WO2010046259A1 - Composés polycycliques pour des applications électroniques - Google Patents

Composés polycycliques pour des applications électroniques Download PDF

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WO2010046259A1
WO2010046259A1 PCT/EP2009/063267 EP2009063267W WO2010046259A1 WO 2010046259 A1 WO2010046259 A1 WO 2010046259A1 EP 2009063267 W EP2009063267 W EP 2009063267W WO 2010046259 A1 WO2010046259 A1 WO 2010046259A1
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alkyl
aryl
group
substituted
interrupted
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Peter Nesvadba
Frédérique Wendeborn
Thomas Schäfer
Beat Schmidhalter
Andrea Ricci
Peter Murer
Natalia Chebotareva
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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 relates to electronic devices, especially electroluminescent devices, comprising polycyclic compounds, especially as host for phosphorescent emitters, electron transporting materials, or emitter materials.
  • the hosts may function with phosphorescent materials to provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.
  • US3243428 relates to compounds of formula , wherein R 13 and R 14 are hydrogen, or lower alkyl, i.e. a straight, or branched chain alkyl group having 1 to 7 carbon atoms, and their use as estrogens.
  • EP0433628 (DE3938282) relates to a process for the preparation of 3,8-dihydroxy-5a,1 Ob-
  • DDCC diphenyl-coumarano-2',3',2,3-coumarane
  • JP10102056 relates to heat resistant stabilisers, such as
  • JP10273659 relates to a polymer stabilizer effective not only to stably keep a polymer in a high-temperature environment but also to develop excellent polymerization inhibiting effect on monomers such as styrene by including a heat- resistant compound having a specific structure.
  • the polymer stabilizer consists of a compound having aromatic rings each having at least one OH group and condensed to each of 2, 3-positions and 4, 5-positions of furo[2,3- b]furan ring.
  • One or both of the above condensed aromatic rings are benzene ring or naphthalene ring.
  • a preferred example of the compound is 7a,12b-dihydronaphtho[2,1- b]benzophthalo [3,2-d]furan-10-ol.
  • JP2004026706 discloses dihydric hydroxy compounds represented by formula
  • R 5 -R 8 are each independently a hydroxy group or a Ci-
  • the dihydric hydroxy compound is suitable as a raw material for a thermosetting resin, a thermoplastic resin, a photosensitive material such as a photoresist for a semiconductor, or a developer for heat-sensitive paper.
  • a thermosetting resin e.g., a thermosetting resin
  • a thermoplastic resin e.g., a thermoplastic resin
  • a photosensitive material such as a photoresist for a semiconductor
  • a developer for heat-sensitive paper e.g., a developer for heat-sensitive paper.
  • EP1847544 relates to an organic semiconductor device comprising an organic semiconductor material satisfying both the requirement of high electron field-effect mobility and high on/off current ratio.
  • the organic semiconductor material is a compound of formula
  • Xi and X 2 are independently a chalcogen atom
  • n is an integer in a range of 1 to 3
  • Ri and R 2 are independently a halogen, a C 1-18 alkyl, a halogenated Ci-i 8 alkyl; a Ci-i 8 alkyloxy, a Ci-i 8 alkylthio, an aryl, or an aryl having at least one selected from the group consisting of a halogen, a Ci-i 8 alkyl, a halogenated Ci_i 8 alkyl, a C 1- i 8 alkyloxy, and a Ci_i 8 alkylthio.
  • JP2007088016 relates to an organic semiconductor device and an organic thin-film transistor having high carrier mobility.
  • the organic semiconductor material can contain, for example, a
  • JP2007119392 relates to an organic electroluminescent element having more excellent performances of luminous efficiency, current efficiency, element life, external quantum efficiency, comprising a polycyclic condensed ring compound has a backbone represented
  • a 1 and A 2 are each sulfur, SO 2 , silicon or carbon, one of A 1 and A 2 is sulfur or SO 2 and the other of A 1 and A 2 is silicon or carbon;
  • ring structures B', C and D' are each independently a 5-membered ring or 6- membered ring;
  • p is a value of 0 or 1 ; when A 1 or A 2 is carbon, p is 1.
  • X, X', Y and Y' are independently of each other O, S, SO 2 , NR , Se, or Te,
  • the ring A represents an optionally substituted aryl group which can optionally contain heteroatoms
  • the ring B represents an optionally substituted aryl group which can optionally contain heteroatoms
  • the ring C represents an optionally substituted aryl group which can optionally contain heteroatoms
  • the ring D represents an optionally substituted aryl group which can optionally contain heteroatoms
  • R 1 R 1 , R 11 and R 11 are independently of each other a group -L 1 -X 1 , or
  • R 1 and R 1 , or R 11 and R 11 together form a ring, or ring system, which may optionally be substituted,
  • R 163 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by CrCi 8 alkyl, or d-Ci 8 alkoxy; Ci-Ci 8 alkyl,
  • Ar is C 6 -Ci 4 aryl, such as phenyl, or naphthyl, which may optionally be substituted by one or more groups selected from CrC 2 5alkyl, which may optionally be interrupted by -O-, or d- C 25 alkoxy,
  • L 1 is a single bond, or a bridging unit BU, such as
  • a 1 and A 1 are independently of each other a C 6 -C 24 aryl group, a C 2 -C 30 heteroaryl group, which can optionally be substituted, or
  • a 1 and A 1 together with the nitrogen atom to which they are bonded form a heteroaromatic
  • ring or ring system, such as m is 0, 1 , or 2;
  • a 4 , A 4 , A 6 , A 7 and A 8 are independently of each other a C 6 -C 24 aryl group, or a C 2 -
  • ml can be the same or different at each occurence and is 0, 1 , 2, 3, or 4, especially 0, 1 , or
  • R 119 and R 120 are independently of each other CrCi 8 alkyl, d-Ci 8 alkyl which is substituted by
  • C 2 -C 20 heteroaryl which is substituted by G, C 2 -d 8 alkenyl, C 2 -d 8 alkynyl, d-d 8 alkoxy, d- d 8 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl, or
  • R 119 and R 120 together form a five or six membered ring, which optionally can be substituted by Ci-Ci 8 alkyl, d-Ci 8 alkyl which is substituted by E and/or interrupted by D, C6-C 24 aryl, C 6 -
  • R 123 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl, Ci-Ci 8 alkyl which is interrupted by -O-;
  • R 127 is H; C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; d-
  • Ci 8 alkyl or Ci-Ci 8 alkyl which is interrupted by -O-,
  • E is -OR 69 , -SR 69 , -NR 65 R 66 , -COR 68 , -COOR 67 , -CONR 65 R 66 , -CN, or halogen
  • G is E, or Ci-Ci 8 alkyl, -SO 2 R 73 ,
  • R 63 and R 64 are independently of each other C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by d-
  • R 65 and R 66 are independently of each other C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by d- Ci 8 alkyl, Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl; or Ci-Ci 8 alkyl which is interrupted by -0-; or
  • R 65 and R 66 together form a five or six membered ring
  • R 67 is C 6 -Ci 8 aryl; C 6 -d 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl; or Ci-Ci 8 alkyl which is interrupted by -0-,
  • R 68 is H; C 6 -Ci 8 aryl; C 6 -d 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; d- Ci 8 alkyl; or Ci-Ci 8 alkyl which is interrupted by -0-,
  • R 69 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl, which is substituted by Ci-Ci 8 alkyl, Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl; or
  • Ci-Ci 8 alkyl which is interrupted by -0-
  • R 70 and R 71 are independently of each other Ci-Ci 8 alkyl, C 6 -d 8 aryl, or C 6 -d 8 aryl, which is substituted by Ci-Ci 8 alkyl, and R 72 is Ci-Ci 8 alkyl, C 6 -d 8 aryl, or C 6 -Ci 8 aryl, which is substituted by Ci-Ci 8 alkyl;
  • R 73 is Ci-Ci 8 alkyl, or Ci-Ci 8 alkyl which is interrupted by -O-; -CF 3 , C 6 -Ci 8 aryl, C 6 -Ci 8 aryl, which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy;
  • the ring A, are not substituted by a hydroxy group, an ester, an ether group, or an epoxy group, and with the further proviso that
  • Y and Y' are a group NR 163 , is different from an acetyl group, and a straight, or branched chain d-C 7 alkyl group.
