KR20160093550A - Fused Polycyclic Heteroaromatic Compound, Organic Thin Film Including Compound and Electronic Device Including Organic Thin Film - Google Patents

Abstract

Provided is a fused polycyclic heteroaromatic compound which is represented by chemical formula 1A or 1B. According to the present invention, the fused polycyclic heteroaromatic compound is highly fused since at least eight rings are fused together, and also allows charges to freely move within molecules due to high planarity. In addition, the present invention further relates to an organic thin film including the fused polycyclic heteroaromatic compound, and to an electronic device including the thin film as a carrier transfer layer.

Description

TECHNICAL FIELD [0001] The present invention relates to a condensed polycyclic aromatic heteroaromatic compound, an organic thin film including the same, and an electronic device including the organic thin film.

The present invention relates to a condensed polycyclic heteroaromatic compound, an organic thin film containing the same, and an electronic device including the organic thin film.

Various flat panel display devices such as liquid crystal display devices and organic electroluminescence display devices are provided with various thin film transistors (TFTs) for driving these devices. The thin film transistor includes a gate electrode, a source and a drain electrode, and a semiconductor layer activated according to driving of the gate electrode, wherein the semiconductor layer includes an organic semiconductor material whose current is controlled between a source electrode and a drain electrode by a gate voltage .

BACKGROUND ART [0002] Recently, as organic semiconducting materials used for channels of thin film transistors, studies have been made on low molecular weight organic materials such as pentacene or high molecular weight organic materials such as polythiophenes. However, the polymer organic material has low charge mobility and high blocking leakage current. On the other hand, low-molecular organic materials such as pentacene have been reported to have a high charge mobility of 3.2 to 5.0 cm ² / Vs or more, but they are not suitable in terms of processability and large-scale production due to the necessity of expensive vacuum deposition equipment in forming a thin film.

Accordingly, there is a continuing need in the art for a new organic semiconductor material that satisfies both superior electrical characteristics and excellent processability.

One embodiment has a compact planar structure in which eight or more aromatic rings are fused to each other, thereby exhibiting high charge mobility, as well as a deposition process or a room temperature (about 24 to 25 ° C) solution process To provide a condensed polycyclic heteroaromatic compound of low molecular weight with excellent processability.

Another embodiment provides an organic thin film comprising the condensed polycyclic heteroaromatic compound.

Another embodiment provides an electronic device comprising the organic thin film as a carrier transporting layer.

According to one embodiment, there is provided a condensed polycyclic heteroaromatic 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 phenylene, naphthalene or anthracene, a corresponds to the number of hydrogen atoms bonded to the carbon atoms of Ar ¹ and Ar ² ,

X ¹ to X ⁴ each independently represents O, S, Se, Te or NR ^a wherein each R ^a is independently selected from the group consisting of hydrogen, a substituted or unsubstituted linear or branched alkyl group having from 1 to 30 carbon atoms, A substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, A substituted or unsubstituted C6 to C30 aryloxy group (-OR ^b , wherein R ^b is a substituted or unsubstituted C6 to C30 aryl group), a substituted or unsubstituted C4 to C30 cycloalkyl group Alkyl group, a substituted or unsubstituted C4 to C30 cycloalkyloxy group (-OR ^c , wherein R ^c is a substituted or unsubstituted C4 to C30 cycloalkyl group), a substituted or unsubstituted C2 to C30 heteroaryl Group, an acyl group (-C (= O) R ^d , wherein R ^d is substituted or (-S (= O) ₂ R ^e , wherein R ^e is a substituted or unsubstituted C1 to C30 alkyl group) or a carbamate group (-NHC (= O) OR ^f , wherein R ^f is a substituted or unsubstituted C1 to C30 alkyl group,

R ¹ to R ¹³ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkenyl 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 arylalkyl group, a substituted or unsubstituted C2 to C30 heteroarylalkyl group, A substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C5 to C30 cycloalkyl group or a substituted or unsubstituted C2 to C30 heterocycloalkyl group,

n1 is 0 or 1,

n2 and n3 are each independently 0, 1, 2 or 3,

When n1 is 0, n2 and n3 are integers of 1, 2, or 3,

When n1 is 1, n1 + n2 + n3? 2 are satisfied. For example, when n1 is 1, n2 and n3 may not be both zero.

R ¹ and R ⁷ are a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, A substituted or unsubstituted C2 to C30 heteroarylalkyl group, a substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, or a substituted or unsubstituted C2 to C30 heterocycloalkyl group .

Wherein R ¹ and R ⁷ may be a C1 to C30 alkyl group substituted with fluoro.

The R ^a is, for example, a substituted or unsubstituted C10 to C30 alkyl group, a substituted or unsubstituted C10 to C30 alkoxy group, a substituted or unsubstituted C10 to C30 alkenyl group or a substituted or unsubstituted C10 to C30 alkynyl group (C _n F _{2n +1} , wherein n is an integer of 1 or more) or a fluorine-substituted C 10 to C 30 alkyl group, preferably a fluorine-substituted C _{1 to} C 30 alkyl group, preferably a C 1 to C 30 perfluoroalkyl group May be a C10 to C30 perfluoroalkyl group (C _n F _{2n +1} , where n is an integer from 10 to 30).

The condensed polycyclic heteroaromatic compound may have an average molecular weight of about 350 to about 3000.

According to another embodiment, there is provided an organic thin film comprising the condensed polycyclic heteroaromatic compound.

According to another embodiment, there is provided an electronic device comprising the condensed polycyclic heteroaromatic compound.

The electronic device may be a transistor, an organic light emitting diode (OLED), a photovoltaic device, a solar cell, a laser device, a memory device, or a sensor.

The electronic device may comprise at least one charge transport layer, and the condensed polycyclic heteroaromatic compound may be included in the charge transport layer.

