KR102505168B1 - Organic compounds, organic light emitting diode and orgnic light emitting device having the compounds - Google Patents

Abstract

The present invention relates to organic compounds having an aromatic ring linked to a bipyridine moiety, either directly or through a linker. The organic compound according to the present invention has a bipyridine moiety having excellent n-type characteristics, thereby minimizing exciton quenching due to an interaction between a triplet exciton of a dopant and a peripheral hole-polaron. Accordingly, it is possible to prevent a decrease in lifespan of the light emitting diode device due to electro-oxidation and photo-oxidation. In addition, in the organic compound of the present invention, at least one of the bipyridine moiety and/or the aromatic ring is substituted with a cyano group, so that the energy band gap and the excited state triplet energy level (T ₁ ) are not lowered, and the luminous efficiency is improved. . Accordingly, the organic compound of the present invention may be used as a host of a light emitting material layer by being used together with, for example, a delayed fluorescence dopant emitting blue light. By applying the organic compound of the present invention, it can be used for organic light emitting diodes and organic light emitting devices with improved luminous efficiency and, in particular, device lifetime.

Description

Organic compounds and organic light emitting diodes and organic light emitting devices containing the same

The present invention relates to an organic compound, and more particularly, to an organic compound that can be applied to an organic material layer of a light emitting diode, an organic light emitting diode and an organic light emitting device including the organic compound.

As one of the currently widely used flat display devices, the technology of an organic light emitting diode device, also called an organic electroluminescent device (OELD), is rapidly developing.

Organic light emitting diodes (OLEDs) are formed of a thin organic thin film of less than 2000 Å, and can implement images in a single direction or in both directions depending on the configuration of electrodes used. In addition, the organic light emitting diode display device can form elements on a flexible transparent substrate such as plastic, so it is easy to implement a flexible or foldable display device. In addition, the organic light emitting diode display can be driven at a low voltage and has excellent color purity, so it has great advantages over a liquid crystal display device (LCD).

An 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. In order to increase luminous efficiency, the organic light emitting layer may include a hole injection layer, a hole transport layer, a light emitting material layer, an electron transport layer, and an electron injection layer sequentially stacked on the hole injection electrode. At this time, holes injected from the anode and electrons injected from the cathode are combined in the light emitting material layer to form an exciton (exciton) to enter an unstable excited state, and then to a stable ground state ( It returns to the ground state and emits light.

The practical efficiency characteristics of OLED devices are finally determined by external quantum efficiency, which measures the amount of light emitted to the outside. The external quantum efficiency (EQE; η _ext ) of the light emitting material applied to the light emitting material layer can be calculated by Equation 1 below.

(η _int is internal quantum efficiency (IQE); г is charge balance factor; Φ is radiative quantum efficiency; η _out-coupling is light-extraction efficiency (out-coupling efficiency)

The internal quantum efficiency (η _int ) is the rate at which the generated excitons are converted into light. Theoretically, when holes and electrons meet to form excitons, a singlet exciton in the form of a paired spin according to the spin arrangement A singlet exciton and a triplet exciton in the form of an unpaired spin are generated at a ratio of 1:3. In fluorescent materials, only singlet excitons participate in light emission, and the remaining 75% of triplet excitons do not participate in light emission. As such, in the case of a general fluorescent material in which the singlet to triplet generation ratio is 1:3 and the triplet exciton cannot be emitted in an OLED device, the internal quantum efficiency (η _int ) is only 0.25 at most.

The charge balance factor (г) means the balance of holes and electrons forming excitons, and generally has a value of '1' assuming a 1:1 matching of 100%. Radiant quantum efficiency (Φ) is a value related to the luminous efficiency of the actual light emitting material, and depends on the photoluminescence (PL) of the dopant in a host-dopant system.

Light-extraction efficiency (η _{out -coupling} ) is a ratio of light extracted to the outside among light emitted from a light emitting material. In general, when a thin film is formed by thermally depositing an isotropic type of light emitting material, individual light emitting molecules do not have a certain directionality and exist in a disordered state. In such a random orientation state, the light-extraction efficiency when no special light extraction technique is applied is about 0.2 to 0.3. Therefore, when the four elements shown in Equation 1 are combined, the maximum luminous efficiency of the organic light emitting diode using the fluorescent material is only 5 to 7.5%.

Phosphorescent materials have been developed to solve the low external quantum efficiency of fluorescent materials. In the case of phosphorescent materials, singlet excitons are mostly transferred to triplet states through intersystem crossing (ISC), and the energy of triplet states is bottomed out by strong spin-orbit coupling by heavy metals. state transition is possible. As such, phosphorescent materials have a light-emitting mechanism that converts both singlet energy and triplet energy into light. Therefore, the phosphorescent material can implement an external quantum efficiency of 20 to 30% at most.

However, metal complexes commonly used as phosphorescent materials are expensive and have a very short lifespan, limiting their commercialization. In particular, in the case of blue phosphorescent materials, the color purity is difficult to apply to high-definition displays, and the lifespan also falls short of the commercialized level, so it is not applied to commercialized OLED panels.

In addition, the blue phosphorescent host material should be higher than the triplet energy of the blue phosphorescent dopant material in order to prevent back energy transfer of the blue phosphorescent dopant material to the host. However, since the triplet energy of an organic aromatic compound is rapidly lowered as conjugation increases or fused rings are formed, organic materials that can be used as blue phosphorescent hosts are extremely limited. Moreover, conventional blue phosphorescent hosts are designed to have a band gap of 3.5 to 4.5 eV or more in order to have high triplet energy. Since a host material having an excessively wide bandgap does not smoothly inject and transport charges, a high driving voltage is required, which may adversely affect the lifespan characteristics of the device.

Therefore, it is necessary to continuously develop light-emitting organic compounds having excellent light-emitting efficiency and improved lifetime characteristics, light-emitting diodes and light-emitting devices to which the organic compounds are applied.

An object of the present invention is to provide an organic compound having a wide band gap and excellent color purity.

Another object of the present invention is to provide an organic light emitting diode and an organic light emitting device having good luminous efficiency and improved lifetime characteristics.

According to one aspect of the present invention, the present invention provides an organic compound wherein at least one of the bipyridine core and/or the aromatic ring is substituted with a cyano group, as a compound in which an aromatic ring is directly or through a linker connected to a bipyridine core. For example, the organic compound may be represented by Formula 1 below.

Formula 1

(In Formula 1, R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a tritium atom or a cyano group (—CN); R ₅ and R ₆ are each independently unsubstituted or substituted C ₅ to C ₃₀ An aryl group or an unsubstituted or substituted C ₄ ~ C ₃₀ heteroaryl group, and when R ₁ to R ₄ are not all cyano groups, at least one selected from R ₅ and R ₆ is a substituted C group substituted with a cyano group; ₅ ~ C ₃₀ Aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted with a cyano group; L ₁ and L ₂ are each independently an unsubstituted or substituted C ₅ ~ C ₃₀ arylene group or an unsubstituted or substituted C ₄ ~C ₃₀ is a hetero arylene group; a and b are each 0 or 1)

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

For example, the organic compound may be used as a host of the light emitting material layer.

The organic compound of the present invention has an aromatic ring moiety connected directly or through a linker to a bipyridine moiety. Since the organic compound according to the present invention has a bipyridine moiety having excellent n-type characteristics, for example, when applied to a light emitting material layer, the triplet exciton of the dopant and the surrounding hole-polaron interaction Exciton quenching is minimized. Accordingly, since the lifetime of the light emitting diode device can be prevented from being reduced due to electro-oxidation and photo-oxidation, a light emitting device with a long lifespan can be implemented.

In addition, the organic compound according to the present invention has a cyano group (-CN) in which one of the bipyridi moiety and/or the aromatic ring has an excellent electron withdrawing property, so that the triplet energy of the organic compound does not decrease. , high-purity blue shift is facilitated.

Therefore, by using the organic compound of the present invention as a host of the organic light emitting layer constituting the organic light emitting diode and using a compound showing delayed fluorescence as a dopant, the luminous efficiency and lifespan of the device are improved, and high purity blue light can be emitted. An organic light emitting diode and an organic light emitting device may be manufactured.

1 is a schematic diagram for explaining a light emitting mechanism of a delayed fluorescent compound used together with an organic compound according to an exemplary embodiment of the present invention.
2 is a schematic diagram for explaining energy levels with a delayed fluorescent compound when an organic compound according to an exemplary embodiment of the present invention is used as a host.
3 is a cross-sectional view schematically illustrating 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.
4 is a cross-sectional view schematically illustrating 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 schematic cross-sectional view of an organic light emitting diode display device as an example of a light emitting device having an organic light emitting diode applied to an organic light emitting layer according to an exemplary embodiment of the present invention.
6 to 9 are graphs showing NMR analysis results of organic compounds synthesized according to exemplary embodiments of the present invention, respectively.

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

[organic compound]

The organic compound according to the present invention may be represented by Formula 1 below.

Formula 1

(In Formula 1, R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a tritium atom or a cyano group (—CN); R ₅ and R ₆ are each independently unsubstituted or substituted C ₅ to C ₃₀ An aryl group or an unsubstituted or substituted C ₄ ~ C ₃₀ heteroaryl group, and when R ₁ to R ₄ are not all cyano groups, at least one selected from R ₅ and R ₆ is a substituted C group substituted with a cyano group; ₅ ~ C ₃₀ Aryl group or C ₄ ~ C ₃₀ heteroaryl group substituted with a cyano group; L ₁ and L ₂ are each independently an unsubstituted or substituted C ₅ ~ C ₃₀ arylene group or an unsubstituted or substituted C ₄ ~C ₃₀ is a hetero arylene group; a and b are each 0 or 1)

In the present specification, 'unsubstituted' or 'unsubstituted' means that a hydrogen atom is substituted, and in this case, the hydrogen atom includes light hydrogen, heavy hydrogen, and tritium.

Substituents in 'substituted' herein include, for example, an unsubstituted or halogen-substituted C ₁ ~ C ₂₀ alkyl group, an unsubstituted or halogen-substituted C ₁ ~ C ₂₀ alkoxy group, a halogen, a cyano group, -CF ₃ , hydroxyl group, carboxy group, carbonyl group, amine group, C ₁ ~ C ₁₀ alkyl-substituted amine group, C ₅ ~ C ₃₀ aryl-substituted amine group, C ₄ ~ C ₃₀ heteroaryl-substituted amine group, nitro group, hydrazyl group (hydrazyl group), sulfonic acid group, C ₁ ~C ₂₀ Alkyl silyl 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 A heteroaryl silyl group, a C ₅ ~C ₃₀ aryl group, a C ₄ ~C ₃₀ heteroaryl group, and the like, but the present invention is not limited thereto. For example, when R ₅ and/or R ₆ in Formula 1 is substituted with an alkyl group, the alkyl group may be a straight-chain or branched C ₁ -C ₂₀ , preferably a C ₁ -C ₁₀ alkyl group.

In the present specification, 'heteroaromatic ring', 'heterocycloalkylene group', 'heteroarylene group', 'heteroarylalkylene group', 'heteroaryloxylene group', 'heterocycloalkyl group', 'heteroaryl group', ' The term 'hetero' used in 'hetero arylalkyl group', 'hetero aryloxyl group', 'hetero aryl amine group', etc. refers to one or more of the carbon atoms constituting these aromatic or alicyclic rings, for example For example, it means that 1 to 5 carbon atoms are substituted with one or more heteroatoms selected from the group consisting of N, O, S, and combinations thereof.

