CN103298800A - 新有机电致发光化合物和使用该化合物的有机电致发光器件 - Google Patents
新有机电致发光化合物和使用该化合物的有机电致发光器件 Download PDFInfo
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- 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
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- 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
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- 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
- C07D333/76—Dibenzothiophenes
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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
- 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
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- 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
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- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
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- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- 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
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
本发明提供了新的有机电致发光化合物和使用该化合物的有机电致发光器件。因为使用有机电致发光化合物作为空穴传输材料或者空穴注入材料的有机电致发光器件具有优良的发光效率和优异的使用寿命特性,它被用于制造具有更好运行寿命以及由于功率效率的提升所导致的能耗减少的OLED器件。
Description
技术领域
本发明涉及新有机电致发光化合物和包含该化合物的有机电致发光器件,更具体地涉及适合用作空穴传输材料或空穴注入材料的新有机电致发光化合物和使用该化合物的有机电致发光器件。
背景技术
目前广泛可用的液晶显示器(LCD)是具有低能耗和轻量化的非发射性显示器,但是其具有复杂的运行系统和包括响应时间和对比度在内的并不令人满意的性能。因此,目前有机电致发光器件作为下一代平板显示器正受到关注,并对它们进行深入研究。
在显示器件中,电致发光(EL)器件是优选的,因为它们作为自发射显示器件提供宽视角、优异的对比度和快速响应速率。伊斯特曼柯达(Eastman Kodak)在1987年首先研制了一种有机EL器件,该器件使用低分子量芳香族二胺和铝配合物以形成电致发光层[Appl.Phys.Lett.51,913,1987]。
有机EL器件的发光机制是:当电荷注入到形成在电子注入电极(阴极)和空穴注入电极(阳极)之间的有机层时,形成电子和空穴配对,电子-空穴对湮灭时发光。所述设备可以在挠性透明基材(例如塑料)上形成,也可在相比等离子体显示平板或无机EL显示器低的电压(10V或更低)下运行,需要较少的功耗并具有优异的色彩。
有机EL器件的有机材料可大致分为发光材料和电荷产生材料。发光材料直接涉及发光颜色和发光效率,需要以下数种特性,包括固相的高荧光量子产率、电子和空穴的高迁移率、真空沉积时的低分解性、并形成均匀稳定的薄膜。
同时,空穴注入和传输材料包括铜酞菁(CuPc)、NPB、TPD、MTDATA(4,4',4"-三(3-甲基苯基苯基氨基)三苯胺)等。在空穴注入和传输层中包含此类材料的器件是有问题的,因为效率和使用寿命变差。该问题的原因在于当有机EL器件以高电流运行时,在阳极和空穴注入层之间会产生热应力,由于该热应力可能会导致器件的使用寿命大幅缩短。同样,用于空穴注入层的有机材料具有非常高的空穴迁移率,从而破坏空穴-电子的电荷平衡,从而降低了量子产量(cd/A)。
为了增加有机EL器件的耐久性,据报道使用具有良好薄膜稳定性的化合物以及具有高非结晶性的化合物展现出较高的薄膜稳定性。因此,玻璃转化温度(Tg)被用作非结晶性的指标。常规MTDATA的Tg为76℃,因此不认为具有非结晶性。此类材料在有机EL器件的耐久性以及基于空穴注入和传输性能的发光效率并不令人满意。
发明内容
技术问题
因此,本发明针对现有技术存在的问题,本发明的一个目的是提供具有比常规空穴注入或空穴传输材料更好的发光效率和器件使用寿命且具有优异主链结构的有机EL化合物,并提供采用此新有机EL化合物作为空穴注入层或空穴传输层的新有机EL器件。
解决问题的方法
本发明提供如下化学式1表示的有机EL化合物,以及包含所述有机EL化合物的有机EL器件。在有机EL器件的空穴注入层或空穴传输层中含有本发明的有机EL化合物,从而降低了装置的运行电压并增加了装置的发光效率。
在一个方面,本发明提供用如下化学式1表述的有机EL化合物。
[化学式1]
在化学式1中,X表示-O-、-S-、-C(R11R12)-或者-Si(R13R14)-,其中R11至R12独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基、取代或未取代的5-元至7-元杂环烷基、或者取代或未取代的(C3-C30)环烷基,或者与相邻取代基连接成环;
R1至R4独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基、取代或未取代的(C3-C30)环烷基、取代或未取代的5-元至7-元杂环烷基、取代或未取代的(C6-C30)芳基(C1-C30)烷基、与一个或多个环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个取代或未取代的芳环稠合的5-元至7-元杂环烷基或者与一个或多个取代或未取代的芳环稠合的(C3-C30)环烷基、取代或未取代的(C1-C30)甲硅烷基、氰基、硝基或羟基,并且当R1至R4表示复数时,它们可以相互连接形成环结构;
R5和R6表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基、或者取代或未取代的5-元至7-元杂环烷基,或者与相邻取代基连接以形成环;
L1和L2独立地表示化学键、取代或未取代的(C6-C30)亚芳基或者取代或未取代的(C3-C30)杂亚芳基,仅排除L1和L2同时表示化学键的情况;
Ar表示取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基(除了咔唑)、取代或未取代的5-元至7-元杂环烷基、与一个或多个环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个取代或未取代的芳环稠合的取代或未取代的(C3-C30)杂芳基、或者与一个或多个取代或未取代的芳环稠合的5-元至7-元杂环烷基,或者通过有或没有稠环的(C3-C30)亚烷基或者有或没有稠环的(C3-C30)亚烯基与相邻取代基相连接以形成脂环和单环或多环芳环;
a至d独立地表示0-4的整数,当a至d是大于或等于2的整数时,R1、R2、R3和R4可以相互相同或不同,并且可与相邻取代基连接形成环;以及
所述杂环烷基和杂芳基包含一个或多个选自B、N、O、S、P(=O)、Si和P的杂原子。
