WO2019216575A1 - Composé cyclique condensé et diode électroluminescente organique le comprenant - Google Patents

Composé cyclique condensé et diode électroluminescente organique le comprenant Download PDF

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WO2019216575A1
WO2019216575A1 PCT/KR2019/004850 KR2019004850W WO2019216575A1 WO 2019216575 A1 WO2019216575 A1 WO 2019216575A1 KR 2019004850 W KR2019004850 W KR 2019004850W WO 2019216575 A1 WO2019216575 A1 WO 2019216575A1
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group
substituted
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cyclic compound
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김장주
임형철
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서울대학교산학협력단
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—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
    • 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
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • It relates to a condensed cyclic compound and an organic light emitting device comprising the same.
  • the organic light-emitting device is a self-luminous device, which has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed, and multicoloring. .
  • the organic light emitting diode may have a structure in which an organic layer including a light emitting layer and a second electrode are sequentially formed on the first electrode. Holes injected from the first electrode and electrons injected from the second electrode may move to the emission layer. Carriers such as holes and electrons may be recombined in the emission layer to generate excitons. The excitons change from excited state to ground state and light is generated.
  • Embodiments of the present invention provide a condensed cyclic compound and an organic light emitting device including the same. Specifically, an organic light emitting device having an improved lifetime is provided.
  • a condensed cyclic compound represented by Formula 1 is provided:
  • R 11 to R 13 are each independently selected from hydrogen and the groups represented by Formulas 2-1 to 2-5;
  • X 11 is N or C (R 14 );
  • X 12 is N or C (R 15 );
  • X 13 is N or C (R 16 );
  • X 21 is selected from O and S;
  • a 21 and A 22 are each independently selected from a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group and a tetrazine group;
  • R 14 to R 15 and R 21 to R 24 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C 1- C 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted C 1 -C 60 alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group
  • b21 is selected from 1, 2 and 3;
  • b22 is selected from 1, 2, 3 and 4;
  • the first electrode Second electrode; An organic layer including an emission layer interposed between the first electrode and the second electrode;
  • the organic layer is provided with an organic light emitting device including a condensed cyclic compound represented by Formula 1.
  • the organic light emitting device including the condensed cyclic compound may have a long lifespan.
  • FIG. 1 is a cross-sectional view schematically showing the structure of an organic light emitting device according to an embodiment of the present invention.
  • FIG. 2 is a graph showing electroluminescence spectra (EL spectra) according to wavelengths of Examples 1, 2 and Comparative Example 1.
  • FIG. 1 is a graph showing electroluminescence spectra (EL spectra) according to wavelengths of Examples 1, 2 and Comparative Example 1.
  • FIG. 3 is a diagram showing 1 H-NMR data of compound 9.
  • FIG. 4 is a diagram showing a mass spectrum of Compound 9.
  • FIG. 5 is a graph of L t / L 0 versus time at 1,000 cd / m 2 of Examples 1 and 2 and Comparative Example 1.
  • FIG. 5 is a graph of L t / L 0 versus time at 1,000 cd / m 2 of Examples 1 and 2 and Comparative Example 1.
  • FIG. 6 is a graph of L t / L 0 versus time at 3,000 cd / m 2 of Examples 1 and 2 and Comparative Example 1.
  • FIG. 6 is a graph of L t / L 0 versus time at 3,000 cd / m 2 of Examples 1 and 2 and Comparative Example 1.
  • the condensed cyclic compound may be represented by Formula 1 below:
  • R 11 to R 13 may be each independently selected from hydrogen and groups represented by Formulas 2-1 to 2-5.
  • R 11 to R 13 may be independently selected from the groups represented by Formulas 2-1 to 2-5, but are not limited thereto.
  • R 11 to R 13 may each independently be a group represented by Formula 2-1, but are not limited thereto.
