[go: up one dir, main page]

WO2018041123A1 - Composé ayant un noyau de fluorène et un hétérocycle contenant de l'azote à six chaînons et son application dans un dispositif électroluminescent organique - Google Patents

Composé ayant un noyau de fluorène et un hétérocycle contenant de l'azote à six chaînons et son application dans un dispositif électroluminescent organique Download PDF

Info

Publication number
WO2018041123A1
WO2018041123A1 PCT/CN2017/099587 CN2017099587W WO2018041123A1 WO 2018041123 A1 WO2018041123 A1 WO 2018041123A1 CN 2017099587 W CN2017099587 W CN 2017099587W WO 2018041123 A1 WO2018041123 A1 WO 2018041123A1
Authority
WO
WIPO (PCT)
Prior art keywords
layer
group
compound
electron
hole
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2017/099587
Other languages
English (en)
Chinese (zh)
Inventor
张兆超
李崇
唐丹丹
张小庆
叶中华
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Sunera Technology Co Ltd
Original Assignee
Jiangsu Sunera Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangsu Sunera Technology Co Ltd filed Critical Jiangsu Sunera Technology Co Ltd
Publication of WO2018041123A1 publication Critical patent/WO2018041123A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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]

Definitions

  • the invention relates to a compound based on ruthenium and a nitrogen-containing six-membered heterocyclic ring and its application in an organic light-emitting device, and belongs to the technical field of semiconductors.
  • OLED Organic Light Emission Diodes
  • the OLED light-emitting device is like a sandwich structure, including an electrode material film layer and an organic functional material sandwiched between different electrode film layers, and various functional materials are superposed on each other according to the purpose to form an OLED light-emitting device.
  • a current device when a voltage is applied to the electrodes of both ends of the OLED light-emitting device, and the positive and negative charges in the film layer of the organic layer functional material are applied by the electric field, the positive and negative charges are further recombined in the light-emitting layer, that is, OLED electroluminescence is generated.
  • OLED display technology has been applied in the fields of smart phones, tablet computers, etc., and will further expand to large-size applications such as televisions.
  • OLED devices have luminous efficiency and service life. Further improvement is needed.
  • Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device.
  • it is not only necessary to innovate from the structure and fabrication process of OLED devices, but also to continuously research and innovate OLED photoelectric functional materials, and to create functional materials with higher performance OLEDs.
  • OLED photoelectric functional materials applied to OLED devices can be divided into two categories, namely, charge injection.
  • the charge injection transport material can also be divided into an electron injection transport material, an electron blocking material, a hole injection transport material and a hole blocking material, and the luminescent material can be divided into a host luminescent material and a blend. Miscellaneous materials.
  • organic functional materials are required to have good photoelectric characteristics.
  • a charge transport material it is required to have good carrier mobility, high glass transition temperature, etc., as a main body of the light-emitting layer.
  • Materials require materials with good bipolarity, appropriate HOMO/LUMO energy levels, and the like.
  • the OLED photoelectric functional material film layer constituting the OLED device includes at least two or more layers, and the industrially applied OLED device structure includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron.
  • a plurality of film layers such as a transport layer and an electron injection layer, that is, an optoelectronic functional material applied to an OLED device includes at least a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material, etc., and the material type and the collocation form are rich. Characteristics of sex and diversity.
  • the optoelectronic functional materials used have strong selectivity, and the performance of the same materials in different structural devices may be completely different.
  • the photoelectric characteristics of the devices must be selected to be more suitable, and high-performance OLED functional materials or material combinations can achieve high efficiency and long device. Comprehensive characteristics of life and low voltage.
