KR20190063648A - Organic compounds, organic light emitting diode and organic light emittid device having the compounds - Google Patents

Abstract

The present invention relates to an organic compound in which condensed hetero aromatic moieties functioning as an electron donor are located at both sides, respectively, and an arylene group moiety substituted with two cyano groups functioning as an electron acceptor between the condensed hetero aromatic moieties is connected by an aromatic ring. Since the organic compound includes both the electron donor and the electron acceptor moiety in one molecule, charges are easily moved in a molecule, thereby improving luminous efficiency. The organic compound of the present invention may be used as a delay fluorescent dopant, and may be used in an organic light emitting device such as an organic light emitting diode, a display device, and a lighting device having low driving voltage and excellent luminous efficiency and color purity.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound, an organic light emitting diode and an organic light emitting device including the same. BACKGROUND ART [0002] Organic light emitting diodes (OLEDs)

The present invention relates to an organic compound, and more particularly, to an organic compound having an excellent luminous efficiency and being applicable to a light emitting layer of an organic light emitting diode, an organic light emitting diode including the same, and an organic light emitting device.

BACKGROUND ART [0002] As one of widely used flat display devices, the technology of an organic light emitting diode device called an organic electroluminescent device (OELD) is rapidly developing. Organic light emitting diodes (OLEDs) are formed of thin organic thin films within 2000 Å, and it is possible to realize images in a single direction or in both directions depending on the configuration of the electrodes used.

In addition, an organic light emitting diode display device, which is one of the organic light emitting devices including an organic light emitting diode, can form a device on a flexible transparent substrate such as a plastic, so that a flexible or foldable display device can be realized. In addition, the organic light emitting diode display device can be driven at a low voltage, has excellent color purity, and has a great advantage over a liquid crystal display device (LCD).

The organic light emitting diode includes a hole injection electrode (anode), an electron injection electrode (cathode), and an organic light emitting layer formed between the anode and the cathode. (EIL), an electron transport layer (ETL), an electron transport layer (ETL), and an electron injection layer (EIL) are sequentially stacked on the hole injection electrode. ). At this time, holes injected from the anode and electrons injected from the cathode combine with each other in the light emitting material layer to form excitons, resulting in an unstable energy state (excited state), and stable ground state ground state and emits light. The external quantum efficiency EQE (eta _ext ) of the luminescent material applied to the luminescent material layer can be calculated by the following equation (1).

Where η _{S / T} is the singlet / triplet ratio, δ is the charge balance factor, Φ is the radiative quantum efficiency, and η _out-coupling is the optical - out-coupling efficiency)

The excitation generation efficiency (η _{S / T} ) has a limiting value of 0.25 at maximum for the fluorescent substance, at a rate at which the generated exciton is converted to the form of light. Theoretically, when holes and electrons meet to form an exciton, a singlet exciton in the form of a paired spin and a triplet exciton in the form of an unpaired spin are formed depending on the arrangement of the spin 1: 3 ratio. In the fluorescent material, only the single-exciton participates in the luminescence and the remaining 75% of the triplet excitons do not participate in the luminescence.

The charge balancing factor (g) means the balance of the electrons and holes forming the exciton, and generally has a value of '1' assuming a 1: 1 matching of 100%. The radiation quantum efficiency (Φ) is a value that is related to the luminous efficiency of a substantial luminescent material and depends on the photoluminescence (PL) of the dopant in a host-dopant system.

The light-extraction efficiency (? _Out-coupling ) is a ratio of light extracted from the light emitted from the light emitting material to the outside. Generally, when a thin film is formed by thermally depositing an isotropic luminescent material, the individual luminescent molecules do not have a certain directionality and exist in a disordered state. The light-extraction efficiency in such a random orientation state is generally assumed to be a value of 0.2. Therefore, when the four elements shown in the formula (1) are combined, the maximum luminous efficiency of the organic light emitting diode using the fluorescent material is only about 5%.

On the other hand, phosphors have a luminescent mechanism that converts both singlet excitons and triplet excitons into light. The phosphor converts single-exciton into triplet exciton through inter system crossing (ISC). Therefore, when a phosphorescent material using both singlet excitons and triplet excitons is used, the low luminous efficiency of the fluorescent material can be improved. When a metal complex containing a heavy metal such as Ir or Pt is used as a phosphorescent material, transition from a triplet state to a singlet state is possible by a strong spin-orbit coupling by a heavy metal element. However, the blue phosphorescent material is difficult to apply to the display device because of its color purity, and its life is also very short, which is not much lower than the commercialization level.

The phosphorescent host, including the blue phosphorescent host, must be higher than the triplet energy of the phosphorescent dopant material to prevent the triplet energy of the phosphorescent dopant from transferring back energy to the host's triplet energy. However, when the conjugated structure of the organic aromatic compound is increased or the fused ring is formed, the organic molecules that can be used as the phosphorescent host are extremely limited because the triplet energy is rapidly lowered. In addition, the phosphorescent host is designed to have a considerably wide energy bandgap in order to have a high triplet energy. The injection and transport of charges are delayed due to the phosphorescent host material having a wide energy bandgap. As a result, the driving voltage of the organic light emitting diode rises, adversely affecting the power consumption, and electric stress is applied to the material constituting the light emitting layer The lifetime characteristics of the device are deteriorated.

It is an object of the present invention to provide an organic compound capable of improving the luminous efficiency and an organic light emitting diode and an organic light emitting device using the organic compound to reduce the driving voltage to reduce the power consumption and the lifetime of the device.

According to one aspect of the present invention, the present invention provides a process for the preparation of a compound of formula (I), which comprises two condensed heteroaromatic moieties having one or two nitrogen atoms functioning as electron donors on both sides, And a central aromatic moiety (core) substituted with two cyano groups (-CN).

For example, the condensed heteroaromatic rings on both sides which function as an electron chan- nel are each an unsubstituted or substituted carbazoyl group (carbazoyl group, acridly group and / or phenoxazinyl group ), And the electron source and the electron acceptor may be connected to each other through a linker having one or two aromatic rings.

According to another aspect of the present invention, there is provided an organic light emitting diode and an organic light emitting device in which the organic compound is applied to the organic light emitting layer.

For example, the organic compound may be applied to the light emitting material layer.

In one exemplary embodiment, the organic compound of the present invention can be used as a dopant in a layer of a light emitting material.

The organic compound according to the present invention is characterized in that a condensed heterocyclic moiety containing 1 to 2 nitrogen atoms is positioned on each side so as to function as an electron donor and an electron acceptor ) In which at least two cyano group-substituted arylene group moieties are connected via an aromatic ring.

A central heteroarylene group moiety substituted by at least two cyano groups is used as an electron acceptor because the condensed heterocyclic moiety consisting of three or more aromatic rings on both sides functions as an electron donor. The steric hindrance between the condensed heterocyclic moieties on both sides constituting the electron donor and the central heteroarylene moiety substituted by at least two cyano groups functioning as an electron acceptor is increased and the surface angle between the electron donor and the electron acceptor is increased . (HOMO) energy of the organic compound is reduced while the formation of the conjugate structure between the bilateral condensed hetero ring moiety functioning as the electron chirality and the central arylene moiety functioning as the electron acceptor is restricted, State and the lowest-level non-occupied molecular orbital (LUMO) energy state, the luminous efficiency can be improved.

In addition, a dipole is formed by an arylene group moiety substituted with at least two cyano groups functioning as an electron acceptor in a condensed heterocyclic moiety functioning as an electron chirality, and a dipole moment inside the molecule is increased The luminous efficiency can be further improved.

The condensed heterocyclic moieties on both sides functioning as electron chirality are connected to an arylene group moiety substituted with at least two cyano groups located at the center via a linking group consisting of one or two aromatic rings. Since the distance between the electron and one electron acceptor increases, so the reduction in overlapping between HOMO and LUMO, it is possible to reduce the difference (Δ _EST) of the triplet energy level and a singlet energy level. The problem of red shift of light emitted from the organic light emitting layer including the organic compound according to the present invention can be minimized by steric hindrance through the coupler.

Furthermore, since the condensed heterocyclic moiety functioning as an electron donor can form a rigid structure, the three-dimensional conformation of the molecule is greatly restricted. When the organic compound according to the present invention emits light, there is no energy loss due to the change of the three-dimensional structure of the molecule, and since the emission spectrum can be limited to a specific range, high color purity can be realized.

