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WO2016003225A2 - Composé pour élément électronique organique, élément électronique organique utilisant ledit composé et dispositif électronique comprenant ledit composé - Google Patents

Composé pour élément électronique organique, élément électronique organique utilisant ledit composé et dispositif électronique comprenant ledit composé Download PDF

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WO2016003225A2
WO2016003225A2 PCT/KR2015/006840 KR2015006840W WO2016003225A2 WO 2016003225 A2 WO2016003225 A2 WO 2016003225A2 KR 2015006840 W KR2015006840 W KR 2015006840W WO 2016003225 A2 WO2016003225 A2 WO 2016003225A2
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group
layer
ring
aryl
organic
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WO2016003225A3 (fr
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박종광
박형근
조혜민
이대원
최연희
이학영
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덕산네오룩스 주식회사
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Publication of WO2016003225A2 publication Critical patent/WO2016003225A2/fr
Publication of WO2016003225A3 publication Critical patent/WO2016003225A3/fr

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    • 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
    • C07D403/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

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 light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. have.
  • the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
  • Efficiency, lifespan, and driving voltage are related to each other, and as the efficiency increases, the driving voltage decreases relatively, and the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases.
  • the lifespan tends to increase.
  • the electron transport material has high temperature stability and high electron mobility (within the full device blue device driving voltage range) and improves the hole blocking ability with a high T 1 value. Need development ( Adv. Funct. Mater. 2013, 23 , 1323)
  • a light emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer, and the light emitting auxiliary layer has a high hole mobility and high T 1 to have a suitable driving voltage. Materials with values and wide bandgaps should be used.
  • a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc.
  • Supported by an efficient material should be preceded, and in particular, there is an urgent need to develop a material that can effectively achieve a charge balance through a combination of materials such as an electron transport layer, a hole transport layer, and a light emitting auxiliary layer.
  • An object of the present invention is to provide a compound capable of improving the luminous efficiency, stability and lifetime of the device, an organic electric device using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • first, second, A, B, (a), and (b) can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be “connected”, “coupled” or “connected”.
  • a component such as a layer, film, region, plate, etc.
  • it is not only when the other component is “on top of” but also another component in between. It is to be understood that this may also include cases.
  • a component is said to be “directly above” another part, it should be understood to mean that there is no other part in the middle.
  • 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.
  • 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.
  • alkoxy group or "alkyloxy group” means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, but is not limited thereto.
  • 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.
  • fluorenyl group or “fluorenylene group” means a monovalent or divalent functional group in which R, R 'and R “are all hydrogen in the following structures, unless otherwise stated, and" Substituted fluorenyl group “or” substituted fluorenylene group “means that at least one of the substituents R, R ', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a carbon It includes the case of forming a compound by spying together.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • the aryl group or arylene group in the present invention includes monocyclic, ring conjugate, conjugated ring system, spiro compound and the like.
  • heterocyclic group includes not only aromatic rings, such as “heteroaryl groups” or “heteroarylene groups,” but also non-aromatic rings, and unless otherwise specified, each carbon number includes one or more heteroatoms. It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom refers to N, O, S, P or Si unless otherwise indicated, and heterocyclic groups are monocyclic, ring conjugates, conjugated multiple ring systems, spies, including heteroatoms. Means a compound or the like.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • ring includes monocyclic and polycyclic rings, includes hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and nonaromatic rings.
  • polycyclic includes ring assemblies, fused multiple ring systems and spiro compounds, such as biphenyl, terphenyl, and the like, including aromatics as well as nonaromatics, hydrocarbons
  • the ring as well includes heterocycles comprising at least one heteroatom.
  • ring assemblies means that two or more ring systems (single or conjugated ring systems) are directly connected to each other through a single bond or a double bond and directly between such rings. It means that the number of linkages is one less than the total number of ring systems in this compound. Ring aggregates may have the same or different ring systems directly connected to each other via a single bond or a double bond.
  • conjugated multiple ring systems refers to fused ring forms that share at least two atoms, including the ring systems of two or more hydrocarbons joined together and at least one heteroatom. And heterocyclic systems having at least one conjugated form. These conjugated several ring systems can be aromatic rings, heteroaromatic rings, aliphatic rings or combinations of these rings.
