[go: up one dir, main page]

WO2013094921A1 - Dérivé aza-indéno-anthracène et élément électroluminescent organique l'utilisant - Google Patents

Dérivé aza-indéno-anthracène et élément électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2013094921A1
WO2013094921A1 PCT/KR2012/010782 KR2012010782W WO2013094921A1 WO 2013094921 A1 WO2013094921 A1 WO 2013094921A1 KR 2012010782 W KR2012010782 W KR 2012010782W WO 2013094921 A1 WO2013094921 A1 WO 2013094921A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compound
condensed
aryl
deuterium
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/KR2012/010782
Other languages
English (en)
Korean (ko)
Inventor
이인혁
이은정
김태형
박호철
신진용
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 WO2013094921A1 publication Critical patent/WO2013094921A1/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
    • H10K85/60—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Definitions

  • the present invention relates to an azaindenoanthracene derivative and an organic electroluminescent device using the same, and more particularly to an organic electroluminescent device exhibiting excellent efficiency, driving voltage, life, etc. by applying azaindenoanthracene derivative to the light emitting layer will be.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using such an organic light emitting phenomenon usually has a structure including an anode, a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), electrons Injection layer and the like.
  • the material used as the organic material layer may be classified into a light emitting material, a charge transport material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the luminescent material may be classified into blue, green, and red luminescent materials and yellow and orange luminescent materials required to achieve better natural colors according to the emission color.
  • a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap than the host mainly constituting the light emitting layer and excellent luminous efficiency is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. In this case, since 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 to be used.
  • a material constituting the organic material layer in the device that is, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • a hole injection material a hole transport material
  • a light emitting material an electron transport material, an electron injection material, etc.
  • Korean Patent Publication No. 10-2011-0024695 discloses an organic electroluminescent device using an anthracene derivative and an amine derivative.
  • the development of a stable and efficient organic material layer for an organic light emitting device has not yet been made sufficiently, and therefore, development of new materials is continuously required.
  • the present invention has been made to solve the above problems, to provide a novel material that can be used as a light emitting layer to improve the luminous efficiency, brightness, power efficiency, thermal stability and device life of the device and to provide an organic electroluminescent device using the same The purpose.
  • the present invention provides a compound represented by the following formula (1), preferably an azaindenoanthracene-based compound.
  • Each X is independently carbon or nitrogen, wherein at least one of X is nitrogen,
  • R 1 to R 12 are the same or different, each independently represent hydrogen, deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 of a heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 6 ⁇ C 40 aryl group, C 6 ⁇ C 40 of the diarylamino group, C aryl group of 6 ⁇ C 40, C 6 ⁇ C 40 of the arylalkenyl Nyl group, C 3 ⁇ C 40 cycloalkyl group and C 3 ⁇ C 40 heterocycloalkyl group, each of which are adjacent groups and condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring or condensed heteroaromatic ring Form or not form
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.
  • the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer.
  • the compound represented by Formula 1 according to the present invention When the compound represented by Formula 1 according to the present invention is adopted as the light emitting layer material of the organic electroluminescent device, it may exhibit an increase in efficiency and an improvement in life compared to conventional light emitting materials.
  • the organic electroluminescent device of the present invention including the compound represented by Formula 1 exhibits excellent characteristics in terms of luminous efficiency, brightness, power efficiency, driving voltage and lifetime, thereby maximizing performance and improving lifetime in full color organic EL panels. It can be effective.
  • the present invention is characterized by introducing an aromatic ring or a heteroaromatic ring at a specific position of the basic skeleton while having an azaindenoanthracene-based basic skeleton having excellent device characteristics.
  • the azaindenonoanthracene compound contains a 5-membered ring structure.
