KR20070115588A - Blue light emitting compound and organic electroluminescent device using the same - Google Patents

Blue light emitting compound and organic electroluminescent device using the same Download PDF

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KR20070115588A
KR20070115588A KR20070020640A KR20070020640A KR20070115588A KR 20070115588 A KR20070115588 A KR 20070115588A KR 20070020640 A KR20070020640 A KR 20070020640A KR 20070020640 A KR20070020640 A KR 20070020640A KR 20070115588 A KR20070115588 A KR 20070115588A
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organic
layer
mol
electroluminescent device
blue light
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KR100874749B1 (en )
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유선근
이상해
임동수
제종태
황석광
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에스에프씨 주식회사
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
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    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5012Electroluminescent [EL] layer
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5048Carrier transporting layer
    • H01L51/5056Hole transporting layer
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5048Carrier transporting layer
    • H01L51/5072Electron transporting layer
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5088Carrier injection layer
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5088Carrier injection layer
    • H01L51/5092Electron injection layer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02BCLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
    • Y02B20/00Energy efficient lighting technologies
    • Y02B20/30Semiconductor lamps, e.g. solid state lamps [SSL] light emitting diodes [LED] or organic LED [OLED]
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/917Electroluminescent

Abstract

A blue light emitting compound is provided to ensure excellent blue color purity and brightness equal to or higher than the conventional light emitting compounds. A blue light emitting compound has a structure represented by the following formula 1. In the formula, each of Ar1 and Ar2 is the formula (a) and the formula (b), and each of A1 and A2 is a C6-14 aryl group or N, S, or O-containing C4-19 heteroaryl group unsubstituted or substituted with a C1-10 alkyl group, C1-10 alkoxy group, or C1-10 heteroalkyl group, wherein each of the substituents is a C1-10 alkyl group, C1-10 alkoxy group, C1-10 alkylamino group, C1-10 alkylsilyl group, C6-14 aryl group, C4-19 heteroaryl group containing N, S, or O, cyano group, or halogen.

Description

청색발광화합물 및 이를 이용한 유기전계발광소자{Blue light emitting compound and organic electroluminescent device using the same} A blue light-emitting compound and an organic light emitting device using the same {Blue light emitting compound and organic electroluminescent device using the same}

도 1은 본 발명의 일 실시예에 따른 유기전계발광소자의 개략도이다. 1 is a schematic view of an organic EL device according to an embodiment of the present invention.

<도면의 주요부분에 대한 부호의 설명> <Description of the Related Art>

10: 기판 20: 애노드 10: substrate 20: anode

30: 정공주입층 40: 정공수송층 30: hole injection layer 40: hole transport layer

50: 유기발광층 60: 전자수송층 50: organic emission layer 60: electron transport layer

70: 전자주입층 80: 캐소드 70: the electron injection layer 80: cathode

본 발명은 유기전계발광소자에 관한 것으로서, 더욱 상세하게는 청색의 색순도가 우수한 청색발광화합물 및 이를 이용하여 제조된 유기전계발광소자에 관한 것이다. The present invention relates to an organic electroluminescent device, and more particularly relates to an organic electroluminescent device manufactured by the color purity of the blue color superior blue light-emitting compound and a means.

최근 표시장치의 대형화에 따라 공간 점유가 작은 평면표시소자의 요구가 증 대되고 있는데, 대표적인 평면표시소자인 액정 디스플레이는 기존의 CRT에 비해 경량화가 가능하다는 장점은 있으나, 시야각(viewing angle)이 제한되고 배면 광(back light)이 반드시 필요하다는 등의 단점을 갖고 있다. The recent display device larger the space occupied by the needs of a small flat display device is increased for in accordance with, an exemplary flat display device is a liquid crystal display, but the advantage of being lightweight is possible compared to the conventional CRT, the viewing angle (viewing angle) is limited and has a disadvantage such that the necessary back light (back light). 이에 반하여, 새로운 평면표시소자인 유기전계발광소자 (organic light emitting diode:OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고, 액정 디스플레이에 비해 경박, 단소해질 수 있으며, 빠른 응답 속도 등의 장점을 가지고 있다. On the other hand, new flat panel display device is an organic electroluminescent device (organic light emitting diode: OLED) is a display using self-emission phenomenon, large viewing angle, can be chancel trifling, in comparison to a liquid crystal display, the advantages of quick response speed to have.

대표적 유기전계발광소자는 1969년 구르니(Gurnee)에 의해서 공지(US3,172,862, US3,173,050)된 이후, 그 성능상의 한계로 인해 다양한 용도에의 사용이 제한되어 왔으나, 1987년 이스트만 코닥사 (Eastman Kodak co.)의 다층 구조의 유기 발광 다이오드 발표 (CW Tang et al., Appl. Phys. Lett ., 51, 913(1987); J. Applied Phys., 65, 3610(1989)) 이 후, 기존의 문제점을 극복하면서 빠른 속도의 발전하여 왔다. Representative organic electroluminescent device since the known (US3,172,862, US3,173,050) by Gurney (Gurnee) 1969 years, due to the performance limitations wateuna restricted to the use of a variety of applications, Eastman Kodak Company 1987 ( released the organic light emitting diode of a multi-layer structure of the Eastman Kodak co) (CW Tang et al, Appl Phys Lett, 51, 913 (1987....);.. J. Applied Phys, 65, after the 3610 (1989)), to overcome the existing problems has been to develop a rapid pace. 현재 유기전계발광소자는 플라즈마 디스플레이 패널(PDP)이나 무기전계발광소자 디스플레이에 비해 낮은 구동전압(예, 10V이하), 넓은 시야각, 고속 응답성, 고 콘트라스트(contrast) 등의 뛰어난 특징을 갖게됨으로서, 그래픽 디스플레이의 픽셀(pixel), 텔레비전 영상 디스플레이나 표면광원(surface light source)의 픽셀로서 사용될 수 있으며, 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있고, 매우 얇고 가볍게 만들 수 있으며, 색감이 좋기 때문에 차세대 평면 디스플레이(flat panel display: FPD)에 적합한 소자로 부상하고 있다. Current organic electroluminescent device by being given the distinctive features, such as a plasma display panel (PDP) or an inorganic electroluminescent low driving voltage compared to the light-emitting device display (for example, 10V or less), wide viewing angle, high-speed responsiveness, high contrast (contrast), be used as the pixels of the pixel (pixel), a television image display or a surface light source (surface light source) of the graphical display, and it is possible to form an element also on the wheel (flexible) a transparent substrate that can, can create a very thin and light, color because they are the next-generation flat-panel display: emerging as element suitable for (flat panel display FPD).

이러한 유기전계발광소자는 정공 주입 전극(양극)인 제 1전극(anode)과 전자 주입 전극 (음극)인 제 2전극(cathode) 사이에 형성된 유기 발광층에 각각 전자와 정공을 주입하면 전자와 정공이 결합하여 쌍을 이루어 생성된 엑시톤(exciton)이 여기 상태로부터 기저 상태로 떨어지면서 소멸하여 발광하는 소자로서, 최근에는 풀-컬러(full-color) 디스플레이에의 응용이 기대되고 있다. When such an organic EL device, respectively inject electrons and holes into the organic light emitting layer formed between a hole injection electrode (anode) of the first electrode (anode) and an electron injection electrode (cathode), a second electrode (cathode), electrons and holes a device for coupling to the exciton (exciton) made of generating a pair of light emission to decay to fall to the ground state from the excited state, in recent years, full-is expected application of a color (full-color) display. 이처럼 풀-컬러(full-color)를 구현하기 위해서는, 녹색(green), 적색(red), 청색(blue)의 3원색의 발광을 나타내는 화소를 패널 위에 배열할 필요가 있는데, 그 방식으로는 i) 청색, 녹색, 적색의 발광을 나타내는 3종류의 유기발광소자를 배열하는 방법, ii) RGB의 혼색인 백색발광을 나타내는 소자로부터의 발광을 컬러 필터를 통해 3원색으로 분리하는 방법 및 iii) 청색발광을 나타내는 유기발광소자로부터의 발광을 형광발광원으로 이용하여 녹색 및 적색의 발광으로 변환시키는 방법 등이 제안되고 있는데, 어느 경우라도 청색 발광은 필수적이며 고휘도, 고효율 및 고색순도의 청색발광물질에 대한 필요성이 절실해지고 있다. Thus, the pull-in order to implement a color (full-color), there is a green (green), red (red), a pixel representing the three primary colors of light emission of the blue color (blue) to be arranged on the panel, the method include i ) blue, green, and how to arrange the three types of organic light-emitting element showing a flashing red, ii) a method and iii separating the light emitted from the element showing a mixed color of the white light emission of RGB into three primary colors through a color filter) blue the light emitted from the organic light-emitting device showing a light-emitting fluorescent there and a method for converting light emission with source emission in the green and red using the have been proposed, either case the blue light emission is required, and a blue light emitting material having high brightness, high efficiency and high chromatic purity this need has become urgent for.

미국등록특허공보 제US 6,455,720호에는 청색발광물질로서, 2,2-(디아릴)비닐포스핀 (2,2-(Diarlyl)vinylphosphine)이 개시되어 있고, 대한민국공개특허공보 제KR 2002-0070333호에는 중심부는 디페닐안트라센 구조를 가지며, 아릴기가 말단에 치환된 청색 발광 화합물 및 이를 이용한 유기전계발광소자가 개시되어 있지만 발광효율 및 휘도가 충분하지 않다는 문제점이 있었다. US Patent No. US 6,455,720 discloses a blue light emitting material, 2,2- (diaryl) vinylphosphine (2,2 (Diarlyl) vinylphosphine) This is disclosed, Republic of Korea KR-A-2002-0070333 No. in the center is a diphenylmethane having an anthracene structure, there is a problem in the aryl group does disclose a blue light-emitting compound and an organic light emitting device using the same substitution at the terminal, but there is insufficient light emission efficiency and brightness.

한편, 미국등록특허공보 제US 6852429호, 대한민국공개특허공보 제2005-0107809호 및 제2006-0006760호에는 치환된 피렌계 화합물을 이용한 유기전계발광소자가 개시되어 있으나, 청색의 색순도가 낮아서 진한 청색(deep blue)의 구현이 어렵기 때문에 천연색의 풀컬러 디스플레이를 구현하는데 문제점이 있었다. On the other hand, US Patent Publication No. US 6852429 call, the Republic of Korea Patent Application Publication No. 2005-0107809 and No. 2006-0006760 discloses substituted pyrene-based compounds, but the organic electroluminescent device is disclosed with, the color purity of the blue color low dark blue there is a problem to realize a full color display of multi-colored, because the implementation of a (deep blue) difficult.

따라서, 본 발명이 이루고자 하는 기술적 과제는 청색의 색순도가 우수한 청색발광화합물을 제공하는 것이다. Accordingly, the object of the present invention is that the color purity of blue color provides a superior blue light-emitting compound.

본 발명이 이루고자 하는 두 번째 기술적 과제는 상기 청색발광화합물을 이용한 유기전계발광소자를 제공하는 것이다. The second object of the present invention is to provide an organic electroluminescent device using the blue light-emitting compound.

본 발명은 상기 첫 번째 기술적 과제를 달성하기 위하여, For the invention to accomplish the above first aspect of the present invention,

하기 화학식 1의 청색발광화합물을 제공한다. To provide a blue light-emitting compound of the formula (I).

