KR20140014956A - Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents

Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same Download PDF

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KR20140014956A
KR20140014956A KR1020120082422A KR20120082422A KR20140014956A KR 20140014956 A KR20140014956 A KR 20140014956A KR 1020120082422 A KR1020120082422 A KR 1020120082422A KR 20120082422 A KR20120082422 A KR 20120082422A KR 20140014956 A KR20140014956 A KR 20140014956A
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현서용
윤용호
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
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Abstract

An organic electroluminescent device compound represented by structural formula 1 below is disclosed. According to the present invention, the organic electroluminescent device which has an outstanding electrical stability and electron- and hole-transporting ability and improves a light-emitting efficiency of phosphorescent light-emitting materials by having a high-level of triplet state energy, and an organic electroluminescent device comprising the same are provided.

Description

새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자{NOVEL COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}TECHNICAL FIELD [0001] The present invention relates to a compound for a novel organic electroluminescent device and an organic electroluminescent device including the same. BACKGROUND OF THE INVENTION [0002]

본 발명은 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자에 관한 것으로, 보다 상세하게는 효율이 높고 구동전압이 낮은 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device including the same, and more particularly, to a compound for an organic electroluminescent device having high efficiency and low driving voltage and an organic electroluminescent device including the same.

정보화 사회로의 움직임이 가속화되면서 평판 디스플레이의 비중이 점차 증가하고 있다. 그 중 LCD(liquid crystal display)가 현재 가장 많이 쓰이고 있지만 액정에 전압을 가해 백라이트로부터의 빛을 컬러필터로 통과시켜 삼원색을 얻음으로써 화면을 만드는 방식이며, 유기EL(OLED; Organic Light Emitting Diodes)은 자체발광 소자로써 시야각 및 대조비 등이 우수하고, 경량 및 박형이 가능하며 휘는 성질의 기판에도 사용할 수 있어, 투명, 플렉서블 디스플레이가 가능하여 차세대 표시소자로서 주목을 받고 있다.As the move to the information society accelerates, the proportion of flat panel displays is gradually increasing. LCD (liquid crystal display) is the most widely used method, but it is a method to make a screen by applying voltage to liquid crystal and passing light from backlight through color filter to obtain three primary colors. Organic light emitting diodes (OLED) As a self-luminous element, it has excellent viewing angle and contrast ratio, is lightweight and thin, can be used for a substrate having a bending property, and is capable of transparent and flexible display, and has attracted attention as a next generation display element.

유기EL은 유기물 박막에 음극과 양극을 통하여 주입된 전자와 정공이 재결합을 통해 여기자를 형성하고, 형성된 그 여기자로부터 특정한 파장의 빛이 발생하는 현상으로 1963년 Pope 등에 의해 안트라센(anthracene)의 단결정으로부터 처음으로 발견되었고 이후 이스트만 코닥사의 탕(C.W Tang)등에 의해 적층형의 유기EL 소자의 보고(C.W Tang, S.A Vanslyke, Applied physics Letters. 51권 913p, 1987) 된 이후 활발히 연구 되고 있다.Organic EL is a phenomenon in which excitons are formed by recombination of electrons and holes injected through a cathode and an anode into an organic thin film, and light of a specific wavelength is generated from the excitons formed. In 1963, Pope et al. Reported that an anthracene single crystal (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, No. 913p, 1987) by Eastman Kodak Co., Ltd. (CW Tang) et al.

유기전계발광소자에 사용되는 유기물질은 크게 고분자와 저분자 형태로 나누어지며 저분자는 순 유기물질과 메탈과 킬레이트를 형성한 메탈 콤플렉스로 나뉘어 질 수 있다.Organic materials used in organic electroluminescent devices are classified into polymer and small molecule, and small molecules can be divided into pure organic material and metal complex which forms metal and chelate.

고분자 물질은 다양한 기능의 유닛을 고분자 체인에 결합하여 다기능의 물질을 만들어 낼 수 있으나, 합성물 정제시나 소자 형성시 어려움이 있고, 저분자 물질은 각 특성의 물질을 합성 할 수 있으나 다기능의 특성을 나타내는 물질 합성에는 한계가 있다. Polymers can combine various functional units into a polymer chain to produce a multifunctional material. However, it is difficult to purify a compound or to form an element, and a low-molecular substance can synthesize a substance having various properties. However, There is a limit to the synthesis.

한편 유기전계발광소자를 적층구조로 형성할 수 있다. 적층구조의 장점으로는 각 기능에 맞게끔 물질을 선택하여 사용할 수 있는 것인데, 일반적으로 소자구조는 양극과 음극 사이에 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층을 형성하여 발광층에서 여기자 형성을 쉽게 하고, 발광 효율을 높이게 되어 있다.On the other hand, the organic electroluminescent devices can be formed in a laminated structure. In general, the device structure is formed by forming a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer between an anode and a cathode to form a light emitting layer Thereby facilitating the formation of excitons and improving the luminous efficiency.

발광물질은 호스트물질과 발광물질(도판트)물질로 크게 나눌 수 있고, 발광물질은 발광 기작에 따라 형광과 인광으로 구별된다. The luminescent material can be roughly divided into a host material and a luminescent material (dopant) material, and the luminescent material is distinguished by fluorescence and phosphorescence depending on the luminescence mechanism.

화합물 내 전자의 여기 상태는 일중항 대 삼중항의 비율이 1:3으로 삼중항 상태가 3배 정도 더 생성된다. 따라서, 일중항 상태에서 기저상태로 떨어지는 형광의 내부양자효율이 25%에 그치는 반면 삼중항 상태에서 기저상태로 떨어지는 인광의 내부양자효율은 75%이다. 또한 일중항 상태에서 삼중항 상태로 계간전이가 일어날 경우 내부양자효율의 이론적 한계치는 100%에 달한다. 이러한 점을 이용해 발광효율을 개선한 발광재료가 인광 발광재료이다.The excited state of the electrons in the compound is 1: 3 ratio of singlet to triplet, and triplet state is generated about 3 times more. Thus, the internal quantum efficiency of phosphorescence falling from the triplet state to the base state is 75% while the internal quantum efficiency of the fluorescence falling from the singlet state to the ground state is only 25%. In addition, the theoretical limit of internal quantum efficiency reaches 100% when the interplanar transition from singlet state to triplet state occurs. A light emitting material that improves the light emitting efficiency by using this point is a phosphorescent material.

유기물의 특성상 인광 발광은 어려움이 있어, 인광 발광재료로는 전이금속(이리듐)을 이용한 유기금속화합물이 개발되고 있으며, 이를 보조하는 호스트 물질로 유기물질이 이용되고 있다. 인광발광물질을 보조하는 물질(호스트)는 밴드갭이 넓고 삼중항 상태 에너지가 높아야 한다. 전류효율과 발광효율이 우수한 인광물질이 각광을 받고 있으나 전자 수송능력과 홀 수송능력, 열적, 전기적으로 안정하고 특히 삼중항 상태에너지가 높은 호스트 물질이 아직 없어 개발이 시급하다.Organic metal compounds using a transition metal (iridium) have been developed as phosphorescent light emitting materials because organic phosphors are difficult to emit phosphorescence due to the nature of organic materials, and organic materials are used as host materials to assist them. The material that assists the phosphorescent material (host) should have a wide bandgap and a high triplet state energy. Although phosphorescent materials having excellent current efficiency and luminous efficiency are in the spotlight, there is no need to develop a host material having high electron transporting ability, hole transporting ability, thermal and electrical stability and especially high triplet state energy.

본 발명은 전기적 안정성 및 전자와 홀 수송능력이 우수하며, 삼중항 상태 에너지가 높아 인광발광재료의 발광효율을 향상시킬 수 있는 호스트로서 발광층에 사용 될 수 있는 유기발광소자용 화합물 및 이를 포함하는 유기전기발광소자를 제공할 수 있다.The present invention relates to a compound capable of being used in a light emitting layer as a host which is excellent in electrical stability and electron and hole transporting ability and has high triplet state energy and can improve the luminous efficiency of a phosphorescent light emitting material, An electroluminescent device can be provided.

또한 본 발명은 유기전기발광소자의 전자수송재료나, 홀수송재료에 사용될 수 있는 유기발광소자용 화합물 및 이를 포함하는 유기전기 발광소자를 제공할 수 있다.In addition, the present invention can provide an organic light emitting device compound and an organic electroluminescent device including the same that can be used for an electron transporting material and a hole transporting material of an organic electroluminescence device.

본 발명의 일 측면에 따르면, 하기 구조식 1로 표시되는 유기전계발광소자용 화합물이 제공될 수 있다.According to an aspect of the present invention, a compound for an organic electroluminescence device represented by the following structural formula 1 may be provided.

[구조식 1][Structural formula 1]

Figure pat00001
Figure pat00001

상기 구조식 1에서,In the above formula 1,

R1 및 R2는 서로 같거나 다를 수 있고, R1 및 R2는 각각 독립적으로 수소원자,

Figure pat00002
R 1 and R 2 may be the same or different from each other, and R 1 and R 2 are each independently a hydrogen atom,
Figure pat00002

치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R1 및 R2 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있고,A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 1 And R < 2 > is a fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group which is further bonded to a neighboring carbon atom of the carbon atom to which it is bonded to form a substituted or unsubstituted fused C6 to C30 aryl group, Lt; / RTI >

Ar1 및 Ar2는 서로 같거나 다를 수 있고, Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴기, 또는 치환 또는 비치환된 C3 내지 C30 시클로알킬기이거나, 또는 Ar1 및 Ar2는 서로 결합되고 그들 사이의 질소원자와 함께 치환 또는 비치환된 C2 내지 C30 헤테로 아릴기 또는 치환 또는 비치환된 C3 내지 C30 시클로알킬기를 형성할 수 있고,Ar 1 and Ar 2 may be the same or different from each other, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, Or Ar 1 and Ar 2 are bonded to each other and together with the nitrogen atom therebetween form a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted C3 to C30 cycloalkyl group Can,

Ar3 내지 Ar5는 서로 같거나 다를 수 있고, Ar3 내지 Ar5는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴기, 또는 치환 또는 비치환된 C3 내지 C30 시클로알킬기이고,Ar 3 to Ar 5 may be the same or different from each other, Ar 3 to Ar 5 each independently represent a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, Lt; / RTI > is a C3 to C30 cycloalkyl group,

R8 내지 R30은 서로 같거나 다를 수 있고, R8 내지 R30은 각각 독립적으로 수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이거나, 또는 R8 내지 R30 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C2 내지 C30 헤테로 아릴기를 형성할 수 있고,R 8 to R 30 may be the same or different from each other, and R 8 to R 30 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group, or any one of R 8 to R 30 may further be bonded to the adjacent carbon atom of the carbon atom to which they are bonded to form a substituted or unsubstituted C 6 to C 30 aryl group, An unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C2 to C30 heteroaryl group,

Y1 내지 Y3은 서로 같거나 다를 수 있고, Y1 내지 Y3은 각각 독립적으로 산소원자 또는 황원자이고,Y 1 to Y 3 may be the same or different from each other, Y 1 to Y 3 are each independently an oxygen atom or a sulfur atom,

m은 0 또는 1이고,m is 0 or 1,

R3 내지 R7은 서로 같거나 다를 수 있고, R3 내지 R7은 각각 독립적으로 수소원자, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R3 내지 R7 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있다.R 3 to R 7 may be the same or different from each other, and each of R 3 to R 7 independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 3 to R 7 Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group have.

