WO2018212435A1 - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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Publication number
WO2018212435A1
WO2018212435A1 PCT/KR2018/002482 KR2018002482W WO2018212435A1 WO 2018212435 A1 WO2018212435 A1 WO 2018212435A1 KR 2018002482 W KR2018002482 W KR 2018002482W WO 2018212435 A1 WO2018212435 A1 WO 2018212435A1
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Prior art keywords
group
light emitting
compound
formula
organic light
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PCT/KR2018/002482
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French (fr)
Korean (ko)
Inventor
차용범
김민준
김연환
김정범
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020170158935A external-priority patent/KR20180125369A/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880004697.6A priority Critical patent/CN110024155B/en
Publication of WO2018212435A1 publication Critical patent/WO2018212435A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer may be formed of a mostly formed in a multilayer structure comprising layers of different materials in order to improve the efficiency and stability of the organic light-emitting device, such as a hole injection layer, a hole transport layer, a light emitting layer, i an electron transporting layer, an electron injection layer, etc.
  • Patent Document 0001 Korean Patent Publication No. 10-2000—0051826
  • the present invention relates to an organic light emitting device having improved driving voltage, efficiency and lifetime.
  • the present invention provides the following organic light emitting device:
  • a light emitting layer between the anode and the cathode A light emitting layer between the anode and the cathode
  • the light emitting layer comprises a compound represented by the following formula (1)
  • the electron suppression layer comprises a compound represented by the following formula (2)
  • an organic light emitting device :
  • Ri to R 4 are each independently hydrogen; Substituted or unsubstituted d-so alkyl or substituted or unsubstituted C 6 -60 aryl, or two adjacent groups combine to form a benzene ring,
  • ⁇ ! ⁇ is substituted or unsubstituted C 6 -60 aryl
  • Ar 3 is a substituted or unsubstituted C 6 -6o aryl
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently hydrogen; Substituted or unsubstituted d- 60 alkyl; Or substituted or unsubstituted C 0 aryl, or two adjacent groups combine to form a benzene ring,
  • L is a bond; Or substituted or unsubstituted CEHSO arylene,
  • Ar 4 to Ar 6 are each independently C 6 -60 aryl.
  • the organic light emitting device described above is excellent in driving voltage, efficiency, and lifetime. [Brief Description of Drawings]
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, an electron suppression layer 3, a light emitting layer 4, and a cathode 5. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole transport layer 6, an electron suppression layer 3, a light emitting layer 4, an electron transport layer 7 and a cathode 5. It is shown.
  • ⁇ or I means a bond connected to another substituent.
  • substituted or unsubstituted in the specification is deuterium; Halogen group; nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; or .
  • the substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group, and can be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine,
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. Work According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl 1-methyl-butyl, 1-ethyl-butyl, pentyl, n- Pentyl, isopentyl, neopentyl, ter t-pentyl, nuclear chamber, n-nuclear chamber, 1—methylpentyl, 2-methylpentyl, 4 one methyl— 2 —pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, Heptyl, n-heptyl, 1-methylnuclear, cyclopentylpentyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhe
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2—butenyl, 3-butenyl, 1-pentenyl, 2—pentenyl, 3-pentenyl, 3-methyl-1′part Tenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2, 2-diphenylvinyl-1xyl, 2-phenyl-2- (naphthyl — 1-yl) vinyl-l-yl, 2,2-bis (diphenyl-l-yl) vinyl-l-yl, stilbenyl groups, styrenyl groups and the like, but not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heterocyclic group containing one or more of 0, N, S i and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group , Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline Group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, Dibenzothiophene group, benzofuranyl group, phenan
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description about the heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • the anode and cathode used in the present invention means an electrode used in the organic light emitting device.
  • a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc, and gold or alloys thereof; Metals such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide ( ⁇ 0) oxide; ⁇ a combination of a metal and an oxide such as ⁇ 0: A1 or SN0 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4— (ethylene—1,2-dioxy) thiophene] (?
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the light emitting layer used in the present invention means a layer capable of emitting light in the visible light region by combining holes and electrons received from the anode and the cathode.
  • the light emitting layer includes a host material and a dopant material
  • the present invention includes the compound represented by Chemical Formula 1 as a host.
  • Ri to all are hydrogen, or two adjacent groups are bonded to each other to form a benzene ring, and the rest are hydrogen. More preferably, the formula is represented by the following formulas 1-2, 1-3, 1-4, 1-5, or 1-6:
  • A, Ar 3 , R 5 to 3 ⁇ 4 are as defined above.
  • ⁇ is phenyl, biphenylyl, naphthyl, or dimethylfluorenyl.
  • Ar 2 is any one selected from the group consisting of
  • Ar 3 is phenyl ⁇ biphenylyl, or naphthyl.
  • Representative examples of the compound represented by Formula 1 are as follows:
  • the compound represented by Chemical Formula 1 may be prepared by the same method as in Preparation.
  • Ri to R4, An, Ar 2> Ar 3 and R 5 to 3 ⁇ 4 are as defined above, and each X is independently halogen.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the dopant material is not particularly limited as long as it is a material used for an organic light emitting device. For example, an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, etc. are mentioned.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the organic light emitting device includes an electron suppression layer between the anode and the light emitting layer.
  • the electron suppression layer is included in contact with the anode side of the light emitting layer.
  • the electron suppression layer serves to improve efficiency of the organic light emitting device by inhibiting electrons injected from the cathode from being transferred toward the anode without recombination in the emission layer.
  • a compound represented by Chemical Formula 2 is used as a material constituting the electron suppression layer.
  • Formula 2 is represented by the following Formula 2-1, or 2-2:
  • Ar 4 , Ar 5 , and ⁇ 6 are as defined above.
  • Ar 4 is phenyl.
  • Ar 5 and Ar 6 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenanthrenyl, phenanthrenylphenyl, or Triphenylenyl.
  • Representative examples of the compound represented by Formula 2 are as follows:
  • the compound represented by Chemical Formula 2 may be prepared by the same method as in Scheme 2 below.
  • the organic light emitting device may include a hole transport layer between the electron suppression layer and the anode.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • a hole transporting material is a material capable of transporting holes from an anode or a hole injection layer to a light emitting layer. This is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a nonconjugated portion together.
  • Hole injection layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • a hole transporting material is a material capable of transporting holes from an anode or a hole injection layer to a light emitting layer. This is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a
  • the organic light emitting device may further include a hole injection layer between the anode and the hole transport layer, if necessary.
  • the hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the movement of the produced excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Also, of hole injection materials
  • H0M0 highest occupied mol ecular orbital
  • the hole injecting material include metal porphyr, oligothiophene, arylamine-based organic matter, nucleonitrile-nucleated azatriphenylten-based organic material, quinacridone-based organic material, and perylene ) Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the organic light emitting device may include an electron transport layer between the light emitting layer and the cathode.
  • the electron transport layer is a layer that receives electrons from the electron injection layer formed on the cathode or the cathode to transport electrons to the light emitting layer, and also suppresses the transfer of holes from the light emitting layer.
  • a material which can receive and transfer to a light emitting layer a material having high mobility to electrons is suitable.
  • Specific examples of the electron transporting material 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 electron transport layer can be used with any desired cathode material, as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • Electron injection layer The organic light emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the cathode as necessary.
  • the electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer It is preferable to use a compound which prevents the movement to a layer and is excellent in thin film formation ability.
  • the material that can be used as the electron injection layer fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preore Nilidene methane, anthrone and the like, derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, but are not limited thereto.
  • the metal complex compound include 8-hydroxy , quinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper and bis (8-hydroxyquinolinato) manganese , Tris (8 ⁇ hydroxyquinolinato) .
  • Organic light emitting device bis (10—hydroxybenzo [h] quinolinato) beryllium, bis (10- Hydroxybenzo [h] quinolinato) zinc, bis (2—methyl-8 ⁇ quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0—cresolato) gallium, bis (2- Methyl-8-quinolinato) (1-naph
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, an electron suppression layer 3, a light emitting layer 4, and a cathode 5.
  • the hole transport layer (6) and The structure of the organic light emitting element in the case of including the electron transport layer 7 is illustrated in FIG. 2.
  • the organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configuration. At this time, a metal oxide or a metal oxide having a conductivity or a metal on a substrate by using a method of physical vapor deposition (PVD) such as sputtering or e-beam evaporat ion.
  • PVD physical vapor deposition
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material on a substrate to an anode material in the reverse order of the above-described configuration (W0 2003/012890).
  • the light emitting layer may be formed of a host and a dopant not only by vacuum deposition but also by solution coating.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the contents of the present invention are not limited thereto.
  • Compound 1-2 was prepared by the same method as the method for preparing compound 1-1, except that compound 1-b was used instead of compound l-a.
  • Compound 1-4 was prepared in the same manner as the method for preparing Compound 1-1, except that Compound 1-d was used instead of Compound 1—a.
  • Compound 1-6 was prepared by the same method as the method for preparing compound 1-3, except that compound 1-f was used instead of compound 1-c.
  • Compound 1-9 was prepared by the same method as the method for preparing compound 1-3, except that compound lh was used instead of compound 1-c.
  • Compound 1-12 was prepared in the same manner as the method for preparing compound 1-3, except that Compound 1-e was used instead of Compound 1-c.
  • a glass substrate coated with a thin film having an indium tin oxide (IT0) thickness of 1,000 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • IT0 indium tin oxide
  • Fischer Co. product was used as the detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • isopropyl alcohol, acetone, and methane were ultrasonically washed with a solvent, dried, and then transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • a compound represented by the following HAT was thermally vacuum deposited to a thickness of 150 A on the IT0 transparent electrode prepared as described above to form a thin film. Subsequently, the compound represented by the following HT-1 on the thin film is deposited to a thickness of 1150 A to form a hole transport layer, and the compound represented by Formula 2-1 prepared above is deposited to a thickness of 100A on the electron blocking layer Formed. Subsequently, 10 wt% of the compound represented by the following RD-1 was doped into the compound represented by the formula (1-2) of the prepared example, and the thickness was 300A. A light emitting layer was formed.
  • a hole blocking layer was formed by evaporating to a thickness of compound 50A represented by the following HB-1, and then a compound represented by ET-1 was deposited to a thickness of '310A to form an electron transporting layer.
  • Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 1,000 A were sequentially deposited on the electron transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3A / sec
  • the aluminum was maintained at the deposition rate of 2A / sec.
  • the degree of vacuum was maintained at 2 ⁇ ⁇ 7 to 5 X 10 "6 torr to fabricate an organic light emitting device. Examples 2 to 24
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 2 below was used instead of the compound represented by 25.1. It is as follows.
  • T97 means the time taken for the luminance to decrease from 3000 nit to 97%.
  • Example 22 1—5 2-6 3.97 23.2 0.651 0.334 380
  • Example 23 1-8 2-6 3.93 23.4 0.652 0.334 385
  • Example 24 1-12 2-6 3.91 23.5 0.653 0.333 385
  • the embodiment using the compound represented by the formula (1) according to the present invention as a host, the compound represented by the formula (2) according to the present invention as an electron suppressing layer, the driving voltage compared to the comparative example It was confirmed that the low, the efficiency and life is improved.
  • the compound represented by the formula (1) according to the present invention when used as the host of the light emitting layer, and the compound represented by the formula (2-3) as the electron suppression layer, the luminous efficiency was the highest.
  • the compound represented by Chemical Formula 1 of the present invention As a host, when the compound represented by Formula 2 of the present invention is used as the electron blocking layer material, it was confirmed that the driving voltage, the luminous efficiency, and the lifetime characteristics were simultaneously improved. .
  • substrate 2 anode

Abstract

Provided is an organic light emitting device having an improved driving voltage, efficiency, and lifetime.

Description

【발명의 명칭】  [Name of invention]
유기 발광 소자 ' Organic Light Emitting Diodes ''
【기술분야】  Technical Field
관련 출원 (들)과의 상호 인용  Cross Citation with Related Application (s)
본 출원은 2017년 5월 15일자 한국 특허 출원 게 10-201그 0060151호 및 2017년 11월 24일자 한국 특허 출원 제 10— 2017— 0158935호에 기초한 우선권의 이익을 주장하며， 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다. 본 발명은 구동 전압, 효율 및 수명이 개선된 유기 발광 소자에 관한 것이다.  This application claims the benefit of priority based on Korean Patent Application No. 10-201 No. 10-201 of May 15, 2017 and Korean Patent Application No. 10—2017— 0158935 of 24 November 2017. All content disclosed in the literature is included as part of this specification. The present invention relates to an organic light emitting device having improved driving voltage, efficiency and lifetime.
【배경기술】  Background Art
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기 에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 웅답 시간을 가지며, 휘도, 구동 전압 및 웅답 속도 특성이 우수하여 많은 연구가 진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며， 예컨대 정공주입층， 정공수송층, 발광층， ᅵ 전자수송층， 전자주입층 등으로 이루어질 수 있다ᅳ 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이， 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 액시톤 (exc i ton)이 형성되며， 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. ■ 상기와 같은 유기 발광 소자에서, 구동 전압, In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted. The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. The organic layer may be formed of a mostly formed in a multilayer structure comprising layers of different materials in order to improve the efficiency and stability of the organic light-emitting device, such as a hole injection layer, a hole transport layer, a light emitting layer, i an electron transporting layer, an electron injection layer, etc. 전압 In the structure of the organic light emitting device, when a voltage is applied between two electrodes, holes are injected into the organic material layer in the anode, and electrons are injected into the organic material layer in the cathode, and axtone (exc i ton) is formed when the injected holes and electrons meet. When the excitons fall back to the ground, they shine. In the organic light emitting device as described above, the driving voltage,
개선된 유기 발광 소자의 개발이 지속적으로 요구되고 있다. 【선행기술문헌】 There is a continuing need for the development of improved organic light emitting devices. Prior Art Documents
【특허문헌】  [Patent literature]
(특허문헌 0001 ) 한국특허 공개번호 제 10-2000— 0051826호  (Patent Document 0001) Korean Patent Publication No. 10-2000—0051826
【발명의 내용】  [Content of invention]
【해결하려는 과제】  [Problem to solve]
본 발명은 구동 전압， 효율 및 수명이 개선된 유기 발광 소자에 관한 것이다.  The present invention relates to an organic light emitting device having improved driving voltage, efficiency and lifetime.
【과제의 해결 수단】  [Measures of problem]
본 발명은 하기의 유기 발광 소자를 제공한다:  The present invention provides the following organic light emitting device:
양극，  anode,
으그  Eug
ᄆ ᄀ ,  Haha
상기 양극과 음극 사이의 발광층, 및  A light emitting layer between the anode and the cathode, and
상기 양극과 발광층 사이의 전자억제층을 포함하고，  An electron suppression layer between the anode and the light emitting layer,
상기 발광층은 하기 화학식 1로 표시되는 화합물을 포함하고， 상기 전자억제층은 하기 화학식 2로 표시되는 화합물올 포함하는 , 유기 발광 소자:  The light emitting layer comprises a compound represented by the following formula (1), the electron suppression layer comprises a compound represented by the following formula (2), an organic light emitting device:
Figure imgf000003_0001
Figure imgf000003_0001
상기 화학식 1에서，  In Chemical Formula 1,
Ri 내지 R4는 각각 독립적으로 수소; 치환 또는 비치환된 d-so 알킬 또는 치환 또는 비치환된 C6-60 아릴이거나, 또는 인접한 2개가 결합하여 벤젠 고리를 형성하 , Ri to R 4 are each independently hydrogen; Substituted or unsubstituted d-so alkyl or substituted or unsubstituted C 6 -60 aryl, or two adjacent groups combine to form a benzene ring,
八！^은 치환 또는 비치환된 C6-60 아릴이고, 八！ ^ is substituted or unsubstituted C 6 -60 aryl,
Figure imgf000004_0001
Figure imgf000004_0001
Ar3은 치환 또는 비치환된 C6-6o 아릴이고， Ar 3 is a substituted or unsubstituted C 6 -6o aryl,
¾ 내지 ¾은 각각 독립적으로， 수소; 치환 또는 비치환된 d-60 알킬; 또는 치환 또는 비치환된 C 0 아릴이거나, 또는 인접한 2개가 결합하여 벤젠 고리를 형성하고, ¾ to ¾ are each independently hydrogen; Substituted or unsubstituted d- 60 alkyl; Or substituted or unsubstituted C 0 aryl, or two adjacent groups combine to form a benzene ring,
[화학식 2]  [Formula 2]
Figure imgf000004_0002
Figure imgf000004_0002
L은 결합; 또는 치환 또는 비치환된 CEHSO 아릴렌이고,  L is a bond; Or substituted or unsubstituted CEHSO arylene,
' Ar4 내지 Ar6는 각각 독립적으로 C6-60 아릴이다. Ar 4 to Ar 6 are each independently C 6 -60 aryl.
【발명의 효과】  【Effects of the Invention】
상술한 유기 발광 소자는, 구동 전압， 효율 및 수명이 우수하다. 【도면의 간단한 설명】  The organic light emitting device described above is excellent in driving voltage, efficiency, and lifetime. [Brief Description of Drawings]
도 1은, 기판 (1), 양극 (2)， 전자억제층 (3)， 발광층 (4), 및 음극 (5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.  FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, an electron suppression layer 3, a light emitting layer 4, and a cathode 5. As shown in FIG.
도 2는, 기판 (1)ᅳ 양극 (2), 정공수송층 (6)， 전자억제층 (3), 발광층 (4), 전자수송층 (7) 및 음극 (5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.  FIG. 2 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole transport layer 6, an electron suppression layer 3, a light emitting layer 4, an electron transport layer 7 and a cathode 5. It is shown.
【발명을 실시하기 위한 구체적인 내용】  [Specific contents to carry out invention]
이하， 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다. ᅳ본— 명세서에서， ^ 또는 I는 다른 치환기에 연결되는 결합을 의미한다. 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기； 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기； 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기 ; 또는 . N , 0 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나， 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대， "2 이상의 치환기가 연결된 치환기 "는 비페닐기일 수 있다. 즉， 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. 본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다. Hereinafter, in order to help the understanding of the present invention will be described in more detail. ᅳ present— In the specification, ^ or I means a bond connected to another substituent. The term "substituted or unsubstituted" in the specification is deuterium; Halogen group; nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; or . It means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, 0 and S atoms, or two or more substituents of the above-described substituents are linked. For example, "the substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and can be interpreted as a substituent to which two phenyl groups are linked. Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
Figure imgf000005_0001
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로， 하기 구조식의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다.
Figure imgf000005_0001
In the present specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
Figure imgf000006_0001
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다ᅳ
Figure imgf000006_0001
In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having the following structure, but is not limited thereto.
