WO2024013709A1 - Compound and an organic electroluminescence device comprising the compound - Google Patents

Compound and an organic electroluminescence device comprising the compound Download PDF

Info

Publication number
WO2024013709A1
WO2024013709A1 PCT/IB2023/057218 IB2023057218W WO2024013709A1 WO 2024013709 A1 WO2024013709 A1 WO 2024013709A1 IB 2023057218 W IB2023057218 W IB 2023057218W WO 2024013709 A1 WO2024013709 A1 WO 2024013709A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
group
carbon atoms
ring
Prior art date
Application number
PCT/IB2023/057218
Other languages
French (fr)
Inventor
Michelle Groarke
Yuichi Nishimae
Chao-chen LIN
Natalia Chebotareva
Original Assignee
Idemitsu Kosan Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co., Ltd. filed Critical Idemitsu Kosan Co., Ltd.
Publication of WO2024013709A1 publication Critical patent/WO2024013709A1/en

Links

Classifications

    • 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 Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

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.
  • US 2022/0020925 A1 and US 2021/0066599 A1 each relate to a compound represented by the following formula (1), wherein one of R 12 to R 28 is bonded with L 2 .
  • R 1 to R 11 which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R 12 to R19 which do not form the substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L 2 are among others independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group in- cluding 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 car- bon atoms, a substituted or unsubstituted cycloalkyl group
  • US 2021/0062078 A1 relates to a compound represented by the following formula (1), wherein in the formula (1), at least one of R 1 to R 8 is a group represented by the following formula (2).
  • R 1 to R 11 which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R 12 and R 13 are among others independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group in- cluding 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 car- bon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a sub- stituted or unsubstituted cycloalkyl group including 3 to 50 carbon atoms that form a ring.
  • WO2021049889 A1 relates to a compound represented by the following formula (1): , wherein Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; or represented by the following formula (2), , wherein when Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group hav- ing 1 to 3 carbon atoms substituted with deuterium.
  • KR20190127529 A relates to an organic electroluminescent device comprising a boron-based organic compound of formula (1) and an anthracene-based organic compound of formula (2) in at least one organic layer included in the organic electroluminescent device.
  • US20200176679 A1 relates to a compound represented by formula 1 as an organic compound having narrow light emission spectrum and full width half the maximum and capable of sup- pressing the concentration quenching phenomenon in spite of high doping concentration.
  • Y is B
  • the compound of formula 1 includes at least one or more substituted or unsubstituted cycloalkyl groups having 1 to 20 carbon atoms.
  • US2022093874 A1 relates to a light emitting device and a polycyclic compound of formula 1 used therein wherein W1 may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and Q1 may be NR16, O, or S.
  • R1 to R16 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms, or a group represented by Formula 2 may be bonded to adjacent groups of R1 to R16.
  • WO2021223688 A1 provides an organic compound of formula I and application as well as elec- tronic components and electronic devices using the same. wherein at least one of R1, R2, R3, R4, and R5 is selected from .
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24 each independently repre- sents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substi- tuted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkyl- halide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20
  • 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. 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
  • hydrogen includes isotopes differing in the number of neutrons, i.e. protium, deuterium and tritium.
  • the substituted or unsubstituted aryl group having 6 to 30, preferably from 6 to 18 ring carbon atoms more preferably having from 6 to 13 ring carbon atoms, may be a non-condensed aro- matic group or a condensed aromatic group.
  • phenyl group examples thereof include phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, fluoranthenyl group, tri- phenylenyl group, phenanthrenyl group, fluorenyl group, indenyl group, anthracenyl, chrysenyl, spirofluorenyl group, benzo[c]phenanthrenyl group, with phenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthryl group, triphenylenyl group, fluorenyl group, indenyl group and fluoranthenyl group being preferred, phenyl group, 1-naphthyl group, 2-naphthyl group, bi- phenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, phenanthrene-9-yl group,
  • Specific examples thereof include the residues of pyrrole ring, isoindole ring, benzofuran ring, isobenzofuran ring, benzothiophene, dibenzothiophene ring, isoquinoline ring, quinoxaline ring, quinazoline, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, indole ring, quinoline ring, acridine ring, carbazole ring, furan ring, thiophene ring, benzoxazole ring, benzothiazole ring, benzimid- azole ring, dibenzofuran ring, triazine ring, oxazole
  • the substituted or unsubstituted N-heteroaryl group having 5 to 30, preferably 5 to 18 ring at- oms, more preferably having from 5 to 13 ring atoms, is described as the substituted or unsub- stituted heteroaryl group mentioned above, wherein at least one of the ring atoms is nitrogen.
  • alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substi- tuted, linear or branched examples include methyl group, ethyl group, n-propyl group, isopropyl group, n- butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, isopentyl, neopentyl, 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
  • alkyl groups having 1 to 8 carbon atoms are preferred. Suitable examples for alkyl groups having 1 to 8 carbon atoms respectively 1 to 4 carbon atoms are mentioned before. Most preferred are methyl, isopropyl and t-butyl.
