KR101595147B1 - Aromatic compound and organic solar cell comprising the same - Google Patents

Abstract

The present invention provides an aromatic compound capable of greatly improving the lifetime, efficiency, electrochemical stability, and thermal stability of an organic solar cell and an organic solar cell comprising the aromatic compound.

Description

TECHNICAL FIELD [0001] The present invention relates to an aromatic compound and an organic solar cell including the same. BACKGROUND ART [0002] AROMATIC COMPOUND AND ORGANIC SOLAR CELL COMPRISING THE SAME [0003]

The present invention relates to aromatic compounds and organic solar cells 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 input to 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 have already been limited in economical efficiency and supply / demand of materials, organic semiconductor solar cells, which are easy to process, have various functions and are inexpensive, are seen 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.

On the other hand, it is important to increase the efficiency of solar cells so that they can output as much electric energy as possible from solar energy. In order to increase the efficiency of such a solar cell, it is also important to generate as many excitons as possible in the semiconductor, but it is also important to draw generated charges out 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.

The possibility of organic solar cells was first suggested in the 1970s, but efficiency was too low to be practical. However, in 1986, Eastman Kodak's CW Tang showed a dual layer structure using copper phthalocyanine (CuPc) and perylene tetracarboxylic acid derivatives, and therefore, Interest in and research on solar cells has been rapidly increasing and has led to many improvements. In 1995, Yu et al. Introduced the concept of BHJ (Bulk heteojunction). Fullerene derivatives such as PCBM, which have improved solubility, have been developed as n-type semiconductors, . Thereafter, development of materials for organic solar cells is continuously required.

US Registration Bulletin: 5,331,183 US Registration Bulletin: 5,454,880

Two-layer organic photovoltaic cells (C. W. Tang, Appl. Phys. Lett., 48, 183. (1996) Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science, 270, 1789. (1995)).

The present disclosure provides novel aromatic compounds.

The present invention also provides an organic solar cell comprising the compound.

The technical problems to be solved in the present invention are not limited to the above-mentioned technical problems, and other technical problems which are not mentioned can be clearly understood by the average technician from the following description.

One embodiment of the present disclosure provides a compound comprising a unit represented by the formula:

[Chemical Formula 1]

In formula (1)

R ₁ to R ₄ and Ra to Rd are each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; A nitrile group; Imide; -N = CHZ _1; Amide group; A hydroxyl group; Ester group; A carbonyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted selenophen group; A substituted or unsubstituted pyrrol group; A substituted or unsubstituted thiazole group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted monocyclic aryl group; And a substituted or unsubstituted polycyclic aryl group,

Z ₁ is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

의 몰분율을 나타내고,l, m, n, and o are, respectively, M ₁ , M ₂ , M ₃ ,

, ≪ / RTI >

l is a real number with 0 < l &lt; 1,

m is a real number satisfying 0 < m &lt; 1,

n is a real number satisfying 0 < n &lt; 1,

o is a real number with 0 <o? 1, l + m + n + o = 1,

p is an integer of 1 to 10,000,

The M ₁ To M &lt; ₃ &gt; are each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic divalent heterocyclic group; A substituted or unsubstituted monocyclic or polycyclic divalent aromatic ring group; Or a substituted or unsubstituted divalent group in which at least two of a monocyclic or polycyclic heterocyclic ring and a monocyclic or polycyclic aromatic ring are condensed.

One embodiment of the present disclosure relates to the above M ₁ To M &lt; ₃ &gt; may each independently be selected from the substituents represented by the following formulas (2) to (24)

In formulas (2) to (24)

X ₁ and X ₂ are each independently selected from the group consisting of CR'R ", SiR'R", GeR'R ", NR ', PR', O, S and Se,

Y ₁ and Y ₂ are each independently selected from the group consisting of CR ', SiR', GeR ', N and P,

R ₅ to R ₃₄ , R ' and R &quot; are each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; A nitrile group; Imide; -N = CHZ _1; Amide group; A hydroxyl group; Ester group; A carbonyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted selenophen group; A substituted or unsubstituted pyrrol group; A substituted or unsubstituted thiazole group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted monocyclic aryl group; And substituted or unsubstituted polycyclic aryl groups, Z ₁ is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and in formulas (3) to (15), The carbon in which the substituent is not shown in the ring constituting the ring may be substituted with hydrogen or other substituent, and the substituent is the same as defined in R ₅ to R ₃₄ .

In addition, one embodiment of the present invention provides an organic solar cell including a first electrode, a second electrode, and at least one photoactive layer, and at least one of the photoactive layers includes an aromatic compound of Formula 1.

One or more of the photoactive layer, the electron transporting layer, and the hole transporting layer may comprise a compound selected from the group consisting of The present invention provides an organic solar cell comprising

One embodiment of the present disclosure provides a method of manufacturing a semiconductor device, comprising: preparing a substrate; Forming a first electrode on the substrate; Forming a photoactive layer including the aromatic compound of Formula 1 on the first electrode; And forming a second electrode on the photoactive layer.

One embodiment of the present disclosure provides a method of manufacturing a semiconductor device, comprising: preparing a substrate; Forming a first electrode on one region of the back surface of the substrate; Forming a hole transport layer on the first electrode; Forming a photoactive layer on the hole transport layer; Forming an electron transport layer on the photoactive layer; And forming a second electrode on the electron transporting layer; Wherein at least one of the hole transporting layer, the photoactive layer, and the electron transporting layer includes the aromatic compound of Formula 1.

The aromatic compound represented by Chemical Formula 1 in the present specification can be used as a material for an organic solar cell.

Organic solar cells containing an aromatic compound according to one embodiment disclosed herein exhibit excellent properties in terms of efficiency and stability.

The aromatic compounds according to one embodiment described herein are excellent in thermal stability.

