KR101625284B1 - Aromatic compounds and organic electronic device using the same - Google Patents

Abstract

The present invention relates to an organic electronic device in which a novel compound capable of improving lifetime, efficiency, driving voltage drop and stability of an organic electronic device is contained in an organic material layer.

Description

TECHNICAL FIELD [0001] The present invention relates to an aromatic compound, and an organic electronic device using the same. BACKGROUND ART [0002] AROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICE USING THE SAME [

The present invention relates to an organic electronic device in which a novel compound capable of improving lifetime, efficiency, driving voltage drop and stability of an organic electronic device is contained in an organic material layer.

An organic electronic device means an element requiring charge exchange between an electrode and an organic material using holes and / or electrons. The organic electronic device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electric device. The second type is an electronic device that injects holes and / or electrons into an organic semiconductor that interfaces with an electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of the organic electronic device include an organic electronic device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like. All of them are used for hole injecting or transporting materials, electron injecting or transporting materials, need. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials act on a similar principle.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electronic device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multi-layer structure composed of different materials, and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of the organic electronic device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic electronic device is known to have characteristics such as self-emission, high luminance, high efficiency, low drive voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic electronic device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic electronic device to sufficiently exhibit the above-described excellent characteristics, it is required that materials constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material are supported by a stable and efficient material However, stable and efficient organic material layer materials for organic electronic devices have not yet been sufficiently developed. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

Korean Patent Publication No. 2000-0051826

Accordingly, the present inventors have found that a compound having a chemical structure capable of fulfilling various conditions required for a material usable in an organic electronic device, such as lifetime, efficiency, driving voltage drop and stability, And an organic electronic device comprising the compound.

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1, X is NR, O or S, and Ring A and Ring B are each independently a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group containing two or more N, R1 to R3 and R are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 aryl group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, and two or more adjacent groups of R1 to R3 and R may be bonded to each other to form a monocyclic or polycyclic ring, , n and o are integers of 0 to 4, m is an integer of 0 to 2, and when the substituents in the parentheses are 2 or more, they are the same or different and at least one of ring A and ring B is a heterocyclic group.

The present invention also relates to an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes the compound The organic electroluminescent device comprising:

The organic electronic device according to one embodiment of the present invention has an advantage of improving lifetime characteristics.

The organic electronic device according to one embodiment of the present invention has an advantage that the light efficiency is improved.

The organic electronic device according to one embodiment of the present invention has an advantage of having a low driving voltage.

The organic electronic device according to one embodiment of the present invention has an advantage of improving electrochemical stability and thermal stability

1 shows an example of an organic electronic device made up of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 shows an example of an organic electronic device composed of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

Hereinafter, the present invention will be described in detail.

The present disclosure provides aromatic compounds, specifically nitrogen-containing heterocyclic compounds.

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1, X is NR, O or S, and Ring A and Ring B are each independently a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group containing two or more N, R1 to R3 and R are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 aryl group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, and two or more adjacent groups of R1 to R3 and R may be bonded to each other to form a monocyclic or polycyclic ring, , n and o are integers of 0 to 4, m is an integer of 0 to 2, and when the substituents in the parentheses are 2 or more, they are the same or different and at least one of ring A and ring B is a heterocyclic group.

In one embodiment of the present invention, Ring A or Ring B may be a substituted or unsubstituted heterocyclic group containing two or more N atoms.

In one embodiment of the present specification, Ring A or Ring B may be a substituted or unsubstituted heterocyclic group containing two N's.

In one embodiment of the present disclosure, when X is NR, R can be a substituted or unsubstituted aryl group.

In one embodiment of the present disclosure, when X is NR, R can be an unsubstituted aryl group.

In one embodiment of the present specification, when X is NR, R may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group or an anthracenyl group.

In one embodiment of the present specification, when X is NR, R may be a phenyl group.

In one embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 2 below.

(2)

Wherein Z 1 to Z 8 are each independently CR 'or N, and at least two of Z 1 to Z 4 are N or Z 5 to Z 8, Two or more of which are N, and R 'is each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 aryl group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, and at least two adjacent groups of R1 to R3, R and R 'are bonded to each other to form a monocyclic or polycyclic ring can do.

In one embodiment of the present invention, the compound represented by the formula (1) may be represented by any one of the following formulas (3) to (8).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

Wherein Z 1 to Z 8 are each independently CR 'or N, and at least two of Z 1 to Z 4 are N or Z 5 to Z 4 are the same as defined in formula And Z < 8 > are N, and R 'is each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 aryl group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, and at least two adjacent groups of R1 to R3, R and R 'are bonded to each other to form a monocyclic or polycyclic ring can do.

