KR20110008892A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

Info

Publication number
KR20110008892A
KR20110008892A KR1020090066446A KR20090066446A KR20110008892A KR 20110008892 A KR20110008892 A KR 20110008892A KR 1020090066446 A KR1020090066446 A KR 1020090066446A KR 20090066446 A KR20090066446 A KR 20090066446A KR 20110008892 A KR20110008892 A KR 20110008892A
Authority
KR
South Korea
Prior art keywords
substituted
unsubstituted
aryl
alkyl
heteroaryl
Prior art date
Application number
KR1020090066446A
Other languages
Korean (ko)
Inventor
조영준
권혁주
김봉옥
김성민
윤승수
Original Assignee
다우어드밴스드디스플레이머티리얼 유한회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 다우어드밴스드디스플레이머티리얼 유한회사 filed Critical 다우어드밴스드디스플레이머티리얼 유한회사
Priority to KR1020090066446A priority Critical patent/KR20110008892A/en
Priority to PCT/KR2010/004697 priority patent/WO2011010843A1/en
Priority to TW099123921A priority patent/TW201111474A/en
Publication of KR20110008892A publication Critical patent/KR20110008892A/en

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Manufacturing & Machinery (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

PURPOSE: An organic electroluminescent compound and an organic electroluminescent device using the same are provided to ensure excellent luminous efficiency and lifetime property of materials and to obtain an OLED devices with good driving durability. CONSTITUTION: An organic electroluminescent compound is represented by chemical formula 1. In chemical formula 1, B1 - B9 are independently CR12 or N; A is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene, and substituted or unsubstituted 5-membered or 7-membered heterocycloalkylene; R1 - R12 are independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, and one or more substituted or unsubstituted (C6-C30) aryl fused with substituted or unsubstituted (C3-C30) cycloalkyl; W is -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-; and m is 1 or 2.

Description

신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자{Novel organic electroluminescent compounds and organic electroluminescent device using the same}Novel organic electroluminescent compounds and organic electroluminescent device using the same

본 발명은 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 상세하게는 본 발명에 따른 유기 발광 화합물은 하기 화학식 1의 화합물인 것을 특징으로 한다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, in detail, the organic light emitting compound according to the present invention is characterized in that the compound of formula (1).

[화학식 1][Formula 1]

Figure 112009044439287-PAT00002
Figure 112009044439287-PAT00002

유기EL소자는 보통 anode/HIL/HTL/EML/ETL/EIL/cathode로 구성되는데 발광층(EML)을 어떻게 형성하느냐에 따라 청색, 녹색, 적색의 유기 전기 발광 소자를 각각 구현할 수가 있다. The organic EL device is usually composed of anode / HIL / HTL / EML / ETL / EIL / cathode. The organic electroluminescent device of blue, green, and red can be realized depending on how the emission layer (EML) is formed.

발광재료는 기능적인 측면에서 호스트 재료와 도판트 재료로 구분될 수 있는 데 일반적으로 EL 특성이 가장 우수한 소자 구조로는 호스트에 도판트를 도핑하여 발광층을 만드는 것으로 알려져 있다. 최근에 고효율, 장수명 유기 EL 소자의 개발이 시급한 과제로 대두되고 있으며, 특히 중대형 OLED 패널에서 요구하고 있는 EL 특성 수준을 고려해 볼 때 기존의 발광재료에 비해 매우 우수한 재료의 개발이 시급한 실정이다.The light emitting material can be classified into a host material and a dopant material in terms of its functional properties. In general, a device structure having the best EL characteristics is known to form a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic EL devices has emerged as an urgent task, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials.

한편, 청색 재료의 경우, 이데미쓰-고산의 DPVBi 이후로 많은 재료들이 개발되어 상업화되어 있으며, 이데미쓰-고산의 청색 재료 시스템과 코닥의 다이나프틸안트라센(dinaphthylanthracen), 테트라(t-부틸)페릴렌(tetra(t-butyl)perlyene) 시스템 등이 알려져 있으나, 아직도 많은 연구 개발이 이루어져야 할 것으로 판단된다. 현재까지 가장 효율이 좋다고 알려진 이데미쓰-고산의 디스트릴(distryl)화합물의 시스템은 파워 효율의 경우, 6 lm/W이고, 소자 수명이 30,000 시간 이상으로 좋기는 하나, 색상이 풀컬러디스플레이로 채용하기에는 부적합한 스카이-블루이다. 일반적으로 청색 발광은 발광 파장이 장파장 쪽으로 조금만 이동해도 발광 효율 측면에서는 유리해지나, 순청색을 만족시키지 못해 고품위의 디스플레이에는 적용이 쉽지 않은 문제점을 갖고 있어서, 색순도, 효율 및 열안정성에 대한 연구 개발이 시급한 부분이라고 하겠다.On the other hand, in the case of blue materials, many materials have been developed and commercialized since Idemitsu-Alpine DPVBi, and Idemitsu-Alpine's blue material system, Kodak's dinaphthylanthracen, tetra (t-butyl) fe Although a tetra (t-butyl) perlyene system is known, much research and development is still required. The system of Idemitsu-high acid disryl compound, which is known to be the most efficient to date, is 6 lm / W for power efficiency, and the device life is over 30,000 hours, but the color is adopted as a full color display. Unsuitable sky-blue below. In general, blue light emission is advantageous in terms of light emission efficiency even when the light emission wavelength is shifted to a longer wavelength, but it is not easy to apply to high-quality displays because it does not satisfy pure blue color, and thus research and development on color purity, efficiency and thermal stability It is an urgent part.

고효율, 장수명의 호스트 재료 개발을 위해 다양한 골격을 가진 디스피로-프롤렌-안트라센(TBSA), 터-스피로플로렌(TSF), 비트라이페닐렌(BTP) 등이 개발되었으나 역시 색순도 및 발광효율은 만족할 만한 수준은 아니었다.In order to develop high-efficiency and long-life host materials, disspiro-prolene-anthracene (TBSA), ter-spirofluorene (TSF), and vitriphenylene (BTP) with various skeletons have been developed. It was not satisfactory.

또한, 녹색 형광 재료로는 Alq를 호스트로 하여, 도판트로는 쿠마린 유도체, 퀴나크리돈 유도체, DPT 등을 수 내지 십수 % 정도로 도핑을 하는 시스템이 개발되어 널리 쓰이고 있다. 그러나, 이들 종래의 발광재료는 초기 발광효율의 경우, 상용화 가능한 수준의 성능을 보이나, 초기 효율 저하가 두드러지며 수명 측면에서 상당한 문제점을 보이고 있어, 대화면의 고성능 패널에서는 채택하기가 힘든 한계를 보이고 있다.In addition, a system for doping coumarin derivatives, quinacridone derivatives, DPT, and the like with about 10 to 10% has been developed and widely used as a green fluorescent material using Alq as a host. However, these conventional light emitting materials show a commercially available level of performance in the case of the initial luminous efficiency, but the initial efficiency decreases remarkably and shows considerable problems in terms of lifespan. .

또한, OLED 소자에서의 수명 측면에서도 결코 만족할만한 수준이 되질 못하여 더욱 안정되고, 더욱 성능이 뛰어난 호스트 재료의 개발이 요구되고 있다.In addition, in terms of lifespan in OLED devices, they are never satisfactory, and development of a more stable and more excellent host material is required.