进一步取代R1至R4、R5和R6、R11至R14、L1、L2和Ar的取代基独立地选自下组中的一个或多个:氘、卤素、被卤素取代或未取代的(C1-C30)烷基、(C6-C30)芳基、被(C6-C30)芳基取代或未取代的(C3-C30)杂芳基、5-元至7-元杂环烷基、与一个或多个芳环稠合的5-元至7-元杂环烷基、(C3-C30)环烷基、与一个或多个芳环稠合的(C6-C30)环烷基、R21R22R23Si-、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、NR24R25、BR26R27、PR28R29、P(=O)R30R31、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、R32S-、R33O-、R34C(=O)-、R35C(=O)O-、羧基、硝基和羟基,其中R21至R33独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基、或者取代或未取代的5-元至7-元杂环烷基,或者通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者有或没有稠环的取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环和单环或多环芳环,所形成的脂环和单环或多环芳环的碳原子可被一个或多个选自氮、氧和硫的杂原子取代;并且R34和R35表示(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳基或者(C6-C30)芳氧基。
在本发明中,“烷基”、以及其他包含“烷基”部分的取代基包含直链和支链类型。在本发明中,“环烷基”包含单环烃以及多环烃,例如取代或未取代的金刚烷基或者取代或未取代的(C7-C30)二环烷基。在本发明中,“芳基”表示通过从芳香烃除去一个氢原子得到的有机基团,可包含4-元至7-元、优选5-元或6-元的单环或稠环,还包含通过单键连接的多个芳基。具体例子包括,但不限于,苯基、萘基、联苯基(biphenyl)、蒽基、茚基、芴基、菲基(phenanthryl)、苯并[9,10]菲基(triphenylenyl)、芘基、苝基(perylenyl)、屈基(chrysenyl)、并四苯基(naphthacenyl)、荧蒽基(fluoranthenyl)等。所述萘基包括1-萘基和2-萘基,所述蒽基包括1-蒽基、2-蒽基和9-蒽基,所述芴基包括1-芴基、2-芴基、3-芴基、4-芴基和9-芴基。在本发明中,“杂芳基”指的是含有1-4个选自B、N、O、S、P、P(=O)、Si和Se的杂原子作为芳环主链原子且余下的芳环主链原子是碳原子的芳基基团,例如与一个或多个苯环缩合的5-元或6-元单环杂芳基和多环杂芳基,其可以是部分饱和的。杂芳基包括二价芳基基团,其中环中的杂原子可被氧化或季铵化,以形成例如N-氧化物或季铵盐。它们的具体例子包括但并不限于,单环杂芳基例如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异唑基、唑基、二唑基、三嗪基、四嗪基、三唑基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等;多环杂芳基例如苯并呋咱基(benzofuranyl)、苯并噻吩基、异苯并呋喃基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异唑基、苯并唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基(cinnolinyl)、喹唑啉基、喹嗪基、喹喔啉基(quinoxalinyl)、咔唑基、菲啶基(phenanthridinyl)、苯并间二氧杂环戊烯基(benzodioxolyl)、萘啶基(naphthylidinyl)、二苯并呋喃基、二苯并苯硫基等;及其N-氧化物(例如吡啶基N-氧化物、喹啉基N-氧化物等)及其季铵盐等。
在本发明中,“(C1-C30)烷基或者(C6-C30)芳基(C1-C30)烷基”的烷基部分包括(C1-C20)烷基,更具体为(C1-C10)烷基。“(C6-C30)芳基和(C6-C30)芳基(C1-C30)烷基”的芳基部分包括(C6-C20)芳基,更具体为(C6-C12)芳基。同样地,“(C3-C30)杂芳基”包括(C3-C20)杂芳基,更具体为(C3-C12)杂芳基,且“(C3-C30)环烷基”包括(C3-C20)环烷基,更具体为(C3-C7)环烷基。同样地,“(C3-C30)亚烷基或亚烯基”包括(C3-C20)亚烷基或亚烯基,更具体为(C3-C10)亚烷基或亚烯基。
在本文所用术语“取代或未取代的”中的表述“取代”指的是未取代的取代基被进一步取代。
此外,本发明的有机EL化合物选自如下化学式2-5表示的化合物。
[化学式2]
[化学式3]
[化学式4]
[化学式5]
在化学式2-5中,X、R1至R4、R5和R6、L1、L2、Ar以及a至d的定义与化学式1中的定义相同。
具体地,Ar选自下述结构,但不限于此:
更具体地,本发明的有机EL化合物的例子是如下化合物,但是本发明并不限于此。
可以根据例如以下方案1所示制备本发明的有机EL化合物,但不限于以下方案。
[方案1]
在方案1中,X、R1至R4、R5和R6、L1、L2、Ar以及a至d的定义与化学式1中的定义相同。
此外,本发明提供一种有机EL器件,其中本发明的有机EL化合物用作空穴注入材料或空穴传输材料。
本发明的有机EL器件包含第一电极;第二电极;插入所述第一电极和第二电极之间的一层或多层有机层,所述有机层包括化学式1表示的一种或多种有机EL化合物。
本发明的有机EL器件包含化学式1表示的有机EL化合物,还可包含一种或多种选自芳胺基化合物和苯乙烯胺基化合物的化合物,所述芳胺基化合物和苯乙烯胺基化合物的具体例子如韩国专利申请第10-2008-0060393号的说明书第212至224段所述,但不限于此。
在本发明的有机EL器件中,除了化学式1表示的有机EL化合物以外,所述有机层还可包含一种或多种选自元素周期表第1族、第2族的有机金属、第四周期和第五周期的过渡金属、镧系金属和d-过渡元素的金属或络合化合物。所述有机层可包括电致发光层和电荷产生层。
可实现具有独立发光模式的像素结构的有机EL器件,其中同时平行图案化(pattern)包含本发明化学式1的有机EL化合物作为子像素的有机EL器件,所述一个或多个子像素包含一种或多种选自Ir、Pt、Pd、Rh、Re、Os、Tl、Pb、Bi、In、Sn、Sb、Te、Au和Ag的金属化合物。
另外,除了所述有机EL化合物之外,所述有机层还可包括一种或多种发射红光、绿光或蓝光的有机电致发光层,以实现发射白光的有机EL器件。发射红光、绿光或蓝光的化合物的例子可以是韩国专利申请第10-2008-0123276、10-2008-0107606或10-2008-0118428号所述的化合物,但不限于此。
在本发明的有机EL器件中,选自硫属化物层、金属卤化物层和金属氧化物层的层(以下称为“表面层”)可设置在电极对中的至少一个电极的内表面上。更具体地,硅或铝的硫属化物(包括氧化物)层可置于电致发光介质层的阳极表面上,而金属卤化物层或金属氧化物层可置于所述电致发光介质层的阴极表面上,从而实现运行稳定性。所述硫属化物可以包括例如SiOx(1≤x≤2)、AlOx(1≤x≤1.5)、SiON、SiAlON等。所述金属卤化物可以包括例如LiF、MgF2、CaF2、稀土金属氟化物等。所述金属氧化物可以包括例如Cs2O、Li2O、MgO、SrO、BaO、CaO等。
在本发明的有机EL器件中,也优选在所制备的电极对的至少一个电极表面上设置电子传输化合物和还原性掺杂剂的混合区,或者空穴传输化合物和氧化性掺杂剂的混合区。在这种情况下,因为所述电子传输化合物被还原成阴离子,所以电子从所述混合区注入并传输到电致发光介质层中变得更加容易。此外,因为所述空穴传输化合物被氧化成阳离子,所以空穴从所述混合区注入并传输到电致发光介质层中变得更加容易。优选的氧化性掺杂剂包括各种路易斯酸和受体化合物。优选的还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属及其混合物。另外,具有两层或更多层电致发光层的发射白光的有机EL器件可使用还原性掺杂剂层作为电荷产生层来制备。
发明的有利效果
根据本发明,有机EL化合物可用作空穴传输材料或者空穴注入材料,从而得到的有机EL器件可以具有良好的发光效率,并具有优异的材料使用寿命性能,并可用于制造具有非常优异运行寿命的OLED器件。
