KR20130007934A - Organic electroluminescence device using the triphenylene derivative - Google Patents
Organic electroluminescence device using the triphenylene derivative Download PDFInfo
- Publication number
- KR20130007934A KR20130007934A KR1020110068609A KR20110068609A KR20130007934A KR 20130007934 A KR20130007934 A KR 20130007934A KR 1020110068609 A KR1020110068609 A KR 1020110068609A KR 20110068609 A KR20110068609 A KR 20110068609A KR 20130007934 A KR20130007934 A KR 20130007934A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- organic
- chemical formula
- compound
- formula
- Prior art date
Links
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
- C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Abstract
Description
본 발명은 특정 구조를 갖는 트리페닐렌 계열 유기 전계 발광 소자용 재료 및 상기 재료를 하나 이상의 유기물 층에 포함함으로써 발광효율, 휘도, 열적 안정성, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a triphenylene-based organic electroluminescent device having a specific structure and an organic electroluminescent device having improved characteristics such as luminous efficiency, luminance, thermal stability, driving voltage and lifetime by incorporating the above material into one or more organic layers .
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광 (electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film luminosity of Bernanose in the 1950s, (Tang) and a functional layer of a light emitting layer. In order to produce high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 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 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. At this time, the material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있으며, 이때 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있기 때문에, 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대한 연구가 많이 진행되고 있다. The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The phosphorescent dopant as well as phosphorescent host materials have been studied extensively.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광 재료로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광 재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료들은 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 blue, green, red 도판트 재료로 사용되고 있으며, 현재까지는 CBP가 인광 호스트 재료로 높은 특성을 나타내고 있다. 그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 OLED 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하는 실정이다. 따라서 더욱 성능이 뛰어난 재료의 개발이 요구되고 있다.Hole injection layer, hole transport layer to date. NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials are metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 , And CBP is a phosphorescent host material. However, existing materials have advantages in terms of light emitting properties, but they are not satisfactory in terms of lifetime in OLED devices because of low glass transition temperature and poor thermal stability. Therefore, development of materials with higher performance is required.
본 발명은 상기 과제를 해결하기 위해서 안출된 것으로, 유리 전이온도 향상 및 우수한 열적 안정성을 갖는 신규 유기 화합물을 제공하는 것을 목적으로 한다.SUMMARY OF THE INVENTION The present invention has been conceived to solve the above-mentioned problems, and an object thereof is to provide a novel organic compound having an improved glass transition temperature and excellent thermal stability.
또한 본 발명은 상기 신규 유기 화합물을 포함하여 발광효율, 휘도, 전력효율, 열적 안정성, 구동전압, 소자 수명 등의 제반 특성이 향상된 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound and having improved various characteristics such as luminous efficiency, luminance, power efficiency, thermal stability, driving voltage, and device lifetime.
본 발명은 하기 화학식 1 로 표시되는 화합물, 바람직하게는 트리페닐렌 계열 유기 전계 발광 소자용 재료를 제공한다. The present invention provides a compound represented by the following formula (1), preferably a triphenylene-based organic electroluminescent device.
X는 CR16R17, O, S, SiR18R19, S(=O), 및 S(=O)2로 이루어진 군에서 선택되고; X is CR 16 R 17, O, S , SiR 18 R 19, S (= O), and S (= O) is selected from the group consisting of 2;
R1 내지 R19는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 아미노기, 니트로기, 니트릴기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C5~C40의 아릴기, C1~C40의 헤테로아릴기, C1~C40의 알콕시기, C5~C40의 아릴옥시기, C1~C40의 알킬아미노기, C5~C40의 아릴아미노기, C5~C40의 디아릴아미노기, C5~C40의 헤테로아릴아미노기, C2~C40의 디헤테로아릴아미노기, C6~C40의 아릴알킬기, C6~C40의 헤테로아릴알킬기, C3~C40의 시클로알킬기, C1~C40의 할로겐알킬기, C3~C40의 헤테로시클로알킬기, C3~C40 의 알킬실릴기, C3~C40의 아릴실릴기, 및 C3~C40의 헤테로아릴실릴기로 이루어진 군에서 선택되며;R 1 to R 19 are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C A C 5 to C 40 aryl group, a C 1 to C 40 heteroaryl group, a C 1 to C 40 alkoxy group, a C 5 to C 40 aryloxy group, a C 1 to C 40 alkyl An amino group, a C 5 to C 40 arylamino group, a C 5 to C 40 diarylamino group, a C 5 to C 40 heteroarylamino group, a C 2 to C 40 diheteroarylamino group, a C 6 to C 40 arylalkyl group , A C 6 to C 40 heteroarylalkyl group, a C 3 to C 40 cycloalkyl group, a C 1 to C 40 halogenalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, a C A C 3 to C 40 arylsilyl group, and a C 3 to C 40 heteroarylsilyl group;
이때 R1 내지 R19는 각각 인접하는 치환기와 축합(fused)되거나 또는 고리를 형성할 수 있다.Wherein R 1 to R 19 may each be fused to adjacent substituents or may form a ring.
또한, 본 발명은 (i) 양극, (ⅱ) 음극, 및 (ⅲ) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물 층을 포함하는 유기 전계 발광 소자로서, 화학식 1로 표시되는 화합물로 이루어진 군에서 선택되는 1종 이상의 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode, wherein the compound And at least one compound selected from the group consisting of an organic electroluminescent device and an organic electroluminescent device.
여기서 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층, 정공 주입층 및 정공 수송층으로 구성된 군으로부터 선택되는 하나 이상인 것이 바람직하며, 특히 발광층의 인광 또는 형광의 호스트 재료인 것이 더욱 바람직하다.Here, the organic material layer containing the compound represented by the formula (1) is preferably at least one selected from the group consisting of a light emitting layer, a hole injecting layer and a hole transporting layer, and more preferably a host material for phosphorescence or fluorescence of the light emitting layer.
본 발명의 화학식 1로 표시되는 화합물은 휘도, 전력효율, 내열성, 정공 또는 전자 수송, 주입 성능이 우수하고, 발광층으로 색순도 및 발광효율의 증가를 나타낼 수 있으므로, 유기 전계 발광 소자의 정공 및 전하 주입층, 수송층 및 발광층의 인광 및 형광의 호스트, 도판트 중 하나 이상에 적용할 수 있다. The compound represented by the general formula (1) of the present invention is excellent in luminance, power efficiency, heat resistance, hole or electron transporting and injection performance, and can exhibit increased color purity and luminous efficiency as a light emitting layer. Layer, a transport layer, and a phosphorescent and fluorescent host or dopant of the light emitting layer.
따라서, 본 발명의 신규 화합물을 사용하는 경우, 낮은 구동전압, 높은 전류효율 및 장수명을 나타내는 매우 양호한 유기 전계 발광소자(OLED)를 제조할 수 있다.Therefore, when using the novel compounds of the present invention, it is possible to produce a very good organic electroluminescent device (OLED) exhibiting low driving voltage, high current efficiency and long life.
도 1은 본 발명의 일 실시예에 따른 유기 EL 소자의 개략적인 단면도이다.1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명에서는 종래 유기 발광소자용 재료 [예, N4,N4′-di(naphthalene-1-yl)-N4,N4′-diphenylbiphenyl-4,4′-diamine (이하 NPB로 표시)와 4,4-dicarbazolybiphenyl (이하 CBP로 표시)] 보다 높은 분자량을 가지면서, 넓은 에너지 밴드갭을 갖는 특정 구조의 트리페닐렌계 화합물(triphenylene-based compound)을 제공하는 것을 특징으로 한다.In the present invention, a material for a conventional organic light emitting device [for example, N4, N4'-di (naphthalene-1-yl) -N4, N4'- diphenylbiphenyl-4,4'- dicarbazolybiphenyl (hereinafter abbreviated as CBP)], and has a wide energy bandgap and a triphenylene-based compound having a specific structure.
상기 화학식 1로 표시되는 화합물은, 트리페닐렌계 기본 골격에 축합(fused) 헤테로환 모이어티가 연결됨으로써, 오비탈 혼성(mixing)을 통해 삼중항 에너지 레벨(Triplet energy state)을 안정하게 형성하는 효과를 유도함과 동시에, 여러 치환체에 의해 에너지 레벨이 조절됨으로써 넓은 밴드갭 (sky blue ~ red)을 갖게 된다. 이로 인해 소자의 인광특성을 개선함과 동시에 전자 및/또는 정공 수송 능력, 발광효율, 구동전압, 수명 특성 등이 개선될 수 있다. 따라서 발광층 뿐만 아니라 여러 치환체의 도입으로 정공 수송층, 전자 수송층, 호스트 등으로 응용될 수 있다. 특히, 트리페닐렌계 기본 골격에서 유래된 넓은 밴드갭으로 인해 호스트 재료로서의 우수한 특성을 나타낼 수 있으며, 3차 아민 등과 같은 치환체 도입으로 인해 정공수송층 (hole transport layer, HTL) 재료로서 우수한 특성을 나타낼 수 있다. The compound represented by Formula 1 has an effect of forming a triplet energy state stably through orbital mixing by connecting a fused heterocyclic moiety to a triphenylene base skeleton At the same time, the energy level is controlled by various substituents, resulting in a broad band gap (sky blue ~ red). As a result, the phosphorescence characteristics of the device can be improved and the electron and / or hole transporting ability, luminous efficiency, driving voltage, lifetime characteristics and the like can be improved. Therefore, it can be applied not only as a light emitting layer but also as a hole transporting layer, an electron transporting layer and a host by introducing various substituents. Particularly, it can exhibit excellent characteristics as a host material due to a wide band gap derived from a triphenylene base skeleton and can exhibit excellent properties as a hole transport layer (HTL) material due to the introduction of a substituent such as a tertiary amine have.
