WO2013094999A2 - Composé organique et dispositif électroluminescent organique l'utilisant - Google Patents

Composé organique et dispositif électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2013094999A2
WO2013094999A2 PCT/KR2012/011158 KR2012011158W WO2013094999A2 WO 2013094999 A2 WO2013094999 A2 WO 2013094999A2 KR 2012011158 W KR2012011158 W KR 2012011158W WO 2013094999 A2 WO2013094999 A2 WO 2013094999A2
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
synthesis
compound
Prior art date
Application number
PCT/KR2012/011158
Other languages
English (en)
Korean (ko)
Other versions
WO2013094999A3 (fr
Inventor
김영배
백영미
배형찬
신진용
박호철
김태형
Original Assignee
주식회사 두산
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 주식회사 두산 filed Critical 주식회사 두산
Publication of WO2013094999A2 publication Critical patent/WO2013094999A2/fr
Publication of WO2013094999A3 publication Critical patent/WO2013094999A3/fr

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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole 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
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
  • a host / dopant system may be used as a light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer
  • anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, and the like. Green and red dopant materials are used, and CBP is a phosphorescent host material.
  • the present invention aims to provide novel organic compounds having good thermal stability due to the high glass transition temperature.
  • an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.
  • the present invention provides a compound represented by Formula 1:
  • a and B each represent a substituted or unsubstituted 6-membered cycle
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heteroatom having 3 to 40 heteroatoms Alkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted A substituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 60 arylsilyl group, or a substituted or unsubstituted C 6 An arylamine group of -C 60 ,
  • one or more substituents each introduced into the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group and arylamine group are each independently deuterium, halogen , Cyano group, C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl Group, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, and a C 6 to C 60 arylamine group, wherein a plurality of substituents may be the same or different;
  • R 1 to R 8 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl groups, substituted or unsubstituted C 6 to C 60 aryl groups, substituted or unsubstituted heteroaryl groups having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyl Oxy group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or unsubstituted C 6 -C 60 arylsilyl group, or substituted Or an unsubstituted C 6 -C 60 arylamine group,
  • one or more substituents each introduced into the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group and arylamine group are each independently deuterium, halogen , Cyano group, C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl Group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 An aryloxy group, and C 6 ⁇ C 60 It is selected from the group consisting of an arylamine group, a plurality of substituents may be the same or different.
  • the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
  • an organic electroluminescent device characterized in that it comprises the compound.
  • the organic material layer including the compound is preferably at least one selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer, more preferably a phosphorescent host or a fluorescent dopant of the light emitting layer.
  • the compound represented by Formula 1 of the present invention has excellent heat resistance, hole injection and transport performance, and luminescence performance
  • the compound represented by Formula 1 may be used in at least one of a hole injection layer, a hole transport layer, a phosphorescent / fluorescent host of a light emitting layer, and a dopant. Applicable
  • the present invention provides a compound represented by Chemical Formula 1 having a higher energy bandcap having a higher molecular weight than that of a conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter, referred to as 'CBP')]. Characterized in that.
  • a conventional organic EL device material for example, 4,4-dicarbazolybiphenyl (hereinafter, referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the indole skeleton is fused at both ends of naphthalene, and the energy level is controlled by various substituents, thereby having a wide bandgap (sky blue to red).
  • the phosphorescent property of the device may be improved, and the hole injection ability and / or the transport ability, the luminous efficiency, the driving voltage, and the lifetime characteristics may be improved. Therefore, the present invention can be applied to a hole transport layer, a hole injection layer, a host, and the like by introducing various substituents as well as the light emitting layer.
  • the compound since the compound has a wide bandgap due to the indole-based skeleton, it may exhibit excellent properties as a light emitting host material compared to the conventional CBP.
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced to the indole-based skeleton, so that the glass transition temperature is improved, thereby having a higher thermal stability than the conventional CBP. . Therefore, the device including the compound of the present invention can greatly improve durability and lifespan characteristics.
