[go: up one dir, main page]

WO2018147638A1 - Composé organique et élément électroluminescent organique l'utilisant - Google Patents

Composé organique et élément électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2018147638A1
WO2018147638A1 PCT/KR2018/001654 KR2018001654W WO2018147638A1 WO 2018147638 A1 WO2018147638 A1 WO 2018147638A1 KR 2018001654 W KR2018001654 W KR 2018001654W WO 2018147638 A1 WO2018147638 A1 WO 2018147638A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
mmol
formula
mol
organic
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2018/001654
Other languages
English (en)
Korean (ko)
Inventor
김홍석
김영배
김회문
손호준
배형찬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Doosan Corp
Original Assignee
Doosan Corp
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
Application filed by Doosan Corp filed Critical Doosan Corp
Publication of WO2018147638A1 publication Critical patent/WO2018147638A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to include a novel organic compound having excellent electron transporting ability and the like as a material of the organic material layer, such as luminous efficiency, driving voltage, lifetime
  • the present invention relates to an organic electroluminescent device having improved characteristics.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • holes move faster than electrons, and excitons generated in the emission layer are transferred to the electron transport layer, resulting in charge unbalance in the emission layer, thereby emitting light at the electron transport layer interface.
  • the color purity and efficiency of the organic EL device is deteriorated, and in particular, when the organic EL device is manufactured, high temperature stability is lowered, thereby shortening the life of the organic EL device. Therefore, it is time to develop an electron transport material having high temperature stability, high T1 value, and fast and efficient hole blocking ability.
  • 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 light emitting auxiliary layer 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 light emitting auxiliary layer material, etc.
  • Supported by an efficient material should be preceded, but development of a stable and efficient organic material layer for an organic electroluminescent device has not been made yet. Therefore, the development of new materials continues to be required, and in particular, the development of material combinations such as a hole transport layer and an electron transport layer is urgently required.
  • An object of the present invention is to provide a novel organic compound which is excellent in electron transport ability, electron injection ability, and the like, which can be used as an organic material layer material.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound having a low driving voltage, high luminous efficiency, and an improved lifetime.
  • an example of the present invention provides a compound represented by the following formula (1).
  • a and B are different from each other, and can be independently represented by the formula (2) to (5)
  • X 1 to X 4 are different from each other, and contain an atom of any one of S, O, N (Ar 1 ), C (Ar 2 ) (Ar 3 ),
  • n is an integer of 0 to 4,
  • Z 1 to Z 5 are the same as or different from each other, represented by N or C (Ar 4 ),
  • R 1 and Ar 1 to Ar 4 are hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent tile to
  • another example of the present invention is an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 above. It provides an organic electroluminescent device comprising the compound represented.
  • the compound represented by Chemical Formula 1 according to an example of the present invention has excellent heat resistance, electron injection ability, electron transport ability, etc., it may be used as an organic material layer material, preferably an electron injection layer material, or an electron transport layer material of an organic EL device. Can be.
  • the organic electroluminescent device including the compound according to an example of the present invention in the electron injection layer or the electron transport layer can be greatly improved in terms of driving voltage, efficiency, lifespan, and the like. It can be effectively applied to the back.
  • the organic compound of the present invention is a compound having a structure in which one or more substituents are linked directly or through a linker group as a basic skeleton to a moiety bonded to a substituent including two or more 5-membered aromatic rings or 5-membered aromatic hetero rings. It is represented by Formula (1).
  • the substituent containing a 5-membered aromatic ring or 5-membered aromatic hetero ring is a benzoheteropentagon compound, such as benzotriazole, indazole, indole, indene, benzofuran ( benzofuran) and the like.
  • the compound represented by the formula (1) of the present invention is a direct linker group (EWG) or a linker group to the moiety bonded to a substituent containing a five-membered aromatic hetero ring, such as two or more benzotriazole, indazole, etc.
  • EWG is attached to a moiety in which a substituent includes a 5-membered aromatic heterocyclic ring such as benzotriazole, indazole, etc., or a substituent including 5-membered aromatic ring such as indene, benzofuran, etc. It has a structure connected directly or through a linker group.
  • the T1 value (2.0 eV) of Alq used as the electron transport layer is significantly lower than the T1 value (2.4 eV) of Ir (ppy) used as the dopant in the light emitting layer, whereas the T1 value of the compound of the present invention is generally higher than Ir (ppy). (2.4 eV or more), not only to improve hole blocking ability, but also to relatively increase the probability that excitons stay well in the light emitting layer.
  • the 5-membered aromatic ring or 5-membered aromatic hetero ring has a lower molecular weight than the conventional compound, it is possible to deposit at a relatively lower temperature than the materials during deposition, thereby improving processability and thermal stability.
  • the compound represented by Formula 1 of the present invention can be used as an organic material layer material of the organic electroluminescent device, preferably an electron transporting layer / injection layer material material.