Figure 112007017564149-PAT00001

(상기 식에서, Ar 1 과 Ar 2 는 각각 (Wherein, Ar 1 and Ar 2 are each

Figure 112007017564149-PAT00002
또는 or
Figure 112007017564149-PAT00003
이고 ego

A 1 과 A 2 는 각각 탄소수 1∼10의 알킬기, 탄소수 1∼10의 알콕시기, 탄소수 1∼10의 헤테로 알킬기, 치환되거나 치환되지 않은 탄소수 6∼14의 아릴기 또는 치환되거나 치환되지 않은 탄소수 4∼19의 N, S, O을 포함하는 헤테로 아릴기이고, 상기 치환기는 각각 탄소수 1∼10의 알킬기, 탄소수 1∼10의 알콕시기, 탄소수 1∼10의 알킬아미노기, 탄소수 1∼10의 알킬실릴기, 탄소수 6∼14의 아릴기, 탄소수 4∼19의 N, S, O을 포함하는 헤테로 아릴기, 시아노기 또는 할로겐임.) A 1 and A 2 are each a carbon number of 1 to 10 carbon atoms that is not an alkyl group, having 1 to 10 carbon atoms in the alkoxy group, a C1-10 heteroaryl group, a substituted or an aryl group having 6 to 14 carbon atoms which is unsubstituted or substituted or a substituted 4 a heteroaryl group containing ~19 of N, S, O, wherein the substituents are each optionally substituted alkoxy group of the alkyl group having 1 to 10 carbon atoms, having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, alkyl of 1 to 10 carbon atoms silyl group, a heteroaryl group, a cyano group or a halogen Im containing N, S, O of the aryl group, having a carbon number of 4-19 having a carbon number of 6-14.)

본 발명의 일 실시예에 의하면 상기 청색발광화합물은 하기 화학식 2로 표시되는 군에서 선택된 어느 하나일 수 있다. According to one embodiment of the present invention, the blue light-emitting compound may be any one selected from the group represented by the formula (2) below.

Figure 112007017564149-PAT00004
, ,

BD1 BD1

Figure 112007017564149-PAT00005
, ,

BD2 BD2

Figure 112007017564149-PAT00006
, ,
Figure 112007017564149-PAT00007
, ,

BD3 BD4 BD3 BD4

Figure 112007017564149-PAT00008
, ,
Figure 112007017564149-PAT00009
, ,

BD5 BD6 BD5 BD6

Figure 112007017564149-PAT00010
, ,
Figure 112007017564149-PAT00011
, ,

BD7 BD8 BD7 BD8

Figure 112007017564149-PAT00012
, ,
Figure 112007017564149-PAT00013
, ,

BD9 BD10 BD9 BD10

Figure 112007017564149-PAT00014
, ,
Figure 112007017564149-PAT00015
, ,

BD11 BD12 BD11 BD12

Figure 112007017564149-PAT00016
, ,
Figure 112007017564149-PAT00017
, ,

BD13 BD14 BD13 BD14

Figure 112007017564149-PAT00018
, ,
Figure 112007017564149-PAT00019
, ,

BD15 BD16 BD15 BD16

Figure 112007017564149-PAT00020
, ,
Figure 112007017564149-PAT00021

BD17 BD18 BD17 BD18

Figure 112007017564149-PAT00022
, ,
Figure 112007017564149-PAT00023

BD19 BD20 BD19 BD20

Figure 112007017564149-PAT00024
, ,
Figure 112007017564149-PAT00025

BD21 BD22 BD21 BD22

Figure 112007017564149-PAT00026
, ,
Figure 112007017564149-PAT00027

BD23 BD24 BD23 BD24

Figure 112007017564149-PAT00028
, ,
Figure 112007017564149-PAT00029

BD25 BD26 BD25 BD26

Figure 112007017564149-PAT00030
, ,
Figure 112007017564149-PAT00031

BD27 BD28 BD27 BD28

Figure 112007017564149-PAT00032
, ,
Figure 112007017564149-PAT00033

BD29 BD30 BD29 BD30

Figure 112007017564149-PAT00034
, ,
Figure 112007017564149-PAT00035

BD31 BD32 BD31 BD32

Figure 112007017564149-PAT00036
, ,
Figure 112007017564149-PAT00037

BD33 BD34 BD33 BD34

Figure 112007017564149-PAT00038
, ,
Figure 112007017564149-PAT00039

BD35 BD36 BD35 BD36

Figure 112007017564149-PAT00040
, ,
Figure 112007017564149-PAT00041

BD37 BD38 BD37 BD38

Figure 112007017564149-PAT00042
, ,
Figure 112007017564149-PAT00043

BD39 BD40 BD39 BD40

Figure 112007017564149-PAT00044
, ,
Figure 112007017564149-PAT00045

BD41 BD42 BD41 BD42

본 발명의 바람직한 실시예에 의하면, 상기 청색발광화합물은 하기 화학식 3으로 표시되는 군에서 선택된 어느 하나일 수 있다. According to a preferred aspect of the present invention, the blue light-emitting compound may be any one selected from the group represented by the formula (3) below.

Figure 112007017564149-PAT00046
, ,

BD1 BD1

Figure 112007017564149-PAT00047

BD2 BD2

Figure 112007017564149-PAT00048
, ,
Figure 112007017564149-PAT00049

BD7 BD9 BD7 BD9

Figure 112007017564149-PAT00050
, ,
Figure 112007017564149-PAT00051

BD17 BD39 BD17 BD39

본 발명은 상기 두 번째 기술적 과제를 달성하기 위하여, For the invention to accomplish the above second aspect of the present invention,

애노드, 유기발광층 및 캐소드를 포함하는 유기전계발광소자에 있어서, 상기 유기발광층은 상기 화학식 1로 표시되는 청색발광화합물을 포함하는 유기전계발광소자를7 제공한다. In the organic electroluminescent device comprising an anode, an organic emission layer and the cathode, the organic light-emitting layer 7 it is provided an organic electroluminescent device including a blue light-emitting compound represented by the formula (1).

본 발명에 따른 유기전계발광소자는 상기 유기발광층에 하기 화학식 4로 표시되는 호스트화합물을 더 포함할 수 있다. The organic EL device according to the present invention may further contain a host compound to the organic light-emitting layer represented by the formula (4).

Figure 112007017564149-PAT00052

BH-1 BH-1

또는 or

Figure 112007017564149-PAT00053

BH-2 BH-2

본 발명에 따른 유기전계발광소자는 상기 애노드와 상기 유기발광층 사이에 정공수송층이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자 수송층이 추가로 적층되어 있는 것일 수 있다. The organic electroluminescent device according to the invention may be one that is a hole transporting layer, and is further laminated to, an electron transporting layer is further laminated in between the cathode and the organic emission layer between the anode and the organic emission layer.

또한, 상기 정공수송층의 하부에 정공주입층이 더 적층되어 있는 것일 수 있다. In addition, it may be one that is a hole injection layer further laminated on a lower portion of the hole transport layer.

또한, 상기 전자수송층의 상부에 전자주입층이 더 적층되어 있는 것일 수 있다. In addition, it may be one that is an electron injection layer is further stacked on top of the electron transport layer.

본 발명의 또 다른 실시예에 의하면, 상기 정공수송층은 N,N'-비스(3-메틸페닐)-N,N'-디페닐 -[1,1-비페닐]-4,4'- 디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD)을 포함하는 것일 수 있다. According to a further embodiment of the invention, the hole transporting layer is N, N'- bis (3-methylphenyl) -N, N'- diphenyl- [1,1-biphenyl] -4,4'-diamine ( It may be one containing TPD) or N, N'- di (naphthalene-1-yl) -N, N'- diphenyl benzidine (α-NPD).

본 발명의 바람직한 실시예에 의하면, 상기 정공주입층은 CuPc, TCTA 또는 m-MTDATA을 포함하는 것일 수 있다. According to a preferred aspect of the present invention, the hole injection layer may be one containing CuPc, TCTA, or m-MTDATA.

이하, 본 발명을 더욱 상세하게 설명한다. A detailed explanation follows below with more detail the present invention.

본 발명에 따른 청색발광화합물은 피렌 유도체의 페닐치환기에 시아노기가 치환됨으로 인해서 색순도를 향상시킬 수 있다는 것을 특징으로 한다 . A blue light-emitting compound according to the invention is characterized in that due doemeuro the cyano group substituted on the phenyl substituent of pyrene derivatives to improve the color purity. 일반적으로 전기음성도가 큰, 다양한 전자끌게(electron-withdrawing group)을 도입하게 되면 색순도가 향상되지만, 효율이 대폭 감소하게 되기 때문에 청색 발광화합물로 사용하기가 불가능한 반면, 시아노기를 치환하는 때에는 효율이 유지되면서도 색순도 향상의 효과를 가져올 수 있다는 장점이 있다. In general, the color purity is improved When introducing the electronegativity of a large, diverse electron withdrawing (electron-withdrawing group), but, on the other hand, since the efficiency is greatly reduced impossible to use a blue light-emitting compound, the efficiency, when substituting a cyano group this has the advantage of keeping while being able to get the effect of improving color purity.

본 발명에 따른 유기전계발광소자는 상기 화학식 1로 표시되는 청색발광화합물을 포함하는 유기발광층과 애노드 및 캐소드를 포함하며, 상기 청색발광화합물의 색순도가 우수하기 때문에 풀컬러 디스플레이의 구현이 가능하다는 것을 특징으로 한다. The organic electroluminescent device according to the invention that includes an organic light-emitting layer and the anode and the cathode including a blue light-emitting compound represented by the formula (1), since the color purity of the blue light-emitting compound solid can be a full-color display implemented It characterized.

본 발명에 따른 유기전계발광소자는 상기 유기발광층에 상기 화학식 4로 표시되는 안트라센계 호스트화합물을 더 포함할 수 있다. The organic EL device according to the present invention may further include an anthracene-based compound represented by the host in the organic light-emitting layer by the above formula (4). 상기 발광층에 상기 안트라센계 화합물이 더 포함되는 경우에는 본 발명에 따른 피렌 유도체는 게스트 재료로서의 기능을 하고, 상기 안트라센계 화합물은 호스트 재료로서의 기능을 하게 된다. When the anthracene-based compound is further included in the emission layer, the pyrene derivatives according to the invention functions as a guest material, and the anthracene-based compound is a function as a host material. 즉, 상기 안트라센계 화합물의 광흡수 파장은 상기 피렌 유도체의 광흡수 파장보다 단파장측에 존재하며, 상기 안트라센계 화합물의 주발광파장은 상기 피렌 유도체의 광흡수 파장과 거의 일치하기 때문에, 양자가 유기발광층 내에 함께 존재하게 되면 호스트 재료는 여기 에너지를 게스트 재료로 전달시키면서 자체적으로 발광하지 않고 기저상태로 돌아가고, 여기 상태가 된 게스트 재료만이 여기 에너지를 청색광으로 발광하기 때문에 청색광의 발광효율이 우수해진다는 장점을 갖게 된다. In other words, the light absorption wavelength of the anthracene-based compound because it is present on the short wavelength side than the light absorption wavelength of the pyrene derivatives, bowls light wavelength of the anthracene-based compound is almost the same as the light absorption wavelength of the pyrene derivatives, both the organic light-emitting layer When present together in a host material is here to go back to the ground state without self-emit light while delivering energy to the guest material, the only guest material, an excited state is becomes the luminous efficiency of the blue light excellent because the light-emitting the excitation energy in the blue light It will have the advantage. 또한, 일반적으로 박막 중에 발광 분자가 단독 또는 고농도로 존재하는 경우에는 발광 분자까리 접근함으로써 발광 분자 사이에서 상호작용이 일어나고 농도소광 이라고 불리우는 발광 효율 저하 현상이 발생할 수 있게 되지만, 상기 유기발광층 내에 호스트 화합물을 함께 사용하게 되면 게스트 화합물이 비교적 저농도로 분산될 수 있으므로 상기와 같은 농도 소광 현상을 효과적으로 억제할 수 있다는 장점도 있다. Further, if a general light-emitting molecules in the thin film exist alone or in high concentration is however able to cause an interaction is occurring, concentration quenching said called luminous efficiency degradation between the light emitting molecules by accessing a light emitting molecule to edge, the host compound in the organic light-emitting layer When used together, because the guest compound can be dispersed at a relatively low concentration it has the advantage that it can effectively suppress the concentration quenching phenomenon as described above.

