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WO2019190101A1 - Composé d'élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé - Google Patents

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

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WO2019190101A1
WO2019190101A1 PCT/KR2019/003116 KR2019003116W WO2019190101A1 WO 2019190101 A1 WO2019190101 A1 WO 2019190101A1 KR 2019003116 W KR2019003116 W KR 2019003116W WO 2019190101 A1 WO2019190101 A1 WO 2019190101A1
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organic
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Korean (ko)
Inventor
문성윤
이선희
박종광
소기호
김원삼
박정환
박치현
채미영
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DukSan Neolux Co Ltd
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DukSan Neolux Co Ltd
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Priority claimed from KR1020190029346A external-priority patent/KR102720177B1/ko
Application filed by DukSan Neolux Co Ltd filed Critical DukSan Neolux Co Ltd
Priority to CN202310372237.1A priority Critical patent/CN116332914B/zh
Priority to CN201980018624.7A priority patent/CN111836872B/zh
Priority to CN202310372220.6A priority patent/CN116332916B/zh
Priority to US17/043,595 priority patent/US11856843B2/en
Publication of WO2019190101A1 publication Critical patent/WO2019190101A1/fr
Anticipated expiration legal-status Critical
Priority to US17/343,040 priority patent/US12063855B2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • 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
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • 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
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material 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, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like according to their functions.
  • the LUMO and HOMO levels of the host material have a great influence on the efficiency and lifespan of the organic EL device. As a result, it is possible to prevent efficiency degradation and lifespan reduction due to charge balance control, dopant quenching, and light emission at the hole transport layer interface in the light emitting layer.
  • the energy transfer in the light emitting layer for thermal activated delayed fluorescent (TADF) and exciplex can be identified by the PL lifetime (TRTP) method.
  • the time resolved transient PL (TRTP) method is a method of observing a decay time of a spectrum after a pulsed light source is irradiated to a host thin film. It is a measuring method.
  • TRTP measurement is a measurement method that can distinguish between fluorescence and phosphorescence, and energy transfer method, exciplex energy transfer method, and TADF energy transfer method within a mixed host material.
  • the present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance control, efficiency and lifetime in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent organic electroluminescent device comprising a phosphorescent dopant Compound which can improve It aims at providing the organic electric element using this and its electronic device.
  • the present invention combines a specific first host material with a specific second host material as a main component to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device, thereby reducing the energy barrier between the light emitting layer and the adjacent layer. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and long life of the organic electric device.
  • the present invention provides an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer.
  • an organic electric device comprising a first host compound represented by 1 and a second host compound represented by Formula 2 below.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electric element, and also to greatly improve the life of the element.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • alkenyl group As used herein, the terms “alkenyl group”, “alkenyl group” or “alkynyl group” have a double or triple bond of 2 to 60 carbon atoms, respectively, unless otherwise stated, and include straight or branched chain groups. It is not limited to this.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 instead of carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consist
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, that is, when a is 0, it means that all of the carbons forming the benzene ring are bonded to hydrogen. Omitted formulas and compounds may be omitted.
  • a is an integer of 1
  • one substituent R 1 is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, each of them is bonded as follows, and R 1 may be the same or different from each other.
  • a is an integer of 4 to 6
  • the present invention provides an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer.
  • an organic electric device comprising a first host compound represented by 1 and a second host compound represented by Formula 2 below.