The aromatic compounds according to one embodiment disclosed herein exhibit deep HOMO levels, various band gaps, various LUMO level states, and electronic stability depending on substituents.

The aromatic compound represented by Chemical Formula 1 in the present specification may be used purely in an organic solar cell including an organic solar cell, or may be mixed with impurities.

The aromatic compound according to one embodiment described herein can be applied by a solution coating method.

The organic solar cell including the aromatic compound according to one embodiment described herein can improve the light efficiency.

The lifetime characteristics of the organic solar battery can be improved by the thermal stability of the aromatic compound according to one embodiment described herein.

1 shows the gas chromatogram-mass spectrum of the compound according to Production Example 1-A.
2 shows the mass spectrum of the compound according to Production Example 1-B.
3 shows the mass spectrum of the compound according to Production Example 1-C.
4 shows a GPC (Gel Permeation Chromatography) chromatogram of the compound according to Preparation Example 2. FIG.
5 shows a GPC (Gel Permeation Chromatography) chromatogram of the compound according to Preparation Example 3. FIG.
Fig. 6 shows the solution phase and film-like UV absorption spectrum of the aromatic compound according to Production Example 2. Fig.
7 shows the solution phase and the film-based UV absorption spectrum of an aromatic compound according to Preparation Example 3. Fig.
8 shows the results of cyclic voltametry of the aromatic compound according to Preparation Example 2. [
9 shows the results of cyclic voltammetry of the aromatic compound according to Production Example 3.
10 and 11 show the current density according to the voltage of the organic solar cell according to Examples 1 to 4.

Hereinafter, the present invention will be described in detail.

는 고분자 주쇄 또는 다른 치환기에 결합되는 부위를 의미한다.In this specification

Quot; means a moiety bonded to a polymer backbone or other substituent.

In this specification, an electron donor is also referred to as an electron donor and generally has a pair of negative or non-covalent electrons, which means donating electrons to a portion lacking a positive charge or an electron pair. Further, the electron donor in the present specification may excite electrons to an electron receiver having a high electronegativity owing to the abundant electron retention property of the molecule itself when light is received in a state of being mixed with the electron acceptor even if it has no negative or non- And the like.

In this specification, an electron acceptor means receiving electrons from an electron donor.

One embodiment of the present invention provides a compound of formula (I) as described above.

The M &lt; 1 _&gt; To M &lt; ₃ &gt; may each independently be a direct bond.

M ₁ to M ₃ in formula (1) may each independently be a substituted or unsubstituted monovalent divalent aromatic ring group.

M ₁ to M ₃ in formula (1) may each independently be a substituted or unsubstituted polycyclic divalent aromatic ring group.

M ₁ to M ₃ in formula (1) may each independently be a substituted or unsubstituted monovalent divalent heterocyclic group.

The M &lt; 1 _&gt; To M &lt; ₃ &gt; may each independently be a substituted or unsubstituted polycyclic divalent heterocyclic group.

The M &lt; 1 _&gt; To M &lt; ₃ &gt; may each independently be a substituted or unsubstituted monocyclic or polycyclic aromatic ring and a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

In the general formulas (1) to (24), the halogen group may be fluorine, chlorine, bromine or iodine.

Z ₁ of -N = CHZ ₁ of Formula 1 may be a hydrogen group, an alkyl group, an aryl group. Specifically, it may be a compound having the following structure, but is not limited thereto.

로 표시되는 이미드로부터 유래된 것으로 나타낼 수 있다. Z₂ 내지 Z₄는 수소, 알킬기 또는 아릴기가 될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the above Formulas 1 to 24,

Lt; RTI ID = 0.0 &gt; denoted &lt; / RTI &gt; Z ₂ to Z ₄ may be hydrogen, an alkyl group or an aryl group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

The term " derived "in this specification, including the above-mentioned" derived ", means that a linking group of the mentioned compound is formed. For example, it is meant that at least one part of the mentioned compound is in a form that it can have a linking group.

로 표시되는 아미드로부터 유래된 것으로 나타낼 수 있다. Z₅ 내지 Z₇은 수소, 알킬기 또는 아릴기가 될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the above general formulas (1) to (24), the amide group

&Lt; / RTI &gt; as shown below. Z ₅ to Z ₇ may be hydrogen, an alkyl group or an aryl group. Specifically, it may be a compound of the following structural formula. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

로 표시되는 에스터로부터 유래된 것으로 나타낼 수 있다. Z₈ 내지 Z₉는 수소, 알킬기 또는 아릴기가 될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the above general formulas (1) to (24), the ester group

As shown in FIG. Z ₈ to Z ₉ may be hydrogen, an alkyl group or an aryl group. Specifically, it may be a compound of the following structural formula. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

으로 표시되는 카보닐로부터 유래된 것으로 나타낼 수 있다. Z₁₀ 및 Z₁₁은 수소, 알킬기 또는 아릴기가 될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the above general formulas (1) to (24), the carbonyl group

Lt; RTI ID = 0.0 &gt; carbonyl &lt; / RTI &gt; Z ₁₀ and Z ₁₁ may be hydrogen, an alkyl group or an aryl group. Specifically, it may be a compound of the following structural formula. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

The alkyl group in the present specification including the above formulas (1) to (24) may be linear, branched or cyclic. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specific examples thereof include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, A cyclopropyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like, but is not limited thereto.

The alkoxy group in the present specification including the above-mentioned formulas 1 to 24 may be a straight chain, a branched chain or a ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a n-propyloxy group, an iso-propyloxy group, a n-butyloxy group, and a cyclopentyloxy group.

The aryl group in the present specification including the above formulas 1 to 24 may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a stilbenyl group.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

The term "substituted or unsubstituted" in the present specification including the above Chemical Formulas 1 to 24 means a group selected from a halogen group, a nitrile group, a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, an aryloxy group, An alkyl group, an aryl group, an aryl group, a fluorenyl group, a carbazole group, an arylalkyl group, an arylalkenyl group, an aryl group, an aryl group, , A heterocyclic group, and an acetylene group, or does not have any substituent (s).