또한 트리페닐렌계 기본골격에, 다수 도입된 다양한 방향족 환 (aromatic ring) 치환체로 인해 화합물의 분자량이 유의적으로 증대됨으로써, 유리전이온도가 향상되고 이로 인해 종래 NPB 또는 CBP 보다 높은 열적 안정성을 가질 수 있다. 따라서 본 발명의 트리페닐렌계 화합물을 포함하는 소자는 내구성 및 수명 향상을 발휘할 수 있다. In addition, the molecular weight of the compound is significantly increased due to various aromatic ring substituents introduced into the triphenylene-based skeleton, whereby the glass transition temperature is improved and thus the polymer has higher thermal stability than the conventional NPB or CBP have. Therefore, the device including the triphenylene compound of the present invention can exhibit improvement in durability and lifetime.
아울러, 상기 화합물을 유기 발광 소자의 정공 수송층 및 청색, 녹색 및/또는 적색의 인광 호스트 재료 또는 형광 호스트 재료로 채택할 경우, NPB 및 CBP 대비 효율 및 수명 면에서 월등히 우수한 효과를 발휘할 수 있다. 따라서 본 발명에 따른 화학식 1의 화합물로 표시되는 화합물은 유기 발광 소자의 성능 개선 및 수명 향상에 크게 기여할 수 있으며, 특히 이러한 소자 수명 향상은 풀 칼라 유기 발광 패널에서의 성능 극대화에도 큰 효과가 있다.In addition, when the compound is used as a hole transporting layer and a blue, green and / or red phosphorescent host material or a fluorescent host material of an organic light emitting device, it is possible to exert an excellent effect in terms of efficiency and life as compared to NPB and CBP. Therefore, the compound represented by the formula (1) according to the present invention can greatly contribute to improvement of the performance and lifetime of the organic light emitting device, and particularly, such lifetime improvement of the device has a great effect in maximizing the performance of the full color organic light emitting panel.
본 발명의 화학식 1로 표현되는 화합물은, 각각 하기 화학식 2 내지 화학식 7 중 어느 하나로 보다 구체화하여 표현될 수 있다.The compounds represented by formula (1) of the present invention may be represented by the following formulas (2) to (7), respectively.
상기 식에서, Where
R1 내지 R19는 상기 화학식 1에서 정의된 바와 동일하다.R 1 to R 19 are the same as defined in the above formula (1).
본 발명에 따른 트리페닐렌계 화합물에서, X로서 S를 포함하는 화학식 1의 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 한정되는 것은 아니다. In the triphenylene compound according to the present invention, the compound of the formula (1) containing S as X can be further formulated by the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.
본 발명에 따른 트리페닐렌계 화합물에서, X로서 O를 포함하는 화학식 1의 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 한정되는 것은 아니다. In the triphenylene type compound according to the present invention, the compound of the formula (1) containing O as X can be further specified by the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.
본 발명에 따른 트리페닐렌계 화합물에서, X로서 CR16R17를 포함하는 화학식 1의 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 한정되는 것은 아니다. In the triphenylene compound according to the present invention, the compound of the formula (1) containing CR 16 R 17 as X can be further formulated into the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.
본 발명에 따른 트리페닐렌계 화합물에서, X로서 SiR18R19를 포함하는 화학식 1의 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 한정되는 것은 아니다. In the triphenylene compound according to the present invention, the compound of the formula (1) containing SiR 18 R 19 as X can be further formulated into the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.
본 발명에 따른 트리페닐렌계 화합물에서, X로서 S=O를 포함하는 화학식 1의 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 한정되는 것은 아니다. In the triphenylene compound according to the present invention, the compound of the formula (1) containing S = O as X can be further formulated into the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.
본 발명에 따른 트리페닐렌계 화합물에서, X로서 SO2를 포함하는 화학식 1의 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 한정되는 것은 아니다. In the triphenylene type compound according to the present invention, the compound of the formula (1) containing SO 2 as X can be further specified by the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.
본 발명의 화학식 1 내지 화학식 7로 표시되는 화합물은 일반적인 합성방법에 따라 합성될 수 있다. (chem. Rev. , 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 참조) 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.The compounds represented by the general formulas (1) to (7) of the present invention can be synthesized according to a general synthesis method. (see Chem . Rev. , 60 : 313 (1960), J. Chem. SOC . 4482 (1955), Chem. Rev. 95: 2457 (1995)). .
본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1, 바람직하게는 화학식 2 내지 화학식 7로 표시되는 화합물을 포함하는 유기 전계 발광 소자에 관한 것이다.Another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by Formula 1, preferably Formula 2 to Formula 7, according to the present invention.
구체적으로, 본 발명은 양극(anode); 음극(cathode); 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 1층 이상의 유기물 층 중 적어도 하나는 상기 화학식 1, 바람직하게는 화학식 2 내지 화학식 7로 표시되는 화합물을 포함하는 것을 특징으로 한다. 이때, 상기 화학식 1 내지 화학식 7의 화합물은 단독 또는 복수로 포함될 수 있다.Specifically, the present invention provides a fuel cell comprising: an anode; A cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1, preferably Formula 2 to Formula 7, Or a compound thereof. At this time, the compounds represented by Chemical Formulas 1 to 7 may be included singly or in plurality.
본 발명의 화학식 1, 바람직하게는 화학식 2 내지 화학식 7로 표시되는 화합물을 포함하는 유기물 층은 정공 주입층, 정공 수송층, 및 발광층 중 어느 하나 이상일 수 있다. 바람직하게는 정공 주입층, 정공 수송층 재료로서 유기 EL 소자에 포함될 수 있다. 이 경우 유기 EL 소자는 정공 주입/수송 능력을 극대화할 수 있다. 또한 유기 EL 소자의 발광층 재료로 사용됨으로써, 향상된 효율 및 수명을 제공할 수 있다.The organic material layer containing the compound represented by the formula (1) of the present invention, preferably the compounds represented by the formulas (2) to (7) may be any one or more of a hole injecting layer, a hole transporting layer, and a light emitting layer. And may be included in the organic EL device as the hole injection layer and the hole transport layer material. In this case, the organic EL device can maximize the hole injection / transport capability. And can be used as a light emitting layer material of an organic EL device, thereby providing an improved efficiency and a service life.
본 발명에서 발광층은 인광 게스트 재료 또는 형광 게스트 재료를 포함할 수 있다. 바람직하게는, 상기 화학식 1 내지 화학식 7로 표시되는 화합물은 청색, 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 정공수송 물질 및/또는 정공전달 물질로서 유기 발광 소자에 포함될 수 있다. In the present invention, the light emitting layer may include a phosphorescent guest material or a fluorescent guest material. Preferably, the compounds represented by Chemical Formulas 1 to 7 may be included in the organic light emitting device as blue, green and / or red phosphorescent host, fluorescent host, hole transport material and / or hole transport material.
이때, 본 발명에 따른 트리페닐렌계 화합물은 호스트 재료로서 바람직하다. 여기에, 3차 아민 등의 치환체가 도입되는 화학식 1의 화합물은 정공 수송층 (HTL) 재료로서 바람직하다. At this time, the triphenylene compound according to the present invention is preferable as a host material. Here, the compound of the formula (1) wherein a substituent such as a tertiary amine is introduced is preferable as a hole transporting layer (HTL) material.
또한 본 발명에 따른 화학식 1, 바람직하게는 화학식 2 내지 화학식 7로 표시되는 화합물은 150℃ 이상의 높은 유리 전이 온도를 가지고 있다. 따라서 상기 화합물을 유기 발광 소자의 유기물 층으로 사용할 경우, 유기 발광 소자 내에서 결정화가 일어나는 것이 최소화되기 때문에, 소자의 구동전압을 낮출 수 있고, 발광효율, 열적 안정성 및 수명 특성을 향상시킬 수 있다.Also, the compound represented by Formula 1 according to the present invention, preferably compounds represented by Formula 2 to Formula 7, has a high glass transition temperature of 150 ° C or higher. Therefore, when the compound is used as the organic material layer of the organic light emitting device, the crystallization in the organic light emitting device is minimized, so that the driving voltage of the device can be lowered and the light emitting efficiency, thermal stability and lifetime characteristics can be improved.