Figure imgf000006_0002
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t -부틸디메틸실릴기， 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기， 페닐실릴기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t -부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서, 할로겐기의 예로는 불소， 염소,
Figure imgf000006_0002
In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto. In the present specification, the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like. In the present specification, examples of the halogen group include fluorine, chlorine,
요오드가 있다. 본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸， 프로필， n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸 1-메틸-부틸, 1-에틸-부틸, 펜틸， n-펜틸， 이소펜틸, 네오펜틸， t er t-펜틸, 핵실， n-핵실, 1—메틸펜틸, 2-메틸펜틸, 4一메틸—2—펜틸， 3 , 3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸， 1-메틸핵실， 사이클로펜틸쩨틸，사이클로핵틸메틸, 옥틸， n—옥틸, tert-옥틸, 1-메틸헵틸， 2—에틸헥실, 2—프로필펜틸， n-노닐, 2 , 2—디메틸헵틸, 1—에틸-프로'필， 1 , 1- 디메틸-프로필, 이소핵실, 2-메틸펜틸， 4-메틸핵실, 5-메틸핵실 등이 있으나， 이들에 한정되지 않는다. 본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나와 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐， 이소프로페닐， 1-부테닐， 2—부테닐， 3-부테닐, 1-펜테닐, 2—펜테닐， 3-펜테닐， 3-메틸 -1ᅳ부테닐, 1 , 3-부타디에닐, 알릴, 1-페닐비닐 -1-일, 2-페닐비닐 -1—일, 2 , 2-디페닐비닐 -1ᅳ일 , 2—페닐 -2- (나프틸— 1-일)비닐 -1—일, 2，2-비스 (디페닐 -1—일)비닐 -1—일, 스틸베닐기， 스티레닐기 등이 있으나 이들에 한정되지 않는다ᅳ 본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸， 사이클로펜틸, 3ᅳ메틸사이클로펜틸, 2，3- 디메틸사이클로펜틸, 사이클로핵실, 3—메틸사이클로핵실, 4- 메틸사이클로핵실, 2 , 3-디메틸사이클로핵실, 3 , 4 , 5-트리메틸사이클로핵실， 4-t ert-부틸사이클로핵실, 사이클로헵틸 사이클로옥틸 등이 있으나, 이에 한정되지 않는다. 본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기， 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기， 안트라세닐기, 페난트릴기， 파이레닐기, 페릴레닐기， 크라이세닐기, 플루오레닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 There is iodine In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. Work According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl 1-methyl-butyl, 1-ethyl-butyl, pentyl, n- Pentyl, isopentyl, neopentyl, ter t-pentyl, nuclear chamber, n-nuclear chamber, 1—methylpentyl, 2-methylpentyl, 4 one methyl— 2 —pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, Heptyl, n-heptyl, 1-methylnuclear, cyclopentylpentyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2, 2—dimethylheptyl, 1-ethyl-propyl ' , 1, 1-dimethyl-propyl, isonuclear chamber, 2-methylpentyl, 4-methylnuclear chamber, 5-methylnuclear chamber, and the like, but is not limited thereto. In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2—butenyl, 3-butenyl, 1-pentenyl, 2—pentenyl, 3-pentenyl, 3-methyl-1′part Tenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2, 2-diphenylvinyl-1xyl, 2-phenyl-2- (naphthyl — 1-yl) vinyl-l-yl, 2,2-bis (diphenyl-l-yl) vinyl-l-yl, stilbenyl groups, styrenyl groups and the like, but not limited thereto. The cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3 ᅳ methylcyclopentyl, 2,3- dimethylcyclopentyl, cyclonuclear chamber, 3—methylcyclonuclear chamber, 4- Methylcyclonuclear chamber, 2, 3-dimethylcyclonuclear chamber, 3, 4, 5-trimethylcyclonuclear chamber, 4-tert-butylcyclonuclear chamber, cycloheptyl cyclooctyl, and the like, but are not limited thereto. In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. The fluorenyl group
Figure imgf000008_0001
Figure imgf000008_0001
수 있다. 다만, 이에 한정되는 것은 아니다. 본 명세서에 있어서, 해테로고리기는 이종 원소로 0 , N , S i 및 S 중 1개 이상을 포함하는 헤테로고리기로서， 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피를기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기， 트리아졸기, 피리딜기, 비피리딜기， 피리미딜기, 트리아진기， 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기， 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기， 카바졸기， 벤조옥사졸기， 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰를린기 (phenanthrol ine) , 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기， 티아디아졸릴기， 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다. 본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기， 알킬아릴기， 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 해테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 해테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 이하， 각 구성 별로 본 발명을 상세히 설명한다. 양극 및 음극 Can be. However, the present invention is not limited thereto. In the present specification, the heterocyclic group is a heterocyclic group containing one or more of 0, N, S i and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group , Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline Group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, Dibenzothiophene group, benzofuranyl group, phenanthrol ine, thiazolyl group, isoxoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzo Furanyl groups and the like, but are not limited thereto. In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description about the heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding. Hereinafter, the present invention will be described in detail for each configuration. Anode and cathode
본 발명에서 사용되는 양극 및 음극은， 유기 발광 소자에서 사용되는 전극을 의미한다. 상기 양극 물.질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크름， 구리， 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물， 인듐 산화물, 인듐주석 산화물 ( IT0) , 인듐아연 산화물 (ΊΖ0)과 같은 금속 산화물; Ζη0:Α1 또는 SN02:Sb와 같은 금속과 산화물의 조합; 폴리 (3- 메틸티오펜), 폴리 [3,4—(에틸렌—1,2-디옥시)티오펜](?£0 1)， 폴리피를 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐， 이트륨， 리튬, 가돌리늄， 알루미늄, 은， 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li02/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. 발광층 The anode and cathode used in the present invention means an electrode used in the organic light emitting device. As the cathode material and the material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, crumb, copper, zinc, and gold or alloys thereof; Metals such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (ΊΖ0) oxide; Η a combination of a metal and an oxide such as η 0: A1 or SN0 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4— (ethylene—1,2-dioxy) thiophene] (? £ 0 1), polypyrrole and polyaniline, but only It is not limited. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto. Light emitting layer
본 발명에서 사용되는 발광층은, 양극과 음극으로부터 전달받은 정공과 전자를 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 층을 의미한다. 일반적으로, 발광층은 호스트 재료와 도편트 재료를 포함하며, 본 발명에는 상기 화학식 1로 표시되는 화합물올 호스트로 포함한다. 상기 화학식 1에서， 바람직하게는, Ri 내지 는 모두 수소이거나， 또는 인접한 2개가 결합하여 벤젠 고리를 형성하고 나머지는 수소이다. 보다 바람직하게는， 상기 화학식 은 하기 화학식 1-2, 1-3, 1-4, 1-5, 또는 1-6으로 표시된다:  The light emitting layer used in the present invention means a layer capable of emitting light in the visible light region by combining holes and electrons received from the anode and the cathode. In general, the light emitting layer includes a host material and a dopant material, and the present invention includes the compound represented by Chemical Formula 1 as a host. In Formula 1, preferably, Ri to all are hydrogen, or two adjacent groups are bonded to each other to form a benzene ring, and the rest are hydrogen. More preferably, the formula is represented by the following formulas 1-2, 1-3, 1-4, 1-5, or 1-6:
[화학식 1-1] [Formula 1-1]
Figure imgf000011_0001
Figure imgf000011_0001
[화학식 1-3] [Formula 1-3]
Figure imgf000012_0001
Figure imgf000012_0001
[화학식 1-6] [Formula 1-6]
Figure imgf000013_0001
상기 화학식 1-1 내지 1-6에서， A , Ar3 , R5 내지 ¾은 앞서 정의한 바와 같다ᅳ 바람직하게는, ^은 페닐, 비페닐릴, 나프틸， 또는 디메틸플루오레닐이다. 바람직하게는, Ar2는 하기로 구성되는 군으로부터 선택되는 어느 하나이다
Figure imgf000013_0001
In Formulas 1-1 to 1-6, A, Ar 3 , R 5 to ¾ are as defined above. Preferably, ^ is phenyl, biphenylyl, naphthyl, or dimethylfluorenyl. Preferably, Ar 2 is any one selected from the group consisting of
Figure imgf000013_0002
바람직하게는. Ar3은 페닐ᅳ 비페닐릴, 또는 나프틸이다. 상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다:
Figure imgf000013_0002
Preferably. Ar 3 is phenyl ᅳ biphenylyl, or naphthyl. Representative examples of the compound represented by Formula 1 are as follows:
Figure imgf000014_0001
Figure imgf000014_0001
Ζ8^ΖΟΟ/8ΐΟΖΗΜ/Χ3<Ι Ζ8 ^ ΖΟΟ / 8ΐΟΖΗΜ / Χ3 <Ι
Figure imgf000015_0001
Figure imgf000015_0001
Z8 ZOO/8lOZW^/13d Z8 ZOO / 8lOZW ^ / 13d
Figure imgf000016_0001
Figure imgf000016_0001
Ζ8^ΖΟΟ/8ΐΟΖΗΜ/Χ3<Ι Ζ8 ^ ΖΟΟ / 8ΐΟΖΗΜ / Χ3 <Ι
Figure imgf000017_0001
상기 화학식 1로 표시되는 화합물은 하기 반웅식 1과 같은 제조 방법으로 제조할 수 있다.
Figure imgf000017_0001
The compound represented by Chemical Formula 1 may be prepared by the same method as in Preparation.
[반웅식 1] [Banungsik 1]
Figure imgf000018_0001
Figure imgf000018_0001
Figure imgf000018_0002
상기 반응식 1에서, Ri 내지 R4 , An , Ar2 > Ar3 및 R5 내지 ¾은 앞서 정의한 바와 같으며, X는 각각 독립적으로 할로겐이다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 상기 도펀트 재료로는 유기 발광 소자에 사용되는 물질이면 특별히 제한되지 않는다. 일례로, 방향족 아민 유도체， 스트릴아민 화합물， 붕소 착체， 플루오란텐 화합물， 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌， 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기， 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민， 스티릴디아민 , 스티릴트리아민 , 스티 ¾테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다. 전자억제층 본 발명에 따른 유기 발광 소자는, 상기 양극과 발광층 사이에 전자억제층을 포함한다. 바람직하게는, 상기 전자억제층은 상기 발광층의 양극 쪽에 접하여 포함된다. 상기 전자억제층은, 음극에서 주입된 전자가 발광층에서 재결합하지 않고 양극 쪽으로 전달되는 것을 억제하여 유기 발광 소자의 효율을 향상시키는 역할을 한다. 본 발명에서는 상기 전자억제층을 구성하는 물질로서 상기 화학식 2로 표시되는 화합물을 사용한다. 바람직하게는， 상기 화학식 2는 하기 화학식 2-1 , 또는 2-2로 표시된다:
Figure imgf000018_0002
In Reaction Scheme 1, Ri to R4, An, Ar 2> Ar 3 and R 5 to ¾ are as defined above, and each X is independently halogen. The manufacturing method may be more specific in the production examples to be described later. The dopant material is not particularly limited as long as it is a material used for an organic light emitting device. For example, an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, etc. are mentioned. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styryl amine, styryl diamine, styryl triamine, sty ¾ tetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like. Electron suppression layer The organic light emitting device according to the present invention includes an electron suppression layer between the anode and the light emitting layer. Preferably, the electron suppression layer is included in contact with the anode side of the light emitting layer. The electron suppression layer serves to improve efficiency of the organic light emitting device by inhibiting electrons injected from the cathode from being transferred toward the anode without recombination in the emission layer. In the present invention, a compound represented by Chemical Formula 2 is used as a material constituting the electron suppression layer. Preferably, Formula 2 is represented by the following Formula 2-1, or 2-2:
[화학식 2-1] [Formula 2-1]
Figure imgf000019_0001
Figure imgf000019_0002
상기 화학식 2-1 및 2-2에서, Ar4 , Ar5 , 및 ^6는 앞서 정의한 바와 같다. 바람직하게는, Ar4는 페닐이다. 바람직하게는， Ar5 및 Ar6는 각각 독립적으로， 페닐， 비페닐릴， 터페닐릴, 나프틸， 페닐나프틸， 나프틸페닐, 디메틸플루오레닐, 페난트레닐, 페난트레닐페닐, 또는 트리페닐레닐이다. 상기 화학식 2로 표시되는 화합물의 대표적인 예는 다음과 같다:
Figure imgf000019_0001
Figure imgf000019_0002
In Formulas 2-1 and 2-2, Ar 4 , Ar 5 , and ^ 6 are as defined above. Preferably, Ar 4 is phenyl. Preferably, Ar 5 and Ar 6 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenanthrenyl, phenanthrenylphenyl, or Triphenylenyl. Representative examples of the compound represented by Formula 2 are as follows:
Figure imgf000021_0001
Figure imgf000021_0001
Ζ8^ΖΟΟ/8ΐΟΖΗΜ/Χ3<Ι Ζ8 ^ ΖΟΟ / 8ΐΟΖΗΜ / Χ3 <Ι
Figure imgf000022_0001
Figure imgf000022_0001
Figure imgf000022_0002
Figure imgf000022_0002
Figure imgf000022_0003
상기 화학식 2로 표시되는 화합물은 하기 반응식 2와 같은 방법으로 제조할 수 있다.
