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WO2013109027A1 - Composé, élément électronique organique l'utilisant et dispositif électronique associé - Google Patents

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

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Publication number
WO2013109027A1
WO2013109027A1 PCT/KR2013/000280 KR2013000280W WO2013109027A1 WO 2013109027 A1 WO2013109027 A1 WO 2013109027A1 KR 2013000280 W KR2013000280 W KR 2013000280W WO 2013109027 A1 WO2013109027 A1 WO 2013109027A1
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group
compound
aryl
substituted
mmol
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Korean (ko)
Inventor
김동하
이선희
최연희
문성윤
박정철
박용욱
지희선
박정환
이범성
황선필
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Duksan Hi Metal Co Ltd
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Duksan Hi Metal Co Ltd
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Priority claimed from KR1020120084503A external-priority patent/KR20130084960A/ko
Priority claimed from KR1020120084945A external-priority patent/KR101292554B1/ko
Priority claimed from KR1020120090101A external-priority patent/KR101251451B1/ko
Application filed by Duksan Hi Metal Co Ltd filed Critical Duksan Hi Metal Co Ltd
Priority to US14/362,883 priority Critical patent/US10026905B2/en
Publication of WO2013109027A1 publication Critical patent/WO2013109027A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • H10K50/805—Electrodes
    • H10K50/81—Anodes
    • H10K50/814—Anodes combined with auxiliary electrodes, e.g. ITO layer combined with metal lines