本发明最佳实施方式
本发明进一步描述了本发明的有机EL化合物、制备该化合物的方法以及使用该化合物的器件的电致发光性质。但是,这些实施例仅仅是为了阐述的目的,而不是为了限制本发明的范围。
[制备例1]制备化合物3
化合物1-1的制备
将30g(128.7mmol)4-溴联苯、27mL(772mmol)氨水、2.45g(12.87mmol)CuI、12.9mL(128.7mmol)乙酰丙酮、83.9g(257.4mmol)Cs2CO3和1000mL DMF在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,然后使用柱色谱法纯化,从而得到15.2g(88.64mmol)化合物1-1。
化合物1-2的制备
将15g(88.64mmol)化合物1-1、24.1g(88.64mmol)2-溴-9,9-二甲基-9H-芴、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)3、25.5g(266mmol)NaOt-Bu以及1000mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,然后使用柱色谱法纯化,从而得到11.2g(30.98mmol)化合物1-2。
化合物1-3的制备
将10g(44mmol)4-二苯并噻吩硼酸、31g(132mmol)1,4-二溴苯、2.5g(2.2mmol)Pd(PPh3)4、132mL(132mmol)1M的Na2CO3、500mL甲苯以及200mL乙醇在120℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,然后使用柱色谱法纯化,从而得到6.7g(19.8mmol)化合物1-3。
化合物3的制备
将7.9g(23.28mmol)化合物1-3、7g(19.4mmol)化合物1-2、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到8.0g(12.9mmol,66%)化合物3。
1H NMR(CDCl3,200MHz)δ=1.72(6H,s),6.58(1H,m),6.69~6.75(5H,m),7.28(1H,m),7.38~7.41(2H,m),7.5~7.62(13H,m),7.87(1H,m),7.98(1H,m),8.2(1H,m),8.41~8.45(2H,m);MS/FAB实验值620,计算值619.82
[制备例2]制备化合物9
化合物2-1的制备
将20.0g(138.8mmol)2-萘酚、28.8g(277.4mmol)NaHSO3、160mL蒸馏水以及31.2mL(166.4mmol)4-溴苯基肼加热到120℃。12小时之后,向反应混合物中加入蒸馏水,对产生的固体进行真空过滤。然后将得到的固体加入盐酸水溶液并加热至100℃。1小时后,用二氯甲烷萃取所得产物,用蒸馏水和NaOH水溶液清洗,并进行柱分离纯化,从而得到9.2g(31.0mmol)化合物2-1。
化合物2-2的制备
混合9.2g(31.0mmol)化合物2-1、2.0g(31.0mmol)Cu、0.4g(1.6mmol)18-冠-6、12.8g(93.2mmol)K2CO3以及100mL的1,2-二氯苯,回流搅拌至180℃,持续12小时。反应混合物冷却至室温,真空蒸馏,用二氯甲烷萃取并用蒸馏水清洗,之后用MgSO4进行干燥,真空蒸馏,并进行柱分离,从而得到7.6g(20.4mmol)化合物2-2。
化合物2-3的制备
将35.2g(128.7mmol)2-溴-9,9-二甲基-9H-芴、27mL(772mmol)氨水、2.45g(12.87mmol)CuI、12.9mL(128.7mmol)乙酰丙酮、83.9g(257.4mmol)Cs2CO3和1000mL DMF在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,然后使用柱色谱法纯化,从而得到11.3g(54mmol)化合物2-3。
化合物2-4的制备
将18.5g(88.64mmol)化合物2-3、33g(88.64mmol)化合物2-2、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)3、25.5g(266mmol)NaOt-Bu以及1000mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,然后使用柱色谱法纯化,从而得到14.2g(28.4mmol)化合物2-4。化合物9的制备
将7.9g(23.28mmol)化合物1-3、9.7g(19.4mmol)化合物2-4、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到7.3g(9.62mmol,50%)化合物9。
1H NMR(CDCl3,200MHz)δ=1.72(6H,s),5.93(1H,m),6.58(1H,m),6.69~6.75(3H,m),7.28(1H,m),7.38(1H,m),7.45(1H,m),7.5(3H,m),7.52(1H,m),7.54~7.62(13H,m),7.87(1H,m),7.98(1H,m),8.16~8.2(2H,m),8.41~8.45(2H,m),8.54(1H,m);MS/FAB实验值759,计算值758.97
[制备例3]制备化合物28
化合物3-1的制备
将5.4g(44mmol)苯基硼酸、18.9g(66mmol)1,4-二溴萘、2.0g(1.76mmol)Pd(PPh3)4、14.0g(132mmol)Na2CO3、200mL甲苯以及100mL乙醇在120℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,然后使用柱色谱法纯化,从而得到9.1g(32.14mmol)化合物3-1。
化合物3-2的制备
将18.6g(88.64mmol)化合物2-3、25g(88.64mmol)化合物3-1、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)3、25.5g(266mmol)NaOt-Bu以及1000mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,然后使用柱色谱法纯化,从而得到14.2g(34.5mmol)化合物3-2。
化合物28的制备
将7.9g(23.28mmol)化合物1-3、8.0g(19.4mmol)化合物3-2、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,然后重结晶,从而得到7.3g(10.9mmol,45%)化合物28。
1H NMR(CDCl3,200MHz)δ=1.72(6H,s),6.58(1H,m),6.69~6.75(3H,m),7.04(1H,m),7.28(1H,m),7.38~7.41(2H,m),7.5~7.53(11H,m),7.78~7.79(3H,m),7.87(1H,m),7.98(1H,m),8.07(1H,m),8.2(1H,m),8.41~8.49(3H,m);MS/FAB实验值670,计算值669.87
[制备例4]制备化合物30
化合物4-1的制备
将8.2g(23.28mmol)2,7-二溴-9,9-二甲基-9H-芴、3.2g(19.4mmol)咔唑、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及200mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,然后重结晶,从而得到5.8g(13.2mmol)化合物4-1。
化合物4-2的制备
将8.3g(88.64mmol)苯胺、38.9g(88.64mmol)化合物4-1、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)3、25.5g(266mmol)NaOt-Bu以及800mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到17.2g(38.2mmol)化合物4-2。
