KR101656560B1 - 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 disclosure provides novel compounds.

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 compound according to one embodiment of the present invention can be represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R1 and R2 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 fluorenyl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,

L is a direct bond; Substituted or unsubstituted with at least one substituent selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heteroaryl, An unsubstituted arylene group,

X is O, S or Se,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,

n and m are each independently an integer of 0 to 8; when n is 2, R1 is the same as or different from each other; when m is 2, R2 is the same as or different from each other;

The compound represented by the formula (1) may be represented by any one of the following formulas (2) to (7).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

R 1, R 2, L, X, Ar 1, Ar 2, n and m are as defined in the formula (1).

In the general formulas (1) to (7), L represents a halogen atom, an alkyl group, an alkenyl group, an alkoxy group, an arylamine group, an aryl group, an arylalkyl group, an arylalkenyl group, a heteroaryl group, a carbazolyl group, a fluorenyl group, Or an arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of R < 1 >

In the general formulas (1) to (7), L is a direct bond; Or an unsubstituted arylene group.

In the general formulas (1) to (7), Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted fluorenyl group.

In the general formulas (1) to (7), Ar1 and Ar2 each independently represent a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted perylenyl group; A substituted or unsubstituted crecenyl group; Or a substituted or unsubstituted fluorenyl group.

In the general formulas (1) to (7), Ar1 and Ar2 each independently represent a phenyl group; Biphenyl group; A terphenyl group; Naphthyl group; Anthracenyl group; Phenanthrene; Pyrenyl; A perylenyl group; A crycenyl group; Or a fluorene group.

In formulas (1) to (7) of the present specification, Ar1 and Ar2 may be the same as each other.

In the general formulas (1) to (7), n and m may each independently be 0 or 1.

Specifically, when n or m is 0, the corresponding R1 or R2 is hydrogen,

when n or m is 1, the corresponding R1 or R2 is 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 fluorenyl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.

In the general formulas (1) to (7), n and m are each independently 0 or 1,

R1 and R2 are each independently selected from the group consisting of hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.

In the formulas (1) to (7) of the present specification, n and m may be 0. Specifically, when n and m are 0, the corresponding R1 or R2 may be hydrogen.

In the general formulas (1) to (7), L is a direct bond; Substituted or unsubstituted with at least one substituent selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heteroaryl, Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted fluorenyl group; R 1 and R 2 are each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, and n and m each independently may be 0 or 1.

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. Specific examples thereof include a cyclopentyl group and a cyclohexyl group, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 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 and a terphenyl group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrene group, a pyrenyl group, a perylenyl group, A fluorene group, and the like, but are not limited thereto.

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

.

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

.

In the present specification, the arylene group means a divalent aryl group, and is the same as the description of the aryl group except that it is a divalent aryl group. Specifically, the arylene group may be substituted with at least one of a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a divalent anthracenyl group, a divalent phenanthrene group, a divalent pyrenyl group, a divalent perylenyl group, And a divalent fluorene group. However, the present invention is not limited thereto.

In this specification, the amine group may be represented by -NR'R ", and the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. The R 'and R" may be the same as or different from each other, Hydrogen; Or an alkyl group. Specific examples thereof include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, an arylamine group means an amine group containing an aryl group in a substituent. Specifically, when an arylamine group is represented by -NR'R ", R 'and R" may be the same or different from each other and represent hydrogen; An alkyl group or an aryl group, and at least one of R 'and R "is an aryl group.

The arylamine group is a substituted or unsubstituted monocyclic arylamine group; A substituted or unsubstituted polycyclic arylamine group; A substituted or unsubstituted monocyclic diarylamine group; A substituted or unsubstituted polycyclic diarylamine group; Or a substituted or unsubstituted mono- and polycyclic diarylamine group. Specific examples thereof include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, Group, a triphenylamine group, and the like, but are not limited thereto.

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

For example, the heterocyclic group is preferably a compound represented by 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.

The term " substituted or unsubstituted " in the present specification means a group selected from the group consisting of deuterium, halogen, alkyl, alkenyl, alkoxy, silyl, arylalkenyl, aryl, Substituted or unsubstituted fluorenyl group and a nitrile group, or has no substituent group.

The compound represented by Formula 1 may be represented by any one of the following formulas.

