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WO2013105747A1 - Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé - Google Patents

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

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WO2013105747A1
WO2013105747A1 PCT/KR2012/011694 KR2012011694W WO2013105747A1 WO 2013105747 A1 WO2013105747 A1 WO 2013105747A1 KR 2012011694 W KR2012011694 W KR 2012011694W WO 2013105747 A1 WO2013105747 A1 WO 2013105747A1
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박정환
이선희
문성윤
김대성
정화순
김원삼
변지훈
이범성
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덕산하이메탈(주)
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    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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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 material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • 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 forming 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 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” have a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, and are 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 specified, but is not limited thereto.
  • an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 3 to 60 carbon atoms, each containing 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 indicated, 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 an atom other than carbon, such as N, O, S, P or Si, unless otherwise noted.
  • 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 herein refers to deuterium, halogen, amino, nitrile, nitro, C 1 -C 20 alkyl, 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 2 ⁇ 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 electric 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 conductive metal oxide or an alloy thereof on the substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer (on the substrate) 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 may be formed 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 device for monochrome or white illumination.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include an electronic device including a display device including the organic electric element of the present invention described above, and 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).
  • X is S or O
  • Y is S or O
  • One ⁇ R 4 And R 7 ⁇ R 10 At the same time, neither can hydrogen.
  • R 7 ⁇ R 10 At least one of is not hydrogen and vice versa 7 ⁇ R 10 R is both hydrogen
  • One ⁇ R 4 At least one of is not hydrogen.
  • X is S One ⁇ R 4 And R 7 ⁇ R 10 At least one of is not hydrogen
  • Y is O
  • R One ⁇ R 4 And R 7 ⁇ R 10 At least one of is not hydrogen.
  • R 1 to R 10 may be ii) adjacent groups may be bonded to each other to form at least one ring, wherein a group not forming a ring is as defined in i).
  • 'neighboring groups combine with each other to form at least one ring' means that R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 and / or R 9 and R 10 are bonded to each other to form at least one ring compound.
  • the scope of the present invention is not limited by what substituents and by what reaction the ring is formed.
  • the ring is a known reaction (Heck reaction or Chem. Eur. J. 2009, 15, 742, Molecules. 2008, 13, 3236-3245, J. Am. Chem. Soc. 2008, 130, 472-480, Tetrahedron Letters, 1997, 38, 4761-4764, etc.).
  • the ring formed by bonding of adjacent groups among R 1 to R 10 may not only be a monocyclic or polycyclic aromatic ring or a hetero ring including at least one hetero atom, but also a fused aromatic ring and an aliphatic ring.
  • neighboring groups of R 1 and R 4 may be bonded to each other to form an aromatic ring such as benzene, naphthalene, phenanthrene, and the like.
  • R 1 and R 2 combine with each other to form a benzene ring
  • R 3 and R 4 combine with each other to form a benzene ring
  • a phenanthrene form may be formed together with the benzene ring of the parent nucleus to which they are bonded.
  • adjacent groups of R 1 to R 10 may be bonded to each other to form a heterocycle such as thiophene, furan, pyridine, indole, quinoline, and the like, wherein the carbon number may be 2 to 60.
  • the ring may be fused to each other, a plurality of rings may not be fused to each other, or a ring in which the fused and non-fused forms are mixed.
  • R 11 And R 12 are independently of each other hydrogen, C 6 ⁇ C 60 C containing at least one heteroatom of an aryl group, fluorenyl group, O, N, S, Si and P 2 ⁇ C 60 Heterocyclic group of -L-N (R ') (R ") or C One ⁇ C 50 It may be an alkyl group of.
  • L is a direct bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And divalent aliphatic hydrocarbon group; may be selected from the group consisting of.
  • the direct bond means that L is absent, and means that Ar 1 is directly bonded to N.
  • Ar 1 is hydrogen, deuterium, tritium, halogen, C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 Heterocyclic group containing at least one heteroatom of O, N, S, Si and P, flu Orenyl, C 1 -C 50 alkyl, C 2 -C 20 alkenyl, C 1 -C 30 alkoxyl and -N (R ') (R''),
  • R 'and R are independently of each other O, N, S, Si and P containing at least one heteroatom of C 2 ⁇ C 60 heterocyclic group, C 6 ⁇ C 60 aryl group, C 1 ⁇ An alkyl group of C 50, an alkenyl group of C 2 to C 20 , or a fluorenyl group.
