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WO2021034089A1 - Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé - Google Patents

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

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WO2021034089A1
WO2021034089A1 PCT/KR2020/011009 KR2020011009W WO2021034089A1 WO 2021034089 A1 WO2021034089 A1 WO 2021034089A1 KR 2020011009 W KR2020011009 W KR 2020011009W WO 2021034089 A1 WO2021034089 A1 WO 2021034089A1
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Korean (ko)
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박형근
이윤석
조민지
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DukSan Neolux Co Ltd
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DukSan Neolux Co Ltd
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • 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
    • C07D405/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D409/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

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.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic electric device using an organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered 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 an organic material layer in an organic electronic device can 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, according to their functions.
  • the light-emitting material may be classified into a high molecular type and a low molecular type according to its molecular weight, and according to a light emitting mechanism, it may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron. have.
  • the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.
  • a host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through.
  • the principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.
  • Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan.
  • simply improving the organic material layer cannot maximize efficiency. This is because long life and high efficiency can be achieved at the same time 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.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer, thereby generating excitons through recombination.
  • the color purity and efficiency of the organic electronic device are deteriorated, and the lifespan is shortened. Therefore, it must be a material having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, has a high T1 value, and has a suitable driving voltage range (within the range of the driving voltage of the blue device of the full device). There is an urgent need to develop a light-emitting auxiliary layer having mobility).
  • the low glass transition temperature of the light-emitting layer and the light-emitting auxiliary layer material decreases the uniformity of the thin film surface when the device is driven, and the material may be deformed due to heat generated when the device is driven, which is reported to have a great effect on the life of the device.
  • An object of the present invention is to provide a compound having high heat resistance, lowering the driving voltage of the device, and improving the luminous efficiency, color purity, and lifespan of the device, an organic electric device using the same, and an electronic device including the organic electric device To do.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.
  • FIG. 1 to 3 schematically illustrate organic electric devices according to embodiments of the present invention.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.
  • first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term.
  • a component such as a layer, film, region, or plate
  • it is not only “directly over” another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is “directly above” another part, it means that there is no other part in the middle.
  • halo or halogen as used in this application includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I) unless otherwise specified.
  • alkyl or "alkyl group” as used in the present application has 1 to 60 carbons connected by a single bond unless otherwise specified, and a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted It means a radical of a saturated aliphatic functional group including a cycloalkyl group and a cycloalkyl-substituted alkyl group.
  • haloalkyl group or "halogenalkyl group” as used in the present application means an alkyl group in which halogen is substituted unless otherwise specified.
  • alkenyl or “alkynyl” used in the present application each have a double bond or a triple bond, unless otherwise specified, include a straight or branched chain group, and have a carbon number of 2 to 60, but are limited thereto. It does not become.
  • cycloalkyl as used in the present application means an alkyl forming a ring having 3 to 60 carbon atoms unless otherwise specified, and is not limited thereto.
  • alkoxy group or "alkyloxy group” used in the present application refers to an alkyl group to which an oxygen radical is bonded, and has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 It has a carbon number of, but is not limited thereto.
  • aryl group and “arylene group” as used in the present application each have 6 to 60 carbon atoms, but are not limited thereto.
  • the aryl group or the arylene group includes a single cyclic type, a ring aggregate, and several cyclic compounds conjugated.
  • the aryl group may include a phenyl group, a biphenyl monovalent functional group, a naphthalene monovalent functional group, a fluorenyl group, and a substituted fluorenyl group
  • the arylene group may include a fluorenylene group, a substituted fluorenylene group It may contain a group.
  • ring assemblies refers to two or more ring systems (single ring or fused ring system) being directly connected to each other through a single bond or a double bond, and between such rings It means that the number of direct linkages is one less than the total number of ring systems in the compound. In the ring aggregate, the same or different ring systems may be directly linked to each other through a single bond or a double bond.
  • the aryl group since the aryl group includes a ring aggregate, the aryl group includes biphenyl and terphenyl in which the benzene ring, which is a single aromatic ring, is connected by a single bond.
