WO2015174682A1 - Composé hétérocyclique contenant un groupe amine aromatique et dispositif électroluminescent organique comportant celui-ci - Google Patents

Composé hétérocyclique contenant un groupe amine aromatique et dispositif électroluminescent organique comportant celui-ci Download PDF

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WO2015174682A1
WO2015174682A1 PCT/KR2015/004552 KR2015004552W WO2015174682A1 WO 2015174682 A1 WO2015174682 A1 WO 2015174682A1 KR 2015004552 W KR2015004552 W KR 2015004552W WO 2015174682 A1 WO2015174682 A1 WO 2015174682A1
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formula
group
carbon atoms
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unsubstituted
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PCT/KR2015/004552
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Korean (ko)
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박석배
송주만
이유림
김희대
박상우
정경석
차순욱
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에스에프씨 주식회사
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Priority claimed from KR1020140072710A external-priority patent/KR102030354B1/ko
Application filed by 에스에프씨 주식회사 filed Critical 에스에프씨 주식회사
Priority to CN201580020254.2A priority Critical patent/CN106458953B/zh
Priority to US15/306,867 priority patent/US11672172B2/en
Priority to JP2016565495A priority patent/JP6367367B2/ja
Priority to EP15793316.9A priority patent/EP3144302B1/fr
Publication of WO2015174682A1 publication Critical patent/WO2015174682A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to a heterocyclic compound including an aromatic amine group and an organic light emitting device including the same, and more particularly, when used as an organic light emitting material, it is excellent in brightness and luminous efficiency, and can show excellent device characteristics of long life. It relates to a heterocyclic compound and an organic light emitting device comprising the same.
  • OLEDs Organic light emitting diodes
  • OLEDs are displays using self-luminous phenomena, and are full-color due to their advantages such as large viewing angles, lighter and simpler, and faster response speeds than liquid crystal displays. Application to display or lighting is expected.
  • an organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon generally 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 to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
  • Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
  • the material used as the organic material layer in the organic light emitting device 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 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.
  • 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 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 shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • Korean Patent Publication No. 10-2008-0015865 discloses an organic light emitting device using an indenofluorene derivative having an aryl amine bonded thereto.
  • No. 10-2012-0047706 discloses a compound having a structure in which dibenzofuran or dibenzothiophenefluorene is present in one molecule or benzofuran or dibenzothiophene is present together with carbazole. The organic light emitting element used is disclosed.
  • the luminance and luminous efficiency are superior to the organic light emitting materials manufactured by the prior art including the prior art, and the necessity of developing a new organic light emitting material having long life characteristics is continuously. It is a required situation.
  • the first technical problem to be achieved by the present invention can be used in the light emitting layer of an organic light emitting diode (OLED), excellent brightness and luminous efficiency, and a novel organic that can show excellent long-life device characteristics It is to provide a light emitting material.
  • OLED organic light emitting diode
  • Another object of the present invention is to provide an organic light emitting device including the organic light emitting material.
  • the present invention provides an amine compound represented by the following [Formula A] or [Formula B] in order to achieve the first technical problem.
  • a 1 , A 2 , E, and F are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or substituted or unsubstituted. Ring aromatic heterocyclic ring having 2 to 40 carbon atoms;
  • Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A 2 form a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R1 and R2, respectively. ;
  • the linking groups L 1 to L 12 are the same as or different from each other, and each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or Unsubstituted C2-C60 alkynylene group, substituted or unsubstituted C3-C60 cycloalkylene group, substituted or unsubstituted C2-C60 heterocycloalkylene group, substituted or unsubstituted C6-C60 An arylene group or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
  • M is any one selected from NR 3 , CR 4 R 5 , SiR 6 R 7 , GeR 8 R 9 , O, S, Se;
  • the substituents R 1 to R 9 , Ar 1 to Ar 8 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 50 carbon atoms.
  • the R 1 and R 2 may be connected to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring are N, O, P, Si, S , Ge, Se, Te may be substituted with any one or more heteroatoms;
  • P1 to p4, r1 to r4, and s1 to s4 are each an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L 1 to L 12 are the same as or different from each other,
  • X is an integer of 1 or 2
  • y and z are the same or different, and each independently an integer of 0 to 3
  • Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 5 and Ar 6 , and Ar 7 and Ar 8 may be connected to each other to form a ring;
  • the ruler is combined with * of Structural Formula Q1 to form a condensed ring.
  • the present invention in another aspect, the present invention, the first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organic light emitting compound represented by Formula A or Formula B of the present invention.
