KR102649050B1 - Organic compound and light emitting diode and organic light emitting diode display device using the same - Google Patents

Abstract

The present invention relates to an organic compound in which at least one diphenylmethylenefluorenyl group is directly or indirectly linked to a nitrogen atom constituting at least one amine group. The organic compound according to the present invention has excellent hole injection characteristics and/or hole transport characteristics and excellent thermal stability. Therefore, when the organic compound of the present invention is used in the hole layer, electron blocking layer, and/or charge generation layer of a light emitting device, the light emitting device can be driven by securing sufficient current density at a low voltage. Even if the temperature rises as the light-emitting device is driven, the compound of the present invention does not deform or deteriorate, and can reduce stress applied to the light-emitting device by low-voltage driving. Therefore, by applying the organic compound of the present invention, light emitting diodes and display devices with good luminous efficiency can be implemented.

Description

Organic compounds and light emitting diodes and organic light emitting diode display devices using the same {ORGANIC COMPOUND AND LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITTING DIODE DISPLAY DEVICE USING THE SAME}

The present invention relates to organic compounds used in organic light-emitting diodes, and more specifically, to organic compounds with excellent hole injection and transport properties and excellent thermal stability, and light-emitting diodes and organic compounds with improved light-emitting properties using these organic compounds. It is about a light emitting diode display device.

Recently, as display devices have become larger, the demand for flat display devices that occupy less space is increasing. One of these flat display devices is an organic light emitting diode display, which includes a light emitting diode and is also called an organic electroluminescent device (OELD). The technology of organic light emitting diode (OLED) display devices is developing at a rapid pace.

A light-emitting diode is a device that emits light when charge is injected into the organic light-emitting layer formed between the electron injection electrode (cathode) and the hole injection electrode (anode), the electrons and holes pair and then disappear. Not only can devices be formed on flexible transparent substrates such as plastic, but they also have the advantage of being able to operate at low voltages (less than 10V), relatively low power consumption, and excellent color purity.

The light emitting diode used in the organic light emitting diode display device is made by injecting charge into the light emitting layer of organic material formed between the electron injection electrode (cathode) and the hole injection electrode (anode), forming a pair of electrons and holes. It is an element that emits light as it dies. In the organic light-emitting layer, electrons and holes meet to form an exciton, and this energy causes the organic compound contained in the organic light-emitting layer to enter an excited state. The organic compound changes energy from the excited state to the ground state. A transition occurs, and the generated energy is emitted as light and emits light.

The organic light-emitting layer may have a single-layer structure of the light-emitting material layer, or may have a multi-layer structure to improve light emission efficiency. For example, the organic light-emitting layer includes a hole injection layer (HIL), a hole transporting layer (HTL), an emitting material layer (EML), an electron transporting layer (ETL), and It may have a multilayer structure composed of an electron injection layer (EIL).

Meanwhile, in order to further improve the performance of the light emitting diode and implement a white light emitting diode, a light emitting diode having a tandem structure manufactured by stacking a plurality of unit devices has been proposed. This tandem structure light emitting diode includes a charge generation layer (CGL) disposed between each unit element to supply positive and negative charges to each unit element, respectively.

Organic materials used in organic light-emitting diodes, including tandem structure organic light-emitting diodes, can be largely divided into light-emitting materials and charge transport materials, and charge transport materials include hole injection materials, hole transport materials, electron transport materials, and electron injection materials. It can be classified by material, etc. In organic light-emitting diodes, high driving voltage and current density apply strong stress to the materials that make up the device, which can adversely affect the stability of the material and the lifespan of the device.

Therefore, research is being conducted to increase the efficiency of the light emitting diode and reduce power consumption by adjusting the energy level of the charge transport layer or charge injection layer that constitutes the organic light emitting diode. For example, Korean Patent Publication No. 10-2010-0103837 describes that poly(norbornene) polymer obtained from norbornene monomer having a carbazole side chain can be applied to the hole transport layer using a solution process.

However, there is still a need for the development of materials that can improve the luminous efficiency of the light-emitting device by improving the current density of the light-emitting device, reducing the driving voltage, and reducing stress on the materials constituting the light-emitting device.

The purpose of the present invention is to provide an organic compound with excellent hole injection and/or hole transport properties and improved thermal stability.

Another object of the present invention is to provide a light emitting diode and organic light emitting diode device that can be driven at low voltage, has less stress on the materials constituting the light emitting device, has improved lifespan of the light emitting device, and has improved luminous efficiency.

According to one aspect of the present invention having the above-described object, the present invention provides an organic compound in which a diphenylmethylenefluorenyl group is directly or indirectly linked to a nitrogen atom constituting at least one amine group.

In one alternative embodiment, the other substituent linked to the amine group may have a condensed aromatic ring.

According to another aspect of the present invention, the present invention also includes a light emitting diode in which the organic compound is applied to an organic material layer, for example, a common layer such as a hole layer, a charge generation layer, and/or an exciton blocking layer, and the light emitting diode as a light emitting device. An organic light emitting diode display device is provided.

The organic compound of the present invention has at least one amine group with excellent hole binding ability and thus has excellent hole injection and hole transport properties.

Since the diphenylmethylene fluorenyl group is directly or indirectly connected to the nitrogen atom constituting at least one amine group, and optionally another condensed aromatic ring is connected, the thermal stability of the organic compound of the present invention can be improved.

Therefore, the organic compound of the present invention can be applied alone or as a host to an organic material layer requiring hole injection and/or hole transport characteristics, hole generation characteristics, and/or electron blocking characteristics in a light emitting diode.

For example, the light emitting diode and organic light emitting diode display device having a single layer structure including a hole layer and/or an electron blocking layer made of an organic compound of the present invention have a good current density and can be driven even at a low voltage, so they emit light. The power consumption of the diode or display device can be reduced. Due to the low-voltage driving characteristics, there is no need to apply a high voltage to the light-emitting diode to which the organic compound according to the present invention is applied, thereby reducing the stress applied to the material constituting the light-emitting diode.

In addition, because the organic compound of the present invention has excellent thermal stability, the organic compound of the present invention is not deformed or deteriorated even when the temperature rises when the light emitting diode is driven. Accordingly, the lifespan of the light-emitting device to which the organic compound according to the present invention is applied can be improved, and the luminous efficiency of the light-emitting device can be improved.

In addition, the tandem structure light emitting diode and organic light emitting diode display device including a charge generation layer and/or an electron blocking layer made of an organic compound of the present invention have reduced power consumption, improved device life, and luminous efficiency by low-voltage driving. It has the advantage of being able to achieve high purity white color.

1 is a cross-sectional view schematically showing a light emitting diode having a single-layer structure to which an organic compound according to a first exemplary embodiment of the present invention can be applied.
Figure 2 is a cross-sectional view schematically showing a light emitting diode having a single-layer structure to which an organic compound according to a second exemplary embodiment of the present invention can be applied.
Figure 3 is a cross-sectional view schematically showing a light emitting diode having a tandem structure to which an organic compound according to a third exemplary embodiment of the present invention can be applied.
Figure 4 is a cross-sectional view schematically showing a light emitting diode having a tandem structure to which an organic compound according to a fourth exemplary embodiment of the present invention can be applied.
Figure 5 is a cross-sectional view schematically showing an organic light emitting diode display device including a light emitting diode to which an organic compound can be applied according to an exemplary embodiment of the present invention.
6 to 11 are graphs showing NMR analysis results for organic compounds synthesized according to exemplary embodiments of the present invention, respectively.
Figure 12 is a graph showing the results of Fourier transform mass spectrometry (FT-MS) analysis of an organic compound synthesized according to an exemplary embodiment of the present invention.
13A to 13C show the results of measuring the voltage-current density, current density-luminous efficiency, and wavelength-electroluminescence (EL) intensity of a light emitting diode having a single-layer structure manufactured according to an exemplary embodiment of the present invention, respectively. It's a graph.
14A to 14C show the results of measuring the voltage-current density, current density-luminous efficiency, and wavelength-electroluminescence (EL) intensity of the light emitting diode having a tandem structure manufactured according to an exemplary embodiment of the present invention, respectively. It's a graph.

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

[Organic Compound]

The present invention relates to an organic compound in which at least one diphenylmethylenefluorenyl group is directly or indirectly linked to a nitrogen atom constituting at least one amine group having excellent hole bonding properties. The organic compound according to the present invention may be represented by the following formula (1).

Formula 1

(In Formula 1, L ₁ to L ₅ are each independently an unsubstituted or substituted C1~C20 alkylene group, an unsubstituted or substituted C3~C30 cycloalkylene group, an unsubstituted or substituted C3~C30 heterocycloalkylene group, or a substituted Unsubstituted or substituted C5~C30 arylene group, unsubstituted or substituted C5~C30 hetero arylene group, unsubstituted or substituted C5~C30 aralkylene group, unsubstituted or substituted C5~C30 hetero aralkylene group, unsubstituted or A substituted C5~C30 oxyarylene group or an unsubstituted or substituted C5~C30 heterooxyarylene group, a, b, c, d, e, and m are each 0 or 1, and A ₁ to A ₄ are each independently Unsubstituted or substituted C1~C20 alkyl group, unsubstituted or substituted C1~C20 alkoxy group, unsubstituted or substituted C1~C20 alkyl group, C5~C30 aryl group or C5~C30 heteroaryl group substituted amine group, unsubstituted or C1 ~C20 alkyl group, C5~C30 aryl group or C5~C30 heteroaryl group substituted silyl group, unsubstituted or substituted C5~C30 aryl group, unsubstituted or substituted C5~C30 heteroaryl group, unsubstituted or substituted C5 ~C30 aralkyl group, unsubstituted or substituted C5~C30 hetero aralkyl group, unsubstituted or substituted C5~C30 oxyaryl group and unsubstituted or substituted C5~C30 hetero oxyaryl group, A ₁ to A ₄ , at least one is a substituent represented by the following formula 2)

Formula 2

(In Formula 2, R ₁ to R ₁₆ are each independently hydrogen, deuterium, tritium, hydroxy group, cyanide group, -CF ₃ , C1 to C20 alkyl group unsubstituted or substituted with fluorine, halogen, unsubstituted or substituted selected from the group consisting of a C1~C20 alkoxy group, an unsubstituted or substituted C5~C30 aryl group, and an unsubstituted or substituted C5~C30 heteroaryl group)

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

In the present specification, the substituents in 'substituted' include, for example, a C1~C20 alkyl group that is unsubstituted or substituted with halogen, a C1~C20 alkoxy group that is unsubstituted or substituted with halogen, halogen, cyano group, -CF ₃ , hydroxy Group, carboxyl group, carbonyl group, amine group, C1~C10 alkyl substituted amine group, C5~C30 aryl substituted amine group, C4~C30 heteroaryl substituted amine group, nitro group, hydrazyl group, sulfonic acid group, C1~ C20 alkyl silyl group, C1~C20 alkoxy silyl group, C3~C30 cycloalkyl silyl group, C5~C30 aryl silyl group, C4~C30 heteroaryl silyl group, C5~C30 aryl group, C4~C30 heteroaryl group, etc. However, the present invention is not limited thereto.

In this specification, 'hetero aromatic ring', 'hetero cycloalkylene group', 'hetero arylene group', 'hetero arylalkylene group', 'hetero aryloxylene group', 'hetero cycloalkyl group', 'hetero aryl group', ' The term 'hetero' used in 'hetero arylalkyl group', 'hetero aryloxyl group', 'hetero aryl amine group', etc. refers to one or more carbon atoms constituting these aromatic or alicyclic rings, e.g. 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 an exemplary embodiment, the substituents not substituted by the diphenylmethylenefluorenyl group represented by Formula 2 among A ₁ to A ₄ in Formula 1 are each independently an unsubstituted or substituted C5 to C30 aryl group, an unsubstituted or substituted C5~C30 heteroaryl group, unsubstituted or substituted C5~C30 aralkyl group, unsubstituted or substituted C5~C30 heteroaralkyl group, unsubstituted or substituted C5~C30 oxyaryl group and unsubstituted or substituted C5~ It may be selected from the group consisting of a C30 heterooxyaryl group. Preferably, the substituent not substituted by the diphenylmethylenefluorenyl group represented by Formula 2 is an unsubstituted or substituted C5~C30 aryl group or an unsubstituted or substituted C5~C30 heteroaryl group.