  • the rings A and B can be the same, or different, but are preferably the same.
  • the electronic device of the present invention is preferably an electroluminescent (EL) device.
  • EL electroluminescent
  • the compounds of formula I, or Il may be used in organic light emitting diodes (OLEDs) as hosts for phosphorescent compounds, as emitting and/or charge transport material.
  • OLEDs organic light emitting diodes
  • X, X', Y and Y' are independently of each other O, S, SO 2 , NR 163 , Se, or Te,
  • R 1 , R 1 , R 11 and R 11 are independently of each other a group X 1 , or -L 1 -X 1 ,
  • R 10 , R 10' , R 16 and R 16' are independently of each other hydrogen, d-Ci 8 alkyl, a group L 1 -X 1 ,
  • R 163 isC 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl;
  • R 168 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl;
  • R 1 and R 1 ' are the same and are a group L 1 -X 1
  • R 11 and R 11 ' are the same and are a group L 1 -X ⁇
  • R 10 and R 10 ' are the same and are hydrogen.
  • the bridging unit BU is, for example, an arylene, or heteroarylene group, which optionally may be substituted.
  • R 47 and R 48 are independently of each other hydrogen, CrC 2 oalkyl, or C 6 -C 24 aryl, which can optionally be substituted by G, m5 is an integer of 1 to 10, m2 is an integer of 1 to 10, m3 is an integer of 1 to 5, m4 is an integer of 1 to 5,
  • Ar 3 and Ar 4 are independently of each other arylene, or heteroarylene, which can optionally be substituted by G, wherein G is as defined above.
  • L 1 is a single bond, or a bridging unit BU of formula
  • R 119 , R 120 , R 123 , ml and R 41 are as defined above.
  • R 170 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl, which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; d-
  • Ci 8 alkyl or Ci-Ci 8 alkyl which is interrupted by -O-, and
  • R 119 , R 120 , R 123 , ml and R 41 are as defined above.
  • a 5 , A 1 , A 1' , A 3 and A 3' are independently of each other a C 6 -C 24 aryl group, or a C 2 - C 30 heteroaryl group, which can optionally be substituted, especially phenyl, naphthyl, anthryl, biphenylyl, 2-fluorenyl, phenanthryl, or perylenyl, which can optionally be substituted, such as
  • n' is 0, 1 , or 2
  • ml can be the same or different at each occurence and is 0, 1 , 2, 3, or 4, especially 0, 1 , or 2, very especially 0 or 1 ;
  • R 65 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by CrCi 8 alkyl, d-Ci 8 alkoxy; Ci-Ci 8 alkyl; or Ci-Ci 8 alkyl which is interrupted by -O-; 7
  • a 4 , A 4 ' , A 6 , A 7 and A 8 are independently of each other a group R
  • R 116 , R 117 and R 117 are independently of each other H, halogen, especially F, -CN, d-
  • R 124 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl,
  • Ci-Ci 8 alkyl which is interrupted by -O-;
  • R 126 and R 127 are independently of each other H; C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl; or Ci-Ci 8 alkyl which is interrupted by -O-,
  • R 119 , R 120 , R 123 , D, E, G, R 41 and ml are as defined above.
  • heteroaromatic ring or ring system, which is formed by A 1 and A 1' , or A 3 and A 3 together with the nitrogen atom to which they are bonded, are examples of a heteroaromatic ring, or ring system, which is formed by A 1 and A 1' , or A 3 and A 3 together with the nitrogen atom to which they are bonded, are examples of a heteroaromatic ring, or ring system, which is formed by A 1 and A 1' , or A 3 and A 3 together with the nitrogen atom to which they are bonded, are examples of a heteroaromatic ring, or ring system, which is formed by A 1 and A 1' , or A 3 and A 3 together with the nitrogen atom to which they are bonded, are examples of a heteroaromatic ring, or ring system, which is formed by A 1 and A 1' , or A 3 and A 3 together with the nitrogen atom to which they are bonded, are examples of a heteroaromatic ring, or ring system, which is formed
  • R 117 , R 119 , R 120 and ml are as defined above. Specific examples are groups AM-1 to AM-13 mentioned in claim 10.
  • the present invention is directed to compounds of formula Ia, or
  • R and R are a group of formula -NA A , or , or a group of formula , wherein R 116 and R 117 are as defined above, R 3 , R 3 ', R 4 and R 4 are a
  • NA 1 A 1' or are compounds AM-1 to AM-13.
  • the present invention is directed to compounds of formula Ia, or Ib, wherein R 1 , R 1 R 3 , R 3 ', R 4 and R 4 are independently of each other a group of
  • Examples of groups of formula -NA 1 A 1 are compounds AM-1 to AM-13.
  • R , R and R are independently of each other a group of formula -NA 1 A ⁇ 1 ' , or
  • Examples of groups of formula -NA 1 A 1 are compounds AM-1 to AM-13.
  • Cisalkyl which is interrupted by O, or phenyl, which is optionally substituted by
  • R 116 , R 117 and R 117' are as defined above and R 116' has the meaning of R 116 .
  • Specific examples are groups AR-1 and AR-2 mentioned in claim 10.
  • Compounds of the formula (I), (II), (III), or (IV) are preferred, wherein L -X is a group
  • R ,117' are as defined above. Specific examples are groups HE-1 to HE-9 mentioned in claim 10.
  • R 116 , R 117 , R 119 , R 120 , and R 123 are as defined above.
  • R 116 and R 117 are independently of each other H, Ci-Ci 2 alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, t-butyl, 2-methylbutyl, n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, or n-heptyl, Ci-Ci 2 alkyl which is substituted by E and/or interrupted by D, such as -CH 2 OCH 3 , -CH 2 OCH 2 CH 3 , -CH 2 OCH 2 CH 2 OCH 3 , or -CH 2 OCH 2 CH 2 OCH 2 CH 3 , C 6 -Ci 4 aryl, such as phenyl, naphthyl, or biphenylyl, C 5 - Ci 2 cycloalkyl, such as cyclohexyl, C 6
  • D is preferably -CO-, -COO-, -S-, -SO-, -SO 2 -, -0-, -NR 25 -, wherein R 25 is C r Ci 2 alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, or sec-butyl, or C 6 -Ci 4 aryl, such as phenyl, naphthyl, or biphenylyl.
  • E is preferably -OR 29 ; -SR 29 ; -NR 25 R 25 ; -COR 28 ; -COOR 27 ; -CONR 25 R 25 ; or -CN; wherein R 25 , R 27 , R 28 and R 29 are independently of each other Ci-Ci 2 alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, hexyl, octyl, or 2-ethyl-hexyl, or C 6 -Ci 4 aryl, such as phenyl, naphthyl, or biphenylyl, which may optionally be substituted.
