WO2024010280A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé - Google Patents

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

Info

Publication number
WO2024010280A1
WO2024010280A1 PCT/KR2023/009098 KR2023009098W WO2024010280A1 WO 2024010280 A1 WO2024010280 A1 WO 2024010280A1 KR 2023009098 W KR2023009098 W KR 2023009098W WO 2024010280 A1 WO2024010280 A1 WO 2024010280A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
sub
compound
layer
Prior art date
Application number
PCT/KR2023/009098
Other languages
English (en)
Korean (ko)
Inventor
곽수진
오경환
유재덕
김대식
이중근
김봉성
오현지
Original Assignee
덕산네오룩스 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020230038683A external-priority patent/KR20240006426A/ko
Priority claimed from KR1020230082036A external-priority patent/KR20240005586A/ko
Application filed by 덕산네오룩스 주식회사 filed Critical 덕산네오룩스 주식회사
Publication of WO2024010280A1 publication Critical patent/WO2024010280A1/fr

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

Definitions

  • the present invention relates to compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic electric devices that utilize the organic light emission phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic electric device, and may be composed 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 organic layers in organic electric devices 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, depending on their function.
  • the light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. there is.
  • light-emitting materials can be divided into blue, green, and red light-emitting materials depending on the color of the light, and yellow and orange light-emitting materials necessary to realize better natural colors.
  • a host/dopant system can be used as a luminescent material.
  • the principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light.
  • the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
  • Efficiency, lifespan, and driving voltage are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined. .
  • the purpose of the present invention is to provide a compound that can lower the driving voltage of the device and improve 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 formula:
  • the present invention provides an organic electric device and an electronic device containing the compound represented by the above formula.
  • the driving voltage of the device can be lowered and the luminous efficiency and lifespan can be improved.
  • 1 to 3 are exemplary diagrams of organic electroluminescent devices according to the present invention.
  • Organic electric element 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 each have 6 to 60 carbon atoms unless otherwise specified, and are not limited thereto.
  • an aryl group or arylene group may include a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc.
  • fluorenyl group used in the present invention refers to a substituted or unsubstituted fluorenyl group
  • fluorenylene group refers to a substituted or unsubstituted fluorenylene group, and the fluorenyl group or
  • the fluorenylene group includes spiro compounds formed by R and R' bonded to each other in the structure below, and also includes compounds formed by adjacent R" bonded to each other to form a ring.
  • Substituted fluorenyl group "substituted The fluorenylene group” means that at least one of R, R', and R" in the structure below is a substituent other than hydrogen, and in the formula below, R" may be 1 to 8.
  • R may be 1 to 8.
  • Fluorenyl group, fluorenylene group, etc. may be referred to as fluorene group or fluorene.
  • spiro compound used in the present invention has a 'spiro connection', and the spiro connection means a connection made by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms in one compound, they are 'monospiro-', 'dispiro-', and 'trispiro-' respectively. 'It is 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, each carbon number containing one or more heteroatoms. It refers to a ring numbered from 2 to 60, but is not limited thereto.
  • heterocyclic groups include single rings containing heteroatoms, ring aggregates, multiple fused ring systems, spiro compounds, etc.
  • aliphatic ring used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes single rings, ring aggregates, fused multiple ring systems, spiro compounds, etc., and has the number of carbon atoms unless otherwise specified. It means 3 to 60 rings, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it is an aliphatic ring.
  • 'silyl group' used in the present invention refers to a substituted or unsubstituted silyl group and a substituent represented by -Si(R) 3 '.
  • the unsubstituted silyl group is -SiH 3
  • the substituted silyl group includes at least one of the H substituents other than H, such as deuterium, an alkyl group, an aryl group, a heterocyclic group, a fluorenyl group, an aliphatic ring, an aromatic ring, and an aliphatic ring. It means that it has been replaced with a substituent such as a fused ring group.
  • the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., as examples of each symbol and its substituent may be written as the 'name of the group reflecting the valence', but is written as the 'parent compound name'. You may.
