WO2014157933A1 - 신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자 - Google Patents

신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자 Download PDF

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WO2014157933A1
WO2014157933A1 PCT/KR2014/002538 KR2014002538W WO2014157933A1 WO 2014157933 A1 WO2014157933 A1 WO 2014157933A1 KR 2014002538 W KR2014002538 W KR 2014002538W WO 2014157933 A1 WO2014157933 A1 WO 2014157933A1
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group
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light emitting
layer
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French (fr)
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김성훈
안현철
김정선
김현명
백선중
이은영
김영덕
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Dongjin Semichem Co Ltd
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Dongjin Semichem Co Ltd
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Priority claimed from KR1020140034898A external-priority patent/KR101527873B1/ko
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Priority to CN201480018568.4A priority Critical patent/CN105102408B/zh
Priority to JP2016505394A priority patent/JP2016521261A/ja
Publication of WO2014157933A1 publication Critical patent/WO2014157933A1/ko
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Definitions

  • the present invention relates to a novel benzophenanthrene derivative compound and an organic light emitting device using the same, and more particularly, to a benzophenanthrene derivative compound capable of manufacturing an organic light emitting device having excellent characteristics such as driving voltage, luminous efficiency and color purity. It relates to an organic light emitting device using the same.
  • the organic light emitting device capable of low-voltage driving by self-emission type has excellent viewing angle, contrast ratio, and the like, and requires no backlight, and is light and thin, and consumed, compared to the liquid crystal display (LCD) which is the mainstream of flat panel display devices. It is also attracting attention as a next-generation display device because it is advantageous in terms of power and has a wide range of color reproduction.
  • LCD liquid crystal display
  • the organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode) and an organic layer between the two electrodes.
  • the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML). It may include an electron injection layer, and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) on the light emission characteristics of the light emitting layer.
  • a light emitting layer may be doped into the light emitting layer (host).
  • the present invention to solve the problems of the prior art as described above is an organic light emitting device comprising a benzophenanthrene derivative compound and the benzophenanthrene derivative compound which can improve the characteristics such as driving voltage, luminous efficiency, color purity of the organic light emitting device
  • the purpose is to provide.
  • the present invention provides a benzophenanthrene derivative compound represented by the following formula (1):
  • R 1 to R 14 are each independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C20 40 aryl groups, substituted or unsubstituted hetero aryl groups having 3 to 40 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkylamino group, substituted or unsubstituted C3-C20 cycloalkylamino group, substituted or unsubstituted C3-C20 heterocycloalkylamino group, substituted or unsubstituted C6-C30
  • the present invention provides an organic light emitting device comprising the benzophenanthrene derivative compound.
  • the organic light emitting device using the novel benzophenanthrene derivative compound of the present invention has excellent effects such as driving voltage, luminous efficiency and color purity.
  • FIG. 1 is a cross-sectional view showing the structure of an organic light emitting device according to an embodiment of the present invention.
  • the present invention provides a benzophenanthrene derivative compound represented by Formula 1 below:
  • R 1 to R 14 are each independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C20 40 aryl groups, substituted or unsubstituted hetero aryl groups having 3 to 40 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkylamino group, substituted or unsubstituted C3-C20 cycloalkylamino group, substituted or unsubstituted C3-C20 heterocycloalkylamino group, substituted or unsubstituted C6-C30
  • alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, A stearyl group, a trichloromethyl group, a trifluoromethyl group, and the like, and at least one hydrogen atom of the alkyl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, or a silyl group (in this case, Alkylsilyl groups ", substituted or unsubstituted amino groups (-NH2, -NH (R), -N (R ') (R”), wherein R, R' and R "are each independently from 1 to 24 alkyl group (in this case referred to as
  • aryl group which is a substituent used in the compound of the present invention are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-ratio Phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group
  • an aromatic group such as an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a tetrahydronaphthyl group, and the like, and may be substituted with the same substituent as in the alkyl
  • alkenyl group which is a substituent used in the compound of the present invention, include an alkenyl group in which an aryl group such as a stybenyl group and a styrenyl group are connected, and specific examples of the cycloalkyl group include a cichloropentyl group and a cyclohexyl group. It is not limited.
  • the arylamine group which is a substituent used in the compound of the present invention is a diphenylamine group, a phenylnaphthylamine group, a phenylbiphenylamine group, a naphthylbiphenylamine group, a dinaphthylamine group, a dibiphenylamine group, a dianthracenylamine Group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine group, 9-methyl- anthracenylamine group, ditolyl amine group, phenyl tolyl amine group, triphenylamino A phenylamine group, a phenyl biphenylamino phenyl amine group, a naphthyl phenylaminophenyl biphenylamine group, etc. are mentioned, but it is not limited to this.
  • substituted or unsubstituted refers to a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aralkyl group, an alkoxy group, an alkylamino group, an arylamino group, a heteroaryl group, It is substituted or unsubstituted with one or more substituents selected from the group consisting of aralkylamino group, alkylsilyl group, arylsilyl group, aryloxy group, aryl group, heteroaryl group, germanium, phosphorus, boron, hydrogen and deuterium. .
  • benzophenanthrene derivative compound of the present invention is preferably selected from the group represented by the following formula, but is not limited thereto.
  • the benzophenanthrene derivative compound can be prepared through the production method of the following schematic diagram.
  • the present invention provides an organic light emitting device comprising the benzophenanthrene derivative compound.
  • the organic light emitting device of the present invention comprises at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode,
  • the phenanthrene derivative compound is characterized in being included in at least one of the layers.
  • the benzophenanthrene derivative compound according to the present invention is preferably included in the light emitting layer between the anode and the cathode.
  • the layer between the anode and the cathode may be formed by a deposition method or a solution process.
  • the present invention can be used in various ways, such as a display device, a display device and a monochromatic or white lighting device including the organic light emitting device.
  • a hole injection layer HIL
  • HTL hole transport layer
  • EML emission layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
  • the substrate may be a substrate used in a conventional organic light emitting device, in particular, it is preferable to use an organic substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
  • the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
  • the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
  • HIL hole injection layer
  • LB Langmuir-Blodgett
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and generally, a deposition temperature of 50-500 ° C., It is preferable to select suitably from the vacuum degree of 10 -8 -10 -3 torr, the deposition rate of 0.01-100 kPa / sec, and the film thickness of 10 kPa-5micrometer.
  • the hole injection layer material may be a known material, for example TCTA (4,4 ', 4 "-tree (N), which is a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Patent No. 4,356,429.
  • TCTA 4,4 ', 4 "-tree (N)
  • N a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Patent No. 4,356,429.
  • HI-406 N1, N1 '-(biphenyl-4,4'-diyl) bis (N1- (naphthalen-1-yl) -N4 , N4-diphenylbenzene-1,4-diamine) may be used as the hole injection layer material.
  • a hole transport layer (HTL) material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, etc., but it is easy to obtain a uniform film quality, and pin holes are generated. It is preferable to form by the vacuum evaporation method from the point which is difficult.
  • the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in a range equivalent to that of the hole injection layer.
  • the hole transport layer material is not particularly limited, but may be used by using a compound represented by the formula (1) according to the present invention, or arbitrarily selected from conventional known materials used in the hole transport layer.
  • the hole transport material is a carbazole derivative such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N, in addition to the compound represented by Formula 1 according to the present invention '-Diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD Ordinary amine derivative etc. which have aromatic condensed ring, such as), etc. can be used.
  • the light emitting layer (EML) material may be formed on the hole transport layer by a method such as a vacuum deposition method, a spin coating method, a cast method, an LB method, etc., but it is easy to obtain a uniform film quality and difficult to generate pin holes. It is preferable to form by the vacuum deposition method.
  • the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition range as the formation of the hole injection layer.
  • the light emitting layer material may be used alone or as a host to the compound represented by the formula (1) of the present invention.
  • a phosphorescent or fluorescent dopant and a host may be used together to form a light emitting layer.
  • a phosphorescent or fluorescent dopant and a host may be used together to form a light emitting layer.
  • the fluorescent dopant IDE102 or IDE105 or BD142, which can be purchased from Idemitsu, may be used.
