WO2023228005A1 - Composé et dispositif électroluminescent organique comprenant le composé - Google Patents

Composé et dispositif électroluminescent organique comprenant le composé Download PDF

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WO2023228005A1
WO2023228005A1 PCT/IB2023/055004 IB2023055004W WO2023228005A1 WO 2023228005 A1 WO2023228005 A1 WO 2023228005A1 IB 2023055004 W IB2023055004 W IB 2023055004W WO 2023228005 A1 WO2023228005 A1 WO 2023228005A1
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substituted
group
unsubstituted
ring
carbon atoms
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PCT/IB2023/055004
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Peter Murer
Chao-chen LIN
Daniela Sustac-Roman
Pierre Boufflet
Thomas Schäfer
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Idemitsu Kosan Co., Ltd.
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Publication of WO2023228005A1 publication Critical patent/WO2023228005A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—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
    • 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

Definitions

  • the present invention relates to specific compounds, a material, preferably an emitter material, for an organic electroluminescence device comprising said specific compounds, an organic electroluminescence device comprising said specific compounds, an electronic equipment com- prising said organic electroluminescence device, a light emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one of said specific com- pounds, and the use of said compounds in an organic electroluminescence device.
  • an organic electroluminescence device When a voltage is applied to an organic electroluminescence device (hereinafter may be re- ferred to as an organic EL device), holes are injected to an emitting layer from an anode and electrons are injected to an emitting layer from a cathode. In the emitting layer, injected holes and electrons are re-combined and excitons are formed.
  • An organic EL device comprises an emitting layer between the anode and the cathode. Further, there may be a case where it has a stacked layer structure comprising an organic layer such as a hole-injecting layer, a hole-transporting layer, an electron-injecting layer, an electron-transpor- ting layer, etc.
  • EP 3109253 A1 relates to a polycyclic aromatic compound represented by the following gen- eral formula (1), or an oligomer of a polycyclic aromatic compound having plural structures each represented by the following general formula (1), and an organic electroluminescent (EL) ele- ment, an organic field effect transistor and an organic thin film solar cell using the polycyclic aro- matic compound, as well as a display apparatus and a lighting apparatus.
  • a polycyclic aromatic compound represented by the following gen- eral formula (1) or an oligomer of a polycyclic aromatic compound having plural structures each represented by the following general formula (1)
  • an organic electroluminescent (EL) ele- ment an organic field effect transistor and an organic thin film solar cell using the polycyclic aro- matic compound, as well as a display apparatus and a lighting apparatus.
  • EL organic electroluminescent
  • ring A, ring B and ring C each independently represent an aryl ring or a heteroaryl ring, while at least one hydrogen atom in these rings may be substituted;
  • X 1 and X 2 each independently represent O, N-R, S or Se, wherein R of the moiety N-R repre- sents an aryl which may be substituted, a heteroaryl which may be substituted, or an alkyl which may be substituted, and R of the moiety N-R may be bonded to the ring A, ring B and/or ring C by a linking group or a single bond; and at least one hydrogen atom in the compound or structure represented by formula (1) may be substituted by a halogen atom or a deuterium atom.
  • EP 3660024 A1 relates to polycyclic aromatic compounds represented by the following formu- lae A-1 and A-2 and organic electroluminescent devices using the same. Specific examples are: WO 2020/217229 A1 relates to specific polycyclic compounds represented by formula (I), a ma- terial for an organic electroluminescence device comprising said polycyclic compound, an or- ganic electroluminescence device comprising said polycyclic compound, an electronic equip- ment comprising said organic electroluminescence device, a process for preparing said polycy- tun compounds, and the use of said polycyclic compounds in an organic electroluminescence. Specific examples are:
  • ring A 1 represents an aromatic group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by o groups R 3 , a heteroaromatic group having 5 to 30 ring atoms which is unsubsti- tuted or substituted by o groups R 3 or a group of formula (II) (II), wherein one * in formula (II) represents a bonding site to B and one * in formula (II) represents a bonding site to X; ring B 1 represents an aromatic group having 6 to 30 ring carbon atoms or a heteroaromatic group having 5 to 30 ring atoms; Y represents NR E , O, S, SiR 4 R 5 or CR 6 R 7 ; X represents NR E , O, S, SiR 4 R 5 or CR 6 R 7
  • the compounds of formula (I) can be in principal used in any layer of an EL device.
  • the compounds of for- mula (I) are used as fluorescent dopants in organic EL devices, especially in the light-emitting layer.
  • organic EL device organic electroluminescence device
  • OLED organic light-emitting diode
  • the compounds of formula (I) according to the present invention preferably have a Full width at half maximum (FWHM) of lower than 30 nm, more preferably lower than 25 nm, more preferably lower than 23 nm. It has further been found that organic EL devices comprising the compounds of the present in- vention are generally characterized by high external quantum efficiencies (EQE) and long life- times, especially when the specific compounds of formula (I) are used as dopants (light emitting material), especially fluorescent dopants in organic electroluminescence devices.
  • EQE external quantum efficiencies
  • H, D halogen, a substituted or unsubstituted alkyl group having 1 to 25 carbon at- oms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms, a substituted or unsubstituted cycloal- kyl group having 3 to 25 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon at- oms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted ar- yloxy group having 6 to 30 ring carbon atoms, a substituted or un
  • hydrogen (H) includes isomers differing in the number of neutrons, i.e. protium, deuterium (D) and tritium.
  • the groups mentioned below therefore include its partly or fully deu- terated analogs.
  • the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably from 6 to 24, more preferably from 6 to 18 ring carbon atoms most preferably having from 6 to 13 ring carbon atoms, may be a non-condensed aromatic group or a condensed aromatic group.
  • Spe- cific examples thereof include phenyl group, d 5 -phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, indenyl group, anthracenyl, chrysenyl, spirofluorenyl group, benzo[c]phe- nanthrenyl group, with phenyl group, naphthyl group, biphenyl group, terphenyl group, phenan- thryl group, triphenylenyl group, fluorenyl group, indenyl group and fluoranthenyl group being preferred, phenyl group, 1-naphthyl group, 2-naphthyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group
  • the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, preferably 5 to 24, more preferably 5 to 18 ring atoms, most preferably having from 5 to 13 ring atoms, may be a non-condensed heteroaromatic group or a condensed heteroaromatic group.
  • Examples of the substituted or unsubstituted alkyl group having 1 to 25 carbon atoms include methyl group, CD3, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n- nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopen- tyl group, 1-methylpentyl group, with methyl group,
  • alkyl groups having 1 to 8 carbon atoms are preferably 1 to 4 carbon atoms. Suitable examples for alkyl groups having 1 to 8 carbon atoms respectively 1 to 4 carbon atoms are mentioned before. Examples of the substituted or unsubstituted fluoroalkyl groups having 1 to 25 carbon atoms in- clude the alkyl groups mentioned above wherein the hydrogen atoms thereof are partly or en- tirely substituted by fluorine atoms, for example CF3.
  • Examples of the substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms include ethene group, n-propene group, isopropene group, n-butene group, isobutene group, n-pentene group, n-hexene group, n-heptene group, n-octene group, n-nonene group, n-decene group, n- undecene group, n-dodecene group, n-tridecene group, n-tetradecene group, n-pentadecene group, n-hexadecene group, n-heptadecene group, n-octadecene group, with ethene group, n- propene group, isopropene group, n-butene group, isobutene group being preferred.
  • alkenyl groups having 2 to 8 carbon atoms are preferred.
  • Suitable examples for alkenyl groups having 2 to 8 carbon atoms respectively 2 to 4 carbon atoms are mentioned before.
  • Examples of the substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms include ethynyl group, n-propynyl group, n-butynyl group, n-pentynyl group, n-hexynyl group, n-heptynyl group, n-octynyl group, with ethynyl group, n-propynyl group, n-butynyl group being preferred.
  • alkynyl groups having 2 to 8 carbon atoms are preferably 2 to 4 carbon atoms. Suitable examples for alkynyl groups having 2 to 8 carbon atoms respectively 2 to 4 carbon at- oms are mentioned before.
  • Examples of the substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, and adamantyl group, with cyclopentyl group, and cyclohexyl group being preferred.
  • Suitable examples for cycloalkyl groups having 3 to 6 carbon atoms are mentioned before.
  • An example for an aralkyl group having from 7 to 50 carbon atoms which is unsubstituted or substituted includes a benzyl group.
  • Examples of halogen atoms include fluorine, chlorine, bromine, and iodine, with fluorine being preferred.
  • Examples of the substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, prefer- ably 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms, include a methoxy group, an ethoxy group, a propoxy group and a butoxy group.
  • Examples of the substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, preferably 6 to 24 ring carbon atoms, more preferably 6 to 18 ring carbon atoms, include those having an aryl portion selected from the aryl groups mentioned above, for example -OPh.
  • Examples of the substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, preferably 6 to 24 ring carbon atoms, more preferably 6 to 18 ring carbon atoms include those having an aryl portion selected from the aryl groups mentioned above, for example -SPh.
  • the silyl group is preferably a C 1-20 alkyl and/or C 6-18 aryl substituted silyl group.
  • C 1-20 alkyl and/or C 6-18 aryl substituted silyl groups include alkylsilyl groups having 1 to 8 carbon atoms in each alkyl residue, preferably 1 to 4 carbon atoms, includ- ing trimethylsilyl group, triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t-butyl- dimethylsilyl group, propyldimethylsilyl group, dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutylsilyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group, and arylsilyl groups having 6 to 18 ring carbon atoms in each aryl residue,
  • the amino group is preferably a C 1-20 alkyl and/or C 6-18 aryl substituted amino group, more preferably a C 6 -18aryl substituted amino group.
  • Preferred examples are a di- phenylamino group, a d10-diphenylamino group, or a bis(4-(tert-butyl)phenyl)amino group.
