KR101842013B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

[화학식 2]

The present invention relates to an organic electroluminescent compound used in an organic electroluminescent device and is characterized by being represented by the following formulas (1) to (2). When the host compound is used as a host compound in a light emitting layer, The organic electroluminescent device having excellent light emission characteristics can be realized.
[Chemical Formula 1]

(2)

Description

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

More particularly, the present invention relates to an organic light emitting compound which is employed as a host compound in a light emitting layer of an organic electroluminescent device, and an organic electroluminescent device which has a remarkably improved long life and luminous efficiency by employing the organic light emitting compound.

The organic electroluminescent device can not only form an element on a transparent substrate but also can operate at a low voltage of 10 V or less as compared with a plasma display panel (Plasma Display Panel) or an inorganic electroluminescence (EL) display, It has the advantage of excellent color and has three colors of green, blue, and red. It has recently become a subject of interest as a next generation display device.

However, in order for such an organic electroluminescent device to exhibit such characteristics, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are materials forming an organic layer in a device, However, until now, stable and efficient development of an organic layer material for an organic electroluminescent device has not been sufficiently achieved yet. Therefore, there is a continuing demand for development of new materials having low-voltage driving, high efficiency and long life.

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.

The present invention provides a novel organic light emitting compound and an organic electroluminescent device including the same that can be used in a light emitting layer of an organic electroluminescent device to realize excellent light emitting characteristics.

The present invention provides an organic light emitting compound represented by the following Chemical Formulas 1 to 2 and an organic electroluminescent device comprising the same, in order to solve the above problems.

[Chemical Formula 1]

(2)

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

The organic luminescent compound according to the present invention has excellent structure flatness and has a high triplet state, so that the luminescent efficiency and the longevity characteristics can be improved as compared with the conventional phosphorescent host compound, And can be used for display devices.

1 to 5 are cross-sectional views illustrating the structure of an organic electroluminescent device according to an embodiment of the present invention.
6 is a schematic diagram showing the structure of an organic luminescent compound according to 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 formulas (1) to (2).

[Chemical Formula 1]

(2)

In the above Chemical Formulas 1 to 2,

R ₁ to R ₁₅ each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms , A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted C3 to C30 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, May be selected from the group consisting of a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted silyl group, an amino group, a thiol group, a cyano group, a hydroxyl group, a nitro group and a halogen group.

The adjacent substituents of R ₁ to R ₁₅ may be connected with each other to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be N, S, Lt; / RTI > may be substituted with any one or more heteroatoms selected from < RTI ID = 0.0 >

Each of R ₁ to R ₁₅ may be further substituted with at least one substituent, and the at least one substituent may be deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, An amino group, a thiol group, a cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group and an ester group.

In the above formulas (1) to (2), at least one of R ₁ to R ₁₅ is selected from the following structural formulas.

[Structural formula 1]

In the above formula 1,

L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, Having 2 to 30 carbon atoms An alkenylene group and a substituted or unsubstituted C2-C30 alkynylene group.

n is an integer of 0 to 4, and when n is 2 or more, plural Ls may be the same or different from each other.

R _a and R _b are the Formula 1 to the same definitions as the R ₁ to R ₁₅ in Formula 2, and m is an integer from 0 to 4, plural R _b when m is 2 or more is equal to each other Or may be different.

The plurality of R _b may combine with each other or adjacent substituents to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring.

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, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl 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.

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, the "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.

The organic luminescent compound according to the present invention represented by the above Chemical Formulas 1 to 2 can be used as an organic layer of an organic electroluminescent device due to its structural specificity and more specifically as a phosphorescent host compound of a luminescent layer.

Specific examples of the organic luminescent compound that may be employed as the phosphorescent host compound of the luminescent layer represented by formulas (1) to (2) according to the present invention include, but are not limited to, the following compounds.

The organic luminescent compound according to the present invention has the inherent characteristics of the substituent group introduced by introducing one or more substituents represented by the above-mentioned [formula 1] into the core structure having the structures represented by the above formulas (1) to (2) 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 the production of an organic electroluminescent device into the above structure, have.

In particular, as described above, the organic luminescent compounds represented by the formulas (1) to (2) according to the present invention have excellent planar structure as a result of introducing a substituent into the characteristic core structure, and a high triplet state It is possible to realize an organic electroluminescent device exhibiting excellent characteristics in terms of efficiency, driving voltage, lifetime and the like when the organic layer is applied to the organic electroluminescent device.

