KR102653731B1 - Organic compound and light emitting diode and organic light emitting diode display device using the same - Google Patents

Abstract

The present invention relates to a conjugated benzene ring constituting a fused ring derivative core and/or another aromatic ring conjugated to the benzene ring and/or an aromatic moiety directly or indirectly connected to the benzene ring. It relates to an organic compound in which an electron withdrawing group (electron acceptor) is substituted and has excellent hole injection and charge generation characteristics, and to a light emitting diode and display device in which the organic compound is applied to at least one organic material layer.

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 that have excellent charge transfer characteristics and hole injection characteristics and can lower the driving voltage of light-emitting diodes, and light-emitting diodes and organic light-emitting diodes using the same. It's about the 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. When electrons and holes meet, they form exciton, and when energy transitions to the ground state, light is generated. The organic light emitting diode display device that adopts this not only can form elements on flexible transparent substrates such as plastic, but can also be driven at low voltage (10V or less), consumes relatively little power, and has excellent color purity. It has the advantage of being outstanding. In addition, since the backlight unit of a liquid crystal display device (LCD) can be replaced with the light-emitting pixel part of a light-emitting diode, a very thin display can be implemented.

The organic light emitting layer may have a single layer structure of the light emitting material layer, or may have a multilayer structure to improve light emitting 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 multi-layer structure consisting of an electron injection layer (EIL).

Briefly looking at the process of manufacturing organic light emitting diodes,

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

(2) A hole injection layer (HIL) is formed on the anode to a thickness of 5 nm to 30 nm.

(3) Next, a hole transport layer is formed on the hole injection layer. This hole transport layer is formed by depositing an organic material such as 4,4'-bis[N-(1-naphthyl)-N-phenylamino]-biphenyl (NPB) to a thickness of approximately 30 nm to 70 nm. In the case of phosphorescent devices, in order to effectively confine triplet excitons within the light-emitting material layer, an exciton blocking layer such as an electron blocking layer (EBL) is sometimes formed between the hole transport layer and the light-emitting material layer.

(4) Next, an emitting material layer (EML) is formed on the hole transport layer. The light emitting material layer may include an appropriate host and dopant.

(5) Next, an electron transport layer (ETL) and an electron injecting layer (EIL) are formed on the light emitting material layer. For example, tris(8-hydroxy-quinolate)aluminum (Alq ₃ ) is used as the electron transport layer, and LiF is used as the electron injection layer. In the case of a phosphorescent device, a hole blocking layer (HBL) may be formed before forming the electron transport layer in order to effectively confine triplet excitons within the light emitting material layer.

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

In conventional light emitting diodes, aromatic diamine derivatives or aromatic condensed diamine derivatives described in U.S. Patent No. 4,720,432 and U.S. Patent No. 5,061,569 are known as materials for the hole injection layer or hole transport layer. Commercially, the diamine or polyamine material used in the hole injection layer or hole transport layer is DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]- Many aromatic diamine derivatives such as biphenyl-4,4'-diamine) and NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine) are known.

However, when forming a hole injection layer using DNTPD or NPB, hole injection becomes difficult due to the difference in HOMO (Highest Occupied Molecular Orbital) energy level between the hole injection layer and the hole transport layer, and the driving voltage of the light emitting diode increases. there is a problem. Additionally, when forming a charge generation layer, charges are not generated due to the high LUMO value (the HOMO value of DNTPD is -5.1 eV and the LUMO value is -2.0 eV). Ultimately, a high applied voltage is required to obtain sufficient luminance, and high driving voltage and current density place strong stress on the materials that make up the device. Therefore, it affects the stability of the material and the lifespan of the device, causing problems such as lowering the lifespan of the device and increasing power consumption.

To solve this problem, US Patent No. 6,566,807 proposed a method of doping the hole transport layer with an electron acceptor compound or forming a separate layer. However, electron-accepting compounds are unstable in handling during the manufacturing process of light-emitting diode devices or lack stability such as heat resistance during operation, which reduces their lifespan.

For example, F4-TCNQ (tetrafluorodicyanoquinodimethane), a representative electron-accepting compound used in light-emitting diode devices, has a small molecular weight and is substituted with fluorine, so it is easily sublimated and diffuses into the device during vacuum deposition. There is a risk of contaminating the device. Additionally, HATCN (1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile) has limitations in deposition thickness due to crystallization and has problems with current leakage.

Meanwhile, in order to further improve the performance of the light emitting diode and implement a white light emitting diode, a tandem type light emitting diode manufactured by stacking a plurality of unit devices has been proposed. In these stacked light emitting diodes, when a pair of holes and electrons are injected from the anode and cathode, the luminous efficiency per current density increases by the number of light emitting material layers, but due to the increased thickness, there are problems with high driving voltage and power consumption. occurs. Therefore, in order to supply positive and negative charges to each unit device, there is a charge generation layer (CGL) disposed between each unit device.

As mentioned above, high driving voltage and high current density can affect the lifespan of the device, so it is necessary to adjust the energy level of the organic layer to increase the efficiency of the light emitting diode and reduce power consumption. In particular, the electrode of a light emitting diode device is made of metal or metal oxide. Therefore, if the interface between the inorganic material and the material used as the charge injection material is not stable, the performance of the device may be significantly deteriorated due to heat applied from the outside, heat generated from the inside, or electric field applied to the device. Therefore, there is a need to develop materials that have high charge transport ability while forming a stable interface with the electrode.

The purpose of the present invention is to provide an organic compound that has excellent charge transport ability and does not damage the organic material layer, and a light emitting diode and display device containing the organic compound in an organic material layer requiring charge transport properties.

Another object of the present invention is to provide an organic compound capable of improving charge transport ability without increasing the driving voltage of the light emitting diode device, and a light emitting diode and display device including the organic compound in an organic material layer.

According to one aspect of the present invention, a conjugated benzene ring constituting the fused ring derivative core and/or another aromatic ring conjugated to the benzene ring and/or directly or indirectly connected to the benzene ring. Provides an organic compound in which a strong electron-withdrawing group is substituted on the aromatic moiety. The organic compound has excellent hole injection and charge generation characteristics.

In particular, this compound has a deep lowest unoccupied molecular orbital (deep LUMO). Therefore, when adjacent to an organic material (Hole Transporting material, HTM) with excellent hole transport ability, electrons can be received from the HTM and moved to the anode, and holes can be moved to the light-emitting material layer. Therefore, in a single light emitting layer, this material can be applied to the hole injection layer and/or hole transport layer, and in a light emitting diode with a stacked structure, it can be applied as a charge generation layer.

Therefore, according to another aspect of the present invention, the present invention relates to a light emitting diode in which the organic compound is included in an organic material layer requiring hole injection and/or charge generation.

That is, the present invention relates to a conjugated benzene ring constituting a fused ring derivative core and/or another aromatic ring conjugated to the benzene ring and/or an aromatic moiety directly or indirectly connected to the benzene ring. A light emitting diode is provided in which an organic compound substituted with a strong electron-attracting group is doped as a dopant in, for example, a hole layer such as a hole injection layer or a charge generation layer, either alone or together with a host material used in these organic layers.

In addition, according to another aspect of the present invention, the present invention relates to a conjugated benzene ring constituting a fused ring derivative core and/or another aromatic ring conjugated to the benzene ring and/or to the benzene ring. Provided is a display device including a light emitting diode in which an organic compound substituted with an aromatic moiety directly or indirectly connected to a strong electron-withdrawing group is contained in an organic material layer requiring hole injection characteristics and/or charge generation characteristics.

The present invention relates to a conjugated benzene ring constituting a fused ring derivative core and/or another aromatic ring conjugated to the benzene ring and/or an aromatic moiety directly or indirectly connected to the benzene ring. We propose an organic compound with excellent hole injection and charge generation characteristics as it has a structure in which a strong electron withdrawing group (electron acceptor) is substituted. That is, electrons strong in the conjugated benzene ring constituting the fused ring derivative core and/or other aromatic rings conjugated to the benzene ring and/or aromatic moieties directly or indirectly connected to the benzene ring. The attractor group is substituted to have a deep lowest unoccupied molecular orbital (deep LUMO), which improves hole transfer characteristics and charge generation characteristics.

Since the light emitting diode and organic light emitting diode display device including the electron injection layer made of the organic compound of the present invention can be driven by low voltage, power consumption is reduced.

In addition, the light emitting diode and organic light emitting diode display device having a stacked structure including a charge generation layer made of an organic compound of the present invention have the advantage of reducing power consumption by driving at a low voltage and realizing high purity white color.

1 is a schematic cross-sectional view of a light emitting diode according to a first exemplary embodiment of the present invention.
Figure 2 is a schematic cross-sectional view of a light emitting diode according to a second exemplary embodiment of the present invention.
Figure 3 is a schematic cross-sectional view of a light emitting diode according to a third exemplary embodiment of the present invention.
Figure 4 is a schematic cross-sectional view of a light emitting diode according to a fourth exemplary embodiment of the present invention.
Figure 5 is a schematic cross-sectional view of a light emitting diode according to a fifth exemplary embodiment of the present invention.
Figure 6 is a schematic cross-sectional view of a light emitting diode according to a sixth exemplary embodiment of the present invention.
Figure 7 is a schematic cross-sectional view of a light emitting diode according to a seventh exemplary embodiment of the present invention.
Figure 8 is a schematic cross-sectional view of a light emitting diode according to an eighth exemplary embodiment of the present invention.
9 is a schematic cross-sectional view of an organic light emitting diode display device according to an exemplary embodiment of the present invention.
10A and 10B are graphs showing the results of measuring the current density of a light emitting diode manufactured according to an exemplary embodiment of the present invention, respectively.
11A and 11B are graphs showing the results of measuring light emission luminance of a light emitting diode manufactured according to an exemplary embodiment of the present invention, respectively.
12A and 12B are graphs showing the results of measuring the luminous efficiency of a light emitting diode manufactured according to an exemplary embodiment of the present invention, respectively.
13A and 13B are graphs showing the results of measuring the external quantum efficiency of a light emitting diode manufactured according to an exemplary embodiment of the present invention, respectively.

According to one aspect of the present invention, the present invention provides an organic compound represented by the following formula (1).

Formula 1

(In Formula 1, R ₁ to R ₆ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl group, C ₁ -C ₂₀ alkylamine group, substituted or unsubstituted C ₅ -C ₃₀ aryl amine group, substituted or unsubstituted In the group consisting of a C ₅ -C ₃₀ heteroaryl amine group, a silyl group substituted with a C ₁ -C ₃₀ alkyl group, a silyl group substituted with a C ₅ -C ₃₀ aryl group, and a silyl group substituted with a C ₅ -C ₃₀ heteroaryl group. _{selected ; X1 to} Hetero arylene group; =Y and =Z are each independently selected from the group consisting of (a) to (d) of the following formula 2)

Formula 2

(In Formula 2, A ₁ and A ₂ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl group, or A ₁ and A ₂ are linked together to form an alicyclic ring, an aromatic ring, or a heteroaromatic ring. Forms a ring; A ₃ is hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or Unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloc selected from the group consisting of actual groups, substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl groups)

In an exemplary embodiment, R ₁ to R ₄ of Formula 1 are each independently selected from the group consisting of hydrogen, deuterium, -CN, and halogen, and R ₅ and R ₆ are each independently unsubstituted or CF ₃ , -CN is an aryl group or heteroaryl group substituted with at least one functional group selected from the group consisting of halogen, and Ar is unsubstituted or is substituted with at least one functional group selected from the group consisting of halogen, -CN, and -CF ₃ It is an arylene group or hetero arylene group substituted with a functional group, and A ₁ and A ₂ in Formula 2 are each independently substituted with at least one functional group selected from the group consisting of CN or halogen, -CF ₃ and -CN. It may be an aryl group or heteroaryl group.

For example, the organic compound may be any one represented by the following formula (3).

Formula 3

According to another aspect of the present invention, the present invention relates to a light emitting diode including the above-described organic compound in the hole layer and/or charge generation layer.

For example, the present invention includes a first electrode; a second electrode facing the first electrode; a light emitting unit located between the first and second electrodes and including a light emitting material layer; A light emitting diode is provided that is located between the first electrode and the light emitting unit and includes a hole layer containing an organic compound represented by Formulas 1 to 3.