  • the development of OLED materials is still far from enough. It is lagging behind the requirements of panel manufacturers, and it is especially important to develop higher performance organic functional materials as material enterprises.
  • the technical problem to be solved by the present invention is to provide a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as its core and its use in an organic electroluminescent device.
  • the compound contains a ruthenium structure with high glass transition temperature and molecular thermal stability, suitable HOMO and LUMO energy levels, and high Eg.
  • the device structure is optimized to effectively improve the photoelectric performance of the OLED device and the lifetime of the OLED device.
  • R 1 , R 2 and R 3 are each a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a phenanolyl group, a benzimidazolyl group, and a benzene group. And one of oxazolyl, pyridoindole, quinoxalinyl or naphthyridinyl;
  • Ar is represented by one of a phenyl group, a biphenyl group, a naphthyl group or a pyridyl group;
  • n 1, 2 or 3.
  • the invention has the beneficial effects that the nitrogen-containing six-membered heterocyclic ring is a strong electron group and is modified by a hydrazine or an aromatic group by a ruthenium group and a nitrogen-containing six-membered heterocyclic ring as a skeleton.
  • the HOMO level can be freely adjusted, used as an electronic luminescent material or used as a hole blocking/electron transport layer material, which can improve the photoelectric performance and service life of the device.
  • the present invention can also be improved as follows.
  • the present invention has a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as a core, and further, in the formula (1)
  • R 2 and R 3 are each independently represented by R 2 and R 3 are each a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a phenanolyl group, a benzimidazolyl group, and a benzene group. And one of oxazolyl, pyridohydrazino, quinoxalinyl or naphthyridinyl.
  • the present invention has a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as a core, and further, in the formula (1)
  • the present invention has a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as a core, and further, the specific structural formula of the compound is:
  • the present invention has a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as a core, and further, the reaction equation in the preparation method is:
  • R 1 , R 2 and R 3 are each a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a phenanolyl group, a benzimidazolyl group, a benzoxazolyl group, a pyridine group.
  • a mercapto group, a quinoxaline group or a naphthyridinyl group is a mercapto group, a quinoxaline group or a naphthyridinyl group;
  • the preparation method uses Br-Ar-Br as a raw material, obtains a Grignard reagent by Grignard reaction, and then reacts with 9-fluorenone to form a tertiary alcohol; then the tertiary alcohol and HR 1 are subjected to a Friedel-Craft reaction to obtain a Brominated compounds, then The compound was prepared by CC coupling.
  • the above preparation method specifically includes the following steps:
  • the crude product of the obtained tertiary alcohol is purified by using a petroleum ether: dichloromethane mixed solvent over a neutral silica gel column.
  • the alcohol purification product preferably the above petroleum ether: dichloromethane volume ratio of 3:2; the tetrahydrofuran in the step 2) is preferably used in an amount of 4-8 ml of tetrahydrofuran per 1 g of 9-fluorenone; 1 g of tertiary alcohol was added to 5-10 ml of diethyl ether.
  • the molar ratio of the Pd(PPh 3 ) 4 to the monobromo compound is (0.005 to 0.02): 1, and the molar ratio of the sodium carbonate to the monobromo compound is (1.5 to 3.0): ;
  • the mixed solution obtained in the step 5) is reacted at 95 to 110 ° C for 10 to 24 hours, naturally cooled to room temperature, and the reaction solution is filtered, and the filtrate is rotary-screwed to a solvent-free, neutral silica gel column.
  • the target product is obtained.
  • the invention relates to the above application of a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as cores in an organic light-emitting device.
  • the present invention provides an organic electroluminescence device comprising at least one functional layer containing the above-mentioned organic compound containing a dibenzo six-membered ring and a nitrogen-containing six-membered heterocyclic ring.
  • the present invention provides an organic light-emitting device comprising a hole blocking/electron transport layer which is a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as a core.