  • the amine compound represented by the above [Formula A] or [Formula B] is excellent in brightness and luminous efficiency compared to the conventional material, and can show excellent device characteristics of long life, an organic light emitting device having improved characteristics It can be used to.
  • FIG. 1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.
  • the present invention provides an amine compound represented by the following [Formula A] or [Formula B] as an organic light emitting compound that can be used in the light emitting layer of the organic light emitting device.
  • a 1 , A 2 , E, and F are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or substituted or unsubstituted. Ring aromatic heterocyclic ring having 2 to 40 carbon atoms;
  • Two carbon atoms adjacent to each other in the aromatic ring of A 1 and two carbon atoms adjacent to each other in the aromatic ring of A 2 are each a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R 1 and R 2 .
  • the linking groups L 1 to L 12 are the same as or different from each other, and each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substitution or Unsubstituted C2-C60 alkynylene group, substituted or unsubstituted C3-C60 cycloalkylene group, substituted or unsubstituted C2-C60 heterocycloalkylene group, substituted or unsubstituted C6-C60 An arylene group or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
  • M is any one selected from NR 3 , CR 4 R 5 , SiR 6 R 7 , GeR 8 R 9 , O, S, Se;
  • the substituents R 1 to R 9 , Ar 1 to Ar 8 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 50 carbon atoms.
  • the R 1 and R 2 may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, O, P, Si, S May be substituted with any one or more heteroatoms selected from Ge, Se, and Te;
  • P1 to p4, r1 to r4, and s1 to s4 are each an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L 1 to L 12 are the same as or different from each other,
  • X is an integer of 1 or 2
  • y and z are the same or different, and each independently an integer of 0 to 3
  • Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 5 and Ar 6 , and Ar 7 and Ar 8 may be connected to each other to form a ring;
  • 'Substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, alkenyl group of 1 to 24 carbon atoms , Alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or heteroarylalkyl group having 2 to 24 carbon atoms , Alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 1 to 24 carbon atoms, heteroaryl group having 1 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms,
  • groups are amine in the case where the structural formula Q 1 is connected to A 2 ring including the Ar 1 and Ar 2 be be bonded to A 2 ring structure has a characteristic, and to be a structural formula Q 2 in the formula (B) connected to the a 1 ring, formula Q 1 a is be an amine group is bonded, including the Ar 1 and Ar 2 wherein a 2 ring when connected to a 2 rings Has structural characteristics.
  • the range of carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms means the total carbon number constituting the alkyl portion or the aryl portion when viewed as unsubstituted without considering the substituted portion.
  • a phenyl group substituted with a butyl group in the para position should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.
  • the aryl group which is a substituent used in the compound of the present invention, means an aromatic system composed of a hydrocarbon including one or more rings, and when the aryl group has a substituent, the aryl group may be fused to each other with neighboring substituents to further form a ring. Can be.
  • aryl group examples include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like, and at least one hydrogen atom of the aryl group may be a Atom, hydroxy group, nitro group, cyano group, silyl group, amino group (-NH 2 , -NH (R), -N (R ') (R''),R' and R "are independently of each other 1 to 10 carbon atoms Alkyl group, in this case an " al
  • the heteroaryl group which is a substituent used in the compound of the present invention, contains 1, 2 or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, Te, and has 2 to 24 carbon atoms where the remaining ring atoms are carbon. Refers to a ring aromatic system, wherein the rings may be fused to form a ring. At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the case of the aryl group.
  • the aromatic heterocycle means that at least one aromatic carbon in the aromatic hydrocarbon ring is substituted with at least one hetero atom selected from N, O, P, Si, S, Ge, Se, Te.
  • alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like, and at least one of the alkyl groups
  • the hydrogen atom can be substituted by the same substituent as the case of the said aryl group.
  • silyl group which is a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl and methylcyclo Butylsilyl, dimethylfurylsilyl, and the like, and at least one hydrogen atom in the silyl group may be substituted with the same substituent as in the case of the aryl group.
  • A1, A2, E, and F in Formula A or Formula B of the present invention may be the same or different, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms.
  • aromatic hydrocarbon The rings may be the same or different and independently of each other, any one selected from [Formula 10] to [Formula 21].
  • R is the same as R 1 and R 2 defined above, m is an integer of 1 to 8, when m is 2 or more or R is 2 or more, each R is It may be the same or different from each other.
