KR101592628B1 - Imidazole compound and organic electronic device using the same - Google Patents

Abstract

The present invention relates to a novel imidazole derivative and an organic electronic device using the same, and more particularly to a new imidazole derivative capable of improving the photoelectric conversion efficiency of an organic solar battery.

Description

(IMIDAZOLE COMPOUND AND ORGANIC ELECTRONIC DEVICE USING THE SAME)

The present invention relates to imidazole derivatives and organic electronic devices 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 electric power generation characteristics using the organic semiconductor as the active layer, much attention has been paid 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 invention provides an imidazole derivative and an organic electronic device using the same.

The present invention provides imidazole derivatives represented by the following formula (1) or containing two or more structures represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Ar ₁ is _{- (L 1) p 1 -} (Y 1) , and q _1, Ar ₂ is _{- (L 2) p 2 -} (Y 2) and q _2, 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 or different and are each independently a direct bond; Oxygen; sulfur; Nitrogen substituted or unsubstituted with an alkyl or aryl group; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent arylamine group; A substituted or unsubstituted divalent triarylphosphine group; A substituted or unsubstituted divalent triarylphosphine oxide group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted alkynylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted carbazolylene group; A substituted or unsubstituted benzocarbazolylene group; A cyclic ketone group of a substituted or unsubstituted divalent aromatic or aliphatic ring; A substituted or unsubstituted divalent aromatic ring group; A divalent substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms; And a condensed ring group of the substituted or unsubstituted divalent aromatic ring and the heterocyclic ring,

Y ₁ to Y ₄ are the same or different 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; 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; A substituted or unsubstituted arylphosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; A 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 condensed ring group of said substituted or unsubstituted aromatic ring and said heterocyclic ring; An imidazole group substituted or unsubstituted by the formula 1-1; Or a compound represented by the following formula (1-1)

 [Formula 1-1]

At least one of Y ₁ to Y ₄ is the above-described formula 1-1,

In 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); A carboxyl group (-CO ₂ R); Fluoro group (-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 Formula 1-1,

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

R, R 'and R "are the same or different and each independently hydrogen, cyano group (-CN), ester group, cyano group (-CN), ester group, carbonyl group (COR'''); Carboxylic group (CO ₂ R '"); fluoro group (-F); or an alkyl group substituted by a group (-F) fluoro; substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms, or substituted or unsubstituted aryl group,

R "" is the same as the definition of R above.

The present invention also relates to an organic electronic device comprising 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 a compound And an organic electroluminescent device.

The imidazole derivative according to the present invention can be used as a material for an organic material layer of an organic electronic device including an organic solar cell, and an organic electronic device including the organic solar cell exhibits excellent characteristics in terms of increase in efficiency and stability.

In particular, the new imidazole derivatives according to the present invention exhibit excellent thermal stability, various band gaps, various HOMO and LUMO level states, and excellent electronic stability.

The derivatives of the formula (1) according to the present invention can be used purely in organic electronic devices including organic solar cells, or mixed with impurities, and can be applied by vacuum deposition, solution coating or the like, improve light efficiency, The lifetime characteristics of the device can be improved by thermal stability.

1 shows an example of an organic solar cell made up of a substrate 101, a first electrode 102, a hole transport layer 103, a photoactive layer 104 and a second electrode 105.
2 is a view showing a mass spectrum of the 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.

The imidazole derivative according to the present invention has two or more structures represented by the above formula (1) or the above formula (1).

In the present specification, * means a linkage with a chemical 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 and is preferably an alkenyl group having 2 to 40 carbon atoms. Specifically, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group, Or an alkenyl group substituted by a cycloalkyl group or a cycloalkenyl group, but is not limited thereto.

In the present specification, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 40, which is a range that does not cause 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 of the alkoxy group is not particularly limited, since it only affects the application of a vacuum deposition method or a solution coating method. And 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 and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluoranthene group, but the scope of the present specification is not limited 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 of the ring compounds 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 an 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 can be selected from the examples of the above-mentioned heterocyclic group.

In the present specification, an arylene group, an alkenylene group, an alkynylene group, a fluorenylene group, a carbazolylene group, and a benzocarbazolylene group are each an aryl group, an alkenyl group, an alkynyl group, a fluorenyl group, Of the 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, a divalent triarylphosphine group is connected to an aryl group via a linking group.

In the present specification, a divalent triarylphosphine oxide group is connected to an aryl group via a linking 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 are. But are not limited thereto.

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 formula (1).

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

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 invention, the above-mentioned Y ₄ is an imidazole derivative represented by the above formula (1-1).

