WO2019054599A1 - Composé électroluminescent organique et dispositif électroluminescent organique utilisant celui-ci - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique utilisant celui-ci Download PDF

Info

Publication number
WO2019054599A1
WO2019054599A1 PCT/KR2018/004664 KR2018004664W WO2019054599A1 WO 2019054599 A1 WO2019054599 A1 WO 2019054599A1 KR 2018004664 W KR2018004664 W KR 2018004664W WO 2019054599 A1 WO2019054599 A1 WO 2019054599A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
substituted
unsubstituted
layer
Prior art date
Application number
PCT/KR2018/004664
Other languages
English (en)
Korean (ko)
Inventor
현서용
윤석근
김하연
Original Assignee
(주)피엔에이치테크
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020180044757A external-priority patent/KR102559642B1/ko
Application filed by (주)피엔에이치테크 filed Critical (주)피엔에이치테크
Publication of WO2019054599A1 publication Critical patent/WO2019054599A1/fr

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • the present invention relates to an organic electroluminescent compound, and more specifically, to an organic electroluminescent device employing an organic electroluminescent compound employed in an organic electroluminescent element in the organic electroluminescent device, and an organic electroluminescent device using the same.
  • the present invention relates to a high efficiency (luminous efficiency 26) without sulfur compound-based semiconductor backplane and cadmium of high performance (mobility 70 cm2 / Vs), which is supported by the Ministry of Industry and Commerce, cd / A) organic hybrid EL material / device technology development).
  • the organic electroluminescent device can not only form an element on a transparent substrate but also can operate at a low voltage of 10 V or less as compared with a plasma display panel (Plasma Display Panel) or an inorganic electroluminescence (EL) display, It has the advantage of excellent color and has three colors of green, blue, and red. It has recently become a subject of interest as a next generation display device.
  • a plasma display panel Plasma Display Panel
  • EL inorganic electroluminescence
  • the present invention provides a novel organic luminescent compound that can be employed as a host compound in an electron blocking layer, a hole transporting layer, or a luminescent layer in an organic electroluminescent device to significantly improve luminescent properties such as longevity and luminous efficiency, and organic electroluminescent Device.
  • the present invention provides an organic electroluminescent compound represented by the following formula (I) and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device employing the organic electroluminescent compound according to the present invention in an electron blocking layer, a hole transporting layer, or a light emitting layer has remarkably excellent luminescent properties such as long life and luminous efficiency as compared with the conventional device, and can be usefully used in various display devices.
  • 1 is a schematic diagram showing the structure of an organic luminescent compound according to the present invention.
  • the present invention relates to an organic electroluminescent compound represented by the following general formula (I), wherein an organic electroluminescent compound having a remarkably improved luminescent property such as a long life and a luminescent efficiency when employed in an organic layer such as a hole transporting layer, It is possible to realize a light emitting device.
  • an organic electroluminescent compound represented by the following general formula (I), wherein an organic electroluminescent compound having a remarkably improved luminescent property such as a long life and a luminescent efficiency when employed in an organic layer such as a hole transporting layer, It is possible to realize a light emitting device.
  • X 1 and X 2 are the same or different and are each independently from each other O, S, NR 3, BR 4, R 5 -CR 6, R 7 -Si-R 8, R 9 -Ge-R 10 and R 11 - Se-R 12 , and each of R 3 to R 12 is independently selected from among hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms .
  • R 1 and R 2 are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 24 or less carbon atoms, a substituted or unsubstituted 3 to 30 A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted
  • X 1 and X 2 are each O, and at least one of R 1 and R 2 is represented by the following formula (1).
  • L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted C2 to C30 heteroaryl
  • Ar 1 to Ar 2 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted 6 to 30 carbon atom A substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, And a substituted or unsubstituted C2 to C50 heteroaryl group in which one or more ring-opened cycloalkyl having 3 to 30 carbon atoms is fused.
  • the Ar 1 to Ar 2 may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring.
  • the organic luminescent compound according to the present invention has excellent skeletal structure and excellent luminescent properties such as longevity and luminescence efficiency of the organic light emitting device employing the organic compound in the organic layer depending on the characteristics of the substituent to be introduced.
