KR20190069083A - Organic compound, organic light emitting diode and organic light emiting device having the compound - Google Patents

Abstract

The present invention relates to: an organic compound comprising a heteroaromatic core excellent in bonding with an electron, triphenylene moieties, in which each of the same is directly or indirectly connected to the heteroaromatic core, and condensed heteroaromatic moieties having carbazole moieties; and an organic light emitting diode and an organic light emitting device using the organic compound in an organic material layer. The organic compound of the present invention has excellent charge transport characteristics, thereby being able to prevent a rise in driving voltage caused by delay of charge injection in a light emitting diode. In addition, since the organic compound can induce luminescence in all regions of a light emitting material layer, it is possible to improve luminous efficiency and a lifespan of the organic light emitting diode.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic light emitting diode (OLED)

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic compound used in an organic light emitting diode, and more particularly, to an organic compound that can be utilized as a material of an organic material layer of an organic light emitting diode, an organic light emitting diode including the same, and an organic light emitting device.

Recently, as the size of a display device has been increased, the demand for a flat display device having a small space occupation has increased. An organic light emitting diode (OLED) display device including a light emitting diode, also referred to as an organic electroluminescent device (OELD), has been attracting attention as one of such flat display devices.

An organic light emitting diode (OLED) display device is a self-emission type display device which does not require a backlight unit required in a liquid crystal display device (LCD) and emits light by a light emitting pixel portion of a light emitting diode. The organic light emitting diode display device is advantageous in that it can realize a lightweight, thin, very thin display because it can simplify the process, can be driven at a low voltage (10 V or less), has a relatively low power consumption and excellent color purity . In addition, the organic light emitting diode display device has a better viewing angle and contrast ratio than an LCD, and is capable of forming a device on a flexible transparent substrate such as a plastic substrate, thereby attracting attention as a next generation display after the LCD .

In a light emitting diode used in an organic light emitting diode display, electrons and holes are paired when charges are injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) It is a device that extinguishes light. In the light emitting layer, electrons and holes meet to form an exciton, and the energy of the organic compound contained in the light emitting layer becomes an excited state. The energy transfer from the excited state to the ground state And emits the generated energy as light to emit light.

The light emitting layer constituting the light emitting diode may have a single layer structure of the light emitting material layer, or may have a multi-layer structure for improving the light emitting efficiency and the lifetime of the device. For example, the light emitting layer of the light emitting diode includes a hole injection layer (HIL), a hole transporting layer (HTL), an emitting material layer (EML), an electron transporting layer (ETL) And an electron injection layer (EIL).

The process of fabricating the organic light emitting diode will be briefly described.

(1) First, a material such as indium tin oxide (ITO) is deposited on a transparent substrate to form an anode.

(2) A hole injection layer is formed on the anode. The hole injection layer may be formed of an organic material such as Dipyrazino [2,3-f: 2 ', 3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HATCN) .

(3) Next, a hole transport layer is formed on the hole injection layer. The hole transport layer is formed by depositing an organic material such as 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB) to a thickness of about 20 nm to 60 nm. In the case of a phosphorescent device, an exciton blocking layer such as an electron blocking layer (EBL) may be formed between the hole transport layer and the light emitting material layer to effectively confine the triplet exciton in the light emitting material layer.

(4) Next, a light emitting material layer, also called an organic light emitting layer, is formed on the hole transporting layer. The light emitting material layer may include a suitable host and a dopant. For example, in the case of blue fluorescence emission, 9,10-Bis (1-naphtyl) anthracene (α-ADN) is commonly used as a host and 4,4'- Phenyl] -amine (BD-1) is reacted with 1 (1, 1, 4,1, To 50% by weight, for example, 1 to 10% by weight, and is deposited to a thickness of 20 nm to 60 nm.

(5) Next, an electron transport layer and an electron injection layer are formed on the light emitting material layer. For example, tris (8-hydroxyquinoline) aluminum tris- (8-hydroxyquinoline aluminum; Alq ₃ ) is used as an electron transporting layer and LiF is used as an electron injecting layer. In the case of a phosphorescent device, a hole blocking layer (HBL) can be formed before the electron transport layer is formed in order to effectively confine the triplet exciton in the light emitting material layer.

(6) Next, a cathode is formed on the electron injection layer.

As described above, the holes and electrons injected from the anode and the cathode, respectively, in the light emitting diode form excitons in the light emitting layer to emit light. When only one material is used as a light emitting material, color purity, luminous efficiency and lifetime of the device may be deteriorated. Therefore, in order to improve the efficiency and lifetime of the device, the light emitting layer is usually composed of a host and a dopant. In a host-dopant binary system, a host generates excitons and transmits energy to the dopant rather than to light itself, generating highly efficient light through the dopant. That is, the energy obtained when the exciton is formed in the light emitting layer and transferred to the bottom state is finally transferred to the dopant through the host. When the light emitting layer is formed of the double material of the host and the dopant, energy to the dopant is intensively transferred, The probability of forming an exciton in the dopant is increased and the luminous efficiency is increased.

The light emitting material used in the organic light emitting device is the most important factor for determining the light emitting efficiency of the device, and in particular, in the host-dopant dual system, the host has a great influence on the efficiency and lifetime of the light emitting device. In this connection, Korean Patent No. 10-1404346 proposes that a vinyl type polynorbornene polymer can be used as a green phosphorescent host.

However, the light emitting material used in the organic light emitting device must have a high quantum efficiency and good electron and hole mobility. Among the currently used light emitting materials, the host has a wide band gap, so that the injection of electric charges is delayed, which causes the driving voltage of the device to rise. In addition, holes and electrons can not be injected into the light-emitting layer in a balanced manner, and light emission occurs at the interface with the layer adjacent to the light-emitting layer, thereby deteriorating the efficiency and lifetime of the device.

In particular, recently, development of an organic light emitting device having high efficiency and long life has become an urgent task. Considering the level of device characteristics required for medium to large-sized OLED panels, the OLED panel is more thermally stable than conventional light emitting materials, and has excellent charge injection and migration characteristics to prevent interfacial luminescence, It is necessary to develop a material capable of improving the surface roughness.

An object of the present invention is to provide an organic compound which is excellent in charge transporting property and can efficiently transfer energy when forming an exciton, an organic light emitting diode using the same, and an organic light emitting device.

Another object of the present invention is to provide an organic compound, an organic light emitting diode and an organic light emitting device using the organic compound, which can induce a low driving voltage of the device by improving the thin film durability of the device, I would like to.

According to an aspect of the present invention, there is provided a method for producing a heteroaromatic core, comprising: reacting a heteroaromatic core having at least one nitrogen atom with a triphenylene moiety directly or indirectly connected to a heteroaromatic core, Lt; RTI ID = 0.0 > heteroaromatic < / RTI >

In one exemplary embodiment, the condensed heteroaromatic moiety may be composed of 3 to 6 aromatic rings, preferably 4 to 6 aromatic rings, including carbazole moieties.

According to another aspect of the present invention, the present invention relates to an organic light emitting diode in which the organic compound is contained in an organic material layer.

According to another aspect of the present invention, the present invention relates to an organic light emitting device including the organic light emitting diode in which the organic compound is included in the organic material layer.

The organic compound of the present invention has a heteroaromatic core having at least one nitrogen atom and a condensed heteroaromatic moiety having a carbazole moiety and a triphenylene moiety bonded directly or indirectly to the heteroaromatic core respectively have.

Because of the structurally rigid condensed heteroaromatic moiety and the triphenylene moiety, the three-dimensional chemical structure between these condensed aromatic rings and the heteroaromatic core is limited. Accordingly, the energy can be transferred without energy loss due to the rotation of the molecules in the vibration mode related to the light emission.

In particular, since the organic compound according to the present invention contains a heteroaromatic core having a high electron density, electrons can be bonded quickly and the transport and transport properties of electrons can be enhanced. Therefore, when the organic compound of the present invention is applied to the organic light emitting layer of the organic light emitting diode, the injection of charge is not delayed, so that the device can be sufficiently driven even at a low voltage.

Particularly, when the organic compound of the present invention is used in the organic light emitting layer of the light emitting diode, holes and electrons are injected into the organic light emitting layer in a balanced manner, so that the charge balance in the organic light emitting layer can be maximized. The light emission can be induced in the entire region of the light emitting material layer without causing light emission at the interface between the organic light emitting layer and the charge transfer layer adjacent to the light emitting material layer. Therefore, the durability, luminous efficiency and / .

Accordingly, the organic compound of the present invention can be utilized not only as an organic light emitting layer of an organic light emitting diode, for example, a light emitting material layer, but also as a material of a common layer such as an electron transporting layer and / or an exciton blocking layer.

1 is a cross-sectional view schematically showing the structure of an organic light emitting diode to which an organic compound is applied, according to an exemplary embodiment of the present invention.
2 is a cross-sectional view schematically showing the structure of an organic light emitting diode having an exciton blocking layer to which an organic compound is applied, according to another exemplary embodiment of the present invention.
3 is a cross-sectional view schematically showing the structure of an organic light emitting diode display device, as an example of an organic light emitting device including an organic light emitting diode using the organic compound of the present invention, according to an exemplary embodiment of the present invention.
4 to 11 are graphs showing NMR analysis results of the organic compounds synthesized according to the exemplary embodiments of the present invention.