  • the alkyl group is unsubstituted, i.e. it does not comprise atoms other than C and H and does not comprise unsaturated or aromatic groups.
  • the alkyl group is linear or branched.
  • alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted include those disclosed as alkyl groups wherein the hydrogen atoms thereof are partly or entirely substituted by halogen atoms.
  • Preferred alkylhalide groups are fluoroalkyl groups having 1 to 20 carbon atoms including the alkyl groups mentioned above wherein the hydrogen atoms thereof are partly or entirely substituted by fluorine atoms, for example CF 3 .
  • alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or sub- stituted include ethene group, n-propene group, isopropene group, n-butene group, isobutene 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-buten
  • 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 car- bon atoms are mentioned before.
  • alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or sub- stituted 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 atoms are mentioned before.
  • Examples of the cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cy- clooctyl group, and adamantyl group, with cyclopentyl group, and cyclohexyl group being pre- ferred.
  • Suitable examples for cyclo- alkyl groups having 3 to 6 carbon atoms are mentioned before.
  • An example for an aralkyl group having from 7 to 30 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.
  • the group OR 30 is preferably a C 1-20 alkoxy group or a C 6-18 aryloxy group.
  • Examples of an alkoxy group having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms include those having an al- kyl portion selected from the alkyl groups mentioned above.
  • Examples of an aryloxy group hav- ing 6 to 18 ring carbon atoms include those having an aryl portion selected from the aryl groups mentioned above, for example -OPh.
  • the group SR 31 is preferably a C 1-20 alkylthio group or a C 6-18 arylthio group.
  • Examples of an al- kylthio group having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, include those having an alkyl portion selected from the alkyl groups mentioned above.
  • Examples of an arylthio group having 6 to 18 ring carbon atoms include those having an aryl portion selected from the aryl groups mentioned above, for example -SPh.
  • the group SiR 34 R 35 R 36 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, including trimethylsilyl propyldimethylsilyl group, dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutyl- silyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group, and arylsilyl groups hav- ing 6 to 18 ring carbon atoms in each aryl residue, preferably triphenylsilyl group, and alkyl/ar- ylsilyl groups, preferably phenyldimethylsilyl group, diphenylmethylsilyl group, and diphenyl
  • the group NR 84 R 85 is an amino group, wherein R 84 and R 85 are described above.
  • R 84 and R 85 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; or a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted, preferably, R 84 and R 85 each independently represents an aryl group having from 6 to 18 ring carbon atoms which is unsubstituted or substituted; or a het- eroaryl group having from 5 to 18 ring atoms which is unsubstituted or substituted.
  • the optional substituents preferably each independently represents an aryl group having from 6 to 18 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 18 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; halogen, CN; SiR 34 R 35 R 36 , SR 31 or OR 30 ; 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 unsubstituted or substituted; a heteroaryl group having from 5 to 18 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; halogen, SiR 34 R 35 R 36 or CN; or two adjacent substituents together form a ring structure which is in turn unsubstituted or substi- tuted.
  • the optional substituents each independently represents an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 6 ring carbon atoms which is unsubstituted or substituted; an aryl group having 6 to 13 ring car- bon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 13 ring at- oms which is unsubstituted or substituted; halogen, SiR 34 R 35 R 36 or CN.
  • R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted or a cycloalkyl group having from 3 to 20 ring car- bon atoms which is unsubstituted or substituted.
  • the optional substituents mentioned above may be further substituted by one or more of the op- tional substituents mentioned above.
  • R 1 , R 2 , R 3 and R 4 preferably at least one of R 2 and R 3 , represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; at least one of R 5 , R 6 , R 7 and R 8 , preferably at least one of R 6 and R 7 , represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; and at least one of R 21 , R 22 and R 23 represents a
  • the compound of formula (I) therefore mandatorily comprises at least 3 substituents, i.e. at least one of R 1 , R 2 , R 3 and R 4 as a first substituent, at least one of R 5 , R 6 , R 7 and R 8 as a sec- ond substituent and at least one of R 21 , R 22 and R 23 as a third substituent.
  • the total number of substituents in the compound of formula (I) is 3, 4, 5, 6, 7 or 8, preferably 3, 4, 5, or 6, i.e. the remaining residues are hydrogen.
  • the “carbon number of a to b” in the expression of “X group having a to b carbon atoms which is substituted or unsubstituted” 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 substituents mentioned above.
  • An index of 0 in the definition in the formulae mentioned above and below means that a hydro- gen atom is present at the position defined by said index. Examples for ring structures formed by two adjacent substituents are shown below:
  • X’ represents O, S or CR 68 R 69 ;
  • R 1 , R 2 , R 3 and R 4 preferably at least one of R 2 and R 3 , represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cyclo- alkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R 1 , R 2 , R 3 and R 4 , preferably R 2 and R 3 together form an alkyl ring which is unsubstituted or substituted.
