KR20140039383A - Imidazole compound and organic electronic device using the same - Google Patents

Abstract

The present invention relates to an imidazole derivative and an organic electronic device using the same, and more specifically, to a novel imidazole derivative capable of enhancing photoelectric conversion efficiency of an organic solar cell. According to one embodiment of the present invention, the imidazole derivative is represented by chemical formula 1. In chemical formula 1, Ar1 is -(L1)p1-(Y1) q1, Ar2 is -(L2)p2-(Y2)q2, Ar3 is -(L3)p3-(Y3)q3, and Ar4 is -(L4)p4-(Y4)q4.

Description

IMIDAZOLE COMPOUND AND ORGANIC ELECTRONIC DEVICE USING THE SAME

The present specification relates to an imidazole derivative and an organic electronic device using the same.

Recently, the development of organic materials with semiconducting properties and various applications using them have been actively studied. Applications of organic semiconductors such as electromagnetic wave shielding films, capacitors, OLED displays, organic thin film transistors (OTFTs), solar cells, and memory devices using multiphoton absorption phenomena continue to expand.

In particular, the OLED field is in the forefront of commercialization of large-sized displays, and thus acts as a catalyst to activate application research using organic materials. Organic semiconductor thin film transistors (OLEDs), which are expected to be used for applications such as next- Are also emerging. In addition, after the announcement of the electrical power generation characteristics using the organic semiconductor as an active layer, it is also drawing a lot of attention to the application as a laser diode. Compared to non-organic materials, the cost of producing devices is remarkably low, so we are anticipating a future change in the solar cell market.

Solar cells are devices that can convert solar energy directly into electrical energy by applying a photovoltaic effect. Solar cells can be divided into inorganic solar cells and organic solar cells depending on the material constituting the thin film.

A typical solar cell is made of p-n junction by doping crystalline silicon (Si), which is an inorganic semiconductor. Electrons and holes generated by absorption of light are diffused to the p-n junction, accelerated by the electric field, and moved to the electrode. The power conversion efficiency of this process is defined as the ratio of the power given to the external circuit to the solar power entering the solar cell, and is achieved up to 24% when measured under the current standardized virtual solar irradiation conditions.

However, since conventional inorganic solar cells have already been limited in terms of economy and supply / demand of materials, organic semiconductor solar cells, which are easy to process, have various functions and are inexpensive, are attracting attention as long-term alternative energy sources.

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

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores [Beilstein J. Org. Chem. 2012, 8, 25-49.]

The present specification provides an imidazole derivative and an organic electronic device using the same.

The present specification provides an imidazole derivative represented by Formula 1 below or including two or more structures of Formula 1 below.

[Chemical Formula 1]

In Formula 1,

Ar ₁ is-(L ₁ ) p _1- (Y ₁ ) q ₁ , Ar ₂ is-(L ₂ ) p _2- (Y ₂ ) q ₂ , and Ar ₃ is-(L ₃ ) p _3- ( Y ₃ ) q ₃ , Ar ₄ is-(L ₄ ) p _4- (Y ₄ ) q ₄ ,

p ₁ to p ₄ each represent an integer of 0 to 10,

q ₁ to q ₄ each represent an integer of 1 to 10,

L ₁ to L ₄ are the same as or different from each other, and each independently a direct bond; Oxygen; sulfur; Nitrogen substituted or unsubstituted with an alkyl or aryl group; A substituted or unsubstituted arylene group; Substituted or unsubstituted divalent arylamine group; Substituted or unsubstituted divalent triaryl phosphine group; Substituted or unsubstituted divalent triaryl phosphine oxide group; A substituted or unsubstituted alkenylene group; Substituted or unsubstituted alkynylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted carbazolylene group; Substituted or unsubstituted benzocarbazolylene group; A substituted or unsubstituted divalent aromatic or aliphatic ring cyclic ketone group; Substituted or unsubstituted divalent aromatic ring group; Divalent substituted or unsubstituted aromatic or aliphatic heterocyclic groups containing at least one of N, O, and S atoms; And a substituted or unsubstituted divalent aromatic ring and a condensed ring group of the heterocycle are selected from the group consisting of

Y ₁ to Y ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Ester group (-CO ₂ R); Carbonyl group (-COR); Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; Substituted or unsubstituted aryl phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; A cyclic ketone group of a substituted or unsubstituted aromatic or aliphatic ring; An imide group of a substituted or unsubstituted aromatic or aliphatic ring; A substituted or unsubstituted aromatic ring group; A substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms; A substituted or unsubstituted condensed ring group of the aromatic ring and the hetero ring; An imidazole group unsubstituted or substituted with Formula 1-1; Or in the following Formula 1-1,

 [Formula 1-1]

At least one of Y ₁ to Y ₄ may be represented by Formula 1-1,

In Chemical Formula 1-1,

n is an integer from 0 to 4,

R _a , R _b and R _c are the same as or different from each other, and each independently hydrogen; Cyano group (-CN); An ester group; Carbonyl group (-COR); Carboxyl group (—CO ₂ R); Fluoro groups (-F); Or an alkyl group substituted with a fluoro group (-F); A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

,

,

,

,

,

및

로 이루어진 군에서 선택되고, Q ₂ is oxygen ( O ),

,

,

,

,

,

And

, ≪ / RTI >

* Is a moiety linked to Chemical Formula 1-1,

a, b, c and d are each an integer of 0 to 4,

R, R 'and R "are the same as or different from each other, and each independently hydrogen; cyano group (-CN); ester group; cyano group (-CN); ester group; carbonyl group (COR'"); Carboxyl group (CO ₂ R '"); fluoro group (-F); or alkyl group substituted with fluoro group (-F); substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted An alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aromatic or aliphatic heterocyclic group including one or more of N, O, and S atoms; or a substituted or unsubstituted aryl group,

R '"is the same as defined above.

In addition, the present specification is an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, at least one of the organic layer is a compound of Formula 1 It provides an organic electronic device comprising a.

The imidazole derivative according to the present specification may be used as a material of an organic material layer of an organic electronic device including an organic solar cell, and the organic electronic device including the organic solar cell using the same exhibits excellent characteristics in efficiency increase and stability increase.

In particular, the new imidazole derivatives according to the present disclosure have excellent thermal stability, various bandgaps, various HOMO and LUMO state states, and electronic stability.

The derivative of Chemical Formula 1 according to the present specification may be used purely in organic electronic devices including organic solar cells, or may be used by mixing impurities, and may be applied by vacuum deposition, solution coating, or the like to improve light efficiency, and Thermal stability can improve the lifetime characteristics of the device.

1 illustrates an example of an organic solar cell including a substrate 101, a first electrode 102, a hole transport layer 103, a photoactive layer 104, and a second electrode 105.
2 is a diagram showing a mass spectrum of Compound 1-a-16.
3 is a diagram showing a mass spectrum of Compound 1-b-12.

Hereinafter, the present invention will be described in detail.

Imidazole derivatives according to the present specification are represented by Formula 1 or include two or more structures of Formula 1.

In the present specification, * means a linking portion with the formula, and does not mean a bond.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

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 20. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

In the present specification, the alkenyl group may be linear or branched, preferably an alkenyl group having 2 to 40 carbon atoms, and specifically, an alkenyl group substituted with an aryl group such as stilbenyl and styrenyl groups. Or an alkenyl group substituted with a cycloalkyl group or a cycloalkenyl group is not limited thereto.

In the present specification, the alkoxy group may be straight or branched chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is 1-40 which is a range which does not give a steric hindrance. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a n-propyloxy group, an iso-propyloxy group, a n-butyloxy group, and a cyclopentyloxy group.

