KR20130075949A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

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

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KR20130075949A
KR20130075949A KR1020110144286A KR20110144286A KR20130075949A KR 20130075949 A KR20130075949 A KR 20130075949A KR 1020110144286 A KR1020110144286 A KR 1020110144286A KR 20110144286 A KR20110144286 A KR 20110144286A KR 20130075949 A KR20130075949 A KR 20130075949A
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nuclear atoms
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이인혁
김홍석
김태형
라종규
백영미
박호철
신진용
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주식회사 두산
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Abstract

PURPOSE: An organic light-emitting compound is provided to have excellent thermal stability, thereby providing an organic electroluminescent device with improved light emitting efficiency, driving voltage, and lifetime. CONSTITUTION: A compound is represented by chemical formula 1. In chemical formula 1 each of X1 and X2 is selected from CR1R2, O, S, NR3, and SiR4R5; each of Ar1 and Ar2 is selected from deuterium, halogen, a substituted or unsubstituted C1-60 alkyl group, a substituted or unsubstituted C2-60 alkenyl, a substituted or unsubstituted C2-60 alkynyl group, a substituted or unsubstituted C6-60 aryl group, a substituted or unsubstituted C5-60 heteroaryl group, a substituted or unsubstituted C1-60 alkoxy group, a substituted or unsubstituted C6-60 aryloxy group, a substituted or unsubstituted C3-60 cycloalkyl group, a substituted or unsubstituted C3-60 heterocycloalkyl group, a substituted or unsubstituted C6-60 arylamine group, and a substituted or unsubstituted silyl group.

Description

유기발광 화합물 및 이를 이용한 유기 전계 발광 소자 {ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME} Organic light emitting compound and organic electroluminescent device using the same {ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

본 발명은 신규의 유기발광 화합물 및 이를 하나 이상의 유기물층, 특히 발광층에 포함함으로써 발광효율, 휘도, 열적 안정성, 구동전압, 수명 등의 특성이 개선된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifetime by including the same in one or more organic material layers, in particular in the light emitting layer.

유기 전계 발광 소자(organic electroluminescent device) (이하, 유기 EL 소자라 함)는 통상 양극과 음극 및 이들 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 EL 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공 주입층(HIL), 정공 수송층(HTL), 발광층(EML), 전자 수송층(ETL), 전자 주입층(EIL) 등을 포함할 수 있다. An organic electroluminescent device (hereinafter referred to as an organic EL device) generally has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic EL device, for example, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) ), An electron injection layer (EIL), and the like.

이러한 유기 EL 소자의 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층으로 주입되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다.When voltage is applied between the two electrodes of the organic EL device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet, and the excitons are brought to the ground state. When it falls, it glows.

유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통해 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도펀트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도펀트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도펀트의 파장대로 이동하므로, 이용하는 도펀트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. The light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. In addition, in order to increase luminous efficiency through increasing color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

일반적으로 인광 호스트 재료로는 CBP(4,4-dicarbazolybiphenyl) 등의 카바졸계 화합물 등이 사용되며, 인광 도펀트 재료로는 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물이 널리 사용되고 있다. Generally, a carbazole compound such as CBP (4,4-dicarbazolybiphenyl) is used as the phosphorescent host material, and a metal complex compound containing heavy atoms such as Ir and Pt is widely used as the phosphorescent dopant material. have.

그러나 현재 사용되는 인광 호스트 재료인 CBP의 경우 유리전이온도(Tg)가 110℃ 정도로 낮으며, 소자 내의 결정화가 쉽게 일어나 유기 EL 소자의 수명이 150시간 정도로 매우 짧은 문제점이 있다.However, CBP, which is currently used phosphorescent host material, has a low glass transition temperature (Tg) of about 110 ° C., and crystallization in the device is easy, resulting in a very short lifespan of about 150 hours.

대한민국 공개특허공보 제2011-0043712호Republic of Korea Patent Publication No. 2011-0043712

본 발명의 목적은 보다 우수한 열적 안정성을 갖는 유기발광 화합물 및 이를 포함하여 발광효율, 휘도, 전력효율, 구동전압, 수명 등의 특성이 향상된 유기 EL 소자를 제공하는 것이다. SUMMARY OF THE INVENTION An object of the present invention is to provide an organic light emitting compound having better thermal stability and an organic EL device having improved characteristics such as luminous efficiency, brightness, power efficiency, driving voltage, and lifetime.

상기 목적을 달성하기 위하여 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다. In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

Figure pat00001
Figure pat00001

상기 식에서,Where

X1 및 X2는 각각 독립적으로 CR1R2, O, S, NR3 및 SiR4R5 로 이루어진 군에서 선택되고;X 1 and X 2 are each independently selected from the group consisting of CR 1 R 2 , O, S, NR 3 and SiR 4 R 5 ;

Ar1 및 Ar2는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기, 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택되며; Ar 1 and Ar 2 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ~ C 60 alkyl group, substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ~ C 60 arylamine group, and a substituted or unsubstituted silyl group;

R1 내지 R5는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택되거나, 인접한 기와 서로 결합하여 축합 고리를 형성하며;R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ~ C 60 alkyl group, substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ~ C 60 aryl group and a substituted or unsubstituted amine selected from the group consisting of unsubstituted silyl, and adjacent groups combine with each other to form a condensed ring;

n 및 m은 각각 독립적으로 1 내지 4의 정수이며;n and m are each independently an integer from 1 to 4;

하나 이상의 Ar3는 서로 같거나 다르고, 하나 이상의 Ar4는 서로 같거나 다르며, 이들은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택된다.At least one Ar 3 is the same or different from each other, at least one Ar 4 is the same or different from each other, and each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 Alkynyl group, substituted or unsubstituted C 6 ~ C 60 Aryl group, substituted or unsubstituted nuclear atoms of 5 to 60 Heteroaryl group, substituted or unsubstituted C 1 to C 60 alkoxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted It is selected from the group consisting of a ring heteronuclear alkyl group having 3 to 60 ring atoms, a substituted or unsubstituted C 6 ~ C 60 arylamine group, and a substituted or unsubstituted silyl group.

본 발명은 또한 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 EL 소자로서, 상기 유기물층 중 적어도 하나는 본 발명의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 EL 소자를 제공한다. 바람직하게는, 본 발명의 화합물은 발광층의 인광 호스트 재료로 이용될 수 있다.The present invention also provides an organic EL device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers is It provides an organic EL device comprising a compound represented by the formula (1). Preferably, the compound of the present invention can be used as a phosphorescent host material of the light emitting layer.

본 발명의 화학식 1로 표시되는 화합물은 우수한 열적안정성, 발광능 등을 가지고 있어, 이를 포함하는 유기 EL 소자는 발광성능, 구동전압, 수명 등의 특성이 크게 향상될 수 있어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다. The compound represented by Chemical Formula 1 of the present invention has excellent thermal stability, light emitting performance, and the like, and the organic EL device including the same may significantly improve characteristics such as light emission performance, driving voltage, and lifetime, so that a full color display panel may be effectively used. Can be applied.

본 발명의 화합물은, 페노티아진(phenothiazine)(화학식 1에서 X1 및 X2 중 하나가 NH이고 다른 하나가 S인 화합물), 페녹사진(phenoxazine)(화학식 1에서 X1 및 X2 중 하나가 NH이고 다른 하나가 O인 화합물), 아크리딘(acridine)(화학식 1에서 X1 및 X2 중 하나가 NH이고 다른 하나가 CH2인 화합물), 페나자실린(phenazasiline)(화학식 1에서 X1 및 X2 중 하나가 NH이고 다른 하나가 SiH2인 화합물) 등을 중심 모이어티로 갖는 화합물로서, 다양한 치환체의 도입이 용이하며 치환체들에 의해 삼중항 에너지 레벨(Triplet energy state)을 안정하게 형성하는 효과를 유도함과 동시에, 에너지 레벨이 조절됨으로써 청색에서부터 적색 발광 재료의 호스트로서 소자의 특성을 개선함과 동시에 전자 및/또는 정공 수송 능력, 발광효율, 구동전압, 수명 특성 등을 개선할 수 있다. 따라서 발광층뿐만 아니라 정공 수송층, 전자 수송층 등으로 응용될 수 있다.The compound of the present invention, phenothiazine (phenothiazine) (Formula 1 in X 1 And a compound in which one of X 2 is NH and the other is S), a phenoxazine (compound of Formula 1, wherein one of X 1 and X 2 is NH and the other is O), and acridine ( In Formula 1, one of X 1 and X 2 is NH and the other is CH 2 ), phenazasiline (Compound in Formula 1, wherein one of X 1 and X 2 is NH and the other is SiH 2 ) It is a compound having a back moiety as a central moiety, and it is easy to introduce various substituents and induces the effect of stably forming triplet energy level by substituents, and at the same time, the energy level is controlled to emit light from blue to red. As the host of the material, the characteristics of the device can be improved, and at the same time, the electron and / or hole transport ability, the luminous efficiency, the driving voltage, and the lifetime characteristics can be improved. Therefore, it can be applied to not only the light emitting layer but also a hole transport layer, an electron transport layer, and the like.