  • the name of the group may be written by distinguishing the valence, such as the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene', but the valence and Regardless, it can also be written as the parent compound name, ‘phenanthrene’.
  • pyrimidine in the case of pyrimidine, it can be written as 'pyrimidine' regardless of the valence, or it can be written as the 'name of the group' of the valence, such as pyrimidineyl group in the case of monovalent group, pyrimidineylene in the case of divalent group, etc. there is.
  • a is an integer of 0, it means that the substituent R 1 is absent. That is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring. In this case, the hydrogen bonded to the carbon is indicated as You can omit it and write the chemical formula or compound.
  • R 1 when a is an integer of 1, one substituent R 1 is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can be bonded as follows, for example, and a is 4 to 6 Even when it is an integer, it is bonded to the carbon of the benzene ring in a similar way, and when a is an integer of 2 or more, R 1 may be the same or different.
  • a ring refers to an aryl ring, heteroaryl ring, fluorene ring, aliphatic ring, etc.
  • a number-ring refers to a condensed ring
  • a number-atom ring refers to the form of a ring. It can mean.
  • naphthalene corresponds to a 2-ring
  • anthracene corresponds to a 3-ring condensed ring
  • thiophene or furan corresponds to a 5-membered heterocycle
  • benzene or pyridine corresponds to a 6-membered aromatic ring.
  • the ring formed by combining adjacent groups is an aromatic ring group of C 6 to C 60 ; fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and an aliphatic ring group of C 3 to C 60 .
  • the aromatic ring group may include an aryl ring
  • the heterocyclic group may include a heteroaryl ring.
  • 'neighboring groups' refers to groups R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 5 using the following chemical formula as an example. and R 6 , as well as R 7 and R 8 that share one carbon, and ring configurations that are not immediately adjacent, such as between R 1 and R 7 , between R 1 and R 8 , or between R 4 and R 5 Substituents bonded to elements (such as carbon or nitrogen) may also be included. In other words, if there are substituents on immediately adjacent ring elements such as carbon or nitrogen, they can become neighboring groups, but if no substituents are bonded to the immediately adjacent ring elements, they can be bonded to the next ring element.
  • the expression 'neighboring groups can combine with each other to form a ring' is used in the same meaning as 'neighboring groups can selectively form a ring by combining with each other', and at least one pair This refers to a case where neighboring groups combine with each other to form a ring.
  • Substituents such as arylthio groups, arylthio groups, etc., rings formed by bonding adjacent groups, etc.
  • C 1 -C 20 alkyl group are each deuterium; halogen; Cyano group; nitro group; siloxane group; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 aliphatic ring group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkyne group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkylthio group; C 6 -C 20 arylthio group; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; and a phosphine oxide group unsubstituted or substituted with a C 1 -C 20
  • a component such as a layer, membrane, region, plate, etc.
  • it means not only that it is “directly above” the other component, but also that there is another component in between. It should be understood that it can also include cases.
  • an element is said to be “right on top” of another part, it should be understood to mean that there is no other part in between.
  • 1 to 3 are exemplary diagrams of organic electric devices according to embodiments of the present invention.
  • the 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, and an inorganic material layer may be included between the first electrode 110 and the second electrode 120.
  • the first electrode 110 may be an anode
  • the second electrode 170 may be a cathode
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic material layer refers to a layer containing at least one organic material.
  • 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 electron injection layer 160 may be an inorganic material layer that does not contain organic materials.
  • 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 may be formed sequentially on the first electrode 110.
  • the luminous efficiency improvement layer 180 may be formed on one side of both sides of the first electrode 110 or both sides of the second electrode 170 that is not in contact with the organic material layer or the inorganic material layer, and the luminous efficiency improvement layer 180 ) is formed, the light efficiency of the organic electric device can be improved.
  • the luminous efficiency improvement layer 180 may be formed on the second electrode 170.
  • the luminous efficiency improvement layer 180 is formed to form the second electrode 170.
  • SPPs surface plasmon polaritons
  • 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 includes a hole injection layer 120, a hole transport layer 130, a buffer layer 210, and a hole injection layer 120 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 improvement layer 180 is formed on the second electrode. It can be.