  • At least one of R 5 , R 6 , R 7 and R 8 preferably at least one of R 6 and R 7 , represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cyclo- alkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R 5 , R 6 , R 7 and R 8 , preferably R 6 and R 7 together form an alkyl ring which is unsubstituted or substituted.
  • At least one of R 21 , R 22 and R 23 represents a group HAr.
  • At least one of R 1 , R 2 , R 3 and R 4 prefera- bly at least one of R 2 and R 3 , and at least one of R 5 , R 6 , R 7 and R 8 , preferably at least one of R 6 and R 7 , each independently represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, more preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted or substituted, most preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted or substituted, further most preferably a methyl group or a t-butyl group.
  • the alkyl group mentioned above is unsubstituted. However, it is linear or branched. Suitable and preferred alkyl rings which are unsubstituted or substituted are mentioned above.
  • two adjacent residues R 1 , R 2 , R 3 and R 4 , preferably R 2 and R 3 and/or R 5 , R 6 , R 7 and R 8 , preferably R 6 and R 7 together form a ring structure (G) or (H) mentioned above.
  • R 1 , R 2 , R 3 and R 4 preferably exactly one of R 2 and R 3
  • R 5 , R 6 , R 7 and R 8 preferably exactly one of R 6 and R 7
  • R 21 , R 22 and R 23 represents a group HAr
  • the group HAr is a group of formula (II) R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is un
  • R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a het- eroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted, wherein suitable and preferred ring structures are mentioned above; one of R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 is a bonding site.
  • R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 each independently represents hydro- gen; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a or two adjacent residues together form a ring structure which is unsubstituted or substituted, wherein suitable and preferred ring structures are mentioned above; one of R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 is a bonding site.
  • R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 each independently represents hydro- gen; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; one of R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 is a bonding site.
  • R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 each independently represents hydrogen; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted and the remaining residues are H; one of R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 is a bonding site.
  • R 14 , R 17 , R 18 , R 19 , R 25 and R 26 are described above, and the dotted line is a bonding site.
  • R 21 , R 22 and R 23 preferably R 22 represents a group HAr.
  • R 21 represents a group HAr.
  • Preferred groups HAr are mentioned above.
  • R 25 , R 26 each independently represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted, more preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted, most preferably methyl; or R 25 and R 26 together form ring structure which is unsubstituted or substituted.
  • R 25 and R 26 do not form together a ring structure which is unsubstituted or More preferably, R 25 , R 26 each independently represents an alkyl group having from 1 to 20 car- bon atoms which is unsubstituted or substituted, preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted, more preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted, most preferably methyl; or an aryl group having from 6 to 30 ring carbon atoms, preferably from 6 to 18 ring carbon atoms, more preferably having from 6 to 13 ring carbon atoms which is unsubstituted or substituted, most preferably a phenyl group which is unsubstituted or substituted, further most preferably a phenyl group which is unsubstituted.
  • alkyl groups having from 1 to 20 carbon atoms which are unsubstituted or substituted, and cycloalkyl groups having from 3 to 20 ring carbon atoms which are unsubstituted or substituted, or two adjacent residues together form an alkyl ring which is unsubstituted or substituted, and as a group HAr each independently represents hydrogen; each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsub- stituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group
  • the remaining groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or NR 84 R 85 ; or two adjacent residues together form a ring structure which is unsubstituted or substituted, pref- erably an alkyl ring which is unsubstituted or substituted.
  • the remaining groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 20 , R 21 , R 22 , R 23 and R 24 each independently represents hydrogen; and at least one of R 9 , R 10 and R 11 , preferably R 10 represents hydrogen, an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; NR 84 R 85 , or R 9 and R 10 and/or R 10 and R 11 together form a ring structure which is unsubstituted or substi- tuted, preferably an alkyl ring which is
  • R 1 , R 4 , R 5 , R 8 , R 9 , R 11 , R 20 and R 24 are hydrogen; or R 1 , R 4 , R 5 , R 8 , R 9 and R 11 are hydrogen, and R 20 and R 24 each independently represents hydrogen or an aryl group having from 6 to 30 ring carbon atoms, preferably from 6 to 18 ring carbon atoms, more preferably having from 6 to 13 ring carbon atoms which is unsubstituted or substituted, most preferably phenyl which is unsub- stituted or substituted, further most preferably phenyl which is unsubstituted.
  • L, n, Y L represents a divalent aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a divalent heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; a divalent alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a divalent cycloalkyl group having from 3 to 20 ring carbon atoms which is un- substituted or substituted; preferably, L represents a divalent aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; or a divalent heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; more preferably, L represents a divalent aryl group having from 6 to 24 ring carbon atoms which is unsubstituted or substituted, preferably 6 to 18 ring atoms, or a divalent heteroary
  • n represents 0, 1, 2 or 3; preferably 0, 1 or 2; more preferably 0 or 1. In the case that n repre- sents 0, there is a direct bond between N and Y.