  • R 11 to R 13 may be each independently selected from the group represented by Formula 2-11 to 2-90, but is not limited thereto:
  • X 21 refers to the description in Formula 2-1 above;
  • R 21a , R 21b , R 21c and R 21d each independently refer to the description for R 21 in Formula 2-1;
  • R 22a , R 22b , R 22c and R 22d each independently refer to the description for R 21 in Formula 2-1 above;
  • R 11 to R 13 may be each independently selected from the group represented by Formula 2-15 to 2-90, but is not limited thereto.
  • X 11 is N or C (R 14 ); X 12 is N or C (R 15 ); X 13 may be N or C (R 16 ).
  • X 11 may be C (R 14 ); X 12 is C (R 15 ); X 13 may be C (R 16 ), but is not limited thereto.
  • X 21 may be selected from O and S.
  • X 21 may be O, but is not limited thereto.
  • a 21 and A 22 may be each independently selected from a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, and a tetrazine group. .
  • a 21 and A 22 may be each independently selected from a benzene group and a pyridine group, but are not limited thereto.
  • At least one of A 21 and A 22 in Formula 2-1 may be a pyridine group, but is not limited thereto.
  • R 14 to R 15 and R 21 to R 24 each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, Cyano group, nitro group, substituted or unsubstituted C 1 -C 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted C 1- C 60 alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or Unsubstituted C 1 -C 10 heterocycloalkenyl group, substituted or Unsubstituted C 1 -C 10 heterocycloalkenyl group, substitute
  • R 14 to R 15 and R 21 to R 24 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group And a substituted or unsubstituted C 1 -C 60 alkyl group, but is not limited thereto.
  • R 14 to R 15 and R 21 to R 24 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I and It may be selected from a C 1 -C 10 alkyl group, but is not limited thereto.
  • B21 in Formulas 2-1 to 2-5 is selected from 1, 2, and 3; b22 may be selected from 1, 2, 3 and 4.
  • * is a binding site with a neighboring atom.
  • the condensed cyclic compound represented by Formula 1 may be represented by the following Formula 1-1, but is not limited thereto:
  • R 11 to R 13 may each be a group represented by Formula 2-1, but are not limited thereto.
  • R 11 to R 13 may be each independently selected from the groups represented by Formulas 2-11 to 2-90, but are not limited thereto.
  • the condensed cyclic compound represented by Formula 1 may be selected from Compounds 1 to 25, but is not limited thereto.
  • the condensed cyclic compound represented by Formula 1 necessarily includes a group represented by Formulas 2-1 to 2-5, the lowest triplet excitation energy level of the condensed cyclic compound may be high.
  • the groups represented by Formulas 2-1 to 2-5 include a pyridine group including N, the lowest excitation triplet energy level of the condensed cyclic compound may be particularly high. Accordingly, the condensed cyclic compound may be useful as an electron transporting layer material of an organic light emitting device that emits dark blue.
  • the condensed cyclic compound represented by Formula 1 may have a high bond dissociation energy (BDE) as the ring consisting of C and X 11 to X 13 and R 11 to R 13 in Formula 1 are each connected to a CC bond. . Therefore, the lifespan of the organic light emitting device including the same may be improved.
  • BDE bond dissociation energy
  • the condensed cyclic compound represented by Chemical Formula 1 is disposed in a ring formed of C and X 11 to X 13 in Chemical Formula 1 and R 11 to R 13 not tilted on the same plane, but bent at a predetermined angle.
  • agglomeration may occur relatively less when deposition is performed. Therefore, the lifespan of the organic light emitting device including the same may be improved.
  • the S1 energy level, T1 energy level, HOMO energy level, LUMO energy level, and binding dissociation energy of some compounds of the condensed cyclic compound represented by Formula 1 are based on B3LYP (DFT: B3LYP, 6-31G ** /
  • the results of evaluation using the Jaguar program accompanied by the molecular structure optimization by the structure optimization at the MIDIX level) are shown in Table 1 below.
  • FIG. 1 is a cross-sectional view schematically showing the structure of an organic light emitting device 10 according to an embodiment of the present invention.