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 are each independently hydrogen; heavy hydrogen; halogen; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si, P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); Or Ar 1 and Ar 2 , or Ar 3 and Ar 4 may be bonded to each other to form a ring,
  • L ' is a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; And a C 2 -C 60 heterocyclic group; selected from the group consisting of R a and R b independently of each other an C 6 -C 60 aryl group; Fluorenyl groups; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; And a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P, and
  • L 1 , L 2 , L 3 , L 4 and L 5 are each independently a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; Or a C 2 to C 60 heteroarylene group including at least one heteroatom of O, N, S, Si, and P;
  • X 1 is O or S
  • Rings A and B are each independently of the other C 6 ⁇ C 20 aryl group; Or a C 2 -C 20 heterocyclic group,
  • X 2 is a single bond, NL 6 -Ar 7 , O, S or CR'R ",
  • R 'and R are each independently hydrogen; C 6 ⁇ C 60 aryl group; Fluorenyl group; C 3 ⁇ C 60 Heterocyclic group; or C 1 ⁇ C 50 Alkyl group; R' and R" Can combine with each other to form a ring as a spy,
  • x is an integer of 0-4, y is an integer of 0-3, R c and R d are each independently hydrogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); Is selected from the group consisting of
  • aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Aryl group of C 6 -C 20 ; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -C 20 heterocyclic group; A cycloalkyl group of C 3 -C 20 ; C 7 -C 20 arylalkyl group and C 8 -C 20
  • the present invention provides an organic electroluminescent device comprising a compound represented by any one of the formulas A-1 to A-7 independently of each other in A and B in the general formula (1).
  • Z 1 to Z 48 are independently of each other CR c or N,
  • Z 1 to Z 48 bonded to L 1 to L 3 are carbon (C),
  • R c is the same as defined above for R a ,
  • the present invention provides an organic electroluminescent device comprising a compound represented by any one of L 1 to L 5 in the formula (1) or formula (2).
  • Y is NL 5 -Ar 7 , O, S or CR d R e ,
  • L 5 is the same as defined above in L 3 ,
  • Ar 7 is the same as defined in Ar 5 ,
  • R d and R e are the same as defined above for R a ,
  • a, c, d and e are each independently an integer from 0 to 4, b is an integer from 0 to 6,
  • f and g are each independently an integer of 0 to 3
  • h is an integer of 0 to 2
  • i is an integer of 0 or 1
  • R 1 , R 2 and R 3 are independently of each other hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L a -N (R f ) (R g ); or when a, b, c, d, e, f and g are 2 or more, and h is 2 or more, respectively A plurality of R
  • L a is a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A C 2 -C 60 heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; And an aliphatic hydrocarbon group of C 3 -C 60 ; wherein R f and R g are independently of each other an aryl group of C 6 -C 60 ; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one hetero atom selected from the group consisting of O, N, S, Si and P; And a fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 .
  • Z 49 , Z 50 and Z 51 are independently of each other CR h or N, and at least one of Z 49 , Z 50 and Z 51 is N,
  • R h is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; And an C 6 -C 30 aryloxy group; adjacent R 1 and R h may be bonded to each other to form an aromatic ring or a heteroaromatic ring.
  • the present invention provides an organic electroluminescent device comprising a compound represented by any one of the following formula (3) to the first host compound represented by the formula (1).
  • X 1 , A, B, L 1 , L 2 , Ar 2 , Ar 3 and Ar 4 are as defined above,
  • W is NL 7 -Ar 8 , O, S, or CR i R j ,
  • L 6 and L 7 are the same as the definition of L 4 ,
  • Ar 8 is the same as defined in Ar 5 ,
  • R i and R j are the same as the definition of R a ,
  • Two Ar 8 are each the same or different, two W are each the same or different, two C are the same or different, and two D are the same or different.
  • the present invention provides an organic electroluminescent device comprising a compound represented by Chemical Formula 1, wherein the first host compound is represented by Chemical Formula 1.
  • X 1 , Ar 2 , Ar 3 and Ar 4 are as defined above,
  • Z 1 , Z 2 , Z 3 and Z 4 are independently of each other CR c or N,
  • Z 1 to Z 4 bonded to N are carbon (C)
  • R c is the same as defined above for R a ,
  • W is NL 7 -Ar 8 , O, S, or CR i R j ,
  • L 7 is the same as defined above in L 4 ,
  • Ar 8 is the same as defined in Ar 5 ,
  • R i and R j is as defined above R a. ⁇
  • the first host compound represented by Chemical Formula 1 provides an organic electric device including the compound represented by Chemical Formula 7, Chemical Formula 8, or Chemical Formula 9 below.
  • X 1 , Ar 2 , Ar 3 and Ar 4 , Z 1 , Z 2 , Z 3 , Z 4 , and W are as defined above.