  • R 1 to R 12 , L and Ar 1 to Ar 2 the substitution or unsubstitution means that R 1 to R 14 , L and Ar 1 to Ar 2 are deuterium, cyano group, halogen group, A nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, , An arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an aryl group having 1 to 24 carbon atoms An amino group, a heteroarylamino group having 1 to 24 carbon atoms,
  • substituted aryl group examples include a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group and an anthracenyl group substituted with other substituents do.
  • the substituted heteroaryl group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and condensed heterocyclic groups thereof such as a benzquinoline group, An imidazole group, a benzoxazole group, a benzothiazole group, a benzoxazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Is
  • aryloxy group used in the present invention include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, indenyloxy and the like, and at least one hydrogen atom contained in the aryloxy group Can be further substituted.
  • silyl group used in the present invention examples include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylpurylsilyl And the like.
  • the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30.
  • Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group.
  • polycyclic aryl group examples include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.
  • At least one hydrogen atom of the aryl group may be substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH 2 , -NH (R), -N (R ') (R “), R' and R" are independently of each other an alkyl group having 1 to 10 carbon atoms and in this case an "alkylamino group”), an amidino group, An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroatom having 1 to 24 carbon atoms, An alkyl group having 6 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 20.
  • Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.
  • the heteroaryl group is a hetero ring group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably 2 to 30 carbon atoms.
  • Examples thereof include a thiophene group, a furan group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group,
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, Methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo An octyl group, and the like, but are not limited thereto.
  • a fluorenyl group is a structure in which two cyclic organic compounds are connected via one atom, , .
  • a fluorenyl group includes a structure of an open fluorenyl group, wherein an open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected via one atom
  • an open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected via one atom
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • arylamine group examples include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.
  • the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the organic luminescent compound according to the present invention represented by the above-mentioned formula (I) can be used as an organic material layer of an organic light emitting device due to its structural specificity as described above. More specifically, A blocking layer, a hole transporting layer, or a host compound of a light emitting layer.
  • Preferred examples of the compound represented by the formula (I) according to the present invention include, but are not limited to, the following compounds.
  • An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, an electron transporting layer material and an electron blocking layer material used in manufacturing an organic electroluminescent device into the above structure,
  • the compound of the formula (I) according to the present invention is employed as a host material of an electron blocking layer, a hole transporting layer or a light emitting layer, and particularly in an electron blocking layer, the luminescence The characteristics can be further improved.
  • the organic luminescent compound according to the present invention can be applied to an organic electroluminescent device according to a conventional production method.
  • the organic electroluminescent device may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.
  • the organic material layer of the organic electroluminescent device according to 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.
  • a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and an electron blocking layer may be included.
  • the organic material layer may include at least one of a hole transporting layer, an electron blocking layer and a light emitting layer, and at least one of the layers may be an organic light emitting ≪ / RTI > compounds.
  • the organic light emitting device may be formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation A hole transporting layer, an electron blocking layer, a light emitting layer, and an electron transporting layer on the anode, and then depositing a material usable as a cathode thereon.
  • PVD physical vapor deposition
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer, but may have a single layer structure.
  • the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.
  • the cathode material a material having a large work function is preferably used so as to smoothly inject holes into the organic material layer.
  • the cathode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof; a multilayer such as LiF / Al or LiO 2 / Structural materials, and the like, but are not limited thereto.