본 발명에 따른 유기전계발광소자는 상기 애노드와 상기 유기발광층 사이에 정공수송층(HTL: Hole Transport Layer)이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층(ETL: Electron Transport Layer)이 추가로 적 층되어 있는 것일 수 있는데, 상기 정공수송층은 애노드로부터 정공을 주입하기 쉽게 하기 위하여 적층되는 것으로서, 상기 정공수송층의 재료로는 이온화 포텐셜이 작은 전자공여성 분자가 사용되는데, 주로 트리페닐아민을 기본골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다. The organic EL device according to the present invention, a hole transport layer between the anode and the organic emission layer (HTL: Hole Transport Layer) may be laminated to additional, an electron transporting layer between the cathode and the organic emission layer (ETL: Electron Transport Layer) There may be, which is laminated to the addition, the hole transport layer as laminated in order to easily inject holes from the anode, a material for the above hole transporting layer is used that is less electron-donating molecular ionization potential, primarily triphenylamine there is a widely used diamine, triamine or tetra-amine derivatives according to the basic skeleton. 본 발명에서도 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는 것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐 -[1,1-비페닐]-4,4'- 디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등을 사용할 수 있다. In one of the present invention it will be commonly used in the art as a material of the hole transport layer is not particularly limited, for example, N, N'- bis (3-methylphenyl) -N, N'- diphenyl-1 , and the like may be used 1-biphenyl] -4,4'-diamine (TPD) or N, N'- di (naphthalene-1-yl) -N, N'- diphenyl benzidine (α-NPD).

상기 정공수송층의 하부에는 정공주입층(HIL: Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 하기 화학식 5에 열거되어 있는 CuPc 또는 스타버스트(Starburst)형 아민류인 TCTA, m-MTDATA 등을 사용할 수 있다. The bottom of the hole transport layer is a hole injection layer: a (HIL Hole Injecting Layer) There additionally further be laminated, and be of use it is not particularly limited to the hole injection layer material is also commonly used in the art, e. It can be used to contain a CuPc or a starburst (starburst) type amines of TCTA, m-MTDATA, such as listed in the general formula (5).

Figure 112007017564149-PAT00054

CuPc, CuPc,

Figure 112007017564149-PAT00055
Figure 112007017564149-PAT00056

TCTA, m -MTDATA TCTA, m -MTDATA

또한, 본 발명에 따른 유기전계발광소자에 사용되는 상기 전자수송층은 캐소드로부터 공급된 전자를 유기발광층으로 원활히 수송하고 상기 유기발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다. Further, the opportunity for the recombination in the light emitting layer by the electron transport layer used in the organic EL device according to the present invention smoothly transport the supplied electrons from the cathode to the organic light emitting layer and suppress transport of holes have not combined in the organic emission layer It serves to increase. 상기 전자수송층 재료로는 당업계에서 통상적으로 사용되는 것이면 특별히 제한되지 않고 사용할 수 있음은 물론이며, 예를 들어, 옥사디아졸 유도체인 PBD, BMD, BND 또는 Alq 3 등을 사용할 수 있다. In the above electron transport material it may be used without particular limitation as long as it is commonly used in the art as well and, for example, can be used such as oxadiazole derivatives of PBD, BMD, BND, or Alq 3.

한편 상기 전자수송층의 상부에는 캐소드로 부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선 시키는 기능을 수행하는 전자주입층(EIL: Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당업계에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예를 들어, LiF, NaCl, CsF, Li 2 O, BaO 등의 물질을 이용할 수 있다. The electron injection layer to a top of the electron transport layer has haejueo facilitates injection of electrons from the cathode serving to ultimately improve the power efficiency as: a (EIL Electron Injecting Layer) There may be further laminated, and the electron injection layer material also can be used without particular limitation as long as it is commonly used in the art, for example, it is possible to use a material such as LiF, NaCl, CsF, Li 2 O, BaO.

도 1은 본 발명의 유기전계발광 소자의 구조를 나타내는 단면도이다. 1 is a cross-sectional view showing the structure of the organic EL device of the present invention. 본 발명에 따른 유기발광 다이오드는 애노드(20), 정공수송층(40), 유기발광층(50), 전 자수송층(60) 및 캐소드(80)을 포함하며, 필요에 따라 정공주입층(30)과 전자주입층(70)을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다. The organic light emitting diode according to the present invention comprises an anode 20, a hole transport layer 40, an organic emission layer 50, electronic transport layer 60 and a cathode 80, a hole injection layer 30, as needed It may further include an electron injection layer 70, and that in addition is also possible to further form an intermediate layer on the first floor or the second floor, it is also possible to further form a hole blocking layer or an electron blocking layer.

도 1을 참조하여 본 발명의 유기전계발광소자 및 그 제조 방법에 대하여 살펴보면, 다음과 같다. Referring to Figure 1, looking for the organic EL device and a manufacturing method of the present invention, as follows. 먼저 기판(10) 상부에 애노드 전극용 물질을 코팅하여 애노드(20)를 형성한다. First, the coating material for an anode electrode on the upper substrate 10 to form anode 20. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. Here substrate 10 is a transparency for a conventional use of the substrate used in the organic EL device, surface smoothness, ease of handling and the excellent organic substrate or a transparent plastic substrate, water resistance is preferred. 그리고 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용한다. And a material for the anode is transparent, use of high conductivity is indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or the like. 상기 애노드(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. To form the anode 20, the hole injection layer material on the upper electrodes vacuum deposited or spin-coated to a hole injection layer 30. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다. Then to form the hole transport layer 40 by vacuum thermal deposition or spin-coating a hole transport layer material on top of the hole injection layer 30. 이어서, 상기 정공수송층(40)의 상부에 유기발광층(50)을 적층하고 상기 유기발광층(50)의 상부에 선택적으로 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. Then, the upper Alternatively (not shown), a hole blocking layer on the hole transport layer 40 is laminated an organic light-emitting layer 50 to the upper and the organic emission layer 50 in the form a thin film as a vacuum evaporation method, or a spin coating method can do. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. The hole blocking layer serves to avoid the problem by the HOMO level using very low because the material, the service life and efficiency of the device decrease when the holes are introduced into the cathode through the organic light emitting layer. 이때 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI등이 사용될 수 있다. The hole-blocking material that is used should have a not particularly limited electron transport while having a high ability ionization potential than the light emitting compound, and the like can be used representatively BAlq, BCP, TPBI. 이러한 정공저지층 위에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층(70)을 형성하고 상기 전자주입층(70)의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드(80) 전극을 형성함으로써 유기 EL 소자가 완성된다. The hole-blocking layer on a vacuum deposited electron transporting layer (60) method, or a spin coating method a, after the electron injection layer 70 to form and open the metal for the cathode to the upper formation of the electron injection layer 70 is vacuum deposited through the organic EL device is completed by deposition to form a cathode (80) electrodes. 여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다. Here, the cathode metal for forming a lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) and the like, in order to obtain a top emission device may be a transmission-type cathodes using ITO, IZO.

이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명하지만, 본 발명이 이에 한정되는 것은 아니다. More specifically described below, the present invention, for the preferred embodiment, but the present invention is not limited thereto.

실시예 1 Example 1

1-(1) 1,6- 디브로모피렌(1,6-dibromopyrene)의 합성 1 (1) Synthesis of 1,6-di-bromo fur alkylene (1,6-dibromopyrene)

3구 둥근 바닥 플라스크에 피렌 (10 g, 0.049 mol)을 투입하고 CCl 4 (300 mL)에 녹인 다음, 상기 용액에 Br 2 In the pyrene (10 g, 0.049 mol) in 3-neck round bottom flask and dissolved in CCl 4 (300 mL), and then, Br 2 to the solution (17.38 g, 0.108 mol)를 CCl 4 로 희석시켜 4시간에 걸쳐 천천히 적가시켰다. A (17.38 g, 0.108 mol) was diluted with CCl 4 was slowly added dropwise over a period of 4 hours. 반응이 종결되면 생성된 침전물을 그대로 여과한 후 이 침전물을 다시 톨루엔으로 재결정하여 1,6-디브로모피렌 (6.05 g, 34 %) 흰색 고체를 얻었다. After the reaction was completed as a filter the resulting precipitate and then the precipitate is recrystallized again with toluene 1,6-bromo fur alkylene (6.05 g, 34%) to obtain a white solid.

1-(2) 4- 시아노페닐 1 - (2) 4-cyanophenyl 페닐아민(4-cyanophenyl phenyl amine)의 합성 Synthesis of phenylamine (4-cyanophenyl phenyl amine)

2구 둥근 바닥 플라스크에 4-브로모시아노벤젠 (20.2 g, 0.11 mol), 아닐린 (12.4 g, 0.13 mol), BINAP (0.7 g, 1% mol), Pd(OAc) 2 (0.5 g, 2% mol) 및 NaO t Bu (21.3 g, 0.22 mol)를 톨루엔 (400 mL)에 녹인후 24시간 환류시켰다. 2-bromo-necked round bottom flask 4-cyano benzene (20.2 g, 0.11 mol), aniline (12.4 g, 0.13 mol), BINAP (0.7 g, 1% mol), Pd (OAc) 2 (0.5 g, 2% after the mol) and NaO t Bu (21.3 g, 0.22 mol) was dissolved in toluene (400 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 다음 깔대기 위의 고체를 MC로 세척하고 여액을 받아 톨루엔을 제거한 후 물과 MC를 사용하여 추출하였다. After the reaction was terminated, toluene was removed by receiving the filtrate and the solid washed as above funnel MC filtered while hot and extracted with water and MC. 다음으로, 유기층의 물을 MgSO 4 로 제거하고 Hx:EA (8:1)을 전개용매로 사용하여 컬럼크로마토그래피로 분리하였다. Were isolated using a (18) as a developing solvent by column chromatography: Next, removal of the water of the organic layer with MgSO 4, and Hx EA.