化合物30的制备
将7.9g(23.28mmol)化合物1-3、8.7g(19.4mmol)化合物4-2、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,然后重结晶,从而得到7.0g(9.9mmol,50%)化合物30。
1H NMR(CDCl3,200MHz)δ=1.72(6H,s),6.37(1H,m),6.54(1H,m),6.63(2H,m),6.69(2H,m),6.81(1H,m),7.17~7.34(7H,m),7.5~7.63(8H,m),7.87(1H,m),7.94~7.98(2H,m),8.12(1H,m),8.2(1H,m),8.41~8.45(2H,m),8.55(1H,m);MS/FAB实验值709,计算值708.91
[制备例5]制备化合物32
化合物5-1的制备
将8.3g(88.64mmol)苯胺、24.1g(88.64mmol)2-溴-9,9-二甲基-9H-芴、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)3、25.5g(266mmol)NaOt-Bu以及800mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到14.2g(49.8mmol)化合物5-1。
化合物5-2的制备
将10g(44mmol)4-二苯并噻吩硼酸、41.2g(132mmol)1,4-二溴联苯、2.5g(2.2mmol)Pd(PPh3)4、132mL(132mmol)1M的Na2CO3、500mL甲苯以及200mL乙醇在120℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到15.3g(36.8mmol)化合物5-2。
化合物32的制备
将9.7g(23.28mmol)化合物5-2、5.54g(19.4mmol)化合物5-1、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到5.8g(9.4mmol,48%)化合物32。
1H NMR(CDCl3,200MHz)δ=1.72(6H,s),6.58~6.63(3H,m),6.69~6.81(4H,m),7.2~7.28(7H,m),7.38(1H,m),7.5~7.62(7H,m),7.87(1H,m),7.98(1H,m),8.2(1H,m),8.41~8.45(2H,m);MS/FAB实验值620,计算值619.82
[制备例6]制备化合物37
化合物6-1的制备
将150g(426mmol)2,7-二溴-9,9-二甲基芴溶于2.1L四氢呋喃,并冷却至-78℃,之后将170mL(2.5M在己烷中,426mmol)n-BuLi缓慢逐滴滴加入其中,并搅拌1小时。
将53mL(469mmol)硼酸三甲酯加入其中,并搅拌12小时。反应完成之后,用2M HCl终止反应,用EA/H2O萃取反应产物,用MgSO4脱水,真空蒸馏,柱分离,从而得到70g(220.8mmol)化合物6-1。
化合物6-2的制备
将70g(220mmol)化合物6-1、50g(200mmol)2-碘硝基苯、7g(6mmol)Pd(PPh3)4、64g(600mmol)Na2CO3、1L甲苯、0.5L乙醇和0.3L水在90℃搅拌7.5小时。反应完成之后,用EA/H2O萃取反应产物,用MgSO4脱水,真空蒸馏,从而得到化合物6-2,然后使其立即进行后续过程而没有额外的纯化。
化合物6-3的制备
将90g化合物6-2和750mL P(OEt)3溶于750mL1,2-二氯苯,在150℃搅拌9小时,之后用蒸馏水清洗经过搅拌的溶液并进行处理以去除溶剂,然后对所得红色液体进行柱分离,从而得到26g(79.69mmol)化合物6-3。
化合物6-4的制备
将2.6g(23.28mmol)氯苯、7.0g(19.4mmol)化合物6-3、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu、200mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,然后重结晶,从而得到6.8g(15.5mmol)化合物6-4。
将18.6g(88.64mmol)化合物2-3、38.9g(88.64mmol)化合物6-4、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)3、25.5g(266mmol)NaOt-Bu以及800mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到15.6g(27.5mmol)化合物6-5。
化合物37的制备
将7.9g(23.28mmol)化合物1-3、11g(19.4mmol)化合物6-5、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到6.9g(8.4mmol,43%)化合物37。
1H NMR(CDCl3,200MHz)δ=1.72(12H,s),6.58~6.81(6H,m),7.28~7.29(2H,m),7.38(1H,m),7.45~7.52(6H,m),7.54(3H,s),7.54~7.63(6H,m),7.84~7.87(2H,m),7.98(1H,m),8.12(1H,m),8.2(1H,m),8.41~8.45(2H,m),8.85(1H,s),(H,);MS/FAB实验值825,计算值825.07
[制备例7]制备化合物43
化合物7-1的制备
将41.7g(128.7mmol)4-溴-N,N-二苯基苯胺、27mL(772mmol)氨水、2.45g(12.87mmol)CuI、12.9mL(128.7mmol)乙酰丙酮、83.9g(257.4mmol)Cs2CO3和1000mL DMF在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到12.2g(46.9mmol)化合物7-1。
化合物7-2的制备
将23.1g(88.64mmol)化合物7-1、24.1g(88.64mmol)2-溴-9,9-二甲基-9H-芴、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)3、25.5g(266mmol)NaOt-Bu以及1000mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到18.4g(40.65mmol)化合物7-2。
化合物43的制备
将7.9g(23.28mmol)化合物1-3、8.8g(19.4mmol)化合物7-2、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到5.7g(8.0mmol,41%)化合物43。
1H NMR(CDCl3,200MHz)δ=1.72(6H,s),6.38(4H,m),6.58~6.63(5H,m),6.69~6.81(5H,m),7.2(4H,m),7.28(1H,m),7.38(1H,m),7.5~7.62(7H,m),7.87(1H,m),7.98(1H,m),8.2(1H,m),8.41~8.45(2H,m);MS/FAB实验值711,计算值710.93
[制备例8]制备化合物69
化合物8-1的制备
将10g(44mmol)2-二苯并噻吩硼酸、31g(132mmol)1,4-二溴苯、2.5g(2.2mmol)Pd(PPh3)4、132mL(132mmol)1M的Na2CO3、500mL甲苯以及200mL乙醇在120℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到12.9g(38.0mmol)化合物8-1。
化合物69的制备
将7.9g(23.28mmol)化合物8-1、7g(19.4mmol)化合物1-2、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到7.1g(11.5mmol,59%)化合物69。
