WO2015076599A1 - Nouveau composé électroluminescent et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé électroluminescent et dispositif électroluminescent organique le comprenant Download PDF

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WO2015076599A1
WO2015076599A1 PCT/KR2014/011225 KR2014011225W WO2015076599A1 WO 2015076599 A1 WO2015076599 A1 WO 2015076599A1 KR 2014011225 W KR2014011225 W KR 2014011225W WO 2015076599 A1 WO2015076599 A1 WO 2015076599A1
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deuterium
halogen
nitrile
amino
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함호완
김봉기
안현철
김동준
한정우
김근태
이형진
임동환
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주식회사 동진쎄미켐
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Priority to CN201480063382.0A priority Critical patent/CN105765030B/zh
Priority claimed from KR1020140162365A external-priority patent/KR102388406B1/ko
Publication of WO2015076599A1 publication Critical patent/WO2015076599A1/fr

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Definitions

  • the present invention relates to a novel light emitting compound and an organic light emitting device comprising the same.
  • an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices.
  • LCD liquid crystal display
  • the material used as the organic material layer in the organic light emitting device can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function.
  • the light emitting material may be classified into a polymer and a low molecule 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. According to the emission color can be divided into blue, green, red light emitting material and yellow and orange light emitting material required to implement a better natural color.
  • a host / dopant system may be used as a light emitting material.
  • the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light.
  • the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host used.
  • the present invention has excellent charge transfer characteristics, and at the same time have a high triplet energy and high Tg, when applied to an organic light emitting device can have a low driving voltage, high efficiency, low power consumption, long life. It is an object to provide a novel light emitting compound.
  • the present invention provides a light emitting compound represented by the following formula (1):
  • A is one of the structures represented by the following A1 to A30, wherein the hydrogen contained in A may be independently substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group,
  • L is deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 C 6-50 aryl group which is optionally substituted with an aryloxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
  • B is one of the structures represented by the following B1 to B10, wherein the hydrogen contained in B may be independently substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group.
  • Ar 1 and Ar 2 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group;
  • the present invention also provides an organic light emitting device comprising the compound represented by Chemical Formula 1 in an organic material layer as a light emitting material.
  • the light emitting compound of the present invention has excellent charge transfer characteristics, and at the same time has a high triplet energy and a high Tg, and can have a low driving voltage, high efficiency, low power consumption, and long life when applied to an organic light emitting device.
  • FIG. 1 schematically illustrates a cross section of an OLED according to an embodiment of the invention.
  • the compound of the present invention is characterized by represented by the following formula (1).
  • A is one of the structures represented by the following A1 to A30, wherein the hydrogen contained in A may be independently substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group,
  • L is deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 C 6-50 aryl group which is optionally substituted with an aryloxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group, preferably L is one of the following structures:
  • B is one of the structures represented by the following B1 to B10, wherein the hydrogen contained in B may be independently substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group.
  • Ar 1 and Ar 2 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C 2-30 heteroaryl group which is
  • the compound represented by Formula 1 is preferably one of the structures shown below.
  • X 1 and X 2 are each independently S, O, Se, Te, or N-Ar 3 , wherein Ar 3 is hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryl group which is optionally substituted with deuterium, halogen, amino group
  • Ar is deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 C 6-50 aryl group which is unsubstituted or substituted with an aryloxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group ; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 6-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group.
  • the compound represented by Chemical Formula 1 is more preferably one of the structures represented below.
  • X 1 and X 2 are each independently S, O, Se, Te, or N-Ar 4 , wherein Ar 4 is hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryl group which is optionally substituted with deuterium, halogen, amino group
  • Y is CR 1 or N wherein R 1 is hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C 2-30 hetero
  • Compound of Formula 1 according to the present invention has excellent charge transfer characteristics, and at the same time have a high triplet energy and high Tg, when applied to the organic light emitting device can have a low drive voltage, high efficiency, low power consumption, long life.
  • Scheme 1-1 may be applied.
  • the present invention provides an organic light emitting device comprising a compound represented by the formula (1) in the organic material layer as a light emitting material.
  • the compound of the present invention may be used alone or in combination with a known organic light emitting compound.
  • the organic light emitting device of the present invention includes one or more organic material layers including the compound represented by Chemical Formula 1, and the method of manufacturing the organic light emitting device is as follows.
  • the organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between an anode and a cathode. It may contain one or more.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emission layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
  • the substrate may be a substrate used in a conventional organic light emitting device, it is particularly preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
  • the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
  • the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
  • the hole injection layer material may be formed on the anode by vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), etc., but it is easy to obtain a uniform film quality and also pinholes. It is preferable to form by the vacuum evaporation method in that it is hard to produce
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and generally, a deposition temperature of 50-500 ° C., It is preferable to select appropriately from a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 kPa / sec, and a layer thickness of 10 kPa to 5 mu m.
  • the hole injection layer material is not particularly limited, and TCTA (4,4 ′, 4 ′′ -tri (N-carbazolyl) tree, which is a phthalocyanine compound or starburst type amine derivative such as copper phthalocyanine disclosed in US Pat. No. 4,356,429.
  • the hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, etc., but it is easy to obtain a uniform film quality and is difficult to generate pin holes. It is preferable to form by a vapor deposition method.