In the present _{specification, - (L n) p- (} Y n) if Y _n is an alkoxy group of q, the number of carbon atoms of the alkoxy group, the conjugation length of the compound, without affecting, but on the organic electronic device of the compounds The number of carbon atoms in the alkoxy group is not particularly limited since it only affects the application of the method, for example, the vacuum deposition method or the solution coating method. N is an integer of 1 to 4.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be mono- or di-substituted by nitrogen of the amide group with hydrogen, a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 6 to 30 carbon atoms or an aryl group having 6 to 25 carbon atoms in the carbon atom of the ester group. Specifically, the oxygen of the ester group is substituted with a primary alkyl group having 6 to 15 carbon atoms or a secondary alkyl group having 6 to 30 carbon atoms.

In the present specification, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the like, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, and tetrasenyl group. , Chrysenyl group, fluorenyl group, acenaphthasenyl group, triphenylene group, fluoranthene group and the like, but the scope of the present specification is not limited only to these examples.

In the present specification, the heterocyclic group is a hetero ring group containing at least one of N, O or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzoxazole group, a benzthiophene group, a dibenzothiophene group, a benzfuranyl group, Naphthyl group, naphthyl group, naphthyl group, naphthyl group, quinacridone group, acridone group and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monocyclic arylamine group, a substituted or unsubstituted monocyclic arylamine group substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted monocyclic arylamine group, Substituted or unsubstituted monocyclic triarylamine groups, unsubstituted monocyclic triarylamine groups, substituted or unsubstituted polycyclic diarylamine groups, substituted or unsubstituted polycyclic triarylamine groups, substituted or unsubstituted monocyclic and polycyclic diarylamines Or a substituted or unsubstituted mono- and polycyclic triarylamine group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monocyclic diarylphosphine group, a substituted or unsubstituted monocyclic tritylphosphine group, a substituted or unsubstituted polycyclic diarylphosphine group, a substituted or unsubstituted monocyclic diarylphosphine group, An unsubstituted polycyclic triarylphosphine group, a substituted or unsubstituted monocyclic or polycyclic diarylphosphine group, or a substituted or unsubstituted monocyclic or polycyclic triarylphosphine group.

In the present specification, examples of the arylphosphine oxide group include a substituted or unsubstituted monocyclic diarylphosphine oxide group, a substituted or unsubstituted monocyclic tritylphosphine oxide group, a substituted or unsubstituted polycyclic dia A substituted or unsubstituted polycyclic triarylphosphine oxide group, a substituted or unsubstituted monocyclic or polycyclic diarylphosphine oxide group, or a substituted or unsubstituted monocyclic or polycyclic monocyclic or polycyclic monocyclic Of the triarylphosphine oxide group.

등이 있다. In the present specification, a fluorenyl group is a structure in which two ring organic compounds are connected via one atom,

.

,

등이 있다. In the present specification, a fluorenyl group includes a structure of an open fluorenyl group, wherein an open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring compounds are connected through one atom, For example,

,

.

In the present specification, the number of carbon atoms of the amine group 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, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present invention, examples of the cyclic ketone group of the aromatic or aliphatic ring include

등이 있으나, 이들에 한정되는 것은 아니다.

And the like, but are not limited thereto.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group and the aralkylamine group is the same as the aforementioned aryl group.

In the present specification, the alkyl group in the alkylthio group, alkylsulfoxy group, alkylamine group, and aralkylamine group is the same as the alkyl group described above.

In the present specification, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heterocyclic group described above.

In the present specification, an arylene group, an alkenylene group, an alkynylene group, a fluorenylene group, a carbazolylene group and a benzocarbazolene group are an aryl group, an alkenyl group, an alkynyl group, a fluorenyl group, a carbazole group and a benzocarbazole group, respectively. It is two. The description of the above-mentioned aryl group, alkenyl group, fluorenyl group and carbazole group can be applied, except that these are two groups each.

In the present specification, the divalent arylamine group may be a divalent monoarylamine group, a divalent diarylamine group or a divalent triarylamine group.

In one embodiment of the present specification, the divalent arylamine group may be connected to an aryl group or a linking group to N.

In the present specification, the divalent triarylphosphine group is linked to an aryl group.

In the present specification, the divalent triaryl phosphine oxide group is linked to the aryl group.

In the present specification, examples of the aromatic ring group include

등이 있으나, 이들에 한정되는 것은 아니다.

And the like, but are not limited thereto.

등이 있으나. 이들에 한정되는 것은 아니다. In the present specification, examples of the condensed ring group of an aromatic ring and a heterocycle include

There is a back. It is not limited to these.

In addition, the condensed ring groups of the aromatic ring and the heterocyclic ring may be linked to the aryl group or other aromatic heterocyclic group shown in the above example in Formula 1.

등이 있으나, 이에 한정되는 것은 아니다. In the present specification, examples of the imide group of the aromatic or aliphatic ring,

And the like, but the present invention is not limited thereto.

In the present specification, the cyclic ketone group of the bivalent aromatic or aliphatic ring, the divalent aromatic ring group, the divalent aromatic or aliphatic heterocyclic group, and the condensed ring group of the divalent aromatic ring and the heterocyclic ring are each 2 except An explanation of the cyclic ketone group, the aromatic ring group, the aromatic or aliphatic heterocyclic group, and the condensed ring group of the aromatic ring and the heterocyclic ring of the aforementioned aromatic or aliphatic ring can be applied.

In one embodiment of the present specification, Y ₄ provides an imidazole derivative having the Formula 1-1.

In another exemplary embodiment, Y ₃ provides an imidazole derivative having Formula 1-1.

In one embodiment of the present specification, Chemical Formula 1 provides an imidazole derivative represented by any one of the following Chemical Formulas 2 and 3.

(2)

(3)

In Chemical Formulas 2 and 3,

Ar ₁ to Ar ₄ , L ₃ and L ₄ are the same as defined in Formula 1,

R _a , R _b , R _c , n and Q ₂ are the same as defined in Formula 1-1.

In one embodiment of the present specification, Y ₁ to Y ₄ are the same as or different from each other, and each independently hydrogen; A nitrile group; A substituted or unsubstituted ester group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A cyclic ketone group of a substituted or unsubstituted aromatic or aliphatic ring; An imide group of a substituted or unsubstituted aromatic or aliphatic ring; A substituted or unsubstituted aromatic ring group; A substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms; A substituted or unsubstituted condensed ring group of the aromatic ring and the hetero ring; An imidazole group unsubstituted or substituted with Formula 1-1; And it provides an imidazole derivative selected from the group consisting of the formula (1-1).

In another exemplary embodiment, Y ₁ to Y ₄ are the same as or different from each other, and each independently a substituted or unsubstituted alkenyl group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted pyrene group; A substituted or unsubstituted quinazoline group; Substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; A cyclic ketone group of a substituted or unsubstituted aromatic or aliphatic ring; An imide group of a substituted or unsubstituted aromatic or aliphatic ring; A substituted or unsubstituted aromatic ring group; A substituted or unsubstituted condensed ring group of the aromatic ring and the hetero ring; Or an imidazole group unsubstituted or substituted with Formula 1-1; And at least one selected from the group consisting of the formula 1-1 provides an imidazole derivative.

In another exemplary embodiment, L ₁ to L ₄ are the same as or different from each other, and are each independently a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Substituted or unsubstituted anthracenylene group; And it provides an imidazole derivative selected from the group consisting of a substituted or unsubstituted benzothiadiazolene group.

According to one embodiment of the present specification, including two or more structures of Formula 1 means that the compounds having the structure of Formula 1 exist in a directly connected structure without a linking group. In this case, it means that each of the same formula or different formulas of Formula 1 may directly combine to include two or more of the formula structure.