  • the organic light emitting diode 10 may include a first electrode 11; Second electrode 19; An organic layer (15) including an emission layer (16) interposed between the first electrode and the second electrode;
  • the organic layer may include a condensed cyclic compound represented by Chemical Formula 1.
  • the organic layer may include an electron transport region between the emission layer and the second electrode, and the electron transport region may include a condensed cyclic compound represented by Formula 1, but is not limited thereto.
  • a substrate may be further included on the lower portion of the first electrode 11 (the opposite side where the organic layer is disposed) or on the upper portion of the second electrode 19 (the opposite side where the organic layer is located).
  • a substrate used in a conventional organic light emitting device may be used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance may be used.
  • the first electrode 11 of the organic light emitting element 10 may be an anode to which a positive voltage is applied, and the second electrode 19 may be a cathode to which a negative voltage is applied. .
  • the first electrode 11 may be a cathode and the second electrode 19 may be an anode.
  • the first electrode 11 is an anode and the second electrode 19 will be described based on the case of a cathode.
  • the first electrode 11 may be formed as a transparent electrode or a reflective electrode, and in the case of a bottom emission type, may be formed as a transparent electrode.
  • ITO, IZO, ZnO or graphene When forming a transparent electrode, ITO, IZO, ZnO or graphene may be used, and when forming a reflective electrode, Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a compound thereof After the reflection film is formed, it can be formed by forming a film thereon with ITO, IZO, ZnO or graphene.
  • the first electrode 11 may be formed using various known methods, for example, a deposition method, a sputtering method, or a spin coating method.
  • the organic layer 15 may further include a hole transport region between the light emitting layer 16 and the first electrode 11, and further include an electron transport region between the light emitting layer 16 and the second electrode 19. Can be.
  • the hole transport region is a region related to the injection and transport of holes from the anode to the light emitting layer
  • the electron transport region is a region related to the injection and transport of electrons from the cathode to the light emitting layer.
  • the hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.
  • the hole transport region may include only a hole injection layer or only a hole transport layer.
  • the hole transport region may have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer, which are sequentially stacked from the first electrode 11.
  • the hole injection layer HIL may be formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, cast, LB, and the like. have.
  • a known hole injection material may be used.
  • a phthalocyanine compound such as copper phthalocyanine, m-MTDATA, TDATA, TAPC (4,4′-Cyclohexylidenebis [N, N-bis (4-methylphenyl) benzenamine]), 2-TNATA (4,4 ', 4' '-Tris [2-naphthyl (phenyl) amino] triphenylamine), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), PANI / CSA (polyaniline / camphorsulfonic acid) or PANI / PSS (polyaniline / poly (4-styrenesulfonate)), HATCN (1,4,5,8,9,11-hexaaza
  • the hole transport layer HIL may be formed on the first electrode 11 or on the hole injection layer by using various methods such as vacuum deposition, spin coating, casting, and LB. Can be formed.
  • the hole transport layer may be a known hole transport material, for example, mCP (1,3-bis (9-carbazolyl) benzene), TCTA (Tris (4-carbazoyl-9-yl-phenyl) amine), CBP (4,4′-Bis (N-carbazolyl) -1,1'-biphenyl), mCBP (3,3-bis (carbazol-9-yl) bipheny), NPB (N, N'-di (1-naphthyl ) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine), m-MTDATA (4,4 ', 4 "-tris [phenyl (m-tolyl) amino] triphenylamine) , TPD (N, N′-bis (3-methylphenyl) -N, N′-diphenylbenzidine) may be used, but is not limited thereto.
  • mCP 1,3-
  • the light emitting layer 16 may be formed on the hole transport region using various methods such as vacuum deposition, spin coating, casting, or LB.
  • the light emitting layer 16 may include a host and a dopant.
  • the host may include a condensed cyclic compound represented by Chemical Formula 1.