  • An organic light-emitting device as described above further comprising a transparent substrate layer, an ITO anode layer, a hole injection layer, a hole transport/electron barrier layer, a light-emitting layer, an electron injection layer, and a cathode reflective electrode layer, Transparent substrate layer, ITO anode layer, hole injection layer, hole transport/electron blocking layer, luminescent layer, The hole blocking/electron transporting layer, the electron injecting layer, and the cathode reflecting electrode layer are stacked in this order from bottom to top.
  • the ITO anode layer has a thickness of 130 to 150 nm; or/and the hole injection layer is a material HAT-CN having a thickness of 10 nm; or/and the hole
  • the transmission/electron blocking layer is a hole transporting material NPB having a thickness of 80 nm, or/and the light emitting layer is made of CBP as a host material, and Ir(ppy) is used as a phosphorescent doping material, the doping mass ratio is 10%, and the thickness is 30 nm.
  • the hole blocking/electron transport layer has a thickness of 40 nm
  • the electron injecting layer is a LiF material having a thickness of 1 nm
  • the cathode reflective electrode layer is a material Al, the thickness thereof It is 100 nm.
  • An organic light-emitting device comprises a light-emitting layer, wherein the light-emitting layer is a compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as a core and a compound GHN as a host material, and the dopant material is Ir(ppy). 3 .
  • the mass ratio of the compound having the ruthenium and the nitrogen-containing six-membered heterocyclic ring as the core, the compound GHN and Ir(ppy) 3 is 60:30:10, wherein the structural formula of the compound GHN is
  • An organic light-emitting device as described above further comprising a transparent substrate layer, an ITO anode layer, a hole injection layer, a hole transport/electron barrier layer, a light-emitting layer, a hole blocking/electron transport layer, and an electron injection layer And a cathode reflective electrode layer, the transparent substrate layer, the ITO anode layer, the hole injection layer, the hole transport/electron barrier layer, the light-emitting layer, the hole blocking/electron transport layer, the electron injection layer, and the cathode reflective electrode layer are The top is stacked in order.
  • An organic light-emitting device as described above further comprising a transparent substrate layer, an ITO anode layer, a hole injection layer, a hole transport/electron barrier layer, a light-emitting layer, a hole blocking/electron transport layer, and an electron injection layer And a cathode reflective electrode layer, the transparent substrate layer, the ITO anode layer, the hole injection layer, the hole transport/electron barrier layer, the light-emitting layer, the hole blocking/electron transport layer, the electron injection layer, and the cathode reflective electrode layer are The top is stacked in order.
  • the ITO layer has an anode layer thickness of 130-150 nm; or/and the hole injection layer is a material HAT-CN having a thickness of 10 nm; or/and the hole transport/electron blocking
  • the layer is a hole transporting material NPB having a thickness of 80 nm, or/and the light emitting layer has a thickness of 30 nm, or/and the hole blocking/electron transporting layer material is TPBI, having a thickness of 40 nm, and/or the electron injecting
  • the layer is a LiF material having a thickness of 1 nm, and/or the cathode reflective electrode layer is a material Al having a thickness of 100 nm.
  • the invention provides a preparation method of an organic light emitting device, comprising the following steps:
  • Step c) depositing a hole transporting material NPB as a hole transporting layer/electron blocking layer on the hole injecting layer by vacuum evaporation;
  • Step d) evaporating a light-emitting layer on the hole transport/electron barrier layer, the light-emitting layer using CBP as a host material and Ir(ppy) as a phosphorescent dopant material;
  • Step e) above the light-emitting layer using the above-mentioned compound having a ruthenium and a nitrogen-containing six-membered heterocyclic ring as a core layer as a hole blocking layer/electron transport layer material;
  • Step g) On top of the electron injecting layer, a cathode Al is vacuum-evaporated as a cathode reflective electrode layer.
  • the compound of the present invention is composed of an anthracene group and a nitrogen-containing six-membered heterocyclic ring, wherein the nitrogen-containing six-membered heterocyclic ring is a strong electron group, and the HOMO level is freed by modification of a ruthenium or an aromatic group.