  • 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 be formed in a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer. This will be explained with reference to FIG. 3 .
  • the organic electric device 300 has two stacks (ST1, ST2) of multi-layered organic material layers between the first electrode 110 and the second electrode 170. More than a set may be formed, and a charge generation layer (CGL) may be formed between the stacks of the organic material layers.
  • ST1, ST2 two stacks of multi-layered organic material layers between the first electrode 110 and the second electrode 170. More than a set may be formed, and a charge generation layer (CGL) may be formed between the stacks of the organic material layers.
  • CGL charge generation layer
  • 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 may include a light efficiency improvement layer (180).
  • the first stack (ST1) is an organic material layer formed on the first electrode 110, which includes a first hole injection layer 320, a first hole transport layer 330, a first light emitting 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 light-emitting layer 440, and a second electron transport layer 450.
  • the first stack and the second stack may be organic material layers with the same stacked structure, or they may be organic material layers with 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.
  • This charge generation 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
  • the second light-emitting layer 440 may include a material doped with a greenish yellow dopant and a red dopant in a green host.
  • the materials of the first light emitting layer 340 and the second light emitting layer 440 according to the embodiment of the present invention are not limited thereto.
  • n may be an integer between 1 and 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 may be included in the organic layer.
  • the compound represented by Formula 1 of the present invention includes a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), an auxiliary light emitting layer (220), an electron transport layer (150, It can be used as a material for the light emitting layer (140, 340, 440), the light emitting layer (140, 340, 440), or the light efficiency improvement layer (180), but is preferably used as a material for the light emitting layer (140, 340, 440) or/and the light efficiency improvement layer (180), More preferably, it can be used as a host for the light emitting layer (140, 340, 440).
  • the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so research on the selection of the core and the combination of sub-substituents attached to it is required, and in particular, when the energy level and T 1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved simultaneously.
  • the compound represented by Formula 1 as a material for the light emitting layer (140, 340, 440), the energy level and T 1 value between each organic material layer, the intrinsic properties of the material (mobility, interface properties, etc.), etc. By optimizing it, the lifespan and efficiency of organic electric devices can be improved simultaneously.
  • An 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, an 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 is formed thereon. , It can be manufactured by 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, and then depositing a material that can be used as the cathode 170 thereon. there is.
  • a deposition method such as PVD or CVD.
  • an 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 is formed thereon.
  • It can be manufactured by 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, and then depositing a material that can be used as the
  • a light-emitting auxiliary layer 220 may be formed between the hole transport layer 130 and the light-emitting layer 140, and an electron transport auxiliary layer (not shown) may be further formed between the light-emitting layer 140 and the electron transport layer 150. As shown, it can also be formed in a stack structure.
  • the organic material layer uses a variety of polymer materials, such as a solution process or solvent process rather than a deposition method, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, and doctor bleed process. It can be manufactured with fewer layers by methods such as a printing process, screen printing process, or 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 front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.
  • the organic electric device may be selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting devices, and quantum dot display devices.
  • 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 that controls 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, navigation devices, game consoles, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • Z 1 to Z 3 are C(R') or N, and at least one of Z 1 to Z 3 is N.
  • R' is independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C 6 to C 60 ; fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 20 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkyne group; C 1 ⁇ C 20 alkoxy group; and a C 6 to C 20 aryloxy group.