2-2

2-1

2-2

2-3

2-5

2-4

2-5

2-7

2-6

2-7

2-9

2-8

2-9

2-11

2-10

2-11

2-13

2-12

2-13

2-15

2-14

2-15

2-17

2-16

2-17

2-19

2-18

2-19

2-20

3-2

3-3

3-1

3-2

3-3

3-5

3-4

3-5

3-7

3-6

3-7

3-9

3-8

3-9

3-11

3-10

3-11

3-13

3-12

3-13

3-15

3-14

3-15

3-17

3-16

3-17

3-18

4-2

4-3

4-1

4-2

4-3

4-5

4-6

4-4

4-5

4-6

4-8

4-9

4-7

4-8

4-9

4-11

4-10

4-11

4-13

4-12

4-13

4-14

4-16

4-15

4-16

4-18

4-17

4-18

5-2

5-3

5-1

5-2

5-3

5-5

5-4

5-5

5-7

5-6

5-7

5-9

5-8

5-9

5-11

5-10

5-11

5-13

5-12

5-13

5-14

6-2 6-3

6-1

6-2 6-3

6-5

6-6

6-4

6-5

6-6

6-8

6-9

6-7

6-8

6-9

6-11

6-10

6-11

6-13

6-12

6-13

6-15

6-14

6-15

6-17

6-16

6-17

7-2

7-3

7-1

7-2

7-3

7-5

7-6

7-4

7-5

7-6

7-8

7-9

7-7

7-8

7-9

7-11

7-12

7-10

7-11

7-12

7-14

7-13

7-14

7-16

7-15

7-16

7-18

7-17

7-18

7-19

7-20

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 HOMO level.

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.

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, and at least one of the layers may be represented by Formula 1 ≪ / 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 electronic device of the present specification, the organic material layer includes a layer that simultaneously transports holes / electrons, a layer that simultaneously transports holes and holes, a layer that simultaneously transports holes and emits light, Layer, and at least one of the layers may include a compound represented by the above formula (1).

The organic electronic device according to the present invention may be formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming an anode, forming an organic material layer including a hole injection 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.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. 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 invention may be a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

For example, the structure of the organic electronic device in this specification may have a structure as shown in Figs. 1 and 2, but 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 electronic 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 stacked 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 organic electronic device according to the present specification may be an organic light emitting device.

In the organic light emitting 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, and at least one of the layers may be represented by the formula ≪ / RTI >

In the organic light emitting device of the present specification, 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).

In the organic light emitting device of the present specification, 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 transportation and electron injection, (1). ≪ / RTI >

The compound according to the present invention can be used in an organic layer of an organic light emitting device, and more specifically, can be used in a light emitting 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 the present invention can be used for an organic layer of an organic solar cell, and more specifically, for 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 the present disclosure 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 the present disclosure 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> Synthesis of Compound of Formula (2-1)

[화학식 2-1A]

[Formula 2-1A]

[화학식 2-1B]

[Formula 2-1B]

[화학식 2-1C]

[Chemical Formula 2-1C]

[Chemical Formula 2-1B] [Chemical Formula 2-1C] [Chemical Formula 2-1]

Preparation of Formula 2-1A

Α-Tetralone (14.6 g, 100 mmol) and 1-naphthyl hydrazinium chloride (19.5 g, 100 mmol) were put in ethanol together with 2-3 drops of acetic acid, followed by boiling and stirring. After boiling for 3 hours, water was added and the resulting solid was filtered and dried to give a brown solid (24 g, 85%). MS: [M + H] &lt; ⁺ &gt; = 270

Preparation of Formula 2-1B

(27.0 g, 100 mmol) was dissolved in acetonitrile (MeCN), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone , 6-dicyano-1,4-benzoquinone, DDQ) (22.7 g, 100 mmol) was slowly added thereto, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed by adding water, the resulting solid was filtered, washed with an aqueous potassium carbonate solution, and dried to obtain the compound of Formula 2-1B (25 g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 268

Preparation of Formula 2-1C

1,4-Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-Butyllithium (n-BuLi) (2.5 M, 37 ml, 93 mmol) was slowly added dropwise thereto, followed by stirring for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise and stirred for 3 hours. After warming to room temperature, water (100 ml) was added, and the mixture was extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized with hexane to obtain a white solid, which was dissolved in trichloromethane (200 ml), hydrogen peroxide solution (20 ml) was added, and the mixture was stirred for 12 hours. Magnesium sulfate (MgSO ₄ ) was added and stirred to remove water, followed by filtration, concentration and recrystallization from hexane to obtain the compound of Formula 2-1C (18 g, yield 85%). MS: [M + H] &lt; ⁺ &gt; = 357

Preparation of Formula 2-1

(26.8 g, 100 mmol) and 2-1C (35.7 g, 100 mmol) were dissolved in toluene, and sodium-t-butoxide (14.4 g, -Butyl) ₃ ) ₂ (Pd (t-Butyl) ₃ ) ₂ ) catalyst was added in an amount of 0.1 equivalent and stirred for 3 hours. After the solution was cooled to room temperature, water was added and stirred, and the resulting solid was filtered. The resulting solid was recrystallized from chloroform and ethanol to obtain the compound of Formula 2-1 (42 g, yield 78%). MS: [M + H] &lt; ⁺ &gt; = 544