In another embodiment, the present invention provides the imidazole derivative wherein Y ₃ is the above-mentioned formula 1-1.

In one embodiment of the present invention, the imidazole derivative represented by Formula 1 is represented by any of Formula 2 and Formula 3 below.

(2)

(3)

In the general 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 as defined in formula (1-1).

In one embodiment of the present invention, Y ₁ to Y ₄ are the same 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 condensed ring group of said substituted or unsubstituted aromatic ring and said heterocyclic ring; An imidazole group substituted or unsubstituted by the formula 1-1; And an imidazole derivative selected from the group consisting of Formula (1-1).

In another embodiment, Y ₁ to Y ₄ are the same or different and each independently represents a substituted or unsubstituted alkenyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted pyrene group; A substituted or unsubstituted quinazoline group; A 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 condensed ring group of said substituted or unsubstituted aromatic ring and said heterocyclic ring; Or an imidazole group substituted or unsubstituted by the above formula (1-1); And an imidazole derivative wherein at least one group selected from the group consisting of Formula (1-1) is selected.

In another embodiment, L ₁ to L ₄ are the same or different and each independently represent a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted anthracenylene group; And a substituted or unsubstituted benzothiadiazolylene group. The present invention also provides an imidazole derivative represented by the formula

According to one embodiment of the present invention, the inclusion of two or more structures of the formula (1) means that the compounds having the structure of the formula (1) exist in a structure directly connected to each other without a linking group. In this case, it is meant that each of the same chemical formulas or different chemical formulas of Chemical Formula 1 may be directly bonded to form two or more chemical structures.

According to another embodiment of the present invention, two or more of the structures represented by the above formula (1) include alkanes having two or more bridging groups; Cycloalkanes having two or more bridging groups; 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 two or more bridging groups; A substituted or unsubstituted heterocycle having a divalent or higher linking group containing at least one of N, O and S atoms; A group having a condensed or non-condensed divalent or higher linking group including a heterocyclic ring or an aromatic ring; Oxygen atom; Hwang Wonjae; A substituted or unsubstituted nitrogen atom; Or a substituted or unsubstituted phosphorus atom may be linked to two or more of the structures of the above formula (1). In this case also, the same chemical formulas or different chemical formulas of the chemical formula 1 may be combined to include two or more chemical structures.

In one embodiment of the present invention, an imidazole derivative having two or more structures represented by the formula (1) is represented by any one of the following formulas (4) to (6).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In formulas (4) to (6)

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

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

Ar ₃ 'is _{- (L 3') p 3} '- (Y 3') q 3 ' , and, Ar ₃ "is _{- (L 3") p 3} "- (Y 3") q 3 " , and, Ar _a is _{- (L a) p a -} (Y a) q a a, Ar _b is _{- (L b) p b -} (Y b) and q _b, Ar _c is _{- (L c) p c -} (Y c ) and q _c, Ar _d is - (L _d), p _d - (Y _d) q _d is, Ar _e is - (L _e) p _e - and (Y _e) q _e, 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 defined for p ₁ to p ₄ in formula

_{q 3 ', q 3 ",} q a, q b, q c, q d, q e q and _f are as defined in formula (1) of q ₁ to q _4,

L ₃ , L ₃ , L _a , L _b , L _c , L _d , L _e and L _f are the same as defined for 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 defined for Y ₁ to Y ₄ in formula (1)

Ar ₃ is the same as defined in Formula 1,

(4) to (6) contain at least one or more of the above-mentioned formula (1-1)

Z represents a divalent linking group, 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 cyclic ketone group of a substituted or unsubstituted divalent aromatic or aliphatic ring; A substituted or unsubstituted divalent aromatic ring group; A substituted or unsubstituted divalent heterocyclic group containing at least one of substituted or unsubstituted N, O, and S atoms; A group having a condensed or non-condensed divalent linking group containing the heterocyclic group or the aromatic ring group; Oxygen; sulfur; Substituted or unsubstituted nitrogen; Or substituted or unsubstituted phosphorus.

When at least one of Y ₃ , Y ₃ ', Y _a and Y _b is represented by the formula (1-1), the repeating number of the substituent represented by the formula (1-1) o or p is 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.

When at least one of Y _c and Y _d is represented by the formula (1-1), the repeating number of the substituent represented by the formula (1-1), for example, t or u is 1 or more it means.

When at least one of Y _e , Y _f and Y ₃ 'is represented by the formula (1-1), the repeating number of the substituent represented by the formula (1-1), for example, v Or w is not less than 1. However, when Y ₃ "in formula (6) is represented by formula (1-1), v and / or w may be 0.

