KR20150115225A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic luminescent compound used in an organic electroluminescent device, which is represented by the following Chemical Formula 1 or Chemical Formula 2. The organic luminescent compound according to the present invention is used as a host compound and/or a dopant compound within a luminescent layer, thereby allowing an organic electroluminescent device having excellent luminescent properties such as a driving voltage, luminescence efficiency, and the like.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same and capable of being driven at a low voltage and having excellent power efficiency and excellent luminescent efficiency characteristics.

An organic light emitting phenomenon is a phenomenon that converts electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered 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 such an organic light emitting 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 light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material, 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 luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has 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.

As a blue light emitting material, US Pat. No. 7053255 discloses a blue light emitting compound having a diphenyl anthracene structure and an aryl group substituted at the terminal thereof, and an organic electroluminescent device using the blue light emitting compound. However, have. On the other hand, US Pat. No. 7233019 and Korean Patent Laid-Open Publication No. 2006-0006760 disclose an organic electroluminescent device using a substituted pyrene compound. However, since the color purity of blue is low, a deep blue It is difficult to realize a full-color full-color display.

The present invention provides a novel organic electroluminescent compound which is employed in an organic layer of an organic electroluminescent device and can realize low voltage driving and excellent luminescent characteristics, and an organic electroluminescent device including the same.

In order to solve the above-described problems, the present invention provides an organic luminescent compound represented by the following formulas (1) to (2).

[Chemical Formula 1]

(2)

The specific structures and substituents of the above formulas (1) to (2) will be described later.

Also, the present invention is an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is represented by Formula 1 Or an organic electroluminescent compound represented by the following formula (2).

The organic electroluminescent device including the organic electroluminescent compound according to the present invention in the organic material layer has excellent color purity and luminous efficiency of blue color and can be driven at low voltage and is excellent in power efficiency and can be used for display and illumination.

1 to 5 are cross-sectional views illustrating the structure of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described more specifically.

The present invention is a luminescent compound employed in an organic layer of an organic electroluminescent device, and is characterized by being represented by the following formula (1) or (2).

In particular, the organic luminescent compound represented by the formula (1) is a host compound in the luminescent layer, and the organic luminescent compound represented by the formula (2) can be employed as a dopant compound in the luminescent layer.

[Chemical Formula 1]

(2)

In the above Chemical Formulas 1 to 2,

L ₁ to L ₄ are the same or different and are each independently a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted Or a substituted or unsubstituted heteroarylene group containing at least one of N, O and S atoms.

Ar ₁ represents 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 aryl A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, An 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, A substituted or unsubstituted carbazole group, or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.

R ₁ to R ₁₃ are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxy, substituted or unsubstituted alkyl, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl 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 heteroaryl group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group or an atom of N, O, S Or a substituted or unsubstituted heterocyclic group.

n, b, c, d, e, f and g are each independently 0 or 1, and m and p are integers of 0 to 7.

Further, in the present invention, the organic luminescent compound represented by the above formula (1) may be represented by any one of the following formulas (1-1) to (1-3).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In the formulas (1-1) to (1-3), R ₁ , R ₂ and Ar ₁ are the same as defined in the formula (1).

In the present invention, the compound represented by the formula (2) may be represented by any one of the following formulas (2-1) to (2-5).

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

In the above formulas (2-1) to (2-5), R ₄ to R ₁₁ are the same as defined in the above formula (2).

In the present invention, examples of the substituents will be specifically described below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.

In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 to 30, which does not cause steric hindrance. Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, a tert- , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n- , A benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.

In the present invention, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.

In the present invention, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofurancyl group, a phenanthroline group, An isothiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group and the like, but is not limited thereto.

In the present invention, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a ptert- Anthryloxy group, 2-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, Anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like. Examples of the arylthioxy group include phenylthioxy group, 2- A 4-tert-butylphenyloxy group, and the like. Examples of the arylsulfoxy group include benzene sulfoxy group and p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, Methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo An octyl group, and the like, but are not limited thereto.

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

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

.

등이 있다.In the present invention, 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 organic compounds are connected via one atom For example,

.

In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.

In the present invention, the silyl group is specifically exemplified by trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, But are not limited thereto.

In the present invention, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present invention, the alkyloxy group in the alkylthio group and the alkyl group in the alkylsulfoxy group are the same as the aforementioned alkyl groups. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In the present invention, "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, alkyl, cycloalkyl, , An arylsulfoxy group, an alkenyl group, a silyl group, a boron group, an alkylamine group, an aralkylamine group, an arylamine group, an aryl group, a fluorenyl group, a carbazole group and at least one of N, O and S atoms Substituted or unsubstituted with at least one substituent in the heterocyclic group.

In the present invention, the substituted arylene group means a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group. Anthracenyl group and the like are substituted with other substituents.

In the present invention, the substituted heteroarylene group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and condensed heterocyclic groups, Such as a benzoquinoline group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzzcarbazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.

In the present invention, L ₁ to L ₄ , Ar ₁ , and R ₁ to R ₁₂ of the above-mentioned formula (1) or (2) may further be substituted with further substituents. Examples thereof include deuterium, A fluorenyl group or a nitrile group substituted or unsubstituted with an alkyl group, an alkenyl group, an alkoxy group, a silyl group, an arylalkenyl group, an aryl group, a heteroaryl group, a carbazole group, an arylamine group, an aryl group, But is not limited thereto.

The organic luminescent compound according to the present invention represented by the above Chemical Formula 1 or 2 can be used as an organic material layer of an organic electroluminescent device due to its structural specificity. More specifically, a host compound and / Can be used.

In particular, the organic luminescent compound represented by the formula (1) is a host compound in the luminescent layer, and the organic luminescent compound represented by the formula (2) can be employed as a dopant compound in the luminescent layer.

Preferred examples of the compound represented by the formula (1) according to the present invention include, but are not limited to, the following compounds.

Further, other preferred specific examples of the compound represented by the formula (1) according to the present invention include, but are not limited to, the following compounds.

In addition, preferred specific examples of the compound represented by the formula (2) according to the present invention include, but are not limited to, the following compounds.

Other preferred examples of the compound represented by the formula (2) according to the present invention include, but are not limited to, the following compounds.

An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic electroluminescent device into the structure, a material meeting the requirements of each organic material layer is manufactured . The compound of the present invention can be applied to a device according to a conventional method of manufacturing an organic electroluminescent device.

The organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.

The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. However, it is not limited to this and may include a smaller number of organic layers.

Therefore, in the organic electroluminescent device according to the present invention, 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, May include a compound represented by formula (1) or (2).

Further, 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). Here, the compound represented by Formula 1 may be included as a host material in the light emitting layer. When the compound represented by the formula (1) is contained as a host material in the light emitting layer, the light emitting layer may include at least one dopant including the compound represented by the formula (2).

Further, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (2). Here, the compound represented by Formula 2 may be included as a dopant in the light emitting layer. When the compound represented by Formula 2 is included as a dopant in the light emitting layer, the light emitting layer may include at least one host material including a compound represented by Formula 1.

In the organic compound layer having such a multi-layer structure, the compound represented by the formula (1) or (2) may be used as a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports holes and emits light, And the like.

For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.

1 shows an organic electroluminescent device 1 in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially laminated on a substrate 1 Are illustrated. In such a structure, the compound represented by Formula 1 or Formula 2 may be included in the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

2 shows a structure of an organic electroluminescent device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5 and a cathode 7 are sequentially laminated on a substrate 1 . In such a structure, the compound represented by Formula 1 or Formula 2 may be included in the hole injecting layer 3, the hole transporting layer 4, or the electron transporting layer 6.

3 illustrates the structure of an organic electroluminescent device in which an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by the formula (1) or (2) may be included in the hole transport layer (4), the light emitting layer (5), or the electron transport layer (6).

4 shows the structure of an organic electroluminescent device in which an anode 2, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by the formula (1) or (2) may be included in the light emitting layer (5) or the electron transport layer (6).

5 illustrates the structure of an organic electroluminescent device in which an anode 2, a light-emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. As shown in FIG. In such a structure, the compound represented by the formula (1) or (2) can be included in the luminescent layer (5).

For example, the organic electroluminescent device according to the present invention can be manufactured by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal oxide or a conductive metal oxide on the substrate, An anode is formed by depositing an alloy on the anode, and an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and then a substance usable as a cathode is deposited thereon.

In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

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, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

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 a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof, a multilayer such as LiF / Al or LiO ₂ / Structural materials, and the like, 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 be 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, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection 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 combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

In addition, the organic electroluminescent compound according to the present invention can act on a principle similar to that applied to an organic electroluminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

Synthesis Example 1: Synthesis of [Compound 1]

(1) Synthesis of [intermediate 1-0]

100 mL of toluene was added to 9-bromoanthracene (5.0 g, 0.019 mol), oxalyl dichloride (2.9 g, 0.022 mol), Pd (dba) ₂ (0.9 g, 0.0010 mol) and sodium tert- And the mixture was reacted at 95 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and the product was separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 4.1 g (70%) of [intermediate 1-0]

(2) Synthesis of [intermediate 1-1]

100 mL of THF was added to a solution of [Intermediate 1-0] (5.0 g, 0.016 mol) and phenylmagnesium bromide (7.0 g, 0.037 mol) and the mixture was reacted at -78 ° C for 5 hours with stirring. After completion of the reaction H ₂ 0: after separation layer MC and column purification (n-HEXANE: MC) to a [Intermediate 1-1 was obtained 6.7g (90%) (m / z = 467)

(3) Synthesis of [intermediate 1-2]

100 mL of MeOH was added to a solution of [Intermediate 1-1] (5.0 g, 0.010 mol), Mg (0.6 g, 0.024 mol), Pd (dba) ₂ (0.5 g, 0.005 mol) Followed by stirring at 25 ° C for 6 hours. After completion of the reaction, the reaction mixture was separated into H ₂ O: MC and purified by column (n-HEXANE: MC) to obtain 3.9 g (90%) of [intermediate 1-2]

(4) Synthesis of [intermediate 1-3]

To a mixture of 1,4-phenylenediboronic acid (2.2 g, 0.013 mol), Pd (pph ₃ ) ₄ (0.6 g, 0.0006 mol) and potassium carbonate (3.0 g, 0.022 mol) in 1-bromonaphthalene (2.5 g, 0.012 mol) And the mixture was reacted at 65 占 폚 for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 3.8 g (72%) of [intermediate 1-3]

(5) Synthesis of [Compound 1]

[Compound 1] was synthesized by the same method as in Synthesis Example 1- (4), except that [Intermediate 1-3] (2.97 g, 0.012 mol) was added to the intermediate 1-2 [5.0 g, 0.011 mol] (Yield: 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / d, 8.01 / d, 7.88 / d, 7.75 / d, 7.61 / m, 7.38 / m 7.26 / m, 7.27 / d) 2H (7.55 / m, 7.27 / m, 5.00 / s) 4H (7.40 /

LC / MS: m / z = 559 [(M + 1) ^< ^{+ &}

Synthesis Example 2: Synthesis of [Compound 12]

(1) Synthesis of [intermediate 12-1]

4-bromonaphthalen-1-ylboronic acid (5.0 g, 0.011 mol) was added to 4-bromonaphthalen-1-ylboronic acid (3.3 g, 0.013 mol) 12-1] (m / z = 298.14) (yield: 72%).

(2) Synthesis of [Compound 12]

[Compound 12] was synthesized in the same manner as in Synthesis Example 1- (4), except that [Intermediate 12-1] (5.0 g, 0.009 mol) was added to [Intermediate 1-2] (5.0 g, 0.011 mol) (Yield: 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.92 / d, 7.88 / d, 7.75 / d, 7.73 / d, 7.58 / d, 7.38 / m, 7.36 / m, 7.26 / m, 7.17 / d ) 2H (8.55 / d, 8.00 / d, 7.59 / m, 7.55 / m, 7.27 /

LC / MS: m / z = 609 [(M + 1) ^< ^{+ &}

Synthesis Example 3: Synthesis of [Compound 29]

(1) Synthesis of [Intermediate 12-2]

bromo-9,9-dimethyl-9H-fluorene (2.45 g, 0.009 mol) was added to naphthalene-1,4-diyldiboronic acid (5.0 g, 0.011 mol) To obtain 4.2 g (yield 69%) of [intermediate 12-2] (m / z: 364.24)

(2) Synthesis of [Compound 29]