  • Ci-Ci 2 alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, hexyl, oct
  • G has the same preferences as E, or is CrCi 8 alkyl, especially Ci-Ci 2 alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, hexyl, octyl, or 2-ethyl-hexyl.
  • the present invention is directed to compounds of formula
  • R 170 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl, which is substituted by CrCi 8 alkyl, or d-Ci 8 alkoxy; d- Ci 8 alkyl; or Ci-Ci 8 alkyl which is interrupted by -O-,
  • R 216 and R 217 are independently of each other H
  • Ci-Ci 8 alkyl or Ci-Ci 8 alkyl which is interrupted by O,
  • R 10 , R 10' , R 16 and R 16' are independently of each other hydrogen, C r Ci 8 alkyl, a group L 1 -X 1 , wherein L 1 -X 1 is as defined above,
  • a , A 1 A , A and A are independently of each other , or A 1 and A 1' , or A 3 and A 3 together with the nitrogen atom to which they are
  • heteroaromatic ring, or ring system such as or
  • a , A , A and A are independently of each other a group
  • R 116 , R 116' , R 117 and R 117' are independently of each other H, d-Ci 8 alkyl, C r Ci 8 alkyl which is interrupted by O,
  • R 123 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by CrCi 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl,
  • R 170 is C 6 -Ci 8 aryl; C 6 -Ci 8 aryl, which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; C r
  • Ci 8 alkyl or Ci-Ci 8 alkyl which is interrupted by -O-,
  • BU is , or , wherein ml is
  • R ->41 is a Ci-C 2 5alkyl group, or a Ci-C 2 5alkoxy group
  • R and R are independently of each other H, , or a group L 1 -X 1 ,
  • R 13 and R 14' are independently of each other H, or a group L 1 -X 1 , wherein L 1 -X 1 , R 216 and R 217 are as defined above.
  • Compounds A-1 to A-74 which are shown in claim 10, are particularly preferred, wherein compounds A-6 to A-9, A-19 to A-21 , A-26 to A-29, A-30, A-31 , A-35, A-59 to A-68 are particularly suitable as hosts for blue triplet emitters, compounds A-1 , A-2, A-3 and A-36 to A-49 are particularly suitable as hosts for red triplet emitters and compounds A-55 and A-56 are particularly suitable as ambipolar hosts for red triplet emitters.
  • Compounds B-1 to B-41 which are shown in claim 10, are particularly preferred, wherein compounds compounds B-6 to B-9 and B-28 to B-37 are particularly suitable as hosts for blue triplet emitters, compounds B-1 , B-2, B-3, B-15 to B-18 are particularly suitable as hosts for red triplet emitters, compounds B-24 and B-25 are particularly suitable as ambipolar hosts for red triplet emitters and compound B-22 is particularly suitable as fluorescent emitter.
  • Compounds C-1 to C-12, which are shown in claim 10 are particularly preferred and can advantageously be used as electron transport material.
  • Compounds D-1 to D-9 which are shown in claim 10, are particularly preferred and can advantageously be used as electron transport material.
  • Halogen is fluorine, chlorine, bromine and iodine.
  • Ci-C 2 5alkyl (d-Ci 8 alkyl) is typically linear or branched, where possible. Examples are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert.
  • Ci-C 8 alkyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert. -butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethyl-propyl, n- hexyl, n-heptyl, n-octyl, 1 ,1 ,3,3-tetramethylbutyl and 2-ethylhexyl.
  • CrC 4 alkyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.
  • Ci-C 2 5alkoxy (Ci-Ci 8 alkoxy) groups are straight-chain or branched alkoxy groups, e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy and octadecyloxy.
  • Ci-C 8 alkoxy examples are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert.-butoxy, n-pentyloxy, 2-pentyloxy, 3-pentyloxy, 2,2-dimethylpropoxy, n- hexyloxy, n-heptyloxy, n-octyloxy, 1 ,1 ,3,3-tetramethylbutoxy and 2-ethylhexyloxy, preferably Ci-C 4 alkoxy such as typically methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert.-butoxy.
  • alkylthio group means the same groups as the alkoxy groups, except that the oxygen atom of the ether linkage is replaced by a sulphur atom.
  • C 2 -C 25 alkenyl (C 2 -Ci 8 alkenyl) groups are straight-chain or branched alkenyl groups, such as e.g. vinyl, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3- methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec- 4-enyl.
  • alkenyl groups such as e.g. vinyl, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3- methyl-but-2-enyl, n-oct
  • C 2-24 alkynyl (C 2 -Ci 8 alkynyl) is straight-chain or branched and preferably C 2-8 alkynyl, which may be unsubstituted or substituted, such as, for example, ethynyl, 1-propyn-3-yl, 1-butyn-4- yl, 1-pentyn-5-yl, 2-methyl-3-butyn-2-yl, 1 ,4-pentadiyn-3-yl, 1 ,3-pentadiyn-5-yl, 1-hexyn-6-yl, cis-3-methyl-2-penten-4-yn-1-yl, trans-3-methyl-2-penten-4-yn-1-yl, 1 ,3-hexadiyn-5-yl, 1-octyn-8-yl, 1-nonyn-9-yl, 1-decyn-10-yl, or 1-tetracosyn-24-yl.
  • Ci-Ci 8 perfluoroalkyl is a branched or unbranched radical such as for example -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -(CF 2 ) 3 CF 3 , and -C(CF 3 ) 3 .
  • haloalkyl, haloalkenyl and haloalkynyl mean groups given by partially or wholly substituting the above-mentioned alkyl group, alkenyl group and alkynyl group with halogen, such as trifluoromethyl etc.
  • aldehyde group, ketone group, ester group, carbamoyl group and amino group include those substituted by an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a heterocyclic group, wherein the alkyl group, the cycloalkyl group, the aryl group, the aralkyl group and the heterocyclic group may be unsubstituted or substituted.
  • silica group means a group of formula -SiR 62 R 63 R 64 , wherein R 62 , R 63 and R 64 are independently of each other a Ci-C 8 alkyl group, in particular a d-C 4 alkyl group, a C 6 -C 24 aryl group or a C 7 -Ci 2 aralkylgroup, such as a trimethylsilyl group.
  • siloxanyl group means a group of formula -0-SiR 62 R 63 R 64 , wherein R 62 , R 63 and R 64 are as defined above, such as a trimethylsiloxanyl group.
  • cycloalkyl group is typically C 4 -Ci 8 cycloalkyl (C 5 -Ci 2 cycloalkyl), such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, preferably cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, which may be unsubstituted or substituted.
  • cycloalkenyl group means an unsaturated alicyclic hydrocarbon group containing one or more double bonds, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl and the like, which may be unsubstituted or substituted.
  • the cycloalkyl group in particular a cyclohexyl group, can be condensed one or two times by phenyl which can be substituted one to three times with Ci-C 4 -alkyl, halogen and cyano.
  • R 1 56 are independently of each other CrC 8 -alkyl, Ci-C ⁇ -alkoxy, halogen and cyano, in particular hydrogen.
  • Aryl is usually C 6 -C 3 oaryl, preferably C 6 -C 24 aryl, which optionally can be substituted, such as, for example, phenyl, 4-methylphenyl, 4-methoxyphenyl, naphthyl, especially 1-naphthyl, or 2- naphthyl, biphenylyl, terphenylyl, pyrenyl, 2- or 9-fluorenyl, phenanthryl, anthryl, tetracyl, pentacyl, hexacyl, or quaderphenylyl, which may be unsubstituted or substituted.
