KR101626524B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound used in an organic electroluminescent device, and is characterized by being represented by the following formula (1), and when it is employed as a phosphorescent host compound in a light emitting layer, And this excellent organic electroluminescent device can be realized.
[Chemical Formula 1]

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 device and an organic electroluminescent device including the same, which have excellent brightness and power efficiency and can realize long-life 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 been sufficiently developed yet. 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.

Further, the most important factor for determining the luminous efficiency in an organic light emitting device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, In particular, CBP is the most widely known phosphorescent host material, and an organic light emitting device using a BALq derivative as a host is known.

However, in the case of using a material such as BAlq or CBP as a host of a phosphorescent material, the organic electroluminescent device using the phosphorescent material has a higher current efficiency than the device using the fluorescent material, There is no great advantage in terms of power efficiency, and the life of the device can not be satisfactory. Thus, development of a more stable and high-performance host material is required.

Korean Patent Publication No. 10-2012-0131870

The present invention provides a novel phosphorescent host compound which can be used in an organic layer of an organic electroluminescent device to realize 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 formula (1).

[Chemical Formula 1]

The specific structure and substituent of the organic luminescent compound according to the formula 1 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 An organic electroluminescent device comprising the organic electroluminescent compound according to the present invention.

The organic electroluminescent compound according to the present invention has excellent thermal stability, has a deep HOMO level, a high triplet state, and a hole stability, and thus can provide an organic electroluminescent device having an organic electroluminescent device exhibiting excellent characteristics in terms of efficiency, drive voltage, It is possible to realize a light emitting device.

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 relates to a novel organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1)

L ₁ to L ₃ , which are the same or different from each other, 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 an unsubstituted carbazolylene group or a substituted or unsubstituted heteroarylene group containing at least one of N, O and S atoms.

Ar ₁ To Ar ₃ are the same or different and each independently 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 Substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxy groups, 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, 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 represents a hydrogen atom, a deuterium atom, a halogen atom, 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 alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl 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 arylamine group, a substituted or unsubstituted arylamine 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, m is 0 to 4 An integer, the plurality of R ₁ if m is the plurality may be the same or different from each other.

In the present invention, the organic luminescent compound represented by the formula (1) may be represented by any one of the following formulas (2) to (6).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas (2) to (6), L ₃ and Ar ₃ are the same as defined in the above formula (1).

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 ₃ , Ar ₁ to Ar ₃ , and R ₁ in the above formula (1) may further be substituted with an additional substituent, and examples thereof include deuterium, a halogen group, an alkyl group, , A halogen atom, an alkoxy group, a silyl group, an arylalkenyl group, an aryl group, a heteroaryl group, a carbazole group, an arylamine group, a fluorenyl group substituted or unsubstituted with an aryl group, a nitrile group and the like .

The organic luminescent compound according to the present invention represented by Formula 1 can be used as an organic material layer of an organic electroluminescent device due to its structural specificity and more specifically can be used as a phosphorescent host compound in a luminescent layer in an organic material 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.

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] [Compound 42]

[Compound 43] [Compound 44]

[Compound 45] [Compound 46]

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.

[Compound 47] [Compound 48]

[Compound 49] [Compound 50]

[Compound 51] [Compound 52]

[Compound 53] [Compound 54]

[Compound 55] [Compound 56]

[Compound 57] [Compound 58]

[Compound 59] [Compound 60]

[Compound 61] [Compound 62]

[Compound 63] [Compound 64]

[Compound 65] [Compound 66]

[Compound 67] [Compound 68]

[Compound 69] [Compound 70]

[Compound 71] [Compound 72]

[Compound 73] [Compound 74]

[Compound 75] [Compound 76]

[Compound 77] [Compound 78]

[Compound 79] [Compound 80]

[Compound 81]

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 of 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 the formula (1).

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 Formula 1 is included as a host material in the light emitting layer, the light emitting layer may include at least one phosphorescent dopant.

On the other hand, when the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

According to an embodiment of the present invention, the light emitting layer may further contain at least one dopant compound selected from the following [structural formulas 1] to [structural formula 7], and a host compound represented by the general formula [1] have.

[Structural formula 1]

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

[Structural Formula 6]

[Structural Formula 7]

In the organic compound layer having such a multilayer structure, the compound represented by the formula (1) may be used in combination with a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports light and emits light, .

