WO2017086706A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé - Google Patents

Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé Download PDF

Info

Publication number
WO2017086706A1
WO2017086706A1 PCT/KR2016/013255 KR2016013255W WO2017086706A1 WO 2017086706 A1 WO2017086706 A1 WO 2017086706A1 KR 2016013255 W KR2016013255 W KR 2016013255W WO 2017086706 A1 WO2017086706 A1 WO 2017086706A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
mmol
sub
ring
compound
Prior art date
Application number
PCT/KR2016/013255
Other languages
English (en)
Korean (ko)
Inventor
문성윤
최연희
이선희
김슬기
전진배
Original Assignee
덕산네오룩스 주식회사
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 덕산네오룩스 주식회사 filed Critical 덕산네오룩스 주식회사
Publication of WO2017086706A1 publication Critical patent/WO2017086706A1/fr

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/02—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 two hetero rings
    • C07D403/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • 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

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the difference in characteristics depending on the material structure is very large and applied to various layers as a material of an organic electric device.
  • the band gap (HOMO, LUMO), electrical properties, chemical properties, and physical properties are different depending on the number of rings, the fused position, and the type and arrangement of heteroatoms. This has been going on.
  • US Patent Application Publication No. US2008 / 0145708A1 discloses an embodiment in which a polycyclic cyclic compound is applied to a hole transport layer or a phosphorescent host of an organic electric device
  • Korean Patent Application Publication No. 10-2007-0012218 discloses an embodiment in which a polycyclic cyclic compound is applied to an electron transport layer of an organic electric device.
  • the development of materials for organic electric devices for the heteroatom type, number and position of polycyclic cyclic compounds is actively progressing.
  • An object of the present invention is to provide a compound capable of improving the luminous efficiency and lifetime of the device while lowering the driving voltage of the device by using the properties of the polycyclic ring compound, an organic electric device using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula. Any one of R 5 and R 6 , R 6 and R 7 , R 8 and R 9, and R 9 and R 10 in Formula 1 may form a condensed ring represented by Formula 1a.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • the compound of the present invention By using the compound of the present invention, not only the driving voltage of the device can be lowered, but also the light emitting efficiency and lifetime of the device can be greatly improved.
  • FIG. 1 is a cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, fluorene group, spirofluorene group, spirobifluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” as used herein refers to deuterium, halogen, amino, nitrile, nitro, C 1 -C 20 alkyl, C 1 -C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of,
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • a protective layer or a light efficiency improving layer Capping layer
  • the compound according to the present invention applied to the organic material layer of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host of the dopant or light efficiency improvement layer of the light emitting layer 150 It may be used as a material.
  • the compound of the present invention may be used as the light emitting layer 150.
  • the light emitting layer is formed using the compound represented by Chemical Formula 1 to optimize the energy level and T1 value between each organic material layer, the intrinsic properties (mobility, interfacial properties, etc.) of the organic layer, and thus the life of the organic electric device. And efficiency can be improved at the same time.
  • the organic light emitting device may be manufactured using a physical vapor deposition (PVD) method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the organic electroluminescent device according to the present invention may be one of an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a device for monochrome or white illumination.
  • OLED organic light emitting diode