본 발명의 화합물은 하기 화학식 1로 표시된 구조를 가진다.The compound of the present invention has a structure represented by the following formula (1).

<화학식 1> &Lt; Formula 1 >

Figure pat00002
Figure pat00002

상기 식에서, X1 및 X2는 각각 독립적으로 CR1R2, O, S, NR3 및 SiR4R5 로 이루어진 군에서 선택된다. 바람직하게는, 발광능, 전압/전류 효율 등을 고려했을 때, X1 및 X2는 각각 독립적으로 CR1R2 또는 SiR4R5이다.Wherein X 1 and X 2 are each independently selected from the group consisting of CR 1 R 2 , O, S, NR 3 and SiR 4 R 5 . Preferably, in consideration of light emitting capability, voltage / current efficiency and the like, X 1 and X 2 are each independently CR 1 R 2 or SiR 4 R 5 .

R1 내지 R5는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기, 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택되며, 인접한 기들은 서로 결합하여 축합 고리를 형성할 수 있다. 바람직하게는, R1 내지 R5는 각각 독립적으로 치환 또는 비치환된 C1~C60의 알킬기 또는 치환 또는 비치환된 C6~C60의 아릴기이다. R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ~ C 60 alkyl group, substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 3 -C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted It is selected from the group consisting of a C 6 ~ C 60 arylamine group, and a substituted or unsubstituted silyl group, adjacent groups may combine with each other to form a condensed ring. Preferably, R 1 to R 5 are each independently a substituted or unsubstituted C 1 to C 60 alkyl group or a substituted or unsubstituted C 6 to C 60 aryl group.

R1 내지 R5는 각각 독립적으로 할로겐, 시아노, C1~C60의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C60의 알콕시기, C6~C60의 아릴옥시기, C3~C60의 시클로알킬기, 핵원자수 3 내지 60의 헤테로시클로알킬기, C6~C60의 아릴아민기 및 실릴기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다.R 1 to R 5 are each independently halogen, cyano, C 1 to C 60 alkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 60 alkoxy group , C aryloxy of 6 ~ C 60, C 3 ~ C 60 cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C 6 ~ C 60 aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.

Ar1 및 Ar2는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기, 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택된다. Ar 1 and Ar 2 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ~ C 60 alkyl group, substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ~ C 60 arylamine group, and a substituted or unsubstituted silyl group.

Ar1 및 Ar2는 각각 독립적으로 할로겐, 시아노, C1~C60의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C60의 알콕시기, C6~C60의 아릴옥시기, C3~C60의 시클로알킬기, 핵원자수 3 내지 60의 헤테로시클로알킬기, C6~C60의 아릴아민기 및 실릴기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다.Ar 1 and Ar 2 are each independently halogen, cyano, C 1 to C 60 alkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 60 alkoxy group , C aryloxy of 6 ~ C 60, C 3 ~ C 60 cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C 6 ~ C 60 aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.

본 발명의 일 실시예에 따르면, Ar1 및 Ar2의 상기 아릴기는 각각 독립적으로 비치환된 C6~C60의 아릴기이거나 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 C6~C60의 아릴기이고, Ar1 및 Ar2의 상기 헤테로아릴기는 각각 독립적으로 비치환된 핵원자수 5 내지 60의 헤테로아릴기이거나 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 핵원자수 5 내지 60의 헤테로아릴기일 수 있다.According to an embodiment of the present invention, the aryl groups of Ar 1 and Ar 2 are each independently an unsubstituted C 6 ~ C 60 aryl group or C 6 ~ C 60 aryl group, a nuclear atom of 5 to 60 hetero A C 6 to C 60 aryl group substituted with an aryl group or an amino group, and the heteroaryl groups of Ar 1 and Ar 2 are each independently an unsubstituted heteroaryl group having 5 to 60 nuclear atoms or a C 6 to C 60 group ; It may be an aryl group, a heteroaryl group having 5 to 60 nuclear atoms or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group.

보다 구체적으로는, Ar1 및 Ar2의 비치환된 아릴기는 각각 독립적으로 페닐(phenyl), 바이페닐(biphenyl), 나프탈렌(naphthalene), 페난트렌(phenanthrene), 안트라센(anthracene), 파이렌(pyrene), 플루오렌(fluorine) 등에서 선택될 수 있고, Ar1 및 Ar2의 비치환된 헤테로아릴기는 각각 독립적으로 피리딘(pyridine), 피리미딘(pyrimidine), 피리다진(pyridazine), 피라진(pyrazine), 트리아진(triazine), 벤즈이미다졸(benzimidazole), 퀴놀린(quinoline), 이소퀴놀린(isoquinoline), 퀴녹살린(quinoxaline), 카바졸(carbazole), 디벤조퓨란(dibenzofuran), 디벤조싸이오펜(dibenzothiophene), 페난트롤린(phenanthroline), 아크리딘(acridine), 페노싸이아진(phenothiazine) 등에서 선택될 수 있다.More specifically, the unsubstituted aryl groups of Ar 1 and Ar 2 are each independently phenyl, biphenyl, naphthalene, phenanthrene, anthracene, pyrene ), Fluorine (fluorine) and the like, and the unsubstituted heteroaryl groups of Ar 1 and Ar 2 are each independently pyridine, pyrimidine, pyridazine, pyrazine, Triazine, benzimidazole, quinoline, isoquinoline, isoquinoline, quinoxaline, carbazole, dibenzofuran, dibenzothiophene , Phenanthroline, acridine, phenothiazine, and the like.

특히 Ar1 및 Ar2가 상기 기재된 치환기일 경우 종래 유기발광 재료[예, 4,4-dicarbazolybiphenyl (이하 CBP로 표시)] 보다 분자량이 유의적으로 증대되어 유리전이온도가 향상되고 이로 인해 높은 열적 안정성을 가질 수 있다. 따라서 본 발명의 화합물을 포함하는 소자는 내구성 및 수명 등의 특성이 향상될 수 있다. 특히 이러한 소자 수명 향상은 풀 칼라 유기 발광 패널에서의 성능 극대화에도 큰 효과가 있다.In particular, when Ar 1 and Ar 2 are the substituents described above, the molecular weight is significantly increased compared to conventional organic light emitting materials (eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)), thereby improving glass transition temperature and thereby high thermal stability. Can have Therefore, the device including the compound of the present invention can be improved in characteristics such as durability and lifespan. In particular, the improvement of device life has a great effect on maximizing performance in full color organic light emitting panel.

이러한 열적 안정성과 함께, 발광능, 전압/전류 효율 등을 고려하여, Ar1 및 Ar2는 각각 독립적으로 비치환된 C6~C60의 아릴기; C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 C6~C60의 아릴기; 비치환된 핵원자수 5 내지 60의 헤테로아릴기; 또는 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 핵원자수 5 내지 60의 헤테로아릴기일 수 있다. 좀더 구체적으로는, Ar1은 비치환된 C6~C60의 아릴기; 또는 C6~C60의 아릴기로 치환된 핵원자수 5 내지 60의 헤테로아릴기이고, Ar2는 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 C6~C60의 아릴기; 비치환된 핵원자수 5 내지 60의 헤테로아릴기; 또는 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기로 치환된 핵원자수 5 내지 60의 헤테로아릴기일 수 있다.In addition to such thermal stability, in consideration of light emitting ability, voltage / current efficiency, etc., Ar 1 and Ar 2 are each independently an unsubstituted C 6 ~ C 60 aryl group; C 6 -C 60 aryl group substituted with a C 6 ~ C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms or an amino group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C 6 -C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group. More specifically, Ar 1 is an unsubstituted C 6 ~ C 60 aryl group; Or a heteroaryl group of 5 to 60 nuclear atoms substituted with an aryl group of C 6 to C 60 , and Ar 2 is substituted with an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms or an amino group C 6 ~ C 60 Aryl group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C 6 to C 60 aryl group or a heteroaryl group having 5 to 60 nuclear atoms substituted with a heteroaryl group having 5 to 60 nuclear atoms.

