WO2014061960A1 - Composé pour dispositif électroluminescent organique, dispositif électroluminescent organique et dispositif électronique l'utilisant - Google Patents

Composé pour dispositif électroluminescent organique, dispositif électroluminescent organique et dispositif électronique l'utilisant Download PDF

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WO2014061960A1
WO2014061960A1 PCT/KR2013/009194 KR2013009194W WO2014061960A1 WO 2014061960 A1 WO2014061960 A1 WO 2014061960A1 KR 2013009194 W KR2013009194 W KR 2013009194W WO 2014061960 A1 WO2014061960 A1 WO 2014061960A1
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aryl
organic
ring
layer
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문성윤
이선희
최연희
이범성
여승원
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덕산하이메탈(주)
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    • H05B33/00—Electroluminescent light sources
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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 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.
  • 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.
  • Efficiency, lifespan, and driving voltage are related to each other, and as efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases. It shows a tendency to increase the life.
  • 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.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • the OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.
  • materials forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting auxiliary layer material, a light emitting material, an electron transport material, an electron injection material, etc., are stable and efficient. Supported by the material should be preceded, but the development of a stable and efficient organic material layer for an organic electric device has not been made enough, and therefore, the development of a new material is still 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 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 Preferably, the compound of the present invention may be used as the light emitting layer 150 and / or the light emitting auxiliary layer 151.
  • the hole transport layer in the organic electroluminescent device it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each of the light emitting layers R, G, and B, It is time to develop different emission auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.
  • a light emitting layer or an auxiliary light emitting layer using a compound represented by the formula (1) by optimizing the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) of the organic material
  • the life and efficiency of the electric device can be improved at the same time.
  • 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).
  • the A ring may be an aromatic ring or a heterocycle fused to a pentagram ring containing neighboring N (nitrogen). That is, ring A shares one side with a pentagram ring containing N.
  • the A ring may be a monocyclic or polycyclic ring. In the case of a polycyclic ring, the ring may be fused to each other, a plurality of rings may be unfused to each other, or a ring in which the fused and non-fused forms are mixed.
  • the aromatic ring and the hetero ring may have 6 to 60 carbon atoms, and preferably 6 to 14 carbon atoms. That is, the A ring may be benzene, naphthalene, phenanthrene, or the like.
  • the A ring when it is a hetero ring, it may be a hetero ring having 2 to 60 carbon atoms, for example, thiophene, furan, pyridine, indole, quinoline and the like.
  • X is CR'R ", NR ', S or O, wherein R' and R" are independently of each other an C 6 ⁇ C 60 aryl group; C 2 ⁇ C 60 Heterocyclic group; Or a C 1 to C 50 alkyl group.
  • R 1 It may be represented as.
  • L and o are integers of 0 or 1, and l + o may be 1 or more.
  • L means absence (also called direct bond or single bond).
  • L may be monovalent or divalent depending on the value of o.
  • L is selected from the group of monovalent substituents consisting of i) a C 6 -C 60 aryl group, a C 2 -C 60 monocyclic heterocyclic group and a fluorenyl group, or ii) a C 6 -C 60 aryl It may be selected from the group of divalent substituents consisting of a ylene group, a divalent heterocyclic group of C 2 to C 60 and a fluorenylene group.
  • Y is hydrogen, deuterium, tritium, halogen group, -N (Ar 3 ) (Ar 4 ), nitro group, nitrile group, amide group, silane group, C 1 ⁇ C 50 alkyl group, C 6 ⁇ In the group consisting of C 60 aryl group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 60 heterocyclic group, and C 6 ⁇ C 60 aromatic ring and C 3 ⁇ C 60 alicyclic ring group Can be selected.
  • p of R ⁇ 1> is an integer of 1 or more.
  • p may be determined according to the A ring.
  • a ring is a benzene ring
  • p may be an integer of 1 to 4 since the benzene ring may have 4 carbon atoms
  • a ring is naphthyl, 1 to 6 may be used.
  • a plurality of R 1 may be the same as or different from each other.
