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WO2013122364A2 - Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique avec celui-ci - Google Patents

Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique avec celui-ci Download PDF

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WO2013122364A2
WO2013122364A2 PCT/KR2013/001089 KR2013001089W WO2013122364A2 WO 2013122364 A2 WO2013122364 A2 WO 2013122364A2 KR 2013001089 W KR2013001089 W KR 2013001089W WO 2013122364 A2 WO2013122364 A2 WO 2013122364A2
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substituted
deuterium
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WO2013122364A3 (fr
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박정환
이선희
김대성
김원삼
정화순
문성윤
변지훈
황선필
이범성
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덕산하이메탈(주)
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Priority claimed from KR1020120014307A external-priority patent/KR20130139412A/ko
Priority claimed from KR1020120088528A external-priority patent/KR20130092939A/ko
Priority claimed from KR1020120131092A external-priority patent/KR102059957B1/ko
Priority claimed from KR1020120131839A external-priority patent/KR102053314B1/ko
Priority claimed from KR1020130012868A external-priority patent/KR102080299B1/ko
Application filed by 덕산하이메탈(주) filed Critical 덕산하이메탈(주)
Publication of WO2013122364A2 publication Critical patent/WO2013122364A2/fr
Publication of WO2013122364A3 publication Critical patent/WO2013122364A3/fr

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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 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.
  • Efficiency, lifespan, and driving voltage are related to each other.As the efficiency increases, the driving voltage decreases relatively, and the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage 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.
  • the materials 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, a light emitting auxiliary layer material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc.
  • the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials is continuously required, and in particular, the development of material combinations of the light emitting auxiliary layer and the hole transport layer is urgently 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 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.
  • the aryl group or arylene group means monocyclic or heterocyclic aromatic.
  • 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.
  • 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, hole transport layer 140 and / or 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.
  • the present invention by forming a light emitting layer, a hole transporting layer or an auxiliary light emitting layer using the compound represented by the formula (1), the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interfacial characteristics, etc.) of the material, etc. By optimizing, the life and efficiency of the organic electric element 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 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.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • R 1 and R 4 independently of one another i) hydrogen, deuterium, tritium, halogen, C 6 ⁇ C 60 aryl group, fluorenyl group, O, N, S, Si and P containing at least one hetero atom Group consisting of C 2 ⁇ C 60 Heterocyclic group, C 1 ⁇ C 50 Alkyl group, C 2 ⁇ C 20 Alkenyl group, C 1 ⁇ C 30 Alkoxyl group and -LN (Ar 1 ) (Ar 2 ) Or ii) adjacent groups combine with each other to form at least one ring, wherein groups that do not form a ring are as defined in i), n is an integer from 1 to 4, and m is An integer of 1 or 2, and when n is 2 or more, a plurality of R 1 may be the same or different from each other, and when m is 2, a plurality of R 4 may be the same or different from each other,
  • R 2 and R 3 independently of each other, hydrogen, deuterium, tritium, halogen, C 6 ⁇ C 60 aryl group, fluorenyl group, containing at least one hetero atom of O, N, S, Si and P
  • C 2 ⁇ C 60 heterocyclic group C 1 ⁇ C 50 Alkyl group, C 2 ⁇ C 20 Alkenyl group, C 1 ⁇ C 30 Alkoxyl group and -LN (Ar 1 ) (Ar 2 ) Selected,
  • X and Y are bonded to adjacent carbons such that the ring containing X and Y forms a pentagonal or hexagonal ring, and X and Y are, independently of each other, NR ', O, S, CR'R “or SiR 'R', a and b are integers of 0 or 1 (where a + b is an integer of 1 or 2, and R 'and R "are i) independently of each other C 6 -C 60 aryl group, flu Orenyl group, O, N, S, Si and P containing at least one hetero atom of C 2 ⁇ C 60 heterocyclic group, C 1 ⁇ C 50 Alkyl group and -LN (Ar 1 ) (Ar 2 ) Or ii) combine with one another to form a compound as a spy),
  • L is a direct bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 Heterocyclic group; A C 3 -C 60 cycloalkylene group; Fused ring group of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And divalent aliphatic hydrocarbon groups, each of which (except for a single bond) is a nitro group, a nitrile group, a halogen group, an alkyl group of C 1 to C 20 , an aryl group of C 6 to C 20 , and C 2 to C a heterocyclic group of 20, C 1 ⁇ C 20, and the optionally substituted with one or more substituents selected from the group consisting of an alkoxy group and an amino group, the R 1 ⁇ R 4, each L in the X and Y are equal to each other, or Can be different.