In one exemplary embodiment, when R ₅ and/or R ₆ is an unsubstituted or substituted C ₅ to C ₃₀ is an aryl group, R ₅ and/or R ₆ are each independently an unsubstituted or substituted phenyl group, bi Phenyl group, terphenyl group, naphthyl group, anthracenyl group, pentanrenyl group, indenyl group, indenoidinyl group, heptalenyl group, biphenylenyl group, indacenyl group, phenalenyl group, phenanthrenyl group, benzophenanthrenyl group, Dibenzophenanthrenyl group, azulenyl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, tetraphenyl group, tetracenyl group, playdaenyl group, phycenyl group, pentaphenyl group, pentacenyl group , It may be an uncondensed or fused aryl group such as a fluorenyl group, an indenofluorenyl group, or a spiro fluorenyl group.

In an alternative embodiment, when R ₅ and/or R ₆ is an unsubstituted or substituted C ₄ -C ₃₀ heteroaryl group, R ₅ and/or R ₆ are each independently an unsubstituted or substituted pyrrolyl group, pyridine Nyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, tetrazinyl group, imidazolyl group, pyrazolyl group, indolyl group, isoindoleyl group, indazolyl group, indolizinyl group, pyrrozinyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl group, quinolinyl group, isoquinoyl group Nyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group, quinazolinyl group, quinozolinyl group, quinozolinyl group, purinyl group, phthalazinyl group, quinoxalinyl group, benzoquinolinyl group, benzoisoquinolinyl group , Benzoquinazolinyl group, benzoquinoxalinyl group, acridinyl group, phenanthrolinyl group, perimidinyl group, phenanthridinyl group, pteridinyl group, sinnolinyl group, naphtharidinyl group, furanyl group, pyranyl group, oxazinyl group, oxazolyl group, oxadiazolyl group, triazolyl group, dioxinyl group, benzofuranyl group, dibenzofuranyl group, thiopyranyl group, xanthenyl group, chromenyl group, isochromenyl group, thioazinyl group, Thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, difuropyrazinyl group, benzofurodibenzofuranyl group, benzothienobenzothiophenyl group, benzothienodibenzothiophenyl group, benzothienobenzofuranyl group, benzothienodibenzo It may be an uncondensed or condensed heteroaryl group such as a furanyl group or an N-substituted spiro fluorenyl group.

Meanwhile, in one non-limiting embodiment, L ₁ and/or L ₂ , which is a linker (linking group) in Formula 1, may each independently be an unsubstituted or substituted aromatic linking group.

For example, when L ₁ and/or L ₂ is an unsubstituted or substituted C ₅ to C ₃₀ arylene group, L ₁ and/or L ₂ are each independently a substituted or unsubstituted phenylene group, bi phenylene group, terphenylene group, tetraphenylene group, indenylene group, naphthylene group, azulenylene group, indacenylene group, acene Acenaphthylene, fluorenylene, spiro-fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthrenylene (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl It may be selected from the group consisting of a pentaphenylene group and a hexacenylene group.

In another optional embodiment, when L ₁ and/or L ₂ is an unsubstituted or substituted C ₄ -C ₃₀ heteroarylene group, L ₁ and/or L ₂ are each independently a substituted or unsubstituted pyrrolylene group. (pyrrolylene), imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, iso Indolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group (benzoquinolinylene), phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, benzoquinolinylene, benzoisoquinolinylene, benzo Quinazolinylene group, benzoquinoxalinylene group, cinnolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, Benzoxazolylene, benzimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolyne (thiazolylene), isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, Trazolyne group, oxadiazolylene group, triazinylene group, benzofuranylene group, dibenzofuranylene group, benzofurodibenzofuranylene group, benzothienobenzofuranylene group, benzo Thienodibenzofuranylene group, benzothiophenylene group, dibenzothiophenylene group, benzothietobenzothiophenylene group, benzothienodibenzothiophenylene group, carbazolylene group, benzocarbazolylene group, dibenzocarbazolyl composed of a rene group, an indolocarbazolylene group, an indenocarbazolylene group, a benzofurocarbazolylene group, a benzothienocarbazolylene group, an imidazopyrimidinylene group and an imidazopyridinylene group. can be selected from the group.

In one exemplary embodiment, when the number of aromatic rings constituting L ₁ and/or L ₂ increases, the conjugated structure in the entire organic compound becomes too long, and the band gap of the organic compound may be excessively reduced. there is. Therefore, the number of aromatic rings constituting L ₁ is preferably 1 to 2, more preferably 1. In addition, with respect to hole or electron injection and transfer characteristics, L ₁ and/or L ₂ may each be a 5-membered ring or a 7-membered ring, particularly a 6-membered ring. A 6-membered ring may be preferred. For example, L ₁ and/or L ₂ is an unsubstituted or substituted phenylene group, biphenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, It may be a pyridazinylene group, a furanylene group, or a thiophenylene group.

The organic compound represented by Formula 1 has a bipyridine moiety with excellent n-type properties. When using a host together with a dopant having a conventional delayed fluorescence characteristic, a recombination zone in which holes and electrons recombine is formed at the interface of the light emitting material layer (EML)-electron transport layer (ETL)/hole blocking layer (HBL). do. Accordingly, the possibility that the triplet excitons of the dopant and the hole-polaron formed around the triplet excitons of the dopant meet and interact increases, and the exciton of the dopant does not contribute to the light emission, so that non-luminescence disappears. , as damage is applied to the light emitting material, the lifetime of the device decreases.

However, when an organic compound having a bipyridine moiety having strong n-type characteristics is used as a host according to the present invention, the recombination zone of holes and electrons is formed in the light emitting material layer (EML)-electron transport layer (ETL). )/hole blocking layer (HBL) to move to the central region of the light emitting material layer. Accordingly, the possibility of meeting the dopant and the hole-polaron is reduced, electro-oxidation and photo-oxidation due to the interaction of the dopant and the hole-polaron are prevented, thereby reducing non-luminescence extinction, and damage to the material is reduced. While decreasing, the life of the device can be improved.

In addition, in the organic compound according to the present invention, at least one of the central bipyridine moiety and/or the aromatic rings on both sides is substituted with a cyano group (-CN). Accordingly, the organic compound according to the present invention has a wide bandgap and high triplet energy, and easy blue shift. Therefore, the organic compound according to the present invention can be used as a host of an organic light emitting layer constituting an organic light emitting diode, and can be applied to a light emitting material layer using a so-called delayed florescence compound as a dopant. Explain.

1 is a schematic diagram for explaining a light emitting mechanism of a delayed fluorescent compound used together with an organic compound according to an exemplary embodiment of the present invention. Delayed fluorescence can be divided into thermally activated delayed fluorescence (TADF) and field activated delayed fluorescence (FADF). It is possible to realize so-called super-fluorescence that exceeds the maximum luminous efficiency in materials.

That is, in the delayed fluorescent compound, triplet excitons are activated by heat or an electric field generated when the device is driven, and the triplet excitons also participate in light emission. In general, a delayed fluorescent compound has both an electron donor moiety and an electron acceptor moiety, and thus an intramolecular charge transfer (ICT) state is possible. When a delayed fluorescent compound capable of an ICT state 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 delayed fluorescent compound move to an intermediate state ICT state, Transitions to the ground state (S ₀ ) (S ₁ →ICT←T ₁ ), and both excitons with singlet energy levels (S ₁ ) and excitons with triplet energy levels (T ₁ ) participate in light emission Therefore, the internal quantum efficiency is improved, and thus the luminous efficiency is improved.

In conventional fluorescent materials, since the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are spread over the entire molecule, there is a transition between singlet and triplet states. Interchangeability is not possible (selection rule). However, since the overlapping of HOMO and LUMO orbitals in the compound having the ICT state is small, the interaction between the orbits of the HOMO state and the orbits of the LUMO state is small. Therefore, the spin state change of an electron does not affect other electrons, and a new charge transfer band (CT band) that does not follow the selection rule is formed.

That is, since the electron acceptor moiety and the electron donor moiety in the delayed fluorescent compound are spaced apart in the molecule, the dipole moment in the molecule exists in a large polarization state. In a state where the dipole moment is polarized, the interaction between the orbitals of the HOMO and LUMO states becomes small, a transition from the triplet state and the singlet state to the intermediate state (ICT) becomes possible, and the singlet energy level (S ₁ ) as well as the exciton and the triplet energy level (T ₁ ) all of the excitons participate in light emission. That is, when the light emitting device is driven, excitons having a singlet energy level (S ₁ ) of 25% and triplet energy levels (T ₁ ) of 75% are transitioned to an intermediate state (ICT) by heat or an electric field Since light emission occurs while falling back to the ground state (S ₀ ), the internal quantum efficiency theoretically becomes 100%.

Dopants and hosts for realizing delayed fluorescence need to have the following characteristics. The delayed fluorescent dopant should have an electron donor moiety and an electron acceptor moiety at the same time in one molecule, so that ICT can be implemented. The delayed fluorescence dopant usually has an ICT complex form, and has an electron donor moiety and an electron acceptor moiety in one molecule at the same time, so electron transfer easily occurs in the molecule. That is, in the ICT complex, one electron moves from the electron-donor moiety to the electron-acceptor portion under specific conditions, and charge separation occurs within the molecule. In addition, in order for energy transfer to occur in both the triplet state and the singlet state, the dopant capable of realizing delayed fluorescence has a difference (ΔE _ST ) between the singlet energy level (S1) and the triplet energy level (T1) of 0.3 eV or less. , for example between 0.05 and 0.3 eV. In this way, when thermal energy at room temperature is applied to a compound with a small ΔE _ST , Reverse Inter System Crossing (RISC) occurs from the triplet state to the singlet state with higher energy, and the singlet state returns to the ground state. can be transferred

Meanwhile, a host for realizing delayed fluorescence should be capable of inducing excitons in a triplet state in a dopant to participate in light emission without quenching (non-emission extinction, quenching). 2 is a schematic diagram for explaining energy levels with a delayed fluorescent compound when an organic compound according to an exemplary embodiment of the present invention is used as a host.

As shown in FIG. 2, the energy level of the host for realizing delayed fluorescence must be adjusted with the dopant. First, the excited-state triplet energy level of the host (T _1h ) should be higher than the excited-state triplet energy level (T _1d ) of the delayed fluorescent dopant. When the excited state triplet energy level of the host (T _1h ) is not sufficiently higher than the energy of the excited state triplet energy level (T _1d ) of the delayed fluorescent dopant, the excited state triplet energy level of the delayed fluorescent dopant (T _1d ) Since the reverse-charge transfer occurs in the excitons of the host to the excited state triplet energy level (T _1h ), and the triplet excitons are non-luminescently annihilated in the host where the triplet excitons cannot emit light, the triplet of the delayed fluorescent dopant State excitons do not contribute to light emission.

In addition, it is necessary to appropriately adjust the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level of the host and the delayed fluorescent 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 delayed fluorescent dopant (|HOMO ^H -HOMO ^D |) or the lowest level unoccupied molecule of the host The difference between the orbital energy level (LUMO ^H ) and the lowest level unoccupied molecular orbital energy level (LUMO ^D ) of the delayed fluorescent dopant (|LUMO ^H -LUMO ^D |) is preferably 0.5 eV or less, for example, 0.1 to 0.5 eV or less. can do. Accordingly, the charge transfer efficiency from the host to the delayed fluorescent dopant is improved, and finally, the luminous efficiency may be improved.