  • the hole injecting material it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes is suitable.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.
  • PV poly (p-phenylene vinylene)
  • the electron transporting material a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable.
  • Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
  • the organic light emitting device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • the organic luminescent compound according to the present invention can act on a principle similar to that applied to an organic luminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.
  • the ITO transparent electrode is formed by patterning an ITO glass substrate having an ITO transparent electrode on a glass substrate of 25 mm x 25 mm x 0.7 mm so as to have a light emitting area of 2 mm x 2 mm And then washed. After the substrate was mounted in a vacuum chamber and the base pressure was adjusted to 1 ⁇ 10 -6 torr, organic matter and metal were deposited on the ITO by the following structure.
  • a blue light emitting organic electroluminescent device having the following device structure was prepared by using a compound represented by the formula [I] according to the present invention as a compound of the electron blocking layer, and the luminescent characteristics including the luminescent efficiency were measured.
  • Electron transport layer (201 nm Liq 30 nm) / LiF (1 nm) / ITO / hole injection layer (HAT_CN 5 nm) / hole transport layer ( ⁇ -NPB 100 nm) / electron blocking layer (10 nm) / Al (100 nm)
  • the hole injection layer was formed to a thickness of 5 nm by vacuum thermal deposition method using [HAT_CN], and then the hole transport layer was formed by using ⁇ -NPB.
  • the electron blocking layer was formed to have a thickness of 10 nm by using the chemical vapor deposition method of the present invention, which is represented by Chemical Formula 1, 10, 17, 38, 56, 70, 82, 93, 113, 129, Further, an electron transport layer (doped with Liq 50% of the following compound [201]) was further formed on the light emitting layer so as to have a thickness of about 20 nm by using [BH1] as a host compound and [BD1] 30 nm, LiF 1 nm and aluminum 100 nm were deposited by a vapor deposition method to produce an organic electroluminescent device.
  • An organic electroluminescent device for Device Comparison Example 1 was fabricated in the same manner except that TCTA was used as an electron blocking layer in the device structure of Example 1.
  • the voltage, current and luminous efficiency of the organic EL device were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research).
  • the current density was 10 mA / Is defined as " driving voltage " The results are shown in Table 1 below.
  • Example Electronic stop layer V cd / A QE (%) CIEx CIEy One One 4.19 8.05 6.80 0.145 0.154 2 10 4.21 8.01 6.77 0.145 0.155 3 17 4.20 8.11 6.85 0.145 0.154 4 38 4.16 8.20 6.95 0.145 0.153 5 56 4.24 8.06 6.81 0.144 0.154 6 70 4.20 8.12 6.85 0.145 0.155 7 82 4.18 8.02 6.78 0.144 0.154 8 93 4.19 8.15 6.89 0.145 0.155 9 113 4.17 8.13 6.86 0.146 0.156 10 129 4.20 8.18 6.93 0.145 0.154 11 137 4.23 8.04 6.80 0.145 0.155 12 158 4.22 8.14 6.88 0.144 0.154 Comparative Example 1 TCTA 4.20 6.40 5.30 0.145 0.156
  • An organic electroluminescent device having the following device structure was manufactured using the compound represented by formula (I) according to the present invention as a compound of the hole transport layer, and the luminescent characteristics including the luminous efficiency were measured.
  • the ZnO nanoparticle solution was spin-coated on the ITO transparent electrode to a thickness of 40 nm, and the solvent was removed in a vacuum oven at 150 ° C. Then, a 10 nm thick PFN solution was spin-coated and heat-treated. Then, an InP QD dispersion was spin-coated to form a film. After that, the substrate is mounted in a vacuum chamber, and the base pressure is adjusted to 1 ⁇ 10 -6 torr. Thereafter, a hole transport layer is formed on the surface of the hole transport layer of Formula 1, 10, 17, 38, 56, 70, 82, 93, , 137, and 158, respectively. MoO 3 was deposited to a thickness of about 10 nm, and aluminum was deposited to a thickness of 100 nm by vapor deposition to prepare an organic electroluminescent device.
  • An organic electroluminescent device for Device Comparison Example 2 was fabricated in the same manner except that TCTA was used as a hole transport layer in the device structure of Example 13.
  • the voltage, current and luminous efficiency of the organic EL device were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research).
  • the current density was 10 mA / Is defined as " driving voltage " The results are shown in Table 2 below.
  • Example Hole transport layer V cd / A EL (nm) 13 One 3.25 13.71 543 14 10 2.98 13.25 542 15 17 2.68 12.54 543 16 38 2.87 12.82 545 17 56 3.14 13.42 540 18 70 3.21 14.61 541 19 82 3.05 13.44 544 20 93 2.94 13.08 542 21 113 3.19 14.63 540 22 129 3.30 15.01 544 23 137 3.12 15.43 547 24 158 3.24 14.04 542 Comparative Example 2 TCTA 3.68 7.7 539
  • the organic electroluminescent device employing the organic electroluminescent compound according to the present invention in an electron blocking layer, a hole transporting layer, or a light emitting layer has remarkably excellent luminescent properties such as long life and luminous efficiency as compared with the conventional device, and can be usefully used in various display devices.

