexane to a concentration of 10 mM for 30 minutes, washed with hexane and ethanol, and dried. Then, the organic compound according to Synthesis Example 1 was evaporated at a deposition rate of 1 Å / To form an active layer of 330 ANGSTROM, and then annealed at 225 DEG C for 2 hours to fabricate an organic thin film transistor. 　

Example  2 to 5 and Comparative Example  1 to 3

An organic thin film transistor was fabricated in the same manner as in Example 1, except that the organic compounds according to Synthesis Examples 2 to 5 and Comparative Synthesis Examples 1 to 2 were used in place of the organic compound according to Synthesis Example 1, respectively.

Electrical Characterization

Current transfer characteristic curves of OTFT devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 3 are measured using Semiconductor Characterization System (4200-SCS) manufactured by KEITHLEY. The charge mobility of the organic thin film transistor according to Example 1 is shown in Table 1.

device Charge mobility (cm ² / Vs) I _on
(On current, A) I _on / I _off Example 1 11.6 6.2 X 10 ^-4 10 ⁶ Comparative Example 1 7 2.0 X 10 ^-4 10 ⁶ Comparative Example 2 7 2.5 X 10 ^-4 10 ⁶

In Table 1, the charge mobility is obtained from the slope by obtaining a graph of (ISD) ^1/2 and V _G as a variable from Equation 1, which is a saturation region current equation.

[Equation 1]

　

　

Where W is the channel width, L is the channel length, V _G is the gate voltage, and V L is the channel length. In this equation, I _SD is the source-drain current, μ or μ _FET is the charge transfer, C _O is the oxide film capacitance, And V _T is the threshold voltage.

The current flicker ratio (I _on / I _off ) was determined by the ratio of the maximum current value (I _on ) in the _on state to the minimum current value (I _off ) in the off state.

It can be seen from the results of Table 1 that the organic thin film transistor according to Example 1 exhibits excellent electrical characteristics as compared with the organic thin film transistor according to Comparative Examples 1 and 2.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

110: substrate 124: gate electrode
140: gate insulating film 154: organic semiconductor
173: source electrode 175: drain electrode

Claims (33)

An organic compound selected from a compound represented by the formula (1A), a compound represented by the formula (1B), and combinations thereof:
&Lt; EMI ID =

&Lt; RTI ID = 0.0 &

In the above formulas 1A and 1B,
Ar ¹ and Ar ² are each independently benzene, naphthalene or anthracene,
X ¹ to X ⁴ each independently represent O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom or a combination thereof,
n1, n2 and n3 are each independently 0 or 1,
R ¹ to R ⁴ are each independently hydrogen, a halogen atom, a substituted or unsubstituted straight or branched chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain or branched C2 to C30 alkenyl group, a substituted or unsubstituted straight- A substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, C30 alkylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, or a combination thereof,
R ¹ and R ² are groups having different structures, or R ³ and R ⁴ are groups having different structures. The method of claim 1,
an organic compound satisfying n2 = n3 = 0 or n2 = n3 = 1 when n1 = 0 and n2 = n3 = 0 when n1 = The method of claim 1,
Any one of R ¹ and R ² is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
The other of R ¹ and R ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,
R ³ and R ⁴ are each independently hydrogen or a halogen atom; or
Either of R ³ and R ⁴ is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
The other of R ³ and R ⁴ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 A substituted or unsubstituted C7 to C30 arylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 A heterocycloalkyl group, or a combination thereof,
R ¹ and R ² are each independently hydrogen or a halogen atom
Organic compounds. 4. The method of claim 3,
X &lt; ⁴ &gt; is S,
R ² is a fluorine-substituted C 6 to C 30 aryl group, a fluorine-substituted C 2 to C 30 heteroaryl group, a fluoro-substituted C 7 to C 30 alkylaryl group, a fluoro-substituted C 2 to C 30 alkylheteroaryl group, Substituted C5 to C30 cycloalkyl groups, fluoro substituted C2 to C30 heterocycloalkyl groups, or combinations thereof
Organic compounds. 4. The method of claim 3,
R ² is a substituted or unsubstituted pentachloro ring, a substituted or unsubstituted hexachloro ring, or a combination thereof. The method of claim 5,
R ² is an organic compound which is a heterocyclic group represented by the following formula (2A) or (2B), a substituted or unsubstituted alkylaryl group represented by the following formula (2C)
(2A)

(2B)

[Chemical Formula 2C]