본 발명의 다른 측면에 따르면 하기 구조식 1로 표시되는 유기전계발광소자용 화합물이 제공될 수 있다. According to another aspect of the present invention, a compound for an organic electroluminescence device represented by the following structural formula 1 may be provided.

[구조식 1][Structural formula 1]

Figure pat00003
Figure pat00003

상기 구조식 1에서,In the above formula 1,

R1 및 R2는 서로 같거나 다를 수 있고, 각각 독립적으로 아래 화학식 U1 내지 U58 중에서 선택된 어느 하나이고,R 1 and R 2, which may be the same or different, are each independently selected from the following formulas (U1) to (U58)

m은 0 또는 1이고,m is 0 or 1,

R3 내지 R7은 서로 같거나 다를 수 있고, R3 내지 R7은 각각 독립적으로 수소원자, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R3 내지 R7 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있다.R 3 to R 7 may be the same or different from each other, and each of R 3 to R 7 independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 3 to R 7 Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group have.

Figure pat00004
Figure pat00004

Figure pat00005
Figure pat00005

Figure pat00006
Figure pat00006

본 발명의 다른 측면에 따르면, 하기 구조식 1 내지 34, 바람직하게는 하기 구조식 1 내지 20으로 표시되는 화합물 중에서 선택된 어느 하나인 유기전계발광소자용 화합물이 제공될 수 있다.According to another aspect of the present invention, there is provided a compound for an organic electroluminescence device, which is selected from the compounds represented by the following Structural Formulas 1 to 34, preferably the compounds represented by the following Structural Formulas 1 to 20.

Figure pat00007
Figure pat00007

Figure pat00008
Figure pat00008

Figure pat00009
Figure pat00009

Figure pat00010
Figure pat00010

Figure pat00011
Figure pat00011

본 발명의 또 다른 측면에 따르면, 본 발명에 따른 유기전계발광소자용 화합물을 포함하는 유기전계발광소자가 제공될 수 있다.According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound for an organic electroluminescent device according to the present invention.

본 발명의 또 다른 측면에 따르면, 제1전극, 제2전극 및 제1전극과 제2전극 사이에 단수 또는 복수의 유기물층을 포함하는 유기전계발광소자에 있어서,According to another aspect of the present invention, there is provided an organic electroluminescent device including a first electrode, a second electrode, and a single or a plurality of organic layers between a first electrode and a second electrode,

상기 단수 또는 복수의 유기물층 중에서 선택된 1종 이상의 유기물층은 본 발명에 따른 유기전계발광소자용 화합물을 포함할 수 있다.The at least one organic material layer selected from the single or plural organic material layers may include the compound for an organic electroluminescence device according to the present invention.

본 발명에서 상기 복수의 유기물층은 발광층을 포함하고, 상기 복수의 유기물층은 전자주입층, 전자수송층, 정공차단층, 전자차단층, 정공수송층, 및 정공주입층 중에서 선택된 1종 이상을 추가로 포함할 수 있다.The plurality of organic layers may include at least one selected from the group consisting of an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer .

본 발명에서 상기 정공수송층 및 정공주입층 중에서 선택된 1종 이상은 본 발명에 따른 유기전계발광소자용 화합물을 포함할 수 있다.In the present invention, at least one selected from the hole transporting layer and the hole injecting layer may include the compound for an organic electroluminescence device according to the present invention.

본 발명에서 상기 발광층은 호스트와 도펀트를 포함하고, 상기 호스트는 본 발명에 따른 유기전계발광소자용 화합물을 포함할 수 있다.In the present invention, the light emitting layer includes a host and a dopant, and the host may include a compound for an organic electroluminescence device according to the present invention.

본 발명은 전기적 안정성 및 전자와 홀 수송능력이 우수하며, 삼중항 상태 에너지가 높아 인광발광재료의 발광효율을 향상시킬 수 있는 호스트로서 발광층에 사용 될 수 있는 유기발광소자용 화합물 및 이를 포함하는 유기전기발광소자를 제공할 수 있다.The present invention relates to a compound capable of being used in a light emitting layer as a host which is excellent in electrical stability and electron and hole transporting ability and has high triplet state energy and can improve the luminous efficiency of a phosphorescent light emitting material, An electroluminescent device can be provided.

또한 본 발명은 유기전기발광소자의 전자수송재료나, 홀수송재료에 사용될 수 있는 유기발광소자용 화합물 및 이를 포함하는 유기전기 발광소자를 제공할 수 있다.In addition, the present invention can provide an organic light emitting device compound and an organic electroluminescent device including the same that can be used for an electron transporting material and a hole transporting material of an organic electroluminescence device.

도 1은 본 발명의 일 실시예에 따른 유기전계발광소자의 단면을 나타낸 단면도이다.
도 2는 본 발명의 다른 일 실시예에 따른 유기전계발광소자의 단면을 나타낸 단면도이다.1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view illustrating an organic electroluminescent device according to another embodiment of the present invention.

본 발명은 다양한 변환을 가할 수 있고 여러 가지 실시예를 가질 수 있는 바, 특정 실시예들을 예시하고 상세한 설명에 상세하게 설명하고자 한다. 그러나, 이는 본 발명을 특정한 실시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술 범위에 포함되는 모든 변환, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다. 본 발명을 설명함에 있어서 관련된 공지 기술에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우 그 상세한 설명을 생략한다.The invention is capable of various modifications and may have various embodiments, and particular embodiments are exemplified and will be described in detail in the detailed description. It is to be understood, however, that the invention is not to be limited to the specific embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

또한, 이하에서 사용될 제1, 제2 등과 같이 서수를 포함하는 용어는 다양한 구성요소들을 설명하는데 사용될 수 있지만, 상기 구성요소들은 상기 용어들에 의해 한정되지는 않는다. 상기 용어들은 하나의 구성요소를 다른 구성요소로부터 구별하는 목적으로만 사용된다. 예를 들어, 본 발명의 권리 범위를 벗어나지 않으면서 제1 구성요소는 제2 구성요소로 명명될 수 있고, 유사하게 제2 구성요소도 제1 구성요소로 명명될 수 있다. Furthermore, terms including an ordinal number such as first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.

또한, 어떤 구성요소가 다른 구성요소 상에 "형성되어" 있다거나 "적층되어" 있다고 언급된 때에는, 그 다른 구성요소의 표면상의 전면 또는 일면에 직접 부착되어 형성되어 있거나 적층되어 있을 수도 있지만, 중간에 다른 구성요소가 더 존재할 수도 있다고 이해되어야 할 것이다.In addition, when a component is said to be "formed" or "laminated" on another component, it may be directly attached to, or laminated to, the front or one surface on the surface of the other component. It will be understood that other components may exist in the.

단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 출원에서, "포함하다" 또는 "가지다" 등의 용어는 명세서상에 기재된 특징, 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms "comprise" or "having" are intended to indicate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, and one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or a combination thereof.

본 명세서에서 "치환"이란 별도의 정의가 없는 한, 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, 할로겐기, 히드록시기, 아미노기, C1 내지 C30 아민기, 니트로기, C1 내지 C30 실릴기, C1 내지 C30 알킬기, C1 내지 C30 알킬실릴기, C3 내지 C30 시클로알킬기, C1 내지 C30 헤테로시클로알킬기, C6 내지 C30 아릴기, C1 내지 C30 헤테로 아릴기, C1 내지 C20 알콕시기, C1 내지 C10 트리플루오로알킬기 또는 시아노기로 치환된 것을 의미한다.As used herein, unless otherwise defined, "substituent" means that at least one hydrogen in the substituent or compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C30 silyl group, An alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, It means that it has been replaced by anger.

또한 상기 치환된 할로겐기, 히드록시기, 아미노기, C1 내지 C30 아민기, C3 내지 C30 실릴기, C1 내지 C30 알킬기, C1 내지 C30 알킬실릴기, C3 내지 C30 시클로알킬기, C6 내지 C30 아릴기, C1 내지 C20 알콕시기, C1 내지 C10 트리플루오로알킬기 또는 시아노기 중 인접한 두 개의 치환기가 융합되어 고리를 형성할 수도 있다.A C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 aryl group, a C1 to C30 aryl group, a C1 to C30 aryl group, An alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group may be fused to form a ring.

본 명세서에서 "헤테로"란 별도의 정의가 없는 한, 하나의 작용기 내에 N, O, S 및 P로 이루어진 군에서 선택되는 헤테로 원자를 1 내지 4개 함유하고, 나머지는 탄소인 것을 의미한다.As used herein, unless otherwise defined, it is meant that one functional group contains 1 to 4 heteroatoms selected from the group consisting of N, O, S, and P, and the remainder is carbon.

본 명세서에서 "이들의 조합"이란 별도의 정의가 없는 한, 둘 이상의 치환기가 연결기로 결합되어 있거나, 둘 이상의 치환기가 축합하여 결합되어 있는 것을 의미한다. In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.

본 명세서에서 "알킬(alkyl)기"란 별도의 정의가 없는 한, 지방족 탄화수소기를 의미한다. As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group.

알킬기는 어떠한 이중결합이나 삼중결합을 포함하고 있지 않은 "포화 알킬(saturated alkyl)기" 일 수 있다. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

알킬기는 적어도 하나의 이중결합 또는 삼중결합을 포함하고 있는 "불포화 알킬(unsaturated alkyl)기"일 수도 있다. The alkyl group may be an "unsaturated alkyl group" comprising at least one double bond or triple bond.

"알케닐렌(alkenylene)기"는 적어도 두 개의 탄소원자가 적어도 하나의 탄소-탄소 이중 결합으로 이루어진 작용기를 의미하며, "알키닐렌(alkynylene)기" 는 적어도 두 개의 탄소원자가 적어도 하나의 탄소-탄소 삼중 결합으로 이루어진 작용기를 의미한다. 포화이든 불포화이든 간에 알킬기는 분지형, 직쇄형 또는 환형일 수 있다. "Alkynylene group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynylene group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

알킬기는 C1 내지 C30 알킬기일 수 있다. 보다 구체적으로 알킬기는 C1 내지 C20 알킬기, C1 내지 C10 알킬기 또는 C1 내지 C6 알킬기일 수도 있다.The alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group, a C1 to C10 alkyl group or a C1 to C6 alkyl group.

예를 들어, C1 내지 C4 알킬기는 알킬쇄에 1 내지 4 개의 탄소원자, 즉, 알킬쇄는 메틸, 에틸, 프로필, 이소-프로필, n-부틸, 이소-부틸, sec-부틸 및 t-부틸로 이루어진 군에서 선택됨을 나타낸다.For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.

구체적인 예를 들어 상기 알킬기는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, t-부틸기, 펜틸기, 헥실기, 에테닐기, 프로페닐기, 부테닐기, 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기 등을 의미한다.Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

"아민기"는 아릴아민기, 알킬아민기, 아릴알킬아민기, 또는 알킬아릴아민기를 포함한다.The "amine group" includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.