  • the present invention provides an organic electroluminescent device including a compound represented by any one of the following Chemical Formulas 10 to 13, wherein the second host compound represented by Chemical Formula 2 is present.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the following formula 14 is the second host compound represented by the formula (2).
  • X 3 is the same as the definition of X 2 above,
  • R e and R f are the same as the definitions of R d and R c ,
  • n is the same as y and m is the definition of x ⁇
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (15) to the second host compound represented by the formula (2).
  • X 2 , L 3 , L 4 , L 5 , Ar 5 , R c , R d , x, y, X 3 , R e , R f , m, n are as defined above ⁇
  • the present invention includes a compound represented by the formula (2), and provides a compound represented by the formula (19).
  • A is the following formula A-1 or formula A-2,
  • X 11 and X 12 are each independently O or S,
  • a ', b', c 'and d' are each independently 0 or 1,
  • Ar 11 , Ar 12 , Ar 13 and Ar 14 are each independently a C 6 -C 18 aryl group. ⁇
  • the compound represented by Chemical Formula 19 includes a compound represented by the following Chemical Formula 20 or Chemical Formula 21.
  • the present invention includes a compound represented by the following Chemical Formula 22, which is a compound represented by Chemical Formula 2, and provides such a compound.
  • Such a compound may be mixed with a second host such as Bis-carbazole, tertiary amine, polycyclic heterocyclic compound, and used in the light emitting layer.
  • a second host such as Bis-carbazole, tertiary amine, polycyclic heterocyclic compound, and used in the light emitting layer.
  • A is the following Formula A-1 or A-2,
  • Ar 11 is an aryl group of C 6 -C 18 ,
  • X 11 , X 12 and X 13 are each independently O or S,
  • n' and n' are each independently 0 or 1
  • a 'and c' are each independently an integer of 0 to 5
  • d represents the integer of any one of 0-4,
  • R 21 is an aryl group of C 6 -C 18 .
  • Ar 13 and Ar 14 are each independently a C 6 -C 18 aryl group. ⁇
  • the compound represented by Chemical Formula 22 may be represented by the following Chemical Formula 23 or Chemical Formula 24, and the present invention provides such a compound.
  • the compound included in Formula 2 may be used in the light emitting layer by mixing with a second host such as Bis-carbazole, tertiary amine, polycyclic heterocyclic compound, and more specifically, the compound included in Formula 19 or Formula 22 may be used. .
  • the first host compound represented by Formula 1 includes the following compound 1-1 to compound 1-175.
  • the second host compound represented by Chemical Formula 2 in the present invention includes the following compound. That is, compound 1'-1 to 1'-84, 2-1 to 2-60, 3-1 to 3-36, P-1 to P-120, 4-1 to 4-12, 5-1 to 5 -20, 6-1 to 6-16 and 7-1 to 7-24.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, and a first electrode 120 and a second electrode formed on a substrate 110.
  • An organic material layer including a compound represented by Chemical Formula 1 is provided between 180.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic material layer may sequentially include the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the light emitting auxiliary layer 151, the electron transport layer 160, and the electron injection layer 170 on the first electrode 120. It may include. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the electron transport auxiliary layer, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 are disposed thereon.
  • the organic material layer including the electron injection layer 170 it can be prepared by depositing a material that can be used as a cathode thereon.
  • the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
  • the present invention includes at least one hole transport band layer between the first electrode and the light emitting layer, the hole transport band layer includes a hole transport layer, a light emitting auxiliary layer or both, the hole transport band layer It provides an organic electric device comprising the compound represented by the formula (1).
  • the present invention provides an organic electroluminescent device included in the light emitting layer by mixing the compound represented by Formula 1 and Formula 2 in any one ratio of 1: 9 to 9: 1, preferably 1: 9 to 5: 5, more preferably, it is mixed in a ratio of 2: 8 or 3: 7 and included in the light emitting layer.
  • the organic electroluminescent device further includes a light efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer.
  • An organic electric device is provided.
  • the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, the organic material layer according to the present invention can be formed in various ways Therefore, the scope of the present invention is not limited by the formation method.
