WO2016141692A1 - 有机电致发光器件 - Google Patents
有机电致发光器件 Download PDFInfo
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- WO2016141692A1 WO2016141692A1 PCT/CN2015/088710 CN2015088710W WO2016141692A1 WO 2016141692 A1 WO2016141692 A1 WO 2016141692A1 CN 2015088710 W CN2015088710 W CN 2015088710W WO 2016141692 A1 WO2016141692 A1 WO 2016141692A1
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- MVAUROMZYBXESS-UHFFFAOYSA-N C1c(cc(cc2)-c(c3c4cccc3)c(cccc3)c3c4-c(nc3)ccc3-c3cc(-c4ncccc4)cc(-c4ccccn4)c3)c2-c2c1cccc2 Chemical compound C1c(cc(cc2)-c(c3c4cccc3)c(cccc3)c3c4-c(nc3)ccc3-c3cc(-c4ncccc4)cc(-c4ccccn4)c3)c2-c2c1cccc2 MVAUROMZYBXESS-UHFFFAOYSA-N 0.000 description 1
- WWNGAURBYZHMAO-UHFFFAOYSA-N C1c(cc(cc2)-c3c(cccc4)c4c(-c(cc4)ccc4-c4cc(-c5ncccc5)cc(-c5ccccn5)c4)c4c3cccc4)c2-c2c1cccc2 Chemical compound C1c(cc(cc2)-c3c(cccc4)c4c(-c(cc4)ccc4-c4cc(-c5ncccc5)cc(-c5ccccn5)c4)c4c3cccc4)c2-c2c1cccc2 WWNGAURBYZHMAO-UHFFFAOYSA-N 0.000 description 1
- XLLCUOCTEIZRMO-UHFFFAOYSA-N CC1c(cc(cc2)-c(c3c4cccc3)c(cccc3)c3c4-c(nc3)ccc3-c3cc(-c4ccccn4)cc(-c(nc4)ccc4-c(cc4)ccc4-c4cc(-c5ccccc5)cc(-c5ccc(-c6c(cccc7)c7c(-c(cc7)cc8c7-c7ccccc7C87c8ccccc8-c8ccccc78)c7c6cccc7)nc5)c4)c3)c2-c2ccccc12 Chemical compound CC1c(cc(cc2)-c(c3c4cccc3)c(cccc3)c3c4-c(nc3)ccc3-c3cc(-c4ccccn4)cc(-c(nc4)ccc4-c(cc4)ccc4-c4cc(-c5ccccc5)cc(-c5ccc(-c6c(cccc7)c7c(-c(cc7)cc8c7-c7ccccc7C87c8ccccc8-c8ccccc78)c7c6cccc7)nc5)c4)c3)c2-c2ccccc12 XLLCUOCTEIZRMO-UHFFFAOYSA-N 0.000 description 1
- RCAILLNISSALLB-UHFFFAOYSA-N c1ccc(C2(c(cc(cc3)-c(c4c5cccc4)c(cccc4)c4c5-c(nc4)ccc4-c4cc(-c5ccccc5)cc(-c5ccccc5)c4)c3-c3ccccc23)c2ccccc2)cc1 Chemical compound c1ccc(C2(c(cc(cc3)-c(c4c5cccc4)c(cccc4)c4c5-c(nc4)ccc4-c4cc(-c5ccccc5)cc(-c5ccccc5)c4)c3-c3ccccc23)c2ccccc2)cc1 RCAILLNISSALLB-UHFFFAOYSA-N 0.000 description 1
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H10K50/14—Carrier transporting layers
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- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection layers
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- H10K50/00—Organic light-emitting devices
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
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- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Definitions
- the invention relates to a novel organic electro-non-doped blue light-emitting device prepared by a novel organic electronic material, and belongs to the technical field of organic electroluminescent device display.
- organic electroluminescent devices As a new display technology, organic electroluminescent devices have self-luminous, wide viewing angle, low power consumption, high efficiency, thin, rich color, fast response, wide temperature range, low driving voltage, flexible and bendable Transparent display panels and environmentally friendly features, therefore, organic electroluminescent device technology can be applied to flat panel displays and next-generation lighting, as well as backlights for LCDs.