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 layer disposed therebetween. The organic electroluminescent compound according to the present invention may be used for an organic layer And can be manufactured using conventional device manufacturing methods and materials.

The organic 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 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 thereto and may include a smaller number of organic layers.

Therefore, in the organic electroluminescent device of the present invention, the organic layer may be a layer including a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously injecting holes and transporting holes, One or more layers may be included, and at least one of the layers may include a compound represented by the above Chemical Formulas 1 to 2.

In particular, the organic luminescent compound according to the present invention may be contained in the hole transporting functional layer or the luminescent layer, and may be included as a host material in the luminescent layer.

When the compound represented by any one of the above Chemical Formulas 1 to 2 is included as a host material in the light emitting layer, the light emitting layer may include at least one phosphorescent dopant, and the light emitting layer includes a host and a dopant The content of the dopant can be selected in the range of about 0.01 to about 20 parts by weight, based on 100 parts by weight of the host.

According to an embodiment of the present invention, a host compound represented by the formulas (1) to (2) according to the present invention and a dopant compound selected from the following [structural formulas 2] to [structural formula 8] More than species can contain.

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

[Structural Formula 6]

[Structural Formula 7]

[Structural formula 8]

In the organic layer having such a multi-layered structure, the compounds represented by the above Chemical Formulas 1 to 2 may be used in combination with a light emitting layer, a layer which simultaneously transports holes and holes, a layer which simultaneously transports holes and 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 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 compounds represented by the above Chemical Formulas 1 to 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 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 compounds represented by the formulas (1) to (2) 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 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 compounds represented by the formulas (1) to (2) may be contained 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 compounds represented by the formulas (1) to (2) may be included in the luminescent layer (5) or the electron transport 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 compounds represented by the formulas (1) to (2) 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 such a structure, the compounds represented by the above Chemical Formulas 1 to 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 compounds represented by the formulas (1) to (2) 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 compounds represented by the formulas (1) to (2) may be contained 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 compounds represented by the formulas (1) to (2) may be included in the luminescent 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 compounds represented by the formulas (1) to (2) may be included in the light emitting 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, Depositing an anode to form an anode, forming an organic layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode, and depositing a material usable as a cathode thereon.

In addition to such a method, an organic electroluminescent device may be fabricated by sequentially depositing a negative electrode material, an organic layer, and a positive electrode material on a substrate. The organic 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 layer may be formed using a variety of polymer materials by using a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

The anode material is preferably a material having a large work function so that injection of holes into the organic layer can be smoothly performed. 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 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 HOMO (highest occupied molecular orbital) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, 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  1: Synthesis of compound 1

(One) Manufacturing example  1: Synthesis of Intermediate 1-0

To a solution of bis (pinacolato) dibron (2.5 g, 0.010 mol), PdCl ₂ (dppf) (0.3 g, 0.0004 mol), potassium acetate (2.2 g, 0.016 mol) in 4-bromo-2-chloroquinazoline ), 80 mL of 1,4-dioxane was added, 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 2.1 g (yield: 71%) of Intermediate 1-0. (m / z = 290)

(2) Manufacturing example  2: Synthesis of intermediate 1-1

Pd (pph ₃ ) ₄ (0.3 g, 0.0003 mol) and potassium carbonate (4.1 g, 0.030 mol) were added to intermediate 1-0 (2.9 g, 0.010 mol) 100 mL of THF was added, 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 2.1 g (m / z = 318)

(3) Manufacturing example  3: Synthesis of intermediate 1-1-1

IPy ₂ BF ₄ (7.5 g, 0.020 mol) was dissolved in dichloromethane and then cooled to -78 ° C. HBF ₄ (6.5 g, 0.040 mol) was added thereto, followed by stirring for 10 minutes. After filtration of the solid, the filtrate was cooled to -60 DEG C, and intermediate 1-1 (3.2 g, 0.010 mol) was dropping slowly. 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 1.9 g (m / z = 317)

(4) Manufacturing example  4: Synthesis of intermediate 1-2

Compound 1-1-1 (3.2 g, 0.010 mol) was dissolved in 100 mL of diethyl ether, and AlCl ₃ (1.6 g, 0.012 mol) was slowly dropped. Stir for 15 min and then cool to 0 < 0 > C. After stirring for 1 hour, when the reaction was completed, slowly cooled to room temperature, and EA was added slowly until no bubbling occurred. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 2.6 g (yield: 85%