1H NMR(CDCl3,200MHz)δ=1.72(6H,s),5.93(1H,m),6.38(4H,m),6.58~6.63(3H,m),6.69~6.81(4H,m),7.2(2H,m),7.28~7.29(2H,m),7.38(1H,m),7.45~7.54(15H,m),7.69(1H,m),7.87(1H,m),7.98(1H,m),8.12(1H,m),8.2(1H,m),8.41~8.45(2H,m);MS/FAB实验值620,计算值619.82
[制备例9]制备化合物76
化合物9-1的制备
将10.5g(44mmol)9,9-二甲基-9H-芴-2-基硼酸、31g(132mmol)1,4-二溴苯、2.5g(2.2mmol)Pd(PPh3)4、132mL(132mmol)1M的Na2CO3、500mL甲苯以及200mL乙醇在120℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到11.5g(32.9mmol)化合物9-2。
将8.1g(23.28mmol)化合物9-1、8.7g(19.4mmol)化合物1-2、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到6.5g(9.0mmol,47%)化合物76。
1H NMR(CDCl3,200MHz)δ=1.72(12H,s),6.58(1H,m),6.69~6.75(5H,m),7.28(2H,m),7.38~7.41(3H,m),7.51~7.55(10H,m),7.62~7.63(2H,m),7.77(1H,m),7.87~7.93(3H,m);MS/FAB实验值630,计算值629.83
[制备例10]制备化合物78
化合物10-1的制备
在双颈烧瓶中装入40g(152.6mmol)2-溴苯甲酸甲酯、31.5g(183.2mmol)萘-1-基硼酸和8.8g(7.62mmol)四(三苯基膦)钯[Pd(PPh3)4]。进行搅拌的同时将1L甲苯加入其中,并将228mL(458mmol)2M的碳酸钾和228mL乙醇加入其中。在100℃进行回流5小时。反应终止之后,反应产物冷却至室温,并用蒸馏水和乙酸乙酯萃取。所得有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用己烷和乙酸乙酯作为洗脱(developing)溶剂进行柱色谱法,从而得到35g(87%)化合物10-1。
化合物10-2的制备
在单颈烧瓶中装入24g(91.49mmol)化合物10-1,使烧瓶真空并填充氩气。向其中加入1L四氢呋喃,在-75℃进行10分钟搅拌。随后,向其中加入257mL(0.41mol)MeLi(1.6M在己烷中),在-75℃搅拌10分钟,在室温下搅拌3小时。反应完成后,用蒸馏水和乙酸乙酯萃取反应产物。所得有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用己烷和乙酸乙酯作为洗脱溶剂进行柱色谱法,从而得到20g(83%)化合物10-2。
化合物10-3的制备
在单颈烧瓶中装入20g(76.23mmol)化合物10-2,并将300mL AcOH加入其中,在0℃搅拌10分钟。向反应混合物加入400mL H3PO4,并在室温搅拌1小时。反应完成后,用NaOH中和反应产物,并用蒸馏水和乙酸乙酯进行萃取。所得有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用己烷和乙酸乙酯作为洗脱溶剂进行柱色谱法,从而得到13.5g(72%)化合物10-3。
化合物10-4的制备
在单颈烧瓶中装入13.5g(55.25mmol)化合物10-3,使烧瓶真空并填充氩气。向其中加入500mL四氢呋喃,在0℃进行10分钟搅拌。随后,反应混合物中加入19.6g(0.11mol)NBS,室温下搅拌一天。反应完成后,用蒸馏水和乙酸乙酯萃取反应产物。所得有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用己烷和乙酸乙酯作为洗脱溶剂进行柱色谱法,从而得到13g(73%)化合物10-4。
化合物10-5的制备
将8.3g(88.64mmol)苯胺、28.6g(88.64mmol)化合物10-4、0.6g(2.7mmol)Pd(OAc)2、3.6mL(8.9mmol)P(t-Bu)、25.5g(266mmol)NaOt-Bu以及800mL甲苯在100℃加热搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,从而得到10.1g(30.1mmol)化合物10-5。
化合物78的制备
将7.9g(23.28mmol)化合物1-3、6.5g(19.4mmol)化合物10-5、0.13g(0.58mmol)Pd(OAc)2、0.94mL(2.32mmol)P(t-Bu)3、6.7g(69.84mmol)NaOt-Bu以及500mL甲苯在100℃回流搅拌12小时。反应完成之后,用蒸馏水清洗反应产物,并用乙酸乙酯萃取,之后所得的有机层用MgSO4干燥,使用旋转蒸发仪蒸发去除溶剂,使用柱色谱法纯化,并重结晶,从而得到6.0g(10.1mmol,52%)化合物78。
1H NMR(CDCl3,200MHz)δ=1.78(6H,s),6.63~6.69(5H,m),6.81(2H,m),7.14(1H,m),7.2(2H,m),7.5~7.58(7H,m),7.84(1H,m),7.98(2H,m),8.09(1H,m),8.2(1H,m),8.41~8.45(2H,m),8.52(1H,m);MS/FAB实验值594,计算值593.78
[实施例1]使用本发明的有机EL化合物制备OLED器件
使用本发明的发光材料制造了OLED器件。首先,将由OLED玻璃(购自三星康宁公司(Samsung-Corning))制成的透明电极ITO薄膜(15Ω/□)依次用三氯乙烯、丙酮、乙醇和蒸馏水进行超声清洗,之后在使用之前储存在异丙醇中。然后,将ITO基片装在真空沉积设备的基片夹(folder)中,将4,4',4"-三(N,N-(2-萘基)-苯基氨基)三苯胺(2-TNATA)置于真空沉积设备的小室(cell)中,然后排气,使室内真空度最高达到10-6托。接着,向所述小室施加电流以蒸发2-TNATA,从而在ITO基片上沉积厚度为60nm的空穴注入层。然后,将本发明的化合物13放入真空沉积设备的另一个小室中,通过向所述小室施加电流蒸发所述化合物13,从而在所述空穴注入层上沉积厚度为20nm的空穴传输层。在形成空穴注入层和空穴传输层后,在形成的层上沉积电致发光层。具体来说,将4,4’-N,N’-4,4'-N,N'-二咔唑-联苯(biphenyl)(CBP)主体放置在真空沉积设备的小室中,并将二-(1-苯基异喹啉基)铱(III)乙酰丙酮酸盐((piq)2Ir(acac))掺杂剂放置在另一室中。然后两种材料以不同的速率蒸发从而以4-10重量%的量进行掺杂,从而在空穴传输层上沉积厚度为30nm的电致发光层。随后,在电致发光层上沉积厚度为10nm的包含二(2-甲基-8-喹啉合(quinolinato))(对-苯基苯酚(phenylphenonate))铝(III)(BAlq)的空穴阻隔层,之后沉积厚度为20nm的包含三(8-羟基喹啉)-铝(III)(Alq)的电子传输层。接着,沉积厚度为1-2nm的喹啉酸锂(Liq)作为电子注入层,通过使用另一真空沉积设备沉积厚度为150nm的Al阴极,从而制得OLED器件。
在OLED器件中用作发光材料的各种化合物通过10-6托的真空升华纯化。
因此,在7.0V电压下的电流流动为15.3mA/cm2,得到1120cd/cm2的红光。
[实施例2]使用本发明的有机EL化合物制备OLED器件
用与实施例1相同方式制备OLED器件,不同之处在于本发明的化合物3用作空穴传输材料。
因此,在7.2V电压下的电流流动为15.1mA/cm2,得到1075cd/cm2的红光。
[实施例3]使用本发明的有机EL化合物制备OLED器件
用与实施例1相同方式制备OLED器件,不同之处在于本发明的化合物35用作空穴传输材料。
因此,在7.3V电压下的电流流动为16.3mA/cm2,得到1115cd/cm2的红光。
[实施例4]使用本发明的有机EL化合物制备OLED器件