The condensed polycyclic heteroaromatic compound is a novel highly-fused compound having high planarity, so that charge transfer between molecules can be smoothly performed, thereby exhibiting improved semiconductor characteristics.

1 is a schematic cross-sectional view of a transistor according to one embodiment.
2 is a schematic cross-sectional view of a transistor according to another embodiment.

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

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

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

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

"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.

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

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

"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.

"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.

"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 >

According to one embodiment, there is provided a condensed polycyclic heteroaromatic compound represented by the following formula (1A) or (1B) having a compact planar structure in which eight or more aromatic rings are fused to each other.

≪ EMI ID =

≪ RTI ID = 0.0 &

In the above formulas 1A and 1B,

Ar ¹ and Ar ² are each independently phenylene, naphthalene or anthracene, a corresponds to the number of hydrogen atoms bonded to the carbon atoms of Ar ¹ and Ar ² ,

X ¹ to X ⁴ each independently represents O, S, Se, Te or NR ^a wherein each R ^a is independently selected from the group consisting of hydrogen, a substituted or unsubstituted linear or branched alkyl group having from 1 to 30 carbon atoms, A substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, A substituted or unsubstituted C6 to C30 aryloxy group (-OR ^b , wherein R ^b is a substituted or unsubstituted C6 to C30 aryl group), a substituted or unsubstituted C4 to C30 cycloalkyl group Alkyl group, a substituted or unsubstituted C4 to C30 cycloalkyloxy group (-OR ^c , wherein R ^c is a substituted or unsubstituted C4 to C30 cycloalkyl group), a substituted or unsubstituted C2 to C30 heteroaryl Group, an acyl group (-C (= O) R ^d , wherein R ^d is substituted or (-S (= O) ₂ R ^e , wherein R ^e is a substituted or unsubstituted C1 to C30 alkyl group) or a carbamate group (-NHC (= O) OR ^f , wherein R ^f is a substituted or unsubstituted C1 to C30 alkyl group,

R ¹ to R ¹³ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkenyl 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 arylalkyl group, a substituted or unsubstituted C2 to C30 heteroarylalkyl group, A substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C5 to C30 cycloalkyl group or a substituted or unsubstituted C2 to C30 heterocycloalkyl group,

n1 is 0 or 1,

n2 and n3 are each independently 0, 1, 2 or 3,

When n1 is 0, n2 and n3 are integers of 1, 2, or 3,

When n1 is 1, n1 + n2 + n3? 2 is satisfied.

In the general formula 1A and 1B, when the Ar ¹ and Ar ² phenylene group and a is is an integer of 0 to 2 is Ar ¹ and Ar ² naphthalene is from 0 to 4 integer, when the Ar ¹ and Ar ² anthracene 0-6 Lt; / RTI >

Wherein R ¹ and R ⁷ are a substituted or unsubstituted C1 to C30 alkyl group such as a substituted or unsubstituted C8 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetero A substituted or unsubstituted C5 to C30 arylalkyl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C2 to C30 heteroarylalkyl group, a substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, A substituted or unsubstituted C2 to C30 heterocycloalkyl group.

Wherein R ¹ and R ⁷ may be a C1 to C30 alkyl group substituted with fluoro.

The R ^a is, for example, a substituted or unsubstituted C10 to C30 alkyl group, a substituted or unsubstituted C10 to C30 alkoxy group, a substituted or unsubstituted C10 to C30 alkenyl group or a substituted or unsubstituted C10 to C30 alkynyl group (C _n F _{2n +1} , wherein n is an integer of 1 or more) or a fluorine-substituted C 10 to C 30 alkyl group, preferably a fluorine-substituted C _{1 to} C 30 alkyl group, preferably a C 1 to C 30 perfluoroalkyl group May be a C10 to C30 perfluoroalkyl group (C _n F _{2n +1} , where n is an integer from 10 to 30).

The condensed polycyclic heteroaromatic compound represented by the above formula (1A) or (1B) has a structure in which 8 or more aromatic rings and heteroaromatic rings are fused. When n1 is 0, n2 and n3 are integers of 1, 2, or 3. When n1 is 1, n1 + n2 + n3? 2 are satisfied. For example, when n1 is 1, n2 and n3 May not all be zero. By having such a compact planar molecular structure, when the condensed polycyclic heteroaromatic compound is applied to an electronic device, not only the oxidation potential is uniform and stable, but also is advantageous for intermolecular packing and stacking, And the synthesis itself is easy, so that it can be usefully used as a semiconductor material or an electron transporting material.

X ¹ and X ² and X ³ and X ⁴ in the above formula (1A) or (1B) may have the same element at positions symmetrical to each other to improve the packing or stacking property.

By locating at least one fused benzene ring between the heterocycles in the above formula (1A) or (1B), it is possible to increase the intermolecular interaction by the extension of 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. In addition, introducing the C10 to a long aliphatic chain group (e.g. an alkenyl group of a substituted or unsubstituted C10 to an alkyl group or a substituted or unsubstituted of C30 unsubstituted C10 to C30) of C30 in the general formula 1A and 1B of R ¹ to R ¹³ The solubility of the condensed polycyclic heteroaromatic compound in an organic solvent can be improved. Such solubility enhancement not only simplifies coating by a room temperature solution process in addition to a deposition process but also is effective in forming a thin film having a large surface area and is effective in terms of processability and workability.