In the above formulas (2A), (2B) and (2C)
X ⁵ is O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom, or a combination thereof,
X &lt; ⁶ &gt; is N,
R ⁵ R ⁶ and R ⁷ are each independently selected from the group consisting of a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
a is an integer of 0 to 3,
b is an integer of 0 to 4,
c is an integer of 0 to 4,
R ^a and R ^b are each independently hydrogen or a C 1 to C 6 alkyl group and m is 0 to 20, and when m is 2 or more, - (CR ^a R ^b ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
R ^c and R ^d are each independently hydrogen or a C 1 to C 6 alkyl group and n is 0 to 20, and when n is 2 or more, - (CR ^c R ^d ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
R ^e and R ^f are each independently hydrogen or a C 1 to C 6 alkyl group and r is 0 to 20, and when r is 2 or more, - (CR ^e R ^f ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
* Is the connection point. The method of claim 1,
Any one of R ¹ and R ² is a substituted or unsubstituted branched C3 to C30 alkyl group, a substituted or unsubstituted branched C4 to C30 alkenyl group, a substituted or unsubstituted branched C4 to C30 alkynyl group, Lt; / RTI &
The other of R ¹ and R ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,
R ³ and R ⁴ are each independently hydrogen or a halogen atom; or
Any one of R ³ and R ⁴ is a substituted or unsubstituted branched C3-C30 alkyl group, a substituted or unsubstituted branched C4-C30 alkenyl group, a substituted or unsubstituted branched C4-C30 alkynyl group, Lt; / RTI &
The other of R ³ and R ⁴ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,
R ¹ and R ² are each independently hydrogen or a halogen atom
Organic compounds. 8. The method of claim 7,
X &lt; ⁴ &gt; is S,
R ² is a fluorine-substituted C 6 to C 30 aryl group, a fluorine-substituted C 2 to C 30 heteroaryl group, a fluoro-substituted C 7 to C 30 alkylaryl group, a fluoro-substituted C 2 to C 30 alkylheteroaryl group, Substituted C5 to C30 cycloalkyl groups, fluoro substituted C2 to C30 heterocycloalkyl groups, or combinations thereof
Organic compounds. 8. The method of claim 7,
R ² is a substituted or unsubstituted pentachloro ring, a substituted or unsubstituted hexachloro ring, or a combination thereof. The method of claim 9,
R ² is a substituted or unsubstituted phenyl group, a heterocyclic group represented by the following formula (2A) or (2B), or a combination thereof:
(2A)

(2B)

[Chemical Formula 2C]

In the above formulas (2A), (2B) and (2C)
X ⁵ is O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom, or a combination thereof,
X &lt; ⁶ &gt; is N,
R ⁵ R ⁶ and R ⁷ are each independently selected from the group consisting of a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
a is an integer of 0 to 3,
b is an integer of 0 to 4,
c is an integer of 0 to 4,
R ^a and R ^b are each independently hydrogen or a C 1 to C 6 alkyl group and m is 0 to 20, and when m is 2 or more, - (CR ^a R ^b ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
R ^c and R ^d are each independently hydrogen or a C 1 to C 6 alkyl group and n is 0 to 20, and when n is 2 or more, - (CR ^c R ^d ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
R ^e and R ^f are each independently hydrogen or a C 1 to C 6 alkyl group and r is 0 to 20, and when r is 2 or more, - (CR ^e R ^f ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
* Is the connection point. The method of claim 1,
Any one of R ¹ and R ² is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
And the other of R ¹ and R ² is a substituted or unsubstituted branched C3-C30 alkyl group, a substituted or unsubstituted branched C4-C30 alkenyl group, a substituted or unsubstituted branched C4-C30 alkynyl group, Lt; / RTI &
R ³ and R ⁴ are each independently hydrogen or a halogen atom; or
Either of R ³ and R ⁴ is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
The other of R ³ and R ⁴ is a substituted or unsubstituted branched C3 to C30 alkyl group, a substituted or unsubstituted branched C4 to C30 alkenyl group, a substituted or unsubstituted branched C4 to C30 alkynyl group, Lt; / RTI &
R ¹ and R ² are each independently hydrogen or a halogen atom
Organic compounds. The method of claim 1,
If n1 = ¹ Ar 1 and Ar ² is benzene, the organic compound. The method of claim 1,
Organic compound having a molecular weight of 300 to 5,000. The method of claim 1,
R ¹ and R ² are from each other when caused by having a different structure, R ³ and R ⁴ are each independently hydrogen or halogen atom, R ³ and R ⁴ are each case caused with the other structures, R ¹ and R ² are independently Hydrogen or a halogen atom. A compound selected from the group consisting of a compound represented by the following formula (1A), a compound represented by the formula (1B), and a combination thereof, wherein the compound exhibits a Smectic phase at a temperature of 300 ° C or higher in a differential scanning calorimetry (DSC) , &Lt; / RTI &gt;
&Lt; EMI ID =

