KR20220136613A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

An electroluminescent compound and an electroluminescent device comprising the same Download PDF

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KR20220136613A
KR20220136613A KR1020210042466A KR20210042466A KR20220136613A KR 20220136613 A KR20220136613 A KR 20220136613A KR 1020210042466 A KR1020210042466 A KR 1020210042466A KR 20210042466 A KR20210042466 A KR 20210042466A KR 20220136613 A KR20220136613 A KR 20220136613A
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윤석근
현서용
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(주)피엔에이치테크
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    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • HELECTRICITY
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    • H10K50/00Organic light-emitting devices
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    • H10K50/14Carrier transporting layers
    • H10K50/15Hole transporting layers
    • HELECTRICITY
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
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Abstract

The present invention relates to a novel organic light emitting compound represented by a chemical formula I that is employed in an organic layer such as an electron transport layer in an organic light emitting device to realize light emitting characteristics such as low voltage driving, excellent light emitting efficiency and the like of the device, and to an organic light emitting device including the same.

Description

유기발광 화합물 및 이를 포함하는 유기발광소자 {An electroluminescent compound and an electroluminescent device comprising the same}An organic light emitting compound and an organic light emitting device comprising the same

본 발명은 유기발광 화합물에 관한 것으로서, 더욱 상세하게는 유기발광소자 내의 유기층 재료로 채용되는 것을 특징으로 하는 유기발광 화합물과 이를 채용하여 소자의 저전압 구동과 우수한 발광 효율 등의 발광 특성이 현저히 향상된 유기발광소자에 관한 것이다.The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound, characterized in that it is employed as an organic layer material in an organic light emitting device, and an organic light emitting property having significantly improved light emitting properties such as low voltage driving and excellent luminous efficiency of the device by employing the same It relates to a light emitting device.

유기발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널 (Plasma Display Panel)이나 무기전계발광 (EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescence (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red, and has recently become a subject of much interest as a next-generation display device.

다만, 이러한 유기발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기발광소자용 유기층 재료의 개발이 충분히 이루어지지 않은 상태이다.However, in order for such an organic light emitting device to exhibit the above characteristics, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed.

따라서, 더욱 안정적인 유기발광소자를 구현하고, 소자의 고효율, 장수명, 대형화 등을 위해서는 효율 및 수명 특성 측면에서 추가적인 개선이 요구되고 있는 상황이고, 특히 유기발광소자의 각 유기층을 이루는 소재에 대한 개발이 절실히 필요한 실정이다.Therefore, in order to realize a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, additional improvements are required in terms of efficiency and lifespan characteristics. It is desperately needed.

따라서, 본 발명은 유기발광소자 내의 유기층에 채용되어 소자의 저전압 구동과 향상된 발광 효율 등의 우수한 발광 특성을 구현할 수 있는 신규한 유기발광 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Accordingly, an object of the present invention is to provide a novel organic light emitting compound capable of implementing excellent light emitting characteristics such as low voltage driving and improved luminous efficiency of the device by being employed in the organic layer in the organic light emitting device, and an organic light emitting device including the same.

본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 제공한다.The present invention provides an organic light emitting compound represented by the following [Formula I] in order to solve the above problems.

[화학식 Ⅰ][Formula Ⅰ]

Figure pat00001
Figure pat00001

상기 [화학식 Ⅰ]의 특징적인 구조와 이에 의하여 구현되는 화합물, X, L 및 A에 대해서는 후술하기로 한다.The characteristic structure of the [Formula I] and the compounds implemented thereby, X, L and A will be described later.

본 발명에 따른 유기발광 화합물을 유기발광소자 내의 전자수송층 등의 유기층 재료로 채용할 경우에 소자의 저전압 구동과 우수한 발광 효율 등의 발광 특성을 구현할 수 있어 다양한 디스플레이 소자에 유용하게 사용될 수 있다.When the organic light emitting compound according to the present invention is employed as a material for an organic layer such as an electron transport layer in an organic light emitting device, it is possible to realize light emitting characteristics such as low voltage driving and excellent luminous efficiency of the device, so it can be usefully used in various display devices.

이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.

본 발명은 유기발광소자의 소자의 저전압 구동과 우수한 발광 효율 등의 발광 특성을 거둘 수 있는 하기 [화학식 Ⅰ]로 표시되는 유기발광 화합물에 관한 것으로서,The present invention relates to an organic light-emitting compound represented by the following [Formula I], which can achieve light-emitting characteristics such as low voltage driving of the organic light-emitting device and excellent light-emitting efficiency,

구조적으로 하기 [화학식 Ⅰ]로 표시되는 골격 구조, 즉 하나 이상의 옥사졸로퀴놀린, 티아졸로퀴놀린, 미미다조퀴놀린 유도체에 연결기(L)을 통하여 특징적 치환기 A를 도입한 것을 특징으로 하고, 이러한 구조적 특징을 통하여 유기발광소자의 저전압 구동 특성, 발광 효율 특성을 향상시킬 수 있다.It is characterized in that a characteristic substituent A is introduced through a linking group (L) into the skeletal structure structurally represented by the following [Formula I], that is, at least one oxazoloquinoline, thiazoloquinoline, or mimidazoquinoline derivative, and these structural features are Through this, it is possible to improve the low voltage driving characteristics and luminous efficiency characteristics of the organic light emitting diode.

[화학식 Ⅰ][Formula Ⅰ]

Figure pat00002
Figure pat00002

상기 [화학식 Ⅰ]에서,In the above [Formula I],

X는 O, S 또는 NR1이며, 상기 R1은 수소, 중수소, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택된다.X is O, S or NR 1 , wherein R 1 is hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, substituted or an unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group.

L은 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기 중에서 선택되는 어느 하나이며, m은 0 내지 3의 정수이고, 상기 m이 2 이상인 경우 복수 개의 L은 서로 동일하거나 상이하다.L is a single bond, or any one selected from a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group, m is an integer from 0 to 3, wherein m In the case of two or more, a plurality of L's are the same as or different from each other.

A는 하기 [구조식 1] 또는 [구조식 2]로 표시되는 것을 특징으로 한다.A is characterized in that it is represented by the following [Structural Formula 1] or [Structural Formula 2].

[구조식 1][Structural Formula 1]

Figure pat00003
Figure pat00003

[구조식 2][Structural Formula 2]

Figure pat00004
Figure pat00004

상기 [구조식 1]과 [구조식 2]에서,In the above [Structural Formula 1] and [Structural Formula 2],

X1 내지 X3은 서로 동일하거나 상이하고, 각각 독립적으로 CH 또는 N이다.X 1 to X 3 are the same as or different from each other, and each independently is CH or N.

L1은 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기 중에서 선택되며, o는 0 내지 3의 정수이고, 상기 o가 2 이상인 경우 복수 개의 L1은 서로 동일하거나 상이하다.L 1 is a single bond, or is selected from a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C3 to C30 heteroarylene group, o is an integer from 0 to 3, wherein o is 2 In the case of more than one, a plurality of L 1 are the same as or different from each other.

Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되며, q 및 r은 0 내지 3의 정수이고, 상기 q 및 r이 각각 2 이상인 경우 상기 복수 개의 Ar1 및 Ar2는 각각 서로 동일하거나 상이하다.Ar 1 and Ar 2 are the same as or different from each other, and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, q and r is an integer of 0 to 3, and when q and r are each 2 or more, the plurality of Ar 1 and Ar 2 are the same as or different from each other, respectively.

Ar3은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되며, p는 0 내지 3의 정수이고, 상기 p가 2 이상인 경우 상기 복수 개의 Ar3은 서로 동일하거나 상이하다.Ar 3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, p is an integer from 0 to 3, and when p is 2 or more, the plurality of Ar 3 is the same as or different from each other.

n은 1 내지 3의 정수이며, 상기 n이 2 이상인 경우 상기 복수 개의 괄호 [ ] 안의 구조는 서로 동일하거나 상이하다.n is an integer of 1 to 3, and when n is 2 or more, the structures in the plurality of parentheses [ ] are the same or different from each other.

l은 1 내지 2의 정수이며, 상기 l이 2인 경우 각각의 A는 서로 동일하거나 상이하다.l is an integer of 1 to 2, and when l is 2, each A is the same as or different from each other.

본 발명의 일 실시예에 의하면, 상기 [화학식 Ⅰ]은 하기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-4] 중에서 선택되는 어느 하나일 수 있다.According to an embodiment of the present invention, the [Formula I] may be any one selected from the following [Formula I-1] to [Formula I-4].

[화학식 Ⅰ-1] [화학식 Ⅰ-2][Formula Ⅰ-1] [Formula Ⅰ-2]

Figure pat00005
Figure pat00006
Figure pat00005
Figure pat00006

[화학식 Ⅰ-3] [화학식 Ⅰ-4][Formula Ⅰ-3] [Formula Ⅰ-4]

Figure pat00007
Figure pat00008
Figure pat00007
Figure pat00008

상기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-4]에서, X, L, A, n 및 m의 정의는 상기 [화학식 Ⅰ]에서의 정의와 동일하다.In the [Formula I-1] to [Formula I-4], the definitions of X, L, A, n and m are the same as the definitions in the [Formula I].