When X ¹ to X ⁴ are NR ^a , R ^a is, for example, a substituted or unsubstituted C 10 to C 30 alkyl group, a substituted or unsubstituted C 10 to C 30 alkoxy group, a substituted or unsubstituted C 10 to C 30 alkenyl group Or a substituted or unsubstituted C10 to C30 alkynyl group, and as another example, a fluorine-substituted C1 to C30 alkyl group, preferably a C1 to C30 perfluoroalkyl group (C _n F _{2n +1} , wherein n is an integer of 1 or more Or a C10 to C30 alkyl group, preferably a C10 to C30 perfluoroalkyl group (C _n F _{2n +1} , where n is an integer of 10 to 30) substituted by fluorine. The introduction of such a substituent increases the intermolecular interaction, which is advantageous for molecular alignment, thereby improving the charge mobility. In addition, by introducing the substituent, the solubility of the condensed polycyclic heteroaromatic compound can be improved to facilitate the synthesis, mass production is easy, and the solution process can be easily carried out during the formation of the thin film.

The condensed polycyclic heteroaromatic compound according to one embodiment has a heteroaromatic ring in the outermost ring to increase the intermolecular interaction, which is advantageous for molecular alignment, thereby improving the charge mobility.

The condensed polycyclic heteroaromatic compounds according to one embodiment have an average molecular weight from about 300 to about 3000. When having an average molecular weight in the above range, handling is easy.

Specific examples of the condensed polycyclic heteroaromatic compound include the following compounds (1) to (58).

[Compounds (1) to (58)]

The hydrogen of each phenyl ring, thiophen ring, selenophen ring or pyrrole ring in the above compounds (1) to (58) is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 A substituted or unsubstituted C2 to C30 alkenyl group, 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 C2 to C30 alkenyl group, A substituted or unsubstituted C5 to C30 arylalkyl group, a substituted or unsubstituted C2 to C30 heteroarylalkyl group, a substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C5 to C30 cycloalkyl group or a substituted or unsubstituted Substituted with a C2 to C30 heterocycloalkyl group.

R ^a1 to R ^a48 in the above compounds (11) to (26) and (35) to (42) are each independently the same as R ^a in the above formulas (1A) and (1B) and are, for example, hydrogen, a substituted or unsubstituted straight- An alkyl group having a branched chain C1 to C30, a substituted or unsubstituted C6 to C30 aryl group, and may be a hydrogen, a methyl group or a phenyl group.

HOMO energy, reorganization energy and predicted mobility of the compounds (1), (3a), (5a), (29a) and (33a) in the above compounds (1) . The HOMO energy and the regrouping energy were calculated at the DFT B3LYP / 6-31G (d, p) level using the Gaussian 09 program and the transfer integral was calculated at PW91-TZP using the ADF (the Amsterdam Density Functional) To calculate the expected mobility. For comparison, the HOMO energies, the regrouping energies and the expected mobilities of the following Ref-1, Ref-2 and Ref-3a compounds are given in Table 1.

Ref-1 Ref-2

Ref-3a

compound E _HOMO
(eV) Regrouping energy (meV) Estimated mobility
cm ² / Vs Ref-1 -5.57 146 14.3 Ref-2 -5.52 130 5.0 Ref-3a -5.69 95 20.4 Compound (1) -5.26 91 23.6 Compound (3a) -5.24 83 37.8 Compound (5a) -5.26 82 26.5 Compound (29a) -5.27 54 26.2 Compound (33a) -5.26 52 49.2

As shown in Table 1, since the recombination energy of the compounds (1), (3a), (5a), (29a) and (33a) is smaller than that of the compounds Ref-1, Ref-2 and Ref-3a, It is expected to be delivered effectively. The expected mobility of the compounds (1), (3a), (5a), (29a) and (33a) was higher than that of the compounds Ref-1, Ref-2 and Ref-3a.

Another embodiment provides an organic thin film comprising the condensed polycyclic heteroaromatic compound and an electronic device comprising the organic thin film.

The organic thin film according to this embodiment can be used as a carrier transport layer such as an organic semiconductor layer and a channel layer of an electronic device by including the condensed polycyclic hetero aromatic compound as described above, And can exhibit excellent electrical characteristics of high charge mobility.

The organic thin film may be formed by depositing the condensed polycyclic aromatic compound on a substrate by a conventional method or by dissolving the condensed polycyclic aromatic compound in an organic solvent or by coating with a common room temperature solution process, If necessary, the thin film can be further improved in denseness and uniformity by performing the above-mentioned vapor deposition or heat treatment after coating.

Specifically, as the organic solvent, one or more conventional organic solvents may be used, and examples thereof include aliphatic hydrocarbon solvents such as hexane and heptane; Aromatic hydrocarbon solvents such as toluene, pyridine, quinoline, anisole, mesitylene and xylene; Ketone solvents such as methyl isobutyl ketone, 1-methyl-2-pyrrolidinone, cyclohexanone and acetone; Ether solvents such as tetrahydrofuran and isopropyl ether; Ethyl acetate, butyl acetate, propylene glycol methyl ether acetate and the like; Alcohol solvents such as isopropyl alcohol and butyl alcohol; Amide solvents such as dimethylacetamide and dimethylformamide; A silicone-based solvent; And a mixture of these solvents may be used. The content of the condensed polycyclic heteroaromatic compound dissolved in the organic solvent may be appropriately selected by a person skilled in the art, but is preferably in the range of about 0.01 to 50% by weight in terms of solubility and coating properties.

The organic thin film may be formed by thermal deposition, vacuum deposition, laser deposition, screen printing, printing, imprinting, spin casting, dipping, ink jetting, roll coating, flow coating, drop casting, Spray coating, roll printing, and the like may be used, but the present invention is not limited thereto. The heat treatment may be performed at 80 to 250 ° C for 1 minute to 2 hours, but is not particularly limited thereto.

The thickness of the organic thin film may be appropriately adjusted depending on the application and the case in consideration of the kind of the compound used by the person skilled in the art and the type of the solvent, but may be in the range of about 200 Å to about 10,000 Å.