Such aromatic substituents include, for example, unsubstituted or substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, pentanelenyl group, indenyl group, indenoindenyl group, hepthalenyl 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 A non-condensed or fused homoaryl group, such as a pleidaenyl group, a phycenyl group, a pentaphenyl group, a pentacenyl group, a fluorenyl group, an indenofluorenyl group, or a spiro fluorenyl group, and/or Pyrrolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, tetrazinyl group, imidazolyl group, pyrazolyl group, indolyl group, isoindolyl group, indazolyl group, indolizinyl group, pyrrolizyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl group, quinoli Nyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cynolinyl group, quinazolinyl group, quinozolinyl group, quinolizinyl 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, cinnolinyl group, naphtharidinyl group, furanyl group, par Iranyl group, oxazinyl group, oxazolyl group, oxadiazolyl group, triazolyl group, deoxynyl 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 , it may be an uncondensed or fused heteroaryl group, such as a benzothienodibenzofuranyl group or an N-substituted spirofluorenyl group.

Meanwhile, in one non-limiting embodiment, L ₁ to L ₅ , which are linkers in Formula 1, may be aromatic linking groups.

Specifically, in Formula 1, L ₁ to L ₅ are each independently a substituted or unsubstituted phenylene group, biphenylene group, terphenylene group, tetraphenylene group, or indenylene group. (indenylene), naphthylene, azulenylene, indacenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, Phenalenylene, phenanthrenylene, anthracenylene, fluoranthrenylene, triphenylenylene, pyrenylene, chrysenylene ( chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pyrrolylene, imidazolylene group (imidazolylene), pyrazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indole Indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group (phthalazinylene), naphthyridinylene, quinoxalinylene, quinazolinylene, benzoquinolinylene, benzoisoquinolinylene, benzoquinazolinylene, benzoquinoxali Nylene group, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoxazolylene, Benzimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene, isothiazolylene (isothiazolylene), benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, Benzofuranylene group, dibenzofuranylene group, benzofurodibenzofuranylene group, benzothienobenzofuranylene group, benzothienodibenzofuranylene group, benzothiophenylene group, dibenzothiophenylene group ), benzothiethobenzothiophenylene group, benzothienodibenzothiophenylene group, carbazyolylene group, benzocarbazolylene group, dibenzocarbazolylene group, indolocarbazolylene group, indenocarbazolylene group, benzofurocarbazolylene It may be selected from the group consisting of a lene group, a benzothienocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group.

At this time, when the number of aromatic rings constituting L ₁ to L ₅ increases, the conjugated structure in the entire organic compound becomes excessively long. Accordingly, the band gap of the organic compound represented by Formula 1 may be reduced, thereby reducing hole injection characteristics, hole transport characteristics, and/or hole generation characteristics. Therefore, the number of aromatic rings constituting L ₁ to L ₅ is preferably 1 to 2, more preferably 1.

In addition, with regard to the injection and movement characteristics of holes, L ₁ to L ₅ may each be a 5-membered ring or a 7-membered ring, and in particular, a 6-membered ring (6 -membered ring) may be preferable. For example, L ₁ to L ₅ are substituted or unsubstituted phenylene group, biphenylene group, pyrrolylene group, imidazolylene group, pyrazoylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyrida. It may be a zynylene group, a furanylene group, or a thiophenylene group.

The organic compound represented by Formula 1 has at least one amine group with excellent hole binding properties and thus has excellent hole injection properties and/or hole transport properties. Additionally, the organic compound represented by Formula 1 has excellent thermal stability because it has a structure in which at least one diphenylmethylene fluorenyl group represented by Formula 2 is substituted on the nitrogen atom constituting the amine group. When the organic compound represented by Formula 1 is applied to the organic layer of the light-emitting device, the hole injection characteristics and hole transport characteristics of the light-emitting device are improved, thereby preventing the driving voltage of the light-emitting device from increasing due to hole injection delay, The light emitting device can be sufficiently driven even at low voltage. Additionally, when the organic compound represented by Formula 1 is applied to the organic material layer constituting the light emitting device, holes and electrons can be injected in a balanced manner in the organic material layer constituting the light emitting device, thereby increasing the luminous efficiency of the device. In addition, since the organic compound represented by Formula 1 has high thermal stability, the organic compound represented by Formula 1 does not deteriorate even if the temperature increases due to driving of the light emitting device. Accordingly, by applying the organic compound represented by Formula 1 to an organic material layer requiring hole injection characteristics and/or hole transport characteristics, a light emitting device capable of achieving excellent luminous efficiency can be manufactured.

As such, the organic compound represented by Formula 1 has at least one amine group with excellent hole binding characteristics. Therefore, applying the organic compound according to the present invention to the hole layer or exciton blocking layer of a light emitting device can improve hole injection or hole transport characteristics into the light emitting material layer and prevent electrons from moving to the area where holes are injected. You can do it.

In addition, since the organic compound of the present invention is very excellent in hole injection ability and hole transport ability, a compound or hole injection having the deep lowest unoccupied molecular orbital function (deep LUMO) is adjacent to an organic material layer made of the organic compound of the present invention. When doping a material into the organic compound of the present invention and using it as a charge generation layer, electrons are moved in the opposite direction (for example, toward the anode) of the organic material layer made of the organic compound of the present invention, and the resulting holes are directed to the organic light-emitting layer. By moving it in the direction of the cathode, it has charge generation characteristics. Therefore, the organic compound represented by Formula 1 can be used in the organic layer of the light emitting device, for example, a hole layer such as a hole transport layer and/or a hole injection layer, an exciton blocking layer, and/or a P-type charge generation layer.

In one exemplary embodiment, the organic compound of the present invention consists of one amine group, the nitrogen atom constituting the amine group is substituted with an aromatic ring, and at least one of the substituted aromatic rings is represented by Formula 2 It may be a phenylmethylene fluorenyl group. These organic compounds can be represented by the following formula (3). In another exemplary embodiment, the organic compound of the present invention consists of two amine groups, the nitrogen atom constituting each amine group is substituted with an aromatic ring, and at least one of the substituted aromatic rings is represented by Formula 2 It may be a diphenylmethylenefluorenyl group. These organic compounds can be represented by the following formula (4).

Formula 3

Formula 4

(In Formula 3 and Formula 4, L ₁ to L ₅ , a, b, c, d, and e are each the same as defined in Formula 1, and in Formula 3, A ₁₁ to A ₁₃ are each independently unsubstituted or substituted. C5~C30 aryl group, unsubstituted or substituted C5~C30 heteroaryl group, unsubstituted or substituted C5~C30 aralkyl group, unsubstituted or substituted C5~C30 heteroaralkyl group, unsubstituted or substituted C5~C30 It is selected from the group consisting of an oxyaryl group and an unsubstituted or substituted C5~C30 heterooxyaryl group, and at least one of A ₁₁ to A ₁₃ is a substituent represented by Formula 2, and in Formula 4, A ₂₁ to A ₂₄ each independently represents an unsubstituted or substituted C5~C30 aryl group, an unsubstituted or substituted C5~C30 heteroaryl group, an unsubstituted or substituted C5~C30 aralkyl group, and an unsubstituted or substituted C5~C30 heteroaralkyl group. , unsubstituted or substituted C5~C30 oxyaryl group and unsubstituted or substituted C5~C30 heterooxyaryl group, and at least one of A ₂₁ to A ₂₄ is a substituent represented by Formula 2)

In one exemplary embodiment, among the remaining aromatic substituents not substituted by the diphenylmethylenefluorenyl group represented by Formula 2 among A ₁₁ to A ₁₃ constituting Formula 3, at least one has 2 or more, preferably 3. It may be an aryl group or hetero aryl group in which two or more aromatic rings are condensed.

The condensed aryl group or condensed heteroaryl group, which may be an aromatic substituent unsubstituted by the diphenylmethylenefluorenyl group represented by Formula 2, is a substituted or unsubstituted naphthyl group, anthracenyl group, pentanelenyl group, indenyl group, indenoin Denyl group, hepthalenyl group, biphenylenyl group, indacenyl group, phenalenyl group, phenanthrenyl group, benzophenanthrenyl group, dibenzophenanthrenyl group, azulenyl group, pyrenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, tetraphenyl group, tetracenyl group, pleiadenyl group, pysenyl group, pyrenyl group, pentaphenyl group, pentacenyl group, fluorenyl group, indenofluorenyl group, or spiro Condensed homoaromatic rings such as spiro fluorenyl group and/or indolyl group, isoindolyl group, indazolyl group, indolizinyl group, pyrrozinyl group, pyridyl group, imidazopyridyl group, pyrimidyl group, carbazole Dibenzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group, quinazolinyl group , quinozolinyl group, quinolizinyl group, purinyl group, quinoxalinyl group, benzoquinolinyl group, benzoisoquinolinyl group, benzoquinazolinyl group, benzoquinoxalinyl group, acridinyl group, phenanthrolinyl group, perimidinyl group, Phenanthridinyl group, pteridinyl group, cinnolinyl group, naphtharidinyl group, deoxynyl group, benzofuranyl group, dibenzofuranyl group, thiopyranyl group, xanthenyl group, chromenyl group, isochromenyl group, benzothio Phenyl group, dibenzothiophenyl group, benzothienobenzothiophenyl group, benzothienodibenzothiophenyl group, benzothienocarbazole group, benzofurobenzothiophenyl group, benzofurodibenzothiophenyl group, benzofurobenzofuranyl group, benzopyu It may contain a condensed heteroaromatic ring such as a rhodibenzofuranyl group, benzofurocarbazole group, difuropyrazinyl group, or N-substituted spiro fluorenyl group.

Additionally, in one exemplary embodiment, in Formula 4, at least one of A ₂₁ and A ₂₂ is substituted with a diphenylmethylenefluorenyl group represented by Formula 2, and at least one of A ₂₃ and A ₂₄ is represented by Formula 2. It may be substituted with the indicated diphenylmethylenefluorenyl group. In other words, each nitrogen atom constituting the amine group in Formula 4 may be directly or indirectly substituted with a diphenylmethylenefluorenyl group represented by Formula 2.

The organic compound represented by Formula 3 or Formula 4 has at least one amine group and has excellent hole injection and/or hole transport properties. In addition, since the nitrogen atom constituting the amine group is substituted with a diphenylmethylenefluorenyl group containing a condensed aromatic ring, the thermal stability is also very excellent. Therefore, when the organic compound represented by Formula 3 or Formula 4 is applied to the hole layer, electron blocking layer, and/or charge generation layer constituting the light emitting device, the hole injection characteristics and/or hole transport characteristics into the light emitting material layer are improved. The driving voltage of the light emitting device can be lowered and power consumption can be reduced. Because low-voltage driving is possible, the stress applied to the materials that make up the light-emitting device is reduced. In addition, even at high temperatures, the organic compounds represented by Formula 3 or Formula 4 do not deteriorate. Therefore, by applying the organic compound represented by Formula 3 or Formula 4 to a light emitting device, the lifespan of the light emitting device can be improved and the luminous efficiency of the light emitting device can be improved.

[Light-emitting diode and display device]

Organic compounds represented by Formulas 1 to 4 have excellent hole injection properties, hole transport properties, and electron blocking properties resulting from these properties. Therefore, the organic compounds represented by Formulas 1 to 4 can be applied to organic layers such as hole layers, electron blocking layers, and/or charge generation layers of light emitting devices. A light emitting diode in which the organic compound according to the present invention is applied to the organic material layer will first be described. 1 is a schematic cross-sectional view of a light emitting diode according to a first exemplary embodiment of the present invention.