< Manufacturing example  2> Synthesis of Compound of Formula 2-2

[화학식 2-2A]

[Formula 2-2A]

[Chemical Formula 2-1B] [Chemical Formula 2-2A] [Chemical Formula 2-2]

Preparation of Formula 2-2A

2-2A was obtained in the same manner as in the production of the compound of the formula 2-1C, except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene. MS: [M + H] &lt; ⁺ &gt; = 407

Preparation of Formula 2-2

(2-2) was obtained in the same manner as in the production of the compound of the formula (2-1), except that the compound of the formula (2-2A) was used instead of the compound of the formula (2-1C). MS: [M + H] &lt; ⁺ &gt; = 594

< Manufacturing example  3> Synthesis of compound of formula 2-3

[Chemical Formula 2-1C] [Chemical Formula 2-3A]

[Chemical Formula 2-1B] [Chemical Formula 2-3A] [Chemical Formula 2-3]

Preparation of Formula 2-3A

4-Chloro-phenyl boronic acid (15.6 g, 100 mmol) was dissolved in tetrahydrofuran (THF), and then calcium carbonate (26.7 g, 100 mmol) Aqueous solution was added thereto, and 0.01 equivalent of palladium (phosphorus (phenyl) ₃ ) ₄ ) (Pd (P (Ph) ₃ ) ₄ ) catalyst was added and boiled while stirring. The mixture was stirred for 12 hours and cooled to room temperature. The organic layer was separated and recrystallized from chloroform and ethanol to obtain a white solid (31 g, yield 78%) of formula 2-3A. MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of Formula 2-3

(2-3) was obtained in the same manner as in the preparation of (2-1), except that (2-3A) was used instead of (2-1C). MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  4> Synthesis of Compound of Formula 2-4

[화학식 2-4A]

[Chemical Formula 2-4A]

[Chemical Formula 2-1B] [Chemical Formula 2-4A] [Chemical Formula 2-4]

Preparation of 2-4A

Was prepared in the same manner as in the preparation of the compound of formula (2-3A), except that 3-chloro-phenyl boronic acid was used instead of 4-chloro-phenyl boronic acid 2-4A was obtained. MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of 2-4

2-4 was obtained in the same manner as in the production of the compound of the formula (2-1), except that the compound of the formula (2-4) was used instead of the compound of the formula (2-1). MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  5> Synthesis of Compound of Formula 2-5

[Formula 2-5A]

[Chemical Formula 2-1B] [Chemical Formula 2-5A] [Chemical Formula 2-5]

Preparation of Formula 2-5A

1,4-Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-Butyllithium (n-BuLi) (2.5 M, 37 ml, 93 mmol) was slowly added dropwise thereto, followed by stirring for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise and stirred for 3 hours, then warmed to room temperature, water (100 ml) was added, and the mixture was extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized with hexane to obtain a white solid, which was then dissolved in trichloromethane (200 ml), 1.1 equivalents of sulfur was added, and the mixture was stirred for 12 hours. It was then filtered, concentrated, and recrystallized with hexane to obtain the compound of formula 2-5A (35 g, yield 85%). MS: [M + H] &lt; ⁺ &gt; = 393

Preparation of Formula 2-5

2-5 was obtained in the same manner as in the production of the compound of the formula (2-1), except that the compound of the formula (2-5A) was used instead of the compound of the formula (2-1C). MS: [M + H] &lt; ⁺ &gt; = 560

< Manufacturing example  6> Synthesis of Compound of Formula 2-6

[화학식 2-6A]

[Chemical Formula 2-6A]

[Chemical Formula 2-1B] [Chemical Formula 2-6A] [Chemical Formula 2-6]

Preparation of Formula 2-6A

2-6A was obtained in the same manner as in the production of 2-5A except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene. MS: [M + H] &lt; ⁺ &gt; = 423

Preparation of Formula 2-6

2-6 was obtained in the same manner as in the production of the compound of the formula (2-1), except that the compound of the formula (2-6A) was used instead of the compound of the formula (2-1C). MS: [M + H] &lt; ⁺ &gt; = 610

< Manufacturing example  7> Synthesis of Compound of Formula 2-7

[Chemical Formula 2-5A] [Chemical Formula 2-7A]

[Chemical Formula 2-1B [Chemical Formula 2-7A] [Chemical Formula 2-7]

Preparation of Formula 2-7A

(2-7A) was obtained in the same manner as in the preparation of the compound of the formula (2-3A), except that the compound of the formula (2-5A) was used instead of the compound of the formula (2-1C). MS: [M + H] &lt; ⁺ &gt; = 405

Preparation of 2-7

(2-7) was obtained in the same manner as in the production of the compound of the formula (2-1), except that the compound of the formula (2-7) was used instead of the compound of the formula (2-7). MS: [M + H] &lt; ⁺ &gt; = 636