1-(3) N, N' - 비스 (4- 시아노페닐 )- N, N' - 디페닐피렌 -1,6-디아민(N, N' - Bis (4- cyanophenyl)-N,N'-diphenylpyrene-1,6-diamine)의 합성 (BD1) 1- (3) N, N ' - bis (4-cyanophenyl) - N, N' - diphenyl-pyrene-1,6-diamine (N, N '- Bis (4-cyanophenyl) -N, N' synthesis of -diphenylpyrene-1,6-diamine) (BD1)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (6.9 g, 0.019 mol), 상기 실시예 1-(2)에서 얻어진 4-시아노페닐 페닐아민 (8.9 g, 0.046 mol), BINAP (0.48 g, 1% mol), Pd(OAc) 2 (0.13 g, 1%mol) 및 NaO t Bu (6.4 g, 0.07 mol)를 톨루엔 (400 mL)에 녹인후 24시간 동안 환류시켰다. The two neck round bottom flask was obtained in the 1,6-bromo fur alkylene (6.9 g, 0.019 mol), Example 1 (2) prepared in Example 1- (1) 4-cyanophenyl phenylamine dissolved in (8.9 g, 0.046 mol), BINAP (0.48 g, 1% mol), Pd (OAc) 2 (0.13 g, 1% mol) and NaO t Bu (6.4 g, 0.07 mol) in toluene (400 mL) after the mixture was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척한 후 용매를 제거하고 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 다음, 메탄올로 재결정하여 노란색의 고체 1.5g을 얻었다. After the reaction was completed, by removing the rear After washing the solid above the funnel to MC solvent was filtered while hot, and by using the MC as a developing solvent separated by column chromatography and then recrystallized with methanol to a yellow solid 1.5 g was obtained.

mp353.31℃, mp353.31 ℃,

λ ABS max : 408nm λ Flu max λ ABS max: 408nm λ Flu max : 453nm, : 453nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.19 (d, 2H, J =9 Hz), 8.09 (d, 2H, J =9 Hz), 8.11 (d, 2H, J =9 Hz), 7.85 (d, 2H, J =9 Hz), 7.40 (d, 4H, J =9 Hz), 7.31 (t, 4H, J =8 Hz), 7.26 (d, 4H, J =9 Hz), 7.14 (t, 2H, J =8 Hz), 6.88 (d, 4H, J =9 Hz)) 1 H NMR (500 MHz, CDCl 3) δ8.19 (d, 2H, J = 9 Hz), 8.09 (d, 2H, J = 9 Hz), 8.11 (d, 2H, J = 9 Hz), 7.85 ( d, 2H, J = 9 Hz ), 7.40 (d, 4H, J = 9 Hz), 7.31 (t, 4H, J = 8 Hz), 7.26 (d, 4H, J = 9 Hz), 7.14 (t, 2H, J = 8 Hz), 6.88 (d, 4H, J = 9 Hz))

1-(4) 유기전계발광소자의 제조 1 - 4 for producing an organic electroluminescent device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 1-(3)에서 제조된 BD1(5%) + BH-1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size and CuPC over and then, the ITO glass, an organic material such that after the pressure is 1X10 -6 torr mounted to the vacuum chamber (650Å), NPD (400Å) , by film formation in the order of the BD1 (5%) + BH-1 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) prepared in example 1- (3) was prepared in the organic EL device .

실시예 2 Example 2

2-(1) 4- 시아노페닐 2 (1) 4-cyanophenyl 나프틸아민(4-cyanophenyl naphtylamine)의 합성 Synthesis of a-naphthylamine (4-cyanophenyl naphtylamine)

2구 둥근 바닥 플라스크에 4-브로모시아노벤젠 (15.3 g, 0.08 mol), 1-나프틸아민 (12.0 g, 0.08 mol), BINAP (0.7 g, 1% mol), Pd(OAc) 2 (0.5 g, 2% mol) 및 NaO t Bu (21.3 g, 0.22 mol)를 톨루엔 (300 mL)에 녹인후 24시간 환류시켰다. A 2-neck round bottom flask, 4-bromo-necked dicyano benzene (15.3 g, 0.08 mol), 1- naphthylamine (12.0 g, 0.08 mol), BINAP (0.7 g, 1% mol), Pd (OAc) 2 (0.5 after g, 2 mol%) and NaO t Bu (21.3 g, 0.22 mol) was dissolved in toluene (300 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 다음 깔대기 위의 고체를 MC로 세척하 고 여액을 받아 톨루엔을 제거한 후 물과 MC를 사용하여 추출하였다. After the reaction was terminated, toluene was removed and then receive the filtrate and the solid washed with the above funnel with MC filtered while hot and extracted with water and MC. 다음으로, 유기층의 물을 MgSO 4 로 제거하고 Hx:EA (10:1)을 전개용매로 사용하여 컬럼크로마토그래피로 분리하였다. Were isolated using a (10: 1) as a developing solvent by column chromatography: Next, removal of the water of the organic layer with MgSO 4, and Hx EA.

2-(2) N, N' - 비스 (4- 시아노페닐 )-N, N' - 디나프틸피렌 -1,6-디아민(N, N' - Bis (4- cyanophenyl)-N,N'-dinaphtylpyrene-1,6-diamine)의 합성 (BD2) 2- (2) N, N ' - bis (4-cyanophenyl) -N, N' - di-naphthyl pyrene-1,6-diamine (N, N '- Bis (4-cyanophenyl) -N, N synthesis of '-dinaphtylpyrene-1,6-diamine) (BD2)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (3.9 g, 0.011 mol), 상기 실시예 2-(1)에서 얻어진 4-시아노페닐 나프틸아민 (6.4 g, 0.026 mol), BINAP (0.3 g, 4% mol), Pd(OAc) 2 (0.1 g, 4%mol) 및 NaO t Bu (6.4 g, 0.07 mol)를 톨루엔 (180 mL)에 녹인후 24시간 동안 환류시켰다. A 2-neck round bottom flask Example 1- (1) manufactured by a 1,6-di-bromo fur alkylene (3.9 g, 0.011 mol), Example 2 (1) 4-cyanophenyl naphthyl obtained in the amine (6.4 g, 0.026 mol), BINAP (0.3 g, 4% mol), Pd (OAc) 2 (0.1 g, 4% mol) and NaO t Bu (6.4 g, 0.07 mol) in toluene (180 mL) It was dissolved the mixture was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척한 후 용매를 제거하고 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 다음, 에테르로 재결정하여 노란색의 고체 0.5g을 얻었다. After the reaction was completed, by removing the rear After washing the solid above the funnel to MC solvent was filtered while hot, and was separated by column chromatography using a MC as a developing solvent was recrystallized in the following, an ether of a yellow solid 0.5 g was obtained.

mp373.7℃, mp373.7 ℃,

λ ABS max : 408nm λ Flu max λ ABS max: 408nm λ Flu max : 450nm, : 450nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.18 (d, 2H, J =9 Hz), 8.12 (d, 2H, J =8 Hz), 8.07 (d, 2H, J =9 Hz), 7.98 (m, 4H), 7.89 (d, 2H, J =9 Hz), 7.83 (t, 2H, 6Hz), 7.55 (t, 2H, J =8 Hz), 7.50 (m, 2H), 7.42 (d, 4H, J =6 Hz), 7.38 (d, 4H, J =9 Hz), 6.62 (m, 4H) 1 H NMR (500 MHz, CDCl 3) δ8.18 (d, 2H, J = 9 Hz), 8.12 (d, 2H, J = 8 Hz), 8.07 (d, 2H, J = 9 Hz), 7.98 ( m, 4H), 7.89 (d , 2H, J = 9 Hz), 7.83 (t, 2H, 6Hz), 7.55 (t, 2H, J = 8 Hz), 7.50 (m, 2H), 7.42 (d, 4H , J = 6 Hz), 7.38 (d, 4H, J = 9 Hz), 6.62 (m, 4H)

2-(3) 유기전계발광소자의 제조 2- (3) Preparation of the organic EL device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 2-(2)에서 제조된 BD2(5%) + BH-1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) by film formation in the order of the embodiments BD2 (5%) + BH-1 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) prepared in 2 (2) preparing an organic EL device It was.

실시예 3 Example 3

3-(1) 4- 시아노페닐 비페닐아민(4- cyanophenyl 3 (1) 4-cyanophenyl-biphenyl amine (4-cyanophenyl biphenylamine )의 합성 Synthesis of biphenylamine)

2구 둥근 바닥 플라스크에 4-브로모비페닐 (30 g, 0.13 mol), 4-아미노벤조니트릴 (15.2 g, 0.13 mol), BINAP (1.6 g, 2% mol), Pd(OAc) 2 (0.6 g, 2% mol) 및 NaO t Bu (24.7 g, 0.26 mol)를 톨루엔 (600 mL)에 녹인후 24시간 환류시켰다. A 2-neck round bottom flask, 4-bromobiphenyl (30 g, 0.13 mol), 4-aminobenzonitrile (15.2 g, 0.13 mol), BINAP (1.6 g, 2% mol), Pd (OAc) 2 (0.6 g after, 2 mol%) and NaO t Bu (24.7 g, 0.26 mol) was dissolved in toluene (600 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 다음 깔대기 위의 고체를 MC로 세척하고 여액을 감압증류 후 톨루엔이 소량 남은 상태에서 헥산을 부어 생긴 결정을 여과하여 10.6g의 고체를 얻었다. After the reaction was completed, the solid washed on the filter funnel and then over a hot state to the MC, and the toluene was evaporated under reduced pressure and then the filtrate was filtered crystals caused by pouring a small amount of hexane in the rest condition to give a solid of 10.6g.

3-(2) N, N' - 비스 (4- 시아노페닐 )-N, N' - 디비페닐피렌 -1,6-디아민(N, N' - Bis (4- cyanophenyl)-N,N'-dibiphenylpyrene-1,6-diamine)의 합성 (BD4) 3- (2) N, N ' - bis (4-cyanophenyl) -N, N' - DB phenyl pyrene-1,6-diamine (N, N '- Bis (4-cyanophenyl) -N, N' synthesis of -dibiphenylpyrene-1,6-diamine) (BD4)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (5.9 g, 0.016 mol), 상기 실시예 3-(1)에서 얻어진 4-시아노페닐 비페닐아민 (10.6 g, 0.039 mol), BINAP (0.41 g, 4% mol), Pd(OAc) 2 (0.1 g, 3% mol) 및 NaO t Bu (5.5 g, 0.06 mol)를 톨루엔 (270 mL)에 녹인후 24시간 동안 환류시켰다. A 2-neck round bottom flask, the above embodiment the 1,6-bromo fur alkylene (5.9 g, 0.016 mol) prepared in 1- (1), 4-cyanophenyl-biphenyl obtained in Example 3- (1) to the amine (10.6 g, 0.039 mol), BINAP (0.41 g, 4% mol), Pd (OAc) 2 (0.1 g, 3% mol) and NaO t Bu (5.5 g, 0.06 mol) in toluene (270 mL) It was dissolved the mixture was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척한 후 용매를 제거하고 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 다음, 메탄올로 재결정하여 고체 4.8g을 얻었다. After the reaction was completed, by removing the rear After washing the solid above the funnel to MC solvent was filtered while hot, and by using the MC as a developing solvent, and then separated by column chromatography, re-crystallization with methanol to a solid 4.8g obtained.

mp325.9℃, mp325.9 ℃,

λ ABS max : 412nm λ Flu max λ ABS max: 412nm λ Flu max : 462nm, : 462nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.22 (d, 2H, J =9 Hz), 8.12 (d, 2H, J =9 Hz), 8.05 (d, 2H, J =9 Hz), 7.91 (d, 2H, J =9 Hz), 7.55 (m, 8H), 7.42 (m, 8H), 7.35 (d, 2H, J =9 Hz), 7.30 (m, 4H), 6.95 (d, 4H, J =9 Hz) 1 H NMR (500 MHz, CDCl 3) δ8.22 (d, 2H, J = 9 Hz), 8.12 (d, 2H, J = 9 Hz), 8.05 (d, 2H, J = 9 Hz), 7.91 ( d, 2H, J = 9 Hz ), 7.55 (m, 8H), 7.42 (m, 8H), 7.35 (d, 2H, J = 9 Hz), 7.30 (m, 4H), 6.95 (d, 4H, J = 9 Hz)

3-(3) 유기전계발광소자의 제조 3 (3) Preparation of the organic EL device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 3-(2)에서 제조된 BD4(5%) + BH- 1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) by film formation in the order of the BD4 (5%) + BH- 1 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) prepared in example 3- (2) preparing an organic EL device It was.