  • the aryl group also includes a compound in which the aromatic ring system conjugated with an aromatic single ring is connected by a single bond, for example, a compound in which fluorene, an aromatic ring system conjugated with an aromatic single ring benzene ring, is connected by a single bond. do.
  • conjugated multiple ring systems refers to a fused ring form that shares at least two atoms, and includes a form in which a ring system of two or more hydrocarbons is fused and at least one heteroatom And at least one conjugated heterocyclic system.
  • fused ring systems may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings.
  • the aryl group may be a naphthalenyl group, a phenanthrenyl group, or a fluorenyl group, but is not limited thereto.
  • spyro compound as used in the present application has a'spiro union', and the spiro linkage refers to a connection made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.
  • fluorenyl group refers to R, R', R" and R'" in the following structures, respectively, unless otherwise stated. It refers to a monovalent, divalent or trivalent functional group
  • substituted fluorenyl group refers to a substituent R, R', R", R' It means that at least one of "is a substituent other than hydrogen, and includes the case where R and R'are bonded to each other to form a spy compound with the carbon to which they are bonded.
  • a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of valence such as monovalent, divalent, or trivalent.
  • R, R', R" and R'" are each independently an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 1 to 20, an aryl group having a carbon number of 6 to 30, 3 to It may be a heterocyclic group having 30 carbon atoms, for example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, imidazole, Triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline.
  • the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene
  • the heterocyclic group may be pyrrole, furan, thi
  • substituted fluorenyl group and fluorenylene group are monovalent of 9,9-dimethylfluorene, 9,9-diphenylfluorene and 9,9'-spirobi[9H-fluorene], respectively. It may be a functional group or a divalent functional group.
  • heterocyclic group used in the present application includes not only an aromatic ring such as a “heteroaryl group” or a “heteroarylene group”, but also a non-aromatic ring, and unless otherwise stated, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom used in the present application represents N, O, S, P or Si unless otherwise specified, and the heterocyclic group is a monocyclic type containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like.
  • ring as used in the present application includes monocyclic and polycyclic rings, including hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and non-aromatic rings.
  • polycyclic as used in the present application includes ring assemblies such as biphenyl, terphenyl, etc., several fused ring systems and spiro compounds, and includes not only aromatic but also non-aromatic, hydrocarbon Rings of course include heterocycles containing at least one heteroatom.
  • aliphatic ring group refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic types, cyclic aggregates, conjugated cyclic systems, spiro compounds, etc., unless otherwise stated, It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring and cyclohexane, which is a non-aromatic ring, are fused, it is an aliphatic ring.
  • arylalkoxy group it means an alkoxy group substituted with an aryl group
  • alkoxycarbonyl group it means a carbonyl group substituted with an alkoxy group
  • arylcarbonylalkenyl group it means an alkenyl group substituted with an arylcarbonyl group, where The arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • substituted or unsubstituted refers to deuterium, halogen, amino group, nitrile group, nitro group, C 1 to C 20 alkyl group, C 1 to C 20 alkoxy group, C 1 to C 20 alkylamine group, C 1 to C 20 alkylthiophene group, C 6 to C 20 arylthiophene group, C 2 to C 20 alkenyl group, C 2 to C 20 alkynyl, C 3 ⁇ C 20 of the 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 at least one heteroatom selected from the group consisting of O, N, S, Si, and P. It means substituted with one or more substituenta compound, a silane group, a boron Group, germanium group, and at least one hetero
  • the'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe the'name of the functional group reflecting the number', but it is described as the'parent compound name' You may.
  • the monovalent'group' is'phenanthryl (group)'
  • the divalent group is named by dividing the valence such as'phenanthrylene (group)', etc.
  • pyrimidine it is described as'pyrimidine' regardless of the valence, or in the case of monovalent, it is referred to as pyrimidinyl (group), and in the case of divalent, the'group of the corresponding valency is expressed as pyrimidinylene (group). It can also be written as'name of'. Therefore, when the type of the substituent is described as the parent compound name in the present application, it may mean an n-valent'group' formed by desorbing a carbon atom and/or a hydrogen atom bonded to a heteroatom of the parent compound.