본 발명에 따른 유기 EL 소자 구조의 비제한적인 예를 들면, 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 것일 수 있다. 이때 상기 발광층, 정공 주입층, 정공 수송층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 상기 전자 수송층 위에는 전자 주입층이 위치할 수도 있다.Non-limiting examples of the structure of the organic EL device according to the present invention may include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode sequentially laminated. In this case, at least one of the emission layer, the hole injection layer, and the hole transport layer may include the compound represented by Chemical Formula 1. An electron injection layer may be positioned on the electron transport layer.
또한, 본 발명에 따른 유기 발광 소자는 전술한 바와 같이 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조 뿐만 아니라, 전극과 유기물 층 계면에 절연층 또는 접착층이 삽입될 수도 있다. In addition, as described above, the organic light emitting device according to the present invention may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic layer.
본 발명의 유기 발광 소자에 있어서, 상기 화학식 1 내지 화학식 7의 화합물을 포함하는 상기 유기물 층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포의 예로는 스핀 코팅, 딥 코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에만 한정되지 않는다. In the organic light emitting device of the present invention, the organic material layer containing the compounds represented by Chemical Formulas 1 to 7 may be formed by a vacuum evaporation method or a solution coating method. Examples of the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
본 발명에 따른 유기 전계 발광 소자는, 유기물층 중 1층 이상을 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 통상적인 재료 및 방법을 이용하여 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device according to the present invention is an organic material layer and an electrode using conventional materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1 above. It can be prepared by forming.
예컨데, 기판으로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름이나 시트 등이 사용될 수 있다.For example, a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합물; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜] (PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에만 한정 되는 것은 아니다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of oxides with metals 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 and polyaniline; Or carbon black, but are not limited thereto.
음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
상기 정공 주입층, 정공 수송층 및 전자 주입층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질이 사용될 수 있다.The hole injecting layer, the hole transporting layer, and the electron injecting layer are not particularly limited, and conventional materials known in the art can be used.
이하, 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.
Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
[[ 합성예Synthetic example 1: 화합물 2- 1: compound 2- bromo-bromo- 7-(2-(7- (2- ( methylsulfinylmethylsulfinyl )) phenylphenyl )) triphenylenetriphenylene 의 합성]Synthesis of
질소 기류하에서 2-(7-bromotriphenylen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5.0 g (11.54 mmol)과 1-bromo-2-(methylsulfinyl) benzene 2.78 g (12.70 mmol)를 톨루엔 75ml에 녹인 후 2M K2CO3 (8ml) 를 넣고 가스를 제거한 다음, 0.73g 의 Pd(PPh3)4 (5mol%)를 넣고, 90℃에서 24시간 교반하였다. 상온으로 온도를 내린 후 디클로로메탄으로 추출하고, MgSO4 로 수분을 제거한 후 EA / Hexane (1:3)을 사용하여 컬럼으로 분리하여 목적 화합물인 2-bromo-7-(2-(methylsulfinyl)phenyl)triphenylene 3.49 g (수율 68 %)을 얻었다. 5.0 g (11.54 mmol) of 2- (7-bromotriphenylen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 1-bromo-2- (methylsulfinyl) benzene 2.78 g (12.70 mmol) was dissolved in 75 ml of toluene, and 2M K 2 CO 3 (8 ml) was added to remove gas. Then 0.73 g of Pd (PPh 3 ) 4 (5 mol%) was added and stirred at 90 ° C for 24 hours. After the reaction mixture was cooled to room temperature, the reaction mixture was extracted with dichloromethane, the water was removed with MgSO 4 , and the residue was purified by column chromatography using EA / Hexane (1: 3) to obtain 2-bromo-7- (2- (methylsulfinyl) ) triphenylene (yield: 68%).
1H NMR : 2.65 (s, 3H), 7.52 (d, 2H), 7.84 (m, 3H), 8.00 (m, 4H), 8.16 (d, 2H), 8.95 (d, 2H), 9.05 (s, 1H).
1 H NMR: 2.65 (s, 3H), 7.52 (d, 2H), 7.84 (m, 3H), 8.00 (m, 4H), 8.16 (d, 2H), 8.95 (d, 2H), 9.05 (s, 1H).
[합성예 2 : 화합물 6-bromobenzo[d]triphenyleno[2,3-b]thiophene의 합성][Synthesis Example 2: Synthesis of compound 6-bromobenzo [d] triphenyleno [2,3-b] thiophene]
질소 기류하에서 2-bromo-7-(2-(methylsulfinyl)phenyl)triphenylene 3.49 g (7.84 mmol) 과 CF3SO3H 100ml, phosphorus pentoxide 0.55g (3.92 mmol)을 플라스크에 넣고, 상온에서 72시간을 교반하였다. Ice-water 500ml 를 플라스크에 넣고, 노란색 침전물은 필터 후에 건조하였다. Pyridine 500ml에 건조되어진 물질을 넣고 12시간 reflux 한 다음, 온도를 내리고 디클로로메탄으로 추출한 후, MgSO4 로 수분을 제거하였다. EA / Hexane (1:7)을 사용하여 컬럼으로 분리하여 목적 화합물인 6-bromobenzo[d]triphenyleno[2,3-b]thiophene 2.87 g (수율 88 %)을 얻었다. 3.49 g (7.84 mmol) of 2-bromo-7- (2- (methylsulfinyl) phenyl) triphenylene, 100 ml of CF 3 SO 3 H and 0.55 g (3.92 mmol) of phosphorus pentoxide were placed in a flask under nitrogen flow for 72 hours Lt; / RTI > 500 ml of ice-water was placed in a flask, and the yellow precipitate was dried after filtration. The dried material was added to 500 ml of pyridine, and the mixture was refluxed for 12 hours. Then, the mixture was cooled, extracted with dichloromethane, and then dehydrated with MgSO 4 . EA / hexane (1: 7) as eluent to obtain 2.87 g (yield: 88%) of 6-bromobenzo [d] triphenyleno [2,3- b] thiophene as a target compound.
1H NMR : 7.52 (d, 2H), 7.84 (m, 3H), 8.00 (m, 4H), 8.16 (d, 2H), 8.95 (s, 1H), 9.05 (s, 1H).
1 H NMR: 7.52 (d, 2H), 7.84 (m, 3H), 8.00 (m, 4H), 8.16 (d, 2H), 8.95
[합성예 3: 화합물 (2-(7-bromotriphenylen-2-yl)phenyl)dimethyl silane의 합성] Synthesis Example 3 Synthesis of Compound (2- (7-bromotriphenylen-2-yl) phenyl) dimethyl silane
7-bromotriphenylen-2-ylboronic acid 10 g (28.49 mmol), (2-bromophenyl)dimethylsilane 5.11 g (23.74 mmol), Pd(PPh3)4 1.37 g (5 mol%), K2CO3 9.84 g (71.23 mmol), 그리고 THF/증류수 (200ml/100ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 (2-(7-bromotriphenylen-2-yl)phenyl)dimethylsilane 7.13 g (수율 68 %)을 획득하였다. 7-bromotriphenylen-2-ylboronic acid 10 g (28.49 mmol), (2-bromophenyl) dimethylsilane 5.11 g (23.74 mmol), Pd (PPh 3) 4 1.37 g (5 mol%), K 2 CO 3 9.84 g (71.23 mmol) and THF / distilled water (200 ml / 100 ml), 7.13 g (yield: 68%) of 2- (7-bromotriphenylen- .
1H NMR : 0.66 (s, 6H), 3.82 (s, 1H), 7.53 (d, 2H), 7.81 (m, 3H), 7.99 (m, 4H), 8.14 (d, 2H), 8.96 (d, 2H), 9.04 (s, 1H).
1 H NMR: 0.66 (s, 6H), 3.82 (s, 1H), 7.53 (d, 2H), 7.81 (m, 3H), 7.99 (m, 4H), 8.14 (d, 2H), 8.96 (d, 2H), 9.04 (s, 1 H).
[합성예 4: 화합물 6-bromo-10,10-dimethyl-10H-benzo[d]triphenyl eno[2,3-b]silole의 합성]Synthesis Example 4 Synthesis of Compound 6-bromo-10,10-dimethyl-10H-benzo [d] triphenyl eno [2,3-b] silole
질소 기류하에서 (2-(7-bromotriphenylen-2-yl)phenyl)dimethylsilane 3.0 g (6.80 mmol)과 RhCl(PPh3)3 31.3 mg (0.034 mmol) 를 1,4-dioxane 10ml에 녹인 후, 135℃에서 1시간 교반하였다. 용매를 제거한 후 EA : Hexane (1:3)으로 컬럼하여 목적 화합물인 6-bromo-10,10-dimethyl-10H-benzo[d]triphenyl eno[2,3-b]silole 2.52 g (수율 83 %)을 얻었다. In a nitrogen atmosphere (2- (7-bromotriphenylen-2 -yl) phenyl) dimethylsilane 3.0 g (6.80 mmol) and RhCl (PPh 3) 3 were dissolved 31.3 mg (0.034 mmol) in 1,4-dioxane 10ml, 135 ℃ Lt; / RTI > for 1 hour. After removal of the solvent, 2.52 g (yield 83%) of the target compound, 6-bromo-10,10-dimethyl-10H-benzo [d] triphenylenol [2,3-b] silole was obtained by column chromatography with EA: Hexane (1: ).