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • R 1 to R 14 are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; -L a -N (R a ) (R b ); An alkoxyl group of C 1 -C 30 ; And C 6 -C 30 It is selected from the group consisting of an aryloxy group or adjacent groups may combine with each other to form a ring, R 1 to R 14 which do not form a ring are the same as defined above,
  • R 5 and R 6 , R 6 and R 7 , R 8 and R 9, and R 9 and R 10 forms a condensed ring represented by Formula 1a,
  • R 5 and R 6 form a condensed ring represented by Formula 1a
  • R 5 represents a bond connected to **
  • R 6 represents a bond connected to *
  • R 6 and R 7 form a condensed ring represented by Formula 1a
  • R 6 represents a bond connected to **
  • R 7 represents a bond connected to *
  • R 8 and R 9 form a condensed ring represented by Formula 1a
  • R 8 represents a bond connected to **
  • R 9 represents a bond connected to *
  • R 9 and R 10 form a condensed ring represented by Formula 1a
  • R 9 represents a bond connected to **
  • R 10 represents a bond connected to *
  • X is one of S, O and C (Ar 2 ) (Ar 3 ),
  • Ar 1 is independently of each other C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; -L a -N (R a ) (R b ); An alkoxyl group of C 1 -C 30 ; And it is selected from the group consisting of C 6 -C 30 aryloxy group,
  • Ar 2 and Ar 3 are each independently i) a C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; And C 6 -C 30 It is selected from the group consisting of an aryloxy group, or ii) Ar 2 and Ar 3 may be bonded to each other to form a spiro compound with the C bonded thereto,
  • R a and R b are each independently a C 6 -C 60 aryl group; Fluorenyl group; A C 2 -C 60 heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; An alkyl group of C 1 -C 50 ; A fused ring group of an aromatic ring of C 6 -C 60 and an aliphatic ring of C 3 -C 60 ; And C 2 -C 20 Alkenyl group; It is selected from the group consisting of,
  • L 1 and L a are each independently a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A C 2 -C 60 divalent heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; Divalent fused ring group of C 3 -C 60 aliphatic ring and C 6 -C 60 aromatic ring; And divalent aliphatic hydrocarbon groups, each of L 1 and L a (excluding single bonds) is deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Aryl group of C 6 -C 20 ; C 6 -C 20 aryl group substituted with
  • R c and R d are each independently a C 6 -C 60 aryl group; Fluorenyl group; It may be selected from the group consisting of; C 2 -C 60 heterocyclic group containing at least one hetero atom of O, N, S, Si and P.
  • the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, each of the aryloxy group is deuterium; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Aryl group of C 6 -C 20 ; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -C 20 heterocyclic group including at least one heteroatom selected
  • the carbon number may be 6 to 60, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, the carbon number is 2 to 60, preferably 2 carbon atoms. ⁇ 30, more preferably a hetero ring having 2 to 20 carbon atoms, and in the case of the alkyl group, the carbon number is 1 to 50, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably It may be an alkyl group of 1 to 10.
  • the aryl group or arylene group is independently of each other a phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group or phenylene group, biphenylene group, terphenylene group, naphthyl Or a phenanthrene group or the like.
  • the compound represented by Formula 1 may be any one of the following compounds, but is not limited to the following compounds.
  • Formula 1 may be represented by one of the following Formula 2 to Formula 5.
  • R 1 to R 14 , X, Ar 1 and L 1 are the same as defined in Chemical Formula 1.
  • Ar 1 of Chemical Formula 1 may be represented by one of Chemical Formulas A-1 to A-3.
  • Q 1 to Q 4 are independently carbon (C) bonded to N, CR e , and L 1 , and one of Q 1 to Q 4 is carbon (C) bonded to L 1 . ego,
  • Q 1 to Q 4 are each independently N and CR e ,
  • Q 5 to Q 9 are independently of each other N, CR e ,
  • Z is C 6 -C 60 monocyclic or polycyclic aromatic ring; Or a C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si, and P,
  • R e is hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Aryl group of C 6 -C 20 ; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -C 20 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; A cycloalkyl group of C 3 -C 20 ; C 7 -C 20 arylalkyl group; And arylalkenyl group of
