WO2014010897A1 - Composé, élément électrique organique l'utilisant, et dispositif électronique le comprenant - Google Patents

Composé, élément électrique organique l'utilisant, et dispositif électronique le comprenant Download PDF

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WO2014010897A1
WO2014010897A1 PCT/KR2013/006046 KR2013006046W WO2014010897A1 WO 2014010897 A1 WO2014010897 A1 WO 2014010897A1 KR 2013006046 W KR2013006046 W KR 2013006046W WO 2014010897 A1 WO2014010897 A1 WO 2014010897A1
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aryl
substituted
alkenyl
deuterium
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Korean (ko)
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박정환
변지훈
이선희
문성윤
이범성
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덕산하이메탈(주)
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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    • C07D498/04—Ortho-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
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    • 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
    • C07F7/0816—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 said ring comprising Si as a ring atom
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • 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
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    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Definitions

  • the present invention relates to a compound, an organic electric element comprising 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 layer is often made of a multi-layer 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.
  • the material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • 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 element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • 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 polycyclic 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 single ring but also multiple rings, and adjacent groups may be formed by combining.
  • heterocycloalkyl includes one or more heteroatoms, unless otherwise indicated, having from 2 to 60 carbon atoms, including single rings as well as multicycles. Adjacent groups may be formed in combination.
  • 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 material layer using a variety of polymer materials is less by a solution process or solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition 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.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • A represents a benzene ring fused to each other by sharing two sides with two adjacent rings, it may be represented by the following formula (2).
  • B is a pentagonal ring condensed with A, including X and Y, and may be represented by the following Formula 3.
  • R 'and R are each independently of each other, hydrogen; C One ⁇ C 20 Alkyl group, C One ⁇ C 20 Alkoxy group, C One ⁇ C 20 Alkylamine groups, C One ⁇ C 20 Alkylthiophene groups, C 6 ⁇ C 20 Arylthiophene group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 3 ⁇ C 20 Cycloalkyl group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 8 ⁇ C 20 Aryl alkenyl group, silane group, boron group, germanium group and C 2 ⁇ C 20 C unsubstituted or substituted with a substituent selected from the group consisting of heterocyclic
  • Chemical Formula 3 may be represented by one of the following Chemical Formulas, and * represents a part condensed with an adjacent ring.
  • R One To R 6 are each independently of the other hydrogen; heavy hydrogen; Tritium; Halogen group; Hydrogen, deuterium, tritium, halogen, 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 C unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group One ⁇ C 50 Alkyl groups; 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,
  • R One To R 4 May each combine with a neighboring group to form a substituted or unsubstituted alicyclic, aromatic or hetero ring.
  • R 2 Is neighboring R One Or R 3 And may form an alicyclic, aromatic or heterocyclic ring.
  • n may be an integer of 0 to 2.
  • a plurality of R 6 may be the same or different from each other, and adjacent R 6 may combine with each other to form a substituted or unsubstituted alicyclic, aromatic or heterocycle.
  • L is nitro, nitrile, halogen, C One ⁇ C 20 Alkyl group, C One ⁇ C 20 Alkoxy group, C 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 C unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic group and an amino group of 6 ⁇ C 60 Arylene group; Hydrogen, deuterium, tritium, halogen, 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 One ⁇ C 50 Alkyl group, C 2 ⁇ C 20 A fluorenylene group unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene
  • Ar 1 and Ar 2 are each independently hydrogen, deuterium, tritium, a halogen group, a C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy group, C 1 ⁇ C 20 alkyl amine group, C 1 ⁇ C 20 alkyl thiophene group, C 6 ⁇ C 20 aryl thiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl group, C 3 ⁇ C 20 of the cycloalkyl of alkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted with a heavy hydrogen aryl, C 8 ⁇ C 20 arylalkenyl group, a silane group, a boron group, a germanium group, and a C 2 ⁇ C 20 of C 6 ⁇ C 60 aryl group unsubstituted or substituted with a substituent selected from the group consisting of a heterocycl
  • the compound represented by Formula 1 may be one of the following compounds 1-1 to 3-25.