Therefore, the organic compound of the present invention can be used as an organic light emitting layer constituting the organic light emitting diode, for example, as a dopant of the light emitting material layer, thereby lowering the driving voltage of the light emitting device and improving the light emitting efficiency. Since the device can be driven at a low voltage, the material constituting the light emitting device does not deteriorate due to heat generated at a high voltage required for driving the light emitting device. Therefore, when the light emitting device is driven, do.

As a result, an organic light emitting diode such as an organic light emitting diode, an organic light emitting diode display, and a lighting device can be realized by applying the organic compound according to the present invention to improve the luminous efficiency and lifetime of the device, .

1 is a schematic diagram for explaining an emission mechanism when an organic compound according to an exemplary embodiment of the present invention is used as a retardation fluorescent material.
2 is a schematic cross-sectional view of an organic light emitting diode in which an organic compound is applied to an organic light emitting layer according to an exemplary embodiment of the present invention.
3 is a schematic diagram for explaining the energy level with a material used as a host when an organic compound according to an exemplary embodiment of the present invention is used as a retardation fluorescent material.
4 is a cross-sectional view schematically showing an organic light emitting diode in which an organic compound is applied to an organic light emitting layer according to another exemplary embodiment of the present invention.
5 is a cross-sectional view schematically showing an organic light emitting diode display as an example of an organic light emitting device having an organic light emitting diode in which an organic compound is applied to an organic light emitting layer according to an exemplary embodiment of the present invention.

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

[Organic compounds]

The organic compound according to the present invention is connected to condensed heteroaromatic moieties on both sides which function as an electron donor with a condensed ring having a strong chemical structure through a suitable aromatic coupler (or linker) to the condensed heteroaromatic moiety , And a central arylene moiety substituted with at least two cyano groups functioning as an electron acceptor. The organic compound according to the present invention can be represented by the following formula (1).

Formula 1

Wherein R ₁ to R ₄ each independently represent an unsubstituted or substituted C ₁₀ to C ₃₀ condensed heteroaromatic substituent comprising one or two nitrogen atoms and consisting of three to five rings; R ₅ to R ₈ are each independently hydrogen, deuterium, tritium, cyano, unsubstituted or substituted C ₁₀ -C ₃₀ condensed homoaromatic substituent consisting of three to five condensed rings, or one or two nitrogen atoms Substituted and unsubstituted C ₁₀ to C ₃₀ condensed heteroaromatic substituent comprising 3 to 5 rings, Ar ₁ and Ar ₂ are each independently a C ₅ to C ₃₀ homoaryl group, a C ₄ to C ₃₀ a heteroaryl group, C ₅ ~ C ₃₀ Homo arylalkyl group, C ₄ ~ C ₃₀ heteroaryl group, C ₅ ~ C ₃₀ Homo aryloxy group, C ₄ ~ C ₃₀ heteroaryloxy group, C ₅ ~ C ₃₀ Homo arylamine Group and a C ₄ to C ₃₀ heteroarylamine group Ar ₃ , L ₁ and L ₂ are each independently a C ₅ to C ₃₀ homoarylene group, a C ₄ to C ₃₀ heteroarylene group, a C ₅ to C ₃₀ homoarylalkylene group, a C ₄ to C ₃₀ heteroarylalkyl A C ₅ to C ₃₀ homoaryloxylene group and a C ₄ to C ₃₀ heteroaryloxylene group, a and b are each independently 0 or 1,

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, a C ₁ -C ₂₀ alkyl group which is unsubstituted or substituted by a halogen atom, cyano group and / or nitro group, unsubstituted or substituted by a halogen atom, cyano group and / a C ₁ ~ C ₂₀ alkoxy group, a halogen atom, a cyano group, an alkyl halide, such as a -CF ₃ group, is optionally substituted with a halogen atom, a cyano group and / or each substituted by a hydroxyl group nitro group, a carboxy group, a carbonyl group, an amine group , C ₁ ~ C ₁₀ alkyl substituted amine group, C ₅ ~ C ₃₀ aryl substituted amine group, a C ₄ ~ C ₃₀ heteroaryl group substituted with an amine group, a nitro group, a hydrazide chewy (hydrazyl group), a sulfonic acid group, C ₁ ~ C ₂₀ alkylsilyl group, C ₁ ~ C ₂₀ alkoxy silyl group, C ₃ ~ C ₃₀ cycloalkyl, silyl group, C ₅ ~ C ₃₀ aryl silyl group, C ₄ ~ C ₃₀ heteroaryl, silyl group, C ₅ ~ C ₃₀ aryl group , C ₄ ~ C ₃₀ heteroaryl group, C ₅ ~ C ₃₀ aralkyl group homo, C ₄ ~ C ₃₀ heteroaryl aralkyl group, C ₅ ~ C ₃₀ homopolymer An aralkoxy group or a C ₄ to C ₃₀ heteroaralkoxy group, but the present invention is not limited thereto.

As used herein, the term "heteroaromatic ring", "heterocycloalkylene group", "heteroaryl group", "heteroarylalkyl group", "heteroaryloxyl group", "heteroarylamine group", "heteroarylene group" The term "hetero" as used in the alkylene group, heteroaryloxylene group and the like means that at least one, for example, 1 to 5 carbon atoms constituting these aromatic or alicyclic rings are N, O , S, and combinations thereof. The term " heteroaryl "

In one exemplary embodiment, R ₁ to R ₄ located on both sides of the organic compound molecule represented by Formula (1) each independently contain 1 to 2 nitrogen atoms, preferably 1 nitrogen atom, and 3 To five heteroaromatic rings, preferably three aromatic rings. For example, R ₁ to R ₄ each independently represent a C ₁₀ to C ₃₀ condensed heteroaryl group, a C ₁₀ to C ₃₀ condensed heteroarylalkyl group, a C ₁₀ to C ₃₀ condensed heteroaryl group, An oxyl group or a C ₁₀ to C ₃₀ condensed heteroarylamine group, preferably a C ₁₀ to C ₃₀ condensed heteroaryl group.

For example, R ₁ to R ₄ are each independently an unsubstituted or substituted carbazoyl moiety, an acridinyl moiety, an acridonyl moiety, and / or a phenoxazinyl moiety ) Can be configured. Specifically, each of R ₁ to R ₄ independently represents an unsubstituted or substituted carbamoyl group, a benzocarbamoyl group, a dibenzocarbamoyl group, an indenocarbazoyl group, an acridinyl group, a benzoacrylydiyl group, An indenoyloxy group, a benzoquinoxanyl group, a dibenzophenoxazinyl group and / or an indenopyranosyl group, an indenoyloxy group, an indenoyloxy group, an indenoyloxy group, an acyloxy group, It is possible to constitute a green knocker. Preferably, R ₁ to R ₄ each independently may have a carbazoyl moiety.

According to one exemplary embodiment, Ar ₁ and Ar ₂ in formula (1) may each independently be a C ₅ -C ₃₀ homoaryl group or a C ₄ -C ₃₀ heteroaryl group. For example, Ar ₁ and Ar ₂ each represent R ₁ to R ₄ , which are located on both sides of the molecule and function as electron donors, and at least two molecules that are positioned at the center of the molecule and function as electron acceptors May function as a linking group mediating between the arylene group (Ar ₃ ) substituted with a cyano group.

In one example, Ar1 and Ar ₂ in the formula (1) is the respective optionally substituted independently or substituted phenyl group, a biphenyl group, a terphenyl group, tetramethylene group, a naphthyl group, an anthracenyl group, a group, a page nalre group, a phenanthrenyl group, an azulenyl An unconjugated or fused homo aromatic ring such as a phenyl group, a pyranyl group, a fluorenyl 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, a dibenzocarbazolyl group, A thiazolinyl group, a quinazolinyl group, a phthalazinyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , Quinoxalinyl group, cyano group, A benzoquinolinyl group, a benzoquinolinyl group, an acridinyl group, a phenanthrolinyl group, a furanyl group, a paranyl group, an oxazinyl group, an oxazolyl group, an oxadiazole group, an oxazolyl group, A non-condensed or condensed heteroaromatic group such as a thiol group, a thiazolyl group, a triazolyl group, a dioxinyl group, a benzofuranyl group, a dibenzofuranyl group, a thiopyranyl group, a thiazinyl group, a thiophenyl group or an N-substituted spirobifluorenyl group It can be a ring.

