KR20200004084A - Heterocyclic compound, composition comprising the same, and organic electronic device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1, a composition comprising the same, and an organic electronic device comprising the same. The organic electronic device comprising the heterocyclic compound represented by the chemical formula 1 according to an embodiment of the present specification has a high open voltage, a high short circuit current, and excellent photoelectric conversion efficiency.

Description

Heterocyclic compound, a composition comprising the same, and an organic electronic device comprising the same TECHNICAL FIELD [0001] AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

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

The organic electronic device refers to a device that requires charge exchange between an electrode and an organic material using holes and / or electrons. The organic electronic device can be divided into two types according to the operating principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a form of electric element. The second type is an electronic device in which holes and / or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

Examples of the organic electronic device include an organic solar cell, an organic photoelectric device, an organic light emitting device, and an organic transistor. Hereinafter, the organic solar cell will be described in detail. However, in the organic electronic device, holes are injected or transported, The injection or transport material of electrons, or the luminescent material, acts on a similar principle.

It is important to increase efficiency so that organic solar cells can output as much electrical energy as possible from solar energy. It is important to generate as much excitons as possible inside the semiconductor to increase the efficiency of such organic solar cells, but it is also important to draw the generated charges to the outside without loss. One of the causes of the loss of charge is that the generated electrons and holes disappear by recombination. Various methods have been proposed as methods for transferring the generated electrons or holes to the electrodes without losing the electrons or holes, but most of the additional processes are required and manufacturing costs may increase accordingly.

US 5331183 US 5454880

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

The present specification provides a heterocyclic compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

X1 to X4 are the same as or different from each other, and each independently S, O, or Se,

R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted linear or branched alkyl group; A substituted or unsubstituted linear or branched alkoxy group; Substituted or unsubstituted linear or branched thioalkoxy group; Substituted or unsubstituted monocyclic or polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group,

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group,

G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxyl group; Or a halogen group,

EW1 and EW2 are the same as or different from each other, and each independently serves as an electron acceptor.

The present specification provides a composition for an organic electronic device including the heterocyclic compound described above.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described composition for organic electronic devices. do.

The organic electronic device including the heterocyclic compound represented by Formula 1 according to an exemplary embodiment of the present specification has a high open voltage, a high short circuit current, and an excellent photoelectric conversion efficiency.

1 is a diagram illustrating an organic electronic device according to an exemplary embodiment of the present specification.
2 is a diagram showing ¹ H-NMR data of Compound 1 of the present specification.
3 is a diagram showing ¹ H-NMR data of Compound 2 of the present specification.
4 is a view showing UV-Vis absorption spectra in the film state of the compound 1 and 2 of the present specification.
5 is a current density graph according to the voltage of Examples 1-1 to 1-4 and 2-1 to 2-3 of the present specification.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a heterocyclic compound represented by Chemical Formula 1.

The heterocyclic compound represented by Formula 1 according to an exemplary embodiment of the present specification is a novel compound such as a 9-ring ring as a core, and has a longer length of conjugation than a compound having a 5- to 7-ring ring as a core. Induction of intermolecular packing (packing) through intermolecular interactions, and absorbs a wide wavelength of light, the organic solar cell comprising the same has a high short-circuit current.

In addition, the heterocyclic compound has a lower energy loss than the conventional compound having five to seven ring rings as a core, and thus has a high open voltage (V _oc ) and excellent photoelectric conversion efficiency.

In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

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

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

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; An alkyl group; An alkoxy group; Thioalkoxy group; Aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, S atoms or do not have any substituents.

The substituents may be substituted or unsubstituted with additional 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 chain, carbon number 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, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl, and the like.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, 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 and p-methylbenzyloxy, and the like, It is not limited.

In the present specification, the description of the alkoxy group may be applied except that O of the alkoxy group is S.

In the present specification, the aryl group 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. In addition, the aryl group in the present specification may mean an aromatic ring.

When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 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.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group and fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group has a structure in which two ring organic compounds are connected through one atom.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And so on. However, the present invention is not limited thereto.

In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heteroaryl group include selenophene group, thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group , Aridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline Group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), isoxazolyl Groups, thiadiazolyl groups, benzothiadiazolyl groups, phenothiazinyl groups, thienothiophene groups, dibenzofuranyl groups, and the like, but are not limited thereto.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

In the present specification, the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group or heterocyclic group except that it is not monovalent.