화학식 1에서, n 및 m은 각각 독립적으로 1 내지 4의 정수이다. 바람직하게는, n 및 m은 각각 1이다.In Formula 1, n and m are each independently an integer of 1-4. Preferably, n and m are each one.

하나 이상의 Ar3는 서로 같거나 다르고, 하나 이상의 Ar4는 서로 같거나 다르다. Ar3 및 Ar4는 각각 독립적으로 수소 또는 임의의 치환체일 수 있는데, 치환체로는 중수소, 할로겐, 시아노기, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기, 치환 또는 비치환된 실릴기 등이 있다.At least one Ar 3 is the same or different from each other, and at least one Ar 4 is the same or different from each other. Ar 3 and Ar 4 may each independently be hydrogen or any substituent, which may include deuterium, halogen, cyano, substituted or unsubstituted C 1 to C 60 alkyl group, substituted or unsubstituted C 2 to C 60 alkenyl group, substituted or unsubstituted C 2 to C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted Or an unsubstituted C 1 to C 60 alkoxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted nuclear atom 3 to 60 heterocycloalkyl groups, substituted or unsubstituted C 6 to C 60 arylamine groups, substituted or unsubstituted silyl groups, and the like.

Ar3 및 Ar4는 각각 독립적으로 할로겐, 시아노, C1~C60의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C60의 알콕시기, C6~C60의 아릴옥시기, C3~C60의 시클로알킬기, 핵원자수 3 내지 60의 헤테로시클로알킬기, C6~C60의 아릴아민기 및 실릴기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다.Ar 3 and Ar 4 are each independently halogen, cyano, C 1 ~ C 60 alkyl group, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ~ C 60 alkoxy group , C aryloxy of 6 ~ C 60, C 3 ~ C 60 cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C 6 ~ C 60 aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.

본 발명에서 Ar1 내지 Ar4, R1 내지 R5의 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 하기에 기재된 구조를 가질 수 있으며, 이들에 한정되는 것은 아니다. In the present invention, the aryl groups, heteroaryl groups and arylamine groups of Ar 1 to Ar 4 , R 1 to R 5 may each independently have a structure described below, but are not limited thereto.

Figure pat00003
Figure pat00003

Figure pat00004
Figure pat00005
Figure pat00004
Figure pat00005

하기 화합물들은 본 발명의 화학식 1의 화합물의 대표적인 예들이나, 본 발명의 화학식 1의 화합물이 하기 예시된 것들에 한정되는 것은 아니다.The following compounds are representative examples of the compound of formula 1 of the present invention, but the compound of formula 1 of the present invention is not limited to those illustrated below.

Figure pat00006
Figure pat00006

Figure pat00007
Figure pat00007

Figure pat00008
Figure pat00008

Figure pat00009
Figure pat00009

Figure pat00010
Figure pat00010

Figure pat00011
Figure pat00011

상기 식에서, Ar1 내지 Ar4, R3 내지 R5는 상술한 바와 같다.In the above formula, Ar 1 to Ar 4 , R 3 to R 5 are as described above.

본 발명의 화합물은 일반적인 합성방법에 따라 합성될 수 있으며, 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.Compound of the present invention can be synthesized according to a general synthesis method, the detailed synthesis process for the compound of the present invention will be described in detail in the synthesis examples to be described later.

본 발명은 또한 (i) 양극(anode); (ii) 음극(cathode); 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 EL 소자로서, 상기 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 EL 소자를 제공한다. 이때, 상기 화학식 1로 표시되는 화합물은 1종 또는 2종 이상이 포함될 수 있다.The present invention also provides for (i) an anode; (ii) a cathode; And (iii) one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers comprises a compound represented by the formula (1). To provide. In this case, the compound represented by Formula 1 may include one kind or two or more kinds.

바람직하게는, 본 발명의 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층, 정공주입층, 정공수송층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있으며, 바람직하게는 발광층일 수 있다.Preferably, the organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer, preferably a light emitting layer.

바람직하게는, 본 발명의 화합물은 청색, 녹색 및/또는 적색의 인광 호스트 및/또는 형광 호스트 재료, 특히 바람직하게는 인광 호스트 재료로서 발광층에 포함될 수 있다. 본 발명에서 발광층은 인광 게스트 재료 또는 형광 게스트 재료를 포함할 수 있다. Preferably, the compounds of the invention may be included in the light emitting layer as blue, green and / or red phosphorescent host and / or fluorescent host materials, particularly preferably as phosphorescent host materials. In the present invention, the light emitting layer may include a phosphorescent guest material or a fluorescent guest material.

본 발명의 유기 EL 소자 구조는 전극간에 유기물층을 1층 또는 2층 이상 적층한 구조이며, 예를 들면 (i) 양극, 발광층, 음극, (ii) 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 음극, (iii) 양극, 정공주입층, 정공수송층, 발광층, 음극 등의 구조를 들 수 있다.The organic EL device structure of the present invention is a structure in which one or two or more organic material layers are laminated between electrodes, and for example, (i) an anode, a light emitting layer, a cathode, (ii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron The structure of a transport layer, an electron injection layer, a cathode, (iii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode is mentioned.

또한, 본 발명에 따른 유기 EL 소자는 전술한 바와 같이 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입될 수 있다. In addition, the organic EL device according to the present invention may have an insulating layer or an adhesive layer inserted into the interface between the electrode and the organic layer as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

본 발명에 따른 유기 EL 소자에 있어서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에만 한정되지 않는다. In the organic EL device according to the present invention, the organic material layer including the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

본 발명에 따른 유기 EL 소자는 유기물층 중 1층 이상을 본 발명의 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다. The organic EL device according to the present invention forms an organic material layer and an electrode by using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Formula 1 of the present invention. Can be prepared.

예컨대, 기판으로는 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 사용될 수 있다. For example, a silicon wafer, quartz or glass plate, a metal plate, a plastic film or a sheet can be used as the substrate.

양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에만 한정되는 것은 아니다. Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.

또한, 정공 주입층, 정공 수송층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당업계에 알려진 통상의 물질이 사용될 수 있다. In addition, the hole injection layer, the hole transport layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.

이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.
Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[[ 준비예Preparation Example 1] 화합물  1] Compound MatMat 1-A의 합성 Synthesis of 1-A

<단계 1> 9,9-<Step 1> 9,9- dimethyldimethyl -10--10- phenylphenyl -9,10--9,10- dihydroacridinedihydroacridine 의 합성Synthesis of

Figure pat00012
Figure pat00012

질소 조건에서 250 ㎖ 둥근 플라스크에 9,9-dimethyl-9,10-dihydroacridine(3.14g, 15mmol), bromobenzene (2.35g, 1당량), sodium tert-butoxide (4.27g, 3당량), tris(dibenzylideneacetone)dipalladium) (0.255g, 3 mol%) 및 1,1'-bis(diphenylphosphino)ferrocene (0.25g, 3 mol%)을 첨가한 후 toluene 75 ㎖에서 밤새 환류 교반하였다. 9,9-dimethyl-9,10-dihydroacridine (3.14 g, 15 mmol), bromobenzene (2.35 g, 1 equiv), sodium tert-butoxide (4.27 g, 3 equiv) and tris (dibenzylideneacetone) in a 250 ml round flask under nitrogen ) dipalladium) (0.255 g, 3 mol%) and 1,1'-bis (diphenylphosphino) ferrocene (0.25 g, 3 mol%) were added, followed by stirring under reflux overnight at 75 ml of toluene.

반응 종료 후, 반응액을 celite를 통해 여과하고 컬럼 크로마토그래피로 정제하여 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3.4g, 수율 80%)을 얻었다. After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to obtain 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3.4g, yield 80%).

<단계 2> 2-&Lt; Step 2 > 2- bromobromo -9,9--9,9- dimethyldimethyl -10--10- phenylphenyl -9,10--9,10- dihydroacridinedihydroacridine 의 합성Synthesis of

상기 <단계 1>에서 얻은 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3g, 10.5mmol)과 n-bromosuccinimide (1.9g, 1당량)을 250 ㎖ 둥근 플라스크에서 50 ㎖ 사염화탄소와 함께 질소분위기 하에서 3시간 동안 교반하였다. 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3 g, 10.5 mmol) and n-bromosuccinimide (1.9 g, 1 equivalent) obtained in <Step 1> together with 50 ml carbon tetrachloride in a 250 ml round flask The mixture was stirred for 3 hours under a nitrogen atmosphere.