As shown in FIG. 1, the light emitting diode 100 according to the first exemplary embodiment of the present invention includes a first electrode 110 and a second electrode 120 facing each other, and first and second electrodes ( It includes a light emitting unit 130 located between 110 and 120. The light emitting unit 130 includes a hole injection layer (HIL, 150) and a hole transport layer (HTL, 160), a hole layer (140), and an emitting material layer (EML, 170). ), an electron transporting layer (ETL, 180), and an electron injection layer (EIL, 190).

The first electrode 110 is made of a conductive material with a relatively high work function and is an anode. For example, the first electrode 110 is made of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), and indium-tin-zinc-oxide (indium). It may be made of -tin-zinc oxide (ITZO), indium-copper-oxide (ICO), or aluminum:zinc oxide (Al:ZnO; AZO).

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

The light emitting material layer 170 constituting the light emitting unit 130 may be formed by doping a host with a dopant. For example, when the light emitting material layer 170 emits blue (B) light, the light emitting material layer 170 is selected from the group consisting of anthracene derivative, pyrene derivative, and perylene derivative. It may be achieved by doping the selected at least one fluorescent host material with a fluorescent dopant.

For example, the blue fluorescent host material is 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl(4,4'-bis(2,2'-diphenylyinyl)-1 ,1'-biphenyl; DPVBi), 9,10-di-(2-naphtyl)anthracene (ADN), 2,5,8,11-tetra-t -Butylperylene (tetra-t-butylperylene; TBADN), 2-tert-butyl-9,10-di(2-naphthyl)anthracene ), 2-methyl-9,10-di(2-naphtyl)anthracene (MADN), and/or 2,2',2"-( 1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole(2,2',2"-(1,3,5-benzinetriyl)-tris(1-phenyl- 1-H-benzimidazole; TBPi), etc.

In addition, as a blue fluorescent dopant material, 4,4'-bis(9-ethyl-3-carbazovinylene)-1,1'-biphenyl (4,4'-bis(9-ethyl-3-carbazovinylene)- 1,1'-biphenyl; BCzVBi) and/or diphenyl-[4-(2-[1,1;4,1]tetraphenyl-4-yl-vinyl)-phenyl]-amine (diphenyl-[4- (2-[1,1;4,1]terphenyl-4-yl-vinyl)-phenyl]-amine; BD-1), etc. may be used.

In addition, when the light-emitting material layer 170 emits green (G) light, the light-emitting material layer 170 is a phosphorescent host material made of a carbazole-based compound and a phosphorescent dopant made of a metal complex (e.g., dp ₂ Ir(acac), op ₂ Ir(acac), etc.) may be doped. In addition, when the light-emitting material layer 170 emits red (R) light, the light-emitting material layer 170 is a phosphorescent host material made of a carbazole-based compound and a phosphorescent dopant made of a metal complex (for example, Btp ₂ Ir (acac), etc.) may be doped. The dopant material may be added at a rate of approximately 1 to 30% by weight based on the host material.

The electron transport layer 180 is located between the light emitting material layer 170 and the second electrode 120, and the electron injection layer 190 is located between the electron transport layer 180 and the second electrode 120. The electron transport layer 180 may be a derivative of oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, benzimidazole, triazine, etc. there is. For example, the electron transport layer 180 is made of tris-(8-hydroxyquinoline aluminum; Alq ₃ ), 2-biphenyl-4-yl-5-(4-tertiary-butyl) Phenyl)-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-benzimidazol), 3-(biphenyl-4-yl)-5-(4-terbutylphenyl)-4-phenyl- 4H-1,2,4-triazole (3-(biphenyl-4-yl)-5-(4-tertbutylphenyl)-4-phenyl-4H-1,2,4-triazole; TAZ), 4,7- Diphenyl-1,10-phenanthroline (4,7-diphenyl-1,10-phenanthroline; Bphen), tris(phenylquinoxaline; TPQ) and 1,3,5-tris(N- It may be made of an electron transport material such as phenylbenzimidazol-2-yl)benzene (1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene; TPBI). However, it is not limited thereto.

If necessary, the electron transport layer 180 may be formed by doping the above-described organic material with a metal such as an alkali metal and/or an alkaline earth metal. Alkali metal or alkaline earth metal may be added in a ratio of approximately 1 to 20% by weight based on the above-mentioned organic compound, but the present invention is not limited thereto. Alkali metal components that can be used as dopants in the electron transport layer 180 include alkali metals such as lithium (Li), sodium (Na), potassium (K), and cesium (Cs) and/or magnesium (Mg) and strontium (Sr). , alkaline earth metals such as barium (Ba) and radium (Ra), but are not limited thereto. If necessary, the electron transport layer 180 may be divided into two or more layers rather than a single layer structure.

In addition, the materials of the electron injection layer 190 include alkaline halide-based materials such as LiF, CsF, NaF, and BaF ₂ and/or Liq (lithium quinolate), lithium benzoate, and sodium stearate. ), etc., may be used, but the present invention is not limited thereto.

Meanwhile, the hole layer 140 is located between the first electrode 110 and the light emitting material layer 170. According to the first embodiment of the present invention, the hole layer 140 includes a hole injection layer 150 located between the first electrode 110 and the light-emitting material layer 170, and the hole injection layer 150 and the light-emitting material. It includes a hole transport layer 160 located between the layers 170.

The hole injection layer 150 improves the interface characteristics between the first electrode 110, which is an inorganic material, and the hole transport layer 160, which is an organic material. In one exemplary embodiment, the hole injection layer 150 may be made of an organic compound represented by Chemical Formulas 1 to 4. In another exemplary embodiment, the hole injection layer 150 may be formed by doping organic compounds of Formulas 1 to 4 with a hole injection material. Hole injection materials that can be used include 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (MTDATA) and copper phthalocyanine. 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; NPD, α-NPB), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile; HATCN) , 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-ethylenedioxythiphene)polystyrene sulfonate; PEDOT/PSS), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (2, 3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane; F4TCNQ) 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. At this time, the hole injection material may be doped at about 0.1 to 50% by weight, but the present invention is not limited thereto.

If necessary, the hole injection layer 150 may be divided into two layers. At this time, the first hole injection layer (not shown) located on the first electrode 110 side may be made only of the hole injection material described above, and the first hole injection layer (not shown) located between the hole transport layer 160 2 The hole injection layer (not shown) may be formed by doping the organic compounds of Formulas 1 to 4 with a hole injection material.

The hole transport layer 160 is located adjacent to the light emitting material layer 170. The hole transport layer 160 includes organic compounds represented by Chemical Formulas 1 and 2. In one exemplary embodiment, the hole transport layer 160 may be made only of organic compounds represented by Chemical Formulas 1 to 4.

In another exemplary embodiment, the hole transport layer 160 may be formed by doping the organic compounds of Formulas 1 to 4 with other hole transport materials. For example, other hole transport materials that can be used in the hole transport layer 160 include NPB, TCTA, tris(trifluorovinyl ether)-tris(4-carbazoyl-9-yl-phenyl)amine (tris(trifluorovinyl ether)- tris(4-carbazoyl-9-yl-phenyl)amine; TFV-TCTA), 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 (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), 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (4,4',4''-tris(3-methylphenylphenylamino)triphenylamine; m- MTDATA), 1,3-bis(N-carbazolyl)benzene (1,3-bis(N-carbazolyl)benzene; mCP), 4,4'-bis(N-carbazolyl)-1,1'-bi Phenyl (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), 1,4-bis(diphenylamino)benzene), N,N'- Bis(3-methylphenyl)-N,N'-diphenylbenzidine (N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine; TPD), N,N'-bis(phenanthrene-9- 1)-N,N'-bis(phenyl)-benzidine (N,N'-bis(phenanthren-9-yl)-N,N'-bis(phenyl)-benzidine), CuPC, 2,2'-dimethyl -N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine(2,2'-dimethyl-N,N '-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine), 9,9-dimethyl-N,N'-di(1-naph) Thyl)-N,N'-diphenyl-9H-fluorene-2,7-diamine (9,9-dimethyl-N,N'-di(1-naphthyl)-N,N'-diphenyl-9H-fluorene -2,7-diamine), N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl)-4,4'-diamine (N, N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl)-4,4'-diamine), N,N'-diphenyl-N,N'-di -p-tolylbenzene-1,4-diamine (N,N'-diphenyl-N,N'-di-p-tolylbenzene-1,4-diamine), 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), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), N,N,N', N'-tetrakis(3-methylphenyl)-3,3'-dimethylbenzidine (N,N,N',N'-tetrakis(3-methylphenyl)-3,3'-dimethylbenzidine), N,N,N' ,N'-tetrakis(2-naphthyl)benzidine (N,N,N',N'-tetrakis(2-naphthyl)benzidine), tetra-N-phenylbenzidine, N,N ,N',N'-tetraphenylnaphthalene-2,6-diamine (N,N,N',N'-tetraphenylnaphthalene-2,6-diamine), tin(IV) 2,3-naphthalocyanine dichloride (tin (IV) 2,3-naphthalocyanine dichloride), titanyl phthalocyanine, 1,3,5-tris(diphenylamino)benzene (TDAB), and/ or 4,4',4''-tris[phenyl(m-tolyl)amino]triphenylamine (4,4',4''-tris[phenyl(m-tolyl)amino]triphenylamine), The present invention is not limited to this.

For example, the hole transport material described above may be used as a dopant for the hole transport layer 160. At this time, the above-described hole transport material used as a dopant may be doped into the hole transport layer 160 in an amount of about 0.1 to 50% by weight, but the present invention is not limited thereto.

In an alternative embodiment, hole transport layer 160 may be comprised of two layers. At this time, the first hole transport layer (not shown) located adjacent to the hole injection layer 150 is made of the hole transport material described above, and the second hole transport layer (not shown) located adjacent to the light emitting material layer 170. It may be made only of organic compounds represented by Formulas 1 to 4, or may be made by doping the organic compounds represented by Formulas 1 to 4 with a hole transport material.

Meanwhile, in the drawing, the hole layer 140 is divided into a hole injection layer 150 and a hole transport layer 160. However, the hole layer 140 is formed by adding the above-described hole injection material to the organic compounds represented by Formulas 1 to 4, such as MTDATA, CuPc, TCTA, NPB (NPD), HATCN, TDAPB, PEDOT/PSS, F4TCNQ, and /or N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine It may consist of a doped first layer.

Since the organic compound of the present invention has excellent hole injection ability and hole transport ability, the hole layer formed by doping the organic compound of the present invention with a hole injection material can serve both as a hole injection layer and a hole transport layer. In other words, even if there is only one layer of hole layer 140 doped with a hole injection material in an organic compound represented by Formula 1 to Formula 4 between the first electrode 110 and the light emitting material layer 170, hole injection and hole injection Sufficient transport characteristics can be obtained. At this time, the hole injection material may be doped, for example, at about 0.1 to 50% by weight, but the present invention is not limited thereto.

That is, the light emitting diode 100 according to the first exemplary embodiment of the present invention is positioned between the first and second electrodes 110 and 120 facing each other and the first and second electrodes 110 and 120. The light emitting unit 130 includes a hole layer 140 between the first electrode 110 and the light emitting material layer 170 to which the organic compound according to the present invention can be applied.

The organic compound of the present invention has excellent hole injection properties, hole transport properties, and thermal stability. Therefore, when the organic compound of the present invention is used alone or together with an appropriate hole injection material and/or hole transport material in the hole layer 140, the light emitting diode 100 is driven at a low voltage. Power consumption can be reduced, the lifespan of the light emitting diode 100 can be improved, and luminous efficiency can be improved.