  • spiro compound has a "spiro union", and a spiro linkage means a linkage formed by two rings sharing one atom only.
  • atoms shared by the two rings are called spiro atoms, and according to the number of spiro atoms in a compound, they are respectively referred to as 'monospyro-', 'diespyro-' and 'trispyro-' It is called a compound.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group
  • an alkenyl group substituted with an arylcarbonyl group is used herein.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • substituted in the term “substituted or unsubstituted” refers to deuterium, halogen, amino groups, nitrile groups, nitro groups, C 1 -C 20 alkyl groups, C 1 -C 20 alkoxy 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 aryl group substituted with a heavy hydrogen, C 8 -C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 -C 20 heterocyclic group means one or more substituents selected from the group consisting of, without being limited to these
  • 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 120, 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 least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like.
  • the electron transport layer 160 may serve as a hole blocking layer. You can do it.
  • 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
  • Compound according to the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting layer 150, light efficiency improvement layer, light emitting auxiliary layer, etc. It can be used as a material. In one example, the compound of the present invention may be used as a material for the hole transport layer 140, the light emitting auxiliary layer 151 and / or the electron transport layer 160.
  • the band gap, the electrical properties, and the interfacial properties may vary depending on which substituents are bonded at which positions, and therefore, the selection of the cores and the combination of sub substituents bonded thereto are very important. Long life and high efficiency can be achieved at the same time when an optimal combination of energy level, T 1 value, and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.
  • a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and correspond to each light emitting layer (R, G, B). Therefore, it is necessary to form different emission auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.
  • the energy level between each organic material layer is formed by forming an electron transport layer using a compound according to Formula 1 or 1a of the present invention, and / or forming a hole transport layer and / or a light emitting auxiliary layer of the compound according to Formula 2 of the present invention.
  • T 1 values and the intrinsic properties (mobility, interfacial properties, etc.) of the material can be optimized to improve the lifetime and efficiency of the organic electronic device.
  • the organic electroluminescent device according to an embodiment of the present invention may be manufactured using a deposition method, for example, each layer may be formed using a deposition method such as PVD, CVD, or the like.
  • the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130 and the hole transport layer 140 thereon. ), And an organic material layer including the emission layer 150, the electron transport layer 160, and the electron injection layer 170, and then deposit a material that can be used as the cathode 180 thereon.
  • the organic layer may be formed using a variety of polymer materials, such as a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, It can be produced in fewer layers by a method such as a screen printing process or a 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 electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • 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.
  • Ar 1 and R 1 are independently of each other an aryl group or fluorenyl group of C 6 -C 24 , m is an integer of 0-4, and when m is 2 or more, R 1 is the same or different from each other.
  • Ar 1 may be a substituted or unsubstituted C 6 -C 18 aryl group, and also preferably substituted or unsubstituted C 6 , C 10 , C 12 , C 14 , C 15 , C 16 or It may be a C 18 aryl group, and also preferably a phenyl group unsubstituted or substituted with methyl or deuterium, a biphenylyl group, naphthyl group, m- or p -terphenylyl group, anthryl group, unsubstituted or substituted with deuterium, Phenanthryl group, pyrenyl group or 9,9-dimethyl-9 H -fluorenyl group.
  • m may be 0 to 2
  • R 1 may be a phenyl group.
  • Ar 1 and R 1 are an aryl group or fluorenyl group, they are deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, alkyl group of C 1 -C 20 Substituted with C 1 -C 20 alkoxy group, C 1 -C 20 alkyl group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 6 -C 20 aryl group, deuterium C 2 -C 20 heterocyclic group, C 3 -C 20 containing at least one heteroatom selected from the group consisting of C 6 -C 20 aryl, fluorenyl, O, N, S, Si and P It may optionally be further substituted with one or more substituents selected from the group consisting of a cycloalkyl group of, a C 7 -C 20 arylalkyl group, and a C 8 -C 20
  • L 1 is a single bond, a C 6 -C 60 arylene group, a fluorenylene group, C 2 -containing at least one hetero atom selected from the group consisting of O, N, S, Si and P It may be selected from the group consisting of C 60 heterocyclic group, C 3 -C 60 aliphatic ring and C 6 -C 60 aromatic ring, and combinations thereof.