  • the Z ring of Chemical Formulas A-1 and A-2 may be independently one of the following Chemical Formulas.
  • the mark * denotes a binding moiety that combines with a ring including Q 1 to Q 4 to form a fused ring.
  • W 1 and W 2 are independently of each other a single bond, NL 2 -Ar 4 , S, O, C (Ar 5 ) (Ar 6 ),
  • V is independently of each other N, CR e ,
  • L 2 is a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A C 2 -C 60 divalent heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; Divalent fused ring group of C 3 -C 60 aliphatic ring and C 6 -C 60 aromatic ring; And it is selected from the group consisting of divalent aliphatic hydrocarbon group,
  • Ar 4 to Ar 6 is a C 6 -C 20 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; And it is selected from the group consisting of C 6 -C 30 aryloxy group,
  • Ar 5 and Ar 6 may be bonded to each other to form a spiro compound together with the carbon (C) to which they are bonded,
  • R e is the same as the definition of R e in Formulas A-1 to A-3.
  • At least one of Q 1 to Q 4 may be N.
  • At least one of Q 1 to Q 4 includes a structure including N may be one of Formulas Z-16 to Z-50.
  • W 1 and W 2 are independently of each other a single bond, NL 2 -Ar 4 , S, O, C (Ar 5 ) (Ar 6 ),
  • R e is hydrogen; heavy hydrogen; halogen;
  • R e in Chemical Formulas Z-16 to Z-50 are the same, but may be identical to or different from each other at each position in each Chemical Formula.
  • five R e are each independently of the other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Aryl group of C 6 -C 20 ; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -C 20 heterocyclic group including at least one heteroatom of O
  • the compound represented by Formula 1 may be any one of the following compounds, but is not limited to the following compounds.
  • the present invention provides a compound for an organic electric device represented by Chemical Formula 1.
  • the present invention provides an organic electric device containing the compound represented by the formula (1).
  • the organic electric element includes a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode.
  • the organic material layer may include a compound represented by Chemical Formula 1, and the compound represented by Chemical Formula 1 may be a hole injection layer or a hole transport layer of the organic material layer.
  • the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may be contained in at least one layer.
  • the compound represented by Formula 1 may be included in the hole transport layer or the light emitting auxiliary layer.
  • the compound represented by Formula 1 may be used as a material of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer or an electron injection layer.
  • the compound represented by Formula 1 may be used as a material of the light emitting layer.
  • an organic electroluminescent device comprising one of the compounds represented by the formula (1) in the organic material layer, more specifically, It provides an organic electroluminescent device comprising a compound represented by the individual formulas (1-1 to 4-38) in the organic material layer.
  • the compound is contained alone or in at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer of the organic material layer,
  • an organic electroluminescent device characterized in that a compound is contained in a combination of two or more different from each other, or the compound is contained in a combination of two or more.
  • each of the layers may include a compound corresponding to Formula 1 alone, and may include a mixture of two or more compounds of Formula 1, the compounds of claims 1 to 6, and compounds not corresponding to the present invention. And mixtures thereof.
  • the compound not corresponding to the present invention may be a single compound or two or more compounds.
  • the other compound when the compound is contained in a combination of two or more kinds of other compounds, the other compound may be a known compound of each organic material layer, or a compound to be developed in the future.
  • the compound contained in the organic material layer may be made only of the same kind of compound, but may be a mixture of two or more kinds of the compound represented by the formula (1).