  • Examples of the optional substituent(s) indicated by “substituted or unsubstituted” and “may be substituted” referred to above or hereinafter include an aryl group having from 6 to 30, prefera- bly from 6 to 24, more preferably from 6 to 18 ring carbon atoms which is in turn unsubstituted or substituted, a heteroaryl group having from 5 to 30, preferably 5 to 24, more preferably 5 to 18 ring atoms which is in turn unsubstituted or substituted, an alkyl group having 1 to 25, prefer- ably 1 to 8 carbon atoms, a cycloalkyl group having 3 to 25, preferably 3 to 6 carbon atoms, a heterocyclic group having 5 to 30, preferably 5 or 6 carbon atoms, an alkenyl group having from 1 to 25 carbon atoms, an alkynyl group having from 1 to 25 carbon atoms, an aryloxy group having from 6 to 30 carbon atoms, an arylthio group having from 6 to 30
  • the optional substituents preferably each independently represents an aryl group having from 6 to 30, preferably from 6 to 24, more preferably from 6 to 18 ring carbon atoms which is in turn unsubstituted or substituted, a heteroaryl group having from 5 to 30, preferably 5 to 24, more preferably 5 to 18 ring atoms which is in turn unsubstituted or substituted, an alkyl group having 1 to 25, preferably 1 to 8 carbon atoms, a cycloalkyl group having 3 to 25, preferably 3 to 6 car- bon atoms; fluorine, CN; SiR 24 R 25 R 26 , NR 84 R 85 , an aryloxy group having from 6 to 30 carbon at- oms; or two adjacent substituents together form a ring structure which is in turn unsubstituted or substi- tuted.
  • the optional substituents each independently represents an aryl group having from 6 to 18 ring carbon atoms which is in turn unsubstituted or substituted, a heteroaryl group having from 5 to 18 ring atoms which is in turn unsubstituted or substituted, an alkyl group hav- ing 1 to 8 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms; fluorine, CN; NR 84 R 85 , or SiR 24 R 25 R 26 ; or two adjacent substituents together form a ring structure which is in turn unsubstituted or substi- tuted.
  • the optional substituents each independently represents an aryl group having from 6 to 13 ring carbon atoms which is in turn unsubstituted or substituted, a heteroaryl group having from 5 to 13 ring atoms which is in turn unsubstituted or substituted, an alkyl group hav- ing 1 to 4 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms; NR 84 R 85 , or SiR 24 R 25 R 26 .
  • R 24 , R 25 and R 26 each independently represents a substituted or unsubstituted aryl group with 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group with 5 to 30 ring atoms, a sub- stituted or unsubstituted alkyl group having from 1 to 25 carbon atoms, a substituted or unsub- stituted cycloalkyl group having from 3 to 25 ring carbon atoms; preferably, R 24 , R 25 and R 26 each independently represents a substituted or unsubstituted aryl group with 6 to 18 ring atoms, a substituted or unsubstituted heteroaryl group with 5 to 18 ring atoms, a substituted or unsubstituted alkyl group having from 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 6 ring carbon atoms.
  • R 84 and R 85 each independently represents a substituted or unsubstituted aryl group with 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group with 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having from 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 25 ring carbon atoms; preferably, R 84 and R 85 each independently represents a substituted or unsubstituted aryl group with 6 to 18 ring atoms, a substituted or unsubstituted heteroaryl group with 5 to 18 ring atoms, a substituted or unsubstituted alkyl group having from 1 to 8 carbon atoms, a substituted or un- substituted cycloalkyl group having from 3 to 6 ring carbon atoms; more preferably, R 84 and R 85 each independently represents a substituted or unsubstituted
  • the amino group is a diphenylamino group, a d 10 -diphenylamino group, or a bis(4- (tert-butyl)phenyl)amine.
  • the optional substituents mentioned above may be further substituted by one or more of the op- tional substituents mentioned above.
  • the number of the optional substituents depends on the group which is substituted by said sub- stituent(s). The maximum number of possible substituents is defined by the number of hydrogen atoms present.
  • the “carbon number of a to b” in the expression of “substituted or unsubstituted X group having a to b carbon atoms” is the carbon number of the unsubstituted X group and does not include the carbon atom(s) of an optional substituent.
  • the term “unsubstituted” referred to by “unsubstituted or substituted” means that a hydrogen atom is not substituted by one the groups mentioned above.
  • An index of 0 in the definition in any formula mentioned above and below means that a hydro- gen atom is present at the position defined by said index.
  • ring structures formed by two adjacent substituents are shown below: wherein X’ represents O, S or CR 68 R 69 ; R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62 , R 63 , R 64 , R 65 , R 66 and R 67 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 and R 78 each independently repre- sents hydrogen, an aryl group having from 6 to 60 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 60 ring atoms which is unsubstituted or substi- tuted; an
  • Preferred examples for ring structures formed by two adjacent substituents are the ring struc- tures (A), (D) and (G), more preferred ring structures formed by two adjacent substituents are , wherein said ring structures are unsubstituted or substituted. Suitable and preferred substitu- ents are mentioned above.
  • the compounds of formula (I) The present invention relates to a compound represented by formula (I): wherein ring A 1 represents an aromatic group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by o groups R 3 , a heteroaromatic group having 5 to 30 ring atoms which is unsubsti- tuted or substituted by o groups R 3 or a group of formula (II) (II) , wherein one * in formula (II) represents a bonding site to B and one * in formula (II) represents a bonding site to X; and the other residues, indices and groups are defined above and below.
  • the compound of formula (I) is represented by any one of formulae (III), (IV), (V), (VI) and (VII)
  • ring A 1 represents an aromatic group having 6 to 30 ring carbon atoms which is unsubstituted or substituted by o groups R 3 , a heteroaromatic group having 5 to 30 ring atoms which is unsubsti- tuted or substituted by o groups R 3 , preferably an aromatic group having 6 to 18 ring carbon at- oms which is unsubstituted or substituted by o groups R 3 , a heteroaromatic group having 5 to 18 ring atoms which is unsubstituted or substituted by o groups R 3 .
  • the compound of formula (I) is represented by any one of formulae (III), (IV), and (V), most preferably by formula (III) or (V), further most preferably by formula (III).
  • the residues, indices and groups are defined above and below.
  • RBN, R 2 and R 3 each independently represents H, D, fluorine, a substituted or unsub- stituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms, or NR 84 R 85 ; wherein two adjacent groups R 2 and/or two adjacent groups R 3 may form together an unsubsti- tuted or substituted ring. More preferably, the residue RBN represents H or D, preferably H.
  • the group formula (I) preferably represents an aromatic group having 6 to 24 ring carbon atoms, preferably 6 to 18 ring carbon atoms, or a heteroaromatic group having 5 to 24 ring atoms, preferably 5 to 18 ring atoms, and the definitions of R 2 and n are mentioned above.
  • the group formula (I) is more preferably represented by a group of for- mula (VIII) (VIII), wherein R 2a , R 2b and R 2c each independently represents H, D, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, a sub- stituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubsti- tuted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a silyl group, an amino group, a substituted or unsubstituted fluoroalkyl group having 1 to 25 carbon atoms; or fluorine; where
  • Preferred residues R 2a , R 2b and R 2c are the same residues as defined for R 2 . More preferably, the group formula (I) is represented by a group of for- mula (VIIIa) (VIIIa), wherein the residue R2 b is defined above.
  • Y in the compound of formula (I) represents NR E , O, S, SiR 4 R 5 or CR 6 R 7 , preferably NR E , O, S or CR 6 R 7 ; more preferably NR E or O, most preferably NR E .
  • X in the compound of formula (I) represents NR E , O, S, SiR 4 R 5 or CR 6 R 7 , preferably NR E , O, S or CR 6 R 7 ; more preferably NR E or O, most preferably NR E .
  • R 4 , R 5 , R 6 , R 7 and R 8 preferably each independently represents, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon at- oms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms; wherein R 4 and R 5 or R 6 and R 7 may form together an unsubstituted or substituted ring.
  • R E in the compound of formula (I) preferably represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or un- substituted heteroaryl group having 5 to 30 ring atoms; a tertiary alkyl group having from 1 to 25 carbon atoms; in the case that X is NR E , R E or a substituent on R E may be bonded to the ring A 1 or to a substit- uent on the ring A 1 and/or to R 2a of the ring B 1 to form a ring structure which is unsubstituted or substituted; suitable examples for such ring structures are shown below; in the case that Y is NR E , R E or a substituent on R E may be bonded to R 2c of the ring B 1 to form a ring structure which is unsubstituted or substituted; suitable examples for such ring structures are shown below; R E may be the same or different when X and
  • R E in the compound of formula (I) represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; a substituted or un- substituted heteroaryl group having 5 to 18 ring atoms; a tertiary alkyl group having from 1 to 8 carbon atoms; in the case that X is NR E , R E or a substituent on R E may be bonded to the ring A 1 or to a substit- uent on the ring A 1 and/or to R 2a of the ring B 1 to form a ring structure which is unsubstituted or substituted; suitable examples for such ring structures are shown below; in the case that Y is NR E , R E or a substituent on R E may be bonded to R 2c of the ring B 1 to form a ring structure which is unsubstituted or substituted; suitable examples for such ring structures are shown below; R E may be the same or different when X and
  • a tertiary alkyl group” R E is in the meaning of the present invention a C 4 to C 25 alkyl group, pref- erably a C 4 to C 8 alkyl group, wherein a tertiary carbon atom of the tertiary alkyl group is con- nected with N.
  • R E is a group of formula (IX): wherein R E1 , R E2 , R E3 , R E4 and R E5 each independently represents H, D, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted het- erocyclic group having 5 to 30 ring atoms, a silyl group, an amino group, a substituted or unsub- stituted fluoroalkyl group having 1 to 25 carbon atoms; or fluorine; and/
  • R E1 , R E2 , R E3 , R E4 and R E5 each independently represents H, D, a substituted or un- substituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms; and/or two adjacent residues R E1 , R E2 , R E3 , R E4 and/or R E5 together form a ring structure which is un- substituted or substituted; suitable ring structures are mentioned above; or R E at X, in the case that X is NR E is a group selected from an C 2 alkenyl group which is unsub- stituted or substituted, a cycloalkyl group which is unsubstituted or substitute
  • R 3a , R 3b , R 3c and R 3d each independently represents H, D, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or un- substituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted heterocy-oul group having 5 to 30 ring atoms, a silyl group, an amino group, a substituted or unsubsti- tuted fluoroalkyl group having 1 to 25 carbon atoms
  • Preferred residues R 3a , R 3b , R 3c and R 3d are the same residues as defined for R 3 .
  • in formula (I) is more preferably represented by a group of formula (XIIa), or by a group of formula (XIIIa) (XIIIa), preferably a group of formula (XIIa).