如实施例1所述相同方法来制造OLED器件,不同之处在于使用本发明的化合物49作为空穴传输材料,并使用有机铱络合物三(2-苯基吡啶)铱(Ir(ppy)3作为电致发光层中的掺杂剂。
因此,在6.8V电压下的电流流动为4.0mA/cm2,得到1160cd/cm2的绿光。
[实施例5]使用本发明的有机EL化合物制备OLED器件
用与实施例4相同方式制备OLED器件,不同之处在于本发明的化合物58用作空穴传输材料。
因此,在7.1V电压下的电流流动为4.2mA/cm2,得到1230cd/cm2的绿光。
[实施例6]使用本发明的有机EL化合物制备OLED器件
用与实施例4相同方式制备OLED器件,不同之处在于本发明的化合物4用作空穴传输材料。
因此,在7.2V电压下的电流流动为5.0mA/cm2,得到1570cd/cm2的绿光。
[实施例7]使用本发明的有机EL化合物制备OLED器件
用与实施例4相同方式制备OLED器件,不同之处在于本发明的化合物61用作空穴传输材料。
因此,在7.0V电压下的电流流动为3.9mA/cm2,得到1300cd/cm2的绿光。
[实施例8]使用本发明的有机EL化合物制备OLED器件
用与实施例1相同方式制备OLED器件,不同之处在于本发明的化合物42用作空穴注入材料,代替2-TNATA(4,4’,4”-三(N,N-(2-萘基)-苯基氨基)三苯基胺)。
因此,在6.8V电压下的电流流动为13.5mA/cm2,得到1040cd/cm2的红光。
[实施例9]使用本发明的有机EL化合物制备OLED器件
用与实施例4相同方式制备OLED器件,不同之处在于本发明的化合物45用作空穴注入材料,代替2-TNATA(4,4’,4”-三(N,N-(2-萘基)-苯基氨基)三苯基胺)。
因此,在6.6V电压下的电流流动为4.0mA/cm2,得到1235cd/cm2的绿光。
[实施例10]使用本发明的有机EL化合物制备OLED器件
用与实施例1相同方式制备OLED器件,不同之处在于本发明的化合物46用作空穴注入材料,代替2-TNATA(4,4’,4”-三(N,N-(2-萘基)-苯基氨基)三苯基胺)。
因此,在7.2V电压下的电流流动为13.7mA/cm2,得到1005cd/cm2的红光。
[比较例1]使用常规发光材料的OLED的发光性能
用与实施例1相同方式制造OLED器件,不同的是在真空沉积设备的一个小室内使用N,N'-二(α-萘基)-N,N'-二苯基-4,4'-二胺(NPB)代替本发明的化合物作为空穴传输材料。
因此,在7.5V电压下的电流流动为15.3mA/cm2,得到1000cd/cm2的红光。
[比较例2]使用常规发光材料的OLED的发光性能
用与实施例4相同方式制造OLED器件,不同的是在真空沉积设备的一个小室内使用N,N'-二(α-萘基)-N,N'-二苯基-4,4'-二胺(NPB)代替本发明的化合物作为空穴传输材料。
因此,在7.5V电压下的电流流动为3.8mA/cm2,得到1000cd/cm2的绿光。
本发明的有机EL化合物相比于传统材料具有更好的发光性能。同样地,使用本发明的有机EL化合物作为空穴传输材料或者空穴注入材料的有机EL器件可以提升LUMO(最低未占分子轨道)和三重峰,从而增强空穴阻隔作用,导致优良的荧光效率和优异的材料使用寿命性能。此外,可以降低运行电压,并提升功率效率,从而制造优异的OLED器件。
虽然出于阐述的目的描述了本发明的优选实施方式,但是本领域技术人员应理解,各种改进、增加和替代方式也是可能的,它们不背离所附权利要求书所限定的本发明的范围和精神。
Claims (10)
1.一种由如下化学式1表示的有机电致发光化合物:
[化学式1]
其中,X表示-O-、-S-、-C(R11R12)-或者-Si(R13R14)-,其中R11至R14独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基、取代或未取代的5-元至7-元杂环烷基、或者取代或未取代的(C3-C30)环烷基,或者与相邻取代基连接成环;
R1至R4独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基、取代或未取代的(C3-C30)环烷基、取代或未取代的5-元至7-元杂环烷基、取代或未取代的(C6-C30)芳基(C1-C30)烷基、与一个或多个环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个取代或未取代的芳环稠合的5-元至7-元杂环烷基或者与一个或多个取代或未取代的芳环稠合的(C3-C30)环烷基、取代或未取代的(C1-C30)甲硅烷基、氰基、硝基或羟基,其中当R1至R4表示复数时,可相互连接形成环结构;
R5和R6表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基或者取代或未取代的5-元至7-元杂环烷基,或者与相邻取代基连接形成环;
L1和L2独立地表示化学键、取代或未取代的(C6-C30)亚芳基或者取代或未取代的(C3-C30)杂亚芳基,其中仅排除L1和L2都是化学键的情况;
Ar表示取代或未取代的(C6-C30)芳基、除了咔唑之外的取代或未取代的(C3-C30)杂芳基、取代或未取代的5-元至7-元杂环烷基、与一个或多个环烷基稠合的取代或未取代的(C6-C30)芳基、与一个或多个取代或未取代的芳环稠合的取代或未取代的(C3-C30)杂芳基、或者与一个或多个取代或未取代的芳环稠合的5-元至7-元杂环烷基,或者通过有或没有稠环的(C3-C30)亚烷基或者有或没有稠环的(C3-C30)亚烯基与相邻取代基相连接以形成脂环和单环或多环芳环;a至d独立地表示0-4的整数,其中当a至d是大于或等于2的整数时,R1、R2、R3和R4相互相同或不同,并与相邻取代基连接成环;以及
所述杂环烷基和杂芳基包含一个或多个选自B、N、O、S、P(=O)、Si和P的杂原子。
2.如权利要求1所述的有机电致发光化合物,其特征在于,所述进一步取代R1至R4、R5和R6、R11至R14、L1、L2和Ar的取代基独立地选自下组中的一个或多个:氘、卤素、被卤素取代或未取代的(C1-C30)烷基、(C6-C30)芳基、被(C6-C30)芳基取代或未取代的(C3-C30)杂芳基、5-元至7-元杂环烷基、与一个或多个芳环稠合的5-元至7-元杂环烷基、(C3-C30)环烷基、与一个或多个芳环稠合的(C6-C30)环烷基、R21R22R23Si-、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、NR24R25、BR26R27、PR28R29、P(=O)R30R31、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、R32S-、R33O-、R34C(=O)-、R35C(=O)O-、羧基、硝基和羟基,其中R21至R33独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(C3-C30)杂芳基、或者取代或未取代的5-元至7-元杂环烷基,或者它们通过有或没有稠环的取代或未取代的(C3-C30)亚烷基或者有或没有稠环的取代或未取代的(C3-C30)亚烯基与相邻取代基相连接以形成脂环和单环或多环芳环,所形成的脂环和单环或多环芳环的碳原子可被一个或多个选自氮、氧和硫的杂原子取代;并且R34和R35表示(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳基或者(C6-C30)芳氧基。
5.一种有机电致发光器件,所述器件包含权利要求1-4中任一项所述的有机电致发光化合物。
6.如权利要求5所述的有机电致发光器件,其特征在于,所述有机电致发光化合物用作空穴注入材料或者空穴传输材料。
7.如权利要求6所述的有机电致发光器件,其特征在于,该器件包含第一电极;第二电极;以及插入所述第一电极和第二电极之间的一层或多层有机层,所述有机层包含化学式1表示的一种或多种有机电致发光化合物。
8.如权利要求7所述的有机电致发光器件,其特征在于,所述有机层还包含选自元素周期表中第1族、第2族的有机金属、第四周期和第五周期过渡金属、镧系金属和d-过渡元素的一种或多种金属或其配合物。
9.如权利要求7所述的有机电致发光器件,其特征在于,所述有机层包含电致发光层和电荷产生层。
10.如权利要求7所述的有机电致发光器件,其特征在于,所述有机层还包含一层或多层发射红光、绿光或蓝光的有机电致发光层,以发射白光。