Non-limiting examples of the electronic device including the organic thin film as the carrier transport layer include a transistor, an organic light emitting diode (OLED), a photovoltaic device, a solar cell, a laser device, a memory device or a sensor, The organic thin film may be applied to each of the above elements by a conventional process known in the art.

For example, the transistor may include a gate electrode located on a substrate; A source electrode and a drain electrode which are positioned opposite to each other to define a channel region; An insulating layer electrically isolating the source electrode and the drain electrode from the gate electrode; And an active layer including the condensed polycyclic hetero aromatic compound formed in the channel region.

The active layer may be formed by depositing the condensed polycyclic aromatic compound or the composition containing the condensed polycyclic aromatic aromatic compound through a solution process such as a screen printing method, a printing method, a spin coating method, a dipping method or an inkjet method . When the active layer is formed by the solution process as described above, the process cost can be reduced and it is useful in manufacturing a large-sized device.

1 and 2 are schematic cross-sectional views of a transistor according to an embodiment of the present invention. The transistor according to an embodiment of the present invention may be a thin film transistor. In case of a thin film transistor, the thickness of the thin film may be several nm to several 탆.

Referring to FIG. 1, a transistor 10 has a gate electrode 14 formed on a substrate 12, and an insulating layer 16 covering the gate electrode 14 is formed. A source electrode 17a and a drain electrode 17b defining a channel region are formed in the insulating layer 16 and an active layer 18 is formed in a channel region. The active layer 18 is formed of the condensed polycyclic hetero aromatic ≪ / RTI >

2, the transistor 20 includes a source electrode 27a and a drain electrode 27b defining a channel region on a substrate 22, an active layer 28 formed in a channel region, (28) comprises the condensed polycyclic heteroaromatic compound. An insulating layer 26 is formed while covering the source electrode 27a and the drain electrode 27b and the active layer 28 and a gate electrode 24 is formed thereon.

The substrate 12, 22 may be an inorganic material, an organic material, or a composite of an inorganic material and an organic material. Examples of the organic material include polyethylenenaphthalate (PEN), polyethylene terephthalate (PET), polycarbonate, polyvinyl alcohol, polyacrylate, polyimide, polynorbornene, polyethersulfone, PES), and the like, and examples of the inorganic material include glass and metal.

As the gate electrodes 14 and 24, the source electrodes 17a and 27a and the drain electrodes 17b and 27b, a commonly used metal may be used. Specifically, gold (Au), silver (Ag) (Al), nickel (Ni) indium tin oxide (ITO), and the like.

The insulating layer can be used with a large dielectric constant insulator which (16, 26) as is conventionally used, specifically Ba _{O. 33 Sr O.66 TiO 3 (BST,} Barium Strontium Titanate), Al 2 O 3, Ta 2 O 5, La 2 O 5, Y 2 O 3, TiO 2 as a ferroelectric insulator sequence and PbZr _{O. 33 Ti O.66 O 3 (PZT)} , Bi 4 Ti 3 O 12, BaMgF 4, SrBi 2 (TaNb) 2 O 9, Ba (ZrTi) O 3 (BZT), BaTiO 3, SrTiO 3, SiO 2, SiN _x (where x is determined by the valence of Si), an inorganic insulator such as AlON, a polyimide, a BCB (benzocyclobutene), a parylene, a polyacrylate, a polyvinylalcohol, Organic insulators such as polyvinylphenol may be used, but the present invention is not limited thereto. Although not mentioned above, the inorganic insulator disclosed in U.S. Patent No. 5,946,551 and the organic insulator described in U.S. Patent No. 6,232,157 can also be used as the insulating layers 16 and 26.

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

Synthetic example  One: Condensed polycyclic Heteroaromatic  Synthesis of Compound (Compound (1a))

[Reaction Scheme 1]

(1) Synthesis of (5-bromo-2-methoxyphenyl) methylsulfane (5-bromo-2-methoxyphenyl) methylsulfane

(20 g, 75 mmol, Compound 1-1) was dissolved in dry diethyl ether (100 mL) under nitrogen atmosphere, and then 2.5M n-BuLi in hexane (332 mL, 0.83 mol) was slowly added dropwise. After stirring at the same temperature for 1 hour, dimethyl disulfide (8.7 mL, 98 mmol) was slowly added. After 30 minutes, the reaction was completed by adding a saturated aqueous solution of ammonium chloride, followed by extraction with diethyl ether. The organic solvent layer was dried over anhydrous MgSO ₄ , concentrated, and then purified by silica gel column chromatography to obtain the desired compound 1-2 (yield: 94%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ ppm 7.20 ~ 7.18 (m, 2H), 6.68 (d, J = 8.4Hz, 1H), 3.86 (s, 3H), 2.42 (s, 3H)

(2) Synthesis of 4-methoxy-3- (methylthio) benzaldehyde 4-methoxy-3- (methylthio) benzaldehyde

Compound 1-2 (17.3 g, 74 mmol) was dissolved in dry diethyl ether (100 mL), and 2.5 M n-BuLi (in hexane) (32.6 mL, 81 mmol) was slowly added dropwise thereto at -78 ° C. After 1 hour, DMF (dimethylformamide, 8.6 mL, 110 mmol) was slowly added at the same temperature and stirred for 1 hour. After the reaction was completed by adding a saturated aqueous solution of ammonium chloride, the reaction mixture was extracted with diethyl ether. The organic solvent layer was dried over anhydrous MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography (EA: hexane = 1: 10) to obtain the desired compound 1-3 (yield: 79%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ 9.87 (s, 1H), 7.67 ~ 7.63 (m, 2H), 6.93 (d, J = 8.0Hz, 1H), 3.98 (s, 3H), 2.49 (s, 3H ).

