WO2011074770A2 - 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 - Google Patents
유기광전소자용 화합물 및 이를 포함하는 유기광전소자 Download PDFInfo
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- 0 *C(*=C(*)*N=*I)c1cc(C2=*C*C([Tl](*)(*)=C)=*2)ccc1 Chemical compound *C(*=C(*)*N=*I)c1cc(C2=*C*C([Tl](*)(*)=C)=*2)ccc1 0.000 description 24
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Definitions
- the present invention relates to a compound for an organic photoelectric device and an organic photoelectric device including the same, which can provide an organic photoelectric device having excellent lifetime, efficiency, electrochemical stability, and thermal stability.
- An organic photoelectric device refers to a device that requires charge exchange between an electrode and an organic material using holes or electrons.
- the organic photoelectric device may be classified into two types according to the operation principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.
- the second is an electronic device in which holes 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 photoelectric device examples include an organic photoelectric device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which are used to inject or transport holes, or inject or transport materials for driving the device. Or a luminescent material.
- organic light emitting diodes are attracting attention as the demand for flat panel displays increases.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- Such an organic photoelectric device is a device that converts electrical energy into light by applying a current to an organic light emitting material and has a structure in which a functional organic material layer is inserted between an anode and a cathode.
- the organic layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic photoelectric 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.
- the document describes a structure in which a thin film of a diamine derivative (hole transport layer) and a thin film of tris (8hydroxyquinolate) aluminum (Alq 3 ) are laminated as an organic layer.
- phosphorescent as well as fluorescent light emitting materials can be used as light emitting materials of organic photoelectric devices (DFO'Brien et al., Applied Physics Letters, 74 (3), 442444, 1999; MA Baldo et al., Applied Physics letters, 75 (1), 46, 1999), and these phosphorescent luminescences triple the singlet excitons through intersystem crossings after electrons transition from the ground state to the excited state. It is composed of a mechanism for non-luminescent transition to anti-exciter, and then triplet excitons to emit light while transitioning to the ground state.
- the material used as the organic material layer in the organic photoelectric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
- a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
- the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
- the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.
- the host / dopant system can be used as a light emitting material.
- a material forming 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, a host and / or a dopant in the light emitting material, etc.
- a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
- This stable and efficient material should be preceded, and development of a stable and efficient organic material layer material for an organic photoelectric device has not been made yet, and therefore, development of new materials is continuously required. The need for such a material development is the same for the other organic photoelectric devices described above.
- a compound for an organic photoelectric device which may serve as light emitting, or electron injection and / or transport, and may serve as a light emitting host with an appropriate dopant.
- An organic photoelectric device excellent in lifespan, efficiency, driving voltage, electrochemical stability, and thermal stability is provided.
- X1 to X9 are the same as or different from each other, and independently heteroatoms or CR, wherein R is selected from the group consisting of hydrogen, C1 to C30 alkyl group, and C6 to C30 aryl group, and among X1 to X3 At least two are heteroatoms, at least one of X4 to X6 is a heteroatom, at least one of X7 to X9 is a heteroatom, and in Formula 1, Ar1 to Ar6 are the same as or different from each other, and are independently substituted Or an unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arylaminilene group, a substituted or unsubstituted carbazoylene group, and a substituted or unsubstituted Selected from the group consisting of fluorenylene groups, Ar7 to Ar12 are the
- the number of heteroatoms of X4 to X6 may be 2.
- the compound for an organic photoelectric device represented by Formula 1 or 2 the compound X2, X3, X5, X6, X7 and X9 are heteroatoms; X 2, X 3, X 5, X 6, X 8 and X 9 are heteroatoms;
- the compound wherein X1, X3, X4, X5, X8 and X9 are heteroatoms; And X1, X3, X4, X5, X7 and X9 may be a compound selected from the group consisting of a heteroatom compound.
- the compound for an organic photoelectric device represented by Formula 1 or 2 is a compound wherein X2, X6, X7 and X9 is a heteroatom, or the compound X3, X5, X7 and X9 is a heteroatom Can be.
