KR101704110B1 - New compounds and organic solar cell comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic solar cell comprising the same. The novel compound according to the present invention can be used as a photoactive layer material of an organic solar cell by introducing various functional groups. In addition, the organic solar cell according to the present invention can be manufactured by a solution process, and can include a photoactive layer having a strong bonding force due to hydrogen bonding and having excellent crystallinity. Accordingly, the organic solar cell according to the present invention can exhibit excellent characteristics in terms of driving voltage, current, and life.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel compound,

The present invention relates to a novel compound and an organic solar cell comprising the same.

Solar cells are devices that can convert solar energy directly into electrical energy by applying a photovoltaic effect. Solar cells can be divided into inorganic solar cells and organic solar cells depending on the material constituting the thin film. A typical solar cell is made of p-n junction by doping crystalline silicon (Si), which is an inorganic semiconductor. Electrons and holes generated by absorption of light are diffused to the p-n junction, accelerated by the electric field, and moved to the electrode. The power conversion efficiency of this process is defined as the ratio of the power given to the external circuit to the solar power entering the solar cell, and is achieved up to 24% when measured under the current standardized virtual solar irradiation conditions. However, since conventional inorganic solar cells already have limitations in terms of economy and supply / demand of materials, organic semiconductor solar cells, which are easy to process, have low cost and various functions, are attracting attention as long-term alternative energy sources.

Organic solar cells use a variety of organic semiconductor materials in small quantities, which can result in cost savings and can be fabricated using an easy method because they can be fabricated using wet processes.

The organic solar cell has a bi-layer pn junction type organic solar cell including a photoactive layer composed of two layers of a p-type semiconductor thin film and an n-type semiconductor thin film, an n-type semiconductor and a p-type semiconductor There is a BHJ (bulk heterojunction) junction-type organic solar cell including a photoactive layer that is blended.

Solar cells are important to increase efficiency so that they can output as much electrical energy as possible from solar energy. In order to increase the efficiency of such a solar cell, it is also important to generate as much excitons as possible in the semiconductor, but it is also important to draw out generated charges without loss. One of the causes of loss of charge is that the generated electrons and holes are destroyed by recombination. Various methods have been proposed as methods for transferring generated electrons and holes to electrodes without loss, but most of them require additional processing, which may increase the manufacturing cost.

Korean Patent Publication No. 10-2010-0011186

An object of the present invention is to provide a photoactive layer material having high photoelectric conversion efficiency characteristics and an organic solar cell including the photoactive layer material having a high HOMO energy level and having a high open circuit voltage due to high hole mobility . Also, it is an object of the present invention to provide an electron donor material capable of mass production by increasing the stability of an organic solar cell and simplifying a manufacturing process.

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

L1 and L2 are the same or different from each other and each independently represents a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted arylene group, Or a substituted or unsubstituted heteroarylene group containing at least one heteroatom,

R 1 to R 12 are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₂ to C ₂₀ alkenyl group, a substituted or unsubstituted C of ₃ ~ C ₂₀ cycloalkyl group, a substituted or unsubstituted alkoxy group, substituted or non-substituted of unsubstituted C ₅ ~ C ₃₀ of the cycloalkenyl group, a substituted or unsubstituted C ₁ ~ C ₃₀ unsubstituted C ₆ ~ aryloxy C _60, substituted or unsubstituted C ₁ ~ C ₃₀ alkyl tiok group, a substituted or unsubstituted C aryl tiok time of ₅ ~ C _60, substituted or unsubstituted C for ₁ ~ C ₃₀ alkyl amine A substituted or unsubstituted C ₅ to C ₆₀ arylamine group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted heteroatom having O, N, P, Se or S C ₃ ~ C ₆₀ heteroaryl group is selected from the group consisting of the groups R1 to be connected adjacent to each other of R12 condensed ring It can be formed.

The present invention also relates to an organic solar cell comprising an anode, a cathode, and at least one photoactive layer disposed between the anode and the cathode, wherein at least one of the photoactive layers comprises a compound represented by Formula 1 Thereby providing a battery.

The novel compound according to the present invention can be used as a photoactive layer material of an organic solar cell by introducing various functional groups. In addition, the organic solar cell according to the present invention can be manufactured by a solution process, and can include a photoactive layer having a strong bonding force due to hydrogen bonding after heat treatment and having excellent crystallinity. Accordingly, the organic solar cell according to the present invention can exhibit excellent characteristics in terms of driving voltage, current, and life.

1 is a diagram showing a UV spectrum of formula (7) according to one embodiment of the present invention.
2 is a diagram showing a UV spectrum of Formula 8 according to one embodiment of the present invention.
FIG. 3 shows a TGA result of Formula 7 according to one embodiment of the present invention. FIG.
FIG. 4 is a diagram showing IR results after the heat treatment process of Chemical Formula 7 according to one embodiment of the present invention. FIG.
FIG. 5 is a graph showing a result of UV spectrum after the heat treatment process of Chemical Formula 7 according to one embodiment of the present invention. FIG.
6 shows NMR data of Compound 5 of Preparation Example 1 according to one embodiment of the present invention.
7 is a chart showing NMR data of Compound 6 of Preparation Example 1 according to one embodiment of the present invention.
8 is a diagram showing MS data of formula (7) of Production example 1 according to one embodiment of the present invention.
9 is a graph showing NMR results of Compound 7 of Production Example 2 according to one embodiment of the present invention.
10 shows MS data of compound 7 of Preparation Example 2 according to one embodiment of the present invention.
11 is a graph showing NMR results of Compound 8 of Production Example 2 according to one embodiment of the present invention.
12 shows MS data of Compound 8 of Preparation Example 2 according to one embodiment of the present invention.
13 is a chart showing NMR results of Compound 9 of Production Example 2 according to one embodiment of the present invention.
Fig. 14 is a graph showing NMR results of Compound 11 of Production Example 2 according to one embodiment of the present invention. Fig.
15 is a diagram showing MS data of Formula 11 of Production Example 2 according to one embodiment of the present invention.
16 shows MS data of compound 2 of Preparation Example 1 according to one embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The novel compound according to the present invention is characterized by being represented by the above formula (1).