  • R 1 to R 12 , Ar 1 , R ′, and R ′′ may be further substituted with other substituents.
  • R 1 to R 12 , Ar 1 , R ′, and R ′′ are fluorenyl groups, they are deuterium, halogen, silane groups, cyano groups, C 1 to C 20 alkyl groups, and C 2 to C 20 alkenyl groups ( alkenyl), C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, C 2 ⁇ C 20 of the heterocyclic group and C 3 ⁇ C 20 from the group consisting of a cycloalkyl group at least one group selected in the It may be substituted with a substituent.
  • R One ⁇ R 1O If is a fused ring group, it 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 ⁇ R 10 And Ar 1 Is an alkoxyl group
  • it is deuterium, halogen, silane group, C 1 ⁇ C 20 Alkyl group, C 6 ⁇ C 20 aryl group, C 6 ⁇ C substituted with deuterium 20 may be substituted with one or more substituents selected from the group consisting of an aryl group, C 2 to C 20 heterocyclic group, and C 3 to C 20 cycloalkyl group,
  • R 1 ⁇ R 10 is an aryloxy group cases, this deuterium, a silane group, a cyano group, C of 1 ⁇ C 20 alkyl group, a C 6 ⁇ C 20 substituted with an aryl group, a heavy hydrogen of C 6 ⁇ C 20 aryl group , C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group and C 3 ⁇ C 20 cycloalkyl group.
  • the compound represented by Formula 1 may be represented by the following formula (2) or formula (3).
  • Formula 1 may be represented by the following compounds.
  • the compounds (final products) according to the present invention may be prepared by reacting one of Sub 1 to Sub 22 with Sub 23 as in Scheme 1 below.
  • Sub 1 may be synthesized by the reaction route of Scheme 2 below.
  • Sub 1-1 was dissolved in carbon disulfide solvent under nitrogen, and bromine was slowly added dropwise. After stirring at room temperature for 12 hours, when the reaction was completed, the resulting product was concentrated by using a depressurizer to recrystallize the product using ethanol solvent to obtain the desired Sub 1-2.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below.
  • Sub 2-1 was dissolved in anhydrous THF, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5M 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 was obtained by concentrating the organic solvent to give the desired Sub 2-2 using column chromatography.
  • n-BuLi 2.5M in hexane
  • Sub 3 may be synthesized by the reaction route of Scheme 4 below.
  • Sub 3-1 is dissolved in acetic acid, and hydrogen peroxide dissolved in acetic acid is dropped dropwise and stirred at room temperature for 6 hours.
  • the reaction was terminated by removing the acetic acid (acetic acid) using a reduced pressure device and separated by column chromatography to obtain the desired Sub 3-2.
  • Sub 3-2 and trifluoromethanesulfonic acid obtained were added, stirred at room temperature for 24 hours, and water and pyridine (8: 1) were slowly added thereto and refluxed for 30 minutes. Lower the temperature, extract with CH 2 Cl 2 and wipe 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 3-3.
  • Sub 4 may be synthesized by the reaction route of Scheme 5 below.
  • Sub 5 may be synthesized by the reaction route of Scheme 6 below.
  • Sub 6 may be synthesized by the reaction pathway of Scheme 7.
  • Sub 7 may be synthesized by the reaction pathway of Scheme 8 below.
  • 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. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 7-2.
  • Sub 7-2 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 7.
  • Sub 8 may be synthesized by the reaction pathway of Scheme 9 below.
  • Sub 8-2 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 8.
  • Sub 9 may be synthesized by the reaction pathway of Scheme 10 below.
  • 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.
  • Sub 10 may be synthesized by the reaction pathway of Scheme 11 below.
  • 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.
  • Sub 11 may be synthesized by the reaction pathway of Scheme 12 below.
  • 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. The resulting product was separated using column chromatography to obtain the desired Sub 11-2.
  • Sub 12 may be synthesized by the reaction pathway of Scheme 13.
  • 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 13 may be synthesized by the reaction pathway of Scheme 14.
  • Sub 14 may be synthesized by the reaction pathway of Scheme 15 below.
  • Sub 14-2 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 14.
  • Sub 15 may be synthesized by the reaction pathway of Scheme 16 below.
  • Sub 15-2 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 15.
  • Sub 16 may be synthesized by the reaction pathway of Scheme 17 below.
  • Sub 16-1, 1-bromo-2-nitrobenzene, 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 16-2.
  • Sub 16-2 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 8.
  • Sub 17 can be synthesized by the reaction pathway of Scheme 18 below.
  • Sub 17-1 1-bromo-2-nitrobenzene, 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 17-2.
  • Sub 18 may be synthesized by the reaction pathway of Scheme 19 below.
  • Sub 18-1, 1-bromo-2-nitrobenzene, 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 18-2.
  • Sub 18-2 and triphenylphosphine obtained were dissolved in o-dichlorobenzene and refluxed for 24 hours. When 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 18.
  • Sub 19 may be synthesized by the reaction pathway of Scheme 20 below.
