WO2010058946A2 - Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés - Google Patents

Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés Download PDF

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WO2010058946A2
WO2010058946A2 PCT/KR2009/006779 KR2009006779W WO2010058946A2 WO 2010058946 A2 WO2010058946 A2 WO 2010058946A2 KR 2009006779 W KR2009006779 W KR 2009006779W WO 2010058946 A2 WO2010058946 A2 WO 2010058946A2
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substituted
unsubstituted
aryl
hetero atom
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WO2010058946A3 (fr
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배재순
김정곤
김지은
장혜영
장준기
전상영
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주식회사 엘지화학
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Priority to EP09827711.4A priority Critical patent/EP2351723B1/fr
Priority to JP2011537356A priority patent/JP5650654B2/ja
Priority to US13/129,768 priority patent/US9200196B2/en
Publication of WO2010058946A2 publication Critical patent/WO2010058946A2/fr
Publication of WO2010058946A3 publication Critical patent/WO2010058946A3/fr

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Definitions

  • the present invention relates to a novel chrysene derivative and an organic electric device using the same.
  • An organic electric device means a device requiring charge exchange between an electrode and an organic material using holes and / or electrons.
  • the organic electric element can be divided into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). Form of electrical elements.
  • the second type is an electrical device in which holes and / or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • organic electric element examples include an organic light emitting element, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like, all of which are used to inject or transport holes, inject or transport electrons, or light emitting materials to drive the device. need.
  • OPC organic photoconductor
  • a hole injection or transport material, an electron injection or transport material, or a light emitting material functions on a similar principle.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes meet the electrons. When it falls back to the ground, it glows.
  • Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
  • Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material which constitutes the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • a stable and efficient material is supported by a stable and efficient material.
  • the present invention is to solve the problems of the prior art as described above, an object of the present invention is to provide a stable and efficient novel chrysene derivative and an organic electric device using the same.
  • One aspect of the present invention for solving the above object provides a compound represented by the following formula (1).
  • R 1 is a substituted or unsubstituted C 1 ⁇ C 40 alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 2 to C 40 heterocycloalkyl group; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S as a hetero atom,
  • R2 is a substituted or unsubstituted C 1 ⁇ C 40 Alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 3 ⁇ C 40 heterocycloalkyl group; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S
  • R3 to R7 are each independently hydrogen; Substituted or unsubstituted C One Through C 40 Alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 2 to C 40 heterocycloalkyl group containing O, N or S as a hetero atom; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And a substituted or unsubstituted and selected from the group consisting
  • X is hydrogen; Substituted or unsubstituted C One Through C 40 Alkyl group; A substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group; A substituted or unsubstituted C 2 to C 40 heterocycloalkyl group containing O, N or S as a hetero atom; Substituted or unsubstituted C 2 Through C 40 Alkenyl group; Substituted or unsubstituted C 1 ⁇ C 40 Alkoxy group; Substituted or unsubstituted amino group; Substituted or unsubstituted C 6 Through C 40 An aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S as a hetero atom, to form
  • R3 to R7 and X are hydrogen.
  • a second aspect of the present invention for achieving the above object is an organic electrical device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, one of the organic material layer Layer or more provides an organic electric device comprising the compound represented by the formula (1).
  • the compound according to the present invention may serve as hole injection, hole transport, electron injection and transport, or a light emitting material in an organic electric device including an organic light emitting device, and the organic electric device according to the present invention has efficiency, driving voltage, and stability. Excellent properties in terms of appearance.
  • FIG. 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an exemplary embodiment of the present invention.
  • FIG. 2 is a graph showing excitation wavelengths and emission wavelengths in the film 200A of Compound 1-18.
  • One aspect of the present invention relates to a compound represented by Chemical Formula 1.
  • alkyl group, cycloalkyl group, heterocycloalkyl group, alkenyl group, alkoxy group, amino group, aryl group, heteroaryl group, arylamine group and heteroarylamine group in R2 to R7 are substituted with other functional groups, halogen, deuterium, amino group, Nitrile group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 1 to C 40 alkoxy group, C 3 to C 40 cycloalkyl group, hetero atoms include O, N or S To C 2 ⁇ C 40 Heterocycloalkyl group, C 6 ⁇ C 40 An aryl group and hetero atoms are substituted with one or more groups selected from the group consisting of C 3 ⁇ C 40 heteroaryl group containing O, N or S,
