KR102703802B1 - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
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- KR102703802B1 KR102703802B1 KR1020180163616A KR20180163616A KR102703802B1 KR 102703802 B1 KR102703802 B1 KR 102703802B1 KR 1020180163616 A KR1020180163616 A KR 1020180163616A KR 20180163616 A KR20180163616 A KR 20180163616A KR 102703802 B1 KR102703802 B1 KR 102703802B1
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 381
- 239000000126 substance Substances 0.000 claims description 104
- 239000010410 layer Substances 0.000 claims description 47
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 18
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
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- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 125000005264 aryl amine group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
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- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
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- 238000002347 injection Methods 0.000 abstract description 18
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- 238000000034 method Methods 0.000 description 130
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- JWWMUTCXVNBWGP-UHFFFAOYSA-N 4-chloro-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=C1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 JWWMUTCXVNBWGP-UHFFFAOYSA-N 0.000 description 2
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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Abstract
본 발명은 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 대한 것으로, 보다 상세하게는 전자 주입 및 수송능, 발광능, 열적 안정성이 우수한 유기 화합물 및 상기 화합물을 포함하여 소자의 발광효율, 구동전압, 수명 등이 향상된 유기 전계 발광 소자에 대한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more specifically, to an organic compound having excellent electron injection and transport ability, luminescence ability, and thermal stability, and an organic electroluminescent device comprising the compound having improved luminescence efficiency, driving voltage, and lifespan.
Description
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 열적 안정성, 발광능력, 전자 주입/수송 능력이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same, and more specifically, to a compound having excellent thermal stability, luminescent ability, and electron injection/transport ability, and an organic electroluminescent device having improved characteristics such as luminescent efficiency, driving voltage, and lifespan by including the compound in one or more organic layers.
유기 전계 발광 소자(이하, '유기 EL 소자'라 함)는 두 전극에 전류, 또는 전압을 인가해 주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어져 빛을 내게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. When current or voltage is applied to two electrodes in an organic electroluminescent device (hereinafter referred to as an "organic EL device"), holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and these excitons fall to the ground state and emit light. At this time, the material used as the organic layer can be classified into a light-emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc., depending on its function.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 재료는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. Up to now, NPB, BCP, Alq 3 , etc. expressed by the following chemical formulas have been widely known as the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant/host materials as luminescent materials. In particular, among luminescent materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc., have been used as blue, green, and red dopant materials as phosphorescent materials that have a great advantage in terms of improving efficiency. Up to now, CBP has shown excellent properties as a phosphorescent host material.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, although existing materials have advantages in terms of luminescence characteristics, they have low glass transition temperatures and very poor thermal stability, and thus are not satisfactory in terms of lifespan in organic EL devices. Therefore, the development of organic layer materials with excellent performance is required.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 열안정성, 발광능 및 전자 주입 및 수송능이 우수한 전자수송층 재료로 사용될 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다. The present invention aims to provide a novel organic compound that can be applied to an organic electroluminescent device and can be used as an electron transport layer material having excellent thermal stability, luminescence ability, and electron injection and transport ability.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동 전압과 높은 발광 효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel organic compound.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:To achieve the above purpose, the present invention provides a compound represented by the following chemical formula 1:
(상기 화학식 1에서,(In the above chemical formula 1,
X1 내지 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR2이고, 다만 X1 내지 X3 중 적어도 하나는 N이고, 이때 CR2가 복수인 경우, 복수의 R2는 서로 동일하거나 상이하며, X 1 to X 3 are identical or different from each other, and are each independently N or CR 2 , provided that at least one of X 1 to X 3 is N, and in this case, when CR 2 is plural, plural R 2 are identical or different from each other,
Y는 O 또는 S이고, Y is O or S,
Z1 내지 Z10은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR3이고, 다만 Z1 내지 Z10 중 적어도 하나는 N이며, 이때 CR3가 복수인 경우, 복수의 R3는 서로 동일하거나 상이하며, Z 1 to Z 10 are identical or different from each other, and are each independently N or CR 3 , provided that at least one of Z 1 to Z 10 is N, and in this case, when CR 3 is plural, plural R 3 are identical or different from each other,
a 및 b는 각각 1 내지 3의 정수이고,a and b are each integers from 1 to 3,
L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C60의 아릴렌기이며,L 1 and L 2 are the same or different from each other, and each independently represents a single bond or an arylene group having C 6 to C 60 ,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되며,Ar 1 and Ar 2 are the same or different from each other, and are each independently selected from the group consisting of an aryl group having C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,
c는 0 내지 4의 정수이고, 이때 복수의 R3는 서로 동일하거나 상이하며,c is an integer from 0 to 4, and multiple R 3 are the same or different from each other,
R1 내지 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,R 1 to R 3 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 Selected from the group consisting of an arylboron group, an arylphosphine group having C 6 to C 60 , an arylphosphine oxide group having C 6 to C 60 , and an arylamine group having C 6 to C 60 ,
상기 L1 및 L2의 아릴렌기, Ar1 및 Ar2의 아릴기 및 헤테로아릴기와, R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).The arylene group of L 1 and L 2 , the aryl group and heteroaryl group of Ar 1 and Ar 2 , and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group , alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 (wherein the aryl group, the heteroaryl group having 5 to 60 nuclear atoms, the C 1 to C 40 alkyloxy group, the C 6 to C 60 aryloxy group, the C 1 to C 40 alkylsilyl group, the C 6 to C 60 arylsilyl group, the C 1 to C 40 alkylboron group, the C 6 to C 60 arylboron group, the C 6 to C 60 arylphosphine group, the C 6 to C 60 arylphosphine oxide group, and the C 6 to C 60 arylamine group are substituted or unsubstituted with one or more substituents selected from the group consisting of, and wherein when there are plural substituents, they are the same as or different from each other.)
또한, 본 발명은 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, the present invention provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.
본 발명의 화합물은 열적 안정성, 발광능, 전자 수송/주입능 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 유용하게 적용될 수 있다.Since the compound of the present invention has excellent thermal stability, luminescence, electron transport/injection ability, etc., it can be usefully applied as an organic layer material of an organic electroluminescent device.
또한, 본 발명의 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상되어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, an organic electroluminescent device including the compound of the present invention in an organic layer has greatly improved aspects such as luminescence performance, driving voltage, lifespan, and efficiency, and can be effectively applied to full-color display panels, etc.
도 1은 본 발명의 일례에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.
도 2는 본 발명의 다른 일례에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
FIG. 2 is a cross-sectional view schematically illustrating an organic electroluminescent device according to another example of the present invention.
이하, 본 발명을 상세히 설명한다. Hereinafter, the present invention will be described in detail.
본 발명은 열안정성, 전자 주입/수송능이 우수하여 고효율 전자수송층 재료로 사용될 수 있는 신규 화합물을 제공한다. The present invention provides a novel compound that can be used as a high-efficiency electron transport layer material due to its excellent thermal stability and electron injection/transport ability.
구체적으로, 본 발명에 따른 화학식 1의 화합물은 디벤조계 모이어티의 일측에 N-함유 6원 헤테로방향족환 및 N-함유 아자(aza) 페난트렌 환이 직접 또는 링커를 통해 결합되어 이루어진 코어(core) 구조를 포함한다. 이에 따라, 본 발명의 화합물은 분자의 장축을 기준으로 하여 비대칭성을 가지면서 판상형 구조를 갖기 때문에, 열적 안정성, 발광능, 전자 수송/주입능 등이 우수하다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자에 적용할 경우, 유기 전계 발광 소자는 낮은 구동전압과 높은 발광 효율 및 전류 효율을 가지며, 장수명을 갖는다. Specifically, the compound of formula 1 according to the present invention includes a core structure in which an N-containing 6-membered heteroaromatic ring and an N-containing aza phenanthrene ring are directly or via a linker bound to one side of a dibenzo moiety. Accordingly, the compound of the present invention has a plate-like structure while having asymmetry with respect to the long axis of the molecule, and therefore has excellent thermal stability, luminescence, electron transport/injection ability, etc. When the compound of formula 1 is applied to an organic electroluminescent device, the organic electroluminescent device has a low driving voltage, high luminescence efficiency and current efficiency, and a long lifespan.
상기 화학식 1의 화합물에서, N-함유 6원 헤테로방향족환(예, 트리아진 환, 피리미딘환 등)은 전자 흡수성이 큰 전자 끌개기(electron withdrawing group, EWG)이고, N-함유 아자 페난트렌 환은 전자 끌개기(electron withdrawing group, EWG)이다. 이러한 N-함유 6원 헤테로방향족환 및 N-함유 아자 페난트렌 환은 디벤조계 모이어티의 일측 벤젠 부위에 도입된다. 이때, N-함유 6원 헤테로방향족환 및 N-함유 아자 페난트렌 환은 디벤조계 모이어티에 대해 서로 메타(meta) 위치로 도입될 수 있다. 이 경우, 본 발명의 화합물은 판상형 구조를 이루어 분자 간의 스택킹(stacking)이 유도되고, 따라서 전자이동도가 증가되어 더 우수한 전자수송성을 가질 수 있다. 뿐만 아니라, 본 발명의 화합물은 N-함유 6원 헤테로방향족환과 N-함유 아자 페난트렌 환 간의 상호작용이 최소화되고, 화합물 자체의 물적, 전기화학적 안정성이 상승될 수 있다. 또한, 본 발명에 따른 화학식 1의 화합물은 N-함유 6원 헤테로방향족환 및 N-함유 아자 페난트렌 환이 서로 오쏘(ortho)나 파라(para) 위치에 도입된 화합물에 비해 유기층의 결정화 억제에도 효과가 있어, 유기 전계 발광 소자의 내구성 및 수명 특성을 크게 향상시킬 수 있다.In the compound of the above chemical formula 1, the N-containing 6-membered heteroaromatic ring (e.g., a triazine ring, a pyrimidine ring, etc.) is an electron withdrawing group (EWG) with high electron absorption, and the N-containing aza phenanthrene ring is an electron withdrawing group (EWG). The N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring are introduced to one benzene portion of the dibenzo moiety. At this time, the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring may be introduced at a meta position to each other with respect to the dibenzo moiety. In this case, the compound of the present invention forms a plate-like structure, inducing stacking between molecules, and thus increasing electron mobility, thereby enabling better electron transport properties. In addition, the compound of the present invention can minimize the interaction between the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring, and increase the physical and electrochemical stability of the compound itself. In addition, the compound of chemical formula 1 according to the present invention is effective in suppressing crystallization of an organic layer compared to a compound in which the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring are introduced at the ortho or para positions to each other, and thus can significantly improve the durability and life characteristics of an organic electroluminescent device.
또한, N-함유 6원 헤테로방향족환이 디벤조계 모이어티의 활성 사이트(active site)인 6번 위치에 도입(결합)될 수 있다. 이 경우, 본 발명의 화합물은 분자의 안정성이 증가될 수 있고, 또 화합물의 입체장애(steric hindrance)가 발생하여 열정 안정성이 유의적으로 증가될 수 있다. 이와 함께, N-함유 아자 페난트렌 환이 N-함유 6원 헤테로방향족환과 메타 위치인 디벤조계 모이어티의 8번 위치에 도입될 경우, 열정 안정성의 상승 효과가 더 발휘될 수 있다.In addition, an N-containing 6-membered heteroaromatic ring may be introduced (bonded) to the 6-position, which is the active site of the dibenzo moiety. In this case, the stability of the molecule of the compound of the present invention may be increased, and steric hindrance of the compound may occur, so that the thermal stability may be significantly increased. In addition, when an N-containing azaphenanthrene ring is introduced to the 8-position of the dibenzo moiety, which is the meta position to the N-containing 6-membered heteroaromatic ring, the synergistic effect of thermal stability may be further exerted.