  • Sub 1-1 was dissolved in anhydrous THF, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5 M in hexane) was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reaction was lowered to -78 °C, trimethyl borate was added dropwise and stirred at room temperature for 12 hours. After the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. Water in the reaction was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the resulting product was concentrated by separation of the organic solvent using column chromatography to obtain the desired product.
  • n-BuLi 2.5 M in hexane
  • Sub 1-1 examples are as follows, but are not limited thereto.
  • Sub 1 examples are as follows, but are not limited thereto, and their FD-MS are shown in Table 1 below.
  • LiF 8-quinolinol aluminum
  • Alq 3 tris (8-quinolinol) aluminum
  • LiF which is an alkali metal halide
  • the organic EL device was fabricated using Al / LiF formed as a cathode by depositing a layer with a thickness of 150 nm.
  • An organic electroluminescent device was manufactured in the same manner as in Example 5, except that Comparative Compound 1 (NPB) was used instead of the compound of the present invention as a material for the hole transport layer.
  • NPB Comparative Compound 1
  • An organic electroluminescent device was manufactured in the same manner as in Example 5, except that Comparative Compound A was used instead of the compound of the present invention as a material for the hole transport layer.
  • Comparative Example 1 and Comparative Example 2 as described above Table 5 is as follows. At this time, the T90 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) is vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 40 nm, followed by 4,4-bis [on the hole injection layer.
  • N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • the compound of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer.
  • Alq 3 tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • An organic light emitting diode was manufactured in the same manner as in Example 6, but the emission auxiliary layer was omitted. That is, an organic light emitting display device was manufactured in the same manner as in Example 6, except that an emission auxiliary layer was not formed.
  • An organic light emitting display device was manufactured in the same manner as in Example 6, except that the Comparative Compound B was used to form the emission auxiliary layer instead of the compound of the present invention.
  • the electroluminescent (EL) characteristics of the organic electroluminescent devices manufactured by Example 6, Comparative Example 4 and Comparative Example 5 were measured by applying a forward bias DC voltage to PR-650 of photoresearch company. Same as At this time, the T90 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.
  • Comparative Example 4 including the light-emitting auxiliary layer formed of Comparative Example 3 and Compound B is not formed It was confirmed that the device characteristics are significantly superior to. That is, the organic electroluminescent device including the light emitting auxiliary layer formed of the compound of the present invention has significantly improved the light emitting efficiency and lifetime while the driving voltage is low.
  • the T1 energy level is high and the HOMO energy level is deep, thereby lowering the driving voltage of the organic electroluminescent device and significantly improving the luminous efficiency and lifetime.
  • 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.
  • the compound according to the present invention is not only an organic electroluminescent device (OLED) but also a display device, an organic solar cell, and an organic photoconductor (OPC). ), Organic transistors (organic TFTs), monochromatic or white lighting elements, and the like.
  • OPC organic photoconductor
  • 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 emitting auxiliary layer, The same effect may be obtained even when used in a hole injection layer, a light emitting layer, an electron injection layer, an electron transport layer.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé nouveau, un élément électrique organique l'utilisant, et un dispositif électronique le comprenant. Selon la présente invention, il est possible d'améliorer l'efficacité lumineuse, la pureté des couleurs et la durée de vie d'un élément et de diminuer une tension de commande.
PCT/KR2013/006046 2012-07-12 2013-07-08 Composé, élément électrique organique l'utilisant, et dispositif électronique le comprenant WO2014010897A1 (fr)

Applications Claiming Priority (2)

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KR10-2012-0075982 2012-07-12
KR20120075982A KR101507421B1 (ko) 2012-07-12 2012-07-12 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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WO2014010897A1 true WO2014010897A1 (fr) 2014-01-16

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CN108699079A (zh) * 2016-02-25 2018-10-23 三星Sdi株式会社 有机化合物、组合物、有机光电子器件和显示器件
CN115340546A (zh) * 2021-05-15 2022-11-15 石家庄诚志永华显示材料有限公司 氨基环状化合物、有机电致发光器件、有机电致发光装置

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CN108699079A (zh) * 2016-02-25 2018-10-23 三星Sdi株式会社 有机化合物、组合物、有机光电子器件和显示器件
CN108699079B (zh) * 2016-02-25 2021-08-13 三星Sdi株式会社 有机化合物、组合物、有机光电子器件和显示器件
CN115340546A (zh) * 2021-05-15 2022-11-15 石家庄诚志永华显示材料有限公司 氨基环状化合物、有机电致发光器件、有机电致发光装置

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