KR20120096382A - Organic light compound and organic light device using the same - Google Patents

Abstract

PURPOSE: An organic photoelectric device is provided to provide high luminous efficiency high luminance, high color purity, and remarkably improved life time. CONSTITUTION: An organic photoelectric device comprises a first electrode, a second electrode, and at least one of organic layer between the first electrode and the second electrode. The organic film comprises organic luminescent compound in chemical formula F. In chemical formula F, P is H, D, F, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydro carbon.

Description

Organic light emitting compound and organic optical device using the same {ORGANIC LIGHT COMPOUND AND ORGANIC LIGHT DEVICE USING THE SAME}

The present invention relates to an organic light emitting compound, in particular dibenzoanthracene, more particularly an asymmetric dibenzoanthracene-based derivative and an organic optical device using the same, and more particularly, excellent luminous efficiency, luminous brightness, color purity and luminous lifetime. The present invention relates to an organic light emitting device that can be implemented, an organic light emitting compound or a photovoltaic device for use in the same, and an optical compound used for the same.

An organic electronic device is an electronic device using an organic semiconductor material and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material. The organic electronic device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form. The second type is an electronic device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor, all of which are electron / hole injection materials, electron / hole extraction materials, electron / holes for driving the device. Requires a transport material or a luminescent material. Hereinafter, the organic light emitting device will be described in detail, but in the organic electronic devices, the electron / hole injecting material, the electron / hole extracting material, the electron / hole transporting material, or the light emitting material all have a similar principle.

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 light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic layer between them. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected into the anode, electrons are injected into the organic layer, electrons are injected into the organic layer, excitons are formed when injected holes and electrons meet, When it falls to a state, it becomes a light. Such organic light emitting diodes are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as the organic material layer in the organic light emitting device 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 luminescent material may be classified into blue, green, and red luminescent materials and yellow and orange luminescent materials required to achieve better natural colors according to the emission color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than a host mainly constituting the light emitting layer is mixed in the light emitting layer, and excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order to fully exhibit the excellent characteristics of the organic light emitting device described above, 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. Must be preceded.

Among them, as the electron transporting material, organometallic complexes having excellent stability to electrons and an electron moving speed as organic monomolecular materials are preferable. Among them, Alq3 having excellent stability and high electron affinity has been reported to be the most excellent, but when used in a blue light emitting device, there is a problem in that color purity is poor due to light emission due to exciton diffusion. In addition, Sanyo's Flavon derivatives or Chiso's germanium and silicon chloropetadiene derivatives are known. (Japanese Patent Laid-Open No. 1998-017860, Japanese Patent Laid-Open No. 1999-087067) ).

In addition, the organic monomolecular substance includes PBD (2-biphenyl-4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole) derivative coupled to a spiro compound and hole blocking ability. And TPBI (2,2 ', 2 "-(benzene-1,3,5-triyl) -tris (1-phenyl-1H-benzimidazole), which have good electron transport ability (Adv. Mater. 10). , 1998, 1136 & Tao et al, Appl. Phys. Lett. 77, 2000, 1575. In particular, benzo imidazole derivatives published by LG Chem are widely known for their excellent durability.

Organic light emitting devices using the organic single molecular material as an electron transporting layer have short lifetime, low storage durability and low reliability. These problems are caused by physical or chemical changes of organic materials, photochemical or electrochemical changes of organic materials, oxidation and peeling of the cathodes, and durability.

Therefore, organic light emitting devices using a method of obtaining an arbitrary emission color by changing the structure of the organic monomolecular material used in the organic light emitting device or obtaining various high efficiency by the host dopant system have been proposed. It lacks properties, life and durability.

As a solution to the above problems, for example, Korean Patent Laid-Open Publication No. 2003-0067773 discloses a compound having a benzoimidazole wheel and anthracene skeleton.

However, there is a continuing need for the development of new materials having improved luminescence brightness, luminescence efficiency, and lifetime, as compared with organic EL devices using such compounds.

The first technical problem to be achieved by the present invention is to provide a new organic optical compound that can be applied to organic optical devices, in particular organic electroluminescent devices.

The second technical problem to be achieved by the present invention is to provide an organic electroluminescent device and a photovoltaic device for photovoltaic power generation, including the novel compound, low driving voltage, improved luminous efficiency, brightness, color purity, thermal stability and lifetime. .