< Manufacturing example  8> Synthesis of Compound of Formula 2-8

[Chemical Formula 2-5A] [Chemical Formula 2-8A]

[Chemical Formula 2-1B] [Chemical Formula 2-8A] [Chemical Formula 2-8]

Preparation of 2-8A

Was prepared in the same manner as in the method for producing 2-74A except that 3-chloro-phenyl boronic acid was used instead of 4-chloro-phenyl boronic acid. 2-8A. MS: [M + H] &lt; ⁺ &gt; = 405

Preparation of 2-8

(2-8) was obtained in the same manner as in the production of the compound of the formula (2-1), except that the compound of the formula (2-8A) was used instead of the compound of the formula (2-1C). MS: [M + H] &lt; ⁺ &gt; = 636

< Manufacturing example  9> Synthesis of Compound of Formula 2-13

[Chemical Formula 2-1B] [Chemical Formula 2-13]

Preparation of Formula 2-13

Formula 2-1B (26.8 g, 100 mmol) and diphenyl phosphine oxide (diphenylphosphine oxide), palladium (a (t- butyl) ₃₎ was dissolved in a (20.2 g, 100 mmol) in toluene ₂ (Pd (P (t -Butyl) ₃ ) ₂ ) The catalyst was added in an amount of 0.1 equivalent and stirred for 12 hours while boiling. After the solution was cooled to room temperature, water was added and stirred, and the resulting solid was filtered. The resulting solid was recrystallized from chloroform and ethanol to obtain the compound of Formula 2-13 (42 g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 468

< Manufacturing example  10> Synthesis of Compound of Formula 2-14

[Chemical Formula 2-1] [Chemical Formula 2-14A]

[Chemical Formula 2-14A] [Chemical Formula 2-14]

Preparation of Formula 2-14A

(54.4 g, 100 mmol) and N-bromosuccinimide (NBS) (17.8 g, 100 mmol) were dissolved in chloroform and the mixture was stirred at room temperature for 12 hours. After reducing the volume of the solvent, the resulting solid was washed with hexane while filtration to obtain the compound of Formula 2-14A (56 g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 622

Preparation of 2-14

Was prepared in the same manner as in the method for producing the compound of the formula (2-3A), except that phenyl boronic acid was used instead of 4-chloro-phenyl boronic acid, instead of the formula 2-14A, (2-14) was obtained. MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  11> Synthesis of Compound of Formula 2-16

[Chemical Formula 2-1] [Chemical Formula 2-16A]

[Chemical Formula 2-16A] [Chemical Formula 2-16]

Preparation of Formula 2-16A

(54.4 g, 100 mmol) and N-bromosuccinimide (NBS) (35.6 g, 200 mmol) were dissolved in chloroform and stirred at room temperature for 12 hours. After reducing the volume of the solvent, the resulting solid was filtered off and washed with hexane to obtain Formula 2-14A (63 g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 700

Preparation of Formula 2-16

(2-16) was obtained in the same manner as in the production of the compound of the formula (2-1), except that the carbazole was used instead of the compound of the formula (2-16A) and the compound of the formula (2-1B). MS: [M + H] &lt; ⁺ &gt; = 874

< Manufacturing example  12> Synthesis of Compound of Formula 2-18

[Chemical Formula 2-16A] [Chemical Formula 2-18]

Preparation of Formula 2-18

9-phenylcarbazole-3-boronic acid was used in place of 4-chloro-phenyl boronic acid in Chemical Formula 2-16A instead of Chemical Formula 2-1C 2-18 were obtained in the same manner as in the preparation of the compound of formula (2-3A). MS: [M + H] &lt; ⁺ &gt; = 1026

< Manufacturing example  13> Synthesis of Compound of Formula 3-1

[화학식 3-1A]

[Formula 3-1A]

[Formula 3-1A] [Formula 3-1B]

[화학식 3-1C]

[Chemical Formula 3-1C]

[Formula 3-1B] [Formula 3-1C] [Formula 3-1]

Preparation of Formula 3-1A

Α-Tetralone (14.6 g, 100 mmol) and 2-naphthyl hydrazinium chloride (19.5 g, 100 mmol) were put in ethanol together with 2-3 drops of acetic acid, followed by boiling and stirring. After boiling for 3 hours, water was added and the resulting solid was filtered and dried to give a brown solid (24 g, 85%). MS: [M + H] &lt; ⁺ &gt; = 270

Preparation of Formula 3-1B

(27.0 g, 100 mmol) was dissolved in acetonitrile (MeCN), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone , 6-dicyano-1,4-benzoquinone, DDQ) (22.7 g, 100 mmol) was slowly added thereto, and the mixture was stirred at room temperature for 3 hours. After the reaction was terminated by adding water, the resulting solid was filtered, washed with an aqueous potassium carbonate solution, and dried to obtain the compound of Formula 3-1B (25 g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 268