반응 종료 후, 반응액을 celite를 통해 여과하고 컬럼 크로마토그래피로 정제하여 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2.3g, 수율 60%)을 얻었다.After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to give 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2.3g, yield 60%).

<단계 3> <Step 3> MatMat 1-A의 합성  Synthesis of 1-A

Figure pat00013
Figure pat00013

상기 <단계 2>에서 얻은 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2g, 5.5mmol), bis(pinacolato)diboron (1.7g, 1.2당량), [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium(Ⅱ) (0.12g, 3 mol%), potassium acetate (1.6g, 3당량) 및 1,4-dioxane (30 ㎖)을 100 ㎖ 둥근 플라스크에서 질소 분위기하에 밤새 환류 교반하였다. 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2g, 5.5mmol), bis (pinacolato) diboron (1.7g, 1.2 equivalents) obtained in <Step 2>, [1,1'-bis ( diphenylphosphino) ferrocene] dichloropalladium (II) (0.12 g, 3 mol%), potassium acetate (1.6 g, 3 equiv) and 1,4-dioxane (30 mL) were stirred under reflux overnight under a nitrogen atmosphere in a 100 mL round flask.

H2O를 넣어 반응을 종료시킨 후, methylene chloride를 첨가하여 H2O층과 유기층을 분리하였다. 감압 승온하여 용매를 제거한 후, 컬럼 크로마토그래피로 정제하여 Mat 1-A (1.8g, 80%)을 얻었다.After put to complete the reaction of H 2 O, by the addition of methylene chloride to separate the H 2 O layer and an organic layer. After heating up under reduced pressure to remove the solvent, the residue was purified by column chromatography to obtain Mat 1-A (1.8 g, 80%).

GC-Mass: 410
GC-Mass: 410

[[ 준비예Preparation Example 2] 화합물  2] Compound MatMat 1-B의 합성 Synthesis of 1-B

<단계 1> 10-(4,6-<Step 1> 10- (4,6- diphenylpyridindiphenylpyridin -2--2- ylyl )-9,9-) -9,9- dimethyldimethyl -9,10-dihydroacridine 의 합성Synthesis of -9,10-dihydroacridine

Figure pat00014
Figure pat00014

질소 조건에서 250 ㎖ 둥근 플라스크에 9,9-dimethyl-9,10-dihydroacridine(3.14g, 15mmol), 2-bromo-4,6-diphenylpyridine (4.65g, 1당량), sodium tert-butoxide (4.27g, 3당량), tris(dibenzylideneacetone)dipalladium) (0.255g, 3 mol%) 및 1,1'-bis(diphenylphosphino)ferrocene (0.25g, 3 mol%)을 첨가한 후 toluene (75 ㎖)에서 밤새 환류 교반하였다. 9,9-dimethyl-9,10-dihydroacridine (3.14 g, 15 mmol), 2-bromo-4,6-diphenylpyridine (4.65 g, 1 equiv), sodium tert-butoxide (4.27 g) in a 250 ml round flask under nitrogen , 3 equiv), tris (dibenzylideneacetone) dipalladium) (0.255 g, 3 mol%) and 1,1'-bis (diphenylphosphino) ferrocene (0.25 g, 3 mol%) were added followed by reflux overnight in toluene (75 mL) Stirred.

반응 종료 후, 반응액을 celite를 통해 여과하고 컬럼 크로마토그래피로 정제하여 10-(4,6-diphenylpyridin-2-yl)-9,9-dimethyl-9,10-dihydroacridine (6.2g, 수율 80%)을 얻었다. After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to obtain 10- (4,6-diphenylpyridin-2-yl) -9,9-dimethyl-9,10-dihydroacridine (6.2g, yield 80% )

<단계 2> <Step 2> MatMat 1-B의 합성 Synthesis of 1-B

Figure pat00015
Figure pat00015

250 ㎖ 둥근 플라스크에서 상기 <단계 1>에서 얻은 10-(4,6-diphenylpyridin-2-yl)-9,9-dimethyl-9,10-dihydroacridine (4.6g, 10.5mmol)과 n-bromosuccin imide (1.9g, 1당량)을 50 ㎖ 사염화탄소와 함께 질소분위기 하에서 3시간 동안 교반하였다. In a 250 ml round flask, 10- (4,6-diphenylpyridin-2-yl) -9,9-dimethyl-9,10-dihydroacridine (4.6 g, 10.5 mmol) and n-bromosuccin imide ( 1.9 g, 1 equiv) was stirred with 50 mL carbon tetrachloride under nitrogen atmosphere for 3 hours.

반응 종료 후, 반응액을 celite를 통해 여과하고 컬럼 크로마토그래피로 정제하여 Mat 1-B (3.26g, 수율 60%)를 얻었다.After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to give Mat 1-B (3.26g, yield 60%).

GC-Mass: 516
GC-Mass: 516

[[ 합성예Synthetic example 1] 화합물  1] Compound MatMat 1의 합성 Synthesis of 1

Figure pat00016
Figure pat00016

준비예 1 에서 합성한 Mat 1-A (5g, 12.2mmol), 준비예 2에서 합성한 Mat 1-B (6.3g, 1당량), tetrakis(triphenylphosphine)palladium(0) (0.7g, 5 mol%) 및 potassium carbonate (5g, 3당량)을 1,4-dioxane (61 ㎖) 및 H2O (18 ㎖)와 함께 250 ㎖ 둥근 플라스크에 넣고 질소 분위기하에서 3시간 동안 환류 교반하였다. Mat 1-A (5 g, 12.2 mmol) synthesized in Preparation Example 1, Mat 1-B (6.3 g, 1 equivalent) synthesized in Preparation Example 2, tetrakis (triphenylphosphine) palladium (0) (0.7 g, 5 mol%) ) And potassium carbonate (5 g, 3 equiv) were added to a 250 mL round flask with 1,4-dioxane (61 mL) and H 2 O (18 mL) and stirred under reflux for 3 hours under a nitrogen atmosphere.

반응 종료 후, 반응액을 celite를 통해 여과하고 컬럼 크로마토그래피로 정제하여 Mat 1 (7g, 수율 80%)을 얻었다.After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to give Mat 1 (7g, 80% yield).

Elemental Analysis: C, 88.18; H, 6.00; N, 5.82/ GC-Mass :720
Elemental Analysis: C, 88.18; H, 6.00; N, 5.82 / GC-Mass: 720

[[ 합성예Synthetic example 2] 화합물  2] Compound MatMat 2의 합성 Synthesis of 2

Figure pat00017
Figure pat00017

<단계 1> <Step 1> MatMat 2-B의 합성 Synthesis of 2-B

2-Bromo-4,6-diphenylpyridine 대신에 2-bromo-4,6-diphenylpyrimidine를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 2-B (3.3g, 수율 60%)를 합성하였다. Mat 2-B (3.3 g, yield 60%) was synthesized in the same manner as in Preparation Example 2, using 2-bromo-4,6-diphenylpyrimidine instead of 2-Bromo-4,6-diphenylpyridine.

GC-Mass: 517GC-Mass: 517

<단계 2> <Step 2> MatMat 2의 합성 Synthesis of 2

Mat 1-B 대신에 Mat 2-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 2(6g, 수율 68%)를 얻었다. Using Mat 2-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 2 (6g, yield 68%).

Elemental Analysis: C, 86.39; H, 5.86; N, 7.75/ GC-Mass : 721
Elemental Analysis: C, 86.39; H, 5. 86; N, 7.75 / GC-Mass: 721

[[ 합성예Synthetic example 3] 화합물  3] Compound MatMat 3의 합성 Synthesis of 3

Figure pat00018
Figure pat00018

<단계 1> <Step 1> MatMat 3-B의 합성 Synthesis of 3-B

2-Bromo-4,6-diphenylpyridine 대신에 2-bromo-4,6-diphenyl-1,3,5-triazine 를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 3-B (3.2g, 수율 60%)를 얻었다.Instead of 2-Bromo-4,6-diphenylpyridine, 2-bromo-4,6-diphenyl-1,3,5-triazine was used to prepare Mat 3-B (3.2 g, yield 60). %) Was obtained.

Elemental Analysis: C, 69.37; H, 4.46; Br, 15.38; N, 10.79 / GC-Mass:518Elemental Analysis: C, 69.37; H, 4. 46; Br, 15.38; N, 10.79 / GC-Mass: 518

<단계 2> <Step 2> MatMat 3의 합성 Synthesis of 3

Mat 1-B 대신에 Mat 3-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 3(5.8g, 수율 66%)를 얻었다.Using Mat 3-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 3 (5.8g, 66% yield).