- the compound for an organic photoelectric device represented by Formula 1 or 2 wherein X2, X6, X7, X8 and X9 is a heteroatom or X3, X5, X7, X8 and X9 is hetero It may be a compound that is an atom.
- the compound for an organic photoelectric device represented by Formula 1 or 2 wherein X2, X3, X5, X6, X7, X8 and X9 is a heteroatom, or the X1, X3, X4, X5 , X7, X8 and X9 may be a heteroatom.
- Ar7 to Ar12 are the same as or different from each other, and independently a phenyl group, a biphenyl group, a terphenyl group, stilbenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group and Selected from the group consisting of a perylene group
- Ar1 to Ar6 are the same as or different from each other, and independently a phenylene group, a biphenylene group, a terphenylene group, a stilbenylene group, a naphthylene group, an anthracenylene group, a phenanthrenylene group, Selected from the group consisting of a pyrenylene group and a peryleneylene group
- Ar13 to Ar18 are the same as or different from each other, and independently a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, naph
- Ar7 to Ar12 are the same as or different from each other, and independently a thiophenyl group, furanyl group, pyrroyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, In the group consisting of a triazolyl group, pyridinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, acridinyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzoquinolinyl group and phenanthrolidinyl group
- Ar13 to Ar18 are the same as or different from each other, and are independently a thiophenyl group, furanyl group, pyrroyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, and triazolyl group , Pyridin
- the organic photoelectric device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least one of the organic thin film layer for the above organic photoelectric device It provides an organic photoelectric device comprising a compound.
- the organic thin film layer may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.
- the compound for an organic photoelectric device may be included in an electron transport layer or an electron injection layer.
- the compound for an organic photoelectric device may be included in a light emitting layer.
- the compound for an organic photoelectric device may be used as a phosphorescent or fluorescent host material in a light emitting layer.
- the compound for an organic photoelectric device may be used as a fluorescent blue dopant material in a light emitting layer.
- the organic photoelectric device may be selected from the group consisting of an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
- a display device including the organic photoelectric device described above is provided.
- 1 to 5 are cross-sectional views illustrating various embodiments of an organic photoelectric device that may be manufactured using the compound for an organic photoelectric device according to an embodiment of the present invention.
- organic photoelectric device 110 cathode
- hole injection layer 230 light emitting layer + electron transport layer
- C1 to C30 alkyl group C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C10 alkoxy group, fluoro group, trifluoro It means substituted by C1-C10 trifluoroalkyl groups, such as a romoxy group, or a cyano group.
- hetero includes one to three heteroatoms selected from the group consisting of N, O, S, and P in one ring group, and the rest is preferably carbon.
- alkyl refers to an aliphatic hydrocarbon group unless otherwise defined.
- the alkyl moiety can be a "saturated alkyl” group, meaning that it does not contain any alkenes or alkyne moieties.
- the alkyl moiety may be an "unsaturated alkyl” moiety, meaning that it contains at least one alkene or alkyne moiety.
- Alkene moiety means a group of at least two carbon atoms consisting of at least one carbon carbon double bond
- an "alkyne” moiety means a group of at least two carbon atoms consisting of at least one carbon carbon triple bond Means.
- the alkyl moiety, whether saturated or unsaturated may be branched, straight chain or cyclic.
- Alkyl groups may have from 1 to 20 carbon atoms.
- the alkyl group may be a medium sized alkyl having 1 to 10 carbon atoms.
- the alkyl group may be lower alkyl having 1 to 6 carbon atoms.
- C1 to C4 alkyl may be selected from the group consisting of 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, isopropyl, nbutyl, isobutyl, secbutyl and tbutyl. Indicates.
- Typical alkyl groups include, individually and from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tbutyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
- aryl means an aryl group including carbocyclicaryl (eg, phenyl) having at least one ring having a shared pi electron system.
- carbocyclicaryl eg, phenyl
- the term includes monocyclic or fused ring polycyclic (ie rings that divide adjacent pairs of carbon atoms) groups.
