WO2013081315A1 - Composé pour un dispositif électronique organique, dispositif électronique organique comprenant celui-ci et dispositif électronique comprenant le dispositif électronique organique - Google Patents

Composé pour un dispositif électronique organique, dispositif électronique organique comprenant celui-ci et dispositif électronique comprenant le dispositif électronique organique Download PDF

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WO2013081315A1
WO2013081315A1 PCT/KR2012/009531 KR2012009531W WO2013081315A1 WO 2013081315 A1 WO2013081315 A1 WO 2013081315A1 KR 2012009531 W KR2012009531 W KR 2012009531W WO 2013081315 A1 WO2013081315 A1 WO 2013081315A1
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group
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substituted
organic
aryl
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PCT/KR2012/009531
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박정환
이선희
문성윤
김대성
정화순
김원삼
변지훈
이범성
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덕산하이메탈(주)
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Priority claimed from KR1020120105232A external-priority patent/KR101497124B1/ko
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Priority to US14/361,268 priority Critical patent/US9905773B2/en
Publication of WO2013081315A1 publication Critical patent/WO2013081315A1/fr
Priority to US15/867,334 priority patent/US10991885B2/en

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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound comprising a five-membered hetero ring, an organic electric element 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.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • 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 host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
  • An object of the present invention is to provide a compound containing an five-membered hetero ring capable of improving the luminous efficiency, low driving voltage, color purity, and lifetime of the device, an organic electric device 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 electric device using the compound represented by the above formula and an electronic device including the organic electric device.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • halo or halogen as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.
  • alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • the aryl group or arylene group in the present invention means a monocyclic or heterocyclic aromatic, for example, the aryl group may be a phenyl group, biphenyl group, fluorene group, 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 at least one of 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 group, C 1 ⁇ C 20 alkyl amine group, C 1 ⁇ C 20 coming of the alkyl group, C 6 ⁇ C 20 coming aryl Ti, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 of the 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, It means that it is substituted with one or more substituents selected from the group consisting of a germanium group, and a C 5 ⁇ C 20 heterocyclic group
  • 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 light emitting layer is formed using the compound represented by Chemical Formula 1 to optimize the energy level and T1 value between each organic material layer, the intrinsic properties (mobility, interfacial properties, etc.) of the organic layers, and thus the lifetime of the organic electric device. And efficiency 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 to R 10 is i) independent of each other, hydrogen, deuterium, halogen, C 6 ⁇ aryl group of C 60, a fluorene group, a fused aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60 C 2 -C 60 heterocyclic group including a ring group, O, N, S, Si and P heteroatoms, -LN (R ') (R "), C 1 ⁇ C 50 Alkyl group, Selected from the group consisting of a C 2 to C 20 alkenyl group, a C 1 to C 30 alkoxy group and a C 6 to C 30 aryloxy group, or ii) adjacent groups combine with each other to form at least one ring Where the groups which do not form a ring are as defined in i).
  • R 1 to R 4 and R 7 to R 10 may be all hydrogen at the same time, and R 5 and R 6 are not bonded to each other to form a ring. Otherwise at least one of R 1 to R 4 and at least one of R 7 to R 10 should not be hydrogen.
  • R One ⁇ R 4 And R 7 ⁇ R 10 Each can be hydrogen, but if they can all be hydrogen at the same time, 5 And R 6 Only when these bond with each other to form a ring.
  • R 5 And R 6 When they form a ring with each other, R One ⁇ R 4 And R 7 ⁇ R 10 At least one of may be a substituent as defined above except for hydrogen.
  • R One ⁇ R 4 At least one of R must be a substituent other than hydrogen and R 7 ⁇ R 10 At least one of (at least one) must be a substituent other than hydrogen.
  • R One ⁇ R 4 Are all hydrogen / hydrogen and R 7 ⁇ R 10 Except when are all hydrogen.
  • adjacent groups of R 1 and R 10 combine with each other to form at least one ring, 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 a ring.
  • 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 a ring.
  • the ring formed by bonding of adjacent groups of R 1 and R 10 to each other may be a monocyclic or polycyclic aromatic ring or a heterocyclic ring containing at least one heteroatom, or a fused aromatic ring with an aliphatic ring.
  • adjacent groups of R 1 and R 10 may be bonded to each other to form an aromatic ring such as benzene, naphthalene, phenanthrene, and the like.
  • a phenanthrene form may be formed together with the benzene ring of the mother nucleus to which they are bonded.
  • R 1 and R 10 may be bonded to each other to form a hetero ring such as thiophene, furan, pyridine, indole, quinoline, etc., 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.
  • X and Y are each independently S, O or SiR 31 R 32 .
  • R 31 and R 32 are independently of each other hydrogen, a C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, Or a C 1 to C 50 alkyl group.
  • L is a single 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; It is selected from the group consisting of.
  • Ar 1 is a C 2 ⁇ C 60 heterocyclic group, a C 6 ⁇ C 60 aryl group, fluorenyl group or -N (R containing at least one hetero atom of O, N, S, Si and P ') (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 or fluorenyl group Can be.