"시클로알킬(cycloalkyl)기"는 모노시클릭 또는 융합고리 폴리시클릭(즉, 탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다."Cycloalkyl group" includes monocyclic or fused-ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

"헤테로시클로알킬(heterocycloalkyl)기"는 시클로알킬기 내에 N, O, S 및 P로 이루어진 군에서 선택되는 헤테로원자를 1 내지 4개 함유하고, 나머지는 탄소인 것을 의미한다. 상기 헤테로시클로알킬기가 융합고리인 경우, 각각의 고리마다 상기 헤테로 원자를 1 내지 4개 포함할 수 있다."Heterocycloalkyl group" means that the cycloalkyl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the remainder is carbon. When the heterocycloalkyl group is a fused ring, it may contain 1 to 4 heteroatoms in each ring.

"방향족(aromatic)기"는 고리 형태인 작용기의 모든 원소가 p-오비탈을 가지고 있으며, 이들 p-오비탈이 공액(conjugation)을 형성하고 있는 작용기를 의미한다. 구체적인 예로 아릴기와 헤테로아릴기가 있다. "An aromatic group" means a functional group in which all elements of a functional group in the form of a ring have a p-orbital, and these p-orbital forms a conjugation. Specific examples thereof include an aryl group and a heteroaryl group.

"아릴(aryl)기"는 모노시클릭 또는 융합 고리 폴리시클릭(즉, 탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다. An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

"헤테로아릴(heteroaryl)기"는 아릴기 내에 N, O, S 및 P로 이루어진 군에서 선택되는 헤테로원자를 1 내지 4개 함유하고, 나머지는 탄소인 것을 의미한다. 상기 헤테로아릴기가 융합고리인 경우, 각각의 고리마다 상기 헤테로 원자를 1 내지 4개 포함할 수 있다. "Heteroaryl group" means that the aryl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 4 heteroatoms in each ring.

아릴기 및 헤테로아릴기에서 고리의 원자수는 탄소수 및 비탄소원자수의 합이다.In the aryl group and the heteroaryl group, the number of atoms in the ring is the sum of carbon number and non-carbon atom number.

"알킬아릴기" 또는 "아릴알킬기"와 같이 조합하여 사용할 때, 상기에 든 각각의 알킬 및 아릴의 용어는 상기 나타낸 의미와 내용을 가진다.When used in combination, such as "alkylaryl" or "arylalkyl group ", the terms alkyl and aryl of each of the above have the meanings and contents indicated above.

"아릴알킬기"이란 용어는 벤질과 같은 아릴 치환된 알킬 라디칼을 의미하며 알킬기에 포함된다.The term "arylalkyl group " means an aryl substituted alkyl radical, such as benzyl, and is included in the alkyl group.

"알킬아릴기"이란 용어는 알킬 치환된 아릴 라디칼을 의미하며 아릴기에 포함된다.The term "alkylaryl group " means an alkyl substituted aryl radical and is included in the aryl group.

이하, 본 발명의 실시예를 첨부도면을 참조하여 설명하기로 하며, 첨부 도면을 참조하여 설명함에 있어, 동일하거나 대응하는 구성 요소는 동일한 도면번호를 부여하고 이에 대한 중복되는 설명은 생략하기로 한다.DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings. Referring to the accompanying drawings, the same or corresponding components are denoted by the same reference numerals, .

이하 본 발명의 유기전계발광소자에 대해 설명하도록 한다.Hereinafter, the organic electroluminescent device of the present invention will be described.

도 1 및 2를 참고하면, 본 발명의 실시예에 따르면 본 발명에 따른 유기전계발광소자용 화합물을 포함하는 유기전계발광소자(1)가 제공될 수 있다.Referring to FIGS. 1 and 2, an organic electroluminescent device 1 including the compound for an organic electroluminescent device according to the present invention can be provided according to an embodiment of the present invention.

또한 본 발명의 다른 실시예에 따르면, 제1전극(110), 제2전극(150) 및 제1전극(110)과 제2전극(150) 사이에 단수 또는 복수의 유기물층(130)을 포함하는 유기전계발광소자(1)에 있어서, 상기 단수 또는 복수의 유기물층(130) 중에서 선택된 1종 이상의 유기물층은 본 발명에 따른 유기전계발광소자용 화합물을 포함할 수 있다.In addition, according to another embodiment of the present invention, the first electrode 110, the second electrode 150, and a single or a plurality of organic layers 130 are provided between the first electrode 110 and the second electrode 150 In the organic electroluminescent device 1, at least one organic material layer selected from the single or plural organic material layers 130 may include the organic electroluminescent device compound according to the present invention.

여기서, 상기 복수의 유기물층(130)은 발광층(134)을 포함하고, 상기 복수의 유기물층은 전자주입층(131), 전자수송층(132), 정공차단층(133), 전자차단층(135), 정공수송층(136) 및 정공주입층(137) 중에서 선택된 1종 이상을 추가로 포함할 수 있다.The plurality of organic layers 130 may include a light emitting layer 134 and the plurality of organic layers may include an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, The hole transporting layer 136 and the hole injecting layer 137 may be further included.

또한 상기 정공수송층(136) 및 정공주입층(137) 중에서 선택된 1종 이상은 본 발명에 따른 유기전계발광소자용 화합물을 포함할 수 있다.Further, at least one selected from the hole transport layer 136 and the hole injection layer 137 may include the compound for an organic electroluminescence device according to the present invention.

또한 상기 발광층(134)은 호스트와 도펀트를 포함하고, 상기 호스트는 본 발명에 따른 유기전계발광소자용 화합물을 포함할 수 있다.The light emitting layer 134 may include a host and a dopant, and the host may include a compound for an organic electroluminescent device according to the present invention.

상기 유기전계발광소자는 바람직하게는 투명기판에 의하여 지지된다. 투명기판의 재료로는 양호한 기계적 강도, 열안정성 및 투명성을 갖는 한 특별한 제한은 없다. 구체적인 예를 들면, 유리, 투명 플라스틱 필름 등을 사용할 수 있다.The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.

본 발명의 유기전계발광소자의 양극재료로서는 4eV 이상의 일함수를 갖는 금속, 합금, 전기전도성 화합물 또는 이의 혼합물을 사용할 수 있다. 구체적으로는 금속인 Au 또는 CuI, ITO(인듐 주석 산화물), SnO2 및 ZnO와 같은 투명 전도성 재료를 들 수 있다. 양극 필름의 두께는 10 내지 200nm 가 바람직하다.As the cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO 2 and ZnO, which are metals, can be mentioned. The thickness of the positive electrode film is preferably 10 to 200 nm.

본 발명의 유기전계발광소자의 음극 재료로서는 4eV 미만의 일함수를 갖는 금속, 합금, 전기 전도성 화합물 또는 이의 혼합물을 사용할 수 있다. 구체적으로는, Na, Na-K 합금, 칼슘, 마그네슘, 리튬, 리튬 합금, 인듐, 알루미늄, 마그네슘 합금, 알루미늄 합금을 들 수 있다. 이외에, 알루미늄/AlO2, 알루미늄/리튬, 마그네슘/은 또는 마그네슘/인듐 등도 사용될 수 있다. 음극필름의 두께는 10 내지 200nm 가 바람직하다.As the anode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV may be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO 2 , aluminum / lithium, magnesium / silver or magnesium / indium may be used. The thickness of the negative electrode film is preferably 10 to 200 nm.

유기 EL 소자의 발광효율을 높이기 위해서는 하나 이상의 전극은 바람직하게는 10% 이상의 광투과율을 가지는 것이 바람직하다. 전극의 쉬트저항은 바람직하게는 수백 Ω/mm 이하이다. 전극의 두께는 10nm 내지 1㎛, 보다 바람직하게는 10 내지 400nm 이다. 이러한 전극은 화학적 기상증착(CVD), 물리적 기상증착(PVD) 등의 기상증착법 또는 스퍼터링법을 통하여 상기한 전극 재료를 박막으로 형성하여 제조할 수 있다.In order to increase the luminous efficiency of the organic EL device, at least one electrode preferably has a light transmittance of 10% or more. The sheet resistance of the electrode is preferably several hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.

또한 본 발명의 목적에 적합하게 본 발명의 유기전계발광소자용 화합물이 사용될 때, 공지된 정공수송 물질, 정공주입 물질, 발광층 물질, 발광층의 호스트 물질, 전자수송 물질, 및 전자주입 물질이 상기 각각의 유기물층에서 단독으로 사용되거나 또는 본 발명의 유기전계발광소자용 화합물과 선택적으로 병행하여 사용될 수 있다.When the compound for an organic electroluminescence device of the present invention is used for the purpose of the present invention, the known hole transporting material, hole injecting material, light emitting layer material, host material of the light emitting layer, electron transporting material, Or may be used in combination with the organic electroluminescent device compound of the present invention selectively.

정공 수송 물질로서 N,N-dicarbazolyl-3,5-benzene(mCP), poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS), N, N’-di(1-naphthyl)-N,N’-diphenylbenzidine(NPD), N,N'-디페닐-N,N'-디(3-메틸페닐)-4,4'-디아미노비페닐(TPD), N,N'-디페닐-N,N'-디나프틸-4,4'-디아미노비페닐, N,N,N'N'-테트라-p-톨릴-4,4'-디아미노비페닐, N,N,N'N'-테트라페닐-4,4'-디아미노비페닐, 코퍼(II)1,10,15,20-테트라페닐-21H,23H-포피린 등과 같은 포피린(porphyrin)화합물 유도체, 주쇄 또는 측쇄내에 방향족 3차아민을 갖는 중합체, 1,1-비스(4-디-p-톨릴아미노페닐)시클로헥산, N,N,N-트리(p-톨릴)아민, 4, 4', 4'-트리스[N-(3-메틸페닐)-N-페닐아미노]트리페닐아민과 같은 트리아릴아민 유도체, N-페닐카르바졸 및 폴리비닐카르바졸과 같은 카르바졸 유도체, 무금속 프탈로시아닌, 구리프탈로시아닌과 같은 프탈로시아닌 유도체, 스타버스트 아민 유도체, 엔아민스틸벤계 유도체, 방향족 삼급아민과 스티릴 아민 화합물의 유도체, 및 폴리실란 등을 들 수 있다.N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'- (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD) N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N'N'N'N'- Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like, aromatic tertiary (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as nonmetal phthalocyanine and copper phthalocyanine, An aminostilbene derivative, a derivative of an aromatic tertiary amine and a styrylamine compound, and polysilane.

전자 수송 물질로서 diphenylphosphine oxide-4-(triphenylsilyl)phenyl (TSPO1), Alq3, 2,5-디아릴 실롤 유도체(PyPySPyPy), 퍼플루오리네이티드 화합물(PF-6P), Octasubstituted cyclooctatetraene 화합물(COTs)을 들 수 있다.The diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3, 2,5- diaryl silole derivatives (PyPySPyPy), perfluoro rineyi suited compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) as an electron transport material .

본 발명의 유기전계발광소자에 있어서, 전자 주입층, 전자 수송층, 정공 수송층 및 정공 주입층은 상기한 화합물의 하나 이상의 종류를 함유하는 단일 층으로 형성되거나, 또는 상호 적층된, 상이한 종류의 화합물을 함유하는 복수의 층으로 구성될 수 있다.In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.