한편, 상기 R1, L, L1 및 Ar1 내지 Ar3의 정의에서, '치환 또는 비치환된'이라 함은, 상기 R1, L, L1 및 Ar1 내지 Ar3이 각각 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 알킬기, 할로겐화된 알킬기, 중수소화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 할로겐화된 알콕시기, 중수소화된 알콕시기, 아릴기 및 헤테로아릴기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.On the other hand, in the definition of R 1 , L, L 1 and Ar 1 to Ar 3 , 'substituted or unsubstituted' means that R 1 , L, L 1 and Ar 1 to Ar 3 are deuterium and halogen, respectively. group, cyano group, nitro group, hydroxyl group, silyl group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, aryl group and heteroaryl It means that it is substituted with one or two or more substituents selected from the group consisting of a group, is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.

구체적인 예를 들면, 치환된 아릴기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기, 안트라센닐기 등이 다른 치환기로 치환된 것을 의미한다.For specific examples, the substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc. are substituted with other substituents do.

또한, 치환된 헤테로아릴기라 함은, 피리딜기, 티오페닐기, 트리아진기, 퀴놀린기, 페난트롤린기, 이미다졸기, 티아졸기, 옥사졸기, 카바졸기 및 이들의 축합헤테로고리기, 예컨대 벤즈퀴놀린기, 벤즈이미다졸기, 벤즈옥사졸기, 벤즈티아졸기, 벤즈카바졸기, 디벤조티오페닐기, 디벤조퓨란기 등이 다른 치환기로 치환된 것을 의미한다.In addition, the substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and a condensed heterocyclic group thereof, such as a benzquinoline group. , a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other substituents.

본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니다.In the present invention, examples of the substituents will be described in detail below, but the present invention is not limited thereto.

본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 20인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 입체적 방해를 주지 않는 범위인 1 내지 20개인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be straight-chain or branched. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20, which is a range that does not cause steric hindrance. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

본 발명에 있어서, 중수소화된 알킬기 또는 알콕시기, 할로겐화된 알킬기 또는 알콕시기는 상기 알킬기 또는 알콕시기가 중수소 또는 할로겐기로 치환된 알킬기 또는 알콕시기를 의미한다.In the present invention, a deuterated alkyl group or alkoxy group, halogenated alkyl group or alkoxy group means an alkyl group or alkoxy group in which the alkyl group or alkoxy group is substituted with deuterium or a halogen group.

본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하다. 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌(fluoranthrene)기 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.

본 발명에 있어서, 플루오레닐기는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조로서, 예로는

Figure pat00009
,
Figure pat00010
,
Figure pat00011
등이 있다.In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example,
Figure pat00009
,
Figure pat00010
,
Figure pat00011
etc.

본 발명에 있어서, 플루오레닐기는 열린 플루오레닐기의 구조를 포함하며, 여기서 열린 플루오레닐기는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조에서 한쪽 고리 화합물의 연결이 끊어진 상태의 구조로서, 예로는

Figure pat00012
,
Figure pat00013
등이 있다.In the present invention, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected through one atom. , for example
Figure pat00012
,
Figure pat00013
etc.

또한, 상기 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며, 예로는

Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
등이 있다.In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example,
Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
etc.

또한, 상기와 같이 표시된 플루오레닐기는 각 벤젠 고리에 지환족 또는 방향족 고리가 더 축합될 수 있다.In addition, the fluorenyl group represented as described above may be further condensed with an alicyclic or aromatic ring on each benzene ring.

본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30인 것이 바람직하며, 본 발명에서 이의 구체적인 예를 들면, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기, 페녹사진기, 페노티아진기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and a specific example thereof in the present invention is a thiophene group , furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyra Zinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia and a zolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazine group, a phenothiazine group, and the like, but are not limited thereto.

본 발명에 있어서, 실릴기는 비치환된 실릴기 또는 알킬기, 아릴기 등으로 치환된 실릴기로서, 이러한 실릴기의 구체적인 예로는 트리메틸실릴, 트리에틸실릴, 트리페닐실릴, 트리메톡시실릴, 디메톡시페닐실릴, 디페닐메틸실릴, 디페닐비닐실릴, 메틸사이클로뷰틸실릴, 디메틸퓨릴실릴 등을 들 수 있으며, 이에 한정되는 것은 아니다.In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but is not limited thereto.

본 발명에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of the halogen group as a substituent used in the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.

본 발명에 있어서, 시클로알킬기는 단환, 다환 및 스피로 알킬 라디칼을 지칭하고, 이를 포함하며, 바람직하게는 탄소수 3 내지 20의 고리 탄소 원자를 함유하는 것으로서, 시클로프로필, 시클로펜틸, 시클로헥실, 비시클로헵틸, 스피로데실, 스피로운데실, 아다만틸 등을 포함하며, 시클로알킬기는 임의로 치환될 수 있다.In the present invention, the cycloalkyl group refers to, and includes, monocyclic, polycyclic and spiro alkyl radicals, preferably containing 3 to 20 ring carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirodecyl, adamantyl, and the like, wherein the cycloalkyl group may be optionally substituted.

본 발명에 있어서, 헤테로시클로알킬기는 하나 이상의 헤테로 원자를 함유하는 방향족 및 비방향족 시클릭 라디칼을 지칭하고, 이를 포함하며, 하나 이상의 헤테로원자는 O, S, N, P, B, Si, 및 Se, 바람직하게는 O, N 또는 S로부터 선택되며, 구체적으로 N을 포함하는 경우 아지리딘, 피롤리딘, 피페리딘, 아제판, 아조칸 등일 수 있다.In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, wherein one or more heteroatoms are O, S, N, P, B, Si, and Se , Preferably it is selected from O, N, or S, and specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.

상기 [화학식 Ⅰ]로 표시되는 본 발명에 따른 유기발광 화합물은 그 구조적 특이성으로 인하여 유기발광소자 내의 전자수송층을 포함하여 다양한 유기층으로 사용될 수 있다.The organic light emitting compound according to the present invention represented by the [Formula I] can be used as various organic layers, including the electron transport layer in the organic light emitting device due to its structural specificity.

본 발명에 따른 [화학식 Ⅰ]로 표시되는 유기발광 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred examples of the organic light emitting compound represented by [Formula I] according to the present invention include the following compounds, but are not limited thereto.

Figure pat00018
Figure pat00018

Figure pat00019
Figure pat00019

Figure pat00020
Figure pat00020

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

Figure pat00025
Figure pat00025

Figure pat00026
Figure pat00026

Figure pat00027
Figure pat00027

Figure pat00028
Figure pat00028

Figure pat00029
Figure pat00029

Figure pat00030
Figure pat00030

Figure pat00031
Figure pat00031

Figure pat00032
Figure pat00032

Figure pat00033
Figure pat00033

Figure pat00034
Figure pat00034

Figure pat00035
Figure pat00035

Figure pat00036
Figure pat00036

Figure pat00037
Figure pat00037

Figure pat00038
Figure pat00038

Figure pat00039
Figure pat00039

Figure pat00040
Figure pat00040

Figure pat00041
Figure pat00041

Figure pat00042
Figure pat00042

Figure pat00043
Figure pat00043

Figure pat00044
Figure pat00044

Figure pat00045
Figure pat00045

Figure pat00046
Figure pat00046

Figure pat00047
Figure pat00047

Figure pat00048
Figure pat00048

Figure pat00049
Figure pat00049

이와 같이, 본 발명에 따른 유기발광 화합물은 고유의 특성을 발휘하는 특징적인 골격과 이에 도입되는 고유의 특성을 갖는 모이어티 (moiety)를 이용하여 다양한 특성을 갖는 유기발광 화합물을 합성할 수 있고, 그 결과 본 발명에 따른 유기발광 화합물을 발광층, 정공수송층, 전자수송층, 전자저지층, 정공저지층 등 다양한 유기층 물질로 적용할 수 있고, 바람직하게는 전자수송 재료로 소자의 발광효율 등의 발광 특성을 더욱 향상시킬 수 있다.As such, the organic light emitting compound according to the present invention can synthesize an organic light emitting compound having various characteristics by using a characteristic skeleton exhibiting intrinsic properties and a moiety having intrinsic properties introduced thereto, As a result, the organic light emitting compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. can be further improved.

또한, 본 발명의 화합물은 일반적인 유기발광소자 제조방법에 따라 소자에 적용할 수 있다.In addition, the compound of the present invention can be applied to a device according to a general organic light emitting device manufacturing method.

본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기발광 화합물을 소자의 유기층에 사용한다는 것을 제외하고는 통상의 소자 제조방법 및 재료를 사용하여 제조될 수 있다.The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween. Except that, it may be manufactured using conventional device manufacturing methods and materials.

본 발명에 따른 유기발광소자의 유기층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 저지층, 정공 저지층 등을 포함할 수 있으며, 유기발광소자에 구비되는 광효율 개선층 (Capping layer)을 포함하는 구조를 가질 수도 있으며, 그러나, 이에 한정되지 않고 더 적은 수, 더 많은 수의 유기층을 포함할 수도 있다.The organic layer of the organic light emitting diode according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked. For example, it may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc., a structure including a light efficiency improving layer (Capping layer) provided in the organic light emitting device It may have, but is not limited thereto, and may include a smaller number or a larger number of organic layers.