(5) Manufacturing example  5: Synthesis of intermediate 1-3

Intermediate 1-2 (3.0 g, 0.010 mol) was dissolved in 50 mL of DMSO, sodium tert-butoxide (4.8 g, 0.050 mol) was added at room temperature, and the mixture was exchanged at 70 ° C for 15 minutes. Then, methyl iodide (7.3 g, 0.050 mol) was slowly dropped and stirred for 1 hour. 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 give 2.0 g (m / z = 330)

(6) Manufacturing example  6: Synthesis of intermediate 1-4

Bromobenzene (1.6 g, 0.010 mol), dibenzo-18-crown-6 (1.1 g, 0.0030 mol) and copper (2) (1.2 g, 0.020 mol) were added to 3-bromo-9H- , potassium acetate (2.8 g, 0.020 mol), and the mixture was reacted at 120 ° C for 4 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 2.3 g (yield: 71%

(7) Manufacturing example  7: Synthesis of intermediate 1-5

Intermediate 1 (2.2 g, 0.010 mol) was subjected to the same procedure as in Example 1 (2) to give 9H-carbazol-3-ylboronic acid (2.5 g, 0.012 mol) -5> 3.0 g (yield: 73%). (M / z = 408)

(8) Manufacturing example  8: Synthesis of compound 1

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 1-5 (4.1 g, 0.010 mol) was added to intermediate 1-3 (3.3 g, 0.010 mol) 76%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.05 / d, 7.98 / d, 7.82 / d, 7.80 / m, 7.54 / m, 7.52 / m, 7.45 / m) 2H (8.55 7.50 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.58 / m, 7.33 / m, 7.25 /

LC / MS: m / z = 703 [(M + 1) ^&lt; ^{+ &}

Example  2: Synthesis of Compound 2

(One) Manufacturing example  1: Synthesis of intermediate 2-1

Was synthesized in the same manner as in Example 1 (6) except that 2-bromo-1,3-dimethylbenzene (1.9 g, 0.010 mol) was added to 3-bromo-9H-carbazole (2.5 g, 0.010 mol) 2.6 g (yield 76%) of Intermediate 2-1 (m / z = 350)

(2) Manufacturing example  2: Synthesis of intermediate 2-2

Intermediate 2-1 (3.5 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that 9H-carbazol-3-ylboronic acid (2.5 g, 0.012 mol) 2> 2.9 g (yield: 67%) was obtained. (M / z = 436)

(3) Manufacturing example  3: Synthesis of Compound 2

Synthesis was conducted in the same manner as in Example 1-Preparation Example (6), except that Intermediate 2-2 (4.4 g, 0.010 mol) was added to Intermediate 1-3 (3.3 g, 0.010 mol) 76%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.05 / d, 7.82 / d, 7.80 / m, 7.54 / m, 7.52 / m, 7.50 / d, 7.43 / m) 2H (8.55 7.39 / d, 7.29 / d, 7.25 / m, 1.92 / s, 1.85 / s)

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

Example  3: Synthesis of Compound 3

(One) Manufacturing example  1: Synthesis of intermediate 3-1

(3.2 g, 0.008 mol) was added to 3-bromo-6,9-diphenyl-9H-carbazole (2.1 g, 0.010 mol) (M / z = 484) (3.5 g, yield 73%) of Intermediate 3-1

(2) Manufacturing example  2: Synthesis of Compound 3

The compound 3-1 (4.8 g, 0.010 mol) was added to Intermediate 1-3 (3.3 g, 0.010 mol) and the compound 3 was synthesized in the same manner as in Example 1- (6) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.05 / d, 8.00 / d, 7.94 / d, 7.82 / d, 7.80 / m, 7.54 / m, 7.52 / m, 7.45 / m 7.51 / m, 7.35 / m) 2H (8.18 / d, 7.98 / d, 7.87 / d, 7.69 / d, 7.58 / / s, 7.50 / d)

LC / MS: m / z = 778 [(M + 1) ^&lt; ^{+ &}

Example  4: Synthesis of compound 4

(One) Manufacturing example  1: Synthesis of Intermediate 4-1

Bromo-9,9-dimethyl-9H-fluorene (2.7 g, 0.010 mol) was added to 6-bromo-9H, 9'H-3,3'-bicarbazole (4.1 g, 0.010 mol) Synthesis was conducted in the same manner as in Production Example 6 to obtain 4.2 g (yield: 70%) of Intermediate 4-1 (m / z = 603)