[Compound 29] was obtained by synthesizing [Intermediate 12-2] (4.8 g, 0.0132 mol) in [Intermediate 1-2] (5.0 g, 0.011 mol) (Yield: 69%). (M / z: 674.87)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / d, 7.88 / d, 7.87 / d, 7.77 / s, 7.75 / d, 7.63 / d, 7.36 / m, 7.28 / m, 7.26 / m D, 7.57 / d) 2H (8.55 / d, 7.38 / m, 7.27 / m, 5.00 / s, 1.72 / s)

LC / MS: m / z = 675 [(M + 1) ^< ^{+ &}

Synthesis Example 4: Synthesis of [Compound 36]

(1) Synthesis of [Intermediate 36-1]

9-bromophenanthrene (2.3 g, 0.009 mol) was added to 9,9-dimethyl-9H-fluorene-2,7-diyldiboronic acid (5.0 g, 0.011 mol) To obtain 4.7 g (yield 72%) of [intermediate 36-1]. (M / z = 414.3)

(2) Synthesis of [Compound 36]

[Compound 36] was synthesized in the same manner as in Synthesis Example 1- (4), except that [Intermediate 1-2] (4.3 g, 0.010 mol) was added to the intermediate 36-1 (5.0 g, 0.012 mol) (Yield: 74%). (M / z = 476)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.01 / d, 7.88 / d, 7.75 / d, 7.38 / m, 7.36 / m, 7.26 / m, 7.17 / d) 2H (8.93 / d, 8.12 d, 7.88 / m, 7.82 / 7.77 / s, 7.63 / d, 7.27 / m, 5.00 / s, 1.72 / s)

LC / MS: m / z = 725 [(M + 1) ^< ^{+ &}

Synthesis Example 5: Synthesis of [Compound 52]

(1) Synthesis of [Intermediate 52-1]

4-bromo-2,5-dimethylphenylboronic acid (6.6 g, 0.029 mol) was added to naphthalen-1-ylboronic acid (5.0 g, 0.029 mol) in the same manner as in Synthesis Example 1- 52-1] (yield: 71%). (m / z = 276.14. 2)

(2) Synthesis of [Compound 52]

4-naphthalen-1-yl) phenylboronic acid (3.03 g, 0.011 mol) was added to the intermediate 1-2 [5.0 g, 0.009 mol] (M / z = 476) of [Compound 52] (yield 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / d, 8.01 / d, 7.88 / d, 7.75 / d, 7.61 / m, 7.38 / m (7.36 / m, 7.26 / 7.17 / d) 2H (7.73 / d, 7.55 / m, 7.27 / m, 5.00 / s, 2.59 / s)

LC / MS: m / z = 587 [(M + 1) ^< ^{+ &}

Synthesis Example 6: Synthesis of [Compound 65]

(1) Synthesis of [intermediate 65-1]

Synthesis of naphthalen-2-ylmagnesium bromide (8.5 g, 0.037 mol) (1.9 g, 0.011 mol) was added to the intermediate 1-0 (5.0 g, 0.016 mol) 8.3 g (yield: 91%) of [intermediate 65-1] was obtained. (M / z = 567)

(2) Synthesis of [Intermediate 65-2]

[Synthesis of Intermediate 6-1] (5.0 g, 0.009 mol) was synthesized in the same manner as in Synthesis Example 1- (3) to give 4.5 g (yield 93% 535)

(3) Synthesis of [Intermediate 65-3]

Synthesis was conducted in the same manner as in Synthesis Example 1- (4), except that naphthalen-1-ylboronic acid (4.2 g, 0.025 mol) was added to 4-bromophenylboronic acid (5.0 g, 0.025 mol) (Yield: 76%). (M / z = 248.08)

(4) Synthesis of [Compound 65]

[Compound 65] was synthesized by the same method as in Synthesis Example 1- (4), except that [Intermediate 65-3] (2.67 g, 0.010 mol) was added to [Intermediate 65-2] (5.0 g, 0.009 mol) (Yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / d, 8.01 / d, 7.88 / d, 7.75 / d, 7.61 / m, 7.38 / m M, 7.56 / m, 7.42 / m, 7.00 / d, 5.00 / s, ) 4H (7.25 / d)

LC / MS: m / z = 659 [(M + 1) ^< ^{+ &}

Synthesis Example 7: Synthesis of [Compound 75]

(1) Synthesis of [Intermediate 75-1]

(1.9 g, 0.011 mol) (4- (trimethylsilyl) phenyl) magnesium bromide (9.4 g, 0.037 mol) was added to a solution of the intermediate 1-0 (5.0 g, 0.016 mol) (M / z = 611) of [Intermediate 75-1] was obtained by the same method as in the synthesis of Intermediate 75-1 (yield: 85%).

(2) Synthesis of [Intermediate 75-2]

[Intermediate 75-1] (5.0 g, 0.008 mol) was synthesized in the same manner as in Synthesis Example 1- (3) to give 4.0 g (yield 86% 579)

(3) Synthesis of [Intermediate 75-3]

4.1 g (yield: 74%) was obtained by synthesizing 9-bromophenanthrene (6.42 g, 0.025 mol) in 4-bromophenylboronic acid (5.0 g, 0.025 mol) in the same manner as in Synthesis Example 1- %). (M / z = 298.14)

(4) Synthesis of [Compound 75]

[Compound 75-3] (2.8 g, 0.009 mol) was added to [Intermediate 75-2] (5.0 g, 0.008 mol) in the same manner as in Synthesis Example 1- (4) (Yield: 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.01 / d, 7.93 / d, 7.88 / d, 7.75 / d, 7.38 / m, 7.36 / m, 7.26 / d, 7.17 / d) 2H (8.93 d, 7.27 / d, 7.25 / d) 6H (0.25 / s)

LC / MS: m / z = 754 [(M + 1) ^< ^{+ &}

Synthesis Example 8: Synthesis of [Compound 18]

(1) Synthesis of [intermediate 18-1]

Bis (pinacolato) dibron (3.6 g, 0.014 mol), PdCl ₂ (dppf) (0.4 g, 0.0006 mol), potassium acetate (3.7 g, 0.036 mol) Was added 100 mL of 1,4-dioxane, and the mixture was reacted at 95 DEG C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 3.8 g (71%) of [Intermediate 18-1]. (m / z = 482)

(2) Synthesis of [Intermediate 18-2]