  • green phosphorescent dopant Ir (ppy) 3 (fac-tris (2-phenylpyridine) iridium), FIrpic (iridium (III) bis [(4,6-difluorophenyl) -pyridinato-N, C2 ′] picolinate), a blue phosphorescent dopant, and a red phosphorescent dopant RD61 from UDC, may be commonly vacuum deposited (doped).
  • the doping concentration of the dopant is not particularly limited, but the concentration of the dopant with respect to 100 parts by weight relative to the host is preferably 0.01-15 parts by weight.
  • the hole-inhibiting material that can be used is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used.
  • an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1), and the like, and typical Balq and phenanthrolines ) -Based compound may be used.
  • An electron transport layer (ETL) material is formed on the light emitting layer formed as above, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, or a casting method, and particularly preferably by a vacuum deposition method.
  • the electron transport layer material has a function of stably transporting electrons injected from an electron injection electrode (Cathode) is not particularly limited in kind, for example, quinoline derivatives, especially tris (8-quinolinorate) aluminum ( Alq3) can be used.
  • an electron injection layer (EIL) which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer material may be LiF, NaCl, CsF, Li 2 O, BaO, or the like. The substance of can be used.
  • the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.
  • an electron injection layer (EIL) material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is preferable to form by the vacuum deposition method.
  • EIL electron injection layer
  • the cathode forming metal is formed on the electron injection layer by a vacuum deposition method or a sputtering method and used as a cathode.
  • the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
  • a transmissive cathode using ITO and IZO may be used to obtain a top emitting device.
  • the organic light emitting device of the present invention has an organic structure of an anode, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), a cathode (cathode) structure
  • HIL hole injection layer
  • HTL hole transport layer
  • EML electron transport layer
  • EIL electron injection layer
  • cathode cathode
  • the thickness of the organic thin film layer formed according to the present invention as described above can be adjusted according to the required degree, preferably 10-1,000 nm, more preferably 20-150 nm.
  • reaction solution was poured into 200 ml of cold sodium carbonate (Na 2 CO 3 ) aqueous solution, and 200 ml of additional methylene chloride was added thereto. Stir until gas evolution ceased. After extraction, the aqueous layer was extracted again with 250 ml of methylene chloride. The organic layer was dried over magnesium sulfate (MgSO 4 ), filtered and concentrated to give 10.5 g of red liquid 1-chloro-3,4-dihydro-2-carbaldehyde (1-chloro-3,4-dihydro-2-carbaldehyde). (54.7 mmol, 91.3%) was obtained.
  • MgSO 4 magnesium sulfate
  • Synthesis was carried out in the same manner as in Synthesis Example 1-6, except that 4-chloro-5,6-dihydrobenzo [c] phenanthrene was used instead of 8-bromo-5,6-dihydrobenzo [c] phenanthrene.
  • ADN ADN: 9,10-di (2-naphthyl)-anthracene
  • BD142 was used as a dopant material of the light emitting layer.
  • An organic light emitting diode was manufactured according to a conventional method using a compound of (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethycrylicene-6,12-diamine). It was.
  • a 650 ⁇ hole injection layer (hole injection layer material: HI-406 (N 1 , N 1 '-(biphenyl-4,4'-diyl) on a 1500 ⁇ thick ITO layer (anode) formed on a glass substrate.
  • hole injection layer material HI-406 (N 1 , N 1 '-(biphenyl-4,4'-diyl) on a 1500 ⁇ thick ITO layer (anode) formed on a glass substrate.
  • the luminescence properties of the organic light emitting diodes were measured and shown in Table 1 below.
  • Examples 1 to 15 are similar in voltage to Comparative Example 1, but it can be seen that the current efficiency and luminance are improved up to 1.5 times, and the color coordinates are relatively excellent.
  • the compound obtained in Synthesis Examples 18 to 23 was used as the light emitting dopant material of the light emitting layer, and the compound of BD142 was used as the comparative dopant material, and ADN (ADN: 9,10-di (2-naphthyl) ) It was prepared in the same manner as in Example except that ananthracene) was used.
  • Examples 18 to 23 are superior in driving voltage to Comparative Examples.
  • the current efficiency shows similar or low characteristics, but this is a result of moving to the short wavelength region as can be seen from the CIEy value check in the color coordinates, and it shows the characteristics up to 1.6 times when considering conversion efficiency.
  • an organic light emitting device having excellent characteristics such as driving voltage, luminous efficiency and color coordinates may be manufactured using the novel benzophenanthrene compound of the present invention.
  • the organic light emitting device using the novel benzophenanthrene derivative compound of the present invention has excellent effects such as driving voltage, luminous efficiency and color purity.

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Abstract

본 발명은 신규한 벤조펜안트렌 유도체 화합물 및 이를 포함하는 유기발광소자에 관한 것으로서, 보다 상세하게는 유기발광소자에 적용시 구동 전압이 낮고, 발광 효율 및 색순도 특성이 우수한 효과가 있는 벤조펜안트렌 유도체 화합물에 관한 것이다.

Description

신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자
본 발명은 신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자에 관한 것으로서, 보다 상세하게는 구동 전압, 발광 효율 및 색순도 등의 특성이 우수한 유기발광소자를 제조할 수 있는 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자에 관한 것이다.
최근 자체 발광형으로 저전압 구동이 가능한 유기발광소자소자는 평판 표시소자의 주류인 액정디스플레이(LCD, liquid crystal display)에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하여 경량 및 박형이 가능하며 소비전력 측면에서도 유리하고 색 재현 범위가 넓어 차세대 표시소자로서 주목을 받고 있다.
일반적으로 유기발광소자는 음극(전자주입전극)과 양극(정공주입전극) 및 상기 두 전극 사이에 유기층을 포함하는 구조를 갖는다. 이때, 유기층은 발광층(EML, light emitting layer) 이외에 정공주입층(HIL, hole injection layer), 정공수송층(HTL, hole transport layer), 전자수송층(ETL, electron transport layer) 또는 전자주입층(EIL, electron injection layer)을 포함할 수 있으며, 발광층의 발광특성상, 전자차단층(EBL, electron blocking layer) 또는 정공차단층(HBL, hole blocking layer)을 추가로 포함할 수 있다.
이러한 구조의 유기발광소자에 전기장이 가해지면 양극으로부터 정공이 주입되고 음극으로부터 전자가 주입되어 정공과 전자는 각각 정공수송층과 전자수송층을 거쳐 발광층에서 재조합(recombination)하게 되어 발광여기자(exitons)를 형성한다. 형성된 발광여기자는 바닥상태(ground states)로 전이하면서 빛을 방출한다. 발광 상태의 효율과 안정성을 증가시키기 위하여 발광 색소(도펀트)를 발광층(호스트)에 도핑하기도 한다.
유기발광소자의 발광층에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 발광물질을 이용한 유기발광소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. 따라서, 우수한 발광특성을 갖는 물질을 이용하여 저전압구동, 고효율 및 긴 수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다.
상기와 같은 종래기술의 문제점을 해결하고자 본 발명은 유기발광소자의 구동 전압, 발광 효율, 색순도 등의 특성을 향상시킬 수 있는 벤조펜안트렌 유도체 화합물 및 상기 벤조펜안트렌 유도체 화합물을 포함하는 유기발광소자를 제공하는 것을 목적으로 한다.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 벤조펜안트렌 유도체 화합물을 제공한다:
[화학식 1]
Figure PCTKR2014002538-appb-I000001
상기 화학식 1에서,
R1 내지 R14는 각각 독립적으로 치환 또는 비치환의 탄소수 1 내지 20의 알킬기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로 아릴기, 치환 또는 비치환의 탄소수 1 내지 30의 알콕시기,　치환 또는 비치환의 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 헤테로아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환의 알케닐기, 치환 또는 비치환의 알키닐기, 시아노기, 할로겐기, 중수소 및 수소로 이루어진 군에서 선택된다.
또한 본 발명은 상기 벤조펜안트렌 유도체 화합물을 포함하는 유기발광소자를 제공한다.
본 발명의 신규한 벤조펜안트렌 유도체 화합물을 이용한 유기발광소자는 구동 전압, 발광 효율 및 색순도 등의 특성이 우수한 효과가 있다.