In one exemplary embodiment, the hole layer is located between a hole transport layer and the hole transport layer and the first electrode and is composed of only the organic compound, or a hole injection layer in which the organic compound is doped into a hole injection host material. It can be included.

In another alternative embodiment, the hole layer includes: a hole transport layer; a first hole injection layer located between the hole transport layer and the first electrode and made of only the organic compound or a hole injection host material doped with the organic compound; It may include a second hole injection layer located between the first electrode and the first hole injection layer and made of a hole injection host material.

In another alternative embodiment, the hole transport layer may include a first hole transport layer formed by doping the organic compound into a hole transport host material.

In another alternative embodiment, the hole transport layer may further include a second hole transport layer located between the first hole transport layer and the light emitting unit and made of a hole transport host material.

In yet another embodiment of the present invention, the present invention includes a 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 first electrode and including a second light emitting material layer; A light emitting diode is provided that includes a P-type charge generation layer located between the first and second light emitting units and containing an organic compound represented by Formulas 1 to 3.

At this time, the P-type charge generation layer may be formed solely of the organic compound or may be formed by doping the organic compound into a hole injection host material.

If necessary, it may further include an N-type charge generation layer, which is an organic layer doped with an alkali metal or an alkaline earth metal and is located between the P-type charge generation layer and the second light-emitting unit.

In one exemplary embodiment, the first light emitting unit includes a first hole transport layer located between the first light emitting material layer and the P-type charge generation layer, and a first hole transport layer located between the first light emitting material layer and the second electrode. It further includes an electron injection layer and a first electron transport layer, wherein the second light-emitting unit includes a second electron transport layer positioned between the N-type charge generation layer and the second light-emitting material layer, and the first electrode. It may further include a first hole injection layer and a second hole transport layer located between the second light emitting material layer.

At this time, the first light emitting unit may further include a second hole injection layer located between the first hole transport layer and the P-type charge generation layer.

In another alternative embodiment, it may further include a second hole injection layer positioned between the P-type charge generation layer and the N-type charge generation layer.

In another alternative embodiment, the first light-emitting unit further includes an electron injection layer and a first electron transport layer positioned between the first light-emitting material layer and the second electrode, and the second light-emitting unit includes: It further includes a second electron transport layer located between the N-type charge generation layer and the second light-emitting material layer, and a hole injection layer and a hole transport layer located between the first electrode and the second light-emitting material layer, and the P The charge generation layer may be formed by doping the organic compound into a hole transport layer host material.

According to another aspect of the present invention, the present invention includes a base substrate; a driving thin film transistor located on the base substrate; the light emitting diode located on the base substrate and connected to the driving thin film transistor; An organic light emitting diode display device is provided including an encapsulation substrate that covers the light emitting diode and is bonded to the base substrate.

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

[Organic compounds]

The organic compound of the present invention is a conjugated benzene ring constituting a fused ring derivative core and/or another aromatic ring conjugated to the benzene ring and/or directly or indirectly connected to the benzene ring. It has a structure in which a strong electron withdrawing group (electron acceptor) is substituted on the aromatic moiety, and has excellent hole injection and charge generation characteristics, and can be represented by the following formula (1).

Formula 1

(In Formula 1, R ₁ to R ₆ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl group, C ₁ -C ₂₀ alkylamine group, substituted or unsubstituted C ₅ -C ₃₀ aryl amine group, substituted or unsubstituted In the group consisting of a C ₅ -C ₃₀ heteroaryl amine group, a silyl group substituted with a C ₁ -C ₃₀ alkyl group, a silyl group substituted with a C ₅ -C ₃₀ aryl group, and a silyl group substituted with a C ₅ -C ₃₀ heteroaryl group. _{selected ; X1 to} Ren group; =Y and =Z are each independently selected from the group consisting of (a) to (d) of the following formula 2)

Formula 2

(In Formula 2, A ₁ and A ₂ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl group, or A ₁ and A ₂ are linked together to form an alicyclic ring, an aromatic ring, or a heteroaromatic ring. Forms a ring; A ₃ is hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or Unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloc selected from the group consisting of actual groups, substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl groups)

As can _be seen in Formula 1, the other aromatic ring conjugated to the conjugated benzene ring constituting the conjugated ring core is a homoaromatic ring (X ₁ to X ₄ are all carbon) or a heteroaromatic ring (X ₁ to at least one may be nitrogen, oxygen, sulfur and/or phosphorus). Other aromatic rings conjugated to the conjugated benzene ring are, for example, the homoaromatic ring phenyl, or the heteroaromatic rings pyridine, pyrazine, pyrimidine, pyridazine, triazine ( It may be triazine, tetrazine, pyran, oxazine, dioxin, thiopyran, thiazine, or phosphine, but the present invention It is not limited to this.

For example, the conjugated ring containing a conjugated benzene ring constituting the core of the organic compound according to the present invention is naphthalene, quinoline, isoquinoline, cinnoline, quinazoline, It includes quinoxaline, phthalazine, chromene, isochromene, etc., but the present invention is not limited thereto.

As described above, the organic compound of the present invention has a fused ring derivative core, and the benzene ring (the ring in Formula 1 where Y and Z are connected through a double bond) constituting this fused ring is conjugated ( It has a conjugated structure, and a strong electron withholding group is connected to the conjugated benzene ring through a double bond. In addition, another aromatic ring conjugated to the conjugated benzene ring (the aromatic ring to which R ₁ to R ₄ in Formula 1 are connected) and/or an aromatic moiety directly or indirectly connected to the conjugated benzene ring (e.g., In 1, a strong electron-withdrawing group may be connected directly or indirectly to Ar, which is directly connected to the conjugated benzene ring, or to R ₅ and R ₆ ), which are connected to the conjugated benzene via Ar. Organic compounds directly substituted with strong electron-withdrawing groups can have improved hollow transport properties.

In one exemplary embodiment, R ₁ to R ₄ of Formula 1 are each independently selected from the group consisting of hydrogen, deuterium, -CN, and halogen, and R ₅ and R ₆ are each independently unsubstituted or CF ₃ , -CN, and halogen. Ar is an aryl group or heteroaryl group substituted with at least one functional group selected from the group consisting of halogen, -CN, and -CF 3. Ar is unsubstituted or at least one selected from the group consisting of halogen, -CN, and -CF ₃ It is an arylene group or hetero arylene group substituted with two functional groups, and A ₁ and A ₂ in Formula 2 are each independently substituted with at least one functional group selected from the group consisting of CN or halogen, -CF ₃ and -CN. It may be an aryl group or a heteroaryl group. At this time, the substituents represented by =Y and =Z in Formula 1 may have stronger electron attracting properties than the substituents represented by R ₁ to R ₆ in Formula 1.

As described above, C ₅ -C ₃₀ aryl group, C ₅ -C ₃₀ heteroaryl group, C ₆ -C ₃₀ aryl group constituting R ₁ to R ₆ of Formula 1 and/or A ₁ to A ₃ of Formula 2 Real group, C ₆ -C ₃₀ heteroaryloxyl group, C ₅ -C ₃₀ aryl amine group, C ₅ -C ₃₀ heteroaryl amine group; The C ₅ -C ₃₀ arylene group and C ₅ -C ₃₀ hetero arylene group constituting Ar of Formula 1 may each independently be substituted or unsubstituted. In one exemplary embodiment, these aryl groups, heteroaryl groups, aryloxyl groups, heteroaryloxyl groups, arylene groups, hetero arylene groups are hydrogen, -OH, -CN, -NO ₂ , -CF ₃ , fluorine. It may be substituted with at least one strong electron-withdrawing group selected from the group consisting of an alkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, and substituted or unsubstituted C ₁ -C ₂₀ alkoxy group. . For example, when these functional groups constituting R ₁ to R ₆ and/or Ar of Formula 1 are strong electron-withdrawing groups and are aromatic groups such as homo aryl group, hetero aryl group, homo aryloxyl group, or hetero aryloxyl group. , strong charge generation characteristics can be improved by reducing orbital overlap.

For example, a homo aryl group or a homo aryloxyl group includes deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C ₁ -C ₂₀ alkyl group. , phenyl, naphthyl, indenyl, anthracenyl, fluorine substituted with at least one strong electron withdrawing group selected from the group consisting of substituted or unsubstituted C ₁ -C ₂₀ alkoxy groups. Fluorenyl, phenalenyl, phenanthrenyl, pyrenyl, tetraphenyl, biphenyl, terphenyl, spiro- It may be selected from the group consisting of fluorenyl, phenoxyl, and naphthalenoxyl, but the present invention is not limited thereto.

In addition, the heteroaryl group or heteroaryloxyl group is an aromatic compound containing heterogeneous elements such as elements other than carbon, for example, nitrogen (N), oxygen (O), and/or sulfur (S). At this time, 1 to 4 heterogeneous elements may be contained. More specifically, the heteroaryl group or heteroaryloxyl group is unsubstituted, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, substituted or unsubstituted C Carbazole, pyridazine, pyrazine substituted with at least one strong electron-withdrawing group selected from the group consisting of ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group. , imidazole, pyrazole, oxadiazole, triazole, furan, pyrimidine, oxazole, pyrrole, pyridine ( pyridine, triazine, thiazole, thiophene, tetrazine, pyran, oxazine, dioxin, thiopyran, It may be selected from the group consisting of thiazine, phosphine, and N-substituted spiro-fluorenyl, but the present invention is not limited thereto.

In addition, the hetero arylene group constituting Ar of Formula 1 is an aromatic compound containing elements other than carbon, for example, heterogeneous elements such as nitrogen (N), oxygen (O), and/or sulfur (S). At this time, 1 to 4 heterogeneous elements may be contained. More specifically, the arylene group or hetero arylene group constituting Ar of Formula 1 is unsubstituted, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, or substituted. Phenylene, naphthylene, substituted with at least one strong electron-withdrawing group selected from the group consisting of unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, It may be selected from the group consisting of fluorenylene, biphenylene, terphenylene, unsubstituted or N-substituted spiro-fluorenylene, etc. For example, Ar in Formula 1 is an arylene group or hetero group connecting the conjugated benzene ring in the core of the conjugated ring derivative and the nitrogen atom constituting the amine (the nitrogen atom to which R ₅ and R ₆ are connected) at the meta or para position. It may be an arylene group.

As described above, the organic compound of the present invention is directly or It has a structure in which a strong electron withdrawing group is substituted on an indirectly connected aromatic moiety. In one exemplary embodiment, a substituent (=Y, =Z) that is bonded to the conjugated benzene ring, which is part of the ring structure of the conjugated ring derivative core, is a substituent (R ₁ ) that is bonded to the left aromatic ring structure of the conjugated phenyl core. to R ₄ ) and the substituents (R ₅ , R ₆ ) that can be bonded to the aromatic (Ar) connected to the right side of the conjugated phenyl core have stronger electron-withdrawing properties.

In such organic compounds, the conjugated benzene ring of the fused derivative core with another aromatic ring fused to it and an aromatic moiety directly or indirectly connected may have high planarity, resulting in thermal stability. hole injection characteristics and charge generation characteristics are improved by the substituent with electron-withdrawing characteristics.

Therefore, the organic compound of the present invention can be used as a hole injection layer, a doped hole transport layer, or a charge generation layer in a laminated structure light emitting diode to increase the luminous efficiency of the light emitting diode and lower the driving voltage.

In addition, the organic compound of the present invention has a deep lowest unoccupied molecular orbital function (deep LUMO), so when used in an organic material layer adjacent to an organic material (Hole Transporting material, HTM) with excellent hole transport ability, the highest occupied molecule of the HTM It receives electrons in the orbital (HOMO) and moves them in the direction opposite to HTM (for example, toward the anode), and the holes generated by this move toward the EML direction (for example, toward the cathode), which has the property of generating charges.

Accordingly, the organic compound of the present invention can be used as a hole injection layer, a doped hole transport layer, or a charge generation layer in a stacked structure light emitting diode, to increase the luminous efficiency of the light emitting diode and lower the driving voltage.

For example, in Formula 1, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen, deuterium, -CN, and halogen, and R ₅ and R ₆ are each independently unsubstituted or CF ₃ , -CN and halogen. Ar is unsubstituted or is substituted with at least one functional group selected from the group consisting of halogen, -CN, and -CF ₃ . It is a substituted arylene group or hetero arylene group, and A ₁ and A ₂ in Formula 2 are each independently an aryl group substituted with at least one functional group selected from the group consisting of CN or halogen, -CF ₃ and -CN. Or it may be a heteroaryl group.