Elemental Analysis: C, 84.62; H, 5.71; N, 9.67/ GC-Mass : 722
Elemental Analysis: C, 84.62; H, 5.71; N, 9.67 / GC-Mass : 722

[[ 합성예Synthetic example 4] 화합물  4] compound MatMat 4의 합성 Synthesis of 4

Figure pat00019
Figure pat00019

<단계 1> <Step 1> MatMat 4-B의 합성 Synthesis of 4-B

2-Bromo-4,6-diphenylpyridine 대신에 2-bromo-5-phenylpyridine를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 4-B(3.5g, 수율 62%)를 얻었다. Instead of 2-Bromo-4,6-diphenylpyridine, using the 2-bromo-5-phenylpyridine was carried out in the same manner as in Preparation Example 2 to obtain Mat 4-B (3.5g, 62% yield).

GC-Mass: 440GC-Mass: 440

<단계 2> <Step 2> MatMat 4의 합성 Synthesis of 4

Mat 1-B 대신에 Mat 4-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 4(5.2g, 수율 67%)를 얻었다.Using Mat 4-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 4 (5.2g, yield 67%).

Elemental Analysis: C, 87.41; H, 6.09; N, 6.51/ GC-Mass: 644
Elemental Analysis: C, 87.41; H, 6.09; N, 6.51 / GC-Mass: 644

[[ 합성예Synthetic example 5] 화합물  5] Compound MatMat 5의 합성 Synthesis of 5

Figure pat00020
Figure pat00020

<단계 1> <Step 1> MatMat 5-B의 합성 Synthesis of 5-B

2-Bromo-4,6-diphenylpyridine 대신에 2-bromo-5-phenylpyrimidine를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 5-B(3.3g, 수율 61%)를 얻었다. Instead of 2-Bromo-4,6-diphenylpyridine, using the 2-bromo-5-phenylpyrimidine was carried out in the same manner as in Preparation Example 2 to obtain Mat 5-B (3.3g, 61% yield).

GC-Mass: 421GC-Mass: 421

<단계 2> <Step 2> MatMat 5의 합성 Synthesis of 5

Mat 1-B 대신에 Mat 5-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 5 (4.8g, 수율 62%)를 얻었다.Using Mat 5-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 5 (4.8g, 62% yield).

Elemental Analysis: C, 85.42; H, 5.92; N, 8.66/ GC-Mass: 645
Elemental Analysis: C, 85.42; H, 5.92; N, 8.66 / GC-Mass: 645

[[ 합성예Synthetic example 6] 화합물  6] compound MatMat 6의 합성 6, composite

Figure pat00021
Figure pat00021

<단계 1> <Step 1> MatMat 6-B의 합성 Synthesis of 6-B

2-Bromo-4,6-diphenylpyridine 대신에 2-(4-bromophenyl)naphthalene를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 6-B(4g, 수율 73%)를 얻었다. Mat 6-B (4g, 73% yield) was obtained by the same procedure as Preparation Example 2, using 2- (4-bromophenyl) naphthalene instead of 2-Bromo-4,6-diphenylpyridine.

GC-Mass: 489GC-Mass: 489

<단계 2> <Step 2> MatMat 6의 합성 6, composite

Mat 1-B 대신에 Mat 6-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 6(5.1g, 수율 61%)을 얻었다.Using Mat 6-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 6 (5.1g, 61% yield).

Elemental Analysis: C, 89.88; H, 6.09; N, 4.03/ GC-Mass: 693
Elemental Analysis: C, 89.88; H, 6.09; N, 4.03 / GC-Mass: 693

[[ 합성예Synthetic example 7] 화합물  7] compound MatMat 7의 합성 7, composite

Figure pat00022
Figure pat00022

<단계 1> <Step 1> MatMat 7-B의 합성 Synthesis of 7-B

2-Bromo-4,6-diphenylpyridine 대신에 3,3'-(5-bromo-1,3-phenylene)dipyridine를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 7-B(3.6g, 수율 66%)를 얻었다. Instead of 2-Bromo-4,6-diphenylpyridine, 3,3 '-(5-bromo-1,3-phenylene) dipyridine was used to carry out Mat 7-B (3.6 g, yield 66). %) Was obtained.

GC-Mass: 517GC-Mass: 517

<단계 2> <Step 2> MatMat 7의 합성 7, composite

Mat 1-B 대신에 Mat 7-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 7(3.2g, 수율 37%)을 얻었다.Using Mat 7-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 7 (3.2g, yield 37%).

Elemental Analysis: C, 86.39; H, 5.86; N, 7.75/ GC-Mass: 721
Elemental Analysis: C, 86.39; H, 5. 86; N, 7.75 / GC-Mass: 721

[[ 합성예Synthetic example 8] 화합물  8] compound MatMat 8의 합성 8, Synthesis

Figure pat00023
Figure pat00023

<단계 1> <Step 1> MatMat 8-B의 합성 Synthesis of 8-B

2-Bromo-4,6-diphenylpyridine 대신에 4-bromo-2,6-diphenylpyridine를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 8-B(3.6g, 수율 66%)를 얻었다. Instead of 2-Bromo-4,6-diphenylpyridine, using 4-bromo-2,6-diphenylpyridine was carried out in the same manner as in Preparation Example 2 to obtain Mat 8-B (3.6g, 66% yield).

GC-Mass: 516GC-Mass: 516

<단계 2> <Step 2> MatMat 8의 합성 8, Synthesis

Mat 1-B 대신에 Mat 8-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 8 (3.6g, 수율 41%)을 얻었다.Using Mat 8-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 8 (3.6g, yield 41%).

Elemental Analysis: C, 88.18; H, 6.00; N, 5.82/ GC-Mass: 720
Elemental Analysis: C, 88.18; H, 6.00; N, 5.82 / GC-Mass: 720

[[ 합성예Synthetic example 9] 화합물  9] Compound MatMat 9의 합성 9, synthesis

Figure pat00024
Figure pat00024

<단계 1> <Step 1> MatMat 9-B의 합성 Synthesis of 9-B

준비예 2에서 2-bromo-4,6-diphenylpyridine 대신에 4-bromo-N,N-diphenylaniline를 사용하여 Mat 9-B(4g, 수율 74%)를 얻었다. In Preparation Example 2, instead of 2-bromo-4,6-diphenylpyridine, 4-bromo-N, N-diphenylaniline was used to obtain Mat 9-B (4 g, 74% yield).

GC-Mass: 530GC-Mass: 530

<단계 2> <Step 2> MatMat 9의 합성 9, synthesis

Mat 1-B 대신에 Mat 9-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 9(5.5g, 수율 62%)를 얻었다.Mat 9-B was used in place of Mat 1-B to obtain Mat 9 (5.5 g, yield 62%).

Elemental Analysis: C, 88.13; H, 6.16; N, 5.71/ GC-Mass: 734
Elemental Analysis: C, 88.13; H, 6. 16; N, 5.71 / GC-Mass: 734

[[ 합성예Synthetic example 10] 화합물  10] compound MatMat 10의 합성 10 composite

Figure pat00025
Figure pat00025

<단계 1> <Step 1> MatMat 10-B의 합성 Synthesis of 10-B

2-Bromo-4,6-diphenylpyridine 대신에 4-bromodibenzo[b,d]thiophene를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 10-B(3g, 수율 54%)를 얻었다. Instead of 2-Bromo-4,6-diphenylpyridine, using 4-bromodibenzo [b, d] thiophene was carried out in the same manner as in Preparation Example 2 to obtain Mat 10-B (3g, 54% yield).

GC-Mass: 469GC-Mass: 469

<단계 2> <Step 2> MatMat 10의 합성 10 composite

Mat 1-B 대신에 Mat 10-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 10(4.9g, 수율 60%)을 얻었다.Using Mat 10-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 10 (4.9g, yield 60%).

Elemental Analysis: C, 85.42; H, 5.68; N, 4.15; S, 4.75/ GC-Mass: 673
Elemental Analysis: C, 85.42; H, 5.68; N, 4.15; S, 4.75 / GC-Mass: 673

[[ 합성예Synthetic example 11] 화합물  11] compound MatMat 11의 합성 11 Synthesis

Figure pat00026
Figure pat00026

<단계 1> <Step 1> MatMat 11-A의 합성 Synthesis of 11-A

Bromobenzene 대신에 2-bromo-4,6-diphenylpyridine를 사용하여 준비예 1과 동일한 과정을 수행하여 Mat 11-A(1.6g, 수율 73%)를 얻었다. Mat 11-A (1.6g, 73% yield) was obtained by performing the same procedure as Preparation Example 1 using 2-bromo-4,6-diphenylpyridine instead of bromobenzene.