  • adjacent R 1 may be bonded to each other to form one or more rings. That is, when p is 2 or more, adjacent R 1 may be bonded to each other to form a fused form with A ring.
  • a ring itself may be a polycyclic ring, even if A ring is a monocyclic ring, substituents R 1 may be bonded to each other to form a polycyclic ring fused to A ring.
  • R 2 to R 5 may be defined to be the same as R 1 . That is, they It may be represented by, wherein L, Y, l, o and the like may be defined the same as defined in R 1 .
  • n and n may be 0 or 1, respectively, but m + n is preferably 1 or more. That is, at least one of Ar 1 and Ar 2 should be present.
  • Ar 1 may have different substituent definitions depending on m and n.
  • Ar 3 and Ar 4 are independently of each other C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heterocyclic group, fluorenyl group, C 1 ⁇ C 50 Alkyl group and C 2 ⁇ C 20 Al It may be selected from the group consisting of a kenyl group, or Ar 3 and Ar 4 may combine with each other to form a heterocycle with N.
  • the aromatic ring of the A ring, R 1 ⁇ R 5 , R ', R "of X, Ar 1 to Ar 4 and the like may be further substituted with other substituents.
  • the heterocyclic groups of C 2 to C 60 of A, L, Y, Ar 1 to Ar 4 , R ′ and R ′′ include a halogen group; an alkyl group of C 1 to C 20 ; an alkenyl group of C 2 to C 20 ; C alkoxy group of 1 ⁇ C20; C 6 ⁇ amine group substituted with a heterocyclic group of C 20 aryl group or a C 2 ⁇ C 20 of the; C 6 ⁇ C 60 aryl group; a C 6 ⁇ C 20 substituted with deuterium It may be substituted with one or more substituents selected from the group consisting of: an aryl group; C 7 ⁇ C 20 aryl alkyl group; C 8 ⁇ C 20 aryl alkenyl group; nitrile group; and an acetylene group.
  • the fluorenyl group of L, Ar 1 , Ar 3 and Ar 4 is a deuterium, a halogen group, a C 2 ⁇ C 20 alkenyl group, C 1 ⁇ C 20 Alkoxy group, C 6 -C 20 aryl group, C 7 -C 20 arylalkyl group, C 8 -C 20 arylalkenyl group, C 1 -C 50 alkyl group, C 2 -C 20 heterocyclic group, nitrile It may be substituted with one or more substituents selected from the group consisting of a group and an acetylene group.
  • the Y, Ar 1 to Ar 4, R 'and R "of the C 1 ⁇ C 50 alkyl group, and a group is alkylene of C 2 ⁇ C 20 of the Ar 1, C 2 ⁇ alkenyl group of C 20; C an alkoxy group of 1 ⁇ C 20; an aryl group of a C 6 ⁇ C 20 substituted with heavy hydrogen;; C 6 ⁇ C 20 aryl group, a C 7 ⁇ arylalkyl group of C 20; C 8 ⁇ C 20 aryl alkenyl; C It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group of 2 to C 20 , a nitrile group, and an acetylene group.
  • Formula 1 may be represented by one of the following formula.
  • a ring when A ring is a benzene ring, it may be represented by Formula 2, in the case where A ring is a benzene ring in Formula 1 and at least one of R 1 ⁇ R 4 is -LN (Ar 3 ) (Ar 4 ) In Formula 1, when A ring is benzene ring and (Ar 2 ) m is —N (Ar 3 ) (Ar 4 ) in Formula 1, it may be represented by Formula 4.
  • R 11 to R 14 may be defined the same as i) R 1 of Formula 1, or ii) adjacent R 11 and R 12 , adjacent R 12 and R 13, and / or neighbor One R 13 and R 14 may combine with each other to form at least one ring. At this time, adjacent pairs of R 11 to R 14 may be bonded to each other, or only some pairs or only one pair may be bonded to each other to form at least one ring, wherein a group not forming a ring is defined in i) Likewise it can be defined the same as R 1 .