  • aralkyl group is typically C 7 -C 24 aralkyl, such as benzyl, 2-benzyl-2-propyl, ⁇ - phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, ⁇ , ⁇ -dimethyl- ⁇ -phenyl-butyl, ⁇ -phenyl- dodecyl, ⁇ -phenyl-octadecyl, ⁇ -phenyl-eicosyl or ⁇ -phenyl-docosyl, preferably C 7 -Ci 8 aralkyl such as benzyl, 2-benzyl-2-propyl, ⁇ -phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, ⁇ , ⁇ -dimethyl- ⁇ -phenyl-butyl, ⁇ -phenyl-dodecyl or ⁇ -phenyl-odec
  • aryl ether group is typically a C 6-24 aryloxy group, that is to say O-C 6-24 aryl, such as, for example, phenoxy or 4-methoxyphenyl.
  • aryl thioether group is typically a C 6 - 24 arylthio group, that is to say S-C 6 - 24 aryl, such as, for example, phenylthio or 4-methoxyphenylthio.
  • carbamoyl group is typically a Ci-i 8 carbamoyl radical, preferably Ci -8 carbamoyl radical, which may be unsubstituted or substituted, such as, for example, carbamoyl, methylcarbamoyl, ethylcarbamoyl, n-butylcarbamoyl, tert- butylcarbamoyl, dimethylcarbamoyloxy, morpholinocarbamoyl or pyrrolidinocarbamoyl.
  • aryl and “alkyl” in alkylamino groups, dialkylamino groups, alkylarylamino groups, arylamino groups and diarylgroups are typically Ci-C 2 5alkyl and C 6 -C 24 aryl, respectively.
  • Alkylaryl refers to alkyl-substituted aryl radicals, especially C 7 -Ci 2 alkylaryl. Examples are tolyl, such as 3-methyl-, or 4-methylphenyl, or xylyl, such as 3,4-dimethylphenyl, or 3,5- dimethylphenyl.
  • Heteroaryl is typically C 2 -C 3 oheteroaryl (C 2 -C 2 6heteroaryl, especially C 2 -C 2 oheteroaryl), i.e. a ring with five to seven ring atoms or a condensed ring system, wherein nitrogen, oxygen or sulphur are the possible hetero atoms, and is typically an unsaturated heterocyclic group with five to 30 atoms having at least six conjugated ⁇ -electrons such as thienyl, benzo[b]thienyl, dibenzo[b,d]thienyl, thianthrenyl, furyl, furfuryl, 2H-pyranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, phenoxythienyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, bipyridyl, triazinyl, pyrimidinyl, pyr
  • Possible substituents of the above-mentioned groups are Ci-C 8 alkyl, a hydroxyl group, a mercapto group, Ci-C 8 alkoxy, Ci-C 8 alkylthio, halogen, halo-Ci-C 8 alkyl, a cyano group, an aldehyde group, a ketone group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group or a silyl group, wherein d-C 8 alkyl, d-C 8 alkoxy, a cyano group, or a silyl group are preferred.
  • a substituent such as, for example R 3 41 occurs more than one time in a group, it can be different in each occurrence.
  • substituted by G means that one, or more, especially one to three groups G might be present.
  • the aforementioned groups may be substituted by E and/or, if desired, interrupted by D. Interruptions are of course possible only in the case of groups containing at least 2 carbon atoms connected to one another by single bonds; C 6 -Ci 8 aryl is not interrupted; interrupted arylalkyl or alkylaryl contains the unit D in the alkyl moiety.
  • CrCisalkyl substituted by one or more E and/or interrupted by one or more units D is, for example, (CH 2 CH 2 O)i-9-R x , where R x is H or d-doalkyl or C 2 -Cioalkanoyl (e.g.
  • R y is d-Ci 8 alkyl, C 5 -d 2 cycloalkyl, phenyl, C 7 -Ci 5 phenylalkyl, and R y ' embraces the same definitions as R y or is H;
  • Preferred arylene radicals are 1 ,4-phenylene, 2,5-tolylene, 1 ,4-naphthylene, 1 ,9 antracylene, 2,7-phenantrylene and 2,7-dihydrophenantrylene.
  • Preferred heteroarylene radicals are 2,5-pyrazinylene, 3,6-pyridazinylene, 2,5-pyridinylene, 2,5-pyrimidinylene, 1 ,3,4-thiadiazol-2,5-ylene, 1 ,3-thiazol-2,4-ylene, 1 ,3-thiazol-2,5-ylene, 2,4-thiophenylene, 2,5-thiophenylene, 1 ,3-oxazol-2,4-ylene, 1 ,3-oxazol-2,5-ylene and 1 ,3,4- oxadiazol-2,5-ylene, 2,5-indenylene and 2,6-indenylene.
  • R 3 , R 3' , R 4 , R 4' , R 13 , R 14' , R 7 and R 7' are a group of formula -0-SO 2 - CF 3 involves reacting compounds of the formula Va, Via, and Vila, wherein R 3 , R 3 , R 4 , R 4 ,
  • R 13 , R 14' , R 7 and R 7' are OH, with a group of formula .
  • Compounds of formula can be prepared by reacting in the presence of an acid, such as hydrochloric acid, sulphuric acid, or methanesulfonic acid.
  • an acid such as hydrochloric acid, sulphuric acid, or methanesulfonic acid.
  • hydroxyl groups are subsequently transformed into trifluoromethanesulfonyl groups under classical conditions (Synthesis (1982) 85-126), which are in turn used as leaving groups in the palladium catalyzed reactions.
  • Synthesis (1982) 85-126) which are in turn used as leaving groups in the palladium catalyzed reactions.
  • R 3 , R 3' , R 4 , R 4' , R 13 , R 14' , R 7 and R 7' are independently of each other -NA 1 A 1' , , or , can, for example, be prepared according to a process, which comprises reacting a compound of formula Va, Vb, Via, Vila, or Villa, wherein R :>3, ⁇ R->3 J ', ⁇ R->4 4 , ⁇ R->4 4 ', 1 R— ,13 , r R- ,1'4 4 ', ⁇ R->7' and R' stands for halogen, such as bromo or iodo,
  • R , R , R and R are independently of each other -NA A , , or 1
  • R 3 , R 3 , R 4 , R 4 , R 13 , R 14 , R 7 and R 7 stands for halogen, such as bromo, with a compound of formula
  • HNA 1 A 1 or in the presence of a base, such as sodium te/f-butylate in a solvent such as toluene or xylene and in the presence of a palladium catalyst such as palladium (II) acetate or palladium (II) tris- (dibenzylidene acetone).
  • a base such as sodium te/f-butylate
  • a palladium catalyst such as palladium (II) acetate or palladium (II) tris- (dibenzylidene acetone.
  • R 13 , R 14' , R 7 and R 7 are independently of each other -NA 1 A 1 , or
  • R 3 , R 3 , R 4 , R 4' , R 13 , R 14' , R 7 and R 7' stands for -0-SO 2 -CF 3 with a compound of formula HNA 1 A 1' ,
  • the reaction of the dibromide with the acetylene is done in the presence a catalyst, such as copper (0), copper (I) (such as copper, copper-bronze, copper iodide, or copper bromide), and/or palladium(O), such as, for example, tetrakis (triphenyl-phosphine) palladium(O), optionally in a solvent, such as toluene, dimethyl formamide, or dimethyl sulfoxide, and optionally a base, such as sodium hydride, potassium carbonate, sodium carbonate, or an amine base, such as piperidine.