For example, Ar ₁ in formula ( ₁₎ and / or Ar ₂ each independently represents a homoaryl group such as a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group or a spirobifluorenyl group and / or a benzoyl group which is a benzothiophenyl group, a dibenzothiophenyl group, A furanyl 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 pyrazolyl group, , Benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, benzofuranocarbazolyl group, benzothienocarbazolyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group A quinazolinyl group, a benzoquinolinyl group, a benzoquinazolinyl group, a benzoquinazolinyl group, a benzoquinazolinyl group, a benzoquinazolinyl group, a benzoquinazolinyl group, a benzoquinazolinyl group, Lt; RTI ID = 0.0 > .

At this time, if the number of aromatic rings constituting Ar ₁ and / or Ar ₂ in formula (1) is increased, the conjugated structure in the entire organic compound becomes excessively long, so that the bandgap of the organic compound can be excessively reduced. Accordingly, the number of aromatic rings constituting each of Ar ₁ and / or Ar ₂ in the formula (1) is preferably 1 to 2, more preferably 1. In addition, with respect to the charge injection and migration characteristics, Ar ₁ and / or Ar ₂ in formula (1) may each be a 5-membered ring to a 7-membered ring, It may be desirable to be a 6-membered ring. For example, in formula (1), Ar ₁ and / or Ar ₂ each independently represents a substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, biphenyl group, pyrrolyl group, imidazole group, pyrazole group, pyridinyl group, A pyrimidinyl group, a pyridazinyl group, a furanyl group or a thiophenyl group.

In one non-limiting embodiment, on the other hand, Ar ₃ , which may be another linker (linker) in formula (1), may be an aromatic arylene group substituted with at least two cyano groups which function substantially as an electron acceptor. Here, Ar ₁ to Ar ₃ may each be a linking group that mediates electron-donating individual condensed heteroaromatic rings (R ₁ to R ₄ ) and at least two cyano groups of the electron main chain. In this case, Ar ₃ constituting the aromatic arylene group may be substituted with R ₅ to R ₈ , which may be hydrogen, deuterium, tritium, another cyano group or another condensed aromatic ring through another aromatic linking group (L ₁ , L ₂ ) Can be connected.

R ₅ to R ₈ are each independently hydrogen, deuterium, tritium, cyano, an unsubstituted or substituted C ₁₀ to C ₃₀ condensed homoaryl group consisting of 3 to 5 condensed rings, or 1 or 2 Or a C ₁₀ to C ₃₀ fused heteroaromatic ring comprising three to five rings containing one nitrogen atom. For example, when a and b are 0, R ₅ to R ₈ each independently may be hydrogen, deuterium, tritium, or cyano, and when a and b are 1, R ₅ to R ₈ are each independently 3 to consisting of five fused ring unsubstituted or substituted C ₁₀ ~ C ₃₀ fused homo aryl groups, or 1 or 2, including the nitrogen atom and C ₁₀ ~ C ₃₀ condensed consisting of three to five ring heteroatoms Aromatic ring.

When R ₅ to R ₈ in the formula (1) are condensed aromatic rings, R ₅ to R ₈ are condensed homoaryl groups having three to five aromatic rings (for example, anthracenyl, phenalenyl, phenanthryl, A furanyl group, a fluorenyl group, an indacenyl group, etc.) or a condensed heteroaryl group consisting of three to five aromatic rings containing one or two nitrogen atoms (e.g., a carbamoyl moiety, acridyl An acridone moiety, or a phenoxylic moiety).

Ar ₃ , L ₁ and / or L ₂ , which mediate between the electron donor moiety and the electron acceptor moiety, may each independently be an unsubstituted or substituted aromatic linking group. For example, when Ar ₃ , L ₁ and / or L ₂ is an unsubstituted or substituted C ₅ -C ₃₀ homoarylene group, Ar ₃ , L ₁ and / or L ₂ are each independently unsubstituted or substituted A phenylene group, a biphenylene group, a terphenylene group, a tetraphenylene group, an indenylene group, a naphthylene group, an azulenylene group, Examples of the anthracenylene group include indenone, acenaphthylene, fluorenylene, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, anthracenylene group, ), Fluororanthrenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenyl, and the like. Perylenylene, pentaphenylene and hexasene, It may be selected from the group consisting of group (hexacenylene).

In another alternative embodiment, when Ar ₃ , L ₁ and / or L ₂ is an unsubstituted or substituted C ₄ -C ₃₀ heteroarylene group, Ar ₃ , L ₁ and / or L ₂ are each independently substituted Or a substituted pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinyl, pyrimidinyl, pyrimidinyl, Examples thereof include pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, isoindolylene, indolylene, Benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, benzoquinolinylene group, benzoisoyl group, benzoquinolinyl group, benzoquinolinyl group, Quinolinylene group, benzoquinazolinylene group, benzoquinone A phenanthridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoxazolylene group, a phenanthrolinylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, Benzimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene, isothiazolyl, isothiazolyl, thiazolyl, thiazolyl, Isoxazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, , Benzofuranylene group, dibenzofuranylene group, benzopureodibenzofuranylene group, benzothienobenzofuranylene group, benzothienodibenzofuranylene group, benzothiophenylene group, dibenzo furanyl group, A dibenzothiophenylene group, a benzothiophenebenzothiophenylene group, a benzothienodibenzothiophenylene group, a carbazolylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an indolocarbazolylene group, an indenocarbazolylene group, A benzothiophenecarbodiimide group, an imidazopyrimidinyl group, and an imidazopyridinylene group, which may be the same or different from each other.

In one exemplary embodiment, if the number of aromatic rings, each of Ar ₃ , L ₁ and / or L ₂ , is increased, the conjugated structure in the entire organic compound becomes excessively long, Can be overshoot. Therefore, the number of aromatic rings constituting each of Ar ₃ , L ₁ and / or L ₂ is preferably 1 to 2, more preferably 1. Also, with respect to charge injection and migration characteristics, Ar ₃ , L ₁ and / or L ₂ can each be a 5-membered ring to a 7-membered ring, - 6-membered ring. For example, Ar ₃ , L ₁ and / or L ₂ each independently represents an unsubstituted or substituted phenylene group, a biphenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, , A pyrimidinylene group, a pyridazinylene group, a furanylene group or a thiophenylene group.

The organic compound represented by the general formula (1) can function as an electron donor and has condensed heteroaromatic moieties (R ₁ to R ₄ ) on both sides having a rigid structure and has a suitable linking group (Ar ₁ to Ar ₃ ) And at least two cyano groups capable of functioning as an electron acceptor are connected to each other. Since the steric hindrance of the condensed heteroaromatic moiety consisting of at least three aromatic rings is large, the three-dimensional structure of the organic compound of the present invention, which is synthesized by forming a chemical bond with the condensed heteroaromatic moiety located on both sides of the molecule The conformation is limited. Accordingly, the organic compound according to the present invention has a rigid structure to improve the thermal stability. When the organic compound represented by the general formula (1) is luminescent, there is no energy loss due to the change of the three-dimensional structure of the molecule and the luminescence spectrum can be limited to a specific range, so that good color purity can be realized.

Particularly, it is possible to realize low-voltage driving using the organic compound according to the present invention, thereby reducing power consumption and improving the luminous efficiency. For example, the organic compound according to the present invention can be used as a dopant of an organic light emitting layer constituting an organic light emitting diode, and particularly has a so-called delayed florescence characteristic.

1 is a schematic diagram for explaining a luminescent mechanism when an organic compound according to the present invention is used as a retardation fluorescent compound. Delayed fluorescence can be divided into thermally activated delayed fluorescence (TADF) and field activated delayed fluorescence (FADF), wherein triplet excitons are activated by heat or an electric field, So-called super-fluorescence exceeding the maximum luminous efficiency in the material can be realized.

That is, the retarded fluorescent compound is activated by triplet exciton due to heat or an electric field generated when the device is driven, so that triplet excitons are involved in light emission. In general, the retarded fluorescent compound has both an electron donor moiety and an electron donor moiety so that it can be converted into an intramolecular charge transfer (ICT) state. When a retarded fluorescent compound capable of ICT is used as a dopant, an exciton having a singlet energy level (S ₁ ) and an exciton having a triplet energy level (T ₁ ) in the retarded fluorescent compound migrate to an intermediate ICT state, Transition to a ground state (S ₀ ) (S ₁ → ICT ← T ₁ ). The exciton having the singlet energy level (S ₁ ) and the exciton having the triplet energy level (T ₁ ) all participate in the luminescence, so that the internal quantum efficiency is improved and thus the luminescence efficiency is improved.