In one embodiment, Z is a substituted or unsubstituted arylene group; A condensed ring of a substituted or unsubstituted aromatic ring and a heterocyclic ring; And a divalent linking group in which two or more of the arylene group and the condensed ring of the aromatic ring and the heterocyclic ring are connected to each other.

In the present specification, the following groups are exemplified as the divalent linking group, but the present invention is not limited thereto.

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 and R ₁ are the same or different 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; And a substituted or unsubstituted aryloxy group.

In one embodiment of the present disclosure, Z is linked to Ar ₄ of formula (1).

In one embodiment of the present specification, Z is linked to Ar ₃ of the above 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 above p ₁ to p ₈ , and x is an integer of 1 to 8.

In one embodiment of the present disclosure, p _x is zero.

In one embodiment of the present disclosure, p _x is one.

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

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

In another embodiment, L _x is a phenylene group.

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

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

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

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

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

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

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

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

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

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

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

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

In another embodiment, L _x is a biphenylene group.

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

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

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

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

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

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

또는

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

or

to be.

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

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

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

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

In another 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 embodiment, q _x is 1.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

In another embodiment, Y _x is pyrene.

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

In another embodiment, Y _x is a pyrenylene group substituted with an alkyl group-substituted phenyl group.

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

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

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

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

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

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

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

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

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

In another embodiment, Y _x is an ester group.

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

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

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

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

In another embodiment, Y < ₄ >

In another embodiment, Y < ₃ >

In another embodiment, Y ₄ and Y ₃ are both represented by formula (1-1).

In another embodiment, n is 2.

In another embodiment, R _a is hydrogen.

In another embodiment, R &_lt; a _> is an alkyl group.

이다. In another embodiment, Q < ₂ >

to be.

이다. In another embodiment, Q < ₂ >

to be.

In another embodiment, R 'is hydrogen.

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

In another embodiment, m is 3.

이다. In one embodiment, when two or more of the structures of Formula 1 are included, Z is

to be.

이다. In one embodiment, when two or more of the structures of Formula 1 are included, Z is

to be.

In another embodiment, R _b and R _c are the same or different and are each independently a straight or branched chain substituted or unsubstituted alkyl group.

Specific preferred examples of the compound represented by the formula (1) include compounds represented by the formulas shown in the following Table 1, but are not limited thereto.

[Table 1]

Specific preferred examples of the compound represented by the formula (1) include compounds represented by the formulas shown in the following Table 2, but are not limited thereto.

 [Table 2]

Specific preferred examples of the compound represented by the formula (1) include compounds represented by the formulas shown in the following Table 3, but the present invention is not limited thereto.

 [Table 3]

Specific preferred examples of the compound represented by the formula (1) include compounds represented by the formulas shown in the following Table 4, but are not limited thereto.

[Table 4]

The present invention also provides a process for preparing an imidazole derivative represented by the above formula (1).

Can be prepared by changing the starting material to the starting material corresponding to Q < ₂ >.

Among the manufacturing methods of the organic solar cell, the vacuum deposition process deposits the material by sublimation at a high vacuum, for example, about 10 ^-6 to 10 ^-7 torr and a high temperature. Therefore, it is important that the compound maintains properties without denaturation at high temperature for a long time and can easily sublimate.

The compound of Formula 1 has a plate-shaped core and can easily be sublimated. An aryl group, a heteroaryl group, an arylamine group, or the like is introduced into a substituent group to easily obtain a compound having desired properties .

Meanwhile, the process of the organic solar cell according to the solution process is a process wherein the structure of Formula 1 is a plate-shaped core, but a substituent capable of enhancing solubility such as an aryl group, a heteroaryl group, an alkyl group, , An alkoxy group, and the like.

In addition, the compounds according to the present invention can be used in various applications in organic electronic devices depending on the kind and nature of the substituent.

For example, when a substituted or unsubstituted aryl group or a heteroaryl group is substituted, or when two or more of the structures of the formula (1) are connected to each other, their properties are represented by the deep HOMO Value and an appropriate LUMO to be able to handle the electron acceptor well. In this case, it is advantageous to use it as a dopant for the photoactive layer, electron injection, electron transfer, or hole blocking layer.

The compound of the present invention can act as an electron acceptor (or electron acceptor or acceptor) material having various LUMO levels because the energy level can be controlled by the core and various substituents.

The present invention also relates to an organic electronic device comprising 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 imidazole And a derivative thereof.

The organic electronic device of the present specification can be produced by a conventional organic electronic device manufacturing method and materials, except that one or more organic compound layers are formed 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 opposing the first electrode; And one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes 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.

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, May include a p-type semiconductor thin film and an n-type semiconductor thin film.