  • the residues and groups in formula (XIIa) and (XIIIa) are the same as defined above.
  • R E or a substituent on R E may be bonded to the ring A 1 and/or to the ring B 1 or to a substituent on the ring A 1 and/or the ring B 1 to form a ring structure which is un- substituted or substituted; and/or in the case that Y is NR E , R E or a substituent on R E may be bonded to the ring B 1 or to a substit- uent on the ring B 1 to form a ring structure which is unsubstituted or substituted, and/or R E and R 1 may together form a linking group L, wherein L is a arylene group having from 6 to 14 ring carbon atoms which is unsubstituted or substituted; a heteroarylene group having from 5 to 14 ring atoms which is unsubstituted or substituted; or an alkylene group having from 1 to 8 carbon atoms which is unsubstituted or substituted.
  • R L is a arylene group having
  • R 12 , R 13 and R 16 each independently represents a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 18 ring atoms; or R 12 and R 13 may form together an unsubstituted or substituted and/or fused ring; and R 14 and R 15 each independently represents a substituted or unsubstituted alkyl group having 1 to 25, preferably 1 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 18 ring atoms; more preferably a substituted or unsubstituted alkyl group having 1 to 25, preferably 1 to 8 carbon atoms; A 1 , B 1 , R 1 , R 2 , R BN
  • U and V are present in the following combinations, wherein U and V in formula (I) and formula (II) are the same or different: More preferably, U and V are present in the following combinations i), ii) or iii), most preferably i) and ii), further most preferably i), wherein U and V in formula (I) and formula (II) are the same or different.
  • R x and R 1 each independently represents a substituted or unsubstituted aryl group with 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group with 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having from 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 25 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted fluoroalkyl group having 1
  • R x1 , R x2 , R x3 , R x4 and R x5 each independently represents H, D, a substituted or un- substituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms; and/or two adjacent residues R x1 , R x2 , R x3 , R x4 and/or R x5 together form a ring structure which is unsub- stituted or substituted; suitable ring structures are mentioned above; and one of R x1 and R x5 at R 1 may be linked with R y1 or R y5 via a single bond.
  • R 1 and R x each independently represent a group of formula (XIa) (XIa), wherein R x2 and R x3 are defined above. Further most preferably, R 1 and R x each independently represent a group of formula (XIaa) (XIaa), wherein R x3 is defined above.
  • R y represents a substituted or unsubstituted aryl group with 6 to 30, preferably 6 to 18 ring at- oms, or a substituted or unsubstituted heteroaryl group with 5 to 30, preferably 5 to 18 ring at- oms; more preferably a group of formula (X) (X), wherein R y1 , R y2 , R y3 , R y4 and R y5 each independently represents H, D, a substituted or unsubstituted al- kyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon at- oms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms
  • R y1 , R y2 , R y3 , R y4 and R y5 each independently represents H, D, a substituted or un- substituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms; and/or two adjacent residues R y1 , R y2 , R y3 , R y4 and/or R y5 together form a ring structure which is unsub- stituted or substituted; suitable ring structures are mentioned above; and one of R y1 and R y5 may be linked with R 1 via a single bond; wherein at least one of R y1 and R y5 is not hydrogen or deuterium; preferably both
  • R y represents a group of formula (Xa) wherein R y1 , R y3 and R y5 are defined above. Most preferably, at least one of R y1 and R y5 is not hydrogen or deuterium; further most preferably both of R y1 and R y5 are not hydrogen or deuter- ium.
  • the compound of formula (I) is represented by one of the following formulae (IA) and (IB) wherein all groups and residues are defined above.
  • R E or a substituent on R E may be bonded to the ring A 1 and/or to the ring B 1 or to a substituent on the ring A 1 and/or the ring B 1 to form a ring structure which is un- substituted or substituted; and/or R E may be bonded to the ring B 1 or to a substituent on the ring B 1 to form a ring structure which is unsubstituted or substituted, and/or R E and R 1 may together form a linking group L, wherein L is a arylene group having from 6 to 14 ring carbon atoms which is unsubstituted or substituted; a heteroarylene group having from 5 to 14 ring atoms which is unsubstituted or substituted; or an alkylene group having from 1 to 8 carbon atoms which is unsubstituted or substituted.
  • Suitable compounds of formula (I) comprising such ring structures are:
  • the compounds of formula (I) are for example prepared by the following step: Borylation by addition of BHal’3 to the intermediate (XIV), whereby the compound of formula (I) is obtained: : wherein Q is halogen, or SiR 79 3 , preferably, Q is halogen, more preferably Cl or Br; and R 79 represents a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substi- tuted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, a substituted or un- substituted alkoxy group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms; Hal’ represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br and most preferably Br; all other residues and indices
  • Suitable Pd catalysts are for example Pd(0) complexes with bidentate ligands like dba (diben- zylideneacetone), or Pd(II) salts like PdCl 2 or Pd(OAc) 2 in combination with bidentate phosphine ligands such as dppf ((diphenylphosphino)ferrocene), dppp ((diphenylphosphino)propane), BINAP (2,2'–Bis(diphenylphosphino)–1,1'–binaphthyl), Xantphos (4,5-Bis(diphenylphosphino)- 9,9-dimethylxanthene), DPEphos (Bis[(2-diphenylphosphino)phenyl] ether) or Josiphos, or in combination with monodentate phosphine-ligands like di-tert.-butyl-(4-dimethylamin
  • Organic electroluminescence device According to one aspect of the present invention a material for an organic electroluminescence device comprising at least one compound of formula (I) is provided. According to another aspect of the present invention, an organic electroluminescence device comprising at least one compound of formula (I) is provided.
  • an organic electroluminescence device comprising a cathode, an anode, and one or more organic thin film layers comprising a light emitting layer disposed between the cathode and the anode, wherein at least one layer of the organic thin film layers comprises at least one compound of formula (I).
  • an organic electroluminescence device is provided, wherein the light emitting layer comprises at least one compound of formula (I).
  • an organic electroluminescence device is provided, wherein the light emitting layer comprises at least one host and at least one dopant, wherein the dopant comprises at least one compound at least one compound of formula (I).
  • an organic electroluminescence device wherein the host comprises at least one substituted or unsubstituted anthracene compound. Suitable anthracene compounds are mentioned below.
  • an electronic equipment provided with the organic electroluminescence device according to the present invention is provided.
  • an emitter material is provided comprising at least one compound of formula (I).
  • a light emitting layer is provided comprising at least one compound of formula (I), preferably comprising at least one host and at least one dopant, wherein the dopant comprises at least one compound of formula (I).
  • the use of a compound of formula (I) according to the present invention in an organic electroluminescence device comprises a hole-transporting layer between the an- ode and the emitting layer.
  • the organic EL device comprises an electron-transporting layer between the cathode and the emitting layer.
  • the “one or more organic thin film layers between the emitting layer and the anode” if only one organic layer is present between the emitting layer and the anode, it means that layer, and if plural organic layers are present, it means at least one layer thereof.
  • an organic layer nearer to the emitting layer is called the “hole-transporting layer”, and an organic layer nearer to the anode is called the “hole-injecting layer”.
  • Each of the “hole-transporting layer” and the “hole-injecting layer” may be a single layer or may be formed of two or more layers. One of these layers may be a single layer and the other may be formed of two or more layers.
  • the “one or more organic thin film layers between the emitting layer and the cathode” if only one organic layer is present between the emitting layer and the cathode, it means that layer, and if plural organic layers are present, it means at least one layer thereof.
  • an organic layer nearer to the emitting layer is called the “electron-transporting layer”, and an organic layer nearer to the cathode is called the “electron-injecting layer”.
  • Each of the “elec- tron-transporting layer” and the “electron-injecting layer” may be a single layer or may be formed of two or more layers. One of these layers may be a single layer and the other may be formed of two or more layers.
  • the “one or more organic thin film layers comprising an emitting layer” mentioned above, prefer- ably the emitting layer comprises a compound represented by formula (I).
  • the compound rep- resented by formula (I) preferably functions as an emitter material, more preferably as a fluores- cent emitter material, most preferably as a blue fluorescent emitter material.
  • organic EL devices characterized by high external quantum efficiencies (EQE) and long lifetimes are pro- vided.
  • the host is not selected from CBP (4,4'-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2- yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenylj ether oxide), 9-[3- (dibenzofuran- 2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothio- phen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole, 9-[3,5-bis(
  • Preferred host materials are substituted or unsubstituted polyaromatic hydrocarbon (PAH) com- pounds, substituted or unsubstituted polyheteroaromatic compounds, substituted or unsubsti- tuted anthracene compounds, or substituted or unsubstituted pyrene compounds.
  • PAH polyaromatic hydrocarbon
  • the organic electroluminescence device comprises in the emitting layer at least one compound of formula (I) as a dopant material and at least one host material selected from the group consisting of substituted or unsubstituted poly- aromatic hydrocarbon (PAH) compounds, substituted or unsubstituted polyheteroaromatic com- pounds, substituted or unsubstituted anthracene compounds, and substituted or unsubstituted pyrene compounds.
  • PAH substituted or unsubstituted poly- aromatic hydrocarbon
  • the at least one host is at least one substituted or unsubstituted anthracene compound.
  • the organic electroluminescence device comprises in the emitting layer at least one compound of formula (I) as a dopant material and at least one host material selected from the group consisting of substituted or un- substituted polyaromatic hydrocarbon (PAH) compounds, substituted or unsubstituted anthra- cene compounds, and substituted or unsubstituted pyrene compounds.
  • PAH polyaromatic hydrocarbon
  • the at least one host is at least one substituted or unsubstituted anthracene compound.
  • an emitting layer of the organic electrolumines- cence device which comprises at least one compound of formula (I) as a dopant ma- terial and an anthracene compound as a host material.
  • Suitable anthracene compounds are represented by the following formula (10): wherein one or more pairs of two or more adjacent R 101 to R 110 may form a substituted or unsubstituted, saturated or unsaturated ring; R 101 to R 110 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 car- bon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or un- substituted alkynyl group including 2 to 50 carbon atoms, a
  • each of these groups may be the same or different; -L 101 -Ar 101 (31) wherein in the formula (31), L 101 is a single bond, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms; Ar 101 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substi- tuted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
  • each substituent, substituents for “substituted or unsubstituted” and the halogen atom in the compound (10) are the same as those mentioned above.