본 발명 목적은 상기한 문제점들을 해결하기 위하여 기존의 호스트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며, 또 다른 목적으로서 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. SUMMARY OF THE INVENTION An object of the present invention is to provide an organic light emitting compound having an excellent luminescence efficiency and device life, and having an appropriate color coordinate, to solve the above problems, and having an appropriate color coordinate. To provide a high efficiency and long life organic electroluminescent device employed as.

본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 발광효율이 좋고 재료의 색순도 및 수명특성이 뛰어나 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has excellent luminous efficiency and excellent color purity and life characteristics of the material OLED very excellent driving life There is an advantage to manufacture the device.

[화학식 1][Formula 1]

Figure 112009044439287-PAT00003
Figure 112009044439287-PAT00003

[상기 화학식 1에서,[In Formula 1,

B1 내지 B9는 서로 독립적으로 CR12 또는 N이고,B 1 to B 9 are each independently CR 12 or N,

A는 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치 환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 (C3-C30)시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 시클로알킬렌, 치환 또는 비치환된 (C2-C30)알케닐렌, 치환 또는 비치환된 (C2-C30)알키닐렌, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬렌, 치환 또는 비치환된 (C1-C30)알킬렌티오, 치환 또는 비치환된 (C1-C30)알킬렌옥시, 치환 또는 비치환된 (C6-C30)아릴렌옥시, 치환 또는 비치환된 (C6-C30)아릴렌티오, -O- 또는 -S-이고;A is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted 5- to 7-membered heterocycloalkylene, substituted or unsubstituted aromatic 5- to 7-membered heterocycloalkylene, at least one ring fused, substituted or unsubstituted (C3-C30) cycloalkylene, cycloalkylene, at least one substituted or unsubstituted aromatic ring, substituted or unsubstituted Substituted (C2-C30) alkenylene, substituted or unsubstituted (C2-C30) alkynylene, substituted or unsubstituted (C6-C30) ar (C1-C30) alkylene, substituted or unsubstituted (C1- C30) alkylenethio, substituted or unsubstituted (C1-C30) alkyleneoxy, substituted or unsubstituted (C6-C30) aryleneoxy, substituted or unsubstituted (C6-C30) arylenethio, -O -Or -S-;

R1 내지 R12는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나이상 융합된 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, 카르복실, 나이트로,

Figure 112009044439287-PAT00004
,
Figure 112009044439287-PAT00005
또는 하이드록시이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌 으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R51 내지 R58 및 R61 내지 R63은 상기 R1 내지 R12에서의 정의와 동일하고; 상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며; 상기 R21 내지 R28은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이고, 상기 Ra, Rb, Rc, Rd는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이며, 상기 Y는 S 또는 O이고, 상기 Re, Rf는 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C6-C30)아릴옥시이며; m은 1 또는 2의 정수이다.]R 1 to R 12 are each independently Substituted or unsubstituted fused with one or more hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Substituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, or substituted or unsubstituted aromatic ring 5 1-7 membered heterocycloalkyl, Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, cyano, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= 0) R 27 R 28 , R a R b R c Si-, R d Y-, R e C (= 0)-, R f C (= 0) O-, substituted or unsubstituted ( C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, carboxyl, nitro,
Figure 112009044439287-PAT00004
,
Figure 112009044439287-PAT00005
Or may be linked to (C3-C30) alkylene or (C3-C30) alkenylene, which may or may not be hydroxy or contain a fused ring with adjacent substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 51 to R 58 and R 61 to R 63 is the same as defined above for R 1 to R 12 ; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; R 21 to R 28 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, and R a , R b , R c , R d are each independently substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl, Y is S or O, and R e , R f is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C6-C30) Aryloxy; m is an integer of 1 or 2.]

본 발명에 기재된 “알킬”, “알콕시” 및 그 외 “알킬”부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, 「시클로알킬」은 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된(C7-C30)바이시클로알킬을 모두 포함한다. 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7원, 바람직하게는 5 또는 6 원을 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 상기 아릴의 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴 또는 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. 상기 헤테로아릴기는 고리 내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 상기 헤테로아릴의 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다.Substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight or crushed forms, and "cycloalkyl" is substituted or unsubstituted adamantyl or substituted or unsubstituted It includes all of the (C7-C30) bicycloalkyl. "Aryl" described in the present invention refers to an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and refers to a single or fused ring system containing 4 to 7 members, preferably 5 or 6 members, to each ring. It also includes a form in which a plurality of aryl is connected by a single bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. Including but not limited to. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. The "heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si, and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. It means an aryl group which is 5-6 membered monocyclic heteroaryl or polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, Monocyclic heteroaryl such as triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl , Benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnaolinyl, quinazolinyl, quinoxalinyl, carbazolyl Polycyclic heteroaryls such as phenantridinyl, benzodioxolyl and the corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like, It is not limited to this.

또한, 본 발명에 기재되어 있는 “(C1-C30)알킬”기는 (C1-C20)알킬 또는 (C1-C10)알킬을 포함하고, “(C6-C30)아릴”기는 (C6-C20)아릴 또는 (C6-C12)아릴을 포함한다. “(C3-C30)헤테로아릴”기는 (C3-C20)헤테로아릴 또는 (C3-C12)헤테로아릴을 포함하고, “(C3-C30)시클로알킬”기는 (C3-C20)시클로알킬 또는 (C3-C7)시클로알킬을 포함한다. “(C2-C30)알케닐 또는 알키닐”기는 (C2-C20)알케닐 또는 알키닐, (C2-C10)알케닐 또는 알키닐을 포함한다.In addition, the "(C1-C30) alkyl" groups described herein include (C1-C20) alkyl or (C1-C10) alkyl, and the "(C6-C30) aryl" group is (C6-C20) aryl or (C6-C12) aryl. “(C3-C30) heteroaryl” group includes (C3-C20) heteroaryl or (C3-C12) heteroaryl, and “(C3-C30) cycloalkyl” group is (C3-C20) cycloalkyl or (C3- C7) cycloalkyl. "(C2-C30) alkenyl or alkynyl" groups include (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.

또한 본 발명에 기재되어 있는 “치환 또는 비치환”에 있어서, 치환은 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카 보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고, 상기 R31 내지 R38은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴인 것을 의미한다.In addition, in the "substituted or unsubstituted" described in the present invention, the substitution is independently of each other deuterium, halogen, halogen substituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30 (C3-C30) heteroaryl substituted or unsubstituted, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl , (C3-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, ( C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR 31 R 32 , BR 33 R 34 , PR 35 R 36 , P (= O) R 37 R 38 , (C6-C30 ) Ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30 ) Arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycar At least one selected from the group consisting of carbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy It may be further substituted, or substituents adjacent to each other may be connected to form a ring, wherein R 31 to R 38 are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl Means that.