게다가, 본 발명의 화합물은 구조적으로 비대칭성을 갖는다. 이러한 분자의 비대칭성은 결정화를 억제하여 본 발명에 따른 화합물의 공정성 및 소자의 내구성이 향상될 수 있다.In addition, the compound of the present invention has structural asymmetry. This molecular asymmetry can suppress crystallization, thereby improving the processability of the compound according to the present invention and the durability of the device.
특히, 본 발명의 화학식 1로 표시되는 화합물을 전자 수송층 재료로 사용시, 종래의 전자 수송층 재료(예, Alq3 등)에 비해 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 고효율 및 장수명 특성이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when the compound represented by the chemical formula 1 of the present invention is used as an electron transport layer material, an organic electroluminescent device having a low driving voltage, high efficiency, and long lifespan can be manufactured compared to conventional electron transport layer materials (e.g., Alq3, etc.), and further, a full-color display panel with improved high efficiency and long lifespan characteristics can also be manufactured.
전술한 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물은 전자 수송/주입 특성이 우수하기 때문에, 유기 전계 발광 소자의 유기물층인 전자 수송층 및 전자 주입층 중 어느 하나의 재료로 사용될 수 있으며, 바람직하게는 전자수송층 재료로 사용될 수 있다. 이에 따라, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 전자 수송층/주입층 재료, 전자수송 보조층 재료, 더 바람직하게는 전자 수송층 재료로 사용될 수 있다. 이러한 화학식 1의 화합물을 포함하는 본 발명의 유기 전계 발광소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.As described above, since the compound represented by the chemical formula 1 according to the present invention has excellent electron transport/injection characteristics, it can be used as a material for either an electron transport layer or an electron injection layer, which are organic layers of an organic electroluminescent device, and preferably can be used as an electron transport layer material. Accordingly, the compound represented by the chemical formula 1 of the present invention can be used as an organic layer material of an organic electroluminescent device, preferably an electron transport layer/injection layer material, an electron transport auxiliary layer material, and more preferably an electron transport layer material. The organic electroluminescent device of the present invention including the compound of the chemical formula 1 can have greatly improved performance and lifespan characteristics, and a full-color organic light-emitting panel to which the organic electroluminescent device is applied can also have its performance maximized.
상기 화학식 1로 표시되는 화합물에서, 디벤조계 모이어티에 도입되는 Y는 O 또는 S일 수 있다. 일례로, 디벤조퓨란계(Y = O) 모이어티, 디벤조티오펜계(Y = S) 모이어티일 수 있다.In the compound represented by the above chemical formula 1, Y introduced into the dibenzo moiety may be O or S. For example, it may be a dibenzofuran moiety (Y = O) or a dibenzothiophene moiety (Y = S).
또, 상기 화학식 1에서, L1 및 L2는
상기 화학식 2에서,In the above chemical formula 2,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in chemical formula 1.
또, 상기 화학식 1에서, L1 및 L2는 2가(divalent)의 연결기(linker)로서, 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C60의 아릴렌기이다. 예를 들어, 상기 화학식 1에서, L1은 C6~C60의 아릴렌기이고, L2는 단일결합일 수 있고, 구체적으로 L1은 페닐렌기이고, L2는 단일결합일 수 있다. 일례에 따르면, 본 발명에 따른 화학식 1의 화합물은 하기 화학식 3 또는 4의 화합물일 수 있다.In addition, in the chemical formula 1, L 1 and L 2 are divalent linkers, which are the same or different from each other, and each independently represents a single bond or a C 6 to C 60 arylene group. For example, in the chemical formula 1, L 1 may be a C 6 to C 60 arylene group and L 2 may be a single bond, specifically, L 1 may be a phenylene group and L 2 may be a single bond. According to an example, the compound of the chemical formula 1 according to the present invention may be a compound of the following chemical formula 3 or 4.
상기 화학식 3 내지 4에서,In the above chemical formulas 3 to 4,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , and R 1 are each as defined in chemical formula 1.
또, 상기 화학식 1에서, Z1 내지 Z10은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR3이고, 다만 Z1 내지 Z10 중 적어도 하나는 N이다. 바람직하게 Z1 내지 Z10 중에서 1개는 N이고, 나머지는 CR3일 수 있고; 또는 Z1 내지 Z10 중에서 2개는 N이고, 나머지는 CR3일 수 있다. 이때, 상기 CR3가 복수인 경우, 복수의 R3는 서로 동일하거나 또는 상이하다.In addition, in the chemical formula 1, Z 1 to Z 10 are the same or different, and are each independently N or CR 3 , provided that at least one of Z 1 to Z 10 is N. Preferably, one of Z 1 to Z 10 may be N, and the rest may be CR 3 ; or two of Z 1 to Z 10 may be N, and the rest may be CR 3 . At this time, when there is a plurality of CR 3 , the plurality of R 3 are the same or different.
다만, 상기 화학식 1에서, Z1 내지 Z4, Z9 및 Z10 중 어느 하나는 CR3로, 탄소(C)가 L2와 결합하고, 이 경우 R3는 존재하지 않는다. 바람직하게, Z1, Z3 및 Z10 중 어느 하나가 CR3로 탄소(C)가 L2와 결합하고, 이 경우 R3는 존재하지 않는다. 일례로, 본 발명에 따른 화학식 1의 화합물은 하기 화학식 5 내지 7 중에서 어느 하나로 표시되는 화합물일 수 있다.However, in the chemical formula 1, any one of Z 1 to Z 4 , Z 9 , and Z 10 is CR 3 , carbon (C) is bonded to L 2 , and in this case, R 3 is not present. Preferably, any one of Z 1 , Z 3 , and Z 10 is CR 3 , carbon (C) is bonded to L 2 , and in this case, R 3 is not present. For example, the compound of chemical formula 1 according to the present invention may be a compound represented by any one of the following chemical formulas 5 to 7.
상기 화학식 5 내지 7에서,In the above chemical formulas 5 to 7,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in chemical formula 1.
또, 상기 화학식 1에서, X1 내지 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR2이고, 다만 X1 내지 X3 중 적어도 하나는 N이고, 이때 CR2가 복수인 경우, 복수의 R2는 서로 동일하거나 상이하다. 바람직하게 X1 내지 X3 중 적어도 2개는 N일 수 있다. 이와 같이, 상기 화학식 1의 화합물에서, N-함유 6원 헤테로방향족환이 트리아진 모이어티 또는 피리미딘 모이어티인 경우, 피리딘 모이어티인 경우에 비해 EWG 특성이 강하고, 전자 이동도도 더 빠르다. 따라서, 본 발명에 따른 화학식 1의 화합물은 N-함유 6원 헤테로방향족환이 트리아진 모이어티 또는 피리미딘 모이어티일 때 더 우수한 전자수송성을 가질 수 있다.In addition, in the chemical formula 1, X 1 to X 3 are the same as or different from each other, and are each independently N or CR 2 , provided that at least one of X 1 to X 3 is N, and in this case, when CR 2 is plural, plural R 2 are the same or different from each other. Preferably, at least two of X 1 to X 3 can be N. As such, in the compound of the chemical formula 1, when the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety, the EWG characteristics are stronger and the electron mobility is also faster than when it is a pyridine moiety. Therefore, the compound of the chemical formula 1 according to the present invention can have better electron transport properties when the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety.
일례로, 본 발명에 따른 화학식 1의 화합물은 하기 화학식 8 또는 9로 표시되는 화합물일 수 있다.For example, the compound of chemical formula 1 according to the present invention may be a compound represented by the following chemical formula 8 or 9.
상기 화학식 8 및 9에서,In the above chemical formulas 8 and 9,
Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , and R 1 are each as defined in chemical formula 1.
또, 상기 화학식 1에서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택된다. 바람직하게, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기 또는 비페닐기(biphenylene group)일 수 있다. 예컨대, Ar1은 페닐기이고, Ar2는 페닐기 또는 비페닐기일 수 있다. 이 경우, 본 발명에 따른 화합물의 화학적 안정성이 향상될 수 있다. 특히, 화학식 1의 화합물에서, N-함유 6원 헤테로방향족환이 트리아진 모이어티 또는 피리미딘 모이어티인 경우, 이들의 화학적 안정성이 페닐기의 블록킹(blocking)으로 인해 향상됨으로써, 화합물 자체의 화학적 안정성이 더 향상될 수 있다.In addition, in the chemical formula 1, Ar 1 and Ar 2 are the same as or different from each other, and are each independently selected from the group consisting of an aryl group having C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms. Preferably, Ar 1 and Ar 2 are the same as or different from each other, and can each independently be a phenyl group or a biphenylene group. For example, Ar 1 can be a phenyl group, and Ar 2 can be a phenyl group or a biphenylene group. In this case, the chemical stability of the compound according to the present invention can be improved. In particular, in the compound of the chemical formula 1, when the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety, the chemical stability thereof is improved due to blocking of the phenyl group, and thus the chemical stability of the compound itself can be further improved.
또, 상기 화학식 1에서,
또, 상기 화학식 1에서, R1 내지 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며, 바람직하게 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기(더 바람직하게 C1~C12의 알킬기), C6~C60의 아릴기(더 바람직하게, C6~C20의 아릴기) 및 핵원자수 5 내지 60의 헤테로아릴기(더 바람직하게, 핵원자수 5 내지 20의 헤테로아릴기)로 이루어진 군에서 선택될 수 있다. 이때, 상기 헤테로시클로알킬기 및 헤테로아릴기는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로원자를 포함한다.In addition, in the chemical formula 1, R 1 to R 3 are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C It is selected from the group consisting of an arylboron group of C 6 to C 60 , an arylphosphine group of C 6 to C 60, an arylphosphine oxide group of C 6 to C 60 , and an arylamine group of C 6 to C 60 , and preferably may be selected from the group consisting of hydrogen, deuterium (D), halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group (more preferably a C 1 to C 12 alkyl group), a C 6 to C 60 aryl group (more preferably, a C 6 to C 20 aryl group), and a heteroaryl group having 5 to 60 nuclear atoms (more preferably, a heteroaryl group having 5 to 20 nuclear atoms). At this time, the heterocycloalkyl group and the heteroaryl group each include at least one heteroatom selected from the group consisting of N, S, O, and Se.
또, 상기 화학식 1에서, 상기 L1 및 L2의 아릴렌기, Ar1 및 Ar2의 아릴기 및 헤테로아릴기와, R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 바람직하게 중수소, 할로겐, 시아노기, 니트로기, C1~C20의 알킬기, C6~C30의 아릴기, 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환될 수 있다. 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이하다.In addition , in the chemical formula 1, the arylene group of L 1 and L 2 , the aryl group and heteroaryl group of Ar 1 and Ar 2 , and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group , alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C An aryl group having a carbon number of 6 to C 60 , a heteroaryl group having a carbon number of 5 to 60, an alkyloxy group having a carbon number of 1 to C 40 , an aryloxy group having a carbon number of 6 to C 60 , an alkylsilyl group having a carbon number of 1 to C 40 , an arylsilyl group having a carbon number of 6 to C 60 , an alkylboron group having a carbon number of 1 to C 40 , an arylboron group having a carbon number of 6 to C 60 , an arylphosphine group having a carbon number of 6 to C 60 , an arylphosphine oxide group having a carbon number of 6 to C 60 , and an arylamine group having a carbon number of 5 to C 60 are substituted or unsubstituted with one or more substituents selected from the group consisting of, and preferably deuterium, halogen, a cyano group, a nitro group, an alkyl group having a carbon number of 1 to C 20 , a heteroaryl group having a carbon number of 5 to 60, a C 1 to C 40 , a C 6 to C 6 ... It may be unsubstituted or substituted with one or more substituents selected from the group consisting of 30 heteroaryl groups. In this case, when there are multiple substituents, the multiple substituents are the same or different from each other.