  • L 1 may be an aryl group of C 1 -C 18 , a heterocyclic group of C 5 -C 13 , or a combination thereof, and preferably, among those represented by the following L-1 to L-8 It can be one.
  • Q 1 to Q 3 are each independently CR a or N, Q 4 is S, O or CR b R c to be.
  • R a , R b and R c each independently include at least one heteroatom selected from the group consisting of hydrogen, an aryl group of C 6 -C 60 , a fluorenyl group, O, N, S, Si and P C 2 -C 60 heterocyclic group, C 3 -C 60 alicyclic ring and C 6 -C 60 aromatic ring fused ring group, C 1 -C 50 Alkyl group, C 2 -C 20 Alkenyl group, An alkynyl group of C 2 -C 20 , an alkoxy group of C 1 -C 30 , and an aryloxy group of C 6 -C 30 .
  • L 1 is a phenylene group, naphthylene group, biphenylene group, anthylene group, phenanthryl group, triphenyleneylene group, pyrenylene group, pyridylene group, quinolylene group unsubstituted or substituted with methyl.
  • L 1 is heavy hydrogen, a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, an alkylthio import of C 1 -C 20, alkoxy group of C 1 -C 20, C 1 alkyl group -C 20, C 2 -C 20 alkene group, an aryl group of C 6 -C 20 substituted alkynyl, aryl, C 6 -C 20 heavy hydrogen of the C 2 -C 20, fluorene group, O, N, S, Si, and the heterocyclic group of C 2 -C 20 containing at least one heteroatom selected from the group consisting of P, a cycloalkyl group of C 3 -C 20, arylalkyl groups, C 7 -C 20, And one or more substituents selected from the group consisting of C 8 -C 20 arylalkenyl groups.
  • R 2 and R 3 are independently a C 6 -C 60 aryl group, fluorenyl group, O, N, S, C 2 -C 60 containing at least one heteroatom selected from the group consisting of Si and P to each other It may be selected from the group consisting of a heterocyclic group, a fused ring group of C 3 -C 60 aliphatic ring and C 6 -C 60 aromatic ring, and combinations thereof.
  • R 2 and R 3 or It may be, and may also preferably be one of those represented by the following A-1 to A-23.
  • R 12 and R 13 are each independently i) at least one heteroatom selected from the group consisting of deuterium, halogen, C 6 -C 60 aryl group, fluorenyl group, O, N, S, Si and P C 2 -C 60 heterocyclic group containing, 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 Alkene Diary, C 2 -C 20 alkynyl group, C 1 -C 30 alkoxy group, and C 6 -C 30 aryloxy group, or ii) adjacent groups are bonded to each other at least one ring
  • R 12 and R 13 which do not form a ring are the same as defined in i) above.
  • the ring formed at this time may be monocyclic or polycyclic.
  • n and o are each independently an integer of 0 to 5, when n is an integer of 2 or more, R 12 is the same or different from each other, when o is an integer of 2 or more, R 13 may be the same or different from each other.
  • the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group of R 12 and R 13 are independently of each other deuterium, halogen, silane group, siloxane group, boron group, a germanium group, a cyano group, a nitro group, C 1 -C 20 coming of the alkylthio, C 1 -C 20 alkoxy group, C 1 -C 20 alkyl, C 2 -C 20 alkenyl group of, C 2 a -C 20 alkynyl, C 6 -C 20 aryl group, of a C 6 -C 20 aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, at least one selected from the group consisting of Si and P of At least one selected from the group consisting of a C 2 -C 20 heterocyclic group, a C 3 -C 20
  • Formula 1 may be represented by the following Formula 1a or 1b.
  • R 12 and R 13 independently of each other i) at least one heteroatom selected from the group consisting of deuterium, halogen, C 6 -C 60 aryl group, fluorenyl group, O, N, S, Si and P C 2 -C 60 heterocyclic group, C 3 -C 60 alicyclic 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, and C 6 -C 30 aryloxy group, or ii) adjacent groups are bonded to each other at least one monocyclic or May form a polycyclic ring, wherein R 12 and R 13 which do not form a ring are the same as defined in i), n and o are each independently an integer of 0 to 5 and n is an integer of 2 or more.