Preparation of Formula 3-1C

1,4-Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-Butyllithium (n-BuLi) (2.5 M, 37 ml, 93 mmol) was slowly added dropwise thereto, followed by stirring for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise and stirred for 3 hours. After warming to room temperature, water (100 ml) was added, and the mixture was extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized with hexane to obtain a white solid, which was then dissolved in trichloromethane (200 ml), followed by addition of hydrogen peroxide solution (20 ml), followed by stirring for 12 hours. Magnesium sulfate (MgSO ₄ ) was added and stirred to remove water, followed by filtration, concentration and recrystallization from hexane to obtain the compound of Formula 3-1C (18 g, yield 85%). MS: [M + H] &lt; ⁺ &gt; = 357

Preparation of Formula 3-1

T-Butoxide (14.4 g, 150 mmol) was added to the solution, and the solution was boiled. Then, palladium (t- Butyl) ₃ ) ₂ (Pd (P (t-Butyl) ₃ ) ₂ ) catalyst was added in an amount of 0.1 equivalent and stirred for 3 hours. After the solution was cooled to room temperature, water was added and stirred, and the resulting solid was filtered. The resulting solid was recrystallized from chloroform and ethanol to obtain the compound of Formula 3-1 (42 g, yield 78%). MS: [M + H] &lt; ⁺ &gt; = 544

< Manufacturing example  14> Synthesis of Compound of Formula 3-2

[화학식 3-2A]

[Formula 3-2A]

[Formula 3-1B] [Formula 3-2A] [Formula 3-2]

Preparation of Formula 3-2A

3-2A was obtained in the same manner as in the production of the compound of the formula 3-1C, except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene. MS: [M + H] &lt; ⁺ &gt; = 407

Preparation of Formula 3-2

(3-2) was obtained in the same manner as in the production of the compound of the formula (3-1), except that the compound of the formula (3-2A) was used instead of the compound of the formula (3-1C). MS: [M + H] &lt; ⁺ &gt; = 594

< Manufacturing example  15> Synthesis of Compound of Formula 3-3

[Formula 3-1C] [Formula 3-3A]

[Formula 3-1B] [Formula 3-3A] [Formula 3-3]

Preparation of Formula 3-3A

4-chloro-phenyl boronic acid (15.6 g, 100 mmol) was dissolved in tetrahydrofuran (THF) and then calcium carbonate Aqueous solution was added, and 0.01 equivalent of palladium (phosphor (Phenyl) ₃ ) ₄ (Pd (P (Ph) ₃ ) ₄ ) catalyst was added and boiled and stirred. The mixture was stirred for 12 hours and cooled to room temperature. The organic layer was separated and recrystallized from chloroform and ethanol to obtain a 3-3A white solid (31 g, yield 78%). MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of 3-3

3-3 was obtained in the same manner as in the production of the compound of the formula (3-1), except that the compound of the formula (3-3A) was used instead of the compound of the formula (3-1C). MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  16> Synthesis of Compound of Formula 3-4

[Chemical Formula 3-1C] [Chemical Formula 3-4A]

[Formula 3-1B] [Formula 3-4A] [Formula 3-4]

Preparation of Formula 3-4A

3-3A, except that 3-chloro-phenyl boronic acid was used in place of 4-chloro-phenyl boronic acid. 3-4A was obtained. MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of 3-4

3-4 was obtained in the same manner as in the production method of the formula (3-1), except that 3-4A was used instead of 3-1C. MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  17> Synthesis of Compound of Formula 3-5

[Formula 3-5A]

[Formula 3-1B] [Formula 3-5A] [Formula 3-5]

Preparation of Formula 3-5A

1,4-Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-Butyllithium (n-BuLi) (2.5 M, 37 ml, 93 mmol) was slowly added dropwise thereto, followed by stirring for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise and stirred for 3 hours. After warming to room temperature, water (100 ml) was added and extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized with hexane to obtain a white solid, which was then dissolved in trichloromethane (200 ml), 1.1 equivalents of sulfur was added, and the mixture was stirred for 12 hours. It was then filtered, concentrated, and recrystallized with hexane to obtain 3-5A (35 g, yield 85%). MS: [M + H] &lt; ⁺ &gt; = 393

Preparation of 3-5

3-5 was obtained in the same manner as in the production of the compound of the formula (3-1), except that the compound of the formula (3-5) was used instead of the compound of the formula (3-1C). MS: [M + H] &lt; ⁺ &gt; = 560

< Manufacturing example  18> Synthesis of Compound of Formula 3-6

[Formula 3-6A]