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화학식 10 내지 15 중 어느 하나로 보다 구체화될 수 있다.The compound represented by chemical formula 1 according to the present invention can be further specified by any one of the following chemical formulas 10 to 15.
상기 화학식 10 내지 15에서,In the above chemical formulas 10 to 15,
Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , and R 1 are each as defined in chemical formula 1.
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화학식 16 내지 27 중 어느 하나로 더 구체화될 수 있다.The compound represented by chemical formula 1 according to the present invention can be further specified by any one of the following chemical formulas 16 to 27.
상기 화학식 16 내지 27에서,In the above chemical formulas 16 to 27,
Y, Z1 내지 Z10, c, Ar1, Ar2, R1은 각각 화학식 1에서 정의된 바와 같다.Y, Z 1 to Z 10 , c, Ar 1 , Ar 2 , and R 1 are each as defined in chemical formula 1.
이상에서 설명한 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 예시 화합물, 예컨대 화합물 A-1 내지 A-12, B-1 내지 B-12, C-1 내지 C-12, D-1 내지 D-12, E-1 내지 E-12, F-1 내지 F-12, G-1 내지 G-12, H-1 내지 H-12, I-1 내지 I-12, 및 J-1 내지 J-12로 보다 구체화될 수 있다. 그러나 본 발명에 따른 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by chemical formula 1 according to the present invention described above can be further specified as the following exemplary compounds, for example, compounds A-1 to A-12, B-1 to B-12, C-1 to C-12, D-1 to D-12, E-1 to E-12, F-1 to F-12, G-1 to G-12, H-1 to H-12, I-1 to I-12, and J-1 to J-12. However, the compound represented by chemical formula 1 according to the present invention is not limited to the following exemplary compounds.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkenyl" means a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.
본 발명에서"알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkynyl" means a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지는 않는다.In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지는 않는다.In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and further, a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, 모노-뿐만 아니라 디-, 트리-알킬실릴을 포함한다. 또, "아릴실릴"은 탄소수 5 내지 60의 아릴로 치환된 실릴을 의미하고, 모노-뿐만 아니라 디-, 트리-아릴실릴 등의 폴리아릴실릴을 포함한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di- and tri-alkylsilyl. In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono- as well as di- and tri-arylsilyl.
본 발명에서 "알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미한다.In the present invention, “alkylboron group” means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and “arylboro group” means a boron group substituted with an aryl having 6 to 60 carbon atoms.
본 발명에서 "알킬포스피닐기"는 탄소수 1 내지 40의 알킬로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-알킬포스피닐기를 포함한다. 또, 본 발명에서 "아릴포스피닐기"는 탄소수 6 내지 60의 모노아릴 또는 디아릴로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-아릴포스피닐기를 포함한다. In the present invention, the "alkylphosphinyl group" means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In addition, the "arylphosphinyl group" in the present invention means a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.
본 발명에서 "아릴아민"은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미하며, 모노-뿐만 아니라 디-아릴아민를 포함한다.In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 40 carbon atoms, and includes not only mono- but also di-arylamine.
<유기 전계 발광 소자><Organic electroluminescent device>
한편, 본 발명의 다른 측면은 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(이하, '유기 EL 소자')에 관한 것이다.Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the aforementioned chemical formula 1.
구체적으로, 본 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, the organic electroluminescent device according to the present invention comprises an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers comprises a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.
일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층, 및 전자주입층을 포함하고, 상기 전자수송층은 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 전자수송층 물질로 유기 전계 발광 소자에 포함된다. 이러한 유기 전계 발광 소자에서, 전자는 화학식 1의 화합물 때문에, 음극에서 전자수송층으로 용이하게 주입되고, 또한 전자수송층에서 발광층으로 빠르게 이동할 수 있고, 따라서 발광층에서의 정공과 전자의 결합력이 높다. 그러므로, 본 발명의 유기 전계 발광 소자는 발광효율, 전력효율, 휘도 등이 우수하다. According to an example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and the electron transport layer includes a compound represented by the chemical formula 1. At this time, the compound represented by the chemical formula 1 is included in an organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode to the electron transport layer due to the compound of the chemical formula 1, and can also quickly move from the electron transport layer to the light-emitting layer, and therefore the binding force between holes and electrons in the light-emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 예컨대 기판 위에, 양극(100), 1층 이상의 유기물층(300) 및 음극(200)이 순차적으로 적층될 수 있다(도 1 및 도 2 참조). 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but for example, an anode (100), one or more organic layers (300), and a cathode (200) may be sequentially laminated on a substrate (see FIGS. 1 and 2). In addition, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.
일례에 따르면, 상기 유기 전계 발광 소자는 도 1에 도시된 바와 같이, 기판 위에, 양극(100), 정공주입층(310), 정공수송층(320), 발광층(330), 전자수송층(340) 및 음극(200)이 순차적으로 적층된 구조를 가질 수 있다. 선택적으로, 도 2에 도시된 바와 같이, 상기 전자수송층(340)과 음극(200) 사이에 전자주입층이 위치할 수 있다. 본 발명의 유기 전계 발광 소자는 상기 유기물층(300) 중 적어도 하나[예컨대, 전자수송층(340)]가 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.According to an example, the organic electroluminescent device may have a structure in which an anode (100), a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport layer (340), and a cathode (200) are sequentially laminated on a substrate, as illustrated in FIG. 1. Optionally, as illustrated in FIG. 2, an electron injection layer may be positioned between the electron transport layer (340) and the cathode (200). The organic electroluminescent device of the present invention may be manufactured by forming organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers (300) [for example, the electron transport layer (340)] includes a compound represented by the chemical formula 1.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The above organic layer can 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 발명에서 사용 가능한 기판은 특별히 한정되지 않으며, 비제한적인 예로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 있다.The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.
또, 양극 물질의 예로는 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 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있는데, 이에 한정되지는 않는다.Further, examples of the anode material include, but are not limited to, 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); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.
또, 음극 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지는 않는다.Further examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer materials such as LiF/Al or LiO 2 /Al.
또한, 정공주입층, 정공수송층, 발광층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, hole transport layer, light emitting layer, and electron transport layer are not particularly limited, and conventional materials known in the art can 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 through examples. However, the following examples are only intended to illustrate the present invention, and the present invention is not limited to the following examples.
[준비예 1] 화합물 A의 합성[Preparation Example 1] Synthesis of Compound A
<단계 1> 화합물 a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine]의 합성<Step 1> Synthesis of compound a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine]
4-bromo-2-chlorodibenzo[b,d]furan (50 g, 177.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (47.6 g, 177.6 mmol), Pd(PPh3)4 (10.3 g, 8.9 mmol), 및 K2CO3 (73.6 g, 532.8 mmol)을 Toluene 500ml, EtOH 100ml 및 H2O 100ml에 넣고, 12시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine] (61.6 g, 수율 80 %)를 얻었다. 4-Bromo-2-chlorodibenzo[b,d]furan (50 g, 177.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (47.6 g, 177.6 mmol), Pd(PPh 3 ) 4 (10.3 g, 8.9 mmol), and K 2 CO 3 (73.6 g, 532.8 mmol) were added to 500 ml of toluene, 100 ml of EtOH, and 100 ml of H 2 O, and heated under reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine] (61.6 g, yield 80%) was obtained using column chromatography.
[LCMS]: 434[LCMS]: 434
<단계 2> 화합물 A [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound A [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine]
상기 <단계 1>에서 합성된 목적 화합물 a (61.6 g, 141.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (43.3 g, 170.4 mmol), Pd(dppf)Cl2 (3.5 g, 4.3 mmol), Xphos (6.7 g, 14.2 mmol), 및 KOAc (27.9 g, 283.9 mmol)을 1,4-Dioxane 500ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 A (52.9 g, 수율 71 %)을 얻었다. In the above <Step 1>, the synthesized target compound a (61.6 g, 141.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (43.3 g, 170.4 mmol), Pd(dppf)Cl 2 (3.5 g, 4.3 mmol), Xphos (6.7 g, 14.2 mmol), and KOAc (27.9 g, 283.9 mmol) were added to 500 ml of 1,4-Dioxane and heated under reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound A (52.9 g, yield 71%) was obtained using column chromatography.
1H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39 (t, 1H), 7.48-7.50 (m, 6H), 7.54 (d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.98 (d, 1H), 8.34-8.38 (m, 4H) 1 H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39 (t, 1H), 7.48-7.50 (m, 6H), 7.54 (d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.98 (d, 1H), 8.34-8.38 (m, 4H)
[LCMS]: 526[LCMS]: 526
[준비예 2] 화합물 B의 합성[Preparation Example 2] Synthesis of Compound B
<단계 1> 화합물 b의 합성<Step 1> Synthesis of compound b
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 b를 얻었다.Except that 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1, the same procedure as <Step 1> of Preparation Example 1 was performed to obtain the target compound b.
<단계 2> 화합물 B [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound B [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine]
준비예 1의 <단계 2에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 b를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 B [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine] (52.1 g, Overall 수율 35%)을 얻었다.Except for using compound b obtained in <Step 1> instead of compound a used in <Step 2> of Preparation Example 1, the same procedure as <Step 2> of Preparation Example 1 was performed to obtain target compound B [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine] (52.1 g, Overall yield 35%).
1H-NMR: δ 1.19 (s, 12H), 7.31 (d, 1H), 7.39 (t, 1H), 7.54 (d, 1H), 7.49-7.50 (m, 6H), 7.61 (d, 1H), 7.73(t, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.94 (s, 1H), 7.98 (d, 1H), 8.36-8.38 (m, 5H) 1 H-NMR: δ 1.19 (s, 12H), 7.31 (d, 1H), 7.39 (t, 1H), 7.54 (d, 1H), 7.49-7.50 (m, 6H), 7.61 (d, 1H), 7.73(t, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.94 (s, 1H), 7.98 (d, 1H), 8.36-8.38 (m, 5H)
[LCMS] : 602[LCMS] : 602
[준비예 3] 화합물 C 의 합성[Preparation Example 3] Synthesis of compound C
<단계 1> 화합물 c의 합성<Step 1> Synthesis of compound c
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 c를 얻었다.Except that 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1, the same procedure as <Step 1> of Preparation Example 1 was performed to obtain the target compound c.
<단계 2> 화합물 C [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound C [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 c를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 c [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine] (55.1 g, Overall 수율 38%)을 얻었다.Except for using compound c obtained in <Step 1> instead of compound a used in <Step 2> of Preparation Example 1, the same procedure as <Step 2> of Preparation Example 1 was performed to obtain the target compound c [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1,3,5-triazine] (55.1 g, Overall yield 38%).
1H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39 (t, 1H), 7.25 (d, 2H), 7.50-7.52 (m, 6H), 7.54(d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.37 (d, 4H) 1 H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39 (t, 1H), 7.25 (d, 2H), 7.50-7.52 (m, 6H), 7.54(d, 1H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.37 (d, 4H)
[LCMS]: 602[LCMS]: 602
[준비예 4] 화합물 D의 합성[Preparation Example 4] Synthesis of Compound D
<단계 1> 화합물 d의 합성<Step 1> Synthesis of compound d
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 d를 얻었다.Except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1, the same procedure as <Step 1> of Preparation Example 1 was performed to obtain the target compound d.