The organic electroluminescent compound according to the present invention and the organic photoconductor using the same are based on the organic electroluminescent compound represented by the following formula (F)

<Formula F>

In the above formula (F)

P is H, D, F, substituted or unsubstituted C6-C50 aryl group, substituted or unsubstituted C2-C50 heteroaryl group, substituted or unsubstituted C2-C50 cycloalkyl group, substituted or unsubstituted C2-C50 Heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon.

Furthermore, the organic optical compound and the organic optical device using the same according to the present invention are based on the organic photo compound corresponding to the following Chemical Formulas 1 to 143.

The organic optical device according to the present invention provides high luminous efficiency, high luminance, high color purity and remarkably improved luminous lifetime,

In addition, the present invention provides an organic light emitting device and an organic light emitting compound, or an organic optical device and a photo compound for photovoltaic power generation.

Hereinafter, the present invention will be described in detail.

The present invention may be modified in various ways and may have various forms, and thus embodiments (or embodiments) will be described in detail in the text. However, this is not intended to limit the present invention to the specific form disclosed, it should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In the present application, the term &quot; comprising &quot; or &quot; consisting of &quot;, or the like, refers to the presence of a feature, a number, a step, an operation, an element, a component, But do not preclude the presence or addition of one or more other features, integers, steps, operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.

The present invention is to develop a dibenzoanthracene, more specifically, an asymmetric dibenzoanthracene-based derivative to form various organic materials between the first electrode and the second electrode, such as an electron transport layer (ETM), a light emitting layer (EML), a hole transport layer (HTM), etc. We will present materials that can be used in various ways, such as films, and improve materials such as increased efficiency and reduced driving voltage, and develop materials that maximize their ability as OLED materials.

In the present specification, an organic photochemical compound is a compound used in an organic optical device, and is not necessarily limited to a compound capable of emitting light, and its application range is not limited to an organic light emitting layer, and an organic photonic compound such as a charge injection layer and a charge transport layer It can be used in any layer that constitutes the ruler.

In this specification, the terms 'optical compound' and 'optical device' are used to cover the case where the present invention is applied to both an organic light emitting device and a device for solar power generation regardless of a dictionary or conventional definition It is a selected term.

An organic optical device according to the first aspect of the present invention, the first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode.

The organic photochemical compound used in the organic photoelectric device of the present invention may have a structure represented by Chemical Formulas 1 to 143 (hereinafter, the chemical formulas are omitted and only numbers are shown), but is not limited thereto.

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The organic photochemical compound according to the present invention represented by the compounds of Formulas 1 to 143 may be synthesized using a conventional synthesis method, and a detailed synthesis route of the compound may be referred to the schemes of the following Synthesis Examples. The compound of the above formula is suitable for use in an organic film of an organic optical device, particularly a hole transporting layer, a hole injecting layer or a light emitting layer. The structure of the organic light emitting device according to the present invention is very diverse. The organic EL device may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron blocking layer, an electron transporting layer, and an electron injecting layer between the first electrode and the second electrode.

More specifically, an embodiment of an organic light emitting device according to the present invention

First, the organic light emitting device may have a structure including a first electrode / a hole injection layer / a light emitting layer / an electron transport layer / an electron injection layer / a second electrode,

The organic light emitting device may have a structure including a first electrode / a hole injection layer / a hole transport layer / a light emitting layer / an electron transport layer / an electron injection layer / a second electrode,

Further, the organic light emitting device may have a structure of a first electrode / a hole injection layer / a hole transport layer / a light emitting layer / a hole blocking layer / an electron transport layer / an electron injection layer / a second electrode.

In this case, at least one of the hole transport layer, the hole injection layer and the light emitting layer may include a compound according to the present invention.

The light-emitting layer of the organic optical device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm. In addition, the compound according to the present invention can also be used as a fluorescent dopant in the light emitting layer.