  • X 1 to X 5 are independently C(R a ) or C(R b ).
  • the R a are the same or different from each other and are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C 6 to C 60 ; fluorenyl group; A C 2 to C 16 heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 30 alkenyl group; C 2 ⁇ C 30 alkyne group; C 1 ⁇ C 30 alkoxy group; and aryloxy groups of C 6 to C 30 , and adjacent groups may be bonded to each other to form a ring.
  • the R b are the same or different from each other and are independently an aryl group of C 6 to C 60 ; fluorenyl group; A C 2 to C 16 heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 30 alkenyl group; C 2 ⁇ C 30 alkyne group; C 1 ⁇ C 30 alkoxy group; and aryloxy groups of C 6 to C 30 , and adjacent groups may be bonded to each other to form a ring.
  • L 1 to L 3 are independently a single bond; C 6 ⁇ C 60 arylene group; fluorenylene group; C 3 ⁇ C 60 aliphatic ring group; and a C 2 to C 60 heterocyclic group containing at least one hetero atom selected from O, N, S, Si, and P.
  • Ar 1 is an aryl group of C 6 to C 60 ; fluorenyl group; C 3 ⁇ C 60 aliphatic ring group; C 2 ⁇ C 60 heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a silyl group.
  • the 9-carbazolyl group refers to a substituted or unsubstituted 9-carbazolyl group, and does not include forms in which the 9-carbazolyl group is fused to a moiety among polycyclic rings.
  • R 1 to R 4 are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; Aryl group of C 6 to C 60 ; fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 20 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkyne group; C 1 ⁇ C 20 alkoxy group; and C 6 to C 20 aryloxy groups, and adjacent groups may be bonded to each other to form a ring.
  • a and b are each integers from 0 to 4
  • c and d are each integers from 0 to 5
  • each of R 1 , each of R 2 , each of R 3 , and each of R 4 are equal to or Different.
  • a ring formed by combining adjacent groups is an aromatic ring group of C 6 to C 60 ; fluorenylene group; C 3 ⁇ C 60 heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a C 6 to C 60 aliphatic ring group.
  • the aromatic ring may be, for example, C 6 to C 20 , C 6 to C 18 , C 6 to C 16 , C 6 to C 14 , C 6 to C 13 , It may be an aromatic ring such as C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 , specifically, benzene, naphthalene, anthracene, and phenene. It may be an aryl ring such as tren, pyrene, etc.
  • the aryl group is, for example, C 6 to C 30 , C 6 to C 29 , C 6 to 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 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18, etc., specifically, phenyl, bi
  • the arylene 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 to 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 , It may be an arylene group such as C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , and specifically, phenylene, biphenyl, naphthylene
  • the heterocyclic group is, for example, C 2 to C 30 , C 2 to 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
  • R 1 to R 4 , Ar 1 , R', R a , and R b is a fluorenyl group, or at least one of L 1 and L 2 is a fluorenylene group, the fluorenyl group or fluorenylene
  • the group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11,9' -fluorene], benzo[ b ]fluorene, 11,11-diphenyl- 11H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H -fluorene, etc. .
  • the aliphatic ring group is, for example, C 3 to C 20 , C 3 to C 19 , C 3 ⁇ C 18 , C 3 ⁇ C 17 , C 3 ⁇ C 16 , C 3 ⁇ C 15 , C 3 ⁇ C 14 , C 3 ⁇ C 13 , C 3 ⁇ C 12 , C 3 ⁇ C 11 , C 3 Aliphatic ring groups such as ⁇ C 10 , C 3 ⁇ C 8 , C 3 ⁇ C 6 , C 6 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18, etc. You can.
  • R 1 to R 4 , R', R a and R b is an alkyl group
  • the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C It may be an alkyl group such as 2 , C 3 , or C 4 , and may be, for example, a methyl group, an ethyl group, or a t-butyl group.
  • the alkoxy group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C It may be an alkoxy group such as 2 , C 3 , or C 4 , and may be, for example, a methoxy group, an ethoxy group, or a t-butoxy group.
  • the alkenyl group is, for example, C 2 to C 20 , C 2 to C 10 , C 2 to C 4 , C 2 It may be an alkene group such as , C 3 , or C 4 .
  • the rings formed by combining neighboring groups each contain deuterium; halogen; Cyano group; nitro group; siloxane group; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 aliphatic ring group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkyne group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; And it may
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other.
  • the aryl group is, 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 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 ,
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other.
  • the heterocyclic group is, for example, C 2 to C 30 , C 2 to C 29 , C 2 to C 28 , C 2 to C 27 , C 2 to C 26 , C 2 to 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, C 2 ⁇ C 4 , C 2 ⁇ C 3 , C 2 , C 3 , C 4 , C 2 ⁇ C 3 , C 2 , C 3 ,
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other.