<단계 2> 화합물 D [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound D [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 d를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 D [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine] (55.5 g, Overall 수율 40%)을 얻었다.Except that the compound d obtained in <Step 1> was used instead of the compound a used in <Step 2> of Preparation Example 1, the same procedure as in <Step 2> of Preparation Example 1 was performed to obtain the target compound D [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine] (55.5 g, Overall yield 40%).
1H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H), 7.75(d, 2H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.36 (d, 2H) 1 H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H) ), 7.75(d, 2H), 7.76 (s, 1H), 7.82 (s, 1H), 7.96 (d, 2H), 7.98 (d, 1H), 8.36 (d, 2H)
[LCMS]: 602[LCMS]: 602
[준비예 5] 화합물 E의 합성[Preparation Example 5] Synthesis of compound E
<단계 1> 화합물 e의 합성<Step 1> Synthesis of compound e
준비예 1의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidin을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 e를 얻었다.Except that 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidin was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 1, the same procedure as <Step 1> of Preparation Example 1 was performed to obtain the target compound e.
<단계 2> 화합물 E [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)pyrimidine]의 합성<Step 2> Synthesis of compound E [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)pyrimidine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 e를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 E [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)pyrimidine] (53.2 g, Overall 수율 37%)을 얻었다.Except that compound e obtained in <Step 1> was used instead of compound a used in <Step 2> of Preparation Example 1, the same procedure as <Step 2> of Preparation Example 1 was performed to obtain the target compound E [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)pyrimidine] (53.2 g, Overall yield 37%).
1H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H), 7.75(d, 2H), 7.76 (s, 1H), 7.82 (s, 1H), 7.85 (d, 2H), 7.98 (d, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H) 1 H-NMR: δ 1.20 (s, 12H), 7.31 (t, 1H), 7.39-7.41 (m, 2H), 7.49-7.50 (m, 5H), 7.54 (d, 1H), 7.75(d, 2H) ), 7.76 (s, 1H), 7.82 (s, 1H), 7.85 (d, 2H), 7.98 (d, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H)
[LCMS]: 601[LCMS]: 601
[준비예 6] 화합물 F의 합성[Preparation Example 6] Synthesis of compound F
<단계 1> 화합물 f의 합성<Step 1> Synthesis of compound f
준비예 1의 <단계 1>에서 사용된 4-bromo-2-chlorodibenzo[b,d]furan 대신 4-bromo-2-chlorodibenzo[b,d]thiophene을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 f를 얻었다.The target compound f was obtained by performing the same procedure as in <Step 1> of Preparation Example 1, except that 4-bromo-2-chlorodibenzo[b,d]thiophene was used instead of 4-bromo-2-chlorodibenzo[b,d]furan used in <Step 1> of Preparation Example 1.
<단계 2> 화합물 F [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound F [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine]
준비예 1의 <단계 2>에서 사용된 화합물 a 대신 상기 <단계 1>에서 얻은 화합물 f를 사용하는 것을 제외하고는, 준비예 1의 <단계 2>와 동일하게 수행하여 목적 화합물 F [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine] (50.4 g, Overall 수율 33%)을 얻었다.Except that compound f obtained in <Step 1> was used instead of compound a used in <Step 2> of Preparation Example 1, the same procedure as <Step 2> of Preparation Example 1 was performed to obtain the target compound F [2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine] (50.4 g, Overall yield 33%).
1H-NMR: δ 1.20 (s, 12H), 7.48-7.49 (m, 6H), 7.50 (t, 1H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.48-7.49 (m, 6H), 7.50 (t, 1H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H)
[LCMS]: 542[LCMS]: 542
[준비예 7] 화합물 G의 합성[Preparation Example 7] Synthesis of compound G
<단계 1> 화합물 g의 합성<Step 1> Synthesis of compound g
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 g를 얻었다.The target compound g was obtained in the same manner as in <Step 1> of Preparation Example 1, except that 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6.
<단계 2> 화합물 G [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound G [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 g를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 G [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine] (54.4 g, Overall 수율 35%)을 얻었다.Except that compound g obtained in <Step 1> was used instead of compound f used in <Step 2> of Preparation Example 6, the same procedure as in <Step 2> of Preparation Example 6 was performed to obtain the target compound G [2,4-diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine] (54.4 g, Overall yield 35%).
1H-NMR: δ 1.20 (s, 12H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.61(d, 1H), 7.73 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.94 (s, 1H), 8.01 (s, 1H), 8.36-8.38 (m, 5H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.61 (d, 1H), 7.73 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.94 (s, 1H), 8.01 (s, 1H), 8.36-8.38 (m, 5H), 8.45 (d, 1H)
[LCMS] : 618[LCMS] : 618
[준비예 8] 화합물 H의 합성[Preparation Example 8] Synthesis of compound H
<단계 1> 화합물 h의 합성<Step 1> Synthesis of compound h
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 h를 얻었다.Except that 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6, the same procedure as <Step 1> of Preparation Example 1 was performed to obtain the target compound h.
<단계 2> 화합물 H [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound H [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 h를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 H [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine] (53.0 g, Overall 수율 32%)을 얻었다.Except that the compound h obtained in the above <Step 1> was used instead of the compound f used in <Step 2> of Preparation Example 6, the same procedure as in <Step 2> of Preparation Example 6 was performed to obtain the target compound H [2,4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)phenyl)-1,3,5-triazine] (53.0 g, Overall yield 32%).
1H-NMR: δ 1.20 (s, 12H), 7.23 (d, 2H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.23 (d, 2H), 7.48-7.50 (m, 7H), 7.56 (t, 1H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 4H), 8.45 (d, 1H)
[LCMS]: 618[LCMS]: 618
[준비예 9] 화합물 I의 합성[Preparation Example 9] Synthesis of Compound I
<단계 1> 화합물 i의 합성<Step 1> Synthesis of compound i
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 i를 얻었다.Except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6, the same procedure as <Step 1> of Preparation Example 1 was performed to obtain the target compound i.
<단계 2> 화합물 I [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine]의 합성<Step 2> Synthesis of compound I [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 i를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 I [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine] (55.2 g, Overall 수율 36%)을 얻었다.Except that the compound i obtained in the above <Step 1> was used instead of the compound f used in <Step 2> of Preparation Example 6, the same procedure as in <Step 2> of Preparation Example 6 was performed to obtain the target compound I [2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine] (55.2 g, Overall yield 36%).
1H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 2H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.25 (d, 2H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.93 (d, 1H), 7.96 (d, 2H), 8.01 (s, 1H), 8.36 (d, 2H), 8.45 (d, 1H)
[LCMS]: 618[LCMS]: 618
[준비예 10] 화합물 J의 합성[Preparation Example 10] Synthesis of compound J
<단계 1> 화합물 j의 합성<Step 1> Synthesis of compound j
준비예 6의 <단계 1>에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine을 사용한 것을 제외하고는, 준비예 1의 <단계 1>과 동일하게 수행하여 목적 화합물 j를 얻었다.Except that 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in <Step 1> of Preparation Example 6, the same procedure as <Step 1> of Preparation Example 1 was performed to obtain the target compound j.
<단계 2> 화합물 J [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)pyrimidine]의 합성<Step 2> Synthesis of compound J [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)pyrimidine]
준비예 6의 <단계 2>에서 사용된 화합물 f 대신 상기 <단계 1>에서 얻은 화합물 j를 사용하는 것을 제외하고는, 준비예 6의 <단계 2>와 동일하게 수행하여 목적 화합물 J [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)pyrimidine] (55.2 g, Overall 수율 36%)을 얻었다.Except that the compound j obtained in the above <Step 1> was used instead of the compound f used in <Step 2> of Preparation Example 6, the same procedure as in <Step 2> of Preparation Example 6 was performed to obtain the target compound J [4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)pyrimidine] (55.2 g, Overall yield 36%).
1H-NMR: δ 1.20 (s, 12H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.85 (d, 2H), 7.93 (d, 1H), 8.01 (s, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H), 8.45 (d, 1H) 1 H-NMR: δ 1.20 (s, 12H), 7.41 (t, 1H), 7.48-7.50 (m, 6H), 7.56 (t, 1H), 7.75 (d, 2H), 7.78 (s, 1H), 7.85 (d, 2H), 7.93 (d, 1H), 8.01 (s, 1H), 8.23 (s, 1H), 8.30 (d, 2H), 8.35 (d, 2H), 8.45 (d, 1H)
[LCMS]: 617[LCMS]: 617
[합성예 1] 화합물 A-1의 합성[Synthesis Example 1] Synthesis of Compound A-1
준비예 1의 목적 화합물 A (5 g, 9.5 mmol), 2-bromophenanthridine (2.5 g, 9.5 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 28.5 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 A-1 (4.1 g, 수율 75 %)을 얻었다.The target compound A (5 g, 9.5 mmol), 2-bromophenanthridine (2.5 g, 9.5 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), K 2 CO 3 (3.9 g, 28.5 mmol) of Preparation Example 1 were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound A-1 (4.1 g, yield 75%) was obtained using column chromatography.
[LCMS]: 577[LCMS]: 577
[합성예 2] 화합물 A-2의 합성[Synthesis Example 2] Synthesis of Compound A-2
합성예 1에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-2 (3.9 g, 수율 72%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-2 (3.9 g, yield 72%).
[LCMS]: 577[LCMS]: 577
[합성예 3] 화합물 A-3의 합성[Synthesis Example 3] Synthesis of Compound A-3
합성예 1에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-3 (3.8 g, 수율 70%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-3 (3.8 g, yield 70%).
[LCMS]: 577[LCMS]: 577
[합성예 4] 화합물 A-4의 합성[Synthesis Example 4] Synthesis of Compound A-4
합성예 1에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-4 (3.5 g, 수율 65%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-4 (3.5 g, yield 65%).
[LCMS]: 577[LCMS]: 577
[합성예 5] 화합물 A-5의 합성[Synthesis Example 5] Synthesis of Compound A-5
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-5 (3.5 g, 수율 65%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-5 (3.5 g, yield 65%).
[LCMS]: 577[LCMS]: 577
[합성예 6] 화합물 A-6의 합성[Synthesis Example 6] Synthesis of Compound A-6
합성예 1에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-6 (3.9 g, 수율 72%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-6 (3.9 g, yield 72%).
[LCMS]: 577[LCMS]: 577
[합성예 7] 화합물 A-7의 합성[Synthesis Example 7] Synthesis of Compound A-7
합성예 1에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-7 (3.7 g, 수율 67%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-7 (3.7 g, yield 67%).
[LCMS]: 577[LCMS]: 577
[합성예 8] 화합물 A-8의 합성[Synthesis Example 8] Synthesis of Compound A-8
합성예 1에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-8 (3.7 g, 수율 67%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1, the same process as Synthesis Example 1 was performed to obtain the target compound A-8 (3.7 g, yield 67%).
[LCMS]: 577[LCMS]: 577
[합성예 9] 화합물 A-9의 합성[Synthesis Example 9] Synthesis of Compound A-9
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-9 (3.4 g, 수율 62%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-9 (3.4 g, yield 62%).