Hereinafter, a method of manufacturing an organic optical device according to the present invention will be described with reference to an organic optical device. First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Herein, a substrate used in a conventional organic optical device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal characteristics of the desired hole injection layer, and the like. In general, A degree of vacuum of 10 &lt; ^-5 &gt; to 10 &lt; ^-3 &gt; torr, a deposition rate of 0.01 to 100 A / sec and a film thickness of 100 to 1 mu m.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is preferably from about 2000 rpm to 5000 rpm , And the heat treatment temperature for removing the solvent after coating is suitably selected within a temperature range of about 80 캜 to 200 캜.

The hole injection layer material may be a compound having the formula as described above.

Or phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or the starburst type amine derivatives described in Advanced Material, 6, p.677 (1994), for example, TCTA, m-MTDATA, m-. MTDAPB, 2-TNATA (4,4 ', 4 "-tris (N- (2-naphtyl) -N-phenylamino) triphenylamine: 4,4,4-tris (N- (naphthyl) -N-phenylamino) Triphenylamine), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (soluble conductive polymer) 3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonicacid: polyaniline / camphorsulfonic acid) or PANI / PSS

(Polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)) and the like can be used.

The thickness of the hole injection layer may be about 100 Å to 10000 Å, preferably 100 Å to 1000 Å. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.

Alternatively, the hole injection layer may be formed by vacuum vapor deposition. Although specific deposition conditions depend on the compound used, they are selected from the range of conditions substantially the same as the formation of a general hole injection layer. For example, DNTPD (N, N-bis- [4- (di-m-tolylamino) phenyl] -N, N-diphenylbiphenyl-4,4-diamine) may be used.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. In the case of forming the hole transporting layer by the vacuum deposition method and the sputtering method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The hole transport layer material may comprise a compound of the formula as described above. Or carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole and the like, N, N'-bis (3-methylphenyl) -N, N'- diphenyl- [ Amine having an aromatic condensed ring such as N, N'-tetramethyldisiloxane, -4,4'-diamine (TPD) and N, N'-di (naphthalen- The hole transporting layer may have a thickness of about 50 Å to 1000 Å, preferably 100 Å to 600 Å. When the thickness of the hole transporting layer is less than 50 Å, the hole transporting property may be degraded. When the thickness of the hole transporting layer is more than 1000 Å, the driving voltage may increase.

Next, the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like. When the light emitting layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The light emitting layer may comprise a compound of the formula according to the present invention as described above. At this time, the compounds of the formula can be used together with suitable known host materials or can be used together with known dopant materials.

It is also possible to use the compound of the above formula alone. In the case of the host material, for example, Alq3 (tris (8-hydroxy-quinolatealuminium) or CBP (4,4'-N, N'-dicarbazole- ) Can be used.

In the case of the dopant material, IDE102, IDE105 and IDE55 available from Idemitsu Co., Ltd. and C545T available from Hayashibara Co., Ltd. can be used. As the phosphorescent dopant, red phosphorescent dopant PtOEP, UDC RD61, green phosphorescent dopant Ir (PPy) 3 (PPy = 2-phenylpyridine), a blue phosphorescent dopant F2Irpic, and a red phosphorescent dopant RD 61 manufactured by UDC. MQD (N-methylquinacridone), coumarine derivatives and the like can also be used.

The doping concentration is not particularly limited, but the content of the dopant is generally 0.01 to 15 parts by weight based on 100 parts by weight of the host. The thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa.

When the thickness of the light emitting layer is less than 100 Å, the light emitting characteristics may be degraded. If the thickness of the light emitting layer is more than 1000 Å, the driving voltage may increase.

When a luminescent compound is used together with a phosphorescent dopant in the luminescent layer, a method such as vacuum deposition, spin coating, casting, LB or the like is performed on the luminescent layer to prevent the triplet excitons or holes from diffusing into the electron transporting layer The hole blocking layer HBL can be formed. In the case of forming the hole blocking layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer. Known hole blocking materials that can be used include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and BCP.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. If the thickness of the hole blocking layer is less than 50 angstroms, the hole blocking characteristics may be deteriorated. If the thickness of the hole blocking layer exceeds 1000 angstroms, the driving voltage may be increased. An organic light emitting element having the structure shown in FIG. 1B is obtained.

Next, an electron transport layer (ETL) is formed by various methods such as a vacuum evaporation method, a spin coating method, and a casting method.

When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer. The electron transport layer material serves to stably transport electrons injected from an electron injection electrode, and is a quinoline derivative, particularly a known material such as tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, Materials may also be used.

