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WO2021246698A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé - Google Patents

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

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WO2021246698A1
WO2021246698A1 PCT/KR2021/006424 KR2021006424W WO2021246698A1 WO 2021246698 A1 WO2021246698 A1 WO 2021246698A1 KR 2021006424 W KR2021006424 W KR 2021006424W WO 2021246698 A1 WO2021246698 A1 WO 2021246698A1
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organic
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Inventor
이범성
조민지
이선희
장재완
문성윤
이윤석
권의식
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DukSan Neolux Co Ltd
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    • 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
    • C07D405/14—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 three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • a material used as an organic layer in an organic electric device 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, etc. according to their function.
  • the light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism.
  • the light emitting material may be divided 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 emission color.
  • a host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through the The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emission layer is mixed in the emission layer, excitons generated in the emission 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 band 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 is relatively decreased. It shows a tendency to increase the lifespan.
  • the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T 1 value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time. .
  • the material constituting 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, etc., is supported by a stable and efficient material.
  • a host material for the light emitting layer is required.
  • An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and lifespan 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 electric device and an electronic device using the compound represented by the above formula.
  • 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
  • organic electric device 110 first electrode
  • first hole transport layer 340 first light emitting layer
  • second charge generation layer 420 second hole injection layer
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto.
  • the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
  • the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.
  • fluorenyl group refers to a substituted or unsubstituted fluorenyl group
  • fluorenylene group refers to a substituted or unsubstituted fluorenyl group
  • the fluorenyl group or The fluorenylene group includes cases in which R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.
  • Substituted fluorenyl group means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the present specification, regardless of the valence, a fluorenyl group , a fluorenylene group, a fluorentriyl group, and the like may all be referred to as a fluorene group.
  • the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.
  • heterocyclic group used in the present invention includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto.
  • the heterocyclic group includes a monocyclic type including a heteroatom, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
  • aliphatic ring group used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms 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 corresponds to an aliphatic ring.
  • the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may.
  • the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'.
  • pyrimidine regardless of the valence, it can be described as 'pyrimidine' or as the 'name of the group' of the valence, such as a pyrimidinyl group in the case of monovalent or pyrimidinylene in the case of divalent. have.
  • the substituent R 1 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring. It can be omitted and the chemical formula or compound can be described.
  • a is an integer of 1
  • one substituent R 1 is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same as or different from each other.
  • the number in 'number-condensed ring' indicates the number of rings to be condensed.
  • a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc. may be expressed as a 3-condensed ring.
  • a ring when expressed in the form of a 'numeric atom', such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring.
  • thiophene or furan may correspond to a 5-membered ring
  • benzene or pyridine may correspond to a 6-membered ring.
  • the ring formed by bonding adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60
  • An aliphatic ring group may be selected from the group consisting of.
  • 'neighboring groups' refers to each other when describing the following chemical formula as an example, R 1 and R 2 each other , R 2 and R 3 each other , R 3 and R 4 each other , It includes not only R 5 and R 6 , but also R 7 and R 8 that share one carbon, R 1 and R 7 , R 1 and R 8 , or R 4 and R 5 that are not immediately adjacent Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included.
  • substituents on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.
  • the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.
  • a component such as a layer, membrane, region, plate, etc.
  • 1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
  • 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). ) and an organic material layer formed between the second electrode 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 light efficiency improving layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and when the light efficiency improving layer 180 is formed Light efficiency of the organic electric device may be improved.
  • the light efficiency improving layer 180 may be formed on the second electrode 170 .
  • the light efficiency improving layer 180 is formed to form the second electrode 170 .
  • the light efficiency improvement layer 180 serves as a buffer for the second electrode 170 . can do.
  • a buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .
  • the organic electric device 200 is a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode.