상기 R1 내지 R12, R21 내지 R28, R51 내지 R58 및 R61 내지 R63은 서로 독립적으로 수소, 중수소, 할로겐, 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸 등의 알킬, 페닐, 나프틸, 플루오레닐, 바이페닐, 페난트릴, 터페닐, 피레닐, 퍼릴레닐, 스피로바이플루오레닐, 플루오란테닐, 크리세닐, 트리페닐레닐 등의 아릴, 1,2-디하이드로아세나프틸 등의 시클로알킬이 하나 이상 융합된 아릴, 디벤조티오페닐, 디벤조퓨릴, 카바졸릴, 피리딜, 퓨릴, 티에닐, 퀴놀릴, 트리아지닐, 피리미디닐, 피리다지닐, 퀴녹살리닐, 페난트롤리닐 등의 헤테로아릴, 벤조피롤리디노, 벤조피페리디노, 디벤조모폴리노, 디벤조아제피노 등의 하나 이상의 방향족고리가 융합된 헤테로시클로알킬, 페닐, 나프틸, 플루오레닐, 바이페닐, 페난트릴, 터페닐, 피레닐, 퍼릴레닐, 스피로바이플루오레닐, 플루오란테닐, 크리세닐, 트리페닐레닐 등의 아릴 또는 디벤조티오페닐, 디벤조퓨릴, 카바졸릴, 피리딜, 퓨릴, 티에닐, 퀴놀릴, 트리아지닐, 피리미디닐, 피리다지닐, 퀴녹살리닐, 페난트롤리닐 등의 헤테로아릴이 치환된 아미노, 비페닐옥시 등의 아릴옥시, 비페닐티오 등의 아 릴티오, 비페닐메틸, 트리페닐메틸 등의 아르알킬,

Figure 112009044439287-PAT00006
또는
Figure 112009044439287-PAT00007
로부터 선택되어지나, 이에 한정되는 것은 아니며, 상기 화학식 1에서와 같이 더 치환될 수 있다.R 1 to R 12 , R 21 to R 28 , R 51 to R 58 and R 61 to R 63 are each independently hydrogen, deuterium, halogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl Aryl, such as alkyl, such as octyl, phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perrylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, and triphenylenyl Aryl, dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, in which at least one cycloalkyl such as 1,2-dihydroacenaphthyl is fused Heterocycloalkyl fused with one or more aromatic rings such as heteroaryl such as pyridazinyl, quinoxalinyl and phenanthrolinyl, benzopyrrolidino, benzopiperidino, dibenzomorpholino and dibenzoazino Phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylene Aryl or dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, such as spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl Aralkyl such as amino substituted with heteroaryl such as pyridazinyl, quinoxalinyl and phenanthrolinyl, aryloxy such as biphenyloxy, biphenylthio, aralkyl such as biphenylmethyl, triphenylmethyl,
Figure 112009044439287-PAT00006
or
Figure 112009044439287-PAT00007
It is selected from, but is not limited thereto, and may be further substituted as in the formula (1).

보다 구체적으로 상기 R1 내지 R12는 하기 구조로 예시되어지나, 이에 한정되는 것은 아니다. More specifically, the R 1 to R 12 is illustrated by the following structure, but is not limited thereto.

Figure 112009044439287-PAT00008
Figure 112009044439287-PAT00008

[R71 내지 R141은 서로 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)시클로알킬이 하나이상 융합된 (C6-C30)아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 아미노, (C1-C30)알킬아미노, (C6-C30)아릴아미노, NR41R42, BR43R44, PR45R46, P(=O)R47R48, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C2-C30)알케닐, (C2-C30)알키닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고, 상기 R41 내지 R48은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이다.][R 71 to R 141 independently of one another are hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 6 -C 30) aryl wherein at least one fused (C 6 -C 30) aryl, ( C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, cyano, amino, (C1-C30) alkylamino, (C6-C30) arylamino, NR 41 R 42 , BR 43 R 44 , PR 45 R 46 , P (= O) R 47 R 48 , tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryl Silyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1- C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy Can be linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring , R 41 to R 48 are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl.]

보다 구체적으로 상기 R1 내지 R12는 하기 구조로 예시되어지나, 이에 한정되는 것은 아니다.More specifically, the R 1 to R 12 is illustrated by the following structure, but is not limited thereto.

Figure 112009044439287-PAT00009
Figure 112009044439287-PAT00009

본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 하기 화합물이 본 발명을 한정하는 것은 아니다.The organic light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.

Figure 112009044439287-PAT00010
Figure 112009044439287-PAT00010

Figure 112009044439287-PAT00011
Figure 112009044439287-PAT00011

Figure 112009044439287-PAT00012
Figure 112009044439287-PAT00012

Figure 112009044439287-PAT00013
Figure 112009044439287-PAT00013

본 발명에 따른 유기 발광 화합물은 하기 반응식 1에 나타난 바와 같이, 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in Scheme 1 below.

[반응식 1]Scheme 1

Figure 112009044439287-PAT00014
Figure 112009044439287-PAT00014

[상기 반응식 1에서 A, B1 내지 B9 및 R1 내지 R11은 상기 화학식 1에서의 정의와 동일하다.][In Scheme 1, A, B 1 to B 9 and R 1 to R 11 are the same as defined in Formula 1 above.]

본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. 상기 유 기 발광 화합물은 발광층의 호스트 물질로 사용되어진다. The present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound of Formula 1. The organic light emitting compound is used as a host material of the light emitting layer.

또한, 상기 유기물층은 발광층을 포함하며, 상기 발광층은 상기 화학식 1의 하나 이상의 유기 발광 화합물 이외에 하나 이상의 도판트를 더 포함하는 것을 특징으로 하며, 본 발명의 유기 발광 소자에 적용되는 도판트는 특별히 제한되지는 않는다.The organic material layer may include a light emitting layer, and the light emitting layer may further include one or more dopants in addition to the one or more organic light emitting compounds of Formula 1, and the dopant applied to the organic light emitting device of the present invention is not particularly limited. Does not.

본 발명의 유기 전계 발광 소자에 적용되는 도판트는 하기 화학식 2 및 화학식 3의 화합물로부터 선택되는 것이 바람직하다.The dopant applied to the organic electroluminescent device of the present invention is preferably selected from the compounds of the formulas (2) and (3).

[화학식 2][Formula 2]

Figure 112009044439287-PAT00015
Figure 112009044439287-PAT00015

[상기 화학식 2에서, [In Formula 2,

Ar11 및 Ar12는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C4-C30)헤테로아릴, 치환 또는 비치환된 (C6-C30)아릴아미노, (C1-C30)알킬아미노, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬이거나 Ar11 및 Ar12는 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고; Ar 11 and Ar 12 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C4-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered substituted (C6-C30) arylamino, (C1-C30) alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring Heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring is one or more fused (C3-C30) cycloalkyl, or Ar 11 and Ar 12 may or may not include fused ring Or (C3-C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

c가 1인 경우 Ar13은 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C4-C30)헤테로아릴 또는 하기 구조에서 선택되는 치환기이고;when c is 1, Ar 13 is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;

Figure 112009044439287-PAT00016
Figure 112009044439287-PAT00016

c가 2인 경우 Ar13는 치환 또는 비치환된 (C6-C30)아릴렌, 치환 또는 비치환된 (C4-C30)헤테로아릴렌 또는 하기 구조에서 선택되는 치환기이고;when c is 2, Ar 13 is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;

Figure 112009044439287-PAT00017
Figure 112009044439287-PAT00017

Ar14 및 Ar15은 서로 독립적으로 치환 또는 비치환된 (C6-C30)아릴렌 또는 치환 또는 비치환된 (C4-C30)헤테로아릴렌이고;Ar 14 and Ar 15 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene;

R201 내지 R203는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 (C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이고;R 201 to R 203 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl;

d는 1 내지 4의 정수이며, d is an integer of 1 to 4,

e는 0 또는 1의 정수이다.]e is an integer of 0 or 1.]