At least one of R ₁ to R ₃₄ , Ra to Rd, R ', and R''in the above Chemical Formulas 1 to 24 is a thiophene group, a selenophene group, a pyrrolyl group, a thiazole group, an arylamine group, When they are cyclic aryl groups, they may be independently substituted or unsubstituted with an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms.

In Formula 1 according to one embodiment of the present invention, p is an integer of 1 to 10,000, and may be an integer of 30 to 100. When the value of p is 10,000 or less, the solubility is improved and the solution application method can be carried out easily. When the value of p is 1 to 10,000, the larger the value, the better the electrical characteristics and the mechanical characteristics. Specifically, when the value of p is in the range of 3 to 100, the solubility is further improved, which is more advantageous in application of the solution coating method.

In the formula (1) according to one embodiment of the present invention, the number average molecular weight may have a number average molecular weight ranging from 500 to 1,000,000, specifically from 10,000 to 100,000.

In the formula (1) according to one embodiment of the present invention, the compound may have a molecular weight distribution of 1 to 100, and more specifically, a molecular weight distribution of 1 to 3.

When the number average molecular weight is 10,000 to 100,000, the electrical characteristics and the mechanical properties are improved, and the solubility is improved, which can be more advantageous in application of the solution coating method.

When the molecular weight distribution is in the range of 1 to 3, the electrical and mechanical properties are improved, and the solubility is improved, which is more advantageous in application of the solution coating method.

When the molecular weight distribution is in the range of 1 to 100, the intermolecular bonding force is enhanced. When the molecular weight distribution is less than 100, the effect is better. Specifically, when the molecular weight distribution is 1 to 3, the effect is more effective in terms of the intermolecular bonding force.

The molecular weight distribution in this specification is a value obtained by dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn).

In the formula (1) according to one embodiment of the present invention, the terminal group may be a heteroaromatic group. Specifically, the terminal group may be thiophene, furan, or the like. The terminal group may be an aromatic group. Specifically, the terminal group may be benzene, naphthalene, anthracene, or the like. Further, the terminal group may be an alkyl group substituted with a halogen or the like. However, the present invention is not limited to these specific examples.

을 포함하는 방향족 화합물이다. The aromatic compound of formula (1) according to one embodiment herein has

&Lt; / RTI &gt;

The aromatic compound of formula (1) according to one embodiment of the present invention may be a compound represented by any one of the following formulas (A) to (D), but is not limited thereto.

The aromatic compound of formula (1) according to one embodiment of the present invention can be prepared by a multistage chemical reaction. After the monomers are prepared through the alkylation reaction, the Grignard reaction, the Suzuki coupling reaction, and the Stille coupling reaction, the final compound (s) is obtained through a carbon-carbon coupling reaction such as a steel coupling reaction Or polymers. When the substituent to be introduced is boronic acid or a boronic ester compound, Suzuki coupling reaction can be used. When the substituent to be introduced is a tributyltin compound, it can be prepared through a steel coupling reaction. However, the manufacturing method is not limited thereto.

Also, there is provided an organic solar cell comprising an aromatic compound represented by Chemical Formula 1 according to an embodiment of the present invention as a photoactive layer.

Further, there is provided an organic solar cell comprising an aromatic compound represented by Chemical Formula 1 according to an embodiment of the present invention in a hole transporting layer and / or an electron transporting layer.

An organic solar cell according to an embodiment of the present invention includes a first electrode, a second electrode, and a photoactive layer. 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 first electrode may be an anode, and the second electrode may be a cathode. The first electrode may be a cathode, and the second electrode may be an anode.

The anode may be a transparent material having excellent conductivity, 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 be a metal having a small work function, but is not limited thereto. Specifically, it may be a metal such as lithium, magnesium, or an alloy thereof, or a multi-layered material such as Al: Li, Al: BaF ₂ , or Al: BaF ₂ : 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 (Alq ₃ ), 1,3,4-oxadiazole derivative PBD (2- (4-bipheyl) -5-phenyl- (3, 4-tris [(3-phenyl-6-trifluoromethyl) quinoxaline-2-yl] benzene), a triazole derivative and the like can be used as the quinoxaline derivative. The hole transport layer material and / or the electron transport layer material may include a compound represented by the formula (1).

The photoactive layer may comprise an electron donor material and an electron acceptor material. As the electron donor, the aromatic compound of Formula 1, which is an embodiment of the present invention, can be used. 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, PC ₆₁ BM (phenyl C ₆₁ -butyric acid methyl ester) or PC ₇₁ BM (phenyl C ₇₁ -butyric acid methyl ester).

The photoactive layer can form a BHJ (Bulk Heterojunction) by an electron donor and an electron acceptor. The electron donor material and the electron acceptor material may be mixed at a ratio (w / w: mass ratio) of 1:10 to 10: 1. After the electron donor and electron donor materials are mixed, annealing may be performed at 30 to 300 ° C for 1 second to 24 hours to maximize the properties.

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

The organic solar battery may be arranged in the order of an anode, a photoactive layer, and a cathode, and may be arranged in the order of a cathode, a photoactive layer, and an anode, but is not limited thereto.

The organic solar battery may be arranged in the order of an anode, a hole transporting layer, a photoactive layer, an electron transporting layer and a cathode, and may be arranged in the order of a cathode, an electron transporting layer, a photoactive layer, a hole transporting layer and an anode.

In the organic solar cell, a p-type semiconductor forms an exciton paired with electrons and holes by photoexcitation, and the exciton can be separated into an electron and a hole at a p-n junction. The separated electrons and holes migrate to the n-type semiconductor thin film and the p-type semiconductor thin film, respectively, and they are collected in the first electrode and the second electrode, respectively, so that they can be used as electric energy from the outside.