- An organic electroluminescent device is a device prepared by spin coating or depositing an organic material between two metal electrodes.
- a classic three-layer organic electroluminescent device comprises a hole transport layer, a light emitting layer and an electron transport layer. The holes generated by the anode pass through the hole transport layer and the electrons generated by the cathode are combined by the electron transport layer to form excitons in the light-emitting layer, and then emit light.
- the organic electroluminescent device can emit red light, green light, and blue light by changing the material of the light emitting layer. Therefore, stable, high-efficiency and color-purity organic electroluminescent materials play an important role in the application and promotion of organic electroluminescent devices, and are also an urgent need for the application of OLEDs for large-area panel displays.
- red and green materials have recently achieved great development and are also in line with the market demand for panels.
- blue light materials there are also a series of commercial materials, among which the distyrylbiphenyl (DPVBi) compounds of Idemitsu Kosan Co., Ltd., which were used in the early days, were prepared from such compounds.
- the devices have higher efficiency, but often the stability of these materials is relatively poor.
- the luminescent color of such compounds belongs to sky blue, and y>0.15 in the CIE value. Therefore, due to its poor temperature and impure color, the application of such compounds in full color display devices is greatly limited.
- Another type of blue light material is Kodak's ADN and tetra-tert-butyl fluorene, but these compounds have relatively poor luminous efficiency and poor stability, so they cannot be used in large quantities.
- the present invention provides an organic electroluminescent non-doped blue light-emitting device which is excellent in electroluminescence efficiency, excellent in color purity, and long in life.
- An organic electroluminescent device comprising an anode, a cathode, and an organic layer, the organic layer being a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and at least a light-emitting layer in the light-emitting layer One or more layers; the luminescent layer consisting of a single compound having the structure of formula (I),
- R 1 -R 17 independently represent a hydrogen, a deuterium atom, a halogen, cyano, nitro, C1-C8 alkyl, C1-C8-alkoxy, C6-C30 substituted or unsubstituted aryl group, C3 a substituted or unsubstituted heteroaryl aryl group of C30, a C2-C8 substituted or unsubstituted olefinic group, a C2-C8 substituted or unsubstituted alkynyl group, wherein Ar 1 -Ar 3 A C6-C60 substituted or unsubstituted aryl group, a C3-C60 substituted or unsubstituted heteroaryl group having one or more hetero atoms, a triaromatic (C6-C30) amine group.
- R 1 - R 17 are independently represented by hydrogen, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C2-C8 substituted or unsubstituted olefinic alkyl, C2- a C8 substituted or unsubstituted alkynyl group, a C1-C4 alkyl substituted or unsubstituted phenyl group, a C1-C4 alkyl substituted or unsubstituted naphthyl group, or a C1-C4 alkyl group substituted or unsubstituted fluorene
- Ar 1 -Ar 3 independently represents a C1-C4 alkyl group or a C6-C30 aryl-substituted phenyl group, a C1-C4 alkyl group or a C6-C30 aryl-substituted naphthyl group, a phenyl group, a
- R 1 -R 2 may independently be preferably represented by hydrogen, halogen, C1-C4 alkyl, C1-C4 alkyl substituted or unsubstituted phenyl, C1-C4 alkyl substituted or unsubstituted naphthalene Or a C1-C4 alkyl-substituted or unsubstituted fluorenyl group; wherein R 3 - R 17 may independently be preferably represented by hydrogen, halogen, C1-C4 alkyl, C1-C4 alkyl substituted or not Substituted phenyl, C1-C4 alkyl substituted or unsubstituted naphthyl, preferably Ar 1 -Ar 3 independently represents phenyl, tolyl, xylyl, tert-butylphenyl, naphthyl, pyridyl, Methylnaphthalene, biphenyl, diphenylphen
- R 3 - R 17 are preferably hydrogen
- R 1 , R 2 may independently and preferably represent hydrogen, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl, biphenyl, naphthalene.