In addition, the organic solar battery according to the present invention includes an anode, a cathode, and at least one photoactive layer disposed between the anode and the cathode, and at least one of the photoactive layers includes a compound represented by Formula 1 .

In general, since the photoactive layer material used for manufacturing organic solar cells is packed only by interaction with van der Waals energy, the intermolecular attractive force is not strong enough, the intermolecular binding force is weak and the intermolecular distance is not sufficiently close, The transfer of the intermolecular carrier is not sufficiently high. Further, since the intermolecular packing is insufficient, air or moisture is easily introduced into the photoactive layer from the outside, which tends to lower the stability of the device.

In order to solve these drawbacks, the present invention is characterized in that a photoactive layer is formed by using a compound capable of hydrogen bonding having stronger bonding force than a van der Waals bond having weak bonding force between photoactive layer materials in manufacturing an organic solar cell do.

Generally, a hydrogen bond interacts with a non-covalent electron pair of atoms such as O, N, S, F, etc. of another neighboring molecule such as O, N, S, F or the like, . These electronegativities of O, N, S, F and the like are considerably larger than the electronegativity of hydrogen atoms, so that a partial positive charge is generated partially in the hydrogen atom and a partial negative charge is generated in the atoms such as O, N, S and F do. Since these partially positively charged hydrogen atoms exhibit a strong attractive force with atoms such as oxygen, nitrogen, sulfur, fluorine, and the like, which are adjacent to a negative charge, the distance between the two molecules is very closely packed and easily arranged. Such intermolecular packing can smooth the carrier movement in the photoactive layer by reducing the intermolecular distance. In addition, the photoactive layer by hydrogen bonding can increase the stability of the organic solar cell by air or moisture.

In the organic solar cell according to the present invention, the photoactive layer may be formed by a method known in the art using a compound having a functional group capable of hydrogen bonding.

Conventionally, the method of forming the photoactive layer during the production of the organic solar cell can be divided into a vacuum deposition method and a solution coating method. Specifically, since the vacuum deposition requires a high temperature and a high degree of vacuum, it is difficult to increase the area, the equipment is relatively expensive, and the process is relatively complicated. On the other hand, the solution coating method represented by the spin coating method, the ink jet printing method, the dip coating method, the roll coating method and the screen printing method can form a thin film of a large area and the process can be performed at room temperature and atmospheric pressure, There are advantages.

Compounds with strong intermolecular interactions, however, tend to make the penetration of organic solvents into the molecule difficult and the solubility of the materials to be low.

Accordingly, in order to utilize the advantage of hydrogen bonding between photoactive layer materials in manufacturing an organic solar cell, the present invention provides a photoactive layer containing a compound having a functional group capable of hydrogen bonding to enhance intermolecular packing and crystallization, A method of forming the photoactive layer by a solution process by increasing the solubility of the photoactive layer material by introducing bulky substituents into a functional group that forms a hydrogen bond to facilitate penetration of the organic solvent into the molecule to provide.

Specifically, the photoactive layer of the organic solar cell according to the present invention may be formed by a compound having a functional group capable of hydrogen bonding.

That is, a substituent which can be removed by heat or light is introduced into the functional group of a compound containing a functional group which is bonded to N, O, S, or F atoms to form a hydrogen bond to remove hydrogen bonds, . In particular, when the substituent is a substituent capable of increasing solubility in a solvent, such as a bulky substituent, the solubility of the compound increases and can be easily prepared as a solution. Therefore, To form a thin film. Subsequently, the formed thin film is heated or light-treated to remove the substituent, thereby generating an organic semiconductor material having strong bonding force capable of forming hydrogen bond again. Accordingly, the above-described method for producing an organic solar cell according to the present invention can form a thin film by a solution process, and the resultant film has high intermolecular packing and crystallinity due to hydrogen bonding, and excellent stability against moisture and air.

The compound having a functional group capable of hydrogen bonding in the present invention is not limited to the compound capable of hydrogen bonding and acting as a semiconductor according to the above-described working principle.

Hereinafter, the compounds that can be used in the present invention will be described in detail by way of the following examples. However, the present invention is not limited to these examples.

The functional group capable of forming a hydrogen bond in the compound having a functional group capable of hydrogen bonding may be a functional group represented by the compound represented by the general formula (1). In particular, R 1 and R 2 in Formula 1 may each be a hydrogen-bonded functional group.

The compound represented by Formula 1 may include an NH group capable of hydrogen bonding with a ketone group. The compounds represented by the above formula (1) can be strongly hydrogen bonded to each other to perform strong interaction. Therefore, these compounds having strong bonding force or the photoactive layer material containing them can be formed into a photoactive layer by vacuum vapor deposition.

In Formula 1, L 1 and L 2 are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted arylene group, and the following functional groups, but the present invention is not limited thereto.

In this functional group, X 1 to X 6 are the same or different from each other, and each independently is S, Se or NR,

R is hydrogen, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkenyl group, a substituted or unsubstituted C ₃ -C ₂₀ cyclo An alkyl group, a substituted or unsubstituted C ₅ to C ₃₀ cycloalkenyl group, a substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a C ₁ ~ C ₃₀ alkyl tiok timing, a substituted or unsubstituted C ₅ ~ C ₆₀ aryl tiok group, a substituted or unsubstituted C ₁ ~ C ₃₀ alkyl amine group, a substituted or unsubstituted C ₅ ~ C of ₆₀ arylamine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, and a substituted or unsubstituted, and two kinds of atoms O, N, P, a hetero group, aryl group of C ₃ ~ C ₆₀ having Se or S .

The formula (1) may be represented by any one of the following formulas (2) to (6), but is not limited thereto.

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the general formulas (2) to (6), R3 to R12 are the same as defined in the above formula (1), and R13 to R24 are as defined in the above R1 to R12.

The formula 1 may be represented by any one of the following formulas (7) to (14), but is not limited thereto.

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

In the compounds according to the present invention, the substituents of the formulas (1) to (6) will be described in more detail as follows.

The alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Examples of the alkyl or alkylene group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a s-butyl group, an isobutyl group, -Hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a 1,3-dihydroxy iso A 1-chloroethyl group, a 2-chloro-isobutyl group, a 1, 2-dihydroxypropyl group, Dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-dichloroethyl group, -Bromo isobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromo group, Profile machine, Iowa Examples of the alkyl group include a methyl group, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodo isobutyl group, a 1,2-diiodoethyl group, a 1,2,3-triiodopropyl group, an aminomethyl group, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutyl group, a 1,2- Aminopropyl group, an aminoisopropyl group, a 2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethyl group, a 1-cyanoethyl group, Dicyanoethyl group, t-butyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyano propyl group, , 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t -Butyl group, 1,2,3-trinitro Propyl group, and the like, but the present invention is not limited thereto.

The alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 20. Examples of the substituent include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butenedianyl group, a 1-methylvinyl group, a styryl group, Phenyl allyl group, 3-phenylallyl group, 3-phenylallyl group, 3-phenylallyl group, 3-phenylallyl group, , 3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group and the like.

The cycloalkyl group preferably has 3 to 20 carbon atoms and does not give steric hindrance. Specific examples thereof include, but are not limited to, a cyclopentyl group, a cyclohexyl group, and the like.

The cycloalkenyl group preferably has 3 to 30 carbon atoms, and more specifically, a cyclic compound having ethenylene in a pentagonal or hexagonal ring, but is not limited thereto.

The alkoxy group preferably has 1 to 30 carbon atoms, more specifically, methoxy, ethoxy, isopropyloxy and the like, but is not limited thereto.

The aryloxy group preferably has 6 to 60 carbon atoms, more specifically, phenyloxy, cyclohexyloxy, naphthyloxy, diphenyloxy and the like, but is not limited thereto.

The alkylamine group preferably has 1 to 30 carbon atoms, and more specifically, it may be a methylamine group, a dimethylamine group, an ethylamine group, or a diethylamine group, but is not limited thereto.

The arylamine group preferably has 5 to 60 carbon atoms. More specifically, examples thereof include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group and the like. But are not limited thereto.

The aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. Examples of the aryl group include a phenyl group, a stilbene group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, Naphthacene group, 9-naphthacene group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrene group, 2-naphthacenyl group, A biphenyl group, a 3-biphenyl group, a 4-biphenyl group, a p-terphenyl-4-yl group, M-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, Methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl- A diary, and the like, but the present invention is not limited thereto.

The heteroaryl group is a ring group containing a hetero atom such as O, N, S, Se or P, and the number of carbon atoms is not particularly limited, but preferably 3 to 60 carbon atoms. Examples of the aryl group include a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, Isoindolyl group, 4-isoindolyl group, 5-indolyl group, 5-indolyl group, 6-indolyl group, A benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 4-benzofuranyl group, a 4-benzofuranyl group, Isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a 4-isobenzofuranyl group, a 4-isobenzofuranyl group, Quinolyl group, 8-quinolyl group, 8-quinolyl group, 1-quinolyl group, 2-quinolyl group, Isooquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7- A 2-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4- A carbazolyl group, a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinyl group, An acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, a thiomorpholino group, , A 9-acridine group, a 1,7-phenanthroline-2-yl group, a 1,7-phenanthroline-3-yl group, a 1,7-phenanthroline- Yl group, a 1,7-phenanthroline-8-yl group, a 1,7-phenanthroline-9-yl group, a 1,7-phenanthroline- Dienes, 1,8-phenanthroline-2-yl groups, 1,8-phenanthroline-3-yl groups, 1,8-phenanthroline- Dienes, 1,8-phenanthroline-6-yl groups, 1,8-phenanthroline-7-yl groups, 1,8- A phenanthroline-10-yl group, a 1,9-phenanthroline-2-yl group, a 1,9-phenanthroline-3-yl group, 6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline- Dienes, 1,10-phenanthroline-2-yl groups, 1,10-phenanthroline-3-yl groups, 1,10- A 2,9-phenanthroline-1-yl group, a 2,9-phenanthroline-3-yl group, a 2,9-phenanthroline- A 2,9-phenanthroline-10-yl group, a 2,9-phenanthroline-10-yl group, A 2,8-phenanthroline-1-yl group, a 2,8-phenanthroline-4-yl group, A phenanthroline-6-yl group, a 2,8-phenanthroline-7-yl group, a 2,8-phenanthroline-9-yl group, a 2,8- Yl group, 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7- A phenanthroline-10-yl group, a phenanthroline-6-yl group, a phenanthroline-8-yl group, A 2-phenothiazinyl group, a 2-phenothiazinyl group, a 2-phenothiazinyl group, a 3-phenothiazinyl group, a 4-phenothiazinyl group, a 10- A 2-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazole group, a 3-phenoxazoyl group, a 4-phenoxazoyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrolidinyl group, 2- Methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrole- Methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, Indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 3-indolyl group, 4-t- butyl-3-indolyl group and the like, but can be, but is not limited thereto only.

The heteroaryl group is preferably a compound having the following structural formula, but is not limited thereto.

Examples of the halogen group include, but are not limited to, fluorine, chlorine, bromine, and iodine.

Specific examples of the arylene group include, but are not limited to, a phenylene group, a biphenylene group, a naphthalenylene group, a binaphthalene group, an anthracenylene group, a fluorenylene group, a klychenylene group and a phenanthrenylene group .

In the present specification, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, cyano, halogen, alkyl, alkenyl, alkoxy, silyl, arylalkenyl, aryl, Substituted or unsubstituted fluorenyl group and nitrile group substituted or unsubstituted with an aryl group, or has no substituent group.

Examples of the substituent which may be further substituted in L 1, L 2 and R 1 to R 24 in the above Chemical Formulas 1 to 6 include a cyano group, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a silyl group, an arylalkenyl group, , A carbazole group, an arylamine group, a fluorenyl group substituted or unsubstituted with an aryl group, a nitrile group, and the like, but the present invention is not limited thereto.