  • 'direct bond' means that L is absent, so that when L is a direct bond, Ar
  • Ar is a C 6 ⁇ C 60 aryl group, fluorenyl group, C 2 ⁇ C 60 heterocyclic group containing at least one hetero atom of O, N, S, Si and P, C 1 ⁇ C 50 Alkyl group , C 2 ⁇ C 20 Alkenyl group, C 1 ⁇ C 30 Alkoxyl group and -N (Ar 1 ) (Ar 2 ) It is selected from the group consisting of,
  • Ar 1 and Ar 2 independently of each other, C 6 ⁇ C 60 aryl group, fluorenyl group, O, N, S, Si and hetero ring containing C 2 ⁇ C 60 containing at least one hetero atom Group, C 1 ⁇ C 50 Alkyl group and C 2 ⁇ C 20 Alkenyl group, each Ar 1 And Ar 2 It may be the same or different from each other, R 1 ⁇ R 4 , X, Y and Each Ar 1 and Ar 2 in Ar may be the same or different from each other.
  • R One ⁇ R 4 , R ', R ", L, Ar, Ar One And Ar 2 When is an aryl group, each of these is deuterium, halogen, silane group, boron group, germanium group, cyano group, nitro group, C One ⁇ C 20 Alkylthio, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R 1 to R 4 , R ′, R ′′, L, Ar, Ar 1, and Ar 2 are fluorenyl groups, each of them is deuterium, halogen, silane group, cyano group, C 1 to C 20 alkyl group, C for 2 ⁇ C 20 of alkenyl groups (alkenyl), C 6 ⁇ C 20 aryl group, a C 6 ⁇ C 20 aryl group, C 2 ⁇ C 20 heterocyclic group and C 3 ⁇ C 20 substituted by deuterium May be substituted with one or more substituents selected from the group consisting of cycloalkyl groups,
  • R One ⁇ R 4 , R ', R ", L, Ar, Ar One And Ar 2 Are heterocycles, each of these is deuterium, halogen, silane, cyano, nitro, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R One ⁇ R 4 , R ', R ", L, Ar, Ar One And Ar 2 When is an alkyl group, each of these is halogen, silane group, boron group, cyano group, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R One ⁇ R 4 , R ', R ", L, Ar, Ar One And Ar 2 Is an alkenyl group, each of these is deuterium, halogen, silane group, cyano group, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R 1 to R 4 , R ′, R ′′, L, and Ar are C 1 to C 30 alkoxy groups, each of these is deuterium, halogen, silane group, C 1 to C 20 alkyl group, C 6 to C 20 It may be substituted with one or more substituents selected from the group consisting of an aryl group, a C 6 ⁇ C 20 aryl group substituted with deuterium, a C 2 ⁇ C 20 heterocyclic group and a C 3 ⁇ C 20 cycloalkyl group.
  • Formula 1 may be represented by the following formula (2) -4.
  • Chemical Formula 2 may be represented by Chemical Formula 5 or 6, Chemical Formula 3 by Chemical Formula 7 or 8, Chemical Formula 4 by Chemical Formula 9 or 10.
  • Chemical Formula 2 may be represented by Chemical Formulas 11 to 28 below.
  • Formula 3 may be represented by the following Chemical Formulas 29 to 44.
  • Formula 4 may be represented by the following formula 45 to 70.
  • Formula 1 may be one of the following compounds.
  • the compound according to the present invention may be prepared by the following Scheme 1, and when adjacent groups of R 1 and R 4 are bonded to each other to form a ring, the compound may be prepared by the following Synthesis Example.
  • the ring is known in other reactions (Chem. Eur. J. 2009, 15, 742, Molecules. 2008, 13, 3236-3245, J. Am. Chem. Soc. 2008, 130, 472-480, Tetrahedron Letters. Reactions described in 1997, 38, 4761-4764, etc.).
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.
  • the Br-substituted heterocyclic compound 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. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to give the desired Sub 1-1.
  • the Br-substituted heterocyclic compound 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. After removal of water in the reaction with anhydrous MgSO 4 and filtration under reduced pressure, the resulting product by concentration of the organic solvent was separated by column chromatography to give the desired Sub 2-1.