(3,5-Diphenylphenyl) boronic acid (3.0 g, 0.011 mol) was added to 1,5-dibromonaphthalene (5.0 g, 0.010 mol) 2] (yield: 74%). (M / z = 435.35)

(3) Synthesis of [Compound 18]

[Compound 18-2] (4.7 g, 0.011 mol) was added to [Intermediate 18-1] (5.0 g, 0.011 mol) and the compound [18] was synthesized in the same manner as in Synthesis Example 1- (Yield: 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.01 / d, 7.88 / d, 7.75 / d, 7.38 / m, 7.36 / m, 7.26 / m, 7.17 / d) 2H (8.51 / d, 8.42 7.51 / m, 7.27 / m, 5.00 / s) 3H (7.66 /

LC / MS: m / z = 711 [(M + 1) ^< ^{+ &}

Synthesis Example 9: Synthesis of [Compound 104]

9,9-dimethyl-9H-fluoren-2-ylboronic acid (3.0 g, 0.011 mol) was added to the intermediate [18-2] (5.0 g, 0.009 mol) in the same manner as in Synthesis Example 1- (4) To obtain 4.3 g (yield: 71%) of [Compound 104].

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.01 / d, 7.93 / d, 7.88 / d, 7.87 / d, 7.77 / s, 7.75 / s, 7.63 / d, 7.55 / d, 7.36 / m M, 7.27 / d) 2H (8.51 / d, 8.42 / d, 7.61 / m, 7.38 / m, 7.27 / m, 5.00 / s, 1.72 / s) / d)

LC / MS: m / z = 675 [(M + 1) ^< ^{+ &}

Synthesis Example 10: Synthesis of [Compound 122]

7-dimethyl-9-phenyl-7H-benzo [c] fluorene (3.2 g, 0.008 mol) was added to a solution of Intermediate 18-1 (5.0 g, 0.010 mol) ) To obtain 3.9 g (yield: 72%) of [Compound 122].

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.56 / d, 8.52 / d, 8.15 / d, 8.01 / d, 7.99 / s, 7.88 / d, 7.83 / s, 7.75 / d, 7.69 / d (7.52 / d, 7.27 / m, 5.00 / s, 1.78 / s) 3H (7.51 / m) (7.40 / m, 7.29 / d)

LC / MS: m / z = 675 [(M + 1) ^< ^{+ &}

Synthesis Example 11: Synthesis of [Compound 149]

(1.9 g, 0.012 mol) was added to a solution of the intermediate [1-3] (5.0 g, 0.010 mol) in the same manner as in Synthesis Example 1- (4) %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.24 / s, 8.70 / d, 8.42 / d, 8.01 / d, 7.88 / d, 7.75 / d, 7.57 / m, 7.38 / m, 7.36 / m (7.27 / m, 5.00 / s) 4H (7.40 / m, 7.29 / d, 7.25 / d)

LC / MS: m / z = 510 [(M + 1) ^< ^{+ &}

Synthesis Example 12: Synthesis of [Compound 158]

(1) Synthesis of [intermediate 158-1]

Tert-butylaniline (1.6 g, 0.011 mol) Pd (dba) ₂ (0.5 g, 0.0006 mol) and sodium-tert-butoxide (2.1 g, 0.022 mol) in DMF ), 80 mL of toluene was added, and the mixture was reacted at 95 DEG C for 6 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and the product was separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 3.8 g (70%) of [intermediate 158-1]

(2) Synthesis of [Compound 158]

4-bromobenzonitrile (1.8 g, 0.010 mol) was added to a solution of the intermediate 158-1 (5.0 g, 0.010 mol) in the same manner as in Synthesis Example 1- (1) %). (M / z = 604)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.75 / d, 7.36 / m, 7.35 / m, 7.26 / m, 7.17 / d, 2.87 / s) 2H (7.39 / d, 7.27 / m, 7.05 / d, 6.81 / d, 6.55 / d, 5.00 / s, 1.20 / s)

LC / MS: m / z = 605 [(M + 1) ^< ^{+ &}

Synthesis Example 13: Synthesis of [Compound 161]

(1) Synthesis of [intermediate 161-0]

7.1 g (yield 75%) of [intermediate 161-0] was synthesized by the same method as in Synthesis Example 1- (1), except that perbromoethene (8.2 g, 0.024 mol) was added to 9-chloroanthracene (M / z = 396).

(2) Synthesis of [intermediate 161-1]

4.5 g (yield 72%) of [intermediate 161-1] was synthesized by the same method as in Synthesis Example 1- (1), except that diphenylamine (2.1 g, 0.013 mol) %). (M / z = 484)

(3) Synthesis of [intermediate 161-2]

Intermediate 161-2 was synthesized by the same method as in Synthesis Example 1- (4), except that 1,4-phenylenediboronic acid (2.2 g, 0.012 mol) was added to the intermediate 161-1 (5.0 g, 0.010 mol) 3.6 g (yield 75%) of the title compound (m / z = 482)

(4) Synthesis of [intermediate 161-3]

Synthesis was conducted in the same manner as in Synthesis Example 1- (1) except that 1-bromo-3,5-difluorobenzene (4.5 g, 0.023 mol) was added to 3,5-difluoroaniline (3.0 g, 0.023 mol) 3] (yield: 70%). (M / z = 241)

(5) Synthesis of [Compound 161]

[Compound 161] was synthesized by the same method as in Synthesis Example 1- (1), except that [Intermediate 161-3] (2.4 g, 0.010 mol) was added to the intermediate 161-2 (5.0 g, 0.010 mol) (Yield: 67%). (M / z = 476)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / s, 7.75 / d, 7.36 / m, 7.35 / d, 7.27 / m, 7.26 / m, 7.17 / d) 2H (7.40 (7.23 / d, 6.77 / m, 6.04 / s, 4.85 / s)

LC / MS: m / z = 687 [(M + 1) ^< ^{+ &}

Synthesis Example 14: Synthesis of [Compound 166]

(1) Synthesis of [intermediate 166-1]

Boronicacid (2.1 g, 0.013 mol) was added to the intermediate 166-0 (5.0 g, 0.013 mol), and 3.6 g (intermediate 166-1) of Intermediate 166-1 was synthesized in the same manner as in Synthesis Example 1- Yield: 70%). (M / z = 393)