  • a light emitting auxiliary layer 220 may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is 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 form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .
  • the organic electric device 300 there are two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.
  • CGL charge generating layer
  • a first electrode 110 a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , and a second electrode 170 and the light efficiency improving layer 180 may be included.
  • CGL charge generation layer
  • second stack ST2 a second electrode 170 and the light efficiency improving layer 180
  • 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 .
  • 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 stacked structure or organic material layers having different stacked 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 generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and to smoothly distribute charges.
  • the first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.
  • n may be an integer of 1 to 5.
  • the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .
  • an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.
  • 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 emitting auxiliary layer 220, an electron transport layer (150, 350) , 450), the electron injection layer 160, the light emitting layers 140, 340, 440, or may be used as a material of the light efficiency improving layer 180, preferably the light emitting layer (140, 340, 440) and / or light efficiency improving layer (180) can be used as a material.
  • the compound represented by Chemical Formula 1 as a material for the light emitting layers 140, 340, 440 and/or the light efficiency improving layer 180, the energy level and T 1 value between each organic material layer, the inherent properties of the material ( Mobility, interface characteristics, etc.) can be optimized to improve the lifetime 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, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be prepared by depositing a material that can be used as the cathode 170 thereon. have.
  • a deposition method such as PVD or CVD
  • an auxiliary light emitting layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140
  • an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.
  • the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, 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, Dr. Blay It can be manufactured with a smaller number of 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 can be formed by various methods, the scope of the present invention is not limited by the formation method.
  • the organic electric device may be a top emission type, a back emission type, or a double-sided emission type depending on a material used.
  • the organic electric device may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.
  • 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/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 control, a navigation system, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • X is O, S or N(-L 1 -Ar 1 ).
  • L is a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • Ar is hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 An aliphatic group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; C 6 ⁇ C 30 Aryloxy group; and -L′-N(R a )(R b );
  • n is an integer of 2 or 3, and when n is 2 or 3, each of a plurality of L and each of a plurality of Y 1 to each of a plurality of Y 16 are the same as or different from each other.
  • Y 1 to Y 16 are each independently N or C(R 1 ).
  • the R 1 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 An aliphatic group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a) ( R b); is selected from the group consisting of, and adjacent these groups may combine with each other to form a ring together, n is at least one from among R 1, if the three neighboring one pairs of the It is preferable to combine with each other to form a ring.
  • Adjacent R 1 may combine with each other to form a ring.
  • a ring formed by bonding adjacent R 1 to each other is a C 6 ⁇ C 60 aromatic ring; fluorene; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 Heterocycle; And C 3 ⁇ C 60 It may be selected from the group consisting of an aliphatic ring.
  • C 6 ⁇ C 30 when adjacent groups are bonded to each other to form an aromatic ring, C 6 ⁇ C 30 , C 6 ⁇ C 20 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 10 , C 6 , etc.
  • An aromatic ring may be formed, and specifically, an aromatic ring such as benzene, naphthalene, or phenanthrene may be formed.
  • the L 1 and L' are each independently a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • the Ar 1 , R a and R b are each independently a C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • the aryl group is, for example, C 6 to C 30 , C 6 to C 29 , C 6 to C 28 , C 6 to C 27 , C 6 ⁇ C 26 , C 6 ⁇ C 25 , C 6 ⁇ C 24 , C 6 ⁇ C 23 , C 6 ⁇ C 22 , C 6 ⁇ C 21 , C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ It may be an aryl group such as C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , and specifically,
  • the arylene group for example, C 6 ⁇ C 30 , C 6 ⁇ C 29 , C 6 ⁇ C 28 , C 6 ⁇ C 27 , C 6 ⁇ C 26 , C 6 ⁇ C 25 , C 6 ⁇ C 24 , C 6 ⁇ C 23 , C 6 ⁇ C 22 , C 6 ⁇ C 21 , C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C 10 , It may be an arylene group such as C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , and specifically, phenylene, biphenyl
  • the heterocycle is, for example, C 2 ⁇ C 30 , C 2 ⁇ C 29 , C 2 ⁇ C 28 , C 2 ⁇ C 27 , C 2 ⁇ C 26 , C 2 ⁇ C 25 , C 2 ⁇ C 24 , C 2 ⁇ C 23 , C 2 ⁇ C 22 , C 2 ⁇ C 21 , C 2 ⁇ C 20 , C 2 ⁇ C 19 , C 2 ⁇ C 18 , C 2 ⁇ C 17 , C 2 ⁇ C 16 , C 2 ⁇ C 15 , C 2 ⁇ C 14 , C 2 ⁇ C 13 , C 2 ⁇ C 12 , C 2 ⁇ C 11 , C 2 ⁇ C 10 , C 2 ⁇ C 9 , C 2 ⁇ C 8 , C 2 ⁇ C 7 , C 2 ⁇ C 6 , C 2 ⁇ C 5
  • At least one of Ar, Ar 1 , R 1 , R a , R b is a fluorenyl group, or L, L 1
  • L' is a fluorenylene group
  • the fluorenyl group or the fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9' - as a by-fluorene, spy spy [benzo [b] fluorene -11,9'- fluorene], benzo [b] fluorene, diphenyl-11,11- -11 H-benzo [b] fluorene, 9- (naphthalen-2-yl) phenyl--9 H - may be a fluorene.
  • the alkoxy group may be, for example, an alkyl group such as C 1 -C 20 , C 1 -C 10 , C 1 -C 4 , for example, methyl, ethyl, propyl, butyl, t-butyl, and the like.
  • R 1 is an aryloxy group
  • the aryloxy group is, for example, C 6 ⁇ C 30 , C 6 ⁇ C 20 , C 6 ⁇ C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , may be an aryloxy group such as C 14 .