In this way, when a strong electron-withdrawing group is connected directly or through an aromatic ring, the hole injection characteristics can be greatly improved, and when such an electron-withdrawing group is substituted through an aromatic ring, the charge generation ability is greatly improved, resulting in light emission. The driving voltage of the diode can be lowered.

In an exemplary embodiment, the organic compound of the present invention may be any one of the organic compounds represented by Formula 3 below.

Formula 3

[Light-emitting diode and display device]

As described above, the organic compound of the present invention has excellent hole injection characteristics and/or charge generation characteristics, so it can be applied as a hole injection layer or charge generation layer of a light emitting diode. The structure of the light emitting diode according to the present invention will be described. do. 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 ( A light emitting unit 130 located between 110 and 120, a hole injection layer 140 located between the first electrode 110 and the light emitting unit 130, and the light emitting unit 130 and the hole injection layer 140. ) and a hole transport layer 150 located between them.

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 may be made of indium-tin-oxide (ITO) or indium-zinc-oxide (IZO).

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 unit 130 includes a light emitting material layer 132, an electron transport layer 134, and an electron injection layer 136. The electron transport layer 134 is located between the second electrode 120 and the light emitting material layer 132, and the electron injection layer 136 is located between the second electrode 120 and the electron transport layer 134.

The light emitting material layer 132 may be formed by doping a host material with a dopant. For example, when the light-emitting material layer 132 emits blue (B) light, the light-emitting material layer 132 is made of anthracene derivative, pyrene derivative, and perylene derivative. At least one fluorescent host material selected from the group (e.g., DPVBi(4,4'-bis(2,2'-diphenylyinyl)-1,1'-biphenyl, AND(9,10-di-(2-naphtyl )anthracene), TBADN(2,5,8,11- tetra-t-butylperylene, 2-tert-butyl-9,10-di(2-naphthyl)anthracene), MADN(2-methyl-9,10-di (2-naphtyl)anthracene), TBPi (2, 2',2"-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), etc.) with a fluorescent dopant (e.g., BCzVBi(4,4'-bis(9-ethyl-3-carbazovinylene)- 1,1'-biphenyl), BD-1(diphenyl-[4-(2-[1,1;4,1]terphenyl-4 -yl-vinyl)-phenyl]-amine) may be doped.

In addition, when the light-emitting material layer 132 emits green (G) light, the light-emitting material layer 132 is a phosphorescent host material (dp ₂ Ir(acac), op ₂ Ir) made of a carbazole-based compound or a metal complex. (acac), etc.) may be doped with a phosphorescent dopant. In addition, when the light-emitting material layer 132 emits red (R) light, the light-emitting material layer 132 is a phosphorescent host material made of a carbazole-based compound or a metal complex (for example, Btp ₂ Ir(acac)). etc.) may be doped with a phosphorescent dopant. The dopant material may be added at a rate of approximately 0.1 to 50% by weight based on the host material.

The electron transport layer 134 is made of oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimidazole (e.g., 2- It may be made of an electron transport material such as [4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole). However, it is not limited to this.

Additionally, the electron injection layer 136 may be made of an electron injection material such as LIF or lithium quinolate (LiQ). However, it is not limited to this.

The hole transport layer 150 is located adjacent to the light emitting material layer 132 of the light emitting unit 130 and is located between the first electrode 110 and the light emitting unit 130. For example, the hole transport layer 150 is TPD (N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-bi-phenyl-4,4'-diamine) or NPB ( It may be composed of N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine), but is not limited thereto.

The hole injection layer 140 is located between the hole transport layer 150 and the first electrode 110, and is made of an organic material represented by Formulas 1 to 3, or an organic material represented by Formulas 1 to 3 in the hole injection host material. The material may be doped.

When the hole injection layer 140 includes a host material and an organic compound represented by Formula 1 to Formula 3, the hole injection host material is MTDATA (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), CuPc (copper phthalocyanine), NPB (N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4-diamine), HATCN(1,4,5,8, It may be 9,11-hexaazatriphenylenehexacarbonitrile) or PEDOT/PSS (poly(3,4-ethylenedioxythiphene)polystyrene sulfonate) and may be doped with about 0.1 to 50% by weight of organic compounds of Formulas 1 to 3. However, it is limited to this. It doesn't work.

In other words, the light emitting diode 100 according to the first exemplary embodiment of the present invention has first and second electrodes 110 and 120 facing each other and between the first and second electrodes 110 and 120. It includes a light emitting unit 130 located in and a hole layer located between the first electrode 110 and the light emitting unit 130 and composed of a hole injection layer 140 and a hole transport layer 150, and the hole injection layer 140 ) may be formed solely from the organic compounds of Formulas 1 to 3 or may be formed by doping the organic compounds of Formulas 1 to 3 into a hole injection host material.

If holes pass through the light-emitting material layer 132 and move to the second electrode 120, or electrons pass through the light-emitting material layer 132 and move to the first electrode 110, the lifespan and efficiency of the device may be reduced. there is. To prevent this, the light emitting diode 100 may include an exciton blocking layer on at least one of the top and bottom of the light emitting material layer 132.

For example, in order to prevent the movement of holes between the light emitting material layer 132 and the electron transport layer 134, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) with a low HOMO level and /or between a hole blocking layer (HBL) laminated with a material such as BAlq (bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III), and the light emitting material layer 132 and the hole transport layer 150 In order to prevent the movement of electrons, at least one of the electron blocking layers (EBL) laminated with a material such as TCTA (4,4',4''-Tris(carbazol-9-yl)-triphenylamine) can be further laminated. there is.

As described above, the organic compound of the present invention is directly or It has a structure in which a strong electron withdrawing group is substituted on an indirectly connected aromatic moiety and has excellent hole injection characteristics. Additionally, the organic compound of the present invention has a deep lowest unoccupied molecular orbital function (deep LUMO). Therefore, for example, when the hole injection layer 140 is made of an organic compound of Formula 1 or is formed by doping a host material with an organic compound of Formulas 1 to 3, the luminous efficiency of the light emitting diode 100 increases.

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, 220), a light emitting unit 230 located between the first electrode 210 and the light emitting unit 230, and a hole injection layer 240 including first and second layers 242 and 244, and , includes a hole transport layer 250 located between the light emitting unit 230 and the hole injection layer 240.

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 unit 230 includes a light emitting material layer 232, an electron transport layer 234, and an electron injection layer 236. The electron transport layer 234 is located between the second electrode 220 and the light emitting material layer 232, and the electron injection layer 236 is located between the second electrode 220 and the electron transport layer 234.

The light emitting material layer 232 may be formed by doping a host material with a dopant. The electron transport layer 234 is made of oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimidazole (e.g., 2- It is made of an electron transport material such as [4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), and the electron injection layer 236 is LIF or LiQ ( It may be made of an electron injection material such as lithium quinolate.

The hole transport layer 250 is located adjacent to the light emitting material layer 232 of the light emitting unit 230 and is located between the first electrode 210 and the light emitting unit 230. For example, the hole transport layer 250 may be made of TPD or NPB.

The hole injection layer 240 includes a first layer 242 and a second layer 244 sequentially stacked on the first electrode 210. That is, the first layer 242 is located between the first electrode 210 and the second layer 244.

The first layer 242 is made of a hole injection material such as MTDATA, CuPc, NPB or PEDOT/PSS, and the second layer 244 is made of a material represented by Formulas 1 to 3 or a hole injection host material with the formula It may be made by doping with materials of formulas 1 to 3.

When the second layer 244 of the hole injection layer 240 includes a host material and an organic compound of Chemical Formulas 1 to 3, the host material may be MTDATA, CuPc, NPB, or PEDOT/PSS and has Chemical Formulas 1 to 3 The organic compound may be doped in an amount of about 0.1 to 50% by weight. However, it is not limited to this.

In contrast, the first layer 242 is made of a material represented by Formula 1 to Formula 3 or is made by doping a hole injection host material with an organic material represented by Formula 1 to Formula 3, and the second layer 244 is made of MTDATA, It can be composed solely of hole injection materials such as CuPc, NPB or PEDOT/PSS.

That is, in the light emitting diode 200 according to the second embodiment of the present invention, the hole injection layer 240 is made of only a hole injection material and an organic compound of Formula 1 to Formula 3, or the hole injection material has Formula 1. It has a double-layer structure of layers doped with organic compounds of formulas 3 through 3.

In other words, the light emitting diode 200 according to the second embodiment of the present invention has first and second electrodes 210 and 220 facing each other and located between the first and second electrodes 210 and 220. It includes a light emitting unit 230 and a hole layer (hole injection layer) located between the first electrode 210 and the light emitting unit 230 and made of first and second layers 242 and 244, and the first layer of the hole layer The second layer 244 may be formed only of the organic compounds of Formulas 1 to 3, or may be formed by doping a hole injection host material with the organic compounds of Formulas 1 to 3.

In addition, a hole blocking layer (HBL) to prevent the movement of holes between the light-emitting material layer 232 and the electron transport layer 234, and a hole blocking layer (HBL) to prevent the movement of electrons between the light-emitting material layer 232 and the hole transport layer 250. At least one exciton blocking layer among the electron blocking layers (EBL) may be further formed.

As described above, the organic compound of the present invention is directly or It has a structure in which a strong electron withdrawing group is substituted on an indirectly connected aromatic moiety and has excellent hole injection characteristics. Additionally, the organic compound of the present invention has a deep lowest unoccupied molecular orbital function (deep LUMO). Therefore, the light emission of the light emitting diode 200 including the hole injection layer 240 is made of an organic compound of Formula 1 to Formula 3 or includes a layer formed by doping a host material with an organic compound of Formula 1 to Formula 3. Efficiency increases.

Figure 3 is a schematic cross-sectional view of a light emitting diode 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, It includes a light emitting unit 330 located between the first electrode 310 and the light emitting unit 330 and a doped hole transport layer (doped-HTL, 350) located between the first electrode 310 and the light emitting unit 330.

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 light emitting unit 330 includes a light emitting material layer 332, an electron transport layer 334, and an electron injection layer 336. The electron transport layer 334 is located between the second electrode 320 and the light emitting material layer 332, and the electron injection layer 336 is located between the second electrode 320 and the electron transport layer 334.

The light emitting material layer 332 may be formed by doping a host material with a dopant. The electron transport layer 334 is made of oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimidazole (e.g., 2- It is made of an electron transport material such as [4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), and the electron injection layer 336 is LIF or LiQ ( It may be made of an electron injection material such as lithium quinolate.

The doped hole transport layer 350 is formed by doping a hole transport host material with an organic compound of Formula 1 to Formula 3. For example, the hole transport host material may be TPD or NPB, and may be doped with an organic compound of Formula 1 to Formula 3 in an amount of about 0.1 to 50% by weight. However, it is not limited to this.

In other words, the light emitting diode 300 according to the third embodiment of the present invention has first and second electrodes 310 and 320 facing each other and located between the first and second electrodes 310 and 320. It is located between the light emitting unit 330, the first electrode 310, and the light emitting unit 330 and includes a single layer of hole layer, and the hole layer is doped with an organic compound of Formula 1 to Formula 3 in a hole transport host material. It is a doped hole transport layer 350 formed by.

In addition, a hole blocking layer (HBL) to prevent the movement of holes between the light emitting material layer 332 and the electron transport layer 334, and a hole blocking layer (HBL) to prevent the movement of electrons between the light emitting material layer 332 and the doped hole transport layer 350. At least one exciton blocking layer among the electron blocking layers (EBL) may be further formed to prevent.

As described above, since the organic compound of the present invention has excellent hole injection properties, the doped hole transport layer 350, which is formed by doping the organic compound of Formula 1 to Formula 3 into a hole transport host material, is formed by doping the hole injection layer and the hole injection layer. It can also serve as a transport layer. Therefore, even if only the hole transport layer 350 doped with the organic compound of Formula 1 to Formula 3 exists between the light emitting unit 330 and the first electrode 310, sufficient hole injection and hole transport characteristics can be obtained. That is, in the light emitting diode 300 according to the third embodiment of the present invention, one side of the doped hole transport layer 350 is in contact with the first electrode 310, and the other side is in contact with the light emitting material layer 332 of the light emitting unit 330. ) is located in contact with the

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 light emitting unit 430 located between the first electrode 410 and the light emitting unit 430, and a hole including a first layer (doped-HTL, 452) and a second layer 454. Includes a transport layer 450.