[Formula 3-1B] [Formula 3-6A] [Formula 3-6]

Preparation of Formula 3-6A

3-6A was obtained in the same manner as in the production of 3-5A except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene. MS: [M + H] &lt; ⁺ &gt; = 423

Preparation of 3-6

3-6 was obtained in the same manner as in the production of the compound of the formula (3-1), except that the compound of the formula (3-6) was used instead of the compound of the formula (3-1C). MS: [M + H] &lt; ⁺ &gt; = 610

< Manufacturing example  19> Synthesis of Compound of Formula 3-7

[Formula 3-5A] [Formula 3-7A]

[Formula 3-1B] [Formula 3-7A] [Formula 3-7]

Preparation of Formula 3-7A

3-7A was obtained in the same manner as in the production of 3-3A, except that 3-5A was used instead of 3-3C. MS: [M + H] &lt; ⁺ &gt; = 405

Preparation of 3-7

(3-7) was obtained in the same manner as in the production of the compound of the formula (3-1), except that the compound of the formula (3-7) was used instead of the compound of the formula (3-1C). MS: [M + H] &lt; ⁺ &gt; = 636

< Manufacturing example  20> Synthesis of Compound of Formula 3-8

[Chemical Formula 3-5A] [Chemical Formula 3-8A]

[Formula 3-1B] [Formula 3-8A] [Formula 3-8]

Preparation of Formula 3-8A

3-7A except that 3-chloro-phenyl boronic acid was used in place of 4-chloro-phenyl boronic acid. 3-8A was obtained. MS: [M + H] &lt; ⁺ &gt; = 405

Preparation of 3-8

3-8 was obtained in the same manner as in the production method of the formula (3-1), except that the compound of the formula (3-1) was used instead of the compound of the formula (3-1). MS: [M + H] &lt; ⁺ &gt; = 636

< Manufacturing example  21> Synthesis of Compound of Formula 5-1

[화학식 5-1A]

[Formula 5-1A]

[화학식 5-1B]

[Formula 5-1B]

[화학식 5-1C]

[Chemical Formula 5-1C]

[Chemical Formula 5-1B] [Chemical Formula 5-1C] [Chemical Formula 5-1]

Preparation of Formula 5-1A

Beta-tetralone (14.6 g, 100 mmol) and 2-naphthyl hydrazinium chloride (19.5 g, 100 mmol) were put in ethanol together with 2-3 drops of acetic acid, followed by boiling and stirring. After boiling for 3 hours, water was added and the resulting solid was filtered and dried to give a brown solid (24 g, 85%). MS: [M + H] &lt; ⁺ &gt; = 270

Preparation of Formula 5-1B

(27.0 g, 100 mmol) was dissolved in acetonitrile (MeCN), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone , 6-dicyano-1,4-benzoquinone, DDQ) (22.7 g, 100 mmol) was slowly added thereto, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed by adding water, the resulting solid was filtered, washed with an aqueous potassium carbonate solution, and dried to obtain the compound of Formula 5-1B (25 g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 268

Preparation of Formula 5-1C

1,4-Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-Butyllithium (n-BuLi) (2.5 M, 37 ml, 93 mmol) was slowly added dropwise thereto, followed by stirring for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise and stirred for 3 hours. After warming to room temperature, water (100 ml) was added, and the mixture was extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized from hexane to obtain a white solid. The residue was dissolved in trichloromethane (200 ml), hydrogen peroxide solution (20 ml) was added, and the mixture was stirred for 12 hours. Magnesium sulfate (MgSO ₄ ) was added and stirred to remove water, followed by filtration, concentration and recrystallization from hexane to obtain the compound of formula 5-1C (18 g, yield 85%). MS: [M + H] &lt; ⁺ &gt; = 357

Preparation of Formula 5-1

The compound of Formula 5-1B (26.8 g, 100 mmol) and the compound of Formula 5-1C (35.7 g, 100 mmol) were dissolved in toluene, sodium-t-butoxide (14.4 g, -Butyl) ₃ ) ₂ (Pd (t-Butyl) ₃ ) ₂ ) catalyst was added in an amount of 0.1 equivalent and stirred for 3 hours. After the solution was cooled to room temperature, water was added and stirred, and the resulting solid was filtered. The resulting solid was recrystallized from chloroform and ethanol to give 5-1 (42 g, yield 78%). MS: [M + H] &lt; ⁺ &gt; = 544

< Manufacturing example  22> Synthesis of Compound of Formula 5-2

[화학식 5-2A]

[Formula 5-2A]

[Formula 5-1B] [Formula 5-2A] [Formula 5-2]

Preparation of Formula 5-2A

5-2A was obtained in the same manner as in the preparation of the compound of the formula 5-1C, except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene. MS: [M + H] &lt; ⁺ &gt; = 407