In the present specification, an electron donative group (EDG) or an electron donor material which acts as an electron donor is a substituent or a substance having a negatively charged or unshared electron pair, and means donating an electron to a portion lacking a positive charge or an electron pair. In addition, the electron donative group (EDG) or electron donor material which acts as an electron donor in the present specification has abundant electron retention property of the molecule itself when it is lighted in a mixed state with an electron acceptor even if it does not have a negative but unshared electron pair. It includes a substituent capable of transferring an electron (excited electron) to the electron acceptor having a large electronegativity.

In this specification, an electron withdrawing group (EWG) or an electron acceptor material serving as an electron acceptor refers to a substituent or substance that accepts an electron from an electron donor group.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms; Linear or branched alkoxy groups having 1 to 10 carbon atoms; Linear or branched thioalkoxy groups having 1 to 10 carbon atoms; Monocyclic aryl groups having 6 to 12 carbon atoms substituted with linear or branched alkyl groups having 1 to 10 carbon atoms; Or a monocyclic heteroaryl group having 2 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms; Linear or branched alkoxy groups having 1 to 10 carbon atoms; Linear or branched thioalkoxy groups having 1 to 10 carbon atoms; A phenyl group substituted with a linear or branched alkyl group having 1 to 10 carbon atoms; A thiophene group substituted with a linear or branched alkyl group having 1 to 10 carbon atoms; Selenophene group substituted with a linear or branched alkyl group having 1 to 10 carbon atoms; Or a furan group substituted with a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently a linear or branched alkoxy group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 is n-octyloxy group.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently selected from the following structures.

In the above structure, R11 to R17 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4 are the same as or different from each other, and each independently selected from the following structures.

In the above structure, R11 to R17 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, the R11 to R17 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the R11 to R17 is n-octyl group.

According to an exemplary embodiment of the present specification, R12 is an n-octyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently a linear or branched alkyl group of 1 to 10 carbon atoms, linear or branched chain of 1 to 10 carbon atoms C6-C12 monocyclic aryl group substituted by the alkoxy group or the C1-C10 linear or branched thioalkoxy group; Or a monocyclic hetero ring having 2 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms, a straight or branched chain alkoxy group having 1 to 10 carbon atoms, or a linear or branched thioalkoxy group having 1 to 10 carbon atoms; It is an aryl group.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently a linear or branched alkyl group of 1 to 10 carbon atoms, linear or branched chain of 1 to 10 carbon atoms An alkoxy group or a phenyl group substituted with a straight or branched thioalkoxy group having 1 to 10 carbon atoms; Thiophene groups substituted with a linear or branched alkyl group having 1 to 10 carbon atoms, a straight or branched alkoxy group having 1 to 10 carbon atoms, or a thioalkoxy group having 1 to 10 carbon atoms as the straight or branched chain; Selenophene groups substituted with a linear or branched alkyl group having 1 to 10 carbon atoms, a straight or branched alkoxy group having 1 to 10 carbon atoms, or a thioalkoxy group having 1 to 10 carbon atoms as the straight or branched chain; Or a furan group substituted with a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a thioalkoxy group having 1 to 10 carbon atoms as a straight or branched chain.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently a linear or branched alkyl group substituted phenyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 to Ar4 is a phenyl group substituted with an n-hexyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 to Ar4 are the same as or different from each other, each independently selected from the following structures.

In the above structure, R18 to R21 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted thioalkoxy group.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 to Ar4 are the same as or different from each other, each independently selected from the following structures.

In the above structure, R18 to R21 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted thioalkoxy group.

According to an exemplary embodiment of the present specification, R18 to R21 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms, a straight or branched alkoxy group having 1 to 10 carbon atoms, or carbon atoms It is 1-10 linear or branched thioalkoxy group.

According to an exemplary embodiment of the present specification, R18 to R21 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the R18 to R21 is n-hexyl group.

According to an exemplary embodiment of the present specification, R18 is an n-hexyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, G1 to G4 is hydrogen.

According to an exemplary embodiment of the present specification, in the general formula 1, EW1 and EW2 are the same as or different from each other, each independently represent a group represented by the formula (a).

[Formula a]

In Chemical Formula a,

Cy 1 is a monocyclic or polycyclic hydrocarbon ring having 6 to 20 carbon atoms unsubstituted or substituted with a halogen group, a straight or branched chain alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms; Or a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms unsubstituted or substituted with a halogen group, a straight or branched chain alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms,

는 상기 화학식 1에 결합되는 부위이다.

Is a site bonded to the formula (1).