The p-type semiconductor forms an exciton paired with electrons and holes by optical excitation, 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 embodiment, the imidazole derivative of Chemical Formula 1 is an electron acceptor material, and the organic active layer further contains an electron donor material.

In particular, in order to use the imidazole derivative of Formula 1 as an electron acceptor of an organic solar cell, the LUMO level of a compound such as P3HT, which is generally used as an electron donor, and the work function of a metal The level of the LUMO of the e-acceptor should be adjusted.

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 Formula 1 prepared by the present specification can be manufactured into an appropriate structure for use as an organic solar cell.

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

In one embodiment of the present invention, when the imidazole derivative of Chemical Formula 1 is used as an electron acceptor in the photoactive layer of an organic solar cell, a higher open-circuit voltage than that of the conventional organic solar cell using PCBM as an electron- The LUMO can be adjusted to expect, and the HOMO can be adjusted to enable the hole blocking function.

Therefore, when the compound of Chemical Formula 1 of the present invention is used as a photoactive layer of an organic solar cell, the energy conversion efficiency can be improved to a great extent, and in the case of a compound having low solubility, a device can be manufactured by a vacuum deposition process, In the case of an excellent compound, a low-cost, 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 using the imidazole derivative represented by the formula (1) of the present invention can increase the energy efficiency by controlling LUMO and HOMO.

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

In one embodiment of the present invention, the representative materials of the electron donor materials include the following polymers including PPV (poly (phenylene vinylene)) polymer or P3HT (poly (3-hexylthiophene) 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; 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.

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

This is advantageous for application to an 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 invention can be produced using a conventional organic solar cell manufacturing method and materials, except that the compound of the above-described formula (1) is used in one or more layers of the organic material layer of the organic solar battery.

For example, the organic solar cell according to the present invention can be manufactured by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate or an alloy thereof To form an anode, then forming an organic material layer on the organic material layer by vacuum deposition or solution coating thereon, and then depositing a material usable as a cathode on the organic material layer.

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

In addition to the sequentially stacked structure, an organic solar cell may be fabricated by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate in order to fabricate an organic solar cell having a reverse structure.

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

In another embodiment, an organic light emitting device comprising 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 an imidazole Or a derivative thereof.

In another embodiment, the organic material layer includes a hole injection layer or a hole transport layer containing the imidazole derivative.

In one embodiment, the organic layer includes an emitting layer containing the imidazole derivative.

In another embodiment, the organic material layer includes an electron transporting layer containing 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 embodiment, the organic material layer includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group, or a benzazole moiety group in addition to the organic material layer including the imidazole derivative. Lt; / RTI >

In another embodiment, the organic material layer containing the imidazole derivative includes the imidazole derivative as a host, and another organic compound, metal or metal compound as a dopant.

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

In another embodiment, there is provided an organic transistor including a source, a drain, a gate, and an organic layer including one or more imidazole derivatives represented by the above formula (1).

In another embodiment, the organic transistor comprises a charge generating layer comprising an imidazole derivative represented by the general formula (1).

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

In one embodiment of the present disclosure, the organic electronic device may be an organophotoreceptor.

In another embodiment, an organophotoreceptor comprising at least one organic layer comprising a first electrode, a second electrode, and an organic photosensitive layer disposed between the first electrode and the second electrode, Layer comprises an imidazole derivative represented by the general formula (1).

In another embodiment, the organophotoreceptor comprises a charge generating layer comprising an imidazole derivative represented by Formula 1 above.

In another embodiment, the organic layer further comprises an ultraviolet light stabilizer which comprises an imidazole derivative represented by the general 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 may be formed by using a variety of monomolecular or polymeric materials, not a vapor deposition method, but a solvent process such as roll to roll, spin coating, dip coating, casting, a roll coating, a flow coating, a doctor blading, a screen printing, an 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 disclosure, 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 a cathode.

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.

As the hole transport layer material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole transport material be between the work function of the anode material and the HOMO of the surrounding organic 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.

Further, a plurality of 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 embodiments and examples are shown to facilitate understanding of the present invention. The following Preparation Examples and Examples are for the purpose of 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 acetic acid (AcOH) (100 mL). After cooling to room temperature, water (H ₂ O) was added to the reaction mixture and stirred, followed by filtration. Washed thoroughly with water, dried in a vacuum oven, and recrystallized from dichloromethane (CH ₂ Cl ₂ ) and n-hexane to obtain solid compound 1-A-1 (9.4 g, yield 37.5%).

MS: [M] ^< ⁺ & gt ^; = 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) were dissolved in tetrahydrofuran Then, 2M potassium carbonate aqueous solution (40 mL) was added, 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 thus-obtained solid was recrystallized from methylene chloride and ethanol, filtered, and then dried to give Compound 1-A-2 (3.47 g, 68%).