  • R One ⁇ R 12 , Ar One When R 'and R "are aryl groups, they are 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 10 , 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 aryl group of 6 ⁇ C 20, of a C 6 ⁇ C 20 substituted by deuterium aryl group, C 2 ⁇ C 20 of the heterocyclic group and C 3 ⁇ one or more substituents selected from the group consisting of a cycloalkyl group of C 20 May be substituted with
  • 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 One ⁇ R 12 When is an alkyl group, it 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 10 When it is an alkenyl group, it is deuterium, a halogen, a silane group, a 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 ⁇ R 10 is an alkoxy group, which is heavy hydrogen, a halogen, a silane group, a C 1 ⁇ C 20 alkyl group, C 6 ⁇ C 20 aryl group, a C 6 ⁇ C 20 substituted with a heavy hydrogen of the 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,
  • 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 Chemical Formula 1 may be represented by one of the following chemical formulas.
  • Chemical Formula 1 may be one of the following compounds.
  • the compound according to the present invention is prepared by reacting one of Sub 1 to Sub 12 with Sub 13, as in Scheme 1 below.
  • Scheme 1 a case where X is S will be described by way of example, but when X is O or Si, it is similar to the following synthesis method and will not be described separately.
  • R 1 corresponds to R 1 to R 4 of Formula 1
  • R 2 corresponds to R 7 to R 10 of Formula 1
  • R 3 corresponds to R 5 and R 6 of Formula 1.
  • Sub 1 to Sub 12 may be synthesized by the following method.
  • the synthesized Sub 2-1 and iron powder were added to ethanol and HCl mixed solvent, and the reaction was refluxed for 6 hours. Then, the reaction was filtered using Celite, extracted with ethyl acetate 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 a silicagel column to give the desired Sub 2-2 (yield: 65%).
  • Sub 2-2 obtained above is dissolved in a mixed solvent of H 2 O and H 2 SO 4 , NaNO 2 and KI are dissolved in H 2 O and slowly added dropwise. After dropping, the mixture was stirred at room temperature for 30 minutes, and then copper powder was refluxed for 30 minutes. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with Na 2 S 2 O 3 . After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the product was concentrated by separation of the organic solvent using a silicagel column to give the desired Sub 2-3 (yield: 63%).
  • NBS N-Bromosuccinimide
  • Sub 1-7 compound (1 equivalent), Sub 1-8 compound (1.1 equivalent), Pd (PPh 3 ) 4 (0.03 equivalent), NaOH (3 equivalent), and water were added to a round bottom flask, followed by stirring. 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 2.
  • Dibenzothiopen-1-ylboronic acid substituted with R 2 and R 3 , Pd 2 (PPh 3 ) 4 and K 2 CO 3 were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 , and concentrated under reduced pressure. The product was then obtained using a silicagel column to obtain product Sub 4-1.
  • Sub 11-1 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 11.
  • Sub 13 is as follows, but is not limited thereto.
  • Sub 1 to 12 and Sub 1-8 or Sub 1-8 ', Sub 13, and Sub 15 were obtained through the method of Method 1 and Method 2 as follows.
  • O-atomic hetero compounds (10.6 g, 20 mmol) and iodobenzene (4.9 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-8, to obtain 8.5 g (yield 70%) of product 1-56.
  • O-atomic hetero compounds (9.5 g, 20 mmol) and 2- (4-bromophenyl) -4,6-diphenylpyrimidine (9.3, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in Synthesis of Product 1-8 to 10.6 g of product 1-69 (yield 68%) Got.
  • O-atomic hetero compounds (9.6 g, 20 mmol) and iodobenzene (4.9 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-8, to obtain 7.2 g (yield 65%) of product 1-129.
  • O-atomic hetero compounds (9.5 g, 20 mmol) with 2-bromo-4,6-diphenylpyrimidine (7.5 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-8, to obtain 9.18 g (yield 65%) of product 2-5.
  • O-atomic hetero compounds (9.5 g, 20 mmol) with 2-bromo-4,6-diphenylpyrimidine (7.5 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-8, to obtain 9.18 g (yield 65%) of product 2-25.
  • O-atomic hetero compounds (6.5 g, 20 mmol) with 2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-8, to obtain 7.2 g (yield 68%) of Product 4-1.
  • O-atomic hetero compounds (6.5 g, 20 mmol) with 2-bromo-4-phenylquinazoline (10.5 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-8, to obtain 8.7 g (64% yield) of Product 4-11.
  • O-atomic hetero compounds (6.5 g, 20 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (8.7 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol) , P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in Synthesis of Product 1-8 to 7.4 g of Product 4-17 (yield 61%). )
  • O-atomic hetero compounds (6.5 g, 20 mmol) with 2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-8, to obtain 7.1 g (yield 67%) of Product 4-25.
  • O-atomic hetero compounds (6.5 g, 20 mmol) and 4-([1,1'-biphenyl] -3-yl) -2-bromopyrido [3,2-d] pyrimidine (8.7 g, 24 mmol), toluene ( 210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) was obtained using the product 1-8. In the same manner as in the synthesis method of 7.5g (yield 62%) of Product 6-4.
  • N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol) and an five-membered hetero compound (13.3 g, 24 mmol), Toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) was added to Product 1 In the same manner as the synthesis method of -8, 10.7 g (64% yield) of Product 1-10 were obtained.
  • 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 vacuum deposited to form a hole injection layer having a thickness of 60 nm.
  • -NPD 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl
  • -NPD 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq was vacuum-deposited on the emission layer to a thickness of 10 nm.
  • a hole blocking layer was formed, and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq 3 ) was deposited to a thickness of 40 nm to form an electron transport layer.