(2) Manufacturing example  2: Synthesis of intermediate 4-2

Intermediate 4-2 (4.4 g, 0.012 mol) was synthesized in the same manner as in Example 1 (2) except that phenylboronic acid (1.4 g, 0.012 mol) was added to Intermediate 4-1 (6.0 g, 0.010 mol) Yield: 73%). (M / z = 600)

(3) Manufacturing example  3: Synthesis of Compound 4

Synthesis was conducted in the same manner as in Example 1-Preparation Example (6), except that Intermediate 4-2 (6.0 g, 0.010 mol) was added to Intermediate 1-3 (3.3 g, 0.010 mol) 76%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.05 / d, 8.00 / d, 7.94 / d, 7.82 / d, 7.80 / m, 7.54 / m, 7.52 / m, 7.50 / d D, 7.51 / m, 7.50 / d, 7.40 / d, 1.85 / s, 7.41 / m, 7.33 / , 1.72 / s) 3H (7.77 / s) 4H (7.87 / d)

LC / MS: m / z = 895 [(M + 1) ^&lt; ^{+ &}

Example  5: Synthesis of Compound 5

(One) Manufacturing example  1: Synthesis of intermediate 5-0

(2.8 g, 0.008 mol) was added to Intermediate 1-0 (2.9 g, 0.010 mol) and 4-bromo-2-iodonaphthalen- (M / z = 385) of <Intermediate 5-0> (yield: 73%).

(2) Manufacturing example  2: Synthesis of Intermediate 5-1

2.3 g (yield: 58%) of Intermediate 5-1 was obtained by the same method as in Example 1 (3), except that Intermediate 5-0 (3.9 g, 0.010 mol) = 395)

(3) Manufacturing example  3: Synthesis of intermediate 5-2

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 5-1 (4.0 g, 0.010 mol) was added to obtain 2.8 g (yield 74%) of Intermediate 5-2 (m / z = 381)

(4) Manufacturing example  4: Synthesis of intermediate 5-3

Synthesis was conducted in the same manner as in Example 1 (5), except that Intermediate 5-2 (3.8 g, 0.010 mol) was added to obtain 2.5 g (yield: 60%) of Intermediate 5-3 (m / z = 409)

(5) Manufacturing example  5: Synthesis of intermediate 5-4

Intermediate 5-4 was synthesized in the same manner as in Example 1- (2), except that phenyl boronic acid (1.4 g, 0.012 mol) was added to Intermediate 5-3 (4.1 g, 0.010 mol) (Yield: 71%). (M / z = 406)

(6) Manufacturing example  6: Synthesis of intermediate 5-5

Dibromobenzene (2.4 g, 0.010 mol) was added to 1H-indol-3-ylboronic acid (1.3 g, 0.008 mol) -5> 1.6 g (yield: 73%). (M / z = 272)

(7) Manufacturing example  7: Synthesis of intermediate 5-6

3-ylboronic acid (3.3 g, 0.012 mol) was added to Intermediate 5-5 (2.7 g, 0.010 mol) and the title compound was synthesized in the same manner as in Example 1- 3.2 g (yield: 73%) of Intermediate 5-6 was obtained. (M / z = 434)

(8) Manufacturing example  8: Synthesis of Compound 5

Intermediate 5-6 (4.3 g, 0.010 mol) was added to Intermediate 5-4 (4.1 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 1- (6) 79%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.52 / d, 8.17 / d, 8.16 / d, 7.98 / d, 7.94 / d, 7.87 / d, 7.80 / m, 7.77 / s 7.71 / d, 7.69 / d, 7.63 / s, 7.54 / m, 7.52 / m, 7.45 / m, 7.41 / m, 7.36 / s, 7.33 / m, 7.25 / , 7.51 / m, 7.42 / m, 1.85 / s) 3H (7.50 / d) 4H (7.25 / d)

LC / MS: m / z = 805 [(M + 1) ^&lt; ^{+ &}

Example  6: Synthesis of Compound 6

(One) Manufacturing example  1: Synthesis of Compound 6

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 1-5 (4.1 g, 0.010 mol) and Intermediate 5-4 (4.1 g, 0.010 mol) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.52 / d, 8.18 / d, 7.98 / d, 7.80 / m, 7.63 / s, 7.54 / m, 7.52 / m, 7.45 / m, 7.41 / m 7.51 / m, 7.33 / m, 7.25 / m, 1.85 / s) 3H (7.50 / d, 7.94 / d, 7.87 / d, 7.79 / d, 7.77 / s, 7.69 / d, 7.58 / / d)