  • the five-membered ring structure has excellent electron withdrawing properties, thereby exhibiting electron injection properties. Therefore, the organic light emitting device using the azaindenoanthracene compound is effective to transport electrons generated from the cathode, and the low driving voltage that can be generated contributes to the improvement of efficiency and lifetime.
  • introduction of an electronically stable substituent may constitute a more stable compound.
  • an aryl group, a heteroaryl group, an alkylaryl group or the like is introduced into the 9-position, as so be able to control the band gap depending on the substituents, as well as the light emitting layer by the introduction of various substituents hole transport layer, an electron transport layer, or a host application Can be.
  • the device containing the azaindenoanthracene compound of this invention can exhibit the durability and lifetime improvement.
  • R 1 , R 2 , R 3 , R 4 , R 9 , R 5 to R 8 , and R 10 to R 12 are all preferably hydrogen or deuterium.
  • R 9 , R 5 to R 8 , and R 10 to R 12 are all preferably hydrogen or deuterium.
  • R 9 position of the azaindenoanthracene is the most reactive substitution position, a more stable compound can be constituted by introducing an electronically stable substituent. Therefore, in the present invention, it is more preferable that all of R 1 to R 8 and R 10 to R 12 except for R 9 are hydrogen or deuterium.
  • R 9 is a C 6 to C 40 aryl group or a C 5 to C 40 heteroaryl group, each of which is adjacent to each other.
  • the aryl group or heteroaryl group is each independently deuterium, halogen, nitrile group, nitro group, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C
  • the aryl group is preferably phenyl, naphthalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, benzofluoranthene, perylene, fluorene, the heteroaryl group is pyridine, pyri Preferred is a case of midine, triazine, carbazole, acridine, dibenzothiophene, dibenzofuran, thianthrene.
  • the compound represented by Chemical Formula 1 of the present invention should be introduced with at least one nitrogen as X, of which one nitrogen atom is preferably introduced as X.
  • nitrogen having a relatively higher electronegativity than carbon is introduced, the electron recruitment of the five-membered ring structure can be enhanced.
  • R 1 to R 3 and R 5 to R 12 are as defined in Chemical Formula 1.
  • R 5 to R 8 , and R 10 to R 12 are all preferably hydrogen or deuterium, and particularly, except R 9 . More preferably, R 1 to R 3 , R 5 to R 8 and R 10 to R 12 are all hydrogen or deuterium.
  • R 9 is a C 6 to C 40 aryl group or a C 5 to C 40 heteroaryl group Wherein they each form or do not form condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings or condensed heteroaromatic rings with adjacent groups;
  • the aryl group or heteroaryl group is each independently deuterium, halogen, nitrile group, nitro group, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C One selected from the group consisting of 1 to C 40 amino group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 6 to C 40 aryl group and C 5 to C 40 heteroaryl group It may be substituted or unsubstituted above.
  • the azaindenoanthracene-based compound represented by the general formula (1) according to the present invention may be more specified by the chemical formulas illustrated below. However, the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compound represented by Chemical Formula 1 may be synthesized according to a general synthesis method, and their detailed synthesis process will be described in detail in the synthesis examples described below.
  • another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device comprises (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein the at least one organic layer At least one of them is characterized in that it comprises a compound represented by the formula (1) of the present invention.
  • the organic material layer including the compound represented by Chemical Formula 1 may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the compound represented by Formula 1 may be included in the organic electroluminescent device as a light emitting layer material.
  • the organic EL device may improve luminous efficiency, brightness, power efficiency, thermal stability, and device life.
  • the compound represented by Formula 1 according to the present invention may be included as a phosphorescent or fluorescent host material or a dopant material thereof.
  • the compound represented by Formula 1 may be included in the organic light emitting device as a phosphorescent host, a fluorescent host, or a dopant material of blue, green, and / or red.
  • organic material layers other than the organic material layer containing the compound of Formula 1 may be a hole injection layer, a hole transport layer, a light emitting layer, and / or an electron transport layer.
  • a substrate, an anode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode may be sequentially stacked, and the light emitting layer may be represented by Formula 1 according to the present invention. It may include a compound represented by.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted between the electrode and the organic material layer interface.