본 발명에 따른 바람직한 유기발광소자의 유기층 구조 등에 대해서는 후술하는 실시예에서 보다 상세하게 설명한다.The organic layer structure of the preferred organic light emitting device according to the present invention will be described in more detail in the following Examples.

또한, 본 발명에 따른 유기발광소자는 스퍼터링 (sputtering)이나 전자빔 증발 (e-beam evaporation)과 같은 PVD (physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층, 전자 수송층을 포함하는 유기층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.In addition, the organic light emitting diode according to the present invention is a metal or conductive metal oxide or an alloy thereof on a substrate by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be prepared by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to this method, an organic light emitting diode may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

상기 양극 물질로는 통상 유기층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물, ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.

상기 음극 물질로는 통상 유기층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금, LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, and multilayers such as LiF/Al or LiO 2 /Al Structural materials and the like, but are not limited thereto.

정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송 받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 본 발명에 따른 유기발광 화합물을 이용하여 소자의 저전압 구동 특성, 발광효율 및 수명 특성을 더욱 향상시킬 수 있다.As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. can be further improved.

발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3), 카르바졸 계열 화합물, 이량체화 스티릴(dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자, 스피로(spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light-emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but is not limited thereto.

전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.

본 발명에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting diode according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.In addition, the organic light emitting compound according to the present invention may act on a principle similar to that applied to the organic light emitting device in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like.

이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않고, 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, the scope of the present invention is not limited thereby, and it is common in the art that various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those with knowledge.

합성예Synthesis example 1 : 화합물 3 합성 1: Synthesis of compound 3

(1) (One) 제조예production example 1 : 중간체 3-1의 합성 1: Synthesis of Intermediate 3-1

Figure pat00050
Figure pat00050

7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 3-1>을 14.3 g (수율 70.4%) 수득하였다.Add 7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), and 200 mL of DMF, and stir at 80 °C for 2 hours. reacted. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 14.3 g (yield 70.4%) of <Intermediate 3-1>.

(2) (2) 제조예production example 2 : 화합물 3의 합성 2: Synthesis of compound 3

Figure pat00051
Figure pat00051

중간체 3-1 (10.0 g, 0.031 mol), 10-Phenylanthracene-9-boronic acid (11.0 g, 0.037 mol), K2CO3 (12.8 g, 0.092 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 3>을 11.3 g (수율 73.7%) 수득하였다.Intermediate 3-1 (10.0 g, 0.031 mol), 10-Phenylanthracene-9-boronic acid (11.0 g, 0.037 mol), K 2 CO 3 (12.8 g, 0.092 mol), Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 11.3 g (yield 73.7%) of <Compound 3> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=498[(M+1)+]LC/MS: m/z=498 [(M+1) + ]

합성예Synthesis example 2 : 화합물 13 합성 2: Synthesis of compound 13

(1) (One) 제조예production example 1 : 중간체 13-1의 합성 1: Synthesis of Intermediate 13-1

Figure pat00052
Figure pat00052

중간체 3-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl2 (1.1 g, 0.002 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 13-1>을 8.2 g (수율 71.6%) 수득하였다.Intermediate 3-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl 2 (1.1 g, 0.002 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.2 g (yield 71.6%) of <Intermediate 13-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) (2) 제조예production example 2 : 화합물 13의 합성 2: Synthesis of compound 13

Figure pat00053
Figure pat00053

중간체 3-1 (10.0 g, 0.027 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.6 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 13>을 9.1 g (수율 70.9%) 수득하였다.Intermediate 3-1 (10.0 g, 0.027 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.6 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.081 mol), Pd (PPh 3 ) 4 (0.6 g, 0.0005 mol) was added to 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 9.1 g (yield 70.9%) of <Compound 13> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=477[(M+1)+]LC/MS: m/z=477 [(M+1) + ]

합성예Synthesis example 3 : 화합물 19의 합성 3: Synthesis of compound 19

(1) (One) 제조예production example 1 : 중간체 19-1의 합성 1: Synthesis of Intermediate 19-1

Figure pat00054
Figure pat00054

2-Chloro-4,6-diphenyl-1,3,5-triazine (10 g, 0.044 mol), 4-Cyanobenzeneboronic acid (7.8 g, 0.053 mol), K2CO3 (18.3 g, 0.133 mol), Pd(PPh3)4 (1.0 g, 0.0009 mol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 19-1>을 7.2 g (수율 55.6%) 수득하였다.2-Chloro-4,6-diphenyl-1,3,5-triazine (10 g, 0.044 mol), 4-Cyanobenzeneboronic acid (7.8 g, 0.053 mol), K 2 CO 3 (18.3 g, 0.133 mol), Pd 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O were added to (PPh 3 ) 4 (1.0 g, 0.0009 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, 7.2 g (yield 55.6%) of <Intermediate 19-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) (2) 제조예production example 2 : 화합물 19의 합성 2: Synthesis of compound 19

Figure pat00055
Figure pat00055

중간체 13-1 (10.0 g, 0.027 mol), 중간체 19-1 (9.4 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 19>를 9.7 g (수율 71.9%) 수득하였다.Intermediate 13-1 (10.0 g, 0.027 mol), Intermediate 19-1 (9.4 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.081 mol), Pd(PPh 3 ) 4 (0.6 g, 0.0005 mol) Toluene 200 mL, EtOH 50 mL, H 2 O 50 mL, and stirred at 100 ℃ for 6 hours to react. After completion of the reaction, 9.7 g (yield 71.9%) of <Compound 19> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=502[(M+1)+]LC/MS: m/z=502[(M+1) + ]

합성예Synthesis example 4 : 화합물 25의 합성 4: Synthesis of compound 25

(1) (One) 제조예production example 1 : 중간체 25-1의 합성 1: Synthesis of Intermediate 25-1

Figure pat00056
Figure pat00056

2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), (4-Naphthalen-2-ylphenyl)boronic acid (8.7 g, 0.035 mol), K2CO3 (12.1 g, 0.088 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 25-1>을 7.7 g (수율 51.7%) 수득하였다.2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), (4-Naphthalen-2-ylphenyl)boronic acid (8.7 g, 0.035 mol), K 2 CO 3 (12.1 g, 0.088 mol), Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) Toluene 200 mL, EtOH 50 mL, H 2 O 50 mL Add 6 hours The reaction was stirred at 100 °C for a while. After completion of the reaction, 7.7 g (yield 51.7%) of <Intermediate 25-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) (2) 제조예production example 2 : 화합물 25의 합성 2: Synthesis of compound 25

Figure pat00057
Figure pat00057

중간체 13-1 (10.0 g, 0.027 mol), 중간체 25-1 (16.4 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 25>를 13.3 g (수율 68.8%) 수득하였다.Intermediate 13-1 (10.0 g, 0.027 mol), Intermediate 25-1 (16.4 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.081 mol), Pd(PPh 3 ) 4 (0.6 g, 0.0005 mol) Toluene 200 mL, EtOH 50 mL, H 2 O 50 mL, and stirred at 100 ℃ for 6 hours to react. After completion of the reaction, 13.3 g (yield 68.8%) of <Compound 25> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=719[(M+1)+]LC/MS: m/z=719[(M+1) + ]

합성예Synthesis example 5 : 화합물 41의 합성 5: Synthesis of compound 41

(1) (One) 제조예production example 1 : 화합물 41의 합성 1: Synthesis of compound 41

Figure pat00058
Figure pat00058

7-Amino-8-hydroxyquinoline (7.9 g, 0.049 mol), Triethylamine 25.7 mL를 NMP에 용해시킨다. 그 후 1,4-Benzenedicarbonyl chloride (10.0 g, 0.049 mol)를 dropwise로 상온에서 첨가하고 160 ℃에서 24시간 동안 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 41>을 6.3 g (수율 30.9%) 수득하였다.Dissolve 7-Amino-8-hydroxyquinoline (7.9 g, 0.049 mol) and 25.7 mL of Triethylamine in NMP. Then, 1,4-Benzenedicarbonyl chloride (10.0 g, 0.049 mol) was added dropwise at room temperature and reacted at 160 °C for 24 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 6.3 g (yield 30.9%) of <Compound 41>.

LC/MS: m/z=414[(M+1)+]LC/MS: m/z=414 [(M+1) + ]

합성예Synthesis example 6 : 화합물 44의 합성 6: Synthesis of compound 44

(1) (One) 제조예production example 1 : 중간체 44-1의 합성 1: Synthesis of intermediate 44-1

Figure pat00059
Figure pat00059

1-Bromo-4-iodonaphthalene (10.0 g, 0.030 mol), 4-Cyanobenzeneboronic acid (5.3 g, 0.036 mol), K2CO3 (12.5 g, 0.090 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 44-1>을 5.6 g (수율 60.5%) 수득하였다.1-Bromo-4-iodonaphthalene (10.0 g, 0.030 mol), 4-Cyanobenzeneboronic acid (5.3 g, 0.036 mol), K 2 CO 3 (12.5 g, 0.090 mol), Pd(PPh 3 ) 4 (0.7 g, 0.0006) mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 5.6 g (yield 60.5%) of <Intermediate 44-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) (2) 제조예production example 2 : 화합물 44의 합성 2: Synthesis of compound 44

Figure pat00060
Figure pat00060

중간체 13-1 (10.0 g, 0.027 mol), 중간체 44-1 (9.9 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 44>를 9.5 g (수율 74.7%) 수득하였다.Intermediate 13-1 (10.0 g, 0.027 mol), Intermediate 44-1 (9.9 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.081 mol), Pd(PPh 3 ) 4 (0.6 g, 0.0005 mol) Toluene 200 mL, EtOH 50 mL, H 2 O 50 mL, and stirred at 100 ℃ for 6 hours to react. After completion of the reaction, 9.5 g (yield 74.7%) of <Compound 44> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=473[(M+1)+]LC/MS: m/z=473 [(M+1) + ]

합성예Synthesis example 7 : 화합물 50의 합성 7: Synthesis of compound 50

(1) (One) 제조예production example 1 : 중간체 50-1의 합성 1: Synthesis of intermediate 50-1

Figure pat00061
Figure pat00061

7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromo-1-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 50-1>을 16.6 g (수율 70.9%) 수득하였다.7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromo-1-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 16.6 g (yield 70.9%) of <Intermediate 50-1>.