  • a catalyst such as copper (0), copper (I) (such as copper, copper-bronze, copper iodide, or copper bromide), and/or palladium(O), such as, for example, tetrakis (triphenyl-phosphine) palladium(O), optionally in a solvent, such as toluene, dimethyl formamide,
  • the dibromide is reacted with the alkine at a temperature of from 50 0 C to 100 0 C , especially 60 to 80°C for 1 h to 48 h hours.
  • This reaction referred to as an Sonogashira reaction (Pd/Cu-catalyzed cross-coupling of organohalides with terminal alkynes), Cadiot-Chodkiewicz coupling or Castro-Stephens reaction (the Castro-Stephens coupling uses stoichiometric copper, whereas the
  • Sonogashira variant uses catalytic palladium and copper), is described by Sonogashira K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467; Richard Heck (discovered the same transformation using palladium but without the use of copper) J. Organomet. Chem. 1975, 93, 259; McCrindle, R.; Ferguson, G.; Arsenaut, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res. (S) 1984, 360; Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Chem.
  • R 7 are a group , are new and form a further subject of the present invention.
  • R and R are a group , can be prepared by reacting compounds of formula
  • R 3 , R 3' , R 4 , R 4' , R 13 , R 14' , R 7 and R 7' are a group of
  • the electronic device of the present invention is preferably an electroluminescent (EL) device.
  • EL electroluminescent
  • the compounds of formula I, or Il may be used in organic light emitting diodes (OLEDs) as hosts for phosphorescent compounds, as emitting and/or charge transport material.
  • OLEDs organic light emitting diodes
  • the EL device comprises a cathode, an anode, and there between a light emitting layer containing a host material and a phosphorescent light-emitting material, wherein the host material is a compound of formula I, or II.
  • the EL device comprises a cathode, an anode, and an electron transport material, wherein the electron transport material is, or comprises a compound of formula I, or II.
  • the EL device comprises a cathode, an anode, and an emitting layer, wherein the emitting layer consists of, or comprises a compound of formula I, or II.
  • the present invention is also directed to the use of the compounds of formula I, or Il for electrophotographic photoreceptors, photoelectric converters, solar cells, image sensors, dye lasers and electroluminescent devices.
  • the light-emitting layer of the OLED device comprises a host material and one or more guest materials for emitting light.
  • One of the host materials may be a compound of formula I, or II.
  • the light-emitting guest material(s) is usually present in an amount less than the amount of host materials and is typically present in an amount of up to 15 wt % of the host, more typically from 0.1 to 10 wt % of the host, and commonly from 2 to 8% of the host.
  • the phosphorescent complex guest material may be referred to herein as a phosphorescent material.
  • the emissive layer may comprise a single material, that combines transport and emissive properties.
  • emissive layer may comprise other materials, such as dopants that tune the emission of the emissive layer.
  • the emissive layer may include a plurality of emissive materials capable of, in combination, emitting a desired spectrum of light.
  • the host material useful in the invention may be used alone or in combination with other host materials.
  • Other host materials should be selected so that the triplet exciton can be transferred efficiently from the host material to the phosphorescent material.
  • Suitable host materials are described in WO00/70655; 01/39234; 01/93642; 02/074015; 02/15645, and US200201 17662.
  • Suitable hosts include certain aryl amines, triazoles, indoles and carbazole compounds.
  • hosts 4,4'-N,N'-dicarbazole-biphenyl (CBP), 2,2'-dimethyl-4,4'- N,N'-dicarbazole-biphenyl, m-(N,N'-dicarbazole)benzene, and poly(N-vinylcarbazole), including their derivatives.
  • CBP 4,4'-N,N'-dicarbazole-biphenyl
  • 2,2'-dimethyl-4,4'- N,N'-dicarbazole-biphenyl 2,2'-dimethyl-4,4'- N,N'-dicarbazole-biphenyl
  • m-(N,N'-dicarbazole)benzene m-(N,N'-dicarbazole)benzene
  • poly(N-vinylcarbazole) including their derivatives.
  • Desirable host materials are capable of forming a continuous film.
  • the light-emitting layer may contain more than one host material in order to improve the device's film morphology, electrical properties, light emission efficiency, and lifetime.
  • the light emitting layer may contain a first host material that has good hole-transporting properties, and a second host material that has good electron-transporting properties.
  • Phosphorescent materials may be used alone or, in certain cases, in combination with each other, either in the same or different layers. Examples of phosphorescent and related materials are described in WO00/57676, WO00/70655, WO01/41512, WO02/15645, US2003/0017361 , WO01/93642, WO01/39234, US6,458,475, WO02/071813, US6.573.651 , US2002/019751 1 , WO02/074015, US6.451.455, US2003/0072964, US2003/0068528, US6,413,656, 6,515,298, 6,451 ,415, 6,097,147, US2003/0124381 , US2003/0059646, US2003/0054198, EP1239526, EP1238981 , EP1244155, US2002/0100906, US2003/0068526, US2003/0068535, JP2003073387, JP2003073388, US2003/
  • IrL 3 and IrL 2 L' such as the green-emitting fac-tris(2-phenylpyridinato-N,C 2 )iridium(lll) and bis(2-phenylpyridinato-N,C 2 )lridium(lll) (acetylacetonate) may be shifted by substitution of electron donating or withdrawing groups at appropriate positions on the cyclometallating ligand L, or by choice of different heterocycles for the cyclometallating ligand L.
  • the emission wavelengths may also be shifted by choice of the ancillary ligand L'.
  • red emitters are the bis(2-(2'-benzothienyl)pyridinato-N,C 3 )iridium(EI)(acetylacetonate) and tris(1-phenylisoquinolinato-N,C)iridium(lll).
  • a blue-emitting example is bis(2-(4,6- ddiifflloouurroopphheennyyll))--ppyyrriiddiinnaattoo--NN,,CC 22 ))llrriiddiiuum(lll)(picolinate), or bis(3,5-difluoro-2-(2-pyridyl)phenyl-
  • phosphorescent materials include cyclometallated Pt(II) complexes such as cis-bis(2-phenylpyridinato-N,C 2 )platinum(ll), cis-bis(2-(2'-thienyl)pyridinato-N,C 3 ) platinum(ll), cis-bis(2-(2'-thienyl)quinolinato-N,C 5' ) platinum(ll), or (2-(4,6-diflourophenyl)pyridinato-NC2') platinum(ll)acetylacetonate.
  • cyclometallated Pt(II) complexes such as cis-bis(2-phenylpyridinato-N,C 2 )platinum(ll), cis-bis(2-(2'-thienyl)pyridinato-N,C 3 ) platinum(ll), cis-bis(2-(2'-thienyl)quinolinato-N,C 5'
  • Pt(ll)porphyrin complexes such as 2,3,7,8,12,13,17,18- octaethyl-21 H, 23H-porphine platinum(H) are also useful phosphorescent materials. Still other examples of useful phosphorescent materials include coordination complexes of the trivalent lanthanides such as Th 3+ and Eu 3+ (J. Kido et al, Appl. Phys. Lett., 65, 2124 (1994)).
  • Examples of phosphorescent materials are compounds A-1 to B-234, B-1 to B-234, C-1 to C- 44 and D-1 to D-234, which are described in WO08/101842, and compounds A1-A144 and B1-B144, which are described in WO09/100991.