  • L is preferably a group of the following formula: wherein R 37 , R 38 , R 39 , R 40 and R 41 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsub- stituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substi- tuted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3
  • Y is a group HAr or R Y .
  • the group HAr is a group of formula (II) defined as described above.
  • R Y represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubsti- tuted or substituted; a N-heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or sub- stituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO 2 ; OR 30 ; SR
  • the adjacent residue at L is preferably one of the residues R 37 , R 38 , R 39 , R 40 and R 41 which is not Y.
  • R Y represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a N-heteroaryl group having from 5 to 30 ring atoms which is un- substituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubsti- tuted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or R Y forms with an adjacent residue at L, preferably one of the residues R 37 , R 38 , R 39 , R 40 and R 41 which is not Y, an alkyl ring which is unsubstituted or substituted.
  • R Y represents hydrogen, an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, more preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted or substituted, most preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted or substituted, further most preferably a methyl group or a t-butyl group; further preferably, the alkyl group mentioned above is unsubstituted, however, it is linear or branched; or R Y forms with an adjacent residue at L, preferably one of the residues R 37 , R 38 , R 39 , R 40 and R 41 which is not Y, an alkyl ring which is unsubstituted or substituted; or R Y represents an aryl group having from 6 to 30 ring carbon atoms, preferably from 6 to 18 ring carbon atoms, more preferably having from 6 to 13 ring carbon atoms which is un
  • Suitable and preferred alkyl rings which are unsubstituted or substituted are mentioned above; more preferred alkyl rings are represented by ring structure (G) or (H) mentioned above, most Preferably, one of R 37 , R 38 , R 39 , R 40 and R 41 , preferably one of R 39 and R 40 , more preferably R 39 represents R Y ; or two adjacent residues R Y and one of R 37 , R 38 , R 39 , R 40 and R 41 which is not Y, preferably R Y at the position of R 39 and R 40 together form an alkyl ring which is unsubstituted or substituted, wherein preferred alkyl rings form a ring structure (G) or (H) as mentioned above, preferably and the remaining residues of R 37 , R 38 , R 39 , R 40 and R 41 are hydrogen.
  • Y is HAr
  • the groups L may be the same or different.
  • L 1 , L 2 and L 3 are defined in the same way as L.
  • L 2 and L 3 are preferably each independently phenyl groups which are unsubstituted or substi- tuted, more preferably 1,2-phenylene, 1,3-phenylene or 1,4 phenylene groups which are are un- substituted or substituted, most preferably 1,2-phenylene, 1,3-phenylene or 1,4 phenylene groups which are are unsubstituted, and further most preferably 1,3-phenylene or 1,4 phenylene groups which are are unsubstituted.
  • groups Y–(L) n - are wherein the residues and groups R Y , R 13 and X are described above and below.
  • Preferred groups Y–(L) n - are:
  • More preferred compounds of formula (I) are the following compounds, wherein the residues, groups and indices are defined above More preferably, in the compounds of formula (Ia), (Ib), (Iaa), (Iba), (Iab) and (Ibb): R 1 , R 4 , R 5 , R 8 , R 9 , R 11 , R 20 and R 24 are hydrogen; or R 1 , R 4 , R 5 , R 8 , R 9 and R 11 are hydrogen and R 20 and R 24 each independently represents hydrogen or an aryl group having from 6 to 30 ring carbon atoms; at least one of R 2 and R 3 represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, and the remaining residue R 2 or R 3 is hydrogen; or R 2 and R 3 together form an alkyl ring which is unsubstituted or
  • the compounds represented by formula (I) can be synthesized in accordance with the reactions conducted in the examples of the present application, and by using alternative reactions or raw materials suited to an intended product, in analogy to reactions and raw materials known in the art.
  • the compounds of formula (I) are for example prepared by the following steps:
  • R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 in BQ 2 -HAr (V) is -BQ 2 ;
  • Q is an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, substituted by one or two unsubstituted alkyl groups having 1 to 8 carbon atoms, a unsubstituted alkoxy group hav- ing 1 to 8 carbon atoms, a hydroxyl group, wherein two alkyl groups Q or two alkoxy groups Q together may form a five or six membered substituted or unsubstituted ring;
  • catalyst preferred catalysts are Pd catalysts; all other residues, groups and indices are as defined before.
  • Josiphos wherein R and R’ are generally substituted or unsubstituted phenyl. It is generally possible to change the sequence of steps (i) and (ii) in the process mentioned above, i.e. to carry out the addition of BQ 2 -HAr (equivalent to step (ii)) first and to carry out the borylation of the obtained intermediate (equivalent to step (i)) subsequently.
  • Suitable reaction conditions are known by a person skilled in the art. Reaction steps for obtain- ing intermediates (III), (IV) and (V) are shown in the examples of the present application. Details of all reaction steps and process conditions are mentioned in the examples of the pre- sent application.
  • 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. According to another aspect of the invention, the following organic electroluminescence device 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 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 compound of formula (I) as a dopant ma- terial and an anthracene compound as a host material.