  • a 1 , A 2 , E, and F in Formula A or Formula B of the present invention may be the same as or different from each other, and may be independently substituted or unsubstituted aromatic hetero rings having 2 to 30 carbon atoms. have.
  • Aromatic hetero rings may be the same or different and may be independently selected from [Formula 31] to [Formula 40].
  • T 1 to T 12 are the same as or different from each other, and each independently, C (R 41 ), C (R 42 ) (R 43 ), N, N (R 44 ), O, S, Se, Te, Si ( R 45 ) (R 46 ) and Ge (R 47 ) (R 48 ), which may be any one of T 1 to T 12 are not all carbon atoms at the same time, wherein R 41 to R 48 are defined above
  • R 1 and R 2 and two adjacent ones of T 1 to T 12 in the aromatic ring form a 5-membered ring including carbon atoms connected to the substituents R 1 and R 2 as carbon atoms, or the structural formula Q Containing a single bond for forming a five-membered ring containing oxygen atoms at 1 and Q 2 ,
  • the [Formula 33] may include a compound represented by the following [Formula 33-1] by the resonance structure according to the movement of electrons.
  • T 1 to T 7 are the same as T 1 to T 12 defined in [Formula 31] to [Formula 40].
  • the [formula 31] to [formula 40] may be selected from heterocycles represented by the following [formula 41].
  • X is the same as R 1 and R 2 defined above, m is an integer of 1 to 11, when m is 2 or more, a plurality of X are the same or different from each other,
  • the aromatic heterocyclic ring is A 1 has two carbon atom the formula Q 1 adjacent to take the ring, if binding to the ring, or A 2, while for the ring structural formula Q 1 or the formula Q 2 of a * and Or by combining with * in formula Q 2 to form a condensed ring.
  • the linking groups L 1 to L 12 in Formula A or Formula B of the present invention are each a single bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted carbon number 2 It may be any one selected from the hetero arylene group of 20.
  • linking group L 1 to L 12 is a single bond, or any one selected from the following [Formula 22] to [Formula 30],
  • p1 to p4, r1 to r4, s1 to s4 are each 1 or 2,
  • x can be one.
  • the carbon site of the aromatic ring may be bonded to hydrogen or deuterium.
  • y may be 1 and z may be zero.
  • the substituents R1 and R2 in the formula (A) or formula (B) of the present invention are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and are connected to each other to form a ring. Or they may not be linked to each other to form a ring.
  • the substituents R 1 to R 9 , Ar 1 to Ar 8 of the present invention are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and substituted. Or an unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, at least one selected from O, N, S and Si, a cyano group and a halogen group It can be any one.
  • 'substituted' substituents in A 1 , A 2 , E, F, Ar 1 to Ar 8 , L 1 to L 12 , and R 1 to R 9 Is a cyano group, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, and 6 carbon atoms It may be any one selected from the group consisting of arylsilyl group of 18 to.
  • amine compound of the present invention may be any one selected from the following [Formula 1] to [Formula 239].
  • the present invention is a first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one organic light emitting compound of the present invention.
  • (organic layer) contains at least one organic compound means "(organic layer) one organic compound belonging to the scope of the present invention or two or more different compounds belonging to the organic compound category. May include. "
  • the organic layer including the organic light emitting compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. have.
  • the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is composed of a host and a dopant, the organic light emitting compound of the present invention may be used as a dopant.
  • a host material may be used as the dopant in the light emitting layer.
  • the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
  • a known electron transport material may be used as a function of stably transporting electrons injected from an electron injection electrode (Cathode).
  • known electron transport materials include quinoline derivatives, particularly tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10-noate) olate: Bebq2), ADN, compound 201, compound 202, BCP, oxadiazole derivatives such as PBD, BMD, BND may be used, but is not limited thereto.
  • the organometallic compound represented by the formula (C) may be used alone or in combination with the electron transport layer material.
  • Y is a portion in which any one selected from C, N, O and S is directly bonded to the M to form a single bond, and any one selected from C, N, O and S forms a coordination bond to the M And a ligand chelated by the single bond and the coordination bond
  • M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination with M,
  • O oxygen
  • A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon group having 2 to 20 carbon atoms
  • the 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It is meant to be substituted with one or more substituents selected from the group consisting of an aryloxy group, an aryl group, a heteroaryl group, germanium, phosphorus and boron.
  • Y is the same or different, and may be any one selected from the following [formula C1] to [formula C39] independently, but is not limited thereto.
  • R is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms and substituted or unsubstituted
  • the organic light emitting device includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, if necessary, the hole injection layer 30 and the electron
  • the injection layer 70 may be further included.