Figure imgf000022_0003
The compound represented by Chemical Formula 2 may be prepared by the same method as in Scheme 2 below.
[반응식 2] Scheme 2
Figure imgf000023_0001
상기 반응식 2에서, L , Ar4 , Ar5 및 Ar6는 앞서 정의한 바와 같으며 X는 할로겐이다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 정공수송층
Figure imgf000023_0001
In Scheme 2, L, Ar 4 , Ar 5 and Ar 6 are as defined above and X is halogen. The manufacturing method may be more specific in the production examples to be described later. Hole transport layer
본 발명에 따른 유기 발광 소자는, 상기 전자억제층과 양극 사이에 정공수송층을 포함할 수 있다. 상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로， 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 상기 정공 수송 물질의 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 정공주입층  The organic light emitting device according to the present invention may include a hole transport layer between the electron suppression layer and the anode. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. A hole transporting material is a material capable of transporting holes from an anode or a hole injection layer to a light emitting layer. This is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a nonconjugated portion together. Hole injection layer
본 발명에 따른 유기 발광 소자는， 필요에 따라 상기 양극과 정공수송층 사이에 정공주입층을 추가로 포함할 수 있다. 상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고， 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 또한, 정공 주입 물질의The organic light emitting device according to the present invention may further include a hole injection layer between the anode and the hole transport layer, if necessary. The hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the movement of the produced excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Also, of hole injection materials
H0M0(highest occupied mol ecular orbi t al )가 양극 물질의 일함수와 주변 유기물 층의 HOMO사이인 것이 바람직하다. . 정공 주입 물질의 구체적인 예로는 금속 포피린 (porphyr in) , 올리고티오펜, 아릴아민 계열의 유기물, 핵사니트릴핵사아자트리페닐텐 계열의 유기물， 퀴나크리돈 (quinacr idone)계열의 유기물, 페릴렌 (perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. 전자수송층 It is preferred that H0M0 (highest occupied mol ecular orbital) is between the work function of the anode material and the HOMO of the surrounding organic layer. . Specific examples of the hole injecting material include metal porphyr, oligothiophene, arylamine-based organic matter, nucleonitrile-nucleated azatriphenylten-based organic material, quinacridone-based organic material, and perylene ) Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto. Electron transport layer
본 발명에 따른 유기 발광 소자는， 상기 발광층과 음극 사이에 전자수송층을 포함할 수 있다. 상기 전자수송층은， 음극 또는 음극 상에 형성된 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하고, 또한 발광층에서 정공이 전달되는 것을 억제하는 층으로， 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 상기 전자 수송 물질의 구체적인 예로는 8-히드록시퀴놀린의 A1 착물; AlQ3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본 -금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. .전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다. 전자주입층 본 발명에 따른 유기 발광 소자는 필요에 따라 상기 전자수송층과 음극 사이에 전자주입층을 추가로 포함할 수 있다. 상기 전자주입층은 전극으로부터 전자를 주입하는 층으로， 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물을 사용하는 것이 바람직하다. 상기 전자주입층으로 사용될 수 있는 물질의 구체적인 예로는， 플루오레논, 안트라퀴노다이메탄， 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸， 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄， 안트론 등과 그들의 유도체， 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나， 이에 한정되지 않는다. 상기 금속 착체 화합물로서는 8-하이드록시,퀴놀리나토 리튬, 비스 (8-하이드록시퀴놀리나토)아연, 비스 (8-하이드록시퀴놀리나토)구리, 비스 (8—하이드록시퀴놀리나토)망간, 트리스 (8一 하이드록시퀴놀리나토).알루미늄 , 트리스 (2ᅳ메틸 -8- 하이드록시퀴놀리나토)알루미늄, 트리스 (8-하이드록시퀴놀리나토)갈륨, 비스 ( 10—하이드록시벤조 [h]퀴놀리나토)베릴륨, 비스 ( 10- 하이드록시벤조 [h]퀴놀리나토)아연, 비스 (2—메틸 -8ᅳ퀴놀리나토)클로로갈륨, 비스 (2-메틸 -8-퀴놀리나토) ( 0—크레졸라토)갈륨， 비스 (2-메틸 -8- 퀴놀리나토) ( 1-나프를라토)알루미늄， 비스 (2—메틸 -8ᅳ퀴놀리나토 ) (2- 나프를라토)갈륨 등이 있으나 이에 한정되지 않는다. 유기 발광 소자 The organic light emitting device according to the present invention may include an electron transport layer between the light emitting layer and the cathode. The electron transport layer is a layer that receives electrons from the electron injection layer formed on the cathode or the cathode to transport electrons to the light emitting layer, and also suppresses the transfer of holes from the light emitting layer. As a material which can receive and transfer to a light emitting layer, a material having high mobility to electrons is suitable. Specific examples of the electron transporting material 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 electron transport layer can be used with any desired cathode material, as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case. Electron injection layer The organic light emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the cathode as necessary. The electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer It is preferable to use a compound which prevents the movement to a layer and is excellent in thin film formation ability. Specific examples of the material that can be used as the electron injection layer, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preore Nilidene methane, anthrone and the like, derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, but are not limited thereto. Examples of the metal complex compound include 8-hydroxy , quinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper and bis (8-hydroxyquinolinato) manganese , Tris (8 一 hydroxyquinolinato) . Aluminum, Tris (2 ᅳ methyl-8-hydroxyquinolinato) Aluminum, Tris (8-hydroxyquinolinato) gallium, bis (10—hydroxybenzo [h] quinolinato) beryllium, bis (10- Hydroxybenzo [h] quinolinato) zinc, bis (2—methyl-8 ᅳ quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0—cresolato) gallium, bis (2- Methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8 -quinolinato) (2-naphtholato) gallium, and the like. Organic light emitting device
본 발명에 따른 유기.발광 소자의 구조를 도 1에 예시하였다. 도 1은, 기판 ( 1) , 양극 (2) , 전자억제층 (3)， 발광층 (4) , 및 음극 (5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 또한, 정공수송층 (6) 및 전자수송층 (7)을 포함하는 경우의 유기 발광 소자의 구조를 도 2에 예시하였다. 본 발명에 따른 유기 발광 소자는 상술한 구성을 순차적으로 적층시켜 제조할 수 있다. 이때， 스퍼터링법 (sput ter ing).이나 전자빔 증발법 (e— beam evaporat ion)과 같은 PVD(phys i cal Vapor Depos i t ion)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 상술한 각 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 상술한 구성의 역순으로 양극 물질까지 차례로 증착시켜 유기 발광 소자를 만들 수 있다 (W0 2003/012890) . 또한, 발광층은 호스트 및 도펀트를 진공 증착법 뿐만 아니라 용액 도포법에 의하여 형성될 수 있다. 여기서， 용액 도포법이라 함은 스핀 코팅, 딥코팅， 닥터 블레이딩, 잉크젯 프린팅， 스크린 프린팅， 스프레이.법， 롤 코팅 등을 의미하지만 이들만으로 한정되는 것은 아니다. 한편, 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형 , 후면 발광형 또는 양면 발광형일 수 있다. 이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐， 이에 의해 본 발명의 내용이 한정되는 것은 아니다ᅳ The structure of the organic light emitting device according to the present invention is illustrated in FIG. 1. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, an electron suppression layer 3, a light emitting layer 4, and a cathode 5. In addition, the hole transport layer (6) and The structure of the organic light emitting element in the case of including the electron transport layer 7 is illustrated in FIG. 2. The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configuration. At this time, a metal oxide or a metal oxide having a conductivity or a metal on a substrate by using a method of physical vapor deposition (PVD) such as sputtering or e-beam evaporat ion. It is possible to prepare by depositing an alloy of to form an anode, and to form each of the above-described layers, and then to deposit a material that can be used as a cathode on it. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material on a substrate to an anode material in the reverse order of the above-described configuration (W0 2003/012890). In addition, the light emitting layer may be formed of a host and a dopant not only by vacuum deposition but also by solution coating. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto. Meanwhile, the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type according to a material used. Hereinafter, preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the contents of the present invention are not limited thereto.