발광재료로서 예를 들면 축광 형광재료, 형광증백제, 레이저 색소, 유기 신틸레이터 및 형광 분석용 시약을 들 수 있다. 구체적으로는, 카바졸계 화합물, 포스핀옥사이드계 화합물, 카바졸계 포스핀옥사이드 화합물, bis((3,5-difluoro-4-cyanophenyl)pyridine) iridium picolinate(FCNIrpic), tris(8-hydroxyquinoline) aluminum(Alq3), 안트라센, 페난트렌, 피렌, 크리센, 페릴렌, 코로넨, 루브렌 및 퀴나크리돈과 같은 폴리아로마틱 화합물, 퀴터페닐과 같은 올리고페닐렌 화합물, 1,4-비스 (2-메틸스티릴)벤젠, 1,4-비스(4-메틸스티릴)벤젠, 1,4-비스(4-메틸-5-페닐-2-옥사졸릴)벤젠, 1,4-비스(5-페닐-2-옥사졸릴)벤젠, 2,5-비스(5-t-부틸-2-벤즈옥사졸릴)사이오펜, 1,4-디페닐-1,3-부타디엔, 1,6-디페닐-1,3,5-헥사트리엔,1,1,4,4-테트라페닐-1,3-부타디엔과 같은 액체신틸레이션용 신틸레이터, 옥신 유도체의 금속착체, 쿠마린 색소, 디시아노메틸렌피란 색소, 디시아노메틸렌사이오피란 색소, 폴리메틴 색소, 옥소벤즈안트라센 색소, 크산텐 색소, 카르보스티릴 색소, 페릴렌 색소, 옥사진 화합물, 스틸벤 유도체, 스피로 화합물, 옥사디아졸 화합물 등을 들 수 있다.Examples of the light emitting material include a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, a carbazole compound, a phosphine oxide compound, a carbazole-based phosphine oxide compound, bis (3,5-difluoro-4-cyanophenyl) pyridine, iridium picolinate (FCNIrpic), tris (8-hydroxyquinoline) aluminum Alq 3 ), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, 1,4- Bis (4-methylstyryl) benzene, 1,4-bis (4-methyl- Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6- Liquid scintillation scintillators such as 3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, dicyanomethylenepyran dyes, dicyanomethylene Cyopyran pigment, polymethine pigment, oxobenzanthracene There may be mentioned a colorant, a xanthene colorant, a carbostyryl colorant, a perylene colorant, an oxazine compound, a stilbene derivative, a spiro compound, and an oxadiazole compound.

본 발명의 유기 EL 소자를 구성하는 각 층은 진공 증착, 스핀 코팅 또는 캐스팅과 같은 공지된 방법을 통하여 박막으로 형성시키거나, 각 층에서 사용되는 재료를 이용하여 제조할 수 있다. 이들 각층의 막두께에 대해서는 특별한 제한은 없으며, 재료의 특성에 따라 알맞게 선택할 수 있으나, 보통 2nm 내지 5,000nm의 범위에서 결정될 수 있다.Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.

본 발명의 따른 유기전계발광소자용 화합물은 진공 증착법에 의하여 형성될 수 있으므로, 박막 형성 공정이 간편하고, 핀홀(pin hole)이 거의 없는 균질한 박막으로 용이하게 얻을 수 있는 장점이 있다.The compound for an organic electroluminescence device according to the present invention can be formed by a vacuum deposition method, so that it is advantageous that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.

[실시예] [Example]

이하, 실시예를 통하여 본 발명에 따른 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자의 제조방법을 더욱 구체적으로 설명한다. 그러나 이는 예시를 위한 것으로서 이에 의하여 본 발명의 범위가 한정되는 것이 아니다.Hereinafter, the compound for an organic electroluminescent device according to the present invention and the method for manufacturing the organic electroluminescent device including the same will be described in more detail with reference to the following examples. However, this is for the purpose of illustration only and is not intended to limit the scope of the invention.

실시예Example 1: 화합물 1의 합성 1: Synthesis of compound 1

(1) (One) 제조예Manufacturing example 1-1 : 중간체 1-1 합성 1-1: Intermediate 1-1 Synthesis

Figure pat00012
Figure pat00012

9-phenyl-9-bromofluoren (15.13g, 0.0471mol/시안(중국))을 정제된 THF용액 200ml에 녹인 후 질소 환류 하에서 -78℃로 낮추고, n-BuLi (3.02g, 0.047mol/시그마알드리치)을 적가한 후 2시간 동안 교반시켜 주었다. 그 후 트리메틸보레이트(8.31g, 0.08mol/시그마알드리치)를 저온에서 천천히 넣어 준 후 온도를 상승시켜 상온에서 24시간 교반하여 반응시켰다. 염산(10M)을 넣어(리트머스 종이로 확인) 중화 후 반응을 종료하였다. 디클로로메탄으로 추출한 후 헥산으로 재결정하여 중간체 1-1을 5.12g수득하였다. (수율: 38%)9-phenyl-9-bromofluorene (15.13 g, 0.0471 mol / cyan (China)) was dissolved in 200 ml of a refluxed THF solution and then cooled to -78 ° C under nitrogen reflux and n-BuLi (3.02 g, 0.047 mol / Sigma Aldrich) And the mixture was stirred for 2 hours. After that, trimethyl borate (8.31 g, 0.08 mol / Sigma Aldrich) was added slowly at a low temperature, and then the temperature was raised, and the mixture was reacted at room temperature for 24 hours with stirring. Hydrochloric acid (10 M) was added (confirmed by litmus paper) and the reaction was terminated after neutralization. After extraction with dichloromethane, recrystallization from hexane gave 5.12 g of intermediate 1-1. (Yield: 38%).

(2) (2) 제조예Manufacturing example 1-2 : 중간체 1-2 합성 1-2: Intermediate 1-2 Synthesis

Figure pat00013
Figure pat00013

중간체 1-1 (25.18g, 0.088mol)과 5-bromo-2-phenyl-1H-benzoimidazole (24g, 0.088mol/시그마알드리치)을 톨루엔 용액에 넣고 Pd(pph)4(팔라듐테트라키스) (0.97g, 0.00084mol/피엔에이치테크), K2CO3 (17.04g, 0.126mol)을 넣고 질소 하에서 12시간 환류 교반하여 반응시켰다. 반응 종료 후 디클로로메탄으로 추출하고 실리카 칼럼 정제(EA:hexane) 하여 중간체 1-2를 38.24g 수득하였다. (수율: 82%)Pd (pph) 4 (palladium tetrakis) (0.97 g, 0.088 mol, Sigma Aldrich) was added to a toluene solution of Intermediate 1-1 (25.18 g, 0.088 mol) and 5-bromo-2-phenyl- , 0.00084mol / Pienza HI Tech), K 2 into a CO 3 (17.04g, 0.126mol) was reacted with stirring for 12 hours under reflux under nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and purified by silica column (EA: hexane) to obtain 38.24 g of intermediate 1-2. (Yield 82%)

(3) (3) 제조예Manufacturing example 1-3 : 화합물 1 합성 1-3: Synthesis of compound 1

Figure pat00014
Figure pat00014

중간체 1-2 (59.2g, 0.137mol)에 4-(3-phenyl)dibenzothiopen (46.48g, 0.137mol/중국) NaOtBu (36.8g, 0.401mol), 촉매 Pd2(dba)3 (6.69g, 0.007mol), P(t-Bu)3 (2.95g, 0.0146mol)과 Toluene 1200ml를 넣고 100℃에서 환류시켜 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 1을 76g 수득하였다. (수율: 80%)4- (3-phenyl) dibenzothiopen (46.48 g, 0.137 mol / in China) NaOtBu (36.8 g, 0.401 mol), catalyst Pd2 (dba) 3 (6.69 g, 0.007 mol ), P (t-Bu) 3 (2.95 g, 0.0146 mol) and Toluene (1200 ml) were added and reacted at 100 ° C under reflux. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 76 g of Compound 1. (Yield: 80%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.43/S, 7.26/M, 7.54/D, 7.47/D, 7.46/D, 7.52/D, 7.41/M, 8.09/D, 8.20/D, 7.58/M, 8.41/D, 7.98/D, 7.50/M, 7.52/M, 8.45/D) 2H (7.55/D, 7.28/M, 7.38/M, 7.87/D, 7.11/D, 7.33/M, 8.28/D) 3H (7.51/M)D, 7.46 / D, 7.52 / D, 7.41 / M, 8.09 / D, 8.20 / D, 7.58 / M, 8.41 / D, 7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D) 2H (7.55 / D, 7.28 / M, 7.38 / M, 7.87 / D, 8.28 / D) 3H (7.51 / M)

LC/Mass [M+H]+: 691.87LC / Mass [M + H] < + >: 691.87

실시예Example 2: 화합물 2의 합성 2: Synthesis of Compound 2

Figure pat00015
Figure pat00015

중간체 1-2 (30g, 0.094mol)에 2-(4-bromophenyl)-1-phenyl-benzoimidazole (35.9g, 0.102mol/시그마알드리치) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 2를 51.5g 수득하였다. (수율: 78%)To the intermediate 1-2 (30 g, 0.094 mol) was added 2- (4-bromophenyl) -1-phenyl-benzoimidazole (35.9 g, 0.102 mol / Sigma Aldrich) NaOtBu (18.4 g, 0.20 mol) (T-Bu) 3 (1.47 g, 0.0078 mol), and Toluene (600 ml) were added and reacted at 100 ° C under reflux. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 51.5 g of Compound 2. (Yield 78%)

H-NMR(200MHz, CDCl3): δ ppm, 1H (8.56/D, 7.59/D, 7.45/M, 7.41/M, 7.43/S, 7.54/D, 7.47/D, 7.26/M) 2H (7.22/M, 7.28/M, 7.38/M, 7.87/D, 7.55/D, 7.11/D, 7.11/D, 7.33/M, 8.28/D, 7.51/M, 7.68/D, 7.79/D, 7.50/D, 7.58/M)7.47 / D, 7.47 / D, 7.26 / M) 2H (7.22 / D, 7.56 / D, 7.59 / D, 7.45 / M, 7.41 / M, 7.28 / M, 7.38 / M, 7.87 / D, 7.55 / D, 7.11 / D, 7.11 / D, 7.33 / M, 8.28 / D, 7.51 / M, 7.68 / D, 7.79 / 7.58 / M)

LC/Mass [M+H]+: 701.84LC / Mass [M + H] < + >: 701.84

실시예Example 3: 화합물 3의 합성 3: Synthesis of Compound 3

Figure pat00016
Figure pat00016

중간체 1-2 (30g, 0.094mol)에 3-(4-bromopenyl)-benzothiopen (34.6g, 0.102mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 반응한다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 3을 55.5g 수득하였다. (수율: 85%)3- (4-bromophenyl) -benzothiopen (34.6 g, 0.102 mol / in China) NaOtBu (18.4 g, 0.20 mol) and catalyst Pd2 (dba) 3 (3.38 g, 0.004 mol ), P (t-Bu) 3 (1.47 g, 0.0078 mol) and Toluene (600 ml) were added and reacted at 100 ° C under reflux. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 55.5 g of Compound 3. (Yield: 85%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/D, 7.41/M, 7.35/S, 7.16/D, 7.26/D, 3.70/D, 3.57/D) 2H (7.28/M, 7.55/D, 7.38/M, 7.87/D, 7.11/D, 7.11/D, 7.33/M, 7.68/D, 8.28/D, 7.51/M, 7.79/D, 5.80/M, 5.90/M)(7.26 / M, 7.54 / D, 7.47 / D, 7.43 / D, 7.41 / M, 7.35 / S, 7.16 / D, 7.26 / D, 3.70 / D, D, 7,11 / D, 7,11 / D, 7.33 / M, 7.68 / D, 8.28 / D, 7.51 / M, 7.79 / D, 5.80 / M, 5.90 / M)