- the term also encompasses spiro compounds having one carbon as a contact.
- heteroaryl refers to an aryl group comprising heterocyclicaryl (eg, pyridine) having at least one ring having a shared pi electron system.
- heterocyclicaryl eg, pyridine
- the term includes monocyclic or fused ring polycyclic (ie rings that divide adjacent pairs of carbon atoms) groups.
- the term also encompasses spiro compounds having one carbon as a contact.
- the compound for an organic photoelectric device may have a structure in which three heteroaryl groups are bonded to a benzene core structure.
- the three substituent bonding positions may be 1, 3 and 5 positions of the core benzene.
- the compound for an organic photoelectric device may synthesize a compound having various energy band gaps by introducing various substituents into the core portion and the two substituents, thereby satisfying the requirements for the emission layer as well as the electron injection layer and the transfer layer.
- the electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent life time when driving the organic photoelectric device due to excellent electrochemical and thermal stability. Properties can be improved.
- a compound for an organic photoelectric device represented by the following Chemical Formula 1 or 2 is provided.
- X1 to X9 are the same as or different from each other, and independently heteroatoms or CR, wherein R is selected from the group consisting of hydrogen, C1 to C30 alkyl group, and C6 to C30 aryl group, and among X1 to X3 At least two are heteroatoms, at least one of X4 to X6 may be a heteroatom, and at least one of X7 to X9 may be a heteroatom.
- the heteroaryl group which is a substituent of the core benzene may be a total of three, and one of the heteroaryl groups may include at least two heteroatoms.
- each combination may be selected according to the properties required.
- the number of heteroatoms of X4 to X6 may be 2.
- two heteroaryl groups in the three heteroaryl groups may include two or more heteroatoms.
- a compound which is an atom and a compound selected from the group consisting of X1, X3, X4, X5, X7 and X9 are heteroatom compounds are possible.
- Preferred heteroatoms may be N. However, it is not limited thereto.
- Ar1 to Ar6 are the same as or different from each other, and independently, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 aryl It may be selected from the group consisting of an aminylene group, a substituted or unsubstituted carbazoylene group, and a substituted or unsubstituted fluorenylene group.
- the compound can be very usefully applied to the light emitting layer of the organic photoelectric device.
- the carbon number exceeds the above range, sufficient effect as the device may not be obtained.
- Ar1 to Ar6 may be a phenylene group, biphenylene group, terphenylene group, stilbenylene group, naphthylene group, anthracenylene group, phenanthrenylene group, pyrenylene group or peryleneylene group.
- Ar7 to Ar12 are the same as or different from each other, and independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, a, b, c, d, e and f is the same as or different from each other, and may independently be an integer of 1 or 2.
- the structure in which the substituent is bonded is excellent in thermal stability or resistance to oxidation, thereby improving lifespan characteristics of the organic photoelectric device.
- the electron transport ability of the compound can be adjusted according to the type of the substituent.
- the structure of the compound can be prepared in bulk, thereby lowering the crystallinity. If the crystallinity of the compound is lowered, the lifetime of the device may be longer.
- Ar7 to Ar12 examples include a phenyl group, biphenyl group, terphenyl group, stilbenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, or perrylenyl group.
- Ar7 to Ar12 include thiophenyl group, furanyl group, pyrroyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, pyridazinyl group, and qui Nolinyl group, isoquinolinyl group, acridinyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzoquinolinyl group or phenanthrolidinyl group.
- Ar13 to Ar18 are the same as or different from each other, and independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 arylamine Groups, substituted or unsubstituted carbazoyl groups, and substituted or unsubstituted fluorenyl groups.
- the structure in which the substituent is bonded is excellent in thermal stability or resistance to oxidation, thereby improving lifespan characteristics of the organic photoelectric device.
- the electron transport ability of the compound can be adjusted according to the type of the substituent.
- the structure of the compound can be prepared in bulk, thereby lowering the crystallinity. If the crystallinity of the compound is lowered, the lifetime of the device may be longer.