Figure 2 is a schematic cross-sectional view of a light emitting diode according to a second exemplary embodiment of the present invention. As shown in FIG. 2, the 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 a first and second electrode 210, It includes a light emitting unit 230 located between 220). The light emitting unit 230 includes a light emitting material layer 270, a hole layer 240 located between the first electrode 210 and the light emitting material layer 270, and the hole layer 240 and the light emitting material layer ( Includes an electron blocking layer (EBL) 266 located between 270), an electron transport layer 280 and an electron injection layer 290 located between the light emitting material layer 270 and the second electrode 220. do. The hole layer 240 includes a hole injection layer 250 and a hole transport layer 260.

As described above, the first electrode 210 is an anode and is made of a conductive material with a relatively high work function, and the second electrode 220 is a cathode and is made of a conductive material with a relatively small work function.

The light emitting material layer 270 may be formed by doping a host with a dopant. The electron transport layer 280 located between the light emitting material layer 270 and the second electrode 220 is made of oxadiazole, triazole, phenanthroline, benzoxazole, and benzoate. It may be made of derivatives such as thiazole (benzothiazole), benzimidazole, and triazine. The electron transport layer 280 may include a dopant such as an alkali metal or an alkaline earth metal.

The electron injection layer 290 located between the electron transport layer 280 and the second electrode 220 is made of an alkaline halide-based material such as LiF, CsF, NaF, and BaF ₂ and/or Liq (lithium quinolate) and lithium benzoate ( It may be made of organometallic materials such as lithium benzoate and sodium stearate.

The hole injection layer 250 improves the interface characteristics between the first electrode 210, which is an inorganic material, and the hole transport layer 260, which is an organic material. In one exemplary embodiment, the hole injection layer 250 may be made of an organic compound represented by Formula 1 to Formula 4. In another optional embodiment, the hole injection layer 250 is formed by adding a hole injection material to an organic compound represented by Formula 1 to Formula 4, such as MTDATA, CuPc, TCTA, NPD (α-NPB), HATCN, TDAPB, PEDOT/ PSS, F4TCNQ and/or N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene- It may be doped with any material selected from 2-amine, etc.

In another exemplary embodiment, the hole injection layer 250 includes a first hole injection layer (not shown) made of a hole injection material, and a second hole injection layer made by doping the organic compounds represented by Formulas 1 to 4 with a hole injection material. It can be divided into a hole injection layer (not shown).

The hole transport layer 260 includes organic compounds represented by Chemical Formulas 1 to 4. In one exemplary embodiment, the hole transport layer 260 may be made only of organic compounds represented by Formulas 1 to 4. In another exemplary embodiment, the hole transport layer 260 may be formed by doping organic compounds represented by Formulas 1 to 4 with a hole transport material. Materials that can be used as hole transport dopants include, but are not limited to, NPB, TCTA, TFV-TCTA, TAPC, m-MTDATA, mCP, TPD, CuPC, DNTPD and/or TDAB.

In an optional embodiment, the hole transport layer 260 includes a first hole transport layer (not shown) located adjacent to the hole injection layer 250 and made solely of the hole transport material described above, and a hole transport layer (not shown) represented by Formulas 1 to 4. It may be composed of a second hole transport layer (not shown) made only of organic compounds or made by doping organic compounds represented by Formulas 1 to 4 with a hole transport material.

Meanwhile, when holes pass through the light-emitting material layer 270 and move to the second electrode 220, or electrons pass through the light-emitting material layer 270 and move to the first electrode 210, the lifespan and efficiency of the device decrease. You can bring it. To prevent this, the light emitting diode 200 according to the second embodiment of the present invention may include an exciton blocking layer at least one of the top and bottom of the light emitting material layer 270.

For example, independently of the hole layer 240, an electron blocking layer 265 capable of controlling and preventing the movement of electrons may be located between the first electrode 210 and the light emitting material layer 270. The organic compounds represented by Formulas 1 to 4 have excellent hole injection and hole transport properties, but have low electron binding properties and thus have excellent electron blocking abilities. In one exemplary embodiment, the electron blocking layer 265 may be made of an organic compound represented by Formula 1 to Formula 4.

In addition, if necessary, a hole blocking layer (HBL, not shown) as another exciton blocking layer is positioned between the light emitting material layer 270 and the electron transport layer 280 to protect the light emitting material layer 270 and the electron transport layer ( 280) prevents the movement of holes between In one exemplary embodiment, oxadiazole, triazole, phenanthroline, and benzoxazole ( Derivatives such as benzoxazole, benzothiazole, benzimidazole, and triazine may be used.

For example, the hole blocking layer (not shown) is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) with a low highest occupied molecular orbital (HOMO) level. and/or bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(BAlq).

The organic compound of the present invention has excellent hole injection properties, hole transport properties, and thermal stability, while its electronic binding properties are low. Therefore, when the organic compound of the present invention is used alone or in combination with an appropriate hole injection material and/or hole transport material in the hole layer 240 and/or the electron blocking layer 265, low voltage By driving the light emitting diode 200, power consumption can be reduced, the lifespan of the light emitting diode 200 can be improved, and luminous efficiency can be improved.

Meanwhile, the organic compound of the present invention can be applied to a light emitting diode having a tandem structure in addition to the light emitting diode having the above-mentioned single-layer structure, and can implement white color at low voltage. Figure 3 is a schematic cross-sectional view of a light emitting diode having a tandem structure according to a third exemplary embodiment of the present invention. As shown in FIG. 3, the light emitting diode 300 according to the third embodiment of the present invention includes a first electrode 310 and a second electrode 320 facing each other, and a first and second electrode 310, 320), a first light-emitting unit (lower light-emitting unit, 330) located between the first light-emitting unit 330 and the second electrode 320, and a second light-emitting unit (upper light-emitting unit, 340), It includes a charge generation layer 350 located between the first and second light emitting units 330 and 340.

As described above, the first electrode 310 is an anode and is made of a conductive material with a relatively high work function, and the second electrode 320 is a cathode and is made of a conductive material with a relatively small work function.

The first light emitting unit 330 includes a hole layer 331, a first light emitting material layer (lower light emitting material layer, 336), and a first electron transport layer (lower electron transport layer, 338). For example, the hole layer 331 may be composed of a hole injection layer 332 and a first hole transport layer (lower hole transport layer, 334).

The hole injection layer 332 is located between the first electrode 310 and the first light emitting material layer 336. In one exemplary embodiment, the hole injection layer 332 may be made of an organic compound represented by Formula 1 to Formula 2. In another optional embodiment, the hole injection layer 332 is an organic compound represented by Formula 1 to Formula 2 containing MTDATA, CuPc, TCTA, α-NPB, HATCN, TDAPB, PEDOT/PSS, F4TCNQ and/or N-( Biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, etc. The material may be doped with a hole injection material. At this time, the hole injection material may be doped at about 0.1 to 50% by weight.

In another exemplary embodiment, the hole injection layer 332 is a hole injection layer (not shown) made of a hole injection material, and a separate layer formed by doping an organic compound represented by Formulas 1 to 4 with a hole injection material. It can be divided into a hole injection layer (not shown).

The first hole transport layer 334 is located between the hole injection layer 332 and the first light-emitting material layer 336, and the first light-emitting material layer 336 is located between the first hole transport layer 334 and the first electron transport layer 338. ), and the first electron transport layer 338 is located between the first light emitting material layer 336 and the charge generation layer 350.

In FIG. 3, the hole layer 331 constituting the first light emitting unit 330 is divided into a hole injection layer 332 and a first hole transport layer 334. However, the hole layer 331 may be composed of one layer. In this case, the hole injection material may be doped into an organic compound represented by Formulas 1 to 4.

The second light-emitting unit 340 includes a second hole transport layer (upper hole transport layer, 342), a second light-emitting material layer (upper light-emitting material layer, 344), a second electron transport layer (upper electron transport layer, 346), and electrons. Includes an injection layer 348.

The second light emitting material layer 344 is located between the second hole transport layer 342 and the second electrode 320, and the second electron transport layer 346 is located between the second light emitting material layer 344 and the second electrode 320. The electron injection layer 348 is located between the second electron transport layer 346 and the second electrode 320.

Each of the first and second light emitting material layers 336 and 344 may be formed by doping a host with a dopant, and emit different colors. For example, the first light-emitting material layer 336 emits blue (B), red (R), green (G), or yellow (Y), and the second light-emitting material layer 344 emits red (R). , it may be any one of green (G), blue (B), and yellow-green (YG) light emitting material layers. In one exemplary embodiment, the first layer of light-emitting material 336 emits blue, and the second layer of light-emitting material 344 emits green, yellow-green (YG), or orange, which has a longer wavelength than blue. You can. For example, when the second light-emitting material layer 344 constitutes a yellow-green light-emitting material layer, CBP may be used as a host material of the second light-emitting material layer 344, and a dopant such as Ir(2-phq) ₃ can be used.

Each of the first and second hole transport layers 334 and 342 includes organic compounds represented by Chemical Formulas 1 to 4. In one exemplary embodiment, each of the first and second hole transport layers 334 and 342 may be made only of organic compounds represented by Formulas 1 to 4. In another exemplary embodiment, each of the first and second hole transport layers 334 and 342 may be formed by doping the organic compounds represented by Formulas 1 to 4 with a hole transport material. Materials that can be used as hole transport dopants include α-NPB, TCTA, TFV-TCTA, TAPC, m-MTDATA, mCP, TPD, CuPC, DNTPD and/or TDAB, but the present invention is not limited thereto.

In an optional embodiment, the first and second hole transport layers 334 and 342 each include a hole transport layer (not shown) composed only of the hole transport material described above, and an organic compound represented by Formula 1 to Formula 4 or Formula 1 It may be composed of a separate hole transport layer (not shown) made by doping the organic compound represented by Formula 4 to 4 with a hole transport material. The first and second hole transport layers 334 and 342 may be made of the same material or may be made of different materials.

The first and second electron transport layers 338 and 346 each contain oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimidazole. (For example, it may be made of an electron transport material such as 2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole). The first and second electron transport layers 338 and 346 may each include a dopant such as an alkali metal or an alkaline earth metal. The first and second electron transport layers 338 and 346 may be made of the same material or may be made of different materials.

The electron injection layer 348 is made of an alkali halide-based material such as LiF, CsF, NaF, and BaF ₂ and/or an organic metal-based material such as Liq (lithium quinolate), lithium benzoate, and sodium stearate. It can be done with

The charge generation layer 350 is located between the first light-emitting unit 330 and the second light-emitting unit 340, and includes an N-type charge generation layer (N-CGL, 352) adjacent to the first light-emitting unit 330. It includes a P-type charge generation layer (P-CGL, 354) adjacent to the second light emitting unit 340. The N-type charge generation layer 352 injects electrons into the first light-emitting unit 330, and the P-type charge generation layer 354 injects holes into the second light-emitting unit 340.

The N-type charge generation layer 352 may be an organic layer doped with an alkali metal such as Li, Na, K, or Cs and/or an alkaline earth metal such as Mg, Sr, Ba, or Ra. For example, the host organic material used in the N-type charge generation layer 352 is 4,7-dipheny-1,10-phenanthroline (Bphen), MTDATA and It may be the same material, and the alkali metal or alkaline earth metal may be doped in an amount of about 0.01 to 30% by weight.

The P-type charge generation layer 354 may include organic compounds represented by Formulas 1 to 4. For example, the P-type charge generation layer 354 may be formed by doping organic compounds represented by Formulas 1 to 4 with a hole injection material. Materials that can be used as dopants for the P-type charge generation layer 354 include MTDATA, CuPc, TCTA, α-NPB, HATCN, TDAPB, PEDOT/PSS, F4TCNQ and/or N-(biphenyl-4-yl)-9. ,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, etc. When the P-type charge generation layer 354 includes an organic compound represented by Formula 1 to Formula 4 and a hole injection material, the hole injection material may be doped at about 0.1 to 50% by weight, but the present invention is not limited thereto. That is not the case.

