WO2016017919A2 - 헤테로고리를 포함하는 축합 플루오렌 유도체 - Google Patents

헤테로고리를 포함하는 축합 플루오렌 유도체 Download PDF

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WO2016017919A2
WO2016017919A2 PCT/KR2015/005801 KR2015005801W WO2016017919A2 WO 2016017919 A2 WO2016017919 A2 WO 2016017919A2 KR 2015005801 W KR2015005801 W KR 2015005801W WO 2016017919 A2 WO2016017919 A2 WO 2016017919A2
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compound
carbon atoms
group
formula
substituted
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WO2016017919A3 (ko
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차순욱
정경석
송주만
이유림
박상우
김희대
박석배
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SFC Co Ltd
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SFC Co Ltd
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Priority to EP15828042.0A priority Critical patent/EP3176158A4/en
Priority to EP22168494.7A priority patent/EP4116297B1/en
Priority to JP2017500825A priority patent/JP6533825B2/ja
Priority to CN201580028545.6A priority patent/CN106458954B/zh
Priority to US15/325,001 priority patent/US11683980B2/en
Publication of WO2016017919A2 publication Critical patent/WO2016017919A2/ko
Publication of WO2016017919A3 publication Critical patent/WO2016017919A3/ko
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene

Definitions

  • the present invention relates to a condensed fluorene derivative including a heterocycle, and more particularly, when used as an organic light emitting material, excellent in brightness and luminous efficiency, and manufacturing a heterocyclic compound that can show excellent long-term device characteristics It relates to an intermediate for.
  • 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 in which an aryl amine is bonded, and the like.
  • No. 10-2012-0047706 discloses a compound having a structure in which dibenzofuran or dibenzothiophene is present with fluorene or benzofuran or dibenzothiophene is present together with carbazole in one molecule.
  • the organic light emitting element used is disclosed.
  • the organic light emitting material has excellent luminance and luminous efficiency compared to the organic light emitting materials manufactured by the prior art including the prior art, and has a long life characteristic. There is a continuing need for development of compounds.
  • the first technical problem to be achieved by the present invention is to provide a novel intermediate compound for preparing a compound that can be used as a material for an organic light emitting diode (OLED).
  • OLED organic light emitting diode
  • the present invention provides a 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 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 .
  • 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 are the same as or different from each other, and independently from each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted A substituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, Substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon
  • 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 and aromatic monocyclic or polycyclic rings are N, O, P, Si, S May be substituted with any one or more heteroatoms selected from Ge, Se, and Te;
  • the s1, s3 and s4 are each independently the same or different integers of 0 to 3, and s2 is an integer of 1 to 3,
  • each of X1 to X4 is the same as or different from each other,
  • X 1 to X 4 are the same as or different from each other independently, and are hydrogen, deuterium, or a leaving group,
  • the compound represented by [Formula A] or [Formula B] can be utilized as an intermediate of an organic light emitting material, and finally the light emitting material obtained when manufacturing the light emitting material using the intermediate is compared with the existing material It is excellent in brightness and luminous efficiency, and can show excellent device characteristics of long life, thereby providing an organic light emitting device having improved characteristics.
  • FIG. 1 is a schematic diagram of an organic light emitting device manufactured according to an embodiment of the present invention.
  • the present invention provides an intermediate compound for producing an organic light emitting material that can be used in an organic light emitting device. More specifically, the intermediate compound is represented by the following [Formula A] or [Formula B].
  • 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 .
  • 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 are the same as or different from each other, and independently from each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted A substituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, Substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon
  • the R1 and R2 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 It may be substituted with any one or more heteroatoms selected from Se, Te;
  • the s1, s3 and s4 are each independently the same or different integers of 0 to 3, and s2 is an integer of 1 to 3,
  • each of X1 to X4 is the same as or different from each other,
  • X 1 to X 4 are the same as or different from each other independently, and are hydrogen, deuterium, or a leaving group,
  • '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,
  • the compound represented by the formula (A) has a structural feature in which the structural formula Q1 is linked to the A 2 ring, in which case X 2 represented by the hydrogen, deuterium or leaving group is necessarily bonded to the A 2 ring.
  • the compound represented by the formula (B) is a structure Q 2 is connected to the A 1 ring, the structure Q 1 is connected to the A 2 ring, in this case X 2 represented by the hydrogen, deuterium or leaving group is necessarily bonded to the A 2 ring 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 in the case where 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 penalenyl group, pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, peryleneyl, chrysenyl, naphthacenyl, acenaphthylenyl group, indasenyl group, fluoranthenyl and the like.
  • One or more hydrogen atoms of the aryl group may be a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH 2 , -NH (R), -N (R ') (R''), R 'And R' are independently of each other an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group”), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, Halogenated alkyl group of 1 to 24 carbon atoms, alkenyl group of 1 to 24 carbon atoms, 1 to 24 carbon atoms Alkynyl group, which may be substituted with a heteroarylalkyl group having 1 to 24 hetero
  • 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.