According to yet an embodiment of the present disclosure, including two or more structures of the formula (1), Alkan having a bivalent or more linking group; Cycloalkane having a divalent or higher linking group; Substituted or unsubstituted aryl having a divalent or higher linking group; Substituted or unsubstituted fluorene having a divalent or higher linking group; Cyclic ketones of aromatic or aliphatic rings having a divalent or higher linking group; Substituted or unsubstituted heterocycle having a bivalent or higher linking group containing at least one of N, O, S atoms; Groups having a condensed or non-condensed divalent or higher linking group comprising a heterocycle or an aromatic ring; Oxygen atom; Hwang Wonjae; Substituted or unsubstituted nitrogen atom; Or it means that two or more structures of the formula (1) may be connected to a substituted or unsubstituted phosphorus atom. In this case, it means that the same or different formulas of Formula 1 may be combined to include two or more formula structures.

In one embodiment of the present specification, the imidazole derivative including two or more structures of Formula 1 provides an imidazole derivative represented by any one of the following Formulas 4 to 6.

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In Chemical Formulas 4 to 6,

r, s and w are integers from 0 to 2,

t, u and v are integers from 0 to 3,

Ar ₃ 'is-(L ₃ ') p ₃ '-(Y ₃ ') q ₃ ', Ar ₃ "is-(L ₃ ") p ₃ "-(Y ₃ ") q ₃ ", and Ar _a Is-(L _a ) p _a- (Y _a ) q _a , Ar _b is-(L _b ) p _b- (Y _b ) q _b , and Ar _c is-(L _c ) p _c- (Y _c ) _c , Ar _d is-(L _d ) p _d- (Y _d ) q _d , Ar _e is-(L _e ) p _e- (Y _e ) q _e , and Ar _f is-(L _f ) p _f- (Y _f ) q _f ,

p ₃ ', p ₃ ", p _a , p _b , p _c , p _d , p _e and p _f are the same as the definition of p ₁ to p ₄ of Formula 1,

q ₃ ′, q ₃ ″, q _a , q _b , q _c , q _d , q _e and q _f are the same as the definitions of q ₁ to q ₄ in Chemical Formula 1,

L ₃ ′, L ₃ ″, L _a , L _b , L _c , L _d , L _e and L _f have the same definitions as L ₁ to L ₄ in Formula 1,

Y ₃ ′, Y ₃ ″, Y _a , Y _b , Y _c , Y _d , Y _e and Y _f are the same as the definitions of Y ₁ to Y ₄ of Chemical Formula 1,

Ar ₃ is the same as defined in Formula 1,

Formulas 4 to 6 include at least one of Formula 1-1,

Z represents a divalent linking group, which is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted cyclic ketone group of a divalent aromatic or aliphatic ring; A substituted or unsubstituted divalent aromatic ring group; A substituted or unsubstituted divalent heterocyclic group including at least one of substituted or unsubstituted N, O, and S atoms; A group having a condensed or non-condensed divalent linking group including the heterocyclic group or the aromatic ring group; Oxygen; sulfur; Substituted or unsubstituted nitrogen; Or substituted or unsubstituted phosphorus.

Formula 4 includes at least one of Formula 1-1 means that at least one of Y ₃ , Y ₃ ′, Y _a and Y _b is Formula 1-1, and a repeating number of substituents represented by Formula 1-1, for example, o or p means 1 or more. However, when Y ₃ and / or Y ₃ ′ in Formula 4 are represented by Formula 1-1, o and / or p may be 0.

Formula 5 includes at least one of Formula 1-1 means that at least one of Y _c and Y _d is Formula 1-1, and the repeating number of substituents represented by Formula 1-1, for example, t or u is 1 or more. it means.

In addition, the formula (6) includes at least one formula (1-1) is at least one of Y _e , Y _f and Y ₃ "is a formula 1-1, the repeating number of substituents represented by formula 1-1, for example, v Or w is greater than or equal to 1. However, when Y ₃ ″ is represented by Formula 1-1 in Formula 6, v and / or w may be 0.

In one embodiment, Z is a substituted or unsubstituted arylene group; Condensed ring of a substituted or unsubstituted aromatic ring with a heterocyclic ring; And a condensed ring of the arylene group and the aromatic ring and the hetero ring is a group selected from a divalent linking group in which two or more are connected.

In this specification, although the following group is mentioned as a bivalent coupling group, It is not limited to these.

a, c, d and g are each an integer of 0 to 4,

e and f are each an integer of 0 to 3,

b is an integer of 0 to 2,

R _f , R _g , R _h , R _i , R _j , R _k , R _l are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group,

R _d and R _e are hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; It is selected from the group consisting of a substituted or unsubstituted aryloxy group.

In one embodiment of the present specification, Z is connected to Ar ₄ of Formula 1.

In one embodiment of the present specification, Z is connected to Ar ₃ of Chemical Formula 1.

The term "substituted or unsubstituted" A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heterocyclic group; Carbazole group; An arylamine group; An aryl group; A fluorenyl group; A nitrile group; A nitro group; A heterocyclic group containing at least one of a hydroxyl group and at least one of N, O and S atoms, or has no substituent group.

In the present specification, p _x is any one of the p ₁ to p ₈ , x is an integer of 1 to 8.

In one embodiment of the present specification, p _x is 0.

In one embodiment of the present specification, p _x is 1.

In another embodiment, p _x is 2.

In the present specification, L _x is any one of L ₁ to L ₈ , and x is an integer of 1 to 8.

In one embodiment of the present specification, L _x is a substituted or unsubstituted arylene group.

In another exemplary embodiment, L _x is a substituted or unsubstituted phenylene group.

In another exemplary embodiment, L _x is a phenylene group substituted with a benzoisoquinoline dione group.

In another exemplary embodiment, L _x is a phenylene group.

In another exemplary embodiment, L _x is a phenylene group substituted with a halogen group.

In another exemplary embodiment, L _x is a phenylene group substituted with a fluoro group.

In another exemplary embodiment, L _x is a phenylene group substituted with a substituted or unsubstituted benzotriazole group.

In another exemplary embodiment, L _x is a phenylene group substituted with a pyrene group.

In another exemplary embodiment, L _x is a phenylene group substituted with an anthracene group.

In another exemplary embodiment, L _x is a phenylene group substituted with a benzotriazole group substituted with a phenyl group.

In another exemplary embodiment, L _x is a phenylene group substituted with a substituted or unsubstituted benzothiadiazole group.

In another exemplary embodiment, L _x is a phenylene group substituted with a benzothiadiazole group substituted with a phenyl group.

In another exemplary embodiment, L _x is a phenylene group substituted with a substituted or unsubstituted anthracenyl group.

In another exemplary embodiment, L _x is a phenylene group substituted with a substituted or unsubstituted chromen group.

In another exemplary embodiment, L _x is a phenylene group substituted with an anthracenyl group substituted with a phenyl group.

In another exemplary embodiment, L _x is a substituted or unsubstituted biphenylene group.

In another exemplary embodiment, L _x is a biphenylene group.

In another exemplary embodiment, L _x is a biphenylene group substituted with a halogen group.

In another exemplary embodiment, L _x is a biphenylene group substituted with a fluoro group.

In another exemplary embodiment, L _x is a biphenylene group substituted with an alkoxy group.

In another exemplary embodiment, L _x is a biphenylene group substituted with a nitro group.

In another exemplary embodiment, L _x is a biphenylene group substituted with a sulfoxy group.

In another exemplary embodiment, L _x is a biphenylene group substituted with an alkoxy group.

또는

이다. In another exemplary embodiment, L _x is a biphenylene group,

or

to be.