[제조예] [Production example]
제조예 1—1 : 화합물 1—1의 제조  Preparation Example 1-1: Preparation of Compound 1-1
단계 1) 화합물 1-a의 제조 Step 1) Preparation of Compound 1-a
Figure imgf000027_0001
질소 분위기에서 500 ml 등근 바닥 플라스크에 2—클로로 -4- (나프탈렌 -2-일)퀴나졸린 (12.00 g, 41.38 mmol), 2-클로로 -5H- 벤조 [b]카바졸 (11.42 g, 45.52 誦 ol)을 DMAC(50 ml )/Xylene(200 ml) 용액에 완전히 녹인 후 K3P04(20.05 g, 62.07 mmol)을 넣은 후 3시간 동안 가열 및 교반하였다. 상온으로 온도를 낮추고 여과한 다음， 물 (500 ml)로 2회 세정하고 에틸 아세테이트 (300 ml)로 세정하고 상온에서 24사간 동안 건조시켜 화합물 l-a(11.07 g, 수율: 53%)를 제조하였다.
Figure imgf000027_0001
2—chloro-4- (naphthalen-2-yl) quinazolin (12.00 g, 41.38 mmol), 2-chloro-5H-benzo [b] carbazole (11.42 g, 45.52 誦) in a 500 ml back bottom flask in a nitrogen atmosphere ol) was completely dissolved in DMAC (50 ml) / Xylene (200 ml) solution, and then K 3 P0 4 (20.05 g, 62.07 mmol) was added thereto, followed by heating and stirring for 3 hours. The mixture was cooled to room temperature, filtered, washed twice with water (500 ml), washed with ethyl acetate (300 ml), and dried at room temperature for 24 hours to prepare compound la (11.07 g, yield: 53%).
MS: [M+H]+ - 637 MS: [M + H] + -637
Figure imgf000027_0002
Figure imgf000027_0002
질소 분위기에서 500 ml 등근 바닥 플라스크에 화합물 l-a(11.07 g, 21.92 隱 ol), ᅳ카바졸(4.03 g, 24.11 隱 ol)을 Xylene (220 ml)에 완전히 녹인 후 소디움 터트—부특사이드 (2.74 g, 28.50 瞧 ol)를 첨가하고， Pd(t_ Bu3P)2(0.22 g, 0.44 画 ol)을 넣은 후 4시간 동안 가열 및 교반하였다. 상온으로 온도를 낮추고 여과하여 base를 제거한 후 감압 하에 농축시키고 에틸 아세테이트 (300 ml)로 재결정을 2회 실시하여 화합물 1—1(7.86 g, 수율: 57%)를 제조하였다. Dissolve compound la (11.07 g, 21.92 隱 ol) and decarbazole (4.03 g, 24.11 隱 ol) in Xylene (220 ml) in a 500 ml isometric bottom flask in a nitrogen atmosphere, and then remove the sodium tert-subside (2.74 g, 28.50 μl ol) was added and Pd (t_Bu 3 P) 2 (0.22 g, 0.44 μl ol) was added thereto, followed by heating and stirring for 4 hours. The mixture was cooled to room temperature, filtered to remove the base, concentrated under reduced pressure, and recrystallized twice with ethyl acetate (300 ml) to prepare compound 1-1 (7.86 g, yield: 57%).
MS: [M+H]+ = 637 제조예 1-2 : 화합물 1-2의 제조 MS: [M + H] + = 637 Preparation Example 1-2: Preparation of Compound 1-2
Figure imgf000028_0001
Figure imgf000028_0001
1-b 1-b
2-클로로 -4- (나프탈렌 -2-일)퀴나졸린 및 2-chloro-4- (naphthalen-2-yl) quinazolin and
벤조 [b]카바졸 대신 각각 . 2-클로로—4-페닐퀴나졸린 Instead of benzo [b] carbazole, respectively. 2-chloro-4-phenylquinazoline
벤조 [b]카바졸을 사용한 것을 제외하고는, 화합물 1- 동일한 방법으로 화합물 1-b를 제조하였다. 1-2의 제조 Compound 1-b was prepared by the same method except that benzo [b] carbazole was used. Manufacture of 1-2
1-2  1-2
1-b  1-b
화합물 l-a 대신 화합물 1— b를 사용하는 것을 제외하고는， 화합물 1-1의 제조 방법과 동일한 방법으로, 화합물 1-2를 제조하였다.  Compound 1-2 was prepared by the same method as the method for preparing compound 1-1, except that compound 1-b was used instead of compound l-a.
MS : [M+H]+ = 587 제조예 1-3: 화합물 1-3의 제조 MS: [M + H] + = 587 Preparation Example 1-3: Preparation of Compound 1-3
단계 1) 화합물 1-c의 제조  Step 1) Preparation of Compound 1-c
Figure imgf000028_0003
Figure imgf000028_0003
1-c 1-c
2ᅳ클로로— 4- (나프탈렌ᅳ 2-일)퀴나졸린 ᄆ J 클로로 벤조 [b]카바졸 대신 각각 2ᅳ클로로 -4—페닐퀴나졸린 및 9—브로모 -11H- 벤조 [a]카바졸을 사용한 것을 제외하고는， 화합물 l-a의 제조 방법과 동일한 방법으로 화합물 1— c를 제조하였다. 2 ᅳ chloro- 4- (naphthalenyl 2-yl) quinazolin Instead of J chloro benzo [b] carbazole, 2 ᅳ chloro-4—phenylquinazolin and 9—bromo-11H-benzo [a] carbazole, respectively, Except for the use, the preparation method of compound la In the same manner, compound 1-c was prepared.
Figure imgf000029_0001
Figure imgf000029_0001
질소 분위기에서 500 ml 등근 바닥 플라스크에 화합물 l-c(12.34 g Compound l-c (12.34 g) in 500 ml equipotential bottom flask under nitrogen atmosphere
24.68 隱 ol), (9-페닐— 9H—카바졸 -2-일)보론산 (8.15 g, 28.38 隱 ol)을 테트라하이드로퓨란 (240 ml)에 완전히 녹인 후 2M 탄산칼륨 수용액 (120 ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.86 g, 0.74 mmol)을 넣은 후 4시간 동안 가열 및 교반하였다. 상온으로 온도를 낮추고 물 층올 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 (240 ml)으로 재결정하여 화합물 1-3(11.36g, 수율: 69%)를 제조하였다. 24.68 μl ol), (9-phenyl—9H—carbazol-2-yl) boronic acid (8.15 g, 28.38 μl) is completely dissolved in tetrahydrofuran (240 ml), followed by 2M aqueous potassium carbonate solution (120 ml). Tetrakis- (triphenylphosphine) palladium (0.86 g, 0.74 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with tetrahydrofuran (240 ml) to prepare compound 1-3 (11.36 g, yield: 69%).
MS: [M+H]+ = 663 제조예 1-4: 화합물 1-4의 제조 MS: [M + H] + = 663 Preparation Example 1-4: Preparation of Compound 1-4
Figure imgf000029_0002
Figure imgf000029_0002
2-클로로 -4— (나프탈렌 -2—일)퀴나졸린 및 2-클로로 5H- 벤조 [b]카바졸 대신 각각 2-클로로 -4-페닐퀴나졸린 및 10-클로로 7H- 벤조 [c]카바졸을 사용한 것을 제외하고는, 화합물 1-a의 제조 방법과 동일한 방법으로 화합물 1-d를 제조하였다.
Figure imgf000030_0001
2-chloro-4-phenylquinazoline and 10-chloro 7H-benzo [c] carbazole instead of 2-chloro-4— (naphthalene-2—yl) quinazolin and 2-chloro 5H-benzo [b] carbazole, respectively Except for using, Compound 1-d was prepared by the same method as the method for preparing Compound 1-a.
Figure imgf000030_0001
화합물 1— a 대신 화합물 1-d를 사용하는 것을 제외하고는, 화합물 1-1의 제조 방법과 동일한 방법으로， 화합물 1—4를 제조하였다.  Compound 1-4 was prepared in the same manner as the method for preparing Compound 1-1, except that Compound 1-d was used instead of Compound 1—a.
MS : [M+H]+ = 587 제조예 1-5 : 화합물 1—5의 제조 MS: [M + H] + = 587 Preparation Example 1-5: Preparation of Compound 1-5
단계 1) 화합물 1-e의 제조  Step 1) Preparation of Compound 1-e
Figure imgf000030_0002
Figure imgf000030_0002
2-클로로—4— (나프탈렌— 2-일)퀴나졸린 및 2-클로로 -5H一 벤조 [b]카바졸 대신 각각 4- (비페닐 -4-일)ᅳ 2-ᅳ클로로퀴나졸린 및 9ᅳ브로모- 4- (biphenyl-4-yl) ᅳ 2- ᅳ chloroquinazolin and 9 ᅳ instead of 2-chloro—4— (naphthalene— 2-yl) quinazolin and 2-chloro-5Hi benzo [b] carbazole, respectively. Bromo
7H-벤조 [c]카바졸을 사용한 것을 제외하고는, 화합물 1-a의 제조 방법과 동일한 방법으로 화합물 1-e를 제조하였다. 단계 2) 화합물 1—5의 제조 Compound 1-e was prepared by the same method as the method for preparing compound 1-a, except that 7H-benzo [c] carbazole was used. Step 2) Preparation of Compound 1-5
Figure imgf000030_0003
Figure imgf000030_0003
화합물 1— a 대신 화합물 1-e를 사용하는 것을 제외하고는, 화합물 1-1의 제조 방법과 동일한 방법으로, 화합물 1-5를 제조하였다. Compound 1—Compound except that Compound 1-e is used instead of a In the same manner as in the preparation method of 1-1, compound 1-5 was prepared.
MS : [M+H]+ = 663 제조예 1—6 : 화합물 1-6의 제조 MS: [M + H] + = 663 Preparation Example 1-6: Preparation of Compound 1-6
Figure imgf000031_0001
Figure imgf000031_0001
2-클로로 -4- (나프탈렌— 2-일)퀴나졸린 및 2-클로로 -5H- 벤조 [b]카바졸 대신 각각 2-클로로 -4-페닐퀴나졸린 및 10—브로모 -7Hᅳ 벤조 [c]카바졸을 사용한 것을 제외하고는, 화합물 l-a의. 제조 방법과 동일한 방법으로 화합물 1-f를 제조하였다.  2-chloro-4-phenylquinazoline and 10—bromo-7H ᅳ benzo [c] instead of 2-chloro-4- (naphthalene— 2-yl) quinazolin and 2-chloro-5H-benzo [b] carbazole, respectively. ], Except that carbazole was used. Compound 1-f was prepared by the same method as the preparation method.