  • R 12 is the same as or different from each other, and
  • the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group of R 12 and R 13 are independently of each other deuterium, halogen, silane group, siloxane group, boron group, a germanium group, a cyano group, a nitro group, C 1 -C 20 coming of the alkylthio, C 1 -C 20 alkoxy group, C 1 -C 20 alkyl, C 2 -C 20 alkenyl group of, C 2 a -C 20 alkynyl, C 6 -C 20 aryl group, of a C 6 -C 20 aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, at least one selected from the group consisting of Si and P of At least one selected from the group consisting of a C 2 -C 20 heterocyclic group, a C 3 -C 20
  • Chemical Formula 2 preferably, in Chemical Formula 2, or May be one of those represented by A-1 to A-23.
  • the compound represented by Formula 1, 1a or 1b may be one of the following compounds.
  • the present invention provides a compound for an organic electric device represented by Formula 1, Formula 1a, or Formula 1b.
  • the present invention provides an organic electric device containing the compound represented by Formula 1, Formula 1a or Formula 1b.
  • 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, Chemical Formula 1a, or Chemical Formula 1b, and may be represented by Chemical Formula 1, Chemical Formula 1a, or Chemical Formula 1b.
  • the compound to be displayed may be contained in at least one of the electron transport layer and the light emitting layer of the organic material layer. That is, the compound represented by the formula (1), (1a) or (1b) may be used as the material of the electron transport layer or the light emitting layer.
  • an organic electroluminescent device including one of the compounds 1-1 to 1-88 is provided in an organic material layer.
  • the compound contained in the organic material layer may be one kind alone or a mixture of two or more represented by Formula 1, Formula 1a, or Formula 1b.
  • the electron transport layer or the light emitting layer of the organic material layer may be formed of Compound 1-1 alone, or may be formed of a mixture of Compound 1-1 and Compound 1-2.
  • the organic material layer of the present invention includes an electron transport layer, a light emitting layer, a light emitting auxiliary layer and a hole transport layer, the light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer, the electron transport layer is the formula 1, 1a or a compound represented by Formula 1b, and at least one of the hole transport layer and the light emitting auxiliary layer contains a compound represented by Formula 2 independently of each other.
  • Ar 2 and Ar 3 independently of each other C 6 -C 60 containing at least one heteroatom selected from the group consisting of an aryl group, fluorenyl group, O, N, S, Si and P Heterocyclic group of 2 -C 60 , fused ring of C 3 -C 60 aliphatic ring and C 6 -C 60 aromatic ring, C 1 -C 50 alkyl group, C 2 -C 20 alkenyl group, C 2 An alkynyl group of -C 20 , an alkoxy group of C 1 -C 30 , and an aryloxy group of C 6 -C 30 .
  • Ar 4 is a C 6 -C 30 aryl group, the formula (2a) or formula (2b).
  • X is NR d , O, S, or CR e R f , wherein R d to R f are independently of each other an C 6 -C 60 aryl group, fluorenyl group, O, N, S, Si, and group of C 2 -C 60 containing at least one heteroatom selected from the group consisting of P heterocycle groups fused ring of an aromatic ring of C 3 -C 60 aliphatic ring with C 6 -C 60, alkyl group of C 1 -C 50, C 2 -C 20 alkenyl group, an alkoxy group of C 2 -C 20 alkynyl, C 1 -C 30 a, and C 6 are each individually selected from the group consisting of aryloxy groups -C 30 of , R e and R f may be bonded to each other to form a spiro compound.
  • L 2 is a single bond, C 6 -C 60 aryl group, a fluorenyl group, O, N, S, C 2 -C 60 containing at least one heteroatom selected from the group consisting of Si and P Heterocyclic group, a fused ring group of C 3 -C 60 aliphatic ring and C 6 -C 60 aromatic ring, and combinations thereof
  • L 3 is an arylene group of C 6 -C 60 , A fluorenylene group, a C 2 -C 60 heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P, an aliphatic ring of C 3 -C 60 and C 6- It may be selected from the group consisting of a fused ring group of C 60 aromatic ring, and combinations thereof.