According to an exemplary embodiment of the present specification, Cy1 is a monocyclic or polycyclic hydrocarbon ring having 6 to 20 carbon atoms unsubstituted or substituted with a halogen group or a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Cy1 is a monocyclic hydrocarbon ring having 6 to 12 carbon atoms which is unsubstituted or substituted with a halogen group or a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Cy1 is a benzene ring unsubstituted or substituted with a halogen group or a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Cy1 is a benzene ring substituted or unsubstituted with fluorine or a methyl group.

According to an exemplary embodiment of the present specification, Cy1 is a benzene ring substituted with fluorine.

According to an exemplary embodiment of the present specification, the EW1 and EW2 are the same as or different from each other, and are each independently selected from the following structure.

이다.According to an exemplary embodiment of the present specification, the EW1 and EW2 is

to be.

이다.According to an exemplary embodiment of the present specification, the EW1 and EW2 is

to be.

According to an exemplary embodiment of the present specification, in the general formula 1, X1 is O.

According to an exemplary embodiment of the present specification, in the general formula 1, X1 is S.

According to an exemplary embodiment of the present specification, in the general formula 1, X1 is Se.

According to an exemplary embodiment of the present specification, in the general formula 1, X2 is O.

According to an exemplary embodiment of the present specification, in the general formula 1, X2 is S.

According to an exemplary embodiment of the present specification, in the general formula 1, X2 is Se.

According to an exemplary embodiment of the present specification, in the general formula 1, X3 is O.

According to an exemplary embodiment of the present specification, in the general formula 1, X3 is S.

According to an exemplary embodiment of the present specification, in the general formula 1, X3 is Se.

According to an exemplary embodiment of the present specification, in the general formula 1, X4 is O.

According to an exemplary embodiment of the present specification, in the general formula 1, X4 is S.

According to an exemplary embodiment of the present specification, in the general formula 1, X4 is Se.

According to an exemplary embodiment of the present specification, in the general formula 1, X1 to X4 is S.

According to an exemplary embodiment of the present specification, in the general formula 1, X1 to X4 is O.

According to an exemplary embodiment of the present specification, in the general formula 1, X1 to X4 is Se.

According to an exemplary embodiment of the present specification, Formula 1 is represented by the following formula 1-1.

[Formula 1-1]

In Chemical Formula 1-1,

Definitions of R1 to R4 and Ar1 to Ar4 are the same as defined in Formula 1

Cy1 and Cy2 are the same as or different from each other, and each independently 6 to 20 carbon atoms unsubstituted or substituted with a halogen group, a straight or branched chain alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms Monocyclic or polycyclic hydrocarbon ring; Or a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms unsubstituted or substituted with a halogen group, a straight or branched chain alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Cy1 and Cy2 are the same as or different from each other, and each independently a monocyclic ring having 6 to 20 carbon atoms unsubstituted or substituted with a halogen group or a linear or branched alkyl group having 1 to 10 carbon atoms. Or a polycyclic hydrocarbon ring.

According to an exemplary embodiment of the present specification, Cy1 and Cy2 are the same as or different from each other, and each independently a monocyclic ring having 6 to 12 carbon atoms unsubstituted or substituted with a halogen group or a linear or branched alkyl group having 1 to 10 carbon atoms. Hydrocarbon ring.

According to an exemplary embodiment of the present specification, Cy1 and Cy2 are the same as or different from each other, and each independently a halogen group or a benzene ring unsubstituted or substituted with a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Cy1 and Cy2 are the same as or different from each other, and each independently a benzene ring unsubstituted or substituted with fluorine or a methyl group.

According to an exemplary embodiment of the present specification, Cy1 and Cy2 are benzene rings substituted with fluorine.

The structure of the EW1 and EW2 by adjusting the energy level of the formula (1), that is, by adjusting the absorption wavelength of light, the organic solar cell comprising the same has a synergistic effect of the open-circuit voltage (V _oc ) and short-circuit current (J _sc ). . Specifically, when Cy1 of Chemical Formula a is a benzene ring substituted with a halogen group, the absorption region of light moves to a longer wavelength to obtain a high short-circuit current, and the benzene ring or unsubstituted benzene where Cy1 is substituted with a halogen group In the case of a ring, the absorption region of light is shifted toward the longer wavelength, thereby obtaining a high short circuit current.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

The present specification provides a composition for an organic electronic device comprising a heterocyclic compound represented by Chemical Formula 1.

According to the exemplary embodiment of the present specification, the composition for an organic electronic device includes an electron donor material and an electron acceptor material, and the electron acceptor material includes the heterocyclic compound.

In addition, the electron donor material in the composition for an organic electronic device may be applied to most electron donor materials having a maximum absorption wavelength in the visible light region, but is not limited thereto.