  • the compound when adopted as a hole injection / transport layer, a blue, green and / or red phosphorescent host material or a fluorescent dopant material of an organic EL device, the compound can have an excellent effect on efficiency and lifetime compared to CBP. Therefore, the compound represented by Formula 1 according to the present invention can greatly contribute to the performance improvement and the lifespan improvement of the organic EL device, and in particular, the device life improvement has a great effect in maximizing the performance in the full color organic light emitting panel.
  • a and B are substituted or unsubstituted 6-membered cycles, respectively, which are simply attached or fused to each other to be substituted or unsubstituted.
  • a and B are substituted or unsubstituted 6-membered cycles, respectively, which are simply attached or fused to each other to be substituted or unsubstituted.
  • the naphthalene derivative is a deuterium, halogen, substituted or unsubstituted C 1 ⁇ C 40 alkyl group, substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms , Substituted or unsubstituted C 6 ⁇ C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 ⁇ C 40 alkyloxy group, substituted or unsubstituted C 6 ⁇ C 60 aryloxy group, substituted or unsubstituted C 1 ⁇ C 40 Alkylsilyl group, substituted or unsubstituted C 6 ⁇ C 60 Arylsilyl group and substituted or unsubstituted C 6 ⁇ C It may be substituted with a substituent selected from the group consisting of 60 ary
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 ⁇ C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, or is a substituted or unsubstituted arylamine group of the unsubstituted C 6 ⁇ C 60 are preferred.
  • the aryl group, heteroaryl group and arylamine group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 ⁇ 40 heterocycloalkyl group , C 6 ⁇ C 60 aryl group, nuclear atom 5 ⁇ 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, and C 6 ⁇ C 60 arylamine It is selected from the group consisting of groups, a plurality of substituents may each be the same or different.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group (pyrimidinyl group), a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, or a substituted or unsubstituted indolyl group group, the phenyl group,
  • One or more substituents respectively introduced to the naphthyl group, pyridyl group, pyridinyl group, triazinyl group, quinolyl group, and indolyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl groups, heterocycloalkyl groups
  • Ar 1 and Ar 2 may each independently be selected from the group consisting of the following substituents S1 to S138.
  • Examples of the compound represented by Formula 1 according to the present invention include a compound represented by Formula 2 to a compound represented by Formula 8, but are not limited thereto.
  • R 1 and Ar 2 are the same as defined in Chemical Formula 1,
  • R 9 to R 12 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl groups, substituted or unsubstituted C 6 to C 60 aryl groups, substituted or unsubstituted heteroaryl groups having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyl Oxy group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or unsubstituted C 6 -C 60 arylsilyl group, or substituted Or an unsubstituted C 6 -C 60 arylamine group,
  • one or more substituents each introduced into the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group and arylamine group are each independently deuterium, halogen , Cyano group, C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl Group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 An aryloxy group, and C 6 ⁇ C 60 It is selected from the group consisting of an arylamine group, a plurality of substituents may be the same or different.
  • unsubstituted alkyl is a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like. Include.
  • Unsubstituted cycloalkyl includes monocyclic or polycyclic non-aromatic hydrocarbon groups having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Unsubstituted heterocycloalkyl means a non-aromatic moiety having 3 to 40 nuclear atoms, in which one or more carbons in the ring, preferably 1 to 3 carbons, are replaced with a hetero atom such as N, O or S .
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • Unsubstituted aryl means an aromatic moiety having 6 to 60 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached in a simple or fused form with one another. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Unsubstituted heteroaryl means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 60 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. It is understood that two or more rings may be attached in a simple or fused form to each other and further include a condensed form with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Unsubstituted alkyloxy means alkyl with 1 to 40 carbon atoms attached to oxygen and is interpreted to include a linear, branched or cyclic structure.
  • Examples of the alkyloxy group may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Unsubstituted aryloxy includes phenyloxy, naphthyloxy, diphenyloxy and the like having 5 to 60 carbon atoms, and "unsubstituted arylamine” means amine substituted with aryl having 6 to 60 carbon atoms.
  • Fused ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1), preferably a compound represented by the formula (2) to (8).
  • the present invention is an anode (anode); 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 a compound represented by Chemical Formula 1, preferably, Chemical Formulas 2 to 8.
  • an organic EL device comprising the compound shown. At this time, the compound of Formula 1 to 8 may be included alone or in plurality.