  • the present invention provides a light efficiency improving layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric element further comprising.
  • Sub 1A to Sub 1D of Schemes 1 to 4 may be synthesized by the reaction routes of Scheme 5 and Scheme 6, but are not limited thereto.
  • R 5 , R 6 , R 8 , R 9 is Br.
  • Sub 1A-II-1 (19.75 g, 66.69 mmol) obtained in the above synthesis was dissolved in THF (220 ml) in a round bottom flask, followed by (2- (methylsulfinyl) phenyl) boronic acid (12.27 g, 66.69 mmol), Pd ( PPh 3 ) 4 (3.08 g, 2.67 mmol), NaOH (8.00 g, 200.06 mmol), water (110 ml) were added and stirred at 80 ° C.
  • Sub 1A-III'-2 (21.62 g, 69.89 mmol) obtained in the above synthesis was added to a round bottom flask together with Pd (OAc) 2 (1.57 g, 6.99 mmol) and 3-nitropyridine (0.87 g, 6.99 mmol).
  • 6 F 6 (105 ml), dissolved in DMI (70 ml), and tert- butyl peroxybenzoate (27.15 g, 139.77 mmol) were added and stirred at 90 ° C.
  • Sub 1C-II-1 (22.26 g, 75.16 mmol) obtained in the above synthesis was added to (4 '-(di ([1,1'-biphenyl] -4-yl) amino) -3- (methylsulfinyl)-[1, 1'-biphenyl] -4-yl) boronic acid (43.56 g, 75.16 mmol), Pd (PPh 3 ) 4 (3.47 g, 3.01 mmol), NaOH (9.02 g, 225.49 mmol), THF (250ml), water ( 125 ml) was added and 32.17 g (yield: 57%) of product was obtained using the Sub 1A-III-1 synthesis method.
  • Sub 1D-II-1 (15.02 g, 50.72 mmol) obtained in the above synthesis was added to (3 '-([1,1'-biphenyl] -3-yl (phenyl) amino) -3- (methylsulfinyl)-[1, 1'-biphenyl] -4-yl) boronic acid (25.53 g, 50.72 mmol), Pd (PPh 3 ) 4 (2.34 g, 2.03 mmol), NaOH (6.09 g, 152.15 mmol), THF (170ml), water ( 85 ml) was added to give 18.48 g (yield: 54%) of product using the Sub 1A-III-1 synthesis.
  • Compounds belonging to Sub 1A to Sub 1D may be the following compounds, but are not limited thereto.
  • Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 1A to Sub 1D.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 22, but is not limited thereto. At this time, Hal 1 and Hal 2 are Br or Cl.
  • Compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 2.
  • FD-MS Field Desorption-Mass Spectrometry
  • Sub 1A to Sub 1D (1 equiv) was dissolved in toluene in a round bottom flask, then Sub 2 (1 equiv), Pd 2 (dba) 3 (0.03 equiv), (t-Bu) 3 P (0.06 equiv), NaOt-Bu (3 equiv) was stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain a final product.
  • Sub 1A-1 (5.74 g, 17.75 mmol) obtained in the above synthesis was dissolved in toluene (180 ml) in a round bottom flask, and then Sub 2-50 (5.16 g, 17.75 mmol), Pd 2 (dba) 3 (0.49 g, 0.53 mmol), 50% P ( t -Bu) 3 (0.5ml, 1.06 mmol), NaO t -Bu (5.12 g, 53.25 mmol) were added and stirred at 100 ° C.
  • Sub 1B-3 (6.73 g, 20.18 mmol) obtained in the above synthesis in Sub 2-50 (5.87 g, 20.18 mmol), Pd 2 (dba) 3 (0.55 g, 0.61 mmol) 50% P ( t -Bu) 3 (0.6 ml, 1.21 mmol), NaO t -Bu (5.82 g, 60.55 mmol), toluene (200 ml) were added and the product P. 1-10 was used to yield 7.12 g (yield: 60%) of the product.
  • Sub 1D-7 (7.38 g, 20.65 mmol) obtained in the above synthesis in Sub 2-22 (7.91 g, 20.65 mmol), Pd 2 (dba) 3 (0.57 g, 0.62 mmol) 50% P ( t -Bu) 3 (0.6 ml, 1.24 mmol), NaO t -Bu (5.95 g, 61.95 mmol), toluene (205 ml) were added and the product P. 1-10 was used to yield 7.49 g (yield: 55%) of the product.
  • the reaction of one of Sub 1A to Sub 1D and Sub 2-> Final Product in Schemes 1 to 4 is based on the Buchwald-Hartwig cross coupling reaction, and in Scheme 5, the Sub 1-II-> Sub 1-III reaction, Sub 1-II-> Sub 1-III 'reaction, Sub 1-II-> Sub 1-III ”reaction, starting materials in Scheme 6-> Sub 1-I reaction, starting materials in Scheme 22-> Sub 2 reaction It is based on the Suzuki cross-coupling reaction (in this case, in the case of a reactant containing an amine, Korean Patent No. 10-1251451 (published on Apr. 5, 2013) and 10-1298483 (Aug. 21, 2013) of the present applicant.
  • An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention as a light emitting host material of a light emitting layer.
  • a 4,4 ', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine (abbreviated as 2-TNATA) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole having a thickness of 60 nm.
  • an NPD film was vacuum deposited to a thickness of 60 nm as a hole transport compound on the hole injection layer to form a hole transport layer.