In addition, in order to secure a sufficient lifetime of a light emitting device to which a delayed fluorescence dopant is applied, the triplet exciton of the dopant and the surrounding hole-polaron meet and interact to cause exciton quenching (exciton quenching). It is necessary to suppress electro-oxidation and/or photo-oxidation by minimizing quenching. In the case of using a host applied to a conventional organic light emitting layer, a recombination zone in which electrons and holes moving from each electrode meet to form excitons is a light emitting material layer (EML, 260, see FIG. 4) and an electron transport layer ( ETL, 270, see FIG. 4) or hole blocking layer (HBL, 265, see FIG. 4) is formed at the interface.

As described above, triplet excitons also contribute to light emission by using delayed fluorescence dopants. Therefore, when the recombination region for forming excitons is formed at the interface between the light emitting material layer and the electron transport layer/hole blocking layer, the possibility that the triplet excitons of the delayed fluorescent dopant and hole-polarons meet and interact with each other increases. Due to the interaction between the triplet excitons and the hole-platon, the triplet triplet energy of the delayed fluorescent dopant does not contribute to the light emission mechanism and becomes non-emitting extinction. When the non-emission extinction increases, stress is applied to the material applied to the organic light emitting layer, causing damage, thereby reducing device lifetime.

On the other hand, according to the present invention, the organic compound represented by Chemical Formula 1 is an n-type organic compound containing a bipyridine moiety that has excellent electron affinity and improves electron transfer speed. According to an exemplary embodiment of the present invention, when the organic compound of the present invention is used as a host of the organic light emitting layer, the recombination region where holes and electrons meet to form excitons is not the interface between the light emitting material layer and the adjacent organic material layer, but the light emitting material layer formed in the center of As a result, the possibility that the triplet excitons of the dopant and the hole-polaron meet and interact is reduced, and the triplet excitons are not extinguished in non-luminescence due to their interaction. Accordingly, damage to the light emitting material caused by non-luminous extinction of the light emitting material is prevented, and a reduction in device life due to damage of the light emitting material is prevented, thereby implementing a light emitting device with a long lifespan.

In addition, in the organic compound according to the present invention, at least one of the bipyridine moiety and the aromatic moiety (R ₅ , R ₆ ) connected to the bipyridine moiety directly or through a linker is a cyano group (—CN) having excellent electron withdrawing properties ) can be substituted. Accordingly, the organic compound of the present invention has an n-type characteristic, a wide band gap, and a high triplet energy level (T _1h ) of an excited state, so that it is suitable for use as a host for an organic light emitting layer. Suitable. That is, when the organic compound according to the present invention is used as a host of the organic light-emitting layer, the exciton of the excited state triplet energy level (T _1d ) of the delayed fluorescent dopant reverses to the triplet energy level (T _1h ) of the host-charge transfer While this is suppressed, and non-luminescence extinction of the triplet excitons in the host is suppressed, the triplet state excitons of the delayed fluorescence dopant contribute to the emission of light, and the luminous efficiency can be improved. In addition, since at least one cyano group is introduced, the color purity is excellent and a blue shift can be realized.

In one exemplary embodiment, the organic compound according to the present invention includes a compound represented by Formula 2 below.

Formula 2

(In Formula 2, R ₁ , R ₂ , R ₃ , R ₄ , a, and b are the same as those defined in Formula 1; R ₇ and R ₈ are each independently an unsubstituted or substituted C4~C30 heteroaryl group, and , When R ₁ to R ₄ are not all cyano groups, at least one selected from R ₇ and R ₈ is a substituted C4-C30 heteroaryl group substituted with a cyano group; L ₃ and L ₄ are each independently unsubstituted unsubstituted or substituted C4~C30 hetero arylene group)

,

또는

일 수 있다. 한편, L₃ 및/또는 L₄는 각각 5-원자 고리(5-membered ring) 내지 7-원자 고리(7-membered ring)일 수 있으며, 특히 6-원자 고리(6-membered ring)인 것이 바람직할 수 있다. 예를 들어, L₃ 및/또는 L₄는 치환되지 않거나 치환된 페닐렌기, 바이페닐렌기일 수 있지만, 본 발명이 이에 한정되는 것은 아니다. According to one exemplary embodiment, in Formula 2, R ₇ and/or R ₈ are each independently unsubstituted or selected from a cyano group, a C ₁ ~C ₂₀ alkyl group, a C ₅ ~C ₃₀ aryl group, and/or a C ₄ ~ It may be a carbazoyl group, an acridyl group, a dihydroacridyl group, a furobipyridyl group, a fluorenyl group, or a xanthenyl group substituted with a C ₃₀ heteroaryl group, but the present invention is not limited thereto. For example, R ₇ and/or R ₈ are each independently

,

or

can be On the other hand, L ₃ and / or L ₄ may each be a 5-membered ring to a 7-membered ring, particularly preferably a 6-membered ring. can do. For example, L ₃ and/or L ₄ may be an unsubstituted or substituted phenylene group or a biphenylene group, but the present invention is not limited thereto.

More specifically, the organic compound according to the present invention may be any one compound represented by Formula 3 below.

Formula 3

The organic compound represented by Formula 2 or Formula 3 has a bipyridine moiety having n-type characteristics. Therefore, when the organic compound represented by Chemical Formula 2 or Chemical Formula 3 is used in the light emitting material layer, a recombination region where electrons and holes meet to form excitons is formed in the center of the light emitting material layer. Accordingly, exciton quenching due to the interaction between the triplet exciton of the dopant and the surrounding hole-polaron can be minimized, and the life span of the light emitting diode device due to electro-oxidation and photo-oxidation can be prevented from deteriorating. there is.

In addition, since at least one of the bipyridine moiety and/or the aromatic ring is substituted with a cyano group in the organic compound of the present invention, the energy band gap and the excited state triplet energy level (T ₁ ) do not decrease, and the luminous efficiency is improved. and excellent color purity can be implemented while blue transition is made. That is, when the organic compound of Formula 2 or Formula 3 is used as a host of the light emitting material layer, since energy can be efficiently transferred to the dopant, the light emitting efficiency of the light emitting device to which the organic compound of the present invention is applied can be improved. In addition, since damage to the material applied to the light emitting material layer is reduced, a long lifespan light emitting device can be manufactured and a light emitting device having excellent color purity can be implemented.

[Organic Light-Emitting Diode and Organic Light-Emitting Diode Display]

As described above, the organic compounds represented by Chemical Formulas 1 to 3 can be used as a light emitting material in an organic light emitting layer constituting an organic light emitting diode to implement a light emitting device having good color purity and improved light emitting efficiency and device lifetime characteristics. there is. explain this. 3 is a cross-sectional view schematically illustrating 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.

As shown in FIG. 3, 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, and the first and second electrodes 110 , 120) and an organic light emitting layer 130 positioned between them. In an exemplary embodiment, the organic light emitting layer 130 may include a hole injection layer (HIL) 140 sequentially stacked from the first electrode 110, a hole transfer layer (HTL) 150, and a light emitting material. It includes 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 supplying holes to the light emitting material layer 160 . The first electrode 110 is preferably formed of a conductive material having a relatively high work function value, for example, transparent conductive oxide (TCO). For example, the first electrode 110 may be indium-tin-oxide (ITO), indium-zinc-oxide (IZO), or indium-tin-zinc-oxide (indium-tin-oxide). -tin-zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO) and aluminum:zinc oxide (Al:ZnO; AZO) there is.

The second electrode 120 may be a cathode supplying electrons to the light emitting material layer 160 . The second electrode 120 is formed of a conductive material having a relatively small work function value, for example, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or an alloy or combination thereof having reflective properties. It can be made of good material.

The hole injection layer 140 is positioned between the first electrode 110 and the hole transport layer 150, and improves interface characteristics between the inorganic first electrode 110 and the organic hole transport layer 150. In one exemplary embodiment, the hole injection layer 140 is 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine; MTDATA), copper phthalocyanine (CuPc), tris (4-carbazoyl-9-yl-phenyl) amine (TCTA), N, N'-diphenyl -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-hexaazatriphenylenehexacarbonitrile (1,4,5,8,9,11- hexaazatriphenylenehexacarbonitrile; HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (1,3,5-tris[4-(diphenylamino)phenyl]benzene; TDAPB), poly(3, 4-ethylenedioxythiophene)polystyrene sulfonate (poly(3,4-ethylenedioxythiophene)polystyrene sulfonate (PEDOT/PSS) and/or N-(biphenyl-4-yl)-9,9-dimethyl-N-(4 -(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(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 positioned 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 N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (N ,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine; TPD), NPD, 4,4'-bis(N-carbazolyl)- 1,1'-biphenyl (4,4'-bis (N-carbazolyl) -1,1'-biphenyl; CBP), 1,3-bis (N-carbazolyl) benzene (1,3-bis (N -carbazolyl)benzene; mCP), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-flu Oren-2-amine (N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine ) And / or N- (biphenyl-4-yl) -N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) biphenyl) -4-amine (N- (biphenyl-4 -yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine), etc., 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 have about 1 to 30% by weight of a dopant added to the host and may emit blue light.

Organic compounds represented by Chemical Formulas 1 to 3 may be used as a host of the light emitting material layer 160 . Meanwhile, the dopant used in the light emitting material layer 160 may be a dopant having delayed fluorescence characteristics.

As described above, the compound having delayed fluorescence is activated by heat or an electric field and has an intermediate energy state such as an ICT complex. Since both excitons with a singlet energy level and excitons with a triplet energy level are involved in light emission, the light emitting efficiency of the organic light emitting diode 100 can be improved. In addition, when the difference (ΔE _ST ) between the excited state singlet energy level (S ₁ ) and the excited state triplet energy level (T ₁ ) of the dopant is 0.3 eV or less, the dopant transitions to an intermediate energy state at these energy levels, and finally Falling to the ground state can improve the quantum efficiency of the dopant. That is, the luminous efficiency may increase as ΔE _ST decreases, and when the difference between the excited state singlet energy level (S _1d ) and the excited state triplet energy level (T _1d ) of the dopant is 0.3 eV or less, heat or an electric field Singlet state excitons and triplet state excitons can transition to an intermediate state, the ICT complex state.

In addition, in order to maximize the luminous efficiency by delayed fluorescence, the excited state triplet energy level (T _1h , see FIG. 2) of the organic compound represented by Chemical Formulas 1 to 3 used as a host is determined by the delayed fluorescent compound used as a dopant. It must be higher than the excited state triplet energy level (T _1d , see FIG. 2) of In particular, 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 unoccupied molecular orbital energy level of the host When the difference between (LUMO ^H ) and the lowest level unoccupied molecular orbital energy level (LUMO ^D ) of the dopant (|LUMO ^H -LUMO ^D |) is 0.5 eV or less, energy is efficiently transferred from the host to the dopant, maximizing luminous efficiency. can do.

According to one exemplary embodiment, when the organic compound represented by Chemical Formulas 1 to 3 is used as a host of the light emitting material layer 160, it is preferable to use a dopant having an appropriate energy level with the host while showing delayed fluorescence characteristics. may be desirable. For example, the delayed fluorescence dopant may be a delayed fluorescence dopant that emits blue light. In order to implement a level of blue light emission applicable to display devices, the excited state singlet energy level (S _1d ) of the delayed fluorescent dopant may be 2.7 to 2.8 eV, and the excited state triplet energy level (T _1d ) may be 2.4 to 2.5 eV or more, but the present invention is not limited thereto.