&Lt; RTI ID = 0.0 &

In the above formulas 1A and 1B,
Ar ¹ and Ar ² are each independently benzene, naphthalene or anthracene,
X ¹ to X ⁴ each independently represent O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom or a combination thereof,
n1, n2 and n3 are each independently 0 or 1,
R ¹ to R ⁴ are each independently hydrogen, a halogen atom, a substituted or unsubstituted straight or branched chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain or branched C2 to C30 alkenyl group, a substituted or unsubstituted straight- A substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, C30 alkylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, or a combination thereof,
R ¹ and R ² are groups having different structures, or R ³ and R ⁴ are groups having different structures. An organic thin film comprising an organic compound according to any one of claims 1 to 15. Gate electrode,
An organic semiconductor superimposed on the gate electrode, and
A source electrode and a drain electrode electrically connected to the organic semiconductor,
/ RTI &gt;
Wherein the organic semiconductor comprises an organic compound selected from a compound represented by the following formula (1A), a compound represented by the formula (1B), and combinations thereof:
&Lt; EMI ID =

&Lt; RTI ID = 0.0 &

In the above formulas 1A and 1B,
Ar ¹ and Ar ² are each independently benzene, naphthalene or anthracene,
X ¹ to X ⁴ each independently represent O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 aryl group, C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom or a combination thereof,
n1, n2 and n3 are each independently 0 or 1,
R ¹ to R ⁴ are each independently hydrogen, a halogen atom, a substituted or unsubstituted straight or branched chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain or branched C2 to C30 alkenyl group, a substituted or unsubstituted straight- A substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, C30 alkylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, or a combination thereof,
R ¹ and R ² are groups having different structures, or R ³ and R ⁴ are groups having different structures. The method of claim 17,
wherein n2 = n3 = 0 or n2 = n3 = 1 when n1 = 0 and n2 = n3 = 0 when n1 = 1. The method of claim 17,
Any one of R ¹ and R ² is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
The other of R ¹ and R ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,
R ³ and R ⁴ are each independently hydrogen or a halogen atom; or
Either of R ³ and R ⁴ is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
The other of R ³ and R ⁴ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 A substituted or unsubstituted C7 to C30 arylheteroaryl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C7 to C30 arylheteroalkyl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 A heterocycloalkyl group, or a combination thereof,
R ¹ and R ² are each independently hydrogen or a halogen atom
Organic thin film transistor. 20. The method of claim 19,
X &lt; ⁴ &gt; is S,
R ² is a fluorine-substituted C 6 to C 30 aryl group, a fluorine-substituted C 2 to C 30 heteroaryl group, a fluoro-substituted C 7 to C 30 alkylaryl group, a fluoro-substituted C 2 to C 30 alkylheteroaryl group, Substituted C5 to C30 cycloalkyl groups, fluoro substituted C2 to C30 heterocycloalkyl groups, or combinations thereof
Organic thin film transistor. 20. The method of claim 19,
R ² is a substituted or unsubstituted pentagonal ring, a substituted or unsubstituted hexagonal ring, or a combination thereof. 22. The method of claim 21,
R ² is a substituted or unsubstituted phenyl group, a heterocyclic group represented by the following formula (2A) or (2B), or a combination thereof:
(2A)

(2B)

