KR20100108120A - Benzoisoquinoline chemiclal and organic electroric element using the same, terminal thererof - Google Patents

Abstract

PURPOSE: A benzo isoquinoline compound and an organic electric device using the same are provided to lower driving voltage of the device and to improve stability of the device. CONSTITUTION: A benzo isoquinoline compound is denoted by chemical formula. An organic electric device comprises one or more organic layer having the benzo isoquinoline compound. The organic layer comprises hole injection/transport layer, light emitting layer, electron injection layer. The light emitting layer contains the benzo isoquinoline compound. A terminal comprises a display device having an organic electric device and a controller driving the display device.

Description

Benzoisoquinoline compound and organic electronic device using same, and terminal thereof {BENZOISOQUINOLINE CHEMICLAL AND ORGANIC ELECTRORIC ELEMENT USING THE SAME, TERMINAL THEREROF}

The present invention relates to a benzoisoquinoline compound, an organic electric device using the same, and a terminal thereof.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.

Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be classified. In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. The principle is that when a small amount of dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.

The present inventors have found a benzo isoquinoline compound having a novel structure, and also found that when the compound is applied to an organic electric device, the luminous efficiency, stability and lifespan of the device can be greatly improved.

Accordingly, an object of the present invention is to provide a novel benzo isoquinoline compound, an organic electric device using the same, and a terminal thereof.

In one aspect, the present invention provides a compound of the formula

The present invention is a compound having a benzo isoquinoline derivative, can be used as a hole injection, hole transport, electron injection, electron transport and light emitting material in organic electronic devices, in particular as a host or dopant in the light emitting material and host / dopant alone Can be used.

The inventors have found that the effect of increasing the efficiency, lowering the driving voltage, increasing the lifetime and increasing the stability of the organic electronic device including the same. Accordingly, an object of the present invention is to provide a benzoisoquinoline derivative, an organic electronic device using the same, and a terminal including the organic electronic device.

The present invention can play a variety of roles in the organic electronic device and the terminal, when applied to the organic electronic device and the terminal can lower the driving voltage of the device, and improve the light efficiency and life, the stability of the device.

Hereinafter, some embodiments of the present invention will be described in detail through exemplary drawings. In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

The present invention provides a compound of Formula 1 below.

In Chemical Formula 1,

(1) L ₁ and L ₂ represent a group selected from a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted hetero arylene group, and a divalent substituted or unsubstituted aliphatic hydrocarbon.

(2) X ₁ and X ₂ are each independently halogen, amino group, nitrile group, nitro group C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxy group, C ₁ to C ₂₀ alkylamine group, C ₁ C ₂₀ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, C ₆ to C ₂₀ aryl group substituted with deuterium, C ₈ to C ₂₀ aryl alkenyl group, substituted or unsubstituted silane group, substituted or unsubstituted boron group, substituted or unsubstituted C ₆ ~ C ₂₀ aryl group unsubstituted or substituted with one or more groups selected from the group consisting of a germanium group and a substituted or unsubstituted C ₅ ~ C ₂₀ heterocyclic group; Of _{halogen, CN, NO 2, C 1} ~ C 20 alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ coming of the alkyl group, C ₂ ~ C ₂₀ of the alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a substituted or unsubstituted silane group , a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C ₅ ~ C ₂₀ by at least one group selected from the group consisting of a heterocyclic-substituted or unsubstituted C ₅ ~ C ₂₀ of the ring Heterocyclic group; Or a condensed ring group of a C ₆ to C ₂₀ aromatic ring and a C ₄ to C ₂₀ aliphatic ring, each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group , A substituted and unsubstituted hetero aryl group. At this time, X ₁ and X ₂ may not be a hydrogen atom at the same time.

At this time, L ₁ and L ₂ may be the same or different from each other, X ₁ and X ₂ may be the same or different from each other.

The present invention provides compounds of formulas (2) and (3) below.

In Formulas 2 and 3 below, L ₁ to L ₂ may be the same as L ₁ and L ₂ defined in Formula 1.

In the formula (2), HAr ₁ and HAr ₂ may be the same or different and represent a group selected from a C6-C60 aryl group which may have a substituent or a C3-C60 teraryl group which may have a substituent.