  • an OLED device employing a phosphorescent material often requires at least one exciton or hole blocking layers to help confine the excitons or electron- hole recombination centers to the light-emitting layer comprising the host and phosphorescent material, or to reduce the number of charge carriers (electrons or holes).
  • a blocking layer would be placed between the electron-transporting layer and the light-emitting layer.
  • the ionization potential of the blocking layer should be such that there is an energy barrier for hole migration from the host into the electron-transporting layer, while the electron affinity should be such that electrons pass more readily from the electron-transporting layer into the light-emitting layer comprising host and phosphorescent material.
  • the triplet energy of the blocking material be greater than that of the phosphorescent material.
  • Suitable hole-blocking materials are described in WO00/70655 and WO01 /93642.
  • Two examples of useful materials are bathocuproine (BCP) and bis(2-methyl-8-quinolinolato)(4- phenylphenolato)aluminum(lll) (BAIQ).
  • Metal complexes other than BaIq are also known to block holes and excitons as described in US20030068528.
  • US20030175553 describes the use of fac-tris(1-phenylpyrazolato-N,C 2)iridium(lll) (Irppz) in an electron/exciton blocking layer.
  • An example of an electron blocking material is 1 ,1-bis[4-[ ⁇ /, ⁇ /-di(p-tolyl)amino]phenyl]- cyclohexane (TAPC).
  • Embodiments of the invention can provide advantageous features such as operating efficiency, higher luminance, color hue, low drive voltage, and improved operating stability.
  • Embodiments of the organometallic compounds useful in the invention can provide a wide range of hues including those useful in the emission of white light (directly or through filters to provide multicolor displays).
  • the compounds of the present invention can be employed in many OLED device configurations using small molecule materials, oligomeric materials, polymeric materials, or combinations thereof. These include very simple structures comprising a single anode and cathode to more complex devices, such as passive matrix displays comprised of orthogonal arrays of anodes and cathodes to form pixels, and active-matrix displays where each pixel is controlled independently, for example, with thin film transistors (TFTs).
  • TFTs thin film transistors
  • OLED organic light-emitting diode
  • cathode an organic light-emitting layer located between the anode and cathode. Additional layers may be employed as more fully described hereafter.
  • a typical structure is comprised of a substrate, an anode, a hole-injecting layer, a hole-transporting layer, a light-emitting layer, optionally a hole- or exciton-blocking layer, an electron-transporting layer, and a cathode.
  • a substrate may alternatively be located adjacent to the cathode, or the substrate may actually constitute the anode or cathode.
  • the organic layers between the anode and cathode are conveniently referred to as the organic EL element.
  • the total combined thickness of the organic layers is desirably less than 500 nm.
  • the device comprises in this order glass substrate, an anode (indium tin oxide (ITO)), optionally a hole injection layer (2-TNATA (4,4 ' ,4 " -tris(N-(naphtha- 2-yl)-N-phenyl-amino)triphenylamine), a hole transport layer (4,4'-bis[N-(1-naphtyl)-N- phenylamino]biphenyl ( ⁇ -NPD) co-evaporated with molybdenum oxide in an ratio of about
  • ITO indium tin oxide
  • 2-TNATA 4,4 ' ,4 " -tris(N-(naphtha- 2-yl)-N-phenyl-amino)triphenylamine
  • a hole transport layer (4,4'-bis[N-(1-naphtyl)-N- phenylamino]biphenyl ( ⁇ -NPD) co-
  • an electron blocking layer (TAPC [1 ,1-bis[4-[ ⁇ /, ⁇ /-di(p-tolyl)amino]phenyl]cyclohexane])
  • an emissive layer (Cpd.
  • A-1 , A-8, B-8, A-30, or A-6 as host doped with 10% of blue emitter (Flrpic [bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(lll)]), a hole blocking layer (BAIq [bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium]), a electron transport layer (BPhen (4,7-diphenyl-1 ,10-phenanthroline) doped with 6% Cs), and a cathode (Al, or LiF/AI).
  • blue emitter Felrpic [bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(lll)]
  • BAIq bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium
  • BPhen
  • the substrate can either be light transmissive or opaque, depending on the intended direction of light emission.
  • the light transmissive property is desirable for viewing the EL emission through the substrate.
  • Transparent glass or plastic is commonly employed in such cases.
  • the substrate can be a complex structure comprising multiple layers of materials. This is typically the case for active matrix substrates wherein TFTs are provided below the OLED layers. It is still necessary that the substrate, at least in the emissive pixilated areas, be comprised of largely transparent materials such as glass or polymers.
  • the transmissive characteristic of the bottom support is immaterial, and therefore can be light transmissive, light absorbing or light reflective.
  • Substrates for use in this case include, but are not limited to, glass, plastic, semiconductor materials, silicon, ceramics, and circuit board materials.
  • the substrate can be a complex structure comprising multiple layers of materials such as found in active matrix TFT designs. It is necessary to provide in these device configurations a light- transparent top electrode.
  • the anode When the desired electroluminescent light emission (EL) is viewed through the anode, the anode should be transparent or substantially transparent to the emission of interest.
  • Common transparent anode materials used in this invention are indium-tin oxide (ITO), indium-zinc oxide (IZO) and tin oxide, but other metal oxides can work including, but not limited to, aluminum- or indium-doped zinc oxide, magnesium-indium oxide, and nickel- tungsten oxide.
  • metal nitrides such as gallium nitride
  • metal selenides such as zinc selenide
  • metal sulfides such as zinc sulfide
  • the transmissive characteristics of the anode are immaterial and any conductive material can be used, transparent, opaque or reflective.
  • Example conductors for this application include, but are not limited to, gold, iridium, molybdenum, palladium, and platinum. Desired anode materials are commonly deposited by any suitable means such as evaporation, sputtering, chemical vapor deposition, or electrochemical means.
  • Anodes can be patterned using well- known photolithographic processes.
  • anodes may be polished prior to application of other layers to reduce surface roughness so as to minimize shorts or enhance reflectivity.
  • the cathode used in this invention can be comprised of nearly any conductive material. Desirable materials have good film- forming properties to ensure good contact with the underlying organic layer, promote electron injection at low voltage, and have good stability. Useful cathode materials often contain a low work function metal ( ⁇ 4.0 eV) or metal alloy. One useful cathode material is comprised of a Mg:Ag alloy wherein the percentage of silver is in the range of 1 to 20%, as described in US- A-4, 885,221.
  • cathode materials include bilayers comprising the cathode and a thin electron-injection layer (EIL) in contact with an organic layer (e.g., an electron transporting layer (ETL)) which is capped with a thicker layer of a conductive metal.
  • EIL electron transporting layer
  • the EIL preferably includes a low work function metal or metal salt, and if so, the thicker capping layer does not need to have a low work function.
  • One such cathode is comprised of a thin layer of LiF followed by a thicker layer of Al as described in US-A- 5,677,572.
  • An ETL material doped with an alkali metal, for example, Li-doped AIq is another example of a useful EIL.
  • Other useful cathode material sets include, but are not limited to, those disclosed in US-A-5,059,861 , 5,059,862 and 6,140,763.
  • the cathode When light emission is viewed through the cathode, the cathode must be transparent or nearly transparent. For such applications, metals must be thin or one must use transparent conductive oxides, or a combination of these materials.
  • Optically transparent cathodes have been described in more detail in US-A-4,885,21 1 , 5,247,190, JP 3,234,963, U.S. Pat. Nos.