LC / MS: m / z = 779 [(M + 1) ^&lt; ^{+ &}

Example  7: Synthesis of Compound 7

(One) Manufacturing example  1: Synthesis of Intermediate 7-1

100 mL of 1,2-dichlorobenzene was added to triphenylphosphine (4.5 g, 0.017 mol) in 2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) and the mixture was reacted at 180 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and the resultant product was separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.2 g (m / z = 246)

(2) Manufacturing example  2: Synthesis of intermediate 7-2

Intermediate 7-2 (2.3 g, Yield 77%) was synthesized by the same method as in Example 1, (6) except that bromobenzene (1.6 g, 0.010 mol) was added to Intermediate 7-1 (2.1 g, 0.010 mol) %). (M / z = 322)

(3) Manufacturing example  3: Synthesis of intermediate 7-3

2.7 g (intermediate 7-3) was obtained in the same manner as in Example 1 (1) except that Intermediate 7-2 (3.2 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, Yield: 73%). (m / z = 369)

(4) Manufacturing example  4: Synthesis of Intermediate 7-4

Intermediate 7-4 (3.1 g, 0.012 mol) was added to Intermediate 5-5 (2.7 g, 0.010 mol) and synthesized in the same manner as in Example 1- (2) (Yield: 72%). (M / z = 434)

(5) Manufacturing example  5: Synthesis of Compound 7

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 7-4 (4.3 g, 0.010 mol) and Intermediate 5-4 (4.1 g, 0.010 mol) 5%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.52 / d, 8.18 / d, 8.17 / d, 7.98 / d, 7.94 / d, 7.80 / m, 7.79 / d, 7.71 / d M, 7.41 / m, 7.33 / m, 7.25 / m) 2H (7.79 / d, 7.58 / m, 7.51 / m , 7.42 / m, 1.85 / s) 3H (7.50 / d) 4H (7.25 / d)

LC / MS: m / z = 805 [(M + 1) ^&lt; ^{+ &}

Example  8: Synthesis of Compound 8

(One) Manufacturing example  1: Synthesis of Intermediate 8-1

N-bromosuccinimide (1.8 g, 0.010 mol) and 100 mL of dmf were added to compound 7 (8.1 g, 0.010 mol), and the mixture was reacted at 20 ° C for 8 hours with stirring. After completion of the reaction H ₂ 0: column purification after separating layer with ethyl acetate: Intermediate 8-1 by (n-Hexane MC) to afford 4.2 g (48%) (m / z = 883).

(2) Manufacturing example  2: Synthesis of Compound 8

The compound 8 was synthesized in the same manner as in Example 1 (2), except that phenyl boronic acid (1.5 g, 0.012 mol) was added to Intermediate 8-1 (8.8 g, 0.010 mol) 76%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.52 / d, 8.18 / d, 8.17 / d, 7.98 / d, 7.94 / d, 7.80 / m, 7.79 / d, 7.71 / d M, 7.42 / m, 7.41 / m, 7.33 / m, 7.25 / m) 2H (7.58 / m, 7.42 / m, 1.85 / ) 3H (7.50 / d) 4H (7.79 / d, 7.51 / m, 7.25 / d)

LC / MS: m / z = 882 [(M + 1) ^&lt; ^{+ &}

Example  9: Synthesis of Compound 9

(One) Manufacturing example  1: Synthesis of intermediate 9-0

Intermediate 9-O was synthesized by the same procedure as in Example 1 (2) except that 5-bromo-2-iodophenol (2.4 g, 0.008 mol) was added to Intermediate 1-0 (2.9 g, 0.010 mol) 0> 2.4 g (yield: 73%). (M / z = 335)

(2) Manufacturing example  2: Synthesis of Intermediate 9-1

2.2 g (yield: 64%) of <Intermediate 9-1> was obtained in the same manner as in Example 1 (3), except that Intermediate 9-0 (3.4 g, 0.010 mol) z = 345)

(3) Manufacturing example  3: Synthesis of intermediate 9-2

2.5 g (yield 76%) of <Intermediate 9-2> was obtained by the same method as employed in the preparation example (4) of Example 1, with the intermediate 9-1 (3.5 g, 0.010 mol) 331)

(4) Manufacturing example  4: Synthesis of intermediate 9-3

2.0 g (yield 55%) of Intermediate 9-3 was obtained by the same procedure as in Example 1 (5), except that Intermediate 9-2 (4.0 g, 0.010 mol) 359)

(5) Manufacturing example  5: Synthesis of intermediate 9-4

Intermediate 9-4 (2.6 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to Intermediate 9-3 (Yield: 73%). (M / z = 356)

(6) Manufacturing example  6: Synthesis of intermediate 9-5

Synthesis was conducted in the same manner as in Example 1 (6), except that 3-bromo-9H-carbazole (2.5 g, 0.010 mol) was added to Intermediate 9-4 (3.6 g, 0.010 mol) (M / z = 566) of 4.3 g (yield: 76%).