- Ar 1 -Ar 3 independently represents phenyl, pyridyl, tolyl, xylyl, naphthyl, methylnaphthalene, biphenyl, diphenylphenyl, naphthylbenzene Base, diphenylbiphenyl, (9,9-dialkyl)fluorenyl, (9,9-dimethyl substituted or unsubstituted phenyl) anthracenyl, 9,9-spiropurinyl.
- R 3 - R 17 are preferably hydrogen; R 1 , R 2 independently represent hydrogen, methyl, or a fluorenyl group; and Ar 1 , Ar 2 , and Ar 3 independently represent a phenyl group, a naphthyl group.
- the compound of formula (I) is the following structural compound
- the organic layer is one or more layers of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, and an electron transport layer. It is to be noted that the above organic layer may not necessarily be present in each layer as needed, but at least has a light-emitting layer.
- the hole transport layer, the electron transport layer and/or the light-emitting layer contain the compound of the formula (I).
- the compound of formula (I) is located in the luminescent layer.
- the organic electroluminescent device of the present invention comprises a light-emitting layer having a light-emitting region of 440 to 490 nm.
- the luminescent layer is an undoped system.
- the organic layer of the electronic device of the present invention has a total thickness of from 1 to 1000 nm, preferably from 1 to 500 nm, more preferably from 50 to 300 nm.
- the organic layer may be formed into a film by steaming or spin coating.
- the hole transport layer and the hole injection layer in the present invention have a good hole transporting property and are capable of efficiently transporting holes from the anode to the organic light-emitting layer.
- small molecules and high molecular organics may be included.
- the material may include, but is not limited to, a triarylamine compound, a biphenyldiamine compound, a thiazole compound, an oxazole compound, an imidazole compound, an anthraquinone compound, a phthalocyanine compound, hexacyanohexaatriphenyl ( Hexanitrile hexaazatriphenylene),2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), polyvinylcarbazole, polythiophene, polyethylene , polybenzenesulfonic acid.
- the organic electroluminescent layer of the present invention employs the compound of the formula (I) of the present invention, and is not incorporated with other materials.
- the organic electron transporting material used in the organic electronic device of the present invention is required to have good electron transporting property, and can efficiently transport electrons from the cathode to the light emitting layer.
- the following compounds can be selected, but are not limited thereto.
- the organic electronic device of the present invention may be provided with an electron injecting layer which can efficiently inject electrons from the cathode into the organic layer, and is mainly selected from an alkali metal or an alkali metal, in addition to the compound of the present invention, as needed.
- the compound, or a compound selected from the group consisting of alkaline earth metals or alkaline earth metals may be selected from, but not limited to, lithium, lithium fluoride, lithium oxide, lithium nitride, lithium quinolate, hydrazine, cesium carbonate, 8- Hydroxyquinolinium, calcium, calcium fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesium oxide.
- the device experiments show that the organic electroluminescent device of the present invention has the advantages of good electroluminescence efficiency, excellent color purity, and long life.
- Figure 1 is a structural view of a device of the present invention
- 10 represents a glass substrate
- 20 represents an anode
- 30 represents a hole injection layer
- 40 represents a hole transport layer
- 50 represents a light-emitting layer
- 60 represents an electron transport layer
- 70 represents an electron injection layer
- 80 represents an electron injection layer. It is a cathode.
- Figure 3 is a 13 C NMR chart of Compound 89.
- Figure 5 is a TGA diagram of Compound 89.
- Example 6 is a graph showing voltage-current density of Example 4, Example 5, and Comparative Example 1.
- Example 7 is a graph of brightness-CIEy of Example 4, Example 5 and Comparative Example 1.
- Example 8 is an electroluminescence spectrum of Example 4, Example 5 and Comparative Example 1.
- Example 9 is a graph showing current density-current efficiency of Example 4, Example 5 and Comparative Example 1.
- the transparent conductive ITO glass substrate 10 (with the anode 20 on the surface) was sequentially washed with a detergent solution and deionized water, ethanol, acetone, deionized water, and then treated with oxygen plasma for 30 seconds.
- NPB was evaporated to form a hole transport layer 40 having a thickness of 30 nm.