When a hydrogen atom forming a hydrogen bond is replaced with a bulky substituent such as a t-butoxycarbonyl group, the compound of the following general formulas (15) to (19) can not form a hydrogen bond.

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

In the above formulas (15) to (19), R3 to R24 are the same as defined in the above formulas (1) to (6).

Therefore, the compounds represented by the above-mentioned formulas (15) to (19) can not be hydrogen-bonded due to the introduction of bulky substituents, which weakens the intermolecular binding force and increases the solubility. Thus, This is possible. The compounds represented by the above general formulas (15) to (19) are obtained by replacing a hydrogen atom with a t-butoxycarbonyl group, and the molecular bond is broken by heat or light treatment.

That is, in the present invention, as shown in the following structural formula, at least two compounds of the general formula (1) can be hydrogen bonded to each other by thermal or light treatment.

The reforming of hydrogen bonding molecules by heat or light is often used in the protection and deprotection of functional groups in organic chemistry. In this case, the substituent which is substituted for the functional group forming the hydrogen bond is not limited only to the t-butoxycarbonyl group which is the substituent of the compound represented by the above general formulas (15) to (19). In general, an alcohol group, a phenol group, a catechol group, a carbonyl group, a thiol group, an amine group, etc. forming a hydrogen bond is preferably an ether bond, an ester bond, a thioether bond, a thioester bond , Amide bond, and the like.

There is no particular limitation on the heat treatment temperature or time in re-inducing the hydrogen bond by heat treatment or light treatment, and the substituents may be selected depending on the kind of the substituents. For example, the temperature is preferably in the range of 20 to 350 DEG C, and the time is preferably treated within 1 minute to 2 hours. More preferably at a temperature of 160 to 250 DEG C, and the time is preferably treated within 1 hour.

In the light treatment, the exposure time is not particularly limited, but it is generally preferred to be less than 30 minutes.

Substituents suitable for each hydrogen-bonding functional group are described below.

When the functional group forming the hydrogen bond is an alcohol group, the functional group to be substituted in place of the alcohol group is methyl ether, methoxymethyl ether, methoxythiomethyl ether, 2-methoxyethoxy But are not limited to, 2-methoxyethoxymethyl ether, bis (2-chloroethoxy) methyl ether, tetrahydropyranyl ether and 4-methoxytetrahydropyranyl ether Methoxytetrahydropyranyl ether, 4-methoxytetrahydropyranyl ether, tetrahydrothiopyranyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxythetrahydrothiopyranyl ether, Tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 1-ethoxyethyl ether, 1-methyl-1-methoxyethyl ether, Ethoxyethyl ether, 2- (phenylselenyl) ethyl ether, t-butyl ether, allyl ether, isopropyl ether, Benzyl ether, o-nitrobenzyl ether, triphenylmethyl ether, a-naphthyldiphenylmethyl ether, p-methoxyphenyldiphenyl methyl ether ( p-methoxyphenyldiphenylmethyl ether, 9- (9-phenyl-10-oxo) anthryl ether, trimethylsilyl ether, isopropyldimethylsilyl ether isopropyldimethylsilyl ether, t-butyldimethylsilyl ether, t-butyldiphenylsilyl ether, tribenzylsilyl ether, triisopropylsilyl ether, formate Formate ester, acetate ester, But are not limited to, trichloroacetate esters, phenoxyacetate esters, isobutyrate esters, pivaloate esters, adamantoate esters, benzoate esters, ester, 2,4,6-trimethylbenzoate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate, Allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, N-phenyl carbonate, Nitrate ester, 2,4-dinitrophenylsulfenate ester, and the like.

Preferably, when the functional group forming the hydrogen bond is an alcohol group, the functional group substituted in place of the alcohol group is trichloroacetate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate (2 2,2-trichloroethyl carbonate, allyl carbonate, pnitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, nitrate ester, and 2,4-dinitrophenylsulfenate ester.

More preferably, when the functional group forming the hydrogen bond is an alcohol group, the functional group substituted in place of the alcohol group is a nitrate ester and a 2,4-dinitrophenylsulfenate ester. .

When the functional group forming the hydrogen bond is a phenol group or a catechol group, the functional group substituted in place of the phenol group or the catechol group is methyl ether, methoxymethyl ether, 2-methoxyethoxymethyl ether (2- methoxyethoxymethyl ether, methoxythiomethyl ether, penacyl ether, allyl ether, cyclohexyl ether, t-butyl ether, benzyl ether benzyl ether, o-nitrobenzyl ether, 9-anthrylmethyl ether, 4-picolyl ether, t-butyldimethylsilyl ether (t -butyldimethylsilyl ether, aryl acetate, aryl pivaloate, aryl benzoate, aryl 9-fluorenecarboxylate, aryl methyl carbonate ), Aryl 2,2,2-trichloro But are not limited to, aryl 2,2,2-trichloroethyl carbonate, aryl vinyl carbonate, aryl benzyl carbonate, aryl methanesulfonate, methylenedioxy derivatives, Acetonide derivatives, diphenylmethylenedioxy derivatives, cyclic borates, cyclic carbonates, and the like.

When the functional group forming the hydrogen bond is carbonyl, the functional group substituted in place of the carbonyl group is dimethyl acetal and ketal, bis (2,2,2-trichloroethyl) acetal and ketal (bis , 2-trichloroethyl acetal and ketal, 1,3-dioxanes, 5-methylene-1,3-dioxanes, Dibromo-1,3-dioxanes, 1,3-dioxolanes, 4-bromomethyl-1,3-dioxolane, 4-bromomethyl-1,3-dioxolanes, 4-o-nitrophenyl-1,3-dioxolanes, S, S'- (S, S'-dimethyl acetal and ketal), 1,3-dithianes, 1,3-dithiolane, 1,3- 3-oxathiolanes, o-trimethylsilyl cyanohydrins, N, Ndimethylhydrazones, 2,4-dinitrophenylhydrazones, o -Phenylthiomethyl oximes, substituted < RTI ID = 0.0 > But are not limited to, substituted methylene derivatives, bismethylenedioxy derivatives, methyl esters, methoxymethyl esters, methylthiomethyl esters, tetrahydropyranyl esters ester, benzyloxymethyl ester, penacyl ester, N-phthalimidomethyl ester, 2,2,2-trichloroethyl ester, 2,2,2- trichloroethyl ester, 2-haloethyl ester, 2- (ptoluenesulfonyl) ethyl ester, t-butyl ester, A mixture of cinnamyl ester, benzyl ester, triphenylmethyl ester, bis (o-nitrophenylmethyl ester), 9-anthrylmethyl ester ester), 2- (9,10-di (9,10-dioxo) anthrylmethyl ester, piperonyl ester, trimethylsilyl ester, t-butyldimethylsilyl ester, t-butyldimethylsilyl ester, s-t-butyl ester, 2-alkyl-1,3-oxazolines, N, N-dimethylamide, N-7 N-7-nitroindoylamide, hydrazide, N-phenylhydrazide, N, N'-diisopropylhydrizide and the like. do.