In another exemplary embodiment, L _x is a substituted or unsubstituted anthracenylene group.

In another exemplary embodiment, L _x is a substituted or unsubstituted fluorenylene group.

In another exemplary embodiment, L _x is a substituted or unsubstituted benzothiadiazolylene group.

In another exemplary embodiment, L _x is a benzothiadiazolylene group substituted with a phenyl group.

In another exemplary embodiment, L _x is a benzothiadiazolylene group substituted with an alkoxy group.

In the present specification, q _x is any one of q ₁ to q ₈ , and x is an integer of 1 to 8.

In another exemplary embodiment, q _x is one.

In the present specification, Y _x is any one of Y ₁ to Y ₈ , and x is an integer of 1 to 8.

In another exemplary embodiment, Y _x is a nitrile group.

In another embodiment, Y _x is a substituted or unsubstituted ester group.

In another embodiment, Y _x is a substituted or unsubstituted acetate group.

In another embodiment, Y _x is an acetate group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted alkenyl group.

In another exemplary embodiment, Y _x is an alkenyl group substituted with a nitrile group.

In another exemplary embodiment, Y _x is an alkenylene group substituted with a thioxothiazolidinone group.

In another embodiment, Y _x is a substituted or unsubstituted aryl group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted phenyl group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a nitrile group.

In another exemplary embodiment, Y _x is a phenyl group substituted with an ester group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a substituted or unsubstituted alkenyl group.

In another exemplary embodiment, Y _x is a phenyl group substituted with an alkenyl group substituted with a cyano group.

In another exemplary embodiment, Y _x is a phenyl group substituted with an alkenyl group substituted with a thioxothiazolidinone group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a nitrile group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a pyrene group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a naphthalenedione group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a quinazoline group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a substituted or unsubstituted benzoimidazole group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a benzoimidazole group substituted with a phenyl group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a substituted or unsubstituted benzothiadiazole group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a benzothiadiazole group substituted with a phenyl group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a halogen group.

In another exemplary embodiment, Y _x is a phenyl group substituted with a fluoro group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted benzoimidazole group.

In another exemplary embodiment, Y _x is a benzoimidazole group substituted with a substituted or unsubstituted phenyl group.

In another exemplary embodiment, Y _x is a benzoimidazole group substituted with a phenyl group substituted with a nitrile group.

In another exemplary embodiment, Y _x is a benzoimidazole group substituted with a phenyl group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted anthracenyl group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with a substituted or unsubstituted phenyl group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with a phenyl group substituted with a nitrile group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with a phenyl group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with a phenyl group substituted with a halogen group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with a phenyl group substituted with a fluoro group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with a naphthyl group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with a pyridine group.

In another exemplary embodiment, Y _x is an anthracenyl group substituted with an alkoxy group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted pyrene group.

In another embodiment, Y _x is a pyrene group.

In another exemplary embodiment, Y _x is a pyrene group substituted with a substituted or unsubstituted phenyl group.

In another exemplary embodiment, Y _x is a pyrene group substituted with a phenyl group substituted with an alkyl group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted anthracenedione group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted naphthalenedione group.

In another embodiment, Y _x is a substituted or unsubstituted fluorene group.

In another embodiment, Y _x is a fluorene group substituted with an alkyl group

In another exemplary embodiment, Y _x is a substituted or unsubstituted fluorenone group.

In another exemplary embodiment, Y _x is a fluorenone group substituted with a nitrile group.

In another exemplary embodiment, Y _x is a fluorenone group substituted with a benzothiazole group.

In another exemplary embodiment, Y _x is a fluorenone group substituted with an ester group.

In another embodiment, Y _x is a fluorenone group substituted with a phenyl group

In another exemplary embodiment, Y _x is a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted quinazoline group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted triazine group.

In another exemplary embodiment, Y _x is a triazine group substituted with a phenyl group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted benzoimidazole group.

In another exemplary embodiment, Y _x is an ester group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted benzothiadiazole group.

In another exemplary embodiment, Y _x is a benzothiadiazole group substituted with a phenyl group.

In another exemplary embodiment, Y _x is a substituted or unsubstituted indenone group.

In another exemplary embodiment, Y _x is an indenone group substituted with a nitrile group.

In another exemplary embodiment, Y ₄ is formula 1-1.

In another exemplary embodiment, Y ₃ is a chemical formula 1-1.

In another exemplary embodiment, Y ₄ and Y ₃ are both Formula 1-1.

In another embodiment, n is 2.

In another embodiment, R _a is hydrogen.

In another exemplary embodiment, R _a is an alkyl group.

이다. In another embodiment, Q ₂ is

to be.

이다. In another embodiment, Q ₂ is

to be.

In another embodiment, R 'is hydrogen.

In one embodiment of the present specification, m is 2.

In another embodiment, m is 3.

이다. In one embodiment, when including the structure of Formula 1 2 or more, Z is

to be.

이다. In one embodiment, when including the structure of Formula 1 2 or more, Z is

to be.

In another embodiment, R _b and R _c are the same as or different from each other, and each independently a linear or branched substituted or unsubstituted alkyl group.

Preferred specific examples of the compound represented by Formula 1 include, but are not limited to, those compounds represented by the formula shown in Table 1 below.

[Table 1]

In addition, preferred specific examples of the compound represented by Formula 1 include compounds represented by the formulas shown in Table 2 below, but are not limited thereto.

 [Table 2]

In addition, preferred specific examples of the compound represented by Formula 1 include compounds represented by the formulas shown in Table 3 below, but are not limited thereto.

 [Table 3]

In addition, preferred specific examples of the compound represented by Formula 1 include compounds represented by the formulas shown in Table 4 below, but are not limited thereto.

[Table 4]

In addition, the present specification provides a method for preparing an imidazole derivative represented by Chemical Formula 1.

It can be prepared by changing the starting material to a starting material corresponding to Q ₂ .

Vacuum deposition (Vacuum deposition) of the method of manufacturing an organic solar cell is deposited by sublimation of the material at high vacuum, such as about 10 ^-6 to 10 ^-7 torr and high temperature. Therefore, the property that the compound can be easily sublimed while maintaining its properties without denaturation at high temperatures for a long time is important.

Since the structure of the compound of Formula 1 has a plate-like core, it may be easily sublimated, and a compound having desired properties may be easily obtained by introducing an aryl group, a heteroaryl group, an arylamine group, etc. into a substituent. .

On the other hand, the process of proceeding to the solution process method of the manufacturing method of the organic solar cell, the structure of the formula (1) is a core of the plate-like structure, substituents that can increase the solubility, for example, aryl group, heteroaryl group, alkyl group, alkylamine group It can be easily obtained by introducing a substituent such as an alkoxy group.

In addition, the compounds according to the present specification may be used for various purposes in organic electronic devices depending on the type and nature of the substituents.

For example, when a substituted or unsubstituted aryl group or a heteroaryl group is substituted, or when two or more structures of Formula 1 are linked, their properties may be deep HOMO due to an increase in electron affinity and electronegativity given by Formula 1. You have the right LUMO to do well with the value and electron acceptor. In this case, it is advantageous to use it as a dopant, an electron injection, an electron transfer, or a hold layer in the photoactive layer.

Compounds of the present disclosure can act as electron acceptor (or electron acceptor or acceptor) materials having various LUMO levels because the energy levels can be controlled by the core and basically various substituents.

In addition, the present specification is an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, at least one layer of the organic layer is the imidazole of Formula 1 It provides an organic electronic device comprising a derivative.

The organic electronic device of the present specification may be manufactured by a conventional method and material for manufacturing an organic electronic device except for forming one or more organic material layers using the above-described compounds.