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Cited By (6)
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Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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WO2014069602A1 (ja) * | 2012-11-02 | 2014-05-08 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US9748492B2 (en) | 2012-11-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
JP2014110315A (ja) | 2012-11-30 | 2014-06-12 | Samsung Display Co Ltd | 有機電界発光素子用正孔輸送材料及びそれを用いた有機電界発光素子 |
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KR102474920B1 (ko) * | 2018-12-20 | 2022-12-05 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
WO2023078824A1 (en) | 2021-11-04 | 2023-05-11 | Dottikon Es Holding Ag | Spiro-(indane-fluorene) type compounds and their use in organic electronics |
Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060121312A1 (en) * | 2004-11-26 | 2006-06-08 | Canon Kabushiki Kaisha | Fluorene compound and organic light-emitting device |
US20070228399A1 (en) * | 2006-03-28 | 2007-10-04 | Canon Kabushiki Kaisha | Full-color organic el panel |
US20070228941A1 (en) * | 2006-03-28 | 2007-10-04 | Canon Kabushiki Kaisha | Amino compound for organic light-emitting device and organic light-emitting device including the same |
US20070252519A1 (en) * | 2006-04-25 | 2007-11-01 | Fuji Xerox Co., Ltd. | Novel thiophene-containing compound and thiophene-containing compound polymer, organic electroluminescent device, production method thereof, and image display medium |
US20080124573A1 (en) * | 2006-11-28 | 2008-05-29 | Canon Kabushiki Kaisha | Amine compound and organic light-emitting device |
US20090066235A1 (en) * | 2007-08-06 | 2009-03-12 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescence device using the same |
EP2067767A1 (en) * | 2007-12-04 | 2009-06-10 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
EP2075309A2 (en) * | 2007-12-31 | 2009-07-01 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
EP2145936A2 (en) * | 2008-07-14 | 2010-01-20 | Gracel Display Inc. | Fluorene and pyrene derivatives and organic electroluminescent device using the same |
WO2010044130A1 (ja) * | 2008-10-17 | 2010-04-22 | 三井化学株式会社 | 芳香族アミン誘導体、及びそれらを用いた有機エレクトロルミネッセンス素子 |
WO2010050778A1 (en) * | 2008-10-31 | 2010-05-06 | Gracel Display Inc. | Novel compounds for organic electronic material and organic electronic device using the same |
CN101993410A (zh) * | 2009-08-10 | 2011-03-30 | 三星移动显示器株式会社 | 杂环化合物和包括该杂环化合物的有机发光装置 |
CN102449106A (zh) * | 2009-03-23 | 2012-05-09 | 罗门哈斯电子材料韩国有限公司 | 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件 |
CN102482215A (zh) * | 2009-08-19 | 2012-05-30 | 出光兴产株式会社 | 芳胺衍生物及使用该芳胺衍生物的有机电致发光元件 |
CN102574790A (zh) * | 2009-10-02 | 2012-07-11 | 出光兴产株式会社 | 芳胺衍生物及有机电致发光元件 |
CN102596907A (zh) * | 2009-11-16 | 2012-07-18 | 出光兴产株式会社 | 芳香族胺衍生物和使用其的有机电致发光元件 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5112601B2 (ja) * | 2003-10-07 | 2013-01-09 | 三井化学株式会社 | 複素環化合物および該化合物を含有する有機電界発光素子 |
JP3983215B2 (ja) * | 2003-10-17 | 2007-09-26 | 三井化学株式会社 | 9,9−ジフェニルフルオレン化合物、および該9,9−ジフェニルフルオレン化合物を含有する有機電界発光素子 |
JP5644063B2 (ja) * | 2008-05-07 | 2014-12-24 | 三菱化学株式会社 | 有機電界発光素子用組成物、高分子膜、有機電界発光素子、有機elディスプレイ及び有機el照明 |
KR101379133B1 (ko) * | 2008-05-29 | 2014-03-28 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그들을 사용한 유기 전기발광 소자 |
-
2010
- 2010-07-29 KR KR1020100073229A patent/KR20120011445A/ko not_active Application Discontinuation
-
2011
- 2011-07-29 JP JP2013521715A patent/JP2013539205A/ja active Pending
- 2011-07-29 WO PCT/KR2011/005584 patent/WO2012015265A1/en active Application Filing