도 1은 본 발명의 하나의 실시예에 따른 유기발광소자의 구조를 나타내는 단면도이다.
이하 본 발명을 상세하게 설명한다.
본 발명은 하기 화학식 1로 표시되는 벤조펜안트렌 유도체 화합물을 제공한다:
[화학식 1]
Figure PCTKR2014002538-appb-I000002
상기 화학식 1에서,
R1 내지 R14는 각각 독립적으로 치환 또는 비치환의 탄소수 1 내지 20의 알킬기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로 아릴기, 치환 또는 비치환의 탄소수 1 내지 30의 알콕시기,　치환 또는 비치환의 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 헤테로아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환의 알케닐기, 치환 또는 비치환의 알키닐기, 시아노기, 할로겐기, 중수소 및 수소로 이루어진 군에서 선택된다.
본 발명에서 사용되는 치환기인 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, tert-부틸기, 펜틸기, iso-아밀기, 헥실기, 헵틸기, 옥틸기, 스테아릴기, 트리클로로메틸기, 트리플루오르메틸기 등을 들 수 있으며, 상기 알킬기 중 하나 이상의 수소 원자는 중수소 원자, 할로겐 원자, 히드록시기, 니트로기, 시아노기, 트리플루오로메틸기, 실릴기(이 경우 "알킬실릴기"라 함), 치환 또는 비치환된 아미노기(-NH2, -NH(R), -N(R')(R"), 여기서 R, R' 및 R"은 각각 독립적으로 탄소수 1 내지 24의 알킬기임(이 경우 "알킬아미노기"라 함)), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 5 내지 24의 아릴기, 탄소수 6 내지 24의 아릴알킬기, 탄소수 3 내지 24의 헤테로아릴기 또는 탄소수 3 내지 24의 헤테로아릴알킬기로 치환될 수 있다.
본 발명의 화합물에서 사용되는 치환기인 알콕시기의 구체적인 예로는 메톡시기, 에톡시기, 프로폭시기, 이소부틸옥시기, sec-부틸옥시기, 펜틸옥시기, iso-아밀옥시기, 헥실옥시기 등을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.
본 발명의 화합물에서 사용되는 치환기인 아릴기의 구체적인 예로는 페닐기, 2-메틸페닐기, 3-메틸페닐기, 4-메틸페닐기, 4-에틸페닐기, o-비페닐기, m-비페닐기, p-비페닐기, 4-메틸비페닐기, 4-에틸비페닐기, o-터페닐기, m-터페닐기, p-터페닐기, 1-나프틸기, 2-나프틸기, 1-메틸나프틸기, 2-메틸나프틸기, 안트릴기, 펜안트릴기, 피레닐기, 플루오레닐기, 테트라히드로나프틸기 등과 같은 방향족 그룹을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.
본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기의 구체적인 예로는 피리디닐기, 피리미디닐기, 트리아지닐기, 인돌리닐기, 퀴놀린닐기, 피롤리디닐기, 피페리디닐기, 모폴리디닐기, 피페라디닐기, 카바졸릴기, 옥사졸릴기, 옥사디아졸릴기, 벤조옥사졸릴기, 치아졸릴기, 치아디아졸릴기, 벤조치아졸릴기, 트리아졸릴기, 이미다졸릴기, 벤조이미다졸기 등이 있으며, 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.
본 발명의 화합물에서 사용되는 치환기인 알케닐기의 구체적인 예로는 스티베닐기, 스티레닐기 등의 아릴기가 연결된 알케닐기고 있고, 시클로알킬기의 구체적인 예로는 시클로로펜틸기, 시클로헥실기 등이 있으나 이에 한정되는 것은 아니다.
본 발명의 화합물에서 사용되는 치환기인 아릴아민기는 디페닐아민기, 페닐나프틸아민기, 페닐비페닐아민기, 나프틸비페닐아민기, 디나프틸아민기, 디비페닐아민기, 디안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디톨릴 아민기, 페닐 톨릴 아민기, 트리페닐아미노페닐아민기, 페닐 비페닐아미노 페닐 아민기, 나프틸 페닐아미노페닐 비페닐아민기 등을 들 수 있으나, 이에만 한정되는 것은 아니다.
본 발명에 있어서, "치환 또는 비치환"이라는 용어는 시아노기, 할로겐기, 히드록시기, 니트로기, 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아르알킬기, 알콕시기, 알킬아미노기, 아릴아미노기, 헤테로 아릴아미노기, 아르알킬아미노기, 알킬실릴기, 아릴실릴기, 아릴옥시기, 아릴기, 헤테로아릴기, 게르마늄, 인, 보론, 수소 및 중수소로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환 되는 것을 의미한다.
구체적으로 본 발명의 상기 벤조펜안트렌 유도체 화합물은 하기 화학식으로 표시되는 군으로부터 선택되는 것이 바람직하며, 이에 국한되는 것은 아니다.
Figure PCTKR2014002538-appb-I000003
Figure PCTKR2014002538-appb-I000004
Figure PCTKR2014002538-appb-I000005
Figure PCTKR2014002538-appb-I000006
Figure PCTKR2014002538-appb-I000007
Figure PCTKR2014002538-appb-I000008
Figure PCTKR2014002538-appb-I000009
Figure PCTKR2014002538-appb-I000010
Figure PCTKR2014002538-appb-I000011
Figure PCTKR2014002538-appb-I000012
Figure PCTKR2014002538-appb-I000013
Figure PCTKR2014002538-appb-I000014
Figure PCTKR2014002538-appb-I000015
Figure PCTKR2014002538-appb-I000016
Figure PCTKR2014002538-appb-I000017
Figure PCTKR2014002538-appb-I000018
Figure PCTKR2014002538-appb-I000019
Figure PCTKR2014002538-appb-I000020
Figure PCTKR2014002538-appb-I000021
Figure PCTKR2014002538-appb-I000022
Figure PCTKR2014002538-appb-I000023
Figure PCTKR2014002538-appb-I000024
Figure PCTKR2014002538-appb-I000025
또한 본 발명은 상기 벤조펜안트렌 유도체 화합물은 하기 모식도 기재의 제조방법을 통하여 제조될 수 있다.
[모식도]
Figure PCTKR2014002538-appb-I000026
또한 본 발명은 상기 벤조펜안트렌 유도체 화합물을 포함하는 유기발광소자를 제공한다.
또한 본 발명의 유기발광소자는 애노드와 캐소드 사이에 발광층, 정공주입층, 정공수송층, 정공저지층, 전자수송층, 전자주입층 및 전자저지층으로 이루어진 군으로부터 선택된 하나 이상의 층을 포함하며, 상기 벤조펜안트렌 유도체 화합물은 상기 층 중 적어도 하나 이상의 층에 포함된 것을 특징으로 한다.
특히 본 발명에 따른 벤조펜안트렌 유도체 화합물은 상기 애노드 및 캐소드 사이의 발광층에 포함되는 것이 바람직하다.
또한, 애노드와 캐소드 사이의 층은 증착방식 또는 용액공정에 의하여 형성될 수 있다.
또한 본 발명은 상기 유기발광소자를 포함하는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자 등 다양하게 사용될 수 있다.
또한 본 발명에 따른 상기 유기발광소자의 제조방법을 보다 상세히 설명하면 다음과 같다.
본 발명에 따른 유기발광소자는 애노드(anode)와 캐소드(cathod) 사이에 정공주입층(HIL), 정공수송층(HTL), 발광층(EML), 전자수송층(ETL), 전자주입층(EIL) 등의 유기박막층을 1 개 이상 포함할 수 있다.
먼저, 기판 상부에 높은 일함수를 갖는 애노드(anode) 전극용 물질을 증착시켜 애노드를 형성한다. 이때, 상기 기판은 통상의 유기발광소자에서 사용되는 기판을 사용할 수 있으며, 특히 기계적 강도, 열적 안정성, 투명성, 표면평활성, 취급용이성, 및 방수성이 우수한 유기기판 또는 투명 플라스틱 기판을 사용하는 것이 좋다. 또한, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용할 수 있다. 상기 애노드 전극용 물질은 통상의 애노드 형성방법에 의해 증착할 수 있으며, 구체적으로 증착법 또는 스퍼터링법에 의해 증착할 수 있다.