Definitions

  • the present invention relates to an organic electric element comprising the compound and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical 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 depending on their functions.
  • the most problematic problem is the life and efficiency of the organic electroluminescent device which is gradually progressing in large areas as life and efficiency.
  • Efficiency, lifespan, and driving voltage are related to each other. If the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage is decreased, the crystallization of organic materials by Joule heating generated during driving decreases, resulting in a longer lifespan. Indicates.
  • simply improving the organic layer may not maximize the efficiency. This is because long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value between each organic material layer and intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved.
  • a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.
  • the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
  • a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
  • An object of the present invention is to provide an organic electric device using the compound which can improve the high luminous efficiency, low driving voltage, high heat resistance, color purity and life of the device and its electronic device.
  • the present invention provides an organic electric device comprising a compound represented by the following formula (1), a light emitting auxiliary layer containing the formula (1) and a hole transport layer represented by the formula (2).
  • the present invention provides an electronic device using an organic electric element containing the compound represented by the above formula.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • halo or halogen as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.
  • alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it 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 a monocyclic or heterocyclic aromatic, 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.
  • 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 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.
  • heterocycloalkyl and “heterocyclic group” include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination.
  • the term 'neighborhood' here means a neighboring flag.
  • heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
  • heteroatom refers to N, O, S, P, and Si unless otherwise indicated.
  • 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.
  • saturated or unsaturated ring as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • 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 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Group, germanium group, and C 5 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • An organic material layer containing a compound represented by the formula (1) between) is provided.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At 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 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 compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • An organic electric device includes an anode, a cathode, and an organic material layer formed therebetween, and the organic material layer comprises a light emitting auxiliary layer containing a compound represented by the following Chemical Formula 1 and a hole transport layer represented by the following Chemical Formula 2. It may include.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • the compound represented by Chemical Formula 1 is applied to the light emitting auxiliary layer according to the present invention.
  • Ar 3 in Formula 2 is , or to be. That is, Formula 2 may be represented by the following formula.
  • the compound represented by Chemical Formula 2 may be applied to the hole transport layer.
  • n, o and p are integers of 1 to 4, m is an integer of 1 or 2, and when m, n, o, p 2 or more, a plurality of R One , R 2 , R 3 or R 4 Are the same as or different from each other, i) R One , R 2 , R 3 And R 4 Each independently of one another is hydrogen; heavy hydrogen; Tritium; Halogen group; C 6 ⁇ C 60 Aryl group; C One ⁇ C 50 Alkyl groups; C 2 ⁇ C 40 Alkenyl group; C 6 ⁇ C 60 Arylamine group; C containing at least one heteroatom of O, N, S, Si and P 2 ⁇ C 60 Heterocyclic group of; C 6 ⁇ C 60 Of aromatic rings and C 4 ⁇ C 60 Condensed ring groups of aliphatic rings of; Amine group; Nitro group; Nitrile group; Amide group And Selected from the group consisting of silane groups; Or ii) neighboring R One Neighboring R 2 Neigh
  • Ar 1 to Ar 7 are each independently a C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heteroaryl group containing at least one heteroatom of O, N, S, Si and P, C 2 ⁇ In the group consisting of C 20 alkenyl group, fluorenyl group, C 1 ⁇ C 30 alkoxy group, C 6 ⁇ C 30 aryloxy group, C 6 ⁇ C 60 arylamine group and C 1 ⁇ C 50 alkyl group Is selected.
  • R 1 to R 4 and Ar 1 to Ar 7 are an aryl group, each of these is hydrogen, deuterium, tritium, halogen, C 1 ⁇ C 60 alkyl group, C 1 ⁇ C 60 alkoxy group, C 1 C 60 -C 60 alkylamine group, C 6 -C 60 arylamine group, C 1 -C 60 alkylthiophene group, C 6 -C 60 aryl thiophene group, C 2 -C 60 alkenyl group, C 2 ⁇ C 60 of the alkynyl group, C 3 ⁇ C 60 cycloalkyl group, C 6 ⁇ C 60 aryl group, of a C 6 ⁇ C 60 substituted by deuterium aryl group, a C 8 ⁇ arylalkenyl group of C 60, a substituted Or may be substituted with one or more groups selected from the group consisting of an unsubstituted silane group, a substituted or unsubstituted boron group,