  • the organic material layer including the compound represented by Formula 1 of the present invention, preferably the compound represented by Formulas 2 to 8 may be any one or more of a hole injection layer, a hole transport layer, and a light emitting layer. Preferably, it may be included in the organic EL element as a material of the hole injection layer and the hole transport layer. In this case, the organic EL device can maximize the hole injection / transport ability.
  • a light emitting layer material of an organic EL element preferably a blue, green and / or phosphorescent host, a fluorescent dopant, it is possible to provide improved efficiency and lifespan.
  • the compound represented by the formula (1), preferably formula (2) to formula (8) according to the present invention has a high glass transition temperature. Therefore, when the compound is used as an organic material layer of the organic light emitting device, since crystallization is minimized in the organic light emitting device, the driving voltage of the device can be lowered, and the luminous efficiency, thermal stability, and lifetime characteristics can be improved. .
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, and the light emitting layer may include the compound represented by Formula 1.
  • the compound of the present invention can be used as a phosphorescent host or fluorescent dopant of the light emitting layer.
  • 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 at an interface between an electrode and an organic material layer.
  • the organic material layer including the compound represented by 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 EL 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 Formula 1 of the present invention. Can be prepared.
  • 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.
  • the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.
  • reaction temperature was cooled to room temperature to obtain a solid product, and then the solid product was filtered. Thereafter, the filtered solid product was recrystallized from dichloromethane and acetone to give 1,5-bis (2-nitrophenyl) naphthalene (12.41 g, 61% yield) as a yellow solid.
  • Phenylboronic acid (1.65 g, 13.57 mmol) was used instead of 1-bromo-2-nitrobenzene (23.31 g, 115.37 mmol) used in ⁇ Preparation 1-2> of Preparation Example 2, and 1,5-bis (4 4,11-dibromo- obtained in ⁇ Preparation Step 2-3> of Preparation Example 2 instead of 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalene (20 g, 54.94 mmol) 1,8-dihydrocarbazolo [4,3-c] carbazole (3 g, 6.46 mmol) is used, except that THF is used instead of toluene, in the same manner as in ⁇ Preparation Step 1-2> of Preparation Example 2 And stirred.
  • ⁇ Preparation step 3- instead of 1,5-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalene used in ⁇ preparation step 1-2> of Preparation Example 1 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalene (20 g, 52.63 mmol) obtained in 1> and THF instead of toluene Except that, in the same manner as in ⁇ Preparation step 1-2> of Preparation Example 1 to obtain 2,7-bis (2-nitrophenyl) naphthalene (11.5 g, 59% yield).
  • the compound Inv-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured by the following method.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 mm 3 was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405), the substrate was cleaned using UV for 5 minutes and the substrate was vacuum-deposited. Was transferred.
  • ITO Indium tin oxide
  • Example 2 Except for using the compounds Inv-2 to Inv-30 synthesized in Synthesis Examples 2 to 30 instead of the compound Inv-1 used as a light emitting host material in Example 1, the same as in Example 1 To an organic EL device.
  • An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Inv-1 used as the light emitting host material in forming the emission layer in Example 1.
  • the structure of CBP is as follows.
  • Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Inv-1 6.78 516 41.4 Example 2 Inv-2 6.77 516 41.6 Example 3 Inv-3 6.64 515 40.2 Example 4 Inv-4 6.69 515 41.1 Example 5 Inv-5 6.70 517 41.3 Example 6 Inv-6 6.75 516 42.1 Example 7 Inv-7 6.77 517 41.5 Example 8 Inv-8 6.79 516 41.2 Example 9 Inv-9 6.86 517 39.4 Example 10 Inv-10 6.85 518 38.8 Example 11 Inv-11 6.65 516 42.0 Example 12 Inv-12 6.68 516 41.3 Example 13 Inv-13 6.69 517 42.2 Example 14 Inv-14 6.74 516 40.9 Example 15 Inv-15 6.84 517 40.0 Example 16 Inv-16 6.83 518 40.3 Example 17 Inv-17 6.78 517 42.4 Example 18 Inv-18 6.86 517 40.6 Example 19 Inv-19 6.89 518 40.3 Example 20 Inv-20 6.85 518 39.8 Example 21 Inv
  • the green organic EL devices of Examples 1 to 30 using the compounds represented by Formula 1 according to the present invention (Inv-1 to Inv-30) as the host material of the light emitting layer were compared with those of Comparative Example 1 using conventional CBP. It was confirmed that the green organic EL device exhibited better performance in terms of current efficiency and driving voltage.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un nouveau composé organique électroluminescent, et un dispositif électroluminescent organique l'utilisant, et plus particulièrement elle concerne un nouveau composé électroluminescent organique qui est utilisé comme matériau d'injection de trou, de transport de trou ou électroluminescent, et un dispositif électroluminescent organique l'utilisant.
PCT/KR2012/011158 2011-12-23 2012-12-20 Composé organique et dispositif électroluminescent organique l'utilisant WO2013094999A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020110141688A KR101506761B1 (ko) 2011-12-23 2011-12-23 유기 화합물 및 이를 이용한 유기 전계 발광 소자
KR10-2011-0141688 2011-12-23