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 light emitting unit 430 includes a light emitting material layer 432, an electron transport layer 434, and an electron injection layer 436. The electron transport layer 434 is located between the second electrode 420 and the light emitting material layer 432, and the electron injection layer 436 is located between the second electrode 420 and the electron transport layer 434.

The light emitting material layer 432 may be formed by doping a host material with a dopant. The electron transport layer 434 is made of oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimidazole (e.g., 2- It is made of an electron transport material such as [4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), and the electron injection layer 436 is LIF or LiQ ( It may be made of an electron injection material such as lithium quinolate.

The hole transport layer 450 includes a first layer 452 and a second layer 454 sequentially stacked on the first electrode 410. That is, the first layer 452 is located between the first electrode 410 and the second layer 454.

The first layer 452 is formed by doping a hole transport host material such as TPD or NPB with an organic compound of Formula 1 to Formula 3. At this time, the organic compounds of Formulas 1 to 3 may be doped in an amount of about 0.1 to 50% by weight. Meanwhile, the second layer 454 is made only of a hole transport material such as TPD or NPB.

That is, compared with the light emitting diode 300 shown in FIG. 3, in the light emitting diode 400 according to the fourth embodiment of the present invention, the first layer 452, which is a doped hole transport layer, and the light emitting unit 430 A second layer 454 made only of a hole transport material is additionally formed between the light emitting material layer 432.

In other words, the light emitting diode 400 according to the fourth embodiment of the present invention has first and second electrodes 410 and 420 facing each other and located between the first and second electrodes 410 and 420. It includes a light emitting unit 430 and a hole layer located between the first electrode 410 and the light emitting unit 430, wherein the hole layer is a first layer 452, which is a hole transport layer doped with the organic compound of the present invention. A second layer 454 made of only a hole transport material is formed between the light emitting material layers 432 of the light emitting unit 430.

In addition, a hole blocking layer (HBL) to prevent the movement of holes between the light emitting material layer 432 and the electron transport layer 434, and a hole blocking layer (HBL) to prevent the movement of electrons between the light emitting material layer 432 and the doped hole transport layer 450. At least one exciton blocking layer among the electron blocking layers (EBL) may be further formed to prevent.

As described above, since the organic compound of the present invention has excellent hole injection properties, the first layer 452 of the doped hole transport layer 450 is formed by doping the organic compound of Formula 1 to Formula 3 into a hole transport host material. ) can serve as both a hole injection layer and a hole transport layer. In addition, since the hole transport layer 450 further includes a second layer 454 made only of a hole transport material between the light emitting material layer 432 and the first layer 452, hole movement into the light emitting material layer 432 The characteristics are further improved.

Figure 5 is a schematic cross-sectional view of a light emitting diode according to a fifth exemplary embodiment of the present invention. As shown in FIG. 5, the light emitting diode 500 according to the fifth embodiment of the present invention includes a first electrode 510 and a second electrode 520 facing each other, and a first and second electrode 510, 520), a first light-emitting unit (upper light-emitting unit, 530) located between the first electrode 510 and the first light-emitting unit 530, and a second light-emitting unit (lower light-emitting unit, 540), It includes a charge generation layer 550 located between the first and second light emitting units 530 and 540.

As described above, the first electrode 510 is an anode and is made of a conductive material with a relatively high work function, and the second electrode 520 is a cathode and is made of a conductive material with a relatively small work function.

The first light-emitting unit 530 includes a first hole transport layer (upper hole transport layer, 532), a first light-emitting material layer (upper light-emitting material layer, 534), a first electron transport layer (upper electron transport layer, 536), and electrons. Includes an injection layer 538. The first light emitting material layer 534 is located between the first hole transport layer 532 and the second electrode 520, and the first electron transport layer 536 is located between the first light emitting material layer 534 and the second electrode 520. The electron injection layer 538 is located between the first electron transport layer 536 and the second electrode 520.

In addition, the second light emitting unit 540 includes a hole injection layer 542, a second hole transport layer (lower hole transport layer, 544), a second light emitting material layer (lower light emitting material layer, 546), and a second electron Includes a transport layer (lower electron transport layer, 548).

The hole injection layer 542 is located between the first electrode 510 and the second hole transport layer 544, and the second hole transport layer 544 is located between the hole injection layer 542 and the second light emitting material layer 546. and the second light emitting material layer 546 is located between the second hole transport layer 544 and the second electron transport layer 548.

Each of the first and second light emitting material layers 534 and 546 may be formed by doping a host material with a dopant and emit different colors.

For example, the second light-emitting material layer 546 may emit blue light, and the first light-emitting material layer 534 may emit green, yellow-green (YG), or orange light, which has a longer wavelength than blue. For example, when constructing a yellow-green light-emitting material layer, CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl) may be used as a host material for the first light-emitting material layer 534. Dopants such as , Ir(2-phq) ₃ can be used.

Each of the first and second hole transport layers 532 and 544 may be made of a hole transport host such as TPD or NPB. The first and second hole transport layers 532 and 544 may be made of the same material or may be made of different materials. In addition, the hole injection layer 542 is made of a hole injection material such as MTDATA, CuPc, NPB, HATCN, or PEDOT/PSS, or these hole injection host materials contain about 0.1 to 50% by weight of organic compounds of Formulas 1 to 3. It can be doped with .

Each of the first and second electron transport layers 536 and 548 is composed of oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimide. It is made of an electron transport material such as azole (e.g., 2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), and the electron injection layer (538) may be made of an electron injection material such as LIF or lithium quinolate (LiQ). The first and second electron transport layers 536 and 548 may be made of the same material or may be made of different materials.

The charge generation layer 550 is located between the first light-emitting unit 530 and the second light-emitting unit 540, and includes an N-type charge generation layer (N-CGL, 552) adjacent to the second light-emitting unit 540. It includes a P-type charge generation layer (P-CGL, 554) adjacent to the first light emitting unit 530.

The N-type charge generation layer 552 injects electrons into the second light-emitting unit 540, and the P-type charge generation layer 554 injects holes into the first light-emitting unit 530.

The N-type charge generation layer 552 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 552 may be a material such as Bphen (4,7-dipheny-1,10-phenanthroline) or MTDATA, and the alkali metal or alkaline earth metal is about 0.01 to 30% by weight. It can be doped with .

The P-type charge generation layer 554 may be made of an organic material of Formulas 1 to 3, or may be formed by doping a hole injection host material with an organic compound of Formulas 1 to 3. When the P-type charge generation layer 554 includes a hole injection host material and an organic compound of Formula 1 to Formula 3, the hole injection host material may be MTDATA, CuPc, NPB, HATCN, or PEDOT/PSS, and may be represented by Formula 1 to Formula 3. The organic compound of 3 may be doped in an amount of about 0.1 to 50% by weight. However, it is not limited to this.

In addition, a hole blocking layer (HBL) to prevent the movement of holes between the light emitting material layers (534, 546) and the electron transport layers (536, 548), and a hole blocking layer (HBL) between the light emitting material layers (534, 546) and the electron transport layers (532, 544) ) At least one exciton blocking layer among the electron blocking layers (EBL) may be further formed to prevent the movement of electrons.

As described above, the organic compound of the present invention is directly or The indirectly connected aromatic moiety is substituted with a strong electron withdrawing group and has a deep LUMO value, resulting in excellent hole injection and charge generation characteristics.

Therefore, it includes a charge generation layer 540 composed of a P-type charge generation layer 544 made of an organic compound of Formula 1 to Formula 3 or formed by doping a host material with an organic compound of Formula 1 to Formula 3. The stacked structure light emitting diode 500 is used for white light emission and increases light emission efficiency.

Figure 6 is a schematic cross-sectional view of a light emitting diode according to a sixth exemplary embodiment of the present invention. As shown in FIG. 6, the light emitting diode 600 according to the sixth embodiment of the present invention includes a first electrode 610 and a second electrode 620 facing each other, and a first and second electrode 610, 620), a first light-emitting unit (upper light-emitting unit, 630) located between the first electrode 610 and the first light-emitting unit 630, and a second light-emitting unit (lower light-emitting unit, 640), It includes a charge generation layer 650 located between the first and second light emitting units 630 and 640.

As described above, the first electrode 610 is an anode and is made of a conductive material with a relatively high work function, and the second electrode 620 is a cathode and is made of a conductive material with a relatively small work function.

The first light-emitting unit 630 includes a first hole injection layer (upper hole injection layer, 631), a first hole transport layer (upper hole transport layer, 633), and a first light-emitting material layer (upper light-emitting material layer, 635). , a first electron transport layer (upper electron transport layer, 637), and an electron injection layer (538).

The first hole transport layer 633 is located between the first hole injection layer 631 and the second electrode 620, and the first light emitting material layer 635 is located between the first hole transport layer 633 and the second electrode 620. It is located in between. The first electron transport layer 637 is located between the first light emitting material layer 635 and the second electrode 620, and the electron injection layer 639 is located between the first electron transport layer 637 and the second electrode 620. It is located in

Additionally, the second light emitting unit 640 includes a second hole injection layer (lower hole injection layer, 642), a second hole transport layer (lower hole transport layer, 644), and a second light emitting material layer (lower light emitting material layer, 646) and a second electron transport layer (lower electron transport layer, 648).

The second hole injection layer 642 is located between the first electrode 610 and the second hole transport layer 644, and the second hole transport layer 644 is located between the second hole injection layer 642 and the second light emitting material layer. (646), and the second light emitting material layer (646) is located between the second hole transport layer (644) and the second electron transport layer (648).

Each of the first and second light emitting material layers 635 and 646 may be formed by doping a host material with a dopant and emit different colors.

For example, the second light-emitting material layer 646 may emit blue light, and the first light-emitting material layer 635 may emit green, yellow-green (YG), or orange light, which has a longer wavelength than blue.

Each of the first and second hole transport layers 633 and 644 may be made of a hole transport host such as TPD or NPB. The first and second hole transport layers 633 and 644 may be made of the same material or may be made of different materials. In addition, the first and second hole injection layers 631 and 642 are made of a hole injection material such as MTDATA, CuPc, HATCN, or PEDOT/PSS, or the organic compounds of Formulas 1 to 3 are added to these hole injection host materials. It may be doped from 0.1 to 50% by weight. The first and second hole injection layers 631 and 642 may be made of the same material or may be made of different materials.

Each of the first and second electron transport layers 637 and 648 is oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimi It is made of an electron transport material such as azole (e.g., 2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), and the electron injection layer (639) may be made of an electron injection material such as LIF or LiQ (lithium quinolate). The first and second electron transport layers 637 and 648 may be made of the same material or may be made of different materials.

The charge generation layer 650 is located between the first light-emitting unit 630 and the second light-emitting unit 640, and includes an N-type charge generation layer (N-CGL, 652) adjacent to the second light-emitting unit 640. It includes a P-type charge generation layer (P-CGL, 654) adjacent to the first light emitting unit 630.

The N-type charge generation layer 652 injects electrons into the second light-emitting unit 640, and the P-type charge generation layer 654 injects holes into the first light-emitting unit 630.

The N-type charge generation layer 652 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 552 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 654 may be made of an organic material of Formulas 1 to 3, or may be formed by doping a hole injection host material with an organic compound of Formulas 1 to 3. When the P-type charge generation layer 654 includes a hole injection host material and an organic compound of Formula 1 to Formula 3, the hole injection host material may be MTDATA, CuPc, HATCN, or PEDOT/PSS and has a hole injection host material of Formula 1 to Formula 3. The organic compound may be doped at about 0.1 to 50% by weight. However, it is not limited to this.

In addition, a hole blocking layer (HBL) to prevent the movement of holes between the light emitting material layers (635, 646) and the electron transport layers (637, 648), and the light emitting material layers (635, 646) and the hole transport layers (633, 644) ) At least one exciton blocking layer among the electron blocking layers (EBL) may be further formed to prevent the movement of electrons.