  • the organic electric element according to an embodiment of the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the present invention is a display device comprising the above-mentioned organic electric element; And a controller for driving the display device.
  • the organic electronic device provides an electronic device according to the present invention, wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • Final product 1 Compound represented by Formula 1 according to the present invention (final product 1) is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1, but is not limited thereto.
  • X 1 , A, B, L 1 , L 2 , Ar 1 to Ar 4 are the same as defined in Formula 1, and Hal 1 is Br or Cl.
  • Sub 1-5-c (7.16 g, 24.06 mmol) obtained in the above synthesis was dissolved in toluene (240 ml) in a round bottom flask, and then Sub 2-11 (5.28 g, 24.06 mmol) and Pd 2 (dba) 3 (0.66) g, 0.72 mmol), P ( t -Bu) 3 (0.49 g, 2.41 mmol), NaO t -Bu (4.62 g, 48.12 mmol) were added and stirred at 80 ° C.
  • the compound belonging to Sub 1 may be, but is not limited to, the following compounds.
  • Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 1.
  • Sub 2 of Scheme 3 may be synthesized by the reaction route of Scheme 3 (disclosed in Korean Patent Registration No. 10-1251451 (published on April 5, 2013) of the present applicant), but is not limited thereto.
  • Z 1 is Ar 1 or Ar 3
  • Z 2 is Ar 2 or Ar 4 .
  • Compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 2.
  • FD-MS Field Desorption-Mass Spectrometry
  • Sub 1-1 (5.97 g, 13.87 mmol) obtained in the synthesis was dissolved in toluene (140 ml) in a round bottom flask, and then Sub 2-17 (3.74 g, 13.87 mmol), Pd 2 (dba) 3 (0.38 g, 0.42 mmol), P ( t -Bu) 3 (0.28 g, 1.39 mmol), NaO t -Bu (2.67 g, 27.74 mmol) were added and stirred at 100 ° C.
  • Compound represented by the formula (2) according to the invention can be prepared by the reaction of Sub 3 and Sub 4, as shown in Scheme 4, but is not limited thereto.
  • Sub 1 (28) (40.8g, 80 mmol) and Sub 2 (10) (37.0g, 80 mmol) were obtained using the synthesis method of 1'-1 to obtain the product (45.4g, 70%).
  • Sub 1 (34) (44.0g, 80 mmol) and Sub 2 (29) (29.6g, 80 mmol) were obtained using the synthesis method of 1'-1 to obtain the product (41.2g, 68%).
  • Sub 1 (38) (50.7g, 80 mmol) and Sub 2 (24) (37.0g, 80 mmol) were obtained using the synthesis method of 1'-1 to give the product (51.6g, 69%).
  • Sub 1 (27) (40.8g, 80 mmol) and Sub 2 (36) (49.2g, 80 mmol) were obtained using the synthesis method of 1'-1 to obtain the product (53.9g, 70%).
  • Sub 1 (25) (34.7g, 80 mmol) and Sub 2 (39) (47.9g, 80 mmol) were obtained using the synthesis method of 1-1 to obtain the product (45.9g, 66%).
  • Sub 1 (37) (28.6g, 80mmol) and Sub 2 (10) (37.0g, 80mmol) were obtained using the synthesis method of 1'-1 to obtain the product (38.9g, 74%).
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm.
  • 2,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 60 nm as a hole transporting compound on the membrane to form a hole transport layer.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq the electron transport layer Tris (8-quinolinol) aluminum
  • Alq3 the electron transport layer Tris (8-quinolinol) aluminum
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 was used alone.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Formula 2 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and the compound represented by Chemical Formula 2 were used as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 and the compound represented by Chemical Formula 2 were used as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 and the compound represented by Chemical Formula 2 were used as a host.
  • Example 1 to Example 56 used as a host by mixing the compound of the formula (1) and formula (2) of the present invention showed a markedly improved effect.
  • the inventors of the present invention determine that each of the substances of the compound of Formula 1 and the compound of Formula 2 have new characteristics other than those of the substances, based on the experimental results, the substance of Formula 1, the substance of Formula 2 , PL lifetime was measured using the mixture of the present invention.