  • the organic electroluminescent device including the compound of Formula 1 may significantly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
  • An organic compound according to one embodiment of the present invention is represented by the following formula (1).
  • a and B are different from each other, and can be independently represented by the formula (2) to (5)
  • X 1 to X 4 are different from each other, and contain an atom of any one of S, O, N (Ar 1 ), C (Ar 2 ) (Ar 3 ),
  • n is an integer of 0 to 4,
  • Z 1 to Z 5 are the same as or different from each other, represented by N or C (Ar 4 ),
  • R 1 and Ar 1 to Ar 4 are hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent tile to
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formulas 7 to 10.
  • X 1 to X 4 , n, R 1 and Z are each as defined in Formula 1 to Formula 6.
  • a in Formula 1 may be selected from the following structures, but is not limited thereto.
  • B of Formula 1 may be selected from the following structures, but is not limited thereto.
  • C may be pyrimidine or triazine.
  • Ar 4 is the same as or different from each other, but may be selected from the following structure, but is not limited thereto.
  • C of Formula 1 may be selected from the following structures, but is not limited thereto.
  • Examples of the compound represented by Formula 1 according to an example of the present invention include compounds R1 to R140, but are not limited thereto.
  • Alkyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, non-limiting examples thereof are methyl, ethyl, propyl, isobutyl, sec-butyl , Pentyl, iso-amyl, hexyl and the like.
  • cycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms.
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • heterocycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and preferably at least one carbon in the ring, preferably 1 Carbon of 3 to 3 is substituted with a hetero atom such as N, O or S.
  • a non-aromatic hydrocarbon saturated cyclic hydrocarbon
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • aryl means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or two or more rings combined. In this case, the two or more rings may be attached in a simple or condensed form with each other.
  • Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.
  • heteroaryl is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 Is substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se).
  • the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group.
  • heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indole Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2- Isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • alkyloxy means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Can be. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • aryloxy means a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms.
  • R ' is aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl refers to silyl substituted with aryl having 6 to 60 carbon atoms
  • alkylboron group is used for 1 to 40 carbon atoms. It means a boron group substituted with 40 alkyl
  • aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms
  • arylphosphine group means a phosphine group substituted with an aryl having 1 to 60 carbon atoms.
  • Arylamine refers to an amine substituted with aryl having 6 to 60 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • an example of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is a compound represented by Formula 1 above. It provides an organic electroluminescent device comprising a.
  • the compound represented by Formula 1 may be used alone, or two or more may be mixed and used.
  • the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1).
  • the organic material layer including the compound of Formula 1 may be an electron transport layer.
  • An organic electroluminescent device according to an example of the present invention is a sugar except that at least one or more of the organic material layer (eg, at least one of the light emitting layer, the electron transporting layer, and the light emitting auxiliary layer) is formed to include the compound represented by Chemical Formula 1, It can be prepared by forming other organic material layers and electrodes using materials and methods known in the art.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • anode material examples include i) metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, ii) metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO), iii) combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb, iv) polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thi Conductive polymers such as OPEN] (PEDT), polypyrrole or polyaniline tube, and v) carbon black and the like can be used, but is not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof
  • metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO)
  • IZO indium zinc oxide
  • ZnO Al or SnO 2 : S
  • the negative electrode material may be magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or metals such as M or alloys thereof, and multilayer structures such as LiF / Al or LiO 2 / Al. Materials and the like may be used, but are not limited thereto.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a green organic EL device was manufactured in the same manner as in Example 1, except that Alq 3 , which is an electron transport layer material, was deposited at 30 nm.
  • Example 1 R1 4.0 515 18.1 Example 2 R3 4.0 515 17.2 Example 3 R4 4.2 515 17.9 Example 4 R5 3.9 515 17.1 Example 5 R6 4.0 515 18.5 Example 6 R7 4.3 515 17.9 Example 7 R11 4.2 515 18.2 Example 8 R14 4.2 515 17.6 Example 9 R18 4.1 515 17.1 Example 10 R21 3.6 515 18.0 Example 11 R23 4.4 515 17.3 Example 12 R25 4.0 515 18.3 Example 13 R26 4.3 515 17.9 Example 14 R27 4.2 515 17.9 Example 15 R31 4.2 515 17.5 Example 16 R41 4.0 515 18.2 Example 17 R45 4.3 515 17.7 Example 18 R47 4.2 515 17.7 Example 19 R51 4.1 515 17.1 Example 20 R61 4.1 515 18.3 Example 21 R67 3.5 515 17.3 Example 22 R71 4.0 515 18.3 Example 23 R81 4.3 515
  • Example 1 when the compound according to the present invention (Examples 1-29) was used as the light emitting layer of the green organic EL device, it was compared with the green organic EL device (Comparative Example 1) using Alq3 as the electron transporting layer. It can be seen that the better performance in terms of efficiency and driving voltage.