  • Compound P 1-1 of the present invention was used as a host on the hole transport layer, and tris (2-phenylpyridine) -iridium (hereinafter, abbreviated as “Ir (ppy) 3 ”) as a dopant material was 95: 5 by weight. Doped to deposit a light emitting layer to a thickness of 30nm.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) aluminum
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of the present invention shown in Table 4 instead of the compound P 1-1 according to Example 1 of the present invention as a green host material of the emission layer. .
  • the device was manufactured.
  • Electroluminescent (EL) characteristics of the photoresearch company PR-650 were applied by applying a forward bias DC voltage to the organic light emitting diodes prepared according to Examples 1 to 25 and Comparative Examples 1 to 3 of the present invention.
  • the T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at 5000 cd / m 2 reference luminance. The measurement results are shown in Table 4 below.
  • the hexagonal rings contain N and the core elements are included in the hexagonal rings than in the case of Comparative Compounds 2 to 4, wherein the hexagonal and pentagonal rings have the same key element as N. It can be seen that the compound of the present invention, which is a heteroatom type containing one of S, O, and CR'R ′′, exhibits higher efficiency and higher lifetime.
  • Comparative Compounds 2 to 4 which are NN-type six-membered heterocyclic compounds, are NN-type heterocyclic cores when the molecules are stacked, so that the intermolecular sequence is edge-to-face. It is believed to cause charge carrier mobility and low oxidative stability.
  • the heteroatoms in the cyclic compound since they have different heterocyclic cores, they have an antiparallelcofacial ⁇ -stacking structure in which the packing structure of the molecules faces in the reverse direction. This makes the arrangement order between molecules into face-to-face shape and due to the steric effect of Ar 1 of asymmetrically arranged heteroatoms N which is the cause of the stacked structure, it is considered to have a high efficiency due to the high carrier mobility. In addition, it has a high oxidative stability and is believed to significantly increase the lifespan.
  • the compound of the present invention that contains N in the hexagonal ring has a more suitable form to accommodate both holes and electrons more stably than Comparative Compound 3, which is a case where N is included in the pentagonal ring. It is judged that the light emission efficiency and lifespan are increased.
  • An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention as a light emitting host material of a light emitting layer.
  • a 2-TNATA film is vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm.
  • the NPD film is vacuum-deposited at a thickness of 60 nm as a hole transport compound on the hole injection layer.
  • a transport layer was formed.
  • Compound P 1-9 of the present invention was used as a host on the hole transport layer, and a light emitting layer was deposited to a thickness of 30 nm by doping a (piq) 2 Ir (acac) at a weight ratio of 95: 5 with a dopant material. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm using a hole blocking layer, and Alq 3 was formed to a thickness of 40 nm using an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to prepare an organic light emitting diode.
  • LiF which is an alkali metal halide
  • An organic light emitting diode was manufactured according to the same method as Example 26 except for using the compound of the present invention shown in Table 5 below instead of the compound P 1-9 according to Example 26 of the present invention as a red host material of the emission layer. .
  • Comparative Compound 4 shown in Table 5 as a host material of the light emitting layer in the same manner as in Example 26 except that An organic light emitting device was manufactured by the method.
  • the electroluminescence (EL) characteristics of the photoresearch company PR-650 were applied by applying a forward bias DC voltage to the organic light emitting diodes manufactured according to Examples 26 to 50 and Comparative Examples 4 to 6.
  • the T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at 2500 cd / m 2 reference luminance. The measurement results are shown in Table 5 below.