  • the substituent R 1 means that the substituent R 1 does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described.
  • a is an integer of 1
  • one substituent R 1 is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6
  • R 1 may be the same or different from each other.
  • a ring means that adjacent groups are bonded to each other to form a single ring or several conjugated rings, and a single ring and a plurality of conjugated rings formed are hydrocarbon rings as well as at least one It includes a heterocycle including a heteroatom, and may include aromatic and non-aromatic rings.
  • a number in'number-condensed ring' indicates the number of condensed rings.
  • a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc. can be expressed as a 3-condensed ring.
  • bridged bicyclic compound used in the present application refers to a compound in which two rings share 3 or more atoms to form a ring unless otherwise specified.
  • the shared atom may include carbon or heteroatom.
  • an organic electric device 100 includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown).
  • An organic material layer including the compound according to the present invention is included between the second electrodes 170.
  • the first electrode 110 may be an anode (anode)
  • the second electrode 170 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic material layer may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160.
  • the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.
  • the capping layer 180 may be formed on one surface of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and when the capping layer 180 is formed, organic electricity The light efficiency of the device can be improved.
  • the capping layer 180 may be formed on the second electrode 170.
  • the capping layer 180 is formed so that the capping layer 180 is formed on the second electrode 170.
  • Optical energy loss due to SPPs (surface plasmon polaritons) of can be reduced, and in the case of a bottom emission organic light emitting device, the capping layer 180 can function as a buffer for the second electrode 170 .
  • a buffer layer 210 or a light emission auxiliary layer 220 may be further formed between the hole transport layer 130 and the emission layer 140, which will be described with reference to FIG. 2.
  • an organic electric device 200 includes a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, A light emission auxiliary layer 220, a light emission layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a capping layer 180 may be formed on the second electrode.
  • an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.
  • the organic material layer may have a plurality of stacks including a hole transport layer, an emission layer, and an electron transport layer. This will be described with reference to FIG. 3.
  • two stacks ST1 and ST2 formed of a multi-layered organic material layer are formed between the first electrode 110 and the second electrode 170.
  • a set or more may be formed, and a charge generation layer CGL may be formed between the stack of organic material layers.
  • the organic electric device includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and a capping layer 180 may be included.
  • the first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer ( 350) may be included.
  • the second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second emission layer 440, and a second electron transport layer 450.
  • the first stack and the second stack may be organic material layers having the same laminated structure, but may be organic material layers having different laminated structures.
  • a charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2.
  • the charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361.
  • the charge generation layer CGL is formed between the first emission layer 340 and the second emission layer 440 to increase the current efficiency generated in each emission layer and smoothly distribute electric charges.
  • the first emission layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 440 is a material doped with a greenish yellow dopant and a red dopant in a green host. May be included, but the materials of the first emission layer 340 and the second emission layer 440 according to the exemplary embodiment of the present invention are not limited thereto.
  • the second hole transport layer 430 includes a second stack ST2 in which the energy level is set higher than the triplet excitation energy level of the second emission layer 440.
  • the second hole transport layer 430 may function as an exciton blocking layer that prevents the tripping of triplet excitons while transporting holes from the inherent second emission layer 440. .
  • first hole transport layer 330 may also be set to an energy level higher than the triplet excitation energy level of the first emission layer 340 for the function of the exciton blocking layer.
  • first electron transport layer 350 is also set to an energy level higher than that of the triplet excited state of the first emission layer 340, and the second electron transport layer 450 is also triplet excitation of the second emission layer 440. It is preferable to set the energy level higher than the energy level of the state.
  • n may be an integer of 1-5.
  • a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.
  • the compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light emission auxiliary layer (220), an electron transport layer (150, 350). , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material of the capping layer 180, but preferably, the hole transport layer 130, 330, 430, the light emission auxiliary layer 220 ), the light emitting layers 140, 340, and 440, and/or the capping layer 180 may be used as a material.
  • the organic electric device according to FIGS. 1 to 3 may further include a protective layer (not shown) and an encapsulation layer (not shown).