  • the adjustment can be used as an electron-type luminescent material or as a hole blocking/electron transport layer material.
  • each group is rigid, has high glass transition temperature and thermal stability, and the compound of the present invention is applied. In the case of OLED devices, the stability of the film after film formation can be maintained, and the service life of the OLED device can be improved.
  • FIG. 1 is a schematic structural view of a material exemplified in the present invention applied to an OLED device;
  • 1 is a transparent substrate layer
  • 2 is an ITO anode layer
  • 3 is a hole injection layer
  • 4 is a hole transport/electricity Sub-barrier layer
  • 5 is a light-emitting layer
  • 6 is a hole blocking/electron transport layer
  • 7 is an electron injection layer
  • 8 is a cathode reflective electrode layer.
  • the synthetic route is as follows:
  • the starting material A2 was prepared according to the synthesis method of the starting material A1 in Example 1, except that 1,4-dibromobenzene was used instead of 3,4'-dibromo-1,1'-biphenyl, and the third step was used in the reaction. Benzene instead of benzene;
  • the starting material A3 was prepared according to the synthesis method of the starting material A1 in Example 1, except that 1,4-dibromobenzene was used instead of 3,4'-dibromo-1,1'-biphenyl;
  • Raw material A4 was prepared according to the synthesis method of starting material A1 in Example 1, except that biphenyl was used instead of benzene in the third step reaction;
  • the starting material A5 was prepared according to the synthesis method of the starting material A1 in Example 1, except that 4,4'-dibromo-1,1'-biphenyl was used instead of 3,4'-dibromo-1,1'-biphenyl. ;
  • the starting material A2 was prepared according to the synthesis method of the starting material A1 in Example 1, except that 1,4-dibromobenzene was used instead of 3,4'-dibromo-1,1'-biphenyl, and the pyridine was used in the third step. Instead of benzene;
  • Elemental analysis structure (Molecular formula C 40 H 27 N 3 ): Theory C, 87.40; H, 4.95; N, 7.64; Tests: C, 87.41; H, 4.95; N, 7.63.
  • HPLC-MS The material had a molecular weight of 549.22 and a molecular weight of 549.45.
  • a 250 ml four-necked flask was charged with 0.01 mol of raw material A3, 0.012 mol of raw material B2, 0.02 mol of sodium carbonate, 1 ⁇ 10 -4 mol of Pd(PPh 3 ) 4 , 150 ml of toluene, and heated to 105 ° C under a nitrogen atmosphere. After refluxing for 24 hours, the spot plate was sampled, indicating that no bromine was left, and the reaction was complete; natural cooling, filtration, and the filtrate was rotary-steamed to a fraction without a fraction, and passed through a neutral silica gel column to obtain a target product with a purity of 99.5% and a yield of 79.2%.
  • HPLC-MS The material had a molecular weight of 548.23 and a molecular weight of 548.49.
  • a 250 ml four-necked flask was charged with 0.01 mol of raw material A1, 0.012 mol of raw material B3, 0.02 mol of sodium carbonate, 1 ⁇ 10 -4 mol of Pd(PPh 3 ) 4 , 150 ml of toluene, and heated to 105 ° C under a nitrogen atmosphere. After refluxing for 24 hours, the spot plate was sampled, indicating that there was no bromine residue remaining, and the reaction was complete; natural cooling, filtration, and the filtrate was rotary-steamed to a fraction without a fraction, and passed through a neutral silica gel column to obtain the desired product, purity 99.3%, yield 78.1%.
  • Elemental Analysis Structure (Molecular Formula C 48 H 33 N): Theory C, 92.42; H, 5.33; N, 2.25; ⁇ / RTI> C, 92.40; H, 5.34; N, 2.26.
  • HPLC-MS The material had a molecular weight of 623.26 and a molecular weight of 623.51.
  • a 250 ml four-necked flask was charged with 0.01 mol of raw material A2, 0.012 mol of raw material B3, 0.02 mol of sodium carbonate, 1 ⁇ 10 -4 mol of Pd(PPh 3 ) 4 , 150 ml of toluene, and heated to 105 ° C under a nitrogen atmosphere. After refluxing for 24 hours, the spot plate was sampled, indicating that there was no bromine residue remaining, and the reaction was completed; natural cooling, filtration, and the filtrate was rotary-steamed to a fraction without a fraction, and passed through a neutral silica gel column to obtain a target product with a purity of 99.5% and a yield of 74.3%.
  • Elemental Analysis Structure (Molecular Formula C 48 H 33 N): Theory C, 92.42; H, 5.33; N, 2.25; Tests: C, 92.43; H, 5.32; N, 2.25.
  • HPLC-MS The material had a molecular weight of 623.26 and a molecular weight of 623.53.