  • L 2 and L 3 are independently of each other deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C 1 -C 20 alkylthio group, C 1 -C 20 Alkoxy group, C 1 -C 20 alkyl group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 6 -C 20 aryl group, C 6 -C 20 aryl substituted with deuterium C 2 -C 20 heterocyclic group, C 3 -C 20 cycloalkyl group, C 7 -containing at least one heteroatom selected from the group consisting of a group, a fluorenyl group, O, N, S, Si and P
  • substituents selected from the group consisting of C 20 arylalkyl groups, and C 8 -C 20 arylalkenyl groups
  • R 4 to R 7 are i) independently of each other deuterium, tritium, halogen, C 6 -C 60 aryl group, fluorenyl group, O, N, S, Si and P C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of, C 3 -C 60 aliphatic ring and C 6 -C 60 aromatic ring fused ring group, C 1 -C 50
  • An alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxy group, and a C 6 -C 30 aryloxy group, or ii) neighboring Groups combine with each other to form at least one ring, wherein the groups that do not form a ring are the same as defined in i) above, p, r and s are each an integer of 0 to 4, q is 0 to 3
  • Ar 2 to Ar 4 , R 4 to R 7 are each an aryl group
  • Ar 2 , Ar 3 , R 4 to R 7 are each a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group , Alkynyl group, alkoxy group or aryloxy group, each of them independently of each other deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C 1 -C 20 alkylthio group, C 1 -C 20 alkoxy group, C 1 -C 20 alkyl group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 6 -C 20 aryl group, deuterium substituted C 6 aryl groups -C 20, fluorene group, O, N, S, Si, and group of C 2 -C 20 containing at least one heteroatom
  • Formula 2 may be one of the following compounds.
  • the compounds disclosed in Korean Patent Nos. 10-1251451 and 10-1298483 may be used as carbazole derivatives or arylamine derivative compounds contained in the hole transport layer or the light emitting auxiliary layer.
  • the organic layer may be formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process.
  • 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.
  • the light efficiency improving layer may include a compound represented by Formula 2.
  • the present invention provides an electronic device including a display device including an organic electric element including an organic material layer containing a compound according to the present invention, and a control unit for controlling the display device.
  • the organic electroluminescent element may be one of an organic electroluminescent element, an organic solar cell, an organic photoconductor, an organic transistor, and a single color or white light emitting element.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • the compound belonging to Sub 1 may be the following compound, but is not limited thereto.
  • Table 1 shows FD-MS values of compounds belonging to Sub 1.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 7, but is not limited thereto.
  • Sub 2 of Scheme 1 may be more specifically synthesized by the reaction route of Scheme 7a or 7b, but is not limited thereto.
  • Sub 2-I-40 (using beta-Aminoatroponitrile (CAS: 33201-99-9) from BOC Sciences) (13.22 g, 0.0917 mol) N, N-dimethylbenzamide (15.05 g, 0.1009 mol), POCl 3 (170ml)
  • the Sub 2-1 synthesis was carried out to obtain 12.23 g (yield: 50%) of the product.
  • the compound belonging to Sub 2 may be the following compound, but is not limited thereto.
  • Table 2 shows FD-MS values of compounds belonging to Sub 2.
  • Sub 1-46 (8 g, 0.0137 mol) obtained in the synthesis above, Sub 2-3 (4.69 g, 0.0137 mmol), Pd (PPh 3 ) 4 (0.63 g, 0.0005 mol), NaOH (1.64 g, 0.0411 mol), THF (80 ml), H 2 O (40 ml) were obtained using the Product 1-1 synthesis method to obtain 6.7 g (yield: 64%) of the product.
  • N -([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9 H -fluoren-2-amine (16.32 g, 45.1 mmol) was added to a round bottom flask and dissolved in toluene (500 ml). Later, 3- (4-bromophenyl) -9-phenyl-9 H -carbazole (21.58 g, 54.2 mmol), Pd 2 (dba) 3 (1.24 g, 1.4 mmol), 50% P ( t -Bu) 3 ( 1.8 ml, 3.6 mmol), NaO t -Bu (13.02 g, 135.4 mmol) were added and stirred at 100 ° C.