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

1 shows an organic electronic device 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 Structure is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, the light emitting layer 5, or the electron transporting layer 6.

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

4 illustrates the structure of an organic electronic 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 FIG. In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates the structure of an organic electronic device in which an anode 2, a light-emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1. As shown in Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

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 this structure, the compound represented by the formula (1) 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 the formula (1) may be included in the hole injection layer (3), the hole transport layer (4), or the electron transport 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) 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) may be included in the light-emitting layer (5) or the electron-transporting 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) may 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.

< Example >

Synthetic example  1: [Compound 1] Synthesis

(1) [Intermediate  1-1]  synthesis

[Intermediate 1-1]

To a solution of 2-chloro-4,6-diphenyl-1,3,5-triazine (6.8 g, 0.026 mol) Pd (dba) ₂ (1.2 g, 0.0013 mol) in 3-bromo-1H- indole ) and sodium-tert-butoxide (5.0 g, 0.052 mol) were added 200 mL of toluene, 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 column-purified (n-hexane: MC) to obtain 7.8 g (70%) of Intermediate 1-1. (m / z = 427)

(2) [Intermediate  1-2]  synthesis

[Intermediate 1-2]

To a solution of bis (pinacolato) dibron (3.6 g, 0.014 mol) PdCl ₂ (dppf) (0.4 g, 0.0006 mol) and potassium acetate (3.7 g, 0.036 mol) in Intermediate 1-1 (5.0 g, 0.012 mol) 4-dioxane was added and the mixture was reacted for 24 hours at 95 ° C. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and purified by column chromatography (n-hexane: MC) %). (m / z &lt; / RTI &gt; = 474)

(3) Compound  1]  synthesis

[Compound 1]

Intermediate 1-2 (5.0 g, 0.010 mol) 2-bromo-4,6-diphenyl-1,3,5-triazine in (2.5 g, 0.008 mol) Pd (pph 3) 4 (0.5 g, 0.0004 mol), Potassium carbonate (2.2 g, 0.016 mol) was added with 100 mL of THF, and the mixture was reacted at 65 DEG C for 18 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 3.4 g (73%) of Compound 1.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.60 / s, 7.33 / m, 7.25 / m) 4H (7.41 / m) 8H (8.28 / d, 7.51 / m )

LC / MS: m / z = 580 [(M + 1) ^&lt; ^{+ &}

Synthetic example  2: Synthesis of [Compound 2]

[Compound 2]

2-Bromotriphenylene (2.7 g, 0.008 mol) was added to Intermediate 1-2 (5.0 g, 0.010 mol) to obtain 3.7 g (yield 72%) of Compound 2 by the same method as in Synthesis Example 1- (3) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.17 / d, 8.04 / d, 7.71 / d, 7.36 / s) 2H (8.93 / d, 8.12 / d, 7.88 / m, 7.82 / m, 7.42 / m, 7.41 / m) 4H (8.28 / d, 7.51 /

LC / MS: m / z = 651 [(M + 1) ^&lt; ^{+ &}

Synthetic example  3: Synthesis of [Compound 3]

[Compound 3]

Synthesis was conducted in the same manner as in Synthesis Example 1- (3) except that 4- (4-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 0.008 mol) was added to Intermediate 1-2 (5.0 g, 0.010 mol) 3.4 g (yield 70%) of Compound 3 was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 8.41 / d, 8.20 / d, 8.17 / d, 7.98 / d, 7.71 / d, 7.58 / m, 7.52 / m, 7.50 / m , 7.36 / s) 2H (7.42 / m, 7.41 / d) 4H (8.28 / d, 7.51 /

LC / MS: m / z = 607 [(M + 1) ^&lt; ^{+ &}

Synthetic example  4: Synthesis of [Compound 4]

(1) Synthesis of [intermediate 4-1]

[Intermediate 4-1]

Synthesis was conducted in the same manner as in Synthesis Example 1- (3) except that 1-bromo-3,5-dichlorobenzene (1.9 g, 0.008 mol) was added to Intermediate 1-2 (5.0 g, 0.010 mol) g (yield: 71%). (m / z = 582)

(2) Synthesis of [Compound 4]

[Compound 4]

Intermediate 4-1 (5.0 g, 0.009 mol) 9H-carbazole (3.1 g, 0.018 mol) was added and the compound 4 was synthesized in the same manner as in Synthesis Example 1- (1) to give 5.1 g (yield 75%).