The organic solar cell may be a bi-layer p-n junction organic solar cell and a bulk heterojunction (BHJ) junction depending on the structure of the photoactive layer. A bi-layer p-n junction type organic solar cell includes a photoactive layer consisting of two layers of a p-type semiconductor thin film and an n-type semiconductor thin film. A BHJ (bulk heterojunction) junction type organic solar cell includes a photoactive layer in which an n-type semiconductor and a p-type semiconductor are blended.

The organic solar cell is characterized in that efficiency is improved remarkably due to a new device configuration and a change in process conditions. Therefore, in order to replace conventional materials, an electron donor material having a low band gap and a new electron donor material having a good charge mobility are included.

Conventional electron donor materials have been studied mainly on p-type conductive polymers, but they have not yet absorbed much of the solar spectrum because the band gap is large. In addition, since the solubility of the polymer is poor, there is a limit in using a spin coating process, a roll-to-roll process, or an inkjet printing process through a solution process. In addition, a BHJ device through combination with an electron acceptor material such as a fullerene derivative has a maximum efficiency of 8%, and thus a novel photoactive material having improved electronic characteristics has been required for commercialization.

However, the organic solar cell according to one embodiment of the present invention exhibits excellent characteristics in terms of an increase in efficiency and an increase in stability. The compound represented by formula (1) of the present invention has excellent thermal stability, deep HOMO level, various bandgaps, various LUMO level states and electronic stability, and exhibits excellent characteristics. The compound represented by the formula (1) of the present invention is excellent in solubility and can be applied by a solution coating method in an organic solar cell. In addition, the organic solar cell using the compound represented by Formula 1 of the present invention has improved light efficiency. Further, the lifetime characteristics of the organic solar battery can be improved by the thermal stability of the compound.

The role of the photoactive material that absorbs light to generate energy in the organic solar cell is mainly performed by the electron donor material. Therefore, it is desirable that the electron donor material is capable of absorbing light in a wide spectral range so as to absorb as much sunlight as possible.

The compound according to one embodiment of the present invention can absorb the wavelength of sunlight corresponding to a wide range of 300 to 700 nm and thus can be used as an electron donor material of an organic solar cell.

The organic solar cell of the present specification can be produced by materials and methods known in the art, except that the photoactive layer contains the compound of the present invention, i.e., the aromatic compound represented by the above formula (1).

The organic solar cell of the present specification can be produced by materials and methods known in the art except that the hole transporting layer and / or the electron transporting layer contains the compound of the present invention, i.e., the aromatic compound represented by the above formula (1) .

A method of fabricating an organic solar cell according to an embodiment of the present invention includes the steps of preparing a substrate, forming an anode on one region of the substrate, forming a photoactive layer on the anode, And forming a cathode.

A method of manufacturing an organic solar cell according to an embodiment of the present invention includes the steps of preparing a substrate, forming a cathode on one region of a back surface of the substrate, forming a photoactive layer on the cathode, And forming an anode.

Further, a method of manufacturing an organic solar cell according to an embodiment of the present invention includes the steps of preparing a substrate, forming an anode on one region of the back surface of the substrate, forming a hole transport layer on the anode, Forming a photoactive layer on the hole transporting layer, forming an electron transporting layer on the photoactive layer, and forming a cathode on the electron transporting layer.

Further, a method of manufacturing an organic solar cell according to an embodiment of the present invention includes the steps of preparing a substrate, forming a cathode on one region of the back surface of the substrate, forming an electron transport layer on the cathode, Forming a photoactive layer on the electron transporting layer, forming a hole transporting layer on the photoactive layer, and forming an anode on the hole transporting layer. The organic solar cell of the present specification can be produced, for example, by sequentially laminating an anode, a photoactive layer and a cathode on a substrate.

The organic solar cell of the present specification can be produced by sequentially laminating an anode, a hole transporting layer, a photoactive layer, an electron transporting layer and a cathode on a substrate. At this time, they may be coated by a wet method such as gravure printing, offset printing, screen printing, ink jet, spin coating, spray coating and the like, but not limited thereto.

The organic solar cell of the present specification can be produced by sequentially laminating an anode, a hole transporting layer, a photoactive layer, an electron transporting layer and a cathode on a substrate. At this time, they may be coated by a wet method such as gravure printing, offset printing, screen printing, ink jet, spin coating, spray coating and the like, but not limited thereto.

< Manufacturing example  1 - A> Monomeric  synthesis ( Bis (4-bromophenyl) fumaronitrile  (Preparation of bis (4-bromophenyl) fumaronitrile)

[ Manufacturing example  1-a]

4-bromophenylacetonitrile (23.0 g, 117 mmol) and iodine (29.8 g, 117 mmol) were added to 400 ml of ether and dissolved therein. Lower. Sodium methoxide (13.3 g, 246 mmol) dissolved in anhydrous methanol (10 wt%) was slowly dropped into anhydrous methanol, the temperature was raised to 0 ° C, and the mixture was stirred for 4 hours. The reaction mixture was filtered, washed with water and cold methanol, and then recrystallized from chloroform and methanol to obtain a white solid .

Yield: 38.4%

MS: [M + H] &lt; ⁺ &gt; = 388

1 shows the gas chromatogram-mass spectrum of bis (4- (5-bromothiophen-2-yl) phenyl) fumaronitrile prepared in Production Example 1-A.

