KR102531257B1 - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present specification relates to a compound including a unit represented by Formula 1 and an organic electronic device including the compound in an organic active layer.

Description

Compound and organic electronic device containing the same {COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME}

The present specification relates to a compound and an organic electronic device including the same.

As a device, it requires the exchange of holes and/or electrons between an electrode and an organic semiconductor material. Organic electronic devices can be largely divided into two types as follows according to the operation principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as a current source (voltage source) It is an electronic device in the form of The second type is an electronic device in which a voltage or current is applied to two or more electrodes to inject holes and/or electrons into an organic semiconductor material layer forming an interface with the electrodes, and operate by the injected electrons and holes.

Examples of organic electronic devices include organic photodiodes, organic solar cells, organic light emitting devices, organic photoconductors (OPCs) and organic transistors, all of which are electron/hole injection materials, electron/hole extraction materials, and electrons for driving devices. /requires a hole transport material or a light emitting material. Hereinafter, an organic solar cell will be described in detail, but in the organic electronic devices, electron/hole injection materials, electron/hole extraction materials, electron/hole transport materials, or light emitting materials all work on a similar principle.

An organic solar cell is a device capable of directly converting solar energy into electrical energy by applying a photovoltaic effect. Solar cells can be divided into inorganic solar cells and organic solar cells according to the materials constituting the thin film. A typical solar cell is made of a p-n junction by doping crystalline silicon (Si), an inorganic semiconductor. Electrons and holes generated by absorbing light diffuse to the p-n junction and are accelerated by the electric field to move to the electrode. The power conversion efficiency of this process is defined as the ratio of the power given to the external circuit and the solar power entered into the solar cell, and has been achieved up to 24% when measured under the currently standardized virtual solar irradiation conditions. However, since conventional inorganic solar cells already show limitations in economic feasibility and supply and demand in terms of materials, organic semiconductor solar cells that are easy to process, inexpensive, and have various functionalities are in the limelight as a long-term alternative energy source.

It is important for a solar cell to increase its efficiency so that it can output as much electrical energy as possible from solar energy. Low-molecular-weight materials (eg, ITIC), which are existing electron acceptor materials, have a low absorption rate in the long wavelength region and low thermal stability. and so on.

Accordingly, many examples of organic solar cells using polymeric materials as electron acceptor materials have recently been published, and in particular, research on compounds capable of designing and synthesizing various molecules is being actively conducted.

Polymer photovoltiac cells: Enhanced Efficiencies via Network of Internal Donor-Acceptor Heterojunctions (G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science, 270, 1789. (1995))

The present specification provides a compound and an organic electronic device including the same.

The present specification provides a compound comprising a unit of Formula 1 below.

[Formula 1]

In Formula 1,

n is an integer from 1 to 10,000;

[D1] is a group acting as an electron donor,

R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Q1 is a substituted or unsubstituted monocyclic or polycyclic aromatic ring; A substituted or unsubstituted monocyclic or polycyclic heterocyclic ring; Or represented by the following formula (2),

[Formula 2]

In Formula 2,

R10 and R11 are the same as or different from each other, and each independently hydrogen; halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

은 화학식 1에 결합되는 부위이다.

Is a site bound to Formula 1.

Another exemplary embodiment of the present specification is a first electrode;

a second electrode provided to face the first electrode; and

It is provided between the first electrode and the second electrode and includes one or more organic material layers including an organic active layer,

The organic active layer provides an organic electronic device including the compound.

A compound according to an exemplary embodiment of the present specification can freely control HOMO/LUMO energy levels.

In addition, when the compound according to an exemplary embodiment of the present specification is applied to an organic electronic device, charge balance can be controlled, and thus excellent performance can be exhibited.

In addition, the compound according to an exemplary embodiment of the present specification can be subjected to a solution process or a deposition process, which is advantageous for device application.

1 is a diagram illustrating an organic electronic device according to an exemplary embodiment of the present specification.
2 is a diagram illustrating an organic solar cell according to an exemplary embodiment of the present specification.
3 to 6 are diagrams illustrating an organic transistor according to an exemplary embodiment of the present specification.
7 is a diagram showing a UV-Vis spectrum of Compound 1 in a film state.
8 is a diagram showing a UV-Vis spectrum of Compound E in a film state.

Hereinafter, this specification will be described in detail.

An exemplary embodiment of the specification provides a compound including a unit of Formula 1 above.

Conventional organic solar cells have used monomolecular materials other than PCBM as electron acceptor materials. However, in one embodiment of the present specification, by using a compound (polymer material, polymer) including a unit of Chemical Formula 1, the conjugation length in the compound is long, so that the absorption region can be extended to a long wavelength region.

In addition, the unit represented by Chemical Formula 1 may exhibit excellent performance when applied to a device by binding D1, which exhibits an electron donor property, to a single molecule to which thiophene is fused.