[LCMS]: 577[LCMS]: 577
[합성예 10] 화합물 A-10의 합성[Synthesis Example 10] Synthesis of Compound A-10
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-10 (3.4 g (수율 62%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1, the same process as Synthesis Example 1 was performed to obtain the target compound A-10 (3.4 g (yield 62%).
[LCMS]: 577[LCMS]: 577
[합성예 11] 화합물 A-11의 합성[Synthesis Example 11] Synthesis of Compound A-11
합성예 1에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-11 (3.3 g, 수율 60%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1, to obtain the target compound A-11 (3.3 g, yield 60%).
[LCMS]: 577[LCMS]: 577
[합성예 12] 화합물 A-12의 합성[Synthesis Example 12] Synthesis of Compound A-12
합성예 1에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 1과 동일한 과정을 수행하여 목적 화합물 A-12 (3.3 g, 수율 61%)을 얻었다.The same procedure as in Synthesis Example 1 was followed, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine, to obtain the target compound A-12 (3.3 g, yield 61%).
[LCMS] : 577[LCMS] : 577
[합성예 13] 화합물 B-1의 합성[Synthesis Example 13] Synthesis of Compound B-1
준비예 2에서 합성된 화합물 B (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol) 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 사용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 B-1 (3.8 g, 수율 70 %)을 얻었다.In Preparation Example 2, compound B (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), and K 2 CO 3 (3.5 g, 24.9 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound B-1 (3.8 g, yield 70%) was obtained using column chromatography.
[LCMS] : 653[LCMS] : 653
[합성예 14] 화합물 B-2의 합성[Synthesis Example 14] Synthesis of Compound B-2
합성예 13에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-2 (3.9 g, 수율 72%)을 얻었다.The same procedure as in Synthesis Example 13 was followed, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine, to obtain the target compound B-2 (3.9 g, yield 72%).
[LCMS]: 653[LCMS]: 653
[합성예 15] 화합물 B-3의 합성[Synthesis Example 15] Synthesis of Compound B-3
합성예 13에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-3 (3.9 g, 수율 73%)을 얻었다.The same procedure as in Synthesis Example 13 was followed, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine, to obtain the target compound B-3 (3.9 g, yield 73%).
[LCMS]: 653[LCMS]: 653
[합성예 16] 화합물 B-4의 합성[Synthesis Example 16] Synthesis of Compound B-4
합성예 13에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-4 (3.9 g, 수율 73%)을 얻었다.The same procedure as in Synthesis Example 13 was followed, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13, to obtain the target compound B-4 (3.9 g, yield 73%).
[LCMS]: 653[LCMS]: 653
[합성예 17] 화합물 B-5의 합성[Synthesis Example 17] Synthesis of Compound B-5
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-5 (3.8 g, 수율 70%)을 얻었다.The same procedure as in Synthesis Example 13 was followed, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13, to obtain the target compound B-5 (3.8 g, yield 70%).
[LCMS]: 653[LCMS]: 653
[합성예 18] 화합물 B-6의 합성[Synthesis Example 18] Synthesis of Compound B-6
합성예 13에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-6 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13, the same procedure as in Synthesis Example 13 was performed to obtain the target compound B-6 (3.7 g, yield 68%).
[LCMS] : 653[LCMS] : 653
[합성예 19] 화합물 B-7의 합성[Synthesis Example 19] Synthesis of Compound B-7
합성예 13에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-7 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13, the same procedure as in Synthesis Example 13 was performed to obtain the target compound B-7 (3.7 g, yield 68%).
[LCMS] : 653[LCMS] : 653
[합성예 20] 화합물 B-8의 합성[Synthesis Example 20] Synthesis of Compound B-8
합성예 13에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-8 (3.5 g, 수율 65%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13, the same procedure as in Synthesis Example 13 was performed to obtain the target compound B-8 (3.5 g, yield 65%).
[LCMS] : 653[LCMS] : 653
[합성예 21] 화합물 B-9의 합성[Synthesis Example 21] Synthesis of Compound B-9
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-9 (3.3 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13, the same procedure as in Synthesis Example 13 was performed to obtain the target compound B-9 (3.3 g, yield 60%).
[LCMS] : 653[LCMS] : 653
[합성예 22] 화합물 B-10의 합성[Synthesis Example 22] Synthesis of Compound B-10
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-10 (3.1 g, 수율 57%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13, the same procedure as in Synthesis Example 13 was performed to obtain the target compound B-10 (3.1 g, yield 57%).
[LCMS] : 653[LCMS] : 653
[합성예 23] 화합물 B-11의 합성[Synthesis Example 23] Synthesis of Compound B-11
합성예 13에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-11 (3.2 g, 수율 59%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13, the same procedure as in Synthesis Example 13 was performed to obtain the target compound B-11 (3.2 g, yield 59%).
[LCMS] : 653[LCMS] : 653
[합성예 24] 화합물 B-12의 합성[Synthesis Example 24] Synthesis of Compound B-12
합성예 13에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 13과 동일한 과정을 수행하여 목적 화합물 B-12 (3.2 g, 수율 59%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13, the same procedure as in Synthesis Example 13 was followed to obtain the target compound B-12 (3.2 g, yield 59%).
[LCMS] : 653[LCMS] : 653
[합성예 25] 화합물 C-1의 합성[Synthesis Example 25] Synthesis of Compound C-1
준비예 3에서 합성된 화합물 C (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol) 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후, 컬럼크로마토그래피를 이용하여 목적 화합물 C-1 (3.9 g, 수율 72 %)을 얻었다.In Preparation Example 3, compound C (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), and K 2 CO 3 (3.5 g, 24.9 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound C-1 (3.9 g, yield 72%) was obtained using column chromatography.
[LCMS] : 653[LCMS] : 653
[합성예 26] 화합물 C-2의 합성[Synthesis Example 26] Synthesis of Compound C-2
합성예 26에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-2 (3.9 g, 수율 72%)을 얻었다.Except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same process as in Synthesis Example 26 was performed to obtain the target compound C-2 (3.9 g, yield 72%).
[LCMS] : 653[LCMS] : 653
[합성예 27] 화합물 C-3의 합성[Synthesis Example 27] Synthesis of Compound C-3
합성예 26에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-3 (3.9 g, 수율 73%)을 얻었다.Except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same process as in Synthesis Example 26 was performed to obtain the target compound C-3 (3.9 g, yield 73%).
[LCMS] : 653[LCMS] : 653
[합성예 28] 화합물 C-4의 합성[Synthesis Example 28] Synthesis of Compound C-4
합성예 26에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-4 (3.9 g, 수율 73%)을 얻었다.Except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same process as in Synthesis Example 26 was performed to obtain the target compound C-4 (3.9 g, yield 73%).
[LCMS]: 653[LCMS]: 653
[합성예 29] 화합물 C-5의 합성[Synthesis Example 29] Synthesis of Compound C-5
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-5 (3.8 g, 수율 70%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same process as in Synthesis Example 26 was performed to obtain the target compound C-5 (3.8 g, yield 70%).
[LCMS] : 653[LCMS] : 653
[합성예 30] 화합물 C-6의 합성[Synthesis Example 30] Synthesis of Compound C-6
합성예 26에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-6 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same procedure as in Synthesis Example 26 was followed to obtain the target compound C-6 (3.7 g, yield 68%).
[LCMS] : 653[LCMS] : 653
[합성예 31] 화합물 C-7의 합성[Synthesis Example 31] Synthesis of Compound C-7
합성예 26에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-7 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same procedure as in Synthesis Example 26 was followed to obtain the target compound C-7 (3.7 g, yield 68%).
[LCMS] : 653[LCMS] : 653
[합성예 32] 화합물 C-8의 합성[Synthesis Example 32] Synthesis of Compound C-8
합성예 26에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-8 (3.5 g, 수율 65%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same procedure as in Synthesis Example 26 was followed to obtain the target compound C-8 (3.5 g, yield 65%).
[LCMS] : 653[LCMS] : 653
[합성예 33] 화합물 C-9의 합성[Synthesis Example 33] Synthesis of Compound C-9
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-9 (3.3 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same procedure as in Synthesis Example 26 was followed to obtain the target compound C-9 (3.3 g, yield 60%).
[LCMS] : 653[LCMS] : 653
[합성예 34] 화합물 C-10의 합성[Synthesis Example 34] Synthesis of Compound C-10
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-10 (3.1 g, 수율 57%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same procedure as in Synthesis Example 26 was followed to obtain the target compound C-10 (3.1 g, yield 57%).
[LCMS] : 653[LCMS] : 653
[합성예 35] 화합물 C-11의 합성[Synthesis Example 35] Synthesis of Compound C-11
합성예 26에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-11 (3.2 g, 수율 59%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same procedure as in Synthesis Example 26 was followed to obtain the target compound C-11 (3.2 g, yield 59%).
[LCMS] : 653[LCMS] : 653
[합성예 36] 화합물 C-12의 합성[Synthesis Example 36] Synthesis of Compound C-12
합성예 26에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 26과 동일한 과정을 수행하여 목적 화합물 C-12 (3.2 g, 수율 59%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26, the same procedure as in Synthesis Example 26 was followed to obtain the target compound C-12 (3.2 g, yield 59%).
[LCMS] : 653[LCMS] : 653
[합성예 37] 화합물 D-1의 합성[Synthesis Example 37] Synthesis of Compound D-1
준비예 4에서 합성된 화합물 D (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 D-1 (3.8 g, 수율 70 %)을 얻었다.In Preparation Example 4, compound D (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), and K 2 CO 3 (3.5 g, 24.9 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound D-1 (3.8 g, yield 70%) was obtained using column chromatography.
[LCMS] : 653[LCMS] : 653
[합성예 38] 화합물 D-2의 합성[Synthesis Example 38] Synthesis of Compound D-2
합성예 37에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-2 (3.9 g, 수율 72%)을 얻었다.The same procedure as in Synthesis Example 37 was followed, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine, to obtain the target compound D-2 (3.9 g, yield 72%).
[LCMS] : 653[LCMS] : 653
[합성예 39] 화합물 D-3의 합성[Synthesis Example 39] Synthesis of Compound D-3
합성예 37에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-3 (3.8 g, 수율 70%)을 얻었다.The same procedure as in Synthesis Example 37 was followed, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine, to obtain the target compound D-3 (3.8 g, yield 70%).
[LCMS] : 653[LCMS] : 653
[합성예 40] 화합물 D-4의 합성[Synthesis Example 40] Synthesis of compound D-4
합성예 37에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-4 (3.6 g, 수율 66%)을 얻었다.The same procedure as in Synthesis Example 37 was followed, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine, to obtain the target compound D-4 (3.6 g, yield 66%).
[LCMS] : 653[LCMS] : 653
[합성예 41] 화합물 D-5의 합성[Synthesis Example 41] Synthesis of Compound D-5
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-5 (3.8 g, 수율 70%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was performed to obtain the target compound D-5 (3.8 g, yield 70%).
[LCMS] : 653[LCMS] : 653
[합성예 42] 화합물 D-6의 합성[Synthesis Example 42] Synthesis of Compound D-6
합성예 37에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-6 (3.8 g, 수율 70%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was followed to obtain the target compound D-6 (3.8 g, yield 70%).
[LCMS] : 653[LCMS] : 653
[합성예 43] 화합물 D-7의 합성[Synthesis Example 43] Synthesis of compound D-7
합성예 37에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-7 (3.1 g (수율 58%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was performed to obtain the target compound D-7 (3.1 g (yield 58%).