  • the protective layer may be located on the capping layer, the encapsulation layer is located on the capping layer, and at least one side portion of the first electrode, the second electrode, and the organic material layer to protect the first electrode, the second electrode, and the organic material layer It can be formed to cover.
  • the protective layer may provide a flattened surface so that the encapsulation layer can be uniformly formed, and may serve to protect the first electrode, the second electrode, and the organic material layer in the manufacturing process of the encapsulation layer.
  • the encapsulation layer may play a role of preventing external oxygen and moisture from penetrating into the organic electronic device.
  • the band gap, electrical characteristics, and interface characteristics may vary depending on which substituent is bonded to any position, so the selection of the core and the combination of sub-substituents bonded thereto In particular, long life and high efficiency can be achieved at the same time when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved.
  • the compound represented by Chemical Formula 1 as a material for the light emission auxiliary layer 220, the light emission layers 140, 340, and 440, and/or the capping layer 180, the energy level and T1 value between each organic material layer, By optimizing the intrinsic properties of the material (mobility, interfacial properties, etc.), it was possible to improve the life and efficiency of the organic electric device at the same time.
  • the organic electroluminescent device may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD.
  • the anode 110 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 120 thereon.
  • 320, 420 hole transport layers (130, 330, 430), light emitting layers (140, 340, 440), electron transport layers (150, 350, 450), and after forming an organic material layer including the electron injection layer 160, It can be manufactured by depositing a material that can be used as the cathode 170 thereon.
  • a light emission auxiliary layer 220 between the hole transport layer (130, 330, 430) and the light emitting layer (140, 340, 440), an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 May be further formed or may be formed in a stack structure as described above.
  • the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blaze. It can be manufactured with fewer layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention may be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.
  • the organic electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.
  • the organic electric device may include an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.
  • Another embodiment of the present invention may include a display device including the organic electric device 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 mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.
  • a compound according to an aspect of the present invention is represented by the following formula (1).
  • X and Y are each independently S, O or a single bond; However, the case where both X and Y are single bonds is excluded.
  • Z 1 to Z 16 are each independently N or CR'; However, at least one of Z 1 to Z 16 is CR',
  • R' is independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; Amanogi; C 6 ⁇ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; Alkynyl group of C 2 ⁇ C 20; An alkoxyl group of C 1 to C 30; C 6 ⁇ C 30 aryloxy group; C 6 ⁇ C 30 arylthio group; Or neighboring groups can be bonded to each other to form a ring,
  • R'and the ring formed by bonding of adjacent groups to each other is deuterium; halogen; A silane group unsubstituted or substituted with a C 1 to C 20 alkyl group or a C 6 to C 20 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C 1 ⁇ C 20 alkylthio group; C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 20 arylalkoxy group; C 1 ⁇ C 20 alkyl group; C 2 ⁇ C 20 alkenyl group; Alkynyl group of C 2 ⁇ C 20; C 6 ⁇ C 20 aryl group; A C 6 ⁇ C 20 aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 ⁇ C 20 aliphatic ring group; C 7 ⁇ C 20 aryl
  • Formula 1 may be represented by any one of Formulas 2 to 6 below, but is not limited thereto.
  • At least one of Z 1 to Z 4 may not be H.
  • At least one of Z 5 to Z 7 may not be H.
  • At least one of Z 8 to Z 11 may not be H.
  • At least one of Z 12 to Z 16 may not be H.
  • R' is the same as defined in Chemical Formula 1.
  • Formula 1 may be represented by any one of Formulas 7 to 10 below, but is not limited thereto.
  • R' may be any one of the following Formulas a-1 to a-3, but is not limited thereto.