Since conventional fluorescent materials have a high level of Occupied Molecular Orbital (HOMO) and a Lowest Unoccupied Molecular Orbital (LUMO) spread throughout the molecule, It is impossible to switch between them (selection rule). However, since the compound having ICT state has a small overlap of HOMO and LUMO orbitals, the interaction between the HOMO state orbit and the LUMO state orbit is small. Therefore, the spin state change of the electrons does not affect other electrons, and a new charge transfer band (CT band) which does not follow the selection rule is formed.

That is, since the electron acceptor moiety and the electron donor moiety are spaced apart in the molecule in the retarded fluorescent compound, the dipole moment in the molecule is present in a highly polarized state. In the polarized state of the dipole moment, the interaction between the HOMO and the LUMO state orbits is reduced and the transition from the triplet state to the intermediate state (ICT) becomes possible. Thus excitons having a triplet energy level (T ₁ ) as well as excitons having a singlet energy level (S ₁ ) participate in light emission. That is, when the light emitting device is driven, excitons having a singlet energy level (S ₁ ) of 25% and excitons having a triplet energy level (T ₁ ) of 75% are converted into intermediate states (ICT) Since the light emission occurs while falling back to the ground state S ₀ , the internal quantum efficiency is theoretically 100%.

The dopant for realizing retarded fluorescence needs to have the following characteristics. The dopant must have an electron donor moiety and an electron acceptor moiety at the same time in one molecule so that the ICT state can be realized. The dopant is usually in the form of a complex (ICT complex) in the ICT state, in which an electron donor moiety and an electron donor moiety are simultaneously present in one bacterium, and electrons move easily within the molecule. That is, in an ICT complex under certain conditions, one electron moves from the electron donor moiety to the electron acceptor moiety, resulting in the separation of charge in the molecule.

In order for the energy transition to occur both in the triplet state and in the singlet state, the dopant for implementing the retarded fluorescence has a difference (ΔE _ST ) between the singlet energy level (S ₁ ) and the triplet energy level (T ₁ ) of 0.3 eV, for example between 0.05 and 0.3 eV. In this case, a material with a small energy difference between singlet and triplet states not only exhibits fluorescence as inter-system crossing (ISC) occurs in which energy is transferred from singlet state to triplet state, Energy or electric field, the energy in the triplet state is reverse inter-system crossing (RISC) to a higher singlet state, and the monophasic state transitions to the ground state and exhibits delayed fluorescence. In the case of delayed fluorescence, efficiency of 100% at the theoretical maximum can be obtained, so that the internal quantum efficiency equivalent to that of a conventional phosphorescent material containing a heavy metal can be realized.

The ICT complex capable of delayed fluorescence is formed by the external environment. This can be easily confirmed by comparing the absorption wavelength and the emission wavelength in the solution state using various solvents, which can be expressed by the following equation (2).

In the above equation, Δν is the stock shift value, and ν _abs and ν _fl are the maximum absorption wavelength and the wave number of the maximum emission wavelength, respectively. Where h is the Planck's constant, c is the velocity of light, a is the onsager cavity radius, and Δμ is the dipole moment and ground state of the excited state. ) (Μ μ = μ _e - μ _g ) of the dipole moment. Δf is a value representing the orientational polarizability of the solvent and is expressed by the dielectric constant (ε) and the refractive index (n) of the solvent as shown in the following equation (3).

At this time, formation of the ICT complex can be confirmed by comparing absorption wavelength and emission wavelength in a solution state using various solvents. This is because the degree of polarization when excited (i. E., The magnitude of the dipole moment) is determined by the surrounding polarity. Specifically, the directional polarizability Δf of the mixed solvent can be calculated by calculating the ratio of the polarizability of the pure solvent to the mole fraction, and the formation of the ICT complex can be calculated using the above equation (Lippert-Mataga equation) Can be determined by checking whether a linear relationship exists between plotting and Δν. That is, the stabilization of the ICT complex occurs depending on the directional polarization degree of the solvent, and the emission wavelength shifts to a long wavelength depending on the degree of stabilization. Therefore, when an ICT complex is formed, Δf and Δν form a linear graph. Conversely, when Δf and Δν form a linear graph, the light emitting material is an ICT complex.

The organic compound represented by the general formula (1) has a condensed heteroaromatic moiety functioning as an electron chirality and a central arylene moiety having at least two cyano groups functioning as an electron acceptor coexist in one molecule, Lt; / RTI > In particular, because of the large steric hindrance between a condensed heteroaromatic moiety and an arylene group moiety substituted with at least two cyano groups, the formation of conjugated structures is limited and easily separated into HOMO and LUMO states. Dipole moments are formed in the central arylene group moiety substituted with at least two cyano groups and the condensed heteroaromatic moiety located on both sides of the molecule, so that the dipole moment inside the molecule is increased and the luminous efficiency is improved. The electrons and the electron acceptors coexist in the molecule, and the superposition of HOMO and LUMO of the molecule decreases.

In addition, since the electrons and the electron donors are connected through appropriate couplers (Ar ₁ to Ar ₃ ), the superposition of HOMO and LUMO in the molecule is further reduced, so that the energy level difference between the triplet energy level and the single- (DELTA _EST ) can be reduced. Particularly, since a condensed hetero aromatic moiety having a rigid structure on both sides is provided, the three-dimensional structure between the arylene group moiety constituting the center electron acceptor and the condensed hetero aromatic moiety constituting the electron donor on both sides is Is limited. There is no energy loss when emitting light, and good green light emission can be realized.

Particularly, when the organic compound represented by the general formula (1) is used as a dopant of the light emitting material layer, the triplet energy level of the organic compound represented by the general formula (1) is lower than the triplet energy of the conventional phosphorescent material, It is narrower than material. Therefore, the organic host to be used together with the organic compound represented by the formula (1) does not need to have a triplet energy level as high as that of a conventional phosphorescent material, and does not need to have a wide band gap. Therefore, there is no need to use a host having a triplet energy higher than that of a conventional phosphorescent material, and it is not necessary to use a phosphorescent host having a wide energy band gap. By using a host having a wide energy band gap, charge injection and transport are delayed, thereby increasing the driving voltage of the light emitting diode, increasing the power consumption, and preventing the lifetime characteristics of the device from deteriorating.

In one exemplary embodiment, the organic compound according to the present invention comprises an organic compound represented by the following formula (2).

(2)

(Wherein R ₁₁ to R ₁₄ are each independently selected from the group consisting of a carbazyl group, a benzocarbamoyl group, a dibenzocarbamoyl group and an indenocarbamoyl group; R ₁₅ and R ₁₆ are each independently selected from the group consisting of hydrogen L ₃ is a phenylene group, a and b are the same as defined in formula (1), and R 1 and R ₂ are independently selected from the group consisting of hydrogen, deuterium, tritium, cyano, carbamoyl, benzocarbamoyl, dibenzocarbamoyl and indenocarbamoyl; Lt; / RTI >

More specifically, the organic compound according to the present invention may be any compound represented by the following general formula (3).

(3)

The organic compounds represented by the general formulas (2) to (3) include condensed heteroaromatic moieties composed of two carbamoylic moieties each of which functions as an electron chan- nel on both sides and has a rigid structure, and a condensed heteroaromatic moiety composed of at least two An arylene group moiety substituted with a cyano group is connected through an aromatic linking group having a suitable conjugated structure. An electron main individual condensed hetero aromatic moiety and an arylene group moiety substituted with at least two cyano groups in the electron acceptor exist in one molecule to increase the dipole moment and easily separate the HOMO and the LUMO to increase the dipole moment Structure. Accordingly, the organic compounds represented by the formulas (2) to (3) can be applied as a retardation fluorescent material, and the organic compounds represented by the formulas (2) to (3) can be used to improve the luminous efficiency and the color purity of the organic light emitting diode . Further, by applying the organic compound represented by the general formulas (2) to (3) to the organic light emitting diode, the driving voltage of the organic light emitting diode can be lowered to reduce power consumption, and the electrical stress on the organic material constituting the light emitting layer can be reduced, Life characteristics can be improved.