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (8.17 / d, 7.71 / d, 7.36 / s, 7.20 / s) 2H (8.55 / d, 8.12 / d, 8.09 / s, 7.94 / d, 7.41 / m, 7.33 / m, 7.29 / m, 7.25 / m) 4H (8.28 / d, 7.51 / m)

LC / MS: m / z = 755 [(M + 1) ^&lt; ^{+ &}

Synthetic example  5: Synthesis of [Compound 5]

[Compound 5]

To the intermediate 1-2 (5.0 g, 0.010 mol) was added 1- (4-bromophenyl) -2-phenyl-1H-benzo [d] imidazole (2.8 g, 0.008 mol) Synthesis was conducted in the same manner to obtain 3.6 g (yield 73%) of Compound 5.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (8.56 / d, 8.17 / d, 7.71 / d, 7.59 / d, 7.36 / s) 2H (7.79 / d, 7.68 / d, 7.42 / m, 7.22 / m) 3H (7.41 / m) 6H (8.28 / d, 7.51 / m)

LC / MS: m / z = 617 [(M + 1) ^&lt; ^{+ &}

Synthetic example  6: Synthesis of [Compound 6]

(1) Synthesis of [intermediate 6-1]

[Intermediate 6-1]

100 mL of ethanol was added to benzoic acid (5.5 g, 0.045 mol), p-methylbenzenesulfonic acid (0.9 g, 0.0045 mol) and pyridazine-4,5-diamine (5.0 g, 0.045 mol) . 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 4.9 g (56%) of Intermediate 6-1. (m / z = 196)

(2) Synthesis of [Intermediate 6-2]

[Intermediate 6-2]

(1.9 g, 0.025 mol) of 5-bromo-2-phenyl-1H-indole was added to the intermediate [6-1] (5.0 g, 0.025 mol) 4.5 g (yield: 73%) of 6-2 was obtained. (m / z = 351)

(3) Synthesis of [Compound 6]

[Compound 6]

Synthesis was conducted in the same manner as in Synthesis Example 1- (3), except that Intermediate 6-2 (1.9 g, 0.008 mol) was added to Intermediate 1-2 (5.0 g, 0.010 mol) .

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (8.17 / d, 7.71 / d, 7.36 / s) 2H (9.24 / s, 7.79 / d, 7.68 / d, 7.42 / m) 3H (7.41 / m) 6H (8.28 / d, 7.51 / m)

LC / MS: m / z = 619 [(M + 1) ^&lt; ^{+ &}

Synthetic example  7: Synthesis of [Compound 7]

(1) Synthesis of [Intermediate 7-1]

[Intermediate 7-1]

Synthesis was conducted in the same manner as in Synthesis Example 1- (1) except that 2,4,6-trichloro-1,3,5-triazine (5.0 g, 0.027 mol) and 9H-carbazole (9.1 g, 0.054 mol) 9.0 g (yield 75%) of Intermediate 7-1 was obtained. (M / z = 445)

(2) Synthesis of [Intermediate 7-2]

[Intermediate 7-2]

11.5 g (0.026 mol) of Intermediate 7-2 was obtained by the same method as in Synthesis Example 1- (1), except that 3-bromo-1H-indole (5.0 g, 0.026 mol) and Intermediate 7-1 Yield: 73%). (M / z = 605)

(3) Synthesis of [Intermediate 7-3]

[Intermediate 7-3]

(2.5 g, 0.010 mol) and bis (pinacolato) dibron (5.0 g, 0.008 mol) in the same manner as in Synthesis Example 1- (2) %). (M / z = 652)

(4) Synthesis of [Compound 7]

[Compound 7]

(3) was obtained in the same manner as in Synthesis Example 1- (3), except that 5'-Chloro-1,1 ': 3', 1 "-benzene-terphenyl (5.0 g, 0.013 mol) and Intermediate 7-3 (10.4 g, Synthesis was conducted in the same manner to obtain 8.1 g of Compound 7 (yield: 75%).