Preparation of Formula 5-2

5-2 was obtained in the same manner as in the production of the compound of the formula 5-1 except that the compound of the formula 5-2A was used instead of the compound of the formula 5-1C. MS: [M + H] &lt; ⁺ &gt; = 594

< Manufacturing example  23> Synthesis of Compound of Formula 5-3

[Formula 5-1C] [Formula 5-3A]

[Formula 5-1B] [Formula 5-3A] [Formula 5-3]

Preparation of Formula 5-3A

4-chloro-phenyl boronic acid (15.6 g, 100 mmol) was dissolved in tetrahydrofuran (THF), and then calcium carbonate Aqueous solution was added thereto, and 0.01 equivalent of palladium (phosphorus (phenyl) ₃ ) ₄ ) (Pd (P (Ph) ₃ ) ₄ ) catalyst was added and boiled while stirring. The mixture was stirred for 12 hours and cooled to room temperature. The organic layer was separated and recrystallized from chloroform and ethanol to obtain a white solid (31 g, yield 78%) represented by the formula 5-3A. MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of 5-3

5-3 was obtained in the same manner as in the production method of the formula 5-1 except that the compound 5-3A was used instead of the compound 5-1C. MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  24> Synthesis of Compound of Formula 5-4

[Chemical Formula 5-1C] [Chemical Formula 5-4A]

[Formula 5-1B] [Formula 5-4A] [Formula 5-4]

Preparation of Formula 5-4A

3-3A, except that 3-chloro-phenyl boronic acid was used in place of 4-chloro-phenyl boronic acid. 5-4A was obtained. MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of 5-4

5-4 was obtained in the same manner as in the production of the compound of the formula 5-1 except that the compound of the formula 5-4A was used instead of the compound of the formula 5-1C. MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  25> Synthesis of Compound of Formula 7-1

[화학식 7-1A]

[Formula 7-1A]

[화학식 7-1B]

[Formula 7-1B]

[화학식 7-1C]

[Chemical Formula 7-1C]

[Formula 7-1-1B] [Formula 7-1-1]

Preparation of Formula 7-1A

2-Aminonaphthalene (14.3 g, 100 mmol) and iron chloride hydrate (1.95 g, 10 mmol) were put in ethanol together with 2-3 drops of acetic acid, followed by boiling and stirring. After boiling for 3 hours, water was added, and the resulting solid was filtered and dried to obtain a brown solid (24 g, 85%) of the formula 7-1A. MS: [M + H] &lt; ⁺ &gt; = 285

Preparation of Formula 7-1B

7-1A (28.5 g, 100 mmol) was dissolved in acetonitrile (MeCN), and 10 ml of hydrochloric acid was slowly added thereto, followed by stirring at room temperature for 3 hours. After the reaction was completed by adding water, the resulting solid was filtered, washed with an aqueous solution of potassium carbonate and dried to obtain the compound of Formula 7-1B (25 g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 268

Preparation of 7-1C

1,4-Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-Butyllithium (n-BuLi) (2.5 M, 37 ml, 93 mmol) was slowly added dropwise thereto, followed by stirring for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise and stirred for 3 hours. After warming to room temperature, water (100 ml) was added, and the mixture was extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized with hexane to obtain a white solid. The residue was dissolved in trichloromethane (200 ml), and hydrogen peroxide solution (20 ml) was added thereto, followed by stirring for 12 hours. Magnesium sulfate (MgSO ₄ ) was added and stirred to remove water, followed by filtration, concentration and recrystallization from hexane to obtain the compound of formula 7-1C (18 g, yield 85%). MS: [M + H] &lt; ⁺ &gt; = 357

Preparation of Formula 7-1

(26.8 g, 100 mmol) and the compound of the formula 7-1C (35.7 g, 100 mmol) were dissolved in toluene, sodium-t-butoxide (14.4 g, 150 mmol) was added, boiled, and palladium -Butyl) ₃ ) ₂ (Pd (t-Butyl) ₃ ) ₂ ) catalyst was added in an amount of 0.1 equivalent and stirred for 3 hours. After the solution was cooled to room temperature, water was added and stirred, and the resulting solid was filtered. The resulting solid was recrystallized from chloroform and ethanol to obtain the compound of Formula 7-1 (42 g, yield 78%). MS: [M + H] &lt; ⁺ &gt; = 544

< Manufacturing example  26> Synthesis of Compound of Formula 7-2

[화학식 7-2A]

[Formula 7-2A]

[Formula 7-1B] [Formula 7-2A] [Formula 7-2]

Preparation of Formula 7-2A

7-2A was obtained in the same manner as in the production of the compound of the formula 7-1C, except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene. MS: [M + H] &lt; ⁺ &gt; = 407