(2) Synthesis of [Intermediate 166-2]

Was synthesized in the same manner as in Synthesis Example 12- (1) except that bis (4-tert-butylphenyl) amine (3.7 g, 0.013 mol) was added to the intermediate 166-1 (5.0 g, 0.013 mol) -2] (yield: 71%). (M / z = 594)

(3) Synthesis of [Compound 166]

Synthesis was carried out in the same manner as in Synthesis Example 12- (1) except that bis (4-tert-butylphenyl) amine (2.3 g, 0.008 mol) was added to the intermediate 166-2 (5.0 g, 0.008 mol) ] (Yield: 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.75 / d, 7.36 / m, 7.35 / m, 7.27 / m, 7.26 / m, 7.17 / d) 2H (7.40 / m, 7.29 / d, 4.85 / s) 8H (7.01 / d, 6.55 / d) 12H (1.35 / s)

LC / MS: m / z = 840 [(M + 1) ^< ^{+ &}

Synthesis Example 15: Synthesis of [Compound 168]

(1) Synthesis of [intermediate 168-1]

Bromobenzene (4.2 g, 0.027 mol) was added to 2-fluorobiphenyl-4-amine (5.0 g, 0.027 mol) in the same manner as in Synthesis Example 12- (1) 82%). (M / z = 263)

(3) Synthesis of [intermediate 168-2]

[Intermediate 168-2] was synthesized by the same method as in Synthesis Example 12- (1), except that [Intermediate 15-1] (3.4 g, 0.013 mol) was added to the intermediate 166-1 (5.0 g, 0.013 mol) 5.3 g (yield: 71%) was obtained. (M / z = 576)

(4) Synthesis of [Compound 168]

[Compound 168-1] (2.3 g, 0.009 mol) was added to the intermediate 168 - [intermediate 168-2] (5.0 g, 0.009 mol) (Yield: 77%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.75 / d, 7.55 / d, 7.36 / m, 7.35 / m, 7.27 / m, 7.26 / m, 7.17 / d M, 6.81 / m, 6.77 / m, 6.60 / d, 6.46 / d, 6.43 / d) 2H (7.41 / m, 7.40 / m, 7.33 / d, 7.29 / d, 7.23 / ) 3H (6.63 / d) 4H (7.51 / m) 5H (7.52 / d)

LC / MS: m / z = 803 [(M + 1) ^< ^{+ &}

Example 16: Synthesis of [Compound 184]

(1) Synthesis of [intermediate 184-1]

[Intermediate 184-1] was synthesized by the same method as in Synthesis Example 12- (1), except that 4- (trimethylsilyl) aniline (2.1 g, 0.011 mol) 3.6 g (yield: 63%) was obtained. (M / z = 519)

(2) Synthesis of [intermediate 184-2]

1,2,5-tribromo-3- (trifluoromethyl) benzene (3.8 g, 0.010 mol) was added to the intermediate 184-1 (5.0 g, 0.010 mol) (M / z = 821) as an intermediate [184-2] (yield: 72%).

(3) Synthesis of [Compound 184]

3.5 g (0.007 mol) of [compound 184-2] was synthesized in the same manner as in Synthesis Example 1- (4), except that 1,4-phenylenediboronic acid (1.1 g, 0.007 mol) (Yield: 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.89 / s, 7.87 / d, 7.75 / m, 7.45 / d, 7.36 / m, 7.35 / m, 7.26 / m, 7.17 / d M), 7.29 / d (7.52 / d, 7.41 / m, 7.27 / d, 7.15 / d, 7.08 / d, 6.61 / d, 5.00 / )

LC / MS: m / z = 817 [(M + 1) ^< ^{+ &}

Synthesis Example 17: Synthesis of [Compound 186]

(1) Synthesis of [intermediate 186-1]

(1.2 g, 0.011 mol) was added to a mixture of the intermediate [1-2] (5.0 g, 0.011 mol) and 3.1 g (intermediate 186-1) of Intermediate 186-1 synthesized in the same manner as in Synthesis Example 12- Yield: 60%). (M / z = 465)

(2) Synthesis of [intermediate 186-2]

Was synthesized in the same manner as in Synthesis Example 12- (1) except that 1-bromo-2,4-dichlorobenzene (2.5 g, 0.011 mol) was added to [Intermediate 1-2] (5.0 g, 0.011 mol) -2] (yield: 72%). (M / z = 610)

(3) Synthesis of [Compound 186]

Synthesis was conducted in the same manner as in Synthesis Example 1- (4), except that 1,4-phenylenediboronic acid (3.4 g, 0.020 mol) was added to the intermediate 186-2 (5.0 g, 0.008 mol) (Yield: 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.75 / d, 7.50 / d, 7.45 / s, 7.36 / m, 7.35 / m, 7.26 / m, 7.17 / d (7.51 / m, 7.40 / m, 7.29 / d), 6.75 / d) 2H (7.52 / d, 7.41 / m, 7.27 / m, 7.08 / d, 6.99 / d, 6.61 /

LC / MS: m / z = 694 [(M + 1) ^< ^{+ &}

Synthesis Example 18: Synthesis of [Compound 194]

(1) Synthesis of [intermediate 194-1]

[Intermediate 194-1] was synthesized by the same method as in Synthesis Example 1- (1), except that 1- (2-chlorophenyl) ethanone (4.0 g, 0.026 mol) was added to 2-bromobenzenethiol (5.0 g, 0.026 mol) g (yield: 70%). (m / z = 307)

(2) Synthesis of [intermediate 194-2]

(3.5 g, 0.019 mol) was added to the intermediate 194-1 (5.0 g, 0.016 mol) in the same manner as in Synthesis Example 1- (2) to obtain 4.6 g of Intermediate 194-2 89%). (M / z = 323)

(3) Synthesis of [intermediate 194-3]

[Synthesis of intermediate 194-2] (5.0 g, 0.015 mol) was synthesized in the same manner as in Synthesis Example 1- (3) to give 4.3 g (yield 93%) of [intermediate 194-3] 305)

(4) Synthesis of [intermediate 194-4]

Was synthesized in the same manner as in Synthesis Example 12- (1) except that 2,4-dibromo-6-fluoroaniline (2.9 g, 0.011 mol) was added to [Intermediate 1-2] (5.0 g, 0.011 mol) -4] (yield: 72%). (M / z = 623)

(5) Synthesis of [intermediate 194-5]

(3.4 g, 0.020 mol) was added to the intermediate 194-4 (5.0 g, 0.008 mol) in the same manner as in Synthesis Example 1- (4) 63%). (M / z = 617)

(6) Synthesis of [Compound 194]

Synthesis was carried out in the same manner as in Synthesis Example 12- (1) except that 4-bromo-9,9-dimethyl-9H-thioxanthene (2.4 g, 0.008 mol) was added to the intermediate 194-5 (5.0 g, 0.008 mol) To obtain 4.0 g (yield: 60%) of [Compound 194].