Hereinafter, the present invention will be described in detail with reference to the accompanying drawings when necessary.

[Organic compounds]

The light emitting material used in the organic light emitting diode should have high luminous efficiency such as quantum efficiency and high electron and hole mobility. The luminescent material must also be uniformly formed in the luminescent material layer, and the luminescence should be stably induced. Recently, development of a high efficiency and long-life organic light emitting device has emerged as an urgent task. A host that acts as an energy transmitter in a light emitting layer of two independent organic compounds has good color purity and can be vacuum deposited It should have a suitable molecular weight. In addition, the glass transition temperature and thermal decomposition temperature are high, so that thermal stability is required and high electrochemical stability is required for longevity. The organic compound according to one aspect of the present invention is configured to satisfy such a characteristic and can be represented by the following formula (1).

Formula 1

(In formula 1, R ₁ and R ₂ are each optionally substituted independently or C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted C ₅ ~ C ₃₀ Homo aryl group, an unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted by a C ₄ ~ C ₃₀ heteroaryl group, unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ substituted C group heteroaryl ₅ ~ C ₃₀ Homo arylalkyl group, unsubstituted or C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted by a C ₄ ~ C ₃₀ heteroaryl group, an unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group, or C ₄ ~ C ₃₀ heteroaryl group substituted C ₅ ~ C ₃₀ Homo aryloxy group and an unsubstituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted C ₄ ~ C ₃₀ heteroaryloxy Wherein one of R ₁ and R ₂ has a carbazole moiety and is selected from the group consisting of 3 to 6 Consisting of ring C ₁₀ ~ C ₃₀ condensed hetero aryl group; R ₃ to R ₅ are each independently a C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ C ₂₀ alkoxy group, o is an integer from 0 to 3, and p q is independently an integer of 0 to 4, L ₁ to L ₃ each independently represent a C ₅ -C ₃₀ homoarylene group which is unsubstituted or substituted by a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group, or C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ substituted C group C ₂₀ alkoxy ₄ ~ C ₃₀ heteroaryl group, is optionally substituted with C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ C ₂₀ alkoxy group substituted C ₅ ~ C ₃₀ And a C ₄ -C ₃₀ heteroaryloxylene group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group, a, b, and c are each independently selected from the group consisting of 0 or 1; X ₁ , X ₂ and X ₃ are each independently -N or -CR ₆ and R ₆ is selected from the group consisting of hydrogen, deuterium, tritium, C ₁ -C ₂₀ alkyl groups and C ₁ -C ₂₀ alkoxy groups , And at least one of X ₁ to X ₃ is N)

As used herein, "unsubstituted" or "unsubstituted" means that a hydrogen atom is substituted, in which case the hydrogen atom includes hydrogen, deuterium, and tritium.

As used herein, the substituent in the term "substituted" includes, for example, an alkyl group which is unsubstituted or substituted by halogen, an alkoxy group which is unsubstituted or substituted by halogen, halogen, cyano group, carboxyl group, carbonyl group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a hydrazyl group, a sulfonic acid group, an alkylsilyl group, an alkoxysilyl group, a cycloalkylsilyl group, But is not limited thereto.

The terms "heteroaromatic ring", "heterocycloalkyl group", "heteroarylene group", "heteroarylalkylene group", "heteroaryloxylene group", "heteroaryl group", "heteroarylalkyl group" The term "hetero" used in the aryloxycarbonyl group, aryloxycarbonyl group, aryloxycarbonyl group, aryloxycarbonyl group, aryloxycarbonyl group, aryloxycarbonyl group, aryloxycarbonyl group and aryloxycarbonyl group means that at least one, ≪ RTI ID = 0.0 > Rl, < / RTI >

According to one exemplary embodiment, R ₁ to R ₂ in Formula (1) are each independently an unsubstituted or substituted phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, anthracenyl, indenyl, A condensed or fused homo aromatic ring such as a phenanthrenyl group, an azulenyl group, a pyrenyl group, a fluorenyl group, a tetracenyl group, an indacenyl group or a spirobifluorenyl group, and / or a pyrrolyl group, A pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a tetrazinyl group, an imidazolyl group, a pyrazolyl group, an indolyl group, a carbazolyl group, a benzocarbazolyl group, , An indolocarbazolyl group, an indenocarbazolyl group, a benzofuranocarbazolyl group, a dibenzofuranocarbazolyl group, a benzothienocarbazolyl group, a dibenzothihenocarbazolyl group, a quinolinocarbazolyl group, an isoquinolinecarbazolyl group, A quinolinocarbazolyl group, A quinolinyl group, a quinolinyl group, a quinazolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, An oxazolyl group, an oxadiazolyl group, a triazolyl group, a dioxinyl group, an oxazolyl group, an oxazolyl group, an oxazolyl group, an oxazolyl group, an oxazolyl group, an oxazolyl group, an oxazolyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, an acridinyl group, a phenanthrolinyl group, a furanyl group, A non-condensed or condensed heteroaromatic ring such as a benzofuranyl, dibenzofuranyl, thiopyranyl, thiazinyl, thiophenyl or N-substituted spiropyranyl group.

For example, when R ₁ and / or R ₂ in formula (1) is substituted with an aromatic functional group, for example a C ₅ -C ₃₀ homoaryl group or a C ₄ -C ₃₀ heteroaryl group, these functional groups are unsubstituted or substituted by a Or a substituted or unsubstituted benzothiophene group in which the phenyl group is substituted with a meta or para position, a dibenzoyl group substituted with a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, or a spirobifluorenyl group, A thiophene group, a benzofuranyl group, a dibenzofuranyl group, a pyrrolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a tetrazinyl group, an imidazolyl group, A carbamoyl group, a diazo group, a carbazole group, a benzocarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, an indenocarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a quinolinyl group, A naphthyl group, a naphthyl group, A quinazolinyl group, a quinazolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinazolinyl group or a benzoquinoxalinyl group and a benzoquinolinyl group, May be the same heteroaryl group.

At this time, the number of aromatic rings which may be substituted for R ₁ and / or R ₂ is 1 to 2, more preferably 1. If the number of these aromatic rings is too large, the triplet energy level of the organic compound becomes low as the conjugated structure becomes longer in the whole molecule, and the band gap energy can be excessively reduced. The aromatic substituent which may be substituted for R ₁ and / or R ₂ is preferably a phenyl group, a biphenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyrimidyl group, A pyridinyl group, a pyranyl group, a pyridazinyl group, a furanyl group or a thiophenyl group.

On the other hand, in formula (1), one of R ₁ and R ₂ is a C ₁₀ -C ₃₀ fused heteroaryl group having a carbazole moiety and consisting of 3 to 6, preferably 3 to 5 aromatic rings. The C ₁₀ -C ₃₀ fused heteroaryl group having a carbazole moiety includes not only a carbazolyl group but also an aryl group fused to the carbazole moiety with other aromatic rings. Condensed heteroaryl groups condensed with other aromatic rings in the carbazole moiety are benzocarbazolyl group, dibenzocarbazolyl group, indenocarbazolyl group, indolocarbazolyl group (indolocarbazolyl group), indolocarbazolyl group a benzofurancarbazolyl group, a dibenzocarbazolyl group, a benzothienoocarbazolyl group and a dibenzothenocarbazolyl group, quinolinol groups, And a quinolinocarbazolyl group. However, the present invention is not limited thereto.

In the formula (1), at least a nitrogen atom in X ₁ to X ₃ forms a heteroaryl core having a high electron affinity at the center of the organic compound molecule according to the present invention. Accordingly, the organic compound represented by the general formula (1) can be used as a so-called " n-type host " in the emissive material layer (EML (ETL) (see FIG. 1) and the hole blocking layer (HBL, see FIG. 2). For example, a centrally located heteroaryl core may have pyridinine, pyrimidine, pyrazine, pyridazine, or triazine moieties depending on the number of nitrogen atoms. have.

On the other hand, in one exemplary embodiment, L ₁ to L ₃ in the general formula (1) include a central heteroaromatic core having an affinity with electrons, a linker that mediates an external triphenylenic moiety and an aromatic ring ). For example, L ₁ to L ₃ may each independently be a C ₅ to C ₃₀ homoarylene group or a C ₄ to C ₃₀ heteroarylene group.