  • Elemental analysis structure (Molecular formula C 42 H 29 N): Theory C, 92.11; H, 5.34; N, 2.56; Tests: C, 92.10; H, 5.35; N, 2.55.
  • HPLC-MS The material had a molecular weight of 547.23 and a molecular weight of 547.49.
  • Elemental analysis structure (Molecular formula C 40 H 27 N 3 ): Theory C, 87.40; H, 4.95; N, 7.64; Tests: C, 87.41; H, 4.965; N, 7.63.
  • HPLC-MS The material had a molecular weight of 549.22 and a molecular weight of 549.47.
  • Elemental analysis structure (Molecular formula C 39 H 26 N 4 ): Theory C, 85.07; H, 4.76; N, 10.17; Tests: C, 85.06; H, 4.78; N, 10.16.
  • HPLC-MS The material had a molecular weight of 550.22 and a molecular weight of 550.43.
  • a 250 ml four-necked flask was charged with 0.01 mol of raw material A4, 0.012 mol of raw material C2, 0.02 mol of sodium carbonate, 1 ⁇ 10 -4 mol of Pd(PPh 3 ) 4 , 150 ml of toluene, and heated to 105 ° C under a nitrogen atmosphere. After refluxing for 24 hours, the spot plate was sampled, indicating that there was no bromine residue remaining, and the reaction was completed; natural cooling, filtration, and the filtrate was rotary-steamed to a fraction without a fraction, and passed through a neutral silica gel column to obtain the desired product, purity 99.1%, yield 65.1%.
  • Elemental Analysis Structure (Molecular Formula C 53 H 36 N 2 ): Theory C, 90.83; H, 5.18; N, 4.40; Tests: C, 90.81; H, 5.17; N, 4.02.
  • HPLC-MS The material had a molecular weight of 700.29 and a molecular weight of 700.55.
  • Elemental analysis structure (Molecular formula C 45 H 30 N 4 ): Theory C, 86.24; H, 4.82; N, 8.94; Tests: C, 86.22; H, 4.83; N, 8.95.
  • HPLC-MS The material had a molecular weight of 626.25 and a molecular weight of 626.52.
  • Elemental Analysis Structure (Molecular Formula C 47 H 32 N 2 ): Theory C, 90.35; H, 5.16; N, 4.48; Tests: C, 90.38; H, 5.15; N, 4.47.
  • HPLC-MS The material had a molecular weight of 624.26 and a molecular weight of 625.54.
  • Elemental analysis structure (Molecular formula C 47 H 32 N 2 ): Theory C, 90.35; H, 5.16; N, 4.48; Tests: C, 90.36; H, 5.17; N, 4.47.
  • HPLC-MS The material had a molecular weight of 624.26 and a molecular weight of 624.53.
  • Elemental Analysis Structure (Molecular Formula C 47 H 32 N 2 ): Theory C, 90.35; H, 5.16; N, 4.48; Tests: C, 90.37; H, 5.15; N, 4.48.
  • HPLC-MS The material had a molecular weight of 624.26 and a molecular weight of 624.57.
  • Elemental analysis structure (molecular formula C 40 H 27 N 3 ): calcd. C, 87.40; H, 4.95; N, 7.64; C, 87.40; H, 4.95; N, 7.65.
  • HPLC-MS The material had a molecular weight of 549.22 and a molecular weight of 549.45.
  • Elemental analysis structure (Molecular formula C 46 H 31 N 3 ): Theory C, 88.29; H, 4.99; N, 6.72; ??????, C, 88.30; H, 5.00; N, 6.70.
  • HPLC-MS The material had a molecular weight of 625.25 and a molecular weight of 625.56.
  • Elemental Analysis Structure (Molecular Formula C 46 H 31 N 3 ): Theory C, 88.29; H, 4.49; N, 6.72; Tests: C, 88.27; H, 5.00; N, 6.73.
  • HPLC-MS The material had a molecular weight of 625.25 and a molecular weight of 625.59.
  • a 250 ml four-necked flask was charged with 0.01 mol of raw material A6, 0.012 mol of raw material D1, 0.02 mol of sodium carbonate, 1 ⁇ 10 -4 mol of Pd(PPh 3 ) 4 , 150 ml of toluene, and heated to 105 ° C under a nitrogen atmosphere. After refluxing for 24 hours, the spot plate was sampled, indicating that there was no bromine residue remaining, and the reaction was complete; natural cooling, filtration, and the filtrate was rotary-steamed to a fraction without a fraction, and passed through a neutral silica gel column to obtain a target product with a purity of 99.4% and a yield of 71.7%.
  • Elemental analysis structure (Molecular formula C 39 H 26 N 4 ): Theory C, 85.07; H, 4.76; N, 10.17; Tests: C, 85.07; H, 4.75; N, 10.18.
  • HPLC-MS The material had a molecular weight of 550.22 and a molecular weight of 550.47.
  • the compound provided by the present invention will be described in detail as a hole blocking or electron transporting layer material and a light emitting layer material by the device examples 1-10 and the device comparative example 1, and applied to an electroluminescent device, and proved by the comparative example 1. Its beneficial effect.
  • the performance test results of the devices obtained in the respective examples are shown in Table 1.
  • An electroluminescent device the preparation steps comprising:
  • the hole injection layer material HAT-CN is deposited by vacuum evaporation, the thickness is 10nm, this layer serves as the hole injection layer 3;