- Ar13 to Ar18 examples include a phenyl group, biphenyl group, terphenyl group, stilbenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, or perrylenyl group.
- Ar13 to Ar18 include thiophenyl group, furanyl group, pyrroyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, pyrazinyl group, qui Nolinyl group, isoquinolinyl group, acridinyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzoquinolinyl group, or phenanthrolidinyl group.
- the compound for an organic photoelectric device including the compound as described above has a glass transition temperature of 120 ° C. or more, and a thermal decomposition temperature of 400 ° C. or more, which is excellent in thermal stability. This makes it possible to implement a high efficiency organic photoelectric device.
- the compound for an organic photoelectric device including the compound as described above may serve as light emission, electron injection and / or transport, and may also serve as a light emitting host with an appropriate dopant. That is, the compound for an organic photoelectric device may be used as a host material of phosphorescence or fluorescence, a blue dopant material, or an electron transport material.
- Compound for an organic photoelectric device according to an embodiment of the present invention is used in the organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic photoelectric device, it is possible to lower the driving voltage.
- one embodiment of the present invention provides an organic photoelectric device comprising the compound for an organic photoelectric device.
- the organic photoelectric device means an organic photoelectric device, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, or the like.
- a compound for an organic photoelectric device according to an exemplary embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency. Can be.
- Another embodiment of the present invention is an organic photoelectric device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least one of the organic thin film layer is an embodiment of the present invention It provides an organic photoelectric device comprising a compound for an organic photoelectric device according to.
- the organic thin film layer which may include the compound for an organic photoelectric device may include a layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a combination thereof. At least one of the layers includes the compound for an organic photoelectric device according to the present invention.
- the electron transport layer or the electron injection layer may include a compound for an organic photoelectric device according to an embodiment of the present invention.
- the compound for an organic photoelectric device when the compound for an organic photoelectric device is included in a light emitting layer, the compound for an organic photoelectric device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material.
- 1 to 5 are cross-sectional views of an organic photoelectric device including the compound for an organic photoelectric device according to an embodiment of the present invention.
- the organic photoelectric device 100, 200, 300, 400, and 500 may be interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.
- the anode 120 includes a cathode material, and a material having a large work function is preferable as the anode material so that hole injection can be smoothly injected into the organic thin film layer.
- the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). And metal oxides such as ZnO and Al or combinations of metals and oxides such as SnO 2 and Sb.
- Thiophene] conductive polymer such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.
- a transparent electrode including indium tin oxide (ITO) may be used as the anode.
- the negative electrode 110 includes a negative electrode material, and the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al.
- Multilayer structure materials such as LiO 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
- a metal electrode such as aluminum may be used as the cathode.
- FIG. 1 illustrates an organic photoelectric device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105.
- the organic thin film layer 105 may exist only as a light emitting layer 130.
- FIG. 2 illustrates a two-layered organic photoelectric device 200 in which an emission layer 230 including an electron transport layer and a hole transport layer 140 exist as an organic thin film layer 105, as shown in FIG. 2.
- the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140.
- the light emitting layer 130 functions as an electron transporting layer
- the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as ITO.
- FIG. 3 is a three-layered organic photoelectric device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, wherein the organic thin film layer 105 is formed.
- the light emitting layer 130 is in an independent form, and has a form in which a film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties or hole transport properties is stacked in separate layers.
- FIG. 4 is a four-layered organic photoelectric device 400 having an electron injection layer 160, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170 as an organic thin film layer 105.
- the hole injection layer 170 may improve adhesion to ITO used as an anode.
- FIG. 5 shows different functions such as the electron injection layer 160, the electron transport layer 150, the light emitting layer 130, the hole transport layer 140, and the hole injection layer 170 as the organic thin film layer 105.
- the five-layered organic photoelectric device 500 having five layers is present, and the organic photoelectric device 500 is effective for lowering the voltage by forming the electron injection layer 160 separately.
- the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection layer 170 forming the organic thin film layer 105 and their Any one selected from the group consisting of a combination includes the compound for an organic photoelectric device.