1H NMR : 0.68 (s, 6H), 7.54 (d, 2H), 7.83 (m, 3H), 7.98 (m, 4H), 8.15 (d, 2H), 8.95 (d, 2H), 9.02 (s, 1H).
1 H NMR: 0.68 (s, 6H), 7.54 (d, 2H), 7.83 (m, 3H), 7.98 (m, 4H), 8.15 (d, 2H), 8.95 (d, 2H), 9.02 (s, 1H).
[합성예 5: 화합물 2-bromo-7-(2-isopropylphenyl)triphenylene의 합성][Synthesis Example 5: Synthesis of compound 2-bromo-7- (2-isopropylphenyl) triphenylene]
7-bromotriphenylen-2-ylboronic acid 10 g (28.5 mmol), 1-bromo-2-isopropylbenzene 6.18 g (34.2 mmol), Pd(PPh3)4 1.98 g (5 mol%), K2CO3 11.82 g (77.7 mmol), 그리고 THF/증류수 (200ml/100ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 2-bromo-7-(2-isopropylphenyl)triphenylene 7.6 g (수율 63 %)을 획득하였다. 7-bromotriphenylen-2-ylboronic acid 10 g (28.5 mmol), 1-bromo-2-isopropylbenzene 6.18 g (34.2 mmol), Pd (PPh 3) 4 1.98 g (5 mol%), K 2 CO 3 11.82 g ( 77.7 mmol) and THF / distilled water (200 ml / 100 ml) were used in the same manner as in Synthesis Example 1 to obtain 7.6 g of 2-bromo-7- (2-isopropylphenyl) triphenylene .
1H NMR : 1.23 (s, 6H) 2.87 (m, 1H), 7.54 (d, 2H), 7.86 (m, 3H), 8.02 (m, 4H), 8.19 (d, 2H), 8.94 (d, 2H), 9.04 (s, 1H).
1 H NMR: 1.23 (s, 6H) 2.87 (m, 1H), 7.54 (d, 2H), 7.86 (m, 3H), 8.02 (m, 4H), 8.19 (d, 2H), 8.94 (d, 2H ), 9.04 (s, 1 H).
[합성예 6: 화합물 6-bromo-10,10-dimethyl-10H-indeno[2,1-b]tri phenylene의 합성]Synthesis Example 6 Synthesis of Compound 6-bromo-10,10-dimethyl-10H-indeno [2,1-b] tri phenylene
2-bromo-7-(2-isopropylphenyl)triphenylene 7.6 g (17.9 mmol)과 RhCl(PPh3)3 164.8 mg (0.18 mmol), 그리고 1,4-dioxane 10ml를 사용하여 합성예 4와 동일한 방법으로 목적 화합물인 6-bromo-10,10-dimethyl-10H-indeno[2,1-b]tri phenylene 6.2 g (수율 82 %)을 얻었다.The purpose with 2-bromo-7- (2- isopropylphenyl) triphenylene 7.6 g (17.9 mmol) and RhCl (PPh 3) 3 164.8 mg (0.18 mmol), and 1,4-dioxane 10ml same manner as in Example 4 using 6.2 g (yield 82%) of 6-bromo-10,10-dimethyl-10H-indeno [2,1-b]
1H NMR : 1.78 (s, 6H), 7.57 (d, 2H), 7.84 (m, 3H), 8.02 (m, 4H), 8.15 (d, 2H), 8.93 (d, 2H), 9.02 (s, 1H).
1 H NMR: 1.78 (s, 6H), 7.57 (d, 2H), 7.84 (m, 3H), 8.02 (m, 4H), 8.15 (d, 2H), 8.93 (d, 2H), 9.02 (s, 1H).
[합성예 7: 화합물 2-(2-benzhydrylphenyl)-7-bromotriphenylene의 합성][Synthesis Example 7: Synthesis of compound 2- (2-benzhydrylphenyl) -7-bromotriphenylene]
7-bromotriphenylen-2-ylboronic acid 10 g (28.5 mmol), ((2-bromophenyl)methylene)dibenzene 11.05 g (34.2 mmol), Pd(PPh3)4 1.98 g (5 mol%), K2CO3 11.82 g (77.7 mmol), 그리고 THF/증류수 (200ml/100ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 2-(2-benzhydryl phenyl)-7-bromotriphenylene 11.95 g (수율 76 %)을 획득하였다. 7-bromotriphenylen-2-ylboronic acid 10 g (28.5 mmol), ((2-bromophenyl) methylene) dibenzene 11.05 g (34.2 mmol), Pd (PPh 3) 4 1.98 g (5 mol%), K 2 CO 3 11.82 (yield: 76%) of the target compound, 2- (2-benzhydrylphenyl) -7-bromotriphenylene, was obtained in the same manner as in Synthesis Example 1, except that the starting material was replaced with THF / distilled water (200 ml / 100 ml) .
1H NMR : 5.48 (s, 1H), 7.55 (d, 2H), 7.87 (m, 5H), 8.11 (m, 6H), 8.18 (d, 2H), 8.52 (m, 6H), 8.87 (d, 2H), 9.03 (s, 1H).
1 H NMR: 5.48 (s, 1H), 7.55 (d, 2H), 7.87 (m, 5H), 8.11 (m, 6H), 8.18 (d, 2H), 8.52 (m, 6H), 8.87 (d, 2H), 9.03 (s, 1 H).
[합성예 8: 화합물 6-bromo-10,10-diphenyl-10H-indeno[2,1-b]tri phenylene의 합성]Synthesis Example 8 Synthesis of Compound 6-bromo-10,10-diphenyl-10H-indeno [2,1-b] tri phenylene
2-(2-benzhydrylphenyl)-7-bromotriphenylene 11.95 g (21.7 mmol)과 RhCl(PPh3)3 200 mg (0.22 mmol), 그리고 1,4-dioxane 10ml를 사용하여 합성예 4와 동일한 방법으로 목적 화합물인 6-bromo-10,10-diphenyl-10H-indeno[2,1-b]triphenylene 9.86 g (수율 83 %)을 얻었다. 2- (2-benzhydrylphenyl) -7- bromotriphenylene 11.95 g (21.7 mmol) and RhCl (PPh 3) 3 200 mg (0.22 mmol), and 1,4-dioxane 10ml purpose in the same manner as in Example 4 using compound 9.86 g (yield: 83%) of 6-bromo-10,10-diphenyl-10H-indeno [2,1- b] triphenylene was obtained.
1H NMR : 7.56 (d, 2H), 7.88 (m, 5H), 8.08 (m, 6H), 8.19 (d, 2H), 8.50 (m, 6H), 8.85 (d, 2H), 9.04 (s, 1H).
1 H NMR: 7.56 (d, 2H), 7.88 (m, 5H), 8.08 (m, 6H), 8.19 (d, 2H), 8.50 (m, 6H), 8.85 (d, 2H), 9.04 (s, 1H).
[합성예 9: 화합물 Inv5-16의 합성]-실시예 1[Synthesis Example 9: Synthesis of compound Inv5-16] - Example 1
6-bromobenzo[d]triphenyleno[2,3-b]thiophene 5 g (12.10 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid 4.17 g (14.52 mmol), Pd(PPh3)4 0.7 g (5 mol%), NaOH 1.45 g (36.29 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv5-16 5.64 g (수율 81 %)을 획득하였다. 6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 5 g (12.10 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid 4.17 g (14.52 mmol), Pd (PPh 3) 4 0.7 g ( (Yield: 81%) of the target compound Inv5-16 was obtained in the same manner as in Synthesis Example 1 using 1.45 g (36.29 mmol) of NaOH and THF / distilled water (100 ml / 50 ml) .
GC-Mass (이론치 : 575.17 g/mol, 측정치 : 575 g/mol)
GC-Mass (calculated: 575.17 g / mol, measured: 575 g / mol)
[합성예 10: 화합물 Inv5-57의 합성]-실시예 2[Synthesis Example 10: Synthesis of compound Inv5-57] - Example 2
6-bromobenzo[d]triphenyleno[2,3-b]thiophene 5 g (12.10 mmol), 4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid 4.56 g (14.52 mmol), Pd(PPh3)4 0.69 g (5 mol%), NaOH 1.45 g (36.29 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv5-57 6.2 g (수율 85 %)을 획득하였다. 4.56 g (14.52 mmol) of 4- (1-phenyl- 1H-benzo [d] imidazol-2-yl) phenylboronic acid were added to a solution of 5 g (12.10 mmol) of 6-bromobenzo [ Pd (PPh 3) 4 0.69 g (5 mol%), NaOH 1.45 g (36.29 mmol), and THF / distilled water (100ml / 50ml) using the test in the same manner as in synthesis example 1, the desired compound 6.2 Inv5-57 g (yield: 85%).