  • the device using the compound according to an embodiment of the present invention as a phosphorescent red host material of the light emitting layer is significantly improved luminous efficiency and lifetime than Comparative Compound 1 and Comparative Compounds 5 to 9 It was confirmed.
  • the heterocyclic atoms in the ring compound have heterocyclic heterocyclic cores and the structure in which the hexagonal ring contains N is used not only in the light emitting layer (used as a host) but also in the red organic light emitting element (used as a host). It can be seen that it acts as a major factor in improving device performance.
  • the compound of the present invention used as a host material in the light emitting layer has high oxidative stability and high charge carrier mobility to achieve more effective charge balance.
  • the introduction of specific substituents, such as benzofuropyrimidine, exhibits the appropriate conformation to accommodate both holes and electrons, and at the same time has an appropriate T1 value to facilitate charge transfer from the host to the dopant. It can be seen that it shows the best device results in luminous efficiency and lifetime.
  • An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention as a hole transport material.
  • a 2-TNATA film is vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and then Compound P-40 of the present invention on the hole injection layer has a thickness of 60 nm.
  • Vacuum deposition was performed to form a hole transport layer.
  • 4,4'-N, N'-dicarbazole-biphenyl (hereinafter abbreviated as “CBP”) was used as a host on the hole transport layer, and dopant was doped with Ir (ppy) 3 in a 90:10 weight ratio.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • a light emitting layer was deposited to a thickness of 30 nm. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm using a hole blocking layer, and Alq 3 was formed to a thickness of 40 nm using an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to use an organic light emitting diode.
  • LiF which is an alkali metal halide
  • An organic light emitting diode was manufactured according to the same method as Example 51 except for using the compound of the present invention shown in Table 6 instead of the compound P 1-40 according to Example 51 of the present invention as a hole transport layer material.
  • An organic light emitting diode was manufactured according to the same method as Example 51 except for using Comparative Compound 6 shown in Table 6 below instead of Compound P 1-00 according to Example 51 of the present invention as a hole transport layer material.
  • Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic light emitting diodes prepared in Examples 51 to 71 and Comparative Example 7 of the present invention. Measurement Results The T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at 5000 cd / m 2 reference luminance, and the measurement results are shown in Table 6 below.
  • This result has a deep HOMO energy level and a high T1 value, which are inherent characteristics of the compound of the present invention, which improves the ability to block electrons and simultaneously transports holes to the light emitting layer. It is believed that the efficiency is improved while being more easily generated within. In addition, it has a high thermal stability it can be seen that the life is extended.
  • the amine group (-L a -N (R a ) (R b )) in the same heterocyclic ring as the compound of the present invention It can be seen that the band gap, electrical characteristics, and interface characteristics can be greatly changed by the introduction, which can be seen as a major factor in improving device performance.
  • the hole transport layer it is necessary to grasp the interrelationship with the light emitting layer (host), and even if a similar core is used, it will be very difficult even for a person skilled in the art to infer the characteristics shown in the hole transport layer in which the compound of the present invention is used.
  • the evaluation results of the above-described device fabrication described the device characteristics of applying the compound of the present invention to the light emitting layer and the hole transporting material as a host material, but the compound of the present invention is applied to the hole injection layer, the light emitting auxiliary layer, the electron transporting layer, The electron injection layer, the light emitting auxiliary layer and the like can be applied to all other layers.