Abstract

La présente invention concerne un nouveau composé électroluminescent organique, et peut mettre en œuvre un dispositif électroluminescent organique présentant d'excellentes caractéristiques électroluminescentes, telles que le rendement lumineux et le rendement quantique, lorsque le nouveau composé électroluminescent organique est appliqué sur une couche de blocage d'électrons, une couche de transport de trous, une couche électroluminescente ou analogue.
PCT/KR2018/004664 2017-09-15 2018-04-23 Composé électroluminescent organique et dispositif électroluminescent organique utilisant celui-ci WO2019054599A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20170118408 2017-09-15
KR10-2017-0118408 2017-09-15
KR1020180044757A KR102559642B1 (ko) 2017-09-15 2018-04-18 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR10-2018-0044757 2018-04-18

Publications (1)

Publication Number Publication Date
WO2019054599A1 true WO2019054599A1 (fr) 2019-03-21

Family

ID=65722918

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/004664 WO2019054599A1 (fr) 2017-09-15 2018-04-23 Composé électroluminescent organique et dispositif électroluminescent organique utilisant celui-ci

Country Status (1)

Country Link
WO (1) WO2019054599A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3502107B1 (fr) * 2017-12-20 2022-01-26 Samsung Display Co., Ltd. Composé basé sur le 1-aminodibenzofurane et dispositif électroluminescent organique le comprenant

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120122812A (ko) * 2011-04-29 2012-11-07 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
WO2013122082A1 (fr) * 2012-02-15 2013-08-22 東レ株式会社 Matériau d'élément électroluminescent et élément électroluminescent
KR101614738B1 (ko) * 2015-11-02 2016-04-22 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20160127429A (ko) * 2015-04-27 2016-11-04 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
WO2017196081A1 (fr) * 2016-05-11 2017-11-16 Sk Chemicals Co., Ltd. Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120122812A (ko) * 2011-04-29 2012-11-07 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
WO2013122082A1 (fr) * 2012-02-15 2013-08-22 東レ株式会社 Matériau d'élément électroluminescent et élément électroluminescent
KR20160127429A (ko) * 2015-04-27 2016-11-04 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR101614738B1 (ko) * 2015-11-02 2016-04-22 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2017196081A1 (fr) * 2016-05-11 2017-11-16 Sk Chemicals Co., Ltd. Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique le comprenant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3502107B1 (fr) * 2017-12-20 2022-01-26 Samsung Display Co., Ltd. Composé basé sur le 1-aminodibenzofurane et dispositif électroluminescent organique le comprenant

Similar Documents

Publication Publication Date Title
WO2019164331A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2020027389A1 (fr) Composé électroluminescent organique et élément électroluminescent organique le comprenant
WO2013009079A1 (fr) Composé à base de triphénylène et diode électroluminescente organique l'utilisant
WO2011149283A2 (fr) Composé comprenant un hétérocycle à cinq chaînons, élément électrique organique l'utilisant et borne correspondante
WO2011139125A2 (fr) Composé de phénanthrocarbazole, et dispositif électroluminescent organique utilisant ce composé
WO2012015265A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique à base de ces composés
WO2011059271A2 (fr) Nouveau composé comprenant un anneau condensé, et dispositif électronique organique qui utilise celui-ci
WO2011081431A2 (fr) Composé émetteur de lumière organique, et dispositif électroluminescent organique l'utilisant
WO2011149240A2 (fr) Composé à base de triphénylène bipolaire et élément électroluminescent organique le comprenant
WO2017061779A1 (fr) Composé amine et dispositif électroluminescent organique le comprenant
WO2020111733A1 (fr) Dispositif électroluminescent organique
WO2011108901A9 (fr) Composé de spiro-carbazole comprenant un squelette spiro, et élément électronique organique utilisant celui-ci et terminal de celui-ci
WO2011139129A2 (fr) Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant
WO2018230854A1 (fr) Nouveau dérivé d'acridine, et dispositif électroluminescent organique le comprenant
WO2020009492A1 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2014098455A1 (fr) Nouveau composé organique et élément électroluminescent organique le comprenant
WO2020040514A1 (fr) Diode électroluminescente organique
WO2019240532A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2019108033A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2019013526A1 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
WO2021187924A1 (fr) Dispositif organique électroluminescent utilisant des composés aromatiques polycycliques
WO2022270835A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2018199699A1 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2021150026A1 (fr) Composé dérivé polycyclique aromatique et dispositif électroluminescent organique l'utilisant
WO2020111586A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18857165

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18857165

Country of ref document: EP

Kind code of ref document: A1