그 다음, 상기 애노드 전극 상부에 정공주입층(HIL) 물질을 진공증착법, 스핀코팅법, 캐스트법, LB(Langmuir-Blodgett)법 등과 같은 방법에 의해 형성할 수도 있지만, 균일한 막질을 얻기 쉽고, 또한 핀정공이 발생하기 어렵다는 등의 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공주입층을 형성하는 경우 그 증착조건은 정공주입층의 재료로서 사용하는 화합물, 목적하는 정공주입층의 구조 및 열적특성 등에 따라 다르지만, 일반적으로 50-500 ℃의 증착온도, 10-8-10-3 torr의 진공도, 0.01-100 Å/sec의 증착속도, 10 Å-5 ㎛의 막두께 범위에서 적절히 선택하는 것이 바람직하다.
상기 정공주입층 물질은 공지의 물질이 사용가능하며, 일예로 미국특허 제4,356,429호에 개시된 구리 프탈로시아닌 등의 프탈로시아닌 화합물 또는 스타버스트형 아민 유도체류인 TCTA(4,4',4"-트리(N-카바졸릴)트리페닐아민),m-MTDATA(4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민), m-MTDAPB(4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠,Advanced Material, 6, p677(1994)), HI-406(N1,N1'-(비페닐-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민) 등을 정공주입층 물질로 사용할 수 있다.
다음으로, 상기 정공주입층 상부에 정공수송층(HTL) 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수도 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공수송층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 대등한 조건 범위에서 선택하는 것이 좋다.
또한 상기 정공수송층 물질은 특별히 제한되지는 않으나, 본 발명에 따른 화학식 1로 표시되는 화합물을 사용하거나, 정공수송층에 사용되고 있는 통상의 공지 물질 중에서 임의로 선택하여 사용할 수 있다. 구체적으로, 상기 정공수송층 물질은 본 발명에 따른 화학식 1로 표시되는 화합물 이외에 N-페닐카바졸, 폴리비닐카바졸 등의 카바졸 유도체, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4‘-디아민(TPD), N.N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등의 방향족 축??환을 가지는 통상의 아민 유도체 등이 사용될 수 있다.
그 후, 상기 정공수송층 상부에 발광층(EML) 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수도 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 또한, 상기 발광층 재료는 본 발명의 화학식 1로 표시되는 화합물을 단독으로 사용하거나 또는 호스트로 사용할 수 있다.
상기 화학식 1로 표시되는 화합물 또는 둘 이상의 혼합물을 발광 호스트 및 도펀트로 사용하는 경우, 인광 또는 형광 도펀트 및 호스트를 함께 사용하여 발광층을 형성할 수 있다. 이때, 형광 도펀트로는 이데미츠사(Idemitsu사)에서 구입 가능한 IDE102 또는 IDE105 또는 BD142를 사용할 수 있으며, 인광 도펀트로는 녹색 인광 도판트 Ir(ppy)3(fac-tris(2-phenylpyridine) iridium), 청색 인광 도펀트인 FIrpic(iridium(Ⅲ) bis[(4,6-di- fluorophenyl)-pyridinato-N,C2'] picolinate), UDC사의 적색 인광 도펀트 RD61 등이 공통 진공증착(도핑) 될 수 있다. 도펀트의 도핑농도는 특별히 제한되지 않으나, 호스트 대비 100 중량부 대비 도펀트의 농도는 0.01-15 중량부인 것이 바람직하다.
또한 발광층에 인광 도펀트와 함께 사용할 경우에는 삼중항 여기자 또는 정공이 전자수송층(HTL)으로 확산되는 현상을 방지하기 위하여 정공억제재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시키는 것이 바람직하다. 이때 사용 할 수 있는 정공억제물질은 특별히 제한되지는 않으나, 정공억제재료로 사용되고 있는 공지의 것에서 임의의 것을 선택해서 이용할 수 있다. 예를 들면, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 또는 일본특개평 11-329734(A1)에 기재되어 있는 정공억제재료 등을 들 수 있으며, 대표적으로 Balq, 페난트롤린(phenanthrolines)계 화합물(예: UDC사 BCP) 등을 사용할 수 있다.
상기와 같이 형성된 발광층 상부에는 전자수송층(ETL) 재료를 형성되는데, 이때 상기 전자수송층은 진공증착법, 스핀코팅법, 또는 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다.
상기 전자수송층 재료는 전자주입전극(Cathode)으로부터 주입된 전자를 안정하게 수송하는 기능을 하는 것으로서 그 종류가 특별히 제한되지는 않으며, 예를 들어 퀴놀린 유도체, 특히 트리스(8-퀴놀리노레이트)알루미늄(Alq3)을 사용할 수 있다. 또한, 전자수송층 상부에 음극으로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층(EIL)이 적층될 수 있으며, 전자주입층 물질로는 LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.
또한, 상기 전자수송층(ETL)의 증착조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다.
그 뒤, 상기 전자수송층 상부에 전자주입층(EIL) 물질을 형성할 수 있으며, 이때 상기 전자수송층은 통상의 전자주입층 물질을 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다.
마지막으로 전자주입층 상부에 캐소드 형성용 금속을 진공증착법이나 스퍼터링법 등의 방법에 의해 형성하고 음극(cathode)으로 사용한다. 여기서 캐소드 형성용 금속으로는 낮은 일함수를 가지는 금속, 합금, 전기전도성 화합물, 및 이들의 혼합물을 사용할 수 있다. 구체적인 예로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 있다. 또한 전면 발광 소자를 얻기 위하여 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.
본 발명의 유기발광소자는 애노드(anode), 정공주입층(HIL), 정공수송층(HTL), 발광층(EML), 전자수송층(ETL), 전자주입층(EIL), 캐소드(cathode) 구조의 유기발광소자 뿐만 아니라, 다양한 구조의 유기발광소자의 구조가 가능하며, 필요에 따라 한층 또는 2층의 중간층을 더 형성하는 것도 가능하다.
상기와 같이 본 발명에 따라 형성되는 유기박막층의 두께는 요구되는 정도에 따라 조절할 수 있으며, 바람직하게는 10-1,000 ㎚이며, 더욱 바람직하게는 20-150 ㎚인 것이 좋다.
이하, 본 발명의 이해를 돕기 위하여 본 발명의 화합물의 바람직한 합성예 및 실시예를 제시하나, 하기 합성예 및 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 합성예 및 실시예에 한정되는 것은 아니다.
[합성예]
합성예 1-1. 1-클로로-3,4-디하이드로-2-카바알데히드 합성
Figure PCTKR2014002538-appb-I000027
질소기류 하에서 반응기에 디메틸포름아마이드 (DMF) 8.4 g(114.9 mmol), 메틸렌클로라이드 (MC) 40 ml를 투입하였다. 반응 온도를 0-5 ℃로 냉각한 다음, 옥시 염화인 (POCl3) 14 g(91.3 mmol)을 천천히 적가하고, 상온에서 2시간 동안 교반하였다. 다시 반응 온도를 0-5 ℃로 냉각한 다음, 메틸렌클로라이드 50 ml에 녹인 α-테트라론 (α-tetralone) 8.76 g (59.9 mmol) 용액을 천천히 투입하였다. 투입 완료 후 상온에서 16시간 동안 교반하였다. 반응 용액을 차가운 탄산나트륨 (Na2CO3) 수용액(satd) 200 ml에 붓고, 추가 메틸렌클로라이드 200 ml를 투입하였다. 가스 발생이 멈출 때까지 교반하였다. 추출한 다음, 수층을 메틸렌클로라이드 250 ml로 다시 추출하였다. 유기층을 황산마그네슘 (MgSO4)로 건조한 다음, 여과 농축하여 빨간색 액체인 1-클로로-3,4-디하이드로-2-카바알데히드 (1-chloro-3,4- dihydro-2-carbaldehyde) 10.5 g(54.7 mmol, 91.3%)을 수득하였다.