According to one embodiment of the present specification, the electron donor material may be a material applied in the art, 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-dioctyl-fluorene) -alt-5,5- (4,7-di 2-thienyl-2,1,3-benzothiadiazole)]), PTB7 (or PTB7-Th) (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]) and poly (benzodithiophene-benzotriazole) (PBDB-T).

According to the exemplary embodiment of the present specification, the composition for an organic electronic device includes an electron donor material and an electron acceptor material, and includes a weight ratio of 1:99 to 99: 1.

According to the exemplary embodiment of the present specification, the photoactive layer includes an electron donor material and an electron acceptor material, and includes a weight ratio of 1: 5 to 5: 1.

According to an exemplary embodiment of the present specification, the electron donor and the electron acceptor constitute a bulk hetero junction (BHJ).

According to an exemplary embodiment of the present specification, the composition for an organic electronic device may further include a solvent.

In one embodiment of the present specification, the composition for an organic electronic device may be a liquid. The "liquid phase" means a liquid state at room temperature and normal pressure.

In one embodiment of the present specification, the solvent is, for example, a chlorine solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; Polyhydric compounds such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin and 1,2-hexanediol Alcohols and derivatives thereof; Alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; Sulfoxide solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; Benzoate solvents such as methyl benzoate, butyl benzoate and 3-phenoxy benzoate; Although solvents, such as tetralin, are illustrated, if the solvent which can melt | dissolve or disperse the compound which concerns on one Embodiment of this specification is sufficient, These are not limited.

In another exemplary embodiment, the solvent may be used alone or in combination of two or more solvents.

In another exemplary embodiment, the boiling point of the solvent is preferably 40 ° C to 250 ° C, more preferably 60 ° C to 230 ° C, but is not limited thereto.

In another exemplary embodiment, the viscosity of the single or mixed solvent is preferably 1 CP to 10 CP, more preferably 3 CP to 8 CP, but is not limited thereto.

In another embodiment, the concentration of the composition for an organic electronic device is preferably 0.1 wt / v% to 20 wt / v%, more preferably 0.5 wt / v% to 5 wt / v%, but It is not limited.

According to an exemplary embodiment of the present specification, the composition for an organic electronic device further comprises an additive.

According to an exemplary embodiment of the present specification, the molecular weight of the additive is 50 g / mol to 1000 g / mol.

According to an exemplary embodiment of the present specification, the additive is included in an amount of 0.1 to 10 parts by weight with respect to the organic electronic composition.

In another embodiment, the boiling point of the additive is an organic material of 30 ℃ to 300 ℃.

In the present specification, the organic material means a material containing at least one carbon atom.

In one embodiment, the additive is 1,8-dioodooctane (DIO: 1,8-diiodooctane), 1-chloronaphthalene (1-CN: 1-chloronaphthalene), diphenyl ether (DPE: diphenylether), Octane dithiol (octane dithiol) and tetrabromothiophene (tetrabromothiophene) may further include one or two kinds of additives selected from the group consisting of.

The present specification provides an organic electronic device formed using the composition for organic electronic devices.

Herein is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the composition for the organic electronic device.

According to an exemplary embodiment of the present specification, the organic electronic device is selected from the group consisting of an organic photoelectric device, an organic transistor, an organic solar cell, and an organic light emitting device.

According to an exemplary embodiment of the present specification, the organic electronic device may be an organic solar cell.

According to an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the composition for the organic electronic device.

According to an exemplary embodiment of the present specification, the organic material layer includes a photoactive layer, and the photoactive layer includes the composition for an organic electronic device.

According to an exemplary embodiment of the present specification, the photoactive layer includes the composition for an organic electronic device, the composition for an organic electronic device includes the aforementioned heterocyclic compound, and the band gap of the heterocyclic compound is 1 eV to 3 eV, specifically 1 eV to 2 eV, and even more specifically 1 eV to 1.6 eV.

The bandgap measured HOMO and LUMO energy levels through cyclo voltammetry (CV), and the difference between the HOMO and LUMO energy levels is the bandgap. Cyclic voltammetry (CV) is measured using 0.1 M [nBu ₄ N] ⁺ [PF ₆ ] ^- , acetonitrile solution using glassy carbon as the working electrode, but not limited thereto. It is not.

The organic solar cell according to the exemplary embodiment of the present specification includes a first electrode, a photoactive layer, and a second electrode. The organic solar cell may further include a substrate, a hole transport layer, and / or an electron transport layer.

According to one embodiment of the present specification, when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron donor and the electron acceptor. The generated holes are transported to the anode through the electron donor layer.