The organic solar cell according to an exemplary embodiment of the present specification includes a polymer electron donor/polymer electron acceptor, so that the mechanical properties of the solar cell are higher than those in the case where a polymer electron donor/low molecular electron acceptor (eg, ITIC) is applied. this is excellent

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In the present specification, a “unit” is a repeating structure included in a monomer of a compound, and means a structure in which a monomer is bonded to a polymer by polymerization.

In the present specification, the meaning of "including a unit" means included in the main chain in the compound.

In this specification, "energy level" means the magnitude of energy. Therefore, even when an energy level is displayed in a negative (-) direction from a vacuum level, the energy level is interpreted as meaning an absolute value of the corresponding energy value. For example, the highest occupied molecular orbital (HOMO) energy level means the distance from the vacuum level to the highest occupied molecular orbital. In addition, the lowest unoccupied molecular orbital (LUMO) energy level means the distance from the vacuum level to the lowest unoccupied molecular orbital.

는 상기 다른 단위 또는 치환기에 연결되는 부위를 의미한다.In this specification,

means a site connected to the other unit or substituent.

Examples of the substituent are described below, but are not limited thereto.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; an alkyl group; cycloalkyl group; alkoxy group; aryl group; heterocyclic group; imide group; amide group; carbonyl group; ester group; alkenyl group; silyl group; And it means that it is substituted with one or more substituents selected from the group consisting of an amine group or does not have any substituents.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl , 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto it is not going to be

In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be, but is not limited thereto.

In the present specification, the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is 10-30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group includes at least one atom or heteroatom other than carbon, and specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Examples include a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, in the amide group, nitrogen of the amide group may be substituted with hydrogen, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an alkyl group having 1 to 25 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

In the present specification, the silyl group is specifically a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, it is not limited thereto.

In the present specification, the amine group is -NH ₂ ; monoalkylamine group; Dialkylamine group; N-alkyl arylamine group; monoarylamine group; Diaryl amine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the like, but are not limited thereto.

In the present specification, the aromatic ring may be selected from examples of the aryl group.

In one embodiment of the present specification, Q1 is a substituted or unsubstituted monocyclic or polycyclic aromatic ring; A substituted or unsubstituted monocyclic or polycyclic heterocyclic ring; Or represented by Formula 2 below.

[Formula 2]

In Formula 2,

R10 and R11 are the same as or different from each other, and each independently hydrogen; halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

은 화학식 1에 결합되는 부위이다.

Is a site bound to Formula 1.

In one embodiment of the present specification, Q1 is a substituted or unsubstituted monocyclic or polycyclic aryl group; A substituted or unsubstituted monocyclic or polycyclic heterocyclic group; or a compound represented by Formula 2 above.

In one embodiment of the present specification, Q1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted thieno[3,2-b]thiophene group, a substituted or unsubstituted dithieno[3,2-b:2',3'- d] thiophene (dithieno [3,2-b: 2', 3'-d] thiophene) group, or a compound represented by Formula 2 above.

In one embodiment of the present specification, the Q1 is any one of the following structures.

In the above structure,

R10 to R13 are the same as or different from each other, and each independently hydrogen; halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

은 화학식 1에 결합되는 부위이다.

Is a site bound to Formula 1.

In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 1-1 to 1-6 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,

n is an integer from 1 to 10,000;

[D1] is a group acting as an electron donor,

R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R10 to R13 are the same as or different from each other, and each independently hydrogen; halogen group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, the [D1] is any one of the following structures.

In the above structure,

R20 to R29 are the same as or different from each other, and each independently hydrogen; halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently represents an aryl group substituted with an alkyl group.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently represents a phenyl group substituted with an alkyl group.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently represents a phenyl group substituted with an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R10 to R13 are the same as or different from each other, and are hydrogen; or a halogen group.

In one embodiment of the present specification, R10 and R11 are hydrogen.

In an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other and are a halogen group.

In one embodiment of the present specification, R10 and R11 are fluorine.

In one embodiment of the present specification, R12 and R13 are hydrogen.

In one embodiment of the present specification, R12 and R13 are the same as or different from each other and are halogen groups.

In one embodiment of the present specification, R12 and R13 are fluorine.

In an exemplary embodiment of the present specification, R20 to R29 are the same as or different from each other, and hydrogen; or a halogen group.

In one embodiment of the present specification, R20 and R21 are hydrogen.

In an exemplary embodiment of the present specification, R20 and R21 are the same as or different from each other and are a halogen group.

In one embodiment of the present specification, R20 and R21 are fluorine.

In one embodiment of the present specification, R22 to R25 are hydrogen.

In one embodiment of the present specification, R26 to R29 are the same as or different from each other, and hydrogen; or a halogen group.

In one embodiment of the present specification, R26 and R29 are hydrogen.

In one embodiment of the present specification, R27 and R28 are hydrogen.