In the above formulas (3) to (8), two of Z1 to Z4 may be N or two of Z5 to Z8 may be N. [

In the above formulas 3 to 8, Z2 and Z4 may be N, or Z5 and Z7 may be N. [

In the above formulas 3 to 8, Z2 and Z4 may be N, and Z1, Z3 and Z5 to Z8 may be CR '.

In the above formulas 3 to 8, Z5 and Z7 may be N, and Z1 to Z4, Z6 and Z8 may be CR '.

In the above Chemical Formulas 3 to 8, Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', and R4 and R5 are each independently a substituted or unsubstituted aryl group.

In the above Formulas 3 to 8, Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', and R4 and R5 are each independently an unsubstituted aryl group.

Wherein Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', R4 and R5 are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, Anthracenyl group.

In the above Formulas 3 to 8, Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', and R4 and R5 are each independently a phenyl group, a biphenyl group or a naphthyl group.

Wherein Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', R' is hydrogen, R4 and R5 are each independently a phenyl group, a biphenyl group, A naphthyl group, or an anthracenyl group.

Wherein Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', R' is hydrogen, R4 and R5 are each independently a phenyl group, Naphthyl group.

In the above formulas 3 to 8, Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', and R6 and R7 are each independently a substituted or unsubstituted aryl group.

In the above formulas 3 to 8, Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', and R6 and R7 are each independently an unsubstituted aryl group.

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', and R6 and R7 each independently represent a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, Anthracenyl group.

In the above formulas 3 to 8, Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', and R6 and R7 are each independently a phenyl group, a biphenyl group or a naphthyl group.

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', R' is hydrogen, R6 and R7 are each independently a phenyl group, a biphenyl group, A naphthyl group, or an anthracenyl group.

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', R' is hydrogen, R6 and R7 are each independently a phenyl group, Naphthyl group.

In the above formulas 3 and 5, Z2 and Z4 may be N, and Z1, Z3 and Z5 to Z8 may be CR '.

In the above formulas 3 and 5, Z5 and Z7 may be N, and Z1 to Z4, Z6 and Z8 may be CR '.

In the above formulas 3 and 5, Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', and R4 and R5 are each independently a substituted or unsubstituted aryl group.

In the above formulas 3 and 5, Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', and R4 and R5 are each independently an unsubstituted aryl group.

Wherein Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', R4 and R5 are each independently phenyl, biphenyl, terphenyl, naphthyl or Anthracenyl group.

In the above formulas 3 and 5, Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', and R4 and R5 are each independently a phenyl group, a biphenyl group or a naphthyl group.

Wherein Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', R' is hydrogen, R4 and R5 are each independently a phenyl group, a biphenyl group, A naphthyl group, or an anthracenyl group.

Wherein Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR ', R' is hydrogen, R4 and R5 are each independently a phenyl group, Naphthyl group.

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', and R6 and R7 are each independently a substituted or unsubstituted aryl group .

In the above formulas 4, 6, 7 and 8, Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', and R6 and R7 are each independently an unsubstituted aryl group .

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', R6 and R7 are each independently a phenyl group, a biphenyl group, a terphenyl group , Naphthyl group or anthracenyl group.

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', and R6 and R7 are each independently a phenyl group, a biphenyl group or a naphthyl group .

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', R' is hydrogen, R6 and R7 are each independently phenyl , A biphenyl group, a terphenyl group, a naphthyl group or an anthracenyl group.

Wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR ', R' is hydrogen, R6 and R7 are each independently phenyl , Biphenyl group or naphthyl group.

In one embodiment of the present disclosure, any one of R 1, R 2, and R 3 may be hydrogen.

In one embodiment of the present disclosure, R1, R2 and R3 may be hydrogen.

In the compounds according to the present specification, the substituents of the above formula (1) will be described in more detail as follows.

In the present specification, examples of the halogen group include, but are not limited to, fluorine, chlorine, bromine, and iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 12. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

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, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 12. Specific examples include a butenyl group; Pentenyl; Or an alkenyl group to which an aryl group such as a stilbenyl group or a styrenyl group is bonded, but is not limited thereto.

In the present specification, the alkoxy group preferably has 1 to 12 carbon atoms, more specifically, methoxy, ethoxy, isopropyloxy, and the like, but is not limited thereto.

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 40. 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 phenanthrene group, a pyrenyl group, a perylenyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group,

등이 있다.In the present specification, a fluorene group is a structure in which two cyclic organic compounds are connected through one atom,

.

등이 있다.In the present specification, a fluorene group includes a structure of an open fluorene group, wherein an open fluorene group has a structure in which one of the ring compounds is disconnected in a structure in which two ring compounds are connected via one atom,

.