1 is a view illustrating an organic electronic device according to an exemplary embodiment of the present specification, and a structure in which the first electrode 10, the photoactive layer 30, and the second electrode 20 are sequentially stacked. Alternatively, an additional organic layer may be provided between the first electrode 10 and the second electrode 20.

According to an exemplary 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 an organic material having several functions at the same time.

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

According to one embodiment of the present specification, the organic solar cell may be arranged in the order of cathode, photoactive layer and anode, or may be arranged in order of anode, photoactive layer and cathode, but is not limited thereto.

In another exemplary embodiment, the organic solar cell may be arranged in order of an anode, a hole transport layer, a photoactive layer, an electron transport layer, and a cathode, or may be arranged in the order of a cathode, an electron transport layer, a photoactive layer, a hole transport layer, and an anode. It is not limited to this.

According to an exemplary embodiment of the present specification, the organic solar cell has a normal structure. In the normal structure, a substrate, an anode, and an organic material layer including a photoactive layer and a cathode may be stacked in this order.

According to an exemplary embodiment of the present specification, the organic solar cell has an inverted structure. In the inverted structure, a substrate, a cathode, an organic material layer including a photoactive layer, and an anode may be stacked in this order.

According to an exemplary embodiment of the present specification, the organic solar cell has a tandem structure.

In the organic solar cell according to the exemplary embodiment of the present specification, the photoactive layer may be one layer or two or more layers. The tandem structure may include two or more photoactive layers.

In another exemplary embodiment, a buffer layer may be provided between the photoactive layer and the hole transport layer or between the photoactive layer and the electron transport layer. In this case, a hole injection layer may be further provided between the anode and the hole transport layer. In addition, an electron injection layer may be further provided between the cathode and the electron transport layer.

In 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 the substrate may be any substrate that is commonly used in organic solar cells. Specifically, there are glass or polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), and triacetyl cellulose (TAC). It is not limited to this.

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

The method of forming the first electrode is not particularly limited, but may be applied to one surface of the substrate or in the form of a film using, for example, sputtering, E-beam, thermal deposition, spin coating, screen printing, inkjet printing, doctor blade or gravure printing. It can be formed by coating.

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

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

Through such surface modification, the bonding surface potential can be maintained at a level suitable for the surface potential of the photoactive layer. In addition, it is easy to form a polymer thin film on the anode electrode when the modification, the quality of the thin film may be improved.

Pretreatment techniques for the first electrode include a) surface oxidation using parallel plate discharge, b) oxidation of the surface through ozone generated using UV ultraviolet light in a vacuum state, and c) oxygen generated by plasma. And oxidation using radicals.

One of the above methods can be selected according to the state of the first electrode or the substrate. In any case, however, it is preferable to prevent oxygen escape from the surface of the first electrode or the substrate and to minimize the residual of moisture and organic matter in common. At this time, the substantial effect of the pretreatment can be maximized.

As a specific example, a method of oxidizing a 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 and dried well, then put into a chamber, and a UV lamp is activated to cause oxygen gas to react with UV light. The patterned ITO substrate can be cleaned.

However, the surface modification method of the patterned ITO substrate in this specification does not need to be specifically limited, Any method may be used as long as it is a method of oxidizing a substrate.

The second electrode may be a metal having a small 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; Or a material having a multilayer structure such as LiF / Al, LiO ₂ / Al, LiF / Fe, Al: Li, Al: BaF ₂ , Al: BaF ₂ : Ba, but is not limited thereto.

The second electrode is 5x10 ^- may be formed is deposited on the internal heat evaporator showing a degree of vacuum of less than ⁷ torr, not limited to this method.

The hole transport layer and / or electron transport layer material plays a role of efficiently transferring electrons and holes separated in the photoactive layer to the electrode, and the material is not particularly limited.

The hole transport layer material may be PEDOT: PSS (Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)), molybdenum oxide (MoO _x ); Vanadium oxide (V ₂ O ₅ ); Nickel oxide (NiO); Tungsten oxide (WO _x ), and the like, but is not limited thereto.

The electron transport layer material may be electron-extracting metal oxides, specifically, a metal complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO _x ); Zinc oxide (ZnO); And cesium carbonate (Cs ₂ CO ₃ ), and the like, but is not limited thereto.

The photoactive layer may be spin coated, dip coated, screen printed, spray coated, doctor blade, brush painting, roll to roll printing, ink jet printing, nozzle printing, offset printing, transfer printing, or the like. Although it can form by screen printing etc., it is not limited to these methods.

The composition for an organic electronic device according to the exemplary embodiment of the present specification has an economical effect in time and cost at the time of manufacturing the device because the solution process is suitable as a structural characteristic.