  • Cathode materials are typically deposited by any suitable method such as evaporation, sputtering, or chemical vapor deposition. When needed, patterning can be achieved through many well known methods including, but not limited to, through-mask deposition, integral shadow masking as described in US-A-5,276,380 and EP0732868, laser ablation, and selective chemical vapor deposition.
  • HIL Hole-Injecting Layer
  • a hole-injecting layer may be provided between anode and hole-transporting layer.
  • the hole- injecting material can serve to improve the film formation property of subsequent organic layers and to facilitate injection of holes into the hole-transporting layer.
  • Suitable materials for use in the hole-injecting layer include, but are not limited to, porphyrinic compounds as described in US-A-4,720,432, plasma-deposited fluorocarbon polymers as described in US- A-6,208,075, and some aromatic amines, for example, m-MTDATA (4,4',4"-tris[(3- methylphenyl)phenylamino]triphenylamine), or 2-TNATA (4,4 ' ,4 " -tris(N-(naphtha-2-yl)-N- phenyl-amino)triphenylamine).
  • Alternative hole-injecting materials reportedly useful in organic EL devices are described in EP0891 121 and EP1029909.
  • HTL Hole-Transporting Layer
  • the hole-transporting layer of the organic EL device contains at least one hole-transporting compound such as an aromatic tertiary amine, where the latter is understood to be a compound containing at least one trivalent nitrogen atom that is bonded only to carbon atoms, at least one of which is a member of an aromatic ring.
  • the aromatic tertiary amine can be an arylamine, such as a monoarylamine, diarylamine, triarylamine, or a polymeric arylamine. Exemplary monomeric triarylamines are illustrated in US-A-3, 180,730.
  • triarylamines substituted with one or more vinyl radicals and/or comprising at least one active hydrogen containing group are disclosed in US-A-3, 567, 450 and 3,658,520.
  • a more preferred class of aromatic tertiary amines are those which include at least two aromatic tertiary amine moieties as described in US-A-4,720,432 and 5,061 ,569.
  • Such compounds include those represented by structural formula , wherein Q 1 and Q 2 are independently selected aromatic tertiary amine moieties and G is a linking group such as an arylene, cycloalkylene, or alkylene group of a carbon to carbon bond.
  • At least one of Q 1 or Q 2 contains a polycyclic fused ring structure, e.g., a naphthalene.
  • G is an aryl group, it is conveniently a phenylene, biphenylene, or naphthalene moiety.
  • a useful class of triarylamines satisfying structural formula (A) and containing two triarylamine moieties is represented by structural formula
  • Q and Q each independently represents a hydrogen atom, an aryl group, or an alkyl group or Q 3 and Q 4 together represent the atoms completing a cycloalkyl group; and Q 5 and Q 6 each independently represents an aryl group, which is in turn substituted with a diaryl substituted amino group, as indicated by structural formula , wherein Q 7 and Q 8 are independently selected aryl groups.
  • at least one of Q 7 or Q 8 contains a polycyclic fused ring structure, e.g., a naphthalene.
  • tetraaryldiamines Another class of aromatic tertiary amines are the tetraaryldiamines. Desirable tetraaryldiamines include two diarylamino groups, such as indicated by formula (C), linked through an arylene group. Useful tetraaryldiamines include those represented by formula (C).
  • each Are is an independently selected arylene group, such as a phenylene or anthracene moiety
  • n is an integer of from 1 to 4
  • Ar, Q 9 , Q 10 , and Q 11 are independently selected aryl groups.
  • at least one of Ar, Q 9 , Q 10 , and Q 11 is a polycyclic fused ring structure, e.g., a naphthalene.
  • the various alkyl, alkylene, aryl, and arylene moieties of the foregoing structural formulae (A), (B), (C), (D), can each in turn be substituted.
  • Typical substituents include alkyl groups, alkoxy groups, aryl groups, aryloxy groups, and halogen such as fluoride, chloride, and bromide.
  • the various alkyl and alkylene moieties typically contain from about 1 to 6 carbon atoms.
  • the cycloalkyl moieties can contain from 3 to about 10 carbon atoms, but typically contain five, six, or seven ring carbon atoms, e.g. cyclopentyl, cyclohexyl, and cycloheptyl ring structures.
  • the aryl and arylene moieties are usually phenyl and phenylene moieties.
  • the hole-transporting layer can be formed of a single or a mixture of aromatic tertiary amine compounds.
  • a triarylamine such as a triarylamine satisfying the formula (B)
  • a tetraaryldiamine such as indicated by formula (D).
  • a triarylamine is employed in combination with a tetraaryldiamine, the latter is positioned as a layer interposed between the triarylamine and the electron injecting and transporting layer.
  • Illustrative of useful aromatic tertiary amines are the following: 1 ,1-Bis(4- di-p-tolylaminophenyl)cyclohexane, 1 ,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, N,N,N',N'-tetraphenyl-4,4'"-diamino-1 ,1 ':4',1 ":4", 1 '"-quaterphenyl bis(4-dimethylamino-2- methylphenyl)phenylmethane, 1 ,4-bis[2-[4-[N,N-di(p-toly)amino]phenyl]vinyl]benzene (BDTAPVB), N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N,N,N',N'-tetrapheny
  • a hole transport layer may be used to enhance conductivity.
  • NPD and TPD are examples of intrinsic hole transport layers.
  • An example of a p-doped hole transport layer is m-MTDATA doped with F 4 -TCNQ at a molar ratio of 50:1 as disclosed in US6,337,102 or DE10058578.
  • Another class of useful hole-transporting materials includes polycyclic aromatic compounds as described in EP1009041. Tertiary aromatic amines with more than two amine groups may be used including oligomeric materials.
  • polymeric hole-transporting materials can be used such as poly(N-vinylcarbazole) (PVK), polythiophenes, polypyrrole, polyaniline, and copolymers such as poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) also called PEDOT/PSS.
  • PVK poly(N-vinylcarbazole)
  • polythiophenes polypyrrole
  • polyaniline polyaniline
  • copolymers such as poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) also called PEDOT/PSS.
  • fluorescent materials In addition to the phosphorescent materials, other light emitting materials may be used in the OLED device, including fluorescent materials.
  • fluorescent is commonly used to describe any light emitting material, in this case we are referring to a material that emits light from a singlet excited state. Fluorescent materials may be used in the same layer as the phosphorescent material, in adjacent layers, in adjacent pixels, or any combination. Care must be taken not to select materials that will adversely affect the performance of the phosphorescent materials. One skilled in the art will understand that triplet excited state energies of materials in the same layer as the phosphorescent material or in an adjacent layer must be appropriately set so as to prevent unwanted quenching.
  • the light-emitting layer (LEL) of the organic EL element includes a luminescent fluorescent or phosphorescent material where electroluminescence is produced as a result of electron-hole pair recombination in this region.
  • the light-emitting layer can be comprised of a single material, but more commonly consists of a host material doped with a guest emitting material or materials where light emission comes primarily from the emitting materials and can be of any color.
  • the host materials in the light-emitting layer can be an electron-transporting material, as defined below, a hole-transporting material, as defined above, or another material or combination of materials that support hole-electron recombination.
  • Fluorescent emitting materials are typically incorporated at 0.01 to 10% by weight of the host material.
  • the host and emitting materials can be small non-polymeric molecules or polymeric materials such as polyfluorenes and polyvinylarylenes (e.g., poly(p-phenylenevinylene), PPV).
  • small molecule emitting materials can be molecularly dispersed into a polymeric host, or the emitting materials can be added by copolymerizing a minor constituent into a host polymer.