In one non-limiting embodiment, when L ₁ to L ₃ in formula (1) are C ₅ -C ₃₀ homoarylene groups which are unsubstituted or substituted by C ₁ -C ₂₀ alkyl groups or C ₁ -C ₂₀ alkoxy groups, L ₁ to L ₃ each independently represent a group selected from the group consisting of phenylene, biphenylene, terphenylene, tetraphenylene, indenylene, naphthylene, And examples thereof include azulenylene, indacenylene, acenaphthylene, fluorenylene, spiro-fluorenylene group, phenalenylene, phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluororanthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, Picenylene group, perylenylene group ne, pentaphenylene, and hexacenylene. < / RTI >

In another alternative embodiment, when L ₁ to L ₃ are C ₄ to C ₃₀ heteroarylene groups which are unsubstituted or substituted by C ₁ to C ₂₀ alkyl groups or C ₁ to C ₂₀ alkoxy groups, L ₁ to L ₃ are each And may be independently substituted with one or more groups selected from the group consisting of pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, isoindolylene, isoindolylene, indolylene, indolylene, There can be mentioned benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, benzoquinolinylene group, benzoisoquinoline group, Norbornylene group, norbornylene group, benzoquinazolinylene group, benzoquinone A phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoxazolylene group, a phenanthrolinylene group, a phenanthrene group, Benzimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene, isothiazolylene, isothiazole, isothiazole, isocyanate group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, Benzopyranyl group, benzofuranyl group, dibenzofuranylene group, benzofurodibenzofuranyl group, benzothienobenzofuranyl group, benzothienodibenzofuranyl group, benzothiophenylene group, dibenzofuranyl group, Examples of the benzene ring include dibenzothiophenylene, benzothiobenzothiophenylene, benzothienodibenzothiophenylene, carbazolylene, benzocarbazolylene, dibenzocarbazolylene, indolocarbazolylene, indenocarbazolyl, And may be selected from the group consisting of a furocarbazolylene group, a benzothienocarbazolylene group, an imidazopyrimidinylene group and an imidazopyridinylene group.

In one exemplary embodiment, when the number of aromatic rings constituting each of L ₁ to L ₃ is increased, the conjugated structure in the entire organic compound becomes excessively long, so that the band gap of the organic compound may be excessively decreased And the triplet energy level can be lowered. Therefore, the number of aromatic rings constituting each of L ₁ to L ₃ is preferably 1 to 2, more preferably 1. Also with respect to charge injection and migration properties, L ₁ to L ₃ can each be a 5-membered ring to a 7-membered ring, -membered ring. For example, each of L ₁ to L ₃ independently represents an unsubstituted or substituted phenylene group, a biphenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group , A pyridazinylene group, a furanylene group or a thiophenylene group.

The organic compound represented by the general formula (1) has a central heteroaromatic core having an affinity with electrons, a triphenylenem moiety having a strong chemical structure in the heteroaromatic core, and a condensed heteroaromatic moiety containing a carbazole moiety Lt; / RTI > The three dimensional chemical structure between the structurally stable triphenylene moiety and / or the condensed heteroaromatic moiety and the central heteroaromatic core is limited and there is no energy loss due to the rotation of the molecule in the luminescent mechanism. Due to the heteroaromatic core located at the center, it is possible to efficiently combine with electrons to improve the movement and transport properties of electrons. Accordingly, when the organic compound represented by the general formula (1) is applied to the organic light emitting layer, holes and electrons can be moved in a balanced manner in the organic light emitting layer and injected into the light emitting material layer. The organic compound represented by the formula (1) can be applied to the organic light emitting layer to realize low-voltage driving, and light emission can be induced in the entire region of the light emitting material layer, thereby improving the durability, luminous efficiency and lifetime of the light emitting diode.

In one exemplary embodiment, the condensed heteroaromatic moiety constituting the carbazole moiety in the organic compound of the present invention may be composed of 4 to 6 aromatic rings. Such an organic compound may be represented by the following general formula (2).

(2)

Wherein R ₇ is an unsubstituted or substituted C ₅ -C ₃₀ homoaryl group or a C ₄ -C ₃₀ heteroaryl group and is a condensed heteroaryl group, the condensed heteroaryl group is a benzocarbazolyl group, a dibenzobacazole group, A diazo group, a diazo group, an indenocarbazoyl group, an indolocarbazolyl group, a benzopureocarbazolyl group, a dibenzofuracarbazolyl group, a benzothienocarbazolyl group, a dibenzothienocarbazolyl group, a quinolinocarbazolyl group, Isoquinolinocarbazolyl group, R ₈ is a C ₅ to C ₃₀ aryl group or a C ₄ to C ₃₀ heteroaryl group, L ₄ and L ₅ are each independently selected from the group consisting of a phenylene group, A and b are independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a propyl group, a propyl group, a propyl group, a butyryl group, Lt; / RTI >

The condensed heteroaromatic moiety (R ₇ ) constituting the organic compound represented by the general formula (2) is composed of 4 to 6 aromatic rings and thus has a stronger chemical structure than the carbazole moiety. Thus, since the three-dimensional chemical structure between these condensed heteroaromatic moieties (R ₇ ) and the central triazine moiety is further limited, energy can be transferred to other molecules, for example, Can be delivered as a luminescent dopant. Since it is not necessary to apply a high voltage to realize effective luminescence, not only low-voltage driving is possible but also stress on the luminescent material or charge transfer material due to application of a high voltage is reduced. Accordingly, the organic compound represented by the general formula (2) can be used to fabricate a light emitting diode having low power consumption, excellent luminous efficiency, and improved device lifetime.

More specifically, the organic compound according to the present invention may include any compound selected from PGH1 to PGH24 represented by the following general formula (3).

(3)

The organic compounds represented by the above-mentioned general formulas (1) to (3) can be efficiently combined with electrons to improve electron transport and transport properties. Also, the chemical structure between the heteroaryl core located at the center of the molecule and the rigid condensed aromatic moiety located outside is limited, and energy can be transferred without energy loss. Accordingly, by using the organic compounds represented by Chemical Formulas 1 to 3, a light emitting diode capable of low-voltage driving, improved luminous efficiency, and improved lifetime can be realized. For example, the organic compounds represented by the general formulas (1) to (3) are excellent in electron transporting properties and can be used as materials for a light emitting material layer, an electron transporting layer and / or a hole blocking layer constituting a light emitting diode.

[Light Emitting Diode and Organic Light Emitting Device]

As described above, for example, the organic compounds represented by the general formulas (1) to (3) are excellent in the binding property to electrons and have a limited three-dimensional structure and can transmit light emission energy without energy loss. Therefore, the organic compounds represented by the general formulas (1) to (3) can be applied to organic light emitting diodes, and will be described. 3 is a schematic cross-sectional view of a light emitting diode to which an organic compound is applied according to the first exemplary embodiment of the present invention.

1, a light emitting diode 100 according to a first exemplary embodiment of the present invention includes a first electrode 110 and a second electrode 120 facing each other, a first electrode 110 and a second electrode 120, 110, and 120, respectively. The organic material layer 130 includes a hole injection layer (HIL) 140, a hole transport layer (HTL) 150, a light emitting material layer (EML) 160, an electron transport layer (ETL) 170, And an electron injection layer (EIL) 180.

The first electrode 110 is made of a conductive material having a relatively large work function and is an anode. For example, the first electrode 110 may be formed of indium-tin-oxide (ITO) or indium-zinc-oxide (IZO).

The second electrode 120 is made of a conductive material having a relatively small work function value and is a cathode. For example, the second electrode 120 may be made of aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or an alloy thereof.

The hole injection layer 140 is located between the first electrode 110 and the hole transport layer 150 and improves the interface characteristics between the first electrode 110 as an inorganic material and the hole transport layer 150 as an organic material. In one exemplary embodiment, the hole-injecting layer 140 is formed of 4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine (4,4' MTDATA), copper phthalocyanine (CuPc), tris (4-carbazoyl-9-yl-phenyl) amine, TCTA), N, N'- N'-diphenyl-N, N'-bis (1-naphthyl) -1, NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (1, 4, 5, 8, 9, 11-hexaazatriphenylenehexacarbonitrile (HAT-CN), 1,3,5-tris [4- (diphenylamino) phenyl] benzene, 1,3,5- (3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), N- (biphenyl-4-yl) -9,9-dimethyl- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene- -phenyl-9H-carba zol-3-yl) phenyl) -9H-fluoren-2-amine, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane N, N ', N'-tetrakis (4-biphenyl) benzidine (N, N'-tetramethyluronium hexafluorophosphate), 6-Tetralfluoro-7,7,8,8-tetracyanoquinodimethane Tetrakis (4-biphenyl) benzidine). Depending on the characteristics of the organic light emitting diode 100, the hole injection layer 140 may be omitted.

The hole transport layer 150 is disposed adjacent to the light emitting material layer 160 between the first electrode 110 and the light emitting material layer 160. In one exemplary embodiment, the hole transport layer 150 is formed of N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-4,4'- (TPD), NPD, 4,4'-bis (N-carbazolyl) -1, 4'-diphenyl-N, N'- N, N ', N'-tetrakis (4-biphenyl) benzidine, N - (4,4'- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene-2-amine (N- (biphenyl-4-yl) ) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) 4-yl) -N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) 9H-carbazol-3-yl) phenyl) biphenyl-4-amine.

The light emitting material layer 160 may be doped with a dopant to increase the luminous efficiency of the device. At least one organic compound represented by any one of Chemical Formulas 1 to 3 may be used as a host of the light emitting material layer 160. For example, the organic compound represented by the general formulas (1) to (3) has a central heteroaromatic moiety that efficiently bonds with electrons and functions as an electron acceptor, and thus can be used as an n- have.