  • the “one pair of two or more adjacent R 101 to R 110 ” is a combination of R 101 and R 102 , R 102 and R 103 , R 103 and R 104 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 101 and R 102 and R 103 or the like, for example.
  • the substituent in “substituted” in the “substituted or unsubstituted” for the saturated or unsatu- rated ring is the same as those for “substituted or unsubstituted” mentioned in the formula (10).
  • the “saturated or unsaturated ring” means, when R 101 and R 102 form a ring, for example, a ring formed by a carbon atom with which R 101 is bonded, a carbon atom with which R 102 is bonded and one or more arbitrary elements.
  • a ring is formed by R 101 and R 102
  • an unsaturated ring is formed by a carbon atom with which R 101 is bonded
  • a carbon atom with R 102 is bonded and four carbon atoms
  • the ring formed by R 101 and R 102 is a benzene ring.
  • the “arbitrary element” is preferably a C element, an N element, an O element or an S element. In the arbitrary element (C element or N element, for example), atomic bondings that do not form a ring may be terminated by a hydrogen atom, or the like.
  • the “one or more arbitrary element” is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less arbitrary elements.
  • R 101 and R 102 may form a ring, and simultaneously, R 105 and R 106 may form a ring.
  • the compound represented by the formula (10) is a compound represented by the following formula (10A), for example:
  • R 101 to R 110 are independently a hydrogen atom, a substituted or unsubsti- tuted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group in- cluding 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms or a group represented by the formula (31).
  • R 101 to R 110 are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group in- cluding 5 to 50 ring atoms or a group represented by the formula (31). More preferably, R 101 to R 110 are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group including 5 to 18 ring atoms or a group represented by the formula (31). Most preferably, at least one of R 109 and R 110 is a group represented by the formula (31).
  • R 109 and R 110 are independently a group represented by the formula (31).
  • the compound (10) is a compound represented by the following formula (10-1): (10-1) wherein in the formula (10-1), R 101 to R 108 , L 101 and Ar 101 are as defined in the formula (10).
  • the compound (10) is a compound represented by the following formula (10-2): (10-2) wherein in the formula (10-2), R 101 , R 103 to R 108 , L 101 and Ar 101 are as defined in the formula (10).
  • the compound (10) is a compound represented by the following formula (10-3): wherein in the formula (10-3), R 101A to R 108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; L 101A is a single bond or a substituted or unsubstituted arylene group including 6 to 30 ring car- bon atoms, and the two L 101A s may be the same or different; Ar 101A is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and the two Ar 101A s may be the same or different.
  • the compound (10) is a compound represented by the following formula (10-4): (10-4) wherein in the formula (10-4), L 101 and Ar 101 are as defined in the formula (10); R 101A to R 108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; X 11 is O, S, or N(R 61’ ); R 61’ is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon at- oms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; one of R 62’ to R 69’ is an atomic bonding that is bonded with L 101 ; one or more pairs of adjacent R 62’ to R 69’ that are not bonded with L 101 may be bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring; and R 62’ to R 69
  • the compound (10) is a compound represented by the following formula (10-4A) wherein in the formula (10-4A), L 101 and Ar 101 are as defined in the formula (10); R 101A to R 108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; X 11 is O, S or N(R 61 ); R 61 is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon at- oms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; one or more pairs of adjacent two or more of R 62A to R 69A may form a substituted or unsubsti- tuted, saturated or unsaturated ring, and adjacent two of R 62A to R 69A form a ring represented by the following formula (10-4A-1); and R 62A to R 69A that do not form a substituted or unsubsti
  • each of the two atomic bondings * is bonded with adjacent two of R 62A to R 69A ; one of R 70’ to R 73’ is an atomic bonding that is bonded with L 101 ; and R 70’ to R 73’ that are not bonded with L 101 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
  • the compound (10) is a compound represented by the following formula (10-6): (10-6) wherein in the formula (10-6), L 101 and Ar 101 are as defined in the formula (10); R 101A to R 108A are as defined in the formula (10-4); R 66’ to R 69’ are as defined in the formula (10-4); and X 12 is O or S.
  • the compound represented by the formula (10-6) is a compound repre- sented by the following formula (10-6H):
  • the compound represented by the formulae (10-6) and (10-6H) is a com- pound represented by the following formula (10-6Ha): (10-6Ha) wherein in the formula (10-6Ha), L 101 and Ar 101 are as defined in the formula (10); and X 12 is O or S.
  • the compound represented by the formulae (10-6), (10-6H) and (10-6Ha) is a compound represented by the following formula (10-6Ha-1) or (10-6Ha-2): wherein in the formula (10-6Ha-1) and (10-6Ha-2), L 101 and Ar 101 are as defined in the formula (10); and X 12 is O or S.
  • the compound (10) is a compound represented by the following formula (10-7): (10-7) wherein in the formula (10-7), L 101 and Ar 101 are as defined in the formula (10); R 101A to R 108A are as defined in the formula (10-4); X 11 is as defined in the formula (10-4); and R 62’ to R 69’ are as defined in the formula (10-4), provided that any one pair of R 66’ and R 67’ , R 67’ and R 68’ , and R 68’ and R 69’ are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring.
  • the compound (10) is a compound represented by the following formula (10-7H): w L 101 and Ar 101 are as defined in the formula (10); X 11 is as defined in the formula (10-4); and R 62’ to R 69’ are as defined in the formula (10-4), provided that any one pair of R 66’ and R 67’ , R 67’ and R 68’ , and R 68’ and R 69’ are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring.
  • the compound (10) is a compound represented by the following formula (10-8):
  • the compound represented by the formula (10-8) is a compound repre- sented by the following formula (10-8H): In the formula (10-8H), L 101 and Ar 101 are as defined in the formula (10).
  • R 66’ to R 69’ are as defined in the formula (10-4), provided that any one pair of R 66’ and R 67’ , R 67’ and R 68’ , as well as R 68’ and R 69’ are bonded with each other to form a substituted or unsubsti- tuted, saturated or unsaturated ring. Any one pair of R 66’ and R 67’ , R 67’ and R 68’ , as well as R 68’ and R 69’ may preferably be bonded with each other to form an unsubstituted benzene ring; and X 12 is O or S.
  • any one pair of R 66’ and R 67’ , R 67’ and R 68’ , as well as R 68’ and R 69’ are bonded with each other to form a ring represented by the following formula (10-8-1) or (10-8-2), and R 66’ to R 69’ that do not form the ring represented by the formula (10-8-1) or (10-8-2) do not form a substituted or unsub- stituted, saturated or unsaturated ring.
  • R 80 to R 83 are independently a hydrogen atom, a substituted or unsubstituted alkyl group includ- ing 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring car- bon atoms; and
  • X 13 is O or S.
  • the compound (10) is a compound represented by the following formula (10-9): (10-9) wherein in the formula (10-9), L 101 and Ar 101 are as defined in the formula (10); R 101A to R 108A are as defined in the formula (10-4); R 66’ to R 69’ are as defined in the formula (10-4), provided that R 66’ and R 67’ , R 67’ and R 68’ , as well as R 68’ and R 69’ are not bonded with each other and do not form a substituted or unsubstituted, saturated or unsaturated ring; and X 12 is O or S.
  • the compound (10) is selected from the group consisting of compounds represented by the following formulae (10-10-1) to (10-10-4).
  • L 101A and Ar 101A are as defined in the formula (10-3).
  • at least one Ar 101 is a monovalent group having a structure represented by the following formula (50).
  • X151 is O, S, or C(R 161 )(R162).
  • R151 to R160 is a single bond which bonds with L 101 .
  • R 151 to R 154 and one or more sets of adjacent two or more of R 155 to R 160 which are not a single bond which bonds with L 101 , form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substi- tuted or unsubstituted, saturated or unsaturated ring.
  • R 161 and R 162 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring.
  • R 161 and R 162 which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R 151 to R 160 which are not a single bond which bonds with L 101 and do not form the substi- tuted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a sub- stituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubsti- tuted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstitute
  • Ar 101 which is not a monovalent group having the structure represented by the formula (50) is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms.
  • the position to be the single bond which bonds with L 101 in the formula (50) is not particularly limited.
  • one of R 151 to R 160 in the formula (50) is a single bond which bonds with L 101 .
  • Ar 101 is a monovalent group represented by the following formula (50-R152), (50-R 153 ), (50-R 154 ), (50-R 157 ), or (50-R 158 ).
  • the emitting layer comprises the compound represented by formula (I) as a do- pant and at least one host, wherein preferred hosts are mentioned above, and the host is more preferably at least one compound represented by formula (10), the content of the at least one compound represented by formula (I) is preferably 0.5 mass% to 70 mass%, more preferably 0.5 to 30 mass%, further preferably 1 to 30 mass%, still further preferably 1 to 20 mass%, and particularly preferably 1 to 10 mass%, further particularly preferably 1 to 5 mass%, relative to the entire mass of the emitting layer.
  • the content of the at least one host is preferably 30 mass% to 99.9 mass%, more preferably 70 to 99.5 mass%, further preferably 70 to 99 mass%, still further preferably 80 to 99 mass%, and particularly preferably 90 to 99 mass%, further particularly preferably 95 to 99 mass %, relative to the entire mass of the emitting layer.
  • An explanation will be made on the layer configuration of the organic EL device according to one aspect of the invention.
  • An organic EL device according to one aspect of the invention comprises a cathode, an anode, and one or more organic thin film layers comprising an emitting layer disposed between the cathode and the anode.
  • the organic layer comprises at least one layer composed of an organic compound.
  • the organic layer is formed by laminating a plurality of layers com- posed of an organic compound.
  • the organic layer may further comprise an inorganic compound in addition to the organic compound.
  • At least one of the organic layers is an emitting layer.
  • the organic layer may be constituted, for example, as a single emitting layer, or may comprise other layers which can be adopted in the layer structure of the organic EL device.
  • the layer that can be adopted in the layer structure of the organic EL device is not particularly limited, but examples thereof include a hole-transport- ing zone (comprising at least one hole-transporting layer and preferably in addition at least one of a hole-injecting layer, an electron-blocking layer, an exciton-blocking layer, etc.), an emitting layer, a spacing layer, and an electron-transporting zone (comprising at least one electron- transporting layer and preferably in addition at least one of an electron-injecting layer, a hole- blocking layer, etc.) provided between the cathode and the emitting layer.