As described above, the organic compound of the present invention is directly or The indirectly connected aromatic moiety is substituted with a strong electron withdrawing group and has a deep LUMO value, resulting in excellent hole injection and charge generation characteristics.

Therefore, it includes a charge generation layer 650 composed of a P-type charge generation layer 654 made of an organic compound of Formula 1 to Formula 3 or formed by doping a host material with an organic compound of Formula 1 to Formula 3. The luminous efficiency of the stacked structure light emitting diode 600 increases.

Figure 7 is a schematic cross-sectional view of a light emitting diode according to a seventh exemplary embodiment of the present invention. As shown in FIG. 7, the light emitting diode 700 according to the seventh embodiment of the present invention includes a first electrode 710 and a second electrode 720 facing each other, and a first and second electrode 710, 720), a first light-emitting unit (upper light-emitting unit, 730) located between the first electrode 710 and the first light-emitting unit 730, and a second light-emitting unit (lower light-emitting unit, 740), It includes a charge generation layer 750 located between the first and second light emitting units 730 and 740.

As described above, the first electrode 710 is an anode and is made of a conductive material with a relatively high work function, and the second electrode 720 is a cathode and is made of a conductive material with a relatively small work function.

The first light-emitting unit 730 includes a first hole transport layer (upper hole transport layer, 732), a first light-emitting material layer (upper light-emitting material layer, 734), a first electron transport layer (upper electron transport layer, 736), and electrons. Includes an injection layer 738. The first light emitting material layer 734 is located between the first hole transport layer 732 and the second electrode 720, and the first electron transport layer 736 is located between the first light emitting material layer 734 and the second electrode 720. The electron injection layer 738 is located between the first electron transport layer 736 and the second electrode 720.

Additionally, the second light emitting unit 740 includes a first hole injection layer (lower hole injection layer, 742), a second hole transport layer (lower hole transport layer, 744), and a second light emitting material layer (lower hole injection layer, 746) and a second electron transport layer (lower electron transport layer, 748).

The first hole injection layer 742 is located between the first electrode 710 and the second hole transport layer 744, and the second hole transport layer 744 is located between the first hole injection layer 742 and the second light emitting material layer. (746), and the second light emitting material layer (746) is located between the second hole transport layer (744) and the second electron transport layer (748).

Each of the first and second light emitting material layers 734 and 746 may be formed by doping a host material with a dopant and emit different colors.

For example, the second light-emitting material layer 746 may emit blue light, and the first light-emitting material layer 734 may emit green, yellow-green (YG), or orange light, which has a longer wavelength than blue.

Each of the first and second hole transport layers 732 and 744 may be made of a hole transport host such as TPD or NPB. The first and second hole transport layers 732 and 744 may be made of the same material or may be made of different materials. In addition, the first hole injection layer 742 is made of a hole injection material such as MTDATA, CuPc, HATCN, or PEDOT/PSS, or these hole injection host materials are doped with about 0.1 to 50% by weight of the compounds of Formulas 1 to 3. It can be.

Each of the first and second electron transport layers 736 and 748 is composed of oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimide. It is made of an electron transport material such as azole (e.g., 2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), and the electron injection layer (738) may be made of an electron injection material such as LIF or lithium quinolate (LiQ). The first and second electron transport layers 736 and 744 may be made of the same material or may be made of different materials.

The charge generation layer 750 is located between the first light-emitting unit 730 and the second light-emitting unit 740, and includes an N-type charge generation layer (N-CGL, 752) adjacent to the second light-emitting unit 740. , a P-type charge generation layer (P-CGL, 754) adjacent to the first light-emitting unit 730, and a second hole injection located between the N-type charge generation layer 752 and the P-type charge generation layer 754. layer (lower hole injection layer, 756).

The N-type charge generation layer 752 injects electrons into the second light-emitting unit 740, and the P-type charge generation layer 754 injects holes into the first light-emitting unit 730.

The N-type charge generation layer 752 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 552 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 754 may be made of an organic material of Formulas 1 to 3, or may be formed by doping a hole injection host material with an organic compound of Formulas 1 to 3. When the P-type charge generation layer 754 includes a hole injection host material and an organic compound of Formula 1 to Formula 3, the hole injection host material may be MTDATA, CuPc, HATCN, or PEDOT/PSS and has a hole injection host material of Formula 1 to Formula 3. The organic compound may be doped at about 0.1 to 50% by weight. However, it is not limited to this.

Additionally, the second hole injection layer 756 is made of a hole injection material. For example, the second hole injection layer 756 may be made of MTDATA, CuPc, HATCN, or PEDOT/PSS.

In addition, a hole blocking layer (HBL) to prevent the movement of holes between the light emitting material layers (734, 746) and the electron transport layers (736, 748), and the light emitting material layers (734, 746) and the hole transport layers (732, 744) ) At least one exciton blocking layer among the electron blocking layers (EBL) may be further formed to prevent the movement of electrons.

As described above, the organic compound of the present invention is directly or The indirectly connected aromatic moiety is substituted with a strong electron withdrawing group and has a deep LUMO value, resulting in excellent hole injection and charge generation characteristics.

Therefore, it includes a charge generation layer 750 composed of an organic compound of Formula 1 to Formula 3 or a P-type charge generation layer 754 formed by doping a host material with an organic compound of Formula 1 to Formula 3. The luminous efficiency of the stacked structure light emitting diode 700 increases.

Figure 8 is a schematic cross-sectional view of a light emitting diode according to an eighth exemplary embodiment of the present invention. As shown in FIG. 8, the light emitting diode 800 according to the eighth embodiment of the present invention includes a first electrode 810 and a second electrode 820 facing each other, and a first and second electrode 810, 820), a first light-emitting unit (upper light-emitting unit, 830) located between the first electrode 810 and the first light-emitting unit 830, and a second light-emitting unit (lower light-emitting unit, 840), It includes a charge generation layer 850 located between the first and second light emitting units 830 and 840.

As described above, the first electrode 810 is an anode and is made of a conductive material with a relatively high work function, and the second electrode 820 is a cathode and is made of a conductive material with a relatively small work function.

The first light emitting unit 830 includes a first light emitting material layer (upper light emitting material layer, 832), a first electron transport layer (upper electron transport layer, 834), and an electron injection layer (836). The first electron transport layer 834 is located between the first light emitting material layer 832 and the second electrode 820, and the electron injection layer 836 is located between the first electron transport layer 834 and the second electrode 820. It is located in

In addition, the second light emitting unit 840 includes a hole injection layer 842, a hole transport layer 844, a second light emitting material layer (lower light emitting material layer, 846), and a second electron transport layer (lower electron transport layer, 848). ) includes.

The hole injection layer 842 is located between the first electrode 810 and the hole transport layer 844, and the hole transport layer 844 is located between the hole injection layer 842 and the second light emitting material layer 846. 2 The light emitting material layer 846 is located between the hole transport layer 844 and the second electron transport layer 848.

Each of the first and second light emitting material layers 832 and 846 may be formed by doping a host material with a dopant and emit different colors.

For example, the second light-emitting material layer 846 may emit blue light, and the first light-emitting material layer 832 may emit green, yellow-green (YG), or orange light, which has a longer wavelength than blue.

The hole transport layer 844 may be made of a hole transport host such as TPD or NPB. In addition, the hole injection layer 842 is made of a hole injection material such as MTDATA, CuPc, HATCN, or PEDOT/PSS, or these hole injection host materials are doped with about 0.1 to 50% by weight of the organic compounds of Formulas 1 to 3. You can.

Each of the first and second electron transport layers 834 and 848 is composed of oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or benzimide. It is made of an electron transport material such as azole (e.g., 2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole), and the electron injection layer (836) may be made of an electron injection material such as LIF or lithium quinolate (LiQ). The first and second electron transport layers 834 and 848 may be made of the same material or may be made of different materials.

The charge generation layer 850 is located between the first light-emitting unit 830 and the second light-emitting unit 840, and includes an N-type charge generation layer (N-CGL, 852) adjacent to the second light-emitting unit 840. It includes a P-type charge generation layer (P-CGL, 854) adjacent to the first light emitting unit 830.

The N-type charge generation layer 852 injects electrons into the second light-emitting unit 840, and the P-type charge generation layer 854 injects holes into the first light-emitting unit 830.

The N-type charge generation layer 852 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 552 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 854 may be made of an organic material of Formulas 1 to 3, or may be formed by doping a hole transport host material with an organic compound of Formulas 1 to 3. When the P-type charge generation layer 854 includes a hole transport host material and an organic compound of Formula 1 to Formula 3, the hole transport host material may be TPD or NPB, and the organic compound of Formula 1 to Formula 3 is about 0.1 to 0.1 It can be doped at 50% by weight. However, it is not limited to this.

In addition, a hole blocking layer (HBL) to prevent the movement of holes between the light emitting material layers (832, 846) and the electron transport layer (834, 848), and a hole blocking layer (HBL) between the light emitting material layers (832, 846) and the electron transport layer (844) At least one exciton blocking layer among the electron blocking layers (EBL) may be further formed to prevent the movement of electrons.

As described above, the organic compound of the present invention is directly or The indirectly connected aromatic moiety is substituted with a strong electron withdrawing group and has a deep LUMO value, resulting in excellent hole injection and charge generation characteristics.

Therefore, the charge generation layer 850 is comprised of a P-type charge generation layer 854 made of an organic compound of Formulas 1 to 3 or formed by doping a hole transport host material with an organic compound of Formulas 1 to 3. The luminous efficiency of the stacked structure light emitting diode 800 including increases.

In FIGS. 5 to 8, the P-type charge generation layer is explained as including the organic compounds of Formulas 1 to 3. However, as in FIGS. 1 to 4, the hole injection layer and/or the hole transport layer include the organic compounds of Formulas 1 to 3. May contain organic compounds.

In addition, although it is explained in FIGS. 5 to 8 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. 9 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. 9, the light emitting diode display device 900 includes a driving thin film transistor (Td), a planarization layer 960 covering the driving thin film transistor (Td), and a driving thin film located on the planarization layer 960. It includes a light emitting diode (E) connected to a transistor (Td).

The driving thin film transistor Td includes a semiconductor layer 940, a gate electrode 944, a source electrode 956, and a drain electrode 958.

Specifically, a semiconductor layer 940 is formed on a substrate 901 made of glass or plastic. For example, the semiconductor layer 940 may be made of an oxide semiconductor material. In this case, a light-shielding pattern (not shown) and a buffer layer (not shown) may be formed under the semiconductor layer 140, and the light-shielding pattern prevents light from entering the semiconductor layer 940, thereby forming the semiconductor layer 940. This prevents deterioration from light. Alternatively, the semiconductor layer 940 may be made of polycrystalline silicon, and in this case, both edges of the semiconductor layer 940 may be doped with impurities.

A gate insulating film 942 made of an insulating material is formed on the entire surface of the substrate 901 on the semiconductor layer 940. The gate insulating film 942 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

A gate electrode 944 made of a conductive material such as metal is formed on the gate insulating film 942 corresponding to the center of the semiconductor layer 940. Additionally, a gate wiring (not shown) and a first capacitor electrode (not shown) may be formed on the gate insulating film 942. The gate wire extends along the first direction, and the first capacitor electrode may be connected to the gate electrode 944.

Meanwhile, the gate insulating film 942 is formed on the entire surface of the substrate 901, but the gate insulating film 942 may be patterned to have the same shape as the gate electrode 944.

An interlayer insulating film 950 made of an insulating material is formed on the entire surface of the substrate 901 above the gate electrode 944. The interlayer insulating film 950 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or may be formed of an organic insulating material such as benzocyclobutene or photo-acryl.

The interlayer insulating film 950 has first and second contact holes 952 and 954 exposing upper surfaces of both sides of the semiconductor layer 940 . The first and second contact holes 952 and 954 are located on both sides of the gate electrode 944 and are spaced apart from the gate electrode 944 . Here, the first and second contact holes 952 and 954 are also formed within the gate insulating film 942. In contrast, when the gate insulating film 942 is patterned to have the same shape as the gate electrode 944, the first and second contact holes 952 and 954 are formed only within the interlayer insulating film 950.

A source electrode 956 and a drain electrode 958 are formed on the interlayer insulating film 950 using a conductive material such as metal. 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 950.