  • an electron injecting layer was formed by depositing LiF, an alkali metal halide, in a thickness of 0.2 nm, on the electron transport layer, and then depositing Al at a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting device. .
  • 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 according to the present invention as a host material of 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 according to the present invention as a host material of 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 according to the present invention as a host material of the emission layer.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except that Comparative Compound 4 was used instead of the compound according to the present invention as a host material of the emission layer.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except that Comparative Compound 5 was used instead of the compound according to the present invention as a host material of the emission layer.
  • the electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices prepared as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measurement result was based on 300 cd / m 2 .
  • the T95 lifetime was measured using a life-time measurement instrument manufactured by McScience Inc. at luminance. Table 4 shows the results of device fabrication and evaluation.
  • Examples 1 to 312 are organic electroluminescent devices of the present invention manufactured according to Experimental Example 1.
  • 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.
  • 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
  • NPD was vacuum deposited at a thickness of 20 nm on the hole injection layer to form a hole transport layer.
  • (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] is used as a host material on the hole transport layer.
  • a light emitting layer having a thickness of 30 nm was deposited by doping at a weight of 95: 5.
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and Alq 3 was formed to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic EL device.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using Comparative Compound 1 as a host material of the emission layer.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using Comparative Compound 2 as a host material of the emission layer instead of the compound according to the present invention.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using Comparative Compound 3 as a host material of the emission layer instead of the compound according to the present invention.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using Comparative Compound 4 as a host material of the emission layer instead of the compound according to the present invention.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using Comparative Compound 5 as a host material of the emission layer instead of the compound according to the present invention.
  • the electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices prepared as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measurement result was based on 300 cd / m 2 .
  • the T95 lifetime was measured using a life-time measurement instrument manufactured by McScience Inc. at luminance. Table 5 shows the results of device fabrication and evaluation.
  • the organic electroluminescent device material of the present invention when used as a light emitting host material of the organic electroluminescent device, the color purity is improved, the luminous efficiency is increased, and the life is remarkably improved.
  • a 60 nm-thick hole injection layer is formed by vacuum-depositing 2-TNATA on an ITO layer (anode) formed on a glass substrate, and a hole transport layer is formed by vacuum depositing NPD on the hole injection layer with a thickness of 20 nm. It was.
  • the compound (1-153-1-163) of this invention was vacuum-deposited at the thickness of 20 nm on the hole transport layer, and the light emission auxiliary layer was formed.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • (piq) 2 Ir (acac) bis- (1-phenylisoquinolyl) iridium (III) 30 nm thick light emitting layer
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and Alq 3 was formed to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic EL device.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except for using Comparative Compound 1 as a light emitting auxiliary layer material.
  • 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 according to the present invention.
  • 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 according to the present invention.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2, except that Comparative Compound 4 was used instead of the compound according to the present invention.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2, except that Comparative Compound 5 was used instead of the compound according to the present invention.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2 except that the emission auxiliary layer was not formed.
  • the electroluminescent (EL) characteristics were measured by the PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared as described above and the comparative examples. T95 life was measured using a life measurement instrument manufactured by McScience. Table 6 shows the results of device fabrication and evaluation.
  • Examples 457 to 467 are the organic light emitting diodes manufactured by Experimental Example 3 of the present invention.
  • the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, an electron injection layer, an electron transport layer, and a hole injection layer, the same effect can be obtained.

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Abstract

La présente invention concerne un nouveau composé comprenant un hétérocycle à cinq chaînons, apte à améliorer le rendement d'émission lumineuse, la stabilité et la durée de vie de service d'un dispositif, un dispositif électronique organique utilisant le composé et un dispositif électronique comprenant le dispositif électronique organique.
PCT/KR2012/009531 2011-11-28 2012-11-13 Composé pour un dispositif électronique organique, dispositif électronique organique comprenant celui-ci et dispositif électronique comprenant le dispositif électronique organique WO2013081315A1 (fr)

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