[화학식 3](3)

Figure 112009044439287-PAT00018
Figure 112009044439287-PAT00018

[상기 화학식 3에서, [In Formula 3,

R211 내지 R214는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, NR301R302, BR303R304, PR305R306, P(=O)R307R308, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알킬옥시, 치환 또는 비치환된 (C1-C30)알킬티오, 치환 또는 비치환된 (C6-C30)아릴옥시, 치환 또는 비치환된 (C6-C30)아릴티오, 치환 또는 비치환된 (C1-C30)알콕시카보닐, 치환 또는 비치환된 (C1-C30)알킬카보닐, 치환 또는 비치환된 (C6-C30)아릴카보닐, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐, 치환 또는 비치환된 (C6-C30)아릴옥시카보닐, 치환 또는 비치환된 (C1-C30)알콕시카보닐옥시, 치환 또는 비치환된 (C1-C30)알킬카보닐옥시, 치환 또는 비치환된 (C6-C30)아릴카보닐옥시, 치환 또는 비치환된 (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로, 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고, 상기 R301 내지 R308은 서로 독립적으로 치환 또는 비치환된 (C1- C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이다.]R 211 to R 214 are each independently Hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5 member 5-7 membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring, wherein one to seven membered heterocycloalkyl, substituted or unsubstituted aromatic rings are fused. Is (C3-C30) cycloalkyl, cyano, NR 301 R 302 , BR 303 R 304 , PR 305 R 306 , P (= 0) R 307 R 308 , substituted or unsubstituted (C1-C30) C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C1-C30) alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6-C30) aryl O, substituted or unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted (C1-C30) alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or unsubstituted ( C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, Substituted or unsubstituted (C1-C30) alkylcarbonyloxy, substituted or unsubstituted (C6-C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxyl, nit And may be linked with (C3-C30) alkylene or (C3-C30) alkenylene, which may be hydroxy, with or without adjacent substituents and fused rings, to form an alicyclic ring and a monocyclic or polycyclic aromatic ring. R 301 to R 308 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or Unsubstituted (C3-C30) heteroaryl.]

상기 발광층의 의미는 발광이 이루어지는 층으로서 단일 층일 수 있으며, 또한 2개 이상의 층이 적층된 복수의 층일 수 있다. 본 발명의 구성에서의 호스트-도판트를 혼합하여 사용하는 경우, 본 발명의 발광 호스트에 의한 발광 효율의 현저한 개선을 확인할 수 있었다. 이는 0.5 내지 10중량%의 도핑 농도로 구성할 수 있는데, 기존의 다른 호스트 재료에 비하여 정공, 전자에 대한 전도성이 매우 뛰어나며, 물질 안정성을 매우 우수하여 발광효율 뿐만 아니라, 수명도 현저히 개선시키는 특성을 보여 주고 있다.The light emitting layer may be a single layer as a light emitting layer, or may be a plurality of layers in which two or more layers are stacked. In the case of using a mixture of the host and dopants in the configuration of the present invention, a significant improvement in the luminous efficiency by the light emitting host of the present invention was confirmed. It can be composed of a doping concentration of 0.5 to 10% by weight, and has excellent conductivity for holes and electrons compared to other host materials, and has excellent material stability, which significantly improves luminous efficiency and lifetime. Is showing.

상기 화학식 2 및 화학식 3의 도판트 화합물은 한국특허출원번호 제10-2009-0023442호에 기재된 화합물로 예시될 수 있으며, 보다 바람직하게는 하기 구조에서 선택될 수 있으나, 이에 한정되는 것은 아니다.The dopant compounds of Chemical Formulas 2 and 3 may be exemplified by the compounds described in Korean Patent Application No. 10-2009-0023442, and more preferably may be selected from the following structures, but are not limited thereto.

Figure 112009044439287-PAT00019
Figure 112009044439287-PAT00019

Figure 112009044439287-PAT00020
Figure 112009044439287-PAT00020

본 발명의 유기 전계 발광 소자는 상기 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있으며, 상기 아릴아민계 화합물 또 는 스티릴아릴아민계 화합물은 한국특허출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시된 것도 포함하나, 이에 한정되지는 않는다. The organic electroluminescent device of the present invention may include one or more compounds selected from the group consisting of an organic light emitting compound of Formula 1 and an arylamine compound or a styrylarylamine compound, and the arylamine compound Or the styrylarylamine-based compound includes, but is not limited to, those exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428.

또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층과 전하생성층을 동시에 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic light emitting compound of Chemical Formula 1, a group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element It may further comprise one or more metal or complex compound selected from, the organic material layer may include a light emitting layer and a charge generating layer at the same time.

또한, 상기 유기물층에 화학식 1의 유기발광 화합물 이외에 청색, 녹색 또는 적색 발광을 하는 유기 화합물층 하나 이상을 동시에 포함하여 백색 유기 전계 발광 소자를 형성할 수 있으며, 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 한국특허출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시된 것도 포함하나, 이에 한정되지는 않는다. In addition, the organic material layer may simultaneously include one or more organic compound layers emitting blue, green, or red light in addition to the organic light emitting compound of Formula 1 to form a white organic electroluminescent device, and the blue, green, or red light emitting compound Examples include, but are not limited to, those disclosed in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428.

본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 "표면층"이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해, 구동의 안정화를 얻을 수 있다.In the organic electroluminescent device of the present invention, at least one inner surface of a pair of electrodes is selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer (hereinafter, these are referred to as "surface layers"). It is preferable to arrange | position the above. Specifically, it is preferable to dispose a chalcogenide (containing oxide) layer of a metal of silicon and aluminum on the anode surface of the light emitting medium layer side and a metal halide or metal oxide layer on the cathode surface of the light emitting medium layer side. Do. As a result, drive stabilization can be obtained.

상기 칼코제나이드로서는 예컨대 SiOx(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON 등을 바람직하게 들 수 있으며, 할로겐화 금속으로서는 예컨대 LiF, MgF2, CaF2, 불화 희토류 금속 등을 바람직하게 들 수 있으며, 금속 산화물로서는 예컨대 Cs2O, Li2O, MgO, SrO, BaO, CaO 등을 바람직하게 들 수 있다.Examples of the chalcogenide include SiO x (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like are preferable. Examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.

또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식으로, 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있다. 바람직한 환원성 도판트로서는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다.Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.

또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 전계 발광 소자를 제작할 수 있다.In addition, a white electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device.

이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.

[제조예 1]화합물 1의 제조Preparation Example 1 Preparation of Compound 1

Figure 112009044439287-PAT00021
Figure 112009044439287-PAT00021

화합물 compound 1-11-1 의 제조Manufacture

메틸-2-브로모벤조에이트(methyl-2-bromobenzoate) 40 g(152.6 mmol), 나프탈렌-1-일보로닉 산(naphthalen-1-ylboronic acid) 31.5 g(183.2 mmol), 테트라키스(트리페닐포스핀)팔라듐[Pd(PPh3)4] 8.8 g(7.62 mmol)을 2구 플라스크에 첨가한 후, 톨루엔 1 L를 첨가하면서 교반 시키고, 2M의 포테슘 카보네이트(Potassuim carbonate) 228 mL(458 mmol), 에탄올 228 mL를 첨가한 후, 100 ℃에서 5시간 동안 환류 교반시켰다. 반응이 종결되면 실온으로 냉각시킨 후 증류수와 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 에틸아세테이트를 전개 용매로 하고 컬럼 분리하여 화합물 1-1 35 g(87 %) 를 얻었다.40 g (152.6 mmol) of methyl-2-bromobenzoate, 31.5 g (183.2 mmol) of naphthalen-1-ylboronic acid, tetrakis (triphenyl 8.8 g (7.62 mmol) of phosphine) palladium [Pd (PPh 3 ) 4 ] was added to a two-necked flask, followed by stirring with the addition of 1 L of toluene, and 228 mL (458 mmol) of 2M Potassium carbonate. ), 228 mL of ethanol was added, followed by stirring under reflux at 100 ° C. for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Then, hexane and ethyl acetate were used as developing solvents, and column separation was performed, to obtain Compound 1-1 35 g (87%).