In the exemplary embodiment, only at least one organic compound represented by any one of Chemical Formulas 1 to 3, which is a compound having excellent hole transporting properties, is used as a host of the light emitting material layer 160 to inject electrons into the light emitting material layer 160 Improve power, and transfer energy to the appropriate luminescent dopant without losing energy associated with luminescence.

In another exemplary embodiment, at least one organic compound represented by any one of Chemical Formulas 1 to 3, which is an n-type host, is used as the host of the light emitting material layer 160, and a p-type host having an electron donating moiety Can be used in combination. The p-type host that can be used in combination with the organic compounds represented by formulas (1) to (3) as the n-type host may be a compound having a carbazole moiety, for example, a bivalent carbazole-based or tricarbazole-based compound.

For example, a p-type host can be a CBP, 3,3-di (9H-carbazol-9-yl) biphenyl, mCBP) Carbazole-9-yl) -2,2'-dimethylbiphenyl (CDBP), 4,4'-bis (carbazole- , 4 "-tris (carbazol-9-yl) triphenylamine, 2T-NATA or TcTa, 1,3,5-tris Carbazole-9-yl) benzene (TCP), 1,3-bis (carbazole-9-yl) benzene -9-yl) benzene; MCP), 9,9'-di (biphenyl-3-yl) -9H, 9'H-3,3'-biphenyl- -9H, 9'H-3,3'-bicarbazole), 9,9'-di ([1,1'-biphenyl] -Bicarbazole (9,9'-di ([1,1'-biphenyl] -4-yl) -9H, 9'H-3,3'- bicarbazole and / or 9- (9-phenyl-3,3'-bicarbazole), but the present invention is not limited thereto.

The HOMO energy level of the p-type host is higher than the HOMO energy level of the n-type host and the lowest unoccupied molecular orbital ; LUMO) energy level may be lower than the LUMO energy level of the p-type host. In addition, the triplet energy level (E _T1 ^H ) of the p-type host and the n-type host is higher than the triplet energy level (E _T1 ^D ) of the dopant, Level (E _S1 ^H ) may be higher than the single-energy level (E _S1 ^D ) of the dopant.

When a p-type host and an n-type host are used in combination, the p-type host and the n-type host represented by Chemical Formulas 1 to 3 are excited state charge transfer complexes, such as an exciplex. The triplet energy level and singlet energy level of the exciplex are higher than the triplet energy level and singlet energy level of the dopant, respectively, so that the energy transfer from the triplet state or singlet state of the exciplex to the dopant can occur.

When the n-type host, which is an organic compound represented by Chemical Formulas 1 to 3, and the p-type host are used in combination as the host of the light emitting material layer 160, the light emitting diode 100 can be driven at a low voltage. In this case, the light emitting diode 100 having high luminous efficiency and long life can be realized by inducing light emission in the entire region of the light emitting material layer 160. At this time, by adopting a dopant having triplet energy lower than the triplet energy of the host, the energy transferred to the dopant can be prevented from being reverse-transferred to the host, so that it can have a high luminous efficiency and charge can be easily transferred from the host to the dopant Can be transferred.

When adopting a combination host of an n-type host and a p-type host represented by Formulas (1) to (3), the n-type host and the p-type host in the whole host are respectively 20 to 80% by weight, To 70% by weight, and more preferably 40% to 60% by weight. By appropriately controlling the mixing ratio of the p-type host and the n-type host, holes and electrons can be injected into the light emitting material layer 160 in a balanced manner, thereby improving the light emitting efficiency and the device lifetime of the light emitting diode 100 Can be improved.

The light emitting material layer 160 includes a dopant in addition to a host and / or a p-type host which is an organic compound represented by Chemical Formulas 1 to 3. For example, the dopant included in the light emitting material layer 160 may be a phosphorescent dopant. The phosphorescent dopant that can be used for the light emitting material layer 160 is not particularly limited and is, for example, a complex compound of a metal atom composed of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). It is preferably a metal complex compound such as iridium (Ir) or platinum (Pt), particularly preferably an iridium (Ir) complex compound.

Considering the use of an organic compound represented by any one of Chemical Formulas 1 to 3 as a host, it is necessary to efficiently transfer charge from these hosts and to prevent energy from being reverse-transferred to the host. In relation to this object, it may be preferable to use a dopant having an energy band gap between the energy band gaps of the organic compounds represented by Chemical Formulas 1 to 3, that is, a dopant whose triplet energy level is lower than the triplet energy level of the host have. In one exemplary embodiment, the dopant that can be used for the light emitting material layer 160 may be at least one material represented by the following Chemical Formula 4 or Chemical Formula 5, but the present invention is not limited thereto.

Formula 4

Formula 5

Wherein R ₁₁ to R ₁₉ are each independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, C ₁ -C ₃₀ alkyl groups unsubstituted or substituted with halogen, cyano group, unsubstituted or substituted C ₃ -C ₃₀ homo An unsubstituted or substituted C ₃ to C ₃₀ heterocycloalkyl group, an unsubstituted or substituted C ₅ to C ₃₀ homoaryl group, an unsubstituted or substituted C ₄ to C ₃₀ heteroaryl group, an unsubstituted or substituted C ₅ -C ₃₀ homoarylalkyl groups, unsubstituted or substituted C ₄ -C ₃₀ heteroarylalkyl groups, unsubstituted or substituted C ₅ -C ₃₀ homoaryloxyl groups, and unsubstituted or substituted C ₄ -C ₃₀ heteroaryl R ₂₀ is hydrogen, deuterium, tritium or an unsubstituted or substituted C ₁ -C ₃₀ alkyl group, r is an integer from 1 to 4, R ₂₁ to R ₂₈ are each independently selected from the group consisting of Independently hydrogen, deuterium, triplet Unsubstituted or substituted C ₃ to C ₃₀ heterocycloalkyl groups, unsubstituted or substituted C ₃ to C ₃₀ heterocycloalkyl groups, substituted or unsubstituted C ₃ to C ₃₀ substituted or unsubstituted C ₁ to C ₃₀ alkyl groups, cyano groups, substituted or unsubstituted C ₃ to C ₃₀ homocycloalkyl groups, Unsubstituted or substituted C ₅ to C ₃₀ homoaryl groups, unsubstituted or substituted C ₄ to C ₃₀ heteroaryl groups, unsubstituted or substituted C ₅ to C ₃₀ arylalkyl groups, unsubstituted or substituted C ₄ to C ₃₀ Substituted or unsubstituted C ₅ -C ₃₀ heteroarylalkyl groups, unsubstituted or substituted C ₅ -C ₃₀ homoaryloxyl groups, and unsubstituted or substituted C ₄ -C ₃₀ heteroaryloxyl groups, or is unsubstituted or substituted with adjacent substituents to form a ring of the substituted C ₅ ~ C _30; in formula 4 and formula 5 is represented by the formula L 6; n is an integer of 1 to 3 in formula 4 and formula 5)

6

Wherein R ₃₁ to R ₃₈ are each independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, C ₁ -C ₃₀ alkyl groups unsubstituted or substituted by halogen, cyano group, unsubstituted or substituted C ₃ -C ₃₀ homo An unsubstituted or substituted C ₃ to C ₃₀ heterocycloalkyl group, an unsubstituted or substituted C ₅ to C ₃₀ homoaryl group, an unsubstituted or substituted C ₄ to C ₃₀ heteroaryl group, an unsubstituted or substituted C ₅ -C ₃₀ homoarylalkyl groups, unsubstituted or substituted C ₄ -C ₃₀ heteroarylalkyl groups, unsubstituted or substituted C ₅ -C ₃₀ homoaryloxyl groups, and unsubstituted or substituted C ₄ -C ₃₀ heteroaryl An oxyl group, or taken together with the adjacent substituents to form an unsubstituted or substituted C ₅ -C ₃₀ aromatic ring)

In one exemplary embodiment, the dopant of the light emitting material layer 160 may be at least one of D1 to D14 represented by the following general formula (7).

Formula 7

When a dopant is used as a host in the light emitting material layer 160 and the energy is received from the host, the dopant may be introduced into the light emitting material layer 160 on the basis of the host applied to the light emitting material layer 160 May be doped at a ratio of 0.1 to 50% by weight, preferably 1 to 20% by weight.

An electron transport layer 170 and an electron injection layer 180 may be sequentially stacked between the light emitting material layer 160 and the second electrode 120. The material forming the electron transport layer 170 requires high electron mobility and stably supplies electrons to the light emitting material layer 160 through smooth electron transport.

In one exemplary embodiment, the electron transporting layer 170 is formed of an imidazole, an oxadiazole, a triazole, a phenanthroline, a benzoxazole, a benzothiazole benzothiazole, benzimidazole, triazine, and the like. For example, the electron transport layer 170 may be formed of tris (8-hydroxyquinoline aluminum) (Alq ₃ ), 2-4-yl-5- (4-tertiary-butylphenyl) 4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate 2-anthracenyl) phenyl] -1-phenyl-1H-benzimidazole (2- [4- (9,10- -Di-2-naphthalenyl-2-anthracenyl phenyl-1H-benzimidazole), 3- (4-biphenyl- 4-yl) -5- (4-tertbutylphenyl) -4-phenyl-4H-1,2,4-triazole (TAZ), 4,7- 4,7-diphenyl-1,10-phenanthrloine (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9- 7-diphenyl-1,10-phenathroline, Bathocuproine, BCP, Tris (phenylquinoxaline; TPQ) and / or 1,3,5-tris (N-phenylbenzimidazol- Benzene (1,3,5-Tris (N-phenylbenzimidazol-2-yl) benzene; TP Bi, etc. However, the present invention is not limited thereto. In another alternative embodiment, the organic compound represented by the general formulas (1) to (3) may be used as the material of the electron transport layer 170.