When the functional group forming the hydrogen bond is a thiol group, the functional group substituted in place of the thiol group is s-benzyl thioether, sp-methoxybenzyl thioether, sp-nitrobenzyl thioether s-p-nitrobenzyl thioether, s-4-picolyl thioether, s-2-picolyl N-oxide thioether, s-9 S-9-anthrylmethyl thioether, s-diphenylmethyl thioether, s-di (p-methoxyphenyl) methyl dithioether, , s-triphenylmethyl thioether, s-2,4-dinitrophenyl thioether, st-butyl thioether, s-isobutyl thioether, S-isobutoxymethyl monothioacetal, s-2-tetrahydropyranyl monothioacetal, s-2-tetrahydropyranyl monothioacetal, S-acetamidomethyl aminothioacetal, s-cyanomethyl thioether, s-2-nitro-1-phenylethyl thioether, , s-2,2-bis (carboethoxy) ethyl thioether, s-benzoyl derivatives, s- (N- (S- (N-ethylcarbamate), s-ethyl disulfide, and the like.

When the functional group forming the hydrogen bond is an amine group, the functional group substituted in place of the amine group is methyl carbamate, 9-fluorenylmethyl carbamate, 2,2,2-trichloroethylcarbamate, 2-trimethylsilyl carbamate, 1,1-dimethylpropynyl carbamate, 1-methyl-1-methylpropylcarbamate, 1-methyl-1-phenylethyl catbamate, 1-methyl-1- (4-biphenylyl) ethyl carbamate, 1,1- Dimethyl-2-haloethyl carbamate, 1,1-dimethyl-2-cyanoethyl carbamate, t- T-butyl carbamate, cyclobutyl carbamate, 1-methylcyclobutyl carbamate, 1-adamantyl carbamate, Vinyl carbamate, allyl carbamate, cinnamyl carbamate, 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate, N-hydroxypiperidinyl carbamate, carbamate, 4,5-diphenyl-3-oxazoline-2-one, benzyl carbamate, p-nitrobenzyl carbamate (p 2,4-dichlorobenzyl carbamate, 3,4-dimethoxy-6-nitrobenzyl carbamate, 2,4-dichlorobenzyl carbamate, 5- Benzisoxazolylmethyl carbamate, 9-anthrylmethyl carbamate, diphenylmethyl carbamate, isonicotinyl carbamate, s-benzyl isoquinolinecarbamate, S-benzyl carbamate, N- (N'-phenylaminothiocarbonyl) derivatice, N-formyl (N -formyl, N-acetyl, N-chloroacetyl, N-trichloroacetyl, N-trifluoroacetyl, No-nitrophenylacetyl, No-nitrophenoxyacetyl, Nacetoacetyl, N-3-phenylpropionyl, N-3- (p- Propionyl, N-2-methyl-2- (onitrophenoxy) propionyl, N-2- Methyl-2- (o-phenylazophenoxy) propionyl, N-4-chlorobutyryl, N-2-nitrocinnamoyl But not limited to, N-quinolinol, N-onitrocinnamoyl, N-picolinoyl, N- (N'-acetylmethionyl), N-benzoyl, N-phthaloyl, Ndithiasuccinoyl, N-allyl, Nphenacyl, N-3-acetoxypropyl, quaternary ammonium Salt (qu a salt thereof, a tertiary ammonium salt, a tertiary ammonium salt, an N-methoxymethyl, an N-benzyloxymethyl, N-pivaloyloxymethyl, Ntetrahydropyranyl, N-2,4-dinitrophenyl, N-benzyl, No-nitrobenzyl, N-di (p-methoxyphenyl) di (pmethoxyphenyl) methyl, N-triphenylmethyl, N- (p-methoxyphenyl) diphenylmethyl, N-diphenyl-4-pyridylmethyl N-diphenyl-4-pyridylmethyl, N-2-picolyl N'-oxide, N, N'-isopropylidene, N- N-benzylidene, Np-nitrobenzylidene, Nsalicylidene, N- (5,5-dimethyl-3-oxo-1-cyclohexenyl) 5,5-dimethyl-3-oxo-1-cyclohexenyl, N-nitro, N-oxide, N-diphenylphosphinyl, N-dimethylthiophosphinyl Ndimethylthiophosphinyl), N-benzenesul N-benzylsulfenyl, N-onitrobenzenesulfenyl, N-2,4,6-trimethylbenzenesulfonyl, Ntoluenesulfonyl, N-benzylsulfonyl, N-trifluoromethylsulfonyl, N-phenacyl sulfonyl and the like.

Preferably, when the functional group forming the hydrogen bond is an amine group, the functional group substituted in place of the amine group is 1,1-dimethyl-2-haloethyl carbamate, 1,1-dimethyl- Dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, and N- (N'-acetylmethionyl N- (N ' -acetylmethionyl)).

More preferably, when the functional group forming the hydrogen bond is an amine group, the functional group substituted in place of the amine group is 1,1-dimethyl-2-haloethyl carbamate and t- And t-butyl carbamate.

Most preferably, when the functional group forming the hydrogen bond is an amine group, the functional group is t-butyl carbamate.