실시예 4 Example 4

4-(1) 4- 시아노페닐 -(2-비페닐)아민(4- cyanophenyl -(2- bipheny ) lamine )의 합 Synthesis of 4 (1) 4-cyano-phenyl- (2-biphenyl) amine ((2-bipheny) lamine 4-cyanophenyl)

2구 둥근 바닥 플라스크에 4-브로모비페닐 (20.2g, 0.087 mol), 4-아미노벤조니트릴 (12.5 g, 0.106 mol), DPPF (2.5 g, 5% mol), Pd(OAc) 2 (5 g, 4% mol) 및 NaO t Bu (17 g, 0.177 mol)를 톨루엔 (400 mL)에 녹인후 24시간 환류시켰다. A 2-neck round bottom flask, 4-bromobiphenyl (20.2g, 0.087 mol), 4-aminobenzonitrile (12.5 g, 0.106 mol), DPPF (2.5 g, 5% mol), Pd (OAc) 2 (5 g after, 4 mol%) and NaO t Bu (17 g, 0.177 mol) was dissolved in toluene (400 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 다음 깔대기 위의 고체를 MC로 세척하고 용매를 제거한 후 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 뒤 과량의 헥산을 가하여 생긴 결정을 여과하여 11g의 고체를 얻었다. After the reaction was terminated, after washing the solid above, and then the funnel was filtered in a hot state to the MC, and after removal of the solvent by using the MC as a developing solvent separated by column chromatography and filtration the crystals caused by adding an excess of hexane to obtain 11g of a solid.

4-(2) N, N' - 비스 (4- 시아노페닐 )-N, N' - 디(2-비페닐)피렌 -1,6- 디아민 (N, N' - Bis (4-cyanophenyl)-N,N'-di(2-biphenyl)pyrene-1,6-diamine)의 합성 (BD5) 4- (2) N, N ' - bis (4-cyanophenyl) -N, N' - di (2-biphenyl) pyrene-1,6-diamine (N, N '- Bis ( 4-cyanophenyl) -N, synthesis of N'-di (2-biphenyl) pyrene-1,6-diamine) (BD5)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (9.85 g, 0.027 mol), 상기 실시예 4-(1)에서 얻어진 4-시아노페닐-(2-비페닐)아민 (14.8 g, 0.055 mol), BINAP (0.68 g, 4% mol), Pd(OAc) 2 (0.25 g, 4% mol) 및 NaO t Bu (10.6 g, 0.11 mol)를 톨루엔 (450 mL)에 녹인후 24시간 동안 환류시켰다. 2-necked round bottom flask was charged with the above-described example, the 1,6-di-bromo fur alkylene prepared in 1- (1) (9.85 g, 0.027 mol), obtained in Example 4 (1) 4-cyano-phenyl- ( a 2-biphenyl) amine (14.8 g, 0.055 mol), BINAP (0.68 g, 4% mol), Pd (OAc) 2 (0.25 g, 4% mol) and NaO t Bu (10.6 g, 0.11 mol) in toluene was dissolved in (450 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척한 후 용매를 제거하고 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 다음, 헥산으로 재결정하여 고체 1.3g을 얻었다. After the reaction was completed, by removing the rear After washing the solid above the funnel to MC solvent was filtered while hot, and was separated into the deployment chromatography using a solvent column our MC then recrystallized from hexane the solid 1.3g obtained.

mp335.84℃, mp335.84 ℃,

λ ABS max : 418nm λ Flu max λ ABS max: 418nm λ Flu max : 453nm, : 453nm,

1 H NMR (500 MHz, CDCl 3 ) δ7.93 (d, 2H, J =8 Hz), 7.65 (d, 2H, J =9 Hz), 7.58 (d, 2H, J =8 Hz), 7.55 (d, 2H, J =9 Hz), 7.42 (m, 4H), 7.35 (m, 4H), 7.25(m, 6H), 7.08 (d, 6H, J =6 Hz), 6.90 (d, 6H, J =6 Hz) 1 H NMR (500 MHz, CDCl 3) δ7.93 (d, 2H, J = 8 Hz), 7.65 (d, 2H, J = 9 Hz), 7.58 (d, 2H, J = 8 Hz), 7.55 ( d, 2H, J = 9 Hz ), 7.42 (m, 4H), 7.35 (m, 4H), 7.25 (m, 6H), 7.08 (d, 6H, J = 6 Hz), 6.90 (d, 6H, J = 6 Hz)

4-(3) 유기전계발광소자의 제조 4 (3) Preparation of the organic EL device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 4-(2)에서 제조된 BD5(5%) + BH-1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) , example 4- (2) by deposition in the order of the BD5 (5%) + BH-1 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) prepared in an organic electroluminescent device It was.

실시예 5 Example 5

5-(1) 4- 시아노페닐 -(2- 메틸페닐 )아민(4- cyanophenyl -(2- methylpheny ) 5 (1) 4-cyano-phenyl- (2-methyl-phenyl) amine (4-cyanophenyl (2-methylpheny)

lamine )의 합성 Synthesis of lamine)

2구 둥근 바닥 플라스크에 4-브로모벤조니트릴 (30g, 0.165 mol), o-톨루이딘 (17.7 g, 0.1653 mol), BINAP (4.1 g, 4% mol), Pd(OAc) 2 (0.7 g, 2% mol) 및 NaO t Bu (31.7 g, 0.33 mol)를 톨루엔 (400 mL)에 녹인후 24시간 환류시켰다. A 2-neck round bottom flask, 4-bromo-benzonitrile (30g, 0.165 mol), o- toluidine (17.7 g, 0.1653 mol), BINAP (4.1 g, 4% mol), Pd (OAc) 2 (0.7 g, 2 after the mol%) and NaO t Bu (31.7 g, 0.33 mol) was dissolved in toluene (400 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 다음 깔대기 위의 고체를 MC로 세척하고 용매를 제거한 후 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 뒤 과량의 헥산을 가하여 생긴 결정을 여과하여 7.9g의 고체를 얻었다. After the reaction was terminated, after washing the solid above, and then the funnel was filtered in a hot state to the MC, and after removal of the solvent by using the MC as a developing solvent separated by column chromatography and filtration the crystals caused by adding an excess of hexane to give 7.9g of a solid.

5-(2) N, N' - 비스 (4- 시아노페닐 )-N, N' - 비스(2-메틸페닐)피렌 -1,6- 디아민 5- (2) N, N ' - bis (4-cyanophenyl) -N, N' - bis (2-methylphenyl) pyrene-1,6-diamine (N,N'-Bis (4-cyanophenyl)-N,N'-bis(2-methylphenyl)pyrene-1,6-diamine)의 합성 (BD7) Synthesis of (N, N'-Bis (4-cyanophenyl) -N, N'-bis (2-methylphenyl) pyrene-1,6-diamine) (BD7)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (5.7 g, 0.016 mol), 상기 실시예 5-(1)에서 얻어진 4-시아노페닐-(2-메틸페닐)아민 (7.9 g, 0.038 mol), BINAP (0.39 g, 1% mol), Pd(OAc) 2 (0.11 g, 3% mol) 및 NaO t Bu (5.3 g, 0.06 mol)를 톨루엔 (260 mL)에 녹인후 24시간 동안 환류시켰다. 2-necked round bottom flask was prepared in Example 1- (1) 1,6-di-bromo fur alkylene (5.7 g, 0.016 mol), obtained in Example 5- (1) 4-cyano-phenyl- ( the 2-methyl-phenyl) amine (7.9 g, 0.038 mol), BINAP (0.39 g, 1% mol), Pd (OAc) 2 (0.11 g, 3% mol) and NaO t Bu (5.3 g, 0.06 mol) in toluene ( was dissolved in 260 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척한 후 용매를 제거하고 소량의 MC를 첨가한 다음, 에테르를 첨가하고 결정을 여과하여 연두색 고체 1.7g을 얻었다. After the reaction was completed, remove the rear After washing the solid above the funnel to MC solvent was filtered while hot and a small amount of MC, and then, ether was added and crystals were filtered off to obtain a yellow-green solid 1.7g.

mp373.1℃, mp373.1 ℃,

λ ABS max : 408nm λ Flu max λ ABS max: 408nm λ Flu max : 450nm, : 450nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.12 (d, 2H, J =8 Hz), 8.0 (d, 2H, J =8 Hz), 7.98 (d, 2H, J =8 Hz), 7.72 (d, 2H, J =8 Hz), 7.38 (d, 4H, J =8 Hz), 7.34 (d, 4H, J = 8 Hz), 7.20 (m, 6H), 6.60 (m, 4H), 2.20 (s, 6H) 1 H NMR (500 MHz, CDCl 3) δ8.12 (d, 2H, J = 8 Hz), 8.0 (d, 2H, J = 8 Hz), 7.98 (d, 2H, J = 8 Hz), 7.72 ( d, 2H, J = 8 Hz ), 7.38 (d, 4H, J = 8 Hz), 7.34 (d, 4H, J = 8 Hz), 7.20 (m, 6H), 6.60 (m, 4H), 2.20 ( s, 6H)

5-(3) 유기전계발광소자의 제조 5 (3) Preparation of the organic EL device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 5-(2)에서 제조된 BD7(5%) + BH-1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) by film formation in the order of the embodiments BD7 (5%) prepared from 5- (2) + BH-1 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) to obtain an organic electroluminescence element It was.

실시예 6 Example 6

6-(1) 4- 시아노페닐 -4-t-부틸페닐아민(4- cyanophenyl -4-t- buthylphenyl 6 (1) 4-cyanophenyl -4-t- butyl-phenylamine (4-cyanophenyl -4-t- buthylphenyl

amine )의 합성 Synthesis of amine)

2구 둥근 바닥 플라스크에 4-브로모벤조니트릴 (15g, 0.08 mol), 4-t-부틸벤젠 (12.3 g, 0.08 mol), BINAP (1 g, 2% mol), Pd(OAc) 2 (0.4 g, 2% mol) 및 NaO t Bu (15.8 g, 0.16 mol)를 톨루엔 (300 mL)에 녹인후 24시간 환류시켰다. A 2-neck round bottom flask, 4-bromo-benzonitrile (15g, 0.08 mol), 4 -t- butyl benzene (12.3 g, 0.08 mol), BINAP (1 g, 2% mol), Pd (OAc) 2 (0.4 after g, 2 mol%) and NaO t Bu (15.8 g, 0.16 mol) was dissolved in toluene (300 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 다음 깔대기 위의 고체를 MC로 세척하고 용매를 감압증류하여 제거한 뒤 MC와 물로 추출하고 유기층을 분리하였다. After the reaction was completed, the solid was washed in the funnel above, and then filtered in the hot state to the MC and extracting the solvent under reduced pressure after the MC and water removed by distillation and the organic phase was separated therefrom. 마지막으로 상기 유기층의 물을 MgSO 4 로 제거한 후 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 뒤 메탄올로 재결정하여 5.5g의 고체를 얻었다. Finally, re-crystallization with methanol to water in the organic layer after separation in the expansion chromatography using a solvent column our MC was removed by MgSO 4 to give a solid 5.5g.