[LCMS] : 653[LCMS] : 653
[합성예 44] 화합물 D-8의 합성[Synthesis Example 44] Synthesis of compound D-8
합성예 37에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-8 (3.5 g, 수율 65%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was followed to obtain the target compound D-8 (3.5 g, yield 65%).
[LCMS] : 653[LCMS] : 653
[합성예 45] 화합물 D-9의 합성[Synthesis Example 45] Synthesis of Compound D-9
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-9 (3.0 g, 수율 55%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was performed to obtain the target compound D-9 (3.0 g, yield 55%).
[LCMS] : 653[LCMS] : 653
[합성예 46] 화합물 D-10의 합성[Synthesis Example 46] Synthesis of compound D-10
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-10 (3.1 g, 수율 58%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was followed to obtain the target compound D-10 (3.1 g, yield 58%).
[LCMS] : 653[LCMS] : 653
[합성예 47] 화합물 D-11의 합성[Synthesis Example 47] Synthesis of Compound D-11
합성예 37에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-11 (3.2 g, 수율 59%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was followed to obtain the target compound D-11 (3.2 g, yield 59%).
[LCMS] : 653[LCMS] : 653
[합성예 48] 화합물 D-12의 합성[Synthesis Example 48] Synthesis of Compound D-12
합성예 37에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 37과 동일한 과정을 수행하여 목적 화합물 D-12 (3.3 g, 수율 62%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37, the same procedure as in Synthesis Example 37 was followed to obtain the target compound D-12 (3.3 g, yield 62%).
[LCMS] : 653[LCMS] : 653
[합성예 49] 화합물 E-1의 합성[Synthesis Example 49] Synthesis of Compound E-1
준비예 5에서 합성된 화합물 E (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), 및 K2CO3 (3.5 g, 24.9 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 E-1 (3.8 g, 수율 70 %)을 얻었다.In Preparation Example 5, compound E (5 g, 8.3 mmol), 2-bromophenanthridine (2.1 g, 8.3 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), and K 2 CO 3 (3.5 g, 24.9 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound E-1 (3.8 g, yield 70%) was obtained using column chromatography.
[LCMS] : 652[LCMS] : 652
[합성예 50] 화합물 E-2의 합성[Synthesis Example 50] Synthesis of Compound E-2
합성예 49에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-2 (3.9 g, 수율 72%)을 얻었다.Except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was performed to obtain the target compound E-2 (3.9 g, yield 72%).
[LCMS] : 652[LCMS] : 652
[합성예 51] 화합물 E-3의 합성[Synthesis Example 51] Synthesis of Compound E-3
합성예 49에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-3 (3.5 g, 수율 64%)을 얻었다.Except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same process as in Synthesis Example 49 was performed to obtain the target compound E-3 (3.5 g, yield 64%).
[LCMS] : 652[LCMS] : 652
[합성예 52] 화합물 E-4의 합성[Synthesis Example 52] Synthesis of Compound E-4
합성예 49에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-4 (3.6 g, 수율 67%)을 얻었다.Except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was performed to obtain the target compound E-4 (3.6 g, yield 67%).
[LCMS] : 652[LCMS] : 652
[합성예 53] 화합물 E-5의 합성[Synthesis Example 53] Synthesis of Compound E-5
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-5 (3.8 g, 수율 71%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was performed to obtain the target compound E-5 (3.8 g, yield 71%).
[LCMS] : 652[LCMS] : 652
[합성예 54] 화합물 E-6의 합성[Synthesis Example 54] Synthesis of compound E-6
합성예 49에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-6 (3.8 g, 수율 71%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was followed to obtain the target compound E-6 (3.8 g, yield 71%).
[LCMS] : 652[LCMS] : 652
[합성예 55] 화합물 E-7의 합성[Synthesis Example 55] Synthesis of Compound E-7
합성예 49에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-7 (3.3 g, 수율 61%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was followed to obtain the target compound E-7 (3.3 g, yield 61%).
[LCMS] : 652[LCMS] : 652
[합성예 56] 화합물 E-8의 합성[Synthesis Example 56] Synthesis of compound E-8
합성예 49에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-8 (3.4 g, 수율 64%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was followed to obtain the target compound E-8 (3.4 g, yield 64%).
[LCMS] : 652[LCMS] : 652
[합성예 57] 화합물 E-9의 합성[Synthesis Example 57] Synthesis of compound E-9
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-9 (3.1 g, 수율 58%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was followed to obtain the target compound E-9 (3.1 g, yield 58%).
[LCMS] : 652[LCMS] : 652
[[ 합성예Synthetic example 58] 화합물 E-10의 합성58] Synthesis of compound E-10
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-10 (3.1 g, 수율 58%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was followed to obtain the target compound E-10 (3.1 g, yield 58%).
[LCMS] : 652[LCMS] : 652
[합성예 59] 화합물 E-11의 합성[Synthesis Example 59] Synthesis of compound E-11
합성예 49에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-11 (3.2 g, 수율 59%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was followed to obtain the target compound E-11 (3.2 g, yield 59%).
[LCMS] : 652[LCMS] : 652
[합성예 60] 화합물 E-12의 합성[Synthesis Example 60] Synthesis of compound E-12
합성예 49에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 49와 동일한 과정을 수행하여 목적 화합물 E-12 (3.2 g, 수율 62%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49, the same procedure as in Synthesis Example 49 was followed to obtain the target compound E-12 (3.2 g, yield 62%).
[LCMS] : 652[LCMS] : 652
[합성예 61] 화합물 F-1의 합성[Synthesis Example 61] Synthesis of Compound F-1
준비예 6에서 합성된 화합물 F (5 g, 9.2 mmol), 2-bromophenanthridine (2.4 g, 9.2 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.8 g, 27.7 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 F-1 (3.7 g, 수율 68 %)을 얻었다.In Preparation Example 6, compound F (5 g, 9.2 mmol), 2-bromophenanthridine (2.4 g, 9.2 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.8 g, 27.7 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound F-1 (3.7 g, yield 68%).
[LCMS] : 593[LCMS] : 593
[합성예 62] 화합물 F-2의 합성[Synthesis Example 62] Synthesis of Compound F-2
합성예 61에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-2 (3.8 g, 수율 69%)을 얻었다.Except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was performed to obtain the target compound F-2 (3.8 g, yield 69%).
[LCMS] : 593[LCMS] : 593
[합성예 63] 화합물 F-3의 합성[Synthesis Example 63] Synthesis of compound F-3
합성예 61에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-3 (3.9 g, 수율 72%)을 얻었다.Except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same process as in Synthesis Example 61 was performed to obtain the target compound F-3 (3.9 g, yield 72%).
[LCMS] : 593[LCMS] : 593
[합성예 64] 화합물 F-4의 합성[Synthesis Example 64] Synthesis of Compound F-4
합성예 61에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-4 (3.9 g, 수율 72%)을 얻었다.Except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was performed to obtain the target compound F-4 (3.9 g, yield 72%).
[LCMS] : 593[LCMS] : 593
[합성예 65] 화합물 F-5의 합성[Synthesis Example 65] Synthesis of Compound F-5
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-5 (3.8 g, 수율 70%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was performed to obtain the target compound F-5 (3.8 g, yield 70%).
[LCMS] : 593[LCMS] : 593
[합성예 66] 화합물 F-6의 합성[Synthesis Example 66] Synthesis of compound F-6
합성예 61에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-6 (3.6 g, 수율 67%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was followed to obtain the target compound F-6 (3.6 g, yield 67%).
[LCMS] : 593[LCMS] : 593
[합성예 67] 화합물 F-7의 합성[Synthesis Example 67] Synthesis of Compound F-7
합성예 61에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-7 (3.6 g, 수율 67%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was followed to obtain the target compound F-7 (3.6 g, yield 67%).
[LCMS] : 593[LCMS] : 593
[합성예 68] 화합물 F-8의 합성[Synthesis Example 68] Synthesis of compound F-8
합성예 61에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-8 (3.4 g, 수율 63%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was followed to obtain the target compound F-8 (3.4 g, yield 63%).
[LCMS] : 593[LCMS] : 593
[합성예 69] 화합물 F-9의 합성[Synthesis Example 69] Synthesis of Compound F-9
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-9 (3.3 g, 수율 62%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was followed to obtain the target compound F-9 (3.3 g, yield 62%).
[LCMS] : 593[LCMS] : 593
[합성예 70] 화합물 F-10의 합성[Synthesis Example 70] Synthesis of compound F-10
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-10 (3.2 g, 수율 58%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was followed to obtain the target compound F-10 (3.2 g, yield 58%).
[LCMS] : 593[LCMS] : 593
[합성예 71] 화합물 F-11의 합성[Synthesis Example 71] Synthesis of compound F-11
합성예 61에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-11 (3.3 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was followed to obtain the target compound F-11 (3.3 g, yield 60%).
[LCMS] : 593[LCMS] : 593
[합성예 72] 화합물 F-12의 합성[Synthesis Example 72] Synthesis of compound F-12
합성예 61에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 61과 동일한 과정을 수행하여 목적 화합물 F-12 (3.2 g, 수율 59%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61, the same procedure as in Synthesis Example 61 was followed to obtain the target compound F-12 (3.2 g, yield 59%).
[LCMS] : 593[LCMS] : 593
[합성예 73] 화합물 G-1의 합성[Synthesis Example 73] Synthesis of Compound G-1
준비예 7에서 합성된 화합물 G (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 G-1 (3.7 g, 수율 69 %)을 얻었다.In Preparation Example 7, compound G (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, 24.3 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound G-1 (3.7 g, yield 69%).
[LCMS] : 669[LCMS] : 669
[합성예 74] 화합물 G-2의 합성[Synthesis Example 74] Synthesis of Compound G-2
합성예 73에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-2 (3.7 g, 수율 69%)을 얻었다.The same procedure as in Synthesis Example 73 was followed, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine, to obtain the target compound G-2 (3.7 g, yield 69%).
[LCMS] : 669[LCMS] : 669
[합성예 75] 화합물 G-3의 합성[Synthesis Example 75] Synthesis of Compound G-3
합성예 73에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-3 (3.8 g, 수율 70%)을 얻었다.Except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was performed to obtain the target compound G-3 (3.8 g, yield 70%).
[LCMS] : 669[LCMS] : 669
[합성예 76] 화합물 G-4의 합성[Synthesis Example 76] Synthesis of Compound G-4
합성예 73에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-4 (3.6 g (수율 67%)을 얻었다.Except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same process as Synthesis Example 73 was performed to obtain the target compound G-4 (3.6 g (yield 67%).
[LCMS] : 669[LCMS] : 669
[합성예 77] 화합물 G-5의 합성[Synthesis Example 77] Synthesis of Compound G-5
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-5 (3.6 g, 수율 67%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was performed to obtain the target compound G-5 (3.6 g, yield 67%).
[LCMS] : 669[LCMS] : 669
[합성예 78] 화합물 G-6의 합성[Synthesis Example 78] Synthesis of compound G-6
합성예 73에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-6 (3.5 g, 수율 65%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was followed to obtain the target compound G-6 (3.5 g, yield 65%).
[LCMS] : 669[LCMS] : 669
[합성예 79] 화합물 G-7의 합성[Synthesis Example 79] Synthesis of Compound G-7
합성예 73에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-7 (3.5 g, 수율 65%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was followed to obtain the target compound G-7 (3.5 g, yield 65%).
[LCMS] : 669[LCMS] : 669
[합성예 80] 화합물 G-8의 합성[Synthesis Example 80] Synthesis of compound G-8
합성예 73에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-8 (3.4 g, 수율 62%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was performed to obtain the target compound G-8 (3.4 g, yield 62%).