  • Sub 19-1 1-bromo-2-nitrobenzene, 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 19-2.
  • Sub 20 may be synthesized by the reaction pathway of Scheme 21 below.
  • Sub 20-1 1-bromo-2-nitrobenzene, 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. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 20-2.
  • Sub 20-2 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 20.
  • Sub 21 may be synthesized by the reaction pathway of Scheme 22 below.
  • Sub 22 may be synthesized by the reaction pathway of Scheme 23.
  • Pd 2 (dba) 3 , PPh 3 , NaOt-Bu were mixed with toluene after mixing five-membered hetero compounds (7.5 g, 20 mmol) and 4- (4-bromophenyl) -2,6-diphenylpyrimidine (9.3 g, 24 mmol) in toluene. After addition, the mixture was stirred at reflux for 24 hours at 100 ° C. After extracting with ether and water, the organic layer was dried over MgSO 4 and concentrated and the resulting organic material was silicagel column and recrystallized to give the product 8.7 g (64% yield).
  • 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.
  • 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) film was vacuum deposited to form a hole injection layer having a thickness of 60 nm, and then 4,4-bis [ 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.
  • NPD N-bis [ N- (1 -Naphthyl) -N -phenylamino] biphenyl
  • the light emitting layer was deposited to a thickness of 30 nm by doping the compound of the present invention as a host material on the hole transport layer with a weight ratio of 95: 5 of Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant.
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium]
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) aluminum
  • a holdoff layer was formed, and an electron transport layer was formed on the holdoff layer with a thickness of 40 nm of tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq 3 ). 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 display device.
  • Alq 3 tris (8-quinolinol) aluminum
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except that Comparative Compound 1 was used instead of the compound of the present invention as a host material in forming the emission layer.
  • 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.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except that Comparative Compound 3 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 Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measured results were measured at 300 cd / m 2 reference luminance. T95 life was measured using a life measurement instrument manufactured by McScience.
  • Table 5 below shows device fabrication and evaluation results of Experimental Example 1 and Comparative Examples 1 to 3 to which the compound according to the invention was applied.
  • the present invention shows higher luminous efficiency and higher lifetime than Comparative Examples 1 to 3, and in particular, relatively low driving voltage, high efficiency and lifetime compared to Comparative Examples 2 and 3 Indicates. It is judged that the core has a deeper HOMO by introducing a substituent in the O-membered heterocyclic backbone, has a suitable HOMO value with HTL, and increases the lifetime by accelerating hole mobility, and also the electron density of LUMO by the backbone substituent. By delocalizing, it is judged to exhibit high efficiency.
  • 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.
  • 2-TNATA 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.
  • the compound of the present invention and the dopant (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] are doped in a weight ratio of 95: 5 on the hole transport layer.
  • the light emitting layer was deposited by.
  • LiF an alkali metal halide
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except that Comparative Compound 2 was used instead of the compound of the present invention as a host material in forming the emission layer.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except that Comparative Compound 3 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 Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measured results were measured at 300 cd / m 2 reference luminance. T95 life was measured using a life measurement instrument manufactured by McScience.
  • Table 6 shows device fabrication and evaluation results of Experimental Example 2 and Comparative Examples 4 to 5 to which the compound according to the present invention was applied.
  • 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.
  • the compound of the present invention in which a substituent is introduced into the five-membered heterocyclic backbone and the quinazoline derivatives are connected, shows higher efficiency and longer lifespan. It was confirmed.
  • 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, a hole transport layer, and a hole injection layer.

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Abstract

Cette invention concerne un nouveau composé capable d'améliorer le rendement lumineux, la stabilité, et la longévité d'un élément. L'invention concerne également un élément électronique organique l'utilisant et un dispositif électronique associé.
PCT/KR2012/011694 2012-01-13 2012-12-28 Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique associé WO2013105747A1 (fr)

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