In addition, since the composition for an organic electronic device includes the heterocyclic compound of Formula 1, the photoactive layer has an effect having a constant excellent photoelectric conversion efficiency within the thickness range of 50 nm to 150 nm.

According to an exemplary embodiment of the present specification, the thickness of the photoactive layer is 50 nm to 150 nm, specifically 100 to 150 nm.

In one embodiment of the present specification, the organic electronic device may be an organic transistor.

According to an exemplary embodiment of the present specification, an organic transistor including a source, a drain, a gate, and one or more organic material layers, wherein at least one of the organic material layers includes the heterocyclic compound.

According to the exemplary embodiment of the present specification, the organic material layer includes an n-type semiconductor layer and a p-type semiconductor layer, and the n-type semiconductor layer includes the heterocyclic compound.

The preparation method of the heterocyclic compound and the preparation of the organic electronic device including the same will be described in detail in the following Preparation Examples and Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Production Example

Preparation Example 1 Preparation of Compound 1

1) Preparation of Compound A-2

Compound A-1 (11.2 g, 18.38 mmol), 2,5-dibromoterephthalate (2.58 g, 7.33 mmol), Pd ₂ (dba) ₃ (0.34 g, 0.37 mmol), P (o-tolyl) ₃ ( 1.34 g, 0.44 mmol) was dissolved in 30 mL of toluene and the resulting reaction mixture was refluxed at 100 ° C. for 12 hours. Toluene in the reaction mixture was dried in vacuo and then purified by column chromatography on silica gel (dichloromethane / n-hexane (3: 7)). 4.6 g of compound A-2 was obtained in 60% yield.

2) Preparation of Compound A-3

1-bromohexylbenzene (4.91 g, 0.02 mol) was dissolved in 60 mL of tetrahydrofuran (THF) under a nitrogen atmosphere and stirred at -78 ° C for 20 minutes. 9 mL of n-BuLi solution was injected into the reaction mixture and after stirring for 10 minutes, Compound A-2 prepared from 1) dissolved in 60 mL of tetrahydrofuran (THF) was injected into the reaction mixture. The resulting reaction mixture was stirred for 8 hours at room temperature. The reaction mixture was extracted with dichloromethane and proceeded to the next reaction without further purification.

3) Preparation of Compound A-4

2.13 mL of boron trifluoride diethyl ether was injected into a solution of Compound A-3 dissolved in 50 mL of chloroform. The resulting reaction mixture was stirred for 8 hours at room temperature. The chloroform was dried in vacuo and then purified by column chromatography on silica gel (dichloromethane / n-hexane (3: 7)). 3.01 g of compound A-4 was obtained in 43% yield.

4) Preparation of Compound A-5

Compound A-4 (3.01 g, 1.84 mmol) was dissolved in 150 mL tetrahydrofuran (THF) solvent and 2.6 mL of n-BuLi were injected under a −78 ° C. nitrogen atmosphere. After stirring for 20 minutes, 1 mL dimethylformamide (DMF) was injected and the resulting reaction mixture was stirred at room temperature for 8 hours. After reaction the product was extracted with dichloromethane and purified by column chromatography on silica gel (dichloromethane / n-hexane (1: 3)). Thereafter, it was recrystallized from dichloromethane / methanol and 1.4 g of Compound A-5 was obtained in 45% yield.

5) Preparation of Compound 1

Compound A-5 (0.7 g, 0.41 mmol), 3- (1,1-dicyanomethylene) -5,6-difluoro-indanone (0.29 g, 1.26 mmol) was dissolved in 50 mL chloroform. Then 2 mL of pyridine was injected and refluxed at 70 ° C. for 8 hours. The reaction mixture was purified by column chromatography on silica gel (dichloromethane / n-hexane (1: 1)) and recrystallized from dichloromethane / methanol. Compound 1, 350 mg, 40% yield.

2 is a diagram showing ¹ H-NMR data of the compound 1.

Preparation Example 2 Preparation of Compound 2

Compound A-5 (0.25 g, 0.15 mmol), 1,1-dicyanomethylene-3-indanone (0.09 mg, 0.44 mmol) was dissolved in 30 mL chloroform. Then 1 mL of pyridine was injected and refluxed at 70 ° C. for 8 hours. The reaction mixture was purified by column chromatography on silica gel (dichloromethane: n-hexane (1: 1)) and recrystallized from dichloromethane / methanol. Compound 2, 150 mg, 50% yield.

3 is a diagram showing ¹ H-NMR data of the compound 2.