  • the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in the same condition range as the formation of the hole injection layer.
  • the hole transport layer material is not particularly limited, and may be arbitrarily selected and used from conventionally known materials used in the hole transport layer.
  • the hole transport layer material is carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Derivatives and the like can be used.
  • carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4
  • the light emitting layer material may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, cast, LB, etc., but the vacuum deposition method is easy to obtain a uniform film quality and hard to generate pin holes. It is preferable to form by.
  • the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same conditions as the formation of the hole injection layer.
  • the light emitting layer material may use the compound represented by Formula 1 of the present invention as a host or dopant.
  • a light emitting layer may be formed by using a phosphorescent or fluorescent dopant together.
  • the fluorescent dopant may be IDE102 or IDE105, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethyrylcrisne- which can be purchased from Idemitsu Co., Ltd.).
  • 6,12-diamine can be used as green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6- Difluorophenyl) -pyridinato-N, C2 '] picolinate), a red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).
  • the doping concentration of the dopant is not particularly limited, but the dopant is preferably doped at 0.01 to 15 parts by weight based on 100 parts by weight of the host.
  • the content of the dopant is less than 0.01 parts by weight, there is a problem in that the color development is not performed properly because the amount of the dopant is not sufficient, and if it exceeds 15 parts by weight, the efficiency is drastically reduced due to the concentration quenching phenomenon.
  • the hole suppression material HBL
  • HBL hole suppression material
  • the hole-suppressing material that can be used at this time is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used.
  • an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1) can be cited.
  • Oxy-2-methylquinolinolato) -aluminum biphenoxide), a phenanthrolines-based compound e.g., BCP (vasocuproin) from UDC
  • BCP vasocuproin
  • An electron transport layer is formed on the light emitting layer formed as above, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.
  • the electron transport layer material functions to stably transport electrons injected from the electron injection electrode, and the type thereof is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3). ), Or ET4 (6,6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine).
  • an electron injection layer (EIL) which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer material may be LiF, NaCl, CsF, Li 2 O, BaO, or the like. The substance of can be used.
  • the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.
  • an electron injection layer material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is preferable to form by.
  • a cathode forming metal is formed on the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode.
  • the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
  • a transmissive cathode using ITO or IZO may be used to obtain the front light emitting device.
  • the organic light emitting device of the present invention is not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device of the cathode structure, but also the structure of an organic light emitting device of various structures, 1 It is also possible to form a layer or two intermediate layers.
  • each organic material layer formed according to the present invention can be adjusted according to the required degree, preferably 10 to 1,000 nm, more preferably 20 to 150 nm.
  • the present invention has an advantage that the organic material layer containing the compound represented by Formula 1 has a uniform surface and excellent shape stability because the thickness of the organic material layer can be adjusted in molecular units.
  • the organic light emitting device of the present invention may implement low driving voltage, high efficiency, low power consumption, and long life, including the compound represented by Formula 1 having excellent charge transfer characteristics and at the same time having a high triplet energy and a high Tg.
  • Compound 2 was synthesized in the same manner as Compound 1, except that Intermediate A1 was used instead of Intermediate A3.
  • Compound 3 was synthesized in the same manner as in compound 1, except that intermediate A2, instead of intermediate A2, and B2 instead of intermediate B1 were used.
  • Compound 10 was synthesized in the same manner as in compound 7, except that intermediate A2, instead of intermediate A2, and B2 instead of intermediate B1 were used.
  • Compound 12 was synthesized in the same manner as in compound 7, except that intermediate A18, instead of intermediate A3, and B2 instead of intermediate B1 were used.
  • An organic light emitting device was manufactured according to the structure of FIG. 1.
  • the organic light emitting element is formed from the bottom of the anode (hole injection electrode 11) / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transfer layer 15 / cathode (electron injection electrode 16) It was laminated in order.
  • the hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of Examples and Comparative Examples used the following materials.
  • ITO 1500 ⁇ thick thin glass substrate was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes by using an oxygen plasma.
  • NPB 250 ⁇ was formed into a hole injection layer HT01 600 ⁇ and a hole transport layer.
  • the light emitting layer was doped with 10% of Compound 1: Ir (ppy) 3 to form 250 ⁇ .
  • ET01: Liq (1: 1) 300 ⁇ was formed into an electron transport layer, followed by LiF 10 ⁇ and aluminum (Al) 1000 ⁇ , which were encapsulated in a glove box to produce a green organic light emitting device. .
  • Example 13 In the same manner as in Example 13, a green organic light emitting diode was manufactured by using Compounds 2 to 12 as light emitting layer hosts.
  • a green organic light emitting diode was manufactured according to the same method as a light emitting layer host of Example 1, except that Compound 1 was used as CBP.
  • a green organic light emitting diode was manufactured according to the same method as Example 1 except that Compound 1 was used as Comparative Compound 1 instead of Compound 1 as the emission layer host.
  • a green organic light emitting diode was manufactured according to the same method as Comparative Example 2, except for using Compound 1 as the emission layer host of Example 1.
  • the embodiment of the present invention can be confirmed that the organic light emitting device physical properties in all aspects compared to Comparative Examples 1 to 3.
  • the light emitting compound of the present invention has excellent charge transfer characteristics, and at the same time has a high triplet energy and a high Tg, and can have a low driving voltage, high efficiency, low power consumption, and long life when applied to an organic light emitting device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Cette invention concerne un composé électroluminescent organique ayant d'excellentes caractéristiques de transport de charges tout en conservant une énergie triplet et une Tg élevées, permettant ainsi d'obtenir un dispositif électroluminescent organique ayant une basse tension d'excitation, un rendement élevé, une alimentation basse consommation, et une longue durée de vie quand ledit composé électroluminescent organique est appliqué à un dispositif électroluminescent organique.
PCT/KR2014/011225 2013-11-20 2014-11-20 Nouveau composé électroluminescent et dispositif électroluminescent organique le comprenant WO2015076599A1 (fr)