MS(EI) (m/z) : [M+] 192
합성예 1-2. 1-페닐-3,4-디하이드로-2-카바알데히드 합성
Figure PCTKR2014002538-appb-I000028
질소기류 하에서 반응기에 1-클로로-3,4-디하이드로-2-카바알데히드 920 mg(4.78 mmol), 페닐보론산 (phenylbronic acid) 640 mg(5.26 mmol), 테트라부틸암모늄 브로마이드 (tetrabutylammonium bromide) 1.54 g (4.78 mmol), 팔라듐(II) 아세테이트 (Pd(OAc)2) 21.5 mg(0.096 mmol), 탄산칼륨 (K2CO3)수용액을 투입한 다음, 45 ℃에서 3시간 동안 교반하였다. 반응이 완료되면 상온으로 냉각한 다음, 물을 투입하고 층분리 하였다. 수층은 에틸 아세테이트 ml를 투입한 다음, 다시 추출하였다. 유기층을 황산마그네슘 (MgSO4)으로 건조한 다음, 여과 농축하고, 실리카겔 컬럼으로 분리하여 노란색의 고체인 1-페닐-3,4-디하이드로-2-카바알데히(1-phenyl-3,4-dihydro- 2-carbaldehyde) 1.0 g(4.42 mmol, 89.4%)을 수득하였다.
MS(EI) (m/z) : [M+] 234
합성예 1-3. 3-에틴닐-4-페닐-1.2-디하이드로나프탈렌 합성
Figure PCTKR2014002538-appb-I000029
질소기류 하에서 반응기에 디이소프로필아민 (diisopropylamine) 753 ul(5.37 mmol)을 투입한 다음 0 ℃로 냉각하였다. n-부틸리튬 (n-butyllithium) 용액 3.2 ml(5.1 mmol, 1.6 M in hexanes)을 천천히 적가한 후, 10분 동안 교반하여 LDA 용액을 합성하였다. 반응 온도를 -78 ℃로 냉각한 후, (트리메틸실릴)디아조메탄 ((trimethylsilyl)diazomethane) 용액 2.5 ml(5.0 mmol, 2 M in hexane)을 천천히 적가 하였다. 같은 온도에서 30분 동안 교반한 다음, 1-페닐-3,4-디하이드로-2-카바알데히드 1.0 g(4.27 mmol)을 테트라하이드로푸란 (THF) 5 ml에 녹인 용액을 천천히 적가 하였다. 천천히 상온으로 승온한 다음, 3시간 동안 교반하여 반응을 완료하고, 물을 투입하여 반응을 종결하였다. 반응 용액을 층분리 한 다음, 수층을 에틸 아세테이트로 2회 추출하였다. 유기층을 황산마그네슘 (MgSO4)으로 건조한 다음, 여과 농축하고, 전개용매 n-헥산:에틸아세테이트 (95:5)로 실리카겔 컬럼으로 분리하여 무색의 투명 액체인 3-에틴닐-4-페닐-1.2-디하이드로나프탈렌 (3-ethynyl-4-phenyl-1,2-dihydronaphthalene) 778 mg(3.38 mmol, 79.1%)을 수득하였다.
MS(EI) (m/z) : [M+] 230
합성예 1-4. 5,6-디하이드로-벤조[ c ]펜안트렌 합성
Figure PCTKR2014002538-appb-I000030
질소기류 하에서 반응기에 3-에틴닐-4-페닐-1.2-디하이드로나프탈렌 528 mg(2.3 mmol), 플라티늄(II) 클로라이드 (PtCl2) 26.6 mg(0.1 mmol), 톨루엔 10 ml를 투입한 다음, 80 ℃에서 24시간 동안 교반하였다. 반응이 완료되면 감압 증류 하여 용매를 제거한 다음, 전개 용매 n-헥산으로 실리카겔 컬럼 분리하여 흰색의 고체인 5,6-디하이드로-벤조[c]펜안트렌 (5,6-dihydro-benzo[c]phenanthrene 380.1 mg(1.65 mmol, 72.1%)을 수득하였다.
MS(EI) (m/z) : [M+] 230
합성예 1-5. 8-브로모-5,6-디하이드로-벤조[ c ]펜안트렌 합성
Figure PCTKR2014002538-appb-I000031
질소기류 하에서 반응기에 5,6-디하이드로-벤조[c]펜안트렌 10 g(43.4 mmol), 메틸렌클로라이드 100 ml를 투입하였다. 반응 온도를 0 ℃로 냉각한 다음, 브로민 (Br2) 7.63 g(47.7 mmol)을 메틸렌클로라이드 76 ml에 희석시킨 용액을 천천히 적가 하였다. 반응 온도를 상온으로 승온한 후, 6시간 교반하였다. 반응기에 티오황산나트륨 (N2S2O3) 수용액을 투입한 후, 층분리 한 다음, 수층을 메틸렌클로라이드로 추출하였다. 유기층을 황산마그네슘 (MgSO4)으로 건조한 다음, 여과 농축하고, 메틸렌클로라이드와 메탄올로 재결정하여 노란색의 고체인 8-브로모-5,6-디하이드로-벤조[c]펜안트렌 (8-bromo-5,6-dihydro-benzo[c]phenanthrene) 11.3 g(36.6 mmol, 84.2%)을 수득하였다.
MS(EI) (m/z) : [M+] 308
합성예 1-6. 화학식 (6) 합성
Figure PCTKR2014002538-appb-I000032
질소기류 하에서 반응기에 8-브로모-5,6-디하이드로-벤조[c]펜안트렌 1.0 g(3.2 mmol), 10-페닐안트라센-9-일 보론산 (10-phenylanthracen-9-yl boronic acid) 1.1 g(3.9 mmol), 테트라키스(트리페닐포스피노)팔라듐(0) (Pd(PPh3)4) 0.19 g(0.16 mmol), 탄산칼륨 (K2CO3) 1.3 g(9.1 mmol), 톨루엔 10 ml, 테트라하이드로퓨란 (THF) 10 ml, 정제수 2 ml를 투입한 다음, 환류 냉각하였다. 반응이 완료되면, 상온으로 냉각하고, 반응 용액을 층분리 하였다. 수층을 에틸 아세테이트로 2회 추출하였다. 유기층을 황산마그네슘 (MgSO4)으로 건조한 다음, 여과 농축하고, 전개용매 n-헥산:에틸아세테이트 (90:10)로 실리카겔 컬럼 분리하여 흰색의 고체인 8-(10'-페닐안트라센-9'-일)-5,6-디하이드로-벤조[c]펜안트렌 (8-(10'-phenylanthracen-9'-yl)-5,6- dihydro-benzo[c]phenanthrene) 1.2 g(2.5 mmol, 77.2%)을 수득하였다.
MS(EI) (m/z) : [M+] 482
합성예 2. 화학식 (31) 합성
Figure PCTKR2014002538-appb-I000033
합성예 1-6과 동일한 방법으로 합성하여 흰색의 고체인 8-(10'-나프틸안트라센-9'-일)-5,6-디하이드로-벤조[c]펜안트렌 (8-(10'-naphthyl-anthracen- 9'-yl)-5,6-dihydro-benzo[c]phenanthrene) 1.1 g(2.1 mmol, 69.1%)을 수득하였다.
MS(EI) (m/z) : [M+] 532
합성예 3. 화학식 (32) 합성
Figure PCTKR2014002538-appb-I000034
합성예 1-6과 동일한 방법으로 합성하여 흰색의 고체인 8-(10`-(2``- 나프틸)안트라센-9`-일)-5,6-디하이드로-벤조[c]펜안트렌 (8-(10'-(2``- naphthryl)-anthracen-9'-yl)-5,6-dihydro-benzo[c]phenanthrene) 1.3 g(2.4 mmol, 75.2%)을 수득하였다.
MS(EI) (m/z) : [M+] 532
합성예 4. 화학식 (33) 합성
Figure PCTKR2014002538-appb-I000035
합성예 1-6과 동일한 방법으로 합성하여 흰색의 고체인 8-(10'-(9``-펜안트릴)안트라센-9'-일)-5,6-디하이드로-벤조[c]펜안트렌 (8-(10'-(9``- phenanthryl)anthracen-9'-yl)-5,6-dihydro-benzo[c]phenanthrene) 1.2 g(2.0 mmol, 62.7%)을 수득하였다.