- 2011-07-29 TW TW100126954A patent/TW201213501A/zh unknown
- 2011-07-29 CN CN2011800470321A patent/CN103298800A/zh active Pending
Patent Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060121312A1 (en) * | 2004-11-26 | 2006-06-08 | Canon Kabushiki Kaisha | Fluorene compound and organic light-emitting device |
US20070228399A1 (en) * | 2006-03-28 | 2007-10-04 | Canon Kabushiki Kaisha | Full-color organic el panel |
US20070228941A1 (en) * | 2006-03-28 | 2007-10-04 | Canon Kabushiki Kaisha | Amino compound for organic light-emitting device and organic light-emitting device including the same |
US20070252519A1 (en) * | 2006-04-25 | 2007-11-01 | Fuji Xerox Co., Ltd. | Novel thiophene-containing compound and thiophene-containing compound polymer, organic electroluminescent device, production method thereof, and image display medium |
US20080124573A1 (en) * | 2006-11-28 | 2008-05-29 | Canon Kabushiki Kaisha | Amine compound and organic light-emitting device |
US20090066235A1 (en) * | 2007-08-06 | 2009-03-12 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescence device using the same |
EP2067767A1 (en) * | 2007-12-04 | 2009-06-10 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
EP2075309A2 (en) * | 2007-12-31 | 2009-07-01 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
EP2145936A2 (en) * | 2008-07-14 | 2010-01-20 | Gracel Display Inc. | Fluorene and pyrene derivatives and organic electroluminescent device using the same |
WO2010044130A1 (ja) * | 2008-10-17 | 2010-04-22 | 三井化学株式会社 | 芳香族アミン誘導体、及びそれらを用いた有機エレクトロルミネッセンス素子 |
WO2010050778A1 (en) * | 2008-10-31 | 2010-05-06 | Gracel Display Inc. | Novel compounds for organic electronic material and organic electronic device using the same |
CN102449106A (zh) * | 2009-03-23 | 2012-05-09 | 罗门哈斯电子材料韩国有限公司 | 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件 |
CN101993410A (zh) * | 2009-08-10 | 2011-03-30 | 三星移动显示器株式会社 | 杂环化合物和包括该杂环化合物的有机发光装置 |
CN102482215A (zh) * | 2009-08-19 | 2012-05-30 | 出光兴产株式会社 | 芳胺衍生物及使用该芳胺衍生物的有机电致发光元件 |
CN102574790A (zh) * | 2009-10-02 | 2012-07-11 | 出光兴产株式会社 | 芳胺衍生物及有机电致发光元件 |
CN102596907A (zh) * | 2009-11-16 | 2012-07-18 | 出光兴产株式会社 | 芳香族胺衍生物和使用其的有机电致发光元件 |
Non-Patent Citations (1)
Title |
---|
JOY E. ROGERS, ET AL.: ""Insight into the Nonlinear Absorbance of Two Related Series of Two-Photon Absorbing Chromophores"", 《J. PHYS. CHEM. A》 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107148408A (zh) * | 2015-12-31 | 2017-09-08 | 材料科学有限公司 | 有机化合物及包含该有机化合物的有机电致发光元件 |
CN107148408B (zh) * | 2015-12-31 | 2019-02-05 | 材料科学有限公司 | 有机化合物及包含该有机化合物的有机电致发光元件 |
US10941108B2 (en) | 2015-12-31 | 2021-03-09 | Material Science Co., Ltd. | Organic compound and organic electroluminescent element comprising same |
CN108352449A (zh) * | 2016-10-18 | 2018-07-31 | 株式会社Lg化学 | 有机发光器件 |
US10461259B2 (en) | 2016-10-18 | 2019-10-29 | Lg Chem, Ltd. | Organic light emitting device |
CN110642819A (zh) * | 2018-06-27 | 2020-01-03 | 东进世美肯株式会社 | 新颖化合物及包含其的有机发光器件 |
CN108948028A (zh) * | 2018-08-22 | 2018-12-07 | 宇瑞(上海)化学有限公司 | 一种含氧硫杂环三芳胺化合物的有机光电器件及其应用 |
CN108948028B (zh) * | 2018-08-22 | 2021-09-14 | 宇瑞(上海)化学有限公司 | 一种含氧硫杂环三芳胺化合物的有机光电器件及其应用 |
CN109867619A (zh) * | 2019-04-02 | 2019-06-11 | 西安瑞联新材料股份有限公司 | 一种OLED中间体11-氯-7H-苯并[c]咔唑及其合成方法 |
CN112079778A (zh) * | 2020-09-18 | 2020-12-15 | 吉林奥来德光电材料股份有限公司 | 一种有机发光化合物及其制备方法和器件 |
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TW201213501A (en) | 2012-04-01 |
KR20120011445A (ko) | 2012-02-08 |
WO2012015265A1 (en) | 2012-02-02 |
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