  • the hole transport material NPB is evaporated by vacuum evaporation, the thickness is 80nm, the layer is a hole transport layer or electron blocking layer 4;
  • the layer is the cathode reflective electrode layer 8;
  • the molecular organization of the relevant material is as follows:
  • This embodiment is different from Device Embodiment 1 in that the hole blocking or electron transport layer 6 material of the electroluminescent device becomes the compound 4 of the present invention.
  • the detection data of the obtained electroluminescent device is shown in Table 1.
  • This embodiment differs from Device Embodiment 1 in that the hole blocking or electron transport layer 6 material of the electroluminescent device becomes the compound 15 of the present invention.
  • the detection data of the obtained electroluminescent device is shown in Table 1.
  • This embodiment differs from Device Embodiment 1 in that the material of the hole blocking or electron transport layer 6 of the electroluminescent device becomes the compound 26 of the present invention.
  • the detection data of the obtained electroluminescent device is shown in Table 1.
  • This embodiment is different from Device Embodiment 1 in that the material of the hole blocking/electron transport layer 6 of the electroluminescent device becomes the compound 35 of the present invention.
  • the detection data of the obtained electroluminescent device is shown in Table 1.
  • This embodiment differs from Device Embodiment 1 in that the hole blocking or electron transport layer 6 material of the electroluminescent device becomes TPBI, the light emitting layer host material becomes the compound 5 of the present invention, and the doping material is Ir (ppy). 3 ) The mass ratio of the compound 5 of the present invention and the doping material Ir(ppy) 3 was 9:1, and the detection data of the obtained electroluminescent device are shown in Table 1.
  • This embodiment differs from Device Embodiment 1 in that the hole blocking or electron transport layer 6 material of the electroluminescent device becomes TPBI, the light emitting layer host material becomes the compound 42 of the present invention, and the doping material is Ir (ppy). 3 , the mass ratio of the compound 42 of the present invention and the doping material Ir(ppy) 3 is 9:1, and the detection data of the obtained electroluminescent device are shown in Table 1.
  • This embodiment differs from Device Embodiment 1 in that the hole blocking or electron transport layer 6 material of the electroluminescent device becomes TPBI, and the light emitting layer host material becomes the compound 51 and the compound GHN of the present invention, and the doping material is Ir(ppy) 3 , the mass ratio of the compound 51 of the present invention, the compound GHN and the doping material to Ir(ppy) 3 is 60:30:10, and the detection data of the obtained electroluminescent device are shown in Table 1.
  • This embodiment differs from Device Embodiment 1 in that the hole blocking or electron transporting layer 6 material of the electroluminescent device becomes TPBI, and the light emitting layer host material becomes the compound 53 and the compound GHN of the present invention, and the doping material is Ir(ppy) 3 , the mass ratio of the compound 53 of the present invention, the compound GHN and the doping material to Ir(ppy) 3 is 60:30:10, and the detection data of the obtained electroluminescent device are shown in Table 1.
  • This embodiment differs from Device Embodiment 1 in that the hole blocking or electron transport layer 6 material of the electroluminescent device becomes two layers, wherein the compound 58 of the present invention is used alone as a hole blocking layer, having a thickness of 5 nm.
  • the following structural compound A and compound B were mixed with each other at a mass ratio of 1:1 as an electron transport layer, and the thickness thereof was 35 nm.
  • the detection data of the obtained electroluminescent device is shown in Table 1.
  • This comparative example is different from Device Embodiment 1 in that the hole blocking or electron transport layer 6 material of the electroluminescent device becomes TPB I.
  • the detection data of the obtained electroluminescent device is shown in Table 1.
  • the device test performance is based on device comparison example 1, and the performance index of the device of comparison example 1 is set to 1.0.
  • the current efficiency of Comparative Example 1 was 28 cd/A (@10 mA/cm 2 ); the CIE color coordinate was (0.33, 0.63); the LT95 lifetime decay at 5000 luminance was 2.5 Hr.
  • the above hole blocking layer is also referred to as an electron transport layer.