6-(2) N, N' - 비스 (4- 시아노페닐 )-N, N' - 비스(4-t-부틸페닐)피렌 -1,6- 디아민 6- (2) N, N ' - bis (4-cyanophenyl) -N, N' - bis (4-t- butylphenyl) pyrene-1,6-diamine (N,N'-Bis (4-cyanophenyl)-N,N'-bis(4-t-buthylphenyl)pyrene-1,6-diamine)의 합성 (BD9) Synthesis of (N, N'-Bis (4-cyanophenyl) -N, N'-bis (4-t-buthylphenyl) pyrene-1,6-diamine) (BD9)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (3.3 g, 0.009 mol), 상기 실시예 6-(1)에서 얻어진 4-시아노페닐-4-t-부틸페닐아민 (5.5 g, 0.022 mol), BINAP (0.23 g, 4% mol), Pd(OAc) 2 (0.08 g, 4% mol) 및 NaO t Bu (3.5 g, 0.06 mol)를 톨루엔 (150 mL)에 녹인후 24시간 동안 환류시켰다. A 2-neck round bottom flask Example 1- (1) a 1,6-di-bromo fur alkylene (3.3 g, 0.009 mol), obtained in Example 6- (1) 4-cyanophenyl -4 manufactured by -t- butylphenyl amine a (5.5 g, 0.022 mol), BINAP (0.23 g, 4% mol), Pd (OAc) 2 (0.08 g, 4% mol) and NaO t Bu (3.5 g, 0.06 mol) in toluene was dissolved in (150 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척한 후 용매를 제거하고 소량의 MC를 첨가한 다음, 메탄올을 첨가하여 결정을 얻었다. After the reaction was completed, remove the rear After washing the solid above the funnel to MC solvent was filtered while hot and a small amount of MC then, methanol was added to obtain a crystal. 다음으로, MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리한 후 에테르로 재결정하여 고체 1.7g을 얻었다. Next, after using the MC as a developing solvent separated by column chromatography and recrystallized with ether to give a solid 1.7g.

mp425.1℃, mp425.1 ℃,

λ ABS max : 410nm λ Flu max λ ABS max: 410nm λ Flu max : 461nm, : 461nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.22 (d, 2H, J =8 Hz), 8.12 (d, 2H, J =9 Hz), 8.05 (d, 2H, J =9 Hz), 7.90 (d, 2H, J =8 Hz), 7.42 (d, 2H, J =8 Hz), 7.35 (d, 4H, J =8 Hz), 7.22 (d, 4H, J =8 Hz), 6.88 (d, 4H, J =8 Hz), 1.30 (s, 18H) 1 H NMR (500 MHz, CDCl 3) δ8.22 (d, 2H, J = 8 Hz), 8.12 (d, 2H, J = 9 Hz), 8.05 (d, 2H, J = 9 Hz), 7.90 ( d, 2H, J = 8 Hz ), 7.42 (d, 2H, J = 8 Hz), 7.35 (d, 4H, J = 8 Hz), 7.22 (d, 4H, J = 8 Hz), 6.88 (d, 4H, J = 8 Hz), 1.30 (s, 18H)

6-(3) 유기전계발광소자의 제조 6 (3) Manufacture of organic electroluminescent device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 6-(2)에서 제조된 BD9(5%) + BH-1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) by film formation in the order of the embodiments BD9 (5%) prepared from 6- (2) + BH-1 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) to obtain an organic electroluminescence element It was.

실시예 7 Example 7

7-(1) 4-브로모페닐트리메틸실란(4- bromophenyltrimethylsilane )의 합성 7 (1) 4-bromo synthesis of certain phenyl-trimethylsilane (4- bromophenyltrimethylsilane)

3구 둥근 바닥 플라스크에 1,4-디브로모벤젠 (12.7 g, 0.053 mol)과 디에틸에테르(300ml)를 넣고 용해시킨 다음, 플라스크의 외부온도를 -78℃로 냉각시키고 n-BuLi을 천천히 적가시켰다. 3-neck round bottom flask was placed the 1,4-dibromobenzene (12.7 g, 0.053 mol) and diethyl ether (300ml) dissolved therein was then cooled to an external temperature of the flask at -78 ℃ slowly to n-BuLi It was dropping. 다음으로 온도를 0℃로 1시간에 걸쳐 승온하고 클로로트리메틸실란(7.51ml, 0.059mol)을 천천히 적가하고 다시 온도를 상온으로 승온하였다. Next, temperature was raised over 1 hour to a temperature of 0 ℃ and slowly added dropwise chlorotrimethylsilane (7.51ml, 0.059mol) and the mixture was heated up to a temperature back to ambient temperature. 반응이 종결된 후 물과 디에틸에테르를 사용하여 추출하고 MgSO 4 로 물을 제 거한 다음 용매를 제거하고 감압하에서 분별증류하여 4-브로모페닐트리메틸실란 (11.3 g, 92 %) 을 얻었다. After the reaction was terminated by extraction with water and diethyl ether and remove the solvent, and then dwelt water as MgSO 4 and fractional distillation under reduced pressure to give the 4-bromophenyl trimethylsilane (11.3 g, 92%).

7-(2)4- 시아노페닐 -4-트리메틸실리페닐아민(4- cyanophenyl -4- trimethyl silylphenylamine)의 합성 7- (2) Synthesis of 4-cyano-4-trimethylsilyoxy phenylamine (4-cyanophenyl-4-trimethyl silylphenylamine)

2구 둥근 바닥 플라스크에 상기 실시예 1-(2)에서 제조된 4-시아노페닐 페닐아민 (1.2ml, 0.0076 mol), 상기 실시예 7-(1)에서 제조된 4-브로모페닐트리메틸실란 (1 g, 0.0044 mol), BINAP (0.03 g, 1% mol), Pd(OAc) 2 (0.01 g, 1% mol) 및 NaO t Bu (1.5 g, 0.016 mol)를 톨루엔 (50 mL)에 녹인후 24시간 환류시켰다. 2-neck round bottom flask was charged with the embodiment in Example 1 (2) 4-cyanophenyl phenylamine prepared in (1.2ml, 0.0076 mol), a 4-bromophenyl trimethylsilane prepared in Example 7 (1) dissolved in (1 g, 0.0044 mol), BINAP (0.03 g, 1% mol), Pd (OAc) 2 (0.01 g, 1% mol) and NaO t Bu (1.5 g, 0.016 mol) in toluene (50 mL) after the mixture was refluxed for 24 hours. 상기 반응이 종결된 후, 플라스크를 냉각시키고 반응용액인 톨루엔을 제거한 다음 헥산을 사용하여 컬럼 분리를 하고 에탄올과 물을 사용하여 침전이 생기면 이것을 여과하여 흰색 고체인 4-시아노페닐-4-트리메틸실릴페닐아민(1.12g, 86%)을 얻었다. After the reaction was completed, cool the flask and removing the reaction solution in toluene and then hexanes to use a separation column using an ethanol and water saenggimyeon precipitate filtered and the white solid of 4-cyano-4-trimethyl to give a silyl-phenylamine (1.12g, 86%).

7-(3)N, N' - 비스 (4- 시아노페닐 )-N, N' - 비스(4-트리메틸실릴페닐)피렌 -1,6- 디아 민 (N,N'-Bis (4-cyanophenyl)-N,N'-bis(4-trimethylsilylphenyl) pyrene-1,6-diamine)의 합성 (BD17) 7- (3) N, N ' - bis (4-cyanophenyl) -N, N' - bis (4-trimethylsilyl-phenyl) pyrene-1,6-diamine (N, N'-Bis (4- cyanophenyl) -N, synthesis of N'-bis (4-trimethylsilylphenyl) pyrene-1,6-diamine) (BD17)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (3.9 g, 0.011 mol), 상기 실시예 7-(2)에서 얻어진 4-시아노페닐-4-트리메틸실릴페닐아민 (6.9 g, 0.026 mol), BINAP (0.27 g, 4% mol), Pd(OAc) 2 (0.10 g, 4% mol) 및 NaO t Bu (4.2 g, 0.04 mol)를 톨루엔 (50 mL)에 녹인후 24시간 동안 환류시켰다. 2-neck round bottom flask Example 1- (1) a 1,6-di-bromo fur alkylene (3.9 g, 0.011 mol), obtained in Example 7 (2) 4-cyanophenyl -4 manufactured by -trimethylsilyl-phenyl amine (6.9 g, 0.026 mol), BINAP (0.27 g, 4% mol), Pd (OAc) 2 (0.10 g, 4% mol) and NaO t Bu (4.2 g, 0.04 mol) in toluene ( was dissolved in 50 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척하였다. After the reaction was completed, the solid was washed in the funnel above the back filtration in the hot state to the MC. 상기 MC 및 톨루엔을 감압하여 제거한 다음 메탄올을 첨가하여 결정을 얻고, 상기 결정을 MC로 컬럼분리하였다. Removed under reduced pressure, the MC and toluene to obtain the following decision by the addition of methanol, and the separation column to the determination by MC. 마지막으로, 상기 MC를 감압하여 제거한 후 소량의 MC에 에테르를 첨가하여 결정을 얻은 다음, MC/MeOH로 재결정하여 2g의 고체를 얻었다. Finally, after removing under reduced pressure the MC obtained crystals by the addition of ether in a small amount of MC, and then, recrystallized with MC / MeOH to give a solid of 2g.

mp361.8℃, mp361.8 ℃,

λ ABS max : 410nm λ Flu max λ ABS max: 410nm λ Flu max : 456nm, : 456nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.18 (d, 2H, J =8 Hz), 8.08 (d, 2H, J =9 Hz), 8.0 (d, 2H, J =9 Hz), 7.42 (d, 4H, J =9 Hz), 7.40 (d, 4H, J =9 Hz), 7.20 (d, 4H, J =9 Hz), 6.92 (d, 4H, J =9 Hz), 0.25(s, 18H) 1 H NMR (500 MHz, CDCl 3) δ8.18 (d, 2H, J = 8 Hz), 8.08 (d, 2H, J = 9 Hz), 8.0 (d, 2H, J = 9 Hz), 7.42 ( d, 4H, J = 9 Hz ), 7.40 (d, 4H, J = 9 Hz), 7.20 (d, 4H, J = 9 Hz), 6.92 (d, 4H, J = 9 Hz), 0.25 (s, 18H)

7-(4) 유기전계발광소자의 제조 7 (4) Preparation of the organic EL device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 7-(3)에서 제조된 BD17(5%) + BH-1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) by film formation in the order of example 7- (3) the BD17 (5%) + BH-1 (200Å) manufactured by, Alq3 (350Å), LiF (5Å), Al (1000Å) to obtain an organic electroluminescence element It was.