(3-bromo-5-methylthiophen-2-yl) (4-methoxy-3- (methylthio) -methoxy-3- (methylthio) phenyl) methanol

Diisopropylamine (4.8 mL, 34 mmol) was dissolved in dry THF (30 mL), and 2.5 M n-BuLi in hexane (12.6 mL, 32 mmol) was slowly added dropwise at -78 ° C and the mixture was stirred for 30 minutes . At the same temperature, 2-bromo-5-methylthiophene (3 mL, 26.3 mmol) was added slowly and the reaction temperature was slowly raised to -10 and stirred for 1 hour. After cooling to -78 again, Compound 1-3 (6.2 g, 34.2 mmol) was added and stirred for 1 hour. After the reaction was completed by adding a saturated aqueous solution of ammonium chloride, the reaction mixture was extracted with diethyl ether, and the organic solvent layer was dried over anhydrous MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography (EA: hexane = 1: 8 by volume) to obtain 9 g of the desired compound 1-4 (yield: 95%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ 7.29 (s, 1H), 7.20 (d, J = 8.4Hz, 1H), 6.80 (d, J = 8.4Hz, 1H), 6.60 (s, 1H), 6.06 ( d, J = 3.2 Hz, 1H), 3.88 (s, 3H), 2.43 (s, 3H), 2.40 (s, 3H).

(4) 3-Bromo-2- (4-methoxy-3- (methylthio) benzyl) -5 -methylthiophene)

Compound 1-4 (9 g, 25 mmol) was dissolved in methylene chloride (500 mL), ZnI ₂ It was added (12 g, 37.5 mmol) and stirred for one day at _{NaBH 3 CN (3.15 g, 50.1} mmol) and the mixture was treated slowly at room temperature (25 ℃) after 10 minutes. After completion of the reaction, the mixture was filtered with Celite and concentrated. The residue was purified by silica gel column chromatography (hexane) to obtain 7.6 g of the desired compound 1-5 (yield: 88%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ 7.05 (s, 1H), 6.99 (d, J = 8.4Hz, 1H), 6.76 (d, J = 8.4Hz, 1H), 6.58 (s, 1H), 3.97 ( (s, 3H), 2.38 (s, 3H)

(5) Synthesis of 2- (4-methoxy-3- (methylthio) benzyl) -5-methylthiophene- 3-carbonitrile)

Compound 1-5 (8.5 g, 22 mmol) and CuCN (22 g, 220 mmol) were dissolved in NMP (25 mL) and the mixture was stirred at 120 for one day. After adding methylene chloride (100 mL), it was subjected to Celite filter to remove inorganic matter, and the organic layer was washed with water. The organic solvent layer was dried over anhydrous MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography (EA: hexane = 1: 10 by volume) to obtain 5.1 g of Compound 1-6 (71%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ 7.05 ~ 7.00 (m, 2H), 6.78 ~ 6.75 (m, 2H), 4.17 (s, 2H), 3.87 (s, 3H), 2.42 (s, 3H), 2.38 (s, 3 H)

(6) Synthesis of 2- (4-methoxy-3- (methylthio) benzyl) -5-methylthiophene-3-carboxaldehyde 3-carbaldehyde)

Compound 1-6 (5.1 g, 17.6 mmol) was dissolved in methylene chloride (40 mL) and 1M DIBAL (diisobutylaluminum in toluene) (19.4 mL, 19.4 mmol) was added slowly in an ice bath Followed by stirring for 3 hours. The reaction was terminated while methanol and water were added in small portions at the same temperature. The organic solvent layer was dried over anhydrous MgSO ₄ , filtered and concentrated. The residue was purified by silica gel column chromatography (EA: hexane = 1: 8 by volume) to obtain 4 g of Compound 1-7 (yield: 78%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ 9.99 (s, 1H), 7.04 ~ 6.99 (m, 3H), 6.76 (d, J = 8.0Hz, 1H), 4.39 (s, 2H), 3.87 (s, 3H ), 2.40 (s, 3 H), 2.39 (s, 3 H)

(7) Synthesis of 6-methoxy-2-methyl-7- (methylthio) naphtho [2,3-b ] thiophene)

Compound 1-7 (4 g, 13.7 mmol) was dissolved in toluene (40 mL), followed by addition of Amberlyst 15 (4 g) and heating and refluxing with Dean-Stark. After 2 hours, it was filtered with Celite and concentrated. Diethyl ether (80 mL) was added to the concentrated compound to precipitate and filter 3 g of compound 1-8 (yield: 80%).

¹ H NMR (300 MHz, CDCl ₃ )? 8.06 (s, IH), 7.96 (s, IH), 7.46 (s, ), 2.60 (s, 3H), 2.55 (s, 3H)

(8) Synthesis of 2-methyl-7- (methylthio) naphtho [2,3-b] thiophen- ol)

Compound 1-8 (3 g, 11 mmol) was dissolved in methylene chloride (30 mL). BBr ₃ (1.6 mL, 16.4 mmol) was slowly added in an ice bath and the mixture was stirred at room temperature (25 ° C) for 2 hours. After the reaction was completed by adding ice water to the reaction mixture, the reaction mixture was diluted with methylene chloride and washed with water. The organic solvent layer was dried over anhydrous MgSO ₄ and concentrated. Diethyl ether (100 mL) was added to the concentrated compound to precipitate and then filtered to obtain 2.3 g of the desired compound 1-9 (yield: 81%).