  • the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobi Fluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11 H -benzo[ b ]fluorene, 9-(naphthalene -2-yl) 9-phenyl-9 H -fluorene, etc.
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other.
  • the aliphatic ring group is, for example, C 3 to C 20 , C 3 to C 19 , C 3 to C 18 , C 3 to C 17 , C 3 to C 16 , C 3 to C 15 , C 3 ⁇ C 14 , C 3 ⁇ C 13 , C 3 ⁇ C 12 , C 3 ⁇ C 11 , C 3 ⁇ C 10 , C 3 ⁇ C 8 , C 3 ⁇ C 6 , C 6 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , and C 18 may be an aliphatic ring group.
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other.
  • the alkyl group may be, for example, an alkyl group such as C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , or C 4 .
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other.
  • the alkoxy group may be, for example, an alkoxy group such as C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , or C 4 .
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, silyl group, and adjacent groups are formed by bonding to each other.
  • 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 , or C 4 .
  • At least one of L 1 to L 3 may be selected from the group consisting of the following formulas (a-1) to (a-15).
  • R 5 , R 6 , R 7 and R 8 are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; siloxane group; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 aliphatic ring group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkyne group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkylthio group; and C 6 -C 20 arylthio groups, and adjacent groups can combine with each other to form a ring, m and n are each integers from 0 to 4, and o' is from 0 to 5. It is an integer, and p' is an integer of
  • L 2 and L 3 may be asymmetric with each other.
  • 'asymmetry' is a concept that includes not only different substituents but also substituents with different bonding positions even for the same substituent. For example, when one of L 2 and L 3 is p-phenylene and the other is m-phenylene. , these substituents are all the same as 'phenylene', but the bonding positions are different, so they are considered asymmetric. Additionally, even when one of L 2 and L 3 is unsubstituted phenylene and the other is substituted phenylene, it is considered asymmetric.
  • L 3 may be a single bond.
  • At least one of R a and R b may be selected from the group consisting of an alkyl group of C 1 to C 20 and the following Formulas 2-1 to 2-7.
  • each symbol may be defined as follows.
  • R 7 to R 12 are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; siloxane group; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 aliphatic ring group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkyne group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkylthio group; and arylthio groups of C 6 -C 20 , and adjacent groups may be bonded to each other to form a ring.
  • l is an integer from 0 to 5
  • o, q, r and s are each an integer from 0 to 4
  • p is an integer from 0 to 3 and when each of these is an integer of 2 or more, each of R 7 , R 8 ,
  • R 9 and R 10 are the same as or different from each other.
  • Y is S or O.
  • R a is a single bond; C 1 -C 20 alkylene group; C 6 -C 30 arylene group; fluorenylene group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C 3 -C 30 aliphatic ring groups.
  • R b is hydrogen; heavy hydrogen; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C 3 -C 30 aliphatic ring groups.
  • Ar 1 may be selected from the group consisting of Formulas 3-1 to 3-8 below.
  • R 13 to R 21 are independently hydrogen; heavy hydrogen; halogen; Cyano group; nitro group; siloxane group; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 aliphatic ring group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkyne group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkylthio group; and arylthio groups of C 6 -C 20 , and adjacent groups may be bonded to each other to form a ring.
  • t, za, zb and zc are each an integer from 0 to 5
  • u, w, x and y are each an integer from 0 to 4
  • v is an integer from 0 to 3 and if they are each an integer of 2 or more, R 13
  • R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are the same as or different from each other.
  • Y is S or O.
  • R a is a single bond; C 1 -C 20 alkylene group; C 6 -C 30 arylene group; fluorenylene group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C 3 -C 30 aliphatic ring groups.
  • R b is hydrogen; heavy hydrogen; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; and C 3 -C 30 aliphatic ring groups.
  • Formula 3-8 corresponds to a silyl group substituted with an aryl group.
  • Formula 1 when Ar1 is Formula 3-8, Formula 1 may be expressed as Formula 1-1 below.
  • Z 1 to Z 3 X 1 to Hydrogen independently; heavy hydrogen; halogen; Cyano group; nitro group; siloxane group; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 aliphatic ring group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkyne group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkylthio group; and an arylthio group of C 6 -C 20 , and adjacent groups can combine with each other to form a ring, and za, zb, and zc are each integers of 0 to 5.
  • L 3 may be a single bond.
  • Chemical Formula 1 may be expressed as Chemical Formula 1-2 below.