The source electrode 956 and the drain electrode 958 are positioned spaced apart from each other around the gate electrode 944 and contact both sides of the semiconductor layer 940 through the first and second contact holes 952 and 954, respectively. . 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 958 and overlaps the first capacitor electrode, thereby forming a storage capacitor using the interlayer insulating film 950 between the first and second capacitor electrodes as a dielectric layer.

Meanwhile, the semiconductor layer 940, the gate electrode 944, the source electrode 956, and the drain electrode 958 form a driving thin film transistor (Td). The driving thin film transistor (Td) is the semiconductor layer 940. It has a coplanar structure in which a gate electrode 944, a source electrode 956, and a drain electrode 958 are located on the top.

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.

In addition, 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 901. The gate electrode 944 of the driving thin film transistor (Td) is connected to the drain electrode (not shown) of the switching thin film transistor (Ts), and the source electrode 956 of the driving thin film transistor (Td) is connected to the power wiring (not shown). connected to Additionally, the gate electrode (not shown) and the source electrode (not shown) of the switching thin film transistor (Ts) are connected to the gate wire and data wire, respectively.

A planarization layer 960 is formed on the entire surface of the substrate 901 above the source electrode 956 and the drain electrode 958. The planarization layer 960 has a flat top surface and has a drain contact hole 962 exposing the drain electrode 958 of the driving thin film transistor (Td). Here, the drain contact hole 962 is shown as being formed directly above the second contact hole 954, but may also be formed spaced apart from the second contact hole 954.

The light emitting diode (E) is located on the planarization layer 960 and includes a first electrode 910 connected to the drain electrode 958 of the driving thin film transistor (Td), and an organic electrode sequentially stacked on the first electrode 910. It includes a light emitting layer 120 and a second electrode 930.

As described above, the first electrode 910 is made of a material with a relatively high work function value and serves as an anode, and the second electrode 930 is made of a material with a relatively low work function value and can serve as a cathode.

Additionally, an encapsulation substrate (not shown) may be bonded to the substrate 101 to cover the light emitting diode (E). At this time, a barrier layer may be formed between the encapsulation substrate and the light emitting diode (E) to bond these substrates and prevent moisture or oxygen from penetrating into the light emitting diode (E).

As explained through the embodiments of FIGS. 1 to 8, the organic light-emitting layer 920 includes a hole injection layer, a hole transport layer, or a charge generation layer consisting only of organic compounds of Formulas 1 to 3, or a host material containing a chemical compound of Formula 3. It is composed of a layer formed by doping organic compounds of formulas 1 to 3.

Although not shown, when the light emitting diode E has a stacked structure as shown in FIGS. 5 to 8 and is used to emit white light, a color filter may be formed.

As described above, the organic compound of the present invention is directly or It has a structure in which a strong electron withdrawing group on the indirectly connected aromatic moiety is substituted directly or through an aryl group, and has excellent hole injection characteristics. In addition, the organic compound of the present invention has a deep lowest unoccupied molecular orbital function (deep LUMO), so when used in an organic material layer adjacent to an organic material (Hole Transporting material, HTM) with excellent hole transport ability, the highest occupied molecular orbital of the HTM It receives electrons in the HOMO and moves them in the direction opposite to HTM (for example, the anode direction), and the resulting holes move in the EML direction (for example, the cathode direction) and have charge generation characteristics. Therefore, an organic light emitting diode display device containing the organic compound of the present invention has the advantage of reduced driving voltage and improved luminous efficiency.

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

Synthesis Example 1: Synthesis of A5 compound

1) Synthesis of Compound A3

Scheme 1-1

A1 (2.00g, 8.44 mmol), A2 (2.68g, 9.28 mmol), tetrakis(triphenylphosphine)palladium(0) (0.49g, 0.42 mmol), and potassium carbonate (5.13g, 37.12 mmol) were added to a 250 ml round bottom flask. It was added to a mixed solution of tetrahydrofuran (60 ml) and water (20 ml) and stirred at 80°C for 4 hours. After completion of the reaction, the extract was extracted using water and ethyl acetate, concentrated, and column separated using methylene chloride and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound A3 (1.50 g, 3.74 mmol).

2) Synthesis of Compound A5

Scheme 1-2

Add A3 (1.50g, 3.74 mmol) and A4 (2.47g, 37.36 mmol) to methylene chloride (200ml) in a 500ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (4.10 ml, 37.36 mol) and pyridine (6.02 ml, 74.73 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound A5 (0.65g, 1.31mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.17 (d, 1H), 8.09 (d, 1H), 7.79~7.74 (m, 2H), 7.51 (s, 1H), 7.31~7.22 (m, 6H), 7.07~7.00 (m, 7H), 6.93 (d, 1H)

Synthesis example 2: Synthesis of Compound B8

1) Synthesis of compound B3

Scheme 2-1

In a 500 ml round bottom flask, B1 (7.00g, 30.55 mmol), B2 (8.65g, 29.51 mmol), Tris(dibenzylideneacetone) dipalladium(0) (0.42g, 0.46 mmol), (ㅁ)-2,2'-Bis (diphenylphosphino)-1,1'-binaphthalene (BINAP) (0.57g, 0.57 mmol) and Sodium tert-butoxide (4.11g, 42.77 mmol) were dissolved in toluene (300 ml) and incubated in a 100°C bath for 24 hours. After stirring, 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 B3 (10.50 g, 23.80 mmol).

2) Synthesis of compound B5

Scheme 2-2

B3 (10.50g, 23.80 mmol), B4 (19.41g, 71.39 mmol), Tris(dibenzylideneacetone) dipalladium(0)(0.33g, 0.36 mmol), BINAP (0.44g, 0.71 mmol) and Sodium in a 500 ml round bottom flask. Dissolve tert-butoxide (3.20 g, 33.32 mmol) in toluene (250 ml) and stir in a 100°C bath for 24 hours. When the reaction is complete, toluene is removed and extracted using dichloromethane and water. After distillation under reduced pressure and silica gel column, the solvent was distilled under reduced pressure to obtain compound B5 (6.68g, 10.57 mmol).

3) Compound B6 synthesis

Scheme 2-3

B5 (6.68g, 10.57 mmol) and diethylether (200 ml) were added to a 500 ml round bottom flask, and cooled to -78°C. Afterwards, 2.5M n-butyl lithium (4.86 ml, 12.15 mml) was added, maintained for 1 hour, and brought to room temperature. After cooling to -78°C again, triethylborate (1.77g, 12.15 mmol) was added, maintained for 30 minutes, and brought to room temperature. After stirring for 24 hours, the reaction was terminated by adding 10M HCl, extracted, distilled under reduced pressure, and filtered using petroleum ether to obtain compound B6 (3.67g, 6.15 mmol).

4) Synthesis of compound B7

Scheme 2-4

In a 250 ml round bottom flask, add A1 (1.30g, 5.48 mmol), B6 (3.60g, 6.03 mmol), tetrakis(triphenylphosphine)palladium(0) (0.32g, 0.27 mmol), and potassium carbonate (3.33g, 24.13 mmol). It was added to a mixed solution of tetrahydrofuran (45 ml) and water (15 ml) and stirred at 80°C for 4 hours. After completion of the reaction, the extract was extracted using water and ethyl acetate, concentrated, and column separated using methylene chloride and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound B7 (1.45 g, 2.04 mmol).

5) Synthesis of compound B8

Scheme 2-5

Add B7 (1.45g, 2.04 mmol) and A4 (1.35g, 20.44 mmol) to methylene chloride (200 ml) in a 500 ml round bottom flask and cool to 0 ^o C. Afterwards, titanium chloride (2.24 ml, 20.44 mol) and pyridine (3.29 ml, 40.88 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound B8 (0.53g, 0.66 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.14 (d, 1H), 8.06 (d, 1H), 7.77~7.66 (m, 5H), 7.49 (s, 1H), 7.32~7.29 (m, 2H), 7.09~7.06 (m, 3H)

The HOMO value of B8 organic compound calculated according to Density Functional Theory is -6.34 eV, and the LUMO value is -4.32 eV (B3LYP/6-31G ^* ).

Synthesis Example 3: Synthesis of Compound C6

1) Synthesis of compound C3

Scheme 3-1

C1 (15.00g, 88.64 mmol), C2 (60.62g, 132.96 mmol), Tris(dibenzylideneacetone) dipalladium(0)(1.22g, 1.33 mmol), BINAP (1.66g, 2.66 mmol) and Sodium in a 1000 ml round bottom flask. After dissolving tert-butoxide (11.93g, 124.10 mmol) in toluene (800 ml), stir in a 100°C bath for 24 hours. When the reaction is complete, toluene is removed and extracted using dichloromethane and water. After distillation under reduced pressure and silica gel column, the solvent was distilled under reduced pressure to obtain compound C3 (13.40 g, 24.62 mmol).

2) Synthesis of compound C4

Scheme 3-2

C3 (13.40 g, 24.62 mmol) and diethylether (300 ml) were added to a 500 ml round bottom flask, and cooled to -78°C. Afterwards, 2.5M n-butyl lithium (11.33 ml, 28.32 mmol) was added, maintained for 1 hour, and brought to room temperature. After cooling to -78°C again, triethylborate (4.13g, 28.32 mmol) was added, maintained for 30 minutes, and brought to room temperature. After stirring for 24 hours, the reaction was terminated by adding 10M HCl, extracted, distilled under reduced pressure, and filtered using petroleum ether to obtain compound C4 (4.80g, 9.43 mmol).

3) Synthesis of compound C5

Scheme 3-3

A1 (2.03g, 8.56 mmol), C4 (4.80g, 9.42 mmol), tetrakis(triphenylphosphine)palladium(0) (0.49g, 0.43 mmol), and potassium carbonate (5.21g, 37.68 mmol) were added to a 250 ml round bottom flask. It was added to a mixed solution of tetrahydrofuran (75 ml) and water (25 ml) and stirred at 80°C for 4 hours. After completion of the reaction, the extract was extracted using water and ethyl acetate, concentrated, and column separated using methylene chloride and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound C5 (1.75 g, 2.82 mmol).

4) Synthesis of compound C6

Scheme 3-4

Add C5 (1.75g, 2.82 mmol) and A4 (1.86g, 28.16 mmol) to methylene chloride (200ml) in a 500ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (3.09 ml, 28.16 mol) and pyridine (4.54 ml, 56.32 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound C6 (0.63g, 0.88 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.15 (d, 1H), 8.06 (d, 1H), 7.78~7.67 (m, 6H), 7.49 (s, 1H), 7.32~7.29 (m, 2H), 7.10~7.07 (m, 4H)

The HOMO value of the C6 organic compound calculated according to Density Functional Theory is -5.59 eV, and the LUMO value is -4.24 eV (B3LYP/6-31G ^* ).

Synthesis example 4: Compound D5 synthesis of

1) Synthesis of Compound D2

Scheme 4-1

C1 (18.00g, 106.37 mmol), D1 (43.38g, 159.56 mmol), Tris(dibenzylideneacetone) dipalladium(0)(1.45g, 1.60 mmol), BINAP (1.99g, 3.19 mmol) and Sodium in a 2000 ml round bottom flask. Dissolve tert-butoxide (14.31g, 148.92 mmol) in toluene (1000 ml), stir in a 100°C bath for 24 hours, and when the reaction is complete, toluene is removed, extracted using dichloromethane and water, and then reduced pressure. After distillation and silica gel column, the solvent was distilled under reduced pressure to obtain compound D2 (12.70 g, 35.26 mmol).

2) Synthesis of compound D3

Scheme 4-2

D2 (12.70g, 35.26 mmol) and diethylether (300 ml) were added to a 500 ml round bottom flask, and cooled to -78°C. Afterwards, 2.5M n-butyl lithium (16.22 ml, 40.55 mmol) was added, maintained for 1 hour, and brought to room temperature. After cooling to -78°C again, triethylborate (5.92g, 40.55 mmol) was added, maintained for 30 minutes, and brought to room temperature. After stirring for 24 hours, the reaction was terminated by adding 10M HCl, extracted, distilled under reduced pressure, and filtered using petroleum ether to obtain compound D3 (6.03g, 18.55 mmol).