¹ H NMR (300 MHz, CDCl ₃ )? 8.08 (s, IH), 8.03 (s, IH), 7.94 (s, IH), 7.37 ), 2.60 (s, 3H), 2.43 (s, 3H)

(9) Synthesis of 2-methyl-7- (methylthio) naphtho [2,3-b] thiophen-6-yl trifluoromethanesulfonate (2-methyl- b] thiophen-6-yl trifluoromethane sulfonate)

A solution of Compound 1-9 (1.04 g, 4 mmol) in methylene chloride (40 ml) was cooled to 0 ° C. and then triethylamine (1.6 ml, 12 mmol) and trifluoromethanesulfonic anhydride ml, 5.5 mmol) were added dropwise in this order. After the reaction was completed at room temperature (25) for 40 hours, 1N aqueous HCl solution was poured and extracted with methylene chloride. And concentrated followed by drying the organic layer over anhydrous MgSO _4. Vacuum drying yielded 1.5 g of the desired compound 1-10 (yield: 95%).

¹ H NMR (300 MHz, CDCl ₃ )? 8.18 (s, IH), 8.08 (s, IH), 7.81 (s, IH), 7.71 ), 2.61 (s, 3H)

(10) Trans-1,2-bis (2-methyl-7- (methylthio) naphtho [2,3-b] thiophen-6-yl) -7- (methylthio) naphtho [2,3-b] thiophen-6-yl) ethene)

1,2-bis (tributylstannyl) ethene (0.91 g, 1.5 mmol) (1.18 g, 3 mmol) and Compound-1-10 ml) dissolved, where the _{Pd (PPh 3) 4 (0.18} g, 0.15 mmol) was added to the. The reaction flask was wrapped with aluminum foil, heated to reflux for 20 hours, and diluted with water. The precipitate was filtered and washed with water and ethanol to give 0.77 g of the desired compound 1-11 as a yellow solid (yield: 50%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ 8.19 (s, 2H), 8.13 (s, 4H), 7.70 (s, 2H), 7.67 (s, 2H), 7.05 (s, 2H), 2.62 (s, 6H ), 2.61 (s, 6H)

(11) Synthesis of di (2-methylthio [7,6-b: 7 ', 6'-f] naphthothieno [3,2- 7 ', 6'-f] naphthothieno [3,2-b] thiophene)

Compound (1-11) (0.62 g, 1.2 mmol) was added to acetic acid (2 ml), iodine powder (7 g, 28 mmol) was added and the mixture was refluxed for 12 hours. Acetic acid was removed by distillation, and a saturated NaHSO ₃ solution was added and stirred for 1 hour to remove excess iodine. The precipitate was filtered off, washed several times with water and acetone, and vacuum dried to give 0.29 g of the desired compound (1a) as a brown solid (yield: 50%).

Maldi-MS m / z = 481 (M + 1).

Synthetic example  2: Condensed polycyclic Heteroaromatic  Synthesis of Compound (Compound (1))

[Reaction Scheme 2]

(1) Synthesis of 7- (methylthio) naphtho [2,3-b] thiophen-6-yltrifluoromethane sulfonate (7- (methylthio) naphtho [ sulfonate

A solution of Compound 1-1 (7 g, 28.41 mmol) in methylene chloride (500 ml) was cooled to 0 ° C. and then triethylamine (10.69 ml, 76.72 mmol) and trifluoromethanesulfonic anhydride ml, 36.94 mmol) were added dropwise in this order. After the reaction was completed at room temperature (25 ° C) for 40 hours, 1N aqueous HCl solution was poured and extracted with methylene chloride. And concentrated followed by drying the organic layer over anhydrous MgSO _4. Vacuum drying afforded 8.37 g of the desired compound 1-2 (yield: 78%).

_{^{1 H NMR (300MHz, CDCl 3}} ) δ 8.32 (s, 1H), 8.28 (s, 1H), 7.85 (s, 1H), 7.72 (s, 1H), 7.56 (d, 1H), 7.43 (d, 1H ), 2.62 (s, 3H)

(2) Trans-1,2-bis (7- (methylthio) naphtho [2,3-b] thiophen- 2,3-b] thiophen-6-yl) ethene)

1,2-bis (tributylstannyl) ethene (5.92 g, 11.06 mmol) and Compound-1-2 (8.37 g, 22.12 mmol) ml) dissolved, where the _{Pd (PPh 3) 4 (3.83} g, 3.32 mmol) was added to the. The reaction flask was wrapped with aluminum foil, heated to reflux for 20 hours, and diluted with water. The precipitate was filtered and washed with water and ethanol to give 2.7 g of the desired compound 1-3 as a yellow solid (yield: 50%).

Maldi-MS m / z = 484.72 (M + 1).

 (3) di (thio [7,6-b: 7 ', 6'-f] naphthothieno [3,2- b] thiophene di [ -f] naphthothieno [3,2-b] thiophene)

Iodine powder (59.5 g, 234.5 mmol) was added to chloroform (350 ml) and the mixture was refluxed for 48 hours. The chloroform was distilled off, and a saturated NaHSO ₃ solution was added and stirred for 1 hour to remove excess iodine. The precipitate was filtered, washed several times with water and acetone, and vacuum dried to give 1.28 g of the desired compound (1) as a brown solid (yield: 50%).

Maldi-MS m / z = 452.03 (M + 1).

Synthetic example  3: Condensed polycyclic Heteroaromatic  Synthesis of Compound (Compound (1c))

[Reaction Scheme 3]

(1) Synthesis of 2-decyl-7- (methylthio) naphtho [2,3-b] thiophen-6-yl trifluoromethanesulfonate b] thiophen-6-yl trifluoromethane sulfonate)

A solution of Compound 1-1 (7 g, 18.10 mmol) in methylene chloride (500 ml) was cooled to 0 ° C. and then triethylamine (6.81 ml, 48.89 mmol) and trifluoromethanesulfonic anhydride ml, 23.54 mmol) were added dropwise in this order. After the reaction was completed at room temperature (25) for 40 hours, 1N aqueous HCl solution was poured and extracted with methylene chloride. And concentrated followed by drying the organic layer over anhydrous MgSO _4. Vacuum drying yielded 8.95 g of the desired compound 1-2 (yield: 95%).