LC/Mass [M+H]+: 693.88LC / Mass [M + H] < + >: 693.88

실시예Example 4: 화합물 4의 합성 4: Synthesis of Compound 4

Figure pat00017
Figure pat00017

중간체 1-2 (59.2g, 0.137mol)에 N-(4-bromobenzen)-N-phenyl-(dibenzothiopen-4yl)amine (58.9g, 0.137mol/중국) NaOtBu (36.8g, 0.401mol), 촉매 Pd2(dba)3 (6.69g, 0.007mol), P(t-Bu)3 (2.95g, 0.0146mol)과 Toluene 1200ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 4를 85.9g 수득하였다. (수율: 80%)4-bromobenzen-N-phenyl- (dibenzothiopen-4yl) amine (58.9 g, 0.137 mol / (dba) 3 (6.69 g, 0.007 mol), P (t-Bu) 3 (2.95 g, 0.0146 mol) and 1,200 ml of toluene were placed and refluxed at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 85.9 g of Compound 4. [ (Yield: 80%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/S, 7.41/M, 6.86/D, 7.27/M, 7.81/D, 8.45/D, 7.52/M, 7.50/M, 7.98/D, 6.81/M) 2H (7.28/D, 7.38/M, 7.87/D, 7.11/D, 7.55/D, 7.33/M, 7.37/D, 8.28/D, 7.51/M, 7.20/M) 4H (6.63/D)(7.26 / M, 7.54 / D, 7.47 / D, 7.43 / S, 7.41 / M, 6.86 / D, 7.27 / M, 7.81 / D, 8.45 / D, 7.38 / D, 7.38 / D, 7.38 / M, 7.87 / D, 7.11 / D, 7.55 / D, 7.33 / M, 7.37 / D, 7.51 / M, 7.20 / M) 4H (6.63 / D)

LC/Mass [M+H]+: 782.98LC / Mass [M + H] < + >: 782.98

실시예Example 5: 화합물 5의 합성 5: Synthesis of Compound 5

Figure pat00018
Figure pat00018

중간체 1-2 (59.2g, 0.137mol)에 2(4-bromobenzen)-triphenylene (52.5g, 0.137mol/시그마알드리치) NaOtBu (36.8g, 0.401mol), 촉매 Pd2(dba)3 (6.69g, 0.007mol), P(t-Bu)3 (2.95g, 0.0146mol)과 Toluene 1200ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 5를 91.87g 수득하였다. (수율: 91%)
To the intermediate 1-2 (59.2 g, 0.137 mol) was added 2 (4-bromobenzen) -triphenylene (52.5 g, 0.137 mol / Sigma Aldrich) NaOtBu (36.8 g, 0.401 mol), catalyst Pd2 (dba) P (t-Bu) 3 (2.95 g, 0.0146 mol) and Toluene (1200 ml) were charged and refluxed at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 91.87 g of Compound 5. (Yield: 91%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (9.15/S, 8.18/D, 8.04/D, 7.41/M, 7.47/D, 7.43/S, 7.54/D, 7.26/M) 2H (7.51/M, 8.28/D, 7.38/M, 7.87/D, 7.55/D, 7.55/D, 7.28/M, 7.11/D, 7.68/D, 7.79/D, 7.82/M, 8.12/D, 8.93/D, 7.88/M, 7.33/M)(7.51 / S, 8.18 / D, 8.04 / D, 7.41 / M, 7.47 / D, 7.43 / S, 7.54 / D, 7.26 / M) M, 8.28 / D, 7.38 / M, 7.87 / D, 7.55 / D, 7.55 / D, 7.28 / M, 7.11 / D, 7.68 / D, 7.79 / D, 7.82 / 7.88 / M, 7.33 / M)

LC/Mass [M+H]+: 735.90LC / Mass [M + H] < + >: 735.90

실시예Example 6: 화합물 6의 합성 6: Synthesis of Compound 6

Figure pat00019
Figure pat00019

중간체 1-2 (30g, 0.094mol)에 N-(4-bromopenyl)-N-penyldipyrolicthiopen (36.9g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 6을 45.6g 수득하였다. (수율: 65%)To the intermediate 1-2 (30 g, 0.094 mol) was added N- (4-bromophenyl) -N-penyldipyrolic thiopen (36.9 g, 0.094 mol / 0.004 mol), P (t-Bu) 3 (1.47 g, 0.0078 mol) and 600 ml of toluene were placed and reacted at 100 ° C under reflux. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 45.6 g of Compound 6. (Yield: 65%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.41/M, 7.45/M, 7.54/D, 7.43/S, 7.47/D, 7.26/M) 2H (7.28/M, 8.28/D, 7.51/M, 7.58/M, 7.50/D, 6.19/D, 7.26/D, 7.87/D, 7.38/M, 7.55/D, 7.33/M, 7.11/D) 4H (7.62)(7.28 / M, 8.28 / D, 7.51 / M, 7.44 / D, 7.46 / M, 7.58 / M, 7.50 / D, 6.19 / D, 7.26 / D, 7.87 / D, 7.38 / M, 7.55 / D, 7.33 / M,

LC/Mass [M+H]+: 745.92LC / Mass [M + H] < + >: 745.92

실시예Example 7: 화합물 7의 합성 7: Synthesis of Compound 7

Figure pat00020
Figure pat00020

중간체 1-2 (30g, 0.094mol)에 N-(biphenyl-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine (48.55g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 4시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 7을 60.52g 수득하였다. (수율: 74%)4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (48.55 g, 0.094 mol / ), P (t-Bu) 3 (1.47 g, 0.0078 mol) and Toluene (600 ml) were added and the mixture was refluxed at 100 ° C for 4 hours Lt; / RTI > After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 60.52 g of Compound 7. (Yield: 74%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/S, 6.75/S, 6.58/D, 7.62/D) 2H (7.11/D, 1.72/S, 7.41/M, 7.33/M, 8.28/D, 6.69/D, 7.54/D, 7.54/D, 7.52/D, 6.63/D, 7.37/D) 3H (7.55/D, 7.87/D, 7.37/M) 4H (7.51/M)(7,11 / D, 1.72 / D), 7.47 / D, 7.43 / S, 6.75 / S, 6.58 / D, 7.62 / D) D, 7.37 / D, 7.37 / D) 3H (7.55 / D, 7.87 / D, 7.37 / D, 7.54 / D, 7.52 / D, M) < / RTI > 4H (7.51 / M)

LC/Mass [M+H]+: 869.09LC / Mass [M + H] < + >: 869.09

실시예Example 8: 화합물 8의 합성 8: Synthesis of Compound 8

Figure pat00021
Figure pat00021

중간체 1-2 (59.2g, 0.137mol)에 N-(4-bromophenyl)-N-(dibenzo[b,d]thiophen-4-yl)dibenzo[b,d]thiophen-4-amine (73.5g, 0.137mol/시안(중국)) NaOtBu (36.8g, 0.401mol), 촉매 Pd2(dba)3 (6.69g, 0.007mol), P(t-Bu)3 (2.95g, 0.0146mol)과 Toluene 1200ml를 넣고 100℃에서 환류시켜 6시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 8을 107.8g 수득하였다. (수율: 88%)Dibenzo [b, d] thiophen-4-amine (73.5 g, 0.137 mol) was added to Intermediate 1-2 (59.2 g, P (t-Bu) 3 (2.95 g, 0.0146 mol) and Toluene (1200 ml) were charged into a reaction vessel equipped with a stirrer, The reaction was refluxed at 100 ° C and allowed to react for 6 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 107.8 g of Compound 8. (Yield: 88%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.41/M, 7.43/S, 7.47/D, 7.54/D, 7.26/M) 2H (7.51/M, 8.28/D, 7.81/D, 7.27/M, 6.86/D, 6.63/D, 7.37/D, 7.87/D, 7.38/M, 7.28/M, 7.55/D, 7.33/M, 7.11/D, 7.98/D, 7.50/M, 7.52/M, 8.45/D)(7.51 / M, 8.28 / D, 7.81 / D, 7.27 / D, 7.47 / D, 7.54 / D, 7.26 / M, 6.86 D, 6.63 D, 7.37 D, 7.87 D, 7.38 M, 7.28 M, 7.55 D, 7.33 M, 7.11 D, 7.98 D, 7.50 M, 7.52 M, 8.45 / D)

LC/Mass [M+H]+: 889.12LC / Mass [M + H] < + >: 889.12

실시예Example 9: 화합물 9의 합성 9: Synthesis of Compound 9

Figure pat00022
Figure pat00022

중간체 1-2 (30g, 0.094mol)에 2-(4-bromophenyl)-1-phenyl-1H-dibenzo[e,g]indole (42.14g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 9를 55.03g 수득하였다. (수율: 73%)Indole (42.14 g, 0.094 mol / in China) NaOtBu (18.4 g, 0.20 mol) was added to Intermediate 1-2 (30 g, 0.094 mol) The catalyst Pd2 (dba) 3 (3.38g, 0.004mol) and P (t-Bu) 3 (1.47g, 0.0078mol) and 600ml of toluene were added and refluxed at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 55.03 g of Compound 9. (Yield 73%)

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/S, 7.45/M, 7.41/M, 6.60/S) 2H (7.28/M, 7.38/M, 7.87/D, 8.28/D, 7.51/M, 7.68/D, 7.79/D, 7.50/D, 7.58/M, 8.12/D, 7.82/M, 7.88/D, 8.93/D, 7.11/D, 7.55/D, 7.33/M)(7.28 / M, 7.38 / M, 7.54 / D, 7.47 / D, 7.43 / S, 7.45 / M, 7.41 / M, 6.60 / M, 7.87 / D, 8.28 / D, 7.51 / M, 7.68 / D, 7.79 / D, 7.50 / D, 7.58 / M, 8.12 / D, 7.82 / M, 7.88 / D, 8.93 / D, 7.55 / D, 7.33 / M)

LC/Mass [M+H]+: 800.97LC / Mass [M + H] < + >: 800.97

실시예Example 10: 화합물 10의 합성 10: Synthesis of Compound 10

Figure pat00023
Figure pat00023

중간체 1-2 (30g, 0.094mol)에 6-(4-bromophenyl)-5-phenyl-5H-pyrrolo[2,3-f][1,10]phenanthroline (42.33g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 10을 61.2g 수득하였다. (수율: 81%)5-pyrrolo [2,3-f] [1,10] phenanthroline (42.33 g, 0.094 mol / in China) NaOtBu (0.2 g, 0.094 mol) was added to Intermediate 1-2 (1.47 g, 0.0078 mol) of Pd (dba) 3 (3.38 g, 0.004 mol) and P (t-Bu) 3 and 600 ml of toluene were placed and reacted at 100 ° C. for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 61.2 g of Compound 10. (Yield: 81%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/S, 7.41/M, 7.45/M, 6.60/S) 2H (7.28/M, 7.38/M, 7.87/D, 7.11/D, 7.55/D, 7.33/M, 8.83/D, 8.38/D, 7.50/D, 7.51/M, 8.28/D, 7.68/D, 7.79/D) 4H (7.58/M)(7.28 / M, 7.38 / M, 7.54 / D, 7.47 / D, 7.43 / S, 7.41 / M, 7.45 / M, 6.60 / D, 7,11 / D, 7.55 / D, 7.33 / M, 8.83 / D, 8.38 / D, 7.50 / D, 7.51 / M, 8.28 / D, 7.68 / D, 7.79 / M)