GC-Mass: 563GC-Mass: 563

<단계 2> <Step 2> MatMat 11의 합성 11 Synthesis

Mat 1-A 대신에 Mat 11-A를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 11(5g, 수율 57%)을 얻었다.Using Mat 11-A instead of Mat 1-A was carried out in the same manner as in Synthesis Example 1 to obtain Mat 11 (5g, yield 57%).

Elemental Analysis: C, 87.84; H, 5.76; N, 6.40/ GC-Mass: 874
Elemental Analysis: C, 87.84; H, 5.76; N, 6.40 / GC-Mass: 874

[[ 합성예Synthetic example 12] 화합물  12] compounds MatMat 12의 합성 12 composite

Figure pat00027
Figure pat00027

<단계 1> <Step 1> MatMat 12-A의 합성 Synthesis of 12-A

Bromobenzene 대신에 2 2-bromonaphthalene를 사용하여 준비예 1과 동일한 과정을 수행하여 Mat 12-A(1.8g, 수율 80%)를 얻었다. Mat 12-A (1.8 g, yield 80%) was obtained in the same manner as in Preparation Example 1, using 2 2-bromonaphthalene instead of bromobenzene.

GC-Mass: 460GC-Mass: 460

<단계 2> <Step 2> MatMat 12의 합성 12 composite

Mat 1-A 대신에 Mat 12-A를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 12(5.6g 수율 72%)를 얻었다.Using Mat 12-A instead of Mat 1-A was carried out the same procedure as in Synthesis Example 1 to obtain Mat 12 (5.6g yield 72%).

Elemental Analysis: C, 88.68; H, 5.88; N, 5.44/ GC-Mass: 770
Elemental Analysis: C, 88.68; H, 5.88; N, 5.44 / GC-Mass: 770

[[ 합성예Synthetic example 13] 화합물  13] compound MatMat 13의 합성 13 Synthesis

Figure pat00028
Figure pat00028

Mat 1-A 대신에 Mat 12-A를 사용하고, Mat 1-B 대신에 Mat 2-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 13(4.2g, 수율 60%)을 얻었다.Mat 12-A was used instead of Mat 1-A and Mat 2-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis Example 1, thereby obtaining Mat 13 (4.2 g, yield 60%).

Elemental Analysis: C, 87.01; H, 5.74; N, 7.25/ GC-Mass: 771
Elemental Analysis: C, 87.01; H, 5.74; N, 7.25 / GC-Mass: 771

[[ 합성예Synthetic example 14] 화합물  14] Compound MatMat 14의 합성 14 Synthesis

Figure pat00029
Figure pat00029

<단계 1> <Step 1> MatMat 14-B의 합성 Synthesis of 14-B

2-Bromo-4,6-diphenylpyridine 대신에 3-bromo-9-(4,6-diphenylpyridin-2-yl)-9H-carbazole를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 14-B(2.3g, 수율 44%)를 얻었다.Instead of 2-Bromo-4,6-diphenylpyridine, 3-bromo-9- (4,6-diphenylpyridin-2-yl) -9H-carbazole was used to carry out Mat 14-B (2.3 g, yield 44%).

GC-Mass: 681 GC-Mass: 681

<단계 2> <Step 2> MatMat 14의 합성 14 Synthesis

Mat 1-B 대신에 Mat 14-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 14(3.9g, 수율 36%)를 얻었다.Using Mat 14-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 14 (3.9g, yield 36%).

Elemental Analysis: C, 88.00; H, 5.68; N, 6.32/ GC-Mass: 885
Elemental Analysis: C, 88.00; H, 5.68; N, 6.32 / GC-Mass: 885

[[ 합성예Synthetic example 15] 화합물  15] compound MatMat 15의 합성 15 composites

Figure pat00030
Figure pat00030

<단계 1> <Step 1> MatMat 15-B의 합성 Synthesis of 15-B

2-Bromo-4,6-diphenylpyridine 대신에 2-(4-bromophenyl)-4,6-diphenylpyridine를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 15-B(3.5g, 수율 65%)를 얻었다. Mat 15-B (3.5 g, yield 65%) was obtained by the same procedure as Preparation Example 2 using 2- (4-bromophenyl) -4,6-diphenylpyridine instead of 2-Bromo-4,6-diphenylpyridine. .

GC-Mass: 592GC-Mass: 592

<단계 2> <Step 2> MatMat 15의 합성 15 composites

Mat 1-B 대신에 Mat 15-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 15(4.8g, 수율 50%)를 얻었다.Using Mat 15-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 15 (4.8g, yield 50%).

Elemental Analysis: C, 88.80; H, 5.94; N, 5.27/ GC-Mass: 796
Elemental Analysis: C, 88.80; H, 5.94; N, 5.27 / GC-Mass: 796

[[ 합성예Synthetic example 16] 화합물  16] compound MatMat 16의 합성 16 composites

Figure pat00031
Figure pat00031

<단계 1> <Step 1> MatMat 16-A,  16-A, MatMat 16-B의 합성 Synthesis of 16-B

9,9-Dimethyl-9,10-dihydroacridine 대신에 10H-phenothiazine를 사용하여 준비예 1과 동일한 과정을 수행하여 Mat 16-A(1.5g, 수율 66%)를 얻고, 2-bromo-4,6-diphenylpyridine 대신에 2-(4-bromophenyl)pyridine를 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 16-B(3.8g, 수율 : 67%)를 얻었다. 10H-phenothiazine was used instead of 9,9-Dimethyl-9,10-dihydroacridine to carry out the same procedure as in Preparation Example 1 to obtain Mat 16-A (1.5 g, yield 66%), 2-bromo-4,6 Mat 16-B (3.8g, yield: 67%) was obtained by performing the same procedure as Preparation Example 2 using 2- (4-bromophenyl) pyridine instead of -diphenylpyridine.

GC-Mass: 400 (Mat 16-A)GC-Mass: 400 (Mat 16-A)

GC-Mass: 440 (Mat 16-B)GC-Mass: 440 (Mat 16-B)

<단계 2> <Step 2> MatMat 16의 합성 16 composites

Mat 1-A 대신에 Mat 16-A를 사용하고, Mat 1-B 대신에 Mat 16-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 16(3.4g, 수율 63%)을 얻었다.Mat 16-A was used instead of Mat 1-A and Mat 16-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis Example 1, thereby obtaining Mat 16 (3.4 g, yield 63%).

Elemental Analysis: C, 83.12; H, 5.23; N, 6.61; S, 5.04/ GC-Mass: 634
Elemental Analysis: C, 83.12; H, 5.23; N, 6.61; S, 5.04 / GC-Mass: 634

[[ 합성예Synthetic example 17] 화합물  17] Compound MatMat 17의 합성 17 Synthesis

Figure pat00032
Figure pat00032

<단계 1> <Step 1> MatMat 17-B의 합성 Synthesis of 17-B

2-Bromo-4,6-diphenylpyridine 대신에 2-methylquinoline을 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 17-B(4.2g, 수율 73%)를 얻었다. Mat 17-B (4.2 g, yield 73%) was obtained by the same procedure as Preparation Example 2 using 2-methylquinoline instead of 2-Bromo-4,6-diphenylpyridine.

GC-Mass: 414GC-Mass: 414

<단계 2> <Step 2> MatMat 17의 합성 17 Synthesis

Mat 1-A 대신에 Mat 16-A를 사용하고, Mat 1-B 대신에 Mat 17-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 17(3.2g, 수율 63%)을 얻었다.Mat 16-A was used instead of Mat 1-A, and Mat 17-B was used instead of Mat 1-B to carry out the same procedure as Synthesis Example 1, thereby obtaining Mat 17 (3.2 g, yield 63%).