GC-Mass (이론치 : 602.18 g/mol, 측정치 : 602 g/mol)
GC-Mass (theory: 602.18 g / mol, measurement: 602 g / mol)
[합성예 11 : 화합물 Inv5-14의 합성] - 실시예 3[Synthesis Example 11: Synthesis of compound Inv5-14] - Example 3
6-bromobenzo[d]triphenyleno[2,3-b]thiophene 6.18 g (14.95 mmol), 9H-carbazole 3 g (17.94 mmol), Pd2(dba)3 0.68 g (5 mol%), P(t-bu)3 0.3 g (1.5 mmol), NaO(t-bu) 3.59 g (37.38 mmol), 그리고 200 ml의 Toluene을 사용하여 합성예 3과 동일한 방법으로 목적 화합물인 Inv5-14 3.06 g (수율 41 %)을 획득하였다. 6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 6.18 g (14.95 mmol), 9H-carbazole 3 g (17.94 mmol), Pd 2 (dba) 3 0.68 g (5 mol%), P (t- 3.06 g (Yield: 41%) of the target compound Inv5-14 was obtained in the same manner as in Synthesis Example 3, except that 0.3 g (1.5 mmol) of 3 , 3.59 g (37.38 mmol) of NaO ).
GC-Mass (이론치 : 499.14 g/mol, 측정치 : 499 g/mol)
GC-Mass (theory: 499.14 g / mol, measurement: 499 g / mol)
[합성예 12 : 화합물 Inv5-35의 합성] - 실시예 4[Synthesis Example 12: Synthesis of compound Inv5-35] - Example 4
6-bromobenzo[d]triphenyleno[2,3-b]thiophene 5 g (12.10 mmol), quinolin-3-ylboronic acid 2.51 g (14.52 mmol), Pd(PPh3)4 0.69 g (5 mol%), NaOH 1.45 g (36.29 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv5-35 4.41 g (수율 79 %)을 획득하였다. 6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 5 g (12.10 mmol), quinolin-3-ylboronic acid 2.51 g (14.52 mmol), Pd (PPh 3) 4 0.69 g (5 mol%), NaOH 1.45 g (36.29 mmol) of the title compound, and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 4.41 g (yield 79%) of the target compound Inv5-35.
GC-Mass (이론치 : 461.58 g/mol, 측정치 : 461 g/mol)
GC-Mass (calculated: 461.58 g / mol, measured: 461 g / mol)
[합성예 13 : 화합물 Inv5-51의 합성] - 실시예 5[Synthesis Example 13: synthesis of compound Inv5-51] - Example 5
6-bromobenzo[d]triphenyleno[2,3-b]thiophene 5 g (12.10 mmol), 4,6-di(pyridin-4-yl)pyrimidin-2-ylboronic acid 4.04 g (14.52 mmol), Pd(PPh3)4 0.69 g (5 mol%), NaOH 1.45 g (36.29 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv5-51 5.69 g (수율 83 %)을 획득하였다. A solution of 4.0 g (14.52 mmol) of 4,6-di (pyridin-4-yl) pyrimidin-2-ylboronic acid, 5 g (12.10 mmol) of 6-bromobenzo [d] triphenyleno [2,3- b] thiophene, 3) 4 0.69 g (5 mol %), NaOH 1.45 g (36.29 mmol), and THF / distilled water (100ml / 50ml) and the experiment in the same manner as in synthesis example 1, the desired compound using the Inv5-51 5.69 g (yield 83%).
GC-Mass (이론치 : 566.16 g/mol, 측정치 : 566 g/mol)
GC-Mass (calculated: 566.16 g / mol, measured: 566 g / mol)
[합성예 14: 화합물 Inv7-35의 합성]-실시예 6[Synthesis Example 14: synthesis of compound Inv7-35] - Example 6
6-bromo-10,10-dimethyl-10H-indeno[2,1-b]triphenylene 5 g (11.188 mmol), quinolin-3-ylboronic acid 2.45 g (14.17 mmol), Pd(PPh3)4 0.68 g (5 mol%), NaOH 1.42 g (35.43 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv7-35 4.34 g (수율 78%)을 획득하였다. 6-bromo-10,10-dimethyl- 10H-indeno [2,1-b] triphenylene 5 g (11.188 mmol), quinolin-3-ylboronic acid 2.45 g (14.17 mmol), Pd (PPh 3) 4 0.68 g ( (Yield: 78%) of the target compound Inv7-35 was obtained in the same manner as in Synthesis Example 1, except that 1.9 g (5 mol%) of NaOH, 1.42 g (35.43 mmol) of NaOH and THF / distilled water .
GC-Mass (이론치 : 471.20 g/mol, 측정치 : 471 g/mol)
GC-Mass (calculated: 471.20 g / mol, measured: 471 g / mol)
[합성예 15: 화합물 Inv7-106의 합성]-실시예 7[Synthesis Example 15: synthesis of compound Inv7-106] - Example 7
6-bromo-10,10-diphenyl-10H-indeno[2,1-b]triphenylene 5 g (9.13 mmol), b 3.04 g (10.96 mmol), Pd(PPh3)4 0.53 g (5 mol%), NaOH 1.10 g (27.40 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv7-106 4.35 g (수율 80 %)을 획득하였다. 6-bromo-10,10-diphenyl- 10H-indeno [2,1-b] triphenylene 5 g (9.13 mmol), b 3.04 g (10.96 mmol), Pd (PPh 3) 4 0.53 g (5 mol%), 4.35 g (yield 80%) of the target compound Inv7-106 was obtained by conducting the same method as in Synthesis Example 1 using 1.10 g (27.40 mmol) of NaOH and THF / distilled water (100 ml / 50 ml)
GC-Mass (이론치 : 595.23 g/mol, 측정치 : 595 g/mol)
GC-Mass (calculated: 595.23 g / mol, measured: 595 g / mol)
[합성예 16: 화합물 Inv8-42의 합성]-실시예 8[Synthesis Example 16: synthesis of compound Inv8-42] - Example 8
6-bromo-10,10-dimethyl-10H-benzo[d]triphenyleno[2,3-b]silole 5 g (11.38 mmol), 2,3'-bipyridin-6-ylboronic acid 2.73 g (13.65 mmol), Pd(PPh3)4 0.66 g (5 mol%), NaOH 1.37 g (34.14 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv8-42 4.55 g (수율 82%)을 획득하였다. A solution of 5 g (11.38 mmol), 2,3'-bipyridin-6-ylboronic acid (2.73 g, 13.65 mmol), 6-bromo-10,10-dimethyl- Pd (PPh 3) 4 0.66 g (5 mol%), NaOH 1.37 g (34.14 mmol), and THF / distilled water (100ml / 50ml) using the test in the same manner as in synthesis example 1, the desired compound 4.55 Inv8-42 g (yield: 82%).
GC-Mass (이론치 : 487.18 g/mol, 측정치 : 487 g/mol)
GC-Mass (calculated: 487.18 g / mol, measured: 487 g / mol)
[합성예 17 : 화합물 Inv9-14의 합성]-실시예 9[Synthesis Example 17: synthesis of compound Inv9-14] - Example 9
질소 기류하에서 Inv5-14 5 g (10.83 mmol)을 디클로로메탄 100 ml에 녹인 후 디클로로메탄에 녹인 mCPBA 1.88 g (10.83 mmol)을 -30 ℃에서 적하하였다. 1시간 교반 후 상온으로 온도를 올리고 소듐카보네이트로 반응을 종결시키고 유기층을 분리하였다. 분리되어진 유기층을 MgSO4로 수분을 제거하고 EA / Hexane (1:1)로 컬럼하여 목적 화합물인 Inv9-14 2.41 g (수율 45 %)을 얻었다. 5 g (10.83 mmol) of Inv 5-14 was dissolved in 100 ml of dichloromethane under nitrogen flow, and 1.88 g (10.83 mmol) of mCPBA dissolved in dichloromethane was added dropwise at -30 ° C. After stirring for 1 hour, the temperature was raised to room temperature, the reaction was terminated with sodium carbonate, and the organic layer was separated. The separated organic layer was dehydrated with MgSO 4 and columned with EA / Hexane (1: 1) to obtain 2.41 g (yield: 45%) of the objective compound Inv9-14.