4 is a view showing UV-Vis absorption spectra of the compounds 1 and 2 in the film state.

Specifically, FIG. 4 was analyzed by using a UV-Vis absorption spectrum (UV-Vis absorption spectrometer) as the UV-Vis absorption spectrum of the film samples prepared by dissolving the compounds 1 and 2 in chlorobenzene, respectively.

Example. Fabrication of Organic Solar Cells

Example 1-1

1) Preparation of Organic Solar Cell Composition

PTB7 and Compound 1 prepared in Preparation Example 1 were dissolved in chlorobenzene (CB) in a 1: 1 ratio to prepare a composite solution. At this time, the concentration was adjusted to 2 wt%.

[PTB7]

2) Fabrication of Organic Solar Cells

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

After spin-coating a ZnO nanoparticle solution (N-10, Nanograde Ltd, 2.5 wt% in 1-butanol, filtered to 0.45 μm PTFE) on the first electrode at 4,000 rpm for 40 seconds, Heat treatment at 80 ° C. for 10 minutes to remove the remaining solvent to form an electron transport layer.

Thereafter, the composite solution prepared in 1) was spin-coated on the electron transport layer at 70 ° C. at 1,300 rpm for 25 seconds to form a photoactive layer having a thickness of 80 to 100 nm, and MoO ₃ was 0.2 μm on the photoactive layer. / s, and 10 ^- a hole transport layer was formed by thermal evaporation to a thickness of 10nm under ⁷ torr vacuum.

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

Example 1-2

An organic solar cell was manufactured in the same manner as in Example 1-1, except that the composite solution was spin-coated at 1,500 rpm instead of 1,300 rpm in 2) of Example 1-1.

Example 1-3

An organic solar cell was manufactured in the same manner as in Example 1-1, except that the composite solution was spin-coated at 1,700 rpm instead of 1,300 rpm in 2) of Example 1-1.

Example 1-4

An organic solar cell was manufactured in the same manner as in Example 1-1, except that the composite solution was spin-coated at 1,900 rpm instead of 1,300 rpm in 2) of Example 1-1.

Example 2-1

An organic solar cell was manufactured in the same manner as in Example 1-1, except that Compound 2 was used instead of Compound 1 in 1) of Example 1-1.

Example 2-2

An organic solar cell was manufactured in the same manner as in Example 1-1, except that the composite solution was spin-coated at 1,500 rpm instead of 1,300 rpm in 2) of Example 2-1.

Example 2-3

An organic solar cell was manufactured in the same manner as in Example 1-1, except that the composite solution was spin-coated at 1,900 rpm instead of 1,300 rpm in 2) of Example 2-1.

The photoelectric conversion characteristics of the organic solar cells prepared in Examples 1-1 to 1-4 and 2-1 to 2-3 were measured under 100 mW / cm ² (AM 1.5), and the results are shown in Table 1 below. Indicated.

5 is a current density graph according to the voltage of Examples 1-1 to 1-4 and 2-1 to 2-3.

Spin-speed (rpm) V _oc
(V) J _sc
(mA / cm ² ) FF η
(%) Average η
(%) Example 1-1 1,300 0.911 10.175 0.466 4.32 4.32 0.901 10.283 0.467 4.32 Example 1-2 1,500 0.867 10.438 0.498 4.51 4.79 0.904 10.884 0.515 5.07 Example 1-3 1,700 0.903 10.434 0.471 4.43 4.78 0.900 11.089 0.513 5.12 Example 1-4 1,900 0.905 10.683 0.512 4.95 4.82 0.896 10.623 0.492 4.68 Example 2-1 1,300 0.896 10.977 0.541 5.32 5.21 0.889 10.937 0.523 5.09 Example 2-2 1,500 0.898 10.715 0.543 5.23 5.25 0.894 10.650 0.553 5.27 Example 2-3 1,900 0.907 11.094 0.542 5.45 5.45

According to Table 1, Examples 1-1 to 1-4 and 2-1 to 2-3 including the heterocyclic compound according to an exemplary embodiment of the present specification as a photoactive layer of an organic solar cell are the heterocyclic compound The length of the conjugation of, the intermolecular packing through the intermolecular interaction (packing) is possible, and absorbs a wide wavelength of light, the organic solar cell comprising a high short-circuit current. In addition, the heterocyclic compound has a low energy loss, so that the organic solar cell including the same has excellent open voltage, short circuit current, charge rate, and efficiency.

5, the organic solar cells of Examples 1-1 to 1-4 and 2-1 to 2-3 including the heterocyclic compound according to one embodiment of the present specification in the photoactive layer of the organic solar cell have an efficiency. This is excellent, and it turns out that current density rises steeply as voltage increases.