  • the aryl group is, for example, C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , It may be an aryl group such as C 17 or C 18 .
  • the heterocyclic group is, for example, C 2 ⁇ C 20 , C 2 ⁇ C 19 , C 2 ⁇ C 18 , C 2 ⁇ C 17 , C 2 ⁇ C 16 , C 2 ⁇ C 15 , C 2 ⁇ C 14 , C 2 ⁇ C 13 , C 2 ⁇ C 12 , C 2 ⁇ C 11 , C 2 ⁇ C 10 , C 2 ⁇ C 9 , C 2 ⁇ C 8 , C 2 ⁇ C 7 , C 2 ⁇ C 6 , C 2 ⁇ C 5 , C 2 ⁇ C 4 , C 2 ⁇ C 3 , C 2 ,
  • L' is, for example, C 6 -C 20 , C 6 -C 19 , C 6 -C 18 , C 6 -C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , It may be an arylene group such as C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , and R a and R
  • the alkenyl group may be, for example, an alkenyl group such as C 2 to C 20 , C 2 to C 10 , C 2 to C 4 , C 2 , C 3 , C 4 .
  • Formula 1 may be represented by Formula 2 or Formula 3 below.
  • Chemical Formula 1 may be represented by Chemical Formula 4 below.
  • X, L, and Ar are as defined in Formula 1, and a to d are each an integer of 0 to 2.
  • a and b is an integer of 1 or more
  • at least one of c and d is an integer of 1 or more
  • at least one of a and b is an integer of 1 or more
  • at least one of c and d is an integer of 1 or more
  • at least one of c and d is an integer of 1 or more
  • Formula 4 may be represented by Formula 5 or Formula 6 below.
  • Formula 5 when c and d are 0, Formula 5 may be represented by Formula 5-1, and in Formula 6, when c and d are 0, Formula 6 may be represented by Formula 6-1 can
  • Chemical Formula 1 may be represented by one of Chemical Formulas 7 to 14 below.
  • the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
  • the present invention provides an organic electric device including an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.
  • the present invention provides an organic electric device comprising an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improving layer.
  • the light efficiency improving layer is formed on one side of both surfaces of the anode or the cathode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improving layer may include the compound represented by Formula 1 above.
  • the organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, preferably the compound is included in the light emitting layer, It can be used as a red phosphorescent host.
  • the organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generating layer formed between the two or more stacks.
  • an electronic device including a display device including the organic electric device represented by Formula 1, and a control unit for driving the display device.
  • the compound represented by Formula 1 according to the present invention may be synthesized as shown in Scheme 1 below, but is not limited thereto.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
  • Sub 1-31-a (30 g, 57.2 mmol), Sub 1-31-b (31.8 g, 57.2 mmol), Pd(PPh 3 ) 4 (3.3 g, 2.9 mmol), K 2 CO 3 (23.7 g, 171.5 mmol), THF (191ml) and water were used in the same manner as in the synthesis method of Sub 1-1 to obtain 36.5 g (yield: 73%) of the product.
  • the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1 below.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto.
  • the compound belonging to Sub 2 may be a compound as follows, but is not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 2 below.
  • 2-TNATA 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine
  • 2-TNATA 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine
  • 2-TNATA 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine
  • 2-TNATA 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine
  • BAlq (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum
  • BAlq (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum
  • BAlq 2 bis(10-hydroxybenzo[h]quinolinato)beryllium
  • BeBq 2 bis(10-hydroxybenzo[h]quinolinato)beryllium
  • LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 0.2 nm
  • Al was deposited to form a cathode having a thickness of 150 nm.
  • An organic electroluminescent device was always prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of Compound P-1 as the host material of the light emitting layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following comparative compounds to comparative compounds 3 was used instead of the compound P-1 of the present invention as a host material for the light emitting layer.
  • the electroluminescence (EL) characteristics were obtained with PR-650 of Photoresearch. It was measured, and the T95 lifespan was measured using the life measuring equipment of McScience at 2500cd/m 2 standard luminance. The measurement results are shown in Table 4 below.
  • Comparative Example 2 or Comparative Example 3 had superior device characteristics, and when the compound according to Formula 1 of the present invention was used as a host of the light emitting layer, the device characteristics were remarkably improved.
  • a simple xanthene moiety in which a xanthene moiety and fluorene are fused to triazine is bonded as a substituent.
  • Comparative Compound 1 Compared to the case of using Comparative Compound 1, when Comparative Compound 2 or Comparative Compound 3 is used as a host, device characteristics are improved. Therefore, the number of xanthenes bonded to triazine, simple xanthene or fused xanthene, etc. are dependent on the electrical properties of the device. It can be seen that the influence This appears to be due to the difference in physical properties such as energy level or T1 value between the comparative compound and the compound of the present invention.
  • Table 5 below shows LUMO values for Comparative Compound 1, Comparative Compound 2, and Compounds P-1 and P-113 of the present invention.
  • the compound of the present invention has a lower LUMO value compared to the comparative compound.
  • the electron transfer to the light emitting layer is easier compared to the case where the comparative compound is used, so that the characteristics of the device are improved.
  • Table 6 below shows the T1 values of Comparative Compound 3 and Compound P-89 of the present invention.
  • Comparative Compound 3 has a T1 value that is out of the red region, so energy transfer to the dopant is not smooth, but since the compound P-89 of the present invention is lower than Comparative Compound 3, energy transfer to the dopant It seems that the device characteristics are improved because light emission occurs more smoothly than this.