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. When the thickness of the electron transporting layer is less than 100 angstroms, the electron transporting characteristics may be deteriorated. When the thickness of the electron transporting layer exceeds 1000 angstroms, the driving voltage may increase.

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited.

As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injection layer may be about 1 A to 100 A, preferably 5 A to 50 A. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode can be formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like.

The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic electroluminescent compound according to another embodiment of the present invention may be represented by the above formula, and more specifically, may be represented by the formula (1) to 143. Details of the compounds are the same as those described for the above-mentioned organic feet and devices.

Hereinafter, the reaction examples and comparative examples of the present invention will be specifically illustrated, but the present invention is not limited to the following synthesis examples and examples. In the following reaction examples, the intermediate compounds are indicated by adding the serial number to the final product number. For example, Compound 1 is represented by the compound [1], and the intermediate compound of the above compound is represented by [1-1] or the like. In the present specification, the chemical number is represented by the chemical number. For example, the compound represented by Formula 1 is represented by Compound 1

[Reaction Example 1] Synthesis of Compound [1]

Synthesis of Intermediate Compound [1-1]

4-bromodibenzo [b, d] thiophene (28.7g, 111.8mmol) was added to 500ml round plaque, dissolved in 300ml of THF, cooled to -78 ℃, and 44.7ml of 2.5M normal butyllithium was added dropwise under nitrogen atmosphere. After stirring for 30 minutes, phthalaldehyde (5g, 37.3mmol) was added and stirred for 4 hours.

Aqueous supersaturated ammonium chloride solution was added to terminate the reaction, washed with a saturated aqueous sodium chloride solution, and separated by a column filled with silica gel to prepare 9.75 g (58%) of an intermediate compound [1-1] in oil form.

 Synthesis of Intermediate Compound [1-2]

 9.75 g of intermediate compound [1-1] was dissolved in 200 ml of dichloromethane, followed by acetic anhydride (8.8 g, 86.4).

mmol), triethylamine (13.1g, 129.6mmol) and DMAP (3.17g, 25.9mmol) were added, and the mixture was stirred under reflux for 10 hours in a nitrogen atmosphere, washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate to give an intermediate compound in the form of an oil. [1-2] 9.4 g (93%) was prepared.

 Synthesis of Intermediate Compound [1-3]

Dissolve 9.4 g of Intermediate Compound [1-2] in 200 ml of dichloromethane, add trichloromethane sulfonic acid (0.3 g, 1.98 mmol) in a nitrogen atmosphere, stir for 10 minutes, and add aqueous sodium bicarbonate solution to terminate the reaction. After washing with an aqueous sodium chloride solution and drying with anhydrous magnesium sulfate, and separated by a column packed with silica gel 7.1g (79%) of a yellow solid intermediate compound [1-3].

 Synthesis of Intermediate Compound [1-4]

Dissolve 7.1 g of Intermediate Compound [1-3] in 150 ml of DMF, add 3.3 g (18.7 mmol) of N-bromosuccinimide, stir at room temperature for 4 hours, and precipitate. The precipitated solid is filtered and washed with purified water and acetone to give a yellow solid. 7.5 g (90%) of an intermediate compound [1-4] was prepared.

  Synthesis of Compound [1]

2-trimethylsilylpyridine (5.32 g, 22 mmol) was dissolved in N, N-dimethylformamide (100 ml), followed by 9-bromo-14- (phenanthrene-9-yl) benzo [f] tetrafen (9.78 g, 18.33 mmol), tetrakisphosphino palladium (0.2 g, 0.183 mmol) was added, stirred at 120 ° C. for 3 hours, cooled to room temperature, 100 ml of methanol was added, the resulting solid was filtered and washed with distilled water and methanol. [1] 6.1 g (63%) was prepared.

Compounds 1 to 143 were prepared according to the method of Reaction Example 1, and the results are shown in the following [Table 1].

[First vote group]

Comparative Example 1

Using compound a represented by the following formula a as a fluorescent green host, compound b represented by the following formula b as a fluorescent green dopant, 2-TNATA (4,4 ', 4 ”-tris (N-naphthalen- 2-yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. An organic light emitting device having the following structure was prepared: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound b (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm). ) / Al (60 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound a represented by Formula a and Compound b represented by Formula b (3% doping) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum deposited on the electron transport layer to prepare an organic light emitting device as shown in Table 3. This is referred to as Comparative Sample 1.