  • the host may be mCP (1,3-bis (9-carbazolyl) benzene), TCTA (Tris (4-carbazoyl-9-ylphenyl) amine), CBP (4,4′-Bis (N-carbazolyl) -1,1'-biphenyl), mCBP (3,3-bis (carbazol-9-yl) bipheny), NPB (N, N'-di (1-naphthyl) -N, N'-diphenyl- (1, 1'-biphenyl) -4,4'-diamine), m-MTDATA (4,4 ', 4 "-tris [phenyl (m-tolyl) amino] triphenylamine), TPD (N, N'-bis (3- methylphenyl) -N, N'-diphenylbenzidine), the following compound pBCb2Cz, B3PYMPM (bis-4,6- (3,5-di-3-
  • the light emitting layer 16 may include a dopant, a first host, and a second host.
  • the first host may be a hole transporting host
  • the second host may be an electron transporting host, but is not limited thereto.
  • the second host may include a condensed cyclic compound represented by Formula 1, but is not limited thereto.
  • the first host may be a carbazole derivative or an aromatic amine compound, but is not limited thereto.
  • the first host may be selected from pBCb2Cz, mCP, TCTA, CBP, mCBP, nNPB, m-MTDATA and TPD, but is not limited thereto.
  • the first host and the second host may form an exciplex.
  • the first host and the second host may be included in the weight ratio of 10:90 to 90:10 in the light emitting layer.
  • the dopant may be a phosphorescent dopant, a fluorescent dopant and / or a delayed fluorescent dopant.
  • the phosphorescent dopant may be, for example, Ir (ppy) 3 , Ir (ppy) 2 (acac), Ir (mppy) 3 , Ir (mpp) 2 acac, F 2 Irpic, (F 2 ppy) 2 Ir (tmd) , Ir (ppy) 2 tmd, Ir (pmi) 3 , Ir (pmb) 3 , FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir (chpy) 3 , PO-01 (C 31 H 23 IrN 2 O 2 S 2 ), Ir (HFP) 2 (pic), Ir (HFP) 2 (mpic), Ir (ppz) 3 and Ir (dfppz) 3 may include at least one selected from, but is not limited thereto.
  • the fluorescent dopant is, for example, perylene, TBPe (2,5,8,11-tetra-tert-butylperylene), BCzVB (1,4-bis [2- (3-N-ethylcarbazoryl) vinyl] benzene), BCzVBi (4,4'-bis (9-ethyl-3-carbazovinylene) -1,1'-biphenyl), BDAVBi (4,4'-bis [4-diphenylamino] styryl) biphenyl), DPAVB (4- (di -p-tolylamino) -4 '-[(di-p-tolylamino) styryl] stilbene), DPAVBi (4,4'-bis [4- (di-p-tolylamino) styryl] bipnehyl), DSA-Ph (1 -4-di- [4- (N, N-diphenyl) amino] styryl-benzen
  • the delayed fluorescent dopant may include, but is not limited to, for example, 4CzIPN, 2CzPN, 4CzTPN-Ph, PXZ-DPS, DTPPDDA, and BDAPM.
  • the electron transport region may be disposed on the emission layer 16, and the electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the electron transport region may have a structure of a hole blocking layer / electron transport layer / electron injection layer or an electron transport layer / electron injection layer, but is not limited thereto.
  • the electron transport layer may have a single layer or a multilayer structure including two or more different materials.
  • the formation conditions of the hole blocking layer, the electron transport layer, and the electron injection layer of the electron transport region may be referred to the formation conditions of the hole injection layer.
  • the electron transport layer may include a condensed cyclic compound represented by Chemical Formula 1.
  • the electron transport layer may be a known electron transport material in addition to the condensed cyclic compound represented by Formula 1, for example, Alq 3 , BCP (Bathocuproine), Bphen (4,7-diphenyl-1,10- phenanthroline), TAZ (3- (Biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1,2,4-triazole), NTAZ (4- (naphthalen-1-yl ) -3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole), Balq (Bis (2-methyl-8-quinolinolato-N1, O8)-(1,1'-Biphenyl-4-olato) aluminum),
  • the electron injection layer may be formed using a material such as LiF, NaCl, CsF, Li 2 O, BaO, Liq, or the like.
  • the second electrode 19 is provided on the organic layer 15.
  • the second electrode 19 is an alkali metal such as lithium, sodium, potassium, rubidium, cesium, alkaline earth metal such as beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium , Metals such as europium, terbium and ytterbium, alloys of two or more of these, or alloys of one or more of these with gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten and tin And it can be formed from a structure containing at least two of these. If necessary, UV-ozone treated ITO may be used.
  • the alloy for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), graphene or the like can be used.
  • the second electrode 19 may be formed of a transparent oxide such as ITO, IZO, ZnO, or graphene.