The organic electronic device may be selected from the group consisting of an organic solar cell, an organic light emitting device, an organic photoconductor (OPC) drum, and an organic transistor.

In one embodiment of the present invention, the organic electronic device is an organic solar cell.

In one embodiment of the present disclosure, the organic solar battery includes a first electrode; A second electrode opposed to the first electrode; Provided is an organic electronic device comprising at least one organic material layer disposed between the first electrode and the second electrode, one or more of the organic material layer comprises the imidazole derivative.

In another embodiment, the organic solar cell may be an organic solar cell having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic solar cell may be an organic solar cell having a reverse structure in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

The organic solar cell according to the present invention is an organic solar cell including a photoactive layer composed of two layers of a p-type semiconductor thin film and an n-type semiconductor thin film, that is, a bi-layer pn junction type Thereby providing an organic solar cell.

The present invention provides an organic solar cell, that is, a bulk heterojunction (BHJ) junction type organic solar cell including a photoactive layer in which an n-type semiconductor and a p-type semiconductor are blended.

Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed in the photoactive layer.

In one embodiment of the present disclosure, the photoactive layer of the organic solar cell is an electron donor material or a mixture layer (bulk heterojunction) of an electron donor material and an electron acceptor material.

A bi-layer p-n junction type organic solar cell is shown in Fig.

Referring to FIG. 1, an organic solar cell includes a substrate 101, a first electrode 102, a hole transport layer 103, a photoactive layer 104, and a second electrode 105, and the photoactive layer 104. The silver may include a p-type semiconductor thin film and an n-type semiconductor thin film.

Photoexcitation causes the p-type semiconductor to form an exciton paired with electrons and holes, and the exciton is separated into electrons and holes at the p-n junction. The separated electrons and holes migrate to the n-type semiconductor thin film and the p-type semiconductor thin film, respectively, and they are collected in the first electrode and the second electrode, respectively, so that they can be used as electric energy from the outside.

In another exemplary embodiment, the imidazole derivative of Chemical Formula 1 is an electron acceptor material, and the organic active layer further provides an electron donor material.

In particular, in order for the imidazole derivative of Formula 1 to be used as an electron acceptor material of an organic solar cell, the LUMO level of compounds such as P3HT, which is generally used as an electron donor, and a work function of a metal Consideration should be given to adjusting the LUMO level of the e-acceptor.

The most widely used electron acceptor material is the {6} -1- (3- (methoxycarbonyl) propyl) - {5} - methanofullerene derivative as disclosed in the Fred Wudl group in 1995 } -1-phenyl [5,6] C61 ({6} -1- (3- (methoxycarbonyl) propyl) Chem. 1995. 60532). PCBM is mixed with representative representative material MDMO-PPV (poly (2-methoxy-5- (3 ', 7'-dimethyl-octyloxy) - p-phenylene vinylene) and P3HT (poly (3-hexylthiophene) The energy conversion efficiency varies depending on the mixing ratio, the annealing condition, and the lamination structure. In the organic solar cell, the maximum efficiency is reported to be about 6%. However, since the manufacturing process is complicated, many.

The imidazole derivative of Chemical Formula 1 prepared by the present specification may be manufactured in a suitable structure so that it may be used as an organic solar cell.

In addition, the derivative of Formula 1 is advantageous to improve various solubility compared with the conventional PCBM series, and has an advantage in reproducibility and productivity.

In an exemplary embodiment of the present specification, when the imidazole derivative of Formula 1 is used as the electron acceptor material in the photoactive layer of the organic solar cell, an open voltage higher than that of the conventional organic solar cell using PCBM as the electron acceptor material in the photoactive layer. The LUMO can be adjusted to be expected, and the HOMO can be adjusted to enable the hole blocking role.

Therefore, when the compound of Formula 1 of the present specification is used as the photoactive layer of the organic solar cell, the energy conversion efficiency can be much improved, and in the case of a compound having low solubility, the device can be manufactured by vacuum deposition, and the solubility is In the case of an excellent compound, a low cost and high efficiency organic solar cell can be manufactured as a material suitable for a low cost printing process.

Solar cells are important to increase efficiency so that they can output as much electrical energy as possible from solar energy. In order to increase the efficiency of such a solar cell, it is also important to generate as much excitons as possible in the semiconductor, but it is also important to draw out generated charges without loss. Therefore, the organic solar cell of the imidazole derivative represented by the general formula (1) of the present specification can increase the energy efficiency by controlling LUMO and HOMO.

In an exemplary embodiment of the present specification, Chemical Formula 1 combined with Chemical Formula 1-1 including Q ₂ has an appropriate LUMO energy level in an organic electronic device.

In an exemplary embodiment of the present specification, representative materials of the electron donor material include the following structures, including a poly (phenylene vinylene) (PPV) -based polymer or a poly (3-hexylthiophene) (P3HT) -based polymer. It is not limited.

n is an integer of 1 to 1000,

Rm is hydrogen, a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group containing one or more of N, O, S atoms, or substituted or unsubstituted aryl group.

The electron donor materials are preferably substances having a small band gap so as to absorb the entire visible light region of sunlight, and polymer compounds are generally used, but the present invention is not limited thereto.

In another exemplary embodiment, the derivative of Formula 1 provides an organic solar cell having an LUMO energy level of -3.0 to -5.0 eV.

This is advantageous for application to the electron acceptor of an organic solar cell.

In one embodiment, the derivative of Formula 1 provides an organic solar cell having a LUMO energy level of -3.3 to -4.5 eV.

The organic solar cell according to the present specification may be manufactured using a conventional method and material for manufacturing an organic solar cell, except that the compound of Formula 1 is used in at least one layer of the organic material layer of the organic solar cell.

For example, the organic solar cell according to the present specification uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to form a metal or conductive metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, and the organic material layer is formed on the organic material layer by vacuum deposition or a solution coating method, and then deposited thereon a material that can be used as a cathode.

The organic solar cell provides an organic solar cell having a reverse structure in addition to the sequentially stacked structure.

In addition to the sequentially stacked structure as described above, in order to manufacture an organic solar cell of the reverse structure, the organic solar cell may be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

In another exemplary embodiment, an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is the imidazole. It is an organic light emitting device comprising a derivative.

In another exemplary embodiment, the organic material layer provides an organic light emitting device including a hole injection layer or a hole transport layer including the imidazole derivative.

In one exemplary embodiment, the organic material layer provides an organic light emitting device including a light emitting layer including the imidazole derivative.

In another exemplary embodiment, the organic material layer provides an organic light emitting device including an electron transport layer including the imidazole derivative.

In one embodiment, the organic material layer further includes at least one selected from the group consisting of a hole injection layer, a hole transporting layer, a hole blocking layer, an electron blocking layer, a charge generating layer, an electron transporting layer and an electron injecting layer.

In another embodiment, when the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or another material.

In one exemplary embodiment, the organic material layer includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group, or a benzcarbazole group, in addition to the organic layer including the imidazole derivative. To provide.

In another exemplary embodiment, the organic material layer including the imidazole derivative includes the imidazole derivative as a host, and provides an organic light emitting device including another organic compound, a metal, or a metal compound as a dopant.

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

In another exemplary embodiment, an organic transistor including a source, a drain, a gate, and an organic material layer including one or more imidazole derivatives represented by Formula 1 is provided.

In another exemplary embodiment, the organic transistor includes a charge generating layer including an imidazole derivative represented by Chemical Formula 1.

In another embodiment, the organic transistor may further include the insulating layer. The insulating layer may be positioned on the substrate and the gate.

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

In another embodiment, an organic photoconductor comprising a first electrode, a second electrode, and at least one organic material layer including an organic photosensitive layer disposed between the first electrode and the second electrode, wherein one of the organic material layers The layer or more provides an organic photoconductor comprising the imidazole derivative represented by the formula (1).