< Manufacturing example  1 - B> Monomeric  Synthesis (bis (4- ( Thiophene -2 days) Phenyl ) Preparation of bis (4- (thiophen-2-yl) phenyl) fumaronitrile)

[ Manufacturing example  1-B]

Bis (4-bromophenyl) fumaronitrile (1.00 g, 2.58 mmol) and 2- (tributylstannyl) thiophene were added to 30 ml of chlorobenzene. thiophene, 2.40 g, 6.44 mmol) and Pd (PPh ₃ ) ₄ (tetrakis (triphenylphosphine) palladium (0), 670 mg, 0.58 mmol) were dissolved and stirred under reflux. After 24 hours, the mixture was cooled to room temperature, extracted with chlorobenzene, washed with water, and water remaining in the solution was removed with MgSO ₄ . The solvent was removed under vacuum, methanol (Methanol) was poured out to precipitate and then filtered to obtain a yellow solid.

Yield: 52.1%

MS: [M + H] &lt; ⁺ &gt; = 394

2 shows the mass spectrum of bis (4- (thiophen-2-yl) phenyl) fumaronitrile prepared by Preparation Example 1-B.

< Manufacturing example  1 - C> Monomeric  Synthesis (bis (4- (5- Bromothiophene -2 days) Phenyl ) Pumaro Nitrile ( Bis (4- (5- bromothiophen -2- yl ) phenyl ) fumaronitrile)

[ Manufacturing example  1-C]

(4- (thiophen-2-yl) phenyl) fumaronitrile (0.500 g, 1.26 mmol) was added to 50 ml of dimethylformamide. N-bromosuccinimide (0.271 g, 1.52 mmol) was added to the solution, and the temperature was raised to 110 ° C, followed by stirring for 24 hours. After cooling to room temperature, the mixture was filtered and the solid washed with cold dimethylformamide.

Yield: 67%

MS: [M + H] &lt; ⁺ &gt; = 552

3 shows the mass spectrum of bis (4- (5-bromothiophen-2-yl) phenyl) fumaronitrile prepared in Production Example 1-C.

< Manufacturing example  2> Polymerization of Polymers (Poly (4,4'-bis (2- Ethylhexyl ) Dissieno [3,2-b: 2 ', 3'-d] Alt -4-( Thiophene -2 days) Phenyl ) Pumaro Nitrile ) (poly (4,4-bis (2- ethylhexyl ) dithieno [3,2-b: 2 ', 3 ' -d] silole - bottom -4-( thiophen -2-yl) phenyl) fumaronitrile)

[ Manufacturing example  2]

In the present invention, 4,4'-bis (2-ethylhexyl) -5,5'-bis (trimethyltin) dithieno [3,2- b: 2 ', 3'- 4'-Bis (2-ethylhexyl) -5,5'-bis (trimethyltin) dithieno [3,2-b: 2 ', 3'-d] silole) was prepared by referring to the previous literatures. (L. Hou, J. Hou, H. Y. Chen, S. Zhang, Y. Jiang, T. L. Chen, Y. Yang, Macromolecules 42, 2009, 6564-6571)

A microwave reactor vial was charged with 10 ml of chlorobenzene, 4,4'-bis (2-ethylhexyl) -5,5'-bis (trimethyltin) dithieno [3,2 bis (2-ethylhexyl) -5,5'-bis (trimethyltin) dithieno [3,2-b: 2 ', 3'-d] silole, 1.14 g, 1.54 mmol) , bis (4-bromophenyl) fumarate as nitrile (bis (4-bromophenyl) fumaronitrile , 0.596 g, 1.54 mmol), Pd (PPh 3) 4 (tetrakis (triphenylphosphine) palladium ( 0), 5 mg), and the mixture was reacted at 170 ° C for 1 hour. The mixture was cooled to room temperature, poured into methanol, and the solids were filtered. Soxhlet extraction was performed on acetone, hexane and chloroform, followed by sedimentation in methanol to remove solids.

Yield: 44%

Number average molecular weight: 7220 g / mol

Weight average molecular weight: 10,800 g / mol

FIG. 4 is a graph showing the results of the measurement of the poly (4,4'-bis (2-ethylhexyl) dithieno [3,2-b: 2 ', 3'- Thiophen-2-yl) phenyl) fumaronitrile.

FIG. 6 is a graph showing the results of the production of poly (4,4'-bis (2-ethylhexyl) dithieno [3,2-b: 2 ', 3'- Thiophen-2-yl) phenyl) fumaronitrile and a film UV absorption spectrum.

The film-based UV absorption spectrum of the film in FIG. 6 was obtained by dissolving each polymer at a concentration of 1 wt% in chlorobenzene, dropping the solution on a glass substrate, and spin-coating the polymer at 1000 rpm for 60 seconds using a UV-Vis spectrometer Respectively.

8 is a graph showing the results of measurement of the activity of poly (4,4'-bis (2-ethylhexyl) dithieno [3,2-b: 2 ', 3'- The cyclic voltammetry of Bu ₀ NBF ₄ was carried out in acetonitrile in the presence of 0.1% (w / w) &lt; RTI ID = 0.0 &gt; M glassy carbon working electrodes, Ag / Agcl reference electrodes, and Pt electrodes were analyzed by a three-electrode method. Each of the polymers was coated on a working electrode by a drop casting method.

The compound synthesized in Preparation Example 2 shows an oxidation potential of 1.1 to 1.2 V as compared to Ag / AgCl. The oxidation level measured by the cyclic voltammetry can be converted to the HOMO energy level by a constant equation (HOMO (eV) = - (4.4 + oxidation potential (V)) in comparison with Ag / , And the HOMO energy level corresponding to the potential value is -5.5 to 5.6 eV. In the organic solar cell, one of the important factors for determining the open-circuit voltage is the HOMO energy level of the electron-injecting polymer and the LUMO energy level difference value of the electron accepting material. That is, as the HOMO energy level of the electron-injecting polymer is located deeper, the open-circuit voltage of the device becomes larger, and the polymer itself becomes oxidative stable. Therefore, the oxidation potential of the preferred polymer is 0.8 V or more as compared to Ag / AgCl. However, if the oxidation potential of the polymer is too high and the HOMO energy level is located too deep, the holes generated during the operation of the device may not be extracted into the anode, and more preferably, the oxidation potential is in the range of 0.7 to 1.2 V . Therefore, the compound synthesized in Preparation Example 2 has a preferable oxidation potential value.