  • R One To R 4 And Ar One To Ar 7 Is a heterocyclic group, each of these is hydrogen, deuterium, tritium, halogen, C One ⁇ C 60 Alkyl group, C 2 ⁇ C 60 Alkenyl, C One ⁇ C 60 Alkoxy group, C One ⁇ C 60 Alkylamine groups, C 6 ⁇ C 60 Arylamine group, C One ⁇ C 60 Alkylthio group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 7 ⁇ C 20 Arylalkyl group, C 8 ⁇ C 20 Aryl alkenyl group, C 2 ⁇ C 20 Heterocyclic group, C 2 ⁇ C 60 It may be substituted with one or more substituents selected from the group consisting of an alkynyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group,
  • R One To R 4 And Ar One To Ar 7 When is an alkyl group, each of these is hydrogen, deuterium, tritium, halogen, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C One ⁇ C 20 Alkoxy group, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 7 ⁇ C 20 Arylalkyl group, C 8 ⁇ C 20 Aryl alkenyl group, C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,
  • R One To R 4 And Ar One To Ar 7 Is an alkenyl group, each of these is hydrogen, deuterium, tritium, halogen, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C One ⁇ C 20 Alkoxy group, C 6 ⁇ C 20 Arylamine group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 7 ⁇ C 20 Arylalkyl group, C 8 ⁇ C 20 Aryl alkenyl group, C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,
  • each of these is C One ⁇ C 60 Alkyl group, C 2 ⁇ C 60 Alkenyl, C 6 ⁇ C 60 Aryl group and C 8 ⁇ C 60 It may be substituted with one or more groups selected from the group consisting of arylalkenyl group of; Arylene group, nitro group, nitrile group, halogen group, C One ⁇ C 2 Alkyl group, C One ⁇ C 2 Alkoxy group, C 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 It may be substituted with one or more groups selected from the group consisting of a hetero ring group and an amino group of;
  • R One To R 4 And Ar One To Ar 7 When is an alkoxy group, each of these is hydrogen, deuterium, halogen, amino, nitrile, nitro, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C One ⁇ C 20 Alkoxy group, C 3 ⁇ C 30 Cycloalkyl group, C 2 ⁇ C 30 Heterocycloalkyl group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 60 Aryl group and C 2 ⁇ C 60 It may be substituted with one or more groups selected from the group consisting of a heteroaryl group of;
  • Ar 1 and Ar 7 are fluorenyl groups, each of them is hydrogen, deuterium, tritium, halogen group, C 2 ⁇ C 20 alkenyl group, C 1 ⁇ C 20 alkoxy group, C 6 ⁇ C 20 Aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 7 ⁇ C 20 arylalkyl group, C 8 ⁇ C 20 aryl alkenyl group, C 1 ⁇ C 50 alkyl group, C 2 ⁇ C 20 hetero May be substituted with one or more substituents selected from the group consisting of a cyclic group, a nitrile group and an acetylene group,
  • Ar 1 to Ar 7 are aryloxy groups, each of them is hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 alkenyl group, C 1 ⁇ C 20 alkoxy group, C 3 ⁇ C 30 cycloalkyl group, C 2 ⁇ C 30 heterocycloalkyl group, C 2 ⁇ C 30 heterocyclic group, C 6 ⁇ C 60 aryl group, C 6 ⁇ substituted with deuterium heteroaryl group of C 60 aryl group and C 2 ⁇ C 60 of which can be optionally substituted with one or more groups selected from the group consisting of;
  • R 1 to R 4 and Ar 1 to Ar 7 arylamine group each of which is a halogen group, an amino group, a nitrile group, a nitro group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 alkenyl group, C 1 C 20 -C 20 alkoxy group, C 3 -C 30 cycloalkyl group, C 2 -C 30 heterocycloalkyl group, C 6 -C 60 aryl group, C 6 -C 20 aryl group substituted with deuterium and C 2 May be substituted with one or more groups selected from the group consisting of C 60 heteroaryl groups)
  • Ar 1 and Ar 2 of Formula 1 may be selected from the following aryl group or fluorenyl group.
  • L of Formula 1 may be selected from the following groups.
  • Formula 1 may be represented by any one of the following Formula 3 to Formula 9 and Formula 15 to Formula 18.
  • Chemical Formulas 6 to 8 correspond to the case where adjacent R 1 combines with each other to form one or more aromatic hydrocarbons.
  • L, Ar 1 and Ar 2 are the same as defined in the formula (1).
  • Formula 15 to Formula 18 is more specifically, in Formula 1,
  • R One And R 2 are the same as or different from each other, i) R One And R 2 Each independently of one another is hydrogen; heavy hydrogen; Tritium; Halogen group; C One ⁇ C 50 Alkyl groups; C containing at least one heteroatom of O, N, S, Si and P 2 ⁇ C 60 Heterocyclic group of; C 2 ⁇ C 20 Alkenyl group; C 6 ⁇ C 60 Aryl group; And C 6 ⁇ C 60 An arylamine group; selected from the group consisting of ii) neighboring R One Companion and neighbor R 2 They combine with each other to form at least one ring (where a group that does not form a ring is as defined in i),
  • L is a C 6 ⁇ C 60 arylene group; Fluorenylene group; C 3 ⁇ C 60 Hetero arylene group; Or a divalent aliphatic hydrocarbon, each of which is nitro, nitrile, halogen, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 20 aryl group, C 2 -C 20 hetero ring May be substituted with a substituent with one or more substituents selected from the group consisting of a group and an amino group,
  • Ar 1 and Ar 2 are C 6 ⁇ C 60 An aryl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 2 -C 20 alkenyl group; And fluorenyl groups; This is the case when it is selected from the group consisting of.
  • each of a and b is an integer of 1 to 5, and when a and / or b are 2 or more, a plurality of R's 4 Or R 5 Are the same as or different from each other, i) R 4 And R 5 Are each independently of each other 6 ⁇ C 25 Aryl group; And C 2 ⁇ C 20 R is selected from the group consisting of alkenyl groups, or ii) 4 Chicks and neighboring R 5 Each group combines with each other to form at least one ring (where a group that does not form a ring is as defined in i),
  • R 4 and R 5 are an aryl group or an alkenyl group , each of them is one selected from the group consisting of hydrogen, C 1 ⁇ C 4 alkyl group, C 2 ⁇ C 6 alkenyl group and C 6 ⁇ C 20 aryl group It may be substituted with the above substituents.