In another exemplary embodiment, the organic photoconductor includes a charge generating layer including an imidazole derivative represented by Chemical Formula 1.

In another exemplary embodiment, the organic layer further includes an ultraviolet light stabilizer including an imidazole derivative represented by Chemical Formula 1.

In another embodiment, the organophotoreceptor may be in the form of, for example, a plate, a flexible belt, a disk, a rigid drum, a sheet around a rigid or flexible drum, and a rigid drum generally used for commercial purposes.

In another embodiment, the organophotoreceptor may comprise an electrically conductive substrate and a photoconductive element, for example, in the form of one or more layers.

The organophotoreceptor is poly and may contain both a charge transport compound and a charge generating compound in the binder, which may or may not be in the same layer.

Similarly, the electron transport compound may or may not be the same layer as the charge generating compound. If the electron transport compound is present in a layer other than the charge generating compound, then the electron transport compound may be an overcoat, i.e., on the opposite side of the electrically conductive substrate, or may be in the form of an undercoat, Can be on the side.

The organic layer of each layer included in the organic electronic device is a solvent process, such as roll to roll, spin coating, dip coating, casting, and roll coating, using various monomolecular or polymer materials, rather than a deposition method. It can manufacture by a method, such as a roll court, flow coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method.

A dry film formation method such as an organic layer of each of the above layers, vacuum deposition, sputtering, plasma, ion plating, or the like.

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.

As the anode material, a material having a large work function is preferably used so as to smoothly inject holes, which are usually formed in the organic material layer. Specific examples of the cathode material that can be used in the present invention include 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate injection of electrons from the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole transport material is a material capable of well injecting holes from the active layer, and the highest occupied molecular orbital (HOMO) of the hole transport material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole transferring material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

In addition, several hole transport layers may be used. At this time, a compound having high mobility to holes is suitable. Specific examples thereof include arylamine-based compounds; Carbazole-based compounds; Anthracene-based compounds; Pyrene-based compounds; A conductive polymer, a block copolymer having a conjugated portion and a non-conjugated portion together, but the present invention is not limited thereto.

Hereinafter, preferred preparation examples and examples are provided to aid the understanding of the present specification. The following Preparation Examples and Examples are intended to aid understanding, but are not limited thereto.

Manufacturing example

Preparation Example 1 Preparation of Compound 1-A-1

4-Bromo-2-fluorobenzaldehyde (10.2 g / 51.7 mmol), benzyl (10.5 g / 51.7 mmol), 4-aminophenol (11.3) g / 103.4 mmol), ammonium acetate (NH ₄ OAc) (6.0 g / 77.6 mmol), and 100 mL of acetic acid (AcOH) were added thereto, followed by heating and stirring for 12 hours. After cooling to room temperature, water (H ₂ O) was added to the reaction mixture, which was then stirred and filtered. After sufficiently washing with water and dried in a vacuum oven, and recrystallized with dichloromethane (CH ₂ Cl ₂ ) and n-hexane (n-Hexane) to prepare a solid compound 1-A-1 (9.4 g, 37.5% yield).

MS: [M] ⁺ = 485

Preparation Example 2 Preparation of Compound 1-A-2

Compound 1-A-1 (4.85 g, 10.0 mmol) and 4-formylphenylboronic acid Compound 1-B-3 (1.65 g, 11.0 mmol) was dissolved in tetrahydrofuran (60 mL). Then, 2M aqueous potassium carbonate solution (40 mL) was added thereto, and tetrakistriphenylphosphinopalladium (231 mg, 2 mol%) was added thereto, followed by stirring under reflux for 8 hours. The temperature was lowered to room temperature, n-hexane was added to the reaction mixture to form a solid, and the resulting solid was filtered and dried. The solid thus obtained was recrystallized with methylene chloride and ethanol, filtered and dried to give compound 1-A-2 (3.47 g, 68%).

MS: [M + H] ⁺ = 511

Preparation Example 3 Preparation of Compound 1-A-3

Compound 1-A-2 (3.22 g, 5.1 mmol) and Compound 1-B-4 (0.91 g, 5.6 mmol), piperidine (1 mL) and acetonitrile solvent 40 mL, tetrahydrofuran solvent 60 Stirring reflux in mL for 18 h. After the temperature was lowered to room temperature and the organic solvent was distilled off, methylene chloride and water were added to extract the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and then vacuum distilled. After purification by column chromatography (EA: n-Hex = 1: 4v / v), ethanol was added to the compound and stirred to form a solid. Filtration and drying of the solid gave compound 1-A-3 (2.35 g, 68%).

MS: [M + H] ⁺ = 679

Preparation Example 4 Preparation of Compound 1-A-4

Compound 1-A-3 (2.35 g, 3.46 mmol), trifluoromethanesulfonic anhydride (10 mL), 6M aqueous potassium carbonate solution (20 mL), and acetonitrile solvent were stirred under reflux for 18 hours. . After the temperature was lowered to room temperature and the acetonitrile solvent was distilled off, methylene chloride and water were added to extract the organic layer. The organic layer was dried over anhydrous magnesium sulfate and then vacuum distilled. The solid produced in this manner was added to ethanol and stirred to form a solid. The solid was filtered and dried to give compound 1-A-4 (1.6 g, 57%).

MS: [M + H] ⁺ = 811

Preparation Example 5 Preparation of Compound 1-A-5

In Preparation Example 2, except that Compound 1-B-1 was used instead of Compound 1-B-3, Compound 1-A-5 was prepared in the same manner as in the same manner.

Preparation Example 6 Preparation of Compound 1-A-7

In Preparation Example 4, except that Compound 1-A-5 was used instead of Compound 1-A-3, the compound was proceeded in the same manner to prepare Compound 1-A-6.

In Preparation Example 2, Compound 1-A-7 was prepared in the same manner as in Example 1, except that Compound 1-A-6 was used instead of Compound 1-A-1.

Preparation Example 7 Preparation of Compound 1-a-16

In Preparation Example 3, Compound 1-a-16 was prepared by the same method except that Compound 1-A-7 was used instead of Compound 1-A-2.

Preparation Example 8 Preparation of Compound 1-b-31

In Preparation Example 2, the compound 4,7-dibromo-2,1,3-benzothiadiazole (4,7-dibromo-2,1,3-benzothiadiazole) instead of compound 1-A-1 Compound 1-b-31 was prepared in the same manner except for using 2.4 equivalents of compound 1-A-20, instead of compound 1-B-3.

MS: [M + H] ⁺ = 1421

Preparation Example 9 Preparation of Compound 1-A-9

Compound 1-A-9 was prepared by the same method as Preparation Example 2, except that Compound 1-A-8 was used instead of Compound 1-A-1 in Preparation Example 2. MS: [M + H] ⁺ = 763

Preparation Example 10 Preparation of Compound 1-b-25

In Preparation Example 3, Compound 1-b-25 was prepared by the same method as Compound 1-A-9, except that Compound 1-A-9 was used.

MS: [M + H] ⁺ = 931

Preparation Example 11 Preparation of Compound 1-b-32

In Preparation Example 5 Compound 1-A-20 instead of Compound 1-A-1, Compound 2,7-dibromo-9,9-dioctylfluorene (2,7-dibromo instead of Compound 1-B-1 -9,9-dioctylfluorene) was prepared in the same manner as in Preparation Example 5, except that Compound 1-b-32 was prepared.

MS: [M + H] ⁺ = 1675

Preparation Example 12 Preparation of Compound 1-b-12

In Preparation Example 3, except that Compound 1-A-7 was used instead of Compound 1-A-2, and proceeded in the same manner to prepare Compound 1-b-12.