Since the compound synthesized in Preparation Example 2 absorbs a wavelength of 300 to 700 nm, it can absorb a wide range of sunlight corresponding to ultraviolet rays, visible rays, and near-infrared rays of sunlight, .

< Manufacturing example  3> Polymerization of poly (N-9- Heptadecanyl carbazole - Alt -4-( Thiophene -2 days) Phenyl ) Pumaro Nitrile ) (poly (N-9- heptadecanylcarbazole - bottom -4-( thiophen -2-yl) phenyl) fumaronitrile)

[ Manufacturing example  3]

In the present invention, 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -N, 9-heptadecanylcarbazole Bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -N, 9-heptadecanylcarbazole) was prepared by referring to the previous literatures. (N.Blouin, A. Michaud, M. Leclerc, Adv. Mater. 19, 2007, 2295-2300)

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -N, 9-heptadecanylcarbazole (787 mg, 1.20 (5-bromothiophen-2-yl) phenyl) fumaronitrile (662 mg, 1.20 mmol), and bis (4- (5-bromothiophen- 20 wt% Et4NOH (tetraethylhydroxide) solution _{30ml, Pd (PPh 3) 4} (tetrakis (triphenylphosphine) palladium (0) after cooling the mixture was stirred under reflux was dissolved into a 50 mg. after 72 hours the mixture to room temperature and poured into methanol Coche , And extracted with acetone, hexane and chloroform, and then precipitated again in methanol to remove the solid.

Yield: 51%

Number average molecular weight: 20,300 g / mol

Weight average molecular weight: 56,600 g / mol

FIG. 5 shows a GPC chromatogram of poly (N-9-heptadecanylcarbazole-alt-4- (thiophen-2-yl) phenyl) fumaronitrile prepared by Preparation Example 3. FIG.

7 shows the film-based UV absorption spectrum of poly (N-9-heptadecanylcarbazole-alt-4- (thiophen-2-yl) phenyl) fumaronitrile prepared in Production Example 3. FIG.

The film-based UV absorption spectrum of the film in FIG. 7 was obtained by dissolving each polymer at a concentration of 1 wt% in chlorobenzene, dropping the solution on a glass substrate, and spin-coating the polymer at 1000 rpm for 60 seconds using a UV-Vis spectrometer Respectively.

9 shows the results of electrochemical cyclic voltammetry of poly (N-9-heptadecanylcarbazole-alt-4- (thiophen-2-yl) phenyl) fumaronitrile prepared in Production Example 3 .

The cyclic voltametry of FIG. 9 was carried out by adding a glassy carbon working electrode and an Ag / Agcl reference electrode to an electrolyte solution obtained by dissolving Bu ₄ NBF ₄ in acetonitrile at 0.1 M, The Pt electrode was deposited and analyzed by the three electrode method. Each of the polymers was coated on a working electrode by a drop casting method.

The compound synthesized in Preparation Example 3 shows an oxidation potential of 1.1 to 1.2 V as compared to Ag / AgCl. The oxidation level measured by the cyclic voltammetry can be converted to the HOMO energy level by a constant equation (HOMO (eV) = - (4.4 + oxidation potential (V)) in comparison with Ag / , And the HOMO energy level corresponding to the potential value is -5.5 to 5.6 eV. In the organic solar cell, one of the important factors for determining the open-circuit voltage is the HOMO energy level of the electron-injecting polymer and the LUMO energy level difference value of the electron accepting material. That is, as the HOMO energy level of the electron-injecting polymer is located deeper, the open-circuit voltage of the device becomes larger, and the polymer itself becomes oxidative stable. Therefore, the oxidation potential of the preferred polymer is 0.8 V or more as compared to Ag / AgCl. However, if the oxidation potential of the polymer is too high and the HOMO energy level is located too deep, the holes generated during the operation of the device may not be extracted into the anode, and more preferably, the oxidation potential is in the range of 0.7 to 1.2 V . Therefore, the compound synthesized in Production Example 3 has a preferable oxidation potential value.

Since the compound synthesized in Preparation Example 3 absorbs a wavelength of 300 to 700 nm, it can absorb a wide range of sunlight corresponding to ultraviolet rays, visible rays, and near-infrared rays of sunlight, .

< Example  1> Manufacture of organic solar cell

The compound prepared in Preparation Example 2 and PCBM were dissolved in 1,2-dichlorobenzene (DCB) at a ratio of 1: 2 to prepare a composite solution. At this time, the concentration was adjusted to 1 to 2 wt%, and the organic solar cell had the structure of ITO / PEDOT: PSS / photoactive layer / LiF / Al. The ITO-coated glass substrate was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was ozone-treated for 10 minutes and spin coated with PEDOT: PSS (baytrom P) Min. In order to coat the photoactive layer, the polymer-PCBM composite solution was filtered with a 0.45 μm PP syringe filter, then spin-coated, and then heat-treated at 120 ° C. for 5 minutes. Using a thermal evaporator under a vacuum of 3 × 10 ^-8 torr LiF was deposited to a thickness of 7 Å, and Al was deposited to a thickness of 200 nm to prepare an organic solar cell.