  • the Br-substituted heterocyclic compound 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. After removal of water in the reaction with anhydrous MgSO 4 and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to obtain the desired Sub 3-1.
  • Sub 3-2 and triphenylphosphine obtained 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 then the concentrated product was separated by column chromatography to obtain the desired Sub 3.
  • the Br-substituted heterocyclic compound 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. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the resulting product by concentration of the organic solvent was separated by column chromatography to give the desired Sub 4-1.
  • Sub 3-1, 9-bromo-10-nitrophenanthrene, Pd (PPh 3 ) 4 , and K 2 CO 3 obtained were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated using column chromatography to obtain the desired Sub 4-2.
  • the heterocyclic compound substituted with Br at position 4 was dissolved in anhydrous THF, the reaction temperature was lowered to -78 ° C, n-BuLi (2.5 M in hexane) was slowly added dropwise, and the reaction was carried out at 0 ° C for 1 hour. Was stirred. 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. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the resulting product by concentration of the organic solvent was separated by column chromatography to give the desired Sub 5-1.
  • the Br-substituted heterocyclic compound 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. After removal of water in the reaction product with anhydrous MgSO 4 and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to obtain the desired Sub 6-1.
  • Sub 6 examples include, but are not limited to, FD-MS values for exemplary compounds of Sub 6 as shown in Table 6.
  • the Br-substituted heterocyclic compound 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. After removal of water in the reaction with anhydrous MgSO 4 and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to give the desired Sub 7-1.
  • Sub 7-1, 9-bromo-10-nitrophenanthrene, Pd (PPh 3 ) 4 and K 2 CO 3 obtained were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired Sub 7-2.
  • Sub 7-2 and triphenylphosphine obtained 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 then the concentrated product was separated by column chromatography to obtain the desired Sub 7.
  • the Br-substituted heterocyclic compound 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. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the resulting product by concentration of the organic solvent was separated by column chromatography to give the desired Sub 8-1.
  • the Br-substituted heterocyclic compound 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. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to give the desired Sub 9-1.
  • Sub 9-1, 9-bromo-10-nitrophenanthrene, Pd (PPh 3 ) 4 , and K 2 CO 3 obtained were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired Sub 9-2.
  • Sub 9-2 and triphenylphosphine obtained 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 then the concentrated product was separated using column chromatography to obtain the desired Sub 9.
  • the Br-substituted heterocyclic compound 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. After removal of water in the reaction with anhydrous MgSO 4 and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to obtain the desired Sub 10-1.
  • Sub 10-2 and triphenylphosphine obtained 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 by column chromatography to obtain the desired Sub 10.
  • the Br-substituted heterocyclic compound 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. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the resulting product by concentration of the organic solvent was separated by column chromatography to give the desired Sub 11-1.
  • the Br-substituted heterocyclic compound 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. After removal of water in the reaction with anhydrous MgSO 4 and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to obtain the desired Sub 12-1.
  • Sub 12-1, 9-bromo-10-nitrophenanthrene, Pd (PPh 3 ) 4 and K 2 CO 3 obtained were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and then the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired Sub 12-2.
  • Sub 12-2 and triphenylphosphine obtained were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was terminated, the solvent was removed by distillation under reduced pressure, and then the concentrated product was separated using column chromatography to obtain the desired Sub 12.
  • Sub 12 examples are as follows, but are not limited thereto, and FD-MS values for exemplary compounds of Sub 12 are shown in Table 12.
  • An organic light emitting diode was manufactured according to a conventional method using a compound obtained through synthesis as a light emitting host material of a light emitting layer.
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl as a hole injection layer ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm.
  • -NPD 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq (2-methyl-8-quinoline oleito) aluminum
  • BAlq 3 tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting device.
  • Comparative Example 1 was prepared as Comparative Compound 1
  • Comparative Example 2 was prepared as Comparative Compound 2
  • Comparative Example 3 was used as a light emitting layer host material.
  • Comparative Example 4 used Comparative Compound 4
  • Comparative Example 5 used Comparative Compound 5.
  • Electroluminescent (EL) characteristics were measured by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices of Example 1 and Comparative Examples 1 to 5, and the measurement result was 300 cd /
  • the T90 life was measured using a life measurement instrument manufactured by McScience Inc. at m2 reference luminance. The measurement results are shown in Table 15 below.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention can be used as a green light emitting layer material can significantly improve the high luminous efficiency, lifetime and color purity.