In an exemplary embodiment of the present specification, R27 and R28 are the same as or different from each other and are a halogen group.

In one embodiment of the present specification, R27 and R28 are fluorine.

In one embodiment of the present specification, Chemical Formula 1 includes any one of the following structures.

In one embodiment of the present specification, the terminal group of the compound is a substituted or unsubstituted halogen group.

In one embodiment of the present specification, the terminal group of the compound is a substituted or unsubstituted thiophene group.

In one embodiment of the present specification, the terminal group of the compound is a thiophene group.

In one embodiment of the present specification, when the compound is applied to a solar cell, since light absorption is possible in two or more regions among green, red, and blue regions, the efficiency of the device is improved.

In one embodiment of the present specification, the green region has a maximum emission wavelength between 500 nm and 570 nm, the red region has a maximum emission wavelength between 630 nm and 780 nm, and the blue region has a maximum emission wavelength between 400 nm and 480 nm. It can mean anything in between.

In one embodiment of the present specification, the compound is capable of absorbing light in the visible light wavelength region and can also absorb light in the infrared region. For example, not only the wavelength range of about 380 nm to 780 nm, but also light in the region of 780 nm or more can be absorbed. Accordingly, when applied to an organic electronic device, the effect of a wide absorption wavelength range of the device can be exhibited.

In one embodiment of the present specification, the compound has a maximum absorption wavelength at 300 nm to 1,000 nm, preferably at 700 nm to 950 nm.

In one embodiment of the present specification, the organic electronic device may include a first electrode;

a second electrode provided to face the first electrode; and

It is provided between the first electrode and the second electrode, and includes one or more organic material layers including an organic active layer, and the organic active layer includes the compound.

The organic electronic device of the present specification may be manufactured by conventional organic electronic device manufacturing methods and materials, except that the compound containing the unit represented by Chemical Formula 1 is included in the organic active layer.

FIG. 2 is a diagram illustrating an organic electronic device 100 including a first electrode 10, an organic active layer 30, and a second electrode 20 according to an exemplary embodiment of the present specification.

In one embodiment of the present specification, the organic electronic device is selected from the group consisting of an organic photodiode, an organic transistor, an organic solar cell, and an organic light emitting device.

In one embodiment of the present specification, the organic active layer includes a photoactive layer or a light emitting layer.

Below, an organic solar cell is illustrated. In the organic solar cell, the organic active layer is a photoactive layer, and as for the organic electronic device, a description of the organic solar cell to be described later can be cited.

An exemplary embodiment of the present specification is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode and including an organic active layer, wherein the organic active layer includes the compound.

In one embodiment of the present specification, the organic active layer includes a photoactive layer,

The photoactive layer includes an electron donor material and an electron acceptor material,

The electron acceptor material includes the compound.

That is, an exemplary embodiment of the present specification includes a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode and including a photoactive layer, wherein the photoactive layer includes an electron donor material and an electron acceptor material, and the electron acceptor material contains the compound It provides an organic solar cell comprising

In one embodiment of the present specification, the description of the compound is the same as that described above.

In one embodiment of the present specification, materials applied in the art may be used as the electron donor material. For example, poly 3-hexyl thiophene (P3HT: poly 3-hexyl thiophene), PCDTBT (poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4'-7'- di-2-thienyl-2',1',3'-benzothiadiazole)]), PCPDTBT (poly[2,6-(4,4-bis-(2-ethylhexyl)-4H-cyclopenta[2,1-b ;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)]), PFO-DBT (poly[2,7-(9,9-dioctylfluorene)-alt-5 ,5-(4,7-bis(thiophene-2-yl)benzo-2,1,3-thiadiazole)]), PTB7(Poly[[4,8-bis[(2-ethylhexyl)oxy]benzo[1 ,2-b:4,5-b']dithiophene-2,6-diyl][3-fluoro-2-[(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl]]), PSiF- DBT (Poly[2,7-(9,9-dioctyl-dibenzosilole)-alt-4,7-bis(thiophen-2-yl)benzo-2,1,3-thiadiazole]), PTB7-Th (Poly[ 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b;4,5-b']dithiophene-2,6-diyl-alt-(4-(2- ethylhexyl)-3-fluorothieno[3,4-b]thiophene-)-2-carboxylate-2-6-diyl)]), PBDB-T(poly[(2,6-(4,8-bis(5- (2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b']dithiophene))-alt-(5,5-(1',3'-di-2-thienyl) -5',7'-bis(2-ethylhexyl)benzo[1',2'-c:4',5'-c']dithiophene-4,8-dione))]) and PBDBT (poly(benzodithiophene- benzotriazole) may include one or more substances selected from the group consisting of.

In one embodiment of the present specification, the electron donor material and the electron acceptor material may be mixed in a mass ratio of 1:10 to 10:1. Specifically, the electron donor material and the electron acceptor material may be mixed in a mass ratio of 1:2 to 5:1, and more specifically, the electron donor material and the electron acceptor material may be mixed in a mass ratio of 1:2 to 2:1. can If necessary, the electron donor material and the electron acceptor material may be mixed in a mass ratio of 1:1.