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US10199584B2 (en) 2016-08-10 2019-02-05 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
EP3444257A4 (fr) * 2016-04-15 2019-12-11 Boe Technology Group Co. Ltd. Matériau électroluminescent organique et dispositif électroluminescent organique

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KR20110048838A (ko) * 2009-11-03 2011-05-12 제일모직주식회사 유기광전소자용 조성물, 이를 이용한 유기광전소자 및 이를 포함하는 표시장치
WO2012016630A1 (fr) * 2010-08-05 2012-02-09 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2012050002A1 (fr) * 2010-10-13 2012-04-19 新日鐵化学株式会社 Composé aromatique azoté, matière semi-conductrice organique et dispositif électronique organique
JP2013058560A (ja) * 2011-09-07 2013-03-28 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置、照明装置、並びに化合物

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KR20110048838A (ko) * 2009-11-03 2011-05-12 제일모직주식회사 유기광전소자용 조성물, 이를 이용한 유기광전소자 및 이를 포함하는 표시장치
WO2012016630A1 (fr) * 2010-08-05 2012-02-09 Merck Patent Gmbh Matériaux pour dispositifs électroniques
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JP2013058560A (ja) * 2011-09-07 2013-03-28 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置、照明装置、並びに化合物

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EP3444257A4 (fr) * 2016-04-15 2019-12-11 Boe Technology Group Co. Ltd. Matériau électroluminescent organique et dispositif électroluminescent organique
US10886475B2 (en) 2016-04-15 2021-01-05 Boe Technology Group Co., Ltd. Organic electroluminescent materials and organic electroluminescent devices
US10199584B2 (en) 2016-08-10 2019-02-05 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same

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