In the above formulas (2A) and (2B)
X ⁵ is O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxy group, a halogen atom, or a combination thereof, and X ⁶ is N,
R ⁵ and R ⁶ are each independently a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 hetero An aryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
a is an integer of 0 to 3,
b is an integer of 0 to 4,
R ^a and R ^b are each independently hydrogen or a C 1 to C 6 alkyl group and m is 0 to 20, and when m is 2 or more, - (CR ^a R ^b ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
R ^c and R ^d are each independently hydrogen or a C 1 to C 6 alkyl group and n is 0 to 20, and when n is 2 or more, - (CR ^c R ^d ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
* Is the connection point. The method of claim 17,
Any one of R ¹ and R ² is a substituted or unsubstituted branched C3 to C30 alkyl group, a substituted or unsubstituted branched C4 to C30 alkenyl group, a substituted or unsubstituted branched C4 to C30 alkynyl group, Lt; / RTI &
The other of R ¹ and R ² is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,
R ³ and R ⁴ are each independently hydrogen or a halogen atom; or
Any one of R ³ and R ⁴ is a substituted or unsubstituted branched C3-C30 alkyl group, a substituted or unsubstituted branched C4-C30 alkenyl group, a substituted or unsubstituted branched C4-C30 alkynyl group, Lt; / RTI &
The other of R ³ and R ⁴ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C7 to C30 alkylaryl group, a substituted or unsubstituted C2 C30 alkylheteroaryl group, a substituted or unsubstituted C7-C30 arylheteroalkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a combination thereof,
R ¹ and R ² are each independently hydrogen or a halogen atom
Organic thin film transistor. 24. The method of claim 23,
X &lt; ⁴ &gt; is S,
R ² is a fluorine-substituted C 6 to C 30 aryl group, a fluorine-substituted C 2 to C 30 heteroaryl group, a fluoro-substituted C 7 to C 30 alkylaryl group, a fluoro-substituted C 2 to C 30 alkylheteroaryl group, Substituted C5 to C30 cycloalkyl groups, fluoro substituted C2 to C30 heterocycloalkyl groups, or combinations thereof
Organic thin film transistor. 24. The method of claim 23,
R ² is a substituted or unsubstituted pentagonal ring, a substituted or unsubstituted hexagonal ring, or a combination thereof. 26. The method of claim 25,
R ² is a heterocyclic group represented by the following formula (2A) or (2B), a substituted or unsubstituted alkylaryl group represented by the following formula (2C), or a combination thereof.
(2A)

(2B)

[Chemical Formula 2C]

In the above formulas (2A), (2B) and (2C)
X ⁵ is O, S, Se, Te or NR ^a wherein R ^a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a hydroxyl group, a halogen atom, or a combination thereof,
X &lt; ⁶ &gt; is N,
R ⁵ and R ⁶ are each independently a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 hetero An aryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
a is an integer of 0 to 3,
b is an integer of 0 to 4,
c is an integer of 0 to 4,
R ^a and R ^b are each independently hydrogen or a C 1 to C 6 alkyl group and m is 0 to 20, and when m is 2 or more, - (CR ^a R ^b ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
R ^c and R ^d are each independently hydrogen or a C 1 to C 6 alkyl group and n is 0 to 20, and when n is 2 or more, - (CR ^c R ^d ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
R ^e and R ^f are each independently hydrogen or a C 1 to C 6 alkyl group and r is 0 to 20, and when r is 2 or more, - (CR ^e R ^f ) - is -O-, -C (= O) , -OC (= O) O- or -C (= O) O-,
* Is the connection point. The method of claim 17,
Any one of R ¹ and R ² is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
And the other of R ¹ and R ² is a substituted or unsubstituted branched C3-C30 alkyl group, a substituted or unsubstituted branched C4-C30 alkenyl group, a substituted or unsubstituted branched C4-C30 alkynyl group, Lt; / RTI &
R ³ and R ⁴ are each independently hydrogen or a halogen atom; or
Either of R ³ and R ⁴ is a substituted or unsubstituted straight-chain C1 to C30 alkyl group, a substituted or unsubstituted straight-chain C2 to C30 alkenyl group, a substituted or unsubstituted straight-chain C2 to C30 alkynyl group,
The other of R ³ and R ⁴ is a substituted or unsubstituted branched C3 to C30 alkyl group, a substituted or unsubstituted branched C4 to C30 alkenyl group, a substituted or unsubstituted branched C4 to C30 alkynyl group, Lt; / RTI &
R ¹ and R ² are each independently hydrogen or a halogen atom
Organic thin film transistor. The method of claim 17,
If n1 = ¹ Ar 1 and Ar ² is benzene, the organic thin film transistor. The method of claim 17,
Wherein the organic compound has a molecular weight of 300 to 5,000. The method of claim 17,
R ¹ and R ² are from each other when caused by having a different structure, R ³ and R ⁴ are each independently hydrogen or halogen atom, R ³ and R ⁴ are each case caused with the other structures, R ¹ and R ² are independently Hydrogen or a halogen atom. An electronic device comprising the organic thin film transistor according to any one of claims 17 to 30. 32. The method of claim 31,
Wherein the electronic device is selected from a solar cell, a liquid crystal display device, an organic light emitting device, an electrophoresis device, an organic photoelectric device, and an organic sensor. An electronic device comprising the organic thin film according to claim 16.

Images