  • an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.
  • the anode 20 is formed by coating an anode electrode material on the substrate 10.
  • a substrate used in a conventional organic EL device is used.
  • An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable.
  • the anode electrode material indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used.
  • the hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode.
  • the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30.
  • the hole injection layer material may be used without particular limitation as long as it is commonly used in the art, for example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine)], TPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine ] Etc.
  • 2-TNATA 4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine
  • the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1- Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD) and the like can be used.
  • TPD N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1- Biphenyl] -4,4'-diamine
  • a-NPD N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine
  • the present invention is not necessarily limited thereto.
  • the organic light emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method. can do.
  • the hole blocking layer prevents such a problem by using a material having a very low highest Occupied Molecular Orbital (HOMO) level because when the hole is introduced into the cathode through the organic light emitting layer is reduced the lifetime and efficiency of the device.
  • the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.
  • the organic EL device is completed by vapor deposition to form a cathode 80 electrode.
  • the metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.
  • the light emitting layer may be formed of a host and a dopant.
  • the thickness of the said light emitting layer is 50-2,000 GPa.
  • the host used in the emission layer may be a compound represented by Formula 1A to Formula 1D.
  • Ar 7, Ar 8 and Ar 9 are the same as or different from each other, and each independently, a single bond, a substituted or unsubstituted C 5 -C 60 aromatic linking group, or a substituted or unsubstituted C 2 -C 60 heteroaromatic linking group;
  • R 21 to R 30 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or Salts thereof, phosphoric acid or salts thereof, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms, substituted or unsubstituted Substituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon
  • E, f and g are the same as or different from each other, and each independently an integer of 0 or 1 to 4;
  • the two sites marked with * of the anthracene may be identical to or different from each other, and may independently combine with the P or Q structure to constitute an anthracene-based derivative selected from Formulas 1Aa-1 to 1Aa-3.
  • the 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, of 1 to 24 carbon atoms Alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, or C2-C24 hetero Arylalkyl group, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 1 to 24 carbon atoms, heteroarylaryl group having 1 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, and 1 to 24 carbon atoms It means substituted with one or more substituents
  • Ar 17 to Ar 20 may be the same as or different from each other, and each independently the same substituent as defined in Ar 7 to Ar 8 in Formula 1A, and R 60 to R 63 may be defined in R 21 to R 30 of Formula 1A. And the same substituent as described above.
  • the w and ww are the same or different from each other, the x and xx are the same or different from each other, the w + ww and x + xx values are the same or different from each other and are each independently an integer of 0-3.
  • y and yy are the same as or different from each other, z and zz are the same as or different from each other, and y + yy to z + zz are 2 or less, and are integers of 0 to 2, respectively.
  • Ar 21 to Ar 24 may be the same as or different from each other, and each independently the same substituent as defined in Ar 7 to Ar 8 of Formula 1A, and R 64 to R 67 may be selected from R 21 to R 30 of Formula 1A. It consists of the same substituent as defined.
  • ee to hh are the same as or different from each other and each independently an integer of 1 to 4
  • ii to ll are the same or different from each other and each independently an integer of 0 to 4.
  • Ar 25 to Ar 27 are the same as or different from each other, and each independently include the same substituent as defined in Ar 7 to Ar 8 of Formula 1A, and R 68 to R 73 are the same as or different from each other, and each independently It consists of the same substituent as defined in R ⁇ 21> -R ⁇ 30> of 1A, and each substituent may form the saturated or unsaturated cyclic structure with adjacent ones.
  • the mm to ss are the same as or different from each other and are each independently an integer of 0 to 4.
  • the host may be represented by any one selected from the group represented by the following [Host 1] to [Host 56], but is not limited thereto.
  • the emission layer may further include various hosts and various dopant materials.
  • one or more layers selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process.
  • the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each layer by heating or the like in a vacuum or low pressure state, and the solution process forms the respective layers.
  • the organic light emitting device in the present invention is a flat panel display device; Flexible display devices; Monochrome or white flat lighting devices; And a solid or white flexible lighting device; can be used in any one device selected from.
  • Methyl 5-bromo-2-iodobenzoate (25.0 g, 73 mmol), 4-dibenzofuranboronic acid (18.7 g, 88 mmol), tetrakis (triphenylphosphine) palladium (1.7 in a 500 mL round bottom flask reactor g, 0.15 mmol) and potassium carbonate (20.2 g, 146.7 mmol) were added, followed by 125 mL of toluene, 125 mL of tetrahydrofuran, and 50 mL of water. The temperature of the reactor was raised to 80 degrees and stirred for 10 hours.