Landscapes

  • 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

La présente invention concerne un composé ayant un noyau d'un fluorène et un hétérocycle contenant de l'azote à six chaînons. Le composé a une formule structurale générale (I), dans laquelle R 1 , R 2 , et R 3 sont respectivement l'un d'un groupe phényle, biphényle, naphtyle, pyridyle, quinolinyle, phénanthrolinyle, benzimidazolyle, benzoxazolyle, pyridoindolyle, quinoxalinyle, ou naphtyridinyle ; Ar représente l'un d'un groupe phényle, biphényle, naphtyle ou pyridyle ; aa représente un hétérocycle contenant de l'azote à six chaînons ; et n est égal à 1, 2 ou 3. La présente invention utilise un fluorène et un hétérocycle contenant de l'azote à six chaînons en tant que squelette, et le fluorène et l'hétérocycle contenant de l'azote à six chaînons sont liés par l'intermédiaire d'un groupe aromatique. L'hétérocycle contenant de l'azote à six chaînons est un groupe électronique fort, et lorsqu'il est modifié par le fluorène et le groupe aromatique, le niveau d'énergie orbitale moléculaire occupée le plus élevé peut être ajusté librement. La présente invention est utilisée en tant que matériau électroluminescent électronique ou en tant que matériau de couche de blocage de trou/couche de transfert d'électrons et peut améliorer la performance photoélectrique et la durée de vie d'un dispositif.
PCT/CN2017/099587 2016-08-31 2017-08-30 Composé ayant un noyau de fluorène et un hétérocycle contenant de l'azote à six chaînons et son application dans un dispositif électroluminescent organique Ceased WO2018041123A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201610799636.6 2016-08-31
CN201610799636.6A CN107778220A (zh) 2016-08-31 2016-08-31 以芴和含氮六元杂环为核心的化合物及在有机发光器件中的应用

Publications (1)

Publication Number Publication Date
WO2018041123A1 true WO2018041123A1 (fr) 2018-03-08

Family

ID=61300120

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2017/099587 Ceased WO2018041123A1 (fr) 2016-08-31 2017-08-30 Composé ayant un noyau de fluorène et un hétérocycle contenant de l'azote à six chaînons et son application dans un dispositif électroluminescent organique

Country Status (2)

Country Link
CN (1) CN107778220A (fr)
WO (1) WO2018041123A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210020842A1 (en) * 2018-06-08 2021-01-21 Lg Chem, Ltd. Organic light-emitting device
JPWO2021152940A1 (fr) * 2020-01-30 2021-08-05
CN114276379A (zh) * 2021-12-16 2022-04-05 西安凯翔光电科技有限公司 一种有机发光化合物及有机电致发光器件
JPWO2022163735A1 (fr) * 2021-01-29 2022-08-04
CN116217546A (zh) * 2022-09-07 2023-06-06 青岛科技大学 一种以菲并咪唑为核心骨架的电子传输层材料及有机电致发光二极管和制备方法
CN116891440A (zh) * 2022-03-30 2023-10-17 江苏三月科技股份有限公司 一种含三嗪结构的化合物及其在有机电致发光器件上的应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111244306A (zh) * 2018-11-29 2020-06-05 宇瑞(上海)化学有限公司 一种顶发射有机发光二极管单元
CN112409243A (zh) * 2019-08-23 2021-02-26 支志明 四齿配体、金(iii)配合物及其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102421868A (zh) * 2009-05-15 2012-04-18 第一毛织株式会社 有机光电装置用化合物和包括该化合物的有机光电装置
CN102977006A (zh) * 2012-12-21 2013-03-20 南京邮电大学 吡啶芴类有机电致磷光主体发光材料及其制备方法
CN106478609A (zh) * 2015-08-31 2017-03-08 上海和辉光电有限公司 一种应用于oled领域的材料

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101311934B1 (ko) * 2009-06-08 2013-09-26 제일모직주식회사 유기광전소자용 조성물 및 이를 이용한 유기광전소자
CN107531650B (zh) * 2015-08-21 2020-10-09 株式会社Lg化学 化合物和包含其的有机电子元件
KR102615638B1 (ko) * 2015-12-22 2023-12-20 삼성디스플레이 주식회사 유기 발광 소자
KR101924086B1 (ko) * 2016-02-26 2018-11-30 삼성에스디아이 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102421868A (zh) * 2009-05-15 2012-04-18 第一毛织株式会社 有机光电装置用化合物和包括该化合物的有机光电装置
CN102977006A (zh) * 2012-12-21 2013-03-20 南京邮电大学 吡啶芴类有机电致磷光主体发光材料及其制备方法
CN106478609A (zh) * 2015-08-31 2017-03-08 上海和辉光电有限公司 一种应用于oled领域的材料