The electron injection layer 180 is located between the second electrode 120 and the electron transport layer 170 and improves the characteristics of the second electrode 120 to improve the lifetime of the device. In one exemplary embodiment, the material of the electron injection layer 180 may be an alkali halide material such as LiF, CsF, NaF, BaF ₂ , and / or Liq, lithium benzoate, sodium stearate stearate and the like may be used, but the present invention is not limited thereto.

That is, the light emitting diode 100 according to the first embodiment of the present invention includes first and second electrodes 110 and 120 facing each other, and a first electrode 110 and a second electrode 120 between the first and second electrodes 110 and 120, An electron transport layer 170, and an electron injection layer 180. The organic light emitting layer 140 includes a hole transport layer 150, a light emitting material layer 160, an electron transport layer 170, and an electron injection layer 180. Since the organic compounds represented by Chemical Formulas 1 to 3 are excellent in electron transporting property, they can be used alone in at least one layer constituting the light emitting material layer 160 and / or the electron transporting layer 170 among the organic material layers 130, ≪ / RTI >

As described above, since the organic compound of the present invention has excellent charge transporting properties, when the organic compound is used for the light emitting material layer 160 and / or the electron transporting layer 170, The light emitting diode 100 can be driven. In particular, when the organic compound represented by the general formulas (1) to (3) is used for the light emitting material layer 160, charges can be injected in a balanced manner to induce light emission in the entire region of the light emitting material layer 160, ) And / or a long life can be induced.

Also in the light emitting diode 100 of the first embodiment, it is possible to induce a low driving voltage, an excellent luminous efficiency, and / or an improved device lifetime by using organic compounds represented by Chemical Formulas 1 to 3 in at least one of the organic layers 130 . The light emitting diode according to another embodiment of the present invention may include an additional organic layer so that charge can be injected and moved more evenly. FIG. 2 schematically shows a light emitting diode 200 according to a second embodiment of the present invention. Fig.

2, a light emitting diode 200 according to a second embodiment of the present invention includes a first electrode 210 and a second electrode 220 facing each other, a first electrode 210 and a second electrode 210, The organic layer 230 is disposed between the organic layer 230 and the organic layer 230. The organic material layer 230 may include a hole injecting layer 240, a hole transporting layer 250, an electron blocking layer (EBL) 310, a light emitting material layer 260, a hole blocking layer HBL 320, an electron transport layer (ETL) 170, and an electron injection layer (EIL) 180.

The first electrode 210 is made of a conductive material having a relatively large work function value and is an anode. For example, the first electrode 110 may be formed of indium-tin-oxide (ITO) or indium-zinc-oxide (IZO).

The second electrode 220 is made of a conductive material having a relatively small work function value and is a cathode. For example, the second electrode 220 may be formed of aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or an alloy thereof.

The hole injecting layer 240 is located between the first electrode 210 and the hole transporting layer 250 and improves the interface characteristics between the inorganic first electrode 210 and the organic hole transporting layer 250. In one exemplary embodiment, the hole-injecting layer 240 is formed of a mixture of MTDATA, CuPc, TCTA, NPB, HAT-CN, TDAPB, PEDOT / PSS, N- (biphenyl- F4TCNQ and / or N, N, N ', N'-tetrakis (4- (9-phenyl-9H- Biphenyl) benzidine, and the like. The hole injection layer 240 may be omitted depending on the characteristics of the organic light emitting diode 200.

The hole transport layer 250 is positioned adjacent to the light emitting material layer 260 between the first electrode 210 and the light emitting material layer 260. In one exemplary embodiment, the hole transport layer 250 is formed of TPD, NPB, CBP, N, N, N'N'-tetrakis (4-biphenyl) benzidine, N- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene-2-amine and / or N- (biphenyl- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) biphenyl) -4-amine.

On the other hand, when the holes move to the second electrode 220 through the light emitting material layer 260 or electrons travel to the first electrode 210 through the light emitting material layer 260, Can be imported. In order to prevent this, the light emitting diode 200 according to the second embodiment of the present invention may include an exciton blocking layer in at least one of the upper and lower portions of the light emitting material layer 260.

For example, the light emitting diode 200 according to the second embodiment of the present invention includes an electron blocking layer 255 between the hole transport layer 250 and the light emitting material layer 260 for controlling the movement of electrons Can be located. In one exemplary embodiment, the electron blocking layer 255 is formed of a metal oxide such as TCTA, tris [4- (diethylamino) phenyl] amine, N - Phenyl-9H-fluorene-2-amine, tri-p-tolylamine, Bis (4- (N, N'-di (p-tolyl) amino) phenyl) cyclohexane, methylphenyl) amino] phenyl] -N, N'-diphenyl- [1,1'-bis (4- methylphenyl) cyclohexane; TAPC), MTDATA, mCP, mCBP, CuPC, N, ] -4,4'-diamine (N, N'-bis [4- [bis (3-methylphenyl) amino] phenyl] -N, N'- diphenyl- [1,1'- -diamine DNTPD), TDAPB, and / or (N- (biphenyl) -2-yl) -N- (9,9-dimethyl-9H-fluoren- (Biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluoren-2-yl) -9,9'-spirobi [fluorene] -2 -amine.

The light emitting material layer 260 may be doped with a dopant to increase the luminous efficiency of the device. As the host of the luminescent material layer 260, organic compounds represented by Chemical Formulas 1 to 3 may be used. For example, at least one of the organic compounds represented by Chemical Formulas 1 to 3 may be used as an n-type host of the light emitting material layer 260. In this case, for example, a p-type host having a carbazole moiety may be included in the light emitting material layer 260.

In this case, the light emitting material layer 260 may include a dopant such as a phosphorescent dopant having a lower triplet energy level than the organic compound represented by the general formulas (1) to (3). For example, the dopant may be the metal complex compound represented by the above formulas (4) to (7). When the light emissive material layer 260 is composed of a host-dopant, the dopant may be doped at a ratio of about 0.1 to 50 wt%, preferably 1 to 20 wt%, based on the host.

In the second embodiment of the present invention, a hole blocking layer 265 is disposed as another exciton blocking layer between the light emitting material layer 260 and the electron transporting layer 270 to form the light emitting material layer 260 and the electron transporting layer 270, Thereby preventing the movement of holes. In one exemplary embodiment, oxadiazole, triazole, phenanthroline, benzoxazole, and the like, which can be used for the electron transport layer 270 as the material of the hole blocking layer 265, ), Benzothiazole, benzimidazole, triazine and the like can be used. For example, a hole blocking layer 265 is compared with the Nora material HOMO energy level lower BCP, Alq _3, Liq, bis (2-methyl-8-quinolinol used for the light emitting material layer 260 Sat -N1, O 8) - (1,1'-Biphenyl-4-olato) aluminum (BAlq), bis (2-methyl- 4,6- (3,5-di-3-pyridylphenyl) -2-methylpyrimidine (B3PYMPM), bis 2-Biphenyl-4-yl-5- (4-t-butylphenyl) -1,3 , 4-oxadiazole (PBD), and / or spiro-PBD, but the present invention is not limited thereto. In another alternative embodiment, the hole blocking layer 265 may be made of the organic compound represented by the general formulas (1) to (3).

Meanwhile, an electron transport layer 270 and an electron injection layer 280 may be sequentially stacked between the light emitting material layer 260 and the second electrode 220. The material of the electron transport layer 270 requires high electron mobility and stably supplies electrons to the light emitting material layer 260 through smooth electron transport.

In one exemplary embodiment, the electron-transporting layer 270 is formed of an imidazole, oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole benzothiazole, benzimidazole, triazine, and the like. For example, the electron transporting layer 270 may be formed of Alq3, PBD, spiro-PBD, Liq, 2- [4- (9,10- -1H-benzimidazole, TAZ, Bphen, BCP, TPQ and / or TPBi, but the present invention is not limited thereto. In another alternative embodiment, the electron transporting layer 270 may be composed of an organic compound represented by the general formulas (1) to (3).

The electron injection layer 280 is located between the second electrode 220 and the electron transport layer 270 and improves the characteristics of the second electrode 220 to improve the lifetime of the device. In one exemplary embodiment, as the material of the electron injection layer 280, an alkali halide-based material such as LiF, CsF, NaF, or BaF ₂ and / or an organometallic material such as Liq, lithium benzoate, or sodium stearate may be used However, the present invention is not limited thereto.