In the present specification, the number of carbon atoms of the alkylamine group is not particularly limited, but is preferably 1 to 30. Specific examples of the alkylamine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, the arylamine group is an amine group having an aryl group as a substituent, and examples thereof include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or a substituted or unsubstituted And may be a mono-cyclic or polycyclic diarylamine group. For example, there may be mentioned a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, -Methyl-anthracenylamine group, and the like, but are not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O and S atoms. 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 benzzcarbazole group, a benzthiophene group, a dibenzothiophene group, a benzfuranyl group, But are not limited to these.

Specifically, the heterocyclic group is preferably a compound having the following structural formula, but is 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, the hydrocarbon ring group is a ring group composed of only carbon and hydrogen, and is not particularly limited. For example, the hydrocarbon ring group may be a fluorene group or an aromatic hydrocarbon ring group composed of an aliphatic hydrocarbon ring group, carbon and hydrogen only. Here, the aliphatic hydrocarbon ring group may be selected from among the examples of the above-mentioned cycloalkyl group, and the aromatic hydrocarbon ring group may be selected from the examples of the above-mentioned aryl group.

The term "substituted or unsubstituted" in the present specification refers to a substituted or unsubstituted group such as a deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a silyl group, an arylalkenyl group, an aryl group, a heteroaryl group, An unsubstituted fluorenyl group, and a nitrile group, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the "monocyclic or polycyclic ring formed by bonding together with adjacent groups" may be a hydrocarbon ring or a heterocyclic ring.

In one embodiment of the present invention, the compound represented by Formula 1 may be represented by any of Formula 1 to Formula 54 below.

The novel compounds according to the present invention have the advantage of excellent thermal stability.

The novel compounds according to the present invention have the advantage of having a deep highest level occupied molecular orbital (HOMO).

The novel compounds according to the present invention have the advantage of having a high triplet state.

The novel compounds according to the present invention have the advantage of having hole stability.

The novel compound according to the present invention can be used purely in an organic electronic device including a light emitting device, or mixed with an impurity.

Further, by introducing various substituent groups into the core structure, it is possible to finely control the energy band gap, and the characteristics at the interface between the organic materials can be improved and the use of the materials can be diversified.

On the other hand, the compound represented by the formula (1) has a high glass transition temperature (Tg) and is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

The organic electronic device according to the present invention has an advantage of improving the light efficiency and improving lifetime characteristics of the device by high thermal stability.

Further, the organic electronic device according to the present invention is an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers And a compound represented by the above formula (1).

Examples of the organic electronic device include, but are not limited to, an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

The organic electronic device of the present invention 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 compound represented by the above-described formula (1).

The compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic electronic device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic electronic device in this specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic electronic device in this specification may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and the like as an organic material layer. However, the structure of the organic electronic device is not limited to this, and may include a smaller number of organic layers.

Therefore, in the organic electronic device of the present specification, the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, Lt; / RTI >

In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).

The organic material layer may include at least one of an electron blocking layer, an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection, and at least one of the layers may be a compound . ≪ / RTI >

In the organic compound layer having such a multi-layer structure, the compound represented by the formula (1) may be used in combination with a light emitting layer, a layer that simultaneously transports holes / electrons, a layer that simultaneously transports holes and holes, A layer simultaneously transporting and emitting light, and the like.

In addition, the compound of the present invention can be used as an organic material layer material in an organic electronic device, particularly, as a light emitting layer, an electron transporting layer, and the like.

The organic electronic device according to the present invention may be formed by depositing a metal or conductive metal oxide or a metal oxide on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Depositing an anode to form an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode, and depositing a material usable as a cathode thereon. In addition to such a method, an organic electronic device may be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into 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; And conductive polymers such as poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

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

The hole injecting material is a material capable of injecting holes from the anode at a low voltage. The highest occupied molecular orbital (HOMO) of the hole injecting material is a function of the work function of the anode material and the highest level It is preferable to be between the occupied molecular orbital. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The organic electronic device according to the present specification may be an organic light emitting device.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 shows a structure of an organic electronic device in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially laminated on a substrate 1. [ In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.

The compound according to one embodiment of the present invention can be used for an organic layer of an organic light emitting device, and more specifically, can be used for a light emitting layer or an electron transporting layer.

The organic solar cell according to the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic material layer may include a hole transporting layer, a photoactive layer, and an electron transporting layer. The compound according to one embodiment of the present invention can be used for an organic layer of an organic solar cell, and more specifically, can be used for a photoactive layer or an electron transporting layer.