(7) Manufacturing example  7: Synthesis of Compound 9

Synthesis was conducted according to the same procedure as in Example 1 (2), except that triphenylen-2-ylboronic acid (3.3 g, 0.012 mol) was added to Intermediate 9-5 (5.7 g, 0.010 mol) g (yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.55 / d, 8.18 / d, 8.04 / d, 7.98 / d, 7.94 / d, 7.92 / s, 7.87 / d, 7.80 / m , 7.50 / d, 7.41 / m, 7.33 / m, 7.25 / m) 2H (8.93 d, 8.12 d, 7.88 m, 7.82 m, 7.77 d, 7.52 d, 7.51 m, )

LC / MS: m / z = 714 [(M + 1) ^&lt; ^{+ &}

Example  10: Synthesis of Compound 10

(One) Manufacturing example  1: Synthesis of Compound 10

Synthesis was conducted in the same manner as in Example 1 (2) except that 6-phenylnaphthalen-2-ylboronic acid (3.0 g, 0.012 mol) was added to Intermediate 9-5 (5.7 g, 0.010 mol) > 5.2 g (yield: 76%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.98 / d, 7.94 / d, 7.92 / s, 7.87 / d, 7.80 / m, 7.69 / d, 7.50 / d, 7.33 / m 7.55 / m, 7.07 / d) 2H (7.92 / d, 7.77 / d, 7.73 / d, 7.58 / s, 7.41 / m, 1.72 / s)

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

Example  11: Synthesis of Compound 11

(One) Manufacturing example  1: Synthesis of Compound 11

3-ylboronic acid (3.3 g, 0.012 mol) was added to Intermediate 9-5 (5.7 g, 0.010 mol) in the same manner as in Example 1 (2) To obtain 5.2 g (yield 71%) of < Compound 11 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / d, 7.92 / s, 7.80 / m, 7.45 / m, 7.41 / m, 7.07 / d) 2H (8.55 / d, 7.94 / d, 7.87 (7.77 / s, 7.50 / d), 7.69 / d, 7.58 / m, 7.52 / d, 7.51 / m, 7.33 /

LC / MS: m / z = 729 [(M + 1) ^&lt; ^{+ &}

Example  12: Synthesis of Compound 12

(One) Manufacturing example  1: Synthesis of Intermediate 12-1

Was synthesized in the same manner as in Example 1 (2) except that phenylboronic acid (1.4 g, 0.012 mol) was added to 2-bromo-3-chloro-1H-indole (2.3 g, 0.010 mol) 12-1> 1.7 g (yield: 73%). (M / z = 227)

(2) Manufacturing example  2: Synthesis of intermediate 12-2

2-ylboronic acid (3.3 g, 0.012 mol) was added to Intermediate 12-1 (2.3 g, 0.010 mol), and the title compound was synthesized by the same method as in Example 1- (M / z = 419) of 3.1 g (yield: 73%).

(3) Manufacturing example  3: Synthesis of Compound 12

The compound 12-2 (4.2 g, 0.010 mol) was added to Intermediate 9-4 (3.6 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 1- (6) 79%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.17 / d, 8.04 / d, 7.98 / d, 7.92 / s, 7.80 / m, 7.77 / d, 7.71 / d 7.50 / d, 7.07 / d) 2H (8.93 d, 8.12 d, 7.88 m, 7.82 m, 7.79 d, 7.52 d, 7.42 m, 7.41 m, 1.72 s) / m)

LC / MS: m / z = 740 [(M + 1) ^&lt; ^{+ &}

Example  13: Synthesis of compound 13

(One) Manufacturing example  1: Synthesis of compound 13

(3.3 g, 0.012 mol) was added to Intermediate 9-5 (5.7 g, 0.010 mol) in the same manner as in Example 1-Preparation Example (2) 13> 5.1 g (yield 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.98 / d, 7.94 / d, 7.92 / s, 7.87 / d, 7.80 / m, 7.69 / d, 7.50 / d, 7.33 / m M, 7.07 / d) 2H (7.77 / s, 1.72 / s) 3H (7.66 / s, 7.41 /