That is, the light emitting diode 200 according to the second embodiment of the present invention differs from the light emitting diode 100 according to the first embodiment in that holes or electrons move in at least one of the upper surface and the lower surface of the light emitting material layer 260 And an electron blocking layer 255 and a hole blocking layer 265 as an exciton blocking layer which can prevent the electron transporting layer 251 and the hole blocking layer 265. [ Since the organic compounds represented by Chemical Formulas 1 to 3 are excellent in electron transporting property, at least one of the organic compound layers 230, the hole blocking layer 265, and / or the electron transporting layer 270, Layer alone or in combination with the dopant.

As described above, since the organic compound of the present invention has excellent charge transport properties, when an organic compound is applied to the light emitting material layer 260, the hole blocking layer 265 and / or the electron transporting layer 270, The light emitting diode 200 can be driven even at a low voltage by improving the transportation ability. In particular, when the organic compound represented by the general formulas (1) to (3) is used for the light emitting material layer 260, charges can be injected in a balanced manner to induce light emission in the entire region of the light emitting material layer 260, ) And / or a long life can be induced.

The organic light emitting diode according to the present invention can be applied to an organic light emitting diode display device or an organic light emitting device such as a lighting device to which the organic light emitting diode is applied. For example, a display device to which the organic light emitting diode of the present invention is applied will be described. 5 is a schematic cross-sectional view of an organic light emitting diode display device according to an exemplary embodiment of the present invention.

3, the organic light emitting diode display 300 includes a driving thin film transistor Td as a driving element, a planarization layer 360 covering the driving thin film transistor Td, And an organic light emitting diode 400 connected to a driving thin film transistor Td as a driving element. The driving thin film transistor Td includes a semiconductor layer 310, a gate electrode 330, a source electrode 352 and a drain electrode 354. In FIG. 5, the driving thin film transistor Td has a coplanar structure, And a transistor Td.

The substrate 302 may be a glass substrate, a thin flexible substrate, or a polymeric plastic substrate. For example, the flexible substrate may be formed of a material such as polyimide (PI), polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), and / or polycarbonate PC). ≪ / RTI > The driving thin film transistor Td as the driving element and the substrate 302 on which the organic light emitting diode 400 is located constitute an array substrate.

A semiconductor layer 310 is formed on the substrate 302. For example, the semiconductor layer 310 may be made of an oxide semiconductor material. In this case, a light shielding pattern (not shown) and a buffer layer (not shown) may be formed under the semiconductor layer 310. The light shielding pattern prevents light from being incident on the semiconductor layer 310, Thereby preventing deterioration of the semiconductor device. Alternatively, the semiconductor layer 310 may be formed of polycrystalline silicon. In this case, impurities may be doped on both edges of the semiconductor layer 310.

A gate insulating layer 320 made of an insulating material is formed on the entire surface of the substrate 302 on the semiconductor layer 310. A gate insulating film 320 may be formed of an inorganic insulating material such as silicon oxide (SiO ₂₎ or silicon nitride (SiNx).

A gate electrode 330 made of a conductive material such as metal is formed on the gate insulating layer 320 to correspond to the center of the semiconductor layer 310. A gate line (not shown) and a first capacitor electrode (not shown) may be formed on the gate insulating layer 320. The gate wiring may extend along the first direction, and the first capacitor electrode may be connected to the gate electrode 330. Although the gate insulating layer 320 is formed on the entire surface of the substrate 302, the gate insulating layer 320 may be patterned to have the same shape as the gate electrode 330.

An interlayer insulating film 340 made of an insulating material is formed on the entire surface of the substrate 302 on the gate electrode 330. The interlayer insulating film 340 may be formed of an inorganic insulating material such as silicon oxide (SiO ₂ ) or silicon nitride (SiN x), or may be formed of an organic insulating material such as benzocyclobutene or photo-acryl have.

The interlayer insulating film 340 has first and second semiconductor layer contact holes 342 and 344 that expose upper surfaces on both sides of the semiconductor layer 310. The first and second semiconductor layer contact holes 342 and 344 are located apart from the gate electrode 330 on both sides of the gate electrode 330. Here, the first and second semiconductor layer contact holes 342 and 344 are also formed in the gate insulating film 320. Alternatively, when the gate insulating film 320 is patterned in the same shape as the gate electrode 330, the first and second semiconductor layer contact holes 342 and 344 are formed only in the interlayer insulating film 340.

A source electrode 352 and a drain electrode 354 made of a conductive material such as metal are formed on the interlayer insulating layer 340. A data line (not shown), a power line (not shown), and a second capacitor electrode (not shown) may be formed on the interlayer insulating layer 340 in the second direction.

The source electrode 352 and the drain electrode 354 are spaced apart from each other around the gate electrode 330 and connected to both sides of the semiconductor layer 310 through the first and second semiconductor layer contact holes 342 and 344, Contact. Although not shown, the data wiring extends along the second direction and intersects the gate wiring to define the pixel region, and the power wiring for supplying the high potential voltage is located apart from the data wiring. The second capacitor electrode is connected to the drain electrode 354 and overlaps the first capacitor electrode to form a storage capacitor with the dielectric layer between the first and second capacitor electrodes as a dielectric layer.

The semiconductor layer 310, the gate electrode 330, the source electrode 352, and the drain electrode 354 constitute a driving thin film transistor Td. The driving thin film transistor Td illustrated in FIG. 3 has a coplanar structure in which a gate electrode 330, a source electrode 352, and a drain electrode 354 are disposed on a semiconductor layer 310. Alternatively, the driving thin film transistor Td may have an inverted staggered structure in which a gate electrode is located below the semiconductor layer and a source electrode and a drain electrode are located above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.

Further, a switching thin film transistor (not shown), which is a switching element having substantially the same structure as the driving thin film transistor Td, is further formed on the substrate 302. [ The gate electrode 330 of the driving thin film transistor Td is connected to a drain electrode (not shown) of a switching thin film transistor (not shown) and the source electrode 352 of the driving thin film transistor Td is connected to a power supply wiring . A gate electrode (not shown) and a source electrode (not shown) of the switching thin film transistor (not shown) are connected to the gate wiring and the data wiring, respectively.

The organic light emitting diode display 300 may include a color filter (not shown) for absorbing light generated in the organic light emitting diode 400. For example, a color filter (not shown) can absorb red (R), green (G), blue (B), and white (W) light. In this case, color filter patterns of red, green, and blue that absorb light may be formed separately for each pixel region, and each of the color filter patterns may include an organic light emitting diode (OLED) 400 and the organic layer 430 in the organic layer 430. By adopting a color filter (not shown), the organic light emitting diode display 300 can realize full-color.

For example, when the organic light emitting diode display 300 is a bottom emission type, a color filter (not shown) for absorbing light may be disposed on the interlayer insulating layer 340 corresponding to the organic light emitting diode 400 . In an alternative embodiment, if the organic light emitting diode display 300 is a top emission type, the color filter may be located on top of the organic light emitting diode 400, i.e., above the second electrode 420.

A planarization layer 360 is formed on the entire surface of the substrate 302 over the source electrode 352 and the drain electrode 354. The planarization layer 360 has a flat upper surface and a drain contact hole 362 that exposes the drain electrode 354 of the driving thin film transistor Td. Here, the drain contact hole 362 is formed directly on the second semiconductor layer contact hole 344, but may be formed apart from the second semiconductor layer contact hole 344. Planarization layer 360 may be formed of an organic insulating material such as silicon oxide (SiO ₂₎ or silicon nitride may be formed of an inorganic insulating material such as (SiNx), benzocyclobutene (benzocyclobutene) or the picture acrylate (photo-acryl) have.

The light emitting diode 400 includes a first electrode 410 located on the planarization layer 360 and connected to the drain electrode 354 of the driving TFT Td, (430) and a second electrode (420).

One electrode 410 is formed separately for each pixel region. The first electrode 410 may be an anode and may be formed of a conductive material having a relatively large work function value. For example, the first electrode 410 may be formed of a transparent conductive material such as ITO, IZO, ITZO, SnO, ZnO, ICO, and AZO.

Meanwhile, when the organic light emitting diode display device 300 of the present invention is a top emission type, a reflective electrode or a reflective layer may be further formed under the first electrode 410. For example, the reflective electrode or the reflective layer may be formed of an aluminum-palladium-copper (APC) alloy.

A bank layer 370 covering the edge of the first electrode 410 is formed on the planarization layer 360. The bank layer 370 exposes the center of the first electrode 410 corresponding to the pixel region.

An organic layer 430 is formed on the first electrode 410. In one exemplary embodiment, the organic layer 430 may have a single layer structure of a light emitting material layer. Alternatively, as shown in FIGS. 1 and 2, the organic material layer 430 may include a plurality of organic materials such as a hole injection layer, a hole transporting layer, an electron blocking layer, a light emitting material layer, a hole blocking layer, an electron transporting layer, and / Or an organic material layer.

A second electrode 420 is formed on the substrate 302 on which the organic material layer 430 is formed. The second electrode 420 is disposed on the front surface of the display region and is made of a conductive material having a relatively small work function value and can be used as a cathode. For example, the second electrode 420 may be formed of any one of an alloy or a combination thereof such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or aluminum- .

An encapsulation film 380 is formed on the second electrode 420 to prevent external moisture from penetrating into the organic light emitting diode 400. The encapsulation film 380 may have a laminated structure of a first inorganic insulating layer 382, an organic insulating layer 384, and a second inorganic insulating layer 386, but is not limited thereto.

