EP3398218A1 - Nouveaux matériaux émetteur et matériaux matriciels pour composants électroniques et optoélectroniques, en particulier des diodes électroluminiscentes organiques (oled) - Google Patents

Nouveaux matériaux émetteur et matériaux matriciels pour composants électroniques et optoélectroniques, en particulier des diodes électroluminiscentes organiques (oled)

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Publication number
EP3398218A1
EP3398218A1 EP16826748.2A EP16826748A EP3398218A1 EP 3398218 A1 EP3398218 A1 EP 3398218A1 EP 16826748 A EP16826748 A EP 16826748A EP 3398218 A1 EP3398218 A1 EP 3398218A1
Authority
EP
European Patent Office
Prior art keywords
compound
group
organic
formula
donor
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.)
Withdrawn
Application number
EP16826748.2A
Other languages
German (de)
English (en)
Inventor
Reinhard Scholz
Ramunas Lygaitis
Paul Kleine
Simone Hofmann
Sebastian Reineke
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.)
Technische Universitaet Dresden
Original Assignee
Technische Universitaet Dresden
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 Technische Universitaet Dresden filed Critical Technische Universitaet Dresden
Publication of EP3398218A1 publication Critical patent/EP3398218A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/34—[b, e]-condensed with two six-membered rings with hetero atoms directly attached to the ring sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/611—Charge transfer complexes
    • 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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention is directed to the use of a compound as described herein in an optoelectronic device, such as an organic electroluminescent device (OLED), an organic integrated circuit (CMC), an organic field effect transistor (O-FET) , an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quenching device (O-FQD) , a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser) as emitter or matrix material.
  • OLED organic electroluminescent device
  • CMC organic integrated circuit
  • O-FET organic field effect transistor
  • OFTFT organic thin film transistor
  • OF-LET organic light emitting transistor
  • O-SC organic solar cell
  • O-SC organic optical detector
  • O-FQD organic field quenching device
  • LEC light-emitting electrochemical cell
  • O-laser organic laser diode
  • A is the respective radicals of the abovementioned compounds, ie dihydroacridinyl, etc.
  • the name of the compound is also used as such, it being understood by the person skilled in the art that the corresponding Rest is meant.
  • B is carbazole or a carbazole-containing compound
  • the carbazole has a bulky pendant group, especially one that provides for the dihedral angle between each A and B to be at least 70 °.
  • the dihedral angle between at least one donor and at least one acceptor group, ie, preferably between (each) A and B is at least 70 °.
  • B in these embodiments is preferably bonded via the group of the abovementioned radicals which corresponds to R 13 and / or R 16 or R 12 and / or R 17 in formula (I).
  • the compound of formula A-B or A-B-A i. of the formula (II I) or (IV) free of carbazole groups or carbazole-derived groups having a carbazole skeleton, i. in particular substituted carbazoles and in particular those having sterically less demanding substituents.
  • the compounds as described herein may be present as the sole emitter and / or matrix material in the light-emitting layer, without further additives. However, it is also possible that, in addition to the compounds used according to the invention, as described herein, further compounds are present in the light-emitting layer. For example, one or more fluorescent dyes may be present to alter the emission color of the emitter molecule present.
  • the person skilled in the art is able to choose the structure of the OLEDs in such a way that it is optimally adapted to the organic compounds used according to the invention as emitter substances.
  • the HOMO (highest occupied molecular orbital) of the hole-transporting layer should be aligned with the work function of the anode and the LUMO (lowest unoccupied molecular orbital) of the electron-transporting layer should be aligned with the work function of the cathode.

Abstract

La présente invention concerne des composés comprenant au moins un groupe donneur et au moins un groupe accepteur, dans lequel l'énergie de transition du triplet le plus faiblement excité vers l'état de base à la fois de la molécule donneuse correspondante et de la molécule accepteuse correspondante est d'au moins 2,2 eV, ainsi que leur utilisation comme matériau émetteur ou porteur dans un composant optoélectronique.
EP16826748.2A 2015-12-28 2016-12-28 Nouveaux matériaux émetteur et matériaux matriciels pour composants électroniques et optoélectroniques, en particulier des diodes électroluminiscentes organiques (oled) Withdrawn EP3398218A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102015122869.6A DE102015122869A1 (de) 2015-12-28 2015-12-28 Neue Emittermaterialien und Matrixmaterialien für optoelektronische und elektronische Bauelemente, insbesondere organische lichtemittierende Dioden (OLEDs)
PCT/EP2016/082763 WO2017114857A1 (fr) 2015-12-28 2016-12-28 Nouveaux matériaux émetteur et matériaux matriciels pour composants électroniques et optoélectroniques, en particulier des diodes électroluminiscentes organiques (oled)

Publications (1)

Publication Number Publication Date
EP3398218A1 true EP3398218A1 (fr) 2018-11-07

Family

ID=57821932

Family Applications (1)

Application Number Title Priority Date Filing Date
EP16826748.2A Withdrawn EP3398218A1 (fr) 2015-12-28 2016-12-28 Nouveaux matériaux émetteur et matériaux matriciels pour composants électroniques et optoélectroniques, en particulier des diodes électroluminiscentes organiques (oled)

Country Status (7)

Country Link
US (1) US20210167304A1 (fr)
EP (1) EP3398218A1 (fr)
JP (1) JP2019505505A (fr)
KR (1) KR20180101430A (fr)
CN (1) CN108604644A (fr)
DE (1) DE102015122869A1 (fr)
WO (1) WO2017114857A1 (fr)

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CN110003208B (zh) * 2019-04-16 2020-10-30 武汉华星光电半导体显示技术有限公司 热活化延迟荧光材料及其制备方法与有机电致发光二极管器件
KR20210051998A (ko) * 2019-10-31 2021-05-10 삼성전자주식회사 발광 소자, 그 제조방법 및 이를 포함한 표시 장치
CN110878062A (zh) * 2019-11-27 2020-03-13 武汉华星光电半导体显示技术有限公司 热活化延迟荧光材料及其制备方法和电致发光器件
KR102493132B1 (ko) * 2020-09-11 2023-01-31 삼성디스플레이 주식회사 발광 소자 및 이를 포함한 전자 장치
JP7196363B2 (ja) * 2020-11-05 2022-12-26 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
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Also Published As

Publication number Publication date
CN108604644A (zh) 2018-09-28
US20210167304A1 (en) 2021-06-03
JP2019505505A (ja) 2019-02-28
KR20180101430A (ko) 2018-09-12
WO2017114857A1 (fr) 2017-07-06
DE102015122869A1 (de) 2017-06-29

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