  • a hole-transport- ing zone comprising at least one hole-transporting layer and preferably in addition at least one of a hole-injecting layer, an electron-blocking layer, an exciton-blocking layer, etc.
  • an emitting layer a spacing layer
  • an electron-transporting zone comprising at least one electron- transporting layer and preferably in addition at least one of an electron-injecting
  • the organic EL device may be, for example, a fluores- cent or phosphorescent monochromatic light emitting device or a fluorescent/phosphorescent hybrid white light emitting device.
  • the organic EL device is a fluorescent monochro- matic light emitting device, more preferably a blue fluorescent monochromatic light emitting de- vice or a fluorescent/phosphorescent hybrid white light emitting device.
  • Blue fluorescence means a fluorescence at 400 to 500 nm (peak maximum), preferably at 430 nm to 490 nm (peak maximum). Further, it may be a simple type device having a single emitting unit or a tandem type device having a plurality of emitting units.
  • the “emitting unit” in the specification is the smallest unit that comprises organic layers, in which at least one of the organic layers is an emitting layer and light is emitted by recombination of injected holes and electrons.
  • the "emitting layer” described in the present specification is an organic layer having an emitting function.
  • the emitting layer is, for example, a phosphorescent emitting layer, a fluo- rescent emitting layer or the like, preferably a fluorescent emitting layer, more preferably a blue fluorescent emitting layer, and may be a single layer or a stack of a plurality of layers.
  • the emitting unit may be a stacked type unit having a plurality of phosphorescent emitting lay- ers or fluorescent emitting layers.
  • a spacing layer for preventing exci- tons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer may be provided between the respective light-emitting layers.
  • a device configuration such as anode/emitting unit/cath- ode can be given. Examples for representative layer structures of the emitting unit are shown below. The layers in parentheses are provided arbitrarily.
  • the organic EL device when the organic EL device has a hole-injecting layer and a hole-transporting layer, it is preferred that a hole-injecting layer be provided between the hole-transporting layer and the anode. Further, when the organic EL device has an electron-injecting layer and an elec- tron-transporting layer, it is preferred that an electron-injecting layer be provided between the electron-transporting layer and the cathode. Further, each of the hole-injecting layer, the hole- transporting layer, the electron-transporting layer and the electron-injecting layer may be formed of a single layer or be formed of a plurality of layers.
  • the plurality of phosphorescent emitting layer, and the plurality of the phosphorescent emitting layer and the fluorescent emitting layer may be emitting layers that emit mutually different col- ors.
  • the emitting unit (f) may include a hole-transporting layer/first phosphorescent layer (red light emission)/ second phosphorescent emitting layer (green light emission)/spacing layer/fluorescent emitting layer (blue light emission)/electron-transporting layer.
  • An electron-blocking layer may be provided between each light emitting layer and the hole- transporting layer or the spacing layer. Further, a hole-blocking layer may be provided between each emitting layer and the electron-transporting layer.
  • the electron-blocking layer or the hole-blocking layer By providing the electron-blocking layer or the hole-blocking layer, it is possible to confine electrons or holes in the emitting layer, thereby to improve the recombination probability of carriers in the emitting layer, and to improve light emitting efficiency.
  • a de- vice configuration such as anode/first emitting unit/intermediate layer/second emitting unit/cath- ode can be given.
  • the first emitting unit and the second emitting unit are independently selected from the above- mentioned emitting units, for example.
  • the intermediate layer is also generally referred to as an intermediate electrode, an intermedi- ate conductive layer, a charge generating layer, an electron withdrawing layer, a connecting layer, a connector layer, or an intermediate insulating layer.
  • the intermediate layer is a layer that supplies electrons to the first emitting unit and holes to the second emitting unit, and can be formed from known materials.
  • FIG.1 shows a schematic configuration of one example of the organic EL device of the inven- tion.
  • the organic EL device 1 comprises a substrate 2, an anode 3, a cathode 4 and an emitting unit 10 provided between the anode 3 and the cathode 4.
  • the emitting unit 10 comprises an emitting layer 5 preferably comprising a host material and a dopant.
  • a hole injecting and trans- porting layer 6 or the like may be provided between the emitting layer 5 and the anode 3 and an electron injecting layer 8 and an electron transporting layer 7 or the like (electron injecting and transporting unit 11) may be provided between the emitting layer 5 and the cathode 4.
  • An elec- tron-barrier layer may be provided on the anode 3 side of the emitting layer 5 and a hole-barrier layer may be provided on the cathode 4 side of the emitting layer 5. Due to such configuration, electrons or holes can be confined in the emitting layer 5, whereby possibility of generation of excitons in the emitting layer 5 can be improved.
  • an explanation will be made on function, materials, etc.
  • the substrate is used as a support of the organic EL device.
  • the substrate preferably has a light transmittance of 50% or more in the visible light region with a wavelength of 400 to 700 nm, and a smooth substrate is preferable.
  • Examples of the material of the substrate include soda- lime glass, aluminosilicate glass, quartz glass, plastic and the like.
  • a flexible substrate can be used as a substrate.
  • the flexible substrate means a substrate that can be bent (flexible), and examples thereof include a plastic substrate and the like.
  • the material for forming the plastic substrate include polycarbonate, polyallylate, polyether sulfone, polypropyl- ene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate and the like.
  • an inorganic vapor deposited film can be used.
  • the anode for example, it is preferable to use a metal, an alloy, a conductive compound, a mixture thereof or the like and having a high work function (specifically, 4.0 eV or more).
  • Spe- cific examples of the material of the anode include indium oxide-tin oxide (ITO: Indium Tin Ox- ide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide or zinc oxide, graphene and the like.
  • ITO Indium Tin Ox- ide
  • the anode is normally formed by depositing these materials on the substrate by a sputtering method.
  • indium oxide-zinc oxide can be formed by a sputtering method by using a target in which 1 to 10 mass% zinc oxide is added relative to indium oxide.
  • indium ox- ide containing tungsten oxide or zinc oxide can be formed by a sputtering method by using a target in which 0.5 to 5 mass% of tungsten oxide or 0.1 to 1 mass% of zinc oxide is added rela- tive to indium oxide.
  • a vacuum deposition method, a coating method, an inkjet method, a spin coating method or the like can be given. When silver paste or the like is used, it is possible to use a coating method, an inkjet method or the like.
  • the hole-injecting layer formed in contact with the anode is formed by using a material that al- lows easy hole injection regardless of the work function of the anode. For this reason, in the an- ode, it is possible to use a common electrode material, e.g. a metal, an alloy, a conductive com- pound and a mixture thereof. Specifically, a material having a small work function such as alka- line metals such as lithium and cesium; alkaline earth metals such as calcium and strontium; al- loys containing these metals (for example, magnesium-silver and aluminum-lithium); rare earth metals such as europium and ytterbium; and an alloy containing rare earth metals.
  • a common electrode material e.g. a metal, an alloy, a conductive com- pound and a mixture thereof.
  • a material having a small work function such as alka- line metals such as lithium and cesium; alkaline earth metals such as calcium and
  • the hole-transporting layer is an organic layer that is formed between the emitting layer and the anode, and has a function of transporting holes from the anode to the emitting layer. If the hole- transporting layer is composed of plural layers, an organic layer that is nearer to the anode may often be defined as the hole-injecting layer.
  • the hole-injecting layer has a function of injecting holes efficiently to the organic layer unit from the anode. Said hole injection layer is generally used for stabilizing hole injection from anode to hole transporting layer which is generally con- sist of organic materials. Organic material having good contact with anode or organic material with p-type doping is preferably used for the hole injection layer.
  • p-doping usually consists of one or more p-dopant materials and one or more matrix materials.
  • Matrix materials preferably have shallower HOMO level and p-dopant preferably have deeper LUMO level to enhance the carrier density of the layer.
  • Specific examples for p-dopants are the below mentioned acceptor materials.
  • Suitable matrix materials are the hole transport materials mentioned below, preferably aromatic or heterocyclic amine compounds. Acceptor materials, or fused aromatic hydrocarbon materials or fused heterocycles which have high planarity, are preferably used as p-dopant materials for the hole injection layer.
  • acceptor materials are, quinone compounds with one or more electron withdrawing groups, such as F 4 TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), and 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane; hexa-azatri- phenylene compounds with one or more electron withdrawing groups, such as hexa-azatri- phenylene-hexanitrile; aromatic hydrocarbon compounds with one or more electron withdrawing groups; and aryl boron compounds with one or more electron withdrawing groups.
  • quinone compounds with one or more electron withdrawing groups such as F 4 TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), and 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)
  • Preferred p- dopants are quinone compounds with one or more electron withdrawing groups, such as F4TCNQ, 1,2,3-Tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane.
  • the ratio of the p-type dopant is preferably less than 20% of molar ratio, more preferably less than 10%, such as 1%, 3%, or 5%, related to the matrix material.
  • the hole transporting layer is generally used for injecting and transporting holes efficiently, and aromatic or heterocyclic amine compounds are preferably used.
  • Ar 1’ to Ar 3’ each independently represents substituted or unsubstituted aryl group having 5 to 50 carbon atoms or substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, preferably phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, triphenylenyl group, fluorenyl group, spirobifluorenyl group, indenofluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazole substituted aryl group, diben- zofuran substituted aryl group or dibenzothiophene substituted aryl group; two or more substitu- ents selected among Ar 1’ to Ar 3’ may be bonded to each other to form a ring structure, such as a carbazole ring structure
  • At least one of Ar 1’ to Ar 3’ have additional one aryl or heterocyclic amine substituent, more preferably Ar 1’ has an additional aryl amino substituent, at the case of that it is preferable that Ar 1’ represents substituted or unsubstituted biphenylene group, substituted or unsubstituted fluorenylene group.
  • Specific examples for the hole transport material are .
  • a second hole transporting layer is preferably inserted between the first hole transporting layer and the emitting layer to enhance device performance by blocking excess electrons or excitons. Specific examples for second hole transporting layer are the same as for the first hole transport- ing layer.