  • 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 comprising at least one host and at least one dopant, wherein the dopant comprises at least one compound of for- mula (I).
  • the use of a compound of formula (I) according to the present invention in an organic electroluminescence device is provided.
  • the organic EL 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. For example, if two or more organic layers are present between the emitting layer 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. For example, if two or more organic layers are present between the emitting layer and the cath- ode, 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.
  • 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.
  • an emitting layer of the organic electrolumines- cence device which comprises at least one compound of formula (I).
  • the emitting layer comprises at least one emitting material (dopant material) and at least one host material, wherein the emitting material is at least one compound of formula (I).
  • 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, a N element, an O element or a 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). Further most preferably, R 109 and R 110 are independently a group represented by the formula (31). In one embodiment, the compound (10) is a compound represented by the following formula (10-1):
  • the compound (10) is a compound represented by the following formula (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): wherein in the formula (10-4), L 101 and Ar 101 are as defined in the formula (10); R 101 A 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’ ); R61’ 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’ that are not
  • 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 unsubstituted, saturated or unsaturated ring are in- dependently a
  • 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):
  • the compound represented by the formula (10-6) is a compound repre- sented by the following formula (10-6H): (10-6H) wherein in the formula (10-6H), 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); and X 12 is O or S.
  • 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), 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): wherein in the formula (10-7H), 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): R 101A to R 108A are as defined in the formula (10-4); X 12 is O or S; and 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.
  • 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 101 A 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 101 A 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).
  • X 151 is O, S, or C(R 161 )(R 162 ).
  • R 151 to R 160 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. In one embodiment, 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-R 152 ), In the formulas (50-R 152 ), (50-R 153 ), (50-R 154 ), (50-R 157 ), and (50-R 158 ), X 151 , R 151 to R 160 are as defined in the formula (50). * is a single bond which bonds with L 101 .
  • the compound represented by the formula (10) the following compounds can be given as specific examples.
  • the compound represented by the formula (10) is not limited to these spe- cific examples. In the following specific examples, "D" represents a deuterium atom.
  • 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 F4TCNQ (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 F4TCNQ (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- 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 can be 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-mPhAFD 7,14-diphenyl-N,N,N’,N’-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10- diamine
  • p-mPhAFD 7,14-diphenyl-N,N,N’,N’-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10- diamine
  • p-mPhAFD 7,14-diphenyl-N,N,N’
  • 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(CF 3 ppy) 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.
  • an iridium complex, a platinum complex, a terbium complex, a europium complex or the like can be given.
  • Ir(btp) 2 (acac) bis(1-phenylisoquinolinato- N,C2’)iridium(III) acetylacetonate
  • Ir(piq) 2 (acac) bis(1-phenylisoquinolinato- N,C2’)iridium(III) acetylacetonate
  • Ir(piq) 2 (acac) bis(1-phenylisoquinolinato- N,C2’)iridium(III) acetylacetonate
  • Ir(piq) 2 (acac) bis(1-phenylisoquinolinato- N,C2’)iridium(III) acetylacetonate
  • Ir(piq) 2 (acac) bis(1-phenylisoquinolinato- N
  • 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.
  • Examples of the alkali metal compound include an alkali oxide such as Li 2 O, Cs 2 O or K 2 O, and an alkali halide such as LiF, NaF, CsF and KF. Among them, LiF, Li 2 O and NaF are preferable.
  • Examples of the alkaline earth metal compound include BaO, SrO, CaO, and mixtures thereof such as Ba x Sr 1-x O (0 ⁇ x ⁇ 1) and Ba x Ca 1-x O (0 ⁇ x ⁇ 1). Among them, BaO, SrO and CaO are prefer- able.
  • Examples of the rare earth metal compound include YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 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 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-
  • Ar p1 to Ar p3 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 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. 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.
  • the method for forming each layer of the organic EL device of the invention is not particularly limited unless otherwise specified.
  • 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.
  • 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. If the film thickness is too large, a high driving voltage is required to be applied, leading to a lowering in efficiency.
  • 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.
  • Toluene (500 mL) was then added and the reaction heated under an atmosphere of nitrogen at an oil bath temperature of 130°C for 16 hours. The reaction was then allowed to cool to room temperature and the mix- ture filtered over hyflo. The mother liquor was washed with aqueous saturated sodium hy- drogencarbonate, water and then saturated aqueous sodium chloride and dried over magne- sium sulphate. The solution was then filtered over a pad of silica flushing through with toluene. The solvent was removed under reduced pressure. The crude product was triturated with 2-pro- panol.
  • Toluene (6mL), EtOH (2.25 mL) and water (2.25 mL) were then added and the reaction heated at an oil bath temperature of 100°C overnight under an atmosphere of N2.
  • the reaction was cooled to room temperature and diluted with toluene and washed sequentially with aqueous saturated sodium hydrogen car- bonate, water and aqueous saturated sodium chloride, dried over magnesium suphate and the solution filtered directly over silica gel washing through with toluene.