  • Formula 1-1, and Formula 1-2 at least one of X 1 to X 5 may be C(R b ).
  • At least one of R a and R b is an aryl group of C 6 to C 30 ; C 1 ⁇ C 4 alkyl group; C 3 ⁇ C 10 cycloalkyl group; carbazolyl group; Dibenzofuryl group; Dibenzothiophene diary; benzocarbazolyl group; Naphthobenzofuryl group; and naphthobenzothiophenyl group.
  • At least one of R a and R b may be an aryl group of C 6 to C 30 substituted with at least one deuterium
  • Ar 1 may be an aryl group of C 2 to C 60 substituted with at least one deuterium. It may be a heterocyclic group.
  • R 5 to R 21 , R a , and R b are each deuterium; halogen; Cyano group; nitro group; siloxane group; C 6 -C 30 aryl group; fluorenyl group; A C 2 -C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 aliphatic ring group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkyne group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkylthio group; And it may be further substituted with one or more substituents selected from the group consisting of C 6 -C 20 arylthio groups.
  • 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 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 .
  • the organic material layer includes a light-emitting layer and a hole transport zone formed between the first electrode and the light-emitting layer, and the hole transport zone includes the compound represented by Formula 1.
  • the hole transport zone includes a light-emitting auxiliary layer, and the light-emitting auxiliary layer may include the compound of Formula 1.
  • 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 first electrode, and in this case, the organic material layer may further include a charge generation layer formed between the two or more stacks. there is.
  • the organic electric device further includes a light efficiency improvement layer, and the light efficiency improvement layer may be formed on both sides of the first electrode or both sides of the second electrode, which is not in contact with the organic material layer.
  • the present invention provides an electronic device including a display device and a control unit that drives the display device.
  • the display device includes an organic electric element containing the compound represented by Chemical Formula 1.
  • the compound (final products) represented by Chemical Formula 1 according to the present invention may be synthesized by the reaction route of Scheme 1-1 or Scheme 1-2 below, but is not limited thereto.
  • Sub 1 of Scheme 1 may be synthesized through the reaction route of Scheme 2-1 or Scheme 2-2 below, but is not limited thereto.
  • Compounds belonging to Sub 1 may be, but are not limited to, the following compounds, and the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1.
  • Sub 2 of Schemes 1-1 and 1-2 can be synthesized by the reaction route of Scheme 3 below, and when Ar 1 is a silyl group (-Si(R) 3 ), by the reaction route of Scheme 4 below. However, it is not limited to this.
  • Sub 2-2a (9.46 g, 30 mmol), Sub 2-81b' (13.87 g, 30 mmol), Pd(PPh 3 ) 4 (1.04 g, 0.9 mmol) and K 2 CO 3 (8.28 g, 60 mmol) was placed in a round bottom flask, dissolved in 75 mL of toluene and 25 mL of H 2 O, and stirred at 130°C for 8 hours. After completion of the reaction, extraction was performed with toluene and water, and the organic layer was dried over MgSO 4 and concentrated. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 13.10 g of product (yield: 71%).
  • Compounds belonging to Sub 2 may be, but are not limited to, the following compounds, and the FD-MS values of the following compounds are shown in Table 2.
  • Dissolve Sub 1-59 (10.0 g, 26.32 mmol) in Tetrahydrofuran (100 ml), bring to -78°C, and add 2.5M n-butyllithium in Hexane (10.53 ml, 26.32 mmol) dropwise. After dropwise, gradually increase to RT and stir for 2 hours.
  • Dissolve Sub 2-3 (12.16 g, 26.32 mmol) in Tetrahydrofuran (200 ml) and make the mixture at -78°C. After Lithiating Sub 1-59, bring it back to -78 °C and dropwise into Sub 2-3. After stirring for 30 minutes, the mixture was stirred at 80°C for 12 hours. When the reaction is complete, it is concentrated to remove the solvent. Afterwards, the concentrate was separated using a silica gel column and recrystallized to obtain 11.0 g of product (yield: 66%).
  • a 60nm thick hole injection layer was created by vacuum depositing 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) on the ITO layer (anode) formed on the glass substrate.
  • 2-TNATA 2-naphthyl(phenyl)amino]triphenylamine
  • NPB N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine
  • compound P-1 of the present invention was applied as a host material, and meridional-tris-(N-phenyl, N-methyl-pyridoimidazol-2-yl)iridium (III) (hereinafter referred to as 'mer') was applied as a dopant material.
  • 'mer' meridional-tris-(N-phenyl, N-methyl-pyridoimidazol-2-yl)iridium (III)
  • 'mer' meridional-tris-(N-phenyl, N-methyl-pyridoimidazol-2-yl)iridium
  • BAlq (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
  • BAlq tris(8-quinolinol) aluminum
  • Alq 3 tris(8-quinolinol) aluminum
  • LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm
  • Al was deposited to form a cathode with a thickness of 150 nm.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds of the present invention shown in Table 4 below were used as host materials instead of Compound P-1 of the present invention.