MS: [M + H] < ⁺ > = 511

PREPARATION EXAMPLE 3 Preparation of Compound 1-A-3

(0.91 g, 5.6 mmol), piperidine (1 mL), 40 mL of acetonitrile solvent, 60 mL of tetrahydrofuran solvent 60 mL < / RTI > for 18 hours. The temperature was lowered to room temperature, the organic solvent was distilled off, and then methylene chloride and water were added to extract the organic layer. The organic layer was dried over anhydrous magnesium sulfate and vacuum distilled under reduced pressure. After purification by tube chromatography (EA: n-Hex = 1: 4 v / v), ethanol was added to the compound and stirred to form a solid. The solid was filtered and dried to give compound 1-A-3 (2.35 g, 68%).

MS: [M + H] < ⁺ > = 679

PREPARATION EXAMPLE 4 Preparation of Compound 1-A-4

The mixture was stirred and refluxed for 18 hours with 1-A-3 (2.35 g, 3.46 mmol), trifluoromethanesulfonic anhydride (10 mL) and 6M aqueous potassium carbonate solution (20 mL) and acetonitrile solvent . The temperature was lowered to room temperature, the acetonitrile solvent was distilled off, and then methylene chloride and water were added to extract the organic layer. The organic layer was dried over anhydrous magnesium sulfate and vacuum distilled under reduced pressure. The solid produced in this way was added with 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

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

Preparation Example 6 Preparation of Compound 1-A-7

Compound 1-A-6 was prepared by proceeding in the same manner as in Production Example 4, except that Compound 1-A-5 was used instead of Compound 1-A-3.

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

PREPARATION EXAMPLE 7 Preparation of Compound 1-a-16

Compound 1-a-16 was prepared in the same manner as in Production Example 3, except that Compound 1-A-7 was used instead of Compound 1-A-2.

PREPARATION EXAMPLE 8 Preparation of Compound 1-b-31

A compound 4,7-dibromo-2,1,3-benzothiadiazole was used instead of the compound 1-A-1 in Production Example 2, , Compound 1-b-31 was prepared by proceeding in the same manner except that Compound 1-A-20 was used in an amount of 2.4 equivalents 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 in the same manner as in Production Example 2, except that Compound 1-A-8 was used instead of Compound 1-A-1 in Production Example 2 above. MS: [M + H] < ⁺ > = 763

PREPARATION EXAMPLE 10 Preparation of Compound 1-b-25

Compound 1-b-25 was prepared by proceeding in the same manner as in Production Example 3, except that Compound 1-A-9 was used instead of Compound 1-A-2.

MS: [M + H] < ⁺ > = 931

PREPARATION EXAMPLE 11 Preparation of Compound 1-b-32

Compound 1-A-20 was used in place of Compound 1-A-1 in Production Example 5, and Compound 2 -7-dibromo-fluorene -9,9-dioctylfluorene) was used in place of the compound 1-b-32.

MS: [M + H] < ⁺ > = 1675

PREPARATION EXAMPLE 12 Preparation of Compound 1-b-12

Compound 1-b-12 was prepared by proceeding in the same manner as in Production Example 3, except that Compound 1-A-7 was used instead of Compound 1-A-2.

MS: [M + H] < ⁺ > = 1091

Experimental Example

<Experimental Example 1-1-1> The electrochemical characteristics of the compound of Formula 1

In order to observe the electrochemical properties of the compounds prepared in Preparation Examples 7, 10 and 12, oxidation / reduction characteristics were observed using a cyclovoltameter (CV). The CV equipment used was Autolab PGSTAT128N cyclovoltametry, 0.1 M tetrabutylammonium tetrafluoroborate (T ₄ NBF ₄ ) (Tetrabutylammonium tetrafluoroborate) and acetonitrile solvent were used as the electrolyte, and the sample was 10 ^-3 M Dissolved in 1,2-dichlorobenzene. A glass carbon electrode (0.3 mm in diameter) was used as a working electrode and a Pt and Ag / AgCl electrode was used as a counter electrode and a reference electrode. The results are shown in the following table Respectively.

 [Table 5] Energy levels of the above compounds

The HOMO and LUMO values are calculated by assuming that the energy level of ferrocene is -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).