< Example  2> Manufacture of organic solar cell

The compound prepared in Preparation Example 2 and PCBM were dissolved in 1,2-dichlorobenzene (DCB) at a ratio of 1: 4 to prepare a composite solution. At this time, the concentration was adjusted to 1 to 2 wt%, and the organic solar cell had the structure of ITO / PEDOT: PSS / photoactive layer / LiF / Al. The ITO-coated glass substrate was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was ozone-treated for 10 minutes and spin coated with PEDOT: PSS (baytrom P) Min. In order to coat the photoactive layer, the polymer-PCBM composite solution was filtered with a 0.45 μm PP syringe filter, then spin-coated, and then heat-treated at 120 ° C. for 5 minutes. Using a thermal evaporator under a vacuum of 3 × 10 ^-8 torr LiF was deposited to a thickness of 7 Å, and Al was deposited to a thickness of 200 nm to prepare an organic solar cell.

< Example  3> Manufacture of organic solar cell

The compound prepared in Preparation Example 3 and PCBM were dissolved in 1,2-dichlorobenzene (DCB) at a ratio of 1: 2 to prepare a composite solution. At this time, the concentration was adjusted to 1 to 2 wt%, and the organic solar cell had the structure of ITO / PEDOT: PSS / photoactive layer / LiF / Al. The ITO-coated glass substrate was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was ozone-treated for 10 minutes and spin coated with PEDOT: PSS (baytrom P) Min. In order to coat the photoactive layer, the polymer-PCBM composite solution was filtered with a 0.45 μm PP syringe filter, then spin-coated, and then heat-treated at 120 ° C. for 5 minutes. Using a thermal evaporator under a vacuum of 3 × 10 ^-8 torr LiF was deposited to a thickness of 7 Å, and Al was deposited to a thickness of 200 nm to prepare an organic solar cell.

< Example  4> Manufacture of organic solar cell

The compound prepared in Preparation Example 3 and PCBM were dissolved in 1,2-dichlorobenzene (DCB) at a ratio of 1: 4 to prepare a composite solution. At this time, the concentration was adjusted to 1 to 2 wt%, and the organic solar cell had the structure of ITO / PEDOT: PSS / photoactive layer / LiF / Al. The ITO-coated glass substrate was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was ozone-treated for 10 minutes and spin coated with PEDOT: PSS (baytrom P) Min. In order to coat the photoactive layer, the polymer-PCBM composite solution was filtered with a 0.45 μm PP syringe filter, then spin-coated, and then heat-treated at 120 ° C. for 5 minutes. Using a thermal evaporator under a vacuum of 3 × 10 ^-8 torr LiF was deposited to a thickness of 7 Å, and Al was deposited to a thickness of 200 nm to prepare an organic solar cell.

< Comparative Example  1> Manufacture of organic solar cell

P3HT and PCBM were dissolved in 1,2-dichlorobenzene (DCB) at a ratio of 1: 1 to prepare a composite solution. At this time, the concentration was adjusted to 1 to 2 wt%, and the organic solar cell had the structure of ITO / PEDOT: PSS / photoactive layer / LiF / Al. The ITO-coated glass substrate was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was ozone-treated for 10 minutes and spin coated with PEDOT: PSS (baytrom P) Min. In order to coat the photoactive layer, the polymer-PCBM composite solution was filtered with a 0.45 μm PP syringe filter, then spin-coated, and then heat-treated at 120 ° C. for 5 minutes. Using a thermal evaporator under a vacuum of 3 × 10 ^-8 torr LiF was deposited to a thickness of 7 Å, and Al was deposited to a thickness of 200 nm to prepare an organic solar cell.

< Test Example  1>

The photoelectric conversion characteristics of the organic solar cells prepared in Examples 1 to 4 and Comparative Example 1 were measured under conditions of 100 mW / cm ² (AM 1.5), and the results are shown in Table 1 below.

Active layer Total thickness
(nm) V _OC
(V) J _SC
(mA / cm ² ) FF PCE
(%) Example 1 A / PC ₆₁ BM = 1: 2 94 0.68 1.61 26.2 0.29 Example 2 A / PC ₆₁ BM = 1: 4 66 0.73 2.20 29.3 0.47 Example 3 Formula B / PC ₆₁ BM = 1: 2 58 0.50 1.53 30.1 0.23 Example 4 Formula B / PC ₆₁ BM = 1: 4 69 0.61 1.79 36.3 0.39 Comparative Example 1 P3HT / PC ₆₁ BM = 1: 1 90 0.72 8.30 45.5 2.81

In Table 1, the total thickness means the thickness of the active layer in the organic solar cell, V _oc is the open voltage, J _sc is the short-circuit current, FF is the fill factor, and PCE is the energy conversion efficiency. The open-circuit voltage and the short-circuit current are the X-axis and Y-axis intercepts in the fourth quadrant of the voltage-current density curve, respectively. The higher the two values, the higher the efficiency of the solar cell. The fill factor is the width of the rectangle that can be drawn inside the curve divided by the product of the short-circuit current and the open-circuit voltage. The energy conversion efficiency can be obtained by dividing these three values by the intensity of the irradiated light, and a higher value is preferable.

10 and 11 show the current density according to the voltage of the organic solar battery according to Examples 1 to 4.

The method of measuring the current density in Figs. 10 and 11 is as follows. The compound prepared in Preparation Examples 2 and 3 and PCBM were dissolved in 1,2-dichlorobenzene (DCB) to prepare a composite solution. At this time, the concentration was adjusted to 1.0 to 2.0 wt%, and the organic solar cell had the structure of ITO / PEDOT: PSS / photoactive layer / LiF / Al. The ITO coated glass substrate was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was ozone-treated for 10 minutes. Spin coating of PEDOT: PSS (baytrom P) Lt; / RTI &gt; In order to coat the photoactive layer, the polymer-PCBM composite solution was filtered with a 0.45 μm PP syringe filter, then spin-coated, heat-treated at 120 ° C. for 5 minutes, and heated under a vacuum of 3 × 10 ^-8 torr using a thermal evaporator LiF was deposited to a thickness of 7 Å, and then Al was deposited to a thickness of 200 nm. The photoelectric conversion characteristics of the organic solar cell thus prepared were measured under the condition of 100 mW / cm ² (AM 1.5).