  • the solvent was evapo- rated under reduced pressure and the crude residue was stirred in acetone at room temperature for 1 hour.
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wave- length
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • Tris(dibenzylideneacetone)dipalladium(0) (0.68g, 0.75 mmol), 9,9- Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (1.7g, 3 mmol) and sodium tert-butoxide (10 g, 105 mmol) were then added.
  • the reaction mixture was heated at an oil bath temperature of 120°C for 2 hours.
  • the reaction mixture was then cooled to room temperature and the insolu- ble precipitate was removed by filtration over a pad of celite.
  • the reaction was then heated at an oil bath temperature of 140°C for 2 hours.
  • the reaction was cooled to room temperature and di-isopropylethylamine (4.2 ml, 23.9 mmol) was then added and the mixture allowed to stir at room temperature for 1 hour.
  • the reaction was then quenched by the addition of 10% aqueous sodium acetate and toluene was added to dis- solve any residual precipitate.
  • the organic phase was separated and sequentially washed with saturated aqueous sodium hydrogen carbonate, water and then saturated aqueous sodium chloride and dried over magnesium sulphate.
  • the solvent was concentrated to 50mL under re- Jerusalem pressure and the crude product was precipitated by the addition of ethanol.
  • the resulting reaction mixture was heated at an oil bath temperature of 100°C overnight under an atomosphere of nitrogen. The reaction mixture was then allowed to cool to room temperature and diluted with ethanol (50mL). The insoluble material was collected by filtration. The filter cake was then dissolved with dichloromethane and filtered over a pad of silica, flushing through with dichloromethane. The solvent was then evaporated to give the desired compound.
  • ESI-MS calcd.
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet ab- sorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultravi- olet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultravi- olet absorption wavelength
  • N-iodosuccinimide Upon complete addition of the N-iodosuccinimide, the ice-water bath was re- moved and the reaction was allowed to continue at room temperature for 6 hours. The reac- tion was then cooled again in a water-ice bath and N-iodosuccinimide (16.9g, 75 mmol) was added portionwise to the reaction followed by trifluoromethane sulfonic acid (12.5mL, 141mmol) and the reaction was allowed to continue overnight coming slowly to room tempera- ture. A further portion of N-iodosuccinimide (2.5g, 11.1 mmol) was added and the reaction al- lowed to continue for another 4 hours.
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultravi- olet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • Inter- mediate 39 was characterized by ESI-MS (electrospray ionisation mass spectrometry). The re- sults are shown below.
  • ESI-MS electrospray ionisation mass spectrometry: The re- sults are shown below.
  • Intermediate 39 Compound 21 The procedure for the synthesis of Compound 1 was repeated except for using Intermediate 39 in place of Intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid in place of dibenzo[b,d]furan- 3-ylboronic acid.
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • ESI-MS electrospray ionisation mass spectrometry
  • UV(PhMe) ⁇ onset maximum ultraviolet absorption wavelength
  • 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.
  • As a hole injection layer 10 nm-thick mixture of Compound HT-1 and 3% by weight of compound HI was applied. Then 80 nm-thick of compound HT-1 and 10 nm of Compound HT-2 were applied as hole-transporting layer 1 and hole-transporting layer 2, respectively.
  • Application Example 3 Application Example 1 was repeated except for using the Compound 4 in place of Compound 1 in the emitter layer.
  • the device results are shown in Table 2.
  • Application Example 4 Application Example 1 was repeated except for using the Compound 5 in place of Compound 1 in the emitter layer.
  • the device results are shown in Table 2.
  • Application Example 5 Application Example 1 was repeated except for using the Compound 6 in place of Compound 1 in the emitter layer.
  • the device results are shown in Table 2.
  • Application Example 6 Application Example 1 was repeated except for using the Compound 7 in place of Compound 1 in the emitter layer.
  • the device results are shown in Table 2.
  • Application Example 7 Application Example 1 was repeated except for using the Compound 8 in place of Compound 1 in the emitter layer.
  • the device results are shown in Table 2.
  • Application Example 8 Application Example 1 was repeated except for using the Compound 11 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 9 Application Example 1 was repeated except for using the Compound 12 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 10 Application Example 1 was repeated except for using the Compound 13 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 11 Application Example 1 was repeated except for using the Compound 14 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 12 Application Example 1 was repeated except for using the Compound 15 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 13 Application Example 1 was repeated except for using the Compound 16 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 14 Application Example 1 was repeated except for using the Compound 17 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 15 Application Example 1 was repeated except for using the Compound 18 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 16 Application Example 1 was repeated except for using the Compound 19 in place of Compound 1 in the emitter layer.
  • the device results are shown in Table 2.