¹ H NMR (300 MHz, CDCl ₃ )? 8.18 (s, IH), 8.08 (s, IH), 7.80 (s, IH), 7.71 ), 2.61 (s, 3H), 1.78 (m, 2H), 1.28 (m, 14H), 0.88

(2) Synthesis of trans-1,2-bis (2-decyl-7- (methylthio) naphtho [2,3-b] thiophen-6-yl) -7- (methylthio) naphtho [2,3-b] thiophen-6-yl) ethene)

1,2-bis (tributylstannyl) ethene (5.23 g, 8.63 mmol) and Compound-1-2 (8.95 g, 17.26 mmol) ml) dissolved, where the _{Pd (PPh 3) 4 (2.99} g, 2.59 mmol) was added to the. The reaction flask was wrapped with aluminum foil, heated to reflux for 20 hours, and diluted with water. The precipitate was filtered and washed with water and ethanol to give 2.36 g of the desired compound 1-3 as a yellow solid (yield: 36%).

¹ H NMR (300 MHz, CDCl ₃ )? 8.19 (s, IH), 8.14 (s, 2H), 7.70 (s, IH), 7.67 ), 2.62 (s, 3H), 1.78 (m, 2H), 1.36 (m,

(3) Synthesis of di (2-decylthio [7,6-b: 7 ', 6'-f] naphthothieno [3,2- 7 ', 6'-f] naphthothieno [3,2-b] thiophene)

Iodine powder (32.48 g, 128 mmol) was added to chloroform (300 ml) and the mixture was refluxed for 48 hours. The chloroform was distilled off, and a saturated NaHSO ₃ solution was added and stirred for 1 hour to remove excess iodine. The precipitate was filtered, washed several times with water and acetone, and vacuum dried to give the desired compound (1c) as a brown solid, 1.1 g (yield: 50%).

Maldi-MS m / z = 733.1 (M + 1).

Synthetic example  4: Condensed polycyclic Heteroaromatic  Synthesis of Compound (Compound (8))

[Reaction Scheme 4]

(1) Synthesis of 8- (methylthio) anthra [2,3-b] thiophen-7-ylthiophen-7-yl trifluoromethane sulfonate ) Synthesis of

A solution of Compound 8-1 (1.0 g, 3.37 mmol) in methylene chloride (100 ml) was cooled to 0 ° C and then triethylamine (1.27 ml, 9.1 mmol) and trifluoromethanesulfonic anhydride 0.74 ml, 4.39 mmol) were added dropwise in this order. After the reaction was completed at room temperature (25) for 40 hours, 1N aqueous HCl solution was poured and extracted with methylene chloride. And concentrated followed by drying the organic layer over anhydrous MgSO _4. Vacuum drying afforded 1.21 g of the desired compound 8-2 (yield: 95%).

¹ H NMR (300 MHz, CDCl ₃ )? 8.57 (s, IH), 8.57 (s, IH), 8.54 (s, IH), 8.47 ), 7.54 (d, IH), 7.43 (d, IH), 2.65 (s, 3H)

(2) Synthesis of trans-1,2-bis (8- (methylthio) anthra [2,3-b] thiophen- , 3-b] thiophen-7-yl) ethene)

(Trans-1,2-bis (tributylstannyl) ethene) (0.63 g, 1.17 mmol) and Compound 8-2 (1.1 g, 2.33 mmol) It is dissolved in ml), where the _{Pd (PPh 3) 4 (0.4} g, 0.35 mmol) was added. The reaction flask was wrapped with aluminum foil, heated to reflux for 20 hours, and diluted with water. The precipitate was filtered and washed with water and ethanol to give 0.26 g of the desired compound 8-3 as a yellow solid (yield: 43%).

Maldi-MS m / z = 584.8 (M + 1).

(3) Synthesis of Compound (8)

Compound 8-3 (0.25 g, 0.45 mmol) was added to chloroform (50 ml), iodine powder (4.56 g, 18.99 mmol) was added, and the mixture was refluxed for 48 hours. The chloroform was distilled off, and a saturated NaHSO ₃ solution was added and stirred for 1 hour to remove excess iodine. The precipitate was filtered, washed several times with water and acetone, and vacuum-dried to obtain 0.12 g (yield: 50%) of the desired compound (8) as a reddish brown solid.

Maldi-MS m / z = 552.7 (M + 1).

Condensed polycyclic Heteroaromatic  Compound Thermal stability

In order to evaluate the thermal stability of the compounds of Synthesis Examples 1 to 4, 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. The decomposition temperature at which 1 wt% of the compound of Synthetic Example 2 disappears is 468 DEG C, and the decomposition temperature at which 1 wt% of the Ref-1 compound disappears is 339 DEG C. From this, it can be confirmed that the compound of Synthesis Example 2 has excellent thermal stability.

Example  1 to 4: Condensed polycyclic Heteroaromatic  Preparation of organic thin film transistor using compound

First, the silicon substrate with the silicon oxide film covering 3000 Å is washed with isopropyl alcohol for 10 minutes and dried. After washing the cleaned silicon substrate with oxygen plasma, it was immersed in octadecyltrichlorosilane solution diluted to 5 mM concentration in hexane for 30 minutes, washed with hexane and ethanol, and baked for 120 to 30 minutes. Then, the substrate was immersed in chloroform solvent, do. The washed silicon substrate was dried, and then the condensed polycyclic aromatic compounds synthesized in Synthesis Examples 1 to 4 were respectively applied to a thickness of 700 Å by a vacuum thermal deposition method. And Au, which is used as a source and a drain electrode, is deposited thereon to a thickness of 1000 Å by sputtering to fabricate an organic thin film transistor (OTFT).