Under the solar irradiation condition, the current density curve according to the voltage of the organic solar cell indicates how efficiently the organic solar cell is producing energy. In the quadrant of the voltage-current density curve, the X-axis and Y-axis intercepts indicate the open-circuit voltage and the short-circuit current, respectively. The higher the two values, the higher the efficiency of the solar cell. Also, a value obtained by dividing the width of a rectangle which can be drawn inside this curve by the product of the short-circuit current and the open-circuit voltage is called a fill factor, and the higher the value, the better the efficiency.

Claims (18)

An aromatic compound comprising a unit represented by the following formula (1):
[Chemical Formula 1]

In formula (1)
R ₁ to R ₄ and Ra to Rd are each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; A nitrile group; Imide; -N = CHZ _1; Amide group; A hydroxyl group; Ester group; A carbonyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted selenophen group; A substituted or unsubstituted pyrrol group; A substituted or unsubstituted thiazole group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted monocyclic aryl group; And a substituted or unsubstituted polycyclic aryl group,
Z ₁ is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
l, m, n, and o are, respectively, M ₁ , M ₂ , M ₃ ,

, &Lt; / RTI &gt;
l is a real number with 0 < l < 1,
m is a real number with 0 < m &lt; 1,
n is a real number satisfying 0 &lt; n &lt; 1,
o is a real number with 0 <o? 1, l + m + n + o = 1,
p is an integer of 1 to 10,000,
M ₁ and M ₃ are each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic divalent heterocyclic group; A substituted or unsubstituted monocyclic or polycyclic divalent aromatic ring group; Or a substituted or unsubstituted divalent group condensed with at least two of monocyclic or polycyclic heterocyclic rings and monocyclic or polycyclic aromatic rings,
M ₂ is the following formula 6, 14 or 15,
[Chemical Formula 14] [Chemical Formula 15]

X ₁ and X ₂ are each independently selected from the group consisting of CR'R ", SiR'R", GeR'R ", NR ', PR', O, S and Se,
Y ₁ is selected from the group consisting of CR ', SiR', GeR ', N and P,
R ₂₀ , R ₂₁ , R ' and R &quot; are each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; A nitrile group; Imide; -N = CHZ _1; Amide group; A hydroxyl group; Ester group; A carbonyl group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted selenophen group; A substituted or unsubstituted pyrrol group; A substituted or unsubstituted thiazole group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted monocyclic aryl group; And a substituted or unsubstituted polycyclic aryl group,
In the formulas (6) and (15), the carbon in which the substituent is not indicated among the carbon atoms constituting the ring may be substituted with hydrogen or other substituent, wherein the substituent is the same as defined for R ₂₀ and R ₂₁ ,
The substitution or non-substitution is preferably a substituent selected from the group consisting of a halogen group, a nitrile group, a nitro group, a hydroxy group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, an aryloxy group, a thiol group, an alkylthio group, An arylalkoxy group, an arylamine group, an alkylamine group, an aryl group, a fluorenyl group, a carbazole group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, and an acetylene group Substituted with one or more substituents, or have no substituent. delete The aromatic compound according to claim 1, wherein the formula (1) is the following formula (a):
(A)

The aromatic compound according to claim 1, wherein the aromatic compound comprises a structure represented by one of the following formulas (A) to (D):

The aromatic compound according to any one of claims 1, 3 and 4, wherein the aromatic compound absorbs the wavelength of sunlight up to 300 to 700 nm. The aromatic compound according to any one of claims 1, 3 and 4, wherein p is an integer from 3 to 100. The aromatic compound according to any one of claims 1, 3 and 4, wherein the molecular weight distribution is 1 to 100. The aromatic compound according to any one of claims 1, 3 and 4, wherein the number average molecular weight is 500 to 1,000,000. Wherein at least one of the photoactive layers comprises an aromatic compound according to any one of claims 1, 3 and 4, wherein the photoactive layer comprises a first electrode, a second electrode and at least one photoactive layer. The organic solar cell according to claim 9, wherein the photoactive layer comprises an electron donor material and an electron acceptor material, and the electron donor material comprises the aromatic compound. 11. The organic solar battery according to claim 10, wherein the electron acceptor material comprises one or more selected from the group consisting of fullerene, fullerene derivative, vasocopherin, semiconductor element, and semiconducting compound. Wherein at least one of the photoactive layer, the electron transport layer and the hole transport layer comprises a first electrode, a second electrode, at least one photoactive layer, an electron transport layer and a hole transport layer, Organic solar cell. The organic solar battery according to claim 12, wherein the photoactive layer comprises an electron donor material and an electron acceptor material, and at least one of the electron donor material, the electron transport layer and the hole transport layer comprises the aromatic compound. 14. The organic solar battery according to claim 13, wherein the electron acceptor material comprises one or more selected from the group consisting of fullerene, fullerene derivative, vasocopherin, semiconductor element, and semiconducting compound. Preparing a substrate;
Forming a first electrode on the substrate;
Forming a photoactive layer comprising an aromatic compound according to any one of claims 1, 3 and 4 on the first electrode; And
And forming a second electrode on the photoactive layer. 16. The method of manufacturing an organic solar battery according to claim 15, wherein a solution coating method is used to form the photoactive layer. Preparing a substrate;
Forming a first electrode on one region of the back surface of the substrate;
Forming a hole transport layer on the first electrode;
Forming a photoactive layer on the hole transport layer;
Forming an electron transport layer on the photoactive layer; And
Forming a second electrode on the electron transporting layer;
Wherein at least one of the hole transporting layer, the photoactive layer, and the electron transporting layer includes the aromatic compound according to any one of claims 1, 3, and 4. 18. The method of manufacturing an organic solar cell according to claim 17, wherein the layer containing the aromatic compound is formed using a solution coating method.

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