WO2020071720A1 - Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé - Google Patents

Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé

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WO2020071720A1
WO2020071720A1 PCT/KR2019/012795 KR2019012795W WO2020071720A1 WO 2020071720 A1 WO2020071720 A1 WO 2020071720A1 KR 2019012795 W KR2019012795 W KR 2019012795W WO 2020071720 A1 WO2020071720 A1 WO 2020071720A1
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문성윤
이형동
이범성
박정환
이윤석
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덕산네오룩스 주식회사
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    • 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
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
    • C07D517/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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 element, an organic electric element using the same, and an electronic device thereof.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on the function.
  • a difference in properties according to a material structure is very large, and thus, it is applied to various layers as a material for an organic electric device.
  • the band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. have different characteristics depending on the number of rings, fused positions, and types and arrangement of heteroatoms. This has been going on.
  • the LUMO and HOMO level of the host material are factors that greatly affect the efficiency and life of the organic electrical device, depending on whether electron and hole injection in the emitting layer can be efficiently controlled.
  • the charge balance in the light emitting layer, dopant quenching (quenching) and the efficiency of the light emission at the interface of the hole transport layer can be prevented from deteriorating.
  • TRTP PL lifetime
  • the TRTP (Time resolved transient PL) measurement method is a method of observing the decay time of the spectrum over time after irradiating a pulsed light source to the host thin film. It is a measurement method.
  • the TRTP measurement is a measurement method capable of distinguishing between fluorescence and phosphorescence, energy transfer method in mixed host material, exciplex energy transfer method, and TADF energy transfer method.
  • the present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent dopant-containing organic electroluminescent device containing a phosphorescent dopant and the efficiency, life span It is an object of the present invention to provide an organic electrical device using the compound and an electronic device thereof.
  • the present invention is to reduce the energy barrier between the light emitting layer and the adjacent layer by containing a specific first host material in combination with a specific first host material as a main component in order to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and high lifespan of the organic electric device.
  • the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer.
  • An organic electroluminescent device comprising a first host compound represented by (1) and a second host compound represented by formula (2).
  • the present invention provides an organic electric device using the compound represented by the above formulas and an electronic device thereof.
  • the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electric device, and also significantly improve the life of the device.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • organic electrical element 110 substrate
  • first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term.
  • a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected to or connected to the other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.
  • halo or halogen as used herein are fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise noted.
  • alkyl or "alkyl group” used in the present invention has a single bond of 1 to 60 carbon atoms, unless otherwise specified, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycle.
  • radicals of saturated aliphatic functional groups including alkyl groups, cycloalkyl-substituted alkyl groups.
  • haloalkyl group or "halogenalkyl group” as used in the present invention means an alkyl group substituted with halogen unless otherwise specified.
  • heteroalkyl group used in the present invention means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.
  • alkenyl group used in the present invention have a double or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include straight or branched chain groups. , But is not limited to this.
  • cycloalkyl means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, but is not limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and 2 to 60 unless otherwise specified. It has a carbon number, and is not limited thereto.
  • aryloxyl group or "aryloxy group” used in the present invention means an aryl group to which an oxygen radical is attached, and has a carbon number of 6 to 60 unless otherwise specified, and is not limited thereto.
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified.
  • an aryl group or an arylene group means a single ring or multi-ring aromatic, and includes an aromatic ring formed by adjacent substituents participating in a bond or reaction.