화합물 compound 1-21-2 의 제조Manufacture

화합물 1-1 24 g(91.49 mmol)를 1구 플라스크에 넣고 진공 분위기로 만든 후, 아르곤으로 채운다. 테트라하이드로퓨란 1 L를 넣고 -75 ℃에서 10분 간 교반하였다. MeLi(1.6M in hexane) 257 mL(0.41 mmol)를 첨가하고 -75 ℃에서 10분 동안 교반한 후, 상온에서 3시간 동안 교반하였다. 반응이 종결되면 증류수와 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 에틸아세테이트를 전개 용매로 하고 컬럼 분리하여 화합물 1-2 20 g(83 %)를 얻었다.24 g (91.49 mmol) of compound 1-1 were placed in a 1-neck flask, and made into a vacuum atmosphere, followed by filling with argon. 1 L of tetrahydrofuran was added and stirred at -75 ° C for 10 minutes. 257 mL (0.41 mmol) of MeLi (1.6 M in hexane) was added and stirred at −75 ° C. for 10 minutes, followed by stirring at room temperature for 3 hours. After the reaction was completed, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Hexane and ethyl acetate were used as developing solvents, and column separation was performed to obtain Compound 1-2 20 g (83%).

화합물 compound 1-31-3 의 제조Manufacture

화합물 1-2 20 g(76.23 mmol)을 1구 플라스크에 넣고 AcOH 300 mL를 넣은 후, 0 ℃에서 10분 간 교반하였다. H3PO4 400 mL를 첨가하고 상온에서 1시간 동안 교반한 후, 반응이 종결되면 NaOH로 중화시키고 증류수와 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 에틸아세테이트를 전개 용매로 하고 컬럼 분리하여 화합물 1-3 13.5 g(72 %)를 얻었다.20 g (76.23 mmol) of Compound 1-2 were placed in a 1-neck flask, and 300 mL of AcOH was added thereto, followed by stirring at 0 ° C. for 10 minutes. 400 mL of H 3 PO 4 was added and stirred at room temperature for 1 hour. After completion of the reaction, the reaction was neutralized with NaOH and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Then, hexane and ethyl acetate were used as developing solvents, and column separation was performed to obtain Compound 1-3 (13.5 g, 72%).

화합물 compound 1-41-4 의 제조Manufacture

화합물 1-3 13.5 g(55.25 mmol)를 1구 플라스크에 넣고 진공 분위기로 만e든 후 아르곤으로 채운다. 테트라하이드로퓨란 500 mL를 넣고 0 ℃에서 10분 간 교반 하였다. NBS 19.6 g(0.11 mmol)를 첨가하고 상온에서 하루 동안 교반하였다. 반응이 종결되면 증류수와 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 에틸아세테이트를 전개 용매로 하고 컬럼 분리하여 화합물 1-4 13 g(73 %)를 얻었다.13.5 g (55.25 mmol) of compound 1-3 are placed in a 1-neck flask, and made into a vacuum atmosphere, followed by filling with argon. 500 mL of tetrahydrofuran was added and stirred at 0 ° C. for 10 minutes. 19.6 g (0.11 mmol) of NBS were added and stirred for 1 day at room temperature. After the reaction was completed, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator. Hexane and ethyl acetate were used as developing solvents, and the mixture was separated by column to obtain compound 1-4 13 g (73%).

화합물 compound 1-51-5 의 제조Manufacture

화합물 1-4 13 g(42.21 mmol)를 1구 플라스크에 넣고 진공 분위기로 만든 후, 아르곤으로 채운다. 테트라하이드로퓨란 500 mL를 넣고 -78 ℃에서 10분 간 교반하였다. n-BuLi(2.5M in hexane) 24.1 mL(60.32 mmol)를 적가하고 1시간 30분 간 -78 ℃에서 교반하였다. 트라이메틸보레이트 6.85 mL(60.32 mmol)를 -78 ℃에서 첨가한 후 30분간 교반하고, 실온에서 4시간 동안 교반하였다. 반응이 종결되면 증류수와 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 에틸아세테이트를 전개 용매로 하고 컬럼 분리하여 화합물 1-5 8 g(69 %)를 얻었다.13 g (42.21 mmol) of Compound 1-4 are placed in a 1-neck flask, and the flask is filled with argon. 500 mL of tetrahydrofuran was added and stirred at -78 ° C for 10 minutes. 24.1 mL (60.32 mmol) of n-BuLi (2.5M in hexane) was added dropwise and stirred at −78 ° C. for 1 hour 30 minutes. 6.85 mL (60.32 mmol) of trimethylborate was added at -78 ° C, then stirred for 30 minutes, and stirred at room temperature for 4 hours. After the reaction was completed, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Hexane and ethyl acetate were used as a developing solvent, and the mixture was separated by column to obtain compound 1-5 8 g (69%).

화합물 compound 1One 의 제조Manufacture

화합물 1-5 5.0 g(13.4 mmol), 9-(4-브로모페닐)-10-페닐안트라센(9-(4-bromophenyl)-10-phenylanthracene) 6.59 g(16.1 mmol), Pd(PPh3)4 0.8 g(0.7 mmol), 2M K2CO3 수용액 20 mL, 톨루엔 100 mL, 에탄올 50 mL를 넣고 12시간 동안 환류 교반하였다. 증류수로 씻어 주고 에틸아세테이트로 추출한 후, 황산 마그네슘으로 건조하고 감압 증류하였다. 컬럼 분리하여 화합물 1 4.3 g(7.5 mmol, 56.1 %) 을 얻었다. Compound 1-5 5.0 g (13.4 mmol), 9- (4- bromophenyl) -10-phenylanthracene (9- (4-bromophenyl) -10 -phenylanthracene) 6.59 g (16.1 mmol), Pd (PPh 3) 4 0.8 g (0.7 mmol), 20 mL of 2M K 2 CO 3 aqueous solution, 100 mL of toluene, and 50 mL of ethanol were added thereto, and the mixture was stirred under reflux for 12 hours. The mixture was washed with distilled water, extracted with ethyl acetate, dried over magnesium sulfate and distilled under reduced pressure. Compound 1 (4.3 g, 7.5 mmol, 56.1%) was obtained by column separation.

상기 제조예 1의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 63을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 63 were prepared using the method of Preparation Example 1, and the 1 H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

[표 1]TABLE 1

Figure 112009044439287-PAT00022
Figure 112009044439287-PAT00022

Figure 112009044439287-PAT00023
Figure 112009044439287-PAT00023

Figure 112009044439287-PAT00024
Figure 112009044439287-PAT00024

[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다.An OLED device having a structure using the light emitting material of the present invention was produced.