Meanwhile, although not shown in the drawing, a second hole is formed between the P-type charge generation layer 354 and the second hole transport layer 342 and/or between the N-type charge generation layer 352 and the P-type charge generation layer 354. An injection layer (upper hole injection layer; not shown) may be located. When the second hole injection layer is adopted, holes generated in the P-type charge generation layer 354 can be efficiently injected and transferred to the second light emitting unit 340.

The second hole injection layer (not shown) may include an organic compound represented by Chemical Formulas 1 to 4. In one optional embodiment, the second hole injection layer (not shown) may be made of an organic compound represented by Formula 1 to Formula 4. In another optional embodiment, the second hole injection layer (not shown) is an organic compound represented by Formula 1 to Formula 4 and a hole injection material, such as MTDATA, CuPc, TCTA, α-NPB, HATCN, TDAPB, PEDOT/ PSS, F4TCNQ and/or N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene- It may be doped with any material selected from 2-amine, etc. At this time, the first hole injection layer 332 and the second hole injection layer (not shown) may be made of the same material or may be made of different materials.

As described above, the organic compound of the present invention has excellent hole injection properties, excellent hole transfer properties, and excellent thermal stability. In particular, when the P-type charge generation layer 354 is formed by doping the organic compounds represented by Formulas 1 to 4 with a hole injection material, holes can be efficiently supplied to the second light emitting unit 340. Therefore, the hole transport layer 334 may be formed by using the organic compounds represented by Formulas 1 to 4 alone, or by doping the organic compounds represented by Formulas 1 to 4 with other appropriate hole injection materials and/or hole transport materials. , 342), the light emitting diode 300 having a tandem structure employing a P-type charge generation layer 354, a hole injection layer 332, and a second hole injection layer (not shown) emits white light that can be driven at a low voltage. It can be used for. By using the organic compound according to the present invention, the light emitting diode 300 can be driven at a low voltage, the lifespan of the light emitting diode 300 can be improved, and the luminous efficiency can be improved.

Figure 4 is a schematic cross-sectional view of a light emitting diode according to a fourth exemplary embodiment of the present invention. As shown in FIG. 4, the light emitting diode 400 according to the fourth embodiment of the present invention includes a first electrode 410 and a second electrode 420 facing each other, and a first and second electrode 410, 420), a first light-emitting unit (lower light-emitting unit, 430), and a second light-emitting unit (upper light-emitting unit, 440) located between the first light-emitting unit 430 and the second electrode 420, It includes a charge generation layer 450 located between the first and second light emitting units 430 and 440.

As described above, the first electrode 410 is an anode and is made of a conductive material with a relatively high work function, and the second electrode 420 is a cathode and is made of a conductive material with a relatively small work function.

The first light emitting unit 430 includes a hole layer 431, a first electron blocking layer (lower electron blocking layer, 435), a first light emitting material layer (lower light emitting material layer, 436), and a first electron transport layer. (lower electron transport layer, 438).

The hole layer 431 may be composed of a hole injection layer 432 and a first hole transport layer (lower hole transport layer, 434). The hole injection layer 432 is located between the first electrode 410 and the first light-emitting material layer 436, and the first hole transport layer 434 is located between the first hole injection layer 432 and the first light-emitting material layer ( 436), and the first electron blocking layer 435 is located between the first hole transport layer 434 and the first light emitting material layer 436. That is, a first electron blocking layer 435 that prevents the movement of electrons independently of the hole layer 431 may be located between the first electrode 410 and the first light emitting material layer 436.

In addition, the first light emitting material layer 436 is located between the first electron blocking layer 435 and the first electron transport layer 438, and the first electron transport layer 438 is connected to the first light emitting material layer 436 and the charge. It is located between the production layers 450. Although not shown, a lower hole blocking layer that can prevent the movement of holes may be located between the first light emitting material layer 436 and the first electron transport layer 438.

In FIG. 4 , the hole layer 431 constituting the first light emitting unit 430 is divided into a hole injection layer 432 and a first hole transport layer 434. However, the hole layer 431 may be composed of one layer. In this case, the hole injection material may be doped into an organic compound represented by Chemical Formulas 1 to 4.

The second light emitting unit 440 includes a second hole transport layer (upper hole transport layer, 442), a second electron blocking layer (upper electron blocking layer, 443), and a second light emitting material layer (upper light emitting material layer, 444). , a second electron transport layer (upper electron transport layer, 646), and an electron injection layer (648). The second hole transport layer 442 is located between the charge generation layer 450 and the second light emitting material layer 444, and the second electron blocking layer 443 is located between the second hole transport layer 442 and the second light emitting material layer ( 444). That is, a second electron blocking layer 443 that prevents the movement of electrons independently of the second hole transport layer 442 may be located between the charge generation layer 450 and the second light emitting material layer 444.

The second electron transport layer 446 is located between the second light emitting material layer 444 and the second electrode 420, and the electron injection layer 448 is located between the second electron transport layer 446 and the second electrode 420. Located. Although not shown, an upper hole blocking layer that can prevent the movement of holes may be located between the second light-emitting material layer 444 and the second electron transport layer 446, and the P-type charge generation layer 454 and the 2 A second hole injection layer (not shown) may be located between the hole transport layer 442 and/or between the N-type charge generation layer 452 and the P-type charge generation layer 454.

Each of the first and second light emitting material layers 436 and 444 may be formed by doping a host with a dopant, and emit different colors. For example, the first light-emitting material layer 436 emits blue (B), red (R), green (G), or yellow (Y), and the second light-emitting material layer 444 emits red (R). , it may be any one of green (G), blue (B), and yellow-green (YG) light emitting material layers. In one exemplary embodiment, the first layer of light-emitting material 436 emits blue, and the second layer of light-emitting material 444 emits green, yellow-green (YG), or orange, which has a longer wavelength than blue. You can. For example, when the second light-emitting material layer 444 constitutes a yellow-green light-emitting material layer, CBP may be used as a host material of the second light-emitting material layer 344, and a dopant such as Ir(2-phq) ₃ can be used.

Each of the first hole injection layer 432 and the second hole injection layer (not shown) includes organic compounds represented by Formulas 1 to 4. In one exemplary embodiment, each of the first hole injection layer 432 and the second hole injection layer (not shown) may be made only of organic compounds represented by Formulas 1 to 4. In another exemplary embodiment, the first hole injection layer 432 and the second hole injection layer (not shown) each contain organic compounds represented by Formulas 1 to 4, such as MTDATA, CuPc, TCTA, α-NPB, HATCN, TDAPB, PEDOT/PSS, F4TCNQ and/or N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H -It may be doped with about 0.1 to 50% by weight of any material selected from fluorene-2-amine. In another exemplary embodiment, the first hole injection layer 432 and the second hole injection layer (not shown) each include a hole injection layer (not shown) made of the above-described hole injection material, and a hole injection layer (not shown) made of the above-described hole injection material, represented by Formulas 1 to 4 It can be divided into a separate hole injection layer (not shown) formed by doping the displayed organic compound with a hole injection material. The first hole injection layer 432 and the second hole injection layer (not shown) may be made of the same material or may be made of different materials.

Each of the first and second hole transport layers 434 and 442 includes organic compounds represented by Chemical Formulas 1 to 4. In one exemplary embodiment, each of the first and second hole transport layers 432 and 444 may be made only of organic compounds represented by Formulas 1 to 4. In another exemplary embodiment, the first and second hole transport layers 434 and 442 may be formed by doping organic compounds represented by Formulas 1 to 4 with a hole transport material. Materials that can be used as hole transport dopants include, but are not limited to, NPB, TCTA, TFV-TCTA, TAPC, m-MTDATA, mCP, TPD, CuPC, DNTPD and/or TDAB.

In an optional embodiment, the first and second hole transport layers 434 and 442 each include a hole transport layer (not shown) made only of the hole transport material described above, and an organic compound represented by Formula 1 to Formula 4 or Formula 1 It may be composed of a separate hole transport layer (not shown) made by doping the organic compound represented by Formula 4 to 4 with a hole transport material. The first and second hole transport layers 434 and 442 may be made of the same material or may be made of different materials.

Each of the first and second electron blocking layers 435 and 443 may be made of an organic compound represented by Chemical Formulas 1 to 4. As described above, since the organic compounds represented by Formulas 1 to 4 have low electron binding ability, they can effectively prevent electrons from moving toward the first electrode 410. The first and second electron blocking layers 435 and 443 may be made of the same material or may be made of different materials.

The first and second electron transport layers 438 and 446 each contain oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimidazole. (For example, it may be made of an electron transport material such as 2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole). The first and second electron transport layers 438 and 446 may each include a dopant such as an alkali metal or an alkaline earth metal. The first and second electron transport layers 438 and 446 may be made of the same material or may be made of different materials.

The electron injection layer 448 is made of an alkali halide-based material such as LiF, CsF, NaF, and BaF ₂ and/or an organic metal-based material such as Liq (lithium quinolate), lithium benzoate, and sodium stearate. It can be done with

The charge generation layer 450 is located between the first light-emitting unit 430 and the second light-emitting unit 440, and includes an N-type charge generation layer (N-CGL, 452) adjacent to the first light-emitting unit 430, and It includes a P-type charge generation layer (P-CGL, 454) adjacent to the second light emitting unit 440. The N-type charge generation layer 452 injects electrons into the first light-emitting unit 430, and the P-type charge generation layer 454 injects holes into the second light-emitting unit 440.

The N-type charge generation layer 452 may be an organic layer doped with an alkali metal such as Li, Na, K, or Cs or an alkaline earth metal such as Mg, Sr, Ba, or Ra. The host organic material used in the N-type charge generation layer 452 may be a material such as Bphen or MTDATA, and may be doped with an alkali metal or alkaline earth metal in an amount of about 0.01 to 30% by weight.

The P-type charge generation layer 354 may include organic compounds represented by Formulas 1 to 4. For example, the P-type charge generation layer 454 may be formed by doping organic compounds represented by Formulas 1 to 4 with a hole injection material. Materials that can be used as dopants for the P-type charge generation layer 454 include MTDATA, CuPc, TCTA, α-NPB, HATCN, TDAPB, PEDOT/PSS, F4TCNQ and/or N-(biphenyl-4-yl)-9. ,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, etc. When the P-type charge generation layer 454 includes an organic compound represented by Formula 1 to Formula 4 and a hole injection material, the hole injection material may be doped at about 0.1 to 50% by weight, but the present invention is not limited thereto. That is not the case.

As described above, the organic compound of the present invention has excellent hole injection properties, hole transfer properties and/or electron blocking properties, and excellent thermal stability. In particular, when the type charge generation layer 454 is formed by doping an organic compound represented by Formula 1 to Formula 4 with a hole injection material, holes can be efficiently supplied to the second light emitting unit 440. Therefore, the hole transport layer (434, 442), a P-type charge generation layer 454, a hole injection layer 432, a second hole injection layer (not shown), and an electron blocking layer 435, 443 are adopted in the tandem structure light emitting diode 400. -Can be used to emit white light that can be driven at any voltage. By using the organic compound according to the present invention, the light emitting diode 400 can be driven at a low voltage, the lifespan of the light emitting diode 400 can be improved, and the luminous efficiency can be improved.

In addition, in FIGS. 3 and 4, the P-type charge generation layer is explained with a focus on including the organic compounds of Formulas 1 and 4. However, as in FIGS. 1 and 2, a hole injection layer, a hole transport layer, and/or an electron blocking layer are used. The layer may include an organic compound of Formula 1 to Formula 4. In addition, although it is explained in FIGS. 3 and 4 that the first and second light emitting units are stacked and a charge generation layer is located between them, it may further include an additional light emitting unit and a charge generation layer located between the light emitting units. there is.