An organophotoreceptor according to the present disclosure may comprise a conductive substrate, a charge transport layer comprising an electron transport material, and a charge generating layer. The compounds according to one embodiment herein can be used in the charge transport layer of an organophotoreceptor.

The organic transistor according to the present invention may include a first electrode, a second electrode, a hole injection layer, an organic thin film layer, an electron injection layer, and an electron transport layer. The compounds according to one embodiment herein can be used in an electron transport layer of an organic transistor.

The method for preparing the compound of Formula 1 and the production of the organic electronic device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

[Example]

< Manufacturing example  1> Preparation of the structural formula 7

[Compound A] [Compound B] [Compound C] [Structural formula 7]

Tetrahydrofuran (200 mL) was added to Compound A (20.0 g, 50.4 mmol) and cooled to -78 ° C. 2.5M n-butyllithium (n-BuLi) (20.1 ml, 50.4 mmol) was added thereto, and the mixture was stirred at -78 ° C for 1 hour. Compound B (15.3 g, 45.8 mmol) was added thereto, stirred at -78 ° C for 30 minutes, and then heated to room temperature. An aqueous ammonium chloride solution (aq NH ₄ Cl) (50 ml) was added and the organic layer was separated. The organic layer was distilled under reduced pressure, adsorbed on silica gel, and then subjected to column chromatography to obtain Compound C (19.1 g, 58%).

Compound C (19.1g, 29.2mmol), it was reflux (reflux) for 5 h then a solution of acetic acid (Acetic acid) (200ml) and concentrated sulfuric acid _{(conc. H 2 SO 4)} (0.1ml). After cooling to room temperature, the resulting solid was filtered. The solid was adsorbed onto silica gel and columned to give structural formula 7 (3.2 g, 17%).

MS: [M + H] &lt; ⁺ &gt; = 635

< Manufacturing example  2> Preparation of the structural formula 8

[Compound D] [Compound B] [Compound E] [Structural formula 8]

Tetrahydrofuran (200 mL) was added to Compound D (20.0 g, 59.2 mmol), and the mixture was cooled to -78 ° C. 2.5M n-butyl lithium (23.7 ml, 59.2 mmol) was added thereto, and the mixture was stirred at -78 ° C for 1 hour. Compound B (18.0 g, 53.8 mmol) was added thereto, and the mixture was stirred at -78 ° C for 30 minutes, and the temperature was raised to room temperature. An ammonium chloride aqueous solution (50 ml) was added and the organic layer was separated. The organic layer was distilled under reduced pressure, adsorbed onto silica gel, and then subjected to column chromatography to obtain Compound E (22.2 g, 63%).

Compound E (22.2 g, 37.3 mmol), acetic acid (200 ml) and concentrated sulfuric acid (0.1 ml) were mixed and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered. The solid was adsorbed onto silica gel and columned to give structural formula 8 (9.7 g, 45%).

MS: [M + H] &lt; ⁺ &gt; = 576

< Manufacturing example  3> Preparation of structural formula 14

[Compound F] [Compound B] [Compound G] [Structural Formula 14]

Tetrahydrofuran (200 mL) was added to Compound F (20.0 g, 50.4 mmol) and cooled to -78 ° C. 2.5M n-butyl lithium (20.1 ml, 50.4 mmol) was added thereto, and the mixture was stirred at -78 ° C for 1 hour. Compound B (15.3 g, 45.8 mmol) was added thereto, stirred at -78 ° C for 30 minutes, and then heated to room temperature. An ammonium chloride aqueous solution (50 ml) was added and the organic layer was separated. The organic layer was distilled under reduced pressure, adsorbed on silica gel, and then subjected to column chromatography to obtain Compound G (17.8 g, 54%).

Compound G (17.8 g, 27.2 mmol), acetic acid (200 ml) and concentrated sulfuric acid (0.1 ml) were mixed and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered. The solid was adsorbed onto silica gel and columned to give structural formula 14 (8.1 g, 47%).

MS: [M + H] &lt; ⁺ &gt; = 635

< Example  1>

A glass substrate coated with a thin film of ITO (indium tin oxide) (thickness 500 Å) was washed with ultrasonic waves in distilled water containing detergent. At this time, a Fischer Co. product was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The indium tin oxide was washed for 30 minutes, then repeated twice with distilled water, and ultrasonically washed for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the thus prepared indium tin oxide transparent electrode to form a hole injection layer.

[LINE] [NPB]

(NPB) (250 Å), hexanitrile hexaazatriphenylene (HAT) (50 Å), and the like were added to the hole injection layer. ) And 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400A) were successively vacuum-deposited to form a hole transport layer.