  • second hole transporting layer has higher triplet energy to block tri- plet excitons, especially for phosphorescent devices, such as bicarbazole compounds, biphenyl- amine compounds, triphenylenyl amine compounds, fluorenyl amine compounds, carbazole substituted arylamine compounds, dibenzofuran substituted arylamine compounds, and diben- zothiophene substituted arylamine compounds.
  • the emitting layer is a layer containing a substance having a high emitting property (emitter ma- terial or dopant material). As the dopant material, various materials can be used.
  • a fluorescent emitting compound fluorescent dopant
  • a phosphorescent emitting compound phosphorescent dopant
  • a fluorescent emitting compound is a com- pound capable of emitting light from the singlet excited state, and an emitting layer containing a fluorescent emitting compound is called a fluorescent emitting layer.
  • a phosphorescent emitting compound is a compound capable of emitting light from the triplet excited state, and an emitting layer containing a phosphorescent emitting compound is called a phosphorescent emit- ting layer.
  • the emitting layer in the organic EL device of the present application comprises a compound of formula (I) as a dopant material.
  • the emitting layer preferably comprises at least one dopant material and at least one host ma- terial that allows it to emit light efficiently.
  • a dopant material is called a guest material, an emitter or an emitting material.
  • a host material is called a matrix material.
  • a single emitting layer may comprise plural dopant materials and plural host materials. Further, plural emitting layers may be present.
  • a host material combined with the fluorescent dopant is referred to as a “fluorescent host” and a host material combined with the phosphorescent dopant is re- ferred to as the “phosphorescent host”. Note that the fluorescent host and the phosphorescent host are not classified only by the molecular structure.
  • the phosphorescent host is a material for forming a phosphorescent emitting layer containing a phosphorescent dopant, but does not mean that it cannot be used as a material for forming a fluorescent emitting layer.
  • the emitting layer comprises the compound represented by formula (I) according to the present invention (hereinafter, these compounds may be referred to as the “compound (I)”). More preferably, it is contained as a dopant material. Further, it is pre- ferred that the compound (I) be contained in the emitting layer as a fluorescent dopant. Even further, it is preferred that the compound (I) be contained in the emitting layer as a blue fluores- cent dopant.
  • the content of the compound (I) as the dopant material in the emitting layer is preferably 0.5 to 70 mass%, more preferably 0.8 to 30 mass%, further preferably 1 to 30 mass%, still further preferably 1 to 20 mass%, and particularly preferably 1 to 10 mass%, further particularly preferably 1 to 5 mass%, even further particularly preferably 2 to 4 mass%, related to the mass of the emitting layer.
  • fluorescent dopant As a fluorescent dopant other than the compound (I), a fused polycyclic aromatic compound, a styrylamine compound, a fused ring amine compound, a boron-containing compound, a pyrrole compound, an indole compound, a carbazole compound can be given, for example. Among these, a fused ring amine compound, a boron-containing compound, carbazole compound is preferable.
  • a diaminopyrene compound As the fused ring amine compound, a diaminopyrene compound, a diaminochrysene com- pound, a diaminoanthracene compound, a diaminofluorene compound, a diaminofluorene com- pound with which one or more benzofuro skeletons are fused, or the like can be given.
  • boron-containing compound a pyrromethene compound, a triphenylborane compound or the like can be given.
  • pyrene compounds As a blue fluorescent dopant, pyrene compounds, styrylamine compounds, chrysene com- pounds, fluoranthene compounds, fluorene compounds, diamine compounds, triarylamine com- pounds and the like can be given, for example.
  • N,N'-bis[4-(9H-carbazol-9-yl)phe- nyl]-N,N’-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4’-(10-phe- nyl-9-anthryl)triphenyamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-car- apelole-3-yl)triphenylamine (abbreviation: PCBAPA) or the like can be given.
  • YGA2S 4-(9H-carbazol-9-yl)-4’-(10-phe- nyl-9-anthryl)triphenyamine
  • PCBAPA 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-car- apelole-3-yl)triphenylamine
  • an aromatic amine compound or the like can be given, for exam- ple.
  • N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine abbreviation: 2PCAPA
  • N-[9,10-bis(1,1’-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine abbreviation: 2PCABPhA
  • N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (ab- breviation: 2DPAPA)
  • N-[9,10-bis(1,1’-biphenyl-2-yl)-2-anthryl]-N,N’,N’-triphenyl-1,4-phenylene- diamine abbreviation: 2DPABPhA
  • a tetracene compound, a diamine compound or the like As a red fluorescent dopant, a tetracene compound, a diamine compound or the like can be given. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p- mPhTD), 7,14-diphenyl-N,N,N’,N’-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10- diamine (abbreviation: p-mPhAFD) or the like can be given.
  • p-mPhTD N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine
  • p-mPhAFD 7,14-diphenyl-N,N,N’,N’-tetraki
  • a phosphorescent dopant As a phosphorescent dopant, a phosphorescent emitting heavy metal complex and a phospho- rescent emitting rare earth metal complex can be given.
  • the heavy metal complex an iridium complex, an osmium complex, a platinum complex or the like can be given.
  • the heavy metal complex is for example an ortho-metalated complex of a metal selected from iridium, osmium and platinum.
  • rare earth metal complexes include terbium complexes, europium complexes and the like.
  • tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac) 3 (Phen)
  • tris(1,3-diphenyl-1,3-propandionate)(monophenanthroline)europium(III) (ab- breviation: Eu(DBM)3(Phen))
  • tris[1-(2-thenoyl)-3,3,3-trifluoroacetonate](monophenanthroli- ne)europium(III) (abbreviation: Eu(TTA)3(Phen)) or the like
  • Tb(acac) 3 (Phen) tris(1,3-diphenyl-1,3-propandionate)(monophenanthroline)europium(III)
  • Eu(TTA)3(Phen) tris[1-(2-thenoyl)-3,3,3-trifluoroacetonate](mon
  • rare earth metal complexes are preferable as phosphorescent dopants since rare earth metal ions emit light due to electronic transition between different multiplicity.
  • a blue phosphorescent dopant an iridium complex, an osmium complex, a platinum com- plex, or the like can be given, for example.
  • bis[2-(4’,6’-difluorophenyl)pyridinate- N,C2’]iridium(III) tetrakis(1-pyrazolyl)borate abbreviation: FIr6
  • bis[2-(4',6'-difluorophenyl) pyri- dinato-N,C2']iridium(III) picolinate abbreviation: Ir(CF3ppy)2(pic)
  • bis[2-(4’,6’-difluorophenyl)pyr- idinato-N,C2’]iridium(III) acetylacetonate abbreviation: FIracac
  • an iridium complex or the like can be given, for example.
  • tris(2-phenylpyridinato-N,C2’) iridium(III) (abbreviation: Ir(ppy) 3 ), bis(1,2-diphenyl- 1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quino- linato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)) or the like can be given.
  • an iridium complex, a platinum complex, a terbium complex, a europium complex or the like can be given.
  • iridium(III) acetylacetonate abbreviation: Ir(btp)2(acac)
  • Ir(piq) 2 (acac) bis(1-phenylisoquinolinato- N,C2’)iridium(III) acetylacetonate
  • Ir(piq) 2 (acac) acetylacetonato)bis[2,3-bis(4- fluorophenyl)quinoxalinato]iridium(III)
  • Ir(Fdpq)2(acac) 2,3,7,8,12,13,17,18-octae- thyl-21H,23H-p
  • the emitting layer preferably comprises at least one compound (I) as a do- pant.
  • host material metal complexes such as aluminum complexes, beryllium complexes and zinc complexes; heterocyclic compounds such as indole compounds, pyridine compounds, pyrimi- dine compounds, triazine compounds, quinoline compounds, isoquinoline compounds, quinazo- line compounds, dibenzofuran compounds, dibenzothiophene compounds, oxadiazole com- pounds, benzimidazole compounds, phenanthroline compounds; fused polyaromatic hydrocar- bon (PAH) compounds such as a naphthalene compound, a triphenylene compound, a carba- zole compound, an anthracene compound, a phenanthrene compound, a pyrene compound, a chrysene compound, a naphthacene compound, a fluoranthene compound; and aromatic amine compound such as a naphthalen
  • Plural types of host materials can be used in combination.
  • a fluorescent host a compound having a higher singlet energy level than a fluorescent do- pant is preferable.
  • a heterocyclic compound, a fused aromatic compound or the like can be given.
  • a fused aromatic compound an anthracene compound, a pyrene com- pound, a chrysene compound, a naphthacene compound or the like are preferable.
  • An anthra- cene compound is preferentially used as blue fluorescent host.
  • preferred host mate- rials are substituted or unsubstituted polyaromatic hydrocarbon (PAH) compounds, substituted or unsubstituted polyheteroaromatic compounds, substituted or unsubstituted anthracene com- pounds, or substituted or unsubstituted pyrene compounds, preferably substituted or unsubsti- tuted anthracene compounds or substituted or unsubstituted pyrene compounds, more prefera- bly substituted or unsubstituted anthracene compounds, most preferably anthracene com- pounds represented by formula (10), as mentioned above.
  • PAH polyaromatic hydrocarbon
  • a compound having a higher triplet energy level as compared with a phosphorescent dopant is preferable.
  • a metal complex, a heterocyclic compound, a fused aromatic compound or the like can be given.
  • an indole compound, a car- apelole compound, a pyridine compound, a pyrimidine compound, a triazine compound, a quino- lone compound, an isoquinoline compound, a quinazoline compound, a dibenzofuran com- pound, a dibenzothiophene compound, a naphthalene compound, a triphenylene compound, a phenanthrene compound, a fluoranthene compound or the like can be given.
  • the electron-transporting layer is an organic layer that is formed between the emitting layer and the cathode and has a function of transporting electrons from the cathode to the emitting layer.
  • an organic layer or an inorganic layer that is nearer to the cathode is often defined as the electron injecting layer (see for exam- ple layer 8 in FIG.1, wherein an electron injecting layer 8 and an electron transporting layer 7 form an electron injecting and transporting unit 11).
  • the electron injecting layer has a function of injecting electrons from the cathode efficiently to the organic layer unit.
  • Preferred electron injec- tion materials are alkali metal, alkali metal compounds, alkali metal complexes, the alkaline earth metal complexes and the rare earth metal complexes.
  • the electron-transporting layer further com- prises one or more layer(s) like a second electron-transporting layer, an electron injection layer to enhance efficiency and lifetime of the device, a hole blocking layer, an exciton blocking layer or a triplet blocking layer.