- the compound for an organic photoelectric device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and among them, a hole blocking layer (not shown) when included in the electron transport layer. It is desirable to provide an organic photoelectric device having a simpler structure since it does not need to be separately formed.
- the compound for an organic photoelectric device when included in the light emitting layers 130 and 230, the compound for an organic photoelectric device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.
- the above-described organic photoelectric device may include a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating after an anode is formed on a substrate;
- the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.
- a display device including the organic photoelectric device is provided.
- the obtained compound for an organic photoelectric device was analyzed by elemental analysis. The results were as follows.
- the obtained compound for an organic photoelectric device was analyzed by elemental analysis. The results were as follows.
- the obtained compound for an organic photoelectric device was analyzed by elemental analysis. The results were as follows.
- the obtained compound for an organic photoelectric device was analyzed by elemental analysis. The results were as follows.
- the obtained compound for an organic photoelectric device was analyzed by elemental analysis. The results were as follows.
- the obtained compound for an organic photoelectric device was analyzed by elemental analysis. The results were as follows.
- the glass transition temperature and pyrolysis temperature of the synthesized materials were measured by DSC and TGA.
- ITO (120 nm) glass substrate with sheet resistance of 15 ⁇ / cm 2 was cut into 50 mm ⁇ 50 mm ⁇ 0.7 mm with an anode and ultrasonically cleaned in isopropyl alcohol and pure water for 5 minutes, and then 30 minutes. UV ozone rinse was used.
- An electron transport layer having a thickness of 30 nm was formed using the same thermal vacuum deposition conditions on the emission layer and using the compound synthesized in Example 1 and LiQ (1: 1 weight ratio).
- An organic light emitting diode was manufactured by sequentially depositing LiQ (0.5 nm) and Al (100 nm) as cathodes using the same thermal vacuum deposition conditions on the electron transport layer.
- Example 7 Except for using the compound synthesized in Example 1 and LiQ (1: 1 weight ratio), instead of forming an electron transport layer, except that the compound represented by the formula (34) and LiQ (1: 1 weight ratio) was used. An organic light emitting device was manufactured in the same manner as in Example 7.
- the current value flowing through the unit device was measured using a current voltmeter (Keithley 2400) while increasing the voltage, and the measured current value was divided by the area to obtain a result.
- the resulting organic photoelectric device was measured using a luminance meter (Minolta Cs1000A) while increasing the voltage to obtain a result.
- Table 1 shows the results of the characteristic evaluation on the organic photoelectric device manufactured by Example 7 and Comparative Example 1.
- the organic light emitting diode manufactured in Example 7 has a lower driving voltage and a very improved current efficiency and power efficiency compared to the organic light emitting diode of Comparative Example 1. It was confirmed that the performance was shown. Compound synthesized in the above example was confirmed to lower the driving voltage of the organic light emitting device, improve the brightness and efficiency.
- the organic photoelectric device according to the embodiment of the present invention shows a low driving voltage and high luminous efficiency, and thus it is confirmed that the device life is also increased. there was.