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.75 / d, 7.69 / d, 7.36 / m, 7.35 / m, 7.34 / m, 7.26 / m, 7.23 / s M, 7.27 / d, 7.11 / m, 7.10 / d, 6.86 / m, 6.46 / d, 6.25 / d) 2H (7.52 / d, 7.41 / , 1.72 / s) 4H (7.51 / m, 7.40 / m, 7.29 / d)

LC / MS: m / z = 843 [(M + 1) ^< ^{+ &}

Synthesis Example 19: Synthesis of [Compound 216]

4.5 g (yield: 72%) was obtained by synthesizing 4-bromobenzonitrile (1.8 g, 0.010 mol) in the intermediate 184-1 (5.0 g, 0.010 mol) %). (M / z = 821)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.75 / d, 7.36 / m, 7.35 / m, 7.26 / m, 7.17 / d) 2H (7.39 / d, 7.27 m), 7.15 / d, 6.81 / d, 6.61 / d, 5.00 /

LC / MS: m / z = 621 [(M + 1) ^< ^{+ &}

Synthesis Example 20: Synthesis of [Compound 237]

(1) Synthesis of [Intermediate 237-1]

9,9-dimethyl-9H-fluoren-2-amine (2.3 g, 0.011 mol) was added to the intermediate 1-2 (5.0 g, 0.011 mol) (M / z = 563) of <Intermediate 237-1> (yield: 70%).

(2) Synthesis of [Compound 237]

(Compound 237) (4.7 g, yield 75%) was synthesized by the same method as in Synthesis Example 12- (1), except that 5-bromoisophthalonitrile (2.3 g, 0.009 mol) %). (M / z = 476)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.75 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.36 / m, 7.35 / m, 7.28 / m, 7.26 / m (7.17 / d, 6.87 / s, 6.75 / s, 6.58 / d) 2H (7.87 / d, 7.27 / m, 7.00 / s, 5.00 / s, 1.72 / s)

LC / MS: m / z = 690 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 21: Synthesis of [Compound 248]

(1) Synthesis of [intermediate 248-1]

3.2 g (yield: 66%) of [intermediate 248-1] was synthesized in the same manner as in Synthesis Example 1- (4), except that phenylboronicacid (1.1 g, 0.007 mol) %). (M / z = 818)

(2) Synthesis of [Compound 248]

(248-1) (5.0 g, 0.006 mol) was added naphthalen-1-ylboronic acid (21.2 g, 0.007 mol) (Yield: 61%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / m, 7.95 / d, 7.87 / d, 7.75 / m, 7.61 / m, 7.41 / d M, 7.35 / m, 7.26 / m, 7.23 / s, 7.22 / s, 7.17 / d) 2H (7.55 / m, 7.51 / m, 7.27 / m, 7.15 / d, 7.08 / d, 6.61 / , 5.00 / s) 3H (0.25 / s) 4H (7.40 / m, 7.29 / d)

LC / MS: m / z = 817 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 22: Synthesis of [Compound 249]

(1) Synthesis of [Intermediate 249-1]

(Intermediate 249-1) was synthesized in the same manner as in Synthesis Example 12- (1), except that 4-aminobenzonitrile (1.3 g, 0.011 mol) was added to the intermediate 1-2 (5.0 g, 0.011 mol) Yield: 72%). (M / z = 472)

(2) Synthesis of [intermediate 249-2]

1,2,5-tribromo-3-fluorobenzene (3.3 g, 0.010 mol) was added to the intermediate 249-1 (5.0 g, 0.010 mol) 5.4 g (yield: 74%) of intermediate 249-2 (m / z = 724)

(3) Synthesis of [intermediate 249-3]

3.5 g (yield: 70%) of [intermediate 249-3] was synthesized in the same manner as in Synthesis Example 1- (4), except that phenylboronic acid (1.4 g, 0.008 mol) %). (M / z = 721)

(4) Synthesis of [Compound 249]

Synthesis was conducted in the same manner as in Synthesis Example 1- (4), except that naphthalen-1-ylboronic acid (2.2 g, 0.008 mol) was added to the intermediate 249-3 (5.0 g, 0.007 mol) (Yield: 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / d, 7.95 / d, 7.87 / d, 7.75 / d, 7.61 / m, 7.41 / d 7.36 / m, 7.35 / m, 7.26 / m, 7.17 / d) 2H (7.55 / m, 7.51 / m, 7.39 / d, 7.27 / m, 7.08 / d, 6.81 / d, 5.00 / / m, 7.29 / d)

LC / MS: m / z = 769 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 23: Synthesis of [Compound 266]

(1) Synthesis of [intermediate 266-1]

[Intermediate 266-1] was synthesized by the same method as in Synthesis Example 12- (1), except that 2,5-dibromobenzonitrile (2.6 g, 0.010 mol) was added to [Intermediate 158-1] (5.0 g, 0.010 mol) g (yield 72%). (m / z = 683)

(2) Synthesis of [Compound 266]

Compound 266] was synthesized by the same method as in Synthesis Example 1- (4), except that naphthalen-1-ylboronic acid (2.2 g, 0.008 mol) was added to the intermediate 266-1 (5.0 g, 0.007 mol) (Yield: 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / d, 7.95 / d, 7.87 / d, 7.75 / d, 7.72 / d, 7.61 / m 7.25 / d, 5.00 / s) 3H (1.35 &lt; RTI ID = 0.0 &gt; / s) 4H (7.40 / m, 7.29 / d)

LC / MS: m / z = 731 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 24: Synthesis of [Compound 277]

(1) Synthesis of [Intermediate 277-1]