As described above, the organic light emitting diode 400 includes the organic compound layer 430 in which the organic compound represented by Chemical Formulas 1 to 3 is used as a host. The organic compounds represented by the general formulas (1) to (3) are excellent in charge transporting property and have a triplet energy level higher than that of the dopant.

Therefore, when the organic compound represented by the general formulas (1) to (3) is used as a host in which the electron transporting property of the organic material layer 430 constituting the organic light emitting diode 400 is improved, the energy transferred to the dopant is reverse- . Since the organic compounds represented by Chemical Formulas 1 to 3 have excellent charge transport properties, when the organic compound layer 430 is applied to the organic compound layer 430, the organic light emitting diode 400 can be driven at a low voltage. Further, charges are injected in a balanced manner in the organic material layer 430, so that interfacial light emission can be prevented. Accordingly, the organic light emitting diode 400 and the organic light emitting diode display device 300 including the organic light emitting diode display 300 are improved in luminous efficiency by using the organic compounds represented by Chemical Formulas 1 to 3 in the organic material layer 430, The light emitting diode 400 can be realized.

Hereinafter, the present invention will be described with reference to exemplary embodiments, but the present invention is not limited to the technical ideas described in the following embodiments.

Synthesis Example 1: Synthesis of PGH1 compound

1) Compound [1] Synthesis

[Reaction Scheme 1a]

6 g (4 mmol) of Pd (PPh ₃ ) ₄ (Tetrakis (triphenylphosphine) palladium (0)), 31 g (88 mmol) of 2-boronic ester triphenylene, mmol) and 26 g (177 mmol) of potassium carbonate were suspended in a mixed solvent of 600 mL of toluene, 200 mL of ethyl alcohol and 200 mL of distilled water, and the mixture was refluxed and stirred for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The reaction solution was refluxed under reduced pressure and then recrystallized to obtain 18 g (yield: 48%) of compound [1].

2) Synthesis of PGH1

[Reaction Scheme 1b]

Compound [1] 12g (28 mmol) , 3- Boro Nick ester 9-phenyl-carbazol-13g (28 mmol), Pd ( PPh 3) 4 2g (1 mmol), potassium carbonate 8g (56 mmmol) in toluene 150 mL , Ethyl alcohol (50 mL), and distilled water (50 mL), followed by stirring with a? Q current for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The reaction mixture was concentrated under reduced pressure and recrystallized to obtain 9 g of PGH1 (yield: 51%). NMR analysis results of the synthesized PGH1 compound are shown in Fig.

Synthesis Example 2: Synthesis of PGH2 compound

[Reaction Scheme 2]

Compound [1] 12g (28 mmol) , 9- dihydro-carbazol 4.7g (28 mmol), Pd ( PPh 3) 4 2g (1 mmol), potassium carbonate 8g (56 mmmol) in toluene 150 mL, 50 mL ethyl alcohol , And 50 mL of distilled water, followed by stirring under reflux for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The reaction mixture was concentrated under reduced pressure and recrystallized to obtain 8.6 g of PGH2 (yield: 56%). The NMR analysis results of the synthesized PGH2 compound are shown in Fig.

Synthesis Example 3: Synthesis of PGH3 compound

[Reaction Scheme 3]

Compound [1] 12g (28 mmol) , 4- Boro Nick carbazole ester 15g (28 mmol), Pd ( PPh 3) 4 2g (1 mmol), potassium carbonate 8g (56 mmmol) in -9-7- phenyl indole Was suspended in a mixed solvent of 150 mL of toluene, 50 mL of ethyl alcohol and 50 mL of distilled water, and the mixture was refluxed and stirred for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The reaction mixture was concentrated under reduced pressure and recrystallized to obtain 10 g of PGH3 (yield: 45%). The NMR analysis results of the synthesized PGH3 compound are shown in Fig.

Synthesis Example 4 Synthesis of PGH4 Compound

[Reaction Scheme 4]

Compound [1] 12g (28 mmol) , 3- Boro Nick carbazole ester 15g (28 mmol), Pd ( PPh 3) 4 2g (1 mmol), potassium carbonate 8g (56 mmmol) in -9-7- phenyl indole Was suspended in a mixed solvent of 150 mL of toluene, 50 mL of ethyl alcohol and 50 mL of distilled water, and the mixture was refluxed and stirred for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The reaction mixture was concentrated under reduced pressure and recrystallized to obtain 11 g of PGH4 (yield: 50%). NMR analysis results of the synthesized PGH4 compound are shown in Fig.

Synthesis Example 5: Synthesis of PGH5 compound

[Reaction Scheme 5]

2 g ( ₂ mmol) of Pd ₂ (dba) ₃ (Tris (dibenzylideneacetone) dipallaium (0)), 9 g (28 mmol) of 9-hydro-7-phenylindolocarbazole, 3 mL (4 mmol) of tert-butylphosphine and 5 g (56 mmol) of sodium tertiary butoxide were suspended in 150 mL of toluene, and the mixture was refluxed with stirring for 12 hours. The organic layer was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed, and the residue was recrystallized from a silica gel column and toluene to obtain 10 g of PGH5 (yield: 50%). NMR analysis results of the synthesized PGH5 compound are shown in FIG.

Synthesis Example 6: Synthesis of PGH6 compound

[Reaction Scheme 6]

Compound [1] 12g (28 mmol) , 9-dihydro-8-phenyl-indole carbazole _{9g (28 mmol), Pd 2} (dba) 3 2g (2 mmol), Tree-tert-butylphosphine 3 mL (4 mmol ) And 5 g (56 mmol) of sodium tertiary butoxide were suspended in 150 mL of toluene, and the mixture was refluxed and stirred for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed and recrystallized from a silica gel column and toluene to obtain 8 g of PGH6 (yield: 40%). NMR analysis results of the synthesized PGH6 compound are shown in Fig.

Synthesis Example 7: Synthesis of PGH15 compound

[Reaction Scheme 7]

12 g (28 mmol) of the compound [1], 8 g (28 mmol) of benzofukarbazole, ₂ g (2 mmol) of Pd ₂ (dba), 3 mL (4 mmol) of triturated butylphosphine, 5 g (56 mmol) of the side was suspended in 150 mL of toluene, and the mixture was refluxed and stirred for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed, and the residue was recrystallized from a silica gel column and toluene to obtain 11 g (yield: 62%) of a compound PGH15. NMR analysis results of the synthesized PGH15 compound are shown in Fig.

Synthesis Example 8: Synthesis of PGH21 Compound

[Reaction Scheme 8]

12 g (28 mmol) of the compound [1], 8 g (28 mmol) of benzothiocarbazole, ₂ g (2 mmol) of Pd ₂ (dba _{) 3} , 3 mL (4 mmol) of triturated butylphosphine, 5 g (56 mmol) was suspended in 150 mL of toluene, and the mixture was refluxed and stirred for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed and recrystallized from a silica gel column and toluene to obtain 9 g of PGH21 (yield: 49%). The NMR analysis results of the synthesized PGH21 compound are shown in Fig.

Example 1: Fabrication of organic light emitting diode

An organic light emitting diode in which ITO (reflector) / hole injecting layer / hole transporting layer / electron blocking layer / light emitting material layer / electron transporting layer / electron injecting layer / cathode / CPL were stacked in this order was fabricated. The ITO substrate was washed with UV ozone prior to use and then loaded into the evaporation system. After substrate cleaning, the substrate was transferred into a vacuum deposition chamber and layers were deposited by evaporation from a heated boat under a vacuum of about 10 ^-7 Torr in the following order.

N, N, N ', N'-tetrakis (4-biphenyl) benzidine was doped with 5% of the hole injection layer (F4TCNQ, (9,9-dimethyl-9H-fluoren-2-yl) -9,9'-biphenylbenzidine, 750A) -Di (biphenyl-3-yl) -9H, 9 ' H- 3,3'-bi-carbazole and n- type host, the second host PGH1 (1: 1) / dopant (Ir (ppy) ₃₎ 10% doping, 350 Å), the electron transport layer (BCP, 350Å), e Injection layer (LiF, 10 Å), cathode (Al, 1000 Å), CPL (capping layer).

After the CPL was formed, it was encapsulated with glass. After deposition of these layers, the film was transferred from the deposition chamber into a dry box for subsequent film formation and subsequently encapsulated using a UV cured epoxy and a getter. This organic light emitting diode has an emission area of 9 mm 2.

Examples 2 to 8: Fabrication of organic light emitting diodes

(Example 2), PGH3 (Example 3), PGH4 (Example 4) and PGH5 (Example 5) synthesized in Synthesis Examples 2 to 8, respectively, instead of PGH1 as the second host of the luminescent material layer, ), PGH6 (Example 6), PGH15 (Example 7), and PGH21 (Example 8) were used.

Comparative Example 1: Fabrication of organic light emitting diode

An organic light emitting diode was fabricated by repeating the procedure of Example 1 except that the n-type host shown below was used in place of PGH1 as the second host of the luminescent material layer.