Figure imgf000031_0002
Figure imgf000031_0002
1-6  1-6
화합물 1— c 대신 화합물 1-f를 사용하는 것을 제외하고는, 화합물 1—3의 제조 방법과 동일한 방법으로， 화합물 1-6을 제조하였다.  Compound 1-6 was prepared by the same method as the method for preparing compound 1-3, except that compound 1-f was used instead of compound 1-c.
MS : [M+H]+ = 663 제조예 1—7 : 화합물 1-7의 제조 MS: [M + H] + = 663 Preparation Example 1-7: Preparation of Compound 1-7
단계 1) 화합물 1— g의 제조
Figure imgf000032_0001
Step 1) Preparation of Compound 1—g
Figure imgf000032_0001
2—클로로 -4- (나프탈렌 -2-일)퀴나졸린 및 2—클로로 -5H- 벤조 [b]카바졸 대신 각각 2-클로로 -4-페닐퀴나졸린 8-브로모 -11H- 벤조 [a]카바졸을 사용한 것을 제외하고는， 화합물 1 제조 방법과 동일한 방법으로 화합물 1-g를 제조하였다. 2-chloro-4-phenylquinazoline 8-bromo-11H-benzo [a] instead of 2—chloro-4- (naphthalen-2-yl) quinazolin and 2—chloro-5H-benzo [b] carbazole, respectively. Except for using carbazole, compound 1-g was prepared by the same method as the method for preparing compound 1.
Figure imgf000032_0002
Figure imgf000032_0002
화합물 1-c 및 9—페닐 -9H—카바졸 -2-일보론산 대신 화합물 1— g 및 9-페닐 -9H-카바졸—3—일보론산을 사용하는 것을 제외하고는, 화합물 1-3의 제조 방법과 동일한 방법으로, 화합물 1-7을 제조하였다.  Compounds 1-c and 9—phenyl-9H—carbazole-2-ylboronic acid, except that Compound 1—g and 9-phenyl-9H-carbazole—3—ylboronic acid are used. In the same manner as in the preparation method, compound 1-7 was prepared.
MS : [M+H] + = 663 제조 1-8 : 화합물 1-8의 제조 MS: [M + H] + = 663 Preparation 1-8: Preparation of Compound 1-8
Figure imgf000032_0003
Figure imgf000032_0003
화합물 1-c 및 9-페닐 -9H-카바졸ᅳ 2—일보론산 대신 화합물 1-b 및 9-페닐— 9H—카바졸—3—일보론산을 사용하는 것을 제외하고는， 화합물 1-3의 제조 방법과 동일한 방법으로 화합물 1-8을 제조하였다. MS : [M+H]+ = 663 제조예 1—9: 화합물 1-9의 제조 Compounds 1-c and 9-phenyl-9H-carbazolyl 2—compounds of compound 1-3, except that compounds 1-b and 9-phenyl—9H—carbazole—3—ilboronic acid are used instead of Compound 1-8 was prepared by the same method as the preparation method. MS: [M + H] + = 663 Preparation Example 1-9: Preparation of Compound 1-9
Figure imgf000033_0001
Figure imgf000033_0001
2-클로로 -4- (나프탈렌— 2-일)퀴나졸린 및 2-클로로 -5Hᅳ 벤조 [b]카바졸 대신 각각 2—클로로 -4-(9，9-디메틸 -9H-플루오렌 -2ᅳ 일)퀴나졸린 및 3—클로로 -5H—벤조 [b]카바졸을 사용한 것을 제외하고는, 화합물 1-a의 제조 방법과 동일한 방법으로 화합물 l-h를 제조하였다. 2-chloro-4- (naphthalene— 2-yl) quinazoline and 2-chloro-5H ᅳ benzo [b] carbazole instead of 2—chloro-4- (9,9-dimethyl-9H-fluorene-2 ᅳ Compound lh was prepared by the same method as the method for preparing compound 1-a, except that one) quinazolin and 3—chloro-5H—benzo [b] carbazole were used.
Figure imgf000033_0002
화합물 1-c 대신 화합물 l-h를 사용하는 것을 제외하고는， 화합물 1-3의 제조 방법과 동일한 방법으로, 화합물 1—9를 제조하였다.
Figure imgf000033_0002
Compound 1-9 was prepared by the same method as the method for preparing compound 1-3, except that compound lh was used instead of compound 1-c.
MS : [M+H]+ = 779 제조예 1-10 : 화합물 1-10의 제조
Figure imgf000034_0001
MS: [M + H] + = 779 Preparation Example 1-10: Preparation of Compound 1-10
Figure imgf000034_0001
화합물 1-c 및 9—페닐— 9H-카바졸—2-일보론산 대신 화합물 1-f 및 9-페닐 -9H-카바졸 3-일보론산을 사용하는 것을 제외하고는， 화합물 1—3의 제조 방법과 동일한 방법으로, 화합물 1-10을 제조하였다.  Preparation of compound 1-3, except for using compound 1-f and 9-phenyl-9H-carbazole 3-ylboronic acid in place of compound 1-c and 9—phenyl—9H-carbazole—2-ylboronic acid In the same manner as the method, compound 1-10 was prepared.
MS: [M+H]+ = 663 MS: [M + H] + = 663
Figure imgf000034_0002
Figure imgf000034_0002
화합물 1-c 및 9-페닐 -9H—카바졸 -2ᅳ일보론산 대신 화합물 1-e 및 9-페닐ᅳ 9H-카바졸 -3-일보론산을 사용하는 것을 제외하고는 화합물 1-3의 제조.방법과 동일한 방법으로, 화합물 1-11을 제조하였다.  Preparation of compound 1-3 except for using compound 1-e and 9-phenyl ᅳ 9H-carbazole-3-ylboronic acid in place of compound 1-c and 9-phenyl-9H—carbazole-2 ᅳ ylboronic acid In the same manner as the method, compound 1-11 was prepared.
MS: [M+H]+.= 663 -12: 화합물 1—12의 제조  MS: [M + H] &lt; + &gt; = 663-12: Preparation of compound 1-12
Figure imgf000034_0003
Figure imgf000034_0003
화합물 1-c 대신 화합물 1— e를 사용하는 것을 제외하고는, 화합물 1-3의 제조 방법과 동일한 방법으로， 화합물 1-12를 제조하였다.  Compound 1-12 was prepared in the same manner as the method for preparing compound 1-3, except that Compound 1-e was used instead of Compound 1-c.
MS: [M+H]+ - 663
Figure imgf000035_0001
MS: [M + H] + -663
Figure imgf000035_0001
질소 분위기에서 500 ml 등근 바닥 플라스크에 화합물 5ᅳ페닐- 5, 12-디하이드로인돌로 [3, 2-a]카바졸 (6.47 g, 19.49 隱 ol), Ν-([1,1'- 비페닐]-4-일)ᅦ—(4-브로모페닐)-[1，1'-비페닐]—4-아민(10.18 g, 21.44 隱 ol)을 Xylene(230 ml)에 완전히 녹인 후 소디움 터트—부톡사이드 (2.43 g, 25.33 mmol)을 첨가하고， Pd(t-Bu3P)2(0.20 g, 0.39 瞧 ol)을 넣은 후 4시간 동안 가열 및 교반하였다. 상온으로 온도를 낮추고 여과하여 base를 제거한 후 감압 하에 농축시키고 에틸 아세테이트 (250 ml)로 재결정을 2회 실시하여 화합물 2-1(10.67 g, 수율: 76%)를 제조하였다. Compound 5 mlphenyl-5, 12-dihydroindolo [3,2-a] carbazole (6.47 g, 19.49 μl), Ν-([1,1'-ratio, in 500 ml isometric bottom flask in nitrogen atmosphere Phenyl] -4-yl) ᅦ — (4-bromophenyl)-[1,1'-biphenyl] —4-amine (10.18 g, 21.44 隱 ol) dissolved in Xylene (230 ml) completely —Butoxide (2.43 g, 25.33 mmol) was added, Pd (t-Bu 3 P) 2 (0.20 g, 0.39 Pa ol) was added thereto, followed by heating and stirring for 4 hours. The mixture was cooled to room temperature, filtered to remove the base, concentrated under reduced pressure, and recrystallized twice with ethyl acetate (250 ml) to give compound 2-1 (10.67 g, yield: 76%).
MS: [M+H]+ = 723 MS: [M + H] + = 723
Figure imgf000035_0002
Figure imgf000035_0002
N- (비페닐— 4—일)— N— (4—브로모페닐)비페닐 -4-아민 대신 Ν,Ν- 디 (비페닐ᅳ 4-일) -4'-브로모비페닐 -4-아민을 사용한 것을 제외하고， 화합물 2-1의 제조 방법과 동일한 방법으로 화합물 2-2를 제조하였다. MS: [M+H]+ = 804 N- (biphenyl— 4—yl) — N— (4—bromophenyl) biphenyl-4-amine instead of Ν, Ν- di (biphenyl ᅳ 4-yl) -4′-bromobiphenyl-4- Except for using an amine, Compound 2-2 was prepared by the same method as the method for preparing Compound 2-1. MS: [M + H] + = 804
Figure imgf000036_0001
Figure imgf000036_0001
N- (비페닐— 4—일) -N-(4-브로모페닐)비페닐 -4-아민 대신 N- (비페닐- N- (biphenyl- 4-yl) -N- (4-bromophenyl) biphenyl-4-amine instead of N- (biphenyl-
4-일) -N-(4-브로모페닐)— 9,9—디메틸 -9H—플루오렌 -2-아민을 사용한 것을 제외하고， 화합물 2—1의 제조 방법과 동일한 방법으로 화합물 2ᅳ 3을 제조하였다. 4-yl) -N- (4-bromophenyl)-9,9-dimethyl-9H-fluorene-2-amine, except that Compound 2-3 was prepared in the same manner as in the preparation of Compound 2-1. Was prepared.