실시예 8 Example 8

8-(1) 디-4- 시아노페닐아민(di-4-cyanophenylamine)의 합성 8 (1) Synthesis of di-4-cyanophenyl amine (di-4-cyanophenylamine)

2구 둥근 바닥 플라스크에 4-브로모벤조니트릴 (30g, 0.16 mol), 4-아미노벤조니트릴 (19.5 g, 0.16 mol), BINAP (2.0 g, 2% mol), Pd(OAc) 2 (0.9 g, 2% mol) 및 NaO t Bu (31.7 g, 0.33 mol)를 톨루엔 (600 mL)에 녹인후 24시간 환류시켰다. 2-necked round bottom flask of 4-bromo benzonitrile (30g, 0.16 mol), 4-aminobenzonitrile (19.5 g, 0.16 mol), BINAP (2.0 g, 2% mol), Pd (OAc) 2 (0.9 g after, 2 mol%) and NaO t Bu (31.7 g, 0.33 mol) was dissolved in toluene (600 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 다음 깔대기 위의 고체를 MC로 세척하고 용매를 제거한 후 MC 및 과량의 메탄올로 세척하고 얻은 용액을 감압하여 용매를 제거한 다음, 톨루엔을 소량 첨가한 후 헥산을 부어 재결정하여 베이지색의 고체 16.7g을 얻었다. After the reaction was terminated, and then filtered while hot, and then washing the solid above the funnel with MC, washed and reduced pressure to remove the solvent added in a small amount and then the toluene to obtain a solution and then removing the solvent by MC and a large excess of methanol pour recrystallized with hexane to give 16.7g of a solid beige.

8-(2)N,N, N' , N' - 테트라시아노페닐피렌 -1,6-디아민(N,N, N' , N' - Tetracyano phenylpyrene-1,6-diamine)의 합성 (BD19) 8- (2) N, N, N ', N' - Synthesis of (BD19 - tetrahydro-dicyano-phenyl pyrene-1,6-diamine (Tetracyano phenylpyrene-1,6-diamine N , N, N ', N') )

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (5.0 g, 0.014 mol), 상기 실시예 8-(1)에서 얻어진 디-4-시아노페닐아민 (7.3 g, 0.033 mol), BINAP (1.73 g, 2% mol), Pd(OAc) 2 (0.16 g, 1% mol) 및 NaO t Bu (5.3 g, 0.06 mol)를 톨루엔 (50 mL)에 녹인후 24시간 동안 환류시켰다. 2 the embodiment in Example 1-neck round bottom flask (1) a 1,6-di-bromo fur alkylene (5.0 g, 0.014 mol), Example 8 (1) Synthesis of di-4-cyanophenyl obtained in Production in the amine (7.3 g, 0.033 mol), BINAP (1.73 g, 2% mol), Pd (OAc) 2 (0.16 g, 1% mol) and NaO t Bu (5.3 g, 0.06 mol) in toluene (50 mL) It was dissolved the mixture was refluxed for 24 hours. 상기 반응이 종결된 후, 뜨거운 상태에서 여과한 뒤 깔대기 위의 고체를 MC로 세척한 후 용매를 제거하고 메탄올을 첨가하여 결정을 얻었다. After the reaction was completed, by removing the rear After washing the solid above the funnel to MC solvent was filtered while hot and added to methanol to obtain a crystal. 다음으로 상기 고체를 MC를 전개용매로 사용하여 컬럼크로마토그래피로 분리하고, MC를 감압하여 제거한 후 소량의 MC 에 에테르를 첨가하여 0.2g의 고체를 얻었다. And then separating the solid by column chromatography using an MC as a developing solvent, and remove under reduced pressure to the MC by the addition of a small amount of ether to give a solid of 0.2g MC.

mp417.4℃, mp417.4 ℃,

λ ABS max : 390nm λ Flu max λ ABS max: 390nm λ Flu max : 441nm, : 441nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.25 (d, 2H, J =8 Hz), 8.05 (d, 2H, J =9 Hz), 7.95 (d, 2H, J =9 Hz), 7.85 (d, 2H, J =8 Hz), 7.52 (d, 8H, J =8 Hz), 7.12 (d, 8H, J =8 Hz) 1 H NMR (500 MHz, CDCl 3) δ8.25 (d, 2H, J = 8 Hz), 8.05 (d, 2H, J = 9 Hz), 7.95 (d, 2H, J = 9 Hz), 7.85 ( d, 2H, J = 8 Hz ), 7.52 (d, 8H, J = 8 Hz), 7.12 (d, 8H, J = 8 Hz)

8-(3) 유기전계발광소자의 제조 8 (3) Preparation of the organic EL device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 8-(2)에서 제조된 BD19(5%) + BH-1(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) by film formation in the order of the embodiments BD19 (5%) prepared from 8- (2) + BH-1 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) to obtain an organic electroluminescence element It was.

실시예 9 Example 9

9-(1)3- 시아노페닐 -4-트리메틸실릴페닐아민(3- cyanophenyl -4- trimethylsilylphenylamine)의 합성 9 (1) Synthesis of 3-cyano-4-trimethylsilyl-phenyl amine (3-cyanophenyl-4-trimethylsilylphenylamine)

2구 둥근 바닥 플라스크에 3-시아노페닐아민 (1.2ml, 0.0076 mol), 상기 실 시예 7-(1)에서 제조된 4-브로모페닐트리메틸실란 (1 g, 0.0044 mol), BINAP (0.03 g, 1% mol), Pd(OAc) 2 (0.01 g, 1% mol) 및 NaO t Bu (1.5 g, 0.016 mol)를 톨루엔 (50 mL)에 녹인후 24시간 환류시켰다. A 2-neck round bottom flask 3-cyanophenyl amine (1.2ml, 0.0076 mol), a 4-bromophenyl trimethylsilane (1 g, 0.0044 mol), BINAP (0.03 g prepared in time is it chamber 7 (1) then dissolved in 1% mol), Pd (OAc ) 2 (0.01 g, 1% mol) and NaO t Bu (1.5 g, 0.016 mol) in toluene (50 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, 플라스크를 냉각시키고 반응용액인 톨루엔을 제거한 다음 물과 MC를 사용하여 추출하고 MgSO 4 로 물을 제거한 다음 MC를 감압으로 제거하였다. After the reaction was completed, the flask was cooled and the reaction solution was removed of toluene and then extracted with water and MC and removed under reduced pressure to remove the water and then to the MC MgSO 4. 다음으로 헥산을 사용하여 실리카겔 쇼트 컬럼을 거치게 하고 에탄올과 물을 사용하여 침전이 생기면 이를 여과하여 흰색 고체를 얻었다. And then subjected to a silica gel short column using hexane as the use of ethanol and water to obtain the white solid filtered saenggimyeon precipitation.

9-(2)N, N' - 비스 (3- 시아노페닐 )-N, N' - 비스(4-트리메틸실릴페닐)피렌 -1,6- 디아 민(N,N'-Bis(3-cyanophenyl)-N,N'-bis(4-trimethylsilylphenyl)pyrene-1,6-diamine)의 합성 (BD39) 9- (2) N, N ' - bis (3-cyanophenyl) -N, N' - bis (4-trimethylsilyl-phenyl) pyrene-1,6-diamine (N, N'-Bis (3- cyanophenyl) -N, synthesis of N'-bis (4-trimethylsilylphenyl) pyrene-1,6-diamine) (BD39)

2구 둥근 바닥 플라스크에 상기 실시예 1-(1)에서 제조된 1,6-디브로모피렌 (5.0 g, 0.014 mol), 상기 실시예 9-(1)에서 얻어진 3-시아노페닐-4-트리메틸실릴페닐아민 (8.9 g, 0.033 mol), DPPF (0.38 g, 5% mol), Pd(PPh 3 ) 4 (0.80 g, 5% mol) 및 NaO t Bu (4 g, 0.04 mol)를 톨루엔 (100 mL)에 녹인후 24시간 동안 환류시켰다. A 2-neck round bottom flask Example 1- (1) a 1,6-di-bromo fur alkylene (5.0 g, 0.014 mol), Example 9 3-cyanophenyl -4 obtained in (1), prepared in -trimethylsilyl-phenyl amine (8.9 g, 0.033 mol), DPPF (0.38 g, 5% mol), Pd (PPh 3) 4 (0.80 g, 5% mol) and NaO t Bu (4 g, 0.04 mol) in toluene was dissolved in (100 mL) was refluxed for 24 hours. 상기 반응이 종결된 후, EA:Hx(1:8)을 전개용매로 사용하여 컬럼크로마토그래피로 분리한 후 메탄올로 재결정하여 1.4g의 고체를 얻었다. After the reaction was terminated, EA: Hx (1: 8) and recrystallized with methanol and then separated by column chromatography using as a developing solvent to obtain 1.4g of solid.

mp282.0℃, mp282.0 ℃,

λ ABS max : 412nm λ Flu max λ ABS max: 412nm λ Flu max : 455nm, : 455nm,

1 H NMR (500 MHz, CDCl 3 ) δ8.18 (d, 2H, J =8 Hz), 8.08 (d, 2H, J =9 Hz), 7.98 (d, 2H, J =9 Hz), 7.84 (d, 2H, J =8 Hz), 7.42 (d, 4H, J =8 Hz), 7.22 (m, 6H), 7.15 (d, 2H, J =8 Hz), 7.12 (d, 4H, J =8 Hz), 0.25 (s, 18H) 1 H NMR (500 MHz, CDCl 3) δ8.18 (d, 2H, J = 8 Hz), 8.08 (d, 2H, J = 9 Hz), 7.98 (d, 2H, J = 9 Hz), 7.84 ( d, 2H, J = 8 Hz ), 7.42 (d, 4H, J = 8 Hz), 7.22 (m, 6H), 7.15 (d, 2H, J = 8 Hz), 7.12 (d, 4H, J = 8 Hz), 0.25 (s, 18H)

9-(3) 유기전계발광소자의 제조 9 (3) Preparation of the organic EL device

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 상기 실시예 9-(2)에서 제조된 BD39(5%) + BH-2(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) , example 9 (2) by deposition in the order of BD39 (5%) + BH-2 (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å) prepared in an organic electroluminescent device It was.

비교예 1 Comparative Example 1

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 하기 화학식 6의 화합물(5%) + BH-2(200Å), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) , to thereby prepare an organic EL device by forming in the order of compound (5%) + BH-2 (200Å) of formula 6, Alq3 (350Å), LiF (5Å), Al (1000Å).

Figure 112007017564149-PAT00057

비교예 2 Comparative Example 2

ITO 글래스의 발광 면적이 3mm X 3mm 크기가 되도록 패터닝한 후 세정하고, 진공 챔버에 장착한 다음, 압력이 1X10 -6 torr가 되도록 한 후 유기물을 상기 ITO 글래스위에 CuPC (650Å), NPD(400Å), 하기 화학식 7의 화합물(5%) + BH-1(200Å), A light emitting area of the ITO glass substrate is patterned to have a 3mm X 3mm in size, and equipped with a vacuum chamber and then, over a CuPC the ITO glass, an organic material such that after the pressure is 1X10 -6 torr (650Å), NPD (400Å) a compound (5%) + BH-1 (200Å) of formula (VII), Alq3(350Å), LiF(5Å), Al(1000Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. The film-forming in order of Alq3 (350Å), LiF (5Å), Al (1000Å) to prepare an organic electroluminescent device.