According to an exemplary embodiment of the present invention, the blue emission-retarding fluorescent dopant that can be used as the dopant of the light-emitting material layer 160 is 10-(4-(4,6-diphenyl-1,3,5-triazine-2 -yl) phenyl) -9,9-dimethyl-9,10-dihydroacridine (10- (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -9 ,9-dimethyl-9,10-dihydroacridine, DMAC-TRZ), 10,10'-(4,4'-sulfonylbis(4,1-phenylene))bis(9,9-dimethyl-9,10 -Dihydroacridine)(10,10'-(4,4'-sulfonylbis(4,1-phenylene))bis(9,9-dimethyl-9,10-dihydroacridine), DMAC-DPS), 10- Phenyl-10H,10'H-spiro[acridine-9,9'-anthracen]-10'-one (10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracen]- 10'-one, ACRSA), 3,6-dibenzoyl-4,5-di (1-methyl-9-phenyl-9H-carbazoyl) -2-ethynylbenzonitrile (3,6-dibenzoyl-4, 5-di(1-methyl-9-phenyl-9H-carbazoyl)-2-ethynylbenzonitrile, Cz-VPN), 9,9',9"-(5-(4,6-diphenyl-1,3,5 -triazin-2-yl)benzene-1,2,3-triyl)tris(9H-carbazole(9,9',9"-(5-(4,6-diphenyl-1,3,5- triazin-2-yl)benzene-1,2,3-triyl) tris(9H-carbazole), TcZTrz), 9,9'-(5-(4,6-diphenyl-1,3,5-triazine -2-yl) -1,3-phenylene) bis (9H-carbazole) (9,9'-(5- (4,6-diphenyl-1,3,5-triazin-2-yl) -1 ,3-phenylene)bis(9H-carbazole), DczTrz), 9,9',9",9"'-((6-phenyl-1,3,5-triazine-2,4-diyl)bis( Benzene-5,3,1-triyl))tetrakis(9H-carbazole)(9,9',9",9"'-((6-phenyl-1,3,5-triazin-2, 4-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole, DDczTrz), bis(4-(9H-3,9'-bicarbazol-9-yl)phenyl)methanone (bis(4-(9H-3,9'-bicarbazol-9-yl)phenyl)methanone, CC2BP), 9'-[4-(4,6-diphenyl-1,3,5-triazine-2 -yl)phenyl]-3,3 ",6,6"-tetraphenyl-9,3',6',9"-tert-9H-carbazole (9'-[4-(4,6-diphenyl- 1,3,5-triazin-2-yl)phenyl]-3,3",6,6"-tetraphenyl-9,3':6',9"-ter-9H-carbazole, BDPCC-TPTA), 9 '-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9,3':6',9"-ter-9H-carbazole (9'- [4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9,3':,6',9"-ter-9H-carbazole, BCC-TPTA),

9,9'-(4,4'-sulfonylbis(4,1-phenylene))bis(3,6-dimethoxy-9H-carbazole)(9,9'-(4,4'-sulfonylbis (4,1-phenylene))bis(3,6-dimethoxy-9H-carbazole), DMOC-DPS), 9-(4-(4,6-diphenyl-1,3,5-triazine-2- yl) phenyl) -3',6'-diphenyl-9H-3,9'-bicarbazole (9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl )-3',6'-diphenyl-9H-3,9'-bicarbazole, DPCC-TPTA), 10-(4,6-diphenyl-1,3,5-triazin-2-yl)-10H- Phenoxazine (10-(4,6-diphenyl-1,3,5-triazin-2-yl)-10H-phenoxazine, Phen-TRZ), 9-(4-(4,6-diphenyl-1,3 ,5-triazin-2-yl)phenyl)-9H-carbazole (9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, Cab -Ph-TRZ), 2,3,4,6-tetra (9H-carbazol-9-yl) -5-fluorobenzonitrile (2,3,4,6-tetra (9H-carbazol-9-yl )-5-fluorobenzonitrile, 4CZFCN), 10-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-10H-spiro[acridine-9,9 '-fluorene](10-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-10H-spiro[acridine-9,9'-fluorene], SpiroAC-TRZ ) or may be represented by Formula 4 below, but the present invention is not limited thereto.

formula 4

For example, a dopant, which may be a delayed fluorescence dopant, may be added in an amount of 1 to 50% by weight in the light emitting material layer 160, but the present invention is not limited thereto.

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 . A material constituting the electron transport layer 170 requires high electron mobility, and electrons are stably supplied to the light emitting material layer 160 through smooth electron transport.

In one exemplary embodiment, the electron transport layer 170 is oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, benzimidazole , may be a derivative such as triazine.

For example, the electron transport layer 170 is tris (8-hydroxyquinoline) aluminum (tris- (8-hydroxyquinoline aluminum; Alq ₃ ), 2-biphenyl-4-yl-5- (4-tert-butylphenyl ) -1,3,4-oxadiazole (2-biphenyl-4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole; PBD), spiro-PBD, lithium quinolate ( lithium quinolate; Liq), 2-[4-(9,10-di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole ((2- [ 4-(9 ,10-di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-bi Phenyl-4-olato)aluminum (Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum; BAlq), 3-(biphenyl-4-yl ) -5- (4-tertbutylphenyl) -4-phenyl-4H-1,2,4-triazole (3- (biphenyl-4-yl) -5- (4-terbutylphenyl) -4-phenyl-4H -1,2,4-triazole; TAZ), 4,7-diphenyl-1,10-phenanthroline (4,7-diphenyl-1,10-phenanthroline; Bphen), tris (phenylquinoxaline) (tris (phenylquinoxaline; TPQ), and/or 1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene; TPBi) and the like, but the present invention is not limited thereto.

The electron injection layer 180 is positioned between the second electrode 120 and the electron transport layer 170, and the life of the device can be improved by improving the characteristics of the second electrode 120. In one exemplary embodiment, as a material of the electron injection layer 180, an alkali halide-based material such as LiF, CsF, NaF, BaF ₂ , and/or lithium quinolate (Liq), lithium benzoate, sodium Organometallic materials such as stearate (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 having a delayed fluorescence characteristic in the light emitting material layer 160 constituting the organic light emitting layer 130 . Since both singlet energy state and triplet energy state excitons are involved in light emission, the light emission efficiency is improved. In addition, the light emitting material layer 160 includes a host made of organic compounds represented by Chemical Formulas 1 to 3.

When the organic compound represented by Chemical Formulas 1 to 3 is used in the light emitting material layer, a recombination region where electrons and holes meet to form excitons is formed at the center of the light emitting material layer, not at the interface between the light emitting material layer and the electron transport layer. Accordingly, exciton quenching due to the interaction between the triplet exciton of the dopant and the surrounding hole-polaron can be minimized, and the life span of the light emitting diode device due to electro-oxidation and photo-oxidation can be prevented from deteriorating. there is. In addition, since at least one of the bipyridine moiety and/or the aromatic ring is substituted with a cyano group in the organic compound of the present invention, the energy band gap widens and the excited state triplet energy level (T _1h ) does not decrease, thereby emitting light. Efficiency is improved, blue transition is performed, and the organic light emitting diode 100 having excellent color purity can be implemented.

Meanwhile, the organic light emitting diode according to the present invention may further include one or more exciton blocking layers. 4 is a schematic cross-sectional view of an organic light emitting diode to which a phosphorescent compound is applied according to a second exemplary embodiment of the present invention. As shown in FIG. 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, and the first and second electrodes 210 , 220) and an organic light emitting layer 230 positioned between them.

In an 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 electron transport layer 270 sequentially stacked from the first electrode 210. An injection layer 280 is included. In addition, the organic light emitting layer 230 includes an electron blocking layer (EBL, 255) and/or a first exciton blocking layer positioned between the hole transport layer 250 and the light emitting material layer 260 and/or the light emitting material layer 260 ) and a hole blocking layer (HBL, 265) as a second exciton blocking layer located between 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, and AZO, which are conductive materials having a relatively high work function value. The second electrode 220 may be a cathode and may be made of Al, Mg, Ca, Ag, or an alloy or combination thereof, which is a conductive material having a relatively low work function value.

The hole injection layer 240 is positioned between the first electrode 210 and the hole transport layer 22 . The hole injection layer 240 is formed of MTDATA, CuPc, TCTA, NPB (NPD), HAT-CN, TDAPB, PEDOT/PSS and/or N-(biphenyl-4-yl)-9,9-dimethyl-N-( 4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and the like. Depending on the characteristics of the organic light emitting diode 200, the hole injection layer 240 may be omitted.

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 is formed of TPD, NPD, CBP, mCP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl) Phenyl)-9H-fluoren-2-amine and/or N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)- It may consist of an aromatic amine compound such as 4-amine.

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 have a dopant added to the host in an amount of about 1 to 50% by weight, and may emit blue light. For example, an organic compound represented by Chemical Formulas 1 to 3 is used as a host of the light emitting material layer 260, and a compound exhibiting delayed fluorescence, for example, DMAC-TRZ, DMAC-DPS, ACRSA, Cz-VPN, TcZTrz, DczTrZ, DDczTrZ, CC2BP, BDPCC-TPTA, BCC-TPTA, DMOC-DPS, DPCC-TPTA, Phen-TRZ, Cab-Ph-TRZ, 4CZFCN, SpiroAC-TRZ and/or the compound represented by Formula 4 can be used as a dopant.

The electron transport layer 270 is positioned between the light emitting material layer 260 and the electron injection layer 280 . For example, the electron transport layer 270 may include oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, benzimidazole, triazine, and the like. may be a derivative. For example, the electron transport layer 270 is Alq ₃ , PBD, spiro-PBD, Liq, 2-[4-(9,10-di-2-naphthalenyl-2-anthracenyl)phenyl]-1- It may consist of phenyl-1H-benzimidazole, BAlq, TAZ , Bphen, TPQ, and/or TPBi, etc., but the present invention is not limited thereto.

The electron injection layer 280 is positioned between the second electrode 220 and the electron transport layer 270 . Alkali halide-based materials such as LiF, CsF, NaF, and BaF ₂ and/or organic metal-based materials such as Liq and lithium benzoate) and sodium stearate may be used as the material of the electron injection layer 280, but the present invention It is not limited to this.

On the other hand, when holes pass through the light emitting material layer 260 and move to the second electrode 220 or when electrons pass through the light emitting material layer 260 and go to the first electrode 210, the lifespan and efficiency of the device are reduced. can bring To prevent this, in the organic light emitting diode 200 according to the second exemplary embodiment of the present invention, at least one exciton blocking layer is positioned 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 has an electron blocking layer capable of controlling or preventing the movement of electrons between the hole transport layer 250 and the light emitting material layer 260. layer, EBL, 255) is located.