우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다.First, a transparent electrode ITO thin film (15 Ω / □) obtained from an OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. It was used after.

다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 하기 구조의 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 하기구조 N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.Next, an ITO substrate is installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2) having the structure -TNATA), evacuated until the vacuum in the chamber reached 10 -6 torr, and then applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. the NPB -diphenyl-4,4'-diamine into the (NPB), by applying a current to the cell - then, to another cell of the vacuum vapor-deposit device structure, N, N 'N, N -bis (α-naphthyl)' A 20 nm thick hole transport layer was deposited on the hole injection layer by evaporation.

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 1를 넣고, 또 다른 셀에는 도판트로서 화합물 E을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 호스트를 기준으로 2 내지 5 중량%로 증착함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 1 according to the present invention is added as a host to one cell in a vacuum deposition apparatus, and Compound E is added as a dopant to another cell, and then the two materials are evaporated at different rates to 2 to 5% by weight based on the host. By depositing, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer.

Figure 112009044439287-PAT00026
Figure 112009044439287-PAT00026

이어서 전자전달층으로써 하기 구조의 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화합물 lithium quinolate (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다. Subsequently, tris (8-hydroxyquinoline) -aluminum (III) (Alq) having the following structure was deposited as an electron transport layer to a thickness of 20 nm, and then the compound lithium quinolate (Liq) having the following structure as the electron injection layer was 1 to 2 nm thick. After deposition, the Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to produce an OLED.

재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each compound was vacuum sublimated and purified under 10 -6 torr to be used as an OLED light emitting material.

[비교예 1] 종래의 발광 재료를 이용한 OLED 소자 제작Comparative Example 1 Fabrication of OLED Device Using Conventional Light-Emitting Material

발광층에 호스트로서 본 발명에 따른 화합물 대신 dinaphthylanthracene (DNA)을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED를 제작하였다. An OLED was manufactured in the same manner as in Example 1, except that dinaphthylanthracene (DNA) was used instead of the compound according to the present invention as a host in the emission layer.

[실시예 2] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 2 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광층에 호스트로서 본 발명에 따른 화합물 1와 도판트로서 하기 화합물 A를 사용한 것을 제외한고는 실시예 1과 동일한 방법으로 OLED를 제작하였다. An OLED was manufactured in the same manner as in Example 1, except that Compound 1 according to the present invention as a host and Compound A as the dopant were used in the light emitting layer.

Figure 112009044439287-PAT00027
Figure 112009044439287-PAT00027

[비교예 2] 종래의 발광 재료를 이용한 OLED 소자 제작Comparative Example 2 Fabrication of OLED Device Using Conventional Light-Emitting Material

발광층에 호스트로서 본 발명에 따른 화합물 대신 dinaphthylanthracene (DNA)을 사용한 것을 제외하고는 실시예 2와 동일한 방법으로 OLED를 제작하였다. An OLED was manufactured in the same manner as in Example 2, except that dinaphthylanthracene (DNA) was used instead of the compound according to the present invention as a host in the emission layer.

상기 실시예 1-2와 비교예 1-2에서 제조된 본 발명에 따른 유기 발광 화합물 과 종래의 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 2에 나타내었다. The luminous efficiency of the organic light emitting compound according to the present invention prepared in Example 1-2 and Comparative Example 1-2 and the conventional light emitting compound containing OLED is measured at 1,000 cd / m 2 and are shown in Table 2 below. It was.

[표 2]TABLE 2

Figure 112009044439287-PAT00028
Figure 112009044439287-PAT00028

상기 표 2에 나타난 바와 같이, 본 발명의 재료를 녹색 발광 소자에 적용한 결과, 비교예 1 대비 동등이상의 색순도를 유지하면서 구동전압도 낮고 발광효율이 개선되었음을 확인할 수 있었다. As shown in Table 2, as a result of applying the material of the present invention to the green light emitting device, it was confirmed that the driving voltage is low and the luminous efficiency was improved while maintaining the color purity equal to or higher than that of Comparative Example 1.

또한 본 발명의 재료를 청색 발광 소자에 적용한 결과, 비교예 1 대비 발광효율이 현저히 개선됨을 확인할 수 있었다.In addition, as a result of applying the material of the present invention to a blue light emitting device, it was confirmed that the luminous efficiency is significantly improved compared to Comparative Example 1.

Claims (10)