  • the organic material layer including the compound represented by Chemical Formula 1 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 organic electroluminescent device according to the present invention forms an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1. It can be manufactured by.
  • a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • materials such as a hole injection layer, a hole transport layer, and an electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.
  • Compound Mat-3 was prepared by following the same procedure as in Synthesis Example 1, except that pyren-1-ylboronic acid was used instead of anthracen-2-ylboronic acid.
  • Compound Mat-4 was prepared by the same procedure as in Synthesis Example 1, except that 9,9-dimethyl-9H-fluoren-2-ylboronic acid was used instead of anthracen-2-ylboronic acid.
  • Compound Mat-12 was prepared by following the same procedure as in Synthesis Example 1, except that 9,10-di (naphthalen-2-yl) anthracen-2-ylboronic acid was used instead of anthracen-2-ylboronic acid. .
  • Compound Mat-13 was prepared by the same procedure as in Synthesis Example 1, except that fluoranthen-3-ylboronic acid was used instead of anthracen-2-ylboronic acid.
  • Compound Mat-14 was prepared in the same manner as in Synthesis Example 1, except that 7,12-diphenylbenzo [k] fluoranthen-3-ylboronic acid was used instead of anthracen-2-ylboronic acid.
  • Compound Mat-16 was prepared by the same procedure as in Synthesis Example 1, except that 4- (phenanthren-9-yl) phenylboronic acid was used instead of anthracen-2-ylboronic acid.
  • Compound Mat-38 was prepared in the same manner as in Synthesis Example 1, except that 9-phenyl-9H-carbazol-3-ylboronic acid was used instead of anthracen-2-ylboronic acid.
  • Compound Mat-44 was prepared in the same manner as in Synthesis Example 1, except that 4- (naphthalen-1-yl) phenylboronic acid was used instead of anthracen-2-ylboronic acid.
  • Compound Mat-52 was prepared by the same procedure as in Synthesis Example 1, except that 4- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid was used instead of anthracen-2-ylboronic acid.
  • a compound was prepared in the same manner as in Synthesis Example 1, except that 9,9'-diphenyl-9H, 9'H-3,3'-bicarbazol-7-ylboronic acid was used instead of anthracen-2-ylboronic acid. Mat-63 was prepared.
  • Compound Mat-77 was prepared by the same procedure as in Synthesis Example 1, except that naphthalen-2-ylboronic acid was used instead of anthracen-2-ylboronic acid.
  • An organic electroluminescent device was manufactured by the following method.
  • the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma and the substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • DS-205 Doosan Co., Ltd. was vacuum-deposited to a thickness of 800 kPa on the prepared ITO (anode) to form a hole injection layer, and ⁇ -NPB ( N , N- , a hole transporting material, on the hole injection layer).
  • An organic electroluminescent device of Examples 2 and 3 was manufactured by the same method as Example 1, except that Compound Mat-3 and Mat-4 were used instead of Compound Mat-1 when forming the emission layer.
  • DS-H522 Doosan Co., Ltd.
  • DS-H522 Doosan Co., Ltd.
  • compounds Mat-9 Example 4
  • Mat-12 Example 5
  • Mat-13 Example 6
  • Mat- The organic electric field of Examples 4-9 was carried out in the same manner as in Example 1, except that 14 (Example 7), Mat-25 (Example 8), and Mat-53 (Example 9) were used, respectively.
  • a green light emitting device was manufactured.
  • Example 11 The same method as in Example 1, except that DS-405 (Doosan Co., Ltd.), blue dopant compound Mat-76 (Example 10), and Mat-77 (Example 11) were used as the blue host to form the emission layer. To perform the organic electroluminescent blue light emitting device was manufactured.
  • the organic light emitting layer was organically formed in the same manner as in Example 1, except that Alq3 and C-545T, which are systems represented by green devices, were used instead of the compound and DS-H522 (Doosan Co., Ltd.). An electroluminescent device was produced.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except for using the blue device system ADN and DS-405 instead of the compound and DS-405 (Doosan Co., Ltd.) used to fabricate the light emitting layer in the present invention. Produced.
  • HIL Hole Injection Layer
  • HTL Hole Transport Layer
  • EML Organic Light Emitting Layer
  • ETL Electron Transport Layer
  • EIL Alq3 Electron Injection Layer
  • NPB, C-545T, ADN is as follows.
  • the organic EL device of Examples 1 to 3 using the compound according to the present invention as a green host was able to confirm slightly improved performance in terms of driving voltage and efficiency.
  • organic EL device of Examples 4 to 9 using the compound according to the present invention as a green dopant was able to confirm a significantly improved performance in terms of driving voltage and efficiency.
  • Example 10-11 For each organic electroluminescent blue light emitting device manufactured in Example 10-11 and Comparative Example 2, the luminous efficiency and driving voltage at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 4 below.

