EP4121432A1 - Composés hétéroaromatiques pour dispositifs électroluminescents organiques - Google Patents

Composés hétéroaromatiques pour dispositifs électroluminescents organiques

Info

Publication number
EP4121432A1
EP4121432A1 EP21711248.1A EP21711248A EP4121432A1 EP 4121432 A1 EP4121432 A1 EP 4121432A1 EP 21711248 A EP21711248 A EP 21711248A EP 4121432 A1 EP4121432 A1 EP 4121432A1
Authority
EP
European Patent Office
Prior art keywords
formula
radicals
group
aromatic
substituted
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.)
Pending
Application number
EP21711248.1A
Other languages
German (de)
English (en)
Inventor
Philipp Stoessel
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP4121432A1 publication Critical patent/EP4121432A1/fr
Pending legal-status Critical Current

Links

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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • C09K2211/1007—Non-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
    • C09K2211/1003—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
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other 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
    • C09K2211/1044—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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms 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
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • 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
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • 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

  • a further object can be seen in providing electronic devices with excellent performance as inexpensively as possible and of constant quality Furthermore, the electronic devices should be able to be used or adapted for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.
  • Z is on each occurrence, identically or differently, N or B;
  • X 1 stands on each occurrence, identically or differently, for N, CR a or CAr, preferably for CR a, with the proviso that not more than two of the groups X 1 , X 2 in one cycle are N;
  • an aromatic ring system contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system for the purposes of this invention contains 2 to 60 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the context of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but also contains several aryl - Or heteroaryl groups through a non-aromatic unit, such as. B. a C, N or O atom can be connected.
  • the abovementioned formulation is also intended to mean that in the event that one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bound to form a ring.
  • the at least two radicals R, R a , R b , R c , R d form one with the further groups to which the two radicals R, R a , R b , R c , R d bond fused ring, where the two radicals R, R a , R b , R c , R d preferably form at least one of the structures of the formulas (RA-1a) to (RA-4f) 5
  • Formula RA-4d Formula RA-4e Formula RA-4f where the dashed bonds represent the attachment points via which the two radicals R, R a , R b , R c , R d bond, the index m 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the symbols R 1 , R 2 , R e and the indices s, and t are those previously, in particular for formula (I) and / or formulas (RA-1) to (RA- 12) have the meaning set out above.
  • At least two radicals R, R a , R b , R c , R d form a condensed ring with the other groups to which the two radicals R, R a , R b , R c , R d bond , wherein the two radicals R, R a , R b , R c , R d form structures of the formula (RB)
  • the compounds particularly preferably comprise at least one structure of the formulas (V-1) to (V-22), the compounds are particularly preferably selected from compounds of the formulas (V-1) to (V-22), the compounds at least one condensed Have ring Formula (V- 7) Formula (V-8) where the symbols Z, R, R a , R c and R d have the meanings given above, in particular for formula (I), the symbol Y 1 and the indices k and j have the meanings given above, in particular for formulas (lla) to (lld ) have mentioned meanings, the symbols Y 2 and Y 3 have the meanings given above, in particular for formulas (purple) to (IIIv), the symbol o stands for the attachment points of the condensed ring and the index m 0, 1, 2, 3 or 4, preferably 0, 1 or 2.
  • the compounds have at least two condensed rings, at least one condensed ring being formed by structures of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and another ring is formed by structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB), the compounds having at least one structure of the formulas (VI-1 ) to (VI-22), preferably the compounds are selected from the compounds of the formulas (VI-1) to (VI-22),
  • the formulas (VI-1) to (VI-22) have at least two condensed rings, the condensed rings being the same and the two radicals R, R a , R b , R c , R d formed part can be represented by at least one structure of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f).
  • Ar 1 is on each occurrence, identically or differently, a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, which can in each case be substituted by one or more radicals R 1;
  • R e is very particularly preferably selected identically or differently on each occurrence from the group consisting of a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms, or a branched alkyl group with 3 to 6 carbon atoms.
  • R e very particularly preferably represents a methyl group or a phenyl group, where two phenyl groups can together form a ring system, a methyl group being preferred over a phenyl group.
  • Ar 4 is preferably an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, which can each be substituted with one or more radicals R 1 .
  • Ar 4 is particularly preferably selected from the group consisting of ortho-, meta- or para-phenylene or ortho-, meta- or para-biphenyl, which can each be substituted by one or more radicals R 1 , but are preferably unsubstituted.
  • Ar 4 is very particularly preferably an unsubstituted phenylene group.
  • Ar 2 and Ar 3 are preferably, identically or differently on each occurrence, an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which can in each case be substituted by one or more radicals R 1.
  • Particularly preferred groups Ar 2 and Ar 3 are selected from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta -, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-,
  • Another object of the present invention is the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device, preferably as an emitter, particularly preferably as a green, red or blue emitter.
  • compounds according to the invention preferably show fluorescent properties and thus preferably provide fluorescent emitters.
  • compounds according to the invention can be used as host materials, electron transport materials and / or hole conductor materials.
  • compounds according to the invention in which the group Z stands for N can advantageously be used as hole conductor material.
  • indenocarbazole derivatives e.g. B. according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, e.g. B. according to WO 2007/137725, silanes, e.g. B. according to WO 2005/111172, aza borole or boronic ester, z. B. according to WO 2006/117052, triazine derivatives, e.g. B.
  • Formulations for applying a compound according to formula (I) or their or their preferred embodiments set out above are new.
  • the present invention therefore also relates to formulations containing at least one solvent and a compound according to formula (I) or their preferred embodiments set out above.
  • Hybrid methods are also possible in which, for example, one or more layers are applied from solution and one or more additional layers are vapor-deposited.
  • OLEDs according to the invention and OLEDs according to the prior art are produced by a general method according to WO 2004/058911, which is adapted to the conditions described here (layer thickness variation, materials used).

Abstract

L'invention concerne des composés hétéroaromatiques qui sont appropriés pour être utilisés dans des dispositifs électroniques, ainsi que des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant lesdits composés.
EP21711248.1A 2020-03-17 2021-03-15 Composés hétéroaromatiques pour dispositifs électroluminescents organiques Pending EP4121432A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20163671 2020-03-17
PCT/EP2021/056443 WO2021185712A1 (fr) 2020-03-17 2021-03-15 Composés hétéroaromatiques pour dispositifs électroluminescents organiques

Publications (1)

Publication Number Publication Date
EP4121432A1 true EP4121432A1 (fr) 2023-01-25

Family

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EP21711248.1A Pending EP4121432A1 (fr) 2020-03-17 2021-03-15 Composés hétéroaromatiques pour dispositifs électroluminescents organiques

Country Status (5)

Country Link
US (1) US20230157170A1 (fr)
EP (1) EP4121432A1 (fr)
KR (1) KR20220154774A (fr)
CN (1) CN115298187A (fr)
WO (1) WO2021185712A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022186390A1 (fr) * 2021-03-05 2022-09-09 出光興産株式会社 Élément électroluminescent organique et dispositif électronique

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