하기 화학식 1로 표시되는 유기 발광 화합물.An organic light emitting compound represented by Formula 1 below. [화학식 1][Formula 1]
Figure 112009044439287-PAT00029
Figure 112009044439287-PAT00029
 [상기 화학식 1에서,[In Formula 1, B1 내지 B9는 서로 독립적으로 CR12 또는 N이고,B 1 to B 9 are each independently CR 12 or N, A는 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 (C3-C30)시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 시클로알킬렌, 치환 또는 비치환된 (C2-C30)알케닐렌, 치환 또는 비치환된 (C2-C30)알키닐렌, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬렌, 치환 또는 비치환된 (C1-C30)알킬렌티오, 치환 또는 비치환된 (C1-C30)알킬렌옥시, 치환 또는 비치환된 (C6-C30)아릴렌옥시, 치환 또는 비치환된 (C6-C30)아릴렌티오, -O- 또는 -S-이고;A is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted 5- to 7-membered heterocycloalkylene, substituted or unsubstituted 5- to 7-membered heterocycloalkylene fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkylene, cycloalkylene with one or more substituted or unsubstituted aromatic rings, substituted or Unsubstituted (C2-C30) alkenylene, substituted or unsubstituted (C2-C30) alkynylene, substituted or unsubstituted (C6-C30) ar (C1-C30) alkylene, substituted or unsubstituted (C1 -C30) alkylenethio, substituted or unsubstituted (C1-C30) alkyleneoxy, substituted or unsubstituted (C6-C30) aryleneoxy, substituted or unsubstituted (C6-C30) arylenethio,- O- or -S-; R1 내지 R12는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나이상 융합된 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, 카르복실, 나이트로,
Figure 112009044439287-PAT00030
,
Figure 112009044439287-PAT00031
또는 하이드록시이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R51 내지 R58 및 R61 내지 R63은 상기 R1 내지 R12에서의 정의와 동일하고; 상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며; 상기 R21 내지 R28은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이고, 상기 Ra, Rb, Rc, Rd는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이며, 상기 Y는 S 또는 O이고, 상기 Re, Rf는 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C6-C30)아릴옥시이며; m은 1 또는 2의 정수이다.]R 1 to R 12 are each independently Substituted or unsubstituted fused with one or more hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Substituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, or substituted or unsubstituted aromatic ring 5 1-7 membered heterocycloalkyl, Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, cyano, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= 0) R 27 R 28 , R a R b R c Si-, R d Y-, R e C (= 0)-, R f C (= 0) O-, substituted or unsubstituted ( C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, carboxyl, nitro,
Figure 112009044439287-PAT00030
,
Figure 112009044439287-PAT00031
Or may be linked with (C3-C30) alkylene or (C3-C30) alkenylene, which may or may not be hydroxy or contain a fused ring with adjacent substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 51 to R 58 and R 61 to R 63 is the same as defined above for R 1 to R 12 ; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; R 21 to R 28 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, and R a , R b , R c , R d are each independently substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl, Y is S or O, and R e , R f is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C6-C30) Aryloxy; m is an integer of 1 or 2.] 제 1항에 있어서,The method of claim 1, 상기 R1 내지 R12, R21 내지 R28, R51 내지 R58 및 R61 내지 R63의 “치환 또는 비치환”에 있어서, 치환은 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥 시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고, 상기 R31 내지 R38은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴인 것을 특징으로 하는 유기 발광 화합물.In the "substituted or unsubstituted" of R 1 to R 12 , R 21 to R 28 , R 51 to R 58, and R 61 to R 63 , the substituents are each independently substituted or unsubstituted with deuterium, halogen, or halogen. (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) heteroaryl substituted or unsubstituted, 5- to 7-membered heterocycloalkyl, aromatic ring fused at least one 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR 31 R 32 , BR 33 R 34 , PR 35 R 36 , P (= 0) R 37 R 38 , (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) alkyloxy, (C1 -C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, ( C6-C30 ) Aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, Further substituted with one or more selected from the group consisting of nitro or hydroxy, or substituents adjacent to each other may be connected to form a ring, wherein R 31 to R 38 may be each independently selected from (C 1 -C 30) alkyl, (C 6 -C30) aryl or (C3-C30) heteroaryl. 제 1항에 있어서, The method of claim 1, 상기 R1 내지 R12는 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.R 1 to R 12 is an organic light emitting compound, characterized in that selected from the following structure.
Figure 112009044439287-PAT00032
Figure 112009044439287-PAT00032
 [R71 내지 R141은 서로 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)시클로알킬이 하나이상 융합된 (C6-C30)아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 아미노, (C1-C30)알킬아미노, (C6-C30)아릴아미노, NR41R42, BR43R44, PR45R46, P(=O)R47R48, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C2-C30)알케닐, (C2-C30)알키닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고, 상기 R41 내지 R48은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이다.][R 71 to R 141 independently of one another are hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 6 -C 30) aryl wherein at least one fused (C 6 -C 30) aryl, ( C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, cyano, amino, (C1-C30) alkylamino, (C6-C30) arylamino, NR 41 R 42 , BR 43 R 44 , PR 45 R 46 , P (= O) R 47 R 48 , tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryl Silyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1- C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy Can be linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring , R 41 to R 48 are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl.] 제 1항에 있어서, The method of claim 1, 상기 R1 내지 R12는 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.R 1 to R 12 is an organic light emitting compound, characterized in that selected from the following structure.
Figure 112009044439287-PAT00033
Figure 112009044439287-PAT00033
 제 1항에 있어서, The method of claim 1, 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.An organic light emitting compound, characterized in that selected from the following structures. 하기 화합물이 본 발명을 한정하는 것은 아니다.The following compounds do not limit the present invention.
Figure 112009044439287-PAT00034
Figure 112009044439287-PAT00034
Figure 112009044439287-PAT00035
Figure 112009044439287-PAT00035
Figure 112009044439287-PAT00036
Figure 112009044439287-PAT00036
Figure 112009044439287-PAT00037
Figure 112009044439287-PAT00037
 제 1항 내지 제 5항에서 선택되는 어느 한 항에 따른 유기 발광 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.An organic electroluminescent device comprising the organic light emitting compound according to any one of claims 1 to 5. 제 6항에 있어서,The method of claim 6, 상기 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 하기 화학식 2 및 화학식 3으로 표시되는 도판트 하나 이상을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The organic electroluminescent device includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound and at least one dopant represented by Formulas 2 and 3 below. Organic electroluminescent device. [화학식 2][Formula 2]
Figure 112009044439287-PAT00038
Figure 112009044439287-PAT00038
 [상기 화학식 2에서, [In Formula 2, Ar11 및 Ar12는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또 는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C4-C30)헤테로아릴, 치환 또는 비치환된 (C6-C30)아릴아미노, (C1-C30)알킬아미노, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬이거나 Ar11 및 Ar12는 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고; Ar 11 and Ar 12 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C4-C30) heteroaryl, substituted or unsubstituted Substituted (C6-C30) arylamino, (C1-C30) alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring, 5- to 7-membered Heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring is a (C3-C30) cycloalkyl fused at least one or Ar 11 and Ar 12 includes or comprises a fused ring Unsubstituted (C3-C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; c가 1인 경우 Ar13은 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C4-C30)헤테로아릴 또는 하기 구조에서 선택되는 치환기이고;when c is 1, Ar 13 is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;
Figure 112009044439287-PAT00039
Figure 112009044439287-PAT00039
 c가 2인 경우 Ar13는 치환 또는 비치환된 (C6-C30)아릴렌, 치환 또는 비치환된 (C4-C30)헤테로아릴렌 또는 하기 구조에서 선택되는 치환기이고;when c is 2, Ar 13 is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;
Figure 112009044439287-PAT00040
Figure 112009044439287-PAT00040
 Ar14 및 Ar15은 서로 독립적으로 치환 또는 비치환된 (C6-C30)아릴렌 또는 치환 또는 비치환된 (C4-C30)헤테로아릴렌이고;Ar 14 and Ar 15 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene; R201 내지 R203는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 (C1- C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이고;R 201 to R 203 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl; d는 1 내지 4의 정수이며, d is an integer of 1 to 4, e는 0 또는 1의 정수이다.]e is an integer of 0 or 1.] [화학식 3](3)
Figure 112009044439287-PAT00041
Figure 112009044439287-PAT00041
 [상기 화학식 3에서, [In Formula 3, R211 내지 R214는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, NR301R302, BR303R304, PR305R306, P(=O)R307R308, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알킬옥시, 치환 또는 비치환된 (C1-C30)알킬티오, 치환 또는 비치환된 (C6-C30)아릴옥시, 치환 또는 비치환된 (C6-C30)아릴티오, 치환 또는 비치환된 (C1-C30)알콕시카보닐, 치환 또는 비치환된 (C1-C30)알킬카보닐, 치환 또는 비치환된 (C6-C30)아릴카보닐, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐, 치환 또는 비치환된 (C6-C30)아릴옥시카보닐, 치환 또는 비치환된 (C1-C30)알콕시카보닐옥시, 치환 또는 비치환된 (C1-C30)알킬카보닐옥시, 치환 또는 비치환된 (C6-C30)아릴카보닐옥시, 치환 또는 비치환된 (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로, 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고, 상기 R301 내지 R308은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이다.]R 211 to R 214 are each independently Hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5 member 5-7 membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring, wherein one to seven membered heterocycloalkyl, substituted or unsubstituted aromatic rings are fused. Is (C3-C30) cycloalkyl, cyano, NR 301 R 302 , BR 303 R 304 , PR 305 R 306 , P (= 0) R 307 R 308 , substituted or unsubstituted (C1-C30) C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkyloxy, substituted or unsubstituted (C1-C30) alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6-C30) aryl O, substituted or unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted (C1-C30) alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or unsubstituted ( C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, Substituted or unsubstituted (C1-C30) alkylcarbonyloxy, substituted or unsubstituted (C6-C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxyl, nit And may be linked with (C3-C30) alkylene or (C3-C30) alkenylene, which may be hydroxy, with or without adjacent substituents and fused rings, to form an alicyclic ring and a monocyclic or polycyclic aromatic ring. and, wherein R 301 through R 308 independently represent a substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or A substituted (C3-C30) heteroaryl] 제 7항에 있어서,The method of claim 7, wherein 상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물 또는 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound or a group 1, 2, 4, 5 cycle transition metal, lanthanum series metal and organic metal of d-transition element in the organic layer An organic electroluminescent device further comprising at least one metal or complex compound selected from the group consisting of: 제 7항에 있어서,The method of claim 7, wherein 상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. 제 7항에 있어서,The method of claim 7, wherein 상기 유기물층은 적색, 녹색 또는 청색 발광을 하는 유기 화합물층 하나 이상을 동시에 포함하는 것을 특징으로 하는 백색 유기 전계 발광 소자.The organic material layer is a white organic electroluminescent device, characterized in that it comprises at least one organic compound layer for emitting red, green or blue light at the same time.
KR1020090066446A 2009-07-21 2009-07-21 Novel organic electroluminescent compounds and organic electroluminescent device using the same KR20110008892A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020090066446A KR20110008892A (en) 2009-07-21 2009-07-21 Novel organic electroluminescent compounds and organic electroluminescent device using the same
PCT/KR2010/004697 WO2011010843A1 (en) 2009-07-21 2010-07-19 Novel organic electroluminescent compounds and organic electroluminescent device using the same
TW099123921A TW201111474A (en) 2009-07-21 2010-07-21 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020090066446A KR20110008892A (en) 2009-07-21 2009-07-21 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Publications (1)