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (8.17 / d, 7.71 / d, 7.36 / s) 2H (8.55 / d, 8.12 / d, 7.94 / d, 7.63 / d, 7.50 / m, 7.41 / m, 7.33 / m, 7.29 / m, 7.25 / m) 3H (7.66 / s) 4H (7.52 / d, 7.51 / m, 7.25 / d)

LC / MS: m / z = 831 [(M + 1) ^&lt; ^{+ &}

Example  8: Synthesis of [Compound 8]

(1) Synthesis of [intermediate 8-1]

[Intermediate 8-1]

The same method as in Synthesis Example 1- (3) was used, except that 2,4,6-trichloro-1,3,5-triazine (5.0 g, 0.027 mol) and biphenyl-4-ylboronic acid (6.3 g, 0.032 mol) To obtain 7.9 g (yield 70%) of [intermediate 8-1]. (M / z = 419)

(2) Synthesis of [Intermediate 8-2]

[Intermediate 8-2]

<Intermediate 8-2> 10.6 g (0.26 mol) was obtained by the same method as in Synthesis Example 1- (1), except that 3-bromo-1H-indole (5.0 g, 0.026 mol) and Intermediate 8-1 g (yield: 71%). (m / z = 576)

(3) Synthesis of [Intermediate 8-3]

[Intermediate 8-3]

(2.5 g, 0.010 mol) and bis (pinacolato) dibron were added to a solution of Intermediate 8-2 (5.0 g, 0.008 mol) and 3.5 g (yield: 71%) of Intermediate 8-3 %). (M / z = 623)

(4) Synthesis of [Compound 8]

[Compound 8]

Synthesis was conducted in the same manner as in Synthesis Example 1- (3), except that Intermediate 8-3 (5.0 g, 0.008 mol) and 4- (4-bromophenyl) dibenzo [b, d] thiophene 3.8 g (yield: 71%) of Compound 8 was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 8.41 / d, 8.20 / d, 8.17 / d, 7.98 / d, 7.71 / d, 7.58 / m, 7.52 / m, 7.50 / m , 7.36 / s) 2H (7.42 / m, 7.41 / m) 4H (7.85 / d, 7.52 / d, 7.51 /

LC / MS: m / z = 759 [(M + 1) ^&lt; ^{+ &}

Synthetic example  9: Synthesis of [Compound 9]

(1) Synthesis of [intermediate 9-1]

[Compound 9-1]

D] imidazol-1-yl) phenylboronic acid (10.0 g, 0.032 mol) was added to a solution of 2,4,6-trichloro-1,3,5-triazine ) Was synthesized in the same manner as in Synthesis Example 1- (3) to give 12.7 g (yield 72%) of Intermediate 9-1 (m / z = 652)

(2) Synthesis of [intermediate 9-2]

[Compound 9-2]

Synthesis was conducted in the same manner as in Synthesis Example 1- (1), except that 3-bromo-1H-indole (5.0 g, 0.026 mol) and Intermediate 9-1 (16.6 g, 0.026 mol) Yield: 74%). (M / z = 811)

(3) Synthesis of [intermediate 9-3]

[Intermediate 9-3]

Synthesis was conducted in the same manner as in Synthesis Example 1- (2), except that Intermediate 9-2 (5.0 g, 0.006 mol) and bis (pinacolato) dibron (1.8 g, 0.007 mol) %). (M / z = 858)

(4) Synthesis of [Compound 9]

[Compound 9]

Synthesis was conducted in the same manner as in Synthesis Example 1- (3), except that Intermediate 9-3 (5.0 g, 0.006 mol) and 2- (4-bromophenyl) triphenylene (2.1 g, 0.005 mol) 74%).

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (9.15 / s, 8.18 / d, 8.17 / d, 8.04 / d, 7.71 / d, 7.36 / s) 2H (8.93 / d, 8.56 / d, 7.8 / d, 7.88 / d, 7.58 / d, 7.49 / d)

LC / MS: m / z = 1036 [(M + 1) ^&lt; ^{+ &}

Example 1: Fabrication of organic electroluminescent device

By depositing NPB on top of a glass substrate coated with ITO was formed a hole-transporting layer of 120 nm, followed by Ir (ppy) the deposition rate of the [compound 1] of Synthesis Example 1 according to the invention by the ₃ as a dopant 0.1 nm / sec , Ir (ppy) _{3 was} deposited at a deposition rate of 0.009 nm / sec, and Ir (ppy) ₃ was doped so as to have a deposition rate of 9% to form a light emitting layer with a thickness of 30 nm on the hole transport layer. BALq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq ₃ was deposited thereon to form an electron transporting layer of 40 nm. Lithium fluoride To form a 1 nm electron injection layer. Aluminum was deposited on the electron injection layer to form a 120 nm negative electrode, thereby fabricating an organic electroluminescent device.