&Lt; Example 1-1-2 > Organic solar cell using P3HT and compound 1-a-16 as a photoactive layer

PEDOT-PSS (Heraeus, CLEVIOS ^TM P) was spin-coated on a cleaned ITO (Indium Tin Oxide) glass substrate (surface resistivity 7 Ω / sq) - (hexylthiophene, P3HT, Rieke Metal Corp.) and the compound 1-a-8 prepared in the present invention were dissolved in 1,2-dichlorobenzene, chlorobenzene, chloroform alone or a mixed solvent thereof in a weight ratio of 1: Coating or the like to form an organic thin film having a thickness of 70 nm. LiF / Al was deposited on the thus formed organic film under the vacuum of 0.7 nm and 120 nm, respectively, and sealed with a glass cap 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

Except that Compound 1-b-12 was used instead of Compound 1-a-16 as the photoactive layer support material, the same as in Example 1-1-2. 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

The same as in Example 1-1-2, except that the compound 1-b-25 was used instead of the compound 1-a-16 as the photoactive layer support 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 the increase in the difference between the HOMO and LUMO values of the electron-donating P3HT compounds of formula (1).

Claims (34)

An imidazole derivative represented by the following formula (1); Or an imidazole derivative having two or more of the above-described structures represented by the following formulas (1) or (2)
[Chemical Formula 1]

In Formula 1,
Ar ₁ is _{- (L 1) p 1 -} (Y 1) , and q _1, Ar ₂ is _{- (L 2) p 2 -} (Y 2) and q _2, 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 or different and are each independently a direct bond; A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An arylene group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A divalent cyclic ketone group of 6 to 60 carbon atoms in aromatic or aliphatic ring of 3 to 60 carbon atoms; A divalent aromatic ring group having 6 to 60 carbon atoms; An aromatic or aliphatic heterocyclic group containing at least one of N, O, and S atoms and having 2 to 60 carbon atoms and substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or an alkoxy group having 1 to 40 carbon atoms; And a condensed ring group of the divalent aromatic ring having 6 to 60 carbon atoms and the heterocyclic ring having 2 to 60 carbon atoms,
At least one of Y ₁ to Y ₄ is represented by the following formula (1-1), and the others are the same or different and each independently hydrogen; A nitrile group; An ester group; Acetate groups; A halogen, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms substituted or unsubstituted with an imide group having 1 to 25 carbon atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of group; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of an aromatic group having 6 to 60 carbon atoms Or a cyclic ketone group of an aliphatic ring having 3 to 60 carbon atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of an aromatic group having 6 to 60 carbon atoms Or an imide group of an aliphatic ring having 3 to 60 carbon atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of an aromatic group having 6 to 60 carbon atoms Ring group; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms , A cyclic ketone group of an aliphatic ring having 3 to 60 carbon atoms and an aromatic group having 6 to 60 carbon atoms, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms An aromatic or aliphatic heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group of the ring, and a heterocyclic group containing at least one of N, O, and S atoms and having 2 to 60 carbon atoms, said substituted or unsubstituted C6 to C60 And a condensed ring group of the above-mentioned heterocyclic ring having 2 to 60 carbon atoms; And an imidazole group substituted or unsubstituted by the formula (1-1), and at least one selected from the group consisting of
[Formula 1-1]

In 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); A carboxyl group (-CO ₂ R); Fluoro group (-F); Or an alkyl group having 1 to 20 carbon atoms substituted with a fluoro group (-F); An alkyl group having 1 to 20 carbon atoms; An alkoxy group having 1 to 40 carbon atoms; An aryl group having 6 to 60 carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms,
Q ₂ is oxygen ( O ),

,

,

,

,

,

And

, &Lt; / RTI &gt;
* Is a moiety linked to Formula 1-1,
a, b, c and d are each an integer of 0 to 4,
R, R 'and R "are the same or different and each independently hydrogen, cyano group (-CN), ester group, cyano group (-CN), ester group, carbonyl group (COR'''); Carboxylic group (CO ₂ R '"); fluoro group (-F); or an alkyl group having 1 to 20 carbon atoms substituted with a group (-F) fluoro; alkyl group having a carbon number of 1 to 20; a cycloalkyl group having a carbon number of 3 to 60; An alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an aromatic or aliphatic heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms, or an aryl group having 6 to 60 carbon atoms ego,
R "&quot; is the same as the definition of R above. 2. The imidazole derivative according to claim 1, wherein Y &lt; ₄ &gt; 2. The imidazole derivative according to claim 1, wherein Y &lt; ₃ &gt; The imidazole derivative according to claim 1, wherein the imidazole derivative represented by formula (1) is represented by any one of formulas (2) and (3)
(2)

(3)