3) Synthesis of compound D4

Scheme 4-3

A1 (4.00g, 16.87 mmol), D3 (6.03g, 18.56 mmol), tetrakis(triphenylphosphine)palladium(0) (0.97g, 0.84 mmol), and potassium carbonate (10.26g, 74.25 mmol) were added to a 250 ml round bottom flask. It was added to a mixed solution of tetrahydrofuran (150 ml) and water (50 ml) and stirred at 80°C for 4 hours. After completion of the reaction, the extract was extracted using water and ethyl acetate, concentrated, and column separated using methylene chloride and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound D4 (2.50 g, 5.72 mmol).

4) Synthesis of compound D5

Scheme 4-4

Add D4 (2.50g, 5.72 mmol) and A4 (3.78g, 57.15 mmol) to methylene chloride (20 0ml) in a 500 ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (6.27 ml, 57.15 mmol) and pyridine (9.21 ml, 114.30 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound D5 (0.98g, 1.84 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.18 (d, 1H), 8.08 (d, 1H), 7.79~7.75 (m, 2H), 7.52 (s, 1H), 7.28~7.24 (m, 5H), 7.07~7.00 (m, 6H), 6.91~6.88 (m, 1H)

The HOMO value of D5 organic compound calculated according to Density Functional Theory is -5.58 eV, and the LUMO value is -4.02 eV (B3LYP/6-31G ^* ).

Synthesis example 5: Compound E5 synthesis of

1) Synthesis of compound E3

Scheme 5-1

E1 (15.00g, 77.69 mmol), E2 (8.79g, 77.69 mmol), and potassium carbonate (12.89g, 93.23 mmol) were added to 150 ml of DMF in a 250 ml round bottom flask, and stirred at room temperature for 4 hours. After completion of the reaction, water and acetic acid were added, stirred for 30 minutes, extracted with chloroform, and concentrated to obtain E3 (21.67g, 75.72 mmol).

2) Synthesis of compound E4

Scheme 5-2

E3 (21.67g, 75.72 mmol) was added to a 100 ml round bottom flask, 50% acetic acid (30 ml) and sulfuric acid (1.50 ml) were added, and stirred at 100°C for 24 hours. After completion of the reaction, the temperature was lowered to room temperature, extracted using water and chloroform, and moisture was removed using magnesium sulfate. Afterwards, it was dried in a vacuum oven to obtain E4 (13.74g, 64.20 mmol).

3) Synthesis of compound E5

Scheme 5-3

Add D4 (2.50g, 5.72 mmol) and E4 (12.24g, 57.15 mmol) to methylene chloride (200 ml) in a 500 ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (6.27 ml, 57.15 mmol) and pyridine (9.21 ml, 114.30 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound E5 (0.73g, 0.88 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.15 (d, 1H), 8.07 (d, 1H), 7.79~7.76 (m, 2H), 7.50 (s, 1H), 7.27~7.24 (m, 5H), 7.06~7.00 (m, 6H), 6.91~6.88(t, 1H)

Synthesis Example 6: Synthesis of Compound F6

1) Synthesis of compound F3

Scheme 6-1

In a 2000 ml round bottom flask, F1 (18.00g, 69.76 mmol), F2 (42.70g, 209.29 mmol), Tris(dibenzylideneacetone) dipalladium(0) (1.92g, 2.09 mmol), BINAP (2.61g, 4.19 mmol) and Sodium. After dissolving tert-butoxide (18.77g, 195.3 4mmol) in toluene (1000 ml), stir in a 100°C bath for 24 hours. When the reaction is complete, toluene is removed and extracted using dichloromethane and water. After distillation under reduced pressure and silica gel column, the solvent was distilled under reduced pressure to obtain compound F3 (8.75 g, 21.33 mmol).

2) Synthesis of compound F4

Scheme 6-2

F3 (8.75g, 21.33 mmol) and diethylether (300 ml) were added to a 500 ml round bottom flask, and cooled to -78°C. Afterwards, 2.5M n-Butyl lithium (9.81 ml, 24.53 mml) was added, maintained for 1 hour, and brought to room temperature. After cooling to -78°C again, triethylborate (3.84g, 24.53 mmol) was added, maintained for 30 minutes, and brought to room temperature. After stirring for 24 hours, the reaction was terminated by adding 10M HCl, extracted, distilled under reduced pressure, and filtered using petroleum ether to obtain compound F4 (4.32g, 11.52 mmol).

3) Synthesis of compound F5

Scheme 6-3

A1 (2.48g, 10.46 mmol), F4 (4.32g, 11.51 mmol), tetrakis(triphenylphosphine) palladium(0) (0.60g, 0.52 mmol), and potassium carbonate (6.36g, 46.03 mmol) were added to a 250 ml round bottom flask. It was added to a mixed solution of tetrahydrofuran (90 ml) and water (30 ml) and stirred at 80°C for 4 hours. After completion of the reaction, the extract was extracted using water and ethyl acetate, concentrated, and column separated using methylene chloride and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound F5 (2.05g, 4.21 mmol).

4) Synthesis of compound F6

Scheme 6-4

Add F5 (2.05g, 4.21 mmol) and A4 (2.78g, 42.06 mmol) to methylene chloride (200 ml) in a 500 ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (4.61 ml, 42.06 mmol) and pyridine (6.78 ml, 84.11 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound F6 (0.85g, 1.46 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.17 (d, 1H), 8.08 (d, 1H), 7.79~7.74 (m, 2H), 7.51 (s, 1H), 7.47~7.41 (m, 2H), 7.28~7.25 (m, 4H), 7.08~6.99 (m, 6H)

The HOMO value of F6 organic compound calculated according to Density Functional Theory is -5.56 eV, and the LUMO value is -4.16 eV (B3LYP/6-31G ^* ).

Synthesis Example 7: Synthesis of Compound G4

1) Synthesis of compound G2

Scheme 7-1

G1 (11.00g, 70.02 mmol), E2 (7.92g, 70.02 mmol), and Potassium carbonate (11.61g, 84.03 mmol) were added to 150 ml of DMF in a 250 ml round bottom flask, and stirred at room temperature for 4 hours. After completion of the reaction, water and acetic acid were added, stirred for 30 minutes, extracted with chloroform, and concentrated to obtain G2 (15.03g, 85.79 mmol).

2) Synthesis of compound G3

Scheme 7-2

G2 (15.03g, 85.79 mmol) was added to a 100 ml round bottom flask, 50% acetic acid (30 ml) and sulfuric acid (1.50 ml) were added, and stirred at 100°C for 24 hours. After completion of the reaction, the temperature was lowered to room temperature, extracted using water and chloroform, and moisture was removed using magnesium sulfate. Afterwards, it was dried in a vacuum oven to obtain G3 (9.12g, 51.20 mmol).

3) Synthesis of compound G4

Scheme 7-3

Add D4 (2.24g, 5.12 mmol) and G3 (9.12g, 51.21 mmol) to methylene chloride (200 ml) in a 500 ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (5.61 ml, 51.21 mol) and pyridine (8.25 ml, 102.41 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound G4 (0.83g, 1.10 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.15 (d, 1H), 8.07 (d, 1H), 7.80~7.75 (m, 2H), 7.51 (s, 1H), 7.42~7.39 (m, 4H), 7.28~7.24 (m, 5H), 7.06~6.88 (m, 6H), 6.91~6.88 (m, 1H)

Synthesis Example 8: Synthesis of Compound H4

1) Synthesis of compound H2

Scheme 8-1

H1 (20.00g, 73.51 mmol), E2 (8.31g, 73.51 mmol), and Potassium carbonate (12.19g, 88.21 mmol) were added to 180 ml of DMF in a 250 ml round bottom flask, and stirred at room temperature for 4 hours. After completion of the reaction, water and acetic acid were added, stirred for 30 minutes, extracted with chloroform, and concentrated to obtain H2 (25.54g, 69.93 mmol).

2) Synthesis of compound H3

Scheme 8-2

H2 (25.54g, 69.93 mmol) was added to a 100 ml round bottom flask, 50% acetic acid (30 ml) and sulfuric acid (1.50 ml) were added, and the mixture was stirred at 100°C for 24 hours. After completion of the reaction, the temperature was lowered to room temperature, extracted using water and chloroform, and moisture was removed using magnesium sulfate. Afterwards, it was dried in a vacuum oven to obtain H3 (13.87g, 47.32 mmol).

3) Synthesis of compound H4

Scheme 8-3

Add D4 (2.00g, 4.57 mmol) and H3 (13.40g, 45.72 mmol) to methylene chloride (200 ml) in a 500 ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (5.01 ml, 45.72 mol) and pyridine (7.37 ml, 91.44 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound H4 (0.67g, 0.68 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.16 (d, 1H), 8.08 (d, 1H), 7.80~7.75 (m, 2H), 7.51 (s, 1H), 7.28~7.24 (m, 5H), 7.06~6.88 (m, 6H), 6.91~6.88 (m, 1H)

Synthesis Example 9: Synthesis of Compound I5

1) Compound I2 synthesis

Scheme 9-1

I1 (10.00g, 48.08 mmol), F2 (29.42g, 144.23 mmol), Tris(dibenzylideneacetone) dipalladium(0) (1.32g, 1.44 mmol), BINAP (1.80g, 2.88 mmol) and Sodium in a 1000 ml round bottom flask. After dissolving tert-butoxide (12.94g, 134.62 mmol) in toluene (500 ml), stir in a 100°C bath for 24 hours. When the reaction is complete, toluene is removed and extracted using dichloromethane and water. After distillation under reduced pressure and silica gel column, the solvent was distilled under reduced pressure to obtain compound I2 (5.47 g, 15.19 mmol).

2) Compound I3 synthesis

Scheme 9-2

I2 (5.47g, 15.19 mmol) and diethylether (300 ml) were added to a 500 ml round bottom flask and cooled to -78°C. Afterwards, 2.5M n-Butyl lithium (6.99 ml, 17.46 mml) was added, maintained for 1 hour, and brought to room temperature. After cooling to -78°C again, triethylborate (2.55g, 17.46 mmol) was added, maintained for 30 minutes, and brought to room temperature. After stirring for 24 hours, the reaction was terminated by adding 10M HCl, extracted, distilled under reduced pressure, and filtered using petroleum ether to obtain compound I3 (3.83g, 11.78mmol).

3) Compound I4 synthesis

Scheme 9-3

A1 (2.50g, 10.55 mmol), I3 (3.77g, 11.60 mmol), tetrakis(triphenylphosphine) palladium(0) (0.61g, 0.53 mmol), and potassium carbonate (6.41g, 46.40 mmol) were added to a 250 ml round bottom flask. It was added to a mixed solution of tetrahydrofuran (90 ml) and water (30 ml) and stirred at 80°C for 4 hours. After completion of the reaction, the extract was extracted using water and ethyl acetate, concentrated, and column separated using methylene chloride and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound I4 (1.95 g, 4.46 mmol).

4) Synthesis of compound I5

Scheme 9-4

Add I4 (1.95g, 4.46 mmol) and A4 (2.94g, 44.58 mmol) to methylene chloride (200 ml) in a 500 ml round bottom flask and cool to 0°C. Afterwards, titanium chloride (4.89 ml, 44.58 mmol) and pyridine (7.18 ml, 89.16 mmol) were slowly added in that order and stirred at 60°C for 24 hours. After completion of the reaction, the extract was extracted using water and methylene chloride, concentrated, and column separated using methylene chloride, ethyl acetate, and n-hexane. Afterwards, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound I5 (0.89g, 1.67 mmol).

¹ HNMR (500MHz, CDCl ₃ ) 8.16 (d, 1H), 8.07 (d, 1H), 7.79-7.73 (m, 2H), 7.51 (s, 1H), 7.32~7.23 (m, 3H), 7.14~7.10 (m, 7H), 6.53 (d, 2H).

Example 1: Fabrication of a light emitting diode device

A light emitting diode device containing the B8 compound synthesized in Synthesis Example 2 was manufactured. The ITO glass was patterned so that the light emitting area was 3 mm x 3 mm in size and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure was set to ¹ Lower blue emitting material layer (host MADN, blue dopant BD-1 (4% by weight), (250Å), lower electron transport layer LGC ETL (2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl) phenyl]-1-phenyl-1H-benzimidazole, 150Å), n-type charge generation layer (Bphen doped with 2% Li, 100Å), p-type charge generation layer (α-NPB doped with 15% B8 compound, 100Å) , upper hole transport layer (α-NPB, 100Å), upper exciton blocking layer (TCTA, 100Å), upper emitting material layer YG emitting material layer (CBP doped with 15% Ir(2-phq) ₃ , 300Å), upper The electron transport layer (LGC ETL, 350Å), electron injection layer (LiF, 7Å), and cathode Al (800Å) were formed in that order.