Subsequently, the compound of Formula 7 and the following dopant compound GD were vapor-deposited at a weight ratio of 10: 1 on the hole transport layer to a film thickness of 300 ANGSTROM to form a light emitting layer.

   [GD] [ET-A] [LiQ]

A compound of the above formula (ET-A) and the above-mentioned lithium quinolin-8-olate (LiQ) were vacuum deposited on the light emitting layer as an electron transporting layer material at a weight ratio of 1: And a transport layer were formed.

Lithium fluoride (LiF) and aluminum having a thickness of 1,000 ANGSTROM were sequentially deposited on the electron injecting and transporting layer to a thickness of 15 ANGSTROM to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode maintained the deposition rate of 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr to produce an organic light emitting device.

< Example  2>

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of Formula 8 was used in place of the compound of Formula 7 of Example 1.

< Example  3>

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of Formula 14 was used in place of the compound of Formula 7 in Example 1.

< Comparative Example  1>

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compound of the formula GH-A was used instead of the compound of the formula 7 of the example 1.

 [GH-A]

When current (10 mA / cm ² ) was applied to the organic light-emitting device fabricated by Example 1-3 and Comparative Example 1, the results shown in Table 1 below were obtained.

From the results of Table 1, it can be seen that the novel compound according to the present invention can be used as a material for a light emitting layer of an organic electronic device including an organic light emitting device, and an organic electronic device including the organic light emitting device can be used It can be seen that it exhibits excellent characteristics. Particularly, it is possible to lower the driving voltage and induce an increase in efficiency, thereby improving the power consumption.

Claims (14)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X is NR, O or S,
Ring A and Ring B each independently represent a substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group containing two or more N,
The ring A or ring B is a substituted or unsubstituted heterocyclic group containing two or more N,
R1 to R3 and R are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 aryl group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, and two or more adjacent groups of R1 to R3 and R may be bonded to each other to form a monocyclic or polycyclic ring, ,
n and o are integers of 0 to 4, m is an integer of 0 to 2,
And when at least two of the substituents in the parentheses are the same or different, at least one of the ring A and the ring B is a heterocyclic group,
The "substituted or unsubstituted" substituent may be a group selected from the group consisting of deuterium, halogen, alkyl, alkenyl, alkoxy, silyl, arylalkenyl, aryl, A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, delete The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2:
(2)

In Formula 2,
X, R1 to R3, n, m and o are the same as defined in formula (1)
Z1 to Z8 are each independently CR 'or N,
At least two of Z1 to Z4 are N, two or more of Z5 to Z8 are N,
R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 aryl group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, and at least two adjacent groups of R1 to R3, R and R 'are bonded to each other to form a monocyclic or polycyclic ring can do. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (8)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above Formulas 3 to 8,
X, R1 to R3, n, m and o are the same as defined in formula (1)
Z1 to Z8 are each independently CR 'or N
At least two of Z1 to Z4 are N, two or more of Z5 to Z8 are N,
R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 aryl group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,
Two or more adjacent groups among R1 to R3, R and R 'may be bonded to each other to form a monocyclic or polycyclic ring. 5. The compound according to claim 4, wherein two of Z1 to Z4 are N or two of Z5 to Z8 are N. 5. The compound according to claim 4, wherein Z2 and Z4 are N or Z5 and Z7 are N. 5. The compound according to claim 4, wherein Z2 and Z4 are N, Z1, Z3 and Z5 to Z8 are CR 'and R' are each independently the same as defined in claim 4. 5. The compound according to claim 4, wherein Z5 and Z7 are N, Z1 to Z4, Z6 and Z8 are CR 'and each R' is independently the same as defined in claim 4. 5. The compound according to claim 4, wherein Z2 and Z4 are N, Z1 is CR4, Z3 is CR5, Z5 to Z8 are CR '
R ' are each independently the same as R ' in claim 4,
R4 and R5 are each independently a substituted or unsubstituted aryl group. 5. The compound according to claim 4, wherein Z5 and Z7 are N, Z6 is CR6, Z8 is CR7, Z1 to Z4 are CR '
R ' are each independently the same as R ' in claim 4,
Lt; 6 &gt; and R &lt; 7 &gt; are each independently a substituted or unsubstituted aryl group. The compound according to claim 1, wherein the compound represented by Formula 1 is any one of the following Formulas 1 to 54:

An organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises the compound of any one of claims 1 and 3 to 11. 13. The organic electroluminescent device according to claim 12, wherein the organic material layer includes at least one of an electron blocking layer, an electron injection layer and an electron transporting layer, and at least one of the electron blocking layer, Electronic device. The organic electronic device according to claim 12, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.

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