In 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 as defined in formula (1-1). [Claim 4] The imidazole derivative according to claim 1, wherein the imidazole derivative having two or more of the structures represented by the formulas (1) and (2) is bonded via a direct or divalent linking group, In imidazole derivatives:
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In formulas (4) to (6)
r, s and w are integers of 0 to 2,
t, u and v are integers of 0 to 3,
Ar ₃ 'is _{- (L 3') p 3} '- (Y 3') q 3 ' , and, Ar ₃ "is _{- (L 3") p 3} "- (Y 3") q 3 " , and, Ar _a is _{- (L a) p a -} (Y a) q a a, Ar _b is _{- (L b) p b -} (Y b) and q _b, Ar _c is _{- (L c) p c -} (Y c ) and q _c, Ar _d is - (L _d), p _d - (Y _d) q _d is, Ar _e is - (L _e) p _e - and (Y _e) q _e, 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 defined for p ₁ to p ₄ in formula
_{q 3 ', q 3 ",} q a, q b, q c, q d, q e q and _f are as defined in formula (1) of q ₁ to q _4,
L ₃ , L ₃ , L _a , L _b , L _c , L _d , L _e and L _f are the same as defined for 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 defined for Y ₁ to Y ₄ in formula (1)
Ar ₃ is the same as defined in Formula 1,
(4) to (6) contain at least one or more of the above-mentioned formula (1-1)
Z represents a divalent linking group, a direct bond; A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An alkylene group having 1 to 20 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, A cycloalkylene group having 3 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An arylene group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, Or a heterocyclic group having 2 to 60 carbon atoms including at least one group selected from the group consisting of a hydrogen atom, A divalent cyclic ketone group of 6 to 60 carbon atoms in aromatic or aliphatic ring of 3 to 60 carbon atoms; A divalent aromatic ring group having 6 to 60 carbon atoms; An aromatic or aliphatic heterocyclic group containing at least one of N, O, and S atoms and having 2 to 60 carbon atoms and substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or an alkoxy group having 1 to 40 carbon atoms; Or a group having a condensed or non-condensed divalent linking group containing the heterocyclic group having 2 to 60 carbon atoms or the aromatic ring group having 6 to 60 carbon atoms. delete The method according to claim 1, wherein Y ₁ to Y _4, at least one of which is represented by the formula 1-1, and the rest are the same or different and are each independently a halogen, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, or carbon atoms, An alkenyl group having 2 to 40 carbon atoms which is substituted or unsubstituted with an imide group having 1 to 25 carbon atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, or a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group of the ring, and a heterocyclic group having 2 to 60 carbon atoms and containing at least one of N, O, and S atoms, or a naphthyl group substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, An anthracenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a cyclic ketone group of the ring and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, or a fluorenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, or a heterocyclic group substituted with at least one substituent selected from the group consisting of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, or a quinazoline group substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, or a triazine group substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A carbazole group substituted or unsubstituted with at least one substituent selected from the group consisting of a cyclic ketone group of the ring and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of an aromatic group having 6 to 60 carbon atoms Or a cyclic ketone group of an aliphatic ring having 3 to 60 carbon atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of an aromatic group having 6 to 60 carbon atoms Or an imide group of an aliphatic ring having 3 to 60 carbon atoms; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group in the ring, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O, and S atoms, which is unsubstituted or substituted with at least one substituent selected from the group consisting of an aromatic group having 6 to 60 carbon atoms Ring group; A halogen atom, a nitrile group, an alkoxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aromatic group having 6 to 60 carbon atoms, A cyclic ketone group of a ring, and a heterocyclic group having 2 to 60 carbon atoms and containing at least one of N, O, and S atoms, and the heterocyclic group having 6 to 60 carbon atoms which is unsubstituted or substituted with at least one substituent A condensed ring group of an aromatic ring and the above-mentioned heterocyclic ring having 2 to 60 carbon atoms; Or an imidazole group substituted or unsubstituted by the above formula (1-1); And at least one member selected from the group consisting of the above-mentioned formula (1-1). delete The compound according to claim 1, wherein L ₁ to L ₄ are the same or different and each independently represents a halogen, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkylsulfoxy group having 1 to 20 carbon atoms, Substituted with at least one substituent selected from the group consisting of an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms A phenylene group; A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, A biphenylene group substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, A heterocyclic group having 2 to 60 carbon atoms and more than one heteroatom group; And a benzothiadiazolylene group substituted or unsubstituted with an aryl group having 6 to 60 carbon atoms or an alkoxy group having 1 to 40 carbon atoms. [6] The compound according to claim 5, wherein Z is a halogen, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkylsulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An arylene group having 6 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of N, O, and S atoms and a heterocyclic group having 2 to 60 carbon atoms; A divalent condensed ring of the aromatic ring having 6 to 60 carbon atoms and the heterocyclic ring having 2 to 60 carbon atoms; And an imidazole derivative wherein the condensed ring of the arylene group having 6 to 60 carbon atoms and the aromatic ring having 6 to 60 carbon atoms and the heterocyclic ring having 2 to 60 carbon atoms is a group selected from a divalent linking group having 2 or more connected thereto. 11. The imidazole derivative according to 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 and R ₁ are the same or different and each independently hydrogen; A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An alkyl group having 1 to 20 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, A cycloalkyl group having 3 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An alkenyl group having 2 to 40 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms and more than 2 carbon atoms; A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, And an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkylsulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, And a heterocyclic group having 2 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms,
R _d and R _e are hydrogen; A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An alkyl group having 1 to 20 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, A cycloalkyl group having 3 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, A halogen atom, a nitrile group, a nitro group, an alkoxy group having 1 to 40 carbon atoms, an alkyl sulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, An alkoxy group having 1 to 40 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, And an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkylsulfoxy group having 1 to 20 carbon atoms, an imide group having 1 to 25 carbon atoms, an aryl group having 6 to 60 carbon atoms, And an aryloxy group having 6 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms and at least 1 carbon atom. 2. The compound according to claim 1, wherein Q &lt; ₂ &gt;