Publications (2)

Publication Number Publication Date
WO2013094999A2 true WO2013094999A2 (fr) 2013-06-27
WO2013094999A3 WO2013094999A3 (fr) 2013-08-22

Family

ID=48669663

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/011158 WO2013094999A2 (fr) 2011-12-23 2012-12-20 Composé organique et dispositif électroluminescent organique l'utilisant

Country Status (2)

Country Link
KR (1) KR101506761B1 (fr)
WO (1) WO2013094999A2 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104403662A (zh) * 2014-11-11 2015-03-11 烟台万润精细化工股份有限公司 一种有机电致发光材料及其制备方法、应用
CN104513662A (zh) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 一种有机发光材料及其应用
WO2015093814A1 (fr) * 2013-12-16 2015-06-25 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
JP2016503761A (ja) * 2012-12-11 2016-02-08 ドク サン ネオルクス カンパニーリミテッド 有機電子素子用化合物、これを用いた有機電子素子及びその電子装置
JP2017526642A (ja) * 2014-07-10 2017-09-14 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物及びそれを含む有機電界発光デバイス
CN108864124A (zh) * 2017-05-12 2018-11-23 株式会社Lg化学 环状化合物及包含其的有机发光元件
CN110229051A (zh) * 2019-06-26 2019-09-13 四川师范大学 纳米石墨烯三苯并苉盘状液晶化合物的合成与发光性
WO2019194481A1 (fr) * 2018-04-02 2019-10-10 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
CN111094295A (zh) * 2017-07-18 2020-05-01 株式会社Lg化学 新的化合物和包含其的有机发光器件
CN111194320A (zh) * 2017-10-20 2020-05-22 株式会社Lg化学 多环化合物和包含其的有机发光元件
CN111902515A (zh) * 2018-04-02 2020-11-06 罗门哈斯电子材料韩国有限公司 有机电致发光化合物以及包含其的有机电致发光装置
CN112142741A (zh) * 2019-06-26 2020-12-29 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102263057B1 (ko) * 2014-05-07 2021-06-09 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20160063259A (ko) 2014-11-26 2016-06-03 삼성전자주식회사 유기 반도체 화합물, 이를 포함하는 유기 박막 및 상기 유기 박막을 포함하는 전자 소자
CN104673276B (zh) * 2014-12-31 2017-05-31 固安鼎材科技有限公司 一种有机发光材料及其应用
CN114940681A (zh) 2016-11-23 2022-08-26 株式会社Lg化学 电活性化合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100007780A (ko) * 2008-07-14 2010-01-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광 소자
WO2010074520A2 (fr) * 2008-12-23 2010-07-01 (주)루미나노 Nouveau composé semi-conducteur organique, procédé de préparation associé, composition semi-conductrice organique, couche mince semi-conductrice organique et élément intégrant le composé
WO2010110553A2 (fr) * 2009-03-23 2010-09-30 Dow Advanced Display Materials, Ltd. Nouveaux composés organiques électroluminescents, et dispositif organique électroluminescent les utilisant
WO2010126234A1 (fr) * 2009-04-29 2010-11-04 Dow Advanced Display Materials,Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100007780A (ko) * 2008-07-14 2010-01-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광 소자
WO2010074520A2 (fr) * 2008-12-23 2010-07-01 (주)루미나노 Nouveau composé semi-conducteur organique, procédé de préparation associé, composition semi-conductrice organique, couche mince semi-conductrice organique et élément intégrant le composé
WO2010110553A2 (fr) * 2009-03-23 2010-09-30 Dow Advanced Display Materials, Ltd. Nouveaux composés organiques électroluminescents, et dispositif organique électroluminescent les utilisant
WO2010126234A1 (fr) * 2009-04-29 2010-11-04 Dow Advanced Display Materials,Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016503761A (ja) * 2012-12-11 2016-02-08 ドク サン ネオルクス カンパニーリミテッド 有機電子素子用化合物、これを用いた有機電子素子及びその電子装置
US10003031B2 (en) 2012-12-11 2018-06-19 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
CN104513662A (zh) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 一种有机发光材料及其应用
WO2015093814A1 (fr) * 2013-12-16 2015-06-25 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
TWI506028B (zh) * 2013-12-16 2015-11-01 羅門哈斯電子材料韓國公司 有機電場發光化合物及包含該化合物之有機電場發光裝置
JP2017526642A (ja) * 2014-07-10 2017-09-14 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物及びそれを含む有機電界発光デバイス
CN104403662A (zh) * 2014-11-11 2015-03-11 烟台万润精细化工股份有限公司 一种有机电致发光材料及其制备方法、应用
CN108864124A (zh) * 2017-05-12 2018-11-23 株式会社Lg化学 环状化合物及包含其的有机发光元件
CN111094295B (zh) * 2017-07-18 2022-05-17 株式会社Lg化学 新的化合物和包含其的有机发光器件
CN111094295A (zh) * 2017-07-18 2020-05-01 株式会社Lg化学 新的化合物和包含其的有机发光器件
CN111194320B (zh) * 2017-10-20 2023-04-04 株式会社Lg化学 多环化合物和包含其的有机发光元件
CN111194320A (zh) * 2017-10-20 2020-05-22 株式会社Lg化学 多环化合物和包含其的有机发光元件
CN111902515A (zh) * 2018-04-02 2020-11-06 罗门哈斯电子材料韩国有限公司 有机电致发光化合物以及包含其的有机电致发光装置
WO2019194481A1 (fr) * 2018-04-02 2019-10-10 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
CN112142741A (zh) * 2019-06-26 2020-12-29 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件
CN110229051A (zh) * 2019-06-26 2019-09-13 四川师范大学 纳米石墨烯三苯并苉盘状液晶化合物的合成与发光性
CN112142741B (zh) * 2019-06-26 2023-05-12 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件