(2) (2) 제조예production example 2 : 중간체 50-2의 합성 2: Synthesis of intermediate 50-2

Figure pat00062
Figure pat00062

중간체 50-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), Pd(dppf)Cl2 (1.0 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 50-2>를 8.3 g (수율 73.8 %) 수득하였다.Intermediate 50-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), dioxane 200 in Pd(dppf)Cl 2 (1.0 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.3 g (yield 73.8%) of <Intermediate 50-2>.

(3) (3) 제조예production example 3 : 화합물 50의 합성 3: Synthesis of compound 50

Figure pat00063
Figure pat00063

중간체 50-2 (10.0 g, 0.024 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (7.6 g, 0.028 mol), K2CO3 (9.8 g, 0.071 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 50>을 9.8 g (수율 78.4%) 수득하였다.Intermediate 50-2 (10.0 g, 0.024 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (7.6 g, 0.028 mol), K 2 CO 3 (9.8 g, 0.071 mol), Pd (PPh 3 ) 4 (0.6 g, 0.0005 mol) was put into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 9.8 g (yield 78.4%) of <Compound 50> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=527[(M+1)+]LC/MS: m/z=527[(M+1) + ]

합성예Synthesis example 8 : 화합물 53의 합성 8: Synthesis of compound 53

(1) (One) 제조예production example 1 : 화합물 53의 합성 1: Synthesis of compound 53

Figure pat00064
Figure pat00064

7-Amino-8-hydroxyquinoline (6.0 g, 0.038 mol), Triethylamine 25.7 mL를 NMP에 용해시킨다. 그 후 1,3,5-Benzenetricarboxylic chloride (10.0 g, 0.038 mol)를 dropwise로 상온에서 첨가하고 160 ℃에서 24시간 동안 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 53>을 7.2 g (수율 32.8%) 수득하였다.Dissolve 7-Amino-8-hydroxyquinoline (6.0 g, 0.038 mol) and 25.7 mL of Triethylamine in NMP. Then, 1,3,5-Benzenetricarboxylic chloride (10.0 g, 0.038 mol) was added dropwise at room temperature and reacted at 160 °C for 24 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.2 g (yield 32.8%) of <Compound 53>.

LC/MS: m/z=582[(M+1)+]LC/MS: m/z=582[(M+1) + ]

합성예Synthesis example 9 : 화합물 69의 합성 9: Synthesis of compound 69

(1) (One) 제조예production example 1 : 중간체 69-1의 합성 1: Synthesis of Intermediate 69-1

Figure pat00065
Figure pat00065

7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 2-Bromo-1-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 69-1>을 15.8 g (수율 67.5%) 수득하였다.7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 2-Bromo-1-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.8 g (yield 67.5%) of <Intermediate 69-1>.

(2) (2) 제조예production example 2 : 중간체 69-2의 합성 2: Synthesis of intermediate 69-2

Figure pat00066
Figure pat00066

중간체 69-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), Pd(dppf)Cl2 (1.0 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 69-2>를 8.5 g (수율 75.5%) 수득하였다.Intermediate 69-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), dioxane 200 in Pd(dppf)Cl 2 (1.0 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.5 g (yield 75.5%) of <Intermediate 69-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) (3) 제조예production example 3 : 화합물 69의 합성 3: Synthesis of compound 69

Figure pat00067
Figure pat00067

중간체 69-2 (10.0 g, 0.024 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (7.6 g, 0.028 mol), K2CO3 (9.8 g, 0.071 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 69>를 7.1 g (수율 56.8%) 수득하였다.Intermediate 69-2 (10.0 g, 0.024 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (7.6 g, 0.028 mol), K 2 CO 3 (9.8 g, 0.071 mol), Pd (PPh 3 ) 4 (0.6 g, 0.0005 mol) was put into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 7.1 g (yield 56.8%) of <Compound 69> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=527[(M+1)+]LC/MS: m/z=527[(M+1) + ]

합성예Synthesis example 10 : 화합물 73의 합성 10: synthesis of compound 73

(1) (One) 제조예production example 1 : 중간체 73-1의 합성 1: Synthesis of Intermediate 73-1

Figure pat00068
Figure pat00068

8-Amino-7-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 73-1>을 13.9 g (수율 68.5%) 수득하였다.Add 8-Amino-7-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), and 200 mL of DMF, and stir at 80 °C for 2 hours. reacted. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.9 g (yield 68.5%) of <Intermediate 73-1>.

(2) (2) 제조예production example 2 : 화합물 73의 합성 2: Synthesis of compound 73

Figure pat00069
Figure pat00069

중간체 73-1 (10.0 g, 0.031 mol), 10-(2-Naphthenyl)anthracene-9-boric acid (12.9 g, 0.037 mol), K2CO3 (12.8 g, 0.092 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 73>을 11.5 g (수율 68.2%) 수득하였다.Intermediate 73-1 (10.0 g, 0.031 mol), 10-(2-Naphthenyl)anthracene-9-boric acid (12.9 g, 0.037 mol), K 2 CO 3 (12.8 g, 0.092 mol), Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) was added to 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 11.5 g (yield 68.2%) of <Compound 73> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=548[(M+1)+]LC/MS: m/z=548[(M+1) + ]

합성예Synthesis example 11 : 화합물 86의 합성 11: Synthesis of compound 86

(1) (One) 제조예production example 1 : 중간체 86-1의 합성 1: Synthesis of Intermediate 86-1

Figure pat00070
Figure pat00070

중간체 73-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl2 (1.1 g, 0.002 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 86-1>을 7.8 g (수율 68.1%) 수득하였다.Intermediate 73-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), dioxane 200 in Pd(dppf)Cl 2 (1.1 g, 0.002 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.8 g (yield 68.1%) of <Intermediate 86-1>.

(2) (2) 제조예production example 2 : 화합물 86의 합성 2: Synthesis of compound 86

Figure pat00071
Figure pat00071

중간체 86-1 (10.0 g, 0.027 mol), 2,4-Bis([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (13.5 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 86>을 12.2 g (수율 72.1%) 수득하였다.Intermediate 86-1 (10.0 g, 0.027 mol), 2,4-Bis([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (13.5 g, 0.032 mol) , K 2 CO 3 (11.1 g, 0.081 mol), Pd(PPh 3 ) 4 (0.6 g, 0.0005 mol) into Toluene 140 mL, EtOH 35 mL, H 2 O 35 mL, and stirred at 100 ° C for 6 hours to react did it After completion of the reaction, 12.2 g (yield 72.1%) of <Compound 86> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=629[(M+1)+]LC/MS: m/z=629 [(M+1) + ]

합성예Synthesis example 12 : 화합물 98의 합성 12: Synthesis of compound 98

(1) (One) 제조예production example 1 : 중간체 98-1의 합성 1: Synthesis of intermediate 98-1

Figure pat00072
Figure pat00072

Cyanuric chloride (10.0 g, 0.054 mol), 4-(2-Benzo[d]oxazolyl)phenylboronicacid (31.1 g, 0.130 mol), K2CO3 (45.0 g, 0.325 mol), Pd(PPh3)4 (1.3 g, 0.001 mol)에 Toluene 140 ml, EtOH 35 ml, H2O 35 ml 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 98-1>을 17.2 g (수율 63.2%) 수득하였다.Cyanuric chloride (10.0 g, 0.054 mol), 4-(2-Benzo[d]oxazolyl)phenylboronicacid (31.1 g, 0.130 mol), K 2 CO 3 (45.0 g, 0.325 mol), Pd(PPh 3 ) 4 (1.3 g, 0.001 mol) into 140 ml of Toluene, 35 ml of EtOH, and 35 ml of H 2 O, followed by stirring at 100° C. for 6 hours to react. After completion of the reaction, 17.2 g (yield 63.2%) of <Intermediate 98-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) (2) 제조예production example 2 : 화합물 98의 합성 2: Synthesis of compound 98

Figure pat00073
Figure pat00073

중간체 86-1 (10.0 g, 0.027 mol), 중간체 98-1 (16.2 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 98>을 13.1 g (수율 68.5%) 수득하였다.Intermediate 86-1 (10.0 g, 0.027 mol), Intermediate 98-1 (16.2 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.081 mol), Pd(PPh 3 ) 4 (0.6 g, 0.0005 mol) Toluene 140 mL, EtOH 35 mL, H 2 O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 13.1 g (yield 68.5%) of <Compound 98> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=711[(M+1)+]LC/MS: m/z=711 [(M+1) + ]

합성예Synthesis example 13 : 화합물 107의 합성 13: Synthesis of compound 107

(1) (One) 제조예production example 1 : 중간체 107-1의 합성 1: Synthesis of intermediate 107-1

Figure pat00074
Figure pat00074

8-Amino-7-hydroxyquinoline (10.0 g, 0.062 mol), 2-Bromo-6-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 107-1>을 16.8 g (수율 71.7%) 수득하였다.8-Amino-7-hydroxyquinoline (10.0 g, 0.062 mol), 2-Bromo-6-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, 16.8 g (yield 71.7%) of <Intermediate 107-1> was obtained by extraction, concentration, and column.