Next, a display device to which the light emitting diode of the present invention is applied will be described. Figure 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 device 500 is located on a driving thin film transistor (Td), a planarization layer 560 covering the driving thin film transistor (Td), and the planarization layer 560 and is driven. It includes a light emitting diode (E) connected to the driving thin film transistor (Td), which is an element. The driving thin film transistor (Td) includes a semiconductor layer 540, a gate electrode 544, a source electrode 556, and a drain electrode 558. In Figure 5, the driving thin film has a coplanar structure. Represents a transistor (Td).

The substrate 501 may be a glass substrate, a thin flexible substrate, or a polymer plastic substrate. The substrate 501 on which the driving thin film transistor (Td), which is a driving element, and the light emitting diode (E) on which the organic light emitting layer 520 is formed, are located, form an array substrate.

A semiconductor layer 540 is formed on the substrate 501. For example, the semiconductor layer 540 may be made of an oxide semiconductor material. In this case, a light blocking pattern (not shown) and a buffer layer (not shown) may be formed under the semiconductor layer 540, and the light blocking pattern prevents light from entering the semiconductor layer 540, thereby preventing light from entering the semiconductor layer 540. prevents deterioration by Alternatively, the semiconductor layer 540 may be made of polycrystalline silicon, and in this case, both edges of the semiconductor layer 540 may be doped with impurities.

A gate insulating film 542 made of an insulating material is formed on the entire surface of the substrate 501 on the semiconductor layer 540. The gate insulating film 542 may be made of an inorganic insulating material such as silicon oxide (SiO ₂ ) or silicon nitride (SiNx).

A gate electrode 544 made of a conductive material such as metal is formed on the gate insulating film 542 corresponding to the center of the semiconductor layer 540. Additionally, a gate wiring (not shown) and a first capacitor electrode (not shown) may be formed on the gate insulating film 542. The gate wire extends along the first direction, and the first capacitor electrode may be connected to the gate electrode 544. Meanwhile, the gate insulating film 542 is formed on the entire surface of the substrate 501, but the gate insulating film 542 may be patterned to have the same shape as the gate electrode 544.

An interlayer insulating film 550 made of an insulating material is formed on the entire surface of the substrate 501 on the gate electrode 544. The interlayer insulating film 550 may be formed of an inorganic insulating material such as silicon oxide (SiO ₂ ) or silicon nitride (SiNx), or may be formed of an organic insulating material such as benzocyclobutene or photo-acryl. there is.

The interlayer insulating film 550 has first and second semiconductor layer contact holes 552 and 554 exposing upper surfaces on both sides of the semiconductor layer 540 . The first and second semiconductor layer contact holes 552 and 554 are located on both sides of the gate electrode 544 and spaced apart from the gate electrode 544 . Here, the first and second semiconductor layer contact holes 552 and 554 are also formed within the gate insulating film 542. In contrast, when the gate insulating film 542 is patterned to have the same shape as the gate electrode 544, the first and second semiconductor layer contact holes 552 and 554 are formed only in the interlayer insulating film 550.

A source electrode 556 and a drain electrode 558 made of a conductive material such as metal are formed on the interlayer insulating film 550. Additionally, a data wire (not shown), a power wire (not shown), and a second capacitor electrode (not shown) extending along the second direction may be formed on the interlayer insulating film 550.

The source electrode 556 and the drain electrode 558 are positioned spaced apart from each other around the gate electrode 544, and are connected to both sides of the semiconductor layer 540 through the first and second semiconductor layer contact holes 552 and 554, respectively. Contact. Although not shown, the data wire extends along the second direction and intersects the gate wire to define the pixel area, and the power wire supplying a high potential voltage is located spaced apart from the data wire. The second capacitor electrode is connected to the drain electrode 558 and overlaps the first capacitor electrode, thereby forming a storage capacitor using the interlayer insulating film 550 between the first and second capacitor electrodes as a dielectric layer.

Meanwhile, the semiconductor layer 540, gate electrode 544, source electrode 556, and drain electrode 558 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 544, a source electrode 556, and a drain electrode 558 are located on the semiconductor layer 540. In contrast, the driving thin film transistor Td may have an inverted staggered structure in which the gate electrode is located at the bottom of the semiconductor layer, and the source electrode and drain electrode are located at the top of the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.

Additionally, a switching thin film transistor (not shown) having substantially the same structure as the driving thin film transistor (Td) is further formed on the substrate 501. The gate electrode 544 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 556 of the driving thin film transistor (Td) is connected to the power wiring (not shown). connected. Additionally, the gate electrode (not shown) and the source electrode (not shown) of the switching thin film transistor (not shown) are connected to the gate wire and data wire, respectively.

Meanwhile, the organic light emitting diode display device 500 may include a color filter (not shown) that absorbs light generated from the light emitting diode (E). 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 can be formed separately for each pixel area, and each of these color filter patterns is a light emitting diode (E) that emits light in the wavelength band to be absorbed. ) may be disposed to overlap each other with the organic light-emitting layer 520 in ). By adopting a color filter (not shown), the organic light emitting diode display device 500 can implement full color.

For example, when the organic light emitting display device 500 is a bottom emitting type, a color filter (not shown) that absorbs light may be located on the interlayer insulating film 550 corresponding to the light emitting diode (E). In an optional embodiment, when the organic light emitting display device 500 is a top emitting type, the color filter may be located on top of the light emitting diode E, that is, on top of the second electrode 530. For example, a color filter (not shown) may be formed to have a thickness of 2 to 5 ㎛. At this time, the light emitting diode (E) may be a white light emitting diode having a tandem structure shown in FIGS. 3 and 4.

A planarization layer 560 is formed on the entire surface of the substrate 501 above the source electrode 556 and the drain electrode 558. The planarization layer 560 has a flat top surface and has a drain contact hole 562 exposing the drain electrode 558 of the driving thin film transistor (Td). Here, the drain contact hole 562 is shown as being formed directly above the second semiconductor layer contact hole 554, but may be formed spaced apart from the second semiconductor layer contact hole 554.

The light emitting diode (E) is located on the planarization layer 560 and includes a first electrode 510 connected to the drain electrode 558 of the driving thin film transistor (Td), and an organic electrode sequentially stacked on the first electrode 510. It includes a light emitting layer 520 and a second electrode 530.

1 Electrode 510 is formed separately for each pixel area. The first electrode 670 may be an anode and may be made of a conductive material with a relatively high work function value. For example, the first electrode 510 may be made of a transparent conductive material such as indium-tin-oxide (ITO) or indium-zinc-oxide (IZO). .

Meanwhile, when the organic light emitting diode display device 500 of the present invention is a top-emission type, a reflective electrode or a reflective layer may be further formed below the first electrode 510. For example, the reflective electrode or the reflective layer may be made of aluminum-palladium-copper (APC) alloy.

Additionally, a bank layer 572 covering the edge of the first electrode 510 is formed on the planarization layer 560. The bank layer 572 exposes the center of the first electrode 510 corresponding to the pixel area.

An organic light-emitting layer 530 is formed on the first electrode 510. The organic light-emitting layer 530 may have a single-layer structure of an emitting material layer made of a light-emitting material.

As explained through the exemplary embodiments of FIGS. 1 to 4, the organic light emitting layer 520 is a layer in which organic compounds represented by Formulas 1 to 4 form a hole layer, an electron blocking layer, and/or a charge generation layer. Includes. For example, the organic light-emitting layer 520 includes a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and optionally a hole blocking layer and an electron blocking layer, respectively located above and below the light emitting material layer. can do.

A second electrode 530 is formed on the substrate 510 on which the organic light emitting layer 530 is formed. The second electrode 530 is located in front of the display area and is made of a conductive material with a relatively low work function value and can be used as a cathode. For example, the second electrode 530 may be made of any one of aluminum (Al), magnesium (Mg), and aluminum-magnesium alloy (AlMg).

An encapsulation film 580 is formed on the second electrode 530 to prevent external moisture from penetrating into the light emitting diode (E). For example, the encapsulation film 580 may have a stacked structure of a first inorganic insulating layer 582, an organic insulating layer 584, and a second inorganic insulating layer 586, but is not limited to this.

As described above, the organic compound of the present invention has at least one amine group with excellent hole binding properties, and the diphenylmethylenefluorenyl group represented by Formula 2 is directly or indirectly connected to the nitrogen atom constituting the amine group to generate heat. Excellent stability. Therefore, when other organic compounds according to the present invention are used alone, or when the organic compounds according to the present invention are doped with appropriate hole injection materials and/or hole transport substances, the hole transport characteristics to the organic light-emitting layer 520 are improved and low -Can be driven at any voltage. Additionally, when the organic compound of the present invention is used in a P-type charge generation layer in a light emitting diode having a tandem structure, it can be applied to move the generated charge to an adjacent common layer. By applying the organic compound according to the present invention to the light emitting diode (E), the light emitting diode (E) can be driven at a low voltage, the lifespan of the light emitting diode (E) can be improved, and the luminous efficiency can be improved.

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

Synthesis Example 1: Synthesis of A4 compound

1) Compound A1 synthesis

Dissolve diphenylmethane (10.00g, 59.44 mmol) in THF (100 mL) in a 250 mL round bottom flask and cool to 0°C. Afterwards, 1.6M n-Butyllithium (37.2 mL, 59.44 mmol) was slowly added and stirred for 1 hour, then 2-bromo-9H-fluorenone (13.86g, 53.50 mmol) was added and stirred at room temperature for 24 hours. . After the reaction was terminated by adding an aqueous solution of ammonium chloride, extraction was performed using dichloromethane and water, and distillation under reduced pressure was performed before proceeding with the next reaction.

2) Compound A2 synthesis

A1 was dissolved in toluene (250 mL) in a 500 mL round bottom flask and then connected to a Dean-Stark trap. p-toluenesulphonic acid (1.84g, 10.70 mmol) was added and stirred at 100°C for 6 hours. After the reaction was terminated by adding 10% NaHCO ₃ aqueous solution, extraction was performed using toluene and water, distillation under reduced pressure was performed, and column separation was performed using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain Compound A2 (16.85g, 41.17 mmol).

3) Synthesis of Compound A3

In a 250 mL round bottom flask, 4-phenylaniline (3.29g, 19.44 mmol), 9-(4-bromophenyl)-9H-carbazole (6.05g, 18.76 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.27g, 0.29 mmol) ), (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene (BINAP) (0.36g, 0.58 mmol) and Sodium tert-butoxide (2.62g, 27.22 mmol), Toluene (150 mL) ), stirred in a bath at 100°C for 24 hours, and when the reaction was completed, toluene was removed, extracted using dichloromethane and water, distilled under reduced pressure, and the solvent was distilled under reduced pressure after using a silica gel column to obtain Compound A3 ( 6.80g, 16.56 mmol) was obtained.

4) Synthesis of Compound A4

In a 100 mL round bottom flask, A3 (1.00g, 2.44 mmol), A2 (1.10g, 2.68 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.03g, 0.04 mmol), Tri-tert-butylphosphine (0.01g, 0.07 mmol) and sodium tert-butoxide (0.33g, 1.52 mmol) were dissolved in toluene (35 mL), stirred in a bath at 100°C for 24 hours, and when the reaction was completed, toluene was removed and dichloromethane and water were used. After extraction, concentration, and column separation using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound A4 (1.12g, 1.52mmol). The NMR analysis results are shown in FIG. 6, and the FT-MS (Fourier Transform Mass Spectrometry) analysis results are shown in FIG. 12. The molecular weight of compound A4 according to FT-MS analysis was 739.31.