[Organic light emitting diode and organic light emitting device]

As described above, the organic compound represented by the general formulas (1) to (3) can be applied to the organic light emitting layer constituting the organic light emitting diode. In particular, high purity luminescent color can be obtained, the driving voltage can be lowered to reduce the power consumption, A light emitting device having improved device lifetime characteristics can be realized. This will be described. 2 is a schematic cross-sectional view of an organic light emitting diode in which an organic compound is applied to an organic light emitting layer according to an exemplary embodiment of the present invention.

2, the organic light emitting diode 100 according to the first 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 110, And 120, respectively. In the exemplary embodiment, the organic light emitting layer 130 includes a hole injection layer (HIL) 140, a hole transfer layer (HTL) 150, and a light emitting material layer 140 sequentially stacked from the first electrode 110. An emissive material layer (EML) 160, an electron transfer layer (ETL) 170, and an electron injection layer (EIL) 180.

The first electrode 110 may be an anode for supplying holes to the light emitting material layer 160. The first electrode 110 is preferably formed of a conductive material having a relatively large work function value, for example, a transparent conductive oxide (TCO). In an exemplary embodiment, the first electrode 110 is formed of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium- (ITO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO) and aluminum: ZnO Lt; / RTI >

The second electrode 120 may be a cathode for supplying electrons to the light emitting material layer 160. The second electrode 120 may have a reflective property such as a conductive material having a relatively low work function value, for example, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag) It can be made of good material.

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 injection layer 140 is formed of a mixture of 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (4,4', 4" -tris (3-methylphenylamino) triphenylamine; MTDATA), 4,4 ', 4 "-tris (N, N-diphenyl-amino) triphenylamine (NATA), 4 , 4 ', 4 "-tris (N- (naphthalen-1-yl) -N-phenyl-amino) phenyl-amino) triphenylamine, 4,4 ', 4 "-tris (N- (naphthalen-2-yl) Tris (Naphthalene-2-yl) -N-phenyl-amino) triphenylamine, 2T-NATA, Copper phthalocyanine (CuPc), Tris (4-Carbamoyl- N, N'-bis (1-naphthyl) -1,1'-biphenyl-4,4'-diamine (N, N'-diphenyl-N, N'-bis (1-naphthyl) -1,1'-biphenyl-4,4'diamine NPB NPD) 1,4,5,8,9,11 - hexaazatriphenylene hexacarbonitrile (1,4,5,8,9,11-Hexaazatriphenylenehexacar HAT-CN), 1,3,5-tris [4- (di (4-fluoropyrimidin-2-yl) Phenyl] benzene (TDAPB), poly (3,4-ethylenedioxythiophene), poly (3,4-ethylenedioxythiophene) (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-pyrrolo [ (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2 -amine, and the like. 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 from N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'- TPD), NPB, 4,4'-bis (N-carbazolyl) - N'-diphenyl- (N-carbazolyl) -1,1'-biphenyl (CBP), poly [N, N'-bis (4-butylphenyl) -N, N'- Bis (phenyl) -benzidine] (Poly-TPD), poly [(9,9-dioxo-N- 2,7-diyl) -co- (4,4 '- (N- (4-sec-butylphenyl) diphenylamine)]) Poly [(9,9-dioctylfluorenyl- ) - co- (4,4'- (N- (4-sec-butylphenyl) diphenylamine))], TFB) (Biphenyl-4-yl) -9,9-dimethyl-N- (4- ( (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene- -9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine and / (9-phenyl-9H-carbazol-3-yl) phenyl) biphenyl-4 -amine, and the like, but the present invention is not limited thereto.

The light emitting material layer 160 may be formed by doping a host with a dopant. For example, the light emitting material layer 160 may be doped with about 1 to 50% by weight of a dopant to the host, and may emit green light.

In one exemplary embodiment, the organic compound represented by Chemical Formulas 1 to 3 can be used as a dopant of the light emitting material layer 160. [ On the other hand, the organic compound represented by Chemical Formulas 1 to 3 used in the light emitting material layer 160 may be a dopant having a delayed fluorescent property.

As described above, a compound having a retarded fluorescence characteristic is activated by heat or an electric field and has an intermediate energy state such as an ICT complex form. Both the exciton having a singlet energy level and the exciton having a triplet energy level are involved in light emission, so that the light emitting efficiency of the organic light emitting diode 100 can be improved.

The difference (ΔE _ST ) between the singlet energy level (S ₁ ) and the triplet energy level (T ₁ ) of the organic compound represented by any one of Chemical Formulas 1 to 3 may be 0.3 eV or less, for example, 0.05 to 0.3 eV. When the difference (DELTA _EST ) between the singlet energy level (S ₁ ) and the triplet energy level (T ₁ ) of the organic compound represented by the general formulas (1) to (3) which can be used as the retardation fluorescent dopant is 0.3 eV or less, And the quantum efficiency of the dopant can be improved as it finally falls to the bottom state. That is, the smaller the ΔE _ST , the greater the luminous efficiency. If the difference between the single-energy level (S ₁ ) and the triplet energy level (T ₁ ) of the dopant is 0.3 eV or less, The exciton and the triplet state exciton can be transferred to an intermediate ICT complex state (ΔE _ST ≤ 0.3).

On the other hand, in order to realize retardation fluorescence, the host included in the light emitting material layer 160 must be able to induce excitons in the triplet state in the dopant to participate in light emission without being quenched (non-luminescence quenching). 3 is a schematic diagram for explaining the energy level with a retarded fluorescent compound when an organic compound according to an exemplary embodiment of the present invention is used as a host.

As shown in FIG. 3, the host for implementing the delayed fluorescence has to appropriately adjust the energy level with the dopant. First, the triplet energy level (T ₁ ^H ) and the singlet energy level (S ₁ ^H ) of the host should be higher than the triplet energy level (T ₁ ^D ) and the singlet energy level (S ₁ ^D ) of the dopant, respectively. In particular, in case the triplet energy level (T _1H) of the host is not high enough than the triplet energy level (T ₁ ^D) of the dopant is, the triplet state exciton of the dopant, the triplet energy level (T ₁ ^H) of the host And the triplet excited state exciton of the dopant does not contribute to luminescence since it is vanished by non-luminescence.

In addition, it is necessary to appropriately adjust the HOMO energy level and the LUMO energy level of the host and the dopant. For example, the difference between the highest level occupied molecular orbital energy level (HOMO ^H ) of the host and the highest level occupied molecular orbital energy level (HOMO ^D ) of the dopant (| HOMO ^H -HOMO ^D |) or the lowest level of host's occupation molecular orbital The difference (LUMO ^H -LUMO ^D |) between the energy level LUMO _H and the lowest level non occupied molecular orbital energy level LUMO ^{D of the} dopant is preferably 0.5 eV or less, for example, 0.1 to 0.5 eV or less have. As a result, the charge transfer efficiency from the host to the dopant is improved, and the luminous efficiency can be finally improved.

In one exemplary embodiment, the host of the luminous material layer 160 is a mixture of 9- (3- (9H-carbazol-9-yl) phenyl) -9H-carbazole- Carbazole-3-carbonitrile, mCP-CN), CBP, 3,3'-bis (N-carbazolyl) -1,1'- 3-bis (carbazol-9-yl) benzene, MCP (1,3-bis (N-carbazolyl) -1,1'-biphenyl, mCBP) Bis (diphenylphosphine oxide) (DPEPO), 2T-NATA, TCTA, 1,3-bis (diphenylphosphine oxide) Tri- [(3-pyridyl) -phen-3-yl] benzene; TmPyPB), 2,6-di (9H-carbazol-9-yl) pyridine PYD-2Cz), 3 ', 5'-di (carbazol-9-yl) - [1 , 1'-biphenyl] -3,5-dicarbonitrile (3 ', 5'-Di (carbazol-9-yl) (9H-carbazol-9-yl) biphenyl-3,5-dicarbonitrile (4 '- (9H-carbazol-9-yl) biphenyl-3,5-dicarbonitrile; pCzB- Carbazol-9-yl) biphenyl-3,5-dicarbonyl 9- (9H-carbazol-9-yl) biphenyl-3,5-dicarbonitrile, mCzB-2CN), 9- (9H-carbazol-9-yl) phenyl) -9H-3,9'-bicarbazole, 9- -9H-3,9'-bicarbazole and / or 4- (3-triphenylene-9-yl) (Triphenyl-2-yl) -phenyl) dibenzo [b, d] thiophene), but the present invention is not limited thereto Do not.