<Formula a> <Formula b>

                <Formula c>

Examples 1 to 143

The same method as Comparative Example 1 except that Compounds 1 to 143 represented by Formulas 1 to 143 disclosed in Synthesis Example were used as electron transport layer compounds instead of Compound c (Alq3) as the electron transport layer compound. ITO / 2-TNATA (80nm) / α-NPD (30nm) / Compound a + Compound b (30nm) / Electron Transport Layer Compound 1 ~ 143 / LiF (0.5nm) / Al (60nm) The device was manufactured. These are referred to as samples 1 to 143, respectively.

Evaluation Example 1: Evaluation of emission characteristics of Comparative Sample 1 and Samples 1 to 143

For Comparative Sample 1 and Samples 1 to 143, luminescence brightness, luminescence efficiency, and luminescence peak were evaluated using Keithley SMU 235 and PR650, respectively, and the results are shown in the following [Table 2]. The samples showed green emission peaks in the range of 514-524 nm.

As shown in [Second Table], Samples 1 to 143 showed improved luminescence properties compared to Comparative Sample 1.

Although the well-known techniques are omitted in the above description, those skilled in the art can easily infer, infer, and reproduce them.

Claims (10)

A first electrode; A second electrode; And an organic optical device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic light emitting compound of Formula F:
<Formula F>

In Formula F
P is H, D, F, substituted or unsubstituted C6-C50 aryl group, substituted or unsubstituted C2-C50 heteroaryl group, substituted or unsubstituted C2-C50 cycloalkyl group, substituted or unsubstituted C2-C50 Heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon. The method of claim 1,
P is a group consisting of C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group Selected from; Or a group forming a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group. The method of claim 1,
Wherein P is a C5 ~ C40 heteroaryl group characterized in that the organic optical device. The method of claim 1,
Wherein P is an organic optical device, characterized in that substituted with a heteroaryl group of C5 ~ C40. The method according to claim 3 or 4,
Wherein said hetero aryl group comprises some or all of N, O and S. The method of claim 1,
The aryl group, heteroaryl group, cycloalkyl group and heterocycloalkyl group
A C1-C50 alkyl group; C1-C50 alkoxy group; A C6-C50 aryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; C2-C50 heteroaryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; A C5-C50 cycloalkyl group unsubstituted or substituted by a C1-C50 alkyl group or a C1-C50 alkoxy group; C5-C50 heterocycloalkyl group which is unsubstituted or substituted with a C1-C20 alkyl group or a C1-C20 alkoxy group; Or one or more substituents selected from the group consisting of silane groups. The method of claim 1,
The aryl group, heteroaryl group, cycloalkyl group and heterocycloalkyl group
Hydrogen, phenyl group, tolyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group, anthracenyl group, benzoanthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group , Methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pisenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentaxenyl group, tetraphenylenyl group, hexaphenyl group, Hexenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, fluorenyl group, pyrantrenyl group, obarenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group , Thiophenyl group, indolyl group, furinyl group, benzimidazolyl group, quinolinyl group, benzothiophenyl group, parathiazinyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, imidazolinyl group, oxazolyl group, thia Zolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , Pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, thianthrenyl, cyclopentyl, cyclohexyl, oxiranyl, pyrrolidinyl, pyrazolidinyl, imidazoli An organic photo device having at least one substituent selected from the group consisting of a diyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a di (C6-C50 aryl) amino group, a silane group and derivatives thereof. The method according to any one of claims 1 to 4,
An organic optical device characterized in that the organic light emitting compound is represented by the formula 1 to 143:

An organic light emitting compound represented by Chemical Formula F:
<Formula F>

In Formula F
P is H, D, F, substituted or unsubstituted C6-C50 aryl group, substituted or unsubstituted C2-C50 heteroaryl group, substituted or unsubstituted C2-C50 cycloalkyl group, substituted or unsubstituted C2-C50 Heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon. The method of claim 9,
An organic light emitting compound, characterized in that the organic light emitting compound is represented by the formula 1 to 143: