KR102633650B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents
Organic compounds and organic electro luminescence device comprising the same Download PDFInfo
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- KR102633650B1 KR102633650B1 KR1020160141054A KR20160141054A KR102633650B1 KR 102633650 B1 KR102633650 B1 KR 102633650B1 KR 1020160141054 A KR1020160141054 A KR 1020160141054A KR 20160141054 A KR20160141054 A KR 20160141054A KR 102633650 B1 KR102633650 B1 KR 102633650B1
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- 150000002894 organic compounds Chemical class 0.000 title description 5
- 238000005401 electroluminescence Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 322
- 230000005525 hole transport Effects 0.000 claims abstract description 22
- 239000011368 organic material Substances 0.000 claims abstract description 19
- 239000010410 layer Substances 0.000 claims description 139
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 125000004429 atom Chemical group 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000004104 aryloxy group Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 36
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- 125000005264 aryl amine group Chemical group 0.000 claims description 36
- 125000005104 aryl silyl group Chemical group 0.000 claims description 36
- 238000002347 injection Methods 0.000 claims description 32
- 239000007924 injection Substances 0.000 claims description 32
- -1 alkylboron group Chemical group 0.000 claims description 31
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 239000012044 organic layer Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005647 linker group Chemical group 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 696
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- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- 230000006872 improvement Effects 0.000 description 10
- 238000004020 luminiscence type Methods 0.000 description 9
- FRIJWEQBTIZQMD-UHFFFAOYSA-N Benzo[c]fluorene Chemical compound C1=CC2=CC=CC=C2C2=C1CC1=CC=CC=C12 FRIJWEQBTIZQMD-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
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- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
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- 125000005842 heteroatom Chemical group 0.000 description 3
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- GJDSGEWWFYYOFU-UHFFFAOYSA-N 1-[1-(9h-carbazol-1-yl)-4-phenylcyclohexa-2,4-dien-1-yl]-9h-carbazole Chemical group C1=CC(C=2C3=C(C4=CC=CC=C4N3)C=CC=2)(C=2C3=C(C4=CC=CC=C4N3)C=CC=2)CC=C1C1=CC=CC=C1 GJDSGEWWFYYOFU-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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Abstract
본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층, 전자 수송층 또는 정공 수송층에 사용됨에 따라 유기 전계 발광 소자의 발광 효율, 구동 전압, 수명 등을 향상시킬 수 있다.The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention is used in an organic material layer, preferably a light-emitting layer, an electron transport layer, or a hole transport layer, to emit light in the organic electroluminescent device. Efficiency, driving voltage, lifespan, etc. can be improved.
Description
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device containing the same.
1950년대 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층 구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Beginning with the observation of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and Tang in 1987. ) presented an organic electroluminescent device with a layered structure divided into a hole layer and a functional layer of the light-emitting layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 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.In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층, 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.To date, NPB, BCP, and Alq 3 are widely known as hole injection layer, hole transport layer, hole blocking layer, and electron transport layer materials, and anthracene derivatives have been reported as light emitting layer materials. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) 3 , and (acac)Ir(btp) 2 , which have advantages in terms of efficiency improvement among light emitting layer materials, produce blue, green, and red colors. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and their thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 정공, 전자 주입 및 수송능, 발광능 등이 모두 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다. The present invention can be applied to organic electroluminescent devices and aims to provide a new organic compound that has excellent hole and electron injection and transport capabilities, luminescence capabilities, etc.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 발광 효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device that includes the novel organic compound, exhibits low driving voltage, high luminous efficiency, and has improved lifespan.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서, In Formula 1,
X는 O, S, Se, N(Ar2), C(Ar3)(Ar4) 및 Si(Ar5)(Ar6)로 구성된 군으로부터 선택되고;X is selected from the group consisting of O, S, Se, N(Ar 2 ), C(Ar 3 )(Ar 4 ) and Si(Ar 5 )(Ar 6 );
환 A 및 B는 각각 독립적으로 각각 독립적으로 C6~C30의 아렌 및 핵원자수 5 내지 30개의 헤테로아렌으로 이루어진 군에서 선택되며;Rings A and B are each independently selected from the group consisting of C 6 to C 30 arenes and heteroarenes with 5 to 30 nuclear atoms;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 is selected from the group consisting of a single bond, an arylene group having C 6 to C 18 and a heteroarylene group having 5 to 18 nuclear atoms;
l 및 o는 각각 독립적으로 0 내지 4의 정수이며;l and o are each independently an integer from 0 to 4;
m 및 n은 각각 독립적으로 0 내지 2의 정수이며;m and n are each independently integers from 0 to 2;
R1 내지 R4는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R1 내지 R4 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 4 are each independently 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 with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 is selected from the group consisting of an arylphosphanyl group, a C 6 ~ C 60 mono or diarylphosphinyl group, and a C 6 ~ C 60 arylamine group, or is combined with an adjacent group to form a condensed ring, and the R 1 to When each of R 4 is plural, they are the same or different from each other;
Ar1 내지 Ar6는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; Ar 1 to Ar 6 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ is selected from the group consisting of a C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylamine group, or is combined with an adjacent group to form a condensed ring;
상기 L1 의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 내지 Ar6 및 R1 내지 R4의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The arylene group and heteroarylene group of L 1 , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, and cycloalkyl group of Ar 1 to Ar 6 and R 1 to R 4 , heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and arylsilyl groups of C 6 to C 60 .
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound of Formula 1. .
본 발명에서의 “알킬”은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다.In the present invention, “alkyl” is a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl. etc., but is not limited to this.
본 발명에서의 “알케닐(alkenyl)”은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다.In the present invention, “alkenyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond, examples of which include vinyl, Examples include allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.
본 발명에서의 “알키닐(alkynyl)”은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다.In the present invention, “alkynyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond, examples of which include ethynyl. , 2-propynyl, etc., but is not limited thereto.
본 발명에서의 “아릴”은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60개일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다.In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a monovalent ring in which two or more rings are condensed with each other, contains only carbon as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule has non-aromaticity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, etc.
본 발명에서의 “헤테로아릴”은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(벤조thiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다.“Heteroaryl” in the present invention refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, contain heteroatoms selected from N, O, P, S, and Se in addition to carbon as ring forming atoms, and the entire molecule is non-aromatic. It is interpreted to include monovalent groups with aromaticity. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polyglycans such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl click hook; Examples include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.
본 발명에서의 “아릴옥시”는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
본 발명에서의 “알킬옥시”는 R’O-로 표시되는 1가의 치환기로, 상기 R’는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.In the present invention, “alkyloxy” is a monovalent substituent represented by R'O-, where R' means 1 to 40 alkyl, and has a linear, branched or cyclic structure. It is interpreted as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
본 발명에서의 “아릴아민”은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다.In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 “시클로알킬”은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.“Cycloalkyl” in the present invention refers to 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 발명에서의 “헤테로시클로알킬”은 핵원자수 3 내지 40개의 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 한정되지 않는다.In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon, preferably 1 to 3 carbons in the ring, is N, O, It is substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.
본 발명에서의 “알킬실릴”은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, “아릴실릴”은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 “축합 고리”는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound represented by Formula 1 of the present invention has excellent thermal stability and luminescence properties, so it can be used as a material for the organic layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, it is possible to manufacture an organic electroluminescent device with excellent light emission performance, low driving voltage, high efficiency, and long lifespan compared to conventional host materials. Full-color display panels with improved performance and lifespan can also be manufactured.
도 1은 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다.
도 2는 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다. Figure 1 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
Figure 2 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. Novel organic compounds
본 발명의 신규 화합물은 하기 화학식 1로 표시될 수 있다:The new compound of the present invention can be represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서, In Formula 1,
X는 O, S, Se, N(Ar2), C(Ar3)(Ar4) 및 Si(Ar5)(Ar6)로 구성된 군으로부터 선택되고;X is selected from the group consisting of O, S, Se, N(Ar 2 ), C(Ar 3 )(Ar 4 ) and Si(Ar 5 )(Ar 6 );
환 A 및 B는 각각 독립적으로 각각 독립적으로 C6~C30의 아렌 및 핵원자수 5 내지 30개의 헤테로아렌으로 이루어진 군에서 선택되며;Rings A and B are each independently selected from the group consisting of C 6 to C 30 arenes and heteroarenes with 5 to 30 nuclear atoms;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 is selected from the group consisting of a single bond, an arylene group having C 6 to C 18 and a heteroarylene group having 5 to 18 nuclear atoms;
l 및 o는 각각 독립적으로 0 내지 4의 정수이며;l and o are each independently an integer from 0 to 4;
m 및 n은 각각 독립적으로 0 내지 2의 정수이며;m and n are each independently integers from 0 to 2;
R1 내지 R4는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R1 내지 R4 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 4 are each independently 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 with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 is selected from the group consisting of an arylphosphanyl group, a C 6 ~ C 60 mono or diarylphosphinyl group, and a C 6 ~ C 60 arylamine group, or is combined with an adjacent group to form a condensed ring, and the R 1 to When each of R 4 is plural, they are the same or different from each other;
Ar1 내지 Ar6는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; Ar 1 to Ar 6 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ is selected from the group consisting of a C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylamine group, or is combined with an adjacent group to form a condensed ring;
상기 L1 의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 내지 Ar6 및 R1 내지 R4의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The arylene group and heteroarylene group of L 1 , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, and cycloalkyl group of Ar 1 to Ar 6 and R 1 to R 4 , heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and arylsilyl groups of C 6 to C 60 .
본 발명에서 제공하는 신규 화합물은 카바졸에 크산텐 모이어티(Xanthene moiety)가 결합되어 기본 골격을 이루며, 구체적으로는 상기 화학식 1로 표시되는 것을 특징으로 한다. 이러한 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-디카바졸릴비페닐(이하, 'CBP'라 함)]보다 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 발광능 등이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 제조 시 사용할 경우, 소자의 구동전압, 효율, 수명 등이 향상될 수 있다.The new compound provided by the present invention forms a basic skeleton by combining carbazole with a xanthene moiety, and is specifically characterized by being represented by the above formula (1). Since the compound represented by Formula 1 has a higher molecular weight than conventional materials for organic electroluminescent devices (e.g., 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')), it has a high glass transition temperature and thus thermal Not only is it excellent in stability, but it is also excellent in carrier transport capacity and luminescence performance. Therefore, when the compound of Formula 1 is used in the manufacture of an organic electroluminescent device, the driving voltage, efficiency, lifespan, etc. of the device can be improved.
일반적으로 유기 전계 발광 소자의 인광 발광층에서, 호스트 물질은 이의 삼중항 에너지 갭이 도펀트의 삼중항 에너지 갭보다 높아야 한다. 즉, 호스트의 가장 낮은 여기 상태가 도펀트의 가장 낮은 방출 상태보다 에너지가 더 높은 경우, 인광 발광 효율이 향상될 수 있다. 본 발명의 상기 화학식 1의 화합물은 삼중항 에너지가 높고, 넓은 일중항 에너지 준위와 높은 삼중항 에너지 준위를 가지는 인돌 유도체가 축합되어 있는 기본 골격에 특정의 치환기가 도입됨으로써, 에너지 준위가 도펀트보다 높게 조절될 수 있어 호스트 물질로 사용될 수 있다.Generally, in the phosphorescent layer of an organic electroluminescent device, the host material must have a triplet energy gap higher than that of the dopant. That is, when the lowest excited state of the host has higher energy than the lowest emission state of the dopant, phosphorescence emission efficiency can be improved. The compound of Formula 1 of the present invention has a high triplet energy, and a specific substituent is introduced into the basic skeleton in which an indole derivative having a wide singlet energy level and a high triplet energy level is condensed, so that the energy level is higher than that of the dopant. It can be controlled and used as a host material.
또한, 본 발명의 화합물은 전술한 바와 같이 높은 삼중항 에너지를 갖기 때문에, 발광층에서 생성된 엑시톤이 발광층에 인접하는 전자 수송층 또는 정공 수송층으로 확산되는 것을 방지할 수 있다. 따라서, 상기 화학식 1의 화합물을 이용하여 정공 수송층과 발광층 사이에 유기물층(이하, '발광 보조층'이라 함)을 형성할 경우, 상기 화합물에 의해서 엑시톤의 확산이 방지되기 때문에, 상기 제1 엑시톤 확산 방지층을 포함하지 않은 종래의 유기 전계 발광 소자와 달리, 실질적으로 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있다. 또한, 상기 화학식 1의 화합물을 이용하여 발광층과 전자 수송층 사이에 유기물층(이하, '수명 개선층'이라 함)을 형성할 경우에도, 상기 화학식 1의 화합물에 의해 엑시톤의 확산이 방지됨으로써, 유기 전계 발광 소자의 내구성 및 안정성이 향상될 수 있고, 이로 인해 소자의 반감 수명이 효율적으로 증가될 수 있다. 이와 같이, 상기 화학식 1로 표시되는 화합물은 발광층의 호스트 이외, 발광 보조층 재료 또는 수명 개선층 재료로 사용될 수 있다.In addition, since the compound of the present invention has high triplet energy as described above, it can prevent excitons generated in the light-emitting layer from diffusing into the electron transport layer or hole transport layer adjacent to the light-emitting layer. Therefore, when an organic material layer (hereinafter referred to as 'light-emitting auxiliary layer') is formed between the hole transport layer and the light-emitting layer using the compound of Formula 1, the diffusion of excitons is prevented by the compound, so the first exciton diffuses. Unlike conventional organic electroluminescent devices that do not include an prevention layer, the number of excitons contributing to light emission in the light-emitting layer is substantially increased, thereby improving the light-emitting efficiency of the device. In addition, even when an organic material layer (hereinafter referred to as 'life improvement layer') is formed between the light emitting layer and the electron transport layer using the compound of Formula 1, diffusion of excitons is prevented by the compound of Formula 1, thereby reducing the organic electric field. The durability and stability of the light emitting device can be improved, and thus the half-life of the device can be efficiently increased. In this way, the compound represented by Formula 1 can be used as a light emitting auxiliary layer material or a lifespan improvement layer material in addition to the host of the light emitting layer.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있어, 넓은 밴드갭을 가질 수 있고, 높은 캐리어 수송성을 가질 수 있다. 예를 들어, 상기 화합물은 상기 기본 골격에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기 등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 양극성(bipolar)의 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있다. 이와 같이, 상기 기본 골격에 EWG가 도입된 상기 화학식 1의 화합물은 우수한 캐리어 수송성 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층 재료 이외, 전자주입/수송층 재료, 또는 수명 개선층 재료로도 사용될 수 있다. 한편, 상기 화학식 1의 화합물이 상기 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에, 발광층 재료 이외, 정공주입/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다.In addition, the compound of Formula 1 can control HOMO and LUMO energy levels depending on the type of substituent introduced into the basic skeleton, can have a wide band gap, and can have high carrier transport. For example, when an electron withdrawing group (EWG) with high electron absorption such as a nitrogen-containing heterocycle (e.g., pyridine group, pyrimidine group, triazine group, etc.) is bonded to the basic skeleton of the compound, the entire molecule is Because it has bipolar characteristics, the binding force between holes and electrons can be increased. As such, the compound of Formula 1 in which EWG is introduced into the basic skeleton has excellent carrier transport properties and excellent light-emitting properties, so it can be used as an electron injection/transport layer material or a lifespan improvement layer material in addition to the light-emitting layer material of an organic electroluminescent device. can be used On the other hand, when the compound of Formula 1 is bonded to the basic skeleton with an electron donating group (EDG) with a large electron donation such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., hole injection and transport are facilitated. Since it is made so that, in addition to the light emitting layer material, it can also be usefully used as a hole injection/transport layer or light emitting auxiliary layer material.
이와 같이, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 발광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 전자 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있다. 따라서, 본 발명에 따른 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(청색, 녹색 및/또는 적색의 인광 호스트 재료), 전자 수송/주입층 재료 및 정공 수송/주입층 재료, 발광 보조층 재료, 수명 개선층 재료, 더 바람직하게는 발광층 재료, 전자 주입층 재료, 발광 보조층 재료, 수명 개선층 재료로 사용될 수 있다.In this way, the compound represented by Formula 1 can improve the luminescence characteristics of the organic electroluminescent device and at the same time improve hole injection/transport ability, electron injection/transport ability, luminous efficiency, driving voltage, lifespan characteristics, etc. . Therefore, the compound of Formula 1 according to the present invention is an organic layer material of an organic electroluminescent device, preferably a light-emitting layer material (blue, green and/or red phosphorescent host material), an electron transport/injection layer material, and a hole transport/injection layer. material, a light emitting auxiliary layer material, a lifespan improvement layer material, and more preferably, a light emitting layer material, an electron injection layer material, a light emitting auxiliary layer material, or a lifespan improvement layer material.
또한, 본 발명의 상기 화학식 1의 화합물은 상기 기본 골격에 다양한 치환기, 특히 아릴기 및/또는 헤테로아릴기가 도입되어 화합물의 분자량이 유의적으로 증대됨으로써, 유리 전이온도가 향상될 수 있고, 이로 인해 종래의 발광 재료(예를 들어, CBP)보다 높은 열적 안정성을 가질 수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에도 효과가 있다. 따라서, 본 발명에 따른 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.In addition, the glass transition temperature of the compound of Formula 1 of the present invention can be improved by significantly increasing the molecular weight of the compound by introducing various substituents, especially aryl groups and/or heteroaryl groups, into the basic skeleton, thereby improving the glass transition temperature. It may have higher thermal stability than conventional light emitting materials (eg, CBP). In addition, the compound represented by Formula 1 is also effective in suppressing crystallization of the organic layer. Therefore, the performance and lifespan characteristics of an organic electroluminescent device containing the compound of Formula 1 according to the present invention can be greatly improved, and the performance of a full-color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.
본 발명의 바람직한 한 구현 예에 따르면, 상기 환 A 및 B는 각각 독립적으로 하기 화학식 2 내지 4 중 어느 하나로 표시될 수 있다:According to a preferred embodiment of the present invention, rings A and B may each independently be represented by any one of the following formulas 2 to 4:
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에서,In Formulas 2 to 4,
점선은 축합이 이루어지는 부분을 의미한다.The dotted line indicates the part where condensation takes place.
본 발명의 바람직한 한 구현 예에 따르면, 상기 환 A 및 B 중 적어도 하나는 상기 화학식 3 또는 4로 표시되는 것이, 구동 전압을 낮추고 발광 효율을 높일 수 있어 바람직하다. According to a preferred embodiment of the present invention, it is preferable that at least one of rings A and B is represented by Formula 3 or 4 because it can lower the driving voltage and increase luminous efficiency.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 5 내지 12 중 어느 하나로 표시될 수 있다. According to a preferred embodiment of the present invention, the compound may be represented by any one of the following formulas 5 to 12.
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
상기 화학식 5 내지 12에서, In Formulas 5 to 12,
X, Ar1, L1, R1, R4, l 및 o 각각은 상기 화학식 1에서 정의된 바와 같다. X, Ar 1 , L 1 , R 1 , R 4 , l and o are each as defined in Formula 1 above.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 특히 상기 화학식 7 내지 12 중 어느 하나로 표시되는 화합물인 것이, 구동 전압을 낮추고 발광 효율을 높일 수 있어 바람직하다. According to a preferred embodiment of the present invention, the compound is preferably a compound represented by any one of Formulas 7 to 12 because it can lower the driving voltage and increase luminous efficiency.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1은 단일결합이거나, 하기 화학식 A-1 내지 화학식 A-3 중 어느 하나로 표시되는 링커일 수 있다:According to a preferred embodiment of the present invention, L 1 may be a single bond or a linker represented by any of the following formulas A-1 to A-3:
상기 화학식 A-1 내지 A-3에서,In the above formulas A-1 to A-3,
*는 결합이 이루어지는 부분을 의미한다.* indicates the part where the combination takes place.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 화학식 13으로 표시되는 치환기일 수 있다:According to a preferred embodiment of the present invention, Ar 1 may be a substituent represented by the following formula (13):
[화학식 13][Formula 13]
상기 화학식 13에서,In Formula 13 above,
*은 결합이 이루어지는 부분을 의미하고;* refers to the part where the combination takes place;
Z1 내지 Z5는 각각 독립적으로 N 또는 C(R5)이며;Z 1 to Z 5 are each independently N or C(R 5 );
R5는 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R5가 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 5 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, nuclear atom Heterocycloalkyl group with 3 to 40 atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, It is selected from the group consisting of a mono or diarylphosphinyl group of C 6 to C 60 and an arylamine group of C 6 to C 60 , or combines with an adjacent group to form a condensed ring, and when there are two or more R 5s , they are the same as each other or different;
상기 R5의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Arylamine group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 is substituted with one or more substituents selected from the group consisting of aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group, and C 6 ~ C 60 arylsilyl group. When unsubstituted and substituted with a plurality of substituents, they are the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R5는 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 5 may be selected from the group consisting of an alkyl group having C 1 to C 30 , an aryl group having C 6 to C 30 , and a heteroaryl group having 5 to 30 nuclear atoms.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R5는 페닐기, 비페닐기, 나프탈레닐기, 피리디닐기, 피리미디닐기 및 트리아지닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 5 may be selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 13으로 표시되는 치환기는 하기 화학식 14로 표시되는 치환기일 수 있다:According to a preferred embodiment of the present invention, the substituent represented by Formula 13 may be a substituent represented by Formula 14 below:
[화학식 14][Formula 14]
상기 화학식 14에서,In Formula 14 above,
*은 결합이 이루어지는 부분을 의미하고;* refers to the part where the combination takes place;
R6 및 R7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 6 and R 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ is selected from the group consisting of a C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylamine group, or is combined with an adjacent group to form a condensed ring;
상기 R6 및 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R 6 and R 7 Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~C 60 arylamine group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~C 40 alkylsilyl group, C 1 ~C 40 alkylboron group, C 6 At least one substituent selected from the group consisting of an aryl boron group of ~C 60 , an arylphosphanyl group of C 6 ~ C 60 , a mono or diarylphosphinyl group of C 6 ~ C 60 , and an arylsilyl group of C 6 ~ C 60 is substituted or unsubstituted, and when substituted with a plurality of substituents, they are the same or different from each other;
Z1, Z3 및 Z5 각각은 상기 화학식 13에서 정의된 바와 같다. Z 1 , Z 3 and Z 5 are each as defined in Formula 13 above.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 화학식 15로 표시되는 치환기일 수 있다:According to a preferred embodiment of the present invention, Ar 1 may be a substituent represented by the following formula (15):
[화학식 15][Formula 15]
상기 화학식 15에서, In Formula 15 above,
*은 결합이 이루어지는 부분을 의미하고;* refers to the part where the combination takes place;
R8 및 R9는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 8 and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ is selected from the group consisting of a C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylamine group, or is combined with an adjacent group to form a condensed ring;
상기 R8 및 R9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다. The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R 8 and R 9 Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~C 60 arylamine group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~C 40 alkylsilyl group, C 1 ~C 40 alkylboron group, C 6 At least one substituent selected from the group consisting of an aryl boron group of ~C 60 , an arylphosphanyl group of C 6 ~ C 60 , a mono or diarylphosphinyl group of C 6 ~ C 60 , and an arylsilyl group of C 6 ~ C 60 When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R8 및 R9는 각각 독립적으로 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 8 and R 9 are each independently selected from the group consisting of an alkyl group of C 1 to C 30 , an aryl group of C 6 to C 30 , and a heteroaryl group of 5 to 30 nuclear atoms. can be selected
본 발명의 바람직한 한 구현 예에 따르면, 상기 R8 및 R9는 각각 독립적으로 페닐기, 비페닐기, 나프탈레닐기 및 플루오레닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 8 and R 9 may each be independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, and a fluorenyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 화학식 B-1 내지 B-8 중 어느 하나로 표시되는 치환기일 수 있다:According to a preferred embodiment of the present invention, Ar 1 may be a substituent represented by any one of the following formulas B-1 to B-8:
상기 화학식 B-1 내지 B-8에서, In the above formulas B-1 to B-8,
*은 결합이 이루어지는 부분을 의미하고;* refers to the part where the combination takes place;
Z5 내지 Z12는 각각 독립적으로 N 또는 C(R12)이며;Z 5 to Z 12 are each independently N or C(R 12 );
상기 화학식 B-1에서 L1에 결합되는 Z5 내지 Z8 중 어느 하나는 C(R12)이고, 이때 상기 R12는 부재이며;In Formula B-1, any one of Z 5 to Z 8 bonded to L 1 is C(R 12 ), wherein R 12 is absent;
T1 및 T2는 각각 독립적으로 단일결합, C(R13)(R14), N(R15), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;T 1 and T 2 are each independently selected from the group consisting of a single bond, C(R 13 )(R 14 ), N(R 15 ), O, and S, but both T 1 and T 2 are not a single bond;
q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers from 0 to 4;
R10 및 R11은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R10 및 R11 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 and R 11 are each independently selected from 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 6 to C 60 Aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C 6 ~ C 60 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 may be selected from the group consisting of an arylphosphanyl group, a C 6 ~ C 60 mono or diarylphosphinyl group, and a C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and the R When each of 10 and R 11 is plural, they are the same or different from each other;
R12 내지 R15는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R12 내지 R15 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 to R 15 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 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, 3 nuclear atoms to 40 heterocycloalkyl groups, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to It may be selected from the group consisting of C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group, and C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, When each of R 12 to R 15 is plural, they are the same or different from each other;
상기 R10 내지 R15의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R 10 to R 15 Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~C 60 arylamine group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~C 40 alkylsilyl group, C 1 ~C 40 alkylboron group, C 6 At least one substituent selected from the group consisting of an aryl boron group of ~C 60 , an arylphosphanyl group of C 6 ~ C 60 , a mono or diarylphosphinyl group of C 6 ~ C 60 , and an arylsilyl group of C 6 ~ C 60 When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 화학식 C-1 내지 C-14 중 어느 하나로 표시되는 치환기일 수 있다:According to a preferred embodiment of the present invention, Ar 1 may be a substituent represented by any one of the following formulas C-1 to C-14:
상기 화학식 C-1 내지 C-14에서, In the above formulas C-1 to C-14,
*은 결합이 이루어지는 부분을 의미하고;* refers to the part where the combination takes place;
q, r 및 s는 각각 독립적으로 0 내지 4의 정수이며;q, r and s are each independently integers from 0 to 4;
R10, R11 및 R16은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R10, R11 및 R18 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 , R 11 and R 16 are each independently selected from 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 6 ~C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 It is selected from the group consisting of an arylphosphanyl group of ~C 60 , a mono or diarylphosphinyl group of C 6 ~C 60 , and an arylsilyl group of C 6 ~C 60 , or may be combined with an adjacent group to form a condensed ring. , when each of R 10 , R 11 and R 18 is plural, they are the same or different from each other;
R12 내지 R15는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 12 to R 15 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 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, 3 nuclear atoms to 40 heterocycloalkyl groups, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to It may be selected from the group consisting of a C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring;
상기 R10 내지 R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R 10 to R 16 Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~C 60 arylamine group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~C 40 alkylsilyl group, C 1 ~C 40 alkylboron group, C 6 At least one substituent selected from the group consisting of an aryl boron group of ~C 60 , an arylphosphanyl group of C 6 ~ C 60 , a mono or diarylphosphinyl group of C 6 ~ C 60 , and an arylsilyl group of C 6 ~ C 60 When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 내지 R16은 각각 독립적으로 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 10 to R 16 are each independently selected from the group consisting of a C 1 to C 30 alkyl group, a C 6 to C 30 aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. can be selected
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 내지 R16은 각각 독립적으로 페닐기, 비페닐기 및 나프탈레닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 10 to R 16 may each be independently selected from the group consisting of a phenyl group, a biphenyl group, and a naphthalenyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R13 및 R14는 각각 독립적으로 수소, C1~C30의 알킬기 및 C6~C30의 아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 13 and R 14 may each independently be selected from the group consisting of hydrogen, a C 1 to C 30 alkyl group, and a C 6 to C 30 aryl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R13 및 R14는 각각 독립적으로 수소, 메틸기, 에틸기, 부틸기 및 페닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 13 and R 14 may each independently be selected from the group consisting of hydrogen, methyl group, ethyl group, butyl group, and phenyl group.
본 발명의 화학식 1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나 이에 한정되는 것은 아니다: The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev ., 60:313 (1960); J. Chem . SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.
The compound of Formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 :313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ), etc.). The detailed synthesis process for the compound of the present invention will be described in detail in the synthesis examples described later.
2. 유기 2. Organic 전계electric field 발광 소자 light emitting element
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) containing the compound represented by Formula 1 according to the above-described present invention.
구체적으로, 본 발명은 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2 이상 혼합되어 사용될 수 있다.Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is It includes a compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 수명 개선층, 전자 수송층, 전자 수송 보조층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic material layers has the formula above. It may include a compound represented by 1.
전술한 본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 일 예시로 도 1을 참고하면, 예컨대 서로 마주하는 양극(10)과 음극(20), 그리고 상기 양극(10)과 음극(20) 사이에 위치하는 유기층(30)을 포함한다. 여기서, 상기 유기층(30)은 정공 수송층(31), 발광층(32) 및 전자 수송층(34)을 포함할 수 있다. 또한, 상기 정공 수송층(31)과 발광층(32) 사이에는 정공 수송 보조층(33)을 포함할 수 있으며, 상기 전자 수송층(34)과 발광층(32) 사이에는 전자 수송 보조층(35)을 포함할 수 있다. The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, but referring to Figure 1 as an example, for example, an anode 10 and a cathode 20 facing each other, and the anode 10 and the cathode ( 20) and includes an organic layer 30 located between them. Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
본 발명의 다른 예시로 도 2를 참고하면, 상기 유기층(30)은 정공 수송층(31)과 양극(10)사이에 정공 주입층(37)을 더 포함할 수 있으며, 전자 수송층(34)과 음극(20)사이에는 전자 주입층(36)을 추가로 더 포함할 수 있다. Referring to FIG. 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode. An electron injection layer 36 may be further included between (20).
본 발명에서 상기 정공 수송층(31)과 양극(10) 사이에 적층되는 정공 주입층(37)은 양극으로 사용되는 ITO와, 정공 수송층(31)으로 사용되는 유기물질 사이의 계면 특성을 개선할 뿐만 아니라 그 표면이 평탄하지 않은 ITO의 상부에 도포되어 ITO의 표면을 부드럽게 만들어주는 기능을 하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, 아민 화합물을 사용할 수 있으나 이에 한정되는 것은 아니다.In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 not only improves the interface characteristics between ITO used as the anode and the organic material used as the hole transport layer 31. Rather, it is a layer that is applied on top of the ITO, which has an uneven surface, and functions to smooth the surface of the ITO. It can be used without particular restrictions as long as it is commonly used in the art. For example, an amine compound can be used. It is not limited to this.
또한, 상기 전자 주입층(36)은 전자 수송층의 상부에 적층되어 음극으로부터의 전자 주입을 용이하게 해주어 궁극적으로 전력효율을 개선시키는 기능을 수행하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, LiF, Liq, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다. In addition, the electron injection layer 36 is a layer that is laminated on the top of the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. It is a special layer that is commonly used in the art. It can be used without limitation, and for example, materials such as LiF, Liq, NaCl, CsF, Li 2 O, BaO, etc. can be used.
또한, 본 발명에서 도면에는 도시하지 않았으나, 상기 정공 수송 보조층(33)과 발광층(32) 사이에 발광 보조층을 더 포함할 수 있다. 상기 발광 보조층은 발광층(32)에 정공을 수송하는 역할을 하면서 유기층(30)의 두께를 조정하는 역할을 할 수 있다. 상기 발광 보조층은 정공 수송 물질을 포함할 수 있고, 정공 수송층(31)과 동일한 물질로 만들어질 수 있다.In addition, although not shown in the drawings, in the present invention, a light-emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light-emitting layer 32. The light-emitting auxiliary layer may serve to transport holes to the light-emitting layer 32 and adjust the thickness of the organic layer 30. The light emitting auxiliary layer may include a hole transport material and may be made of the same material as the hole transport layer 31.
또한, 본 발명에서 도면에는 도시하지 않았으나, 상기 전자 수송 보조층 (35)과 발광층(32) 사이에 수명 개선층을 더 포함할 수 있다. 상기 발광층(32)으로 유기 발광 소자 내에서 이온화 포텐셜 레벨을 타고 이동하는 정공이 수명개선층의 높은 에너지 장벽에 막혀 전자 수송층으로 확산, 또는 이동하지 못해, 결과적으로 정공을 발광층에 제한시키는 기능을 한다. 이렇게 정공을 발광층에 제한시키는 기능은 환원에 의해 전자를 이동시키는 전자 수송층으로 정공이 확산되는 것을 막아, 산화에 의한 비가역적 분해반응을 통한 수명저하 현상을 억제하여, 유기 발광 소자의 수명 개선에 기여할 수 있다.In addition, although not shown in the drawings, in the present invention, a lifespan improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes moving through the ionization potential level in the organic light-emitting device to the light-emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer and cannot diffuse or move to the electron transport layer, thereby limiting the holes to the light-emitting layer. . This function of limiting holes to the light-emitting layer prevents holes from diffusing into the electron transport layer, which moves electrons through reduction, and suppresses the phenomenon of lifespan reduction through irreversible decomposition reactions due to oxidation, contributing to improving the lifespan of organic light-emitting devices. You can.
본 발명에서 제공하는 신규 화합물은 카바졸에 크산텐 모이어티(Xanthene moiety)가 결합되어 기본 골격을 이루며, 구체적으로는 상기 화학식 1로 표시되는 것을 특징으로 한다. 이러한 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-디카바졸릴비페닐(이하, 'CBP'라 함)]보다 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 발광능 등이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 제조 시 사용할 경우, 소자의 구동전압, 효율, 수명 등이 향상될 수 있다. The new compound provided by the present invention forms a basic skeleton by combining carbazole with a xanthene moiety, and is specifically characterized by being represented by the above formula (1). Since the compound represented by Formula 1 has a higher molecular weight than conventional materials for organic electroluminescent devices (e.g., 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')), it has a high glass transition temperature and thus thermal Not only is it excellent in stability, but it is also excellent in carrier transport capacity and luminescence performance. Therefore, when the compound of Formula 1 is used in the manufacture of an organic electroluminescent device, the driving voltage, efficiency, lifespan, etc. of the device can be improved.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있어, 넓은 밴드갭을 가질 수 있고, 높은 캐리어 수송성을 가질 수 있다. 예를 들어, 상기 화합물은 상기 기본 골격에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기 등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 양극성(bipolar)의 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있다. 이와 같이, 상기 기본 골격에 EWG가 도입된 상기 화학식 1의 화합물은 우수한 캐리어 수송성 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층 재료 이외, 전자주입/수송층 재료, 또는 수명 개선층 재료로도 사용될 수 있다. 한편, 상기 화학식 1의 화합물이 상기 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에, 발광층 재료 이외, 정공주입/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다.In addition, the compound of Formula 1 can control HOMO and LUMO energy levels depending on the type of substituent introduced into the basic skeleton, can have a wide band gap, and can have high carrier transport. For example, when an electron withdrawing group (EWG) with high electron absorption such as a nitrogen-containing heterocycle (e.g., pyridine group, pyrimidine group, triazine group, etc.) is bonded to the basic skeleton of the compound, the entire molecule is Because it has bipolar characteristics, the bonding force between holes and electrons can be increased. As such, the compound of Formula 1 in which EWG is introduced into the basic skeleton has excellent carrier transport properties and excellent light-emitting properties, so it can be used as an electron injection/transport layer material or a lifespan improvement layer material in addition to the light-emitting layer material of an organic electroluminescent device. can be used On the other hand, when the compound of Formula 1 is bonded to the basic skeleton with an electron donating group (EDG) with a large electron donation such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., hole injection and transport are facilitated. Since it is made so that, in addition to the light emitting layer material, it can also be usefully used as a hole injection/transport layer or light emitting auxiliary layer material.
이와 같이, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 발광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 전자 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있다. 따라서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택되는 것이 바람직하며, 보다 바람직하게는 발광층, 전자 수송층 또는 정공 수송층일 수 있다.In this way, the compound represented by Formula 1 can improve the luminescence characteristics of the organic electroluminescent device and at the same time improve hole injection/transport ability, electron injection/transport ability, luminous efficiency, driving voltage, lifespan characteristics, etc. . Therefore, the organic layer containing the compound represented by Formula 1 is preferably selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, and an electron injection layer, and more preferably a light-emitting layer and an electron injection layer. It may be a transport layer or a hole transport layer.
또한, 본 발명에 따른 화합물을 발광층 재료로 사용하는 경우, 구체적으로는 상기 화학식 1로 표시되는 화합물을 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료로 사용할 수 있으며, 바람직하게는 인광 호스트(청색, 녹색 및/또는 적색의 인광 호스트 재료)로 사용할 수 있다.In addition, when using the compound according to the present invention as a light-emitting layer material, specifically, the compound represented by Formula 1 can be used as a phosphorescent host, fluorescent host, or dopant material of the light-emitting layer, preferably a phosphorescent host (blue, green) and/or a red phosphorescent host material).
또한, 본 발명에서 상기 유기 전계 발광 소자는 상기한 바와 같이 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층을 추가로 포함할 수 있다. In addition, in the present invention, the organic electroluminescent device not only includes an anode, one or more organic material layers, and a cathode sequentially stacked as described above, but may additionally include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 적어도 하나 이상(예컨대, 전자 수송 보조층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic layers (e.g., electron transport auxiliary layer) includes the compound represented by Formula 1 above. It can be manufactured by forming other organic layers and electrodes.
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 한정되지 않는다.The organic material layer may be formed by vacuum deposition or solution application. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.There is no particular limitation on the substrate that can be used in the present invention, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.
또, 양극 물질로는 예컨대 정공 주입이 원활하도록 일 함수가 높은 도전체로 만들어질 수 있으며, 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 있으나, 이에 한정되지는 않는다.In addition, the anode material may be made of, for example, a conductor with a high work function to facilitate hole injection, and may include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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, but are not limited thereto.
또, 음극 물질로는 예컨대 전자 주입이 원활하도록 일 함수가 낮은 도전체로 만들어질 수 있으며, 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 있으나, 이에 한정되지는 않는다.
In addition, the cathode material can be made of a conductor with a low work function to facilitate electron injection, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. Same metals or alloys thereof; and multilayer structure materials such as LiF/Al or LiO 2 /Al, etc., but are not limited thereto.
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 only illustrate the present invention, and the present invention is not limited by the following examples.
[준비예 1][Preparation example 1]
3-(스피로[플루오렌-9,9'-크산텐]-3-일)-9H-카바졸의 합성Synthesis of 3-(spiro[fluorene-9,9'-xanthene]-3-yl)-9H-carbazole
14,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-크산텐]-3-일)-1,3,2-디옥사보로란 10g(21.8mmol)과 3-브로모-9H-카바졸 4.47g (18.18mmol)에 자일렌 250 mL를 가하였다. Pd(PPh3)4 1.25g (1.09mmol), K2CO3 7.53g (54.5mmol)을 첨가 후 120℃에서 24시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 7.4g(수율 82%)을 얻었다. 10 g (21.8 mmol) of 14,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthene]-3-yl)-1,3,2-dioxabororane 250 mL of xylene was added to 4.47 g (18.18 mmol) of 3-bromo-9H-carbazole. Pd( PPh3 ) 4 1.25 g (1.09 mmol) and 7.53 g (54.5 mmol) of K 2 CO 3 were added and heated and refluxed at 120°C for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated by adding 500 mL of ammonium chloride aqueous solution to the reaction solution. The mixed solution was extracted with 500 mL of MC and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 7.4 g of the target compound (yield 82%).
1H-NMR: δ 11.66 (br, 1H), 8.19~8.18(m, 2H), 7.99~7.90(m, 3H), 7.77~7.5(m, 5H), 7.31~7.17(m, 9H), 7.01(m, 2H); 1 H-NMR: δ 11.66 (br, 1H), 8.19~8.18(m, 2H), 7.99~7.90(m, 3H), 7.77~7.5(m, 5H), 7.31~7.17(m, 9H), 7.01 (m, 2H);
GC-Mass (이론치: 497.60 g/mol, 측정치: 497.18 g/mol)
GC-Mass (theoretical value: 497.60 g/mol, measured value: 497.18 g/mol)
[준비예 2][Preparation example 2]
3-(스피로[플루오렌-9,9'-크산텐]-2-일)-9H-카바졸의 합성Synthesis of 3-(spiro[fluorene-9,9'-xanthene]-2-yl)-9H-carbazole
반응물로 14,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-크산텐]-2-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 497.18
Except for using 14,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthene]-2-yl)-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 6.9 g of the target compound; HRMS [M]+: 497.18
[준비예 3][Preparation example 3]
3-(스피로[플루오렌-9,9'-티오크산텐]-3-일)-9H-카바졸의 합성Synthesis of 3-(spiro[fluorene-9,9'-thioxanthene]-3-yl)-9H-carbazole
반응물로 4,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-티오크산텐]-3-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 513.66
4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-thioxanthene]-3-yl)-1,3,2-dioxabororane was used as a reactant. The same process as [Preparation Example 1] was performed except that 6.5 g of the target compound was obtained; HRMS [M]+: 513.66
[준비예 4][Preparation example 4]
3-(스피로[플루오렌-9,9'-티오크산텐]-2-일)-9H-카바졸의 합성Synthesis of 3-(spiro[fluorene-9,9'-thioxanthene]-2-yl)-9H-carbazole
반응물로 4,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-티오크산텐]-2-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 513.66
4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-thioxanthene]-2-yl)-1,3,2-dioxabororane was used as a reactant. The same procedure as in [Preparation Example 1] was performed except that 7.1 g of the target compound was obtained; HRMS [M]+: 513.66
[준비예 5][Preparation example 5]
3'-(9H-카바졸-3-일)-10-페닐-10H-스피로[아크리딘-9,9'-플루오렌]의 합성Synthesis of 3'-(9H-carbazol-3-yl)-10-phenyl-10H-spiro[acridine-9,9'-fluorene]
반응물로 10-페닐-3'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,9'-플루오렌]을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.7g을 얻었다.; HRMS [M]+: 572.71
As a reactant, 10-phenyl-3'-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-10H-spiro[acridine-9,9' -Fluorene] was used, and the same process as [Preparation Example 1] was performed to obtain 7.7 g of the target compound; HRMS [M]+: 572.71
[준비예 6][Preparation example 6]
3'-(9H-카바졸-3-일)-10-페닐-10H-스피로[아크리딘-9,9'-플루오렌]의 합성Synthesis of 3'-(9H-carbazol-3-yl)-10-phenyl-10H-spiro[acridine-9,9'-fluorene]
반응물로 10-페닐-2'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,9'-플루오렌]을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 572.71
As a reactant, 10-phenyl-2'-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-10H-spiro[acridine-9,9' -Fluorene] was used, and the same process as [Preparation Example 1] was performed to obtain 7.0 g of the target compound; HRMS [M]+: 572.71
[준비예 7][Preparation example 7]
10-(스피로[플루오렌-9,9'-크산텐]-3-일)-7H-벤조[c]카바졸의 합성Synthesis of 10-(spiro[fluorene-9,9'-xanthene]-3-yl)-7H-benzo[c]carbazole
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 547.66
The same procedure as [Preparation Example 1] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.0 g of the target compound; HRMS [M]+: 547.66
[준비예 8][Preparation example 8]
10-(스피로[플루오렌-9,9'-크산텐]-2-일)-7H-벤조[c]카바졸의 합성Synthesis of 10-(spiro[fluorene-9,9'-xanthene]-2-yl)-7H-benzo[c]carbazole
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 2]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 547.66
The same procedure as [Preparation Example 2] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.2 g of the target compound; HRMS [M]+: 547.66
[준비예 9][Preparation example 9]
3-(스피로[플루오렌-9,9'-티오크산텐]-3-일)-9H-벤조[c]카바졸의 합성Synthesis of 3-(spiro[fluorene-9,9'-thioxanthene]-3-yl)-9H-benzo[c]carbazole
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 3]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 563.72
The same procedure as [Preparation Example 3] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.1 g of the target compound; HRMS [M]+: 563.72
[준비예 10][Preparation example 10]
3-(스피로[플루오렌-9,9'-티오크산텐]-2-일)-9H-벤조[c]카바졸의 합성Synthesis of 3-(spiro[fluorene-9,9'-thioxanthene]-2-yl)-9H-benzo[c]carbazole
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 4]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 563.72
The same procedure as [Preparation Example 4] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.0 g of the target compound; HRMS [M]+: 563.72
[준비예 11][Preparation example 11]
3'-(7H-3'-(7H- 벤조[c]카바졸Benzo[c]carbazole -10-일)-10-페닐-10H--10-yl)-10-phenyl-10H- 스피로[아크리딘-9,9'-플루오렌]의Spiro[acridine-9,9'-fluorene] 합성 synthesis
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 5]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 622.77
The same procedure as [Preparation Example 5] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.8 g of the target compound; HRMS [M]+: 622.77
[준비예 12][Preparation example 12]
3'-(9H-3'-(9H- 벤조[c]카바졸Benzo[c]carbazole -3-일)-10-페닐-10H--3-yl)-10-phenyl-10H- 스피로[아크리딘-9,9'-플루오렌]의Spiro[acridine-9,9'-fluorene] 합성 synthesis
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 6]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 622.77
The same procedure as [Preparation Example 6] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.5 g of the target compound; HRMS [M]+: 622.77
[준비예 13][Preparation example 13]
3-(스피로[벤조[c]플루오렌-7,9'-크산텐]-10-일)-9H-카바졸의 합성Synthesis of 3-(spiro[benzo[c]fluorene-7,9'-xanthene]-10-yl)-9H-carbazole
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-크산텐]-10-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 547.66
4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-10-yl)-1,3,2-dioxabororane as reactant The same process as [Preparation Example 1] was performed except that 6.6 g of the target compound was obtained; HRMS [M]+: 547.66
[준비예 14][Preparation example 14]
3-(스피로[벤조[c]플루오렌-7,9'-크산텐]-9-일)-9H-카바졸의 합성Synthesis of 3-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-9H-carbazole
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-크산텐]-9-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 2]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 547.66
As a reactant, 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxabororane The same process as [Preparation Example 2] was performed except that 6.4 g of the target compound was obtained; HRMS [M]+: 547.66
[준비예 15][Preparation example 15]
3-(스피로[벤조[c]플루오렌-7,9'-티오크산텐]-10-일)-9H-카바졸의 합성Synthesis of 3-(spiro[benzo[c]fluorene-7,9'-thioxanthene]-10-yl)-9H-carbazole
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-티오크산텐]-10-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 3]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 563.72
4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-thioxanthene]-10-yl)-1,3,2-dioxaboro as reactant The same process as [Preparation Example 3] was performed except that eggs were used, and 6.9 g of the target compound was obtained; HRMS [M]+: 563.72
[준비예 16][Preparation example 16]
3-(스피로[벤조[c]플루오렌-7,9'-티오크산텐]-9-일)-9H-카바졸의 합성Synthesis of 3-(spiro[benzo[c]fluorene-7,9'-thioxanthene]-9-yl)-9H-carbazole
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-티오크산텐]-9-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 4]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 563.72
4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-thioxanthene]-9-yl)-1,3,2-dioxaboro as reactant The same process as [Preparation Example 4] was performed except that eggs were used to obtain 7.5 g of the target compound; HRMS [M]+: 563.72
[준비예 17][Preparation example 17]
10'-(9H-10'-(9H- 카바졸Carbazole -3-일)-10-페닐-10H--3-yl)-10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플루오렌]의Spiro[acridine-9,7'-benzo[c]fluorene] 합성 synthesis
반응물로 10-페닐-10'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,7'-벤조[c]플루오렌]을 사용한 것을 제외하고는 [준비예 5]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 622.77
As a reactant, 10-phenyl-10'-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-10H-spiro[acridine-9,7' -7.8g of the target compound was obtained by performing the same process as [Preparation Example 5] except that benzo[c]fluorene] was used; HRMS [M]+: 622.77
[준비예 18][Preparation example 18]
9'-(9H-9'-(9H- 카바졸Carbazole -3-일)-10-페닐-10H--3-yl)-10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플루오렌]의Spiro[acridine-9,7'-benzo[c]fluorene] 합성 synthesis
반응물로 10-페닐-9'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,7'-벤조[c]플루오렌]을 사용한 것을 제외하고는 [준비예 6]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 622.77
As a reactant, 10-phenyl-9'-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-10H-spiro[acridine-9,7' -7.5 g of the target compound was obtained by performing the same process as [Preparation Example 6] except that benzo[c]fluorene] was used; HRMS [M]+: 622.77
[준비예 19][Preparation example 19]
10-(스피로[벤조[c]플루오렌-7,9'-크산텐]-10-일)-7H-벤조[c]카바졸의 합성Synthesis of 10-(spiro[benzo[c]fluorene-7,9'-xanthene]-10-yl)-7H-benzo[c]carbazole
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 13]과 동일한 과정을 수행하여 목적 화합물 7.59g을 얻었다.; HRMS [M]+: 597.72
The same procedure as [Preparation Example 13] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.59 g of the target compound; HRMS [M]+: 597.72
[준비예 20][Preparation example 20]
10-(스피로[벤조[c]플루오렌-7,9'-크산텐]-9-일)-7H-벤조[c]카바졸의 합성Synthesis of 10-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-7H-benzo[c]carbazole
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 14]과 동일한 과정을 수행하여 목적 화합물 7.9g을 얻었다.; HRMS [M]+: 597.72
The same procedure as [Preparation Example 14] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.9 g of the target compound; HRMS [M]+: 597.72
[[ 준비예Preparation example 21] 21]
10-(10-( 스피로spiro [[ 벤조[c]플루오렌Benzo[c]fluorene -7,9'--7,9'- 티오크산텐thioxanthen ]-10-일)-7H-]-10-day)-7H- 벤조[c]카바졸의Benzo[c]carbazole 합성 synthesis
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 15]과 동일한 과정을 수행하여 목적 화합물 8.0g을 얻었다.; HRMS [M]+: 613.78
The same procedure as [Preparation Example 15] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 8.0 g of the target compound; HRMS [M]+: 613.78
[[ 준비예Preparation example 22] 22]
10-(10-( 스피로spiro [[ 벤조[c]플루오렌Benzo[c]fluorene -7,9'--7,9'- 티오크산텐thioxanthen ]-9-일)-7H-]-9-day)-7H- 벤조[c]카바졸의Benzo[c]carbazole 합성 synthesis
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 16]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 613.78
The same procedure as [Preparation Example 16] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.6 g of the target compound; HRMS [M]+: 613.78
[[ 준비예Preparation example 23] 23]
10'-(7H-10'-(7H- 벤조[c]카바졸Benzo[c]carbazole -10-일)-10-페닐-10H--10-yl)-10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플루오렌]의Spiro[acridine-9,7'-benzo[c]fluorene] 합성 synthesis
10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 17]과 동일한 과정을 수행하여 목적 화합물 7.9g을 얻었다.; HRMS [M]+: 672.83
The same procedure as [Preparation Example 17] was performed except that 10-bromo-7H-benzo[c]carbazole was used to obtain 7.9 g of the target compound; HRMS [M]+: 672.83
[[ 준비예Preparation example 24] 24]
9'-(7H-9'-(7H- 벤조[c]카바졸Benzo[c]carbazole -10-일)-10-페닐-10H--10-yl)-10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플루오렌]의Spiro[acridine-9,7'-benzo[c]fluorene] 합성 synthesis
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 18]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 672.83
The same procedure as [Preparation Example 18] was performed except that 10-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 7.5 g of the target compound; HRMS [M]+: 672.83
[[ 합성예Synthesis example 1] One] MatMat 1의 합성 synthesis of 1
준비예 1 5g (10.04mmol)과 3-요오드-1,1'-비페닐 3.37g (12.04mmol)에 자일렌 250 mL를 가하였다. Pd2(dba)3 0.45g (0.5mmol), Xphos 0.47g (1mmol), NaOtBu 2.4g (25.1mol)을 첨가 후 120℃에서 24시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 5.6g (수율 86%)을 얻었다. Preparation Example 1 250 mL of xylene was added to 5 g (10.04 mmol) of 3-iodine-1,1'-biphenyl and 3.37 g (12.04 mmol) of 3-iodine-1,1'-biphenyl. After adding 0.45 g (0.5 mmol) of Pd 2 (dba) 3 , 0.47 g (1 mmol) of Xphos, and 2.4 g (25.1 mol) of NaOtBu, the mixture was heated and refluxed at 120°C for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated by adding 500 mL of ammonium chloride aqueous solution to the reaction solution. The mixed solution was extracted with 500 mL of MC and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 5.6 g of the target compound (yield 86%).
1H-NMR: δ 8.3 (d, 1H), 8.21~8.13(m, 4H), 7.90~7.89(m, 2H), 7.68~7.17(m, 22H), 7.01(m, 2H); HRMS [M]+: 649.79
1 H-NMR: δ 8.3 (d, 1H), 8.21-8.13 (m, 4H), 7.90-7.89 (m, 2H), 7.68-7.17 (m, 22H), 7.01 (m, 2H); HRMS [M] + : 649.79
[[ 합성예Synthesis example 2] 2] MatMat 2의 합성 Composition of 2
반응물로 4-요오드-1,1'-비페닐을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 649.79
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that 4-iodine-1,1'-biphenyl was used as a reactant; HRMS [M]+: 649.79
[[ 합성예Synthesis example 3] 3] MatMat 5의 합성 synthesis of 5
반응물로 2-브로모트리페닐렌을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 723.88
The same process as [Synthesis Example 1] was performed except that 2-bromotriphenylene was used as a reactant to obtain 6.7 g of the target compound; HRMS [M]+: 723.88
[[ 합성예Synthesis example 4] 4] MatMat 7의 합성 Composition of 7
반응물로 요오드벤젠을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 573.70
The same process as [Synthesis Example 1] was performed except that iodobenzene was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 573.70
[[ 합성예Synthesis example 5] 5] MatMat 8의 합성 Composition of 8
반응물로 2-브로모디벤조[b,d]퓨란을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 663.78
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that 2-bromodibenzo[b,d]furan was used as a reactant; HRMS [M]+: 663.78
[[ 합성예Synthesis example 6] 6] MatMat 13의 합성 Composition of 13
반응물로 4-브로모디벤조[b,d]퓨란을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 663.78
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that 4-bromodibenzo[b,d]furan was used as a reactant; HRMS [M]+: 663.78
[[ 합성예Synthesis example 7] 7] MatMat 20의 합성 combination of 20
반응물로 2-클로로-4,6-디페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 728.86
The same procedure as [Synthesis Example 1] was performed except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used as a reactant to obtain 4.5 g of the target compound; HRMS [M]+: 728.86
[[ 합성예Synthesis example 8] 8] MatMat 21의 합성 Composition of 21
반응물로 2-([1,1'-비페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 804.95
Same process as [Synthesis Example 1] except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used as a reactant. was performed to obtain 5.7g of the target compound; HRMS [M]+: 804.95
[[ 합성예Synthesis example 9] 9] MatMat 23의 합성 Composition of 23
반응물로 4-([1,1'-비페닐]-4-일)-6-클로로-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 803.97
The same procedure as [Synthesis Example 1] was performed except that 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine was used as a reactant, and 4.8 g of the target compound was obtained. got; HRMS [M]+: 803.97
[[ 합성예Synthesis example 10] 10] MatMat 24의 합성 Composition of 24
반응물로 2-클로로-4-페닐퀴나졸린을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 701.83
The same process as [Synthesis Example 1] was performed except that 2-chloro-4-phenylquinazoline was used as a reactant to obtain 4.2 g of the target compound; HRMS [M]+: 701.83
[[ 합성예Synthesis example 11] 11] MatMat 26의 합성 Composition of 26
반응물로 [준비예 2] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 701.83
4.2 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 701.83
[[ 합성예Synthesis example 12] 12] MatMat 27의 합성 Composition of 27
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 649.79
The same process as [Synthesis Example 2] was performed except that [Preparation Example 2] was used as a reactant to obtain 5.8 g of the target compound; HRMS [M]+: 649.79
[[ 합성예Synthesis example 13] 13] MatMat 30의 합성 composite of 30
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 723.88
The same process as [Synthesis Example 3] was performed except that [Preparation Example 2] was used as a reactant to obtain 6.7 g of the target compound; HRMS [M]+: 723.88
[[ 합성예Synthesis example 14] 14] MatMat 32의 합성 Composition of 32
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 573.70
The same process as [Synthesis Example 4] was performed except that [Preparation Example 2] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 573.70
[[ 합성예Synthesis example 15] 15] MatMat 33의 합성 Composition of 33
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 663.78
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 663.78
[[ 합성예Synthesis example 16] 16] MatMat 38의 합성 Composition of 38
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 663.78
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 663.78
[[ 합성예Synthesis example 17] 17] MatMat 45의 합성 synthesis of 45
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 728.86
4.5 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 728.86
[[ 합성예Synthesis example 18] 18] MatMat 46의 합성 synthesis of 46
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 804.95
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 804.95
[[ 합성예Synthesis example 19] 19] MatMat 48의 합성 Composition of 48
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 803.97
The same process as [Synthesis Example 9] was performed except that [Preparation Example 2] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 803.97
[[ 합성예Synthesis example 20] 20] MatMat 49의 합성 synthesis of 49
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 701.83
The same process as [Synthesis Example 10] was performed except that [Preparation Example 2] was used as a reactant to obtain 4.2 g of the target compound; HRMS [M]+: 701.83
[[ 합성예Synthesis example 21] 21] MatMat 51의 합성 synthesis of 51
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 665.85
5.3 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 665.85
[[ 합성예Synthesis example 22] 22] MatMat 52의 합성 synthesis of 52
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 665.85
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 665.85
[[ 합성예Synthesis example 23] 23] MatMat 55의 합성 synthesis of 55
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 739.94
The same process as [Synthesis Example 3] was performed except that [Preparation Example 3] was used as a reactant to obtain 6.4 g of the target compound; HRMS [M]+: 739.94
[[ 합성예Synthesis example 24] 24] MatMat 57의 합성 synthesis of 57
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 589.76
The same process as [Synthesis Example 4] was performed except that [Preparation Example 3] was used as a reactant to obtain 4.4 g of the target compound; HRMS [M]+: 589.76
[[ 합성예Synthesis example 25] 25] MatMat 58의 합성 synthesis of 58
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 679.84
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 679.84
[[ 합성예Synthesis example 26] 26] MatMat 63의 합성 synthesis of 63
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 679.84
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 679.84
[[ 합성예Synthesis example 27] 27] MatMat 70의 합성 synthesis of 70
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 744.92
4.8 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 744.92
[[ 합성예Synthesis example 28] 28] MatMat 71의 합성 synthesis of 71
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 821.01
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 821.01
[[ 합성예Synthesis example 29] 29] MatMat 73의 합성 synthesis of 73
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 820.03
The same process as [Synthesis Example 9] was performed except that [Preparation Example 3] was used as a reactant to obtain 4.1 g of the target compound; HRMS [M]+: 820.03
[[ 합성예Synthesis example 30] 30] MatMat 74의 합성 synthesis of 74
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 717.89
The same process as [Synthesis Example 10] was performed except that [Preparation Example 3] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 717.89
[[ 합성예Synthesis example 31] 31] MatMat 76의 합성 synthesis of 76
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 665.85
5.3 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 665.85
[[ 합성예Synthesis example 32] 32] MatMat 77의 합성 Composition of 77
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 665.85
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 665.85
[[ 합성예Synthesis example 33] 33] MatMat 80의 합성 synthesis of 80
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 739.94
6.4 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 739.94
[[ 합성예Synthesis example 34] 34] MatMat 82의 합성 synthesis of 82
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 589.76
The same process as [Synthesis Example 4] was performed except that [Preparation Example 4] was used as a reactant to obtain 4.4 g of the target compound; HRMS [M]+: 589.76
[[ 합성예Synthesis example 35] 35] MatMat 83의 합성 synthesis of 83
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 679.84
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 679.84
[[ 합성예Synthesis example 36] 36] MatMat 88의 합성 synthesis of 88
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 679.84
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 679.84
[[ 합성예Synthesis example 37] 37] MatMat 95의 합성 synthesis of 95
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 744.92
4.8 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 744.92
[[ 합성예Synthesis example 38] 38] MatMat 96의 합성 synthesis of 96
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 821.01
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 821.01
[[ 합성예Synthesis example 39] 39] MatMat 98의 합성 synthesis of 98
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 820.03
The same process as [Synthesis Example 9] was performed except that [Preparation Example 4] was used as a reactant to obtain 4.1 g of the target compound; HRMS [M]+: 820.03
[[ 합성예Synthesis example 40] 40] MatMat 99의 합성 synthesis of 99
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 717.89
The same process as [Synthesis Example 10] was performed except that [Preparation Example 4] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 717.89
[[ 합성예Synthesis example 41] 41] MatMat 51의 합성 synthesis of 51
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 724.91
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 724.91
[[ 합성예Synthesis example 42] 42] MatMat 52의 합성 synthesis of 52
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 724.91
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 724.91
[[ 합성예Synthesis example 43] 43] MatMat 55의 합성 synthesis of 55
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 798.99
6.5 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 798.99
[[ 합성예Synthesis example 44] 44] MatMat 57의 합성 synthesis of 57
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 648.81
The same process as [Synthesis Example 4] was performed except that [Preparation Example 5] was used as a reactant to obtain 4.1 g of the target compound; HRMS [M]+: 648.81
[[ 합성예Synthesis example 45] 45] MatMat 58의 합성 synthesis of 58
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 738.89
The same process as [Synthesis Example 5] was performed except that [Preparation Example 5] was used as a reactant to obtain 5.7 g of the target compound; HRMS [M]+: 738.89
[[ 합성예Synthesis example 46] 46] MatMat 63의 합성 synthesis of 63
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 738.89
The same process as [Synthesis Example 6] was performed except that [Preparation Example 5] was used as a reactant to obtain 5.6 g of the target compound; HRMS [M]+: 738.89
[[ 합성예Synthesis example 47] 47] MatMat 101의 합성 synthesis of 101
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 724.91
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 6] was used as a reactant; HRMS [M]+: 724.91
[[ 합성예Synthesis example 48] 48] MatMat 102의 합성 synthesis of 102
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 724.91
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 6] was used as a reactant; HRMS [M]+: 724.91
[[ 합성예Synthesis example 49] 49] MatMat 105의 합성 synthesis of 105
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 798.99
The same process as [Synthesis Example 3] was performed except that [Preparation Example 6] was used as a reactant to obtain 6.3 g of the target compound; HRMS [M]+: 798.99
[[ 합성예Synthesis example 50] 50] MatMat 107의 합성 synthesis of 107
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 648.81
The same process as [Synthesis Example 4] was performed except that [Preparation Example 6] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 648.81
[[ 합성예Synthesis example 51] 51] MatMat 108의 합성 synthesis of 108
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 738.89
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 6] was used as a reactant; HRMS [M]+: 738.89
[[ 합성예Synthesis example 52] 52] MatMat 113의 합성 synthesis of 113
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 738.89
The same process as [Synthesis Example 6] was performed except that [Preparation Example 6] was used as a reactant to obtain 5.6 g of the target compound; HRMS [M]+: 738.89
[[ 합성예Synthesis example 53] 53] MatMat 131의 합성 synthesis of 131
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 699.85
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 699.85
[[ 합성예Synthesis example 54] 54] MatMat 132의 합성 synthesis of 132
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 699.85
The same process as [Synthesis Example 2] was performed except that [Preparation Example 7] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 699.85
[[ 합성예Synthesis example 55] 55] MatMat 134의 합성 synthesis of 134
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 773.94
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 773.94
[[ 합성예Synthesis example 56] 56] MatMat 135의 합성 synthesis of 135
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 629.76
The same process as [Synthesis Example 4] was performed except that [Preparation Example 7] was used as a reactant to obtain 4.2 g of the target compound; HRMS [M]+: 629.76
[[ 합성예Synthesis example 57] 57] MatMat 136의 합성 synthesis of 136
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 713.84
4.4 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 713.84
[[ 합성예Synthesis example 58] 58] MatMat 141의 합성 synthesis of 141
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 713.84
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 713.84
[[ 합성예Synthesis example 59] 59] MatMat 145의 합성 synthesis of 145
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 778.92
The same process as [Synthesis Example 7] was performed except that [Preparation Example 7] was used as a reactant to obtain 4.4 g of the target compound; HRMS [M]+: 778.92
[[ 합성예Synthesis example 60] 60] MatMat 146의 합성 synthesis of 146
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 855.01
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 855.01
[[ 합성예Synthesis example 61] 61] MatMat 148의 합성 synthesis of 148
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 854.03
The same process as [Synthesis Example 9] was performed except that [Preparation Example 7] was used as a reactant to obtain 4.5 g of the target compound; HRMS [M]+: 854.03
[[ 합성예Synthesis example 62] 62] MatMat 149의 합성 synthesis of 149
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 751.89
The same process as [Synthesis Example 10] was performed except that [Preparation Example 7] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 751.89
[[ 합성예Synthesis example 63] 63] MatMat 151의 합성 synthesis of 151
반응물로 [준비예 8] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 699.85
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 699.85
[[ 합성예Synthesis example 64] 64] MatMat 152의 합성 synthesis of 152
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 699.85
5.3 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 699.85
[[ 합성예Synthesis example 65] 65] MatMat 155의 합성 synthesis of 155
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 773.94
The same process as [Synthesis Example 3] was performed except that [Preparation Example 8] was used as a reactant to obtain 5.7 g of the target compound; HRMS [M]+: 773.94
[[ 합성예Synthesis example 66] 66] MatMat 157의 합성 synthesis of 157
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 623.76
The same process as [Synthesis Example 4] was performed except that [Preparation Example 8] was used as a reactant to obtain 4.1 g of the target compound; HRMS [M]+: 623.76
[[ 합성예Synthesis example 67] 67] MatMat 158의 합성 synthesis of 158
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 713.84
4.4 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 713.84
[[ 합성예Synthesis example 68] 68] MatMat 163의 합성 synthesis of 163
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 713.84
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 713.84
[[ 합성예Synthesis example 69] 69] MatMat 170의 합성 synthesis of 170
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 778.92
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 778.92
[[ 합성예Synthesis example 70] 70] MatMat 171의 합성 synthesis of 171
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 855.01
4.7 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 855.01
[[ 합성예Synthesis example 71] 71] MatMat 173의 합성 synthesis of 173
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 854.03
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 854.03
[[ 합성예Synthesis example 72] 72] MatMat 174의 합성 synthesis of 174
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 751.89
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 751.89
[[ 합성예Synthesis example 73] 73] MatMat 176의 합성 synthesis of 176
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 715.91
6.3 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 715.91
[[ 합성예Synthesis example 74] 74] MatMat 177의 합성 synthesis of 177
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 715.91
The same process as [Synthesis Example 2] was performed except that [Preparation Example 9] was used as a reactant to obtain 4.4 g of the target compound; HRMS [M]+: 715.91
[[ 합성예Synthesis example 75] 75] MatMat 179의 합성 synthesis of 179
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 790.00
6.1 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 790.00
[[ 합성예Synthesis example 76] 76] MatMat 180의 합성 synthesis of 180
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 639.82
The same process as [Synthesis Example 4] was performed except that [Preparation Example 9] was used as a reactant to obtain 4.5 g of the target compound; HRMS [M]+: 639.82
[[ 합성예Synthesis example 77] 77] MatMat 181의 합성 synthesis of 181
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 729.90
4.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 729.90
[[ 합성예Synthesis example 78] 78] MatMat 186의 합성 synthesis of 186
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 729.90
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 729.90
[[ 합성예Synthesis example 79] 79] MatMat 190의 합성 synthesis of 190
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 794.98
4.4 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 794.98
[[ 합성예Synthesis example 80] 80] MatMat 191의 합성 synthesis of 191
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 871.07
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 871.07
[[
합성예Synthesis example
81] 81]
MatMat
193의 합성 synthesis of 193
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 합물 6.1g을 얻었다.; HRMS [M]+: 870.09
The same process as [Synthesis Example 9] was performed except that [Preparation Example 9] was used as a reactant, and 6.1 g of the target compound was obtained; HRMS [M]+: 870.09
[[
합성예Synthesis example
82] 82]
MatMat
194의 합성 synthesis of 194
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 767.95
The same process as [Synthesis Example 10] was performed except that [Preparation Example 9] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 767.95
[[ 합성예Synthesis example 83] 83] MatMat 196의 합성 synthesis of 196
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 715.91
The same process as [Synthesis Example 1] was performed except that [Preparation Example 10] was used as a reactant to obtain 4.3 g of the target compound; HRMS [M]+: 715.91
[[ 합성예Synthesis example 84] 84] MatMat 197의 합성 synthesis of 197
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 715.91
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 715.91
[[ 합성예Synthesis example 85] 85] MatMat 200의 합성 combination of 200
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 790.00
6.5 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 790.00
[[ 합성예Synthesis example 86] 86] MatMat 202의 합성 synthesis of 202
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 639.82
4.8 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 639.82
[[ 합성예Synthesis example 87] 87] MatMat 203의 합성 synthesis of 203
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 729.90
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 729.90
[[ 합성예Synthesis example 88] 88] MatMat 208의 합성 synthesis of 208
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 729.90
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 729.90
[[ 합성예Synthesis example 89] 89] MatMat 215의 합성 synthesis of 215
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 794.98
The same process as [Synthesis Example 7] was performed except that [Preparation Example 10] was used as a reactant to obtain 4.3 g of the target compound; HRMS [M]+: 794.98
[[ 합성예Synthesis example 90] 90] MatMat 216의 합성 synthesis of 216
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 871.07
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 871.07
[[ 합성예Synthesis example 91] 91] MatMat 218의 합성 synthesis of 218
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 870.09
The same process as [Synthesis Example 9] was performed except that [Preparation Example 10] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 870.09
[[ 합성예Synthesis example 92] 92] MatMat 219의 합성 synthesis of 219
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 767.95
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 767.95
[[ 합성예Synthesis example 93] 93] MatMat 221의 합성 synthesis of 221
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 774.97
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 774.97
[[ 합성예Synthesis example 94] 94] MatMat 222의 합성 synthesis of 222
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 774.97
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 774.97
[[ 합성예Synthesis example 95] 95] MatMat 225의 합성 synthesis of 225
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 849.05
6.8 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 849.05
[[ 합성예Synthesis example 96] 96] MatMat 227의 합성 Composition of 227
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 698.87
The same process as [Synthesis Example 4] was performed except that [Preparation Example 11] was used as a reactant to obtain 4.5 g of the target compound; HRMS [M]+: 698.87
[[ 합성예Synthesis example 97] 97] MatMat 228의 합성 Composition of 228
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 788.95
The same process as [Synthesis Example 5] was performed except that [Preparation Example 11] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 788.95
[[ 합성예Synthesis example 98] 98] MatMat 233의 합성 synthesis of 233
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 788.95
The same process as [Synthesis Example 6] was performed except that [Preparation Example 11] was used as a reactant to obtain 6.6 g of the target compound; HRMS [M]+: 788.95
[[ 합성예Synthesis example 99] 99] MatMat 240의 합성 synthesis of 240
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 854.03
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 854.03
[[ 합성예Synthesis example 100] 100] MatMat 241의 합성 synthesis of 241
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 930.13
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 930.13
[[ 합성예Synthesis example 101] 101] MatMat 243의 합성 synthesis of 243
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 929.14
The same process as [Synthesis Example 9] was performed except that [Preparation Example 11] was used as a reactant to obtain 4.3 g of the target compound; HRMS [M]+: 929.14
[[ 합성예Synthesis example 102] 102] MatMat 244의 합성 244 synthesis
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 827.00
The same process as [Synthesis Example 10] was performed except that [Preparation Example 11] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 827.00
[[ 합성예Synthesis example 103] 103] MatMat 246의 합성 synthesis of 246
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 774.97
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 774.97
[[ 합성예Synthesis example 104] 104] MatMat 247의 합성 synthesis of 247
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 774.97
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 774.97
[[ 합성예Synthesis example 105] 105] MatMat 250의 합성 composite of 250
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 849.05
The same process as [Synthesis Example 3] was performed except that [Preparation Example 12] was used as a reactant to obtain 6.9 g of the target compound; HRMS [M]+: 849.05
[[ 합성예Synthesis example 106] 106] MatMat 252의 합성 synthesis of 252
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 698.87
4.8 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 698.87
[[ 합성예Synthesis example 107] 107] MatMat 253의 합성 synthesis of 253
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 788.95
The same process as [Synthesis Example 5] was performed except that [Preparation Example 12] was used as a reactant to obtain 5.1 g of the target compound; HRMS [M]+: 788.95
[[ 합성예Synthesis example 108] 108] MatMat 258의 합성 synthesis of 258
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 788.95
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 788.95
[[ 합성예Synthesis example 109] 109] MatMat 265의 합성 synthesis of 265
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 854.03
The same process as [Synthesis Example 7] was performed except that [Preparation Example 12] was used as a reactant to obtain 4.5 g of the target compound; HRMS [M]+: 854.03
[[ 합성예Synthesis example 110] 110] MatMat 266의 합성 synthesis of 266
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 930.13
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 930.13
[[ 합성예Synthesis example 111] 111] MatMat 268의 합성 Composition of 268
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 929.14
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 929.14
[[ 합성예Synthesis example 112] 112] MatMat 269의 합성 synthesis of 269
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 827.00
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 827.00
[[ 합성예Synthesis example 113] 113] MatMat 271의 합성 synthesis of 271
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 699.85
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 699.85
[[ 합성예Synthesis example 114] 114] MatMat 172의 합성 synthesis of 172
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 699.85
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 699.85
[[ 합성예Synthesis example 115] 115] MatMat 175의 합성 synthesis of 175
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 773.94
The same process as [Synthesis Example 3] was performed except that [Preparation Example 13] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 773.94
[[ 합성예Synthesis example 116] 116] MatMat 177의 합성 synthesis of 177
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 629.76
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 629.76
[[ 합성예Synthesis example 117] 117] MatMat 178의 합성 synthesis of 178
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 713.84
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 713.84
[[ 합성예Synthesis example 118] 118] MatMat 183의 합성 synthesis of 183
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 713.84
The same process as [Synthesis Example 6] was performed except that [Preparation Example 13] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 713.84
[[ 합성예Synthesis example 119] 119] MatMat 190의 합성 synthesis of 190
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 778.92
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 778.92
[[ 합성예Synthesis example 120] 120] MatMat 191의 합성 synthesis of 191
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 855.01
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 855.01
[[ 합성예Synthesis example 121] 121] MatMat 193의 합성 synthesis of 193
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 854.03
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 854.03
[[ 합성예Synthesis example 122] 122] MatMat 194의 합성 synthesis of 194
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 751.89
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 751.89
[[ 합성예Synthesis example 123] 123] MatMat 196의 합성 synthesis of 196
반응물로 [준비예 14] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 699.85
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 699.85
[[ 합성예Synthesis example 124] 124] MatMat 197의 합성 synthesis of 197
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 699.85
The same process as [Synthesis Example 2] was performed except that [Preparation Example 14] was used as a reactant to obtain 4.3 g of the target compound; HRMS [M]+: 699.85
[[ 합성예Synthesis example 125] 125] MatMat 300의 합성 composite of 300
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 773.94
The same process as [Synthesis Example 3] was performed except that [Preparation Example 14] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 773.94
[[ 합성예Synthesis example 126] 126] MatMat 302의 합성 synthesis of 302
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 623.76
6.1 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 623.76
[[ 합성예Synthesis example 127] 127] MatMat 303의 합성 synthesis of 303
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 713.84
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 713.84
[[ 합성예Synthesis example 128] 128] MatMat 308의 합성 synthesis of 308
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 713.84
6.0 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 713.84
[[ 합성예Synthesis example 129] 129] MatMat 315의 합성 synthesis of 315
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 778.92
The same process as [Synthesis Example 7] was performed except that [Preparation Example 14] was used as a reactant to obtain 4.5 g of the target compound; HRMS [M]+: 778.92
[[ 합성예Synthesis example 130] 130] MatMat 316의 합성 synthesis of 316
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 855.01
The same process as [Synthesis Example 8] was performed except that [Preparation Example 14] was used as a reactant to obtain 4.2 g of the target compound; HRMS [M]+: 855.01
[[ 합성예Synthesis example 131] 131] MatMat 318의 합성 synthesis of 318
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 854.03
The same process as [Synthesis Example 9] was performed except that [Preparation Example 14] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 854.03
[[ 합성예Synthesis example 132] 132] MatMat 319의 합성 synthesis of 319
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 751.89
6.2 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 751.89
[[ 합성예Synthesis example 133] 133] MatMat 321의 합성 synthesis of 321
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 715.91
5.3 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 715.91
[[ 합성예Synthesis example 134] 134] MatMat 322의 합성 synthesis of 322
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 715.91
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 715.91
[[ 합성예Synthesis example 135] 135] MatMat 325의 합성 synthesis of 325
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 790.00
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 790.00
[[ 합성예Synthesis example 136] 136] MatMat 327의 합성 synthesis of 327
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 639.82
The same process as [Synthesis Example 4] was performed except that [Preparation Example 15] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 639.82
[[ 합성예Synthesis example 137] 137] MatMat 328의 합성 synthesis of 328
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 729.90
The same process as [Synthesis Example 5] was performed except that [Preparation Example 15] was used as a reactant to obtain 4.5 g of the target compound; HRMS [M]+: 729.90
[[ 합성예Synthesis example 138] 138] MatMat 333의 합성 synthesis of 333
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 729.90
6.0 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 729.90
[[ 합성예Synthesis example 139] 139] MatMat 340의 합성 synthesis of 340
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 794.98
The same process as [Synthesis Example 7] was performed except that [Preparation Example 15] was used as a reactant to obtain 4.1 g of the target compound; HRMS [M]+: 794.98
[[ 합성예Synthesis example 140] 140] MatMat 341의 합성 synthesis of 341
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 871.07
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 871.07
[[ 합성예Synthesis example 141] 141] MatMat 343의 합성 synthesis of 343
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 합물 5.1g을 얻었다.; HRMS [M]+: 870.09
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 870.09
[[ 합성예Synthesis example 142] 142] MatMat 344의 합성 synthesis of 344
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 767.95
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 767.95
[[ 합성예Synthesis example 143] 143] MatMat 346의 합성 synthesis of 346
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 715.91
The same process as [Synthesis Example 1] was performed except that [Preparation Example 16] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 715.91
[[ 합성예Synthesis example 144] 144] MatMat 347의 합성 synthesis of 347
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 715.91
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 715.91
[[ 합성예Synthesis example 145] 145] MatMat 350의 합성 synthesis of 350
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 790.00
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 790.00
[[ 합성예Synthesis example 146] 146] MatMat 352의 합성 synthesis of 352
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 639.82
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 639.82
[[ 합성예Synthesis example 147] 147] MatMat 353의 합성 synthesis of 353
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 729.90
The same process as [Synthesis Example 5] was performed except that [Preparation Example 16] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 729.90
[[ 합성예Synthesis example 148] 148] MatMat 358의 합성 synthesis of 358
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 729.90
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 729.90
[[ 합성예Synthesis example 149] 149] MatMat 365의 합성 Composition of 365
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 794.98
The same process as [Synthesis Example 7] was performed except that [Preparation Example 16] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 794.98
[[ 합성예Synthesis example 150] 150] MatMat 366의 합성 Composition of 366
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 871.07
The same process as [Synthesis Example 8] was performed except that [Preparation Example 16] was used as a reactant to obtain 4.2 g of the target compound; HRMS [M]+: 871.07
[[ 합성예Synthesis example 151] 151] MatMat 368의 합성 Composition of 368
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 870.09
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 870.09
[[ 합성예Synthesis example 152] 152] MatMat 369의 합성 Composition of 369
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 767.95
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 767.95
[[ 합성예Synthesis example 153] 153] MatMat 371의 합성 synthesis of 371
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 774.97
6.1 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 774.97
[[ 합성예Synthesis example 154] 154] MatMat 372의 합성 synthesis of 372
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 774.97
The same process as [Synthesis Example 2] was performed except that [Preparation Example 17] was used as a reactant to obtain 4.3 g of the target compound; HRMS [M]+: 774.97
[[ 합성예Synthesis example 155] 155] MatMat 375의 합성 synthesis of 375
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 849.05
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 849.05
[[ 합성예Synthesis example 156] 156] MatMat 377의 합성 Composition of 377
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 698.87
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 698.87
[[ 합성예Synthesis example 157] 157] MatMat 378의 합성 synthesis of 378
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 788.95
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 788.95
[[ 합성예Synthesis example 158] 158] MatMat 383의 합성 synthesis of 383
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 788.95
The same process as [Synthesis Example 6] was performed except that [Preparation Example 17] was used as a reactant to obtain 6.4 g of the target compound; HRMS [M]+: 788.95
[[ 합성예Synthesis example 159] 159] MatMat 390의 합성 synthesis of 390
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 854.03
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 854.03
[[ 합성예Synthesis example 160] 160] MatMat 391의 합성 synthesis of 391
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 930.13
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 930.13
[[ 합성예Synthesis example 161] 161] MatMat 393의 합성 synthesis of 393
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 929.14
The same process as [Synthesis Example 9] was performed except that [Preparation Example 17] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 929.14
[[ 합성예Synthesis example 162] 162] MatMat 394의 합성 synthesis of 394
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 827.00
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 827.00
[[ 합성예Synthesis example 163] 163] MatMat 396의 합성 synthesis of 396
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 774.97
6.6 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 774.97
[[ 합성예Synthesis example 164] 164] MatMat 397의 합성 synthesis of 397
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물6.1g을 얻었다.; HRMS [M]+: 774.97
The same process as [Synthesis Example 2] was performed except that [Preparation Example 18] was used as a reactant to obtain 6.1 g of the target compound; HRMS [M]+: 774.97
[[ 합성예Synthesis example 165] 165] MatMat 400의 합성 synthesis of 400
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 849.05
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 849.05
[[ 합성예Synthesis example 166] 166] MatMat 402의 합성 synthesis of 402
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 698.87
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 698.87
[[ 합성예Synthesis example 167] 167] MatMat 403의 합성 synthesis of 403
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 788.95
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 788.95
[[ 합성예Synthesis example 168] 168] MatMat 408의 합성 synthesis of 408
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 788.95
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 788.95
[[ 합성예Synthesis example 169] 169] MatMat 415의 합성 synthesis of 415
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 854.03
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 854.03
[[ 합성예Synthesis example 170] 170] MatMat 416의 합성 synthesis of 416
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 930.13
4.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 930.13
[[ 합성예Synthesis example 171] 171] MatMat 418의 합성 synthesis of 418
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 929.14
The same process as [Synthesis Example 9] was performed except that [Preparation Example 18] was used as a reactant to obtain 4.9 g of the target compound; HRMS [M]+: 929.14
[[ 합성예Synthesis example 172] 172] MatMat 419의 합성 synthesis of 419
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 827.00
6.2 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 827.00
[[ 합성예Synthesis example 173] 173] MatMat 421의 합성 synthesis of 421
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 749.91
The same process as [Synthesis Example 1] was performed except that [Preparation Example 19] was used as a reactant to obtain 6.7 g of the target compound; HRMS [M]+: 749.91
[[ 합성예Synthesis example 174] 174] MatMat 422의 합성 synthesis of 422
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 749.91
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 19] was used as a reactant; HRMS [M]+: 749.91
[[ 합성예Synthesis example 175] 175] MatMat 425의 합성 synthesis of 425
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 824.00
The same process as [Synthesis Example 3] was performed except that [Preparation Example 19] was used as a reactant to obtain 6.7 g of the target compound; HRMS [M]+: 824.00
[[ 합성예Synthesis example 176] 176] MatMat 427의 합성 synthesis of 427
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 673.82
6.2 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 19] was used as a reactant; HRMS [M]+: 673.82
[[ 합성예Synthesis example 177] 177] MatMat 428의 합성 synthesis of 428
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 763.90
The same process as [Synthesis Example 5] was performed except that [Preparation Example 19] was used as a reactant to obtain 6.4 g of the target compound; HRMS [M]+: 763.90
[[ 합성예Synthesis example 178] 178] MatMat 433의 합성 synthesis of 433
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 763.90
The same process as [Synthesis Example 6] was performed except that [Preparation Example 19] was used as a reactant to obtain 5.8 g of the target compound; HRMS [M]+: 763.90
[[ 합성예Synthesis example 179] 179] MatMat 440의 합성 synthesis of 440
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 828.98
The same process as [Synthesis Example 7] was performed except that [Preparation Example 19] was used as a reactant to obtain 4.4 g of the target compound; HRMS [M]+: 828.98
[[ 합성예Synthesis example 180] 180] MatMat 441의 합성 synthesis of 441
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 905.07
The same process as [Synthesis Example 8] was performed except that [Preparation Example 19] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 905.07
[[ 합성예Synthesis example 181] 181] MatMat 443의 합성 synthesis of 443
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 904.09
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 19] was used as a reactant; HRMS [M]+: 904.09
[[ 합성예Synthesis example 182] 182] MatMat 444의 합성 synthesis of 444
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 801.95
The same process as [Synthesis Example 10] was performed except that [Preparation Example 19] was used as a reactant to obtain 6.9 g of the target compound; HRMS [M]+: 801.95
[[ 합성예Synthesis example 183] 183] MatMat 446의 합성 synthesis of 446
반응물로 [준비예 20] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 749.91
5.6 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 749.91
[[ 합성예Synthesis example 184] 184] MatMat 447의 합성 synthesis of 447
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 749.91
5.3 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 749.91
[[ 합성예Synthesis example 185] 185] MatMat 450의 합성 synthesis of 450
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 824.00
5.7 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 824.00
[[ 합성예Synthesis example 186] 186] MatMat 452의 합성 synthesis of 452
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 673.82
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 673.82
[[ 합성예Synthesis example 187] 187] MatMat 453의 합성 synthesis of 453
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 763.90
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 763.90
[[ 합성예Synthesis example 188] 188] MatMat 458의 합성 synthesis of 458
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 763.90
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 763.90
[[ 합성예Synthesis example 189] 189] MatMat 465의 합성 synthesis of 465
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 828.98
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 828.98
[[ 합성예Synthesis example 190] 190] MatMat 466의 합성 synthesis of 466
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 905.07
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 905.07
[[ 합성예Synthesis example 191] 191] MatMat 468의 합성 synthesis of 468
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 904.90
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 904.90
[[ 합성예Synthesis example 192] 192] MatMat 469의 합성 synthesis of 469
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 801.95
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 801.95
[[ 합성예Synthesis example 193] 193] MatMat 471의 합성 synthesis of 471
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 765.97
5.3 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 765.97
[[ 합성예Synthesis example 194] 194] MatMat 472의 합성 synthesis of 472
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 765.97
6.4 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 765.97
[[ 합성예Synthesis example 195] 195] MatMat 475의 합성 synthesis of 475
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 840.06
The same process as [Synthesis Example 3] was performed except that [Preparation Example 21] was used as a reactant to obtain 4.1 g of the target compound; HRMS [M]+: 840.06
[[ 합성예Synthesis example 196] 196] MatMat 477의 합성 synthesis of 477
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 689.88
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 689.88
[[ 합성예Synthesis example 197] 197] MatMat 478의 합성 synthesis of 478
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 779.96
5.5 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 779.96
[[ 합성예Synthesis example 198] 198] MatMat 483의 합성 synthesis of 483
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 779.96
5.0 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 779.96
[[ 합성예Synthesis example 199] 199] MatMat 490의 합성 synthesis of 490
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 845.04
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 845.04
[[ 합성예Synthesis example 200] 200] MatMat 491의 합성 synthesis of 491
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 921.13
The same process as [Synthesis Example 8] was performed except that [Preparation Example 21] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 921.13
[[ 합성예Synthesis example 201] 201] MatMat 493의 합성 synthesis of 493
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 합물 6.1g을 얻었다.; HRMS [M]+: 920.15
The same process as [Synthesis Example 9] was performed except that [Preparation Example 21] was used as a reactant to obtain 6.1 g of the target compound; HRMS [M]+: 920.15
[[ 합성예Synthesis example 202] 202] MatMat 494의 합성 synthesis of 494
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 818.01
The same process as [Synthesis Example 10] was performed except that [Preparation Example 21] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 818.01
[[ 합성예Synthesis example 203] 203] MatMat 496의 합성 synthesis of 496
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 765.97
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 765.97
[[ 합성예Synthesis example 204] 204] MatMat 497의 합성 synthesis of 497
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 765.97
6.5 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 765.97
[[ 합성예Synthesis example 205] 205] MatMat 500의 합성 synthesis of 500
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 740.06
4.5 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 740.06
[[ 합성예Synthesis example 206] 206] MatMat 502의 합성 synthesis of 502
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 689.88
The same process as [Synthesis Example 4] was performed except that [Preparation Example 22] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 689.88
[[ 합성예Synthesis example 207] 207] MatMat 503의 합성 synthesis of 503
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 779.96
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 779.96
[[ 합성예Synthesis example 208] 208] MatMat 508의 합성 synthesis of 508
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 4.6g을 얻었다.; HRMS [M]+: 779.96
The same process as [Synthesis Example 6] was performed except that [Preparation Example 22] was used as a reactant to obtain 4.6 g of the target compound; HRMS [M]+: 779.96
[[ 합성예Synthesis example 209] 209] MatMat 515의 합성 synthesis of 515
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 845.04
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 845.04
[[ 합성예Synthesis example 210] 210] MatMat 516의 합성 synthesis of 516
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 921.13
5.2 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 921.13
[[ 합성예Synthesis example 211] 211] MatMat 518의 합성 synthesis of 518
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 920.15
The same process as [Synthesis Example 9] was performed except that [Preparation Example 22] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 920.15
[[ 합성예Synthesis example 212] 212] MatMat 519의 합성 synthesis of 519
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 818.01
The same process as [Synthesis Example 10] was performed except that [Preparation Example 22] was used as a reactant to obtain 6.6 g of the target compound; HRMS [M]+: 818.01
[[ 합성예Synthesis example 213] 213] MatMat 521의 합성 synthesis of 521
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 825.03
5.1 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 825.03
[[ 합성예Synthesis example 214] 214] MatMat 522의 합성 synthesis of 522
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 825.03
5.3 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 825.03
[[ 합성예Synthesis example 215] 215] MatMat 525의 합성 synthesis of 525
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 899.11
The same process as [Synthesis Example 3] was performed except that [Preparation Example 23] was used as a reactant to obtain 4.8 g of the target compound; HRMS [M]+: 899.11
[[ 합성예Synthesis example 216] 216] MatMat 527의 합성 synthesis of 527
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 748.93
4.5 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 748.93
[[ 합성예Synthesis example 217] 217] MatMat 528의 합성 synthesis of 528
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 839.01
The same process as [Synthesis Example 5] was performed except that [Preparation Example 23] was used as a reactant to obtain 4.7 g of the target compound; HRMS [M]+: 839.01
[[ 합성예Synthesis example 218] 218] MatMat 533의 합성 synthesis of 533
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 839.01
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 839.01
[[ 합성예Synthesis example 219] 219] MatMat 540의 합성 synthesis of 540
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 904.09
The same process as [Synthesis Example 7] was performed except that [Preparation Example 23] was used as a reactant to obtain 4.2 g of the target compound; HRMS [M]+: 904.09
[[ 합성예Synthesis example 220] 220] MatMat 541의 합성 synthesis of 541
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 980.19
The same process as [Synthesis Example 8] was performed except that [Preparation Example 23] was used as a reactant to obtain 4.4 g of the target compound; HRMS [M]+: 980.19
[[ 합성예Synthesis example 221] 221] MatMat 543의 합성 synthesis of 543
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 979.20
5.8 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 979.20
[[ 합성예Synthesis example 222] 222] MatMat 544의 합성 synthesis of 544
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 877.06
The same process as [Synthesis Example 10] was performed except that [Preparation Example 23] was used as a reactant to obtain 6.8 g of the target compound; HRMS [M]+: 877.06
[[ 합성예Synthesis example 223] 223] MatMat 546의 합성 synthesis of 546
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 825.03
The same process as [Synthesis Example 1] was performed except that [Preparation Example 24] was used as a reactant to obtain 6.6 g of the target compound; HRMS [M]+: 825.03
[[ 합성예Synthesis example 224] 224] MatMat 547의 합성 synthesis of 547
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 825.03
The same process as [Synthesis Example 2] was performed except that [Preparation Example 24] was used as a reactant to obtain 7.1 g of the target compound; HRMS [M]+: 825.03
[[ 합성예Synthesis example 225] 225] MatMat 550의 합성 synthesis of 550
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 899.11
The same process as [Synthesis Example 3] was performed except that [Preparation Example 24] was used as a reactant to obtain 6.9 g of the target compound; HRMS [M]+: 899.11
[[ 합성예Synthesis example 226] 226] MatMat 552의 합성 synthesis of 552
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 748.93
The same process as [Synthesis Example 4] was performed except that [Preparation Example 24] was used as a reactant to obtain 6.8 g of the target compound; HRMS [M]+: 748.93
[[ 합성예Synthesis example 227] 227] MatMat 553의 합성 synthesis of 553
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 839.01
6.6 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 839.01
[[ 합성예Synthesis example 228] 228] MatMat 558의 합성 synthesis of 558
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 839.01
The same process as [Synthesis Example 6] was performed except that [Preparation Example 24] was used as a reactant to obtain 6.1 g of the target compound; HRMS [M]+: 839.01
[[ 합성예Synthesis example 229] 229] MatMat 565의 합성 synthesis of 565
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 904.09
6.5 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 904.09
[[ 합성예Synthesis example 230] 230] MatMat 566의 합성 synthesis of 566
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 980.19
5.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 980.19
[[ 합성예Synthesis example 231] 231] MatMat 568의 합성 synthesis of 568
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 979.20
5.9 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 979.20
[[ 합성예Synthesis example 232] 232] MatMat 569의 합성 synthesis of 569
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 877.06
The same process as [Synthesis Example 10] was performed except that [Preparation Example 24] was used as a reactant to obtain 6.2 g of the target compound; HRMS [M]+: 877.06
[[ 실시예Example 1 ~ 24] 녹색 유기 1 to 24] Green Organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
합성예 1~52에서 합성한 화합물 Mat 1 ~ Mat 129를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.Compounds Mat 1 to Mat 129 synthesized in Synthesis Examples 1 to 52 were purified to high purity by sublimation using a commonly known method, and then a green organic electroluminescent device was manufactured according to the process below.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaning the substrate for 5 minutes using UV, and vacuum evaporation. The substrate was transferred to .
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ Mat 1 ~ Mat 129의 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/each compound of Mat 1 to Mat 129 + 10% Ir(ppy) 3 (30nm)/BCP (10 nm)/Alq 3 ( An organic EL device was manufactured by stacking in the following order: 30 nm)/LiF (1 nm)/Al (200 nm).
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir(ppy) 3 , CBP and BCP are as follows.
[[ 비교예Comparative example 1] 녹색 유기 1] Green Organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 화합물 Mat 1 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.
A green organic electroluminescent device was manufactured in the same process as Example 1, except that CBP was used instead of compound Mat 1 as the light-emitting host material when forming the light-emitting layer.
[[ 평가예Evaluation example 1] One]
실시예 1 ~ 35 및 비교예 1에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.
For each green organic electroluminescent device manufactured in Examples 1 to 35 and Comparative Example 1, the driving voltage, current efficiency, and luminescence peak at a current density (10) mA/cm2 were measured, and the results are shown in Table 1 below. indicated.
(V)driving voltage
(V)
(nm)EL peak
(nm)
(cd/A)Current efficiency
(cd/A)
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물 (Mat 1~Mat 129)을 녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우(실시예 1~35) 종래 CBP를 사용한 녹색 유기 전계 발광 소자(비교예1)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.
As shown in Table 1, when the compounds according to the present invention (Mat 1 to Mat 129) were used as the emitting layer of a green organic electroluminescent device (Examples 1 to 35), the green organic electroluminescent device using conventional CBP (comparison) Compared to example 1), it can be seen that it shows better performance in terms of efficiency and driving voltage.
[[ 실시예Example 36 ~ 57] 적색 유기 36 ~ 57] Red organic 전계electric field 발광 소자의 제조 Manufacturing of light emitting devices
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in the synthesis example was purified by sublimation to high purity using a commonly known method, and then a red organic electroluminescent device was manufactured according to the process below.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate is ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). Then, the substrate is cleaned using UV for 5 minutes and then vacuum evaporated. The substrate was transferred to .
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ Mat 24 ~ Mat 569의 화합물 + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.
On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/Compound of Mat 24 ~ Mat 569 + 10% (piq) 2 Ir(acac) (30nm)/BCP (10 nm)/Alq 3 An organic electroluminescent device was manufactured by stacking (30 nm)/LiF (1 nm)/Al (200 nm) in that order.
[[ 비교예Comparative example 2] 2] 적색 유기 red organic 전계electric field 발광 소자의 제조 Manufacturing of light emitting devices
발광층 형성시 발광 호스트 물질로서 상기 Mat 24의 화합물 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 36와 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same process as Example 36, except that CBP was used instead of the compound of Mat 24 as the light-emitting host material when forming the light-emitting layer.
상기 실시예 36 ~ 57 및 비교예2 에서 사용된 m-MTDATA, (piq)2Ir(acac), CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, (piq) 2 Ir(acac), CBP, and BCP used in Examples 36 to 57 and Comparative Example 2 are as follows.
[[ 평가예Evaluation example 2] 2]
실시예 36 ~ 57 및 비교예2 에서 제작한 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.
The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each organic electroluminescent device manufactured in Examples 36 to 57 and Comparative Example 2, and the results are shown in Table 2 below.
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 적색 유기 전계 발광 소자의 발광층의 재료로 사용하였을 경우(실시예 36~57) 종래 CBP를 발광층의 재료로 사용한 적색 유기 전계 발광 소자(비교예2)와 비교해 볼 때 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2, when the compound according to the present invention was used as a material for the light-emitting layer of a red organic electroluminescent device (Examples 36 to 57), a red organic electroluminescent device using conventional CBP as a material for the light-emitting layer (Comparative Example) Compared to 2), it can be seen that it shows excellent performance in terms of efficiency and driving voltage.
10: 양극 20: 음극
30: 유기층 31: 정공 수송층
32: 발광층 33: 정공 수송 보조층
34: 전자 수송층 35: 전자 수송 보조층
36: 전자 주입층 37: 정공 주입층10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transport auxiliary layer
34: electron transport layer 35: electron transport auxiliary layer
36: electron injection layer 37: hole injection layer
Claims (14)
[화학식 5]
[화학식 6]
[화학식 7]
[화학식 8]
[화학식 9]
[화학식 10]
[화학식 11]
[화학식 12]
상기 화학식 5 내지 12에서,
X는 O, S 및 N(Ar2)으로 구성된 군으로부터 선택되고;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;
l 및 o는 각각 독립적으로 0 내지 4의 정수이며;
R1 및 R4는 각각 수소 또는 중수소이며;
Ar2는 C6의 아릴기이며;
Ar1은 수소, 중수소, 할로겐, 시아노기, 니트로기, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합고리를 형성하며;
단, L1이 헤테로아릴렌기 또는 Ar1이 헤테로아릴인 경우 L1또는 Ar1은 다이아진, 트리아진, 퀴놀린, 퀴나졸린, 벤조이미다졸, 페녹사진, 아크리딘, 카바졸, 디벤조퓨란 및 피리딘에서 선택되고;
상기 L1의 아릴렌기 및 헤테로아릴렌기와 상기 Ar1 내지 Ar2의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 C1~C40의 알킬기 및 C6~C60의 아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며;
단, X가 N(Ar2)인경우 Ar1은 아민기, 트리페닐레닐기, 나프틸기, 플루오렌기, 터페닐기, 디벤조싸이오펜, 페난트릴기, 퀴나졸린기, 퀴놀린기, 벤조이미다졸기, 페녹사진기, 아크리딘기, 카바졸기 및 디벤조퓨란기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합고리를 형성한다.
Compounds represented by any of the following formulas 5 to 12:
[Formula 5]
[Formula 6]
[Formula 7]
[Formula 8]
[Formula 9]
[Formula 10]
[Formula 11]
[Formula 12]
In Formulas 5 to 12,
X is selected from the group consisting of O, S and N(Ar 2 );
L 1 is selected from the group consisting of a single bond, an arylene group having C 6 to C 18 and a heteroarylene group having 5 to 18 nuclear atoms;
l and o are each independently an integer from 0 to 4;
R 1 and R 4 are each hydrogen or deuterium;
Ar 2 is an aryl group of C 6 ;
Ar 1 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C 6 to C 60 , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C 1 to C 40 , aryloxy group with C 6 to C 60 , C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphospha It is selected from the group consisting of a nyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or is combined with an adjacent group to form a condensed ring;
However, when L 1 is a heteroarylene group or Ar 1 is heteroaryl, L 1 or Ar 1 is diazine, triazine, quinoline, quinazoline, benzoimidazole, phenoxazine, acridine, carbazole, or dibenzofuran. and pyridine;
The arylene group and heteroarylene group of L 1 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, and arylamine of Ar 1 to Ar 2 group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group each independently consists of a C 1 to C 40 alkyl group and a C 6 to C 60 aryl group. It is substituted or unsubstituted with one or more substituents selected from the group, and when substituted with a plurality of substituents, they may be the same or different from each other;
However , when It is selected from the group consisting of a polyazole group, a phenoxazine group, an acridine group, a carbazole group, and a dibenzofuran group, or is combined with an adjacent group to form a condensed ring.
상기 L1은 단일결합이거나, 하기 화학식 A-1 내지 화학식 A-3 중 어느 하나로 표시되는 링커인, 화합물:
상기 화학식 A-1 내지 A-3에서,
*는 결합이 이루어지는 부분을 의미한다.According to paragraph 1,
The compound wherein L 1 is a single bond or a linker represented by any one of the following formulas A-1 to formula A-3:
In the above formulas A-1 to A-3,
* indicates the part where the combination takes place.
상기 Ar1은 하기 화학식 15로 표시되는 치환기인, 화합물:
[화학식 15]
상기 화학식 15에서,
*은 결합이 이루어지는 부분을 의미하고;
R8 및 R9는 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며;
상기 R8 및 R9의 아릴기, 헤테로아릴기는 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤 테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.
According to paragraph 1,
A compound in which Ar 1 is a substituent represented by the following formula (15):
[Formula 15]
In Formula 15 above,
* refers to the part where the combination takes place;
R 8 and R 9 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, or are combined with adjacent groups to form a condensed ring;
The aryl group and heteroaryl group of R 8 and R 9 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups of C 6 to C 60 and heteroaryl groups of 5 to 60 nuclear atoms, and , when substituted with a plurality of substituents, they are the same or different from each other.
상기 Ar1은 하기 화학식 B-1 내지 B-8 중 어느 하나로 표시되는 치환기인, 화합물:
상기 화학식 B-1 내지 B-8에서,
*은 결합이 이루어지는 부분을 의미하고;
Z5 내지 Z12는 각각 독립적으로 N 또는 C(R12)이며;
상기 화학식 B-1에서 L1에 결합되는 Z5 내지 Z8 중 어느 하나는 C(R12)이고, 이때 상기 R12는 부재이며;
T1 및 T2는 각각 독립적으로 단일결합, C(R13)(R14), N(R15), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;
q 및 r은 각각 독립적으로 0 내지 4의 정수이며;
R10 및 R11은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R10 및 R11 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;
R12 내지 R15는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R12 내지 R15 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;
상기 R10 내지 R15의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.According to paragraph 1,
A compound in which Ar 1 is a substituent represented by any one of the following formulas B-1 to B-8:
In the above formulas B-1 to B-8,
* refers to the part where the combination takes place;
Z 5 to Z 12 are each independently N or C(R 12 );
In Formula B-1, any one of Z 5 to Z 8 bonded to L 1 is C(R 12 ), wherein R 12 is absent;
T 1 and T 2 are each independently selected from the group consisting of a single bond, C(R 13 )(R 14 ), N(R 15 ), O, and S, but both T 1 and T 2 are not a single bond;
q and r are each independently integers from 0 to 4;
R 10 and R 11 are each independently selected from 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 6 to C 60 Aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C 6 ~ C 60 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 may be selected from the group consisting of an arylphosphanyl group, a C 6 ~ C 60 mono or diarylphosphinyl group, and a C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and the R When each of 10 and R 11 is plural, they are the same or different from each other;
R 12 to R 15 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 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, 3 nuclear atoms to 40 heterocycloalkyl groups, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to It may be selected from the group consisting of C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group, and C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, When each of R 12 to R 15 is plural, they are the same or different from each other;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R 10 to R 15 Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~C 60 arylamine group, C 3 ~C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~C 40 alkylsilyl group, C 1 ~C 40 alkylboron group, C 6 At least one substituent selected from the group consisting of an aryl boron group of ~C 60 , an arylphosphanyl group of C 6 ~ C 60 , a mono or diarylphosphinyl group of C 6 ~ C 60 , and an arylsilyl group of C 6 ~ C 60 When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other.
상기 Ar1은 하기 화학식 C-1 내지 C-14 중 어느 하나로 표시되는 치환기인, 화합물:
상기 화학식 C-1 내지 C-14에서,
*은 결합이 이루어지는 부분을 의미하고;
q, r 및 s는 각각 독립적으로 0 내지 4의 정수이며;
R10, R11 및 R16은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R10, R11 및 R18 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;
R12 내지 R15는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;
상기 R10 내지 R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.According to paragraph 1,
A compound in which Ar 1 is a substituent represented by any one of the following formulas C-1 to C-14:
In the above formulas C-1 to C-14,
* refers to the part where the combination takes place;
q, r and s are each independently integers from 0 to 4;
R 10 , R 11 and R 16 are each independently 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 6 Aryl group of ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 ~ C 60 , alkyloxy group of C 1 ~ C 40 , cycloalkyl group of C 3 ~ C 40 , number of nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 It is selected from the group consisting of an arylphosphanyl group of ~C 60 , a mono or diarylphosphinyl group of C 6 ~C 60 , and an arylsilyl group of C 6 ~C 60 , or may be combined with an adjacent group to form a condensed ring. , when each of R 10 , R 11 and R 18 is plural, they are the same or different from each other;
R 12 to R 15 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 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, 3 nuclear atoms to 40 heterocycloalkyl groups, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to It may be selected from the group consisting of a C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R 10 to R 16 Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkylboron group, C 6 At least one substituent selected from the group consisting of an aryl boron group of ~C 60 , an arylphosphanyl group of C 6 ~ C 60 , a mono or diarylphosphinyl group of C 6 ~ C 60 , and an arylsilyl group of C 6 ~ C 60 When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other.
상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물:
According to paragraph 1,
The compound is characterized in that it is selected from the group consisting of the following compounds:
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 5 내지 12 중 어느 하나로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the one or more organic layers includes a compound represented by any one of Formulas 5 to 12 of claim 1.
상기 유기물층은 정공 주입층, 정공 수송층, 정공 수송 보조층, 전자 수송층, 전자 수송 보조층 및 발광층으로 이루어진 군에서 선택되는 하나 이상의 층을 포함하는, 유기 전계 발광 소자.According to clause 13,
The organic material layer includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer.
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