In one embodiment of the present specification, the electron donor and electron acceptor may constitute a bulk heterojunction (BHJ).

A bulk heterojunction means that an electron donor material and an electron acceptor material are mixed with each other in the photoactive layer.

In one embodiment of the present specification, the photoactive layer is formed through a solution process.

In one embodiment of the present specification. The photoactive layer may be formed by dissolving a photoactive material such as an electron donor and/or an electron acceptor in an organic solvent and then using a method such as spin coating, dip coating, screen printing, spray coating, doctor blade or brush painting, It is not limited only to these methods.

An organic solar cell according to an embodiment of the present specification includes a first electrode, a photoactive layer, and a second electrode.

In one embodiment of the present specification, the organic solar cell may further include a substrate, a hole transport layer, and/or an electron transport layer.

In one embodiment of the present specification, the organic solar cell may further include an additional organic material layer. The organic solar cell may reduce the number of organic material layers by using organic materials having multiple functions at the same time.

In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode. In another embodiment, the first electrode is a cathode, and the second electrode is an anode.

In one embodiment of the present specification, the organic solar cell has a normal structure. In the normal structure, a substrate, a first electrode, a hole transport layer, an organic material layer including a photoactive layer, an electron transport layer, and a second electrode may be sequentially stacked.

In one embodiment of the present specification, the organic solar cell has an inverted structure. In the inverted structure, a substrate, a first electrode, an electron transport layer, an organic material layer including a photoactive layer, a hole transport layer, and a second electrode may be sequentially stacked.

In one embodiment of the present specification, a passivation layer may be further included on the second electrode.

The passivation layer may be formed on an exposed surface of the organic solar cell, and may absorb shock and stress generated during removal of the substrate as well as protect the organic solar cell.

2 is a diagram showing an organic solar cell according to an exemplary embodiment of the present specification including a substrate 101, a first electrode 10, a hole transport layer 102, a photoactive layer 103, and a second electrode 20. am.

In one embodiment of the present specification, the organic solar cell may be used without limitation of materials and/or methods in the art except for using the compound as a photoactive layer.

In one embodiment of the present specification, 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 limited as long as it is a substrate commonly used in organic solar cells. It doesn't work. Specifically, there are glass, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), and triacetyl cellulose (TAC). It is not limited to this.

The material of the first electrode may be a material that is transparent and has excellent conductivity, but is not limited thereto. For example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto. .

The method of forming the first electrode is not particularly limited, but, for example, sputtering, E-beam, thermal evaporation, spin coating, screen printing, inkjet printing, doctor blade or gravure printing may be used.

When the first electrode is formed on the substrate, it may undergo cleaning, moisture removal, and hydrophilic modification.

For example, the patterned ITO substrate is sequentially cleaned with detergent, acetone, and isopropyl alcohol (IPA), and then heated on a heating plate at 100° C. to 150° C. for 1 minute to 30 minutes, preferably at 120° C. for 10 minutes to remove moisture. After drying and when the substrate is completely cleaned, the surface of the substrate is modified to be hydrophilic.

Through the surface modification as described above, the junction surface potential can be maintained at a level suitable for the surface potential of the photoactive layer. In addition, when reforming, it is easy to form a polymer thin film on the first electrode, and the quality of the thin film may be improved.

Pretreatment technologies for the first electrode include a) surface oxidation using parallel plate discharge, b) surface oxidation using ozone generated using UV rays in a vacuum state, and c) oxygen generated by plasma. There are methods of oxidation using radicals.

One of the above methods may be selected according to the state of the first electrode or substrate. However, regardless of which method is used, it is desirable to prevent oxygen escape from the surface of the first electrode or the substrate and to suppress the remaining moisture and organic matter as much as possible. At this time, the practical effect of the pretreatment can be maximized.

As a specific example, a method of oxidizing the surface through ozone generated using UV may be used. At this time, after ultrasonic cleaning, the patterned ITO substrate is baked on a hot plate, dried well, put into a chamber, and a UV lamp is operated to generate oxygen gas by reacting with UV light to generate ozone. The patterned ITO substrate can be cleaned.

However, the surface modification method of the patterned ITO substrate in the present specification does not need to be particularly limited, and any method may be used as long as the method oxidizes the substrate.

The second electrode may be a metal having a low work function, but is not limited thereto. Specifically, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; Alternatively, it may be a material having a multilayer structure such as LiF/Al, LiO ₂ /Al, LiF/Fe, Al:Li, Al:BaF ₂ , and Al:BaF ₂ :Ba, but is not limited thereto.

The second electrode may be deposited and formed inside a thermal evaporator exhibiting a vacuum degree of 5x10 ^{- 7} torr or less, but is not limited to this method.