Comparative Example Host

Experimental Example 2: Evaluation of physical properties of organic light emitting diode

The driving voltage, luminous efficiency and lifetime of the organic light emitting diode fabricated in each of Examples 1 to 8 and Comparative Examples were evaluated. The fabricated organic light emitting diode was connected to an external power supply (KEITHLEY) and evaluated at room temperature using a photometer (PR 650). The results of the lifetime of the organic light emitting diode at a constant current of 8,000 nL at a constant current based on the driving voltage, the luminous efficiency and the luminance of 20,000 nit are shown in Table 1 below. The efficiency and lifetime were evaluated on the basis of comparative examples.

Measurement of physical properties of organic light emitting diodes Sample Voltage (V) Relative efficiency Relative life Comparative Example 3.98 1.00 1.00 Example 1 3.94 0.99 1.11 Example 2 4.09 0.99 1.69 Example 3 3.61 1.02 2.40 Example 4 3.68 1.02 2.84 Example 5 3.80 1.00 4.69 Example 6 3.64 1.02 9.47 Example 7 3.83 1.01 4.53 Example 8 3.74 1.02 4.82

As shown in Table 1, when the organic compound synthesized according to the present invention is used as an n-type host of the light emitting material layer as compared with the case where the conventional n-type host is used as a host of the light emitting material layer, The driving voltage of the diode was reduced by up to 9.3%, the luminous efficiency increased by up to 2%, and the device lifetime increased by up to 9.47 times. These results indicate that the organic compound synthesized according to the present invention improves the charge transport ability in the light emitting material layer and is caused by inducing light emission in the entire region of the light emitting material layer.

Although the present invention has been described based on the exemplary embodiments and examples of the present invention, the present invention is not limited to the technical ideas described in the above embodiments and examples. Those skilled in the art will appreciate that various modifications and changes may be made without departing from the spirit and scope of the present invention as defined by the appended claims. It is apparent, however, that the appended claims are intended to cover all such modifications and changes as fall within the true scope of the invention.

100, 200, 400: organic light emitting diode
110, 210, 410: a first electrode
120, 220, 420: the second electrode
130, 230, 430: organic layer
140, 240: Hole injection layer
150, 250: hole transport layer
160, 260: light emitting material layer
170, 270: electron transport layer
180, 280: electron injection layer
255: electron blocking layer
265: hole blocking layer
300: Organic Light Emitting Diode Display
Td: driving thin film transistor

Claims (10)

An organic compound represented by the following formula (1).
Formula 1

(In formula 1, R ₁ and R ₂ are each optionally substituted independently or C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted C ₅ ~ C ₃₀ Homo aryl group, an unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted by a C ₄ ~ C ₃₀ heteroaryl group, unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ substituted C group heteroaryl ₅ ~ C ₃₀ Homo arylalkyl group, unsubstituted or C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted by a C ₄ ~ C ₃₀ heteroaryl group, an unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group, or C ₄ ~ C ₃₀ heteroaryl group substituted C ₅ ~ C ₃₀ Homo aryloxy group and an unsubstituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted C ₄ ~ C ₃₀ heteroaryloxy Wherein one of R ₁ and R ₂ has a carbazole moiety and is selected from the group consisting of 3 to 6 Consisting of ring C ₁₀ ~ C ₃₀ condensed hetero aryl group; R ₃ to R ₅ are each independently a C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ C ₂₀ alkoxy group, o is an integer from 0 to 3, and p q is independently an integer of 0 to 4, L ₁ to L ₃ each independently represent a C ₅ -C ₃₀ homoarylene group which is unsubstituted or substituted by a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group, or C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ substituted C group C ₂₀ alkoxy ₄ ~ C ₃₀ heteroaryl group, is optionally substituted with C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ C ₂₀ alkoxy group substituted C ₅ ~ C ₃₀ And a C ₄ -C ₃₀ heteroaryloxylene group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group, a, b, and c are each independently selected from the group consisting of 0 or 1; X ₁ , X ₂ and X ₃ are each independently -N or -CR ₆ and R ₆ is selected from the group consisting of hydrogen, deuterium, tritium, C ₁ -C ₂₀ alkyl groups and C ₁ -C ₂₀ alkoxy groups , And at least one of X ₁ to X ₃ is N)
The method according to claim 1,
Wherein the compound represented by the formula (1) comprises a compound represented by the following formula (2).
(2)

Wherein R ₇ is an unsubstituted or substituted C ₅ -C ₃₀ homoaryl group or a C ₄ -C ₃₀ heteroaryl group and is a condensed heteroaryl group, the condensed heteroaryl group is a benzocarbazolyl group, a dibenzobacazole group, A diazo group, a diazo group, an indenocarbazoyl group, an indolocarbazolyl group, a benzopureocarbazolyl group, a dibenzofuracarbazolyl group, a benzothienocarbazolyl group, a dibenzothienocarbazolyl group, a quinolinocarbazolyl group, Isoquinolinocarbazolyl group, R ₈ is a C ₅ to C ₃₀ aryl group or a C ₄ to C ₃₀ heteroaryl group, L ₄ and L ₅ are each independently selected from the group consisting of a phenylene group, A and b are independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a propyl group, a propyl group, a propyl group, a butyryl group, Lt; / RTI >
The method according to claim 1,
Wherein the compound represented by Formula 1 comprises any one of PGH1 to PGH24 represented by Formula 3 below.
(3)

The first electrode,
A second electrode facing the first electrode,
And at least one organic layer positioned between the first electrode and the second electrode,
Wherein the organic material layer comprises an organic compound represented by the following formula (1).
Formula 1

(In formula 1, R ₁ and R ₂ are each optionally substituted independently or C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted C ₅ ~ C ₃₀ Homo aryl group, an unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted by a C ₄ ~ C ₃₀ heteroaryl group, unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ substituted C group heteroaryl ₅ ~ C ₃₀ Homo arylalkyl group, unsubstituted or C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted by a C ₄ ~ C ₃₀ heteroaryl group, an unsubstituted or substituted C ₅ ~ C ₃₀ Homo aryl group, or C ₄ ~ C ₃₀ heteroaryl group substituted C ₅ ~ C ₃₀ Homo aryloxy group and an unsubstituted C ₅ ~ C ₃₀ Homo aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted C ₄ ~ C ₃₀ heteroaryloxy Wherein one of R ₁ and R ₂ has a carbazole moiety and is selected from the group consisting of 3 to 6 Consisting of ring C ₁₀ ~ C ₃₀ condensed hetero aryl group; R ₃ to R ₅ are each independently a C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ C ₂₀ alkoxy group, o is an integer from 0 to 3, and p q is independently an integer of 0 to 4, L ₁ to L ₃ each independently represent a C ₅ -C ₃₀ homoarylene group which is unsubstituted or substituted by a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group, or C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ substituted C group C ₂₀ alkoxy ₄ ~ C ₃₀ heteroaryl group, is optionally substituted with C ₁ ~ C ₂₀ alkyl group or a C ₁ ~ C ₂₀ alkoxy group substituted C ₅ ~ C ₃₀ And a C ₄ -C ₃₀ heteroaryloxylene group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group, a, b, and c are each independently selected from the group consisting of 0 or 1; X ₁ , X ₂ and X ₃ are each independently -N or -CR ₆ and R ₆ is selected from the group consisting of hydrogen, deuterium, tritium, C ₁ -C ₂₀ alkyl groups and C ₁ -C ₂₀ alkoxy groups , And at least one of X ₁ to X ₃ is N)
5. The method of claim 4,
Wherein the compound represented by Formula 1 comprises a compound represented by Formula 2 below.
(2)

Wherein R ₇ is an unsubstituted or substituted C ₅ -C ₃₀ homoaryl group or a C ₄ -C ₃₀ heteroaryl group and is a condensed heteroaryl group, the condensed heteroaryl group is a benzocarbazolyl group, a dibenzobacazole group, A diazo group, a diazo group, an indenocarbazoyl group, an indolocarbazolyl group, a benzopureocarbazolyl group, a dibenzofuracarbazolyl group, a benzothienocarbazolyl group, a dibenzothienocarbazolyl group, a quinolinocarbazolyl group, Isoquinolinocarbazolyl group, R ₈ is a C ₅ to C ₃₀ aryl group or a C ₄ to C ₃₀ heteroaryl group, L ₄ and L ₅ are each independently selected from the group consisting of a phenylene group, A and b are independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a propyl group, a propyl group, a propyl group, a butyryl group, Lt; / RTI >
5. The method of claim 4,
Wherein the compound represented by Formula 1 comprises any one of PGH1 to PGH24 represented by Formula 3 below.
(3)

5. The method of claim 4,
Wherein the organic material layer includes at least one of a light emitting material layer, an electron blocking layer, and an electron transporting layer.
5. The method of claim 4,
Wherein the organic compound is used as a host of the light emitting material layer.
Board,
A driving thin film transistor positioned on the substrate,
An organic light emitting device comprising the organic light emitting diode according to any one of claims 4 to 8, which is located on the substrate and connected to the driving thin film transistor.
10. The method of claim 9,
Wherein the organic light emitting device includes an organic light emitting diode display.

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