  • a ring is bonded to the core. It was confirmed that the invented compound in which the pentagonal ring containing X is bonded to the core exhibits higher efficiency and longer life than the structure that is not formed and the structure in which the benzene ring is bonded to the core.
  • 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 2-TNATA film is vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and then a NPD is vacuum-deposited at a thickness of 20 nm on the hole injection layer to form a hole transport layer. It was.
  • the compound of the present invention is doped in a weight ratio of 95: 5 by using a compound of the present invention as a light emitting host material and (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] as a dopant material on the hole transport layer.
  • a compound of the present invention As a light emitting host material and (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] as a dopant material on the hole transport layer.
  • a light emitting layer By depositing a light emitting layer to a thickness of 30nm. Thereafter, BAlq was vacuum deposited to a thickness of 10 nm to form a holdoff layer, and Alq 3 was formed to a thickness of 40 nm to form an electron transport layer.
  • LiF which is a halogenated alkali metal
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting display device.
  • An organic light emitting diode was manufactured in the same manner as in Experimental Example 2, except that Comparative Example 6 was used as Comparative Compound 1, Comparative Example 7 was used as Comparative Compound 2, and Comparative Example 8 was used as the light emitting layer host material.
  • Comparative Example 9 used Comparative Compound 4
  • Comparative Example 10 used Comparative Compound 5.
  • the electroluminescent (EL) characteristics of the organic electroluminescent elements of Experimental Example 2 and Comparative Examples 6 to 10 were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measurement result was 300 cd /
  • the T90 life was measured using a life measurement instrument manufactured by McScience at m2 reference brightness. The measurement results are shown in Table 16 below.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention can be used as a red light emitting layer material can significantly improve the high luminous efficiency, lifetime and color purity.
  • pentagonal rings containing X are bonded to the core rather than the structure in which the ring is not bonded to the core and the structure in which the benzene ring is bonded to the core. It has been confirmed that the self-invented compound to which the quinazoline derivatives are linked has higher efficiency and higher lifetime.
  • a 2-TNATA film was vacuum deposited on an ITO layer (anode) formed on an organic substrate to form a hole injection layer having a thickness of 60 nm, and then a compound of the present invention was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium] was used as a dopant material.
  • a light emitting layer of 30 nm thickness was deposited by doping at 10 weights.
  • BAlq was vacuum deposited to a thickness of 10 nm to form a holdoff layer, and Alq 3 was formed to a thickness of 40 nm to form an electron transport layer.
  • LiF which is an alkali metal halide, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting device.
  • Comparative Example 11 was Comparative Compound 6
  • Comparative Example 12 was Comparative Compound 7
  • Comparative Example 13 was compared to the compound of the present invention as a hole transport layer material.
  • Comparative Example 14 used Comparative Compound 9
  • Comparative Example 15 used Comparative Compound 10 below.
  • the electroluminescent (EL) characteristics of the organic electroluminescent elements of Experimental Example 3 and Comparative Examples 11 to 15 were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measurement result was 300 cd /
  • the T90 life was measured using a life measurement instrument manufactured by McScience at m2 reference brightness. The measurement results are shown in the table below.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention can be used as a hole transport layer material can significantly improve the low driving voltage, high luminous efficiency and lifetime, color purity.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention can be used as a hole transport layer material can significantly improve the low driving voltage, high luminous efficiency and lifetime, color purity.
  • pentagonal rings containing X are bonded to the cores rather than the structure in which the ring is bonded to the core and the structure in which the benzene ring is bonded to the core. It was found that the present invention compounds exhibit higher efficiency, higher lifetime and lower driving voltage.
  • a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and NPD was then vacuum-deposited to a thickness of 20 nm on the hole injection layer to form a hole transport layer. . Thereafter, 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. After the emission auxiliary layer was formed, CBP [4,4'-N, N'-dicarbazole-biphenyl] was used as a host material and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] was formed on the emission auxiliary layer.
  • a 30 nm thick light emitting layer was deposited by doping at 95: 5 weight using the dopant material. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a holdoff layer, and Alq 3 was formed to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting device.
  • Comparative Example 16 had a difference in that there was no light emitting auxiliary layer, and Comparative Example 17 was a light emitting auxiliary layer material instead of the compound of the present invention.
  • Comparative Example 18 used Comparative Compound 7
  • Comparative Example 19 used Comparative Compound 8
  • Comparative Example 20 used Comparative Compound 21, and Comparative Example 21 used Comparative Compound 10.