  • the aryl group may be a phenyl group, biphenyl group, fluorene group, dimethylfluorene group, diphenylfluorene group, or spirofluorene 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
  • a radical substituted with an aryl group has a carbon number described herein.
  • arylalkoxy group it means an alkoxy group substituted with an aryl group
  • alkoxycarbonyl group it means a carbonyl group substituted with an alkoxyl group
  • arylcarbonyl alkenyl group it means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means alkyl containing one or more heteroatoms, unless otherwise specified.
  • heteroaryl group or “heteroarylene group” means an aryl group or an arylene group having 2 to 60 carbon atoms each containing at least one heteroatom, unless otherwise specified, and is not limited thereto. No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional devices.
  • heterocyclic group used in the present invention includes at least one heteroatom, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, heteroaliphatic ring and hetero, unless otherwise specified. Aromatic rings. Adjacent functional groups may also be formed by bonding.
  • heteroatom refers to N, O, S, P or Si, unless otherwise stated.
  • heterocyclic group may include a ring containing SO 2 instead of carbon forming a ring.
  • heterocyclic group includes the following compounds.
  • aliphatic refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms or a combination thereof, and It contains a saturated or unsaturated ring.
  • hetero compounds or hetero radicals other than the above-described hetero compounds include one or more hetero atoms, but are not limited thereto.
  • carbonyl used in the present invention is represented by -COR ', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms. Is a 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 used in the present invention is represented by -RO-R ', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or 6 to 30 carbon atoms. It is an aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, 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 group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, substituted with deuterium C 6 ⁇ C 20 aryl group, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Means a group, a germanium group, and one or more substituents selected from the group consisting of C 2 to C 20 heterocyclic groups, and is not limited
  • the substituent R 1 means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring.
  • the formula or compound may be omitted.
  • a is an integer of 1
  • one substituent R 1 is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, each of them is bonded as follows, where R 1 may be the same or different from each other.
  • a is an integer of 4 to 6 it binds to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bound to the carbon forming the benzene ring is omitted.
  • the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer.
  • An organic electroluminescent device comprising a first host compound represented by (1) and a second host compound represented by formula (2).
  • X and Y are each independently O; S; CR'R “; SiR'R” or Se ;
  • a and b are each independently 0 or 1, provided that a + b is 1 or more,
  • R 'and R are each independently hydrogen; an alkyl group of C 1 to C 50 ; an aryl group of C 6 to C 60 ; and a heteroaryl group of C 2 to C 60 ; or R' And R "form a ring with each other to form a spiro ring,
  • L 1 , L 2 and L ' are each independently a single bond; C 6 ⁇ C 60 Arylene group; Or a C 2 ⁇ C 60 heteroarylene group; and
  • Ar 1 and Ar 2 are each independently hydrogen; heavy hydrogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-NR'R ";
  • Z is NR ', O, S, CR'R ", SiR'R", or Se,
  • R 1 to R 6 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,
  • R a and R b are independently of each other C 6 ⁇ C 60 aryl group; Fluorenyl group; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; And O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom; is selected from the group consisting of,
  • l, m, n, o, p, and q are 2 or more, they are the same as or different from each other, and a plurality of R 1 , a plurality of R 2 , a plurality of R 3 , a plurality of R 4 , and a plurality of R 5 to each other, a plurality of R 6 to each other can be combined to form an aromatic and heteroaromatic ring,
  • the A and B rings are each independently an aryl group of C 6 to C 60 or a heteroaryl group of C 2 to C 60 , and one of A and B is an aryl group of C 10 to C 60 ,
  • n, l, p and q are any integers from 0 to 4, m is 0 or 1, o is any integer from 0 to 3,
  • the compound represented by the formula (1) in the present invention provides an organic electric device comprising a compound represented by the following formula (3) or (4).
  • the present invention provides an organic electric device in which the compound represented by the formula (1) includes a compound represented by any one of the following formulas (5) to (12).
  • the present invention provides an organic electric device including a compound in which all of l, m, n, o and p are 0 in the formula (1).
  • any one of the R 1 , R 2 , R 3 , R 4 and R 5 is an organic electric device comprising a compound in which a pair of neighboring pairs to each other to form a ring
  • the present invention in the formula (1), provides an organic electric device comprising a compound of S or O.