¹ HNMR (500MHz, CD ₂ Cl ₂ ) 8.14 (d, 2H), 7.63~7.20 (m, 30H), 7.08~7.00 (m, 5H), 6.59(d, 1H)

Synthesis Example 2: Synthesis of B3 compound

1) Synthesis of compound B1

A3 (2.50g, 6.09 mmol), 1-bromo-4-iodobenzene (2.58g, 9.13 mmol), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.04g, 0.06 mmol) in a 100 mL round bottom flask. ), Palladium(II) acetate (0.01g, 0.06 mmol) and Sodium tert-butoxide (0.88g, 9.20 mmol) were dissolved in toluene (60 mL) and stirred in a bath at 100°C for 24 hours to complete the reaction. Upon completion, toluene was removed, extraction was performed using dichloromethane and water, distillation was performed under reduced pressure, and column separation was performed using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound B1 (2.75 g, 4.86 mmol).

2) Compound B2 synthesis

Dissolve A2 (3.00g, 7.33 mmol) in Diethyl Ether (100 mL) in a 250 mL round bottom flask and cool to -78°C. Afterwards, 2.5M n-Butyllithium (3.52 mL, 8.80 mmol) was slowly added and stirred for 1 hour, and then stirred at room temperature for 1 hour. After cooling to -78°C, triethylborate (1.48 mL, 8.80 mmol) was slowly added and stirred for 1 hour, and then stirred at room temperature for 24 hours. After the reaction was terminated by adding an aqueous hydrochloric acid solution, diethyl ether was removed by blowing, and the precipitate was filtered using petroleum ether to obtain compound B2 (1.24 g, 3.31 mmol).

3) Synthesis of compound B3

B1 (1.50g, 2.65 mmol), B2 (1.19g, 3.18 mmol), tetrakis(triphenylphosphine)palladium(0) (0.15g, 0.13 mmol), and potassium carbonate (2.07g, 15.00 mmol) were added to a 100 mL round bottom flask. Toluene (28 mL), Ethanol (7 mL), and water (7 mL) were added to a mixed solution and stirred at 100°C for 24 hours. After completion of the reaction, the extract was extracted using water and dichloromethane, concentrated, and column separated using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound B3 (1.41g, 1.73 mmol). The NMR analysis results are shown in Figure 7, and the FT-MS analysis results are shown in Figure 12. The molecular weight of compound B3 according to FT-MS analysis was 815.34.

¹ HNMR (500MHz, CD ₂ Cl ₂ ) 8.14 (d, 2H), 7.73 (m, 2H), 7.76~7.19 (m, 35H), 6.92 (t, 1H), 6.86 (s, 1H), 6.65(d) , 1H)

Synthesis Example 3: Synthesis of C2 compound

1) Synthesis of compound C1

4,4'-dibromobiphenyl (5.00g, 16.03 mmol), aniline (3.73g, 40.06 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.29g, 0.32 mmol), and Tri-tert-butylphosphine in a 250 mL round bottom flask. (0.03g, 0.16 mmol) and Sodium tert-butoxide (4.62g, 48.08 mmol) were dissolved in toluene (160 mL) and stirred in a bath at 100°C for 24 hours. When the reaction was completed, toluene was removed and dichloromethane was added. After extraction using and water, it was concentrated and column separated using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound C1 (4.00g, 11.89 mmol).

2) Synthesis of compound C2

In a 100 mL round bottom flask, C1 (0.85g, 2.53 mmol), A2 (2.28g, 5.56 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.07g, 0.08 mmol), Tri-tert-butylphosphine (0.03g, 0.15 mmol) and sodium tert-butoxide (0.68g, 7.07 mmol) were dissolved in toluene (40 mL), stirred in a 100°C bath for 24 hours, and when the reaction was completed, toluene was removed and dichloromethane and water were used. After extraction, concentration, and column separation using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound C2 (1.75g, 1.76mmol). The NMR analysis results are shown in Figure 8, and the FT-MS analysis results are shown in Figure 14. The molecular weight of C2 compound according to FT-MS analysis was 993.43.

¹ HNMR (500MHz, CD ₂ Cl ₂ ) 7.41~7.32 (m, 18H), 7.21~6.84 (m, 30H), 6.56 (d, 2H), 6.20 (s, 2H)

Synthesis Example 4: Synthesis of D3 compound

1) Synthesis of Compound D1

Dibenzofuran-4-boronic acid (3.00g, 14.15 mmol), 1-bromo-4-iodobenzene (4.00g, 14.15 mmol), tetrakis(triphenylphosphine) palladium(0) (0.82g, 0.71 mmol) in a 250 mL round bottom flask. , potassium carbonate (4.84g, 35.00 mmol) was added to a mixed solution of Toluene (80 mL), Ethanol (20 mL), and water (20 mL), and stirred at 100°C for 24 hours. After completion of the reaction, the extract was extracted using water and dichloromethane, concentrated, and column separated using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound D1 (3.95 g, 12.22 mmol).

2) Compound D2 synthesis

In a 250 mL round bottom flask, 4-phenylaniline (1.80g, 10.64 mmol), D1 (3.78g, 11.70 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.15g, 0.16 mmol), (±)-2,2' -Bis(diphenylphosphino)-1,1'-binaphthalene (BINAP) (0.20g, 0.32 mmol) and Sodium tert-butoxide (1.43g, 14.89 mmol) were dissolved in toluene (100 mL) and then placed in a bath at 100°C. After stirring for 24 hours, when the reaction was completed, toluene was removed, extraction was performed using dichloromethane and water, distillation was performed under reduced pressure, and the solvent was distilled under reduced pressure after a silica gel column to obtain compound D2 (3.05 g, 7.41 mmol).

3) Synthesis of compound D3

In a 100 mL round bottom flask, D2 (1.00g, 2.43 mmol), A2 (1.09g, 2.67 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.03g, 0.04 mmol), Tri-tert-butylphosphine (0.01g, 0.07 mmol) and Sodium tert-butoxide (0.33g, 3.40 mmol) were dissolved in toluene (40 mL) and stirred in a bath at 100°C for 24 hours. When the reaction was completed, toluene was removed and dichloromethane and water were used. After extraction, concentration, and column separation using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound D3 (1.45g, 1.96 mmol). The NMR analysis results are shown in Figure 9, and the FT-MS analysis results are shown in Figure 12. The molecular weight of compound D3 according to FT-MS analysis was 740.29.

¹ HNMR (500MHz, CDCl ₃ ) 8.00 (d, 1H), 7.93 (d, 1H), 7.80 (d, 2H), 7.63 (m, 6H), 7.49~6.89 (m, 25H), 6.64 (d, 1H) ), 6.29 (s, 1H)

Synthesis Example 5: Synthesis of E2 compound

1) Compound E1 synthesis

In a 250 mL round bottom flask, 4-phenylaniline (2.00g, 11.82 mmol), 2-bromodibenzothiophene (3.42g, 13.00 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.16g, 0.18 mmol), (±)-2, 2'-Bis(diphenylphosphino)-1,1'-binaphthalene (BINAP) (0.22g, 0.35 mmol) and Sodium tert-butoxide (1.59g, 16.55 mmol) were dissolved in toluene (110 mL) and incubated at 100°C. After stirring in a bath for 24 hours, when the reaction was completed, toluene was removed, extracted using dichloromethane and water, distilled under reduced pressure, and the solvent was distilled under reduced pressure after a silica gel column to obtain compound E1 (3.05 g, 8.68 mmol).

2) Compound E2 synthesis

In a 100 mL round bottom flask, A2 (1.28g, 3.13 mmol), E1 (1.00g, 2.85 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.04g, 0.04 mmol), Tri-tert-butylphosphine (0.02g, 0.09 mmol) and Sodium tert-butoxide (0.38g, 3.98 mmol) were dissolved in toluene (40 mL) and stirred in a bath at 100°C for 24 hours. When the reaction was completed, toluene was removed and dichloromethane and water were used. After extraction, concentration, and column separation using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound E2 (1.08g, 1.59 mmol). The NMR analysis results are shown in Figure 10, and the FT-MS analysis results are shown in Figure 12. The molecular weight of E2 compound according to FT-MS analysis was 680.24.

¹ HNMR (500MHz, CDCl ₃ ) 7.97 (d, 1H), 7.88 (d, 1H), 7.73 (s, 1H), 7.69 (d, 1H), 7.64~7.59 (m, 4H), 7.46~7.03 (m , 20H), 6.87 (t, 1H), 6.71 (t, 1H), 6.60 (d, 1H), 6.52 (t, 1H), 6.22 (s, 1H)

Synthesis Example 6: Synthesis of F2 compound

1) Synthesis of compound F1

In a 250 mL round bottom flask, 4-phenylaniline (3.00g, 17.73 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.33g, 19.50 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.24g, 0.27 mmol), (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene (BINAP) (0.33g, 0.53 mmol) and Sodium tert-butoxide (2.39g, 24.82 mmol), Toluene ( 100 mL), stirred in a 100°C bath for 24 hours, and when the reaction is completed, toluene is removed, extracted using dichloromethane and water, distilled under reduced pressure, and the solvent is distilled under reduced pressure after a silica gel column, yielding Compound F1. (5.24g, 14.50 mmol) was obtained.

2) Synthesis of compound F2

In a 100 mL round bottom flask, A2 (1.00g, 2.43 mmol), F1 (0.80g, 2.21 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.03g, 0.03 mmol), Tri-tert-butylphosphine (0.01g, 0.07 mmol) and Sodium tert-butoxide (0.30g, 3.10 mmol) were dissolved in toluene (35 mL) and stirred in a bath at 100°C for 24 hours. When the reaction was completed, toluene was removed and dichloromethane and water were used. After extraction, concentration, and column separation using dichloromethane and n-hexane. Afterwards, a precipitate was prepared using dichloromethane and petroleum ether, and then filtered to obtain compound F2 (1.13g, 1.66 mmol). The NMR analysis results are shown in Figure 11, and the FT-MS analysis results are shown in Figure 12. The molecular weight of F3 compound according to FT-MS analysis was 690.32.

¹ HNMR (500MHz, CDCl ₃ ) 7.67~7.53 (m, 6H), 7.46~6.80 (m, 25H), 6.60 (d, 1H), 6.28 (s, 1H), 1.41 (s, 6H)

Example 1: Production of single-layer structure light emitting diode (A4)

A light emitting diode device with a single-layer structure containing the A4 compound synthesized in Synthesis Example 1 was manufactured. The indium-tin-oxide (ITO) glass was patterned to have an emission area of 3 mm x 3 mm and then cleaned. After transferring the substrate to the vacuum chamber, the base pressure is set to 10 ^-6 Torr, and then a hole injection layer (HAT-CN, 50Å), a hole transport layer (α-NPB; 500~1500Å), and an exciton blocking layer are placed on the ITO. Blocking layer (A4, 150Å), blue emitting material layer (host MADN doped with 4% by weight of dopant BD-1, 250Å), first electron transport layer (2-[4-(9,10-Di-2-naphthalenyl- 2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole, 100~300Å), second electron transport layer (Bphen doped with 2% by weight of Li, 100Å), electron injection layer (LiF, 5~10Å), cathode ( Al, 800~1000Å) was formed into a film.

After deposition, it was transferred from the deposition chamber into a dry box to form a film and subsequently encapsulated using UV cured epoxy and a moisture getter. This organic light emitting diode has an emission area of 9㎟.

Example 2: Fabrication of a single-layer structure light emitting diode (B3)

A light emitting diode with a single-layer structure was manufactured by repeating the procedure of Example 1, except that B3 synthesized in Synthesis Example 2 was used as the electron blocking layer instead of A4.

Example 3: Fabrication of a single-layer structure light emitting diode (C2)

A light emitting diode with a single-layer structure was manufactured by repeating the procedure of Example 1, except that C2 synthesized in Synthesis Example 3 was used as the electron blocking layer instead of A4.

Example 4: Fabrication of single-layer structure light emitting diode (D3)

A light emitting diode with a single-layer structure was manufactured by repeating the procedure of Example 1, except that D3 synthesized in Synthesis Example 4 was used instead of A4 as the electron blocking layer.