2, 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 may comprise at least one of oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, benzimidazole, , Triazine, and the like. For example, the electron transport layer 170 may be formed of tris (8-hydroxyquinoline aluminum; Alq ₃ ), 2-biphenyl-4-yl-5- (4- ), 1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate ( lithium quinolate (Liq), 1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene, TPBi), bis 2-methyl-8-quinolinolato-N1, O8) - (1, 1'-biphenyl- 1'-biphenyl-4-olato) aluminum; BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9- Naphthalene-2-yl) 4,7-diphenyl-1,10-phenanthroline (NBphen), 2, Dimethyl-4,7-diphenyl-1,10-phenathroline (BCP), 3- (4-biphenyl) -4 Phenyl-5-tert-butylphenyl-1,2,4-triazole (3- (4-Biphenyl) -4-phe naphthalen-1-yl) -3,5-diphenyl-4H-1,2,4-triazole (4- ( Naphthalen-1-yl) -3,5-diphenyl-4H-1,2,4-triazole; NTAZ), 1,3,5-tri (p- 3, 5-Tri (p-pyrid-3-yl-phenyl) benzene; TpPyPB), 2,4,6-tris Triazine (2,4,6-Tris (3 '- (pyridin-3-yl) biphenyl-3-yl) 1,3,5-triazine; TmPPPyTz), poly [(9,9-bis (3 '- ((N, N- dimethyl- (9,9-bis (3 '- (N, N-dimethyl) -N-ethylammonium) -propyl) -2,7-fluorene] (9,9-dioctylfluorene)] PFNBr) and / or tris (phenylquinoxaline) (TPQ), but the present invention is not limited thereto.

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 based material such as LiF, CsF, NaF, BaF ₂ , and / or lithium quinolate (Liq), lithium benzoate, An organic metal-based material such as sodium stearate may be used, but the present invention is not limited thereto.

The organic light emitting diode 100 according to the exemplary embodiment of the present invention has a dopant which is an organic compound represented by Chemical Formula 1 to Chemical Formula 3 having retardation fluorescence characteristics in a light emitting material layer 160 constituting the organic light emitting layer 130 have. Since the excitons in the singlet energy state and the triplet energy state are all involved in luminescence, the luminescence efficiency is improved.

Since the electron donor moiety and the electron acceptor moiety coexist in the organic compounds represented by Chemical Formulas 1 to 3, the dipole moment increases, the HOHO and the LUMO are easily separated, and the dipole moment can be increased , And has a retarded fluorescence characteristic. In addition, the stereostructure between the condensed heteroaromatic moiety having a rigid structure on both sides and the arylene group moiety substituted with at least two cyano groups in the center is greatly restricted, thereby achieving good green luminescence while reducing energy loss when luminescing .

Further, as compared with the case of using a conventional phosphorescent material containing a heavy metal, organic hosts included in the light emitting material layer (EML) 160 together with the organic compounds represented by Chemical Formulas 1 to 3 have high triplet energy levels And the band gap need not be wide. Therefore, the problems caused by using an organic host having a wide energy band gap, that is, the injection and transport of electric charges are delayed, the driving voltage of the light emitting diode 100 rises and the power consumption increases, It is possible to prevent degradation of characteristics.

Meanwhile, the organic light emitting diode according to the present invention may further include at least one exciton blocking layer. 4 is a cross-sectional view schematically showing an organic light emitting diode to which a phosphorescent compound is applied according to a second exemplary embodiment of the present invention. 4, the organic light emitting diode 200 according to the 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 And 220, respectively.

In the exemplary embodiment, the organic light emitting layer 230 includes a hole injection layer 240, a hole transport layer 250, a light emitting material layer 260, an electron transport layer 270, and an electron transport layer 270 sequentially stacked from the first electrode 210. And an injection layer 280. The organic light emitting layer 230 may include an electron blocking layer (EBL) 255 and / or a light emitting material layer 260, which is a first exciton blocking layer positioned between the hole transporting layer 250 and the light emitting material layer 260. And a hole blocking layer (HBL) 265 which is a second exciton blocking layer positioned between the electron transport layer 270 and the electron transport layer 270.

As described above, the first electrode 210 may be an anode, and may be made of ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, or the like having a relatively large work function value. The second electrode 220 may be a negative electrode and may be made of a conductive material having a relatively low work function value such as Al, Mg, Ca, Ag, or an alloy or combination thereof.

The hole injection layer 240 is located between the first electrode 210 and the hole transport layer 22. The hole injection layer 240 may be formed of at least one material selected from the group consisting of MTDATA, NATA, 1T-NATA, 2T-NATA, CuPc, TCTA, NPB, HAT-CN, TDAPB, PEDOT / PSS and / -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene-2-amine and the like.

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. The hole transport layer 250 may be formed of TPD, NPD (NPB), CBP, Poly-TPD, TFB, TAPC, N- (biphenyl- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H- fluorene-2-amine and / -Yl) phenyl) biphenyl) -4-amine, and other aromatic amine compounds.

The light emitting material layer 260 may be formed by doping a host with a dopant. For example, the light emitting material layer 260 may be doped with about 1 to 50% by weight of a dopant to the host, and may emit green light. For example, organic compounds represented by Chemical Formulas 1 to 3 are used as dopants for the light emitting material layer 260, and mCP-CN, CBP, mCBP, MCP, DPEPO, 2T-NATA, TCTA, TmPyPB, PYD- (9H-carbazol-9-yl) phenyl) -9H-3,9'-bicarbazole, 9- (3- (9H-carbazol- Dibenzo [b, d] thiophene, or the like, is used as a luminescent material 0.0 > 260 < / RTI >

The electron transport layer 270 is located between the light emitting material layer 260 and the electron injection layer 280. For example, the electron transport layer 270 may be formed of a material selected from the group consisting of oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, benzimidazole, Derivative. For example, the electron transport layer 270 may be made of Alq ₃ , PBD, spiro-PBD, Liq, BAlq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr and / The invention is not limited thereto.

The electron injection layer 280 is located between the second electrode 220 and the electron transport layer 270. As the material of the electron injection layer 280, an alkali halide-based material such as LiF, CsF, NaF, BaF ₂ and / or an organometallic material such as Liq, lithium benzoate, and sodium stearate may be used. But is not limited thereto.

On the other hand, when the hole moves the light emitting material layer 260 to the second electrode 220 or electrons move to the first electrode 210 through the light emitting material layer 260, . In order to prevent this, the organic light emitting diode 200 according to the second exemplary embodiment of the present invention includes at least one exciton blocking layer adjacent to the light emitting material layer 260.

For example, the organic light emitting diode 200 according to the second embodiment of the present invention includes an electron blocking layer (not shown) capable of controlling the movement of electrons between the hole transport layer 250 and the light emitting material layer 260, layer, EBL, 255).

For example, the electron blocking layer 255 may comprise at least one of TCTA, tris [4- (diethylamino) phenyl] amine, N- (biphenyl- TAPC, MTDATA, mCP, mCBP, CuPC, N, N'-tetramethyl-N- Bis [4- [bis (3-methylphenyl) amino] phenyl] -N, N'-diphenyl- [1,1'-biphenyl] -4,4'- (DNTPD), and / or TDAPB, etc. [0035] The term " bis (3-methylphenyl) amino] phenyl] -N, N'- diphenyl- [1,1'- biphenyl] -4,4'-

A hole blocking layer 265 is disposed as a second exciton blocking layer between the light emitting material layer 260 and the electron transporting layer 270 to prevent movement of holes between the light emitting material layer 260 and the electron transporting layer 270. do. In one exemplary embodiment, oxadiazole, triazole, phenanthroline, benzoxazole, benzoquinone, and the like, which can be used for the electron transport layer 270 as the material of the hole blocking layer, Benzothiazole, benzimidazole, triazine and the like can be used.

For example, the hole blocking layer 265 may be formed of BCP, BAlq, Alq ₃ , PBD, spy which has a highest occupied molecular orbital (HOMO) energy level as compared with the material used for the light emitting material layer 260 -PBD, Liq and / or bis-4,6- (3,5-di-3-pyridylphenyl) -2-methylpyrimidine (bis- -2-methylpyrimidine, B3PYMPM), and combinations thereof.