GC-Mass (이론치 : 493.11 g/mol, 측정치 : 493 g/mol)
GC-Mass (calculated: 493.11 g / mol, measured: 493 g / mol)
[합성예 18: 화합물 Inv9-51의 합성]-실시예 10[Synthesis Example 18: Synthesis of Compound Inv9-51] - Example 10
Inv5-51 5 g (8.82 mmol), mCPBA 1.53 g (8.82 mmol), 그리고 디클로로메탄 150 ml를 사용하여 합성예 88과 동일한 방법으로 실험하여 목적 화합물인 Inv9-51 2.36 g (수율 46 %)을 얻었다. In the same manner as in Synthesis Example 88, 5 g (8.82 mmol) of Inv5-51, 1.53 g (8.82 mmol) of mCPBA and 150 ml of dichloromethane were used to obtain 2.36 g (yield 46%) of the target compound Inv9-51 .
GC-Mass (이론치 : 582.67 g/mol, 측정치 : 582 g/mol)
GC-Mass (calculated: 582.67 g / mol, measured: 582 g / mol)
[합성예 19: 화합물 Inv10-35의 합성]-실시예 11[Synthesis Example 19: synthesis of compound Inv10-35] - Example 11
Inv5-35 5 g (10.83 mmol), mCPBA 4.7 g (27.08 mmol), 그리고 디클로로메탄 150 ml를 사용하여 합성예 88과 동일한 방법으로 실험하여 목적 화합물인 Inv10-35 2.36 g (수율 35 %)을 얻었다. In the same manner as in Synthesis Example 88, 5 g (10.83 mmol) of Inv5-35, 4.7 g (27.08 mmol) of mCPBA and 150 ml of dichloromethane were used to obtain 2.36 g (yield 35%) of the target compound Inv10-35 .
GC-Mass (이론치 : 493.11 g/mol, 측정치 : 493 g/mol)
GC-Mass (calculated: 493.11 g / mol, measured: 493 g / mol)
[합성예 20 : 화합물 Inv5-20의 합성]-실시예 12[Synthesis Example 20: Synthesis of compound Inv 5-20] - Example 12
6-bromobenzo[d]triphenyleno[2,3-b]thiophene 7.85 g (19.00 mmol), N-phenylnaphthalen-2-amine 5 g (22.80 mmol), Pd2(dba)3 0.87 g (5 mol%), P(t-bu)3 0.38 g (1.90 mmol), NaO(t-bu) 4.57 g (47.50 mmol), 그리고 200 ml의 Toluene을 사용하여 합성예 3과 동일한 방법으로 목적 화합물인 Inv5-20 6.92 g (수율 66 %)을 획득하였다. A mixture of 7.85 g (19.00 mmol) of 6-bromobenzo [d] triphenyleno [2,3-b] thiophene, 0.87 g (5 mol%) of Pd 2 (dba) 3 , 5 g (22.80 mmol) of N-phenylnaphthalen- In the same manner as in Synthesis Example 3, using 0.38 g (1.90 mmol) of P (t-bu) 3 , 4.57 g (47.50 mmol) of NaO (t-bu) and 200 ml of toluene, (Yield 66%).
GC-Mass (이론치 : 551.17 g/mol, 측정치 : 551 g/mol)
GC-Mass (calculated: 551.17 g / mol, measured: 551 g / mol)
[합성예 21 : 화합물 Inv5-64의 합성]-실시예 13[Synthesis Example 21: synthesis of compound Inv5-64] - Example 13
6-bromobenzo[d]triphenyleno[2,3-b]thiophene 5 g (12.10 mmol), 4-(naphthalen-2-yl(phenyl)amino)phenylboronic acid 4.92 g (14.51 mmol), Pd(PPh3)4 0.7 g (5 mol%), NaOH 1.45 g (36.29 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv5-64 5.92 g (수율 78 %)을 획득하였다. GC-Mass (이론치 : 627.20 g/mol, 측정치 : 627 g/mol)
6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 5 g (12.10 mmol), 4- (naphthalen-2-yl (phenyl) amino) phenylboronic acid 4.92 g (14.51 mmol), Pd (PPh 3) 4 5.92 g (yield 78%) of the target compound Inv5-64 was obtained in the same manner as in Synthesis Example 1, except that 0.7 g (5 mol%) of NaOH, 1.45 g (36.29 mmol) of NaOH and THF / distilled water (100 ml / . GC-Mass (calculated: 627.20 g / mol, measured: 627 g / mol)
[합성예 22: 화합물 Inv7-18의 합성]-실시예 14[Synthesis Example 22: synthesis of compound Inv7-18] - Example 14
6-bromo-10,10-dimethyl-10H-indeno[2,1-b]triphenylene 6.55 g (15.47 mmol), dinaphthalen-2-ylamine 5 g (18.56 mmol), Pd2(dba)3 0.71 g (5 mol%), P(t-bu)3 0.31 g (1.55 mmol), NaO(t-bu) 3.72 g (38.67 mmol), 그리고 200 ml의 Toluene을 사용하여 합성예 3과 동일한 방법으로 목적 화합물인 Inv7-18 6.15 g (수율 65 %)을 획득하였다. 6-bromo-10,10-dimethyl- 10H-indeno [2,1-b] triphenylene 6.55 g (15.47 mmol), dinaphthalen-2-ylamine 5 g (18.56 mmol), Pd 2 (dba) 3 0.71 g (5 mol%), P (t- bu) 3 0.31 g (1.55 mmol), NaO (t-bu) 3.72 g (38.67 mmol), and the target compound in the same manner as in Preparation example 3 using Toluene of 200 ml Inv7 -18 (6.15 g, yield 65%).
GC-Mass (이론치 : 611.26 g/mol, 측정치 : 611 g/mol)
GC-Mass (calculated: 611.26 g / mol, measured: 611 g / mol)
[합성예 23: 화합물 Inv7-127의 합성]-실시예 15[Synthesis Example 23: synthesis of compound Inv7-127] - Example 15
6-bromo-10,10-diphenyl-10H-indeno[2,1-b]triphenylene 5 g (9.13 mmol), 4-(naphthalen-1-yl(phenyl)amino)phenylboronic acid 3.72 g (10.96 mmol), Pd(PPh3)4 0.53 g (5 mol%), NaOH 1.10 g (27.40 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv7-127 5.5 g (수율 79%)을 획득하였다. GC-Mass (이론치 : 761.31 g/mol, 측정치 : 761 g/mol)
A solution of 3.72 g (10.96 mmol) of 6-bromo-10,10-diphenyl-10H-indeno [2,1-b] triphenylene 5 g (9.13 mmol), 4- (naphthalen- Pd (PPh 3) 4 0.53 g (5 mol%), NaOH 1.10 g (27.40 mmol), and THF / distilled water (100ml / 50ml) using the test in the same manner as in synthesis example 1, the desired compound 5.5 Inv7-127 g (yield: 79%). GC-Mass (calculated: 761.31 g / mol, measured: 761 g / mol)
[합성예 24: 화합물 Inv8-61의 합성]-실시예 16[Synthesis Example 24: synthesis of compound Inv8-61] - Example 16
6-bromo-10,10-dimethyl-10H-benzo[d]triphenyleno[2,3-b]silole 5 g (11.38 mmol), 4-(diphenylamino)phenylboronic acid 3.95 g (13.65 mmol), Pd(PPh3)4 0.66 g (5 mol%), NaOH 1.37 g (34.14 mmol), 그리고 THF/증류수 (100ml/50ml)를 사용하여 합성예 1과 동일한 방법으로 실험하여 목적 화합물인 Inv8-61 5.57 g (수율 81 %)을 획득하였다. GC-Mass (이론치 : 603.24 g/mol, 측정치 : 603 g/mol)
A solution of 5 g (11.38 mmol) of 4- (diphenylamino) phenylboronic acid, 3.95 g (13.65 mmol), Pd (PPh 3 ), and 3 -bromo-10,10- ) 4 0.66 g (5 mol% ), NaOH 1.37 g (34.14 mmol), and THF / distilled water (100ml / 50ml) Inv8-61 5.57 of the aimed compound by experiment in the same manner as in synthesis example 1 by using g (yield: 81 %). GC-Mass (theory: 603.24 g / mol, measured: 603 g / mol)
[실시예 1~11] 유기 EL 소자의 제조 및 평가[Examples 1 to 11] Preparation and evaluation of organic EL devices
하기와 같은 방법으로 유기 EL 소자를 제조하였다. An organic EL device was prepared in the following manner.
ITO (Indium tin oxide)가 1500Å의 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 이송하였다. The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO (양극) 위에 본 발명의 화합물들을 호스트로 이용하여 NPB(40nm) / Inv 화합물 + 10%Ir(ppy)3(20nm) / BCP(10nm) /Alq3(40nm) /LiF(1nm) /Al 순으로 발광 소자를 구성한 다음 이들의 발광 특성을 평가하였고, 그 결과를 하기 표 1에 기재하였다. 여기서, 호스트에 적용되는 화합물은 하기 표 1과 같다.