Preparation of Formula 7-2

7-2 was obtained in the same manner as in the production of the compound of the formula 7-1 except that the compound of the formula 7-2A was used instead of the compound of the formula 7-1C. MS: [M + H] &lt; ⁺ &gt; = 594

< Manufacturing example  27> Synthesis of Compound of Formula 7-3

[Chemical Formula 7-1C] [Chemical Formula 7-3A]

[Formula 7-1B] [Formula 7-3A] [Formula 7-3]

Preparation of Formula 7-3A

4-Chloro-phenyl boronic acid (15.6 g, 100 mmol) was dissolved in tetrahydrofuran (THF) and then calcium carbonate (26.7 g, 100 mmol) Aqueous solution was added thereto, and Pd (P (Ph3) 4) catalyst was added in an amount of 0.01 equivalent, and the mixture was stirred while boiling. After stirring for 12 hours, the mixture was cooled to room temperature and the organic layer was separated, and recrystallized from chloroform and ethanol to obtain a white solid (31 g, 78%), MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of Formula 7-3

7-3 was obtained in the same manner as in the production of the compound of the formula 7-1 except that the compound of the formula 7-3A was used instead of the compound of the formula 7-1C. MS: [M + H] &lt; ⁺ &gt; = 620

< Manufacturing example  28> Synthesis of Compound of Formula 7-4

[Chemical Formula 7-1C] [Chemical Formula 7-4A]

[Chemical Formula 7-1B] [Chemical Formula 7-4A] [Chemical Formula 7-4]

Preparation of Formula 7-4A

7-3A, except that 3-chloro-phenyl boronic acid was used in place of 4-chloro-phenyl boronic acid. 7-4A was obtained. MS: [M + H] &lt; ⁺ &gt; = 389

Preparation of Formula 7-4

7-4 was obtained in the same manner as in the preparation of compound of formula (7-1), except that compound of formula (7-4A) was used instead of compound of formula (7-1-1C). MS: [M + H] &lt; ⁺ &gt; = 620

< Example  1>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. The detergent was a product of Fischer Co., and the distilled water was distilled water secondarily filtered with a filter manufactured by Millipore Co. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, ultrasonic washing was performed in the order of solvent of isopropyl alcohol, acetone, and methanol, and dried.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. A compound (400 ANGSTROM) represented by the following NPB, which is a material for transporting holes, was vacuum-deposited thereon, and as a host, a compound represented by Formula 2-1 synthesized in Preparation Example 1 and a compound represented by D1 shown below as a dopant 10 wt% of the total composition of the light emitting layer) was vacuum-deposited on the light emitting layer to a thickness of 300 ANGSTROM. Then, the compound represented by the following E1 and lithium quinolate (LiQ) were thermally vacuum-deposited together with a (200 A) electron transporting layer. Lithium quinolate (LiQ) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium quinolate was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

[Hexanitrile hexaazatriphenylene] [NPB]

[D1] [E1]

< Example  2>

The same experiment was carried out as in Example 1 except that the compound represented by Formula 2-3 was used in place of the compound represented by Formula 2-1 as the light emitting layer host.

< Example  3>

The same experiment was conducted as in Example 1 except that the compound represented by Formula (3-1) was used in place of the compound represented by Formula (2-1) as the light emitting layer host.

< Example  4>

The same experiment was conducted as in Example 1 except that the compound represented by Formula 7-1 was used in place of the compound represented by Formula 2-1 as a host for the light emitting layer.

< Comparative Example  1>

The same experiment was carried out as in Example 1 except that the compound represented by the following CBP was used in place of the compound represented by the formula (2-1) as the host for the light emitting layer.

[CBP]

Table 1 shows the results of an experiment on an organic light emitting device manufactured by using each compound as a light emitting layer host as in the above embodiment.

Claims (11)

A compound represented by any one of the following formulas (2) to (7);
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 2 to 7,
R1 and R2 are each independently hydrogen,
L is an arylene group having 6 to 12 carbon atoms,
X is O,
Ar 1 and Ar 2 are each independently a phenyl group,
n and m are each independently 6. delete delete delete delete delete delete The compound according to claim 1, wherein the compound represented by any one of formulas (2) to (7) is represented by any one of the following formulas:
2-1

2-3

2-4

3-1

3-2

3-3

3-4

4-1

4-2

4-3

4-4

5-1

5-2

5-3

5-4

6-1

6-2

6-3

6-4

7-1

7-2

7-3

7-4

1. 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 comprises a compound according to any one of claims 1 and 8 Organic electronic device. The organic EL device according to claim 9, wherein the organic material layer includes at least one of an electron blocking layer, an electron injecting layer and an electron transporting layer, and at least one of the electron blocking layer, the electron injecting layer, Electronic device. The organic electronic device according to claim 9, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.

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