An organic solar cell according to an embodiment of the present invention includes an anode, a photoactive layer, and a cathode electrode. The organic solar cell may further include a substrate, a hole transporting layer, and / or an electron transporting layer.

The substrate may be a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness, but is not limited thereto and is not limited as long as it is a substrate commonly used in organic solar cells.

The anode may comprise a material that is transparent and highly conductive, but is not limited thereto. Specifically, it may be indium tin oxide (ITO), tin oxide (SnO ₂ ), and zinc oxide (ZnO), but is not limited thereto.

The cathode may include, but is not limited to, a metal having a low work function. Specifically, it may be a metal such as lithium, magnesium, or an alloy thereof, or a multilayered material such as Al: Li, Al: BaF2, or Al: BaF2: Ba.

The hole transporting layer and / or the electron transporting layer material may be a material for efficiently transferring electrons and holes to the photoactive layer, thereby increasing the probability that the generated charge moves to the electrode. However, the hole transporting layer and / or the electron transporting layer material are not particularly limited. The hole transport layer material may be selected from the group consisting of poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid), N, N'-bis (3-methylphenyl) -N, N'- '-Biphenyl] -4,4'-diamine (TPD). The electron transport layer material may be selected from the group consisting of aluminum trihydroxyquinolate (Alq3), 1,3,4-oxadiazole derivative PBD (2- (4-bipheyl) -5- (3-phenyl-6-trifluoromethyl) qunoxaline-2-yl] benzene), a triazole derivative, and the like.

In the present invention, the photoactive layer may be a structure sequentially including an organic material layer including an electron donor material, an organic material layer including an electron donor material and an electron donor material, and an organic material layer including an electron donor material. At this time, the electron donor may be a compound having a functional group capable of hydrogen bonding as described above, and more specifically, a compound represented by the formula (1).

The electron acceptor material may be a fullerene, a fullerene derivative, a heterocyclic compound, a semiconducting element, a semiconducting compound, or a combination thereof. Specifically, the electron accepting material may be selected from the group consisting of PC61BM (phenyl C61-butyric acid methyl ester) or PC71BM (phenyl C71- acid methyl ester.

In the organic layer comprising the electron donor material and the electron donor material, the electron donor material and the electron donor material may be mixed in a ratio (w / w) of 1:10 to 10: 1, and after mixing, Lt; RTI ID = 0.0 > 400 C < / RTI > for 1 second to 24 hours.

The thickness of the photoactive layer may be 10 to 10,000 angstroms, but is not limited thereto.

In the present invention, the photoactive layer is formed in a three-layer structure including an organic material layer including an electron donor material, an electron donor material, an organic material layer including an electron donor material, and an organic material layer including an electron donor material, The formation of the hole transporting layer and the electron transporting layer can increase the charge extraction and the charge transporting, thereby increasing the overall charge mobility. In addition, it is possible to freely adjust the energy level, thereby facilitating the movement of holes and electrons, and forming an ideal p-n structure.

In the photoactive layer of the three-layer structure, the thickness of the organic material layer including the electron donor material may be 20 to 400 nm, the thickness of the organic material layer including the electron donor material and the electron acceptor material may be 20 to 400 nm, The thickness of the organic material layer including the electron-accepting material may be greater than 0 and less than or equal to 300 nm, but is not limited thereto.

The organic solar cell may be arranged in the order of an anode electrode, a hole transporting layer, a photoactive layer, an electron transporting layer, and a cathode electrode, and may be arranged in the order of a cathode electrode, an electron transporting layer, a photoactive layer, a hole transporting layer and an anode electrode. Do not.

The organic solar cell according to the present invention is an organic solar cell according to the present invention, except that the photoactive layer contains a compound of the present invention, that is, a compound having a functional group capable of forming a hydrogen bond, for example, Materials and methods.

More specifically, a method of fabricating an organic solar cell according to one embodiment of the present invention includes sequentially forming an anode, a photoactive layer, and a cathode on a substrate, wherein the photoactive layer has a hydrogen And forming a thin film using a compound having a substituent group which is removed by heat treatment or light treatment to form a thin film, and then heat-treating or light-treating the thin film. do.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

< Example >

< Manufacturing example  1> Preparation of formula (7)

(1) Compound 1 (3,6-bis (4- Bromophenyl ) Pirolo [3,4-c] pyrrole-1,4 (2H, 5H) -dione ))

Compound 1 is Cai, Xiaofei; Wang, Aili; Wang, Limin; Yu, Jianjun; Zhang, Guanjun; Zhang, Liang Dyes and Pigments, 2013, vol. 98, # 2 p. 232-237. &Lt; / RTI &gt;

(2) Compound 2 (di- Rat -Butyl 3,6- Bis (4- Bromophenyl ) -1,4- Dioxo-pyrrolo [3,4-c] pyrrole -2,5 (1H, 4H) -dicarboxylate ( Di - tert - butyl  3,6- bis (4- bromophenyl ) -1,4- dioxopyrrolo [3,4-c] pyrrole-2,5 (1H, 4H) -dicarboxylate))

To a solution of 3,6-bis (4-bromophenyl) pyrrolo [3,4-c] pyrrole-1,4 (2H, 5H) 4- (dimethylamino) pyridine, as catalyst) and 4- (4-bromophenyl) pyrrolo [3,4-c] pyrrole- (DMAP) were stirred at room temperature. After a few minutes, di-tert-butyl dicarbonate (1.50 mL, 1.54 mmol) (Boc2O) was added at room temperature. After 1 hour, the mixture was stirred at 40 ° C for 18 hours. The solvent and excess Boc2O were removed from the reaction solution under reduced pressure to obtain a yellow solid (yield: 99%).

MS data of the compound 2 is shown in FIG.

(3) Synthesis of Compound 3

2-hexylthiophene (2.0 g, 11.8 mmol) was dissolved in 150 ml of tetrahydrofuran (THF) and the temperature was lowered to -78 ° C. At this temperature, 2.5 M n-BuLi (5.7 ml, 14.2 mmol) dissolved in hexane was slowly added and stirred for 1 hour. To this solution was added 1M trimethyltinchloride in hexane (17.0 ml, 17.0 mmol) dissolved in hexane in one portion, and the mixture was stirred for 12 hours while being warmed to room temperature. Water was poured into this solution, extracted with hexane, and then the residue was removed with magnesium sulfate (MgSO4). The remaining solution was removed under reduced pressure and used directly in the next reaction (yield: 87%).