  • the compound of the present invention in which the pentagonal ring including X is bonded to the core, is used alone as a light emitting auxiliary layer, and has a low voltage, high luminous efficiency and high luminous efficiency due to the deep HOMO energy level. This can be explained by improving device life.
  • the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, it is obvious that the same effect can be obtained.

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Abstract

La présente invention porte sur un nouveau composé qui peut améliorer le rendement d'émission de lumière, la stabilité et la durée de vie d'un élément, sur un élément électrique organique l'utilisant et sur un dispositif électronique avec celui-ci.
PCT/KR2013/001089 2012-02-13 2013-02-12 Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique avec celui-ci WO2013122364A2 (fr)

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WO2015111942A3 (fr) * 2014-01-23 2015-10-01 주식회사 두산 Composé organique et élément électroluminescent organique le contenant
KR20150121394A (ko) * 2014-04-18 2015-10-29 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2015190718A1 (fr) * 2014-06-09 2015-12-17 주식회사 두산 Dispositif électroluminescent organique
WO2016017684A1 (fr) * 2014-07-31 2016-02-04 コニカミノルタ株式会社 Matériau d'élément électroluminescent organique, élément électroluminescent organique, film mince émettant de la lumière, dispositif d'affichage et dispositif d'éclairage
US20160155961A1 (en) * 2014-11-27 2016-06-02 Samsung Display Co., Ltd. Monoamine derivative and organic electroluminescent device including the same
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EP3192848A4 (fr) * 2014-09-12 2018-05-09 LG Chem, Ltd. Diode électroluminescente organique
EP3192847A4 (fr) * 2014-09-12 2018-05-09 LG Chem, Ltd. Diode électroluminescente organique
JP2018514081A (ja) * 2015-03-13 2018-05-31 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 複数のホスト材料及びそれを含む有機電界発光デバイス
CN109096254A (zh) * 2017-06-20 2018-12-28 江西师范大学 喹唑啉衍生物及其制备方法和应用
US11271170B2 (en) * 2019-03-13 2022-03-08 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
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WO2015190718A1 (fr) * 2014-06-09 2015-12-17 주식회사 두산 Dispositif électroluminescent organique
JPWO2016017684A1 (ja) * 2014-07-31 2017-05-18 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、発光性薄膜、表示装置及び照明装置
WO2016017684A1 (fr) * 2014-07-31 2016-02-04 コニカミノルタ株式会社 Matériau d'élément électroluminescent organique, élément électroluminescent organique, film mince émettant de la lumière, dispositif d'affichage et dispositif d'éclairage
EP3192848A4 (fr) * 2014-09-12 2018-05-09 LG Chem, Ltd. Diode électroluminescente organique
EP3192847B1 (fr) * 2014-09-12 2021-03-03 LG Chem, Ltd. Diode électroluminescente organique
EP3192847A4 (fr) * 2014-09-12 2018-05-09 LG Chem, Ltd. Diode électroluminescente organique
US10050206B2 (en) 2014-09-12 2018-08-14 Lg Chem, Ltd. Organic light emitting device
US20160155961A1 (en) * 2014-11-27 2016-06-02 Samsung Display Co., Ltd. Monoamine derivative and organic electroluminescent device including the same
US9960372B2 (en) * 2014-11-27 2018-05-01 Samsung Display Co., Ltd. Monoamine derivative and organic electroluminescent device including the same
CN107231801B (zh) * 2015-02-12 2021-03-23 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含有机电致发光化合物的有机电致发光装置
JP2018510495A (ja) * 2015-02-12 2018-04-12 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物及びそれを含む有機電界発光デバイス
CN107231801A (zh) * 2015-02-12 2017-10-03 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含有机电致发光化合物的有机电致发光装置
WO2016129819A1 (fr) * 2015-02-12 2016-08-18 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositifs électroluminescents organiques les comprenant
JP2018514081A (ja) * 2015-03-13 2018-05-31 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 複数のホスト材料及びそれを含む有機電界発光デバイス
CN109096254A (zh) * 2017-06-20 2018-12-28 江西师范大学 喹唑啉衍生物及其制备方法和应用
CN109096254B (zh) * 2017-06-20 2021-07-06 江西师范大学 喹唑啉衍生物及其制备方法和应用
US11271170B2 (en) * 2019-03-13 2022-03-08 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
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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