The organic light emitting diode 200 according to the second embodiment of the present invention has a dopant that is an organic compound represented by Chemical Formula 1 to Chemical Formula 3 having retardation fluorescence properties in the light emitting material layer 160. The organic compounds represented by the general formulas (1) to (3) have a structure in which the electron donor moiety and the electron acceptor moiety coexist in one molecule, the dipole moment increases, the HOHO and the LUMO are easily separated, and the dipole moment Therefore, it has delayed fluorescence characteristics. In addition, the steric structure between the condensed hetero aromatic moiety constituting the electron donor and the arylene group moiety substituted by at least two cyano groups constituting the electron acceptor is limited. Accordingly, when the organic compound represented by any one of Chemical Formulas 1 to 3 is used as a dopant of the light emitting device, the organic light emitting diode 200 having improved light emitting efficiency and good color purity can be produced. It is not necessary to use an organic host having a high triplet energy and a wide bandgap so that the driving voltage of the light emitting diode 200 can be lowered to reduce the power consumption and the lifetime of the device can be improved. In addition, since the organic light emitting diode 200 according to the second embodiment of the present invention includes at least one exciton blocking layer 255 and 265, the charge transporting layer 250 and 270 adjacent to the light emitting material layer 260, The light emitting efficiency and lifetime of the organic light emitting diode 200 can be further improved.

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.

5, 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 polycarbonate (PC) As shown in FIG. 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. 5 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 light emitting layer 430 in the organic light emitting layer 400. 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.

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, A light emitting layer 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 310. 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 light emitting layer 430 is formed on the first electrode 410. In one exemplary embodiment, the organic light emitting layer 430 may have a single layer structure of a light emitting material layer. Alternatively, the organic light emitting layer 430 may include a hole injecting 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 electron injecting layer And may be composed of a plurality of organic material layers.

A second electrode 420 is formed on the substrate 302 on which the organic light emitting 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 is represented by Chemical Formula 1 to Chemical Formula 3 in the organic light emitting layer 430 and an organic compound having a delayed fluorescence characteristic is used as a dopant to improve the light emitting efficiency. Organic compounds represented by the general formulas (1) to (3) have delayed fluorescence properties because an electron donor moiety and an electron acceptor moiety coexist within one molecule. In addition, the steric structure between the condensed hetero aromatic moiety constituting the electron donor and the arylene group moiety substituted by at least two cyano groups constituting the electron acceptor is limited. Accordingly, when the organic compound represented by any one of Chemical Formulas 1 to 3 is used as a dopant of the light emitting device, the organic light emitting diode 400 having improved luminous efficiency and good color purity can be manufactured. It is not necessary to use an organic host having a high triplet energy and a wide bandgap so that the driving voltage of the light emitting diode 400 and the organic light emitting diode display device 300 including the organic light emitting diode display device 300 can be lowered to reduce power consumption, It is possible to improve the life of the device.

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 Compound 1

(1) Synthesis of compound a

Carbazole (13.5 g, 0.0808 mol) was dissolved in DMF under a nitrogen atmosphere and stirred. 3.52 g (0.0808 mol) of NaH was added thereto and stirred until no gas was generated. Then, 5 g (0.0261 mol) of 3,5-difluorobromobenzene was added thereto, followed by stirring at 130 ° C for 15 hours. After completion of the reaction, the reaction solution was filtered using distilled water, acetone, and ethyl acetate as a washing solution. After thoroughly washing, 9.4 g of yellow solid compound a was obtained (yield: 74%).

(2) Compound b Synthesis

A 9.40 g (0.0193 mol) of a was dissolved in a solvent of diethyl ether under nitrogen atmosphere, and the mixture was stirred. 11.57 mL (0.0289 mol) of n-BuLi was added slowly at -78 ° C, and the mixture was stirred at room temperature for 30 minutes. 4.91 mL (0.0289 mol) of triethyl borate was slowly added thereto at -78 ° C and then stirred at room temperature for 15 hours. After completion of the reaction, two drops of HCl were added to make an acidic atmosphere, and then distilled water was added. The solvent of diethyl ether was removed and extracted with methylene chloride and distilled water to remove water and solvent. After recrystallization using methylene chloride and hexane solvent, 7 g of white solid b was obtained (yield: 80%).

(3) Synthesis of compound 1

Potassium carbonate (2.9 g, 0.0209 mol) was dissolved in methanol (30 mL) under nitrogen atmosphere and stirred. 1.5 g (0.00525 mol) of 2,5-dibromoterephthalonitrile and 5.22 g (0.0115 mol) of b were dissolved in 60 mL of tetrahydrofuran solvent. 0.24 g (0.00107 mol) of palladium acetate and 0.55 g (0.00230 mol) of triphenylphosphine were further added and stirred. After stirring for 12 hours under reflux conditions, the reaction was terminated and extracted with ethyl acetate and distilled water. Purification by column chromatography using chloroform and hexane, and recrystallization with methylene chloride and hexane to complete the wet purification. 0.61 g of a pink solid compound 1 (yield: 12%).

Synthesis Example 2: Synthesis of Compound 2

Potassium carbonate (2.9 g, 0.0209 mol) was dissolved in methanol (30 mL) under nitrogen atmosphere and stirred. 1.5 g (0.00525 mol) of 4,6-dibromoterephthalonitrile and 5.22 g (0.0115 mol) of b were dissolved in 60 mL of tetrahydrofuran solvent. 0.24 g (0.00107 mol) of palladium acetate and 0.55 g (0.00230 mol) of triphenylphosphine were further added and stirred. After stirring for 12 hours under reflux conditions, the reaction was terminated and extracted with ethyl acetate and distilled water. Purification by column chromatography using chloroform and hexane, and recrystallization with methylene chloride and hexane to complete the wet purification. 0.8 g of a yellow solid compound 2 was obtained (yield: 16%).

Synthesis Example 3: Synthesis of Compound 3

Potassium carbonate (2.9 g, 0.0209 mol) was dissolved in methanol (30 mL) under nitrogen atmosphere and stirred. 1.5 g (0.00525 mol) of 4,5-dibromophthalonitrile and 5.22 g (0.0115 mol) of b were dissolved in 60 mL of tetrahydrofuran solvent. 0.24 g (0.00107 mol) of palladium acetate and 0.55 g (0.00230 mol) of triphenylphosphine were further added and stirred. After stirring for 12 hours under reflux conditions, the reaction was terminated and extracted with ethyl acetate and distilled water. Purification by column chromatography using chloroform and hexane, and recrystallization with methylene chloride and hexane to complete the wet purification. 0.5 g of a yellow solid compound 2 was obtained (yield: 10%).

Example 1: Fabrication of light emitting diode

An organic light emitting diode was prepared by applying the compound 1 synthesized in Synthesis Example 1 as a dopant of a light emitting material layer. First, the glass substrate with 40 mm x 40 mm x 0.5 mm thick ITO (with reflector) electrodes was ultrasonically cleaned with isopropyl alcohol, acetone, DI water for 5 minutes, and then dried in an oven at 100 ° C. After the substrate was cleaned, it was subjected to an O ₂ plasma treatment in a vacuum for 2 minutes and transferred to a deposition chamber for deposition of other layers on the top. An organic layer was deposited by evaporation from a heated boat under a vacuum of about 10 ^-7 Torr in the following order.

A hole injection layer (HAT-CN, 7 nm), a hole transport layer (NPB, 55 nm), an electron blocking layer (mCBP, 10 nm) (B3PYMPM, 10 nm), an electron transport layer (TPBi, 20 nm), and an electron injection layer (35 nm) were used as the host, dibenzo [b, d] LiF), and a cathode (Al).

A capping layer (CPL) was formed and 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.

Example 2: Fabrication of light emitting diode

Emitting diode was prepared by repeating the procedure of Example 1 except that Compound 2 synthesized in Synthesis Example 2 was used instead of Compound 1 as a dopant of the light-emitting substance layer.

Example 3: Fabrication of light emitting diode

The procedure of Example 1 was repeated except that Compound 3 synthesized in Synthesis Example 3 was used in place of Compound 1 as a dopant of the light emitting material layer to prepare a light emitting diode.

Comparative Examples 1 and 2: Light Emitting Diode Fabrication

The procedure of Example 1 was repeated except that the following compounds were used in place of the compound 1 as the dopant of the light emitting material layer, respectively, to fabricate the light emitting diode.