  • Ar 1 to Ar 4 , R 2 to R 5 , X, L, m, and n may be defined in the same manner as defined in Chemical Formula 1.
  • L is a single bond; C 6 ⁇ C 60 arylene group; C 2 ⁇ C 60 Heterocyclic group; And it may be selected from the group consisting of divalent aliphatic hydrocarbon, Ar 3 and Ar 4 are independently of each other i) a C 6 ⁇ C 60 aryl group; C 2 ⁇ C 60 Heterocyclic group; Fluorenyl groups; Or an alkyl group of C 1 to C 50 ; and an alkenyl group of C 2 to C 20 , or ii) Ar 3 and Ar 4 may be bonded to each other to form a heterocycle with N.
  • the arylene group, heterocyclic group, aliphatic hydrocarbon group of L, the aryl group, heterocyclic group, pulluorenyl group, alkyl group and alkenyl group of Ar 3 and Ar 4 may be further substituted with a substituent.
  • they may be a deuterium, a halogen group, a C 1 to C 20 alkyl group, a C 1 to C 20 alkoxy group, a C 6 to C 20 aryl group or a C 2 to C 20 heterocyclic group substituted with an amine group, C 1 ⁇ C 20 coming of the alkyl amine group, C 1 ⁇ alkyl group of C 20, C 6 ⁇ of the C 20 arylthio group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl group, C 3 ⁇ C of 20 cycloalkyl group, C 6 -C 60 aryl group;
  • formula represented by Formula 1 may be represented by one of the following formula.
  • Ar 1 to Ar 4 , R 2 to R 5 , m, n, X and L are the same as defined in Formula 1.
  • Formula 1 may be represented by one of the following formula.
  • Formula 1 may be one of the following compounds.
  • the compound according to the present invention may be prepared by reacting one of Sub 1 or Sub 3 with Sub 2, or by reacting Sub 1 with Sub 4, as shown in Scheme 1 below.
  • Sub 1-1-1 examples are as follows and their FD-MS values are shown in Table 1, but are not limited thereto.
  • Sub 1-1-1 (1 equiv) was dissolved in anhydrous Ether, the temperature of the reactant was lowered to -78 ° C, n-BuLi (2.5 M in hexane) (1.1 equiv) was slowly added dropwise, and then the reaction was carried out for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 °C and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1-1-2.
  • Sub 1-1-2 (1 equivalent) obtained in the synthesis was dissolved in THF, and then Sub 1-1-3 (1.1 equivalent), Pd (PPh 3 ) 4 (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was stirred under reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-1-4.
  • Sub 1-1 examples are as follows, FD-MS values are shown in Table 2, but is not limited thereto.
  • Sub 1-2-1 (1 equiv) was dissolved in anhydrous Ether, the reactant temperature was lowered to -78 ° C, n-BuLi (2.5M in hexane) (1.1 equiv) was slowly added dropwise, and the reaction was allowed to proceed for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 °C and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1-2-2.
  • Sub 1-2-3 and (1 equivalent) and triphenylphosphine (2.5 equivalents) obtained in the synthesis were dissolved in o-dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-2.
  • Sub 1-2 examples are as follows, and FD-MS values are shown in Table 3, but are not limited thereto.
  • Sub 1-3-1 (1 equiv) was dissolved in anhydrous Ether, the temperature of the reactant was lowered to -78 ° C, n-BuLi (2.5 M in hexane) (1.1 equiv) was slowly added dropwise, and the reaction was then added for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 °C and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain Sub1-3-2.
  • Sub 1-4-1 (1 equiv) was dissolved in anhydrous Ether, the reaction temperature was lowered to -78 ° C, n-BuLi (2.5 M in hexane) (1.1 equiv) was slowly added dropwise, and then the reaction was carried out for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 °C and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub 1-4-2.
  • Sub 1-4-2 (1 equivalent) obtained in the synthesis was dissolved in THF, and then Sub 1-1-3 (1.1 equivalent), Pd (PPh 3 ) 4 (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was refluxed with stirring. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-4-3.