For example, the electron blocking layer 255 is TCTA, tris [4- (diethylamino) phenyl] amine (tris [4- (diethylamino) phenyl] amine), N- (biphenyl-4-yl) -9, 9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, tri-p-tolylamine, 1 ,1-bis (4- (N, N-di (p-tolyl) amino) phenyl) cyclohexane (1,1-bis (4- (N, N'-di (ptolyl) amino) phenyl) cyclohexane; TAPC ), MTDATA, mCP, 3,3'-bis (N-carbazolyl) -1,1'-biphenyl (3,3'-bis (N-carbazolyl) -1,1'-biphenyl; mCBP), TPD , CuPC, N, N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (N ,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine; DNTPD) and/or TDAPB, etc. can be made with

In addition, a hole blocking layer 265 is positioned as a second exciton blocking layer between the light emitting material layer 260 and the electron transport layer 270 to prevent movement of holes between the light emitting material layer 260 and the electron transport layer 270 do. In one exemplary embodiment, as a material for the hole blocking layer, oxadiazole, triazole, phenanthroline, benzoxazole, and benzo that may be used in the electron transport layer 270 may be used. Derivatives such as benzothiazole, benzimidazole, and triazine may be used.

For example, the hole blocking layer 265 is 2,9-dimethyl-4,7-di, which has a lower highest occupied molecular orbital (HOMO) energy level compared to the material used for the light emitting material layer 260. phenyl-1,10-phenanthroline (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline; BCP), BAlq, Alq3, PBD, spiro-PBD, and/or Liq. .

Since the organic light emitting diode 200 according to the second embodiment of the present invention has a dopant having a delayed fluorescence characteristic in the light emitting material layer 260, the light emitting efficiency is improved. In addition, the light emitting material layer 260 includes a host made of organic compounds represented by Chemical Formulas 1 to 3.

When the organic compound represented by Chemical Formulas 1 to 3 is used in the light emitting material layer, a recombination region where electrons and holes meet to form excitons is formed at the center of the light emitting material layer, not at the interface between the light emitting material layer and the hole blocking layer. . Accordingly, exciton quenching due to the interaction between the triplet exciton of the dopant and the surrounding hole-polaron can be minimized, and the life span of the light emitting diode device due to electro-oxidation and photo-oxidation can be prevented from deteriorating. there is. In addition, since at least one of the bipyridine moiety and/or the aromatic ring is substituted with a cyano group in the organic compound of the present invention, the energy band gap and the excited state triplet energy level (T ₁ ) do not decrease, and the luminous efficiency is improved. It is possible to implement the organic light emitting diode 200 having improved color purity and excellent color purity while a blue transition is achieved.

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 or 265, the charge transport layers 250 or 270 adjacent to the light emitting material layer 260 By preventing light emission at the interface with the organic light emitting diode 200, the light emitting efficiency and life of the device can be further improved.

The organic light emitting diode according to the present invention may be applied to an organic light emitting device such as an organic light emitting diode display device or a lighting device to which the above organic light emitting diode is applied. As an example of the organic light emitting device according to the present invention, a display device to which the organic light emitting diode described above 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.

As shown in FIG. 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 a planarization layer 360 on and an organic light emitting diode 400 connected to the 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. 3, the driving thin film has a coplanar structure. Indicates the transistor Td.

The substrate 302 may be a glass substrate, a thin flexible substrate, or a polymeric plastic substrate. For example, flexible substrates include polyimide (PI), polyethersulfone (PES), polyethylenenaphthalate (PEN), polyethylene terephthalate (PET) and polycarbonate (PC). It can be formed by any one of them. The driving thin film transistor (Td), which is a driving element, and the substrate 302 on which the organic light emitting diode 400 are positioned form 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, and the light-shielding pattern prevents light from entering the semiconductor layer 310 so that the semiconductor layer 310 is not exposed to light. prevent degradation by Alternatively, the semiconductor layer 310 may be made of polycrystalline silicon, and in this case, both edges of the semiconductor layer 310 may be doped with impurities.

A gate insulating film 320 made of an insulating material is formed on the entire surface of the substrate 302 on the semiconductor layer 310 . The gate insulating layer 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 top of the gate insulating film 320 to correspond to the center of the semiconductor layer 310 . In addition, a gate wiring (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 . Meanwhile, although the gate insulating film 320 is formed on the entire surface of the substrate 302 , the gate insulating film 320 may be patterned in 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 above 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 (SiNx), or an organic insulating material such as benzocyclobutene or photo-acryl. there is.

The interlayer insulating film 340 has first and second semiconductor layer contact holes 342 and 344 exposing top surfaces of both sides of the semiconductor layer 310 . The first and second semiconductor layer contact holes 342 and 344 are spaced 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 layer 320 . In contrast, 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 film 340 . In addition, a data wire (not shown), a power supply wire (not shown), and a second capacitor electrode (not shown) may be formed on the interlayer insulating film 340 and extend along the second direction.

The source electrode 352 and the drain electrode 354 are spaced apart from each other with respect to the gate electrode 330, and both sides of the semiconductor layer 310 and each other through the first and second semiconductor layer contact holes 342 and 344, respectively. make contact Although not shown, the data line extends along the second direction and intersects the gate line to define a pixel area, and the power line supplying a high potential voltage is spaced apart from the data line. The second capacitor electrode is connected to the drain electrode 354 and overlaps the first capacitor electrode, so that the interlayer insulating film 340 between the first and second capacitor electrodes serves as a dielectric layer to form a storage capacitor.

Meanwhile, the semiconductor layer 310, the gate electrode 330, the source electrode 352, and the drain electrode 354 form 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 positioned on a semiconductor layer 310 . Alternatively, the driving thin film transistor Td may have an inverted staggered structure in which a gate electrode is positioned below the semiconductor layer and a source electrode and a drain electrode are positioned above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.

In addition, 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 the drain electrode (not shown) of the switching thin film transistor (not shown), and the source electrode 352 of the driving thin film transistor (Td) is connected to a power wiring (not shown). Connected. In addition, the gate electrode (not shown) and the source electrode (not shown) of the switching thin film transistor (not shown) are respectively connected to the gate wiring and the data wiring.

Meanwhile, the organic light emitting diode display 300 may include a color filter (not shown) absorbing light generated by the organic light emitting diode 400 . For example, a color filter (not shown) may absorb red (R), green (G), blue (B), and white (W) light. In this case, red, green, and blue color filter patterns that absorb light may be separately formed for each pixel area, and each of these color filter patterns is an organic light emitting diode (OLED) that emits light of a wavelength band to be absorbed. 400) may be disposed to overlap each other with the organic light emitting layer 430. By adopting a color filter (not shown), the organic light emitting diode display 300 can implement full-color.

For example, when the organic light emitting diode display device 300 is a bottom emission type, a color filter (not shown) absorbing light may be positioned above the interlayer insulating layer 340 corresponding to the organic light emitting diode 400. . In an optional embodiment, when the organic light emitting diode display device 300 is a top emission type, the color filter may be positioned above the organic light emitting diode 400, that is, above the second electrode 420.

A planarization layer 360 is formed on the entire surface of the substrate 302 on the source electrode 352 and the drain electrode 354 . The planarization layer 360 has a flat upper surface and has a drain contact hole 362 exposing the drain electrode 354 of the driving thin film transistor Td. Here, the drain contact hole 362 is illustrated as being formed right above the second semiconductor layer contact hole 344, but may be formed spaced apart from the second semiconductor layer contact hole 344.

The light emitting diode 400 includes a first electrode 410 positioned on the planarization layer 360 and connected to the drain electrode 354 of the driving thin film transistor Td, and an organic layer sequentially stacked on the first electrode 410. A light emitting layer 430 and a second electrode 420 are included.

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

Meanwhile, when the organic light emitting diode display 300 of the present invention is a top-emission type, a reflective electrode or a reflective layer may be further formed below the first electrode 310 . For example, the reflective electrode or the reflective layer may be made of an aluminum-palladium-copper (APC) alloy.

In addition, a bank layer 370 covering an 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 area.

An organic emission 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 light-emitting material layers. On the other hand, as shown in FIGS. 3 and 4 , the organic light emitting layer 430 includes multiple layers such as a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting material layer, a hole blocking layer, an electron transport layer, and/or an electron injection layer. It may be made of an organic material layer of.

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 located on the front surface of the display area and is made of a conductive material having a relatively low work function value and can be used as a cathode. For example, the second electrode 420 is made of any one of aluminum (Al), magnesium (Mg), calcium (ca), silver (Ag), or an alloy or combination thereof such as an aluminum-magnesium alloy (AlMg). can

An encapsulation film 380 is formed on the second electrode 420 to prevent penetration of external moisture into the organic light emitting diode 400 . The encapsulation film 380 may have a stacked 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, since the organic light emitting diode 400 has a dopant having a delayed fluorescence characteristic in the organic light emitting layer 430, light emitting efficiency is improved. In addition, the organic light emitting layer 430 includes organic compounds represented by Chemical Formulas 1 to 3 as a host.

When the organic compounds represented by Chemical Formulas 1 to 3 are used in the light emitting material layer, a recombination region where electrons and holes meet to form excitons is formed in the center of the light emitting material layer. Exciton quenching due to the interaction between the triplet excitons of the dopant and the surrounding holes-polarons is minimized, thereby preventing the lifespan of the light emitting diode device from deteriorating. In addition, since at least one of the bipyridine moiety and/or the aromatic ring is substituted with a cyano group in the organic compound of the present invention, the energy band gap and the excited state triplet energy level (T _1h ) do not decrease, and the blue transition can be implemented. Therefore, by applying the organic compounds represented by Chemical Formulas 1 to 3 to the organic light emitting layer 430, the color purity and luminous efficiency of the organic light emitting diode 400 and the organic light emitting diode display 300 may be improved, and device lifespan may be improved. can improve

Hereinafter, the present invention will be described in more detail through exemplary examples, but the present invention is not limited to the technical idea described in the following examples.

synthesis example 1: Synthesis of Compound 1

1) Synthesis of Compound 1B

Under a nitrogen environment (N ₂ purging), 1A and 0.8 equivalents of CuCN were put into dimethyl formamide (DMF) and stirred at 150°C. After 14 hours, the reactant was slowly poured into ice water at 0°C, stirred for 30 minutes, and extracted with aqueous ammonia. After removing the solvent from the solvent layer and adsorbing it to silica, 1B as an ivory solid was obtained after a column using MC: Hexane (1:3) as a developing solvent.

2) Synthesis of Compound 1

In a nitrogen environment (N ₂ purging), 1B, 2.2 equivalents of 1C, 0.1 equivalents of Tris(dibenzylideneacetone)dipalladium(0)(Pd ₂ (dba) ₃ ), 0.2 equivalents of triphenylphosphine, 4.0 equivalents of sodium tert-butoxide were mixed with Toluene. and stirred in a 100° C. oil bath. After 16 hours, water was added to the reaction mixture, and after extraction, compound 1 was obtained as a white solid after column using Hexane: MC (2:1) as a developing solvent. The results of NMR analysis of synthesized Compound 1 are shown in FIG. 6 .

synthesis example 2: Synthesis of Compound 2

1) Synthesis of Compound 2C

In a nitrogen environment (N ₂ purging), 2A, 0.6 equivalent of 2B, 0.1 equivalent of CuI, 3.5 equivalent of diaminocyclohexane, and 4.0 equivalent of potassium phosphate were added to 1,4-dioxane and stirred in a 90° C. oil bath. After 12 hours, water was added to the reactant, and after extraction, 2C was obtained as a white solid after column using Hexane:MC (5:1) developing solvent.