The passivation layer may be made of inorganic materials such as silicon oxide (SiOx) and silicon nitride (SiNx), or organic materials such as benzocyclobutene (BCB) and photoacryl, but is not limited thereto.

The passivation layer may be formed on the exposed surface of the organic solar cell using plasma enhanced chemical vapor deposition (PECVD).

The material of the hole transport layer and/or the electron transport layer serves to efficiently transfer electrons and holes separated from the photoactive layer to the electrode, and the material is not particularly limited.

Materials applied to the hole transport layer include PEDOT:PSS (Poly(3,4-ethylenediocythiophene) doped with poly(styrenesulfonic acid)), molybdenum oxide (MoOx); vanadium oxide (V ₂ O ₅ ); nickel oxide (NiO); and tungsten oxide (WO _x ), but are not limited thereto.

The material applied to the electron transport layer may be bathocuproine (BCP) or electron-extracting metal oxides, and specifically, a metal complex of bathocuproine (BCP) and 8-hydroxyquinoline; Complexes containing Alq ₃ ; metal complexes including Liq; LiF; Ca; titanium oxide (TiOx); zinc oxide (ZnO); and cesium carbonate (Cs ₂ CO ₃ ), but are not limited thereto.

Below, organic transistors are exemplified.

In one embodiment of the present specification, the organic electronic device may be an organic transistor. Specifically, the organic electronic device may include a gate electrode; source electrode; drain electrode; and one or more organic material layers including an organic active layer, wherein the organic active layer includes the compound.

In one embodiment of the present specification, the organic transistor may have a top gate structure. Specifically, the source electrode 70 and the drain electrode 80 are first formed on the substrate 40, and then the organic layer 90, the insulating layer 60, and the gate electrode 50 may be sequentially formed. 2 shows an organic transistor structure accordingly.

In one embodiment of the present specification, the organic transistor may be a bottom contact structure among bottom gate structures. Specifically, the gate electrode 50 and the insulating layer 60 are sequentially formed on the substrate 40, then the source electrode 70 and the drain electrode 80 are formed on the insulating layer 60, and finally An organic material layer 90 may be formed on the source electrode 70 and the drain electrode 80 . 4 and 5 show organic transistor structures accordingly.

In one embodiment of the present specification, the organic transistor may be a top contact structure among bottom gate structures. Specifically, the gate electrode 50 and the insulating layer 60 are sequentially formed on the substrate 40, then the organic material layer 90 is formed on the insulating layer 60, and finally, the organic material layer 90 is formed. A source electrode 70 and a drain electrode 80 may be formed. 6 shows an organic transistor structure accordingly.

In the present specification, the gate electrode may have a pattern shape, but is not limited thereto. The gate electrode is selected from gold (Au), nickel (Ni), copper (Cu), silver (Ag), aluminum (Al), aluminum alloy (Al-alloy), molybdenum (Mo), and molybdenum alloy (Mo-alloy) can be formed into any one.

In the present specification, the gate electrode may be formed using a method selected from photolithography, offset printing, silk screen printing, inkjet printing, thermal evaporation, and a method using a shadow mask. It is not limited to this.

The thickness of the gate electrode may be 10 nm to 300 nm, preferably 10 nm to 50 nm.

In the present specification, the insulating layer is composed of a single film or a multi-layered organic insulating film or an inorganic insulating film, or an organic-inorganic hybrid film. As the inorganic insulating layer, one or more selected from silicon oxide, silicon nitride, Al ₂ O ₃ , Ta ₂ O ₅ , BST, and PZT may be used. Examples of the organic insulating film include CYTOP ^TM , polymethylmethacrylate (PMMA), polystyrene (PS, polystyrene), phenol-based polymers, acrylic polymers, imide-based polymers such as polyimide, arylether-based polymers, amide-based polymers, Any one or more selected from fluorine-based polymers, p-xyrene-based polymers, vinyl alcohol-based polymers, and parylene may be used, but is not limited thereto.

In the present specification, the insulating layer may be formed through a solution process, and may be applied over a large area through spin coating, bar coating, slit die coating, doctor blade, and the like. Preferably, the insulating layer may be formed through spin coating, but is not limited thereto. When the insulating layer is formed, heat treatment is performed at 100° C. to 150° C. for 30 minutes or more so that the solvent used can be completely evaporated.

In the present specification, the source electrode and the drain electrode may be made of a conductive material, for example, carbon, aluminum, vanadium, chromium, copper, zinc, silver, gold, magnesium, calcium, sodium, potassium, titanium, indium, yttrium , lithium, gadolinium, tin, lead, neodymium, platinum, nickel, similar metals and alloys thereof; p- or n-doped silicon; zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, similar tin oxide and tin oxide indium-based complex compounds; mixtures of oxides and metals such as ZnO:Al, SnO ₂ :Sb; and poly(3-methylthiophene), poly[3,4-(ethylene-1,2-deoxy)thiophene] (poly[3,4-(ethylene-1,2 -dioxy) thiophene]), polypyrrole, and conductive polymers such as polyaniline, but are not limited thereto.