  • the formula (1) in the present invention includes the following compound.
  • the present invention provides an organic electric device in which the compound represented by the formula (2) includes a compound represented by the following formula (13) or (14).
  • the present invention provides an organic electric device comprising a compound represented by any one of the following (A-1) to (A-9) of the A and B rings of the compound represented by the formula (2).
  • R 10 is the same as R 1 above,
  • the present invention includes compounds represented by any one of the following formulas (15) to (28).
  • R 12 and R 13 are the same as R 1 defined above,
  • s and u are each independently an integer from 0 to 6
  • t is an integer from 0 to 4,
  • v and w are each independently an integer of 0 to 8.
  • the present invention provides an organic electric device comprising a compound in which R 6 of the compound represented by the formula (2) is hydrogen.
  • the formula (2) in the present invention includes the following compound.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180 and a first electrode 120 and a second electrode formed on the substrate 110. Between (180) it is provided with an organic layer containing the compound represented by the formula (1) and (2).
  • 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 material layer sequentially comprises a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, a light emitting auxiliary layer 151, an electron transport layer 160 and an electron injection layer 170 on the first electrode 120. It can contain. At this time, layers other than the emission layer 150 may not be formed.
  • a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc. may also serve as a hole blocking layer.
  • the organic electric device according to the present invention may further include a protective layer formed on one surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.
  • the compound containing Formula 1 of the present invention may be used as a material for the light efficiency improving layer or the protective layer.
  • the band gap, electrical properties, and interfacial properties may vary depending on which substituents are attached to which positions, so the selection of the core and the combination of sub-substituents coupled thereto are also very good. It is important, especially when the energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.
  • the organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method.
  • PVD physical vapor deposition
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer 160 are formed thereon.
  • After forming an organic material layer including the electron injection layer 170 it can be manufactured by depositing a material that can be used as a cathode thereon.
  • the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150
  • the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
  • the present invention provides a compound represented by the formula (1) and the formula (2) in an ratio of any one of 1: 9 to 9: 1 to provide an organic electric device included in the light emitting layer, preferably Is 1: 9 to 5: 5, more preferably mixed in a ratio of 2: 8 to 3: 7 and included in the light emitting layer.
  • the present invention further comprises a light efficiency improving layer formed on at least one of 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 from one side of the first electrode in the organic electric device.
  • a light efficiency improving layer formed on at least one of 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 from one side of the first electrode in the organic electric device.
  • the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, and the organic material layer according to the present invention can be formed by various methods Therefore, the scope of the present invention is not limited by the forming method.
  • the organic electric device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • WOLED White Organic Light Emitting Device
  • RGB Red
  • Green Green
  • B Blue
  • the R, G, and B light emitting units are arranged in a mutually planar side-by-side manner, and the stacking method in which the R, G, and B light-emitting layers are stacked up and down.
  • CCM color conversion material
  • the present invention is a display device comprising the above-described organic electric device; And a control unit for driving the display device.
  • the present invention provides an electronic device characterized in that the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.
  • the compound represented by Chemical Formula (1) according to the present invention (final product 1) is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.
  • Sub 1 of Scheme 1 may be synthesized by the following Reaction Scheme 2, but is not limited thereto.
  • the compound belonging to Sub 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.
  • Sub 2 of Scheme 1 may be synthesized by the following Reaction Scheme 3, but is not limited thereto.
  • Sub 2-II-37 (23g, 89mmol), N-Bromosuccinimide (16g, 89mmol), and Methylene chloride (300mL) were synthesized using the synthesis method of Sub 2-III-1. 37 (21 g, 70%).