Publication Number Publication Date
KR20110008892A true KR20110008892A (en) 2011-01-27

Family

ID=43499251

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020090066446A KR20110008892A (en) 2009-07-21 2009-07-21 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Country Status (3)

Country Link
KR (1) KR20110008892A (en)
TW (1) TW201111474A (en)
WO (1) WO2011010843A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140089259A (en) * 2013-01-04 2014-07-14 삼성디스플레이 주식회사 Carbazole-based compound and organic light emitting diode comprising the same
KR20150034665A (en) * 2013-09-26 2015-04-03 주식회사 엘지화학 Heterocyclic compound and organic light emitting device using the same
WO2016105141A3 (en) * 2014-12-24 2016-10-06 주식회사 두산 Organic compound and organic electroluminescent element comprising same
US10087145B2 (en) 2014-05-02 2018-10-02 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device comprising the same
CN111925314A (en) * 2020-07-23 2020-11-13 大同煤矿集团有限责任公司 Carbazole and anthracene-based blue host material capable of emitting light from host
EP3753928A1 (en) * 2014-12-24 2020-12-23 Doosan Solus Co., Ltd. Triazine compound and organic electroluminescent element comprising same

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130025190A (en) * 2011-09-01 2013-03-11 롬엔드하스전자재료코리아유한회사 Novel compounds for organic electronic material and organic electroluminescent device using the same
KR20130127014A (en) * 2012-01-16 2013-11-22 롬엔드하스전자재료코리아유한회사 Organic electroluminescent device using the organic electroluminescent compounds
CN102757793B (en) * 2012-07-27 2014-01-15 江苏和成显示科技股份有限公司 Liquid crystal compound and application thereof
JP2015233024A (en) * 2012-09-03 2015-12-24 出光興産株式会社 Organic electroluminescent device
CN105441066B (en) * 2015-11-20 2017-08-08 中节能万润股份有限公司 A kind of electroluminescent organic material and its application
KR20180057109A (en) 2016-11-21 2018-05-30 주식회사 두산 Organic light-emitting compound and organic electroluminescent device using the same
KR102640489B1 (en) * 2018-11-16 2024-02-26 에스에프씨 주식회사 Novel boron compounds and Organic light emitting diode including the same
CN111825518B (en) * 2019-12-30 2021-06-11 陕西莱特光电材料股份有限公司 Organic compound, organic electroluminescent device, and electronic device
CN111548348A (en) * 2020-04-17 2020-08-18 苏州久显新材料有限公司 Fluorenoazanaphthalene derivative, synthesis method thereof and electronic device thereof
CN112142548B (en) 2020-09-30 2021-09-24 陕西莱特光电材料股份有限公司 Organic compound, and electronic element and electronic device using same
KR20220094620A (en) * 2020-12-29 2022-07-06 엘지디스플레이 주식회사 Emitting compound and orgnic light emitting device including the same
WO2022144018A1 (en) * 2021-01-04 2022-07-07 浙江光昊光电科技有限公司 Organic mixture and application thereof in organic electronic device
WO2023219071A1 (en) * 2022-05-13 2023-11-16 出光興産株式会社 Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5361237B2 (en) * 2007-05-16 2013-12-04 キヤノン株式会社 Benzo [a] fluoranthene compound and organic light-emitting device using the same
KR100940938B1 (en) * 2007-12-04 2010-02-08 다우어드밴스드디스플레이머티리얼 유한회사 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140089259A (en) * 2013-01-04 2014-07-14 삼성디스플레이 주식회사 Carbazole-based compound and organic light emitting diode comprising the same
KR20150034665A (en) * 2013-09-26 2015-04-03 주식회사 엘지화학 Heterocyclic compound and organic light emitting device using the same
US10087145B2 (en) 2014-05-02 2018-10-02 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device comprising the same
KR20230007265A (en) * 2014-05-02 2023-01-12 삼성디스플레이 주식회사 Condensed-cyclic compound and organic light emitting device comprising the same
WO2016105141A3 (en) * 2014-12-24 2016-10-06 주식회사 두산 Organic compound and organic electroluminescent element comprising same
EP3753928A1 (en) * 2014-12-24 2020-12-23 Doosan Solus Co., Ltd. Triazine compound and organic electroluminescent element comprising same
US10916709B2 (en) 2014-12-24 2021-02-09 Doosan Solus Co., Ltd. Organic compound and organic electroluminescent element comprising same
US11832514B2 (en) 2014-12-24 2023-11-28 Solus Advanced Materials Co., Ltd. Organic compound and organic electroluminescent element comprising same
US11997924B2 (en) 2014-12-24 2024-05-28 Solus Advanced Materials Co., Ltd. Organic compound and organic electroluminescent element comprising same
CN111925314A (en) * 2020-07-23 2020-11-13 大同煤矿集团有限责任公司 Carbazole and anthracene-based blue host material capable of emitting light from host

Also Published As

Publication number Publication date
TW201111474A (en) 2011-04-01
WO2011010843A1 (en) 2011-01-27

Similar Documents

Publication Publication Date Title
KR20110008892A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR101427605B1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
JP5797672B2 (en) Novel organic electroluminescent compound and organic electroluminescent device using the same
JP5710491B2 (en) Novel organic light-emitting compound and organic light-emitting device using the same
JP5781499B2 (en) Novel organic electroluminescent compound and organic electroluminescent device using the same
KR20100109050A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100108914A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100137198A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100118700A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110008784A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR101645949B1 (en) Electroluminescent device using the electroluminescent compounds
KR20110112098A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110116635A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110015836A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100118690A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
JP2015159288A (en) Electroluminescence element adopting electroluminescent compound as light-emitting material
KR20100137188A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100108924A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110121147A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20120020816A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
KR20110132721A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20120122812A (en) Novel organic electroluminescence compounds and organic electroluminescence device using the same
KR20110008723A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20120020901A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
KR20100108909A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same

Legal Events

Date Code Title Description
N231 Notification of change of applicant
A201 Request for examination
E902 Notification of reason for refusal
E601 Decision to refuse application