MS: [M + H] ⁺ = 1091

Experimental Example

Experimental Example 1-1-1 Electrochemical Properties of the Chemical Formula 1 Compounds

In order to observe the electrochemical properties of the compounds prepared in Preparation Examples 7, 10, and 12, oxidation / reduction properties were observed using a Cyclovoltameter (CV). CV equipment was used Autolab PGSTAT128N cyclovoltametry, 0.1M tetrabutylammonium tetrafluoroborate (Bu ₄ NBF ₄ ) (Tetrabutylammonium tetrafluoroborate) and acetonitrile (Acetonitrile) solvent was used as a sample, the sample was 10 ^-3 M It was dissolved in 1,2-dichlorobenzene at the concentration of. Measured at a scanning speed of 100 mV / s under Ar at room temperature, a glass carbon electrode (0.3 mm in diameter) was used as a working electrode, Pt and Ag / AgCl electrode as a counter electrode and a reference electrode the results are shown in the following table 5 is shown.

 TABLE 5 Energy levels of the compounds

The HOMO and LUMO are calculated by calculating the energy level of ferrocene (Ferrocene) as -4.8 eV.

In general, the open-circuit voltage (Voc) of an organic solar cell is known to be caused by the difference between the HOMO energy level of the donor material and the LUMO energy level of the donor material (CJ Brabec et al., Adv. Func. 374).

Example 1-1-2 An organic solar cell using P3HT and compound 1-a-16 as a photoactive layer

After spin coating PEDOT-PSS (Heraeus, CLEVIOS ^TM P) by about 40 nm on an indium tin oxide (ITO) glass substrate (surface resistance of 7 Ω / sq), poly (3-hexylthiophene) [Poly-3 -(hexylthiophene), P3HT, Rieke Metal Co., Ltd.] and Compound 1-a-8 prepared herein in a weight ratio of 1: 0.6 in 1,2-dichlorobenzene, chlorobenzene, chloroform alone or a mixed solvent thereof and spin An organic thin film having a thickness of 70 nm was formed by coating or the like. LiF / Al was deposited on the organic film thus formed as an electrode at 0.7 nm and 120 nm under vacuum, and then encapsulated with a glass cap attached with a moisture absorbent.

The encapsulated device was annealed at 150 ° C. for 10 minutes and then measured IV characteristics under a light source of AM 1.5G 100 mW / cm ² using a-bet b class artificial solar simulator.

Example 1-1-3 An organic solar cell using P3HT and compound 1-b-12 as a photoactive layer

As in Example 1-1-2, except that Compound 1-b-12 was used instead of Compound 1-a-16 as the photoactive layer receiving material. As a result, the electrochemical characteristics of the organic solar cell are shown in Table 6 below.

Example 1-1-4 An organic solar cell using P3HT and compound 1-b-25 as a photoactive layer

As in Example 1-1-2, except that Compound 1-b-25 was used instead of Compound 1-a-16 as the photoactive layer receiving material.

As a result, the electrochemical characteristics of the organic solar cell are shown in Table 6 below.

[Table 6]

The solar cell manufactured as shown in Table 6 showed a relatively high value of Voc. This is due to an increase in the difference between HOMO and LUMO of P3HT, the compound of formula (I).

Claims (34)

An imidazole derivative represented by Formula 1 or comprising two or more structures of Formula 1:
[Chemical Formula 1]

In Formula 1,
Ar ₁ is-(L ₁ ) p _1- (Y ₁ ) q ₁ , Ar ₂ is-(L ₂ ) p _2- (Y ₂ ) q ₂ , and Ar ₃ is-(L ₃ ) p _3- ( Y ₃ ) q ₃ , Ar ₄ is-(L ₄ ) p _4- (Y ₄ ) q ₄ ,
p ₁ to p ₄ each represent an integer of 0 to 10,
q ₁ to q ₄ each represent an integer of 1 to 10,
L ₁ to L ₄ are the same as or different from each other, and each independently a direct bond; Oxygen; sulfur; Nitrogen substituted or unsubstituted with an alkyl or aryl group; A substituted or unsubstituted arylene group; Substituted or unsubstituted divalent arylamine group; Substituted or unsubstituted divalent triaryl phosphine group; Substituted or unsubstituted divalent triaryl phosphine oxide group; A substituted or unsubstituted alkenylene group; Substituted or unsubstituted alkynylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted carbazolylene group; Substituted or unsubstituted benzocarbazolylene group; A substituted or unsubstituted divalent aromatic or aliphatic ring cyclic ketone group; Substituted or unsubstituted divalent aromatic ring group; Divalent substituted or unsubstituted aromatic or aliphatic heterocyclic groups containing at least one of N, O, and S atoms; And a substituted or unsubstituted divalent aromatic ring and a condensed ring group of the heterocycle are selected from the group consisting of
Y ₁ to Y ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Ester group (-CO ₂ R); Carbonyl group (-COR); Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; Substituted or unsubstituted aryl phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; A cyclic ketone group of a substituted or unsubstituted aromatic or aliphatic ring; An imide group of a substituted or unsubstituted aromatic or aliphatic ring; A substituted or unsubstituted aromatic ring group; A substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms; A substituted or unsubstituted condensed ring group of the aromatic ring and the hetero ring; An imidazole group unsubstituted or substituted with Formula 1-1; Or in the following Formula 1-1,
[Formula 1-1]

At least one of Y ₁ to Y ₄ may be represented by Formula 1-1,
In Chemical Formula 1-1,
n is an integer from 0 to 4,
R _a , R _b and R _c are the same as or different from each other, and each independently hydrogen; Cyano group (-CN); An ester group; Carbonyl group (-COR); Carboxyl group (—CO ₂ R); Fluoro groups (-F); Or an alkyl group substituted with a fluoro group (-F); A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Q ₂ is oxygen ( O ),

,

,

,

,

,

And

, ≪ / RTI >
* Is a moiety linked to Chemical Formula 1-1,
a, b, c and d are each an integer of 0 to 4,
R, R 'and R "are the same as or different from each other, and each independently hydrogen; cyano group (-CN); ester group; cyano group (-CN); ester group; carbonyl group (COR'"); Carboxyl group (CO ₂ R '"); fluoro group (-F); or alkyl group substituted with fluoro group (-F); substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted An alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aromatic or aliphatic heterocyclic group including one or more of N, O, and S atoms; or a substituted or unsubstituted aryl group,
R '"is the same as defined above. The imidazole derivative according to claim 1, wherein Y ₄ is Formula 1-1. The imidazole derivative of claim 1, wherein Y ₃ is the chemical formula 1-1. The imidazole derivative of claim 1, wherein the imidazole derivative represented by Formula 1 is represented by any one of Formulas 2 and 3:
(2)

(3)