  • 2-Penoxyaniline (25.0, 0.135mol), hydrochloric acid and 30ml of water were added to a 1L round-bottomed reactor, and the mixture was cooled to 0 ° C and stirred for 1 hour.
  • 75 ml of an aqueous solution of sodium nitride (11.2 g, 0.162 mol) was added dropwise to the reaction solution, followed by stirring for 1 hour.
  • 75 ml of an aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise, the reaction solution was added dropwise so that the temperature of the reaction solution did not exceed 5 degrees.
  • ⁇ Intermediate 6-k> (2.2g, 90.4%) was obtained by the same method as in Synthesis Example 1- (6), except that ⁇ Intermediate 6-j> was used instead of ⁇ Intermediate 1-e>.
  • ⁇ Intermediate 10-d> (3g, 62.5%) was obtained by the same method as in Synthesis Example 1- (4), except that ⁇ Intermediate 10-c> was used instead of ⁇ Intermediate 1-c>.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention se rapporte à un composé hétérocyclique contenant un groupe amine aromatique et à un dispositif électroluminescent organique comportant celui-ci et, plus précisément, à un composé hétérocyclique et à un dispositif électroluminescent organique comportant celui-ci, le composé hétérocyclique étant excellent en termes de luminance et de rendement d'électroluminescence et pouvant présenter une longue durée de vie et d'excellentes caractéristiques de dispositif lorsqu'il est utilisé comme matériau électroluminescent organique.
PCT/KR2015/004552 2014-05-13 2015-05-07 Composé hétérocyclique contenant un groupe amine aromatique et dispositif électroluminescent organique comportant celui-ci WO2015174682A1 (fr)

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CN201580020254.2A CN106458953B (zh) 2014-05-13 2015-05-07 包含芳香族胺基的杂环化合物及包含该化合物的有机发光元件
US15/306,867 US11672172B2 (en) 2014-05-13 2015-05-07 Heterocyclic compound comprising aromatic amine group and organic light-emitting diode including the same
JP2016565495A JP6367367B2 (ja) 2014-05-13 2015-05-07 芳香族アミン基を含む複素環式化合物およびこれを含む有機発光素子
EP15793316.9A EP3144302B1 (fr) 2014-05-13 2015-05-07 Composé hétérocyclique contenant un groupe amine aromatique et dispositif électroluminescent organique comportant celui-ci

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WO2016108419A1 (fr) * 2014-12-31 2016-07-07 에스에프씨 주식회사 Diode électroluminescente organique ayant une efficacité élevée et une longue durée de vie
US20160204355A1 (en) * 2015-01-13 2016-07-14 Sfc Co., Ltd. Organic Light-Emitting Diode With High Efficiency And Long Lifetime
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WO2016126022A1 (fr) * 2015-02-04 2016-08-11 에스에프씨 주식회사 Élément organique électroluminescent apte à commande basse tension et ayant une longue durée de vie
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WO2017122649A1 (fr) * 2016-01-14 2017-07-20 日産化学工業株式会社 Composé contenant des atomes de fluor et leur utilisation
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WO2017146397A1 (fr) * 2016-02-22 2017-08-31 에스에프씨 주식회사 Nouveau composé amine et diode électroluminescente organique le comprenant
EP3232490A1 (fr) 2016-04-12 2017-10-18 Novaled GmbH Diode électroluminescente organique comprenant une couche semi-conductrice organique
JP2017204492A (ja) * 2016-05-09 2017-11-16 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
CN107619402A (zh) * 2016-07-14 2018-01-23 Sfc株式会社 具有高效率特性的有机发光元件
JP2018507909A (ja) * 2015-02-16 2018-03-22 メルク パテント ゲーエムベーハー 電子素子のための材料
EP3425692A1 (fr) 2017-07-07 2019-01-09 Novaled GmbH Dispositif électroluminescent organique comprenant une couche d'injection d'électrons avec métal à valence nulle
JP2019503364A (ja) * 2015-12-24 2019-02-07 ドゥーサン コーポレイション 有機化合物およびこれを含む有機電界発光素子
JP2019512476A (ja) * 2016-03-03 2019-05-16 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイスのための材料
WO2019101833A1 (fr) * 2017-11-24 2019-05-31 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2019101835A1 (fr) * 2017-11-24 2019-05-31 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US10312449B2 (en) 2015-05-27 2019-06-04 Samsung Display Co., Ltd. Organic light-emitting device