Elemental Analysis: C, 82.73; H, 5.12; N, 6.89; S, 5.26/ GC-Mass: 608
Elemental Analysis: C, 82.73; H, 5.12; N, 6.89; S, 5.26 / GC-Mass: 608

[[ 합성예Synthetic example 18] 화합물  18] compound MatMat 18의 합성 18 composites

Figure pat00033
Figure pat00033

<단계 1> <Step 1> MatMat 18-B의 합성 Synthesis of 18-B

9,9-Dimethyl-9,10-dihydroacridine 대신에 10H-phenothiazine을 사용하고, 2-bromo-4,6-diphenylpyridine 대신에 3-bromo-9-phenyl-9H-carbazole을 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 18-B(2.1g, 수율 38%)를 얻었다. 10H-phenothiazine instead of 9,9-Dimethyl-9,10-dihydroacridine and 3-bromo-9-phenyl-9H-carbazole instead of 2-bromo-4,6-diphenylpyridine Mat 18-B (2.1 g, yield 38%) was obtained by the procedure.

GC-Mass: 518GC-Mass: 518

<단계 2> <Step 2> MatMat 18의 합성 18 composites

Mat 1-A 대신에 Mat 16-A를 사용하고, Mat 1-B 대신에 Mat 18-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 18(3.6g, 수율 58%)을 얻었다.Mat 16-A was used instead of Mat 1-A, and Mat 18-B was used instead of Mat 1-B, and Mat 18 (3.6 g, yield 58%) was obtained in the same manner as in Synthesis example 1.

Elemental Analysis: C, 80.75; H, 4.38; N, 5.89; S, 8.98/ GC-Mass: 712
Elemental Analysis: C, 80.75; H, 4.38; N, 5.89; S, 8.98 / GC-Mass: 712

[[ 합성예Synthetic example 19] 화합물  19] Compound MatMat 19의 합성 19 Synthesis

Figure pat00034
Figure pat00034

<단계 1> <Step 1> MatMat 19-A의 합성 Synthesis of 19-A

9,9-Dimethyl-9,10-dihydroacridine 대신에 9,9-diphenyl-9,10-dihydroacridine를 사용하여 준비예 1과 동일한 과정을 수행하여 Mat 19-A(1.1g, 수율 50%)를 얻었다.Mat 19-A (1.1 g, yield 50%) was obtained in the same manner as in Preparation Example 1, using 9,9-diphenyl-9,10-dihydroacridine instead of 9,9-Dimethyl-9,10-dihydroacridine. .

GC-Mass: 534 GC-Mass: 534

<단계 2> <Step 2> MatMat 19의 합성 19 Synthesis

Mat 1-A 대신에 Mat 19-A를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 19(2.3g, 수율 41%)를 얻었다.Using Mat 19-A instead of Mat 1-A was carried out the same procedure as in Synthesis Example 1 to obtain Mat 19 (2.3g, 41% yield).

Elemental Analysis: C, 89.43; H, 5.60; N, 4.97 / GC-Mass: 845
Elemental Analysis: C, 89.43; H, 5. 60; N, 4.97 / GC-Mass: 845

[[ 합성예Synthetic example 20] 화합물  20] compound MatMat 20의 합성 20 composites

Figure pat00035
Figure pat00035

<단계 1> <Step 1> MatMat 20-A, 20-B의 합성 Synthesis of 20-A, 20-B

9,9-Dimethyl-9,10-dihydroacridine 대신에 10H-phenothiazine을 사용하고 bromobenzene 대신에 2-bromonaphthalene을 사용하여 준비예 1과 동일한 과정을 수행하여 Mat 20-A(1.3g, 수율 45%)를 합성하고, 9,9-dimethyl-9,10-dihydroacridine 대신에 10H-phenothiazine을 사용하고 2-bromo-4,6-diphenylpyridine 대신에 2-(4-bromophenyl)pyridine을 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 20-B(1g, 수율 40%)를 합성하였다. 10H-phenothiazine instead of 9,9-Dimethyl-9,10-dihydroacridine and 2-bromonaphthalene instead of bromobenzene were used to carry out Mat 20-A (1.3 g, yield 45%). Synthesis was carried out in the same manner as in Preparation Example 2 using 10H-phenothiazine instead of 9,9-dimethyl-9,10-dihydroacridine and 2- (4-bromophenyl) pyridine instead of 2-bromo-4,6-diphenylpyridine Mat 20-B (1 g, yield 40%) was synthesized.

GC-Mass: 584 (Mat 20-A) GC-Mass: 584 (Mat 20-A)

GC-Mass: 564 (Mat 20-B)GC-Mass: 564 (Mat 20-B)

<단계 2> <Step 2> MatMat 20의 합성 20 composites

Mat 1-A 대신에 Mat 20-A를 사용하고 Mat 1-B 대신에 Mat 20-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 20(2.1g, 수율 32%)을 얻었다.Using Mat 20-A instead of Mat 1-A and Mat 20-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 20 (2.1 g, yield 32%).

Elemental Analysis: C, 90.32; H, 5.23; N, 4.45 / GC-Mass: 943
Elemental Analysis: C, 90.32; H, 5.23; N, 4.45 / GC-Mass: 943

[[ 합성예Synthetic example 21] 화합물  21] compound MatMat 21의 합성 Synthesis of 21

Figure pat00036
Figure pat00036

<단계 1> <Step 1> MatMat 21-B의 합성 Synthesis of 21-B

9,9-Dimethyl-9,10-dihydroacridine 대신에 10H-phenoxazine을 사용하여 준비예 2와 동일한 과정을 수행하여 Mat 21-B(4.2g, 수율 76%)를 얻었다. Mat 21-B (4.2 g, yield 76%) was obtained in the same manner as in Preparation Example 2, using 10H-phenoxazine instead of 9,9-Dimethyl-9,10-dihydroacridine.

GC-Mass: 491GC-Mass: 491

<단계 2> <Step 2> MatMat 21의 합성 Synthesis of 21

Mat 1-B 대신에 Mat 21-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 21(4.6g, 수율 55%)을 얻었다.Mat 21-B was used in place of Mat 1-B to obtain Mat 21 (4.6 g, 55% yield).

Elemental Analysis: C, 84.46; H, 5.21; N, 8.04; O, 2.30 / GC-Mass : 695
Elemental Analysis: C, 84.46; H, 5.21; N, 8.04; O, 2.30 / GC-Mass: 695

[[ 합성예Synthetic example 22] 화합물  22] compound MatMat 22의 합성 22 composite

Figure pat00037
Figure pat00037

<단계 1> <Step 1> MatMat 22-A의 합성 Synthesis of 22-A

9,9-Dimethyl-9,10-dihydroacridine 대신에 5,10-dihydrophenazine를 사용하고 bromobenzene을 2 당량 사용하여 준비예 1과 동일한 과정을 수행하여 Mat 22-A(1.3g, 수율 45%)를 얻었다. Mat 22-A (1.3 g, yield 45%) was obtained by the same procedure as in Preparation Example 1, using 5,10-dihydrophenazine instead of 9,9-dimethyl-9,10-dihydroacridine and using 2 equivalents of bromobenzene. .

GC-Mass: 459GC-Mass: 459

<단계 2> <Step 2> MatMat 22의 합성 22 composite

Mat 1-A 대신에 Mat 22-A를 사용하고, Mat 1-B 대신에 Mat 2-B를 사용하여 합성예 1과 동일한 과정을 수행하여 Mat 22(4.6g, 수율 55%)를 얻었다.Mat 22-A was used instead of Mat 1-A and Mat 2-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis Example 1 to obtain Mat 22 (4.6 g, yield 55%).

Elemental Analysis: C, 85.57; H, 5.35; N, 9.07 / GC-Mass: 770
Elemental Analysis: C, 85.57; H, 5. 35; N, 9.07 / GC-Mass: 770

[[ 실시예Example 1 ~ 22] 녹색 유기  1 to 22] green organic ELEL 소자의 제작 Device fabrication

합성예 1-22에서 합성한 화합물 Mat1 ~ Mat22를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 EL 소자를 제작하였다.After a high purity sublimation tablet of Compounds Mat1 to Mat22 synthesized in Synthesis Example 1-22 by a commonly known method, a green organic EL device was manufactured according to the following procedure.

먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/합성예 1 ~ 합성예 22의 각각의 화합물 + 10 % Ir(ppy)3 (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / Compound Compounds of Synthesis Examples 1 to 22 + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq on the thus prepared ITO transparent electrode An organic EL device was fabricated by stacking 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.

Figure pat00038
Figure pat00038

Figure pat00039

Figure pat00039

[[ 비교예Comparative example 1] 녹색 유기  1] Green organic ELEL 소자의 제작 Device fabrication

발광층 형성시 발광 호스트 물질로서 본 발명의 화합물 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 유기 EL 소자를 제작하였다.An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound of the present invention as a light emitting host material in forming the emission layer.

CBP의 구조는 하기와 같다.The structure of CBP is as follows.