In formula 3, X ₁ and X ₂ is NR if _two days each R is a substituted unsubstituted, same or represents another group, C alkyl group of _{1 ~ C 20, C 1 ~} C 20 alkoxy group, C ₁ ~ C ₂₀ Alkylamine groups, C ₁ to C ₂₀ alkyl thiophene groups, C ₆ to C ₂₀ aryl thiophene groups, C ₂ to C ₂₀ alkenyl groups, C ₂ to C ₂₀ alkynyl groups, C ₃ to C ₂₀ a cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted with a heavy hydrogen aryl, C ₈ ~ C ₂₀ arylalkenyl group, a group a heterocyclic of substituted or unsubstituted C ₅ ~ C ₂₀ ring Any group selected from the group consisting of:

,

,

,

,

,

,

,

,

,

구성된 그룹으로부터 선택된 하나일 수 있다. Meanwhile, in Formulas 2 and 3, R ¹ to R ⁴ are

,

,

,

,

,

,

,

,

,

It may be one selected from the configured group.

,

,

,

,

,

,

으로 구성된 그룹으로부터 선택된 하나일 수 있다. In Formulas 2 and 3, L ₁ and L ₂ are

,

,

,

,

,

,

It may be one selected from the group consisting of.

으로 구성된 그룹으로부터 선택된 하나일 수 있다. In Formulas 2 and 3 above, HAr ₁ and HAr ₂ are

It may be one selected from the group consisting of.

In the above formulas, the atom in each heterocycle may have a C6-C60 aryl group which may have a substituent, a C3-C60 heteroaryl group which may have a substituent, or C1-C20 which may have a substituent The bonding group which may be a C1-C20 alkoxy group which may have an alkyl group or a substituent may be couple | bonded, or the case where there are many bond groups may mutually be same or different. Specific examples of the benzo isoquinoline derivatives are described below from the above formula, but are not limited thereto.

As a specific example of the benzo isoquinoline derivative according to an embodiment of the present invention, there are compounds of the formula (4) as a specific example of the benzo isoquinoline compound belonging to formula (2), but the present invention is not limited thereto.

As a specific example of the benzo isoquinoline compound according to an embodiment of the present invention, specific examples of the benzo isoquinoline compound belonging to the formula (3), but the compounds of the formula (5) below, but the present invention is not limited thereto.

Various organic electronic devices exist in which the benzoisoquinoline compounds described with reference to Chemical Formulas 1 to 5 are used as the organic material layer. The organic electronic device in which the benzo isoquinoline compounds described with reference to Chemical Formulas 1 to 5 may be used, for example, an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, an organic transistor (organic TFT) Organic semiconductor materials such as photodiodes, organic lasers, and laser diodes may be used.

As an example of the organic electroluminescent device to which the benzo isoquinoline compounds described with reference to Chemical Formulas 1 to 5 may be applied, the present invention is not limited thereto, and the present invention is not limited thereto. Derivative compounds can be applied.

Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formula 1 to 5 Provided is a light emitting device.

An organic light emitting display device according to another embodiment of the present invention, except that at least one layer of the organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer to form the compound of Formula 1 to 5 It can be prepared in a structure known in the art using conventional manufacturing methods and materials in the art. The structure of the organic light emitting display device according to the present invention is illustrated in FIGS. 1 to 5, but is not limited thereto. In this case, reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer, 104 a hole transport layer, 105 a light emitting layer, 106 an electron injection layer, 107 represents a cathode.

In this case, the isoquinoline derivative compound described with reference to Chemical Formulas 1 to 5 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer. Specifically, the isoquinoline derivative compound described with reference to Chemical Formulas 1 to 5 may be used instead of one or more of the hole injection layer, hole transport layer, light emitting layer, and electron transport layer described below, or may be used by forming a layer with them. Of course, the organic layer may be used not only in one layer but also in two or more layers.

In particular, the benzo isoquinoline compounds described with reference to Formulas 1 to 5 may be used as hosts or dopants in luminescent materials and host / dopants. That is, the benzo isoquinoline compound described with reference to Chemical Formulas 1 to 5 may replace the existing materials or form the corresponding layers with the existing materials in the light emitting layer, respectively.

For example, the organic light emitting device according to another embodiment of the present invention is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation It can be prepared by depositing an oxide or an alloy thereof to form an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. .

In addition to the above method, an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

The organic electroluminescent device according to another embodiment of the present invention may form an organic material layer, for example, a light emitting layer, by a soluble process of the benzoisoquinoline compound described above.

The substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.

An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon. As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

The hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is positioned on the hole injection layer. The hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons. In addition to these general requirements, when applied for vehicle body display, heat resistance to the device is required, and a material having a glass transition temperature (Tg) of 70 ° C. or higher is preferable. Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene and silicon germanium oxide. Compounds, silicone arylamine compounds and the like.

The organic light emitting layer is positioned on the hole transport layer. The organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.

Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3) in order to increase blue light emission efficiency. A small amount of '[(1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine) can be used. In the case of red, DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H A small amount of doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile) is used. When forming a light emitting layer using a process such as inkjet printing, roll coating, or spin coating, a polymer of polyphenylene vinylene (PPV) -based polymer or poly fluorene may be used for the organic light emitting layer. .