  • Application Example 17 Application Example 1 was repeated except for using the Compound 21 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 18 Application Example 1 was repeated except for using the Compound 23 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 19 Application Example 1 was repeated except for using the Compound 24 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 20 Application Example 1 was repeated except for using the Compound 25 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Application Example 21 Application Example 1 was repeated except for using the Compound 26 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Comparative Application Example 2 Application Example 1 was repeated except for using the Comparative Compound 2 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
  • Table 2 Results of the application examples 2) EQE of the device measured at a current density of 10 mA/cm 2 relative to the EQE of Comparative Example 2 calculated using the following formula 3) device lifetime measured at a current density of 50 mA/cm 2 up to 95% of the initial lumi- nance (at 50mA/cm 2 ), relative to the device lifetime of Comparative Example 2 calcu- lated using the following formula

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

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. (I) wherein at least one of at least one of R21, R22 and R23 represents a group HAr; HAr is a group of formula (II)

Description

Compound and an organic electroluminescence device comprising the compound Description 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. 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. US 2022/0020925 A1 and US 2021/0066599 A1 each relate to a compound represented by the following formula (1), wherein one of R12 to R28 is bonded with L2.
Figure imgf000002_0001
R1 to R11 which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R12 to R19 which do not form the substituted or unsubstituted, saturated or unsaturated ring and which are not bonded with L2 are among others independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group in- cluding 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 car- bon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 carbon atoms that form a ring. US 2021/0062078 A1 relates to a compound represented by the following formula (1), wherein in the formula (1), at least one of R1 to R8 is a group represented by the following formula (2).
Figure imgf000003_0001
R1 to R11 which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R12 and R13 are among others independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group in- cluding 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 car- bon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a sub- stituted or unsubstituted cycloalkyl group including 3 to 50 carbon atoms that form a ring. WO2021049889 A1 relates to a compound represented by the following formula (1):
Figure imgf000003_0002
, wherein Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; or represented by the following formula (2),
Figure imgf000004_0001
, wherein when Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group hav- ing 1 to 3 carbon atoms substituted with deuterium. KR20190127529 A relates to an organic electroluminescent device comprising a boron-based organic compound of formula (1) and an anthracene-based organic compound of formula (2) in at least one organic layer included in the organic electroluminescent device.
Figure imgf000004_0002
US20200176679 A1 relates to a compound represented by formula 1 as an organic compound having narrow light emission spectrum and full width half the maximum and capable of sup- pressing the concentration quenching phenomenon in spite of high doping concentration. , wherein
Figure imgf000004_0003
Y is B, P(=O) or P(=S) and X1 and X2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, Se and N(R12). The compound of formula 1 includes at least one or more substituted or unsubstituted cycloalkyl groups having 1 to 20 carbon atoms. US2022093874 A1 relates to a light emitting device and a polycyclic compound of formula 1 used therein
Figure imgf000005_0002
wherein W1 may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and Q1 may be NR16, O, or S. R1 to R16 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 20 ring-forming carbon atoms, or a group represented by Formula 2 may be bonded to adjacent groups of R1 to R16.
Figure imgf000005_0001
WO2021223688 A1 provides an organic compound of formula I and application as well as elec- tronic components and electronic devices using the same.
Figure imgf000006_0001
wherein at least one of R1, R2, R3, R4, and R5 is selected from
Figure imgf000006_0002
. The specific structure and substitution pattern of compounds has a significant impact on the performance of the compounds in organic electronic devices. Notwithstanding the developments described above, there remains a need for organic electrolu- minescence devices comprising new materials, especially dopant (= emitter) materials, to pro- vide improved performance of electroluminescence devices. Accordingly, it is an object of the present invention, with respect to the aforementioned related art, to provide materials suitable for providing organic electroluminescence devices which en- sure good performance of the organic electroluminescence devices, especially a long lifetime and/or a high efficiency. More particularly, it should be possible to provide dopant (= emitter) materials, especially blue light emitting dopant materials having a narrow spectrum (small FWHM), i.e. good color purity when used as dopant in organic electroluminescence devices. Said object is according to one aspect of the present invention solved by a compound repre- sented by formula (I):
wherein
Figure imgf000007_0001
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R20, R21, R22, R23 and R24 each independently repre- sents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substi- tuted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkyl- halide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group hav- ing from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36, NR84R85, or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted, pref- erably an alkyl ring which is unsubstituted or substituted; wherein at least one of R1, R2, R3 and R4, preferably at least one of R2 and R3, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R1, R2, R3 and R4, preferably R2 and R3 together form an alkyl ring which is unsubsti- tuted or substituted; at least one of R5, R6, R7 and R8, preferably at least one of R6 and R7, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R5, R6, R7 and R8, preferably R6 and R7 together form an alkyl ring which is unsubsti- tuted or substituted; and at least one of R21, R22 and R23 represents a group HAr; Y represents a group HAr or RY, wherein RY represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubsti- tuted or substituted; a N-heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or sub- stituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36, NR84R85, or halogen; or RY forms with an adjacent residue at L a ring which is unsubstituted or substituted; and HAr represents a group of formula (II)