[LCMS] : 669[LCMS] : 669
[합성예 81] 화합물 G-9의 합성[Synthesis Example 81] Synthesis of Compound G-9
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-9 (3.3 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was followed to obtain the target compound G-9 (3.3 g, yield 60%).
[LCMS] : 669[LCMS] : 669
[합성예 82] 화합물 G-10의 합성[Synthesis Example 82] Synthesis of compound G-10
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-10 (2.9 g, 수율 54%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was followed to obtain the target compound G-10 (2.9 g, yield 54%).
[LCMS] : 669[LCMS] : 669
[합성예 83] 화합물 G-11의 합성[Synthesis Example 83] Synthesis of compound G-11
합성예 73에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-11 (2.8 g, 수율 53%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was followed to obtain the target compound G-11 (2.8 g, yield 53%).
[LCMS] : 669[LCMS] : 669
[합성예 84] 화합물 G-12의 합성[Synthesis Example 84] Synthesis of Compound G-12
합성예 73에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 73과 동일한 과정을 수행하여 목적 화합물 G-12 (2.8 g, 수율 53%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73, the same procedure as in Synthesis Example 73 was followed to obtain the target compound G-12 (2.8 g, yield 53%).
[LCMS] : 669[LCMS] : 669
[합성예 85] 화합물 H-1의 합성[Synthesis Example 85] Synthesis of compound H-1
준비예 8에서 합성된 화합물 H (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 H-1 (3.7 g, 수율 69 %)을 얻었다.In Preparation Example 8, compound H (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, 24.3 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound H-1 (3.7 g, yield 69%) was obtained using column chromatography.
[LCMS] : 669[LCMS] : 669
[합성예 86] 화합물 H-2의 합성[Synthesis Example 86] Synthesis of compound H-2
합성예 85에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-2 (3.7 g, 수율 69%)을 얻었다.Except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-2 (3.7 g, yield 69%).
[LCMS] : 669[LCMS] : 669
[합성예 87] 화합물 H-3의 합성[Synthesis Example 87] Synthesis of compound H-3
합성예 85에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-3 (3.8 g, 수율 70%)을 얻었다.Except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was performed to obtain the target compound H-3 (3.8 g, yield 70%).
[LCMS] : 669[LCMS] : 669
[합성예 88] 화합물 H-4의 합성[Synthesis Example 88] Synthesis of compound H-4
합성예 85에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-4 (3.6 g, 수율 67%)을 얻었다.Except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was performed to obtain the target compound H-4 (3.6 g, yield 67%).
[LCMS] : 669[LCMS] : 669
[합성예 89] 화합물 H-5의 합성[Synthesis Example 89] Synthesis of compound H-5
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-5 (3.6 g, 수율 67%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was performed to obtain the target compound H-5 (3.6 g, yield 67%).
[LCMS] : 669[LCMS] : 669
[합성예 90] 화합물 H-6의 합성[Synthesis Example 90] Synthesis of compound H-6
합성예 85에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-6 (3.5 g, 수율 65%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-6 (3.5 g, yield 65%).
[LCMS] : 669[LCMS] : 669
[합성예 91] 화합물 H-7의 합성[Synthesis Example 91] Synthesis of compound H-7
합성예 85에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-7 (3.5 g, 수율 65%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-7 (3.5 g, yield 65%).
[LCMS] : 669[LCMS] : 669
[합성예 92] 화합물 H-8의 합성[Synthesis Example 92] Synthesis of compound H-8
합성예 85에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-8 (3.4 g, 수율 62%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-8 (3.4 g, yield 62%).
[LCMS] : 669[LCMS] : 669
[합성예 93] 화합물 H-9의 합성[Synthesis Example 93] Synthesis of compound H-9
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-9 (3.3 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-9 (3.3 g, yield 60%).
[LCMS] : 669[LCMS] : 669
[합성예 94] 화합물 H-10의 합성[Synthesis Example 94] Synthesis of compound H-10
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-10 (2.9 g, 수율 54%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-10 (2.9 g, yield 54%).
[LCMS] : 669[LCMS] : 669
[합성예 95] 화합물 H-11의 합성[Synthesis Example 95] Synthesis of compound H-11
합성예 85에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-11 (2.8 g, 수율 53%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-11 (2.8 g, yield 53%).
[LCMS] : 669[LCMS] : 669
[합성예 96] 화합물 H-12의 합성[Synthesis Example 96] Synthesis of compound H-12
합성예 85에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 85와 동일한 과정을 수행하여 목적 화합물 H-12 (2.8 g, 수율 53%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85, the same procedure as in Synthesis Example 85 was followed to obtain the target compound H-12 (2.8 g, yield 53%).
[LCMS] : 669[LCMS] : 669
[합성예 97] 화합물 I-1의 합성[Synthesis Example 97] Synthesis of Compound I-1
준비예 9에서 합성된 화합물 I (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 I-1 (4.2 g, 수율 78 %)을 얻었다.In Preparation Example 9, compound I (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, 24.3 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound I-1 (4.2 g, yield 78%) was obtained using column chromatography.
[LCMS] : 669[LCMS] : 669
[합성예 98] 화합물 I-2의 합성[Synthesis Example 98] Synthesis of Compound I-2
합성예 97에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-2 (4.1 g, 수율 76%)을 얻었다.Except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-2 (4.1 g, yield 76%).
[LCMS] : 669[LCMS] : 669
[합성예 99] 화합물 I-3의 합성[Synthesis Example 99] Synthesis of Compound I-3
합성예 97에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-3 (4.1 g, 수율 76%)을 얻었다.Except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-3 (4.1 g, yield 76%).
[LCMS] : 669[LCMS] : 669
[합성예 100] 화합물 I-4의 합성[Synthesis Example 100] Synthesis of Compound I-4
합성예 97에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-4 (3.8 g, 수율 70%)을 얻었다.Except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-4 (3.8 g, yield 70%).
[LCMS] : 669[LCMS] : 669
[합성예 101] 화합물 I-5의 합성[Synthesis Example 101] Synthesis of Compound I-5
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-5 (3.6 g, 수율 67%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-5 (3.6 g, yield 67%).
[LCMS] : 669[LCMS] : 669
[합성예 102] 화합물 I-6의 합성[Synthesis Example 102] Synthesis of Compound I-6
합성예 97에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-6 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-6 (3.7 g, yield 68%).
[LCMS] : 669[LCMS] : 669
[합성예 103] 화합물 I-7의 합성[Synthesis Example 103] Synthesis of Compound I-7
합성예 97에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-7 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-7 (3.7 g, yield 68%).
[LCMS] : 669[LCMS] : 669
[합성예 104] 화합물 I-8의 합성[Synthesis Example 104] Synthesis of Compound I-8
합성예 97에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-8 (3.4 g, 수율 62%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-8 (3.4 g, yield 62%).
[LCMS] : 669[LCMS] : 669
[합성예 105] 화합물 I-9의 합성[Synthesis Example 105] Synthesis of Compound I-9
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-9 (3.2 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was followed to obtain the target compound I-9 (3.2 g, yield 60%).
[LCMS] : 669[LCMS] : 669
[합성예 106] 화합물 I-10의 합성[Synthesis Example 106] Synthesis of Compound I-10
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-10 (2.9 g, 수율 54%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was followed to obtain the target compound I-10 (2.9 g, yield 54%).
[LCMS] : 669[LCMS] : 669
[합성예 107] 화합물 I-11의 합성[Synthesis Example 107] Synthesis of Compound I-11
합성예 97에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-11 (3.3 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was performed to obtain the target compound I-11 (3.3 g, yield 60%).
[LCMS] : 669[LCMS] : 669
[합성예 108] 화합물 I-12의 합성[Synthesis Example 108] Synthesis of Compound I-12
합성예 97에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 97과 동일한 과정을 수행하여 목적 화합물 I-12 (2.9 g, 수율 54%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97, the same procedure as in Synthesis Example 97 was followed to obtain the target compound I-12 (2.9 g, yield 54%).
[LCMS] : 669[LCMS] : 669
[합성예 109] 화합물 J-1의 합성[Synthesis Example 109] Synthesis of Compound J-1
준비예 10에서 합성된 화합물 J (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), 및 K2CO3 (3.4 g, 24.3 mmol)을 Toluene 50ml, EtOH 10ml, 및 H2O 10ml에 넣고, 12 시간 동안 가열 환류하였다. 반응 종결 후 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 이용하여 필터링하였다. 필터링된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 J-1 (4.2 g, 수율 78 %)을 얻었다.In Preparation Example 10, compound J (5 g, 8.1 mmol), 2-bromophenanthridine (2.1 g, 8.1 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), and K 2 CO 3 (3.4 g, 24.3 mmol) were added to 50 ml of toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated and refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound J-1 (4.2 g, yield 78%) was obtained using column chromatography.
[LCMS] : 668[LCMS] : 668
[합성예 110] 화합물 J-2의 합성[Synthesis Example 110] Synthesis of compound J-2
합성예 109에서 사용된 2-bromophenanthridine 대신 3-bromophenanthridine을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-2 (4.1 g, 수율 76%)을 얻었다.Except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-2 (4.1 g, yield 76%).
[LCMS] : 668[LCMS] : 668
[합성예 111] 화합물 J-3의 합성[Synthesis Example 111] Synthesis of compound J-3
합성예 109에서 사용된 2-bromophenanthridine 대신 6-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-3 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was performed to obtain the target compound J-3 (3.7 g, yield 68%).
[LCMS] : 668[LCMS] : 668
[합성예 112] 화합물 J-4의 합성[Synthesis Example 112] Synthesis of compound J-4
합성예 109에서 사용된 2-bromophenanthridine 대신 8-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-4 (3.8 g, 수율 70%)을 얻었다.Except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was performed to obtain the target compound J-4 (3.8 g, yield 70%).
[LCMS] : 668[LCMS] : 668
[합성예 113] 화합물 J-5의 합성[Synthesis Example 113] Synthesis of compound J-5
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromophenanthridine 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-5 (3.6 g, 수율 67%)을 얻었다.Except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was performed to obtain the target compound J-5 (3.6 g, yield 67%).
[LCMS] : 668[LCMS] : 668
[합성예 114] 화합물 J-6의 합성[Synthesis Example 114] Synthesis of compound J-6
합성예 109에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-6 (3.7 g, 수율 68%)을 얻었다.Except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-6 (3.7 g, yield 68%).
[LCMS] : 668[LCMS] : 668
[합성예 115] 화합물 J-7의 합성[Synthesis Example 115] Synthesis of compound J-7
합성예 109에서 사용된 2-bromophenanthridine 대신 6-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-7 (3.8 g, 수율 70%)을 얻었다.Except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-7 (3.8 g, yield 70%).
[LCMS] : 668[LCMS] : 668
[합성예 116] 화합물 J-8의 합성[Synthesis Example 116] Synthesis of compound J-8
합성예 109에서 사용된 2-bromophenanthridine 대신 5-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-8 (3.2 g, 수율 60%)을 얻었다.Except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-8 (3.2 g, yield 60%).
[LCMS] : 668[LCMS] : 668
[합성예 117] 화합물 J-9의 합성[Synthesis Example 117] Synthesis of compound J-9
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[h]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-9 (3.2 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-9 (3.2 g, yield 60%).
[LCMS] : 668[LCMS] : 668
[합성예 118] 화합물 J-10의 합성[Synthesis Example 118] Synthesis of compound J-10
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-10 (3.1 g, 수율 54%)을 얻었다.Except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-10 (3.1 g, yield 54%).