  • the compounds of the present invention were mixed with Chemical Formula 1 and Chemical Formula 2, it was confirmed that a new PL wavelength was formed differently from a single compound. It was confirmed that the decrease and disappearance time increased from about 60 times to as much as about 360 times.
  • the mixed thin film is an important example showing the exciplex energy transfer and the light emission process.
  • the combination of the present invention is superior to Comparative Examples 6 to 8 used as a phosphorescent host mixed with a comparative compound by using a compound represented by the formula (1) in which one more amine group is added in Comparative Compounds 2 and 3 to improve the hole characteristics.
  • Electrochemically synergistic effect with the compound represented by the general formula (2) having a strong electron properties thereby increasing the charge balance in the light emitting layer of holes and electrons, thereby emitting light in the light emitting layer rather than the hole transport layer interface, thereby the HTL interface Deterioration is also reduced, which maximizes the driving voltage, efficiency and lifetime of the device.
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm.
  • 2,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 60 nm as a hole transporting compound on the membrane to form a hole transport layer.
  • the inventive compound represented by the formula (19) or (21) was used as a host, and the dopant was 30 nm thick on the hole transport layer by doping Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] at a 5: 5 weight.
  • the light emitting layer of was deposited.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq the electron transport layer Tris (8-quinolinol) aluminum
  • Alq3 the electron transport layer Tris (8-quinolinol) aluminum
  • the electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage.
  • the T95 life was measured using a life measurement instrument manufactured by McScience.
  • the following table shows the results of device fabrication and evaluation.
  • the organic electroluminescent device was manufactured by the same method as Experimental Example 3, except that Comparative Compounds 4 to 7 were used as single hosts.
  • the organic electroluminescent device using the compound of the present invention as a phosphorescent host significantly improves driving voltage, efficiency, and lifetime as compared to the organic electroluminescent device using the comparative compound.
  • the difference between Comparative Compound 4 and the present invention is the difference in the presence or absence of a linking group of m-phenylene
  • Comparative Compound 5 and Comparative Compound 6 is the difference in the presence or absence of secondary substituents such as phenyl and biphenyl in dibenzouran
  • Comparative Compound 7 is substituted for dibenzofuran There is a difference depending on the number.
  • the linkage of m-phenylene has the effect of improving the efficiency, and the dibenzouran secondary substituent has the effect of significantly improving the life.
  • the energy level (HOMO level, LUMO level, T1 level) of the compound is remarkably changed as the specific substituent is substituted even in the same core, and the difference in the physical properties of the compound is a major factor in improving device performance during device deposition (for example, such as energy balance), suggesting that these different device results can be derived.
  • the present invention it is possible to manufacture an organic device having excellent device characteristics of high brightness, high light emission and long life, and there is industrial applicability.

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Abstract

La présente invention concerne : un nouveau mélange permettant d'améliorer l'efficacité d'émission de lumière, la stabilité et la durée de vie d'un élément ; un élément électrique organique l'utilisant et un dispositif électronique associé.