US20200176695A1 (en) * 2018-07-12 2020-06-04 Sfc Co., Ltd. Organic light-emitting diode with High efficiency and low voltage
WO2020171480A1 (fr) 2019-02-20 2020-08-27 주식회사 엘지화학 Dérivés d'anthracène et dispositif électronique organique l'utilisant
CN112794833A (zh) * 2019-11-14 2021-05-14 石家庄诚志永华显示材料有限公司 一种蓝光染料化合物及其应用
US20210184119A1 (en) * 2015-11-26 2021-06-17 Samsung Display Co., Ltd. Organic light-emitting device
US11453680B2 (en) 2016-11-25 2022-09-27 Merck Patent Gmbh Bisbenzofuran-fused indeno[1,2-B]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED)
EP4116297A1 (fr) * 2014-07-28 2023-01-11 SFC Co., Ltd. Dérivé de fluorène condensé comprenant un anneau hétérocyclique
US11584753B2 (en) 2016-11-25 2023-02-21 Merck Patent Gmbh Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED)

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WO2016108419A1 (fr) * 2014-12-31 2016-07-07 에스에프씨 주식회사 Diode électroluminescente organique ayant une efficacité élevée et une longue durée de vie
US10014479B2 (en) * 2015-01-13 2018-07-03 Sfc Co., Ltd. Organic light-emitting diode with high efficiency and long lifetime
US20160204355A1 (en) * 2015-01-13 2016-07-14 Sfc Co., Ltd. Organic Light-Emitting Diode With High Efficiency And Long Lifetime
WO2016126022A1 (fr) * 2015-02-04 2016-08-11 에스에프씨 주식회사 Élément organique électroluminescent apte à commande basse tension et ayant une longue durée de vie
JP2018507909A (ja) * 2015-02-16 2018-03-22 メルク パテント ゲーエムベーハー 電子素子のための材料
EP3098873A1 (fr) * 2015-05-27 2016-11-30 Samsung Display Co., Ltd. Dispositif électroluminescent organique
US10312449B2 (en) 2015-05-27 2019-06-04 Samsung Display Co., Ltd. Organic light-emitting device
US10367147B2 (en) 2015-05-27 2019-07-30 Samsung Display Co., Ltd. Organic light-emitting device
WO2016200080A1 (fr) * 2015-06-12 2016-12-15 에스에프씨 주식회사 Élément électroluminescent organique ayant une efficacité élevée
CN106977479A (zh) * 2015-11-13 2017-07-25 Sfc株式会社 新型胺化合物及包括此的有机发光元件
US11563181B2 (en) 2015-11-13 2023-01-24 Sfc Co., Ltd. Amine compounds for organic light-emitting diode and organic light-emitting diode including the same
US20210184119A1 (en) * 2015-11-26 2021-06-17 Samsung Display Co., Ltd. Organic light-emitting device
US11066382B2 (en) 2015-12-24 2021-07-20 Solus Advanced Materials Co., Ltd. Organic compound and organic electroluminescent device comprising same
JP2019503364A (ja) * 2015-12-24 2019-02-07 ドゥーサン コーポレイション 有機化合物およびこれを含む有機電界発光素子
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TWI726036B (zh) * 2016-01-14 2021-05-01 日產化學工業股份有限公司 含有氟原子之化合物及其利用
WO2017122649A1 (fr) * 2016-01-14 2017-07-20 日産化学工業株式会社 Composé contenant des atomes de fluor et leur utilisation
US10336686B2 (en) 2016-01-14 2019-07-02 Nissan Chemical Industries, Ltd. Fluorine atom-containing compound and use thereof
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EP3232490A1 (fr) 2016-04-12 2017-10-18 Novaled GmbH Diode électroluminescente organique comprenant une couche semi-conductrice organique
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JP2017204492A (ja) * 2016-05-09 2017-11-16 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
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US11584753B2 (en) 2016-11-25 2023-02-21 Merck Patent Gmbh Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED)
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EP3425692A1 (fr) 2017-07-07 2019-01-09 Novaled GmbH Dispositif électroluminescent organique comprenant une couche d'injection d'électrons avec métal à valence nulle
CN111417639A (zh) * 2017-11-24 2020-07-14 默克专利有限公司 用于有机电致发光器件的材料
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US11639339B2 (en) 2017-11-24 2023-05-02 Merck Patent Gmbh Materials for organic electroluminescent devices
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