  • U is CR a R b , O, S or NL a -Ar a ,
  • L 1 , L 2 and L a are each independently a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60; A divalent aliphatic hydrocarbon group; Or a combination thereof,
  • Ar a , Ar 1 and Ar 2 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; Alkynyl group of C 2 ⁇ C 20; An alkoxyl group of C 1 to C 30; C 6 ⁇ C 30 aryloxy group; Or a combination thereof; Or neighboring groups can be bonded to each other to form a ring,
  • Q 1 to Q 5 are each independently N or CR e ,
  • R a , R b and R e are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C 1 to C 20 alkyl group or a C 6 to C 20 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C 1 ⁇ C 20 alkylthio group; An alkoxyl group of C 1 to C 20; C 1 ⁇ C 20 alkyl group; C 2 ⁇ C 20 alkenyl group; Alkynyl group of C 2 ⁇ C 20; C 6 ⁇ C 20 aryl group; A C 6 ⁇ C 20 aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; A C 3 ⁇ C 20 cycloalkyl group; C 7 ⁇ C 20 arylalkyl group; C 8 ⁇ C 20
  • a and B may be each independently represented by one of the following Z-1 to Z-15:
  • the * is a bonding site that forms a fused ring by bonding with the ring containing X of Formula 1,
  • W 1 and W 2 are each independently a single bond, NL 3 -Ar 3 , S, O or C(R f )(R g ),
  • V is independently of each other N or CR h ,
  • L 3 is the same as the definition of L 1 and L 2 above,
  • Ar 3 is the same as the definition of Ar 1,
  • R f , R g and R h are the same as the definitions of R a , R b and R e; However, R f and R g may be bonded to each other to form a spy compound with C to which they are bonded,
  • Ar a , Ar 1 , Ar 2 , Ar 3 , R a , R b , R e , R f , R g , R h and the rings formed by bonding with each other and neighboring groups are deuterium, respectively; halogen; A silane group unsubstituted or substituted with a C 1 to C 20 alkyl group or a C 6 to C 20 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C 1 ⁇ C 20 alkylthio group; C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 20 arylalkoxy group; C 1 ⁇ C 20 alkyl group; C 2 ⁇ C 20 alkenyl group; Alkynyl group of C 2 ⁇ C 20; C 6 ⁇ C 20 aryl group; A C 6 ⁇ C 20 aryl group substituted with deuterium; Fluorenyl group; O, N, S, Si, and C 2 hal
  • the compound represented by Formula 1 may be one of the following P-1 to P-160, but is not limited thereto.
  • the present invention provides 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 compound represented by Formula 1 alone or in combination.
  • the present invention provides a first electrode; A second electrode; An organic material layer formed between the first electrode and the second electrode; And a capping layer, wherein the capping layer is formed on one surface of both surfaces of the first electrode and the second electrode not in contact with the organic material layer, and the organic material layer or the capping layer is represented by Formula 1
  • the compound to be used alone or as a mixture is included.
  • the organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. That is, at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, or an electron injection layer included in the organic material layer may include a compound represented by Formula (1). .
  • the organic material layer includes at least one of the hole transport layer, an emission auxiliary layer, and an emission layer. That is, the compound may be included in at least one of the hole transport layer, the light emitting auxiliary layer, and the light emitting layer.
  • the organic material layer includes two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode.
  • the organic material layer further includes a charge generation layer formed between the two or more stacks.
  • the present invention provides an electronic device including a display device including an organic electric device including a compound represented by Formula 1 and a control unit for driving the display device.
  • the compound of Formula 1 may be included alone, the compound may be included in a combination of two or more different from each other, or the compound may be included in a combination of two or more different compounds.
  • the final product represented by Formula 1 according to the present invention may be synthesized as shown in Schemes 1 and 2 below, but is not limited thereto.
  • Sub 1 of Scheme 1 may be synthesized by the reaction paths of Schemes 3-1 to 3-4, but is not limited thereto.
  • Sub 1-I (8.8 g, 27.1 mmol) was dissolved in 300 mL of THF in a round bottom flask, and then 2-(trimethylsilyl)-phenyl 2-methylpropane-2-sulfonate (7.76g, 27.1 mmol), Indium(III)trifluoromethanesulfonate (1.5 g, 2.71 mmol) was added and stirred at room temperature for 20 minutes.
  • the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 7.5 g (yield: 72%) of the product.
  • Table 1 below shows the FD-MS values of compounds belonging to Sub 1.
  • Table 2 shows the FD-MS values of compounds belonging to Sub 2.
  • Table 3 shows the FD-MS values of the compounds belonging to Sub 3.