MS: [M+H]+ = 768 MS: [M + H] + = 768
Figure imgf000036_0002
Figure imgf000036_0002
N- (비페닐 -4-일)— N-(4—브로모페닐)비페닐 -4—아민 대신 N- (비페닐- 4-일)— N-(4-브로모페닐) -9,9-디메틸—9?1-플루오렌-2-아민을 사용한 것을 제외하고, 화합물 2—1의 제조 방법과 동일한 방법으로 화합물 2— 4를 제조하였다.  N- (biphenyl-4-yl) — N- (4—bromophenyl) biphenyl-4—amine instead of N- (biphenyl-4-yl) — N- (4-bromophenyl) -9, Compound 2-4 was prepared by the same method as the method for preparing compound 2-1, except that 9-dimethyl—9? 1-fluoren-2-amine was used.
MS: [M+H]+ = 844 제조예 2-5 : 화합물 2-5의 제조 MS: [M + H] + = 844 Preparation Example 2-5: Preparation of Compound 2-5
Figure imgf000037_0001
Figure imgf000037_0001
N— (비페닐 -4-일) -N-(4—브로모페닐)비페닐—4-아민 대신 N-(4- 브로모페닐) -N—페닐비페닐— 4-아민을 사용한 것을 제외하고， 화합물 2—1의 제조 방법과 동일한 방법으로 화합물 2— 5를 제조하였다.  N— (biphenyl-4-yl) -N- (4—bromophenyl) biphenyl—except the use of N- (4-bromophenyl) -N—phenylbiphenyl—4-amine instead of 4-amine And the compound 2-5 was manufactured by the same method as the compound 2-1 manufacturing method.
. MS : [M+H] + = 652 제조예 2-6 : 화합물 2-6의 제조 . MS: [M + H] + = 652 Preparation Example 2-6: Preparation of Compound 2-6
Figure imgf000037_0002
Figure imgf000037_0002
N— (비페닐ᅳ 4-일) -Nᅳ (4-브로모페닐)비페닐 -4—아민 대신 N-(4- 브로모페닐)—Nᅭ페닐터페닐—4-아민을 사용한 것을 제외하고, 화합물 2—1의 제조 방법과 동일한 방법으로 화합물 2-6을 제조하였다. Except for using N- (biphenyl-eu 4-yl) -N eu (4-bromophenyl) biphenyl-4-amine instead of N- (4-bromophenyl) -N-phenyl yo terphenyl-4-amine And the compound 2-6 was manufactured by the method similar to the manufacturing method of compound 2-1.
MS : [M+H] + = 723 [실시예] MS: [M + H] + = 723 EXAMPLE
실시예 1  Example 1
IT0( indium tin oxide)가 1,000 A의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사 (Millipore Co.) 제품의 필터 (Filter)로 2차로 걸러진 증류수를 사용하였다. IT0를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜， 아세톤， 메탄을의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다. 상기와 같이 준비된 IT0 투명 전극 위에 하기 HAT로 표시되는 화합물을 150A의 두께로 열 진공 증착하여 박막을 형성하였다. 이어서, 상기 박막 위에 하기 HT-1으로 표시되는 화합물을 1150 A의 두께로 증착하여 정공 수송층을 형성하고, 그 위에 앞서 제조한 화학식 2-1로 표시되는 화합물을 100A의 두께로 증착하여 전자 차단층을 형성하였다. 이어서， 앞서 제조한 제조예의 화학식 1—2로 표시되는 화합물에 하기 RD- 1으로 표시되는 화합물을 10 중량 % 도핑하여 두께 300A의. 발광층을 형성하였다. 그 위에 하기 HB— 1으로 표시되는 화합물 50A의 두께로 증착하여 정공 차단층을 형성하고, 이어서 하기 ET-1으로 표시되는 화합물을 '310A의 두께로 증착하여 전자 수송층을 형성하였다. 상기 전자 수송층 위에 순차적으로 12A 두께의 리륨 플루오라이드 (LiF)와 1,000A 두께의 알루미늄을 증착하여 음극을 형성하였다. A glass substrate coated with a thin film having an indium tin oxide (IT0) thickness of 1,000 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as the detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water. After washing IT0 for 30 minutes, the ultrasonic cleaning was performed twice with distilled water for 10 minutes. After the distilled water was washed, isopropyl alcohol, acetone, and methane were ultrasonically washed with a solvent, dried, and then transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. A compound represented by the following HAT was thermally vacuum deposited to a thickness of 150 A on the IT0 transparent electrode prepared as described above to form a thin film. Subsequently, the compound represented by the following HT-1 on the thin film is deposited to a thickness of 1150 A to form a hole transport layer, and the compound represented by Formula 2-1 prepared above is deposited to a thickness of 100A on the electron blocking layer Formed. Subsequently, 10 wt% of the compound represented by the following RD-1 was doped into the compound represented by the formula (1-2) of the prepared example, and the thickness was 300A. A light emitting layer was formed. A hole blocking layer was formed by evaporating to a thickness of compound 50A represented by the following HB-1, and then a compound represented by ET-1 was deposited to a thickness of '310A to form an electron transporting layer. Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 1,000 A were sequentially deposited on the electron transport layer to form a cathode.
Figure imgf000039_0001
Figure imgf000039_0001
Figure imgf000039_0002
Figure imgf000039_0002
HB-1 ET-1 상기의 과정에서 유기물의 증착속도는 0.4~ 0.7 A/sec를 유지하였고, 음극의 리튬플로라이드는 0.3A/sec , 알루미늄은 2A/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2 Χ ΚΓ7 ~ 5 X 10"6 torr를 유지하여 , 유기 발광 소자를 제작하였다. 실시예 2 내지 24 HB-1 ET-1 In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 A / sec, the lithium fluoride of the cathode was maintained at 0.3A / sec, and the aluminum was maintained at the deposition rate of 2A / sec. The degree of vacuum was maintained at 2 Χ ΓΓ 7 to 5 X 10 "6 torr to fabricate an organic light emitting device. Examples 2 to 24
상기 실시예 1에서 화학식 1—2로 표시되는 화합물 및 /또는 화학식 2-1로 표시되는 화합물 대신, 하기 표 1에 기재된 앞서 제조예에서 제조한 화합물을 사용하는 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 비교예 1 내지 18  Except for using the compound prepared in Preparation Example shown in Table 1, instead of the compound represented by Formula 1-2 and / or the compound represented by Formula 2-1 in Example 1, An organic light emitting device was manufactured in the same manner. Comparative Examples 1 to 18
상기 실시예 1에서 화학식 1-2로 표시되는 화합물 및 /또는 화학식 Compound represented by Formula 1-2 in Example 1 and / or formula
2一 1로 표시되는 화합물 대신, 하기 표 2에 기재된 화합물을 사용하는 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 같다. An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 2 below was used instead of the compound represented by 25.1. It is as follows.
Figure imgf000040_0001
Figure imgf000040_0001
RH-1 EB-1 실험예  RH-1 EB-1 Experimental Example
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때 구동 전압, 발광 효율, 발광 피크 및 수명홀 측정하고 그 결과를 하기 표 1에 나타내었다. T97은 휘도가 3000 ni t에서 97%로 감소되는데 소요되는 시간을 의미한다.  When a current was applied to the organic light emitting diodes manufactured in Examples and Comparative Examples, the driving voltage, the luminous efficiency, the emission peak, and the lifetime of the holes were measured, and the results are shown in Table 1 below. T97 means the time taken for the luminance to decrease from 3000 nit to 97%.
【표 11  Table 11
Figure imgf000040_0002
실시예 22 1—5 2-6 3.97 23.2 0.651 0.334 380 실시예 23 1-8 2-6 3.93 23.4 0.652 0.334 385 실시예 24 1-12 2-6 3.91 23.5 0.653 0.333 385
Figure imgf000040_0002
Example 22 1—5 2-6 3.97 23.2 0.651 0.334 380 Example 23 1-8 2-6 3.93 23.4 0.652 0.334 385 Example 24 1-12 2-6 3.91 23.5 0.653 0.333 385
【표 2】 Table 2
전자억제 전압 효율 CIEx CIEy T97 호스트  Electronic Suppression Voltage Efficiency CIEx CIEy T97 Host
(V) (Cd/A) (cd/ra2) (cd/m2) (hr) 비교예 1 RH-1 EB-1 4.71 19.5 0.651 0.332 285 비교예 2 RH-1 2-1 4.19 24.2 0.651 0.332 315 비교예' 3 RH-1 2-2 4.23 23.5 0.653 0.334 - 320 비교예 4 RH-1 2-3 4.15 24.6 0.654 0.336 325 비교예 5 H-1 2-4 4.28 23.7 0.655 0.331 320 비교예 6 RH-1 2-5 4.22 24.8 0.651 0.333 310 비교예 7 RH-1 2-6 4.20 23.9 0.655 0.330 325 비교예 8 1-1 EB1 4.32 22.1 0.654 0.335 335 비교예 9 1-2 EB1 4.32 21.5 0.653 0.336 340 비교'예 10 1-3 EB1 4.34 22.5 0.652 0.334 355 비교예 11 1-4 EB1 4.45 22.4 0.651 0.335 365 비교예 12 1-5 EB1 4.23 21.5 0.652 0.334 360 비교예 13 1-6 EB1 4.36 21.1 0.653 0.332 355 비교예 14 1-7 EB1 4.44 22.0 0.654 0.333 355 비교예 15 1-8 EB1 4.39 22.3 0.652 0.331 350 비교예 16 1-9 EB1 4.31 22.4 0.653 0.335 345 비교예 17 1-10 EB1 4.41 22.5 0.651 0.336 355 비교예 18 1-11 EB1 4.32 22.9 0.653 0.334 360 비교예 19 1-12 EB1 4.43 22.4 0.652 0.335 355 . 상기 표 1 및 2에 나타난 바와 같이 , 본 발명에 따른 화학식 1로 표시되는 화합물을 호스트로， 본 발명에 따른 화학식 2로 표시되는 화합물을 전자억제층으로 사용한 실시예는, 비교예 대비 구동 전압이 낮고， 효율 및 수명이 향상됨을 확인하였다. 특히, 실시예 9 내지 12에서, 본 발명에 따른 화학식 1로 표시되는 화합물을 발광층의 호스트로 사용하고, 화학식 2— 3으로 표시되는 화합물을 전자억제층으로 사용하였을 때 발광 효율이 가장 높았다. 또한 실시예 '5, 9， 13, 17, 및 21에서 화학식 1-2를 발광층의 호스트로 사용하였을 때 수명이 가장 긴 결과를 얻었다. 이를 통하여 본 발명의 화학식 1로 표시되는 화합물을 발광층의 호스트로， 본 발명의 화학식 2로 표시되는 화합물을 전자차단층 재료로 사용하는 경우, 구동 전압， 발광 효율 및 수명 특성이 동시에 개선됨을 확인하였다. . (V) (Cd / A) (cd / ra 2 ) (cd / m 2 ) (hr) Comparative Example 1 RH-1 EB-1 4.71 19.5 0.651 0.332 285 Comparative Example 2 RH-1 2-1 4.19 24.2 0.651 0.332 315 Comparative example '3 RH-1 2-2 4.23 23.5 0.653 0.334 - 320 Comparative example 4 RH-1 2-3 4.15 24.6 0.654 0.336 325 Comparative example 5 H-1 2-4 4.28 23.7 0.655 0.331 320 Comparative example 6 RH- 12-5 4.22 310 24.8 0.651 0.333 Comparative example 7 RH-1 2-6 4.20 23.9 0.655 0.330 325 Comparative example 8 1-1 EB1 4.32 22.1 0.654 0.335 335 Comparative example 9 1-2 EB1 4.32 21.5 0.653 0.336 340 Comparative yes 10 1-3 EB1 4.34 22.5 0.652 0.334 355 Comparative Example 11 1-4 EB1 4.45 22.4 0.651 0.335 365 Comparative Example 12 1-5 EB1 4.23 21.5 0.652 0.334 360 Comparative Example 13 1-6 EB1 4.36 21.1 0.653 0.332 355 Comparative Example 14 1 -7 EB1 4.44 22.0 0.654 0.333 355 Comparative Example 15 1-8 EB1 4.39 22.3 0.652 0.331 350 Comparative Example 16 1-9 EB1 4.31 22.4 0.653 0.335 345 Comparative Example 17 1-10 EB1 4.41 22.5 0.651 0.336 355 Comparative Example 18 1-11 EB1 4.32 22.9 0.653 0.334 360 Comparative Example 19 1-12 EB1 4.43 22.4 0.652 0.335 355. As shown in Table 1 and 2, the embodiment using the compound represented by the formula (1) according to the present invention as a host, the compound represented by the formula (2) according to the present invention as an electron suppressing layer, the driving voltage compared to the comparative example It was confirmed that the low, the efficiency and life is improved. In particular, in Examples 9 to 12, when the compound represented by the formula (1) according to the present invention was used as the host of the light emitting layer, and the compound represented by the formula (2-3) as the electron suppression layer, the luminous efficiency was the highest. Further embodiments, 5, 9, 13, 17, and 21 to obtain a service life of the longest results when used in the formula 1-2 as a host of the light emitting layer from. Through this, the compound represented by Chemical Formula 1 of the present invention As a host, when the compound represented by Formula 2 of the present invention is used as the electron blocking layer material, it was confirmed that the driving voltage, the luminous efficiency, and the lifetime characteristics were simultaneously improved. .