Example 2: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that the C6 compound synthesized in Synthesis Example 3 was used instead of B8 as the dopant of the P-type charge generation layer.

Example 3: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that the D5 compound synthesized in Synthesis Example 4 was used instead of B8 as the dopant of the P-type charge generation layer.

Example 4: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that the E5 compound synthesized in Synthesis Example 5 was used instead of B8 as the dopant of the P-type charge generation layer.

Example 5: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that the F6 compound synthesized in Synthesis Example 6 was used instead of B8 as the dopant of the P-type charge generation layer.

Example 6: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that the G4 compound synthesized in Synthesis Example 7 was used instead of B8 as the dopant of the P-type charge generation layer.

Example 7: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that the H4 compound synthesized in Synthesis Example 8 was used instead of B8 as the dopant of the P-type charge generation layer.

Example 8: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that the I5 compound synthesized in Synthesis Example 9 was used instead of B8 as the dopant of the P-type charge generation layer.

Comparative Example 1: Fabrication of light emitting diode device

A light emitting diode device was manufactured by repeating the procedure of Example 1, except that HATCN was used instead of G-1 as the dopant of the P-type charge generation layer.

Example 9: Measurement of electrical and optical properties of light emitting diode devices

Current density, luminance, luminous efficiency, and external quantum efficiency were measured for the light emitting diode devices manufactured in Examples 1-8 and Comparative Examples. Figures 10a and 10b show the results of the current density measurement, Figures 11a and 11b show the results of the luminance measurement, Figures 12a and 12b show the results of the luminous efficiency measurement, and Figures 13a and 13b shows the external quantum efficiency measurement results. Additionally, Table 1 below displays the measurement results according to this example as a whole.

As shown in Table 1 and Figures 10a to 13b, compared to a light emitting diode (comparative example, Ref) consisting of a P-type charge generation layer doped with HATCN, P-type charge generation doped with the organic compound of the present invention It was confirmed that the driving voltage was greatly reduced in the layered light emitting diode, and the luminance, current density, external quantum efficiency, and luminous efficiency were greatly improved.

Table 1: Light-emitting characteristics of light-emitting diode devices

Although the present invention has been described above with reference to preferred embodiments, those skilled in the art can make various modifications and changes to the present invention without departing from the technical spirit and scope of the present invention as set forth in the claims below. You will understand that you can do it.

110, 210, 310, 410, 510, 610, 710, 810, 910: first electrode
120, 220, 320, 420, 520, 620, 720, 820, 920: second electrode
130, 230, 330, 430, 530, 540, 630, 640, 730, 740, 830, 840: Light emitting unit
132, 232, 332, 432, 534, 546, 635, 646, 734, 746, 832, 846: Emitting material layer
134, 234, 334, 434, 536, 548, 637, 648, 736, 748, 834, 848: Electron transport layer
136, 236, 336, 436, 538, 639, 738, 836: Electron injection layer
140, 240, 542, 631, 642, 742, 756, 842: Hole injection layer
150, 250, 350, 450, 532, 544, 633, 644, 732, 744, 844: hole transport layer
550, 650, 750, 850: Charge generation layer
552, 652, 752, 852: N-type charge generation layer
554, 654, 754, 854: P-type charge generation layer

Claims (18)

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

(In Formula 1, R ₁ to R ₆ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or substituted Unsubstituted C ₆ -C ₃₀ heteroaryloxyl group, C ₁ -C ₂₀ alkylamine group, C ₅ -C ₃₀ aryl amine group, C ₅ -C ₃₀ heteroaryl amine group, C ₁ -C ₃₀ silyl substituted with alkyl group selected from the group consisting of a silyl group substituted with a C ₅ -C ₃₀ aryl group and a silyl group substituted with a C ₅ -C ₃₀ heteroaryl group;
X1 to X4 are each independently selected from the group consisting of carbon, nitrogen, oxygen, sulfur and phosphorus; Ar is a substituted or unsubstituted C ₅ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ hetero arylene group; =Y and =Z are each independently selected from the group consisting of (a), (b), and (d) of Formula 2 below; The C ₅ -C ₃₀ aryl group, the C ₅ -C ₃₀ heteroaryl group, the C ₆ -C ₃₀ aryloxyl group, and the C ₆ -C ₃₀ heteroaryloxy group constituting R ₁ to R ₆ and Ar. The actual group, the C ₅ -C ₃₀ arylene group, and the C ₅ -C ₃₀ hetero arylene group are each independently unsubstituted, or deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, substituted with at least one substituent selected from the group consisting of a carboxyl group, a carbonyl group, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group)
Formula 2

(In Formula 2, A ₁ and A ₂ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or substituted is selected from the group consisting of a C ₆ -C ₃₀ heteroaryloxyl group, or A ₁ and A ₂ are linked together to form an alicyclic ring, an aromatic ring, or a heteroaromatic ring; A ₃ is hydrogen, Deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, a group consisting of a substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl group selected from; the C ₅ -C ₃₀ aryl group, the C ₅ -C ₃₀ heteroaryl group, the C ₆ -C ₃₀ aryloxyl group and the C ₆ -C ₃₀ heteroaryloxy group constituting A ₁ to A ₃ The actual groups are each independently unsubstituted or composed of deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group. is substituted with at least one substituent selected from the group
According to clause 1,
In Formula 1, R ₁ to R ₄ are each independently selected from the group consisting of hydrogen, deuterium, -CN, and halogen, and R ₅ and R ₆ are each independently unsubstituted or composed of CF ₃ , -CN, and halogen. Ar is an aryl group or heteroaryl group substituted with at least one functional group selected from the group consisting of, and Ar is unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, -CN, and -CF ₃ It is a ren group or hetero arylene group,
A ₁ and A ₂ of Formula 2 are each independently an aryl or heteroaryl group substituted with at least one functional group selected from the group consisting of CN, halogen, -CF ₃ and -CN. An organic compound.
According to clause 1,
The organic compound is any one represented by the following formula (3).
Formula 3





















a first electrode;
a second electrode facing the first electrode;
a light emitting unit located between the first and second electrodes and including a light emitting material layer;
A hole layer located between the first electrode and the light emitting unit and comprising the organic compound according to claim 1.
A light emitting diode containing a.
According to clause 4,
The hole layer is located between a hole transport layer and the first electrode and includes a hole injection layer made of only the organic compound or a hole injection host material doped with the organic compound.
According to clause 4,
The hole layer is,
A hole transport layer;
a first hole injection layer located between the hole transport layer and the first electrode and made of only the organic compound or a hole injection host material doped with the organic compound;
A light emitting diode comprising a second hole injection layer located between the first electrode and the first hole injection layer and made of a hole injection host material.
According to clause 4,
The hole layer is a light emitting diode including a first hole transport layer formed by doping the organic compound into a hole transport host material.
According to clause 7,
The hole layer is,
The light emitting diode further includes a second hole transport layer located between the first hole transport layer and the light emitting unit and made of a hole transport host material.
a 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 first electrode and including a second light emitting material layer;
A P-type charge generation layer located between the first and second light-emitting units and comprising the organic compound according to claim 1.
A light emitting diode containing a.
According to clause 9,
The P-type charge generation layer is a light emitting diode made of only the organic compound or by doping the organic compound into a hole injection host material.
According to clause 9,
The light emitting diode is located between the P-type charge generation layer and the second 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 11,
The first light emitting unit includes a first hole transport layer located between the first light emitting material layer and the P-type charge generation layer, an electron injection layer located between the first light emitting material layer and the second electrode, and a first hole transport layer located between the first light emitting material layer and the second electrode. 1 further comprising an electron transport layer,
The second light emitting unit includes a second electron transport layer located between the N-type charge generation layer and the second light emitting material layer, and a first hole injection layer located between the first electrode and the second light emitting material layer. and a light emitting diode further comprising a second hole transport layer.
According to clause 12,
The first light emitting unit further includes a second hole injection layer located between the first hole transport layer and the P-type charge generation layer.
According to claim 11,
A light emitting diode further comprising a second hole injection layer located between the P-type charge generation layer and the N-type charge generation layer.
According to claim 11,
The first light emitting unit further includes an electron injection layer and a first electron transport layer located between the first light emitting material layer and the second electrode,
The second light emitting unit includes a second electron transport layer located between the N-type charge generation layer and the second light emitting material layer, a hole injection layer and a hole located between the first electrode and the second light emitting material layer. Further comprising a transport layer,
The P-type charge generation layer is a light emitting diode formed by doping the organic compound into a hole transport layer host material.
a base substrate;
a driving thin film transistor located on the base substrate;
a light emitting diode according to any one of claims 4 to 15 located on the base substrate and connected to the driving thin film transistor;
An encapsulation substrate that covers the light emitting diode and is bonded to the base substrate.
An organic light emitting diode display device comprising a. An organic compound represented by the following formula (1).
Formula 1

(In Formula 1, R ₁ to R ₄ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or substituted Unsubstituted C ₆ -C ₃₀ heteroaryloxyl group, C ₁ -C ₂₀ alkylamine group, C ₅ -C ₃₀ aryl amine group, C ₅ -C ₃₀ heteroaryl amine group, C ₁ -C ₃₀ silyl substituted with alkyl group selected from the group consisting of a silyl group substituted with a C ₅ -C ₃₀ aryl group and a silyl group substituted with a C ₅ -C ₃₀ heteroaryl group;
R ₅ and R ₆ are each independently a C ₅ -C ₃₀ aryl group, substituted or substituted with at least one functional group selected from the group consisting of C ₁ -C ₂₀ alkoxy group, halogen, -CN and -CF ₃ Unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl group, C ₁ -C ₂₀ alkylamine group, C ₅ -C ₃₀ aryl amine group, C ₅ -C ₃₀ heteroaryl amine group, silyl group substituted with C ₁ -C ₃₀ alkyl group, silyl group substituted with C ₅ -C ₃₀ aryl group and C ₅ -C ₃₀ heteroaryl group. selected from the group consisting of substituted silyl groups;
X ₁ to X ₄ are each independently selected from the group consisting of carbon, nitrogen, oxygen, sulfur and phosphorus; Ar is a substituted or unsubstituted C ₅ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ hetero arylene group;
=Y and =Z are each independently selected from the group consisting of (a), (b), and (d) of Formula 2 below;
The C ₅ -C ₃₀ aryl group constituting R ₁ to R ₄ , the C ₅ -C ₃₀ heteroaryl group constituting R ₁ to R ₆ and Ar, the C ₆ -C ₃₀ aryloxyl group, The C ₆ -C ₃₀ heteroaryloxyl group, the C ₅ -C ₃₀ arylene group, and the C ₅ -C ₃₀ hetero arylene group are each independently unsubstituted or substituted with deuterium, -OH, -CN, -NO ₂ , - CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ substituted with at least one substituent selected from the group consisting of alkoxy group.)
Formula 2

(In Formula 2, A ₁ and A ₂ are each independently hydrogen, deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, substituted or substituted is selected from the group consisting of a C ₆ -C ₃₀ heteroaryloxyl group, or A ₁ and A ₂ are linked together to form an alicyclic ring, an aromatic ring, or a heteroaromatic ring; A ₃ is hydrogen, Deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₅ -C ₃₀ aryl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ aryloxyl group, a group consisting of a substituted or unsubstituted C ₆ -C ₃₀ heteroaryloxyl group selected from; the C ₅ -C ₃₀ aryl group, the C ₅ -C ₃₀ heteroaryl group, the C ₆ -C ₃₀ aryloxyl group and the C ₆ -C ₃₀ heteroaryloxy group constituting A ₁ to A ₃ The actual groups are each independently unsubstituted or composed of deuterium, -OH, -CN, -NO ₂ , -CF ₃ , fluoroalkyl group, halogen, carboxyl group, carbonyl group, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group. is substituted with at least one substituent selected from the group
According to clause 17,
The organic compound is any one of the following compounds.

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