  • Sub 2-II-144 (30g, 89mmol), N-Bromosuccinimide (18.8 g, 105.9 mmol), Methylene chloride (318 mL) was synthesized using the synthesis method of Sub 2-III-1. -III-144 (18.24 g, 53%).
  • the compound belonging to Sub 2 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS value of the compound belonging to Sub 2.
  • the compound belonging to Sub 3 may be the following compound, but is not limited thereto, and Table 3 shows the FD-MS value of the compound belonging to Sub 3.
  • the compound represented by the formula (2) according to the present invention (final product 2) is prepared by reacting Sub 4 and Sub 5 as shown in Reaction Scheme 4.
  • Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 5 below, but is not limited thereto.
  • (A and B are as defined in the above formula 2)
  • Sub 4 examples are as follows, but are not limited thereto, and Table 5 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 4.
  • -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm.
  • NPB N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine
  • the hole blocking layer (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm.
  • an organic electroluminescent device was manufactured by depositing LiF, an alkali metal halide as an electron injection layer, to a thickness of 0.2 nm, and then depositing Al to a thickness of 150 nm to use as a cathode.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 2 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 and Comparative Compound 1 were used as a mixture.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 2 and Comparative Compound 2 or Comparative Compound 3 were used as a mixture.
  • the electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a direct bias DC voltage to the organic electroluminescent elements of the Examples and Comparative Examples prepared as described above, and the measurement result showed a luminance of 2500 cd / m2.
  • T95 life was measured by a life measurement equipment manufactured by Max Science. The following table shows the results of device fabrication and evaluation.
  • Comparative Examples 8 to 10 used as a phosphorescent host by mixing Comparative Compound 1 or Comparative Compound 2 rather than (Comparative Examples 1 to 7)
  • the results were generally excellent in terms of efficiency and life, rather than Examples 1 to 18 in which the compounds of the present invention represented by Formula 1 and Formula 2 were mixed show remarkably excellent effects in terms of driving voltage, efficiency and life. Able to know.
  • the present inventors determined that the substance of the substance of Formula 1 and the substance of Formula 2 has new characteristics other than the characteristics of the substance, respectively, and the substance of Formula 1 and the substance of Formula 2 , PL and PL lifetime were measured using the mixture of the present invention, respectively.
  • the compounds of the present invention, Formula 1 and Formula 2 were mixed, it was confirmed that a new PL wavelength was formed unlike that of a single compound, and the decrease and extinction time of the newly formed PL wavelength was determined for each of Formula 1 and Formula 2 materials. It was confirmed that it was increased than the reduction and extinction time.
  • the compound of the present invention When the compound of the present invention is used in combination, not only electrons and holes are moved through the energy level of each substance, but also electrons, hole movement or energy due to exciplex of new regions having new energy levels formed due to mixing. It is judged that the efficiency and life of the furnace are increased. As a result, when using the mixture of the present invention, it can be said that the mixed thin film is an important example of exciplex energy transfer and luminescence processes.
  • the reason why the combination of the present invention is superior to Comparative Examples 8 to 10 used as a phosphorescent host mixed with a comparative compound is not only electron but also a polycyclic ring compound represented by Chemical Formula 2, which is characterized by high hole stability and high T1.
  • the compound represented by Chemical Formula 1 having strong hole characteristics is mixed, the electron blocking ability is improved due to the high T1 and high LUMO energy values, and more holes move quickly and easily in the light emitting layer.
  • the mixture of the compounds of the present invention was measured by fabricating the device by ratio (2: 8, 3: 7, 4: 6).
  • the present invention it is possible to manufacture an organic device having excellent device characteristics of high brightness, high light emission and high life, and thus there is industrial applicability.

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

Abstract

La présente invention concerne : un nouveau mélange capable d'améliorer l'efficacité d'émission de lumière, la stabilité et la durée de vie d'un élément ; un élément électrique organique utilisant ledit mélange et un dispositif électronique correspondant.
PCT/KR2019/012795 2018-10-01 2019-10-01 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé WO2020071720A1 (fr)

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CN113801057B (zh) * 2021-08-13 2023-04-18 浙江大学 䓛基氮杂[7]螺烯类化合物、制备方法及应用
CN115636823B (zh) * 2022-10-18 2024-05-28 上海和辉光电股份有限公司 一种有机电致发光化合物及其应用

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