LC / MS: m / z = 716 [(M + 1) ^&lt; ^{+ &}

Example  14: Synthesis of compound 14

(One) Manufacturing example  1: Synthesis of Intermediate 14-0

Intermediate 14-0> was synthesized by the same method as in Example 1 (2), except that 2-iodophenol (2.2 g, 0.010 mol) was added to Intermediate 1-0 (3.5 g, 0.012 mol) (Yield: 73%). (M / z = 256)

(2) Manufacturing example  2: Synthesis of Intermediate 14-1

1.4 g (yield: 52%) of <Intermediate 14-1> was obtained by the same method as in Example 1- (3), except that Intermediate 14-0 (2.6 g, 0.010 mol) = 266)

(3) Manufacturing example  3: Synthesis of intermediate 14-2

2.1 g (yield 82%) of Intermediate 14-2 was obtained by the same procedure as in Example 1 (4), except that Intermediate 14-1 (2.7 g, 0.010 mol) 252)

(4) Manufacturing example  4: Synthesis of intermediate 14-3

1.5 g (yield 55%) of <Intermediate 14-3> was obtained by the same method as in Example 1- (5), except that Intermediate 14-2 (2.5 g, 0.010 mol) 280)

(5) Manufacturing example  5: Synthesis of intermediate 14-4

Synthesis was conducted in the same manner as in Example 1 (6) except that 9H, 9'H-3,3'-bicarbazole (3.3 g, 0.010 mol) was added to Intermediate 14-3 (2.8 g, 0.010 mol) 4.4 g (yield 76%) of Intermediate 14-4 (m / z = 576)

(6) Manufacturing example  6: Synthesis of Compound 14

Synthesis was conducted in the same manner as in Example 1 (6), except that 2-bromodibenzo [b, d] furan (2.5 g, 0.010 mol) was added to Intermediate 14-4 (5.8 g, 0.010 mol) (Yield: 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / d, 7.89 / d, 7.80 / m, 7.60 / d, 7.50 / d, 7.50 / s, 7.38 / m, 7.36 / d, 7.32 / m , 7.20 / d) 2H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.66 / d, 7.33 / m, 7.25 /

LC / MS: m / z = 743 [(M + 1) ^&lt; ^{+ &}

Example  15: Synthesis of compound 15

(One) Manufacturing example  1: Synthesis of compound 15

Synthesis was carried out in the same manner as in Example 1 (6) except that 3-bromo-9-phenyl-9H-carbazole (3.2 g, 0.010 mol) was added to Intermediate 14-4 (5.8 g, 0.010 mol) To obtain 4.4 g (yield: 68%) of Compound 15.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.98 / d, 7.80 / m, 7.60 / d, 7.45 / m, 7.36 / d) 2H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 (7.50 / d, 7.58 / m, 7.25 / m, 1.72 / s)

LC / MS: m / z = 653 [(M + 1) ^&lt; ^{+ &}

Example  16: Synthesis of Compound 16

(One) Manufacturing example  1: Synthesis of intermediate 16-0

Phenylboronic acid (1.4 g, 0.012 mol) was added to 4-bromo-2-chloro-7-iodoquinazoline (3.7 g, 0.010 mol) in the same manner as in Example 1- 2.3 g (yield: 73%) of intermediate 16-0 (m / z = 319)

(2) Manufacturing example  2: Synthesis of intermediate 16-00

2.7 g (Intermediate 16-00) was obtained in the same manner as in Example 1 (1) except that Intermediate 16-0 (3.2 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, Yield: 73%). (m / z = 366)

(3) Manufacturing example  3: Synthesis of intermediate 16-1

Intermediate 16-1 was synthesized in the same manner as in Example 1 (2) except that 2-iodophenol (2.6 g, 0.012 mol) was added to Intermediate 16-00 (3.7 g, 0.010 mol) (Yield: 73%). (M / z = 332)

(4) Manufacturing example  4: Synthesis of intermediate 16-2

2.0 g (yield: 58%) of <Intermediate 16-2> was obtained by adding the intermediate 16-1 (3.3 g, 0.010 mol) in the same manner as in Example 1- = 342)

(5) Manufacturing example  5: Synthesis of intermediate 16-3

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 16-2 (3.4 g, 0.010 mol) was added to obtain 2.7 g (yield 82%) of Intermediate 16-3 (m / z = 328)