  • alkyl group, cycloalkyl group, heterocycloalkyl group, alkenyl group, alkoxy group, amino group, aryl group, heteroaryl group and heteroarylamine group in R1 and X are substituted with other functional groups, halogen, deuterium, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 2 ⁇ C 40 containing O, N or S as a hetero atom It is substituted with at least one group selected from the group consisting of a heterocycloalkyl group, C 6 ⁇ C 40 aryl group and C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom.
  • the alkyl group and the alkoxy group preferably have 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Moreover, it is preferable that carbon number is 2-40, and, as for an alkenyl group, it is more preferable that it is 2-20.
  • the aryl group preferably has 6 to 40 carbon atoms, and more preferably 6 to 20 carbon atoms.
  • the heterocyclic group preferably has 4 to 40 carbon atoms, and more preferably 4 to 20 carbon atoms.
  • the aryl amine group preferably has 6 to 60 carbon atoms, and more preferably 6 to 24 carbon atoms.
  • the heteroarylamine group preferably has 4 to 60 carbon atoms, and more preferably 4 to 20 carbon atoms.
  • substituted or unsubstituted is halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heterocyclic, carbazolyl, flu It is preferable to be substituted or unsubstituted with one or more substituents selected from the group consisting of an orenyl group, a nitrile group and an acetylene group, but is not limited thereto.
  • R 1 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And a substituted or unsubstituted and selected from the group consisting of C 3 ⁇ C 40 heteroarylamine group containing O, N or S as a hetero atom,
  • R2 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And it may be selected from the group consisting of a substituted or unsubstituted heteroarylamine group of C 3 ⁇ C 40 including O, N or S as a hetero atom.
  • R1 is a C 6 ⁇ C 20 aryl group; An aryl group of C 6 ⁇ C 40 aryl group or a heteroatom as O, N, or the containing S C 3 ⁇ C 40 heteroaryl group substituted by a C 6 ⁇ C 20; And it is selected from the group consisting of C 3 ⁇ C 20 heteroaryl substituted with an aryl group of C 6 ⁇ C 20 and containing O, N or S as a hetero atom,
  • R2 is C 6 ⁇ C 20 An aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it may be selected from the group consisting of C 6 ⁇ C 20 arylamine group.
  • R1 is preferably selected from the group consisting of substituents represented by the following structural formulas, but are not limited thereto.
  • R2 are preferably selected from the group consisting of substituents represented by the following structural formulas, but are not limited thereto.
  • R3 to R7 may be hydrogen, or four of R3 to R7 and X may be hydrogen.
  • X is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; And it is preferably selected from the group consisting of a substituted or unsubstituted heteroarylamine group of C 3 ⁇ C 40 containing O, N or S as a hetero atom.
  • X is a C 6 ⁇ C 20 aryl group; An aryl group of C 6 ⁇ C 40 aryl group or a heteroatom as O, N, or the containing S C 3 ⁇ C 40 heteroaryl group substituted by a C 6 ⁇ C 20; And it is more preferably selected from the group consisting of C 3 ⁇ C 20 heteroaryl group substituted with a C 6 ⁇ C 20 aryl group and containing O, N or S as a hetero atom.
  • X are preferably selected from the group consisting of substituents represented by the following structural formulas, but are not limited thereto.
  • R3 to R7 and X are hydrogen
  • the substituent except for hydrogen in R3 to R7 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group; C 3 ⁇ C 40 heteroaryl group which is substituted or unsubstituted and contains O, N or S as a hetero atom; Substituted or unsubstituted C 5 Through C 40 An arylamine group; And it is preferably selected from the group consisting of a substituted or unsubstituted heteroarylamine group of C 3 ⁇ C 40 containing O, N or S as a hetero atom.
  • R3 to R7 and X when four of R3 to R7 and X is hydrogen, the substituent except for hydrogen in R3 to R7 is a C 6 ⁇ C 20 aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is more preferably selected from the group consisting of C 6 ⁇ C 20 arylamine groups.
  • R3 to R7 and X are hydrogen
  • the substituent except for hydrogen in R3 to R7 is preferably selected from the group consisting of substituents represented by the following structural formulas, but is not limited thereto.
  • R1 is a C 6 ⁇ C 20 aryl group; An aryl group of C 6 ⁇ C 40 aryl group or a heteroatom as O, N, or the containing S C 3 ⁇ C 40 heteroaryl group substituted by a C 6 ⁇ C 20; And C 6 ⁇ C 20 aryl group which is substituted heteroatom as O, N, or is selected from the group consisting of C 3 ⁇ C 20 heteroaryl group containing S; R2 is C 6 ⁇ C 20 An aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is selected from the group consisting of C 6 ⁇ C 20 aryl group; An aryl group of
  • X and R7 are hydrogen, and at least one of R3 to R6 is an aryl group of C 6 to C 20 ; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is preferably selected from the group consisting of C 6 ⁇ C 20 arylamine group.
  • R1 is a C 6 ⁇ C 20 aryl group; An aryl group of 6 C ⁇ C 40 aryl group or a heteroatom as O, N or S containing the C ⁇ 3 C 40 heteroaryl group substituted by a C 6 ⁇ 20 C; And C 6 ⁇ C 20 aryl group which is substituted heteroatom as O, N, or is selected from the group consisting of C 3 ⁇ C 20 heteroaryl group containing S; R2 is C 6 ⁇ C 20 An aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is selected from the group consisting of C 6 ⁇ C 20 arylamine group;