In the present specification, the organic active layer may be formed through a solution process. At this time, the organic active layer may be applied to a large area through spin coating, bar coating, slit die coating, doctor blade coating, inkjet coating, etc., but is not limited thereto.

In the present specification, when forming the source electrode and the drain electrode on the substrate, the source electrode and the drain electrode may be formed using a thermal evaporation method, but is not limited thereto, and other methods known in the art can be formed by At this time, the distance between the source electrode and the drain electrode typically has a channel length of 2 μm to hundreds of μm, and the channel width may be configured to be about 10 to 1000 times the channel length. The source and drain electrodes are usually made of gold and nickel, but other electrodes such as silver, copper, and molybdenum may also be used.

In the present specification, when forming the source electrode and the drain electrode on the organic active layer, the source electrode and the drain electrode may be formed using a photolithography process or a shadow mask process, but is not limited thereto, and the related art It can be formed by other methods known in

An exemplary embodiment of the present specification provides an organic image sensor including the organic electronic element.

An organic image sensor according to an exemplary embodiment of the present specification may be applied to an electronic device, for example, a mobile phone, a digital camera, etc., but is not limited thereto.

Hereinafter, examples will be described in detail in order to specifically describe the present specification. However, the embodiments according to the present specification may be modified in many different forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments herein are provided to more completely explain the present specification to those skilled in the art.

manufacturing example 1. Preparation of Compound 1

(1) Preparation of Compound A

In a round flask equipped with a condenser, 5 g of 2,5-bis(trimethylstenyl)thieno[3,2-b]thiophene, Tris (dibenzylideneacetone) dipalladium (0) (tris (dibenzylideneacetone) dipalladium (0), Pd ₂ (dba ₃ )) 0.43 g and tri (o-tolyl) phosphine (tri (o-tolyl) phosphine) 0.57 g were dissolved together in 150 mL of toluene and refluxed. When the temperature reached 100 ° C., 5.15 g (2.5 eq) of ethyl 2-bromothiophene-3-carboxylate was dissolved in 5 mL of toluene, slowly injected, and refluxed for 12 hours. After the reaction was completed, compound A (diethyl 2,2'-(4,8-bis((triisopropylsilyl)ethynyl)benzo[1,2-b:4,5-b']dithiophene- 2,6-diyl)bis(thiophene-3-carboxylate)) was obtained.

(2) Preparation of compound B

After dissolving 8.16g (5.3eq) of 1-bromo-4-hexylbenzene in 200mL of THF in a round flask, slowly add 13.5mL of n-butyllithium (n-BuLi) at -78℃. After injection, the mixture was stirred at the same temperature for 1 hour. After dissolving 5 g of Compound A prepared in (1) in 50 mL of THF, it was slowly injected into a round flask under stirring, followed by stirring at room temperature for 12 hours. After extracting the organic layer with chloroform, the solvent was removed, and the mixture was dissolved in 100 mL of octane, 10 mL of acetic acid, and 1 mL of sulfuric acid, and then refluxed at 65° C. for 4 hours. The reaction was terminated with distilled water, and compound B was obtained through column chromatography.

(3) Preparation of compound C

In a round flask, 1 g of Compound B prepared in (2) above was dissolved in 100 mL of THF, and then 0.76 mL of n-BuLi was slowly injected at -78 °C. After stirring at the same temperature for 1 hour, 0.5 mL of DMF was slowly injected and stirred for 12 hours. After completion of the reaction with distilled water, the organic layer was extracted and compound C was obtained through column chromatography.

(4) Preparation of compound D

In a round flask equipped with a condenser, 1 g of compound C prepared in (3) above and 2-(6-bromo-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile After dissolving 0.7 g of (2-(6-bromo-3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile) in 10 mL of chloroform and injecting 1 mL of pyridine, the mixture was refluxed at 60 °C for 12 hours. After filtration through methanol, compound D was obtained through column chromatography.

However, 2-(6-bromo-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile used here has bromine positions 5 and 6 mixed in a mass ratio of 3:7, respectively. is a compound

(5) Preparation of Compound 1

In a round flask equipped with a condenser, 300 mg of compound D prepared in 4) above, 80 mg (1.0eq) of 2,5-bis (trimethylstenyl) thiophene and tetrakis (trimethylstenyl) thiophene Phenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) 0.01 g (0.03 eq) was injected, and then 10 mL of toluene was injected. Thereafter, the mixture was refluxed at 100° C. for 17 hours, the reaction was terminated with methanol, and the synthesized compound 1 was purified using methanol, nucleic acid and acetone to obtain compound 1. At this time, by measuring the number average molecular weight (Mn), it was confirmed that Compound 1 was prepared. <Mn: 19,000 g/mol, PDI: 1.25>

The UV-Vis spectrum of the prepared compound 1 in a film state is shown in FIG. 7 .