- a compound 3 having a thickness of 30 nm was vapor-deposited on the hole transport layer as the light-emitting layer 50.
- the prepared device had a voltage of 3.58 V at an operating current density of 20 mA/cm 2 , a current efficiency of 3.21 cd/A, and a CIEy coordinate of 0.0853 at a luminance of 1000 cd/m 2 to emit blue light.
- the prepared device had a voltage of 3.84 V at an operating current density of 20 mA/cm 2 , a current efficiency of 2.83 cd/A, a CIEy coordinate of 0.0888 at a luminance of 1000 cd/m 2 , and emission of blue light.
- the prepared device had a voltage of 4.00 V at an operating current density of 20 mA/cm 2 , a current efficiency of 2.46 cd/A, a CIEy coordinate of 0.0952 at a luminance of 1000 cd/m 2 , and emission of blue light.
- Examples 4 and 5 are specific applications of the materials of the present invention.
- the devices produced, which emit blue light, have higher efficiency and brightness than the comparative examples.
- the material of the present invention has high stability, and the organic electroluminescent device prepared by the present invention has high efficiency and light purity.
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Abstract
Description
Claims (10)
- 一种有机电致发光器件,包含阳极,阴极,和有机层,所述有机层为空穴注入层、空穴传输层、电子注入层、电子传输层、发光层中至少包括发光层在内的一层或多层;所述发光层由具有式(I)所述结构的单一化合物组成,其中,R1-R17独立地表示为氢,氘原子,卤素,氰基,硝基,C1-C8烷基、C1-C8烷氧基,C6-C30的取代或者未取代的芳基,C3-C30的取代或者未取代的含有一个或者多个的杂原子芳基,C2-C8取代或者未取代的烯烷基,C2-C8取代或者未取代的炔烷基,其中,Ar1-Ar3独立地表示C6-C60取代或者未取代的芳基,C3-C60的取代或者未取代的带有一个或者多个杂原子的杂芳基,三芳香(C6-C30)胺基。
- 根据权利要求1所述的有机有机电致发光器件,其中,R1-R17独立地表示为氢,卤素,氰基,硝基,C1-C8烷基、C1-C8烷氧基,C2-C8取代或者未取代的烯烷基,C2-C8取代或者未取代的炔烷基,C1-C4烷基取代或未取代的苯基,C1-C4烷基取代或未取代的萘基,或结合成C1-C4烷基取代或未取代的芴基;Ar1-Ar3独立地表示C1-C4烷基或者C6-C30芳基取代的苯基,C1-C4烷基或者C6-C30芳基取代的萘基,苯基,萘基,吡啶基,N-C6-C30的芳基或者C1-C4的烷基取代的咔唑基,二苯并噻吩基,二苯并呋喃基,蒽基,菲基,芘基,苝基,荧蒽基,(9,9-二烷基)芴基,(9,9-二烷基取代或未取代芳基)芴基,9,9-螺芴基。
- 根根据权利要求2所述的有机电致发光器件,其中,R1-R2可以独立地优选表示为氢,卤素,C1-C4的烷基,C1-C4烷基取代或未取代的苯基,C1-C4烷基取代或未取代的萘基,或结合成C1-C4烷基取代或未取代的芴基;其中,R3-R17可以独立地优选表示为氢,卤素,C1-C4的烷基,C1-C4烷基取代或未取代的苯基,C1-C4烷基取代或未取代的萘基,Ar1-Ar3为独立地表示苯基,甲苯基,叔丁基苯基,萘基,吡啶基,甲基萘,联苯基,二苯基苯基, 萘基苯基,二苯基联苯基,二芳香胺基苯基,N-苯基咔唑基,(9,9-二烷基)芴基,(9,9-二烷基取代或未取代苯基)芴基,9,9-螺芴基。
- 根据权利要求3所述的有机电致发光器件,其中,R3-R17优选为氢,R1,R2可以独立优选表示为氢,甲基,乙基,丙基,异丙基,叔丁基,苯基,萘基,或结合成芴基;Ar1-Ar3为独立地表示苯基,吡啶基,甲苯基,萘基,甲基萘,联苯基,二苯基苯基,萘基苯基,二苯基联苯基,(9,9-二烷基)芴基,(9,9-二甲基取代或未取代苯基)芴基,9,9-螺芴基。
- 根据权利要求4所述的有机电致发光器件,R3-R17优选为氢;R1,R2为独立地表示氢,甲基,或结合成芴基;Ar1,Ar2,Ar3为独立地表示苯基,萘基。
- 根据权利要求1-7任一所述的有机电致发光器件,所述式(I)所述结构的化合物还位于空穴注入层、空穴传输层、电子传输层和/或电子注入层中。
- 根据权利要求8所述的有机电致发光器件,所述式(I)所述结构的化合物还位于空穴传输层和电子传输层。