Abstract
Description
소자종류 | 1000 cd/m2에서의 측정 결과 | |||
구동전압(V) | 전류효율(cd/A) | 전력효율(lm/W) | 색좌표(x, y) | |
실시예 7 | 3.8 | 10.81 | 8.94 | 0.15, 0.19 |
비교예 1 | 4.4 | 7.65 | 5.46 | 0.15, 0.20 |
Claims (18)
- 하기 화학식 1 또는 2로 표시되는 유기광전소자용 화합물:[화학식 1] [화학식 2]상기 화학식 1 및 2에서,X1 내지 X9는 서로 동일하거나 상이하며, 독립적으로 헤테로원자 또는 CR이되, 상기 R은 수소, C1 내지 C30 알킬기 및 C6 내지 C30 아릴기로 이루어진 군에서 선택되고,X1 내지 X3 중 적어도 둘은 헤테로원자이며, 상기 X4 내지 X6 중 적어도 하나는 헤테로원자이며, 상기 X7 내지 X9 중 적어도 하나는 헤테로원자이고,상기 화학식 1에서,Ar1 내지 Ar6는 서로 동일하거나 상이하며, 독립적으로, 치환 또는 비치환된 C6 내지 C30 아릴렌기, 치환 또는 비치환된 C3 내지 C30 헤테로아릴렌기, 치환 또는 비치환된 C6 내지 C30 아릴아미닐렌기, 치환 또는 비치환된 카바조릴렌기, 및 치환 또는 비치환된 플루오레닐렌기로 이루어진 군에서 선택되고,Ar7 내지 Ar12는 서로 동일하거나 상이하며, 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 C3 내지 C30 헤테로아릴기리고,a, b, c, d, e 및 f는 서로 동일하거나 상이하며, 독립적으로 1 또는 2의 정수이고,상기 화학식 2에서,Ar13 내지 Ar18는 서로 동일하거나 상이하며, 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C3 내지 C30 헤테로아릴기, 치환 또는 비치환된 C6 내지 C30 아릴아민기, 치환 또는 비치환된 카바조릴기 및 치환 또는 비치환된 플루오레닐기로 이루어진 군에서 선택된다.
- 제 1 항에 있어서,상기 X4 내지 X6 의 헤테로원자의 수는 2인 것인 유기광전소자용 화합물.
- 제 1 항에 있어서,상기 화학식 1 또는 2로 표시되는 유기광전소자용 화합물은,상기 X2, X3, X5, X6 및 X7이 헤테로원자인 화합물 또는,상기 X2, X3, X5, X6 및 X9가 헤테로원자인 화합물인 것인 유기광전소자용 화합물.
- 제 1 항에 있어서,상기 화학식 1 또는 2로 표시되는 유기광전소자용 화합물은,상기 X2, X3, X5, X6, X7 및 X9가 헤테로원자인 화합물;상기 X2, X3, X5, X6, X8 및 X9가 헤테로원자인 화합물;상기 X1, X3, X4, X5, X8 및 X9가 헤테로원자인 화합물; 및상기 X1, X3, X4, X5, X7 및 X9가 헤테로원자 화합물로 이루어진 군에서 선택되는 화합물인 것인 유기광전소자용 화합물.
- 제 1 항에 있어서,상기 화학식 1 또는 2로 표시되는 유기광전소자용 화합물은,상기 X2, X6, X7 및 X9가 헤테로원자인 화합물 또는,상기 X3, X5, X7 및 X9가 헤테로원자인 화합물인 것인 유기광전소자용 화합물.
- 제 1 항에 있어서,상기 화학식 1 또는 2로 표시되는 유기광전소자용 화합물은,상기 X2, X6, X7, X8 및 X9가 헤테로원자인 화합물 또는,상기 X3, X5, X7, X8 및 X9가 헤테로원자인 화합물인 것인 유기광전소자용 화합물.
- 제 1 항에 있어서,상기 화학식 1 또는 2로 표시되는 유기광전소자용 화합물은,상기 X2, X3, X5, X6, X7, X8 및 X9가 헤테로원자인 화합물 또는,상기 X1, X3, X4, X5, X7, X8 및 X9가 헤테로원자인 화합물인 것인 유기광전소자용 화합물.
- 제 1 항에 있어서,상기 화학식 1에서,Ar7 내지 Ar12는 서로 동일하거나 상이하며, 독립적으로 페닐기, 비페닐기, 터페닐기, 스틸베닐기, 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기 및 페릴레닐기로 이루어진 군에서 선택되고,Ar1 내지 Ar6는 서로 동일하거나 상이하며, 독립적으로 페닐렌기, 비페닐렌기, 터페닐렌기, 스틸베닐렌기, 나프틸렌기, 안트라세닐렌기, 페난트레닐렌기, 파이레닐렌기 및 페릴레닐렌기로 이루어진 군에서 선택되고,상기 화학식 2에서,Ar13 내지 Ar18은 서로 동일하거나 상이하며, 독립적으로 페닐기, 비페닐기, 터페닐기, 스틸베닐기, 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기 및 페릴레닐기로 이루어진 군에서 선택되는 것인 유기광전소자용 화합물.