  • Formula 2 may be represented by any one of the following Formula 10 to Formula 14, all of the corresponding R 3 or R 4 are bonded to each other to form one or more aromatic hydrocarbons.
  • the compound represented by Chemical Formula 1 may be one of the following Compounds 1-1 to 1-150, and the compound represented by Chemical Formula 2 may be the following Compounds 3-1 to 3-76, 4-1 to 4 -108, 5-1 to 5-52, 6-1 to 6-52, 7-1 to 7-64, 8-1 to 8-63, 9-1 to 9-64, 10-1 to 10-52 It may be one of the.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 16 below.
  • 2-TNATA a -N 1 -phenylbenzene-1,4-diamine
  • the dopant is doped by 90:10 by weight of CBP [4,4'-N, N'-dicarbazole-biphenyl] as a light emitting layer host and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium] as a dopant.
  • a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer.
  • BAlq (1,1'-bisphenyl) -4-oleato) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq (1,1'-bisphenyl) -4-oleato) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq Tris (8-quinolinol) aluminum
  • Alq 3 Tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to use an organic light emitting device.
  • An organic light emitting diode was manufactured in the same manner as in Example 6, but the hole transport layer was formed using the following Comparative Compound 1 instead of the compound of the present invention.
  • 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, and the measured results were measured at 300 cd / m 2 reference luminance.
  • the T90 life was measured using a life measurement instrument manufactured by McScience.
  • Table 5 below shows device fabrication and evaluation results of Examples and Comparative Examples to which the compound according to the present invention is applied.
  • the indole compound exhibits relatively higher efficiency and lifespan than the compounds of Formula 2.
  • the organic electroluminescent device was manufactured by using the compound 4-45 showing the low driving voltage and the indole compound having good efficiency and lifetime as the hole transporting layer and the light emitting auxiliary layer, respectively.
  • 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm, and then compound 4-45 was vacuum-deposited to a thickness of 20 nm as a hole transport compound on the hole injection layer. A hole transport layer was formed. Next, the compound according to the present invention and the comparative compound were vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • a dopant material as a host material (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] was doped in a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm.
  • (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum hereinafter abbreviated as BAlq
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a transport layer to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to use an organic light emitting device.
  • An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 2 instead of the compound of the present invention.
  • An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 3 instead of the compound of the present invention.
  • An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 4 instead of the compound of the present invention.
  • An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 5 instead of the compound of the present invention.
  • 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, and the measured results were measured at 300 cd / m 2 reference luminance.
  • the T90 life was measured using a life measurement instrument manufactured by McScience.
  • Table 6 below shows device fabrication and evaluation results of Examples and Comparative Examples to which the compound according to the present invention is applied.
  • the compounds of the present invention have a high T1 energy level and a deep HOMO energy level, holes are more smoothly transported from the hole transport layer to the light emitting layer, and excitons are confined in the light emitting layer, thereby realizing excellent organic electroluminescent devices. Because this is possible.
  • the indole core substituted with a phenyl group has improved efficiency and lifespan than the unsubstituted indole core, and the compound 1-5 of the present invention is an indole core substituted with a phenyl group at position 5,
  • the 1-6 lights showed low driving voltage, high efficiency and long life.
  • the compound according to the present invention when the compound according to the present invention is applied to an organic electroluminescent device, the device exhibits excellent device characteristics. ), Organic transistors (organic TFTs), monochromatic or white lighting elements, and the like.
  • the compound according to the present invention in addition to the hole transport layer or the light emission auxiliary layer, The same effect may be obtained even when used in a hole injection layer, a light emitting layer, a buffer layer, an electron injection layer, an electron transport layer, and the like.

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PCT/KR2013/000280 2012-01-18 2013-01-14 Composé, élément électronique organique l'utilisant et dispositif électronique associé Ceased WO2013109027A1 (fr)

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US14/362,883 US10026905B2 (en) 2012-01-18 2013-01-14 Compound, organic electric element using the same, and an electronic device thereof

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
KR20120005563 2012-01-18
KR10-2012-0005563 2012-01-18
KR1020120084503A KR20130084960A (ko) 2012-01-18 2012-08-01 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
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