PCT/KR2019/003116 2018-03-29 2019-03-18 Composé d'élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé Ceased WO2019190101A1 (fr)

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CN202310372237.1A CN116332914B (zh) 2018-03-29 2019-03-18 用于有机电气元件的化合物、使用所述化合物的有机电气元件及其电子装置
CN201980018624.7A CN111836872B (zh) 2018-03-29 2019-03-18 用于有机电气元件的化合物、使用所述化合物的有机电气元件及其电子装置
CN202310372220.6A CN116332916B (zh) 2018-03-29 2019-03-18 用于有机电气元件的化合物、使用所述化合物的有机电气元件及其电子装置
US17/043,595 US11856843B2 (en) 2018-03-29 2019-03-18 Compound for organic electric element, organic electric element using the same, and electronic device therefor
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113950474A (zh) * 2019-11-05 2022-01-18 Lt素材株式会社 杂环化合物以及包括其的有机发光装置
JP2022025483A (ja) * 2020-07-29 2022-02-10 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子及び電子機器
EP3909946A3 (fr) * 2020-05-11 2022-02-23 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composés polycycliques pour dispositif électroluminescent organique
EP3972001A4 (fr) * 2020-03-11 2022-07-27 LG Chem, Ltd. Dispositif électroluminescent organique
WO2023052377A1 (fr) 2021-09-30 2023-04-06 Merck Patent Gmbh Appareil électroluminescent organique
WO2023052376A1 (fr) 2021-09-30 2023-04-06 Merck Patent Gmbh Appareil électroluminescent organique
US11760761B2 (en) 2020-08-17 2023-09-19 Aligos Therapeutics, Inc. Methods and compositions for targeting PD-L1
US11878968B2 (en) 2021-07-09 2024-01-23 Plexium, Inc. Aryl compounds and pharmaceutical compositions that modulate IKZF2
US12435073B2 (en) 2019-08-19 2025-10-07 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140101661A (ko) * 2011-11-22 2014-08-20 이데미쓰 고산 가부시키가이샤 방향족 복소고리 유도체, 유기 일렉트로루미네선스 소자용 재료 및 유기 일렉트로루미네선스 소자
KR20160107975A (ko) * 2015-03-06 2016-09-19 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
KR20170089599A (ko) * 2016-01-27 2017-08-04 에스에프씨 주식회사 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2018012780A1 (fr) * 2016-07-14 2018-01-18 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique
WO2018016742A1 (fr) * 2016-07-20 2018-01-25 주식회사 엘지화학 Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101170666B1 (ko) 2009-03-03 2012-08-07 덕산하이메탈(주) 비스카바졸 화합물 및 이를 이용한 유기전기소자, 그 단말
KR101729660B1 (ko) * 2014-05-09 2017-04-26 (주)씨엠디엘 신규한 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자 및 전자 기기
US10297762B2 (en) * 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10749113B2 (en) * 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
KR102338428B1 (ko) * 2016-02-03 2021-12-14 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR101849747B1 (ko) * 2016-07-20 2018-05-31 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR102018685B1 (ko) * 2016-07-29 2019-09-04 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102199075B1 (ko) * 2017-09-29 2021-01-07 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
CN111527616B (zh) * 2017-12-29 2024-03-08 三星Sdi株式会社 用于有机光电二极管的化合物、用于有机光电二极管的组合物、有机光电二极管和显示装置

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140101661A (ko) * 2011-11-22 2014-08-20 이데미쓰 고산 가부시키가이샤 방향족 복소고리 유도체, 유기 일렉트로루미네선스 소자용 재료 및 유기 일렉트로루미네선스 소자
KR20160107975A (ko) * 2015-03-06 2016-09-19 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
KR20170089599A (ko) * 2016-01-27 2017-08-04 에스에프씨 주식회사 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2018012780A1 (fr) * 2016-07-14 2018-01-18 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique
WO2018016742A1 (fr) * 2016-07-20 2018-01-25 주식회사 엘지화학 Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12435073B2 (en) 2019-08-19 2025-10-07 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
CN113950474A (zh) * 2019-11-05 2022-01-18 Lt素材株式会社 杂环化合物以及包括其的有机发光装置
CN113950474B (zh) * 2019-11-05 2024-12-10 Lt素材株式会社 杂环化合物以及包括其的有机发光装置
EP3972001A4 (fr) * 2020-03-11 2022-07-27 LG Chem, Ltd. Dispositif électroluminescent organique
EP3909946A3 (fr) * 2020-05-11 2022-02-23 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composés polycycliques pour dispositif électroluminescent organique
JP2022025483A (ja) * 2020-07-29 2022-02-10 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子及び電子機器
US11760761B2 (en) 2020-08-17 2023-09-19 Aligos Therapeutics, Inc. Methods and compositions for targeting PD-L1
US11878968B2 (en) 2021-07-09 2024-01-23 Plexium, Inc. Aryl compounds and pharmaceutical compositions that modulate IKZF2
WO2023052377A1 (fr) 2021-09-30 2023-04-06 Merck Patent Gmbh Appareil électroluminescent organique
WO2023052376A1 (fr) 2021-09-30 2023-04-06 Merck Patent Gmbh Appareil électroluminescent organique

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