  • 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 hydrocarbon rings having 6 to 50 carbon atoms. have.
  • a 1 , A 2 , E, and F in Formula A or Formula B are the same or different, and each independently correspond to a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms
  • the aromatic hydrocarbon ring is the same or different, and may be any one selected from [formula 10] to [formula 21] independently of each other.
  • 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, each R may be the same or different from each other. .
  • the leaving groups X 1 to X 4 are the same as or different from each other independently, and are hydrogen, deuterium, or a leaving group.
  • the leaving group may be used without limitation as long as the leaving group can be separated to introduce a desired substituent instead of the leaving group to design a molecular structure to be used as a material for an organic light emitting device. Do.
  • the leaving group may be released when reacting with the secondary amine, so that the substituent to be introduced may be released so as to be converted into the tertiary amine.
  • a boric acid group having an aryl group or an alkyl group may be used. It may be a leaving group which can be separated so that an aryl group such as anthracene or the like is introduced by the Suzuki coupling reaction.
  • a halogen selected from Cl, Br, F, I, alkyl sulfonate of 1 to 30 carbon atoms, aryl sulfonate of 6 to 40 carbon atoms, aryl of 7 to 40 carbon atoms Any one selected from alkyl sulfonates and halogenated alkyl sulfonates having 1 to 30 carbon atoms can be used, and preferably halogen selected from Cl, Br, F, and I can be used.
  • s2 is 1, s1, s3 and s4 are the same or different, and may each be 0 or 1 independently of each other. That is, in Formulas A and B, the halogen bonded to the A 2 ring is one, and the halogen bonded to the A 1 ring or the E ring or the F ring may be absent or one.
  • the substituents R 1 and R 2 in Formula A or Formula B of the present invention may be the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and are connected to each other to a ring It may form a, or may not be connected to each other to form a ring.
  • the substituents R 1 to R 9 of the present invention are the same as or different from each other, and independently of each other hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted carbon number 3 It may be any one selected from a cycloalkyl group of 30 to 30, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms having at least one selected from O, N, S and Si as a hetero atom, a cyano group, a halogen group. .
  • the substituents substituted in A 1 , A 2 , E, F, and R 1 to R 9 may be a cyano group, a halogen group, or an alkyl group having 1 to 6 carbon atoms.
  • the compound according to the present invention may be any one selected from the following [Compound 1] to [Compound 108].
  • the compound represented by Formula A or Formula B according to the present invention may react with an amine to generate an amine derivative.
  • the amine may be a primary amine or a secondary amine, and may react with the secondary amine to form a tertiary amine for use as a material for an organic light emitting device.
  • Ra and Rb in the secondary amine may each be an aryl group having 6 to 40 carbon atoms.
  • the secondary amine is preferably used more than the content of the leaving group contained in the formula (A) or formula (B).
  • a linking group may be provided between the secondary amine and the tertiary amine.
  • an alkylene group, an alkenylene group, an alkynylene group, a cycloalkylene group, a heterocycloalkylene group, an arylene group, or a heteroarylene group can be used, and are preferably the same as or different from each other, and are each independently substituted or Unsubstituted C1-C60 alkylene group, substituted or unsubstituted C2-C60 alkenylene group, substituted or unsubstituted C2-C60 alkynylene group, substituted or unsubstituted C3-C60 cyclo
  • An alkylene group, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms is an A 1 ring, It may be bonded between an A 2 ring,
  • reaction of the compounds represented by the formula (A) and the formula (B) with a substituent to be introduced such as the secondary amine, an aryl group, etc. can be easily produced by, for example, Suzuki coupling.
  • a substituent R such as an amine group, an aryl group, or the like may be introduced by the following reaction.
  • the organic light emitting compound synthesized by the Suzuki coupling may be used as a material for an organic light emitting device in the present invention. More specifically, 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 comprises at least one organic light emitting compound as described above.
  • a compound having an amine group introduced therein as the prepared final compound may be used as a material for an organic light emitting device in the present invention.
  • the term "(organic layer) includes 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 category of the organic compound. It can be included ”.
  • 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 finally prepared compound of the present invention is an organic light emitting compound is a dopant Can be used.
  • 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, in particular 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 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 light emitting layer may be displayed as 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.
  • ⁇ Intermediate 1-b> (14.5g, 39mmol) and 145ml of methanesulfonic acid were added to a 250ml round bottom flask reactor, and the temperature was raised to 80 degrees and stirred for 3 hours. After completion of the reaction by thin layer chromatography, the reaction mixture was cooled to room temperature. The reaction solution was slowly added dropwise to 150 ml of ice water and stirred for 30 minutes. The resulting solid was filtered and washed with water and methanol to obtain ⁇ Intermediate 1-c> (11.50g, 83.4%).
  • 2-Penoxyaniline (25.0, 0.135 mol), 30 ml of hydrochloric acid and 150 ml of water were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 degrees and stirred for 1 hour. At the same temperature, 75 ml of an aqueous solution of sodium nitride (11.2 g, 0.162 mol) was added dropwise, followed by stirring for 1 hour. 75 ml of an aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise, noting that the temperature of the reaction solution did not exceed 5 degrees.
  • ⁇ Formula 7> (3.0 g, 36.1%) was obtained using the same method as in Synthesis Example 1- (7) except that ⁇ Compound 58> was used instead of ⁇ Compound 1>.

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