LC/Mass [M+H]+: 802.95LC / Mass [M + H] < + >: 802.95

실시예Example 11: 화합물 11의 합성 11: Synthesis of Compound 11

Figure pat00024
Figure pat00024

중간체 1-2 (30g, 0.094mol)에 4-bromobiphenyl(D:중수소) (23.34g, 0.094mol/시그마알드리치) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 11을 45g 수득하였다. (수율: 81%)To the intermediate 1-2 (30 g, 0.094 mol) was added 4-bromobiphenyl (D: deuterium) (23.34 g, 0.094 mol / Sigma Aldrich) NaOtBu (18.4 g, 0.20 mol), catalyst Pd2 (dba) 3 (3.38 g, 0.004 mol ), P (t-Bu) 3 (1.47 g, 0.0078 mol) and 600 ml of toluene were added, and the mixture was refluxed at 100 ° C for reaction for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 45 g of Compound 11. (Yield: 81%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/S, 7.41/M) 2H (8.28/D, 7.51/M, 7.68/D, 7.79/D, 7.11/D, 7.55/D, 7.33/M, 7.87/D, 7.38/M, 7.28/M)(8.28 / D, 7.51 / M, 7.68 / D, 7.79 / D, 7.47 / D, 7.43 / D, 7.11 / D, 7.55 / D, 7.33 / M, 7.87 / D, 7.38 /

LC/Mass [M+H]+: 590.75LC / Mass [M + H] < + >: 590.75

실시예Example 12: 화합물 12의 합성 12: Synthesis of Compound 12

Figure pat00025
Figure pat00025

중간체 1-2 (30g, 0.094mol)에 2-(4-bromophenyl)pyrido[2,3-f][1,7]phenanthroline (36.3g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 12를 56.33g 수득하였다. (수율: 81%)Pyridine [2,3-f] [1,7] phenanthroline (36.3g, 0.094mol / China) NaOtBu (18.4g, 0.20mol) in Intermediate 1-2 (30g, 0.094mol) The catalyst Pd2 (dba) 3 (3.38g, 0.004mol) and P (t-Bu) 3 (1.47g, 0.0078mol) and 600ml of toluene were added and refluxed at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 56.33 g of Compound 12. (Yield: 81%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (8.10/D, 7.35/D, 7.41/M, 7.47/D, 7.54/D, 7.43/S, 7.26/M) 2H (7.55/D, 7.11/D, 7.28/M, 7.33/M, 7.38/M, 7.87/D, 7.71/D, 8.30/D, 8.28/D, 7.51/M, 8.38/D, 8.83/D, 7.58/M)7.35 / D, 7.47 / D, 7.54 / D, 7.43 / S, 7.26 / M) 2H (7.55 / D, 7.11 / D, 7.28 / M, 7.33 / M, 7.38 / M, 7.87 / D, 7.71 / D, 8.30 / D, 8.28 / D, 7.51 / M, 8.38 / D, 8.83 / D, 7.58 /

LC/Mass [M+H]+: 738.86LC / Mass [M + H] < + >: 738.86

실시예Example 13: 화합물 13의 합성 13: Synthesis of compound 13

Figure pat00026
Figure pat00026

중간체 1-2 (30g, 0.094mol)에 N-(4-bromophenyl)-N-(pyridin-3-yl)pyridin-3-amine (30.66g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 13을 53.66g 수득하였다. (수율: 84%) Pyridin-3-yl) pyridin-3-amine (30.66g, 0.094mol / China) NaOtBu (18.4g, 0.20mol) was added to Intermediate 1-2 (30g, 0.094mol) (3.78 g, 0.004 mol), P (t-Bu) 3 (1.47 g, 0.0078 mol) and 600 ml of toluene were placed in a reactor and reacted at 100 ° C. for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 53.66 g of Compound 13. (Yield: 84%)

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.41/M, 7.47/D, 7.54/D, 7.43/S, 7.26/M) 2H (7.28/M, 7.38/M, 7.55/D, 7.11/D, 7.33/M, 7.87/D, 8.28/D, 7.51/M, 7.37/D, 6.63/D, 7.27/D, 6.63/D, 7.27/D, 7.36/M, 8.09/D, 8.04/D)M, 7.38 / M, 7.55 / D, 7.11 / D, 7.44 / D, 7.54 / D, 7.43 / S, 7.26 / D, 7.33 / M, 7.87 / D, 8.28 / D, 7.51 / M, 7.37 / D, 6.63 / D, 7.27 / D, 6.63 / D, 7.27 / D, 7.36 / M, 8.09 /

LC/Mass [M+H]+: 678.81LC / Mass [M + H] < + >: 678.81

실시예Example 14: 화합물 14의 합성 14: Synthesis of compound 14

Figure pat00027
Figure pat00027

중간체 1-2 (59.2g, 0.137mol)에 N-(2,3'-bipyridin-5-yl)-N-(4-bromophenyl)-2,3'-bipyridin-5-amine (65.8g, 0.137mol/시안(중국)) NaOtBu (36.8g, 0.401mol), 촉매 Pd2(dba)3 (6.69g, 0.007mol), P(t-Bu)3 (2.95g, 0.0146mol)과 Toluene 1200ml를 넣고 100℃에서 환류시켜 6시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 14를 100.54g 수득하였다. (수율: 88%)Bipyridin-5-yl) -N- (4-bromophenyl) -2,3'-bipyridin-5-amine (65.8 g, 0.137 mol) was added to Intermediate 1-2 (59.2 g, 0.137 mol) (2.69 g, 0.0146 mol) of Pd (dba) 3 (6.69 g, 0.007 mol) and Pd (t-Bu) Lt; 0 > C and reacted for 6 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 100.54 g of Compound 14. (Yield: 88%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.41/M, 7.43/S, 7.47/D, 7.54/D, 7.26/M) 2H (7.28/M, 7.55/D, 7.11/D, 7.38/M, 7.87/D, 7.33/M, 7.37/D, 6.63/D, 8.28/D, 7.51/M, 8.95/D, 8.53/D, 7.14/D, 7.70/D, 9.30/D, 7.01/S, 7.65/S)(7.28 / M, 7.55 / D, 7.11 / D, 7.38 / M, 7.47 / D, 7.54 / D, 7.26 / D, 7.03 / D, 7.33 / D, 6.63 / D, 8.28 / D, 7.51 / M, 8.95 / D, 8.53 / D, 7.14 / D, 7.70 / D, 7.65 / S)

LC/Mass [M+H]+: 832.98LC / Mass [M + H] < + >: 832.98

실시예Example 15: 화합물 15의 합성 15: Synthesis of compound 15

Figure pat00028
Figure pat00028

중간체 1-2 (30g, 0.094mol)에 2-(4-bromophenyl)(dipyridin-4-yl)thiophen (29.54g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 15를 54.86g 수득하였다. (수율: 84%)2- (4-bromophenyl) (dipyridin-4-yl) thiophen (29.54g, 0.094mol / China) NaOtBu (18.4g, 0.20mol), Catalyst Pd2 (dba) 3 (1.47 g, 0.0078 mol) of P (t-Bu) 3 and 600 ml of toluene were placed, and the mixture was refluxed at 100 ° C and reacted for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 54.86 g of Compound 15. (Yield: 84%)

H-NMR(200MHz, CDCl3): δ ppm, 1H (9.51/S, 8.43/D, 7.38/D, 8.98/S, 9.24/S, 7.41/M, 7.26/M, 7.47/D, 7.54/D, 7.43/S) 2H (7.28/M, 7.55/D, 7.38/M, 7.87/D, 7.11/D, 7.33/M, 8.28/D, 7.51/M, 7.68/D, 7.79/D)7.47 / D, 7.54 / D, 7.38 / D, 8.98 / S, 9.24 / S, 7.41 / M, 7.26 / M, 7.38 / D, 7.33 / M, 8.28 / D, 7.51 / M, 7.68 / D, 7.79 / D)

LC/Mass [M+H]+: 693.84LC / Mass [M + H] < + >: 693.84

실시예Example 16: 화합물 16의 합성 16: Synthesis of Compound 16

Figure pat00029
Figure pat00029

중간체 1-2 (30g, 0.094mol)에 N-(4-bromophenyl)(dipyrimidin-4-yl)pyrole (30.66g, 0.094mol/중국) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 16을 53.67g 수득하였다. (수율: 84%)4-yl) pyrole (30.66 g, 0.094 mol / in China) NaOtBu (18.4 g, 0.20 mol) and the catalyst Pd2 (dba) 3 (30 g, 0.094 mol) (1.47 g, 0.0078 mol) of P (t-Bu) 3 and 600 ml of toluene were placed, and the mixture was refluxed at 100 ° C and reacted for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 53.67 g of Compound 16. (Yield: 84%)

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/S, 7.41/M) 2H (7.28/M, 7.38/M, 7.55/D, 7.11/D, 7.87/D, 7.33/M, 8.28/D, 7.51/M, 8.78/S, 9.26/S) 4H (7.62/D)M, 7.38 / M, 7.55 / D, 7.11 / D, 7.47 / D, 7.43 / D, 7.87 / D, 7.33 / M, 8.28 / D, 7.51 / M, 8.78 /

LC/Mass [M+H]+: 678.77LC / Mass [M + H] < + >: 678.77

실시예Example 17: 화합물 17의 합성 17: Synthesis of Compound 17

Figure pat00030
Figure pat00030

중간체 1-2 (59.2g, 0.137mol)에 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (53.2g, 0.137mol/중국) NaOtBu (36.8g, 0.401mol), 촉매 Pd2(dba)3 (6.69g, 0.007mol), P(t-Bu)3 (2.95g, 0.0146mol)과 Toluene 1200ml를 넣고 100℃에서 환류시켜 6시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 17을 89.44g 수득하였다. (수율: 88%)2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (53.2 g, 0.137 mol / (2.69g, 0.0146mol) of Pd (dba) 3 (6.69g, 0.007mol) and P (t-Bu) 3 and 1200ml of toluene were added and the mixture was refluxed at 100 ° C for 6 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 89.44 g of Compound 17. (Yield: 88%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.26/M, 7.54/D, 7.47/D, 7.43/S) 2H (7.28/M, 7.38/M, 7.55/D, 7.11/D, 7.87/D, 7.33/M, 7.68/D, 7.79) 3H (7.41/M) 6H (8.28/D, 7.51/M)(7.28 / M, 7.38 / M, 7.55 / D, 7.11 / D, 7.87 / D, 7.47 / D, 7.43 / D, 7.33 / M, 7.68 / D, 7.79) 3H (7.41 / M) 6H (8.28 / D, 7.51 /

LC/Mass [M+H]+: 740.88LC / Mass [M + H] < + >: 740.88

실시예Example 18: 화합물 18의 합성 18: Synthesis of compound 18

Figure pat00031
Figure pat00031

중간체 1-2 (59.2g, 0.137mol)에 4-(4-bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole (51.56g, 0.137mol/중국) NaOtBu (36.8g, 0.401mol), 촉매 Pd2(dba)3 (6.69g, 0.007mol), P(t-Bu)3 (2.95g, 0.0146mol)과 Toluene 1200ml를 넣고 100℃에서 환류시켜 6시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 18을 57g 수득하였다. (수율: 58%)4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole (51.56 g, 0.137 mol / in China) NaOtBu (36.8 g, 0.401 (2.69 g, 0.0146 mol) of Pd (dba) 3 (6.69 g, 0.007 mol) and P (t-Bu) 3 and 1200 ml of toluene were added and refluxed at 100 ° C. for 6 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 57 g of Compound 18. (Yield: 58%).