In Table 1, V _oc represents an open voltage, J _sc represents a short circuit current, FF represents a fill factor, and η represents an energy conversion efficiency. The open-circuit and short-circuit currents are the X- and Y-axis intercepts in the four quadrants of the voltage-current density curve, respectively. The higher these two values, the higher the efficiency of the solar cell. Also, the fill factor is the area of the rectangle drawn inside the curve divided by the product of the short circuit current and the open voltage. By dividing these three values by the intensity of the emitted light, the energy conversion efficiency can be obtained, and higher values are preferable.

10: first electrode
20: second electrode
30: photoactive layer
100: organic electronic device

Claims (14)

Heterocyclic compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
X1 to X4 are the same as or different from each other, and each independently S, O, or Se,
R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted linear or branched alkyl group; A substituted or unsubstituted linear or branched alkoxy group; Substituted or unsubstituted linear or branched thioalkoxy group; Substituted or unsubstituted monocyclic or polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group,
G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxyl group; Or a halogen group,
EW1 and EW2 are the same as or different from each other, and each independently serves as an electron acceptor. The method according to claim 1, wherein R1 to R4 are the same as or different from each other, each independently a linear or branched alkyl group having 1 to 10 carbon atoms; Linear or branched alkoxy groups having 1 to 10 carbon atoms; Linear or branched thioalkoxy groups having 1 to 10 carbon atoms; Monocyclic aryl groups having 6 to 12 carbon atoms substituted with linear or branched alkyl groups having 1 to 10 carbon atoms; Or a monocyclic heteroaryl group having 2 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms. The method according to claim 1, Ar1 to Ar4 are the same as or different from each other, each independently a linear or branched alkyl group of 1 to 10 carbon atoms, a straight or branched chain alkoxy group of 1 to 10 carbon atoms, or 1 to 10 carbon atoms C6-C12 monocyclic aryl group substituted by the linear or branched thioalkoxy group; Or a monocyclic hetero ring having 2 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms, a straight or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched thioalkoxy group having 1 to 10 carbon atoms; Heterocyclic compound which is an aryl group. The heterocyclic compound of claim 1, wherein G 1 to G 4 are hydrogen. The heterocyclic compound according to claim 1, wherein EW1 and EW2 are the same as or different from each other, and are each independently a group represented by the following Formula:
[Formula a]

In Chemical Formula a,
Cy 1 is a monocyclic or polycyclic hydrocarbon ring having 6 to 20 carbon atoms unsubstituted or substituted with a halogen group, a linear or branched alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms; Or a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms unsubstituted or substituted with a halogen group, a straight or branched chain alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms,

Is a site bonded to the formula (1). The heterocyclic compound of claim 1, wherein Formula 1 is represented by Formula 1-1:
[Formula 1-1]

In Chemical Formula 1-1,
Definitions of R1 to R4 and Ar1 to Ar4 are the same as defined in Formula 1,
Cy1 and Cy2 are the same as or different from each other, and each independently 6 to 20 carbon atoms unsubstituted or substituted with a halogen group, a straight or branched chain alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms Monocyclic or polycyclic aromatic hydrocarbon rings; Or a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms unsubstituted or substituted with a halogen group, a straight or branched chain alkyl group having 1 to 10 carbon atoms, or a straight or branched chain alkoxy group having 1 to 10 carbon atoms. The heterocyclic compound of claim 1, wherein Formula 1 is selected from the following compounds:

An organic electronic device composition comprising the heterocyclic compound according to any one of claims 1 to 7. The composition of claim 8, wherein the composition for an organic electronic device comprises an electron donor material and an electron acceptor material, and the electron acceptor material includes the heterocyclic compound. The composition of claim 9, wherein the electron donor material and the electron acceptor material constitute a bulk hetero junction (BHJ). A first electrode;
A second electrode provided to face the first electrode; And
An organic electronic device comprising at least one organic material layer provided between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic electronic device comprising the composition for an organic electronic device according to claim 8. The organic electronic device of claim 11, wherein the organic electronic device is selected from the group consisting of an organic photoelectric device, an organic transistor, an organic solar cell, and an organic light emitting device. The method of claim 11, wherein the organic electronic device comprises: a first electrode;
A second electrode provided to face the first electrode; And
An organic solar cell comprising at least one organic material layer provided between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic electronic device comprising the composition for an organic electronic device. The organic electronic device of claim 13, wherein the organic material layer includes a photoactive layer, and the photoactive layer includes the composition for organic electronics.

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