The film state means that a solution in which Compound 1 was dissolved in a chloroform solution was spin-coated and then dried to form a film state .

manufacturing example 2. Preparation of Compound 2

In the preparation of Compound 1, (3,4-difluorothiophene-2,5-diyl)bis(trimethylstannane ((3,4-difluorothiophene-2,5-diyl) instead of 2,5-bis(trimethylstannyl)thiophene Except for using bis(trimethylstannane)), compound 2 was prepared in the same manner as in the preparation method of compound 1. At this time, it was confirmed that compound 2 was prepared by measuring the number average molecular weight (Mn). <Mn: 17,000 g/mol, PDI: 1.30>

manufacturing example 3. Preparation of compound 3

In the preparation of Compound 1, 5,5'-bis(trimethylstannyl)-2,2'-bithiophene (5,5'-bis(trimethylstannyl)-2,2' instead of 2,5-bis(trimethylstannyl)thiophene -bithiophene) was used, and compound 3 was prepared in the same manner as in the preparation method of compound 1. At this time, by measuring the number average molecular weight (Mn), it was confirmed that Compound 3 was prepared. <Mn: 18,500 g/mol, PDI: 1.40>

manufacturing example 4. Preparation of compound 4

In the preparation of Compound 1, (3,3'-difluoro-[2,2'-bithiophene] -5,5'-diyl)bis(trimethylstannane) instead of 2,5-bis(trimethylstannyl)thiophene ( Compound 4 was prepared in the same manner as in Compound 1, except that (3,3'-difluoro-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)) was used. manufactured. At this time, by measuring the number average molecular weight (Mn), it was confirmed that Compound 4 was prepared. <Mn: 17,000 g/mol, PDI: 1.60>

manufacturing example 5. Preparation of Compound E (Comparative Compound 1)

In a round flask equipped with a condenser, 1 g of Compound C prepared in (3) of Preparation Example 1 and 2- (3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile (2 After dissolving 0.7 g of -(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) in 10 mL of chloroform and injecting 1 mL of pyridine, the mixture was refluxed at 60 °C for 12 hours. After filtration through methanol, compound E was obtained through column chromatography.

The UV-Vis spectrum of the prepared compound E in a film state is shown in FIG. 8 .

The film state means that a solution in which compound E was dissolved in a chloroform solution was spin-coated and then dried to form a film state .

<Example: Preparation of Organic Solar Cell>

Example One.

(1) Preparation of composite solution

The compound poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b']dithiophene) )-Alt-(5,5-(1',3'-di-2-thienyl-5',7'-bis(2-ethylhexyl)benzo[1',2'-c:4',5 '-c']dithiophene-4,8-dione))](poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)- benzo[1, 2-b:4,5-b']dithiophene))-alt-(5,5-(1',3'-di-2-thienyl-5',7'- bis(2-ethylhexyl)benzo[1 ',2'-c:4',5'-c']dithiophene-4,8-dione))], PBDB-T) (Mn: 25,000 g/mol, Solarmer Co.) as an electron donor material, prepared above Compound 1 synthesized in Example was used as an electron acceptor material and dissolved in chlorobenzene (CB) at a mass ratio of 1:1 to prepare a composite solution having a concentration of 2 wt%.

(2) Manufacture of organic solar cells

A glass substrate (11.5Ω/□) coated with a 1.5×1.5cm ² bar type of ITO was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was treated with ozone for 10 minutes to remove it. 1 electrode was formed.

After spin-coating a ZnO nanoparticle solution (N-10, Nanograde Ltd, 2.5 wt% in 1-butanol, filtered through 0.45 μm PTFE) at 4,000 rpm for 40 seconds on the first electrode, An electron transport layer was formed by removing the remaining solvent by heat treatment at 80° C. for 10 minutes.

Thereafter, the composite solution prepared in (1) was spin-coated for 25 seconds at 700 rpm at 70° C. on the electron transport layer to form a photoactive layer, and MoO ₃ was applied on the photoactive layer at a rate of 0.2 Å/s and 10 ^- A hole transport layer was formed by thermal evaporation to a thickness of 10 nm under a vacuum of ⁷ torr.

Thereafter, Ag was deposited to a thickness of 100 nm at a rate of 1 Å/s inside a thermal evaporator to form a second electrode, thereby manufacturing an organic solar cell having an inverted structure.

Example 2.

An organic solar cell was manufactured in the same manner as in Example 1, except that the composite solution prepared in (1) was spin-coated at 900 rpm when the photoactive layer was formed in Example 1.

Example 3.

An organic solar cell was manufactured in the same manner as in Example 1, except that the composite solution prepared in (1) was spin-coated at 1,100 rpm when the photoactive layer was formed in Example 1.

Example 4.