MS(EI) (m/z) : [M+] 582
합성예 5. 화학식 (46) 합성
Figure PCTKR2014002538-appb-I000036
합성예 1-6과 동일한 방법으로 합성하여 흰색의 고체인 8-(4'-(10``-페닐안트라센-9``-일)페닐)-5,6-디하이드로-벤조[c]펜안트렌 (8-(4`-(10``- phenylanthracen-9``-yl)phenyl)-5,6-dihydro-benzo[c]phenanthrene) 1.2 g(2.2 mmol, 66.1%)을 수득하였다.
MS(EI) (m/z) : [M+] 559
합성예 6. 화학식 (51) 합성
Figure PCTKR2014002538-appb-I000037
합성예 1-6과 동일한 방법으로 합성하여 흰색의 고체인 8-(3'-(10``-페닐안트라센-9``-일)페닐)-5,6-디하이드로-벤조[c]펜안트렌 (8-(3`-(10``-phenyl- anthracen-9``-yl)phenyl)-5,6-dihydro-benzo[c]phenanthrene) 1.0 g(1.7 mmol, 53.7%)을 수득하였다.
MS(EI) (m/z) : [M+] 559
합성예 7. 화학식 (1) 합성
Figure PCTKR2014002538-appb-I000038
8-브로모-5,6-디하이드로벤조[c]펜안트렌 대신 4-클로로-5,6- 디하이드로벤조[c]펜안트렌 사용하는 것 이외에는 합성예 1-6과 동일한 방법으로 합성하여 연한 연두색 고체인 4-(10-페닐안트라센- 9-일)-5,6-디하이드로-벤조[c]펜안트렌 (4-(10- phenylanthracen-9-yl)- 5,6-dihydrobenzo[c]phenanthrene) 0.8 g(1.7 mmol, 33.7%)을 수득하였다.
MS(EI) (m/z) : [M+]483
합성예 8. 화학식 (8) 합성
Figure PCTKR2014002538-appb-I000039
8-브로모-5,6-디하이드로벤조[c]펜안트렌 대신 10-브로보-5,6- 디하이드로벤조[c]펜안트렌 사용하는 것 이외에는 합성예 1-6과 동일한 방법으로 합성하여 연한 흰색 고체인 10-(10-페닐안트라센- 9-일)-5,6-디하이드로-벤조[c]펜안트렌 (10-(10-phenylanthracen-9-yl)- 5,6-dihydrobenzo[c]phenanthrene) 1.5 g(3.1 mmol, 57.4%)을 수득하였다.
MS(EI) (m/z) : [M+]483
합성예 9. 화학식 (12) 합성
Figure PCTKR2014002538-appb-I000040
8-브로모-5,6-디하이드로벤조[c]펜안트렌 대신 10-브로보-5,6- 디하이드로벤조[c]펜안트렌 사용하는 것 이외에는 합성예 1-6과 동일한 방법으로 합성하여 연한 연두색 고체인 3-(10-(2-나프틸)- 안트라센-9-일)-5,6-디하이드로-벤조[c]펜안트렌 (3-(10-(2-naphthyl)- anthracen-9-yl)-5,6-dihydrobenzo[c]phenanthrene) 1.1 g(2.1 mmol, 43.8%)을 수득하였다.
MS(EI) (m/z) : [M+]533
합성예 10. 화학식 (165) 합성
Figure PCTKR2014002538-appb-I000041
8-브로모-5,6-디하이드로벤조[c]펜안트렌 대신 5-요오드-5,6- 디하이드로벤조[c]펜안트렌 사용하는 것 이외에는 합성예 1-6과 동일한 방법으로 합성하여 연한 연두색 고체인 7-(10-(2-나프틸)- 안트라센-9-일)-5,6-디하이드로-벤조[c]펜안트렌 (7-(10-(2-naphthyl)- anthracen-9-yl)-5,6-dihydrobenzo[c]phenanthrene) 0.9 g(1.7 mmol, 71.7%)을 수득하였다.
MS(EI) (m/z) : [M+]533
합성예 11. 화학식 (191) 합성
Figure PCTKR2014002538-appb-I000042
8-브로모-5,6-디하이드로벤조[c]펜안트렌 대신 2-브로보-5,6- 디하이드로벤조[c]펜안트렌 사용하는 것 이외에는 합성예 1-6과 동일한 방법으로 합성하여 연한 연두색 고체인 2-(10-(2-나프틸)- 안트라센-9-일)-5,6-디하이드로-벤조[c]펜안트렌 (2-(10-(2-naphthyl)- anthracen-9-yl)-5,6-dihydrobenzo[c]phenanthrene) 1.0 g(1.9 mmol, 54.3%)을 수득하였다.
MS(EI) (m/z) : [M+]533
합성예 12. 화학식 (18) 합성
Figure PCTKR2014002538-appb-I000043
질소기류 하에서 반응기에 (7,8-디하이드로벤조[c]펜안트렌-3-일)- 보론산 3.00 g(10.9 mmol), 9,10-디브로모안트라센 1.5 g(4.6 mmol), 테트라키스(트리페닐포스피노)팔라듐(0) (Pd(PPh3)4) 0.21 g(0.2 mmol), 탄산칼륨(K2CO3) 3.8 g(27.4 mmol), 톨루엔 60 ml, 테트라하이드로퓨란(THF) 60 ml, 정제수 12 ml를 투입한 다음, 환류 냉각하였다. 반응이 완료되면, 상온으로 냉각하고, 반응 용액을 층분리 하였다. 수층을 에틸 아세테이트로 2회 추출하였다. 유기층을 황산마그네슘(MgSO4)으로 건조한 다음, 여과 농축하고, 전개용매 n-헥산: 에틸아세테이트 (60:10)로 실리카겔 컬럼 분리하여 흰색의 고체인 9,10-비스(5,6-디하이드로벤조[c]펜안트렌-3-일)안트라센 (9,10-bis- (5,6-dihydrobenzo[c]phenanthren-3-yl)anthracene) 1.2 g(1.9 mmol, 41.5%)을 수득하였다.
MS(EI) (m/z) : [M+]635
합성예 13. 화학식 (183) 합성
Figure PCTKR2014002538-appb-I000044
(7,8-디하이드로벤조[c]펜안트렌-3-일)보론산 대신 (7,8-디하이드로- 벤조[c]펜안트렌-6-일)보론산을 사용하는 것 이외에는 합성예 11과 동일한 방법으로 합성하여 흰색의 고체인 9,10-비스(7,8-디하이드로벤조[c]-펜안트렌-5-일)안트라센 (9,10-bis(7,8-dihydrobenzo[c]phenanthren-5-yl)- anthracene) 0.9 g(1.4 mmol, 31.1%)을 수득하였다.
MS(EI) (m/z) : [M+]635
합성예 14. 화학식 (200) 합성
Figure PCTKR2014002538-appb-I000045
(7,8-디하이드로벤조[c]펜안트렌-3-일)보론산 대신 (7,8-디하이드로- 벤조[c]펜안트렌-6-일)보론산을 사용하는 것 이외에는 합성예 11과 동일한 방법으로 합성하여 흰색의 고체인 9,10-비스(5,6-디하이드로벤조[c]-펜안트렌-2-일)안트라센 (9,10-bis(5,6-dihydrobenzo[c]phenanthren-2-yl)- anthracene) 1.7 g(2.7 mmol, 58.7%)을 수득하였다.
MS(EI) (m/z) : [M+]635
합성예 15-1. 3,8-디브로모-5,6-디하이드로-벤조[c]펜안트렌 합성
Figure PCTKR2014002538-appb-I000046
질소기류 하에서 반응기에 5,6-디하이드로-벤조[c]펜안트렌 10 g(43.4 mmol), 메틸렌클로라이드 100 ml를 투입하였다. 반응 온도를 0 ℃로 냉각한 다음, 브로민 (Br2) 15.26 g(95.4 mmol)을 메틸렌클로라이드 150 ml에 희석시킨 용액을 천천히 적가 하였다. 반응 온도를 상온으로 승온한 후, 6시간 교반하였다. 반응기에 티오황산나트륨 (N2S2O3) 수용액을 투입한 후, 층분리 한 다음, 수층을 메틸렌클로라이드로 추출하였다. 유기층을 황산마그네슘 (MgSO4)으로 건조한 다음, 여과 농축하고, 메틸렌클로라이드와 메탄올로 재결정하여 노란색의 고체인 3,8-디브로모-5,6-디하이드로-벤조[c]펜안트렌 (3,8-dibromo-5,6-dihydro-benzo[c]phenanthrene) 12.0 g(31.0 mmol, 71.4%)을 수득하였다.