2) Compound 2D synthesis

In a nitrogen environment (N ₂ purging), 2C, 1.5 equivalents of Bu—Li was added to ether and stirred at -78°C. After the reaction for 2 hours, 1.2 equivalents of Trimethyl borate was added, stirred at -78 ° C for 30 minutes, and then the reaction temperature was raised to room temperature by removing the dry ice bath. After 8 hours of reaction, 30 ml of HCl in DI water was added and the organic solvent was removed. 2D, a white solid precipitated in water after all the organic solvents were removed, was obtained by filtering.

3) Synthesis of Compound 2

Under a nitrogen environment (N ₂ purging), 1B, 2.3 equivalents of 2D, 0.1 equivalents of Pd ₂ (dba) ₃ , and 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reaction mixture, and after extraction, Compound 2 was obtained as a white solid after column using Hexane:EA (7:1) as a developing solvent. The results of NMR analysis of the synthesized compound 2 are shown in FIG. 7 .

synthesis example 3: Synthesis of Compound 3

1) 3B compound synthesis

In a nitrogen environment (N ₂ purging), 3A and 0.8 equivalents of CuCN were added to DMF and stirred at 150°C. After 48 hours, the reactant was slowly poured into ice water at 0 ° C, stirred for 30 minutes, and then extracted with aqueous ammonia. After removing the solvent from the solvent layer and adsorbing it to silica, ivory solid 3B was obtained after column using MC: Hexane (1:1) developing solvent.

2) Synthesis of Compound 3

In a nitrogen environment (N ₂ purging), 3B, 2.2 equivalents of 1C, 0.1 equivalents of Pd ₂ (dba) ₃ , 0.2 equivalents of triphenylphosphine, and 4.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 16 hours, water was added to the reactant, and after extraction, Hexane: MC (2: 1) was used as a developing solvent to obtain Compound 3 as a white solid after column.

synthesis example 4: synthesis of compound 4

Under a nitrogen environment (N ₂ purging), 3B, 2.3 equivalents of 2D, 0.1 equivalents of Pd ₂ (dba) ₃ , and 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reaction mixture, and after extraction, Hexane: EA (7: 1) was used as a developing solvent to obtain Compound 4 as a white solid after column.

synthesis example 5: Synthesis of Compound 5

1) Synthesis of Compound 5B

In a nitrogen environment (N ₂ purging), 5A and 1.9 equivalents of CuCN were added to DMF and stirred at 150°C. After 24 hours, the reactant was slowly poured into ice water at 0 ° C, stirred for 30 minutes, and then extracted with aqueous ammonia. After removing the solvent from the solvent layer and adsorbing it to silica, ivory solid 5B was obtained after column using MC: Hexane (3:2) developing solvent.

2) Synthesis of Compound 5

In a nitrogen environment (N ₂ purging), 5B, 2.2 equivalents of 1C, 0.1 equivalents of Pd ₂ (dba) ₃ , 0.2 equivalents of triphenylphosphine, and 4.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 24 hours, water was added to the reaction mixture, and after extraction, Hexane: MC (1:1) was used as a developing solvent to obtain Compound 5 as a white solid after column.

synthesis example 6: synthesis of compound 6

Under a nitrogen environment (N ₂ purging), 5B, 2.3 equivalents of 2D, 0.1 equivalents of Pd ₂ (dba) ₃ , 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reactant, and after extraction, Hexane: EA (4: 1) was used to obtain a white solid compound 6 after column using a developing solvent.

synthesis example 7: synthesis of compound 7

1) Synthesis of Compound 7B

In a nitrogen environment (N ₂ purging), 7A and 2.8 equivalents of CuCN were added to DMF and stirred at 150°C. After 36 hours, the reactant was slowly poured into ice water at 0 ° C, stirred for 30 minutes, and then extracted with aqueous ammonia. After removing the solvent from the solvent layer and adsorbing it to silica, ivory solid 7B was obtained after column using MC developing solvent.

2) Synthesis of Compound 7

In a nitrogen environment (N ₂ purging), 7B, 2.2 equivalents of 1C, 0.1 equivalents of Pd ₂ (dba) ₃ , 0.2 equivalents of triphenylphosphine, and 4.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in a 100°C oil bath. After 26 hours, water was added to the reactant, and after extraction, Hexane: MC (2:3) was used to obtain a white solid compound 7 after column using a developing solvent.

synthesis example 8: Synthesis of Compound 8

Under a nitrogen environment (N ₂ purging), 7B, 2.3 equivalents of 2D, 0.1 equivalents of Pd ₂ (dba) ₃ , 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 27 hours, water was added to the reaction mixture, and after extraction, Hexane: EA (2:1) was used as a developing solvent to obtain Compound 8 as a white solid after column.

synthesis example 9: synthesis of compound 9

1) Synthesis of Compound 9B

In a nitrogen environment (N ₂ purging), 9A and 3.9 equivalents of CuCN were added to DMF and stirred at 150°C. After 72 hours, the reactant was slowly poured into ice water at 0 ° C, stirred for 30 minutes, and then extracted with aqueous ammonia. After removing the solvent from the solvent layer and adsorbing it to silica, ivory solid 9B was obtained after column using MC:EA (1:1) developing solvent.

2) Synthesis of compound 9

In a nitrogen environment (N ₂ purging), 9B, 2.2 equivalents of 1C, 0.1 equivalents of Pd ₂ (dba) ₃ , 0.2 equivalents of triphenylphosphine, and 4.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 26 hours, water was added to the reactant, and after extraction, a white solid compound 9 was obtained after column using Hexane:MC (2:7) developing solvent.

synthesis example 10: synthesis of compound 10

Under a nitrogen environment (N ₂ purging), 9B, 2.3 equivalents of 2D, 0.1 equivalents of Pd ₂ (dba) ₃ , 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 32 hours, water was added to the reaction mixture, and after extraction, Hexane: EA (1:1) was used as a developing solvent to obtain Compound 10 as a white solid after column.

synthesis example 11: synthesis of compound 11

1) Synthesis of Compound 11B

In a nitrogen environment (N ₂ purging), 11A and 1.5 equivalents of CuCN were added to DMF and stirred at 150°C. After 48 hours, the reactant was slowly poured into ice water at 0 ° C, stirred for 30 minutes, and then extracted with aqueous ammonia. After removing the solvent from the solvent layer and adsorbing it to silica, ivory solid 11B was obtained after column using MC: Hexane (1:1) developing solvent.

2) Compound 11 synthesis

In a nitrogen environment (N ₂ purging), 11C, 2.2 equivalents of 11B, 0.1 equivalents of Pd ₂ (dba) ₃ , 0.2 equivalents of triphenylphosphine, and 4.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 16 hours, water was added to the reaction mixture, and after extraction, Hexane: MC (1:1) was used as a developing solvent to obtain Compound 11 as a white solid after column.

synthesis example 12: synthesis of compound 12

1) Synthesis of Compound 12A

2A, 0.6 equivalent of 11B, 0.1 equivalent of CuI, 3.5 equivalent of diaminocyclohexane, and 4.0 equivalent of potassium phosphate were added to 1,4-dioxane under a nitrogen environment (N ₂ purging) and stirred in a 90° C. oil bath. After 12 hours, water was added to the reaction mixture, and after extraction, a white solid 12A was obtained after column using Hexane: MC (5:1) developing solvent.

2) Synthesis of Compound 12B

In a nitrogen environment (N ₂ purging), 12A, 1.5 equivalents of Bu-Li was added to ether and stirred at -78°C. After reacting for 2 hours, 1.2 equivalents of Trimethyl borate was added, stirred at -78 ° C for 30 minutes, and then the reaction temperature was raised to room temperature by removing the dry ice bath. After 8 hours of reaction, 30 ml of HCl in DI water was added and the organic solvent was removed. All organic solvents were removed and 12B as a white solid precipitated in water was obtained by filtering.

3) Synthesis of Compound 12

Under a nitrogen environment (N ₂ purging), 11C, 2.3 equivalents of 12B, 0.1 equivalents of Pd ₂ (dba) ₃ , and 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reaction mixture, and after extraction, Compound 12 was obtained as a white solid after column using Hexane:EA (4:1) as a developing solvent. The results of NMR analysis of the synthesized compound 12 are shown in FIG. 8 .

synthesis example 13: synthesis of compound 13

1) Synthesis of Compound 13A

In a nitrogen environment (N ₂ purging), 1B, 0.6 equivalent of 11B, 0.05 equivalent of Pd ₂ (dba) ₃ , 0.1 equivalent of triphenylphosphine, and 3.0 equivalent of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 12 hours, water was added to the reaction mixture, and after extraction, Hexane: MC (2: 1) was used as a developing solvent to obtain 13A as a white solid.

2) Synthesis of compound 13

In a nitrogen environment (N ₂ purging), 13A, 1.2 equivalents of 1C, 0.05 equivalents of Pd ₂ (dba) ₃ , 0.1 equivalents of triphenylphosphine, and 3.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 15 hours, water was added to the reactant, and after extraction, Hexane: MC (2: 1) was used as a developing solvent to obtain Compound 13 as a white solid after column.

synthesis example 14: synthesis of compound 14

1) Synthesis of Compound 14A

Under a nitrogen environment (N ₂ purging), 1B, 0.6 equivalent of 2D, 0.05 equivalent of Pd ₂ (dba) ₃ , 4.0 equivalent of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reaction mixture, and after extraction, Hexane: EA (7: 1) was used as a developing solvent to obtain 14A as a white solid.

2) Synthesis of Compound 14

Under a nitrogen environment (N ₂ purging), 14A, 1.3 equivalents of 12B, 0.05 equivalents of Pd ₂ (dba) ₃ , and 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reactants, and after extraction, Hexane: EA (5: 1) was used as a developing solvent to obtain Compound 14 as a white solid after column.

synthesis example 15: synthesis of compound 15

1) Synthesis of Compound 15A

Under a nitrogen environment (N ₂ purging), 3B, 0.6 equivalent of 11B, 0.05 equivalent of Pd ₂ (dba) ₃ , 0.1 equivalent of triphenylphosphine, and 3.0 equivalent of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 12 hours, water was added to the reaction mixture, and after extraction, Hexane: MC (2:1) was used as a developing solvent to obtain 15A as a white solid.

2) Synthesis of Compound 15

In a nitrogen environment (N ₂ purging), 15A, 1.2 equivalents of 1C, 0.05 equivalents of Pd ₂ (dba) ₃ , 0.1 equivalents of triphenylphosphine, and 3.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 15 hours, water was added to the reaction mixture, and after extraction, Hexane: MC (2:1) was used to obtain Compound 15 as a white solid after column using a developing solvent.

synthesis example 16: synthesis of compound 16

1) Synthesis of Compound 16A

Under a nitrogen environment (N ₂ purging), 3B, 0.7 equivalent of 2D, 0.1 equivalent of Pd ₂ (dba) ₃ , 4.0 equivalent of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reaction mixture, and after extraction, Hexane: EA (7: 1) was used as a developing solvent to obtain 16A as a white solid.

2) Synthesis of compound 16

Under a nitrogen environment (N ₂ purging), 16A, 1.2 equivalents of 12B, 0.1 equivalents of Pd ₂ (dba) ₃ , and 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 32 hours, water was added to the reaction mixture, and after extraction, Hexane: EA (5: 1) was used as a developing solvent to obtain Compound 16 as a white solid.

synthesis example 17: synthesis of compound 17

1) 17B compound synthesis

In a nitrogen environment (N ₂ purging), 17A and 1.8 equivalents of CuCN were added to DMF and stirred at 150°C. After 36 hours, the reactant was slowly poured into ice water at 0 ° C, stirred for 30 minutes, and then extracted with aqueous ammonia. After removing the solvent from the solvent layer and adsorbing it to silica, ivory solid 17B was obtained after column using MC: Hexane (3:2) developing solvent.