  • Example I-1 red organic electroluminescent device (electron transport layer)
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as an electron transport layer material.
  • To form a hole injection layer and then vacuum 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as "NPD”) to a thickness of 60 nm on the hole injection layer. It was deposited to form a hole transport layer.
  • NPD 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • (piq) bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate
  • (piq) bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate
  • 2 Ir (acac) ′′) was doped in a 95: 5 weight ratio to deposit a 30 nm thick light emitting layer.
  • (1,1'bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum hereinafter abbreviated as "BAlq" was vacuum-deposited on the emission layer to a thickness of 10 nm.
  • a hole blocking layer was formed, and the electron transport layer was formed by vacuum depositing Compound 1-1 of the present invention on the hole blocking layer to a thickness of 40 nm. Thereafter, LiF, which is a halogenated alkali metal, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form an organic electroluminescent device.
  • LiF which is a halogenated alkali metal
  • An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that the compound of the present invention shown in Table 5 was used instead of the compound 1-1 of the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compound 1 was used instead of Compound 1-1 of the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compound 2 was used instead of Compound 1-1 of the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compound 3 was used instead of Compound 1-1 of the present invention as an electron transport layer material.
  • Electroluminescence with photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples I-1 to I-74 and Comparative Examples 1 to 3 of the present invention (EL) characteristics were measured and the T95 life was measured using a life measurement instrument manufactured by McScience at 2500 cd / m 2 reference brightness. The measurement results are shown in Table 5 below.
  • the compound of the present invention When the compound of the present invention is used as an electron transporting layer, it has a higher T 1 value than the dopant, so the efficiency of the exciton stays in the light emitting layer is relatively increased. As a result, the driving voltage is lowered, and the high T 1 value can reduce the flow of holes.
  • Comparative Compounds 2 and 3 containing similar quinazolines similar to the compounds of the present invention appear to have lower LUMO values than the compounds of the present invention. This means that the compound of the present invention can transfer electrons into the light emitting layer more easily and quickly than the comparative compound 2 and the comparative compound 3, and thus, the charge balance in the light emitting layer is increased, and as a result, the efficiency increases.
  • the compound of the present invention used as the electron transport layer was found to have a higher T 1 value as the structure becomes a more twisted structure when introducing a phenyl group bent to the linking group L 1 .
  • Example II-1 Red organic electroluminescent device (electron transport layer, hole transport layer)
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as an electron transport layer material.
  • 2-TNATA is vacuum deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate to form a hole injection layer
  • Compound 2-5 of the present invention is vacuum deposited to a thickness of 60 nm on the hole injection layer.
  • a hole transport layer was formed.
  • a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping CBP with a host material and (piq) 2 Ir (acac) with a dopant material at a 95: 5 weight ratio.
  • BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer
  • Compound 1-1 of the present invention was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • LiF which is a halogenated alkali metal
  • Al was deposited to a thickness of 150 nm to form an organic electroluminescent device.
  • Example II-2 to [ Example II-6] Red Organic Electroluminescent Device ( Electron Transport Layer , Hole Transport Layer)
  • An organic electroluminescent device was manufactured in the same manner as in Example II-1, except that the compound of the present invention shown in Table 6 was used instead of the compound 1-1 of the present invention as an electron transport layer material.
  • Example II-7 Red Organic Electroluminescent Device (Electron Transport Layer, Hole Transport Layer)
  • An organic electroluminescent device was manufactured in the same manner as in Example II-1 except for using Compound 2-102 of the present invention shown in Table 6 below instead of Compound 2-5 of the present invention as a hole transport layer material.
  • Example II-8 to [ Example II-12] Red Organic Electroluminescent Device ( Electron Transport Layer , Hole Transport Layer)
  • An organic electroluminescent device was manufactured in the same manner as in Example II-7, except that the compound of the present invention shown in Table 6 was used instead of the compound 1-1 of the present invention as an electron transport layer material.