MS(EI) (m/z) : [M+] 388
합성예 15. [화학식 203] 합성
Figure PCTKR2014002538-appb-I000047
(7,8-디하이드로벤조[c]펜안트렌-3-일)보론산과 9,10-디브로모안트라센 대신 (10-(2-나프틸)안트라센-9-일)보론산과 3,8-디브로모-5,6-디하이드로- 벤조[c]펜안트렌을 사용하는 것 이외에는 합성예 11과 동일한 방법으로 합성하여 연한 연두색 고체인 3,8-비스(10-(2-나프틸)안트라센-9-일)- 5,6-디하이드로-벤조[c]펜안트렌 (2-(10-(2-naphthyl)anthracen-9-yl)-5,6- dihydrobenzo[c]phenanthrene) 1.2 g(1.4 mmol, 40.0%)을 수득하였다.
MS(EI) (m/z) : [M+]836
합성예 16. 화학식 (131) 합성
Figure PCTKR2014002538-appb-I000048
질소 기류 하에서 반응기에 3,8-디브로모-5,6-디하이드로-벤조 [c]펜안트렌 10 g(25.8 mmol), 9H-carbazole 10.9 g(57.3 mmol), CuI 1.1 g(5.7 mmol), 인산삼칼륨 24.3 g(114.6 mmol), 1,2-디아미노시클로헥산 0.7 g(5.7 mmol), 1,4-디옥산 100 ml를 투입한 다음, 환류 냉각하면서 36시간 동안 교반하였다. 반응이 완료되면 여과한 후, 감압으로 용매를 제거하였다. 반응물을 실리카겔 컬럼 분리하여 밝은 연두색의 고체인 9,9'-(5,6-디하이드로벤조[c]-펜안트렌-3,8-디일)-비스(9H-카바졸)(9,9'-(5,6-dihydrobenzo[c]phenanthrene-3,8-diyl)bis(9H-carbazole) 3.2 g(5.6 mmol, 21.9%)을 수득하였다.
MS(EI) (m/z) : [M+]561
합성예 17. 화학식 (134) 합성
Figure PCTKR2014002538-appb-I000049
합성예 15와 동일한 방법으로 합성하여 밝은 연두색의 고체인 3,3'-(5,6-디하이드로-벤조[c]펜안트렌-3,8-디일)비스(9-페닐-9H-카 바졸) (3,3'-(5,6-dihydrobenzo[c]phenanthrene-3,8-diyl)bis(9- phenyl-9H-carbazole)) 5.4 g(9.5 mmol, 36.7%)을 수득하였다.
MS(EI) (m/z) : [M+]713
합성예 18. 화학식 (147) 합성
Figure PCTKR2014002538-appb-I000050
질소 기류 하에서 반응기에 5,6-디하이드로-벤조[c]펜안트렌 1 g (2.6 mmol), 디페닐아민 1.1 g(6.5 mmol), 팔라듐(II) 아세테이트 0.03 g (0.13 mmol), BINAP 0.08 g(0.13 mmol), sodium tert-butoxide 1.0 g(10.3 mmol), 톨루엔 100 ml를 투입한 다음, 환류 냉각하면서 12시간 동안 교반하였다. 반응이 완료되면 여과한 후, 감압으로 용매를 제거하였다. 반응물을 실리카겔 컬럼 분리하여 밝은 연두색의 고체인 3,8-디(N,N-디페닐아미노)-5,6-디하이드로-벤조[c]펜안트렌 (3,8-di(N,N-diphenylamino)-5,6- dihydro-benzo[c]- phenanthrene) 0.8 g(1.4 mmol, 55.2%)을 수득하였다.
MS(EI) (m/z) : [M+] 565
합성예 19. 화학식 (151) 합성
Figure PCTKR2014002538-appb-I000051
합성예 18과 동일한 방법으로 합성하여 밝은 연두색의 고체인 3,8-디(N,N-디(4`-톨릴)아미노)-5,6-디하이드로-벤조[c]펜안트렌 (3,8-di(N,N-di(4`- tolyl)amino)-5,6-dihydro-benzo[c]phenanthrene) 0.7 g(1.1 mmol, 42.7%)을 수득하였다.
MS(EI) (m/z) : [M+] 621
합성예 20. 화학식 (153) 합성
Figure PCTKR2014002538-appb-I000052
합성예 18과 동일한 방법으로 합성하여 흰색의 고체인 3,8-디(N,N-디(4`-t-부틸페닐)아미노)-5,6-디하이드로-벤조[c]펜안트렌 (3,8-di(N,N-di(4`-tert-butylphenyl)amino)-5,6-dihydro-benzo[c]- phenanthrene) 0.9 g(1.2 mmol, 45.3%)을 수득하였다.
MS(EI) (m/z) : [M+] 790
합성예 21. 화학식 (161) 합성
Figure PCTKR2014002538-appb-I000053
합성예 18과 동일한 방법으로 합성하여 흰색의 고체인 3,8-디(N-페닐-N-2`-나프틸아미노)-5,6-디하이드로-벤조[c]펜안트렌 (3,8-di(N-phenyl- N-2`-naphthylamino)-5,6-dihydro-benzo[c]phenanthrene) 0.9 g(1.32 mmol, 51.1%)을 수득하였다.
MS(EI) (m/z) : [M+] 665
합성예 22. 화학식 (163) 합성
Figure PCTKR2014002538-appb-I000054
합성예 18과 동일한 방법으로 합성하여 밝은 연두색의 고체인 3,8-디(N-페닐-N-(9`,9`-dimethyl-2`-플루오렌닐)아미노)-5,6-디하이드로-벤조[c]펜안트렌 (3,8-di(N-phenyl-N-(9`,9`-dimethyl-2`-fluorenyl)amino)-5,6- dihydro-benzo[c]-phenanthrene) 0.9 g(1.1 mmol, 43.7%)을 수득하였다.
MS(EI) (m/z) : [M+] 797
합성예 23. 화학식 (164) 합성
Figure PCTKR2014002538-appb-I000055
합성예 18과 동일한 방법으로 합성하여 밝은 연두색의 고체인 3,8-디(N-페닐-N-(3`-피리딜)아미노)-5,6-디하이드로-벤조[c]펜안트렌 (3,8-di(N-phenyl-N-(3`-pyridyl)amino)-5,6-dihydro-benzo[c]-phenanthrene) 0.4 g(0.7 mmol, 50.1%)을 수득하였다.
MS(EI) (m/z) : [M+] 567
[실시예] 본 발명에 따른 유기발광소자의 제조
상기 합성예 1 내지 15에서 얻은 화합물을 발광층의 발광 호스트 물질로 사용하였고, 비교 호스트 화합물로 ADN (ADN : 9,10-di(2-naphthyl)- anthracene)을 사용하였으며, 발광층의 도펀트 물질로 BD142 (N6,N12-비스(3,4-디메틸페닐)-N6,N12-디메시틸크리센-6,12-디아민)의 화합물을 이용하여 통상적인 방법에 따라 유기발광소자를 제작하였다.
먼저, 유리 기판에 형성된 1500 Å 두께의 ITO층(애노드) 위에 650 Å 두께의 정공주입층(정공주입층 물질: HI-406(N1,N1'-(비페닐-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민)), 200 Å 두께의 정공수송층(정공수송층 물질: 비스(N-(1-나프틸-n-페닐))벤지딘(α-NPB)), 본 발명에서의 화합물에 BD142 (N6,N12-비스(3,4-디메틸페닐)-N6,N12-디메시틸크리센-6,12-디아민)가 도핑 된 350 Å 두께의 발광층, 200 Å 두께의 전자수송층(전자수송층 물질: ET4(6,6'-(3,4-디메시틸-1,1-디메틸-1H-실올-2,5-디일)디-2,2'-비피리딘)) 및 10 Å 두께의 LiF, 1000Å 두께의 알루미늄 캐소드를 순차적으로 증착시켜 유기발광소자를 제작하였다.