- 根据权利要求1所述的,所述有机层可以通过蒸渡或旋涂形成薄膜。
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US15/557,093 US10533129B2 (en) | 2015-03-09 | 2015-09-01 | Organic electroluminescent device |
JP2017547521A JP6581664B2 (ja) | 2015-03-09 | 2015-09-01 | 有機電界発光素子 |
DE112015006273.4T DE112015006273B4 (de) | 2015-03-09 | 2015-09-01 | Organische Elektrolumineszenz-Bauelemente |
KR1020177025537A KR20170118785A (ko) | 2015-03-09 | 2015-09-01 | 유기전계발광소자 |
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CN108269947A (zh) * | 2016-12-30 | 2018-07-10 | 广东阿格蕾雅光电材料有限公司 | 有机发光二极管器件 |
CN108299389A (zh) * | 2017-12-26 | 2018-07-20 | 上海道亦化工科技有限公司 | 一种基于菲和咔唑的化合物及其用途和有机电致发光器件 |
KR102518416B1 (ko) * | 2018-07-31 | 2023-04-06 | 삼성디스플레이 주식회사 | 저굴절층 및 이를 포함하는 전자 장치 |
CN111320636B (zh) * | 2018-12-17 | 2022-09-02 | 广东阿格蕾雅光电材料有限公司 | 一种有机电致发光材料及其应用 |
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CN1871324A (zh) * | 2003-10-24 | 2006-11-29 | 伊斯曼柯达公司 | 具有不对称主体的有机发光二极管装置 |
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CN103456897A (zh) * | 2012-05-30 | 2013-12-18 | 京东方科技集团股份有限公司 | 有机电致发光器件 |
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JP4080213B2 (ja) * | 2002-02-01 | 2008-04-23 | 三井化学株式会社 | 有機電界発光素子 |
JP4025137B2 (ja) * | 2002-08-02 | 2007-12-19 | 出光興産株式会社 | アントラセン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
US7901793B2 (en) * | 2005-09-23 | 2011-03-08 | Samsung Mobile Display Co., Ltd. | Organic light-emitting compound and organic light-emitting device containing the same |
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US8642190B2 (en) * | 2009-10-22 | 2014-02-04 | Semiconductor Energy Laboratory Co., Ltd. | Fluorene derivative, light-emitting element, light-emitting device, electronic device, and lighting device |
KR101681214B1 (ko) * | 2010-01-08 | 2016-12-01 | 에스에프씨 주식회사 | 호스트 화합물 및 이를 이용한 유기전계발광소자 |
US10026905B2 (en) * | 2012-01-18 | 2018-07-17 | Duk San Neolux Co., Ltd. | Compound, organic electric element using the same, and an electronic device thereof |
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US10533129B2 (en) | 2020-01-14 |
CN106033798B (zh) | 2017-11-14 |
DE112015006273B4 (de) | 2022-02-10 |
JP6581664B2 (ja) | 2019-09-25 |
CN106033798A (zh) | 2016-10-19 |
TW201632487A (zh) | 2016-09-16 |
KR20170118785A (ko) | 2017-10-25 |
DE112015006273T5 (de) | 2018-01-18 |
TWI561499B (en) | 2016-12-11 |
JP2018514080A (ja) | 2018-05-31 |
US20180171218A1 (en) | 2018-06-21 |
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