Figure 112007017564149-PAT00058

시험예 1 Test Example 1

실시예 1∼9와 비교예 1∼2에 따라 제조된 유기전계발광소자에 대하여, 전압, 전류, 휘도 및 색좌표를 측정하고 그 결과를 하기 표 1에 나타내었다. Examples 1 to 9 and Comparative Examples 1 and 2 with respect to the organic electroluminescent device prepared in accordance with the voltage, measuring the current, the luminance and chromaticity coordinate and are shown in the following Table 1 as a result.

전압 (V) Voltage (V) 전류 (mA) Current (mA) 휘도 (cd/m 2 ) Luminance (cd / m 2) CIE(X) CIE (X) CIE(Y) CIE (Y)
실시예1 Example 1 4.9 4.9 0.9 0.9 580 580 0.14 0.14 0.11 0.11
실시예2 Example 2 5.4 5.4 0.9 0.9 620 620 0.15 0.15 0.12 0.12
실시예3 Example 3 5.3 5.3 0.9 0.9 800 800 0.15 0.15 0.17 0.17
실시예4 Example 4 5.1 5.1 0.9 0.9 600 600 0.14 0.14 0.12 0.12
실시예5 Example 5 5.2 5.2 0.9 0.9 670 670 0.14 0.14 0.12 0.12
실시예6 Example 6 4.5 4.5 0.9 0.9 830 830 0.15 0.15 0.16 0.16
실시예7 Example 7 4.9 4.9 0.9 0.9 580 580 0.14 0.14 0.11 0.11
실시예8 Example 8 5.2 5.2 0.9 0.9 410 410 0.13 0.13 0.12 0.12
실시예9 Example 9 5.1 5.1 0.9 0.9 610 610 0.14 0.14 0.12 0.12
비교예1 Comparative Example 1 5.4 5.4 0.9 0.9 550 550 0.15 0.15 0.21 0.21
비교예2 Comparative Example 2 5.2 5.2 0.9 0.9 630 630 0.15 0.15 0.20 0.20

상기 시험예의 결과에서 알 수 있는 바와 같이, 본 발명에 따른 유기전계발광소자는 색순도가 종래의 청색발광화합물을 사용한 경우보다 우수하면서도 종래의 발광화합물과 비교할 때에 동등하거나 우수한 수준의 휘도를 가지기 때문에 풀컬러 디스플레이에 유용하게 사용될 수 있다는 것을 확인할 수 있다. As can be seen in the test example results, the organic EL device according to the present invention, since color purity while still superior to the case of using a conventional blue light-emitting compound gajigi an equivalent or superior level of brightness of the time compared to the conventional light-emitting compound pool We can see that it can be useful on a color display.

상기에서 살펴본 바와 같이, 본 발명에 따른 유기전계발광소자는 휘도의 감소 없이 청색의 색순도가 우수하기 때문에 풀컬러 디스플레이에 유용하게 사용될 수 있다. As described above, the organic EL device according to the present invention may be useful in full-color display because of its excellent color purity of blue light without reducing the luminance.

Claims (10)

  1. 하기 식 1의 청색발광화합물. A blue light-emitting compound of the formula 1.
    Figure 112007017564149-PAT00059
    (1) (One)
    (상기 식에서, Ar 1 과 Ar 2 는 각각 (Wherein, Ar 1 and Ar 2 are each
    Figure 112007017564149-PAT00060
    또는 or
    Figure 112007017564149-PAT00061
    이고 ego
    A 1 과 A 2 는 각각 탄소수 1∼10의 알킬기, 탄소수 1∼10의 알콕시기, 탄소수 1∼10의 헤테로 알킬기, 치환되거나 치환되지 않은 탄소수 6∼14의 아릴기 또는 치환되거나 치환되지 않은 탄소수 4∼19의 N, S, O을 포함하는 헤테로 아릴기이고, 상기 치환기는 각각 탄소수 1∼10의 알킬기, 탄소수 1∼10의 알콕시기, 탄소수 1∼10의 알킬아미노기, 탄소수 1∼10의 알킬실릴기, 탄소수 6∼14의 아릴기, 탄소수 4∼19의 N, S, O을 포함하는 헤테로 아릴기, 시아노기 또는 할로겐임.) A 1 and A 2 are each a carbon number of 1 to 10 carbon atoms that is not an alkyl group, having 1 to 10 carbon atoms in the alkoxy group, a C1-10 heteroaryl group, a substituted or an aryl group having 6 to 14 carbon atoms which is unsubstituted or substituted or a substituted 4 a heteroaryl group containing ~19 of N, S, O, wherein the substituents are each optionally substituted alkoxy group of the alkyl group having 1 to 10 carbon atoms, having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, alkyl of 1 to 10 carbon atoms silyl group, a heteroaryl group, a cyano group or a halogen Im containing N, S, O of the aryl group, having a carbon number of 4-19 having a carbon number of 6-14.)
  2. 제 1항에 있어서, 상기 청색발광화합물은 하기 식 2로 표시되는 군에서 선택 The method of claim 1 wherein the blue light-emitting compound is selected from the group represented by the formula 2
    Figure 112007017564149-PAT00062
    , ,
    Figure 112007017564149-PAT00063
    BD1 BD2 BD1 BD2
    Figure 112007017564149-PAT00064
    , ,
    Figure 112007017564149-PAT00065
    BD3 BD4 BD3 BD4
    Figure 112007017564149-PAT00066
    , ,
    Figure 112007017564149-PAT00067
    BD5 BD6 BD5 BD6
    Figure 112007017564149-PAT00068
    , ,
    Figure 112007017564149-PAT00069
    BD7 BD8 BD7 BD8
    Figure 112007017564149-PAT00070
    , ,
    Figure 112007017564149-PAT00071
    BD9 BD10 BD9 BD10
    Figure 112007017564149-PAT00072
    , ,
    Figure 112007017564149-PAT00073
    BD11 BD12 BD11 BD12
    Figure 112007017564149-PAT00074
    , ,
    Figure 112007017564149-PAT00075
    BD13 BD14 BD13 BD14
    Figure 112007017564149-PAT00076
    , ,
    Figure 112007017564149-PAT00077
    BD15 BD16 BD15 BD16
    Figure 112007017564149-PAT00078
    , ,
    Figure 112007017564149-PAT00079
    BD17 BD18 BD17 BD18
    Figure 112007017564149-PAT00080
    , ,
    Figure 112007017564149-PAT00081
    BD19 BD20 BD19 BD20
    Figure 112007017564149-PAT00082
    , ,
    Figure 112007017564149-PAT00083
    BD21 BD22 BD21 BD22
    Figure 112007017564149-PAT00084
    , ,
    Figure 112007017564149-PAT00085
    BD23 BD24 BD23 BD24
    Figure 112007017564149-PAT00086
    , ,
    Figure 112007017564149-PAT00087
    BD25 BD26 BD25 BD26
    Figure 112007017564149-PAT00088
    , ,
    Figure 112007017564149-PAT00089
    BD27 BD28 BD27 BD28
    Figure 112007017564149-PAT00090
    , ,
    Figure 112007017564149-PAT00091
    BD29 BD30 BD29 BD30
    Figure 112007017564149-PAT00092
    , ,
    Figure 112007017564149-PAT00093
    BD31 BD32 BD31 BD32
    Figure 112007017564149-PAT00094
    , ,
    Figure 112007017564149-PAT00095
    BD33 BD34 BD33 BD34
    Figure 112007017564149-PAT00096
    , ,
    Figure 112007017564149-PAT00097
    BD35 BD36 BD35 BD36
    Figure 112007017564149-PAT00098
    , ,
    Figure 112007017564149-PAT00099
    BD37 BD38 BD37 BD38
    Figure 112007017564149-PAT00100
    , ,
    Figure 112007017564149-PAT00101
    BD39 BD40 BD39 BD40
    Figure 112007017564149-PAT00102
    , ,
    Figure 112007017564149-PAT00103
    BD41 BD42 BD41 BD42
    (2) (2)
  3. 제 1항에 있어서, 상기 청색발광화합물은 하기 식 3으로 표시되는 군에서 선택된 어느 하나인 것을 특징으로 하는 청색발광화합물. The method of claim 1 wherein the blue light-emitting compound is a blue light-emitting compound, characterized in that at least one selected from the group represented by the following equation (3).
    Figure 112007017564149-PAT00104
    , ,
    Figure 112007017564149-PAT00105
    BD1 BD2 BD1 BD2
    Figure 112007017564149-PAT00106
    , ,
    Figure 112007017564149-PAT00107
    BD7 BD9 BD7 BD9
    Figure 112007017564149-PAT00108
    , ,
    Figure 112007017564149-PAT00109
    BD17 BD39 BD17 BD39
    (3) 3
  4. 애노드, 유기발광층 및 캐소드를 포함하는 유기전계발광소자에 있어서, 상기 유기발광층은 상기 청구항 제 1항 내지 제3항 중 어느 한 항에 따른 청색발광화합물을 포함하는 유기전계발광소자. In the organic electroluminescent device comprising an anode, an organic emission layer and the cathode, the organic emission layer is an organic light emitting device comprising a blue light-emitting compound according to any one of claim 1 to claim 3.
  5. 제 4항에 있어서, 상기 유기발광층은 호스트화합물로서 하기 식 4의 화합물을 더 포함하는 것을 특징으로 하는 유기전계발광소자. The method of claim 4, wherein the organic emission layer is an organic electroluminescent device according to claim 1, further comprising a compound of the formula 4 as a host compound.
    Figure 112007017564149-PAT00110
    또는 or
    Figure 112007017564149-PAT00111
    (4) (4)
  6. 제 4항에 있어서, 상기 유기전계발광소자는 상기 애노드와 상기 유기발광층 사이에 정공수송층이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층이 추가로 적층되어 있는 것을 특징으로 하는 유기전계발광소자. The method of claim 4, wherein the organic light emitting device is the anode and the and the organic is a hole transport layer is further laminated in between the light emitting layer, the organic characterized in that the electron-transporting layer between the cathode and the organic thin film layer is further laminated to electroluminescent device.
  7. 제 6항에 있어서, 상기 정공수송층의 하부에 정공주입층이 더 적층되어 있는 것을 특징으로 하는 유기전계발광소자. The method of claim 6, wherein the organic electroluminescent device, characterized in that the hole injection layer further laminated on a lower portion of the hole transport layer.
  8. 제 6항에 있어서, 상기 전자수송층의 상부에 전자주입층이 더 적층되어 있 는 것을 특징으로 하는 유기전계발광소자. The method of claim 6, wherein the organic electroluminescent device on top of the electron transport layer, wherein the electron injection layer is can be further laminated.
  9. 제 6항에 있어서, 상기 정공수송층은 N,N'-비스(3-메틸페닐)-N,N'-디페닐 -[1,1-비페닐]-4,4'- 디아민(TPD) 또는 , N,N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD)을 포함하는 것을 특징으로 하는 유기전계발광소자. 7. The method of claim 6 wherein the hole transporting layer is N, N'- bis (3-methylphenyl) -N, N'- diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD) or, N, N'- di (naphthalene-1-yl) -N, N'- di organic electroluminescent device comprising the phenyl benzidine (α-NPD).
  10. 제 7항에 있어서, 상기 정공주입층은 CuPc, TCTA 또는 m-MTDATA를 포함하는 것을 특징으로 하는 유기전계발광소자. The method of claim 7, wherein the hole injection layer is an organic electroluminescent device comprising the CuPc, TCTA, or m-MTDATA.
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