  • R5 is C 6 ⁇ C 20 aryl group; C 6 ⁇ C 40 aryl group, C 6 ⁇ C 20 aryl group substituted with C 3 ⁇ C 40 heteroaryl group containing O, N or S as a hetero atom or C 5 ⁇ C 40 arylamine group; Heteroaryl group is substituted with a C 6 ⁇ C 20 aryl C 3 ⁇ containing O, N or S as heteroatom C 20; And it is selected from the group consisting of C 6 ⁇ C 20 arylamine group,
  • R3, R4, R6, R7 and X are hydrogen, but are not limited thereto.
  • the compound represented by Chemical Formula 1 according to the present invention includes a functional group specific to at least one of R3 to R7, and X as well as R1 and R2, thereby having a compound having at least three functional groups centered on the chrysene core as a whole. Can be.
  • the organic electronic device containing such a compound in the case of including a specific functional group in the R1, R2 and R5 of the formula (1), can exhibit characteristics such as improved efficiency, drive voltage, stability have.
  • X and R3 to R7 may all be hydrogen.
  • the compound represented by Chemical Formula 1 may be prepared according to the method described below. First, Compound A is prepared according to the method of Journal of Organic Chemistry 2005,70, 3511-3517 as follows.
  • Compound A synthesized as described above connects two R1 and R2 functional groups through Suzuki coulpling to obtain Compound B or Compound C as a final target.
  • a second aspect of the present invention is an organic electrical device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is the chemical formula It relates to an organic electric element comprising the compound of (1).
  • the organic material layer may include a hole injection layer and a hole transport layer, and the hole injection layer and the hole transport layer may include the compound of Formula 1.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1.
  • the organic material layer may include an electron transport layer
  • the electron transport layer may include the compound of Formula 1.
  • the organic electric element is preferably selected from the group consisting of an organic light emitting element, an organic solar cell, an organic photoconductor (OPC) and an organic transistor.
  • OPC organic photoconductor
  • the compound of Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of an organic electrical device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • the organic electric device of the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present invention, that is, the compound of Formula 1.
  • the organic material layer of the organic electric device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic electric device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic electric device is not limited thereto and may include a smaller number of organic material layers.
  • the organic electric element of the present invention may be manufactured by, for example, sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation may be used, but is not limited thereto.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention 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), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer.
  • a material having high mobility to electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compounds according to the present invention can also operate on principles similar to those applied to organic light emitting devices in organic electrical devices, including organic solar cells, organic photoconductors, organic transistors, and the like.
  • the compound represented by the formula (1) according to the present invention can generally be prepared by a multistage chemical reaction. That is, some intermediate compounds are prepared first, and compounds of formula 1 are prepared from the intermediate compounds. Exemplary intermediate compounds are the compounds described below. In these compounds, "Br" may be substituted with any other reactive atom or functional group.
  • Compound 1-7 (4.8 g, 73%) was prepared by the same method as Preparation Example 5, except that Compound S-7 (4.4 g, 8.7 mmol) was used instead of Compound S-4 in Preparation Example 5. It was.
  • the glass substrate coated with ITO indium tin oxide
  • ITO indium tin oxide
  • distilled water filtered secondly was used as a filter of the Millipore Co. company.
  • ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma and then transferred to a vacuum evaporator.
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • NPB 400 kPa
  • the compound 1-18 which was a host
  • the D1 compound which was a dopant
  • the following E1 compound was vacuum deposited to a thickness of 200 kPa on the light emitting layer to form an electron injection and transport layer.
  • a cathode was formed by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron injection and transport layer.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • Table 7 The results of evaluating the characteristics of the manufactured organic light emitting device are shown in Table 7 below.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 1-61, 1-6, 1-7, or 1-14 described in Table 7 was deposited instead of Compound 1-18.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • Table 7 The results of evaluating the characteristics of the manufactured organic light emitting device are shown in Table 7 below.
  • the organic electric device including the compound according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.
  • Example 1-1 except that using Compound 1-6, 1-7 or 1-14 shown in Table 8 as a host material in place of Compound 1-18 and using the following formula D2 as a dopant Example 1
  • An organic light emitting device was manufactured in the same manner as in ⁇ 1.
  • Example 1-1 an organic light emitting device was manufactured in the same manner as in Example 1-1, except for using Compound H2 as a host material as a dopant instead of Compound 1-18.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