(9.0-dimethyl-9H-fluoren-2-yl) magnesium bromide (11.0 g, 0.037 mol) was added to a solution of the intermediate 1-0 (5.0 g, 0.016 mol) Synthesis was conducted in the same manner to obtain 9.5 g (yield: 85%) of [intermediate 277-1] (m / z = 700)

(2) Synthesis of [intermediate 277-2]

[Synthesis of Intermediate 277-1] (5.0 g, 0.007 mol) was synthesized in the same manner as in Synthesis Example 1- (3) to give 4.2 g (yield 90% 667)

(3) Synthesis of [Intermediate 277-3]

3.9 g of Intermediate 277-3 (yield 72%) was synthesized according to the same method as that of Synthesis Example 12- (1), except that aniline (0.8 g, 0.008 mol) was added to Intermediate 277-2 (5.0 g, 0.008 mol) %). (M / z = 684)

(4) Synthesis of [intermediate 277-4]

1,2,5-tribromo-3-fluorobenzene (2.2 g, 0.007 mol) was added to the intermediate 277-2 (5.0 g, 0.007 mol) (M / z = 936) of intermediate 277-4 (yield: 64%).

(5) Synthesis of [Compound 277]

Compound 277] was obtained in a yield of 3.6 g (yield: 97%) in the same manner as in Synthesis Example 1- (4), except that m-tolylboronic acid (0.9 g, 0.006 mol) 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.82 / d, 7.79 / s, 7.75 / d, 7.69 / d, 7.41 / s, 7.36 / m, 7.35 / m 7.7 / d, 7.55 / d, 7.39 / m, 7.38 / m, 7.27 / d, 7.23 / , 7.33 / d, 7.28 / m, 7.19 / d, 5.00 / s) 4H (1.72 / s)

LC / MS: m / z = 960 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 25: Synthesis of [Compound 288]

(1) Synthesis of [intermediate 288-1]

[Intermediate 288-1] was synthesized by the same method as in Synthesis Example 1- (4), except that 3,5-dibromophenylboronic acid (3.6 g, 0.013 mol) was added to [Intermediate 1-2] (5.0 g, 0.011 mol) (M / z = 590) of 4.7 g (yield 72%).

(2) Synthesis of [intermediate 288-2]

Synthesis was conducted in the same manner as in Synthesis Example 1- (4), except that phenylboronic acid (2.1 g, 0.017 mol) was added to 1,2,5-tribromo-3-fluorobenzene (5.0 g, 0.015 mol) ] (M / z = 327) (yield: 73%).

(3) Synthesis of [intermediate 288-3]

4.1 g (intermediate 288-3) of 4-aminobenzonitrile (1.8 g, 0.015 mol) was added to the intermediate 25-2 (5.0 g, 0.015 mol) Yield: 75%). (M / z = 364)

(4) Synthesis of [Compound 288]

[Compound 288] was synthesized in the same manner as in Synthesis Example 12- (1), except that [Intermediate 288-3] (3.1 g, 0.016 mol) was added to the intermediate 288-2 (5.0 g, 0.008 mol) (Yield: 70%). (M / z = 476)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.01 / d, 7.38 / m, 7.36 / d, 7.26 / m, 7.17 / d, 5.73 / s) 2H (7.39 / d, 7.27 / m, 7.23 m, 7.40 / m, 7.29 / d). [0050]

LC / MS: m / z = 1158 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 26: Synthesis of [Compound 316]

(1) Synthesis of [intermediate 316-1]

4.2 g (0.013 mol) of 4-bromophenylboronic acid was added to a solution of the intermediate [1-2] (5.0 g, 0.011 mol) and the intermediate 316-1 was synthesized in the same manner as in Synthesis Example 1- (4) (Yield: 75%). (M / z = 511)

(2) Synthesis of [Intermediate 316-2]

4.2 g of Intermediate 316-2 was synthesized in the same manner as in Synthesis Example 12- (1) except that 4-isopropylaniline (1.4 g, 0.010 mol) was added to the intermediate 316-1 (5.0 g, 0.010 mol) Yield: 75%). (M / z = 565)

(3) Synthesis of [Compound 316]

Synthesis was conducted in the same manner as in Synthesis Example 12- (1) except that 3-bromodibenzo [b, d] thiophene (2.3 g, 0.009 mol) was added to the intermediate 316-2 (5.0 g, 0.009 mol) ] (Yield 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 8.01 / d, 7.98 / d, 7.88 / d, 7.80 / d, 7.75 / d, 7.52 / m, 7.50 / m, 7.38 / m D, 7.26 / m, 7.05 / d, 7.06 / s, 6.88 / d, 2.87 / , 1.20 / s) 4H (7.40 / m, 7.29 / d)

LC / MS: m / z = 748 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 27: Synthesis of [Compound 333]

(1) Synthesis of [intermediate 333-1]

(4-tert-butyl-N-phenylaniline (5.0 g, 0.022 mol) was added naphthalen-1-ylboronic acid (4.5 g, 0.026 mol) -1] (m / z = 308) (yield: 70%).

(2) Synthesis of [intermediate 333-2]

[Intermediate 333-2] 3.3 g of 4-tert-butylaniline (1.8 g, 0.012 mol) was added to the intermediate 333-1 (3.7 g, 0.012 mol) g (yield: 73%). (m / z = 376)

(3) Synthesis of [intermediate 333-3]

The intermediate [333-3] was synthesized by the same method as in Synthesis Example 12- (1), except that 3-bromophenylboronic acid (2.6 g, 0.013 mol) was added to the intermediate 333-2 (5.0 g, 0.013 mol) (Yield: 73%). (M / z = 496)

(4) Synthesis of [intermediate 333-4]

[Intermediate 333-4] (7.4 g, 0.015 mol) was added to the intermediate [166-1] (5.0 g, 0.013 mol) 7.1 g (yield 72%) was obtained. (M / z = 765)

(5) Synthesis of [Compound 333]

[Compound 333] (4.0 g, 0.008 mol) was added to a solution of the intermediate 333-4 (5.0 g, 0.007 mol) in the same manner as in Synthesis Example 1- (4) (Yield: 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.95 / d, 7.87 / d, 7.75 / s, 7.36 / m, 7.35 / m, 7.27 / m, 7.26 / m, 7.17 / d) 2H (8.55 d, 8.42 / d, 8.08 / d, 8.04 / d, 7.72 d, 7.61 m, 7.40 m, 7.29 d, 7.04 d, 6.97 d, 6.78 s, 6.58 d, ) 4H (7.55 / m, 7.01 / d, 6.55 / d) 6H (1.35 / s)

LC / MS: m / z = 1106 [(M + 1) ^&lt; ^{+ &}

Device Embodiment 1

An organic electroluminescent device was fabricated using the organic luminescence [Compound 1] according to the present invention as a fluorescent blue host material in the luminescent layer.

CuPc was deposited to 80 nm and α-NPD was deposited to 30 nm on a glass substrate coated with ITO, and 25% of [Compound 1] + [Compound B] 6% was mixed and the deposition rate was 0.1 m / sec. Alq ₃ was formed in a thickness of 40 nm, LiF was formed in a thickness of 1 nm, and Al was formed in a thickness of 120 nm. Thus, an organic electroluminescent device was fabricated. At this time, deposition rates of CuPc, α-NPD, Alq ₃ , LiF and Al were 0.5 nm / sec, 0.1 nm / sec, 0.01 nm / sec and 0.5 nm / sec, respectively.

Device Embodiments 2 to 15

Organic electroluminescent devices of Device Examples 2 to 15 were fabricated in the same manner as in Example 1 except that the compound described in [Table 1] was used in place of [Compound 1].

Device Comparative Example 1

The organic light emitting diode device for the comparative example 1 was fabricated in the same manner except that the compound [A] (ADN), which is generally used as a fluorescent host material, was used in place of the compound prepared by the present invention in the device structure of the embodiment .

Device Embodiment 16

An organic electroluminescent device was prepared using the organic luminescence [Compound 158] according to the present invention as a fluorescent blue dopant material of the light emitting layer.

CuPc was deposited to 80 nm and α-NPD was deposited to 30 nm on a glass substrate coated with ITO, and then 6% of [Compound A] + [Compound 158] was mixed to form a film with a deposition rate of 0.1 m / sec at 25 nm Alq ₃ was formed in a thickness of 40 nm, LiF was formed in a thickness of 1 nm, and Al was formed in a thickness of 120 nm. Thus, an organic electroluminescent device was fabricated. At this time, deposition rates of CuPc, α-NPD, Alq ₃ , LiF and Al were 0.5 nm / sec, 0.1 nm / sec, 0.01 nm / sec and 0.5 nm / sec, respectively.

Device Examples 17 to 35

Organic electroluminescent devices of Device Examples 17 to 35 were fabricated in the same manner as in Device Example 16, except that the compound described in [Table 2] was used instead of [Compound 158].

Device Comparative Example 2

The organic light emitting diode device for the comparative example 2 was fabricated in the same manner except that the compound [B], which is generally used as a fluorescent dopant material instead of the compound prepared by the present invention, was used in the device structure of the above- A] and [Compound B] have the following structures.

[Compound A] [Compound B]

Hereinafter, the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 35 and the microcavity fabrication examples 1 and 2 are compared, and the results are shown in [Table 1] and [Table 2] below.

[Table 1]

[Table 2]

[Measurement of driving voltage and luminous efficiency]

After fixing the organic light emitting device (substrate size: 25 × 25 mm 2 / deposition area: 2 × 2 mm 2) to the IVL measurement set (CS-2000 + jig + IVL program), the current was increased by 1 mA / The luminance (cd / m 2), the driving voltage (V) and the luminous efficiency (cd / A) were measured and shown in Table 1 and Table 2, respectively.

From the results of Examples 1 to 35 and Comparative Examples 1 and 2 and [Table 1] and [Table 2], it was found that the compound of the present invention exhibited lower voltage than that of the conventional blue fluorescent light emitting material (Compound A and Compound B) It can be used for a display device, a display device, an illumination, and the like.

Claims (13)

An organic luminescent compound represented by the following Chemical Formulas 1 to 2:
[Chemical Formula 1]

(2)

In the above Chemical Formulas 1 to 2,
L ₁ to L ₄ are the same or different and are each independently a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted Or a substituted or unsubstituted heteroarylene group containing at least one of N, O and S atoms,
Ar ₁ represents 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 aryl A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, An 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, A substituted or unsubstituted carbazole group or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,
R ₁ to R ₁₃ are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxy, substituted or unsubstituted alkyl, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl 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 heteroaryl group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group or an atom of N, O, S A substituted or unsubstituted heterocyclic group,
n, b, c, d, e, f and g are each independently 0 or 1, and m and p are integers of 0 to 7. The method according to claim 1,
The organic luminescent compound represented by the formula (1) is represented by any one of the following formulas (1-1) to (1-3):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In the formulas (1-1) to (1-3), R ₁ , R ₂ and Ar ₁ are the same as defined in the formula (1). The method according to claim 1,
(2) is represented by any one of the following formulas (2-1) to (2-5): &lt; EMI ID =
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

In the above formulas (2-1) to (2-5), R ₄ to R ₁₁ are the same as defined in the above formula (2). The method according to claim 1,
(1) to (2) are any one selected from the group consisting of the following compounds 1 to 51:

The method according to claim 1,
(1) to (2) are any one selected from the group consisting of the following compounds 52 to 153:

The method according to claim 1,
(1) to (2) are any one selected from the group consisting of the following compounds 154 to 183:

The method according to claim 1,
The compounds represented by the above formulas (1) to (2) are any one selected from the group consisting of the following compounds 184 to 342:

1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers contains an organic light emitting compound represented by any of formulas (1) to (2) according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, wherein at least one of the layers is an organic light emitting layer represented by the following Formula 1 or Formula 2 Wherein the organic compound is a compound represented by the following formula (1). 9. The method of claim 8,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises an organic light emitting compound represented by Formula 1 or Formula 2. 11. The method of claim 10,
Wherein the organic luminescent compound represented by Formula 1 or Formula 2 is a host compound or a dopant compound in the luminescent layer. 9. The method of claim 8,
Wherein the organic material layer includes at least one of an electron transporting layer, an electron injecting layer, and a layer simultaneously carrying out electron transport and electron injection, and at least one of the layers is an organic light emitting layer represented by the above Chemical Formula 1 or 2 Wherein the organic compound is a compound represented by the following formula (1). 9. The method of claim 8,
Wherein at least one of the organic light emitting layers emitting red, green or blue light is further included in the organic material layer to emit white light.

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