(2) (2) 제조예production example 2 : 중간체 107-2의 합성 2: Synthesis of intermediate 107-2

Figure pat00075
Figure pat00075

중간체 107-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), Pd(dppf)Cl2 (1.0 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 107-2>를 8.2 g (수율 72.9%) 수득하였다.Intermediate 107-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), Pd(dppf)Cl 2 (1.0 g, 0.001 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.2 g (yield 72.9%) of <Intermediate 107-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) (3) 제조예production example 3 : 화합물 107의 합성 3: Synthesis of compound 107

Figure pat00076
Figure pat00076

중간체 107-1 (10.0 g, 0.027 mol), 중간체 107-2 (13.5 g, 0.032 mol), K2CO3 (11.1 g, 0.080 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 107>을 11.8 g (수율 75.0%) 수득하였다.Intermediate 107-1 (10.0 g, 0.027 mol), Intermediate 107-2 (13.5 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.080 mol), Pd(PPh 3 ) 4 (0.6 g, 0.0005 mol) Toluene 140 mL, EtOH 35 mL, H 2 O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 11.8 g (yield 75.0%) of <Compound 107> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=590[(M+1)+]LC/MS: m/z=590[(M+1) + ]

합성예Synthesis example 14 : 화합물 115의 합성 14: Synthesis of compound 115

(1) (One) 제조예production example 1 : 화합물 115의 합성 1: Synthesis of compound 115

Figure pat00077
Figure pat00077

2,4-Dichloro-6-(4-phenylphenyl)-1,3,5-triazine (10.0 g, 0.033 mol), 중간체 98-2 (29.6 g, 0.079 mol), K2CO3 (27.4 g, 0.199 mol), Pd(PPh3)4 (0.8 g, 0.0007 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 115>를 17.5 g (수율 73.3%) 수득하였다.2,4-Dichloro-6-(4-phenylphenyl)-1,3,5-triazine (10.0 g, 0.033 mol), intermediate 98-2 (29.6 g, 0.079 mol), K 2 CO 3 (27.4 g, 0.199) mol), Pd(PPh 3 ) 4 (0.8 g, 0.0007 mol) was added with 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 17.5 g (yield 73.3%) of <Compound 115> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=721[(M+1)+]LC/MS: m/z=721 [(M+1) + ]

합성예Synthesis example 15 : 화합물 124의 합성 15: Synthesis of compound 124

(1) (One) 제조예production example 1 : 중간체 124-1의 합성 1: Synthesis of Intermediate 124-1

Figure pat00078
Figure pat00078

2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), 9,9'-Spirobi(9H-fluorene)-2-boronic acid (12.6 g, 0.035 mol), K2CO3 (12.1 g, 0.088 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 124-1>을 8.8 g (수율 48.4%) 수득하였다.2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), 9,9'-Spirobi(9H-fluorene) Toluene 140 mL, EtOH 35 mL, H 2 O in -2-boronic acid (12.6 g, 0.035 mol), K 2 CO 3 (12.1 g, 0.088 mol), Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) 35 mL was added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, 8.8 g (yield 48.4%) of <Intermediate 124-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) (2) 제조예production example 2 : 화합물 124의 합성 2: Synthesis of compound 124

Figure pat00079
Figure pat00079

중간체 124-1 (10.0 g, 0.029 mol), 중간체 98-2 (12.6 g, 0.035 mol), K2CO3 (12.1 g, 0.088 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 124>를 11.4 g (수율 68.2%) 수득하였다.To Intermediate 124-1 (10.0 g, 0.029 mol), Intermediate 98-2 (12.6 g, 0.035 mol), K 2 CO 3 (12.1 g, 0.088 mol), Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) Toluene 140 mL, EtOH 35 mL, H 2 O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 11.4 g (yield 68.2%) of <Compound 124> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=830[(M+1)+]LC/MS: m/z=830 [(M+1) + ]

합성예Synthesis example 16 : 화합물 131의 합성 16: Synthesis of compound 131

(1) (One) 제조예production example 1 : 중간체 131-1의 합성 1: Synthesis of intermediate 131-1

Figure pat00080
Figure pat00080

7-Amino-6-quinolinol (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 131-1>을 13.2 g (수율 65.0%) 수득하였다.Add 7-Amino-6-quinolinol (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), and 200 mL of DMF, and stir at 80 °C for 2 hours. reacted. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 13.2 g (yield: 65.0%) of <Intermediate 131-1>.

(2) (2) 제조예production example 2 : 중간체 131-2의 합성 2: Synthesis of intermediate 131-2

Figure pat00081
Figure pat00081

중간체 131-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl2 (1.1 g, 0.002 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 131-2>를 7.7 g (수율 67.3%) 수득하였다.Intermediate 131-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl 2 (1.1 g, 0.002 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 7.7 g (yield 67.3%) of <Intermediate 131-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) (3) 제조예production example 3 : 화합물 131의 합성 3: Synthesis of compound 131

Figure pat00082
Figure pat00082

중간체 131-2 (10.0 g, 0.027 mol), 4-Chloro-2,6-diphenylpyridine (8.6 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 131>을 9.2 g (수율 72.0%) 수득하였다.Intermediate 131-2 (10.0 g, 0.027 mol), 4-Chloro-2,6-diphenylpyridine (8.6 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.081 mol), Pd(PPh 3 ) 4 (0.6 g , 0.0005 mol) into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 9.2 g (yield 72.0%) of <Compound 131> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=475[(M+1)+]LC/MS: m/z=475[(M+1) + ]

합성예Synthesis example 17 : 화합물 133의 합성 17: Synthesis of compound 133

(1) (One) 제조예production example 1 : 중간체 133-1의 합성 1: Synthesis of Intermediate 133-1

Figure pat00083
Figure pat00083

7-Amino-6-quinolinol (10.0 g, 0.062 mol), 3',5'-Dibromo[1,1'-biphenyl]-4-carboxaldehyde (21.2 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 133-1>을 20.1 g (수율 67.1%) 수득하였다.7-Amino-6-quinolinol (10.0 g, 0.062 mol), 3',5'-Dibromo[1,1'-biphenyl]-4-carboxaldehyde (21.2 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), 200 mL of DMF was added, and the reaction was stirred at 80 °C for 2 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 20.1 g (yield: 67.1%) of <Intermediate 133-1>.

(2) (2) 제조예production example 2 : 화합물 133의 합성 2: Synthesis of compound 133

Figure pat00084
Figure pat00084

중간체 133-1 (10.0 g, 0.021 mol), 4-(pyridin-3-yl)phenylboronic acid (10.0 g, 0.050 mol), K2CO3 (17.3 g, 0.125 mol), Pd(PPh3)4 (0.5 g, 0.0004 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 133>을 9.8 g (수율 74.8%) 수득하였다.Intermediate 133-1 (10.0 g, 0.021 mol), 4-(pyridin-3-yl)phenylboronic acid (10.0 g, 0.050 mol), K 2 CO 3 (17.3 g, 0.125 mol), Pd(PPh 3 ) 4 ( 0.5 g, 0.0004 mol) into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 9.8 g (yield 74.8%) of <Compound 133> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=628[(M+1)+]LC/MS: m/z=628[(M+1) + ]

합성예Synthesis example 18 : 화합물 190의 합성 18: Synthesis of compound 190

(1) (One) 제조예production example 1 : 중간체 190-1의 합성 1: Synthesis of intermediate 190-1

Figure pat00085
Figure pat00085

7-Amino-6-quinolinol (10.0 g, 0.062 mol), 3-Formyl-1-bromobenzene (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 190-1>을 12.8 g (수율 63.1%) 수득하였다.7-Amino-6-quinolinol (10.0 g, 0.062 mol), 3-Formyl-1-bromobenzene (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.8 g (yield 63.1%) of <Intermediate 190-1>.