(4) Synthesis of Compound 5

To a solution of compound 3 (1.0 g, 3.02 mmol), compound 4 (0.74 g, 3.02 mmol), tetrakis (triphenylphosphine) palladium (0) (Pd (PPh3) 4,0.1 g ). The solution was stirred and refluxed for 12 hours. The solution was poured into water, extracted twice with methylene chloride, washed twice with water, and the residue was removed with magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica column chromatography (eluent: hexane / MC = 10: 1) (yield: 57%).

The NMR data of the compound 5 is shown in FIG.

(5) Synthesis of Compound 6

The compound 6 was synthesized by the method described in Jounal of Polymer Science Part A: Polymer Chemistry, 49, 1156-1162 (2011).

The NMR data of the compound 6 is shown in FIG.

(6) Synthesis of formula (7)

Compound 2 (0.5 g, 0.7736 mmol), Compound 6 (1.2 g, 1.9340 mmol), tetrakis (triphenylphosphine) palladium (0) (Pd (PPh3) 4,1 mol %, 0.1g) was added and dissolved. This solution was reacted at 90 ° C for 12 hours. The solution was cooled to room temperature, and the solvent was then removed under reduced pressure at 80 ° C., poured into water, extracted twice with methylene chloride, washed twice with water, and the residue was removed with magnesium sulfate. The solvent was removed from the remaining solution under reduced pressure, and the residue was precipitated with acetonitrile and washed several times with water to obtain a clear formula (7) (yield: 73%).

The MS data of the above formula (7) is shown in FIG.

< Manufacturing example  2> Preparation of the compound of formula (11)

(1) Synthesis of Compound 7

TPP (4.0 g, 13.3 mmol) was dissolved in anhydrous THF in a 2-neck round bottom flask, and then dimethylammonopyridine was added as a catalyst and stirred for about one hour . Then, di- (t-butyl) -dicarbonate (7.26 g, 33.2 mmol) was dissolved in anhydrous THF under nitrogen atmosphere using a syringe and stirred at RT for 12 hours . After the reaction was confirmed by TLC, the THF was reduced in pressure. After silica packing with hexane + Et3N as an eluent and loading the reaction mixture, impurities were removed by flowing Hx: EA = 4: 1 and chloroform was added. Respectively. After the completion of the column, the solvent was removed by decompression, followed by washing with hexane and drying well in a vacuum oven to obtain 4.0 g (yield: 60%) of a dark brown solid compound t-Boc TPP.

The NMR results of the compound 7 are shown in FIG. 9, and MS data is shown in FIG.

(2) Synthesis of Compound 8

T-Boc TPP (2.36 g, 4.71 mmol) was added to CF in a 2-neck round bottom flask and stirred at room temperature. After light protection using aluminum foil, NBS (2.09 g, 2.5 eq.) Was added and stirred for 40 hours or more. When the reaction proceeded, the crude mixture was immediately evaporated and recrystallized using CF / EtOH to obtain 1.6 g (yield: 50%) of a dark brown needle-like compound 8. [ ).

The NMR results of the compound 8 are shown in FIG. 11, and the MS data is shown in FIG.

(3) Synthesis of Compound 9

Compound (8) (1.00 g, 1.5189 mmol), 4- (Cyanomethyl) benzeneboronic acid (0.61 g, 1.5189 mmol) was added to a 250 ml 2-neck round bottom flask, 3.7971 mmol) were dissolved in 150 ml of toluene and stirred. The temperature was raised to ~ 50 ° C and Pd (0) (0.52mg, 3 mol%) was added. After stirring for several minutes, 2M aq. K ₂ CO ₃ was added thereto, and the mixture was stirred at a temperature of 90 ° C. After the reaction, the temperature was lowered to room temperature, the solvent was evaporated under reduced pressure at 80 ° C, washed several times with water, and recrystallized with MC / EtOH to obtain Compound 9 (yield: 83%).

The NMR results of the compound 9 are shown in FIG.

(4) Synthesis of Compound 11

To a 250 ml 2-neck round bottom flask was added compound 10 (4 g, 7.1875 mmol), 5-bromo-2-thiophenecarboxaldehyde (2.06 g, mmol) were dissolved in 150 ml of toluene and stirred. The temperature was raised to ~ 50 ° C and Pd (0) (0.37mg, 3mol%) was added. After stirring for several minutes, 2M aq. K2CO3 was added thereto, and the temperature was raised to 90 DEG C and stirred. After the reaction, the solution was reacted at 90 DEG C for 12 hours. The solution was poured into water, extracted twice with chloroform, washed twice with water, and the residue was removed with magnesium sulfate (MgSO4). The solvent was distilled off under reduced pressure, and a fine powder was obtained through a silica column (hexane / EA = 10: 4) (yield: 78%).

The NMR results of the compound 11 are shown in Fig.

(5) Synthesis of Compound 12

To a 250 ml 2-neck round bottom flask was added compound 10 (4 g, 7.1875 mmol), 5-bromo-2,2'-bithiophene-5 -Carboxaldehyde, 2.94 g, 10.7813 mmol) were placed in 150 ml of toluene and stirred. The temperature was raised to ~ 50 ° C and Pd (0) (0.37 mg, 3 mol%) was added. After stirring for several minutes, 2M aq. K2CO3 was added thereto, and the temperature was raised to 90 DEG C and stirred. After the reaction, the solution was reacted at 90 DEG C for 12 hours. This solution was poured into water, extracted twice with chloroform, washed twice with water, and the residue was removed with magnesium sulfate (MgSO4). The solvent was distilled off under reduced pressure, and a fine powder was obtained through a silica column (eluent: hexane / EA = 10: 5) (yield: 71%).