Experimental Example: Measurement of luminescence characteristics of organic light emitting diode

The properties of the organic light emitting diodes fabricated in Examples 1 to 3 and Comparative Examples 1 and 2 were measured. Each organic light emitting diode having an emission area of 9 mm < 2 > was connected to an external power source, and device characteristics were evaluated at room temperature using a current source (KEITHLEY) and a photometer (PR 650). (V), current efficiency (cd / A), power efficiency (lm / W), external quantum efficiency (EQE,%) of each LED measured at a current density of 10 mA / The CIE color coordinate measurement results are shown in Table 1 below.

Evaluation of luminescence characteristics of light emitting diodes Sample V cd / A lm / W EQE (%) CIEx Comparative Example 1 4.96 11.67 7.39 6.94 (0.170, 0.263) Comparative Example 2 5.55 8.94 5.06 5.74 (0.170, 0.234) Example 1 4.51 37.31 25.97 12.91 (0.381, 0.581) Example 2 4.72 40.85 27.22 13.99 (0.373, 0.586) Example 3 4.83 46.22 30.08 15.65 (0.330, 0.598)

As shown in Table 1, when the organic compound synthesized according to the present invention was used as a dopant of the light emitting material layer as compared with the case where the organic compound of Comparative Example 1 was used as a dopant of the light emitting material layer, , And the current efficiency, power efficiency, and external quantum efficiency were improved by up to 296.1%, 307.0%, and 125.5%, respectively. Further, as compared with the case where the organic compound of Comparative Example 2 was used as a dopant of the light emitting material layer, when the organic compound synthesized according to the present invention was used as a dopant of the light emitting material layer, the driving voltage was reduced by a maximum of 18.7% , Power efficiency and external quantum efficiency were increased by 417.0%, 494.4% and 172.6%, respectively. In particular, the compounds used in Comparative Example 1 and Comparative Example 2 emitted blue light, but the organic compounds synthesized according to the present invention showed green light emission and different luminescent properties. As a result, it has been confirmed that the organic compound of the present invention can be applied to the light emitting layer to greatly reduce the driving voltage and to fabricate an organic light emitting diode having good light emitting efficiency. Accordingly, by using the organic light emitting diode to which the organic compound of the present invention is applied, it is possible to realize a light emitting device such as an organic light emitting diode display device and / or a lighting device with improved luminous efficiency and low driving voltage.

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: first electrode 120, 220, 420: second electrode
130, 230, 430: an organic light emitting layer 140, 240: a 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, 265: exciton blocking layer 300: organic light emitting diode display device

Claims (12)

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

Wherein R ₁ to R ₄ each independently represent an unsubstituted or substituted C ₁₀ to C ₃₀ condensed heteroaromatic substituent comprising one or two nitrogen atoms and consisting of three to five rings; R ₅ to R ₈ are each independently hydrogen, deuterium, tritium, cyano, unsubstituted or substituted C ₁₀ -C ₃₀ condensed homoaromatic substituent consisting of three to five condensed rings, or one or two nitrogen atoms Substituted and unsubstituted C ₁₀ to C ₃₀ condensed heteroaromatic substituent comprising 3 to 5 rings, Ar ₁ and Ar ₂ are each independently a C ₅ to C ₃₀ homoaryl group, a C ₄ to C ₃₀ a heteroaryl group, C ₅ ~ C ₃₀ Homo arylalkyl group, C ₄ ~ C ₃₀ heteroaryl group, C ₅ ~ C ₃₀ Homo aryloxy group, C ₄ ~ C ₃₀ heteroaryloxy group, C ₅ ~ C ₃₀ Homo arylamine Group and a C ₄ to C ₃₀ heteroarylamine group Ar ₃ , L ₁ and L ₂ are each independently a C ₅ to C ₃₀ homoarylene group, a C ₄ to C ₃₀ heteroarylene group, a C ₅ to C ₃₀ homoarylalkylene group, a C ₄ to C ₃₀ heteroarylalkyl A C ₅ to C ₃₀ homoaryloxylene group and a C ₄ to C ₃₀ heteroaryloxylene group, a and b are each independently 0 or 1,
The method according to claim 1,
Wherein the organic compound comprises an organic compound represented by the following formula (2).
(2)

Wherein R ₁₁ to R ₁₄ are each independently selected from the group consisting of a carbazyl group, a benzocarbamoyl group, a dibenzocarbamoyl group, and an indenocarbamoyl group; R ₁₅ to R ₁₈ are each independently selected from the group consisting of hydrogen L ₃ is a phenylene group, a and b are the same as defined in formula (1), and R 1 and R ₂ are independently selected from the group consisting of hydrogen, deuterium, tritium, cyano, carbamoyl, benzocarbamoyl, dibenzocarbamoyl and indenocarbamoyl; Lt; / RTI >
The method according to claim 1,
Wherein the organic compound is any organic compound represented by the following general formula (3).
(3)

A first electrode and a second electrode facing each other;
And an organic light emitting layer disposed between the first electrode and the second electrode,
Wherein the organic light emitting layer comprises an organic compound represented by Formula 1 below.
Formula 1

Wherein R ₁ to R ₄ each independently represent an unsubstituted or substituted C ₁₀ to C ₃₀ condensed heteroaromatic substituent comprising one or two nitrogen atoms and consisting of three to five rings; R ₅ to R ₈ are each independently hydrogen, deuterium, tritium, cyano, unsubstituted or substituted C ₁₀ -C ₃₀ condensed homoaromatic substituent consisting of three to five condensed rings, or one or two nitrogen atoms Substituted and unsubstituted C ₁₀ to C ₃₀ condensed heteroaromatic substituent comprising 3 to 5 rings, Ar ₁ and Ar ₂ are each independently a C ₅ to C ₃₀ homoaryl group, a C ₄ to C ₃₀ a heteroaryl group, C ₅ ~ C ₃₀ Homo arylalkyl group, C ₄ ~ C ₃₀ heteroaryl group, C ₅ ~ C ₃₀ Homo aryloxy group, C ₄ ~ C ₃₀ heteroaryloxy group, C ₅ ~ C ₃₀ Homo arylamine Group and a C ₄ to C ₃₀ heteroarylamine group Ar ₃ , L ₁ and L ₂ are each independently a C ₅ to C ₃₀ homoarylene group, a C ₄ to C ₃₀ heteroarylene group, a C ₅ to C ₃₀ homoarylalkylene group, a C ₄ to C ₃₀ heteroarylalkyl A C ₅ to C ₃₀ homoaryloxylene group and a C ₄ to C ₃₀ heteroaryloxylene group, a and b are each independently 0 or 1,
5. The method of claim 4,
Wherein the organic compound comprises an organic compound represented by the following formula (2).
(2)

Wherein R ₁₁ to R ₁₄ are each independently selected from the group consisting of a carbazyl group, a benzocarbamoyl group, a dibenzocarbamoyl group, and an indenocarbamoyl group; R ₁₅ to R ₁₈ are each independently selected from the group consisting of hydrogen L ₃ is a phenylene group, a and b are the same as defined in formula (1), and R 1 and R ₂ are independently selected from the group consisting of hydrogen, deuterium, tritium, cyano, carbamoyl, benzocarbamoyl, dibenzocarbamoyl and indenocarbamoyl; Lt; / RTI >
5. The method of claim 4,
Wherein the organic compound is any organic compound represented by the following formula (3).
(3)

5. The method of claim 4,
Wherein the organic light emitting layer includes a light emitting material layer including a light emitting material, and the organic compound is used as a dopant of the light emitting material layer.
8. The method of claim 7,
Wherein the light emitting material layer further comprises a host.
9. The method of claim 8,
(HOMO ^H -HOMO ^D |) between the highest level occupied molecular orbital energy level (HOMO ^H ) of the host and the highest level occupied molecular orbital energy level (HOMO ^D ) of the dopant or the lowest level non occupied molecular orbital Wherein the difference (LUMO ^H -LUMO ^D ) between the energy level (LUMO ^H ) and the lowest level non occupied molecular orbital energy level (LUMO ^D ) of the dopant is 0.5 eV or less.
5. The method of claim 4,
Wherein the difference (DELTA E _ST ) between the singlet energy level (S ₁ ) and the triplet energy level (T ₁ ) of the organic compound is 0.3 eV or less.
Board;
An organic light emitting diode according to any one of claims 4 to 10, which is disposed on the substrate; And
And a driving unit connected to the first electrode of the organic light emitting diode,
And an organic light emitting device.
12. The method of claim 11,
Wherein the organic light emitting device includes an organic light emitting diode display.

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