  • Example II-13 Red Organic Light Emitting Diode (Electron Transport Layer, Hole Transport Layer)
  • An organic electroluminescent device was manufactured according to the same method as Example II-1 except for using Compound 2-129 of the present invention as shown in Table 6 instead of Compound 2-5 of the present invention as a hole transport layer material.
  • red organic electroluminescent device an electron transport layer, positive hole transport layer
  • An organic electroluminescent device was manufactured in the same manner as in Example II-13, except that the compound of the present invention shown in Table 6 was used instead of the compound 1-1 of the present invention as an electron transport layer material.
  • the electroluminescence (EL) characteristics were measured by the PR-650 of photoresearch, and 2500cd was measured.
  • the T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at / m 2 reference luminance. The measurement results are shown in Table 6 below.
  • red organic electroluminescent device an electron transport layer, a hole transport layer, a light-emitting auxiliary layer
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as an electron transport layer material.
  • 2-TNATA is vacuum deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate to form a hole injection layer
  • Compound 2-5 of the present invention is vacuum deposited to a thickness of 60 nm on the hole injection layer.
  • a hole transport layer was formed.
  • the compound 2-46 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light emitting auxiliary layer, and then CBP as a host material and a dopant material (piq) on the light emitting auxiliary layer.
  • red organic electroluminescent device an electron transport layer, positive hole transport layer, a light-emitting auxiliary layer
  • An organic electroluminescent device was manufactured in the same manner as in Example III-1, except that Compound 1-1 of the present invention was used instead of Compound 1-1 of the present invention as an electron transporting material.
  • red organic electroluminescent device an electron transport layer, a hole transport layer, a light-emitting auxiliary layer
  • An organic electroluminescent device was manufactured in the same manner as in Example III-1, except that Compound 2-49 of the present invention shown in Table 7 was used instead of Compound 2-46 of the present invention.
  • Example III-8 to [ Example III-12] Red Organic Electroluminescent Device ( electron transport layer , hole transport layer, light emitting auxiliary layer)
  • An organic electroluminescent device was manufactured in the same manner as in Example III-7, except that the compound of the present invention shown in Table 7 was used instead of the compound 1-1 of the present invention as an electron transporting material.
  • red organic electroluminescent device an electron transport layer, a hole transport layer, a light-emitting auxiliary layer
  • An organic electroluminescent device was manufactured in the same manner as in Example III-1, except that Compound 2-130 of the present invention shown in Table 7 was used instead of Compound 2-46 of the present invention as a light-emitting auxiliary layer material.
  • Example III-14 to [ Example III-18] Red Organic Electroluminescent Device ( electron transport layer , hole transport layer, light emitting auxiliary layer)
  • An organic electroluminescent device was manufactured in the same manner as in Example III-13, except that Compound 1-1 of the present invention was used instead of Compound 1-1 of the present invention as an electron transporting material.
  • the electroluminescence (EL) characteristics of the photoresearch company PR-650 were measured and 2500cd.
  • the T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at / m 2 reference luminance. The measurement results are shown in Table 7 below.
  • Example III Examples I-1 to I-74
  • Example II Examples II-1 to II-2-18
  • Example III-1 to Example III-18 Example III-1 to Example III-18
  • the compound represented by Formula 1, 1a or 1b of the present invention is used as the electron transport layer material and the compound represented by Formula 2 is used as the hole transport layer and / or the light emitting auxiliary layer. It is difficult to infer the performance of the device combination having even those skilled in the art to which the present invention belongs.

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Abstract

L'invention concerne un composé représenté par la formule chimique 1. L'invention concerne également un élément électronique organique comprenant une première électrode, une seconde électrode et une couche de matière organique située entre la première électrode et la seconde électrode, la couche de matière organique comprenant quant à elle le composé représenté par la formule chimique 1. Si le composé représenté par la formule chimique 1 est compris dans la couche de matière organique, l'efficacité et la stabilité lumineuses ainsi que la durée de vie de l'élément électronique organique peuvent être renforcés.
PCT/KR2015/006840 2014-07-03 2015-07-02 Composé pour élément électronique organique, élément électronique organique utilisant ledit composé et dispositif électronique comprenant ledit composé WO2016003225A2 (fr)

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