상기 제조된 유기발광소자의 발광특성을 측정하여 하기 표 1에 나타내었다.
표 1
분류 호스트 전압(V) 전류효율(cd/A) 휘도(cd/m2) CIEx CIEy
실시예1 합성예1 5.44 9.44 944 0.135 0.175
실시예2 합성예2 5.59 9.62 962 0.146 0.177
실시예3 합성예3 5.51 9.55 955 0.139 0.178
실시예4 합성예4 5.65 9.43 943 0.140 0.173
실시예5 합성예5 5.66 8.89 889 0.140 0.169
실시예6 합성예6 5.61 8.86 886 0.146 0.168
실시예7 합성예7 5.62 8.53 853 0.141 0.167
실시예8 합성예8 5.55 7.95 795 0.140 0.160
실시예9 합성예9 5.70 9.30 930 0.143 0.172
실시예10 합성예10 5.65 8.98 898 0.142 0.167
실시예11 합성예11 5.65 9.11 911 0.140 0.171
실시예12 합성예12 5.73 9.21 921 0.141 0.169
실시예13 합성예13 5.52 8.88 888 0.140 0.165
실시예14 합성예14 5.50 8.73 873 0.140 0.160
실시예15 합성예15 5.63 9.20 920 0.145 0.188
비교예 ADN 5.75 6.30 630 0.141 0.169
상기 표 1에 나타낸 바와 같이, 실시예 1 내지 15는 비교예 1 보다 전압은 유사하지만, 전류효율 및 휘도는 최대 1.5배 향상되었음을 알 수 있고, 색좌표도 상대적으로 우수하다.
또한, 상기 합성예 18 내지 23 에서 얻은 화합물을 발광층의 발광 도펀트 물질로 사용하였고, 비교 도펀트 물질로 BD142의 화합물을 사용하였으며, 발광층의 발광 호스트로 ADN (ADN : 9,10-di(2- naphthyl)anthracene)을 사용한 것을 제외하고는 상기 실시예와 동일하게 제작하였다.
표 2
분류 도펀트 전압(V) 전류효율(cd/A) 휘도(cd/m2) CIEx CIEy
실시예18 화합물18 4.64 5.41 541 0.143 0.111
실시예19 화합물19 4.34 5.78 578 0.146 0.111
실시예20 화합물20 4.55 5.94 594 0.139 0.122
실시예21 화합물21 4.88 6.43 643 0.140 0.124
실시예22 화합물22 4.72 5.79 579 0.140 0.123
실시예23 화합물23 4.11 5.86 586 0.146 0.101
비교예 BD142 5.75 6.30 630 0.141 0.169
상기 표 2에 나타낸 바와 같이, 실시예 18 내지 23은 비교예보다 구동전압이 우수하다. 전류효율은 유사하거나 낮은 특성을 보이고 있지만, 이는 색좌표에서 CIEy 값 확인으로 알 수 있듯이 단파장 영역으로의 이동에 따른 결과이며, 환산효율을 고려하면 최대 1.6배 향상된 특성을 보이고 있다.
상기 실시예에 따른 유기발광소자의 결과인 표 1과 2에 따르면 본 발명의 신규한 벤조펜안트렌 화합물을 이용하여 구동 전압, 발광 효율 및 색좌표 등의 특성이 우수한 유기발광소자를 제작할 수 있다.
본 발명의 신규한 벤조펜안트렌 유도체 화합물을 이용한 유기발광소자는 구동 전압, 발광 효율 및 색순도 등의 특성이 우수한 효과가 있다.

Claims (8)

  1. 하기 화학식 1로 표시되는 화합물:
    [화학식 1]
    Figure PCTKR2014002538-appb-I000056
    상기 화학식 1에서,
    R1 내지 R14는 각각 독립적으로 치환 또는 비치환의 탄소수 1 내지 20의 알킬기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로 아릴기, 치환 또는 비치환의 탄소수 1 내지 30의 알콕시기,　치환 또는 비치환의 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 헤테로아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환의 알케닐기, 치환 또는 비치환의 알키닐기, 시아노기, 할로겐기, 중수소 및 수소로 이루어진 군에서 선택된다.
  2. 제1항에 있어서,
    상기 화합물이 하기 화학식으로 표시되는 화합물 중 하나인 것을 특징으로 하는 화합물:
    Figure PCTKR2014002538-appb-I000057
    Figure PCTKR2014002538-appb-I000058
    Figure PCTKR2014002538-appb-I000059
    Figure PCTKR2014002538-appb-I000060
    Figure PCTKR2014002538-appb-I000061
    Figure PCTKR2014002538-appb-I000062
    Figure PCTKR2014002538-appb-I000063
    Figure PCTKR2014002538-appb-I000064
    Figure PCTKR2014002538-appb-I000065
    Figure PCTKR2014002538-appb-I000066
    Figure PCTKR2014002538-appb-I000067
    Figure PCTKR2014002538-appb-I000068
    Figure PCTKR2014002538-appb-I000069
    Figure PCTKR2014002538-appb-I000070
    Figure PCTKR2014002538-appb-I000071
    Figure PCTKR2014002538-appb-I000072
    Figure PCTKR2014002538-appb-I000073
    Figure PCTKR2014002538-appb-I000074
    Figure PCTKR2014002538-appb-I000075
    Figure PCTKR2014002538-appb-I000076
    Figure PCTKR2014002538-appb-I000077
    Figure PCTKR2014002538-appb-I000078
    Figure PCTKR2014002538-appb-I000079
  3. 하기 모식도의 단계를 포함하는 것을 특징으로 하는 제1항 기재의 화학식 1의 화합물을 제조하는 방법:
    [모식도]
    Figure PCTKR2014002538-appb-I000080
  4. 제1항 기재의 화학식 1의 화합물을 포함하는 것을 특징으로 하는 유기발광소자.
  5. 제4항에 있어서,
    제1항의 화합물을 상기 애노드와 캐소드 사이의 정공주입층(HIL)또는 정공수송층(HTL) 또는 발광층(EML)에 포함하는 것을 특징으로 하는 유기발광소자.
  6. 제5항에 있어서,
    상기 애노드와 캐소드 사이에 발광층, 정공주입층, 정공수송층, 전자저지층, 전자수송층, 전자주입층, 정공저지층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기발광소자.
  7. 제4항에 있어서,
    상기 애노드와 캐소드 사이의 발광층, 정공주입층, 정공수송층, 전자저지층, 전자수송층, 전자주입층, 정공저지층으로부터 선택된 하나 이상의 층은 진공증착방식 또는 용액공정에 의하여 형성되는 것을 특징으로 하는 유기발광소자.
  8. 제4항에 있어서,
    상기 유기발광소자는 표시소자, 디스플레이 소자, 조명소자용인 것을 특징으로 하는 유기발광소자.
PCT/KR2014/002538 2013-03-26 2014-03-26 신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자 Ceased WO2014157933A1 (ko)

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JP2016505394A JP2016521261A (ja) 2013-03-26 2014-03-26 新規なベンゾフェナントレン誘導体化合物およびこれを用いた有機発光素子

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KR1020140034898A KR101527873B1 (ko) 2013-03-26 2014-03-25 신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009263260A (ja) * 2008-04-23 2009-11-12 Tokuyama Corp スピロ化合物の製造方法
JP2010270092A (ja) * 2009-05-25 2010-12-02 Tokuyama Corp アセチル化合物、該アセチル化合物の製造方法、および該アセチル化合物を使用したナフトール化合物の製造方法

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JP2009263260A (ja) * 2008-04-23 2009-11-12 Tokuyama Corp スピロ化合物の製造方法
JP2010270092A (ja) * 2009-05-25 2010-12-02 Tokuyama Corp アセチル化合物、該アセチル化合物の製造方法、および該アセチル化合物を使用したナフトール化合物の製造方法

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PADWA, ALBERT ET AL.: "Synthesis and ring-opening reactions in the 1,3'-bicyclopropenyl series", J. ORG. CHEM., vol. 49, no. 5, 1984, pages 856 - 862 *

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