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210020842A1 (en) * 2018-06-08 2021-01-21 Lg Chem, Ltd. Organic light-emitting device
US12415801B2 (en) * 2018-06-08 2025-09-16 Lg Chem, Ltd. Organic light-emitting device
KR102618174B1 (ko) 2020-01-30 2023-12-28 도레이 카부시키가이샤 화합물, 유기 박막 발광 소자, 표시 장치 및 조명 장치
JPWO2021152940A1 (fr) * 2020-01-30 2021-08-05
WO2021152940A1 (fr) * 2020-01-30 2021-08-05 東レ株式会社 Composé, élément électroluminescent à couche mince organique, dispositif d'affichage, et dispositif d'éclairage
JP7052885B2 (ja) 2020-01-30 2022-04-12 東レ株式会社 化合物、有機薄膜発光素子、表示装置および照明装置
KR20220133191A (ko) * 2020-01-30 2022-10-04 도레이 카부시키가이샤 화합물, 유기 박막 발광 소자, 표시 장치 및 조명 장치
JPWO2022163735A1 (fr) * 2021-01-29 2022-08-04
WO2022163735A1 (fr) * 2021-01-29 2022-08-04 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
JP7606539B2 (ja) 2021-01-29 2024-12-25 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
CN114276379A (zh) * 2021-12-16 2022-04-05 西安凯翔光电科技有限公司 一种有机发光化合物及有机电致发光器件
CN116891440A (zh) * 2022-03-30 2023-10-17 江苏三月科技股份有限公司 一种含三嗪结构的化合物及其在有机电致发光器件上的应用
CN116217546A (zh) * 2022-09-07 2023-06-06 青岛科技大学 一种以菲并咪唑为核心骨架的电子传输层材料及有机电致发光二极管和制备方法

Also Published As

Publication number Publication date
CN107778220A (zh) 2018-03-09

Similar Documents

Publication Publication Date Title
WO2018041123A1 (fr) Composé ayant un noyau de fluorène et un hétérocycle contenant de l'azote à six chaînons et son application dans un dispositif électroluminescent organique
WO2020135687A1 (fr) Composé contenant du bore, son procédé de préparation et son utilisation
WO2018108034A1 (fr) Dispositif électroluminescent organique ayant une structure à double corps principal
WO2018113538A1 (fr) Composé organique avec homobenzène en tant que noyau et son utilisation dans un dispositif à électroluminescence organique
CN106967021A (zh) 一种以均苯为核心的有机化合物及其应用
WO2017215549A1 (fr) Composé organique électroluminescent et son application
CN109748909A (zh) 一种含螺氧杂蒽芴和含氮六元杂环的化合物、其制备方法及其在有机电致发光器件中的应用
CN106478611B (zh) 一种以氧杂蒽为核心的有机化合物及其应用
CN105837498A (zh) 一种含有二甲基蒽结构的有机化合物及其应用
CN107057681A (zh) 一种含有氧杂蒽结构的光电材料及其在oled领域的应用
WO2019196948A1 (fr) Composé utilisant une arylcétone en tant que noyau, son procédé de préparation et son application dans une oled
CN106467486A (zh) 一种含有二甲基蒽的有机化合物及其应用
CN107337680A (zh) 一种以芴为核心的有机化合物及其在oled器件上的应用
CN107868090A (zh) 含有9,9’‑螺二芴的有机化合物及有机发光电致器件
CN116396277B (zh) 有机化合物、有机电致发光器件及电子装置
CN107868048A (zh) 一种含有芴的化合物及其应用
CN110577488A (zh) 一种以咔唑为核心的化合物及其在有机电致发光器件上的应用
CN110526901A (zh) 一种有机发光材料及其制备有机电致发光器件的应用
WO2019085683A1 (fr) Composé hétérocyclique contenant de l'anthrone et contenant de l'azote et ses applications dans des diodes électroluminescentes organiques
CN108203427A (zh) 一种以咔唑为核心的化合物及其在有机电致发光器件上的应用
CN107868084A (zh) 一种以9,9’‑螺二芴为主体的有机化合物及其应用
CN108203428A (zh) 一种以咔唑为核心的化合物及其应用
CN107602397B (zh) 一种以二苯并环庚烯为核心的化合物及其应用
CN108218853A (zh) 一种以二苯并含氮六元杂环为核心的化合物及其在有机电致发光器件上的应用
WO2019085759A1 (fr) Composé comportant un noyau aza-spirofluorène et arylcétone, son procédé de préparation et son application dans des diodes électroluminescentes organiques

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17845425

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 17845425

Country of ref document: EP

Kind code of ref document: A1