Figure pat00040

Figure pat00040

[[ 평가예Evaluation example 1] One]

실시예 1-22 및 비교예 1에서 제작한 각각의 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each organic EL device produced in Example 1-22 and Comparative Example 1, the driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

샘플Sample 호스트Host 구동 전압
(V)Driving voltage
(V) EL 피크
(nm)EL peak
(nm) 전류효율
(cd/A)Current efficiency
(cd / A) 실시예 1Example 1 Mat1Mat1 5.705.70 517517 42.842.8 실시예 2Example 2 Mat2Mat2 5.815.81 516516 41.741.7 실시예 3Example 3 Mat3Mat3 5.805.80 519519 40.940.9 실시예 4Example 4 Mat4Mat4 5.815.81 515515 41.541.5 실시예 5Example 5 Mat5Mat5 5.815.81 517517 40.940.9 실시예 6Example 6 Mat6Mat6 5.735.73 516516 42.542.5 실시예 7Example 7 Mat7Mat7 5.785.78 518518 41.841.8 실시예 8Example 8 Mat8Mat8 5.705.70 514514 40.940.9 실시예 9Example 9 Mat9Mat9 5.795.79 518518 41.541.5 실시예 10Example 10 Mat10Mat10 5.755.75 516516 40.940.9 실시예 11Example 11 Mat11Mat11 5.775.77 515515 42.142.1 실시예 12Example 12 Mat12Mat12 5.795.79 518518 41.541.5 실시예 13Example 13 Mat13Mat13 5.805.80 517517 40.940.9 실시예 14Example 14 Mat14Mat14 5.845.84 518518 40.940.9 실시예 15Example 15 Mat15Mat15 5.815.81 516516 41.441.4 실시예 16Example 16 Mat16Mat16 5.795.79 516516 41.541.5 실시예 17Example 17 Mat17Mat17 5.805.80 517517 40.440.4 실시예 18Example 18 Mat18Mat18 5.865.86 515515 40.640.6 실시예 19Example 19 Mat19Mat19 5.895.89 516516 39.339.3 실시예 20Example 20 Mat20Mat20 5.845.84 517517 39.839.8 실시예 21Example 21 Mat21Mat21 6.066.06 518518 39.239.2 실시예 22Example 22 Mat22Mat22 6.126.12 518518 39.539.5 비교예 1Comparative Example 1 CBPCBP 6.936.93 516516 38.238.2

상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 유기 EL 소자의 발광층으로 사용하였을 경우(실시예 1~22) 종래 CBP를 사용한 유기 EL 소자(비교예 1)와 비교해 볼 때 전압 및 효율 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.
As shown in Table 1 above, when the compound according to the present invention was used as the light emitting layer of the organic EL device (Examples 1 to 22), the voltage and efficiency in comparison with the organic EL device using the conventional CBP (Comparative Example 1) It can be seen that the better performance in the.

Claims (7)

하기 화학식 1로 표시되는 화합물:
<화학식 1>
Figure pat00041

상기 식에서,
X1 및 X2는 각각 독립적으로 CR1R2, O, S, NR3 및 SiR4R5 로 이루어진 군에서 선택되고;
Ar1 및 Ar2는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기, 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택되며;
R1 내지 R5는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택되거나, 인접한 기와 서로 결합하여 축합 고리를 형성하며;
n 및 m은 각각 독립적으로 1 내지 4의 정수이며;
하나 이상의 Ar3는 서로 같거나 다르고, 하나 이상의 Ar4는 서로 같거나 다르며, 이들은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환된 C1~C60의 알킬기, 치환 또는 비치환된 C2~C60의 알케닐기, 치환 또는 비치환된 C2~C60의 알키닐기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 치환 또는 비치환된 C1~C60의 알콕시기, 치환 또는 비치환된 C6~C60의 아릴옥시기, 치환 또는 비치환된 C3~C60의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 60의 헤테로시클로알킬기, 치환 또는 비치환된 C6~C60의 아릴아민기 및 치환 또는 비치환된 실릴기로 이루어진 군에서 선택된다.A compound represented by the following formula (1):
&Lt; Formula 1 >
Figure pat00041

In this formula,
X 1 and X 2 are each independently selected from the group consisting of CR 1 R 2 , O, S, NR 3 and SiR 4 R 5 ;
Ar 1 and Ar 2 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ~ C 60 alkyl group, substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ~ C 60 arylamine group, and a substituted or unsubstituted silyl group;
R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ~ C 60 alkyl group, substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ~ C 60 aryl group and a substituted or unsubstituted amine selected from the group consisting of unsubstituted silyl, and adjacent groups combine with each other to form a condensed ring;
n and m are each independently an integer from 1 to 4;
At least one Ar 3 is the same as or different from each other, at least one Ar 4 is the same as or different from each other, and each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 ~ C 60 alkenyl group, substituted or unsubstituted C 2 ~ C 60 Alkynyl group, substituted or unsubstituted C 6 ~ C 60 Aryl group, substituted or unsubstituted nuclear atoms of 5 to 60 Heteroaryl group, substituted or unsubstituted C 1 to C 60 alkoxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted It is selected from the group consisting of a ring heteronuclear alkyl group having 3 to 60 ring atoms, a substituted or unsubstituted C 6 ~ C 60 arylamine group, and a substituted or unsubstituted silyl group. 제1항에 있어서,
Ar1 및 Ar2의 상기 아릴기는 각각 독립적으로 비치환된 C6~C60의 아릴기이거나 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 C6~C60의 아릴기이고, Ar1 및 Ar2의 상기 헤테로아릴기는 각각 독립적으로 비치환된 핵원자수 5 내지 60의 헤테로아릴기이거나 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 핵원자수 5 내지 60의 헤테로아릴기인 것을 특징으로 하는 화합물.The method of claim 1,
The aryl groups of Ar 1 and Ar 2 are each independently unsubstituted C 6 ~ C 60 aryl group or C 6 ~ C 60 aryl group, C 6 ~ 60 heteroaryl group or C 6 substituted with an amino group An aryl group of ~ C 60 , and each of the heteroaryl groups of Ar 1 and Ar 2 is independently an unsubstituted heteroaryl group having 5 to 60 nuclear atoms, or an aryl group having 6 to C 60 atoms, and 5 to 60 nuclear atoms. A heteroaryl group or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group. 제1항에 있어서,
Ar1 및 Ar2는 각각 독립적으로 비치환된 C6~C60의 아릴기; C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 C6~C60의 아릴기; 비치환된 핵원자수 5 내지 60의 헤테로아릴기; 또는 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 핵원자수 5 내지 60의 헤테로아릴기인 것을 특징으로 하는 화합물.The method of claim 1,
Ar 1 and Ar 2 are each independently an unsubstituted C 6 ~ C 60 aryl group; C 6 -C 60 aryl group substituted with a C 6 ~ C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms or an amino group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group. 제1항에 있어서,
Ar1은 비치환된 C6~C60의 아릴기; 또는 C6~C60의 아릴기로 치환된 핵원자수 5 내지 60의 헤테로아릴기이고, Ar2는 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 또는 아미노기로 치환된 C6~C60의 아릴기; 비치환된 핵원자수 5 내지 60의 헤테로아릴기; 또는 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기로 치환된 핵원자수 5 내지 60의 헤테로아릴기인 것을 특징으로 하는 화합물.The method of claim 1,
Ar 1 is an unsubstituted C 6 ~ C 60 aryl group; Or a heteroaryl group of 5 to 60 nuclear atoms substituted with an aryl group of C 6 to C 60 , and Ar 2 is substituted with an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms or an amino group C 6 ~ C 60 Aryl group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C 6 to C 60 aryl group or a heteroaryl group having 5 to 60 nuclear atoms substituted with a heteroaryl group having 5 to 60 nuclear atoms. 제1항에 있어서,
X1 및 X2는 각각 독립적으로 CR1R2 또는 SiR4R5인 것을 특징으로 하는 화합물.The method of claim 1,
And X 1 and X 2 are each independently CR 1 R 2 or SiR 4 R 5 . (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,
상기 유기물층 중에서 적어도 하나는 제1항 내지 제5항 중 어느 한 항에 따른 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
At least one of the organic layer is an organic electroluminescent device comprising a compound according to any one of claims 1 to 5. 제 6 항에 있어서,
상기 화합물은 발광층에 포함되는 것을 특징으로 하는 유기 전계 발광 소자.
The method according to claim 6,
The compound is an organic electroluminescent device, characterized in that contained in the light emitting layer.
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