Landscapes

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

Abstract

La présente invention concerne un nouveau composé organique et un élément électroluminescent organique l'utilisant et, plus particulièrement, un nouveau composé organique ayant d'excellente capacité de transfert d'électrons et un élément électroluminescent organique contenant le nouveau composé dans au moins une couche de matériau organique. L'élément électroluminescent organique de l'invention présente des caractéristiques améliorées, telles qu'une efficacité d'émission de lumière, une tension d'attaque et une durée de vie.
PCT/KR2018/001654 2017-02-08 2018-02-07 Composé organique et élément électroluminescent organique l'utilisant Ceased WO2018147638A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2017-0017298 2017-02-08
KR1020170017298A KR102729197B1 (ko) 2017-02-08 2017-02-08 유기 화합물 및 이를 이용한 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2018147638A1 true WO2018147638A1 (fr) 2018-08-16

Family

ID=63107732

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/001654 Ceased WO2018147638A1 (fr) 2017-02-08 2018-02-07 Composé organique et élément électroluminescent organique l'utilisant

Country Status (2)

Country Link
KR (1) KR102729197B1 (fr)
WO (1) WO2018147638A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112789273A (zh) * 2018-11-27 2021-05-11 株式会社Lg化学 新型化合物及包含其的有机发光器件
CN116490502A (zh) * 2021-02-22 2023-07-25 株式会社Lg化学 新型化合物及包含其的有机发光器件
US11746117B2 (en) 2018-11-27 2023-09-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising same
US12022730B2 (en) 2018-11-27 2024-06-25 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12435073B2 (en) 2019-08-19 2025-10-07 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020111601A1 (fr) * 2018-11-27 2020-06-04 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
WO2022177405A1 (fr) * 2021-02-22 2022-08-25 주식회사 엘지화학 Nouveau composé, et dispositif électroluminescent organique l'utilisant

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009158848A (ja) * 2007-12-27 2009-07-16 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2010044607A1 (fr) * 2008-10-14 2010-04-22 Cheil Industries Inc. Composés de benzimidazole et dispositif photoélectrique organique les comprenant
KR20150068282A (ko) * 2013-12-09 2015-06-19 주식회사 엠비케이 신규한 유기전기발광 화합물, 이를 포함하는 유기전기발광소자 및 전자 기기
KR20150121626A (ko) * 2014-04-21 2015-10-29 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20160149879A (ko) * 2015-06-19 2016-12-28 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20170060823A (ko) * 2015-11-25 2017-06-02 에스케이케미칼주식회사 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
CN107188852A (zh) * 2016-03-15 2017-09-22 上海和辉光电有限公司 一种应用于oled领域的化合物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101666825B1 (ko) 2014-03-11 2016-10-18 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009158848A (ja) * 2007-12-27 2009-07-16 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2010044607A1 (fr) * 2008-10-14 2010-04-22 Cheil Industries Inc. Composés de benzimidazole et dispositif photoélectrique organique les comprenant
KR20150068282A (ko) * 2013-12-09 2015-06-19 주식회사 엠비케이 신규한 유기전기발광 화합물, 이를 포함하는 유기전기발광소자 및 전자 기기
KR20150121626A (ko) * 2014-04-21 2015-10-29 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20160149879A (ko) * 2015-06-19 2016-12-28 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20170060823A (ko) * 2015-11-25 2017-06-02 에스케이케미칼주식회사 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
CN107188852A (zh) * 2016-03-15 2017-09-22 上海和辉光电有限公司 一种应用于oled领域的化合物

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112789273A (zh) * 2018-11-27 2021-05-11 株式会社Lg化学 新型化合物及包含其的有机发光器件
US11746117B2 (en) 2018-11-27 2023-09-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising same
CN112789273B (zh) * 2018-11-27 2023-12-29 株式会社Lg化学 化合物及包含其的有机发光器件
US12022730B2 (en) 2018-11-27 2024-06-25 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12037337B2 (en) 2018-11-27 2024-07-16 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12098156B2 (en) 2018-11-27 2024-09-24 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12275736B2 (en) 2018-11-27 2025-04-15 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US12435073B2 (en) 2019-08-19 2025-10-07 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
CN116490502A (zh) * 2021-02-22 2023-07-25 株式会社Lg化学 新型化合物及包含其的有机发光器件

Also Published As

Publication number Publication date
KR20180092035A (ko) 2018-08-17
KR102729197B1 (ko) 2024-11-12

Similar Documents

Publication Publication Date Title
WO2021182775A1 (fr) Dispositif électroluminescent organique
WO2020141949A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2017179809A1 (fr) Composé organique électroluminescent et élément électroluminescent organique l'utilisant
WO2021029616A1 (fr) Dispositif électroluminescent organique
WO2018038401A1 (fr) Composé organique et dispositif à électroluminescence organique comprenant un tel composé
WO2018147638A1 (fr) Composé organique et élément électroluminescent organique l'utilisant
WO2020027463A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2013094999A2 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2014142488A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2020153713A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2019135665A1 (fr) Dispositif électroluminescent organique
WO2019004584A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2018212463A1 (fr) Composé électroluminescent organique, et élément électroluminescent organique l'utilisant
WO2014027814A1 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2015125986A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020159333A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2020159334A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2022045743A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2021132956A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2019013503A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2023132668A1 (fr) Composé organique 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: 18750899

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 15.11.2019)

122 Ep: pct application non-entry in european phase

Ref document number: 18750899

Country of ref document: EP

Kind code of ref document: A1