(40 nm) / Inv compound + 10% Ir (ppy) 3 (20 nm) / BCP (10 nm) / Alq 3 (40 nm) / LiF (10 nm) using the compounds of the present invention as a host on the ITO 1 nm) / Al, and then their luminescent characteristics were evaluated. The results are shown in Table 1 below. Here, the compounds to be applied to the host are shown in Table 1 below.
[비교예 1]Comparative Example 1
상기 실시예와 동일한 방법으로 준비된 전극 위에 NPB(40nm)/CBP + 10%Ir(ppy)3(20nm)/BCP(10nm)/Alq3(40nm)/LiF(1nm)/Al 순으로 발광 소자를 구성한 후, 실시예 1~11과 동일한 방법으로 발광특성을 평가하였다.(40 nm) / CBP + 10% Ir (ppy) 3 (20 nm) / BCP (10 nm) / Alq 3 (40 nm) / LiF (1 nm) / Al on the electrode prepared in the same manner as in the above- And the luminescent characteristics were evaluated in the same manner as in Examples 1 to 11.
참고로, NPB, CBP 및 Ir(ppy)3, BCP의 구조는 각각 아래와 같다.
For reference, the structures of NPB, CBP and Ir (ppy) 3 and BCP are as follows.
NPBNPB
CBPCBP
IrIr (( ppyppy )33
BCPBCP
실험 결과, 본 발명의 트리페닐렌 계열 화합물을 사용하는 실시예1~11의 유기 발광 소자는 종래 CBP를 사용하는 비교예 1의 유기 EL 소자 보다 전압 및 효율면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.
As a result of the experiment, it was confirmed that the organic light emitting devices of Examples 1 to 11 using the triphenylene type compound of the present invention showed superior performance in terms of voltage and efficiency as compared with the organic EL device of Comparative Example 1 using CBP .
[실시예 12~16] 유기 EL 소자의 제조 및 평가[Examples 12 to 16] Preparation and evaluation of organic EL devices
하기와 같은 방법으로 유기 EL 소자를 제조하였다. An organic EL device was prepared in the following manner.
ITO (Indium tin oxide)가 1500Å의 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 이송하였다. The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the washing of distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO (양극) 위에 본 발명의 화합물들을 정공 수송층으로 이용하여 Inv 화합물/CBP + 10%Ir(ppy)3(20nm) / BCP(10nm) /Alq3(40nm) /LiF(1nm) /Al 순으로 발광 소자를 구성한 다음 이들의 발광 특성을 평가하였고, 그 결과를 하기 표 2에 기재하였다. 여기서, 정공 수송층으로 적용되는 화합물은 하기 표 2과 같다.
(Invol) / CBP + 10% Ir (ppy) 3 (20 nm) / BCP (10 nm) / Alq 3 (40 nm) / LiF (1 nm) using the compounds of the present invention as the hole transport layer on the ITO / Al, and their luminescent properties were evaluated. The results are shown in Table 2 below. Here, the compound to be used as the hole transporting layer is shown in Table 2 below.
[비교예 2]Comparative Example 2
상기 실시예에서와 동일한 방법으로 준비된 전극 위에 NPB(40nm)/CBP + 10%Ir(ppy)3(20nm)/BCP(10nm)/Alq3(40nm)/LiF(1nm)/Al 순으로 발광 소자를 구성한 후, 실시예 1과 동일한 방법으로 발광특성을 평가하였다.(40 nm) / CBP + 10% Ir (ppy) 3 (20 nm) / BCP (10 nm) / Alq 3 (40 nm) / LiF (1 nm) / Al on the electrode prepared in the same manner as in the above- , And then the luminescent characteristics were evaluated in the same manner as in Example 1. [
실험 결과, 본 발명에 따른 트리페닐렌 계열 화합물을 사용하는 실시예 12~16의 유기 발광 소자는, 종래 NPB를 사용하는 비교예의 유기 EL 소자 보다 전압 및 효율면에서 월등히 우수한 성능을 나타내는 것을 확인할 수 있었다. As a result of the experiment, it was confirmed that the organic light emitting devices of Examples 12 to 16 using the triphenylene type compound according to the present invention had far superior performance in terms of voltage and efficiency than the organic EL devices of the comparative example using NPB there was.
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속하는 것은 당연하다.Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.
Claims (7)
[화학식 1]
상기 화학식에서,
X는 CR16R17, O, S, SiR18R19, S(=O), 및 S(=O)2로 이루어진 군에서 선택되고,
R1 내지 R19는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 아미노기, 니트로기, 니트릴기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C5~C40의 아릴기, C1~C40의 헤테로아릴기, C1~C40의 알콕시기, C5~C40의 아릴옥시기, C1~C40의 알킬아미노기, C5~C40의 아릴아미노기, C5~C40의 디아릴아미노기, C5~C40의 헤테로아릴아미노기, C2~C40의 디헤테로아릴아미노기, C6~C40의 아릴알킬기, C6~C40의 헤테로아릴알킬기, C3~C40의 시클로알킬기, C1~C40의 할로겐알킬기, C3~C40의 헤테로시클로알킬기, C3~C40 의 알킬실릴기, C3~C40의 아릴실릴기, 및 C3~C40의 헤테로아릴실릴기로 이루어진 군에서 선택되며,
이때 R1 내지 R19는 각각 인접하는 치환기와 축합(fused)되거나 또는 고리를 형성할 수 있다.A material for an organic electroluminescent device represented by Formula 1 below:
[Formula 1]
In the above formulas,
X is selected from the group consisting of CR 16 R 17 , O, S, SiR 18 R 19 , S (= 0), and S (= 0) 2 ,
R 1 to R 19 are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group each other, C 2 ~ C 40 alkynyl group, C 5 ~ C 40 aryl group, C 1 ~ C 40 heteroaryl group, C 1 ~ C 40 alkoxy group, C 5 ~ C 40 aryloxy group, C 1 ~ C 40 Alkylamino group, C 5 to C 40 arylamino group, C 5 to C 40 diarylamino group, C 5 to C 40 heteroarylamino group, C 2 to C 40 diheteroarylamino group, C 6 to C 40 aryl An alkyl group, a C 6 to C 40 heteroarylalkyl group, a C 3 to C 40 cycloalkyl group, a C 1 to C 40 halogenalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, C 3 ~ C 40 aryl silyl group, and a C 3 ~ is selected from the heteroaryl group consisting of a silyl group of C 40,
Wherein R 1 to R 19 may each be fused to adjacent substituents or may form a ring.
[화학식 2]
[화학식 3]
상기 화학식에서, R1 내지 R14는 제1항에서 정의된 바와 동일하다. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by one of the following Chemical Formula 2 or Chemical Formula 3:
(2)
(3)
In the above formula, R 1 to R 14 are the same as defined in claim 1.
[화학식 4]
[화학식 5]
상기 화학식에서, R1 내지 R19는 제1항에서 정의된 바와 동일하다. The organic electroluminescent device material of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formula 4 or Chemical Formula 5.
[Chemical Formula 4]
[Chemical Formula 5]
In the above formula, R 1 to R 19 are the same as defined in claim 1.
[화학식 6]
[화학식 7]
상기 화학식에서, R1 내지 R14는 제1항에서 정의된 바와 동일하다. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by one of the following Chemical Formulas 6 and 7.
[Chemical Formula 6]
(7)
In the above formula, R 1 to R 14 are the same as defined in claim 1.