  • Sub 1-4-3 and (1 equivalent) and triphenylphosphine (2.5 equivalents) obtained in the synthesis were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-4.
  • Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below.
  • An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention obtained through synthesis as a light emitting host material of a light emitting layer.
  • a phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was formed by vacuum deposition to a thickness of 60 nm to form a hole injection layer, followed by 4,4-bis [ N- (1-nap) on the hole injection layer.
  • Til) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant material. .
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq (2-methyl-8-quinoline oleito) aluminum
  • a blocking layer was formed and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq 3 ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm
  • an organic light emitting diode was manufactured by forming an Al / LiF cathode.
  • An organic light emitting display device was manufactured in the same manner as in Experiment 1, except that Comparative Compound 1 (CBP) was used instead of the compound of the present invention as a host material in forming the emission layer.
  • CBP Comparative Compound 1
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except that Comparative Compound 2 was used instead of the compound of the present invention as a host material in forming the emission layer.
  • the electroluminescent (EL) characteristics of the organic electroluminescent devices prepared by Experimental Example 1, Comparative Example 1 and Comparative Example 2 of the present invention was applied to the PR-650 by photoresearch by applying a forward bias DC voltage. Is shown in Table 10 below. At this time, the T90 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.
  • the organic electroluminescent device using the compound according to the present invention as the light emitting layer material not only significantly improved the luminous efficiency and lifespan, but also the color purity.
  • the organic light emitting display device according to Examples 134 to 201, where X is S exhibits low driving voltage, high efficiency, and high lifetime, and has the best results as a phosphorescent host.
  • a 2-TNATA film is vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer by forming a hole injection layer, and then a NPD is vacuum deposited on the hole injection layer by 20 nm thickness to form a hole transport layer. Formed.
  • 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.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl]
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium
  • a 30 nm thick light emitting layer was deposited by doping by weight. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq 3 was deposited to a thickness of 40 nm to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.
  • An organic light emitting display device was manufactured in the same manner as in Experimental Example 2, except that Comparative Compound 3 was used instead of the compound of the present invention when forming the emission auxiliary layer.
  • An organic light emitting display device was manufactured in the same manner as in Experimental Example 2, except that Comparative Compound 4 was used instead of the compound of the present invention when forming the emission auxiliary layer.
  • Examples 328 to 356 where X is S the driving voltage was remarkably low, and the daytime efficiency and the lifespan were remarkably improved. Thus, the device characteristics were very excellent.
  • the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, the same effect can be obtained.

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  • Organic Chemistry (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention porte sur un nouveau composé qui peut améliorer l'efficacité d'électroluminescence, la stabilité, et la durée de vie d'un dispositif, sur un dispositif électroluminescent utilisant le composé, et sur un dispositif électronique du dispositif électroluminescent.
PCT/KR2013/009194 2012-10-18 2013-10-15 Composé pour dispositif électroluminescent organique, dispositif électroluminescent organique et dispositif électronique l'utilisant WO2014061960A1 (fr)

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WO2015125679A1 (fr) * 2014-02-18 2015-08-27 保土谷化学工業株式会社 Dérivé de benzofuroindole et élément électroluminescent organique
WO2016017594A1 (fr) * 2014-07-29 2016-02-04 保土谷化学工業株式会社 Élément électroluminescent (el) organique
WO2016027687A1 (fr) * 2014-08-20 2016-02-25 保土谷化学工業株式会社 Élément électroluminescent organique
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EP3244464A4 (fr) * 2015-01-07 2018-09-12 Hodogaya Chemical Co., Ltd. Élément électroluminescent organique
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WO2014196556A1 (fr) * 2013-06-06 2014-12-11 保土谷化学工業株式会社 Dérivé d'indéno-indole et élément électroluminescent organique
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US20200052224A1 (en) * 2018-08-10 2020-02-13 Samsung Display Co., Ltd. Organic electroluminescence device and condensed cyclic compound for organic electroluminescence device

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