Also Published As

Publication number Publication date
KR101506761B1 (ko) 2015-03-30
KR20130073700A (ko) 2013-07-03
WO2013094999A3 (fr) 2013-08-22

Similar Documents

Publication Publication Date Title
WO2013094999A2 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2017179809A1 (fr) Composé organique électroluminescent et élément électroluminescent organique l'utilisant
WO2018038401A1 (fr) Composé organique et dispositif à électroluminescence organique comprenant un tel composé
WO2018093107A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018110958A1 (fr) Composé électroluminescent organique et élément électroluminescent organique l'utilisant
WO2014142488A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2014010810A1 (fr) Nouveau composé et dispositif électroluminescent le comprenant
WO2014092354A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2014025209A1 (fr) Nouveau composé et dispositif électroluminescent organique comprenant celui-ci
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2016105054A2 (fr) Composé organique luminescent et élément électroluminescent organique faisant appel audit composé
WO2017209488A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
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
WO2017023125A1 (fr) Composé organique photoémetteur et dispositif électroluminescent organique l'utilisant
WO2014046392A1 (fr) Composé organique et élément électroluminescent le comportant
WO2020027463A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2014027822A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2015111942A2 (fr) Composé organique et élément électroluminescent organique le contenant
WO2013191355A1 (fr) Nouveau composé et élément électroluminescent organique le comprenant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2014081134A1 (fr) Nouveau composé et élément électroluminescent organique comprenant ledit composé
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2015133808A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé

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: 12859531

Country of ref document: EP

Kind code of ref document: A2

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 10/10/2014)

122 Ep: pct application non-entry in european phase

Ref document number: 12859531

Country of ref document: EP

Kind code of ref document: A2