【부호의 설명】  [Explanation of code]
1: 기판 2： 양극  1: substrate 2: anode
3: 전자억제층 4: 발광층  3: electron suppression layer 4: light emitting layer
5： 음극 6: 정공수송층  5: cathode 6: hole transport layer
7： 전자수송층  7: electron transport layer

Claims

【특허청구범위】 [Patent Claims]
【청구항 11 [Claim 11
Figure imgf000043_0001
Figure imgf000043_0001
상기 양극과 음극 사이의 발광충, 및 · 상기 양극과 발광층 사이의 전자억제층을 포함하고,  A light emitting charge between the anode and the cathode, and an electron suppression layer between the anode and the light emitting layer,
상기 발광층은 하기 화학식 1로표시되는 화합물을 포함하고, 상기 전자억제층은 하기 화학식 2로 표시되는 화합물을 포함하는, 유기 발광 소자: ■  The emission layer includes a compound represented by Formula 1, and the electron suppression layer comprises a compound represented by Formula 2 below:
Figure imgf000043_0002
Figure imgf000043_0002
상기 화학식 1에서,  In Chemical Formula 1,
Ri 내지 R4는 각각 독립적으로 수소; 치환 또는 비치환된 d-60 알킬 또는 치환 또는 비치환된 C6-60 아릴이거나, 또는 인접한 2개가 결합하여 벤젠 고리를 형성하고， Ri to R 4 are each independently hydrogen; Substituted or unsubstituted d- 60 alkyl or substituted or unsubstituted C 6 -60 aryl, or two adjacent groups combine to form a benzene ring,
An^ -6o 아릴이  An ^ -6o aryl
Ar2는
Figure imgf000043_0003
, 또는 이고,Ar 2 is
Figure imgf000043_0003
, Or
Ar3은 치환 또는 비치환된 C6-60 아릴이고, Ar 3 is substituted or unsubstituted C 6 -60 aryl,
R5 내지 은 각각 독립적으로, 수소; 치환 또는 비치환된 알킬; 또는 치환 또는 비치환된 C6— 60 아릴이거나, 또는 인접한 2개가 결합하여 벤젠 고리를 형성하고 R 5 to are each independently hydrogen; Substituted or unsubstituted alkyl; Or substituted or unsubstituted C 6 — 60 aryl, or two adjacent groups To form a benzene ring
[화학식  Formula
Figure imgf000044_0001
Figure imgf000044_0001
L은 결합; 또는 치환 또는 비치환된 C6— 60 아릴렌이고, L is a bond; Or substituted or unsubstituted C 6 — 60 arylene,
Ar4 내지 Ar6는 각각 독립적으로 C6-60 아릴이다. Ar 4 to Ar 6 are each independently C 6 -60 aryl.
【청구항 2] [Claim 2]
제 1항에 있어서,  The method of claim 1,
상기 화학식 1은 하기 화학식 1-1， 1-2', 1-3 , 1-4， 1-5 , 또는 1- 6으로 표시되는, Formula 1 is represented by the following formula 1-1, 1-2 ' , 1-3, 1-4, 1-5, or 1-6,
유기 발광 소자:  Organic light emitting device:
Figure imgf000044_0002
Figure imgf000044_0002
[화학식 1ᅳ 2]
Figure imgf000045_0001
[Formula 1 ᅳ 2]
Figure imgf000045_0001
Figure imgf000045_0002
Figure imgf000046_0001
Figure imgf000045_0002
Figure imgf000046_0001
【청구항 3】  [Claim 3]
제 1항에 있어서, The method of claim 1,
은 페닐, 비페닐릴, 나프틸, 또는 디메틸플루오레닐^ 유기 발광 소자.  Silver phenyl, biphenylyl, naphthyl, or dimethylfluorenyl ^ organic light emitting device.
【청구항 4] [Claim 4]
제 1항에 있어서,  The method of claim 1,
Ar2는 하기로 구성되는 군으로부터 선택되는 어느 하나^ 유기 발광 소자: Ar 2 is any one selected from the group consisting of ^ Organic light emitting device:
Figure imgf000047_0001
Figure imgf000047_0001
【청구항 5】 [Claim 5]
저 U항에 있어서，  In that U term,
Ar3은 페닐， 비페닐릴, 또 Ar 3 is phenyl, biphenylyl, or
유기 발광 소자.  Organic light emitting device.
【청구항 6】 [Claim 6]
제 1항에 있어서  The method of claim 1
Λ기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,  Compound represented by the Λ group Formula 1 is any one selected from the group consisting of
유기 발광 소자: Organic light emitting device:
Figure imgf000048_0001
Figure imgf000048_0001
Ζ8^ΖΟΟ/8ΐΟΖΗΜ/Χ3<Ι Ζ8 ^ ΖΟΟ / 8ΐΟΖΗΜ / Χ3 <Ι
Figure imgf000049_0001
Figure imgf000049_0001
Ζ8^ΖΟΟ/8ΐΟΖΗΜ/Χ3<Ι 6 Ζ8 ^ ΖΟΟ / 8ΐΟΖΗΜ / Χ3 <Ι 6
Figure imgf000050_0001
Figure imgf000050_0001
Ζ8^ΖΟΟ/8ΐΟΖΗΜ/Χ3<Ι Ζ8 ^ ΖΟΟ / 8ΐΟΖΗΜ / Χ3 <Ι
Figure imgf000051_0001
Figure imgf000051_0002
Figure imgf000051_0001
Figure imgf000051_0002
Figure imgf000051_0003
Figure imgf000051_0003
【청구항 7] [Claim 7]
제 1항에 있어서，  The method of claim 1,
상기 화학식 2는 하기 화학식 2-1， 또는 2— 2로 표시되 유기 발광 소자:  Chemical Formula 2 is represented by the following Chemical Formula 2-1, or 2-2:
[화학식 2-1] [Formula 2-1]
Figure imgf000052_0001
Figure imgf000052_0001
【청구항 8] [Claim 8]
제 1항에 있어서,  The method of claim 1,
Ar4는 페닐인， Ar 4 is phenyl ，
유기 발광 소자.  Organic light emitting device.
【청구항 9】 [Claim 9]
제 1항에 있어서，  The method of claim 1,
Ar5 및 Ar6는 각각 독립적으로, 페닐， 비페닐릴， 터페닐릴， 나프틸 페닐나프틸, 나프틸페닐, 디메틸플루오레닐, 페난트레닐 페난트레닐페닐 또는 트리페닐레닐인, Ar 5 and Ar 6 are each independently phenyl, biphenylyl, terphenylyl, naphthyl phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenanthrenyl phenanthrenylphenyl or triphenylenyl;
유기 발광 소자. 【청구항 10】 Organic light emitting device. [Claim 10]
저 U항에 있어서，  In that U term,
상기 화학식 2로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인，  The compound represented by Formula 2 is any one selected from the group consisting of
Figure imgf000053_0001
Figure imgf000053_0001
Figure imgf000053_0002
Figure imgf000053_0002
Figure imgf000054_0001
Figure imgf000054_0001
Ζ8^ΖΟΟ/8ΐΟΖΗΜ/Χ3<Ι Ζ8 ^ ΖΟΟ / 8ΐΟΖΗΜ / Χ3 <Ι
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