Examples 2 to 29: Manufacture of organic electroluminescent device

An organic electroluminescent device was produced in the same manner as in Example 1 except that the luminescent compound described in [Table 1] was used instead of [Compound 1] in the above-mentioned examples.

Comparative Example 1

Except that CBP ((4,4-N, N-dicarbazole) biphenyl) was used instead of the organic luminescent compound according to the present invention of Examples 1 to 29 in the same manner as in the organic electroluminescent device .

The results of the comparison of the characteristics of the organic electroluminescent devices manufactured according to Examples 1 to 20 and Comparative Example 1 are shown in Table 1 below.

division Emitting material The driving voltage (V)
(1000 cd / m 2) Luminous efficiency
(cd / A)  (CIE (x, y)) Example 1 Compound 1 5.1 58 (0.31, 0.63) Example 2 Compound 2 6.1 46 (0.31, 0.63) Example 3 Compound 3 5.8 47 (0.32, 0.64) Example 4 Compound 4 4.5 61 (0.32, 0.64) Example 5 Compound 5 5.5 45 (0.32, 0.64) Example 6 Compound 6 5.9 45 (0.32, 0.64) Example 7 Compound 7 5.9 45 (0.34, 0.62) Example 8 Compound 8 5.9 46 (0.35, 0.63) Example 9 Compound 9 4.7 60 (0.33, 0.62) Example 10 Compound 10 5.6 50 (0.31, 0.62) Example 11 Compound 11 5.5 45 (0.31, 0.63) Example 12 Compound 12 4.3 61 (0.32, 0.62) Example 13 Compound 13 5.5 49 (0.33, 0.64) Example 14 Compound 14 5.8 46 (0.31, 0.63) Example 15 Compound 15 5.8 46 (0.31, 0.63) Example 16 Compound 16 4.1 60 (0.32, 0.62) Example 17 Compound 17 5.8 45 (0.33, 0.62) Example 18 Compound 18 5.9 48 (0.32, 0.64) Example 19 Compound 19 5.8 48 (0.31, 0.63) Example 20 Compound 20 4.5 58 (0.31, 0.63) Example 21 Compound 21 5.7 48 (0.32, 0.62) Example 22 Compound 22 5.5 47 (0.32, 0.64) Example 23 Compound 23 5.9 45 (0.33, 0.62) Example 24 Compound 24 4.2 59 (0.32, 0.64) Example 25 Compound 25 4.3 60 (0.34, 0.62) Example 26 Compound 26 4.1 61 (0.35, 0.63) Example 27 Compound 27 5.8 46 (0.34, 0.64) Example 28 Compound 28 5.8 48 (0.33, 0.63) Example 29 Compound 29 5.6 45 (0.34, 0.62) Comparative Example 1 CBP 6.8 37 (0.33, 0.62)

As shown in Table 1, when the organic electroluminescent compound according to the present invention is used as a host compound for a light emitting layer of an organic electroluminescent device, the luminous efficiency is significantly improved compared with the conventional CBP used as a light emitting material, This is possible.

Claims (10)

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
L ₃ is a single bond or a phenylene group, Ar ₃ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted A triazine group, and any one of the following Structural Formula 1 (when Ar ₃ is substituted, it is substituted with one or two phenyl groups)
[Structural formula 1]

In the above structural formula 1, R ₁ and R ₂ are each independently a methyl group or a phenyl group. delete delete delete 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 Formula 1 according to Claim 1. delete 6. The method of claim 5,
Wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises an organic light emitting compound represented by the following formula (1). 8. The method of claim 7,
The organic electroluminescent compound represented by Formula 1 is used as a host compound in the light emitting layer, and the light emitting layer further includes at least one dopant compound. delete 6. The method of claim 5,
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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