  • an electron-donating dopant be contained in the interfacial region between the cathode and the emitting unit. Due to such a configuration, the organic EL device can have an increased luminance or a long life.
  • the electron-donat- ing dopant means one having a metal with a work function of 3.8 eV or less.
  • a metal with a work function of 3.8 eV or less at least one selected from an alkali metal, an alkali metal complex, an alkali metal compound, an alkaline earth metal, an alkaline earth metal complex, an alkaline earth metal compound, a rare earth metal, a rare earth metal complex and a rare earth metal compound or the like can be mentioned.
  • the alkali metal Li (work function: 2.9 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV) and the like can be given.
  • One having a work function of 2.9 eV or less is particularly preferable. Among them, K, Rb and Cs are preferable. Rb or Cs is further preferable. Cs is most preferable.
  • As the alkaline earth metal Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV) and the like can be given.
  • One having a work function of 2.9 eV or less is particularly prefer- able.
  • As the rare-earth metal Sc, Y, Ce, Tb, Yb and the like can be given.
  • One having a work function of 2.9 eV or less is particularly preferable.
  • alkali metal compound examples include an alkali oxide such as Li2O, Cs2O or K2O, and an alkali halide such as LiF, NaF, CsF and KF. Among them, LiF, Li 2 O and NaF are preferable.
  • alkaline earth metal compound examples include BaO, SrO, CaO, and mixtures thereof such as BaxSr1-xO (0 ⁇ x ⁇ 1) and BaxCa1-xO (0 ⁇ x ⁇ 1). Among them, BaO, SrO and CaO are prefer- able.
  • the rare earth metal compound examples include YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3 and TbF 3 .
  • the alkali metal complexes, the alkaline earth metal complexes and the rare earth metal com- plexes are not particularly limited as long as they contain, as a metal ion, at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions.
  • ligand examples include, but are not limited to, quinolinol, benzoquinolinol, acridinol, phenanthridi- nol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthi- adiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxy- fluborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, and azomethines.
  • the electron-do- nating dopant be formed in a shape of a layer or an island in the interfacial region.
  • a preferred method for the formation is a method in which an organic compound (a light emitting material or an electron-injecting material) for forming the interfacial region is deposited simultaneously with deposition of the electron-donating dopant by a resistant heating deposition method, thereby dispersing the electron-donating dopant in the organic compound.
  • the electron-donating dopant is formed into the shape of a layer
  • the light-emit- ting material or electron-injecting material which serves as an organic layer in the interface is formed into the shape of a layer.
  • a reductive dopant is solely deposited by the re- sistant heating deposition method to form a layer preferably having a thickness of from 0.1 nm to 15 nm.
  • the electron-donating dopant is formed into the shape of an island
  • the emitting material or the electron-injecting material which serves as an organic layer in the interface is formed into the shape of an island.
  • the electron-donating dopant is solely deposited by the resistant heating deposition method to form an island preferably having a thickness of from 0.05 nm to 1 nm.
  • an aromatic heterocyclic compound having one or more hetero atoms in the molecule may preferably be used.
  • a nitro- gen-containing heterocyclic compound is preferable.
  • the electron-transporting layer comprises a nitrogen-containing heterocyclic metal chelate.
  • the electron-transporting layer compri- ses a substituted or unsubstituted nitrogen containing heterocyclic compound.
  • 6-membered azine compounds such as pyridine compounds, pyrimidine compounds, triazine compounds, pyrazine compounds, preferably pyrimidine compounds or triazine compounds; 6-membered fused azine compounds, such as quinolone compounds, isoquinoline compounds, quinoxaline compounds, quinazoline compounds, phenanthroline compounds, benzoquinoline compounds, benzoisoquinoline compounds, dibenzoquinoxaline compounds, preferably quinolone com- pounds, isoquinoline compounds, phenanthroline compounds; 5-membered heterocyclic com- pounds, such as imidazole compounds, oxazole compounds, oxadiazole compounds, triazole compounds, thiazole compounds, thiadiazole compounds; fused imidazole compounds, such as benzimidazole compounds, imidazopyridine compounds, naphthoimidazole compounds, benzi-
  • Arp1 to Arp3 are the substituents of phosphor atom and each independently represent substituted or unsubstituted above mentioned aryl group or substituted or unsubstituted above mentioned heterocyclic group.
  • the electron-transporting layer comprises aromatic hydrocarbon compounds.
  • aromatic hydrocarbon com- pounds for the electron-transporting layer are, oligo-phenylene compounds, naphthalene com- pounds, fluorene compounds, fluoranthenyl group, anthracene compounds, phenanthrene com- pounds, pyrene compounds, triphenylene compounds, benzanthracene compounds, chrysene compounds, benzphenanthrene compounds, naphthacene compounds, and benzochrysene compounds, preferably anthracene compounds, pyrene compounds and fluoranthene com- pounds.
  • a metal, an alloy, an electrically conductive compound, and a mixture thereof, each having a small work function (specifically, a work function of 3.8 eV or less) are preferably used.
  • a material for the cathode include an alkali metal such as lithium and cesium; an alkaline earth metal such as magnesium, calcium, and strontium; aluminum, an alloy containing these metals (for example, magnesium-silver, aluminum-lithium); a rare earth metal such as europium and ytterbium; and an alloy containing a rare earth metal.
  • the cathode is usually formed by a vacuum vapor deposition or a sputtering method.
  • a coating method, an inkjet method, or the like can be employed.
  • various electrically conductive materials such as silver, ITO, graphene, indium oxide- tin oxide containing silicon or silicon oxide, selected independently from the work function, can be used to form a cathode.
  • These electrically conductive materials are made into films using a sputtering method, an inkjet method, a spin coating method, or the like.
  • Insulating layer In the organic EL device, pixel defects based on leakage or a short circuit are easily generated since an electric field is applied to a thin film. In order to prevent this, it is preferred to insert an insulating thin layer between a pair of electrodes.
  • Examples of materials used in the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, tita- nium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ru- thenium oxide, and vanadium oxide.
  • a mixture thereof may be used in the insulating layer, and a laminate of a plurality of layers that include these materials can be also used for the insulating layer.
  • a spacing layer is a layer provided between a fluorescent emitting layer and a phosphorescent emitting layer when a fluorescent emitting layer and a phosphorescent emitting layer are stacked in order to prevent diffusion of excitons generated in the phosphorescent emitting layer to the fluorescent emitting layer or in order to adjust the carrier balance. Further, the spacing layer can be provided between the plural phosphorescent emitting layers. Since the spacing layer is provided between the emitting layers, the material used for the spac- ing layer is preferably a material having both electron-transporting capability and hole-transport- ing capability.
  • the spacing layer In order to prevent diffusion of the triplet energy in adjacent phosphorescent emit- ting layers, it is preferred that the spacing layer have a triplet energy of 2.6 eV or more.
  • the same materials as those used in the above-mentioned hole-transporting layer can be given.
  • An electron-blocking layer, a hole-blocking layer, an exciton (triplet)-blocking layer, and the like may be provided in adjacent to the emitting layer.
  • the electron-blocking layer has a function of preventing leakage of electrons from the emitting layer to the hole-transporting layer.
  • the hole-blocking layer has a function of preventing leakage of holes from the emitting layer to the electron-transporting layer.
  • a material having a deep HOMO level is preferably used.
  • the exciton-blocking layer has a function of preventing diffusion of excitons generated in the emitting layer to the ad- jacent layers and confining the excitons within the emitting layer.
  • a material having a high triplet level is preferably used.
  • a known film-forming method such as a dry film-forming method, a wet film-forming method or the like can be used.
  • Specific examples of the dry film- forming method include a vacuum deposition method, a sputtering method, a plasma method, an ion plating method, and the like.
  • Specific examples of the wet film-forming method include various coating methods such as a spin coating method, a dipping method, a flow coating method, an inkjet method, and the like.
  • the film thickness of each layer of the organic EL device of the invention is not particularly lim- ited unless otherwise specified. If the film thickness is too small, defects such as pinholes are likely to occur to make it difficult to obtain a sufficient luminance.
  • the film thickness is preferably 0.1 nm to 10 ⁇ m, and more preferably 5 nm to 0.2 ⁇ m.
  • the present invention further relates to an electronic equipment (electronic apparatus) compris- ing the organic electroluminescence device according to the present application.
  • the electronic apparatus include display parts such as an organic EL panel module; display de- vices of television sets, mobile phones, smart phones, and personal computer, and the like; and emitting devices of a lighting device and a vehicle lighting device.
  • the reaction mixture was filtered and the solid dissolved in 400 ml of dichloromethane.
  • the solution was treated with 200 ml of water and 200 ml of saturated aque- ous sodium bicarbonate solution, followed by stirring during 5 minutes.
  • the organic layer was washed with 300 ml of water and 200 ml of saturated aqueous sodium chloride solution.
  • the or- ganic layer was dried over magnesium sulfate and concentrated under vacuum.
  • the product was heated in 500 ml of methanol until a clear solution formed.
  • the solution was cooled down to room temperature and stirred until a suspen- sion formed.
  • the suspension was filtered to give 67.0 g of a white solid.
  • the suspension was degassed using 3 freeze-pump-thaw cycles, and 777 mg (0.85 mmol) of tris(dibenzyli- deneacetone)dipalladium(0) and 982 mg (1.70 mmol) of Xantphos were added to the reaction mixture. After two additional freeze-pump-thaw cycles, the reaction mixture was heated to 90 °C for 19 hours. The reaction was cooled to room temperature and diluted with toluene. The or- ganic layer was washed with water and dried over magnesium sulfate, filtered, and the solution was concentrated.
  • the brown suspension was three times evac- uated and backfilled with argon and heated at 95 °C during 9 hours.
  • the reaction mixture was cooled down to room temperature, then diluted with 50 ml of toluene and filtered through a 4 cm layer of silica gel.
  • the silica gel layer was rinsed with 100 ml of toluene and the collected elu- ents concentrated under vacuum.
  • the solid was stirred in 100 ml of ethanol during 3 hours.
  • the suspension was filtered and the solid washed with 50 ml of ethanol to give 8.9 g (91% yield) of Intermediate 2-3 as a white solid.
  • the brown suspension was three times evacuated and backfilled with argon and heated at 77 °C during 23 hours.