Comparative Example  1 to 4: Condensed polycyclic Heteroaromatic  Preparation of organic thin film transistor using compound

Organic thin film transistors (OTFTs) were fabricated in the same manner as in Examples 1 to 4, using the compounds shown in the following Table 2 instead of the condensed polycyclic aromatic heteroaromatic compounds synthesized in Synthesis Examples 1 to 4.

The charge mobility of the organic thin film transistors according to Examples 1 to 4 and Comparative Examples 1 to 4 is calculated.

Charge carrier mobility of the organic thin film transistor is a graph of the gain (I _SD) ^1/2 and V _G as a variable from the saturation region (saturation region) current type was determined from the slope:

[Equation 1]

In Equation 1, I _SD is the source-and-drain current, μ or μ _FET is also the charge transfer, C ₀ is the capacitance of the gate insulating film, W is a channel width, L is channel length, V _G is Gate voltage, and V _T is the threshold voltage.

The results of the measurement of the charge mobility of Example 2 and Comparative Examples 1 to 4 are shown in Table 2.

The Mobility (cm ² / Vs) Comparative Example 1

10 Comparative Example 2

3.1 Comparative Example 3

2 Comparative Example 4

3.0 Example 2

13

Referring to Table 2, the mobility of the organic thin film transistor of Example 2 including the compound of Synthesis Example 2 including 8 aromatic rings was evaluated as the compound (Ref-1, Ref-2) containing six aromatic rings The organic thin film transistor of Comparative Example 1 or Comparative Example 2 and the organic thin film transistor of Comparative Example 3 including 7 aromatic rings are superior in mobility. The mobility of the organic thin film transistor of Example 2 including the compound of Synthesis Example 2 in which thiophene ring is present is superior to that of the organic thin film transistor of Comparative Example 4 including a compound in which the phenylene ring is present in the outermost ring can confirm.

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.

10, 20: transistor
12, 22: substrate
16, 26: insulating layer
18, 28:
14, 24: Gate electrode
17a, 27a: source electrode
17b, 27b: drain electrode

Claims (11)

A condensed polycyclic heteroaromatic compound 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 phenylene, naphthalene or anthracene, a corresponds to the number of hydrogen atoms bonded to the carbon atoms of Ar ¹ and Ar ² ,
X ¹ to X ⁴ each independently represents O, S, Se, Te or NR ^a wherein each R ^a is independently selected from the group consisting of hydrogen, a substituted or unsubstituted linear or branched alkyl group having from 1 to 30 carbon atoms, A substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, A substituted or unsubstituted C6 to C30 aryloxy group (-OR ^b , wherein R ^b is a substituted or unsubstituted C6 to C30 aryl group), a substituted or unsubstituted C4 to C30 cycloalkyl group Alkyl group, a substituted or unsubstituted C4 to C30 cycloalkyloxy group (-OR ^c , wherein R ^c is a substituted or unsubstituted C4 to C30 cycloalkyl group), a substituted or unsubstituted C2 to C30 heteroaryl Group, an acyl group (-C (= O) R ^d , wherein R ^d is substituted or (-S (= O) ₂ R ^e , wherein R ^e is a substituted or unsubstituted C1 to C30 alkyl group) or a carbamate group (-NHC (= O) OR ^f , wherein R ^f is a substituted or unsubstituted C1 to C30 alkyl group,
R ¹ to R ¹³ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkenyl 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 arylalkyl group, a substituted or unsubstituted C2 to C30 heteroarylalkyl group, A substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C5 to C30 cycloalkyl group or a substituted or unsubstituted C2 to C30 heterocycloalkyl group,
n1 is 0 or 1,
n2 and n3 are each independently 0, 1, 2 or 3,
When n1 is 0, n2 and n3 are each independently an integer of 1, 2, or 3
When n1 is 1, n1 + n2 + n3? 2 is satisfied. The method according to claim 1,
When n1 is 1, n2 and n3 are not both 0, a condensed polycyclic heteroaromatic compound. The method according to claim 1,
R ¹ and R ⁷ are a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, A substituted or unsubstituted C2 to C30 heteroarylalkyl group, a substituted or unsubstituted C2 to C30 alkylheteroaryl group, a substituted or unsubstituted C5 to C30 cycloalkyl group, or a substituted or unsubstituted C2 to C30 heterocycloalkyl group, Heteroaromatic compounds. The method according to claim 1,
Wherein R < ¹ > and R < ⁷ > are C1 to C30 alkyl groups substituted by a fluorine atom The method according to claim 1,
R ^a is a substituted or unsubstituted C10 to C30 alkyl group, a substituted or unsubstituted C10 to C30 alkoxy group, a substituted or unsubstituted C10 to C30 alkenyl group or a substituted or unsubstituted C10 to C30 alkynyl group, Aromatic compounds. The method according to claim 1,
And R < a > is a C1 to C30 alkyl group substituted by ^a fluorine atom. The method according to claim 1,
Wherein the condensed polycyclic heteroaromatic compound has an average molecular weight of 350 to 3000. < Desc / Clms Page number 24 > An organic thin film comprising a condensed polycyclic heteroaromatic compound according to any one of claims 1 to 7. An electronic device comprising the condensed polycyclic heteroaromatic compound according to any one of claims 1 to 7. 10. The method of claim 9,
Wherein the electronic device is a transistor, an organic light emitting diode (OLED), a photovoltaic device, a solar cell, a laser device, a memory device or a sensor. 10. The method of claim 9,
Wherein the electronic device comprises at least one charge transport layer,
Wherein the condensed polycyclic heteroaromatic compound is contained in the charge transport layer.

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