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

Abstract

La présente invention concerne : un composé représenté par la formule chimique 1; un élément électrique organique comprenant une première électrode, une seconde électrode et une couche de matériau organique entre la première électrode et la seconde électrode; et un dispositif électronique comprenant l'élément électrique organique. La présence du composé représenté par la formule chimique 1 dans la couche de matériau organique permet à la tension de commande de l'élément électrique organique d'être abaissée, et à son rendement d'émission de lumière et sa durée de vie d'être améliorés.
PCT/KR2021/006424 2020-06-05 2021-05-24 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé Ceased WO2021246698A1 (fr)

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CN107417676A (zh) * 2017-07-04 2017-12-01 信阳师范学院 均三嗪螺环芳烃位阻型双极性发光材料及其合成方法
WO2018038401A1 (fr) * 2016-08-23 2018-03-01 주식회사 두산 Composé organique et dispositif à électroluminescence organique comprenant un tel composé
KR20180069423A (ko) * 2016-12-15 2018-06-25 (주)씨엠디엘 스파이로플루오렌 잔텐닐 유도체 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101987256B1 (ko) * 2018-12-14 2019-06-10 주식회사 엘지화학 축합환 화합물 및 이를 포함하는 유기 발광 소자

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WO2018038401A1 (fr) * 2016-08-23 2018-03-01 주식회사 두산 Composé organique et dispositif à électroluminescence organique comprenant un tel composé
KR20180069423A (ko) * 2016-12-15 2018-06-25 (주)씨엠디엘 스파이로플루오렌 잔텐닐 유도체 화합물 및 이를 포함하는 유기 전계 발광 소자
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CN116925090A (zh) * 2023-07-24 2023-10-24 上海天马微电子有限公司 一种螺环化合物及其在有机发光器件和面板中的应用

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