Lt; RTI ID = 0.0 &gt; imidazole &
Wherein * is a moiety linked to Formula 1-1. 2. The compound according to claim 1, wherein Q &lt; ₂ &gt;

Lt; RTI ID = 0.0 &gt; imidazole &
* Is a moiety linked to 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; A carbonyl group (COR '''), a carboxyl group (CO ₂ R'''); Fluoro group (-F); Or an alkyl group having 1 to 20 carbon atoms substituted with a fluoro group (-F); An alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 60 carbon atoms; An alkoxy group having 1 to 20 carbon atoms; An alkenyl group having 2 to 40 carbon atoms; An aromatic or aliphatic heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms; Or an aryl group having 6 to 60 carbon atoms,
R "&quot; is the same as defined above for R '. The imidazole derivative according to claim 1, wherein the formula (1) is selected from the formulas shown in the following Table 1:
[Table 1]

. The imidazole derivative according to claim 1, wherein the formula (1) is selected from the formulas shown in the following Table 2:
[Table 2]

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

. The imidazole derivative according to claim 1, wherein the formula (1) is selected from the formulas shown in the following Table 4:
[Table 4]

. 1. An organic electronic device comprising 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 formed by the method according to any one of claims 1 to 5, And an imidazole derivative according to any one of claims 1 to 17. 19. The organic electronic device according to claim 18, wherein the organic electronic device is an organic solar cell, an organic light emitting device, an organophotoreceptor or an organic transistor. 19. The organic electroluminescent device according to 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,
Wherein at least one of the organic material layers comprises the imidazole derivative. 21. The organic electronic device according to claim 20, wherein the organic solar cell is a bi-layer p-n junction type. 21. The organic electronic device according to claim 20, wherein the organic solar cell is a bulk heterojunction (BHJ) junction type. The organic electronic device according to claim 20, wherein the imidazole derivative is an electron acceptor material, and the organic material layer further contains an electron donor material. 26. The organic electronic device according to claim 23, wherein the electron donor material is one or more of the following structures:

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; 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. The organic electronic device according to claim 20, wherein the imidazole derivative has a LUMO energy level of -3 to -5 eV. 19. The organic electroluminescent device according to claim 18, wherein the organic electronic device is an organic light emitting 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 material layers comprises the imidazole derivative. 27. The organic electronic device according to claim 26, wherein the organic layer includes a hole injection layer or a hole transport layer containing the imidazole derivative. 27. The organic electronic device according to claim 26, wherein the organic layer includes a light emitting layer containing the imidazole derivative. 27. The organic electronic device according to claim 26, wherein the organic layer comprises an electron transport layer containing the imidazole derivative. 27. The organic electronic device according to claim 26, wherein the organic material layer includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group, or a benzazole group in addition to the organic material layer containing the imidazole derivative. 27. The organic electronic device according to claim 26, wherein the organic compound layer containing the compound includes the imidazole derivative as a host and includes another organic compound, metal or metal compound as a dopant. 19. The organic electroluminescent device according to claim 18, wherein the organic electronic device is an organic transistor including a source, a drain, a gate and one or more organic layers,
Wherein the organic layer comprises the imidazole derivative. 33. The organic electronic device according to claim 32, wherein the organic layer comprises a charge generation layer containing the compound of Formula (1). 19. The organophotoreceptor according to claim 18, wherein the organic electronic device comprises at least one organic layer comprising a first electrode, a second electrode, and an organic photosensitive layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises an imidazole derivative represented by the general formula (1).

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