As described above, the benzo isoquinoline compound described with reference to Chemical Formulas 1 to 5 may replace the existing materials or form the corresponding layers with the existing materials in the light emitting layer, respectively.

As described above, the benzoisoquinoline compound described with reference to Chemical Formulas 1 to 5 may be a hole injection material, a hole transport material, and / or suitable for fluorescent and phosphorescent devices of all colors, such as red, green, blue, and white, depending on the synthesized compound. It can also be used as a luminescent material.

For example, the benzo isoquinoline compounds described with reference to Formulas 1 to 5 may be used as dopants or host materials of fluorescent or phosphorescent in various colors.

The electron transport layer is positioned on the organic light emitting layer. The electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The cathode is positioned on the electron transport layer. This cathode serves to inject electrons into the electron transport layer. As the material used as the cathode, it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection. In particular, a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used. In addition, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 μm or less may also be used.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.

Meanwhile, the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, various computers, and the like.

Example

Hereinafter, the present invention will be described in more detail with reference to Preparation Examples and Experimental Examples. However, the following Preparation Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Production Example

Hereinafter, the preparation or synthesis examples of the benzo isoquinoline compounds belonging to formulas (4) and (5) will be described. However, only one or two of the benzo isoquinoline compounds belonging to the general formula (4) and (5) because of the large number of benzo isoquinoline compounds belonging to the general formula (4) and 5 will be described as an example. Those skilled in the art, that is, those skilled in the art, may prepare isoquinoline compounds belonging to the present invention which are not illustrated through the preparation examples described below.

의 제조)Preparation Example 1 Compound belonging to the group of Formula 2

Manufacture)

In a flask containing 3-Bromoquinoline (4.77 g, 22.94 mmol) dissolved in THF, iPrMgCl (11.47 ml, 22.94 mmol) was slowly dropped at 0 ° C. and stirred for 2 hours to form a grirnard reagent. Drop benzo [g] isoquinoline-5,10-dione (2.00 g, 9.56 mmol) dissolved in THF and stir at room temperature for 24 hours. Concentrate the reaction solvent, add SnCl ₂ -2H ₂ O (6.50 g, 29.00 mmol) and Acetonitrile and stir at reflux for 4 hours. The reaction was terminated with water, extracted with MC, dried over MgSO ₄ , and then 2.50 g of a product was obtained on a silica gel column.

MS: m / z = 433.27 [M ⁺ ]

의 제조)Preparation Example 2 Compounds belonging to the group of formula 3

Manufacture)

In a round flask, 5,10-Bis (4-bromophenyl) benzo [g] isoquinoline (3.0 g, 6.13 mmol), Diphenylamine (2.08 g, 12.27 mmol), t-BuONa (1.78 g, 18.39 mmol), Pd (dba) ₃ (0.3 g, 5 mol%) and P (t-Bu) ₃ (0.06 g, 5 mol%) were added, toluene was added, and the mixture was stirred under reflux at 110 ° C for 12 hours. Toluene was concentrated, extracted with MC, water, dried over MgSO ₄ , celite filter, columned with hexane, and recrystallized with hexane and MeOH to obtain 1.5 g of the product.

MS: m / z = 665.77 [M ⁺ ]

Comparative Example 1

(200Å)/ LiF / Al로 소자를 구성하고, 비교예의 소자구조는 ITO/ 4,4’,4”-Tris[2-naphthyl(phenyl)amino]-triphenylamine (2-TNATA) (600Å) / NPB (300Å) / ADN (300Å ): BD025x (7 %) / Alq3 (200Å)/ LiF / Al로 소자를 구성하였다. 청색 도판트(Blue Dopant)로 측정시에는 상기 전극에 2-TNATA (600Å) / NPB (30Å) / ADN (9,10-디(나프탈렌-2-일)안트라센, 300Å): 화합물 2-1

(7 %) / Alq3 (200Å)/ LiF / Al로 소자를 구성하고, 비교예의 소자구조는 ITO/ 2-TNATA (600Å) / NPB (300Å) / ADN (300Å): BD025x (7 %) / Alq3 (200Å)/ LiF / Al로 소자를 구성하였다. The organic substrate having an ITO transparent electrode having a thickness of 25 mm x 75 mm width x 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. 2-TNATA (600Å) / NPB (300Å) / ADN (300Å): BD025x (7%) / Compound 1-1

(200 구조) / LiF / Al, and the device structure of the comparative example is ITO / 4,4 ', 4 ”-Tris [2-naphthyl (phenyl) amino] -triphenylamine (2-TNATA) (600Å) / NPB (300 Hz) / ADN (300 Hz): The device was constructed of BD025x (7%) / Alq3 (200 Hz) / LiF / Al. When measured with a blue dopant, 2-TNATA (600 kPa) / NPB (30 kPa) / ADN (9,10-di (naphthalen-2-yl) anthracene, 300 kPa) on the electrode: Compound 2-1

The device is composed of (7%) / Alq3 (200 mW) / LiF / Al, and the device structure of the comparative example is ITO / 2-TNATA (600 mW) / NPB (300 mW) / ADN (300 mW): BD025x (7%) / Alq3 The device was constructed with (200 mA) / LiF / Al.