  • the reaction mixture was cooled down to room temperature and filtered through a 3 cm layer of silica gel, followed by rinsing the silica gel layer with 50 ml of toluene.
  • the collected eluents were concentrated under vacuum and the product was further purified by MPLC with the CombiFlash Companion (silica gel, heptane/0-6% gradient of ethyl acetate) to give 2.5 g (70% yield) of Intermediate 2-4 as a white solid.
  • the brown suspension was three times evacuated and backfilled with argon and heated at 106 °C during 3 hours.22 mg of tris(dibenzylideneacetone)dipalladium(0) and 28 mg (0.19 mmol) of tri-tert-butylphosphonium tetrafluoroborate were added and heating was contin- ued at 106 °C during 2 hours.
  • the reaction mixture was cooled down to room temperature and filtered through a 3 cm layer of silica gel, followed by rinsing the silica gel layer with 50 ml of tol- uene. The collected eluents were concentrated under vacuum and the product dissolved in 30 ml of dichloromethane and 70 ml of ethanol.
  • the brown suspension was warmed up to room tem- perature during 15 minutes.1.29 ml (7.40 mmol) of N,N-diisopropylethylamine were slowly added and the reaction mixture heated up to 162 °C during 4 hours.
  • the reaction mixture was cooled down to room temperature followed by the addition of 150 ml of ethanol.
  • the solution was stirred during one hour.
  • the resulting suspension was filtered and the solid washed with ethanol and heptane.
  • the product was further purified by MPLC with the CombiFlash Compan- ion (silica gel, heptane/0-40% gradient of toluene).
  • the suspension was three times evacuated and backfilled with argon, and the green suspension was heated to 90 °C for 22 hours.1.40 g (14.1 mmol) of copper(I) chloride, and 0.88 ml (8.5 mmol) of pentane-2,4- dione were then added once again. The reaction was stirred at 90 °C for a further 19 hours. 0.560 g (5.66 mmol) of copper(I) chloride, 0.35 ml (3.4 mmol) of pentane-2,4-dione, and 13.82 g (42.4 mmol) of cesium carbonate were then added once again, and the reaction stirred at 90 °C for a further 19h.
  • reaction was cooled to 0 °C, and 1.92 ml (10.97 mmol) of N,N-diisopropylethylamine were slowly added and the reaction mixture heated up to 162 °C during 19 hours.
  • the reaction mixture was cooled down to room tempera- ture followed by the addition of 10 ml of saturated aqueous sodium acetate solution.
  • the reac- tion mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate.
  • the green suspension was heated to 100 °C for 20 hours.0.72 g (1.91 mmol) of 1,2-dibromo-3-iodo-5-methylbenzene, 1.04 g (3.18 mmol) of cesium carbonate, 0.076 g (0.76 mmol) of copper(I) chloride, and 0.13 ml (1.27 mmol) of pentane-2,4-dione were then added once again.
  • the reaction was poured onto 12 mL water and 12 ml toluene, and the layers were separated. The aqueous layer was further extracted with 5 ml toluene. The combined organic layers were dried with sodium sulfate, filtered and evapo- rated in vacuo. The resulting solid was dissolved in 5 ml tert-butylbenzene and cooled to 0 °C. 1.25 ml (1.25 mmol) of tribromoborane (1 M in hexanes) was added dropwise, followed by 0.26 ml (1.5 mmol) of N-ethyl-N-isopropylpropan-2-amine.
  • the resulting brown suspension was heated at 140 °C for 23 h.
  • the reaction was poured onto 15 ml water and 10 ml toluene, and the layers were separated.
  • the aqueous layer was further extracted with 7 ml toluene.
  • the combined organic layers were washed with 12 ml brine, dried with sodium sulfate, filtered and evaporated in vacuo.
  • the residue was purified by MPLC with the CombiFlash Companion (silica gel, heptane/30-45% gradient of toluene), then purified again on silica gel reverse phase col- umn (methanol/20-30% gradient of tetrahydrofuran).
  • the reaction mix- ture was cooled down to room temperature and filtered through a 3 cm layer of silica gel, fol- lowed by rinsing the silica gel layer with 50 ml of toluene.
  • the collected eluents were concen- trated under vacuum and the product was further purified by MPLC with the CombiFlash Com- panion (silica gel, heptane/0-30% gradient of toluene).
  • the product was dissolved in 50 ml of dichloromethane and diluted with 100 ml of Ethanol. The solution was concentrated under vac- uum until a suspension formed.
  • the suspension was degassed using three freeze-pump-thaw cycles, and 576 mg (0.63 mmol) of tris(dibenzyli- deneacetone)dipalladium(0) and 1.46 g (2.52 mmol) of Xantphos were added to the reaction mixture. After two additional freeze-pump-thaw cycles, the reaction mixture was heated to a temperature of 74 °C for 15 minutes. The reaction mixture was cooled down to room tempera- ture and filtered through a 4 cm layer of silica gel. The silica gel layer was rinsed with 100 ml of toluene and the collected eluents concentrated under vacuum.
  • reaction mixture was heated to 87 °C for three hours.
  • the reac- tion mixture was cooled down to room temperature and filtered through a 4 cm layer of silica gel.
  • the silica gel layer was rinsed with 100 ml of toluene and the collected eluents concen- trated under vacuum.
  • the solid was dissolved in 50 ml of dichloromethane and 200 ml of etha- nol. The solution was concentrated under vacuum until a suspension formed.
  • the brown suspension was three times evacuated and backfilled with argon and heated up to 76 °C during two hours.4.6 mg (0.005 mmol) of tris(dibenzylideneacetone)dipalla- dium(0) and 5.8 mg (0.02 mmol) of tri-tert-butyl-phosphonium tetrafluoroborate were added, and heating continued up to 96 °C during 42 hours.4.6 mg (0.005 mmol) of tris(dibenzylideneace- tone)dipalladium(0) and 5.8 mg (0.02 mmol) of tri-tert-butyl-phosphonium tetrafluoroborate were added, and heating continued up to 108 °C during 27 hours.
  • the orange-red suspension was stirred up to a tem- perature of 68 °C during 40 minutes, then stirred at a temperature of 125 °C during 45 minutes, and then cooled down to room temperature.0.35 ml (2.0 mmol) of N,N-diisopropylethylamine were slowly added and the reaction mixture stirred at room temperature during 30 minutes.100 ml of ethanol were added. The yellow solution was stirred during one hour until a yellow sus- pension formed. The suspension was filtered and the solid washed with 30 ml of ethanol. The solid was dissolved in 30 ml of dichloromethane and filtered through a 4 cm layer of silica gel.
  • the brown suspension was three times evacuated and backfilled with argon and heated at 91 °C during 15 minutes.
  • the re- action mixture was cooled down to room temperature and filtered through a 4 cm layer of silica gel.
  • the silica gel layer was rinsed with 300 ml of toluene and the combined eluents concen- trated under vacuum.
  • the product was further purified by MPLC with the CombiFlash Compan- ion (silica gel, heptane/0-4 % gradient of ethyl acetate) to give 25.5 g (97% yield) of Intermedi- ate 8-2 as a white solid.
  • the orange suspension was stirred up to 125 °C during 4 hours, and then cooled down to room temperature.2.0 ml (11 mmol) of N,N- diisopropylethylamine were slowly added and the reaction mixture stirred at room temperature during 15 minutes. The reaction mixture was diluted with 600 ml of ethanol and stirred during one hour until a suspension formed. The suspension was filtered and the solid washed with 300 ml of ethanol. Both the solid and the filtrate were combined and concentrated under vacuum. The product was further purified by MPLC with the CombiFlash Companion (silica gel, hep- tane/0-20% gradient of dichloromethane).
  • the organic EL devices were prepared and evaluated as follows: Application Examples A glass substrate with 130 nm-thick indium-tin-oxide (ITO) transparent electrode (manufactured by Geomatec Co., Ltd.) used as an anode was first treated with N2 plasma for 100 sec. This treatment also improved the hole injection properties of the ITO. The cleaned substrate was mounted on a substrate holder and loaded into a vacuum chamber. Thereafter, the organic ma- terials specified below were applied by vapour deposition to the ITO substrate at a rate of approx. 0.2-1 ⁇ /sec at about 10 -6 -10 -8 mbar.
  • ITO indium-tin-oxide

Abstract

La présente invention concerne des composés spécifiques, un matériau, de préférence un matériau émetteur, pour un dispositif électroluminescent organique comprenant lesdits composés spécifiques, un dispositif électroluminescent organique comprenant lesdits composés spécifiques, un équipement électronique comprenant ledit dispositif électroluminescent organique, une couche électroluminescente comprenant au moins un hôte et au moins un dopant, le dopant comprenant au moins l'un desdits composés spécifiques, et l'utilisation desdits composés dans un dispositif électroluminescent organique.
PCT/IB2023/055004 2022-05-24 2023-05-16 Composé et dispositif électroluminescent organique comprenant le composé WO2023228005A1 (fr)

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EP22175144.9 2022-05-24

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3109253A1 (fr) 2014-02-18 2016-12-28 Kwansei Gakuin Educational Foundation Composé aromatique polycyclique
EP3660024A1 (fr) 2018-11-30 2020-06-03 SFC Co., Ltd. Composés aromatiques polycycliques et dispositifs électroluminescents organiques les utilisant
WO2020217229A1 (fr) 2019-04-26 2020-10-29 Idemitsu Kosan Co., Ltd. Composé polycyclique et dispositif électroluminescent organique comprenant le composé polycyclique ou une composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3109253A1 (fr) 2014-02-18 2016-12-28 Kwansei Gakuin Educational Foundation Composé aromatique polycyclique
EP3109253B1 (fr) * 2014-02-18 2018-10-24 Kwansei Gakuin Educational Foundation Composés aromatiques polycycliques et leur utilisation comme matériau pour dispositifs organiques
EP3660024A1 (fr) 2018-11-30 2020-06-03 SFC Co., Ltd. Composés aromatiques polycycliques et dispositifs électroluminescents organiques les utilisant
WO2020217229A1 (fr) 2019-04-26 2020-10-29 Idemitsu Kosan Co., Ltd. Composé polycyclique et dispositif électroluminescent organique comprenant le composé polycyclique ou une composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ORGANIC ELECTRONICS, vol. 111, 2022, pages 106658

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