Abstract

L'invention concerne un composé capable d'augmenter l'efficacité d'émission élevée, la faible tension d'attaque et la durée de vie d'un élément ; un élément électrique organique utilisant ce composé ; et un dispositif électronique associé.
PCT/KR2016/013255 2015-11-17 2016-11-17 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé WO2017086706A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2015-0160797 2015-11-17
KR1020150160797A KR102469742B1 (ko) 2015-11-17 2015-11-17 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Publications (1)

Publication Number Publication Date
WO2017086706A1 true WO2017086706A1 (fr) 2017-05-26

Family

ID=58717521

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2016/013255 WO2017086706A1 (fr) 2015-11-17 2016-11-17 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé

Country Status (2)

Country Link
KR (1) KR102469742B1 (fr)
WO (1) WO2017086706A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109749735A (zh) * 2017-11-08 2019-05-14 Sfc株式会社 胺取代的萘衍生物和包含其的有机发光二极管
CN110526896A (zh) * 2018-05-25 2019-12-03 北京鼎材科技有限公司 一种发光材料及应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102607419B1 (ko) * 2016-02-16 2023-11-30 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN109824522A (zh) * 2019-03-29 2019-05-31 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080145708A1 (en) * 2005-04-14 2008-06-19 Merck Patent Gmbh Compounds For Organic Electronic Devices
US20080193797A1 (en) * 2005-08-26 2008-08-14 Merck Patent Gmbh Novel Materials for Organic Electroluminescent Devices
KR20100007780A (ko) * 2008-07-14 2010-01-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광 소자
WO2013100497A1 (fr) * 2011-12-28 2013-07-04 주식회사 두산 Composé organique électroluminescent, et dispositif organique électroluminescent utilisant le composé
KR20150065383A (ko) * 2013-12-05 2015-06-15 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080145708A1 (en) * 2005-04-14 2008-06-19 Merck Patent Gmbh Compounds For Organic Electronic Devices
US20080193797A1 (en) * 2005-08-26 2008-08-14 Merck Patent Gmbh Novel Materials for Organic Electroluminescent Devices
KR20100007780A (ko) * 2008-07-14 2010-01-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광 소자
WO2013100497A1 (fr) * 2011-12-28 2013-07-04 주식회사 두산 Composé organique électroluminescent, et dispositif organique électroluminescent utilisant le composé
KR20150065383A (ko) * 2013-12-05 2015-06-15 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109749735A (zh) * 2017-11-08 2019-05-14 Sfc株式会社 胺取代的萘衍生物和包含其的有机发光二极管
CN110526896A (zh) * 2018-05-25 2019-12-03 北京鼎材科技有限公司 一种发光材料及应用
CN110526896B (zh) * 2018-05-25 2022-07-15 北京鼎材科技有限公司 一种发光材料及应用

Also Published As

Publication number Publication date
KR102469742B1 (ko) 2022-11-22
KR20170057544A (ko) 2017-05-25

Similar Documents

Publication Publication Date Title
WO2016167491A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et appareil électronique
WO2015182872A1 (fr) Composé pour élément électro-organique, et élément électro-organique et dispositif électronique utilisant celui-ci
WO2016190600A1 (fr) Composé pour élément électrique organique, élément électrique organique utilisant ce composé, et dispositif électronique correspondant
WO2015194791A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
WO2016148425A2 (fr) Composé pour dispositif électrique organique, dispositif électrique organique utilisant ce composé, et dispositif électronique correspondant
WO2016122150A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé
WO2017204557A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2016003225A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ledit composé et dispositif électronique comprenant ledit composé
WO2017095075A1 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et dispositif électronique associé
WO2017043835A1 (fr) Composé pour diode électronique organique, diode électronique organique utilisant celui-ci, et dispositif associé
WO2016200070A2 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit composé
WO2016175533A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique comprenant celui-ci
WO2016032150A2 (fr) Composé pour élément électrique organique, élément électrique organique utilisant ledit composé, et dispositif électronique comprenant ceux-ci
WO2015041428A1 (fr) Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé
WO2015178585A1 (fr) Composé pour dispositif électro-organique, dispositif électro-organique utilisant celui-ci, et dispositif électronique associé
WO2016003202A2 (fr) Composé pour élément électronique organique, élément électronique organique ayant recours à ce composé, et dispositif électronique comportant cet élément
WO2017030307A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et appareil électronique comprenant celui-ci
WO2015115756A1 (fr) Composé destiné à un élément électrique organique, élément électrique organique ayant recours à ce composé, et dispositif électronique correspondant
WO2020130392A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique
WO2014178532A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2014129764A1 (fr) Composé pour élément électronique organique, élément électronique organique employant le composé et dispositif électronique avec celui-ci
WO2017119654A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et appareil électronique correspondant
WO2016129861A1 (fr) Nouveau composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit composé
WO2017052099A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et dispositif électronique associé
WO2017135717A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique le comprenant

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: 16866658

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16866658

Country of ref document: EP

Kind code of ref document: A1