[LCMS] : 668[LCMS] : 668
[합성예 119] 화합물 J-11의 합성[Synthesis Example 119] Synthesis of compound J-11
합성예 109에서 사용된 2-bromophenanthridine 대신 9-bromobenzo[f]isoquinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-11 (3.3 g, 수율 60%)을 얻었다.Except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-11 (3.3 g, yield 60%).
[LCMS] : 668[LCMS] : 668
[합성예 120] 화합물 J-12의 합성[Synthesis Example 120] Synthesis of compound J-12
합성예 109에서 사용된 2-bromophenanthridine 대신 2-bromobenzo[f]quinoline 을 사용한 것을 제외하고는, 합성예 109과 동일한 과정을 수행하여 목적 화합물 J-12 (3.0 g, 수율 56%)을 얻었다.Except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109, the same procedure as in Synthesis Example 109 was followed to obtain the target compound J-12 (3.0 g, yield 56%).
[LCMS] : 668[LCMS] : 668
[실시예 1] 청색 유기 전계 발광 소자의 제작[Example 1] Fabrication of a blue organic electroluminescent device
합성예에서 합성된 화합물 A-1를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제작하였다.In the synthetic example, compound A-1 was purified to high purity by sublimation using a commonly known method, and then a blue organic electroluminescent device was produced as follows.
먼저, ITO (Indium tin oxide)가 1500 Å 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 a 1500 Å thick ITO (Indium tin oxide) film was ultrasonically washed in distilled water. After the distilled water washing was completed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자, 80 nm)/NPB (15 nm)/95 wt%의 ADN + 5 wt%의 DS-405(㈜두산전자)(30 nm)/화합물 A-1(30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.On the ITO transparent electrode prepared as described above, an organic electroluminescent device was manufactured by stacking DS-205 (Doosan Electronics Co., Ltd., 80 nm)/NPB (15 nm)/95 wt% of ADN + 5 wt% of DS-405 (Doosan Electronics Co., Ltd.) (30 nm)/compound A-1 (30 nm)/LiF (1 nm)/Al (200 nm) in that order.
이때, 사용된 NPB, ADN의 구조는 각각 하기와 같다.At this time, the structures of NPB and ADN used are as follows.
[실시예 2~120] 청색 유기 전계 발광 소자의 제작[Examples 2-120] Fabrication of blue organic electroluminescent device
실시예 1에서 전자 수송층 물질로 사용된 화합물 A-1 대신 하기 표 1에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds described in Table 1 below was used instead of Compound A-1 used as an electron transport layer material in Example 1.
[비교예 1] 청색 유기 전계 발광 소자의 제작[Comparative Example 1] Fabrication of a Blue Organic Electroluminescent Device
실시예 1에서 전자 수송층 물질로 사용된 화합물 A-1 대신 Alq3을 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때, 사용된 Alq3의 구조는 각각 하기와 같다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3 was used instead of compound A-1 used as an electron transport layer material in Example 1. At this time, the structure of Alq3 used is as follows, respectively.
[비교예 2] 청색 유기 전계 발광 소자의 제작[Comparative Example 2] Fabrication of a Blue Organic Electroluminescent Device
실시예 1에서 전자 수송층 물질로 사용된 화합물 A-1을 사용하지 않은 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that compound A-1, which was used as an electron transport layer material in Example 1, was not used.
[평가예 1][Evaluation Example 1]
실시예 1 내지 120 및 비교예 1~2 에서 제작된 각각의 청색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For each blue organic electroluminescent device manufactured in Examples 1 to 120 and Comparative Examples 1 to 2, the driving voltage, current efficiency, and luminescence peak at a current density of 10 mA/cm2 were measured, and the results are shown in Table 1 below.
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물(A-1~J-12)을 전자 수송층 재료로 사용한 실시예 1~120의 청색 유기 전계 발광 소자는 종래 전자 수송층 재료인 Alq3를 사용한 비교예 1의 청색 유기 전계 발광 소자 및 전자 수송층이 없는 비교예 2의 청색 유기 전계 발광 소자에 비해 구동전압, 발광 피크 및 전류효율 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 120 using the compounds (A-1 to J-12) according to the present invention as electron transport layer materials exhibited better performance in terms of driving voltage, emission peak, and current efficiency than the blue organic electroluminescent device of Comparative Example 1 using Alq 3 as a conventional electron transport layer material and the blue organic electroluminescent device of Comparative Example 2 without an electron transport layer.
Claims (15)
[화학식 1]
(상기 화학식 1에서,
X1 내지 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR2이고, 다만 X1 내지 X3 중 적어도 하나는 N이고, 이때 CR2가 복수인 경우, 복수의 R2는 서로 동일하거나 상이하며,
Y는 O 또는 S이고,
Z1 내지 Z10은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR3이고, 다만 Z1 내지 Z10 중 어느 하나는 N이며, 이때 CR3가 복수인 경우, 복수의 R3는 서로 동일하거나 상이하며,
a 및 b는 각각 1 내지 3의 정수이고,
L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C60의 아릴렌기이며,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되며,
c는 0 내지 4의 정수이고,
R1은 수소이고,
R2 및 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,
상기 L1 및 L2의 아릴렌기, Ar1 및 Ar2의 아릴기 및 헤테로아릴기와, R2 및 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).A compound represented by the following chemical formula 1:
[Chemical Formula 1]
(In the above chemical formula 1,
X 1 to X 3 are identical or different from each other, and are each independently N or CR 2 , provided that at least one of X 1 to X 3 is N, and in this case, when CR 2 is plural, plural R 2 are identical or different from each other,
Y is O or S,
Z 1 to Z 10 are identical or different from each other, and are each independently N or CR 3 , provided that one of Z 1 to Z 10 is N, and in this case, when CR 3 is plural, plural R 3 are identical or different from each other,
a and b are each integers from 1 to 3,
L 1 and L 2 are the same or different from each other, and each independently represents a single bond or an arylene group having C 6 to C 60 ,
Ar 1 and Ar 2 are the same or different from each other, and are each independently selected from the group consisting of an aryl group having C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,
c is an integer from 0 to 4,
R 1 is hydrogen,
R 2 and R 3 are the same or different and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 Selected from the group consisting of an arylboron group, an arylphosphine group having C 6 to C 60 , an arylphosphine oxide group having C 6 to C 60 , and an arylamine group having C 6 to C 60 ,
The arylene group of L 1 and L 2 , the aryl group and heteroaryl group of Ar 1 and Ar 2 , and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R 2 and R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 (wherein the aryl group, the heteroaryl group having 5 to 60 nuclear atoms, the C 1 to C 40 alkyloxy group, the C 6 to C 60 aryloxy group, the C 1 to C 40 alkylsilyl group, the C 6 to C 60 arylsilyl group, the C 1 to C 40 alkylboron group, the C 6 to C 60 arylboron group, the C 6 to C 60 arylphosphine group, the C 6 to C 60 arylphosphine oxide group, and the C 6 to C 60 arylamine group are substituted or unsubstituted with one or more substituents selected from the group consisting of, and wherein when there are plural substituents, they are the same as or different from each other.)
상기 화학식 1에서,
상기 L1 및 L2는
In the above chemical formula 1,
The above L 1 and L 2
상기 화학식 1로 표시되는 화합물은 하기 화학식 2로 표시되는 화합물:
[화학식 2]
(상기 식에서,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 2:
[Chemical formula 2]
(In the above formula,
X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1).
L1은 페닐렌인 화합물.In the first paragraph,
L 1 is a phenylene compound.
상기 화학식 1로 표시되는 화합물은 하기 화학식 3 또는 4로 표시되는 화합물:
[화학식 3]
[화학식 4]
(상기 식에서,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 3 or 4:
[Chemical Formula 3]
[Chemical Formula 4]
(In the above formula,
X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1).
상기 화학식 1로 표시되는 화합물은 하기 화학식 5 내지 7 중 어느 하나로 표시되는 화합물:
[화학식 5]
[화학식 6]
[화학식 7]
(상기 식에서,
X1 내지 X3, Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 5 to 7:
[Chemical Formula 5]
[Chemical formula 6]
[Chemical formula 7]
(In the above formula,
X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1).
X1 내지 X3 중 적어도 2개는 N인 화합물.In the first paragraph,
A compound wherein at least two of X 1 to X 3 are N.
상기 화학식 1로 표시되는 화합물은 하기 화학식 8 또는 9로 표시되는 화합물:
[화학식 8]
[화학식 9]
(상기 식에서,
Y, Z1 내지 Z10, a, b, c, L1, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 8 or 9:
[Chemical formula 8]
[Chemical formula 9]
(In the above formula,
Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in claim 1).
상기 화학식 1로 표시되는 화합물은 하기 화학식 10 내지 15 중 어느 하나로 표시되는 화합물:
[화학식 10]
[화학식 11]
[화학식 12]
[화학식 13]
[화학식 14]
[화학식 15]
(상기 식에서,
Y, Z1 내지 Z10, a, b, c, L2, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 10 to 15:
[Chemical Formula 10]
[Chemical Formula 11]
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
(In the above formula,
Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in Article 1).
상기 화학식 1로 표시되는 화합물은 하기 화학식 16 내지 27 중 어느 하나로 표시되는 화합물:
[화학식 16]
[화학식 17]
[화학식 18]
[화학식 19]
[화학식 20]
[화학식 21]
[화학식 22]
[화학식 23]
[화학식 24]
[화학식 25]
[화학식 26]
[화학식 27]
(상기 식에서,
Y, Z1 내지 Z10, c, Ar1, Ar2, R1은 각각 제1항에서 정의된 바와 같음).In the first paragraph,
The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 16 to 27:
[Chemical Formula 16]
[Chemical Formula 17]
[Chemical Formula 18]
[Chemical Formula 19]
[Chemical formula 20]
[Chemical Formula 21]
[Chemical Formula 22]
[Chemical Formula 23]
[Chemical Formula 24]
[Chemical Formula 25]
[Chemical Formula 26]
[Chemical Formula 27]
(In the above formula,
Y, Z 1 to Z 10 , c, Ar 1 , Ar 2 , R 1 are each as defined in claim 1).
상기 화학식 1에서,
.In the first paragraph,
In the above chemical formula 1,
.
상기 화학식 1에서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기 또는 비페닐기인 화합물.In the first paragraph,
A compound in the above chemical formula 1, wherein Ar 1 and Ar 2 are the same or different and each independently a phenyl group or a biphenyl group.
상기 화학식 1로 표시되는 화합물은 하기 화합물 A-1 내지 A-12, B-1 내지 B-12, C-1 내지 C-12, D-1 내지 D-12, E-1 내지 E-12, F-1 내지 F-12, G-1 내지 G-12, H-1 내지 H-12, I-1 내지 I-12, 및 J-1 내지 J-12로 이루어진 군에서 선택된 화합물:
.In the first paragraph,
The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds A-1 to A-12, B-1 to B-12, C-1 to C-12, D-1 to D-12, E-1 to E-12, F-1 to F-12, G-1 to G-12, H-1 to H-12, I-1 to I-12, and J-1 to J-12:
.
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제13항 중 어느 한 항에 기재된 유기 화합물을 포함하는 유기 전계 발광 소자. An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises an organic compound as described in any one of claims 1 to 13.
상기 유기 화합물을 포함하는 유기물층은 전자 수송층인 유기 전계 발광 소자.In Article 14,
An organic electroluminescent device, wherein the organic layer containing the organic compound is an electron transport layer.
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