(2) (2) 제조예production example 2 : 중간체 190-2의 합성 2: Synthesis of intermediate 190-2

Figure pat00086
Figure pat00086

중간체 190-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl2 (1.1 g, 0.002 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 190-2>를 8.1 g (수율 70.8%) 수득하였다.Intermediate 190-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), dioxane 200 in Pd(dppf)Cl 2 (1.1 g, 0.002 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.1 g (yield 70.8%) of <Intermediate 190-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) (3) 제조예production example 3 : 화합물 190의 합성 3: Synthesis of compound 190

Figure pat00087
Figure pat00087

중간체 190-2 (10.0 g, 0.027 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.6 g, 0.032 mol), K2CO3 (11.1 g, 0.081 mol), Pd(PPh3)4 (0.6 g, 0.0005 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 190>을 15.3 g (수율 74.0%) 수득하였다.Intermediate 190-2 (10.0 g, 0.027 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.6 g, 0.032 mol), K 2 CO 3 (11.1 g, 0.081 mol), Pd (PPh 3 ) 4 (0.6 g, 0.0005 mol) was put into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 15.3 g (yield 74.0%) of <Compound 190> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=477[(M+1)+]LC/MS: m/z=477 [(M+1) + ]

합성예Synthesis example 19 : 화합물 337의 합성 19: Synthesis of compound 337

(1) (One) 제조예production example 1 : 중간체 337-1의 합성 1: Synthesis of intermediate 337-1

Figure pat00088
Figure pat00088

7-Bromo-8-nitroquinoline (10.0 g, 0.040 mol), Aniline (5.5 g, 0.059 mol), NaOtBu (7.6 g, 0.079 mol), Pd(dba)2 (1.1 g, 0.002 mol), t-Bu3P (0.8 g, 0.004 mol)에 Toluene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 337-1>을 7.7 g (수율 73.5%) 수득하였다.7-Bromo-8-nitroquinoline (10.0 g, 0.040 mol), Aniline (5.5 g, 0.059 mol), NaOtBu (7.6 g, 0.079 mol), Pd(dba) 2 (1.1 g, 0.002 mol), t-Bu 3 150 mL of toluene was added to P (0.8 g, 0.004 mol), and the reaction was stirred at 70 °C for 4 hours. After completion of the reaction, 7.7 g (yield 73.5%) of <Intermediate 337-1> was obtained by extraction, concentration, and column.

(2) (2) 제조예production example 2 : 중간체 337-2의 합성 2: Synthesis of intermediate 337-2

Figure pat00089
Figure pat00089

중간체 337-1 (10.0 g, 0.038 mol), Pd/C (12.0 g, 0.113 mol)를 Hydrazine hydrate (45.7 g, 1.425 mol)에 천천히 적가한 후 1시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 337-2>를 7.5 g (수율 84.6%) 수득하였다.Intermediate 337-1 (10.0 g, 0.038 mol), Pd/C (12.0 g, 0.113 mol) was slowly added dropwise to Hydrazine hydrate (45.7 g, 1.425 mol) and stirred for 1 hour to react. After completion of the reaction, 7.5 g (yield 84.6%) of <Intermediate 337-2> was obtained by extraction, concentration, and column.

(3) (3) 제조예production example 3 : 중간체 337-3의 합성 3: Synthesis of intermediate 337-3

Figure pat00090
Figure pat00090

중간체 337-2 (10.0 g, 0.043 mol), 4-bromobenzaldehyde (7.9 g, 0.043 mol), p-Toluenesulfonic acid (1.5 g, 0.009 mol), DMF 200 mL 넣고 80 ℃에서 2시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 337-3>을 11.8 g (수율 69.4%) 수득하였다.Intermediate 337-2 (10.0 g, 0.043 mol), 4-bromobenzaldehyde (7.9 g, 0.043 mol), p-Toluenesulfonic acid (1.5 g, 0.009 mol), 200 mL of DMF was added, and the reaction was stirred at 80 °C for 2 hours. After completion of the reaction, 11.8 g (yield 69.4%) of <Intermediate 337-3> was obtained by extraction and concentration by column.

(4) (4) 제조예production example 4 : 중간체 337-4의 합성 4: Synthesis of intermediate 337-4

Figure pat00091
Figure pat00091

중간체 337-3 (10.0 g, 0.025 mol), Bis(pinacolato)diboron (7.6 g, 0.030 mol), KOAc (7.4 g, 0.075 mol), Pd(dppf)Cl2 (0.9 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 337-4>를 8.3 g (수율 74.3%) 수득하였다.Intermediate 337-3 (10.0 g, 0.025 mol), Bis(pinacolato)diboron (7.6 g, 0.030 mol), KOAc (7.4 g, 0.075 mol), Pd(dppf)Cl 2 (0.9 g, 0.001 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.3 g (yield 74.3%) of <Intermediate 337-4> was obtained by extraction and concentration by column.

(5) (5) 제조예production example 5 : 중간체 337-5의 합성 5: Synthesis of intermediate 337-5

Figure pat00092
Figure pat00092

2,4-Dichloro-6-(4-phenylphenyl)-1,3,5-triazine (10.0 g, 0.033 mol), (9,9-Dimethyl-9H-fluoren-2-yl)boronic acid (9.5 g, 0.040 mol), K2CO3 (13.7 g, 0.099 mol), Pd(PPh3)4 (0.8 g, 0.0007 mol)에 oluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 337-5>를 8.1 g (수율 53.2%) 수득하였다.2,4-Dichloro-6-(4-phenylphenyl)-1,3,5-triazine (10.0 g, 0.033 mol), (9,9-Dimethyl-9H-fluoren-2-yl)boronic acid (9.5 g, 0.040 mol), K 2 CO 3 (13.7 g, 0.099 mol), Pd(PPh 3 ) 4 (0.8 g, 0.0007 mol) in oluene 140 mL, EtOH 35 mL, H 2 O 35 mL, and at 100 °C for 6 hours The reaction was stirred. After completion of the reaction, 8.1 g (yield 53.2%) of <Intermediate 337-5> was obtained by extraction and concentration, followed by column and recrystallization.

(6) (6) 제조예production example 6 : 화합물 337의 합성 6: Synthesis of compound 337

Figure pat00093
Figure pat00093

중간체 337-4 (10.0 g, 0.015 mol), 중간체 337-5 (4.3 g, 0.018 mol), K2CO3 (16.3 g, 0.118 mol), Pd(PPh3)4 (0.9 g, 0.0008 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 337>을 15.3 g (수율 74.0%) 수득하였다.Intermediate 337-4 (10.0 g, 0.015 mol), Intermediate 337-5 (4.3 g, 0.018 mol), K 2 CO 3 (16.3 g, 0.118 mol), Pd(PPh 3 ) 4 (0.9 g, 0.0008 mol) Toluene 140 mL, EtOH 35 mL, H 2 O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 15.3 g (yield 74.0%) of <Compound 337> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=744[(M+1)+]LC/MS: m/z=744[(M+1) + ]

소자 device 실시예Example ( ( ETLETL ))

본 발명에 따른 실시예에서, ITO 투명 전극은 25 mm × 25 mm × 0.7 mm의 유리 기판 위에, ITO 투명 전극이 부착된 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1 × 10-6 torr 이상 되도록 한 후 유기물을 상기 ITO위에 하기 구조로 유기물과 금속을 증착하였다.In an embodiment according to the present invention, the ITO transparent electrode is patterned so that the light emitting area is 2 mm × 2 mm on a glass substrate of 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate to which an ITO transparent electrode is attached. and then washed. After the substrate was mounted in a vacuum chamber, the base pressure was set to 1 × 10 -6 torr or more, and the organic material and the metal were deposited on the ITO in the following structure.

소자 device 실시예Example 1 내지 83 1 to 83

본 발명에 따라 구현되는 화합물을 전자수송층 재료로 사용하였으며, 하기와 같은 소자 구조를 갖는 유기발광소자를 제작 후, 본 발명에 따라 구현되는 화합물이 갖는 발광 및 구동 특성을 측정하였다.The compound implemented according to the present invention was used as an electron transport layer material, and an organic light emitting device having the following device structure was fabricated, and then light emission and driving characteristics of the compound implemented according to the present invention were measured.

ITO / 정공주입층 (HAT-CN, 5 nm) / 정공수송층 (α-NPB, 100 nm) / 전자저지층 (EBL1 10 nm) / 발광층 (20 nm) / 전자수송층 (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EBL1 10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

ITO 투명 전극에 정공주입층을 형성하기 위해 [HAT-CN]을 이용하여 5 nm 두께로 증착하고, 이후 정공수송층은 α-NPB를 사용하여 100 nm 성막하였다. 전자저지층은 [EBL1]을 사용하여 10 nm의 두께로 증착하였다. 또한, 발광층에는 호스트 화합물로 [BH1]을 사용하고, 도판트 화합물은 [BD1]을 사용하여 두께가 20 nm 되도록 공증착하였으며, 전자수송층은 하기 [표 1]에 표시된 바와 같은 본 발명에 따른 화합물을 사용하여 30 nm (Liq 도핑) 증착 후, LiF를 1 nm의 두께로 성막하여 전자주입층을 형성하였다. 이 후, Al을 100 nm의 두께로 성막하여 유기발광소자를 제작하였다.To form a hole injection layer on the ITO transparent electrode, [HAT-CN] was used to deposit a thickness of 5 nm, and then the hole transport layer was deposited at 100 nm using α-NPB. The electron blocking layer was deposited to a thickness of 10 nm using [EBL1]. In addition, [BH1] was used as the host compound for the light emitting layer, and the dopant compound was co-deposited to a thickness of 20 nm using [BD1], and the electron transport layer was a compound according to the present invention as shown in [Table 1] below. After 30 nm (Liq doping) deposition using Thereafter, Al was deposited to a thickness of 100 nm to fabricate an organic light emitting diode.