  • An organic electroluminescent device was manufactured in the same manner as Example 1, except that Comparative Compounds A to Comparative Compounds E below were used instead of Compound P-1 of the present invention as the host material.
  • Electroluminescence (EL) characteristics were obtained using PR-650 from PhotoResearch by applying a forward bias direct current voltage to the organic electroluminescent devices manufactured in Examples 1 to 25 and Comparative Examples 1 to 5 of the present invention.
  • the T95 lifespan was measured using a lifespan measuring device manufactured by McScience at a standard luminance of 1,000 cd/m 2 . The measurement results are shown in Table 4 below.
  • An organic electroluminescent device was manufactured in the same manner as Example 1, except that BD-052X (manufactured by Idemitsu Kosan) was used as a dopant material, and the dopant was doped so that the weight ratio of host and dopant was 96:4. did.
  • BD-052X manufactured by Idemitsu Kosan
  • An organic electroluminescent device was manufactured in the same manner as Example 24, except that the compound of the present invention shown in Table 5 below was used as the host material instead of the compound P-1 of the present invention.
  • Organic compound was prepared in the same manner as in Example 24, except that the following comparative compound F and comparative compounds B, C, and E used in Comparative Examples 2, 3, and 5 were used as the host material instead of the compound P-1 of the present invention.
  • An electroluminescent device was manufactured.
  • Electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch by applying a forward bias direct current voltage to the organic electroluminescent devices manufactured in Examples 26 to 46 and Comparative Examples 6 to 9 of the present invention.
  • the T95 lifespan was measured using a lifespan measuring device manufactured by McScience at a standard luminance of 500 cd/m 2 . The measurement results are shown in Table 5 below.
  • the efficiency and lifespan are significantly improved while the driving voltage of the organic electric device is lowered compared to the Comparative Example.
  • the azine moiety contains 9- It is similar to the compound of the present invention in that the carbazole group and the tetraphenylsilyl group are substituted, but the compound of the present invention differs in that at least one of the phenyl groups of the tetraphenylsilyl group is substituted with a substituent other than hydrogen or deuterium. Due to this difference, the compound of the present invention has greater steric hindrance than comparative compound B.
  • the Dexter energy transfer effect between the host and the dopant decreases and the Forster energy transfer effect increases, especially TTA (triplet -triplet annihilation) is reduced.
  • TTA triplet -triplet annihilation
  • Comparative Compound C and Comparative Compound D are similar to the compounds of the present invention in that an additional substituent is introduced to the phenyl of the tetraphenylsilyl group, but the packing density is reduced due to excessive hindrance effect during material deposition, resulting in a decrease in packing density. Electron mobility decreases and the characteristics of the device deteriorate compared to the present invention.
  • Comparative compound E is similar to the compound of the present invention, but differs in that both the silyl group and the azine group are substituted with 9-carbazolyl group.
  • the LUMO values of comparative compounds E and P-157 were measured using the DFT method (B3LYP/6-31g(D)) of the Gaussian program. The measurement results are shown in Table 6 below.
  • the compound P-157 of the present invention shows a lower LUMO value than the comparative compound E. Therefore, when the compound of the present invention is used as a host, electron injection from the electron transport layer to the light-emitting layer is smoother than that of comparative compound E, and thus excitons are better generated in the light-emitting layer, thereby improving device characteristics.
  • Comparative Compound F is a commonly used host, and it can be seen that the device characteristics are significantly improved when the compound of the present invention is used as a host compared to this general host.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (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. Du fait que le composé représenté par la formule chimique 1 est inclus dans la couche de matériau organique, la tension d'attaque de l'élément électrique organique peut être abaissée et l'efficacité d'émission de lumière et la durée de vie de celui-ci peuvent être améliorées.
PCT/KR2023/009098 2022-07-05 2023-06-29 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé WO2024010280A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR10-2022-0082269 2022-07-05
KR20220082269 2022-07-05
KR10-2023-0038683 2023-03-24
KR1020230038683A KR20240006426A (ko) 2022-07-05 2023-03-24 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR1020230082036A KR20240005586A (ko) 2022-07-05 2023-06-26 유기전기 소자용 화합물, 이를 이용한 유기전기소자및 그 전자 장치
KR10-2023-0082036 2023-06-26