(6) Synthesis of compound (11)

Compound 9 (0.5 g, 0.6841 mmol) and compound 11 (0.78 g, 1.4366 mmol) were dissolved in 300 ml THF / MeOH (10: 1) in a 500 ml 2-neck round bottom flask and heated . Sodium methoxide (NaOMe, as catalyst) was added to the solution and refluxed / stirred. The reaction proceeded and the temperature was lowered to room temperature to obtain a precipitated solid. Washed several times with water or alcohol, or washed with an organic solvent and dried well to obtain the compound (11) (yield: 91%).

MS data of the above formula (11) is shown in FIG.

< Manufacturing example  3> Preparation of the compound of formula (12)

Compound 9 (0.5 g, 0.6841 mmol) and compound 12 (0.89 g, 1.4366 mmol) were dissolved in 400 ml THF / MeOH (10: 1) in a 500 ml 2-neck round bottom flask and heated . Sodium methoxide (NaOMe, as catalyst) was added to the solution and refluxed / stirred. The reaction proceeded and the temperature was lowered to room temperature to obtain a precipitated solid. Washed several times with water or alcohol or washed with an organic solvent and dried well to obtain the compound (12) (yield: 93%).

< Experimental Example >

The UV spectrum of the formula (7) is shown in FIG. 1, and the UV spectrum of the formula (8) is shown in FIG.

The characteristics of the above formula (7) are as follows.

- Band gap: 2.18 eV

- Electrochemical properties: HOMO (-5.37 eV), LUMO (-3.22 eV)

- the torsion angle of a, b, and c: a (32.2 degrees), b (14.7 degrees), c (36.4 degrees)

Planarity: 1.8975

The characteristics of the above formula (8) are as follows.

- Band gap: 1.70 eV

- Electrochemical properties: HOMO (-5.49 eV), LUMO (-3.80 eV)

- Torsion angle of a: a (5.3 degrees), b (14.7 degrees), c (36.4 degrees)

Planarity: 2.60

The TGA results of the formula (7) are shown in FIG. The IR results of the above formula (7) are shown in FIG.

From the results of FIG. 4, it can be seen that the hydrogen bond is formed through the heat treatment process at a certain temperature or higher in the formula (7).

After the heat treatment process of Chemical Formula 7, UV spectrum results are shown in Table 1 and FIG.

[Table 1]

Heat treatment above a certain temperature may induce a blue-shift of the material. This phenomenon is due to the removal of the side chain, which inhibits p-p stacking but increases the bandgap due to intramolecular twisted as strong intermolecular interaction (hydrogen bonding) takes place. However, after the heat treatment process, a structure similar to a crystalline polymer can be formed and used as a new hole transport layer and an electron injection layer to improve charge mobility and stability, thereby improving the efficiency of the organic solar cell.

Claims (14)

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

In Formula 1,
L 1 and L 2 are the same or different and are each independently a direct bond, a substituted or unsubstituted alkenylene group having ₂ to ₂₀ carbon atoms, or a substituted or unsubstituted heteroarylene group containing S,
R 1 and R 2 are the same or different and each independently hydrogen or a substituted or unsubstituted carbonyl group,
R3 to R12 are the same or different and each is independently hydrogen, substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, and a substituted or unsubstituted, and consisting of a heteroaryl group of C ₃ ~ C ₆₀ having a heterologous atom S another , Provided that when R 1 and R 2 are hydrogen and L 1 and L 2 are direct bonds, R 5 and R 10 are C ₃ to C ₆₀ heteroaryl groups having a substituted or unsubstituted heteroatom S, Adjacent groups in R12 may be connected to each other to form a condensed ring. The compound according to claim 1, wherein L1 and L2 are each independently selected from the group consisting of a direct bond or the following functional groups:

In this functional group, X1 to X6 are S; The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (2) to (6)
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the general formulas (2) to (6), R 3 to R 12 are the same as defined in the above formula (1), R 13 to R 24 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group. The compound according to claim 1, wherein R 1 and R 2 in the formula (1) are each a functional group which is a hydrogen bond. The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (7) to (14):
(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

And at least one photoactive layer disposed between the anode and the cathode, wherein at least one of the photoactive layers includes a compound represented by the formula (1) as defined in any one of claims 1 to 5 Organic solar cell. 7. The organic solar battery according to claim 6, wherein the photoactive layer sequentially includes an organic material layer including an electron donor material, an organic material layer including an electron donor material and an electron acceptor material, and an organic material layer including an electron acceptor material. [Claim 7] The organic solar battery according to claim 7, wherein the electron donor material is a compound represented by Chemical Formula (1). [7] The method of claim 7, wherein the organic material layer including the electron donor material includes a step of forming a thin film using a compound introduced with a substituent group removed by heat treatment or light treatment on the compound represented by Chemical Formula 1, followed by heat treatment or light treatment Wherein the organic solar cell is formed by a method comprising: The organic solar battery according to claim 9, wherein the substituent group removed by the heat treatment or the light treatment is selected from the group consisting of an alcohol group, a phenol group, a catechol group, a carbonyl group, a thiol group and an amine group. The organic solar battery according to claim 9, wherein the substituent removed by the heat treatment or the light treatment is a tert-butylcarbonyl group. The organic solar battery according to claim 7, wherein the electron acceptor material is selected from the group consisting of fullerene, fullerene derivative, vasocopherin, semiconductor element, semiconductor compound, and combinations thereof. 7. The organic solar battery according to claim 6, wherein the organic solar cell further comprises at least one of a hole transporting layer and an electron transporting layer. [Claim 12] The organic solar battery according to claim 9, wherein the compound introduced with the substituent removed by the heat treatment or the light treatment is a compound represented by any one of Chemical Formulas (15) to (19)
[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

In the above formulas 15 to 19,
R3 to R12 are the same or different and each is independently hydrogen, substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, and a substituted or unsubstituted, and consisting of a heteroaryl group of C ₃ ~ C ₆₀ having a heterologous atom S another And adjacent groups of R 3 to R 12 may be connected to each other to form a condensed ring,
R13 to R24 are the same or different and each independently represent a substituted or unsubstituted of C _{6 ~} C ₆₀ aryl group to each other.

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