소자 device 비교예comparative example 1 One

소자 비교예 1을 위한 유기발광소자는 상기 실시예 1 내지 83의 소자구조에서 전자수송층 재료로 본 발명에 따른 화합물 대신 하기 [ET1]을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner as in the device structures of Examples 1 to 83, except that the following [ET1] was used instead of the compound according to the present invention as the electron transport layer material.

소자 device 비교예comparative example 2 2

소자 비교예 2를 위한 유기발광소자는 상기 실시예 1 내지 83의 소자구조에서 전자수송층 재료로 본 발명에 따른 화합물 대신 하기 [ET2]를 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 2 was prepared in the same manner as in the device structures of Examples 1 to 83, except that the following [ET2] was used instead of the compound according to the present invention as the electron transport layer material.

실험예Experimental example 1 : 소자 1: element 실시예Example 1 내지 83의 발광 특성 1 to 83 luminescent properties

상기 실시예에 따라 제조된 유기발광소자는 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 전압, 전류 및 발광 효율을 측정하였고, 1000 nit 기준의 결과값은 하기 [표 1]과 같다.The organic light emitting device manufactured according to the above example was measured for voltage, current and luminous efficiency using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the result value based on 1000 nit was It is shown in [Table 1] below.

실시예Example 전자수송층electron transport layer VV cd/Acd/A CIExCIEx CIEyCIEy 1One 화학식 1Formula 1 3.93.9 7.77.7 0.1320.132 0.1470.147 22 화학식 2Formula 2 3.83.8 8.18.1 0.1340.134 0.1480.148 33 화학식 3Formula 3 4.14.1 7.47.4 0.1320.132 0.1480.148 44 화학식 5Formula 5 3.93.9 7.77.7 0.1320.132 0.1470.147 55 화학식 9Formula 9 3.73.7 7.87.8 0.1290.129 0.1530.153 66 화학식 13Formula 13 3.73.7 7.77.7 0.1300.130 0.1500.150 77 화학식 14Formula 14 3.63.6 7.87.8 0.1330.133 0.1450.145 88 화학식 17Formula 17 3.63.6 7.67.6 0.1310.131 0.1490.149 99 화학식 19Formula 19 4.14.1 7.67.6 0.1340.134 0.1450.145 1010 화학식 20Formula 20 3.83.8 7.77.7 0.1330.133 0.1460.146 1111 화학식 21Formula 21 3.93.9 7.57.5 0.1320.132 0.1470.147 1212 화학식 22Formula 22 3.93.9 7.97.9 0.1310.131 0.1500.150 1313 화학식 23Formula 23 4.04.0 7.77.7 0.1320.132 0.1480.148 1414 화학식 24Formula 24 3.73.7 7.57.5 0.1330.133 0.1450.145 1515 화학식 25Formula 25 4.14.1 7.47.4 0.1330.133 0.1500.150 1616 화학식 27Formula 27 3.83.8 7.77.7 0.1330.133 0.1460.146 1717 화학식 29Formula 29 4.14.1 7.57.5 0.1330.133 0.1460.146 1818 화학식 30Formula 30 4.14.1 7.27.2 0.1310.131 0.1490.149 1919 화학식 33Formula 33 4.04.0 7.57.5 0.1330.133 0.1470.147 2020 화학식 35Formula 35 4.04.0 7.57.5 0.1360.136 0.1440.144 2121 화학식 41Formula 41 3.93.9 7.37.3 0.1320.132 0.1480.148 2222 화학식 43Formula 43 3.93.9 7.37.3 0.1310.131 0.1470.147 2323 화학식 44Formula 44 4.04.0 7.57.5 0.1310.131 0.1500.150 2424 화학식 49Formula 49 4.14.1 7.77.7 0.1300.130 0.1500.150 2525 화학식 50Formula 50 4.04.0 7.47.4 0.1320.132 0.1480.148 2626 화학식 53Formula 53 3.83.8 7.87.8 0.1310.131 0.1450.145 2727 화학식 57chemical formula 57 3.93.9 7.57.5 0.1320.132 0.1460.146 2828 화학식 61Formula 61 3.83.8 7.37.3 0.1310.131 0.1420.142 2929 화학식 62Formula 62 4.04.0 7.87.8 0.1300.130 0.1450.145 3030 화학식 67Formula 67 3.93.9 7.57.5 0.1310.131 0.1460.146 3131 화학식 68Formula 68 3.83.8 7.97.9 0.1300.130 0.1450.145 3232 화학식 69Formula 69 4.14.1 7.27.2 0.1300.130 0.1450.145 3333 화학식 73Formula 73 3.93.9 7.57.5 0.1300.130 0.1450.145 3434 화학식 79Formula 79 3.73.7 7.87.8 0.1370.137 0.1500.150 3535 화학식 80Formula 80 3.83.8 7.57.5 0.1380.138 0.1470.147 3636 화학식 84Formula 84 3.73.7 7.57.5 0.1310.131 0.1420.142 3737 화학식 86Formula 86 3.73.7 7.47.4 0.1350.135 0.1460.146 3838 화학식 88Formula 88 4.24.2 7.27.2 0.1320.132 0.1420.142 3939 화학식 91Formula 91 3.93.9 7.57.5 0.1310.131 0.1430.143 4040 화학식 92Formula 92 4.04.0 7.57.5 0.1300.130 0.1440.144 4141 화학식 93Formula 93 3.93.9 7.77.7 0.1390.139 0.1470.147 4242 화학식 94Formula 94 3.73.7 7.97.9 0.1300.130 0.1450.145 4343 화학식 98Formula 98 4.04.0 7.47.4 0.1310.131 0.1420.142 4444 화학식 99Formula 99 4.14.1 7.57.5 0.1310.131 0.1470.147 4545 화학식 100Formula 100 3.63.6 7.97.9 0.1310.131 0.1430.143 4646 화학식 101Formula 101 4.04.0 7.57.5 0.1310.131 0.1430.143 4747 화학식 106Formula 106 4.04.0 7.47.4 0.1290.129 0.1460.146 4848 화학식 107Formula 107 3.93.9 7.67.6 0.1300.130 0.1450.145 4949 화학식 110Formula 110 3.93.9 7.77.7 0.1340.134 0.1460.146 5050 화학식 112Formula 112 4.04.0 7.57.5 0.1310.131 0.1450.145 5151 화학식 115Formula 115 3.93.9 7.57.5 0.1290.129 0.1440.144 5252 화학식 124Formula 124 4.04.0 7.67.6 0.1290.129 0.1470.147 5353 화학식 125Formula 125 4.14.1 7.97.9 0.1280.128 0.1470.147 5454 화학식 131Formula 131 4.04.0 7.47.4 0.1320.132 0.1480.148 5555 화학식 133Formula 133 4.04.0 7.37.3 0.1310.131 0.1480.148 5656 화학식 137Formula 137 4.04.0 7.57.5 0.1340.134 0.1490.149 5757 화학식 139Formula 139 3.83.8 7.37.3 0.1330.133 0.1450.145 5858 화학식 141Formula 141 3.93.9 7.87.8 0.1320.132 0.1480.148 5959 화학식 142Formula 142 3.83.8 7.57.5 0.1320.132 0.1440.144 6060 화학식 143Formula 143 3.73.7 7.97.9 0.1300.130 0.1450.145 6161 화학식 144Formula 144 4.04.0 7.27.2 0.1300.130 0.1450.145 6262 화학식 187Formula 187 3.83.8 7.57.5 0.1350.135 0.1490.149 6363 화학식 189Formula 189 3.73.7 7.57.5 0.1370.137 0.1500.150 6464 화학식 190Formula 190 3.73.7 7.57.5 0.1380.138 0.1470.147 6565 화학식 212Formula 212 3.63.6 7.77.7 0.1310.131 0.1420.142 6666 화학식 229Formula 229 3.63.6 7.67.6 0.1390.139 0.1460.146 6767 화학식 233Formula 233 4.14.1 7.67.6 0.1320.132 0.1420.142 6868 화학식 237Formula 237 3.83.8 7.77.7 0.1310.131 0.1430.143 6969 화학식 242Formula 242 3.93.9 7.77.7 0.1300.130 0.1440.144 7070 화학식 247Formula 247 4.04.0 7.97.9 0.1390.139 0.1470.147 7171 화학식 255Formula 255 4.14.1 7.67.6 0.1300.130 0.1450.145 7272 화학식 267Formula 267 3.83.8 7.47.4 0.1310.131 0.1420.142 7373 화학식 279Formula 279 4.24.2 7.57.5 0.1310.131 0.1470.147 7474 화학식 289Formula 289 4.24.2 7.97.9 0.1310.131 0.1430.143 7575 화학식 293Formula 293 4.04.0 7.77.7 0.1360.136 0.1450.145 7676 화학식 318Formula 318 4.04.0 7.27.2 0.1380.138 0.1460.146 7777 화학식 336Formula 336 3.93.9 7.57.5 0.1300.130 0.1420.142 7878 화학식 337Formula 337 3.93.9 7.57.5 0.1330.133 0.1450.145 7979 화학식 342Formula 342 4.04.0 7.27.2 0.1320.132 0.1480.148 8080 화학식 345Formula 345 4.14.1 7.37.3 0.1310.131 0.1470.147 8181 화학식 348Formula 348 3.93.9 7.57.5 0.1330.133 0.1500.150 8282 화학식 354Formula 354 4.24.2 7.77.7 0.1300.130 0.1500.150 8383 화학식 355Formula 355 4.14.1 7.47.4 0.1320.132 0.1480.148 비교예 1Comparative Example 1 ET1ET1 4.74.7 6.66.6 0.1350.135 0.1510.151 비교예 2Comparative Example 2 ET2ET2 4.64.6 6.56.5 0.1380.138 0.1560.156

상기 [표 1]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 전자수송층 재료로 소자에 적용한 경우에 종래 전자수송 재료로 사용된 화합물과 본 발명에 따른 화합물이 갖는 특징적 구조와 대비되는 화합물을 각각 채용한 소자 (비교예 1 내지 2)에 비하여 저전압 구동 특성과 발광 효율, 양자 효율 등의 발광 특성이 현저히 우수함을 확인할 수 있다.Looking at the results shown in [Table 1], when the compound according to the present invention is applied to a device as an electron transport layer material, the compound used as the conventional electron transport material and the compound in contrast to the characteristic structure of the compound according to the present invention, respectively It can be seen that the light-emitting properties such as low voltage driving characteristics, light-emitting efficiency, and quantum efficiency are significantly superior to those of the employed devices (Comparative Examples 1 and 2).