L'invention concerne de nouveaux dérivés de chrysène et un dispositif électrique organique utilisant ces dérivés. Les dérivés de chrysène selon l'invention servent de substances pour injection et transport de trous, injection et transport d'électrons, ou émission de lumière dans un dispositif électrique organique comprenant un dispositif électroluminescent organique, et servent d'hôte électroluminescent ou de dopant, lorsqu'elles sont utilisées seules.
PCT/KR2009/006779 2008-11-18 2009-11-18 Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés WO2010058946A2 (fr)

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EP09827711.4A EP2351723B1 (fr) 2008-11-18 2009-11-18 Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés
JP2011537356A JP5650654B2 (ja) 2008-11-18 2009-11-18 新規なクリセン誘導体およびこれを用いた有機電子素子
US13/129,768 US9200196B2 (en) 2008-11-18 2009-11-18 Chrysene derivatives and organic electrical device using the same

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KR102191991B1 (ko) 2013-09-06 2020-12-17 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
US9985579B2 (en) 2016-04-12 2018-05-29 Preformed Line Products Co. Mounting assembly for mounting a solar panel
KR102536248B1 (ko) 2017-06-21 2023-05-25 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자
KR102415376B1 (ko) 2017-08-04 2022-07-01 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR102536246B1 (ko) 2018-03-23 2023-05-25 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함한 유기 발광 소자
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US20110227053A1 (en) 2011-09-22
EP2351723B1 (fr) 2014-02-26
JP5650654B2 (ja) 2015-01-07
KR101137197B1 (ko) 2012-04-20
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JP2012509317A (ja) 2012-04-19
US9200196B2 (en) 2015-12-01

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