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제4항 중 어느 한 항에 기재된 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.An organic electroluminescent device comprising: (i) a cathode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
At least one of the one or more organic material layers comprises an compound represented by the formula (1) according to any one of claims 1 to 4.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020110068609A KR101470055B1 (en) | 2011-07-11 | 2011-07-11 | Organic electroluminescence device using the triphenylene derivative |
| PCT/KR2012/005474 WO2013009079A1 (en) | 2011-07-11 | 2012-07-11 | Triphenylene-based compound and organic electroluminescent diode using same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020110068609A KR101470055B1 (en) | 2011-07-11 | 2011-07-11 | Organic electroluminescence device using the triphenylene derivative |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020140048891A Division KR101548076B1 (en) | 2014-04-23 | 2014-04-23 | Organic electroluminescence device using the triphenylene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20130007934A true KR20130007934A (en) | 2013-01-21 |
| KR101470055B1 KR101470055B1 (en) | 2014-12-08 |
Family
ID=47506265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020110068609A KR101470055B1 (en) | 2011-07-11 | 2011-07-11 | Organic electroluminescence device using the triphenylene derivative |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR101470055B1 (en) |
| WO (1) | WO2013009079A1 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101503796B1 (en) * | 2014-05-08 | 2015-03-18 | 성균관대학교산학협력단 | Organic electroluminescent compound, producing method of the same and organic electroluminescent device including the same |
| US20160190472A1 (en) * | 2014-12-30 | 2016-06-30 | Luminescence Technology Corp. | Organic material and organic electroluminescent device using the same |
| US9478748B2 (en) | 2013-07-01 | 2016-10-25 | Samsung Display Co., Ltd. | Organic light emitting diode device |
| CN106748621A (en) * | 2015-11-23 | 2017-05-31 | 机光科技股份有限公司 | Organic compound and use its organic electroluminescent element |
| US10032990B2 (en) | 2013-07-10 | 2018-07-24 | Samsung Sdi Co., Ltd. | Organic composition, and organic optoelectronic element and display device |
| US10147887B2 (en) | 2014-03-10 | 2018-12-04 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
| WO2019013509A1 (en) * | 2017-07-10 | 2019-01-17 | 주식회사 엘지화학 | Novel heterocyclic compound and organic light-emitting device using same |
| KR20190006448A (en) * | 2017-07-10 | 2019-01-18 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| US10312451B2 (en) * | 2015-01-26 | 2019-06-04 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
| US10446760B2 (en) | 2014-05-12 | 2019-10-15 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectric diode, and display device |
| JP2020068383A (en) * | 2018-10-24 | 2020-04-30 | 北京夏禾科技有限公司 | Silicon-containing electron transport material and use thereof |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014094954A1 (en) * | 2012-12-18 | 2014-06-26 | Merck Patent Gmbh | Indenophenanthrene based compounds |
| US20160211456A1 (en) * | 2015-01-19 | 2016-07-21 | Luminescence Technology Corp. | PHENANTHRO[9,10-b]TETRAPHENYLENE DERIVATIVE AND USE THEREOF |
| US10164194B2 (en) * | 2015-01-26 | 2018-12-25 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
| US9812649B2 (en) * | 2015-02-17 | 2017-11-07 | Luminescence Technology Corp. | Indenotriphenylene-based amine derivative for organic electroluminescent device |
| KR20170007648A (en) * | 2015-07-10 | 2017-01-19 | 삼성디스플레이 주식회사 | Organic light emitting device |
| TWI617547B (en) * | 2015-12-03 | 2018-03-11 | Luminescence Technology Corporation | Organic material and organic electroluminescence device using the same |
| TWI605033B (en) * | 2016-01-06 | 2017-11-11 | 機光科技股份有限公司 | Indenotriphenylene-based amine derivative for organic electroluminescent device |
| KR102018238B1 (en) | 2016-09-21 | 2019-09-04 | 삼성에스디아이 주식회사 | Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric device and display device |
| KR101962756B1 (en) | 2016-09-29 | 2019-03-27 | 삼성에스디아이 주식회사 | Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric device and display device |
| US11177446B2 (en) * | 2017-09-14 | 2021-11-16 | Beijing Summer Sprout Technology Co., Ltd. | Silicon containing organic fluorescent materials |
| CN110526825B (en) * | 2018-05-25 | 2023-04-07 | 江苏三月科技股份有限公司 | Compound with structure of isoflexor and triarylamine as core and application thereof |
| US10807972B2 (en) * | 2018-10-15 | 2020-10-20 | Feng-wen Yen | Indenotriphenylene-based amine derivative and organic electroluminescence device using the same |
| US11296282B2 (en) * | 2018-12-17 | 2022-04-05 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
| US11108001B2 (en) * | 2019-01-17 | 2021-08-31 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
| TWI792166B (en) * | 2021-01-29 | 2023-02-11 | 機光科技股份有限公司 | Organic compound and application in red organic electroluminescent device thereof |
| CN113004261B (en) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | Compound containing multi-heterocyclic structure and application thereof |
| CN113004243B (en) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | Heterocyclic compound containing naphthoquinone and application thereof |
| CN113004262B (en) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | Organic material and application thereof |
| CN112961140B (en) * | 2021-02-08 | 2023-02-17 | 北京云基科技股份有限公司 | Naphthoquinone heterocyclic compound and application thereof |
| CN116003356A (en) * | 2022-12-30 | 2023-04-25 | 宁波卢米蓝新材料有限公司 | Triphenylene-containing polycyclic heteroaromatic group-containing compound, organic electroluminescent material and application thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435436A (en) * | 2005-05-31 | 2013-12-11 | 通用显示公司 | Triphenylene hosts in phosphorescent light emitting diodes |
| ATE552227T1 (en) * | 2007-09-20 | 2012-04-15 | Basf Se | ELECTROLUMINESCENCE DEVICE |
| JP2009114068A (en) * | 2007-11-01 | 2009-05-28 | Canon Inc | Triphenylene compound and organic light-emitting device by using the same |
| KR101023623B1 (en) * | 2008-10-24 | 2011-03-22 | 주식회사 이엘엠 | Organic Light Emitting Material and Organic Light Emitting Diode Having The Same |
| TWI448534B (en) * | 2009-09-28 | 2014-08-11 | Ritdisplay Corp | Organic electroluminescence device |
| KR101866851B1 (en) * | 2010-12-24 | 2018-06-14 | 에스에프씨 주식회사 | Heterocyclic compounds and organic light-emitting diode including the same |
-
2011
- 2011-07-11 KR KR1020110068609A patent/KR101470055B1/en active IP Right Grant
-
2012
- 2012-07-11 WO PCT/KR2012/005474 patent/WO2013009079A1/en active Application Filing
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9478748B2 (en) | 2013-07-01 | 2016-10-25 | Samsung Display Co., Ltd. | Organic light emitting diode device |
| US10032990B2 (en) | 2013-07-10 | 2018-07-24 | Samsung Sdi Co., Ltd. | Organic composition, and organic optoelectronic element and display device |
| US10147887B2 (en) | 2014-03-10 | 2018-12-04 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
| KR101503796B1 (en) * | 2014-05-08 | 2015-03-18 | 성균관대학교산학협력단 | Organic electroluminescent compound, producing method of the same and organic electroluminescent device including the same |
| US10446760B2 (en) | 2014-05-12 | 2019-10-15 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectric diode, and display device |
| US20160190472A1 (en) * | 2014-12-30 | 2016-06-30 | Luminescence Technology Corp. | Organic material and organic electroluminescent device using the same |
| US9793493B2 (en) * | 2014-12-30 | 2017-10-17 | Luminescence Technology Corp. | Organic material and organic electroluminescent device using the same |
| US10312451B2 (en) * | 2015-01-26 | 2019-06-04 | Luminescence Technology Corporation | Compound for organic electroluminescent device |
| CN106748621A (en) * | 2015-11-23 | 2017-05-31 | 机光科技股份有限公司 | Organic compound and use its organic electroluminescent element |
| KR20190006448A (en) * | 2017-07-10 | 2019-01-18 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| WO2019013509A1 (en) * | 2017-07-10 | 2019-01-17 | 주식회사 엘지화학 | Novel heterocyclic compound and organic light-emitting device using same |
| JP2020068383A (en) * | 2018-10-24 | 2020-04-30 | 北京夏禾科技有限公司 | Silicon-containing electron transport material and use thereof |
| KR20200049593A (en) * | 2018-10-24 | 2020-05-08 | 베이징 썸머 스프라우트 테크놀로지 컴퍼니 리미티드 | A silicon-containing electron transporting material and its application |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101470055B1 (en) | 2014-12-08 |
| WO2013009079A1 (en) | 2013-01-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101470055B1 (en) | Organic electroluminescence device using the triphenylene derivative | |
| KR101244599B1 (en) | Bipolar triphenylene-based compound and organic electroluminescent device comprising the same | |
| KR101218029B1 (en) | Triphenylene-based compounds that substitute aryl amine compounds and organic electroluminescent device comprising same | |
| KR101452578B1 (en) | Novel compounds and organic electro luminescence device using the same | |
| KR20120088644A (en) | Organic light-emitting compound and organic electroluminescent device using the same | |
| KR101601355B1 (en) | Novel organic compounds and organic electro luminescence device comprising the same | |
| KR102192691B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101567112B1 (en) | Compound having substituted pyridyl group and pyridoindole ring structure linked through phenylene group, and organic electroluminescent device | |
| KR101601356B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR101298397B1 (en) | Organic lightemitting compound and organic electroluminescent device using the same | |
| KR102263822B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR20200022963A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101577104B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR20140145451A (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR101548076B1 (en) | Organic electroluminescence device using the triphenylene derivative | |
| KR20190001967A (en) | Compound for organic electric element, organic electric element comprising the same and electronic device thereof | |
| KR101634852B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR101577112B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR102120916B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101548040B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR101612158B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR101576566B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR101390616B1 (en) | Novel compounds and organic electro luminescence device using the same | |
| KR101319631B1 (en) | Azaindenoanthracene derivative and organic electroluminescence device using the same | |
| KR101434726B1 (en) | Anthracene derivative and organic electroluminescence device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E902 | Notification of reason for refusal | ||
| A107 | Divisional application of patent | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20171114 Year of fee payment: 4 |
|
| FPAY | Annual fee payment |
Payment date: 20191202 Year of fee payment: 6 |