  • Sub 1-1 (8.8 g, 22.99 mmol) was put in a round bottom flask and dissolved with toluene (100 mL), then Sub 3-2 (5.64 g, 22.99 mmol), Pd 2 (dba) 3 (0.6 g, 0.69 mmol) ), P(t-Bu) 3 (0.28 g, 1.38 mmol), NaOt-Bu (6.6 g, 68.96 mmol) were added and stirred at 100°C. When the reaction was completed, extraction was performed with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 9.8 g (yield: 72%) of the product.
  • Example 1 Red organic electroluminescent device (light emission auxiliary layer)
  • An organic electroluminescent device was manufactured according to a conventional method by using the compound of the present invention as a light emitting auxiliary layer material.
  • 2-TNATA -phenylbenzene-1,4-diamine
  • 4-TNATA 4,4-bis[N-(1) as a hole transport compound on the hole injection layer -Naphthyl)-N-phenylamino]biphenyl
  • CBP bis-(1-phenylisoquinolyl)iridium ( III) acetylacetonate
  • piq bis-(1-phenylisoquinolyl)iridium ( III) acetylacetonate
  • BAlq was vacuum deposited on the emission layer to a thickness of 5 nm to form a hole blocking layer, and Bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter, BeBq 2 ) was added to a thickness of 40 nm on the hole blocking layer.
  • BeBq 2 Bis(10-hydroxybenzo[h]quinolinato)beryllium
  • LiF a halogenated alkali metal
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 5 below was used instead of the compound P-7 of the present invention as the light emitting auxiliary layer material of Example 1. .
  • Example 2 An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light emission auxiliary layer of Example 1 was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and Comparative Compound 2 were used as the light emitting auxiliary layer materials of Example 1.
  • Electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch company by applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 1 to 18 and Comparative Examples 1 to 3, and the measurement As a result, the T95 life was measured using a life measurement equipment manufactured by McScience at a reference luminance of 2500 cd/m 2. Table 5 below shows the results of device fabrication and evaluation.
  • Comparative Examples 2 and 3 in which the light-emitting auxiliary layers were formed using Comparative Compounds 1 and 2 having a similar basic skeleton to Formula 1 of the present invention than Comparative Example 1 in which the light-emitting auxiliary layer was not formed, the electrical characteristics of the device were Compared to Comparative Examples 2 and 3, the luminous efficiency, lifetime, and driving voltage of the organic electroluminescent device using the compound of the present invention as a light emitting auxiliary layer material were significantly improved.
  • the compound of the present invention has the same core skeleton as that of Comparative Compound 1, but Comparative Compound 1 differs in that the core does not have a substituent.
  • the compounds of the present invention and Comparative Compound 2 are the same in that they are 5-ring condensed rings, but the element constituting the condensed ring is C in the present invention, whereas Comparative Compound 2 is composed of N.
  • Comparative Compounds 1 and 2 and the compounds of the present invention are similar or identical cores, the physical properties of the compounds significantly differ depending on the presence or absence of a substituent or the type of elements constituting the condensed ring.
  • the condensed ring is formed through C and has a substituent, like the compound of the present invention, hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO level, T1 level), hole injection & mobility characteristics, Electron It is suggested that the physical properties of the compound, such as the blocking property, are more suitable for the red light-emitting auxiliary layer, and thus the device results of Examples 1 to 18, which are completely different from the device characteristics of Comparative Examples 2 and 3, can be derived. Are doing.
  • a 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm, and then NPD was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer.
  • the present invention compound P-13 as a host material on the hole transport layer, [bis-(1-phenylisoquinolyl) iridium(III)acetylacetonate] (hereinafter, abbreviated as “(piq) 2 Ir(acac)”) as a dopant
  • the light emitting layer was deposited with a thickness of 30 nm by doping with a material at a weight ratio of 95:5.
  • BAlq was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer, and BeBq2 was formed on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.
  • An organic light emitting diode was manufactured in the same manner as in Example 19, except that the compound of the present invention described in Table 6 was used instead of the compound P-13 of the present invention as the host material of Example 19.