Example 5: Fabrication of a single-layer structure light emitting diode (E2)

A light emitting diode with a single-layer structure was manufactured by repeating the procedure of Example 1, except that E2 synthesized in Synthesis Example 5 was used as the electron blocking layer instead of A4.

Example 6: Production of single-layer structure light emitting diode (F2)

A light emitting diode with a single-layer structure was manufactured by repeating the procedure of Example 1, except that F2 synthesized in Synthesis Example 6 was used as the electron blocking layer instead of A4.

Comparative Example 1: Fabrication of single-layer structure light emitting diode (TCTA)

A light emitting diode with a single-layer structure was manufactured by repeating the procedure of Example 1, except that TCTA was used instead of A4 as the electron blocking layer.

Experimental Example 1: Evaluation of single-layer structure light emitting diode characteristics

The characteristics of the light emitting diodes manufactured in Examples 1 to 6 and Comparative Example 1 were evaluated. The organic light emitting diodes prepared in Examples 1 to 6 and Comparative Example 1 were connected to an external power source. The EL characteristics (driving voltage, current density, current efficiency (Cd/A), power efficiency (lm/W), external quantum efficiency (EQE), color coordinate) of all light emitting diodes manufactured in the present invention were measured using a constant current source (KEITHLEY). and was evaluated at room temperature using a photometer PR 650. The voltage-current density measurement results of the light emitting diode having a single-layer structure are shown in FIG. 13a, the voltage-current efficiency measurement results are shown in FIG. 13b, and the electroluminescence (EL) intensity measurement results are shown in FIG. 13c. In addition, the measurement results for driving voltage, current efficiency, power efficiency, external quantum efficiency (EQE), and color coordinate for each light emitting diode are shown in Table 1 below.

[Table 1]

According to Experimental Example 1, the driving voltage of the light emitting diode having a single-layer structure to which the compound according to the present invention was applied as an electron blocking layer was up to 13% compared to the light-emitting diode having a single-layer structure of the comparative example to which TCTA was applied as an electron blocking layer. decreased, current efficiency improved by up to 63%, power efficiency by up to 86%, and EQE by up to 66%. In other words, it was confirmed that the driving voltage can be lowered and the luminous efficiency can be improved in a light emitting diode having a single layer structure to which the organic compound according to the present invention is applied.

Example 7: Fabrication of a tandem structure light emitting diode device (A4)

A light emitting diode having a tandem structure containing the A4 compound synthesized in Synthesis Example 1 was manufactured. The indium-tin-oxide (ITO) glass was patterned to have an emission area of 3 mm x 3 mm and then cleaned. After transferring the substrate to the vacuum chamber, the base pressure is set to 10 ^-6 Torr, and then a hole injection layer (HAT-CN; 50Å), a lower hole transport layer (α-NPB, 500~1500Å), and a lower exciton blocking layer are placed on the ITO. Phosphorus electron blocking layer (TCTA, 150Å), blue emitting material layer (host MADN doped with 4% by weight of dopant BD-1, 250Å), lower electron transport layer (2-[4-(9,10-Di-2-naphthalenyl -2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole, 100~300Å), N-type charge generation layer (Bphen doped with 2% by weight of Li, 100Å), P-type charge generation layer (10% by weight of dopant F4TCNQ) % doped A4, 100Å), upper hole transport layer (A4, 100~300Å), upper emitting material layer YG emitting material layer (CBP doped with 5~20% Ir(2-phq) ₃ , 300Å), upper electron Transport layer (2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole, 300~400Å), electron injection layer (LiF, 5~10Å), Al Films were formed in the order of (800~1000Å).

After deposition, it was transferred from the deposition chamber into a dry box to form a film and subsequently encapsulated using UV cured epoxy and a moisture getter. This organic light emitting diode has an emission area of 9 mm ² .

Example 8: Fabrication of a tandem structure light emitting diode device (B3)

A light emitting diode with a tandem structure was manufactured by repeating the procedure of Example 7, except that B3 synthesized in Synthesis Example 2 was used instead of A4 as the host of the P-type charge generation layer and the upper hole transport layer.

Example 9: Fabrication of a tandem structure light emitting diode device (C2)

A light emitting diode with a tandem structure was manufactured by repeating the procedure of Example 7, except that C2 synthesized in Synthesis Example 3 was used instead of A4 as the host of the P-type charge generation layer and the upper hole transport layer.

Example 10: Fabrication of a tandem structure light emitting diode device (D3)

A light emitting diode with a tandem structure was manufactured by repeating the procedure of Example 7, except that D3 synthesized in Synthesis Example 4 was used instead of A4 as the host of the P-type charge generation layer and the upper hole transport layer.

Example 11: Fabrication of a tandem structure light emitting diode device (E2)

A light emitting diode with a tandem structure was manufactured by repeating the procedure of Example 7, except that E2 synthesized in Synthesis Example 5 was used instead of A4 as the host of the P-type charge generation layer and the upper hole transport layer.

Example 12: Fabrication of a tandem structure light emitting diode device (F2)

A light emitting diode with a tandem structure was manufactured by repeating the procedure of Example 7, except that F2 synthesized in Synthesis Example 6 was used instead of A4 as the host of the P-type charge generation layer and the upper hole transport layer.

Comparative example 2: Fabrication of a tandem structure light emitting diode device (α- NPB )

A light emitting diode with a tandem structure was manufactured by repeating the procedure of Example 7, except that α-NPB was used instead of A4 as the host of the P-type charge generation layer and the upper hole transport layer.

Experimental Example 2: Evaluation of tandem structure light emitting diode characteristics

The characteristics of the light emitting diodes manufactured in Examples 7 to 12 and Comparative Example 2 were evaluated by repeating the procedure of Experimental Example 1. The voltage-current density measurement results of the light emitting diode having a tandem structure are shown in FIG. 14a, the voltage-current efficiency measurement results are shown in FIG. 14b, and the electroluminescence (EL) intensity measurement results are shown in FIG. 14c. In addition, the measurement results for current efficiency, power efficiency, external quantum efficiency (EQE), and color coordinate for each light emitting diode are shown in Table 2 below.

[Table 2]

According to Experimental Example 2, a light emitting diode having a tandem structure in which the organic compound according to the present invention is applied as a P-type charge generation layer and an upper hole transport layer, in a comparative example in which α-NPB is applied as a P-type charge generation layer and an upper hole transport layer Compared to the manufactured light emitting diode with a tandem structure, the driving voltage was reduced by up to 12%, current efficiency was improved by up to 19%, power efficiency was improved by up to 28%, and EQE was improved by up to 24%. That is, it was confirmed that luminous efficiency can be improved in a light emitting diode having a tandem structure to which the organic compound according to the present invention is applied.

Summarizing the results of Experimental Example 1 and Experimental Example 2, the organic compound synthesized according to the present invention can be used alone in the hole injection layer, hole transport layer, exciton blocking layer, and P-type charge generation layer, or in combination with an appropriate hole injection/transport dopant. When used together, these organic compounds can have excellent current densities even at low voltages, allowing them to drive light-emitting diodes even at low voltages. That is, due to the excellent hole injection and hole transport characteristics of the organic compound synthesized according to the present invention, the organic compound of the present invention can be used as a hole layer, electron blocking layer, and/or charge generation layer to inject, transport, and transport holes. /Or when applied to a common layer that requires charge generation, the driving voltage of the light emitting diode can be lowered, and luminous efficiency such as current efficiency, power efficiency, and quantum efficiency, as well as luminous brightness and electric field strength, can be improved. I confirmed that it can be done.

Although the present invention has been described above based on exemplary embodiments and examples of the present invention, the present invention is not limited to the technical ideas described in the above embodiments and examples. For example, in the above-described embodiments and examples, the description was focused on the use of the compound of the present invention in an organic light-emitting diode display device, but the compound of the present invention and/or the light-emitting diode to which the compound of the present invention is applied is an organic light-emitting diode. It can also be applied to lighting devices, etc. As such, a person skilled in the art to which the present invention pertains can easily make various modifications and changes based on the above-described embodiments and examples. However, the fact that all such modifications and changes fall within the scope of rights of the present invention is more clear from the attached patent claims.

100, 200, 300, 400, 500, E: Light emitting diode
110, 210, 310, 410, 510: first electrode
120, 220, 320, 420, 520: second electrode
130, 230, 330, 430, 530: Light-emitting unit (organic light-emitting layer)
140, 240, 331, 431: hole layer
150, 250, 332, 432: hole injection layer
160, 260, 334, 342, 434, 442: Hole transport layer
170, 270, 336, 344, 436, 444: Light-emitting material layer
180, 280, 338, 346, 438, 446: Electron transport layer
190, 290, 348, 448: Electron injection layer
266, 435, 443: Electronic blocking layer
350, 450: Charge generation layer
352, 452: N-type charge generation layer
354, 454: P-type charge generation layer
500: Organic light emitting diode display device

Claims (20)

delete delete delete delete delete delete delete first electrode;
a second electrode facing the first electrode;
a first light emitting unit located between the first and second electrodes and including a first light emitting material layer;
a second light emitting unit located between the first light emitting unit and the second electrode and including a second light emitting material layer; and
P-type charge generation layer located between the first and second light emitting units
Including,
The P-type charge generation layer is a light emitting diode containing an organic compound represented by the following formula (3).
Formula 3

(In Formula 3, L ₁ to L ₃ are each independently a C6 to C30 arylene group;
A ₁₁ is an unsubstituted or substituted dibenzofuranyl group, dibenzothiophenyl group, or fluorenyl group, respectively;
A ₁₂ is an unsubstituted or substituted C6~C30 aryl group;
A ₁₃ is a substituent represented by the following formula (2);
a and b are each 0 or 1, at least one of a and b is 1, and c is 0;
In the above substitution, the substituent is a C1~C20 alkyl group or a C6~C30 aryl group)
Formula 2

(In Formula 2, R ₁ to R ₁₆ are each independently selected from the group consisting of hydrogen, deuterium, tritium, and C1 to C20 alkyl groups)

According to clause 8,
The P-type charge generation layer is a light emitting diode formed by doping the organic compound with a hole injection material.
According to clause 8,
The light emitting diode is located between the P-type charge generation layer and the first light-emitting unit and further includes an N-type charge generation layer that is an organic layer doped with an alkali metal or alkaline earth metal.
According to clause 10,
The first light emitting unit includes a hole injection layer and a first hole transport layer located between the first electrode and the first light emitting material layer, and a first light emitting layer located between the first light emitting material layer and the N-type charge generation layer. 1 further comprising an electron transport layer,
The second light emitting unit includes a second hole transport layer located between the second light emitting material layer and the P-type charge generation layer, a second electron transport layer located between the second light emitting material layer and the second electrode, and A light emitting diode further comprising an electron injection layer.
According to clause 11,
The second hole transport layer is a light emitting diode containing the organic compound.
According to clause 11,
It further includes a second hole injection layer located between the P-type charge generation layer and the second hole transport layer or between the N-type charge generation layer and the P-type charge generation layer,
The second hole injection layer is a light emitting diode formed by doping the organic compound with a hole injection material.
According to clause 11,
The second light emitting unit further includes an electron blocking layer located between the second hole transport layer and the second light emitting material layer,
A light emitting diode wherein the electron blocking layer is made of the organic compound.
delete Board;
a driving element located on the substrate;
The light emitting diode according to any one of claims 8 to 14, located on the substrate and connected to the driving element.
An organic light emitting diode display device comprising a.
delete delete According to clause 8,
In Formula 3, L ₁ to L ₃ are each independently a phenylene group, and A ₁₁ is a dibenzofuranyl group, dibenzothiophenyl group, or fluorenyl group that is unsubstituted or substituted with a C1-C20 alkyl group or a C6-C30 aryl group. Light emitting diode.
According to clause 19,
The organic compound represented by Formula 3 is any one of the following compounds: a light emitting diode.

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