2) Synthesis of Compound 17

In a nitrogen environment (N ₂ purging), 17B, 2.2 equivalents of 1C, 0.1 equivalents of Pd ₂ (dba) ₃ , 0.2 equivalents of triphenylphosphine, and 4.0 equivalents of sodium tert-butoxide were added to Toluene and stirred in an oil bath at 100°C. After 16 hours, water was added to the reactant, and after extraction, Hexane: MC (1:1) was used to obtain a white solid compound 17 after column using a developing solvent.

synthesis example 18: synthesis of compound 18

Under a nitrogen environment (N ₂ purging), 17B, 2.3 equivalents of 2D, 0.1 equivalents of Pd ₂ (dba) ₃ , and 4.0 equivalents of potassium carbonate were added to Toluene and stirred in an 80° C. oil bath. After 24 hours, water was added to the reaction mixture, and after extraction, Hexane: EA (4: 1) was used as a developing solvent to obtain Compound 18 as a white solid after column.

Example 1: compound 1 was applied organic light emitting diode produce

An organic light emitting diode was fabricated using Compound 1 as a host for the light emitting material layer. First, a 40 mm x 40 mm x 0.5 mm thick ITO (including reflector) electrode-attached glass substrate was ultrasonically cleaned with isopropyl alcohol, acetone, and DI water for 5 minutes, and then dried in an oven at 100 °C. After cleaning the substrate, it was treated with O ₂ plasma for 2 minutes in a vacuum state and transferred to a deposition chamber to deposit other layers thereon. Organic layers were deposited in the following order by evaporation from a heating boat under a vacuum of about 10 ⁻⁷ Torr.

A hole injection layer (NPB, 50 Å), a hole transport layer (mCP, 500 Å), an electron blocking layer (mCBP, 100 Å), a light emitting material layer (Compound 1 is used as a host and the material of Formula 4 is 30% by weight doped, 250Å), electron transport layer (TPBI, 300Å), electron injection layer (LiF), cathode (Al).

After forming a capping layer (CPL), it was encapsulated with glass. After deposition of these layers, they were transferred from the deposition chamber into a dry box for film formation and subsequently encapsulated using UV curing epoxy and a moisture getter.

Example 2: Compound 2 was applied organic light emitting diode produce

An organic light emitting diode was fabricated by repeating the procedure of Example 1 except for using Compound 2 instead of Compound 1 as a host of the light emitting material layer.

Example 3: Compound 12 was applied organic light emitting diode produce

An organic light emitting diode was manufactured by repeating the procedure of Example 1, except that Compound 12 was used instead of Compound 1 as a host of the light emitting material layer.

comparative example : organic light emitting diode produce

An organic light emitting diode was manufactured by repeating the procedure of Example 1, except that the material represented by Chemical Formula 5 was used instead of Compound 1 as a host of the light emitting material layer.

Formula 5

Experimental example : organic light emitting diode Measurement of luminescence properties

Physical properties were measured for the organic light emitting diodes manufactured in Examples 1 to 3 and Comparative Example, respectively. 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). Table 1 shows the measurement results of current efficiency, power efficiency, external quantum efficiency (EQE), CIE color coordinates, and life time (T ₉₅ ) falling from 100% to 95% at a constant current based on 300 nit luminance of the manufactured organic light emitting diode. .

Physical Properties of Organic Light-Emitting Diodes device current efficiency
(Cd/A) power efficiency
(lm/W) EQE
(%) CIE
(X) CIE
(Y) T95
(hr) Example 1 24.12 19.77 11.12 0.152 0.220 32 Example 2 26.30 20.91 13.23 0.157 0.232 45 Example 3 25.31 20.43 13.17 0.150 0.231 43 comparative example 23.03 19.69 12.88 0.161 0.297 5.5

As shown in Table 1, compared to the case where the organic compound of Comparative Example was used as a host of the light emitting material layer, when the organic compound synthesized according to the present invention was used as a host of the light emitting material layer, the current efficiency was up to 14.2%, the power Efficiency improved by up to 6.1% and external quantum efficiency by up to 2.7%. In particular, device lifespan increased by a minimum of 4.8 times and a maximum of 7.2 times. In addition, it was confirmed from the color coordinates that high color purity blue can be obtained when the organic compound of the present invention is used as a host. As a result, by applying the organic compound of the present invention to the organic light emitting layer, it is possible to manufacture an organic light emitting diode with improved light emitting efficiency and significantly improved color purity and lifespan. Accordingly, the organic light emitting diode to which the organic compound of the present invention is applied can be used for a light emitting device such as an organic light emitting diode display and/or a lighting device.

In the above, the present invention has been described based on exemplary embodiments and examples of the present invention, but the scope of the present invention is not limited to the technical idea described in the embodiments and examples. Those skilled in the art to which the present invention pertains can easily consider various modifications and changes based on the above-described embodiments and examples. However, it is clear through the appended claims that all of these modifications and changes fall within the scope of the present invention.

100, 200, 400: organic light emitting diode 110, 210, 410: first electrode
120, 220, 420: second electrode 130, 230, 430: organic light emitting 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

Claims (22)

An organic compound represented by Formula 1 below.
Formula 1

(In Formula 1, R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a tritium atom or a cyano group (—CN); R ₅ and R ₆ are each independently unsubstituted or substituted C ₅ to C ₃₀ An aryl group or an unsubstituted or substituted C ₄ ~C ₃₀ heteroaryl group, wherein the C ₅ ~C ₃₀ aryl group is each independently an unsubstituted or substituted biphenyl group, a terphenyl group, a naphthyl group, anthracenyl group, or a pentanrenyl group. , indenyl group, indenoidinyl group, heptalenyl group, biphenylenyl group, indacenyl group, phenalenyl group, phenanthrenyl group, benzophenanthrenyl group, dibenzophenanthrenyl group, azulenyl group, pyrenyl group, fluoro Lanthenyl group, triphenylenyl group, chrysenyl group, tetraphenyl group, tetracenyl group, playdaenyl group, phicenyl group, pentaphenyl group, pentacenyl group, fluorenyl group, indenofluorenyl group or spiro fluorene and the C ₄ ~C ₃₀ heteroaryl group is each independently an unsubstituted or substituted pyrrolyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a tetrazinyl group, an imidazolyl group, and a pyrazole group. diyl, indole group, isoindole group, indazole group, indolizinyl group, pyrrozinyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, Benzofurocarbazolyl group, benzothienocarbazolyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group, quinazolinyl group, quinozolinyl group, quinolizinyl group, fury Nyl group, phthalazinyl group, quinoxalinyl group, benzoquinolinyl group, benzoisoquinolinyl group, benzoquinazolinyl group, benzoquinoxalinyl group, acridinyl group, phenanthrolinyl group, perimidinyl group, phenanthridinyl group, fr Teridinyl group, cinnolinyl group, naphtharidinyl group, furanyl group, pyranyl group, oxazinyl group, oxazolyl group, oxadiazolyl group, triazolyl group, dioxynyl group, benzofuranyl group, dibenzofuranyl group, thio Pyranyl group, xanthenyl group, chromenyl group, isochromenyl group, thioazinyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, difuropyrazinyl group, benzofurodibenzofuranyl group, benzothienobenzo Thiophenyl group, benzothienodibenzothiophenyl group , A benzothienobenzofuranyl group, a benzothienodibenzofuranyl group, or an N-substituted spirofluorenyl group, and when R ₁ to R ₄ are not all cyano groups, at least one selected from R ₅ and R ₆ is A C ₅ ~ C ₃₀ aryl group substituted with a cyano group or a C ₄ ~ C ₃₀ hetero aryl group substituted with a cyano group; L ₁ and L ₂ are each independently an unsubstituted or substituted C ₅ -C ₃₀ arylene group or an unsubstituted or substituted C ₄ -C ₃₀ hetero arylene group; a and b are 0 or 1 respectively)
According to claim 1,
The organic compound represented by Formula 1 is an organic compound represented by Formula 2 below.
Formula 2

(In Formula 2, R ₁ , R ₂ , R ₃ , R ₄ , a, and b are the same as those defined in Formula 1; R ₇ and R ₈ are each independently an unsubstituted or substituted C4~C30 heteroaryl group, and , When R ₁ to R ₄ are not all cyano groups, at least one selected from R ₇ and R ₈ is a substituted C4-C30 heteroaryl group substituted with a cyano group; L ₃ and L ₄ are each independently unsubstituted unsubstituted or substituted C4~C30 hetero arylene group)
According to claim 1,
The organic compound represented by Formula 1 is any one compound represented by Formula 3 below.
Formula 3

a first electrode and a second electrode facing each other; and
An organic light emitting layer positioned between the first electrode and the second electrode,
The organic light emitting layer is an organic light emitting diode including an organic compound represented by Formula 1 below.
Formula 1

(In Formula 1, R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a tritium atom or a cyano group (—CN); R ₅ and R ₆ are each independently unsubstituted or substituted C ₅ to C ₃₀ An aryl group or an unsubstituted or substituted C ₄ ~C ₃₀ heteroaryl group, wherein the C ₅ ~C ₃₀ aryl group is each independently an unsubstituted or substituted biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, and a pentane group. Nyl group, indenyl group, indenoidinyl group, heptalenyl group, biphenylenyl group, indacenyl group, phenalenyl group, phenanthrenyl group, benzophenanthrenyl group, dibenzophenanthrenyl group, azulenyl group, pyrenyl group, Fluoranthenyl group, triphenylenyl group, chrysenyl group, tetraphenyl group, tetracenyl group, playdaenyl group, phycenyl group, pentaphenyl group, pentacenyl group, fluorenyl group, indenofluorenyl group or spiroflu orenyl group, and the C ₄ ~ C ₃₀ heteroaryl group is each independently unsubstituted or substituted pyrrolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, tetrazinyl group, already Dazolyl group, pyrazolyl group, indolyl group, isoindoleyl group, indazolyl group, indolizinyl group, pyrrozinyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, inde Nocarbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group, quinazolinyl group, quinozolinyl group, quinazolinyl group Nolizinyl group, purinyl group, phthalazinyl group, quinoxalinyl group, benzoquinolinyl group, benzoisoquinolinyl group, benzoquinazolinyl group, benzoquinoxalinyl group, acridinyl group, phenanthrolinyl group, perimidinyl group, phenan Tridinyl group, pteridinyl group, sinnolinyl group, naphtharidinyl group, furanyl group, pyranyl group, oxazinyl group, oxazolyl group, oxadiazolyl group, triazolyl group, dioxynyl group, benzofuranyl group, di Benzofuranyl group, thiopyranyl group, xanthenyl group, chromenyl group, isochromenyl group, thioazinyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, difuropyrazinyl group, benzofurodibenzofuranyl group , benzothienobenzothiophenyl group, benzothie A nodibenzothiophenyl group, a benzothienobenzofuranyl group, a benzothienodibenzofuranyl group, or an N-substituted spirofluorenyl group, and when R ₁ to R ₄ are not all cyano groups, selected from R ₅ and R ₆ at least one of which is a C ₅ ~ C ₃₀ aryl group substituted with a cyano group or a C ₄ ~ C ₃₀ heteroaryl group substituted with a cyano group; L ₁ and L ₂ are each independently an unsubstituted or substituted C ₅ -C ₃₀ arylene group or an unsubstituted or substituted C ₄ -C ₃₀ hetero arylene group; a and b are 0 or 1 respectively)
According to claim 4,
The organic light-emitting diode is a compound represented by the following formula (2).
Formula 2