  • the organic light emitting device has been described above with reference to FIG. 1, but is not limited thereto.
  • the C 1 -C 60 alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include methyl group, ethyl group, propyl group, isobutyl group, and sec-butyl group. Groups, tert-butyl groups, pentyl groups, iso-amyl groups, hexyl groups and the like.
  • a C 2 -C 60 alkenyl group refers to a hydrocarbon group including at least one carbon double bond in the middle or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, and a butenyl group. Etc. are included.
  • a C 2 -C 60 alkynyl group refers to a hydrocarbon group including at least one carbon triple bond in the middle or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, and the like. Included.
  • the C 1 -C 60 alkoxy group refers to a monovalent group having a chemical formula of —OA 101 (where A 101 is the C 1 -C 60 alkyl group), and specific examples thereof include a methoxy group and an ethoxy group. , Isopropyloxy group and the like.
  • a C 3 -C 10 cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclo Heptyl group and the like.
  • a C 1 -C 10 heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P, and S as a ring-forming atom, Specific examples thereof include 1,2,3,4-oxatriazolidinyl group (1,2,3,4-oxatriazolidinyl), tetrahydrofuranyl group, tetrahydrothiophenyl group and the like.
  • a C 3 -C 10 cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one double bond in a ring, but having no aromaticity, and examples thereof Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like.
  • a C 1 -C 10 heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P, and S as a ring-forming atom, Have at least one double bond in it.
  • Specific examples of the C 1 -C 10 heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-hydrofuranyl group, and 2,3-hydrothiophenyl group Etc. are included.
  • a C 6 -C 60 aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms.
  • Specific examples of the C 6 -C 60 aryl group include a phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group and the like.
  • the C 6 -C 60 aryl group includes two or more rings, the two or more rings may be condensed with each other.
  • C 1 -C 60 heteroaryl group used herein includes a monovalent group having at least one hetero atom selected from N, O, Si, P, and S as a ring-forming atom and having a heterocyclic aromatic system having 1 to 60 carbon atoms. Means.
  • Specific examples of the C 1 -C 60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like.
  • the C 1 -C 60 heteroaryl group includes two or more rings, two or more rings may be condensed with each other.
  • C 6 -C 60 aryloxy group -OA point 102 (where, A 102 is the C 6 -C 60 aryl group), C 6 -C 60 arylthio group (arylthio) is -SA 103 (where, A 103 is a C 6 -C 60 aryl group.
  • the C 1 -C 60 heteroaryloxy group refers to -OA 104 (wherein A 104 is the C 1 -C 60 heteroaryl group), and the C 1 -C 60 heteroarylthio group is represented by -SA 105 (where A 105 represents a C 1 -C 60 heteroaryl group.
  • Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, or AMI. Dino group, hydrazino group, hydrazono group, C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 1 -C 60 heteroaryl group, monovalent non-aromatic It may be selected from a condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl
  • DMAc is Dimethylacetamide and DMF is Dimethylformamide.
  • a 70 nm thick ITO patterned glass substrate as an anode electrode was pre-washed with isopropyl alcohol and acetone and exposed to UV-ozone for 10 minutes.
  • NPB was deposited on the glass substrate to form a hole transport layer having a thickness of 60 nm.
  • Ir (ppy) 3 was co-deposited to form a 5% sum of the weights of pBCb2Cz and Compound 14 to form a light emitting layer having a thickness of 30 nm.
  • ET1 was deposited on the emission layer to form an electron transport layer having a thickness of 55 nm.
  • An organic light emitting device was manufactured by depositing LiF on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and then depositing Al to form a cathode having a thickness of 100 nm. At this time, the layers were thermally deposited while maintaining a vacuum of 5 ⁇ 10 ⁇ 7 Torr.
  • An organic light-emitting device of Example 2 was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 14.
  • An organic light-emitting device of Comparative Example 1 was manufactured in the same manner as in Example 1, except that B4PYMPM was used instead of Compound 14.