  • An organic electroluminescent device was manufactured in the same manner as in Example 19, except that CBP, Comparative Compound 1, and Comparative Compound 3 were used as host materials of Example 19, respectively.
  • Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 19 to 40 and Comparative Examples 4 to 6 of the present invention with PR-650 of photoresearch was measured, and the T95 life was measured through a life measurement equipment of McScience at a reference luminance of 2500 cd/m2, and the measurement results are shown in Table 6 below.
  • the organic electroluminescent device using the material for an organic electroluminescent device of the present invention as a phosphorescent host significantly improved luminous efficiency, lifespan, and driving voltage. That is, the present invention compared to Comparative Examples 4 to 6 in which CBP mainly used as a host material, Comparative Compound 1 having the same core as Formula 1 of the present invention, and Comparative Compound 3 having a similar structure with a 5-ring condensation skeleton as a host material.
  • the compound of is used as a host material, the luminous efficiency, lifespan, and driving voltage of the organic electroluminescent device are significantly improved.
  • Comparative Compound 1 and Comparative Compound 3 having a 5-ring condensed ring were used as host materials, device characteristics were superior to CBP, which is generally used as a host material.
  • Comparative Compound 1 and Comparative Compound 3 had only the same core as the present invention, but had excellent driving and life characteristics of the device, and Comparative Compound 3 had similar basic skeletons to the present invention, but elements constituting a condensed ring. Even when is N, it can be seen that the device has excellent efficiency characteristics.
  • the condensed ring is formed through C and has a substituent as in the compound of the present invention, hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO level, T1 level), hole injection & mobility characteristics, electron blocking characteristics It is suggested that the physical properties of the compound such as are more suitable for the red light emitting layer, and thus the device characteristics of Examples 19 to 40, which are significantly improved than the device characteristics of Comparative Examples 4 to 6, can be derived.
  • organic electric device 110 first electrode
  • capping layer 210 buffer layer
  • first hole transport layer 340 first emission layer
  • second charge generation layer 420 second hole injection layer
  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

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Abstract

La présente invention concerne un composé pour un élément électrique organique, un élément électrique organique l'utilisant et un dispositif électronique comprenant l'élément électrique organique. Selon la présente invention, un élément électrique organique ayant une efficacité lumineuse élevée, une faible tension de commande et une résistance à la chaleur élevée peut être fourni, et la pureté des couleurs et la durée de vie de l'élément électrique organique peuvent être améliorées.
PCT/KR2020/011009 2019-08-21 2020-08-19 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé Ceased WO2021034089A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140076519A (ko) * 2012-12-12 2014-06-20 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
CN105367603A (zh) * 2015-12-04 2016-03-02 河南省科学院化学研究所有限公司 一种基于蒽的双膦杂六元环有机电致发光化合物、合成方法及其应用
WO2018186462A1 (fr) * 2017-04-07 2018-10-11 コニカミノルタ株式会社 Composé fluorescent, composition de matériau organique, film électroluminescent, matériau d'élément électroluminescent organique et élément électroluminescent organique
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KR20140076519A (ko) * 2012-12-12 2014-06-20 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
CN105367603A (zh) * 2015-12-04 2016-03-02 河南省科学院化学研究所有限公司 一种基于蒽的双膦杂六元环有机电致发光化合物、合成方法及其应用
WO2018186462A1 (fr) * 2017-04-07 2018-10-11 コニカミノルタ株式会社 Composé fluorescent, composition de matériau organique, film électroluminescent, matériau d'élément électroluminescent organique et élément électroluminescent organique
CN109192874A (zh) * 2018-08-31 2019-01-11 昆山国显光电有限公司 一种有机电致发光器件和显示装置

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ROY DEBLINA; PANDA GAUTAM: "A dehydrative arylation and thiolation of tertiary alcohols catalyzed byin situgenerated triflic acid - Viable protocol for CC and CS bond formation", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 74, no. 43, 12 September 2018 (2018-09-12), AMSTERDAM, NL, pages 6270 - 6277, XP085489400, ISSN: 0040-4020, DOI: 10.1016/j.tet.2018.09.009 *

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