Figure pat00094
Figure pat00094

[HAT_CN] [α-NPB] [BH1] [BD1] [EBL1][HAT_CN] [α-NPB] [BH1] [BD1] [EBL1]

Figure pat00095
Figure pat00095

[ET1] [ET2][ET1] [ET2]

Claims (7)

하기 [화학식 Ⅰ]로 표시되는 유기발광 화합물:
[화학식 Ⅰ]
Figure pat00096

상기 [화학식 Ⅰ]에서,
X는 O, S 또는 NR1이고,
상기 R1은 수소, 중수소, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이며,
L은 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기 중에서 선택되는 어느 하나이며,
m은 0 내지 3의 정수이고, 상기 m이 2 이상인 경우 복수 개의 L은 서로 동일하거나 상이하며,
A는 하기 [구조식 1] 또는 [구조식 2]로 표시되고,
[구조식 1]
Figure pat00097

[구조식 2]
Figure pat00098

상기 [구조식 1]과 [구조식 2]에서,
X1 내지 X3은 서로 동일하거나 상이하고, 각각 독립적으로 CH 또는 N이고,
L1은 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기 중에서 선택되는 어느 하나이며,
o는 0 내지 3의 정수이고, 상기 o가 2 이상인 경우 복수 개의 L1은 서로 동일하거나 상이하며,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이며,
q 및 r은 0 내지 3의 정수이고, 상기 q 및 r이 각각 2 이상인 경우 상기 복수 개의 Ar1 및 Ar2는 각각 서로 동일하거나 상이하고,
Ar3은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이며,
p는 0 내지 3의 정수이고, 상기 p가 2 이상인 경우 상기 복수 개의 Ar3은 서로 동일하거나 상이하고,
n은 1 내지 3의 정수이며, 상기 n이 2 이상인 경우 상기 복수 개의 괄호 [ ] 안의 구조는 서로 동일하거나 상이하고,
l은 1 내지 2의 정수이며, 상기 l이 2인 경우 각각의 A는 서로 동일하거나 상이하다.
An organic light emitting compound represented by the following [Formula I]:
[Formula Ⅰ]
Figure pat00096

In the [Formula I],
X is O, S or NR 1 ,
Wherein R 1 is hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl Any one selected from a group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
L is a single bond, or any one selected from a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group,
m is an integer from 0 to 3, and when m is 2 or more, a plurality of L's are the same or different from each other,
A is represented by the following [Structural Formula 1] or [Structural Formula 2],
[Structural Formula 1]
Figure pat00097

[Structural Formula 2]
Figure pat00098

In the [Structural Formula 1] and [Structural Formula 2],
X One To X 3 Are the same as or different from each other, each independently CH or N,
L 1 is a single bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms,
o is an integer of 0 to 3, and when o is 2 or more, a plurality of L 1 are the same as or different from each other,
Ar 1 and Ar 2 are the same as or different from each other and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
q and r are integers of 0 to 3, and when q and r are each 2 or more, the plurality of Ar 1 and Ar 2 are the same as or different from each other,
Ar 3 is any one selected from a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group,
p is an integer from 0 to 3, and when p is 2 or more, the plurality of Ar 3 are the same as or different from each other,
n is an integer of 1 to 3, and when n is 2 or more, the structures in the plurality of parentheses [ ] are the same or different from each other,
l is an integer of 1 to 2, and when l is 2, each A is the same as or different from each other.
제1항에 있어서,
상기 [화학식 Ⅰ]은 하기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-4] 중에서 선택되는 어느 하나인 유기발광 화합물:
[화학식 Ⅰ-1] [화학식 Ⅰ-2]
Figure pat00099
Figure pat00100

[화학식 Ⅰ-3] [화학식 Ⅰ-4]
Figure pat00101
Figure pat00102

상기 [화학식 Ⅰ-1] 내지 [화학식 Ⅰ-4]에서, X, L, A, n 및 m의 정의는 상기 [화학식 Ⅰ]에서의 정의와 동일하다.
According to claim 1,
The [Formula I] is an organic light emitting compound which is any one selected from the following [Formula 1-1] to [Formula 1-4]:
[Formula Ⅰ-1] [Formula Ⅰ-2]
Figure pat00099
Figure pat00100

[Formula Ⅰ-3] [Formula Ⅰ-4]
Figure pat00101
Figure pat00102

In the [Formula I-1] to [Formula I-4], the definitions of X, L, A, n and m are the same as the definitions in the [Formula I].
제1항에 있어서,
상기 R1, L, L1 및 Ar1 내지 Ar3의 정의에서, '치환 또는 비치환된'이라 함은, 상기 R1, L, L1 및 Ar1 내지 Ar3이 각각 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 알킬기, 할로겐화된 알킬기, 중수소화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 할로겐화된 알콕시기, 중수소화된 알콕시기, 아릴기 및 헤테로아릴기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것인 것을 특징으로 하는 유기발광 화합물.
According to claim 1,
In the definition of R 1 , L, L 1 and Ar 1 to Ar 3 , 'substituted or unsubstituted' means that R 1 , L, L 1 and Ar 1 To Ar 3 are deuterium, a halogen group, A cyano group, a nitro group, a hydroxyl group, a silyl group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group and a heteroaryl group. An organic light-emitting compound, characterized in that it is substituted with one or two or more substituents selected from the group, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
제1항에 있어서,
상기 [화학식 Ⅰ]은 하기 [화합물 1] 내지 [화합물 360] 중에서 선택되는 어느 하나인 것을 특징으로 하는 유기발광 화합물:
Figure pat00103

Figure pat00104

Figure pat00105

Figure pat00106

Figure pat00107

Figure pat00108

Figure pat00109

Figure pat00110

Figure pat00111

Figure pat00112

Figure pat00113

Figure pat00114

Figure pat00115

Figure pat00116

Figure pat00117

Figure pat00118

Figure pat00119

Figure pat00120

Figure pat00121

Figure pat00122

Figure pat00123

Figure pat00124

Figure pat00125

Figure pat00126

Figure pat00127

Figure pat00128

Figure pat00129

Figure pat00130

Figure pat00131

Figure pat00132

Figure pat00133

Figure pat00134
According to claim 1,
The [Formula I] is an organic light emitting compound, characterized in that any one selected from the following [Compound 1] to [Compound 360]:
Figure pat00103

Figure pat00104

Figure pat00105

Figure pat00106

Figure pat00107

Figure pat00108

Figure pat00109

Figure pat00110

Figure pat00111

Figure pat00112

Figure pat00113

Figure pat00114

Figure pat00115

Figure pat00116

Figure pat00117

Figure pat00118

Figure pat00119

Figure pat00120

Figure pat00121

Figure pat00122

Figure pat00123

Figure pat00124

Figure pat00125

Figure pat00126

Figure pat00127

Figure pat00128

Figure pat00129

Figure pat00130

Figure pat00131

Figure pat00132

Figure pat00133

Figure pat00134
제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기층을 포함하는 유기발광소자로서,
상기 유기층 중 1 층 이상은 제1항에 따른 [화학식 Ⅰ]의 유기발광 화합물을 포함하는 것인 유기발광소자.
An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device comprising the organic light emitting compound of [Formula I] according to claim 1.
제5항에 있어서,
상기 유기층은 정공 주입층, 정공 수송층, 정공 주입과 정공 수송 기능을 동시에 하는 층, 전자 수송층, 전자 주입층, 전자 수송과 전자 주입 기능을 동시에 하는 층, 전자 저지층, 정공 저지층 및 발광층 중에서 선택되는 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.
6. The method of claim 5,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer and a light emitting layer including one or more floors that become
At least one of the layers comprises an organic light emitting compound represented by the [Formula I].
제6항에 있어서,
상기 전자 수송층, 전자 주입층 및 전자 수송과 전자 주입 기능을 동시에 하는 층 중 어느 하나에 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.
7. The method of claim 6,
An organic light emitting device comprising an organic light emitting compound represented by the above [Formula I] in any one of the electron transport layer, the electron injection layer, and the layer performing both electron transport and electron injection functions.
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