H-NMR(200MHz, CDCl3): δ ppm, 1H(7.26/M, 7.54/D, 7.47/D, 7.43/S) 2H (7.55/D, 7.11/D, 7.28/M, 7.38/M, 7.87/D, 7.33/M) 3H (7.41/M) 4H (7.62/D) 6H (8.28/D, 7.51/M) (7.56 / D, 7.11 / D, 7.28 / M, 7.38 / M, 7.87 / D, 7.47 / D, 7.43 / D, 7.33 / M) 3H (7.41 / M) 4H (7.62 / D) 6H (8.28 / D, 7.51 /

LC/Mass [M+H]+: 728.87LC / Mass [M + H] < + >: 728.87

실시예Example 19: 화합물 19의 합성 19: Synthesis of Compound 19

Figure pat00032
Figure pat00032

중간체 1-2 (30g, 0.094mol)에 2,2'-(4'-bromobiphenyl-3,5-diyl)bis(1-phenyl-1H-benzo[d]imidazole) (58g, 0.094mol/TCI) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 19를 79.7g 수득하였다. (수율: 84%)(4-bromobiphenyl-3,5-diyl) bis (1-phenyl-1H-benzo [d] imidazole) (58g, 0.094mol / TCI) was added to Intermediate 1-2 (30g, 0.094mol) (1.47 g, 0.0078 mol) of Pd (t-Bu) 3 and 600 ml of toluene were added to the reaction mixture, and the reaction was refluxed at 100 ° C. for 8 hours. . After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and purified by column (n-hexane: methylene chloride) to obtain 79.7 g of Compound 19. (Yield: 84%)

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.41/M, 7.47/D, 7.54/D, 7.26/M, 7.43/S) 2H (7.11/D, 7.33/M, 7.28/M, 7.38/M, 7.87/D, 7.55/D, 7.68/D, 7.79/D, 8.28/D, 7.51/M, 7.45/M, 7.59/D, 8.56/D) 3H (7.66/S) 4H (7.50/D, 7.58/M, 7.22/M)7.31 / D, 7.38 / M, 7.38 / M, 7.47 / D, 7.54 / D, 7.26 / M, 7.43 / D, 7.57 / D, 7.68 / D, 7.79 / D, 8.28 / D, 7.51 / M, 7.45 / M, 7.59 / D, 8.56 / D) 7.58 / M, 7.22 / M)

LC/Mass [M+H]+: 970.15LC / Mass [M + H] < + >: 970.15

실시예Example 20: 화합물 20의 합성 20: Synthesis of Compound 20

Figure pat00033
Figure pat00033

중간체 1-2 (30g, 0.094mol)에 6-(4-bromophenyl)-2,3-diphenylquinoxaline (42.85g, 0.094mol/TCI) NaOtBu (18.4g, 0.20mol), 촉매 Pd2(dba)3 (3.38g, 0.004mol), P(t-Bu)3 (1.47g, 0.0078mol)과 Toluene 600ml를 넣고 100℃에서 환류시켜 8시간 반응시켰다. 반응 종료 후 냉각하여 증류수를 넣고 추출하여 칼럼 정제(n-Hexane : methylene chloride)하여 화합물 20을 49.72g 수득하였다. (수율: 74%)To the intermediate 1-2 (30 g, 0.094 mol) was added 6- (4-bromophenyl) -2,3-diphenylquinoxaline (42.85 g, 0.094 mol / TCI) NaOtBu (18.4 g, 0.20 mol), catalyst Pd2 g, 0.004 mol), P (t-Bu) 3 (1.47 g, 0.0078 mol) and Toluene (600 ml) were added and refluxed at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled, distilled water was added thereto, and the mixture was extracted and subjected to column purification (n-hexane: methylene chloride) to obtain 49.72 g of Compound 20. (Yield: 74%).

H-NMR(200MHz, CDCl3): δ ppm, 1H (7.67/D, 7.28/D, 8.10/S, 7.47/D, 7.54/D, 7.43/S, 7.26/M) 2H (7.11/D, 7.33/M, 7.28/M, 7.38/M, 7.87/D, 7.55/D, 8.28/D) 3H (7.41/M) 4H (7.47/D) 6H(7.51/M)D (7.31 / D, 7.34 / D, 7.54 / D, 7.43 / S, 7.26 / M) M, 7.28 / M, 7.38 / M, 7.87 / D, 7.55 / D, 8.28 / D)

LC/Mass [M+H]+: 713.85
LC / Mass [M + H] < + >: 713.85

본 발명의 시험예에서 쓰이는 약어는 아래와 같다.The abbreviations used in the test examples of the present invention are as follows.

NPB: N,N'-Bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidineNPB: N, N'-bis (naphthalen-1-yl) -N,

Ir(ppy)3: Iridium, tris(2-phenylpyidine)Ir (ppy) 3 : Iridium, tris (2-phenylpyidine)

Balq: Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminumBalq: Bis (2-methyl-8-quinolinolato-N1, O8) - (1,1'-Biphenyl-4-olato) aluminum

Alq3: tris(8-quinolinolato)-aluminium(III)Alq 3 : tris (8-quinolinolato) -aluminium (III)

CBP: (4,4-N,N-dicarbazole)biphenylCBP: (4,4-N, N-dicarbazole) biphenyl

시험예Test Example 1 One

ITO로 코팅된 유리기판 위에 NPB를 증착하여 120nm 두께의 정공수송층을 형성하였으며, 이어서 Ir(ppy)3을 도펀트로 하여 화합물 1의 증착속도를 0.1nm/sec, Ir(ppy)3 증착속도를 0.009nm/sec로 증착하여, 증착속도 비율이 9%가 되도록 Ir(ppy)3을 도핑하여 정공수송층 상에 발광층을 30nm 두께로 형성하였다. 그 위에 Balq를 10nm 두께로 증착하여 정공이 발광층을 지나 전자수송층으로 이동하는 것을 방지하는 정공차단층을 형성하고, 그 위에 Alq3를 증착하여 40nm두께의 전자수송층을 형성하였으며, 그 위에 불화리튬을 증착하여 1nm두께의 전자주입층을 형성하였다. 전자주입층 상에 알루미늄을 증착하여 120nm두께의 음극을 형성하여 유기전계발광소자를 제조하였다.Depositing NPB on the glass substrate coated with ITO to a thickness of 120nm was formed a hole-transport layer, followed by Ir (ppy) 3 as a dopant by a vapor deposition rate of 0.009 to a compound 1 0.1nm / sec, Ir (ppy ) 3 deposition rate nm / sec, and Ir (ppy) 3 was doped so that the deposition rate ratio was 9% to form a light emitting layer having a thickness of 30 nm on the hole transport layer. Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer to prevent holes from moving to the electron transporting layer through the light emitting layer, and Alq 3 was deposited thereon to form an electron transporting layer having a thickness of 40 nm. Lithium fluoride Thereby forming an electron injection layer having a thickness of 1 nm. Aluminum was deposited on the electron injecting layer to form a cathode having a thickness of 120 nm to prepare an organic electroluminescent device.

이때, 각 물질의 증착속도는 유기물질인, 화합물 1, NPB, Alq3, Balq는 0.1 nm/sec의 속도로 증착하였고, 불화리튬은 0.01 nm/sec, 알루미늄은 0.5 nm/sec의 속도로 증착하였다.At this time, the deposition rate of each material was evaporated at a rate of 0.1 nm / sec for the compound 1, NPB, Alq 3 , and Balq, 0.01 nm / sec for lithium fluoride, and 0.5 nm / sec for aluminum Respectively.

시험예Test Example 2 2

화합물 1대신에 화합물 2를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was fabricated in the same manner as in Test Example 1, except that Compound 2 was used instead of Compound 1.

시험예Test Example 3 3

화합물 1대신에 화합물 3을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 3 was used instead of Compound 1.

시험예Test Example 4 4

화합물 1대신에 화합물 4를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in Test Example 1, except that Compound 4 was used instead of Compound 1.

시험예Test Example 5 5

화합물 1대신에 화합물 5를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic light emitting diode device was manufactured according to the same method as Test Example 1 except that Compound 5 was used instead of Compound 1.

시험예Test Example 6 6

화합물 1대신에 화합물 6을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 6 was used instead of Compound 1.

시험예Test Example 7 7

화합물 1대신에 화합물 7을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was fabricated in the same manner as in Test Example 1, except that Compound 7 was used instead of Compound 1.

시험예Test Example 8 8

화합물 1대신에 화합물 8을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 8 was used instead of Compound 1.

시험예Test Example 9 9

화합물 1대신에 화합물 9를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in Test Example 1, except that Compound 9 was used instead of Compound 1.

시험예Test Example 10 10

화합물 1대신에 화합물 10을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic light emitting diode was manufactured according to the same method as Test Example 1 except for using Compound 10 instead of Compound 1.

시험예Test Example 11 11

화합물 1대신에 화합물 11을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 11 was used instead of Compound 1.

시험예Test Example 12 12

화합물 1대신에 화합물 12를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was fabricated in the same manner as in Test Example 1, except that Compound 12 was used instead of Compound 1.

시험예Test Example 13 13

화합물 1대신에 화합물 13을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in Test Example 1 except that Compound 13 was used instead of Compound 1.

시험예Test Example 14 14

화합물 1대신에 화합물 14를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 14 was used instead of Compound 1.

시험예Test Example 15 15

화합물 1대신에 화합물 15를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was fabricated in the same manner as in Test Example 1, except that Compound 15 was used instead of Compound 1.

시험예Test Example 16 16

화합물 1대신에 화합물 16을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 16 was used instead of Compound 1.

시험예Test Example 17 17

화합물 1대신에 화합물 17을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 17 was used instead of Compound 1.

시험예Test Example 18 18

화합물 1대신에 화합물 18을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 18 was used instead of Compound 1.

시험예Test Example 19 19

화합물 1대신에 화합물 19를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 19 was used instead of Compound 1.

시험예Test Example 20 20

화합물 1대신에 화합물 20을 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that Compound 20 was used instead of Compound 1.