An organic solar cell was manufactured in the same manner as in Example 1, except that the composite solution prepared in (1) was spin-coated at 1,300 rpm when the photoactive layer was formed in Example 1.

comparative example One.

An organic solar cell was prepared in the same manner as in Example 1, except that Comparative Compound 1 was used instead of Compound 1 when preparing the composite solution in Example 1.

[Comparative Compound 1]

comparative example 2.

An organic solar cell was manufactured in the same manner as in Comparative Example 1, except that the composite solution was spin-coated at 900 rpm when forming the photoactive layer in Comparative Example 1.

comparative example 3.

An organic solar cell was manufactured in the same manner as in Comparative Example 1, except that the composite solution was spin-coated at 1,100 rpm when forming the photoactive layer in Comparative Example 1.

comparative example 4.

An organic solar cell was manufactured in the same manner as in Comparative Example 1, except that the composite solution was spin-coated at 1,300 rpm when forming the photoactive layer in Comparative Example 1.

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

Spin-speed (rpm) V _oc
(V) Jsc
(mA/cm ² ) FF η
(%) mean η
(%) PBDB-T
+ compound 1 Example
One 700 0.919 17.032 0.580 9.07 8.85 0.916 16.628 0.566 8.63 Example
2 900 0.925 17.168 0.629 9.98 10.07 0.924 17.202 0.639 10.16 Example
3 1,100 0.926 16.502 0.650 9.94 9.90 0.924 16.372 0.652 9.86 Example
4 1,300 0.910 16.053 0.644 9.40 9.09 0.901 15.766 0.618 8.78 PBDB-T
+ comparative compound 1 comparative example
One 700 0.739 17.869 0.523 6.91 6.91 0.736 17.932 0.522 6.90 comparative example
2 900 0.733 18.340 0.568 7.63 7.63 0.729 18.552 0.564 7.62 comparative example
3 1,100 0.750 17.323 0.605 7.86 7.87 0.746 17.627 0.598 7.87 comparative example
4 1,300 0.744 16.563 0.616 7.59 7.72 0.748 16.596 0.632 7.84

In Table 1, the Spin-speed is the rotational speed of the equipment when forming the photoactive layer by spin-coating the composite solution on the electron transport layer, V _OC is the open circuit voltage, J _SC is the short circuit current, and FF is the charging rate (Fill factor), η means 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, and the higher these two values are, the higher the efficiency of the solar cell is. In addition, the fill factor is a value obtained by dividing the area of a rectangle that can be drawn inside the curve by the product of the short circuit current and the open circuit voltage. The energy conversion efficiency (η) can be obtained by dividing the product of the open-circuit voltage (Voc), the short-circuit current (Jsc), and the charge factor (FF) by the intensity of incident light (Pin), and a higher value is preferable.

Looking at the results of Table 1, the organic solar cells of Examples 1 to 4 using Compound 1 according to an exemplary embodiment of the present specification as an electron acceptor have an open circuit voltage compared to the organic solar cells of Comparative Examples 1 to 4 using a comparative compound. It can be seen that this is high, the device efficiency such as filling factor is excellent, and the energy conversion efficiency is excellent. Specifically, in the case of an organic solar cell using a compound according to an exemplary embodiment of the present specification, the energy conversion efficiency was measured to be 8% or more, preferably 9% or more.

In addition, it can be seen from FIGS. 7 and 8 that Compound 1 according to an exemplary embodiment of the present specification exhibits a red-shifted tendency compared to Comparative Compound 1. This tendency can be seen as a result of the polymerization of Compound 1 as the conjugation length increases, and as a result, it can contribute to high FF and lead to excellent energy conversion efficiency.

10: first electrode
20: second electrode
30: organic active layer
40: substrate
50: gate electrode
60: insulating layer
70: source electrode
80: drain electrode
90: organic active layer
100: organic electronic element
101: substrate
102: hole transport layer
103: photoactive layer

Claims (7)

A compound containing a unit represented by Formula 1-2:
[Formula 1-2]

In Formula 1-2,
n is an integer from 1 to 10,000;
R1 to R4 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms,
D1 is any one of the following structures,

In the above structure,
R20 to R29 are the same as or different from each other, and each independently hydrogen; or a halogen group. delete delete The method of claim 1,
Formula 1-2 is a compound comprising any one of the following structures:

a first electrode;
a second electrode provided to face the first electrode; and
It is provided between the first electrode and the second electrode and includes one or more organic material layers including an organic active layer,
The organic active layer is an organic electronic device comprising the compound according to claim 1 or 4. The method of claim 5,
The organic electronic device is selected from the group consisting of an organic photodiode, an organic transistor, an organic solar cell, and an organic light emitting device. The method of claim 5,
The organic active layer includes a photoactive layer,
The photoactive layer includes an electron donor material and an electron acceptor material,
The electron acceptor material is an organic electronic device comprising the compound.

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