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)

Abstract

La présente invention concerne un dérivé aza-indéno-anthracène et un élément électroluminescent organique l'utilisant. Dans la présente invention, le dérivé aza-indéno-anthracène est appliqué à une couche luminescente de l'élément électroluminescent organique pour apporter une meilleure efficacité, une meilleure tension de commande et une meilleure durée de vie de service.
PCT/KR2012/010782 2011-12-19 2012-12-12 Dérivé aza-indéno-anthracène et élément électroluminescent organique l'utilisant Ceased WO2013094921A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020110137332A KR101319631B1 (ko) 2011-12-19 2011-12-19 아자인데노안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
KR10-2011-0137332 2011-12-19

Publications (1)

Publication Number Publication Date
WO2013094921A1 true WO2013094921A1 (fr) 2013-06-27

Family

ID=48668755

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/010782 Ceased WO2013094921A1 (fr) 2011-12-19 2012-12-12 Dérivé aza-indéno-anthracène et élément électroluminescent organique l'utilisant

Country Status (2)

Country Link
KR (1) KR101319631B1 (fr)
WO (1) WO2013094921A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015050140A1 (fr) * 2013-10-03 2015-04-09 出光興産株式会社 Composé, matériau d'élément électroluminescent organique utilisant celui-ci, élément électroluminescent organique utilisant ce matériau, et dispositif électronique
CN105272961A (zh) * 2014-06-06 2016-01-27 昱镭光电科技股份有限公司 电子传输化合物及使用该化合物的有机电致发光元件
WO2016163372A1 (fr) * 2015-04-08 2016-10-13 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques comprenant ce dernier, et élément électroluminescent organique et dispositif électronique comprenant chacun ce dernier

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090118859A (ko) * 2008-05-14 2009-11-18 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
KR20100007143A (ko) * 2008-07-11 2010-01-22 주식회사 엘지화학 신규한 안트라센 유도체 및 이를 이용한 유기전자소자
KR20110016033A (ko) * 2009-08-10 2011-02-17 삼성모바일디스플레이주식회사 축합환 화합물 및 이를 포함한 유기층을 구비한 유기 발광 소자
KR20110085784A (ko) * 2010-01-21 2011-07-27 (주)씨에스엘쏠라 유기발광화합물 및 이를 구비한 유기발광소자

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101120917B1 (ko) * 2009-06-19 2012-02-27 주식회사 두산 아미노 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
KR101121677B1 (ko) * 2009-06-22 2012-02-28 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090118859A (ko) * 2008-05-14 2009-11-18 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
KR20100007143A (ko) * 2008-07-11 2010-01-22 주식회사 엘지화학 신규한 안트라센 유도체 및 이를 이용한 유기전자소자
KR20110016033A (ko) * 2009-08-10 2011-02-17 삼성모바일디스플레이주식회사 축합환 화합물 및 이를 포함한 유기층을 구비한 유기 발광 소자
KR20110085784A (ko) * 2010-01-21 2011-07-27 (주)씨에스엘쏠라 유기발광화합물 및 이를 구비한 유기발광소자