비교시험예Comparative test example 1 One

상기 화합물 1대신 (4,4 -N,N -dicarbazole)biphenyl (CBP)를 사용한 것을 제외하고는 시험예 1과 동일한 방법으로 유기전계발광소자를 제조하였다.
An organic electroluminescent device was prepared in the same manner as in Test Example 1, except that (4,4-N, N-dicarbazole) biphenyl (CBP)

이하, 상기 시험예와 비교시험예에 따라 제조된 유기전계발광소자의 특성을 비교한 결과를 하기 표 1에 나타내었다.Table 1 below shows the results of comparing the characteristics of the organic electroluminescent device manufactured according to the test examples and the comparative test examples.

호스트 물질Host substance 구동전압
(at 1000cd/m2)Driving voltage
(at 1000 cd / m 2 ) 발광효율
(cd/A)Luminous efficiency
(cd / A) 색좌표 CIE(x,y)Color coordinates CIE (x, y) 시험예 1Test Example 1 화합물 1Compound 1 5.25.2 3333 0.30, 0.630.30, 0.63 시험예 2Test Example 2 화합물 2Compound 2 5.55.5 3232 0.33, 0.630.33, 0.63 시험예 3Test Example 3 화합물 3Compound 3 5.45.4 2525 0.29, 0.600.29, 0.60 시험예 4Test Example 4 화합물 4Compound 4 5.95.9 3030 0.30, 0.620.30, 0.62 시험예 5Test Example 5 화합물 5Compound 5 6.06.0 4343 0.32, 0.630.32, 0.63 시험예 6Test Example 6 화합물 6Compound 6 4.24.2 4242 0.33, 0.640.33, 0.64 시험예 7Test Example 7 화합물 7Compound 7 4.54.5 4040 0.32, 0.650.32, 0.65 시험예 8Test Example 8 화합물 8Compound 8 5.25.2 2828 0.33, 0.630.33, 0.63 시험예 9Test Example 9 화합물 9Compound 9 4.34.3 2525 0.32, 0.600.32, 0.60 시험예 10Test Example 10 화합물 10Compound 10 5.25.2 3535 0.30, 0.620.30, 0.62 시험예 11Test Example 11 화합물 11Compound 11 4.94.9 3535 0.32, 0.630.32, 0.63 시험예 12Test Example 12 화합물 12Compound 12 5.05.0 4545 0.33, 0.620.33, 0.62 시험예 13Test Example 13 화합물 13Compound 13 5.85.8 4747 0.33, 0.630.33, 0.63 시험예 14Test Example 14 화합물 14Compound 14 4.54.5 4444 0.32, 0.620.32, 0.62 시험예 15Test Example 15 화합물 15Compound 15 4.44.4 4545 0.33, 0.630.33, 0.63 시험예 16Test Example 16 화합물 16Compound 16 4.34.3 4040 0.30, 0.620.30, 0.62 시험예 17Test Example 17 화합물 17Compound 17 4.24.2 3535 0.29, 0.630.29, 0.63 시험예 18Test Example 18 화합물 18Compound 18 5.25.2 3131 0.33, 0.630.33, 0.63 시험예 19Test Example 19 화합물 19Compound 19 5.55.5 3030 0.33, 0.630.33, 0.63 시험예 20Test Example 20 화합물 20Compound 20 4.64.6 2828 0.32, 0.620.32, 0.62 비교시험예 1Comparative Test Example 1 CBPCBP 6.56.5 1919 0.33, 0.630.33, 0.63

유기전계발광소자Organic electroluminescent device 특성분석 Character analysis

위에서 만든 유기발광소자(기판크기:25×25mm2/증착면적:2×2mm2)를 IVL 측정셋트(CS-2000+지그+IVL프로그램)에 고정한 후 전류를 1mA/m2씩 상승시키며 증착면의 발광 휘도(cd/m2), 구동전압(V), 전류밀도(A/m2), 발광효율(cd/A)를 측정하여 휘도가 1000cd/m2 일 때 구동전압과 발광효율을 표 1에 나타내었다.The organic light emitting device (substrate size: 25 × 25 mm 2 / deposition area: 2 × 2 mm 2 ) was fixed on the IVL measurement set (CS-2000 + jig + IVL program), and the current was increased by 1 mA / m 2 in the light emission luminance (cd / m 2), driving voltage (V), current density (a / m 2), luminous efficiency (cd / a) by measuring the brightness of 1000cd / m 2 il table for drive voltage and luminous efficiency when Respectively.

표 1을 참고하면, 본 발명에 따른 유기전계발광소자용 화합물이 유기전계발광소자의 발광층의 호스트 물질로 사용될 때 종래의 CBP를 사용할 때 보다 구동전압이 상당히 떨어지고, 발광효율이 상당히 우수함을 보여주고 있다.Referring to Table 1, when the compound for an organic electroluminescent device according to the present invention is used as a host material of a light emitting layer of an organic electroluminescent device, the driving voltage is significantly lowered and the luminescent efficiency is remarkably superior to that of the conventional CBP have.

Claims (9)

하기 구조식 1로 표시되는 유기전계발광소자용 화합물.
[구조식 1]
Figure pat00034

상기 구조식 1에서,
R1 및 R2는 서로 같거나 다를 수 있고, R1 및 R2는 각각 독립적으로 수소원자,
Figure pat00035

치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R1 및 R2 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있고,
Ar1 및 Ar2는 서로 같거나 다를 수 있고, Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴기, 또는 치환 또는 비치환된 C3 내지 C30 시클로알킬기이거나, 또는 Ar1 및 Ar2는 서로 결합되고 그들 사이의 질소원자와 함께 치환 또는 비치환된 C2 내지 C30 헤테로 아릴기 또는 치환 또는 비치환된 C3 내지 C30 시클로알킬기를 형성할 수 있고,
Ar3 내지 Ar5는 서로 같거나 다를 수 있고, Ar3 내지 Ar5는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴기, 또는 치환 또는 비치환된 C3 내지 C30 시클로알킬기이고,
R8 내지 R30은 서로 같거나 다를 수 있고, R8 내지 R30은 각각 독립적으로 수소원자, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로아릴기이거나, 또는 R8 내지 R30 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C2 내지 C30 헤테로 아릴기를 형성할 수 있고,
Y1 내지 Y3은 서로 같거나 다를 수 있고, Y1 내지 Y3은 각각 독립적으로 산소원자 또는 황원자이고,
m은 0 또는 1이고,
R3 내지 R7은 서로 같거나 다를 수 있고, R3 내지 R7은 각각 독립적으로 수소원자, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R3 내지 R7 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있다.A compound for an organic electroluminescence device represented by Structural Formula (1) below.
[Structural formula 1]
Figure pat00034

In the above formula 1,
R 1 and R 2 may be the same or different from each other, and R 1 and R 2 are each independently a hydrogen atom,
Figure pat00035

A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 1 And R < 2 > is a fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group which is further bonded to a neighboring carbon atom of the carbon atom to which it is bonded to form a substituted or unsubstituted fused C6 to C30 aryl group, Lt; / RTI >
Ar 1 and Ar 2 may be the same or different from each other, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, Or Ar 1 and Ar 2 are bonded to each other and together with the nitrogen atom therebetween form a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted C3 to C30 cycloalkyl group Can,
Ar 3 to Ar 5 may be the same or different from each other, Ar 3 to Ar 5 each independently represent a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, Lt; / RTI > is a C3 to C30 cycloalkyl group,
R 8 to R 30 may be the same or different from each other, and R 8 to R 30 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group, or any one of R 8 to R 30 may further be bonded to the adjacent carbon atom of the carbon atom to which they are bonded to form a substituted or unsubstituted C 6 to C 30 aryl group, An unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C2 to C30 heteroaryl group,
Y 1 to Y 3 may be the same or different from each other, Y 1 to Y 3 are each independently an oxygen atom or a sulfur atom,
m is 0 or 1,
R 3 to R 7 may be the same or different from each other, and each of R 3 to R 7 independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 3 to R 7 Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group have. 하기 구조식 1로 표시되는 유기전계발광소자용 화합물.
[구조식 1]
Figure pat00036

상기 구조식 1에서,
R1 및 R2는 서로 같거나 다를 수 있고, 각각 독립적으로 아래 화학식 U1 내지 U58 중에서 선택된 어느 하나이고,
m은 0 또는 1이고,
R3 내지 R7은 서로 같거나 다를 수 있고, R3 내지 R7은 각각 독립적으로 수소원자, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로 아릴기이거나, 또는 R3 내지 R7 중 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로 아릴기를 형성할 수 있다.
Figure pat00037

Figure pat00038

Figure pat00039
A compound for an organic electroluminescence device represented by Structural Formula (1) below.
[Structural formula 1]
Figure pat00036

In the above formula 1,
R 1 and R 2, which may be the same or different, are each independently selected from the following formulas (U1) to (U58)
m is 0 or 1,
R 3 to R 7 may be the same or different from each other, and each of R 3 to R 7 independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 3 to R 7 Either of which may be further fused with a neighboring carbon atom of the carbon atom to which it is attached to form a substituted or unsubstituted fused C6 to C30 aryl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group have.
Figure pat00037

Figure pat00038

Figure pat00039
 하기 구조식으로 표시되는 화합물 중에서 선택된 어느 하나인 유기전계발광소자용 화합물.
Figure pat00040

Figure pat00041

Figure pat00042

Figure pat00043

Figure pat00044
A compound for an organic electroluminescence device, wherein the compound is any one selected from compounds represented by the following structural formulas.
Figure pat00040

Figure pat00041

Figure pat00042

Figure pat00043

Figure pat00044
 제3항에 있어서,
상기 유기전계발광소자용 화합물은 하기 구조식으로 표시되는 화합물 중에서 선택된 어느 하나인 것을 특징으로 하는 유기전계발광소자용 화합물.
Figure pat00045

Figure pat00046

Figure pat00047
The method of claim 3,
Wherein the organic electroluminescent device compound is any one selected from compounds represented by the following structural formulas.
Figure pat00045

Figure pat00046

Figure pat00047
 제1항 내지 제4항 중 어느 한 항에 따른 유기전계발광소자용 화합물을 포함하는 유기전계발광소자.An organic electroluminescent device comprising the compound for organic electroluminescent device according to any one of claims 1 to 4. 제1전극, 제2전극 및 제1전극과 제2전극 사이에 단수 또는 복수의 유기물층을 포함하는 유기전계발광소자에 있어서,
상기 단수 또는 복수의 유기물층 중에서 선택된 1종 이상의 유기물층은 제1항 내지 제4항 중 어느 한 항에 따른 유기전계발광소자용 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자.A first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, the organic electroluminescent device comprising:
The organic electroluminescent device according to any one of claims 1 to 4, wherein the at least one organic layer selected from the single or plural organic layers includes the compound for organic electroluminescent devices. 제6항에 있어서,
상기 복수의 유기물층은 발광층을 포함하는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein the plurality of organic layers includes a light emitting layer. 제7항에 있어서,
상기 복수의 유기물층은 전자주입층, 전자수송층, 정공차단층, 전자차단층, 정공수송층, 및 정공주입층 중에서 선택된 1종 이상을 추가로 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 7, wherein
Wherein the plurality of organic layers further include at least one selected from the group consisting of an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer. 제7항에 있어서,
상기 발광층은 호스트와 도펀트를 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 7, wherein
Wherein the light emitting layer comprises a host and a dopant.
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