- 제 1 항에 있어서,상기 화학식 1에서,Ar7 내지 Ar12는 서로 동일하거나 상이하며, 독립적으로 티오페닐기, 퓨라닐기, 피롤일기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 트리아졸릴기, 피리디닐기, 피라다지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 아크리디닐기, 이미다조피리디닐기, 이미다조피리미디닐기, 벤조퀴놀리닐기 및 페난트롤리디닐기로 이루어진 군에서 선택되고,상기 화학식 2에서,Ar13 내지 Ar18은 서로 동일하거나 상이하며, 독립적으로 티오페닐기, 퓨라닐기, 피롤일기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 트리아졸릴기, 피리디닐기, 피라다지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 아크리디닐기, 이미다조피리디닐기, 이미다조피리미디닐기, 벤조퀴놀리닐기 및 페난트롤리디닐기로 이루어진 군에서 선택되는 것인 유기광전소자용 화합물.
- 하기 화학식 3 내지 33 중 어느 하나로 표시되는 유기광전소자용 화합물.[화학식 3] [화학식 4][화학식 5] [화학식 6][화학식 7] [화학식 8][화학식 9] [화학식 10][화학식 11] [화학식 12][화학식 13] [화학식 14][화학식 15] [화학식 16][화학식 17] [화학식 18][화학식 19] [화학식 20][화학식 21] [화학식 22][화학식 23] [화학식 24][화학식 25] [화학식 26][화학식 27] [화학식 28][화학식 29] [화학식 30][화학식 31] [화학식 32][화학식 33]
- 양극, 음극 및 상기 양극과 음극 사이에 개재되는 적어도 한 층 이상의 유기박막층을 포함하는 유기광전소자에 있어서,상기 유기박막층 중 적어도 어느 한 층은 상기 제 1 항 내지 제 10 항 중 어느 한 항에 따른 유기광전소자용 화합물을 포함하는 것인 유기광전소자.
- 제 11 항에 있어서,상기 유기박막층은 발광층, 정공수송층, 정공주입층, 전자수송층, 전자주입층, 정공차단층 및 이들의 조합을 이루어진 군에서 선택되는 것인 유기광전소자.
- 제 11 항에 있어서,상기 유기광전소자용 화합물은 전자수송층 또는 전자주입층 내에 포함되는 것인 유기광전소자.
- 제 11 항에 있어서,상기 유기광전소자용 화합물은 발광층 내에 포함되는 것인 유기광전소자.
- 제 11 항에 있어서,상기 유기광전소자용 화합물은 발광층 내에 인광 또는 형광 호스트 재료로서 사용되는 것인 유기광전소자.
- 제 11 항에 있어서,상기 유기 광전 소자용 화합물은 발광층 내에 형광 청색 도펀트 재료로서 사용되는 것인 유기광전소자.
- 제 11 항에 있어서,상기 유기광전소자는 유기 발광 소자, 유기 태양 전지, 유기 트랜지스터, 유기 감광체 드럼 및 유기 메모리 소자로 이루어진 군에서 선택되는 것인 유기광전소자.
- 제 11 항의 유기광전소자를 포함하는 것인 표시장치.
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Also Published As
Publication number | Publication date |
---|---|
EP2514798A2 (en) | 2012-10-24 |
US20120256174A1 (en) | 2012-10-11 |
US9093652B2 (en) | 2015-07-28 |
JP5782045B2 (ja) | 2015-09-24 |
CN102803437A (zh) | 2012-11-28 |
KR101288566B1 (ko) | 2013-07-22 |
KR20110068514A (ko) | 2011-06-22 |
EP2514798A4 (en) | 2014-04-16 |
CN102803437B (zh) | 2015-06-17 |
WO2011074770A3 (ko) | 2011-11-03 |
JP2013514348A (ja) | 2013-04-25 |
EP2514798B1 (en) | 2016-09-28 |
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