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

Abstract

Selon un aspect, la présente invention concerne un composé cyclique condensé représenté par la formule chimique 1. Selon un autre aspect, la présente invention concerne une diode électroluminescente organique comprenant : une première électrode ; une seconde électrode ; et une couche organique comprenant une couche électroluminescente interposée entre la première électrode et la seconde électrode, la couche organique contenant le composé cyclique condensé représenté par la formule chimique 1.
PCT/KR2019/004850 2018-05-08 2019-04-23 Composé cyclique condensé et diode électroluminescente organique le comprenant WO2019216575A1 (fr)

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KR10-2018-0052797 2018-05-08
KR20180052797 2018-05-08
KR1020190042189A KR102218664B1 (ko) 2018-05-08 2019-04-10 축합환 화합물 및 이를 포함하는 유기 발광 소자
KR10-2019-0042189 2019-04-10

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CN114315869A (zh) * 2020-09-28 2022-04-12 北京绿人科技有限责任公司 一种有机化合物及其在有机电致发光器件中的应用
CN114315845A (zh) * 2020-09-28 2022-04-12 江苏绿人半导体有限公司 一种有机化合物及在有机电致发光器件中的应用
CN117143108A (zh) * 2023-08-31 2023-12-01 蒲城欧得新材料有限公司 一种8-溴-2-甲基苯并呋喃并[2,3-b]吡啶及合成方法

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WO2012115034A1 (fr) * 2011-02-22 2012-08-30 コニカミノルタホールディングス株式会社 Élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage
KR20120127256A (ko) * 2011-05-13 2012-11-21 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자 및 발광 장치
KR20140027315A (ko) * 2011-04-29 2014-03-06 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 착체, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
KR20160030402A (ko) * 2013-08-16 2016-03-17 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자, 전자 디바이스, 발광 장치 및 발광 재료
WO2018079459A1 (fr) * 2016-10-25 2018-05-03 コニカミノルタ株式会社 Élément à électroluminescence organique et matériau d'électroluminescence organique

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Publication number Priority date Publication date Assignee Title
WO2012115034A1 (fr) * 2011-02-22 2012-08-30 コニカミノルタホールディングス株式会社 Élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage
KR20140027315A (ko) * 2011-04-29 2014-03-06 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 착체, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
KR20120127256A (ko) * 2011-05-13 2012-11-21 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자 및 발광 장치
KR20160030402A (ko) * 2013-08-16 2016-03-17 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자, 전자 디바이스, 발광 장치 및 발광 재료
WO2018079459A1 (fr) * 2016-10-25 2018-05-03 コニカミノルタ株式会社 Élément à électroluminescence organique et matériau d'électroluminescence organique

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114315869A (zh) * 2020-09-28 2022-04-12 北京绿人科技有限责任公司 一种有机化合物及其在有机电致发光器件中的应用
CN114315845A (zh) * 2020-09-28 2022-04-12 江苏绿人半导体有限公司 一种有机化合物及在有机电致发光器件中的应用
CN117143108A (zh) * 2023-08-31 2023-12-01 蒲城欧得新材料有限公司 一种8-溴-2-甲基苯并呋喃并[2,3-b]吡啶及合成方法
CN117143108B (zh) * 2023-08-31 2024-03-19 蒲城欧得新材料有限公司 一种8-溴-2-甲基苯并呋喃并[2,3-b]吡啶及合成方法

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