Tables 1 and 2 show driving voltages, current density diagrams, efficiency, and color coordinates. As a result of the device evaluation, it was found that the material of the electron transport layer showed the efficiency increase, the driving voltage drop, the lifetime increase, and the stability increase effect, and the blue dopant material showed excellent color purity.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention are not limited by these embodiments.

The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

1 to 5 show examples of the organic electric device to which the compound of the present invention can be applied.

Claims (12)

Benzo isoquinoline compound represented by the following formula.

Wherein (1) L ₁ and L ₂ represent a group selected from a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted hetero arylene group, and a divalent substituted or unsubstituted aliphatic hydrocarbon, and (2 ) X ₁ and X ₂ are each independently halogen, amino group, nitrile group, nitro group C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkyl thiophene groups, C ₆ to C ₂₀ aryl thiophene groups, C ₂ to C ₂₀ alkenyl groups, C ₂ to C ₂₀ alkynyl groups, C ₃ to C ₂₀ cycloalkyl groups, C ₆ to C ₂₀ Aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ aryl alkenyl group, substituted or unsubstituted silane group, substituted or unsubstituted boron group, substituted or unsubstituted germanium group , and the aryl group a substituted or unsubstituted C ₅ ~ C ₂₀ by at least one group selected from the group consisting of heterocyclic ring groups is substituted or unsubstituted C ₆ ~ C ₂₀ of; Of _{halogen, CN, NO 2, C 1} ~ C 20 alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ coming of the alkyl group, C ₂ ~ C ₂₀ of the alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a substituted or unsubstituted silane group , a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C ₅ ~ C ₂₀ by at least one group selected from the group consisting of a heterocyclic-substituted or unsubstituted C ₅ ~ C ₂₀ of the ring Heterocyclic group; Or a condensed ring group of a C ₆ to C ₂₀ aromatic ring and a C ₄ to C ₂₀ aliphatic ring, each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group , A substituted and unsubstituted hetero aryl group. Benzo isoquinoline compound represented by the following formula.

Wherein (1) L ₁ and L ₂ represent a group selected from a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted hetero arylene group, and a divalent substituted or unsubstituted aliphatic hydrocarbon, and (2 ) HAr ₁ and HAr ₂ may be the same as or different from each other, and represent a group selected from an aryl group having 6 to 60 carbon atoms which may have a substituent or a teraryl group having 3 to 60 carbon atoms which may have a substituent. Benzo isoquinoline compound represented by the following formula.

Wherein (1) L ₁ and L ₂ represent a group selected from a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted hetero arylene group, and a divalent substituted or unsubstituted aliphatic hydrocarbon, and (2 R ₁ to R ₄ represent a substituted or unsubstituted same or different group, C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxy group, C ₁ to C ₂₀ alkylamine group, C ₁ to C ₂₀ Alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ Any group selected from the group consisting of an aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ aryl alkenyl group, a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group. The method of claim 3, R ¹ to R ⁴ are

,

,

,

,

,

,

,

,

,

Benzo isoquinoline compound, characterized in that one selected from the group consisting of. The method according to any one of claims 1 to 3, L ₁ and L ₂ are

,

,

,

,

,

,

Benzo isoquinoline compound, characterized in that one selected from the group consisting of. The method of claim 2, HAr ₁ and HAr ₂ is

Benzo isoquinoline compound, characterized in that one selected from the group consisting of. An organic electronic device comprising at least one organic material layer comprising a compound of any one of claims 1 to 3. The method of claim 7, wherein The organic electronic device is an organic electroluminescent device comprising a first electrode, the at least one organic material layer and the second electrode in a stacked form sequentially. The organic electronic device of claim 8, wherein the organic material layer includes a hole injection / transport layer, a light emitting layer, and an electron injection layer, and the compound of claim 1 is included in the light emitting layer. 10. The method of claim 9, An organic electronic device comprising the compound of claim 1 to form the light emitting layer by a solution process (soluble process). The organic electronic device of claim 9, wherein the compound is used as a dopant material in the emission layer. A display device comprising the organic electric element of claim 7; And a control unit for driving the display device.

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