(In Formula 2, R ₁ , R ₂ , R ₃ , R ₄ , a, and b are the same as those defined in Formula 1; R ₇ and R ₈ are each independently an unsubstituted or substituted C4~C30 heteroaryl group, and , When R ₁ to R ₄ are not all cyano groups, at least one selected from R ₇ and R ₈ is a substituted C4-C30 heteroaryl group substituted with a cyano group; L ₃ and L ₄ are each independently unsubstituted unsubstituted or substituted C4~C30 hetero arylene group)
According to claim 4,
The organic compound is an organic light emitting diode used as a host of a light emitting material layer.
According to claim 6,
The light emitting material layer further comprises a dopant organic light emitting diode.
According to claim 7,
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 unoccupied molecular orbital energy level of the host The organic light emitting diode, wherein a difference (|LUMO ^H -LUMO ^D |) between the level (LUMO ^H ) and the lowest level unoccupied molecular orbital energy level (LUMO ^D ) of the dopant is 0.5 eV or less.
According to claim 7,
An organic light-emitting diode having a difference (ΔE _ST ) between an excited state singlet energy level (S ₁ ) and an excited state triplet energy level (T ₁ ) of the dopant is 0.3 eV or less.
Board;
an organic light emitting diode disposed on the substrate and described in any one of claims 4 to 9; and
A driving element located on the substrate and connected to the first electrode of the organic light emitting diode
An organic light emitting device comprising a.
According to claim 10,
The organic light emitting device includes an organic light emitting diode display device. According to claim 2,
The C4-C30 heteroaryl group constituting R ₇ and R ₈ in Formula 2 is selected from the group consisting of a carbazolyl group, an acridinyl group, a dihydroacridinyl group, a furobipyridyl group, and a xanthenyl group, and A zolyl group, an acridinyl group, a dihydroacridinyl group, a furobipyridyl group, and a xanthenyl group are each independently unsubstituted, or a cyano group, a C ₁ ~C ₂₀ alkyl group, a C ₅ ~C ₃₀ aryl group, and a C ₄ ~C An organic compound substituted with at least one of ₃₀ heteroaryl groups.
According to claim 5,
The C ₄ ~C ₃₀ heteroaryl group constituting R ₇ and R ₈ in Formula 2 is selected from the group consisting of a carbazolyl group, an acridinyl group, a dihydroacridinyl group, a furobipyridyl group, and a xanthenyl group, The carbazolyl group, acridinyl group, dihydroacridinyl group, furobipyridyl group, and xanthenyl group are each independently unsubstituted or cyano group, C ₁ ~ C ₂₀ alkyl group, C ₅ ~ C ₃₀ aryl group and C ₄ An organic light emitting diode substituted with at least one of ~C ₃₀ heteroaryl groups.
An organic compound represented by Formula 1 below.
Formula 1

(In Formula 1, R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a tritium atom or a cyano group (-CN), and at least one of R ₁ to R ₄ is a cyano group; R ₅ and R ₆ are Each independently represents an unsubstituted or substituted C ₅ ~C ₃₀ aryl group or an unsubstituted or substituted C ₄ ~C ₃₀ heteroaryl group, wherein the C ₄ ~C ₃₀ heteroaryl group is each independently an unsubstituted or substituted pyrrolyl group. , Pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, tetrazinyl group, imidazolyl group, pyrazolyl group, indolyl group, isoindolyl group, indazolyl group, indolizinyl group, pyrrozinyl group , Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl group, quinolinyl group, isoquinolinyl Group; L ₁ and L ₂ are each independently an unsubstituted or substituted C ₅ ~ C ₃₀ arylene group or an unsubstituted or substituted C ₄ ~ C ₃₀ hetero arylene group; a and b are each 0 or 1)
According to claim 14,
R ₅ and R ₆ in Formula 1 are each independently an unsubstituted or cyano group-substituted C ₅ ~ C ₃₀ aryl group or a cyano group-substituted C ₄ ~ C ₃₀ heteroaryl group.
According to claim 14,
R ₅ and R ₆ in Formula 1 are each independently selected from the group consisting of a carbazolyl group, an acridinyl group, a dihydroacridinyl group, a furobipyridyl group, a fluorenyl group, and a xanthenyl group, and the carbazolyl group , Acridinyl group, dihydroacridinyl group, furobipyridyl group, fluorenyl group, and xanthenyl group are each independently unsubstituted or cyano group, C ₁ ~ C ₂₀ alkyl group, C ₅ ~ C ₃₀ aryl group and C ₄ An organic compound substituted with at least one of ~C ₃₀ heteroaryl groups.
According to claim 14,
The organic compound represented by Formula 1 is an organic compound represented by Formula 2 below.
Formula 2

(In Formula 2, R ₁ , R ₂ , R ₃ , R ₄ , a, and b are the same as those defined in Formula 1; R ₇ and R ₈ are each independently an unsubstituted or substituted C4~C30 heteroaryl group; L ₃ and L ₄ are each independently an unsubstituted or substituted C ₅ ~ C ₃₀ arylene group or an unsubstituted or substituted C ₄ ~ C ₃₀ hetero arylene group)
a first electrode and a second electrode facing each other; and
An organic light emitting layer positioned between the first electrode and the second electrode,
The organic light emitting layer includes an organic light emitting diode comprising an organic compound according to any one of claims 14 to 17.
According to claim 18,
wherein the organic light emitting layer includes a light emitting material layer, and the light emitting material layer includes the organic compound.
Board;
an organic light emitting diode according to claim 18 positioned on the substrate; and
A driving element located on the substrate and connected to the first electrode of the organic light emitting diode
An organic light emitting device comprising a. An organic compound represented by Formula 1 below.
Formula 1

(In Formula 1, R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a tritium atom or a cyano group (—CN); R ₅ and R ₆ are each independently unsubstituted or substituted C ₅ to C ₃₀ An aryl group or an unsubstituted or substituted C ₄ ~C ₃₀ heteroaryl group, wherein the C ₅ ~C ₃₀ aryl group is each independently an unsubstituted or substituted biphenyl group, a terphenyl group, a naphthyl group, anthracenyl group, or a pentanrenyl group. , indenyl group, indenoidinyl group, heptalenyl group, biphenylenyl group, indacenyl group, phenalenyl group, phenanthrenyl group, benzophenanthrenyl group, dibenzophenanthrenyl group, azulenyl group, pyrenyl group, fluoro Lanthenyl group, triphenylenyl group, chrysenyl group, tetraphenyl group, tetracenyl group, playdaenyl group, phicenyl group, pentaphenyl group, pentacenyl group, fluorenyl group, indenofluorenyl group or spiro fluorene and the C ₄ ~C ₃₀ heteroaryl group is each independently an unsubstituted or substituted pyrrolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a tetrazinyl group, and an imidazole group. diary, pyrazolyl group, indolyl group, isoindoleyl group, indazoyl group, indolizinyl group, pyrrozinyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indeno Carbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group, quinazolinyl group, quinozolinyl group, quinoly Jinyl group, purinyl group, phthalazinyl group, quinoxalinyl group, benzoquinolinyl group, benzoisoquinolinyl group, benzoquinazolinyl group, benzoquinoxalinyl group, acridinyl group, phenanthrolinyl group, perimidinyl group, phenantri Denyl group, pteridinyl group, sinnolinyl group, naphtharidinyl group, furanyl group, pyranyl group, oxazinyl group, oxazolyl group, oxadiazolyl group, triazolyl group, dioxynyl group, benzofuranyl group, dibenzo Furanyl group, thiopyranyl group, xanthenyl group, chromenyl group, isochromenyl group, thioazinyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, difuropyrazinyl group, benzofurodibenzofuranyl group, Benzothienobenzothiophenyl group, benzothienodi A benzothiophenyl group, a benzothienobenzofuranyl group, a benzothienodibenzofuranyl group, or an N-substituted spirofluorenyl group, and when R ₁ to R ₄ are not all cyano groups, R ₅ and R ₆ are selected from At least one is a C ₅ ~ C ₃₀ aryl group substituted with a cyano group or a C ₄ ~ C ₃₀ hetero aryl group substituted with a cyano group; L ₁ and L ₂ are each independently an unsubstituted or substituted C ₅ ~ C ₃₀ arylene group or an unsubstituted or substituted C ₄ ~ C ₃₀ hetero arylene group, and the C ₄ ~ C ₃₀ hetero arylene group is each independently unsubstituted or substituted Pyrrolylene, imidazolylene, pyrazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene ( isoindolylene), indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, Phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, benzoquinolinylene group, benzoisoquinolinylene group, benzoquinazolinylene group , Benzoquinoxalinylene group, cinnolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group (benzoxazolylene), benzimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene, Isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetrazolyne, oxadiazolylene, triazinylene (triazinylene), benzofuranylene group, dibenzofuranylene group, benzofurodibenzofuranylene group, benzothienobenzofuranylene group, benzothieno Dibenzofuranylene group, benzothiophenylene group, dibenzothiophenylene group, benzothietobenzothiophenylene group, benzothienodibenzothiophenylene group, carbazolylene group, benzocarbazolylene group, dibenzocarbazolylene group A group consisting of an indolocarbazolylene group, an indenocarbazolylene group, a benzofurocarbazolylene group, a benzothienocarbazolylene group, an imidazopyrimidinylene group and an imidazopyridinylene group selected from; a and b are each 1)
An organic compound represented by Formula 1 below.
Formula 1

(In Formula 1, R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a tritium atom or a cyano group (-CN), and at least one of R ₁ to R ₄ is a cyano group; R ₅ and R ₆ are Each independently represents an unsubstituted or substituted C ₅ -C ₃₀ aryl group or an unsubstituted or substituted C ₄ -C ₃₀ heteroaryl group; L ₁ and L ₂ are each independently an unsubstituted or substituted C ₅ -C ₃₀ aryl group A rene group or an unsubstituted or substituted C ₄ ~ C ₃₀ heteroarylene group, wherein the C ₄ ~ C ₃₀ heteroarylene group is each independently unsubstituted or substituted Pyrrolylene, imidazolylene, pyrazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene ( isoindolylene), indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, Phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, benzoquinolinylene group, benzoisoquinolinylene group, benzoquinazolinylene group , Benzoquinoxalinylene group, cinnolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group (benzoxazolylene), benzimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene, Isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetrazolyne, oxadiazolylene, triazinylene (triazinylene), benzofuranylene group, dibenzofuranylene group, benzofurodibenzofuranylene group, benzothienobenzofuranylene group, benzothieno Dibenzofuranylene group, benzothiophenylene group, dibenzothiophenylene group, benzothietobenzothiophenylene group, benzothienodibenzothiophenylene group, carbazolylene group, benzocarbazolylene group, dibenzocarbazolylene group A group consisting of an indolocarbazolylene group, an indenocarbazolylene group, a benzofurocarbazolylene group, a benzothienocarbazolylene group, an imidazopyrimidinylene group and an imidazopyridinylene group selected from; a and b are each 1)

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