(6) Manufacturing example  6: Synthesis of intermediate 16-4

Synthesis was conducted in the same manner as in Example 1 (5), except that Intermediate 16-3 (3.3 g, 0.010 mol) was added to obtain 2.2 g (yield: 61%) of Intermediate 16-4 (m / z = 356)

(7) Manufacturing example  7: Synthesis of Compound 16

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 1-5 (4.1 g, 0.010 mol) and Intermediate 16-4 (3.6 g, 0.010 mol) 76%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.28 / d, 8.10 / s, 7.90 / s, 7.87 / d, 7.77 / s, 7.69 / d, 7.60 / d, 7.46 / d, 7.36 / d , 6.93 / s) 2H (8.55 / d, 7.94 / d, 7.41 / m, 7.25 /

LC / MS: m / z = 733 [(M + 1) ^&lt; ^{+ &}

device Example  1: Compound 1 The light-  As a red host material Organic electroluminescence Device Manufacturing

CuPc was deposited to 80 nm and α-NPD was deposited to 30 nm on a glass substrate coated with ITO, followed by mixing 25% of Compound 1 and 6% of Ir (btp) ₂ (acac) sec. Then, Alq ₃ was deposited to a thickness of 40 nm, LiF was deposited to a thickness of 1 nm, and Al was deposited to a thickness of 120 nm to form an organic electroluminescent device. 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 Example  2 to 18

The organic electroluminescent devices of the device embodiments 2 to 16 were fabricated in the same manner as in the device example 1, except that the compound described in [Table 1] was used instead of the compound 1 described above.

device Comparative Example  One

The organic light emitting diode device for the comparative example was fabricated in the same manner except that CBP, which is generally used as a host material, was used instead of the compound manufactured by the invention in the device structure of the embodiment. The structures of the hole injection layer material CuPc, the hole transport material NPB, the light emitting host material CBP, and the red dopant Ir (btp) ₂ (acac) used in the device embodiment are respectively as follows.

[Table 1]

Measurement of driving voltage and luminous efficiency

The organic light emitting device (substrate size: 25 × 25 mm 2 / deposition area: 2 × 2 mm 2) according to the examples and the comparative examples was fixed to an IVL measurement set (CS-2000 + jig + IVL program) And the driving voltage (V) and the luminous efficiency (cd / A) of the deposition surface were measured and shown in Table 1 above. From the results of the above Examples, Comparative Examples and Table 1, it can be seen that the compounds represented by Chemical Formulas 1 to 16 according to the present invention show better characteristics such as driving voltage and luminescence efficiency than conventional red light emitting materials , A display element, a display element, an illumination, and the like.

Claims (8)

An organic light-emitting compound represented by the following Chemical Formula 1 or Chemical Formula 2:
[Chemical Formula 1]

(2)

In the above Chemical Formulas 1 to 2,
R ₁ to R ₇ each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms , A substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms,
R ₃ and R ₄ and R ₅ and R ₆ may be connected to each other to form a single ring or polycyclic ring of alicyclic or aromatic,
Among R ₁ to R ₇ , R ₅ is hydrogen except when R ₅ is linked to R ₆ to form a ring,
At least one of R ₈ to R ₁₅ is selected from the following [structural formula 1], all others are hydrogen,
[Structural formula 1]

In the above formula 1,
L is a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroarylene group having 6 to 24 carbon atoms (n is an integer of 0 to 2, and n 2 &gt; are the same or different from each other),
R _a and R _b are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, A substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, m is an integer of 0 to 4, m Is 2 or more, a plurality of R & lt _{; a} & gt _; and R &lt; _b & gt _; are each the same or different from each other)
Wherein each of L, R ₁ to R ₇ , R _a and R _b may be further substituted with at least one substituent, and at least one of the substituents may be deuterium, a halogen group, a cyano group, an alkylsilyl group having 1 to 10 carbon atoms , An alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 24 carbon atoms. delete delete An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic layers comprises an organic light emitting compound represented by Formula 1 or Formula 2 according to Claim 1. 5. The method of claim 4,
The organic layer includes at least one of a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously carrying out electron transport and electron injection, and a light emitting layer. Wherein at least one layer comprises an organic light-emitting compound represented by the above Chemical Formula (1) or (2). 6. The method of claim 5,
Wherein the light emitting layer comprises an organic light emitting compound represented by the formula (1) or (2). The method according to claim 6,
The organic electroluminescent compound represented by Formula 1 or Formula 2 is used as a host compound in the light emitting layer, and the light emitting layer further includes at least one dopant compound. delete

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