Publications (1)

Publication Number Publication Date
WO2024010280A1 true WO2024010280A1 (fr) 2024-01-11

Family

ID=89453707

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2023/009098 WO2024010280A1 (fr) 2022-07-05 2023-06-29 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé

Country Status (2)

Country Link
KR (1) KR20240005609A (fr)
WO (1) WO2024010280A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20200062465A (ko) * 2018-11-26 2020-06-04 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자
US20210122765A1 (en) * 2019-10-25 2021-04-29 Universal Display Corporation Organic electroluminescent materials and devices
KR20220008442A (ko) * 2020-07-13 2022-01-21 삼성디스플레이 주식회사 발광 소자 및 이를 포함한 전자 장치
KR20220069721A (ko) * 2020-11-20 2022-05-27 단국대학교 천안캠퍼스 산학협력단 실레인 화합물 및 이를 포함하는 유기 발광 다이오드 소자
KR20220078000A (ko) * 2020-12-02 2022-06-10 삼성디스플레이 주식회사 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20200062465A (ko) * 2018-11-26 2020-06-04 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자
US20210122765A1 (en) * 2019-10-25 2021-04-29 Universal Display Corporation Organic electroluminescent materials and devices
KR20220008442A (ko) * 2020-07-13 2022-01-21 삼성디스플레이 주식회사 발광 소자 및 이를 포함한 전자 장치
KR20220069721A (ko) * 2020-11-20 2022-05-27 단국대학교 천안캠퍼스 산학협력단 실레인 화합물 및 이를 포함하는 유기 발광 다이오드 소자
KR20220078000A (ko) * 2020-12-02 2022-06-10 삼성디스플레이 주식회사 발광 소자

Also Published As

Publication number Publication date
KR20240005609A (ko) 2024-01-12

Similar Documents

Publication Publication Date Title
WO2019151682A1 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et dispositif électronique associé
WO2018004187A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2023003234A1 (fr) Composé pour élément électrique organique, élément électrique organique faisant appel à celui-ci, et dispositif électronique associé
WO2021261851A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique comprenant cet élément électrique organique
WO2021015555A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique comprenant ledit élément électrique organique
WO2019212289A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant un tel composé et dispositif électronique correspondant
WO2021112403A1 (fr) Élément électronique organique comprenant un composé organique, et dispositif électronique le comprenant
WO2013105747A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2019190101A1 (fr) Composé d'élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé
WO2021101247A1 (fr) Composé pour élément électrique organique, élément électrique organique contenant ledit composé et dispositif électronique associé
WO2022010305A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé
WO2021182893A1 (fr) Dispositif électroluminescent organique
WO2023096210A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé
WO2021201449A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant
WO2022075746A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé
WO2021230651A1 (fr) Élément électronique organique comprenant un composé pour élément électronique organique et dispositif électronique associé
WO2022004994A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique le comprenant
WO2024039119A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2021029675A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique
WO2016089165A2 (fr) Nouveau composé et élément électroluminescent le comprenant
WO2024080655A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique le comprenant
WO2021020873A1 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et dispositif électronique associé
WO2021230714A1 (fr) Élément électroluminescent organique
WO2016021923A2 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
WO2021162384A1 (fr) Composé pour dispositif électrique organique, dispositif électrique organique faisant appel à celui-ci, et dispositif électronique associé

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23835747

Country of ref document: EP

Kind code of ref document: A1