In Chemical Formulas 2 and 3,
Ar ₁ to Ar ₄ , L ₃ and L ₄ are the same as defined in Formula 1,
R _a , R _b , R _c , n and Q ₂ are the same as defined in Formula 1-1. The imidazole derivative according to claim 1, wherein the imidazole derivative including two or more structures of Formula 1 is represented by any one of the following Formulas 4 to 6.
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In Chemical Formulas 4 to 6,
r, s and w are integers from 0 to 2,
t, u and v are integers from 0 to 3,
Ar ₃ 'is-(L ₃ ') p ₃ '-(Y ₃ ') q ₃ ', Ar ₃ "is-(L ₃ ") p ₃ "-(Y ₃ ") q ₃ ", and Ar _a Is-(L _a ) p _a- (Y _a ) q _a , Ar _b is-(L _b ) p _b- (Y _b ) q _b , and Ar _c is-(L _c ) p _c- (Y _c ) _c , Ar _d is-(L _d ) p _d- (Y _d ) q _d , Ar _e is-(L _e ) p _e- (Y _e ) q _e , and Ar _f is-(L _f ) p _f- (Y _f ) q _f ,
p ₃ ', p ₃ ", p _a , p _b , p _c , p _d , p _e and p _f are the same as the definition of p ₁ to p ₄ of Formula 1,
q ₃ ′, q ₃ ″, q _a , q _b , q _c , q _d , q _e and q _f are the same as the definitions of q ₁ to q ₄ in Chemical Formula 1,
L ₃ ′, L ₃ ″, L _a , L _b , L _c , L _d , L _e and L _f have the same definitions as L ₁ to L ₄ in Formula 1,
Y ₃ ′, Y ₃ ″, Y _a , Y _b , Y _c , Y _d , Y _e and Y _f are the same as the definitions of Y ₁ to Y ₄ of Chemical Formula 1,
Ar ₃ is the same as defined in Formula 1,
Formulas 4 to 6 include at least one of Formula 1-1,
Z represents a divalent linking group, which is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted cyclic ketone group of a divalent aromatic or aliphatic ring; Substituted or unsubstituted divalent aromatic ring group; A substituted or unsubstituted divalent heterocyclic group including at least one of substituted or unsubstituted N, O, and S atoms; A group having a condensed or non-condensed divalent linking group including the heterocyclic group or the aromatic ring group; Oxygen; sulfur; Substituted or unsubstituted nitrogen; Or substituted or unsubstituted phosphorus. The method according to claim 1, wherein Y ₁ to Y ₄ are the same as or different from each other, and each independently hydrogen; A nitrile group; A substituted or unsubstituted ester group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A cyclic ketone group of a substituted or unsubstituted aromatic or aliphatic ring; An imide group of a substituted or unsubstituted aromatic or aliphatic ring; A substituted or unsubstituted aromatic ring group; A substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms; A substituted or unsubstituted condensed ring group of the aromatic ring and the hetero ring; An imidazole group unsubstituted or substituted with Formula 1-1; And imidazole derivatives selected from the group consisting of Chemical Formula 1-1. The method according to claim 1, wherein Y ₁ to Y ₄ are the same as or different from each other, each independently represent a substituted or unsubstituted alkenyl group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted pyrene group; A substituted or unsubstituted quinazoline group; Substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; A cyclic ketone group of a substituted or unsubstituted aromatic or aliphatic ring; An imide group of a substituted or unsubstituted aromatic or aliphatic ring; A substituted or unsubstituted aromatic ring group; A substituted or unsubstituted condensed ring group of the aromatic ring and the hetero ring; Or an imidazole group unsubstituted or substituted with Formula 1-1; And at least one imidazole derivative selected from the group consisting of Chemical Formula 1-1. The method according to claim 1, wherein L ₁ to L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent aromatic or aliphatic ring cyclic ketone group; Substituted or unsubstituted divalent aromatic ring group; Divalent substituted or unsubstituted aromatic or aliphatic heterocyclic groups containing at least one of N, O, and S atoms; And a substituted or unsubstituted divalent aromatic ring with a heterocyclic condensed ring group. The method according to claim 1, wherein L ₁ to L ₄ are the same as or different from each other, each independently represent a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Substituted or unsubstituted anthracenylene group; And a substituted or unsubstituted benzothiadiazolene group. The method according to claim 5, wherein Z is a substituted or unsubstituted arylene group; Condensed ring of a substituted or unsubstituted aromatic ring with a heterocyclic ring; And a condensed ring of the arylene group and the aromatic ring and the hetero ring is a group selected from a divalent linking group in which two or more are connected. The imidazole derivative of claim 10, wherein Z is a group selected from the following divalent linking groups:

a, c, d and g are each an integer of 0 to 4,
e and f are each an integer of 0 to 3,
b is an integer of 0 to 2,
R _f , R _g , R _h , R _i , R _j , R _k , R _l are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group,
R _d and R _e are hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; It is selected from the group consisting of a substituted or unsubstituted aryloxy group. The method according to claim 1, Q ₂ of Formula 1 is

Imidazole derivatives that are:
* Is a part connected to the formula (1-1). The method according to claim 1, Q ₂ of Formula 1 is

Imidazole derivatives that are:
* Is a moiety linked to Chemical Formula 1-1,
a is an integer of 0 to 4,
R 'is hydrogen; Cyano group (-CN); An ester group; Cyano group (-CN); An ester group; Carbonyl group (COR '"), carboxyl group (CO ₂ R'"); Fluoro groups (-F); Or an alkyl group substituted with a fluoro group (-F); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms; Or a substituted or unsubstituted aryl group,
R '"is the same as defined above. The imidazole derivative according to claim 1, wherein Formula 1 is selected from the formulas shown in Table 1 below:
[Table 1]

. The imidazole derivative according to claim 1, wherein Formula 1 is selected from the formulas shown in Table 2 below:
[Table 2]

. The imidazole derivative according to claim 1, wherein Formula 1 is selected from the formulas shown in Table 3 below:
[Table 3]

. The imidazole derivative according to claim 1, wherein Formula 1 is selected from the formulas shown in Table 4 below:
[Table 4]

. An organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is in accordance with any one of claims 1 to 17. An organic electronic device comprising an imidazole derivative. The organic electronic device of claim 18, wherein the organic electronic device is an organic solar cell, an organic light emitting device, an organic photoconductor, or an organic transistor. The device of claim 18, wherein the organic electronic device comprises: a first electrode; A second electrode facing the first electrode; And at least one organic material layer disposed between the first electrode and the second electrode,
One or more layers of the organic material layer includes the imidazole derivative. The organic electronic device of claim 20, wherein the organic solar cell is a bilayer p-n junction type. The organic electronic device of claim 20, wherein the organic solar cell is a bulk heterojunction (BHJ) junction type. The organic electronic device of claim 20, wherein the imidazole derivative is an electron acceptor material, and the organic material layer further contains an electron donor material. The organic electronic device of claim 23, wherein the electron donor material is selected from one or more of the following structures:

n is an integer from 1 to 1000,
Rm is hydrogen, a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group containing one or more of N, O, S atoms, or substituted or unsubstituted aryl group. The organic electronic device of claim 20, wherein the imidazole derivative has a LUMO energy level of -3 to -5 eV. The method of claim 18, wherein the organic electronic device is an organic light emitting device including a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode.
One or more layers of the organic material layer includes the imidazole derivative. The organic electronic device of claim 26, wherein the organic material layer comprises a hole injection layer or a hole transport layer including the imidazole derivative. The organic electronic device of claim 26, wherein the organic material layer comprises a light emitting layer including the imidazole derivative. The organic electronic device of claim 26, wherein the organic material layer includes an electron transport layer including the imidazole derivative. The organic electronic device of claim 26, wherein the organic material layer includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group, or a benzcarbazole group, in addition to the organic material layer including the imidazole derivative. The organic electronic device of claim 26, wherein the organic material layer including the compound includes the imidazole derivative as a host, and includes another organic compound, a metal, or a metal compound as a dopant. The organic transistor of claim 18, wherein the organic electronic device is an organic transistor including a source, a drain, a gate, and one or more organic material layers.
The organic material layer is an organic electronic device comprising the imidazole derivative. The organic electronic device of claim 32, wherein the organic material layer includes a charge generating layer including the compound of Formula 1. The method of claim 18, wherein the organic electronic device is an organic photoconductor comprising a first electrode, a second electrode, and at least one organic layer including an organic photosensitive layer disposed between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic photoconductor comprising an imidazole derivative represented by the formula (1).

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