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015050140A1 (fr) * 2013-10-03 2015-04-09 出光興産株式会社 Composé, matériau d'élément électroluminescent organique utilisant celui-ci, élément électroluminescent organique utilisant ce matériau, et dispositif électronique
JPWO2015050140A1 (ja) * 2013-10-03 2017-03-09 出光興産株式会社 化合物、これを用いた有機エレクトロルミネッセンス素子用材料、及びこれを用いた有機エレクトロルミネッセンス素子並びに電子機器
US10217945B2 (en) 2013-10-03 2019-02-26 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescent element material using same, organic electroluminescent element using this material, and electronic device
US10763442B2 (en) 2013-10-03 2020-09-01 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescent element material using same, organic electroluminescent element using this material, and electronic device
CN105272961A (zh) * 2014-06-06 2016-01-27 昱镭光电科技股份有限公司 电子传输化合物及使用该化合物的有机电致发光元件
CN105272961B (zh) * 2014-06-06 2018-06-01 昱镭光电科技股份有限公司 电子传输化合物及使用该化合物的有机电致发光元件
WO2016163372A1 (fr) * 2015-04-08 2016-10-13 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques comprenant ce dernier, et élément électroluminescent organique et dispositif électronique comprenant chacun ce dernier
US10629821B2 (en) 2015-04-08 2020-04-21 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements using same, and organic electroluminescent element and electronic device each using same

Also Published As

Publication number Publication date
KR101319631B1 (ko) 2013-10-17
KR20130070151A (ko) 2013-06-27

Similar Documents

Publication Publication Date Title
WO2010071362A2 (fr) Dérivé d'anthracène deutéré et dispositif électroluminescent organique comprenant ce dérivé
WO2012173370A2 (fr) Composés originaux et dispositif électronique organique utilisant ces composés
WO2020027389A1 (fr) Composé électroluminescent organique et élément électroluminescent organique le comprenant
WO2011081431A2 (fr) Composé émetteur de lumière organique, et dispositif électroluminescent organique l'utilisant
WO2014142472A1 (fr) Composé pour élément électrique organique, élément électrique organique utilisant celui-ci, et dispositif électronique associé
WO2013009079A1 (fr) Composé à base de triphénylène et diode électroluminescente organique l'utilisant
WO2011059271A2 (fr) Nouveau composé comprenant un anneau condensé, et dispositif électronique organique qui utilise celui-ci
WO2015009102A1 (fr) Composé organique luminescent et élément électroluminescent organique faisant appel audit composé
WO2011037429A2 (fr) Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique
WO2013051875A2 (fr) Dispositif électroluminescent organique et son procédé de fabrication
WO2011139125A2 (fr) Composé de phénanthrocarbazole, et dispositif électroluminescent organique utilisant ce composé
WO2010114267A2 (fr) Dispositif électronique organique, composés pour celui-ci et terminal
WO2013129836A1 (fr) Diode électroluminescente organique
WO2012015265A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique à base de ces composés
WO2014142467A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant le composé, et dispositif électronique comprenant l'élément électronique organique
WO2011081429A2 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2011149283A2 (fr) Composé comprenant un hétérocycle à cinq chaînons, élément électrique organique l'utilisant et borne correspondante
WO2011139129A2 (fr) Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant
WO2014098455A1 (fr) Nouveau composé organique et élément électroluminescent organique le comprenant
WO2014123369A1 (fr) Nouveau composé et élément électronique organique l'utilisant
WO2011108901A2 (fr) Composé de spiro-carbazole comprenant un squelette spiro, et élément électronique organique utilisant celui-ci et terminal de celui-ci
WO2011149284A2 (fr) Composé contenant des hétéroatomes dans lequel un carbazole et un fluorène sont condensés, élément électrique organique l'utilisant et borne correspondante
WO2014084612A1 (fr) Nouveau composé et élément électronique organique l'utilisant
WO2019066607A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2010058946A2 (fr) Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés

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: 12860110

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 17-10-2014 )

122 Ep: pct application non-entry in european phase

Ref document number: 12860110

Country of ref document: EP

Kind code of ref document: A1