  • Host materials may be mixed together in order to improve film formation, electrical properties, light emission efficiency, lifetime, or manufacturability.
  • the host may comprise a material that has good hole-transporting properties and a material that has good electron-transporting properties.
  • Host and emitting materials known to be of use include, but are not limited to, those disclosed in US-A-4,768,292, 5,141 ,671 , 5,150,006, 5,151 ,629, 5,405,709, 5,484,922, 5,593,788, 5,645,948, 5,683,823, 5,755,999, 5,928,802, 5,935,720, 5,935,721 , and 6,020,078.
  • Form E Metal complexes of 8-hydroxyquinoline and similar derivatives constitute one class of useful host compounds capable of supporting electroluminescence, and are particularly suitable for light emission of wavelengths longer than 500 nm, e.g., green, yellow, orange, and red.
  • the metal can be monovalent, divalent, trivalent, or tetravalent metal.
  • the metal can, for example, be an alkali metal, such as lithium, sodium, or potassium; an alkaline earth metal, such as magnesium or calcium; an earth metal, such aluminum or gallium, or a transition metal such as zinc or zirconium.
  • alkali metal such as lithium, sodium, or potassium
  • alkaline earth metal such as magnesium or calcium
  • earth metal such aluminum or gallium, or a transition metal such as zinc or zirconium.
  • any monovalent, divalent, trivalent, or tetravalent metal known to be a useful chelating metal can be employed.
  • ZZ completes a heterocyclic nucleus containing at least two fused aromatic rings, at least one of which is an azole or azine ring. Additional rings, including both aliphatic and aromatic rings, can be fused with the two required rings, if required. To avoid adding molecular bulk without improving on function the number of ring atoms is usually maintained at 18 or less.
  • CO-1 Aluminum trisoxine [alias, tris(8-quinolinolato)aluminum(lll)]
  • CO-2 Magnesium bisoxine [alias, bis(8-quinolinolato)magnesium(ll)]
  • CO-3 Bis[benzo ⁇ f ⁇ -8-quinolinolato]zinc(ll)
  • CO-4 Bis(2-methyl-8-quinolinolato)aluminum(lll)- ⁇ -oxo-bis(2-methyl-8-quinol- inolato)aluminum(lll)
  • CO-5 Indium trisoxine [alias, tris(8-quinolinolato)indium]
  • CO-6 Aluminum tris(5-methyloxine) [alias, tris(5-methyl-8-quinolinolato) aluminum(lll)]
  • CO-7 Lithium oxine [alias, (8-quinolinolato)lithium(l)]
  • CO-8 Gallium oxine [alias, tris(8-quinolinolato)gallium(lll)]
  • Useful fluorescent emitting materials include, but are not limited to, derivatives of anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, and quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrilium and thiapyrilium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, and carbostyryl compounds.
  • Illustrative examples of useful materials include, but are not limited to, compounds L1 to L52 described in US7,090,930B2.
  • ETL Electron-Transporting Layer
  • Preferred thin film-forming materials for use in forming the electron-transporting layer of the organic EL devices of this invention are metal chelated oxinoid compounds, including chelates of oxine itself (also commonly referred to as 8-quinolinol or 8-hydroxyquinoline). Such compounds help to inject and transport electrons and exhibit both high levels of performance and are readily fabricated in the form of thin films.
  • Exemplary of contemplated oxinoid compounds are those satisfying structural formula (E), previously described.
  • Other electron-transporting materials include various butadiene derivatives as disclosed in US4,356,429 and various heterocyclic optical brighteners as described in US4,539,507. Benzazoles satisfying structural formula (G) are also useful electron transporting materials.
  • Triazines are also known to be useful as electron transporting materials. Doping may be used to enhance conductivity.
  • AIq 3 is an example of an intrinsic electron transport layer.
  • An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1 :1 , as disclosed in US 6,337,102.
  • the organic materials mentioned above are suitably deposited by any means suitable for the form of the organic materials.
  • they are conveniently deposited through thermal evaporation, but can be deposited by other means such as from a solvent with an optional binder to improve film formation.
  • solution processing is usually preferred e.g. spin-coating, ink-jet printing. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Patterned deposition can be achieved using shadow masks, integral shadow masks (US5,294,870), spatially-defined thermal dye transfer from a donor sheet (US5,688,551 , 5,851 ,709 and 6,066,357) and inkjet method (US6,066,357).
  • OLED devices are sensitive to moisture or oxygen, or both, so they are commonly sealed in an inert atmosphere such as nitrogen or argon, along with a desiccant such as alumina, bauxite, calcium sulfate, clays, silica gel, zeolites, alkaline metal oxides, alkaline earth metal oxides, sulfates, or metal halides and perchlorates.
  • a desiccant such as alumina, bauxite, calcium sulfate, clays, silica gel, zeolites, alkaline metal oxides, alkaline earth metal oxides, sulfates, or metal halides and perchlorates.
  • Methods for encapsulation and desiccation include, but are not limited to, those described in US6,226,890.
  • barrier layers such as SiO x , Teflon, and alternating inorganic/polymeric layers are known in the art for encapsulation.
  • Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signalling, fully transparent displays, flexible displays, laser printers, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, theatre or stadium screen, or a sign.
  • PDAs personal digital assistants
  • Various control mechanism may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix.
  • Example 6 a) 40.0 g (109 mmol) of 4,4-dibromobenzyl and 24.0 g (218 mmol) of resorcinol are stirred in a mixture of 185 ml of xylene and 45 ml of ethyl acetate. The medium is heated at 55°C and HCI gas bubbled through the reaction mixture during eight hours. After cooling, a beige suspension is obtained. This suspension is filtered, washed with 90 ml of cold xylene and 170 ml of water. The product is dried at 90 0 C under reduced pressure. 54.2 g of a beige-gray powder are obtained (90%).
  • Devices are fabricated by thermal evaporation under high vacuum ( ⁇ 10 "6 mbar).
  • the anode consists of 120 nm of indium tin oxide (ITO) previously deposited on a glass substrate.
  • the cathode consisted of 100 nm of aluminium. All devices were tested immediately after preparation, without encapsulation, in a nitrogen atmosphere of a glove box ( ⁇ 1 ppm of H 2 O and O 2 ). All materials used were of sublimed quality.
  • the organic stack consists sequentially, from the ITO surface, of 60 nm of HTM composed of ⁇ /, ⁇ /'-bis(naphthalen-1-yl)- ⁇ /, ⁇ /'-bis(phenyl)-2,2'-dimethylbenzidine (NPD) co-evaporated in a
  • the emissive layer consists of 20 nm of compound A-2, A-8, B-8, A-30, or A-6 as host doped with 10% of blue emitter
  • Flrpic bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(lll)]
  • BAIq bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium
  • ETM composed of BPhen (4,7-diphenyl-1 ,10-phenanthroline) doped with 6%

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Abstract

La présente invention concerne des dispositifs électroniques, en particulier des dispositifs électroluminescents, comprenant des composés de formule (I) et/ou (II), en particulier comme hôtes pour des émetteurs phosphorescents, des matériaux transporteurs d’électrons, ou des matériaux émetteurs. Les hôtes peuvent fonctionner avec des matériaux phosphorescents afin d’améliorer l’efficacité, la stabilité, l’aisance de fabrication ou les caractéristiques spectrales des dispositifs électroluminescents.
PCT/EP2009/063267 2008-10-21 2009-10-12 Composés polycycliques pour des applications électroniques WO2010046259A1 (fr)

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