Figure imgf000008_0001
wherein R12, R13, R14, R15, R16, R17, R18 and R19 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36; NR84R85, or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted; one of R12, R13, R14, R15, R16, R17, R18 and R19 is a bonding site; X is O, S or CR25R26; L represents a divalent aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a divalent heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; a divalent alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a divalent cycloalkyl group having from 3 to 20 ring carbon atoms which is un- substituted or substituted; R30, R31, R32, R33 , R34, R35 and R36 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted or a cycloalkyl group having from 3 to 20 ring car- bon atoms which is unsubstituted or substituted; R25, R26 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubsti- tuted or substituted or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsub- stituted or substituted; or R25 and R26 together form a ring structure which is unsubstituted or substituted; R84 and R85 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubsti- tuted or substituted or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsub- stituted or substituted; or R84 and R85 together form a ring structure which is unsubstituted or substituted; n represents 0,1, 2 or 3; preferably 0, 1 or 2; more preferably 0 or 1. The compounds of formula (I) can be in principal used in any layer of an EL device. Preferably, the compound of formula (I) is a dopant (= emitter) in organic EL elements, especially in the light-emitting layer, more preferably a fluorescent dopant. Particularly, the compounds of for- mula (I) are used as fluorescent dopants in organic EL devices, especially in the light-emitting layer. The term organic EL device (organic electroluminescence device) is used interchangeably with the term organic light-emitting diode (OLED) in the present application. It has been found that the specific compounds of formula (I) show a narrow emission character- istic, preferably a narrow fluorescence, more preferably a narrow blue fluorescence. Such a nar- row emission characteristic is suitable to prevent energy losses by outcoupling. The compounds of formula (I) according to the present invention preferably have a Full width at half maximum (FWHM) of lower than 30 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. 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 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 18 ring atoms which is in turn unsubstituted or substituted, an alkyl group having 1 to 20, preferably 1 to 8 carbon atoms, a cycloalkyl group having 3 to 20, preferably 3 to 6 carbon atoms, a group OR30, an alkylhalide group having 1 to 20, preferably 1 to 8 carbon atoms, an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted, a halogen atom (fluorine, chlorine, bromine, iodine), CN, C(=O)R32, COOR33, a silyl group SiR34R35R36, a group SR31, NO2 and NR84R85; or two adjacent substituents together form a ring structure which is in turn unsubstituted or substi- tuted; R30, R31, R32, R33, R34, R35, R36, R84 and R85 are defined above. The terms hydrogen, halogen, an alkyl group having from 1 to 20 carbon atoms which is unsub- stituted or substituted, an alkylhalide group having from 1 to 20 carbon atoms which is unsubsti- tuted or substituted, a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubsti- tuted or substituted, a substituted or unsubstituted aryl group having 6 to 30, preferably from 6 to 18 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30, prefera- bly 5 to 18 ring atoms, C(=O)R32, OR30, SR31, C(=O)R32, COOR33, SiR34R35R36, an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted, an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted and an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted, and NR84R85; are known in the art and generally have the following meaning, if said groups are not further specified in specific embodiments mentioned below. In the invention, hydrogen includes isotopes differing in the number of neutrons, i.e. protium, deuterium and tritium. The substituted or unsubstituted aryl group having 6 to 30, preferably from 6 to 18 ring carbon atoms more preferably having from 6 to 13 ring carbon atoms, may be a non-condensed aro- matic group or a condensed aromatic group. Specific examples thereof include phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, fluoranthenyl group, tri- phenylenyl group, phenanthrenyl group, fluorenyl group, indenyl group, anthracenyl, chrysenyl, spirofluorenyl group, benzo[c]phenanthrenyl group, with phenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthryl group, triphenylenyl group, fluorenyl group, indenyl group and fluoranthenyl group being preferred, phenyl group, 1-naphthyl group, 2-naphthyl group, bi- phenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, phenanthrene-9-yl group, phenan- threne-3-yl group, phenanthrene-2-yl group, triphenylene-2-yl group, fluorene-2-yl group, espe- cially a 9,9-di-C1-20alkylfluorene-2-yl group, like a 9,9-dimethylfluorene-2-yl group, a 9,9-di-C6- 18arylfluorene-2-yl group, like a 9,9-diphenylfluorene-2-yl group, or a 9,9-di-C5-18heteroarylfluo- rene-2-yl group, fluorene-4-yl group, especially a 9,9-di-C1-20alkylfluorene-4-yl group, like a 9,9- dimethylfluorene-4-yl group, a 9,9-di-C6-18arylfluorene-4-yl group, like a 9,9-diphenylfluorene-4-yl group, or a 9,9-di-C5-18heteroarylfluorene-4-yl group, 1,1-dimethylindenyl group, fluoranthene-3- yl group, fluoranthene-2-yl group and fluoranthene-8-yl group being more preferred, and phenyl group being most preferred. The substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 18 ring atoms, or a condensed heteroaromatic group. Specific examples thereof include the residues of pyrrole ring, isoindole ring, benzofuran ring, isobenzofuran ring, benzothiophene, dibenzothiophene ring, isoquinoline ring, quinoxaline ring, quinazoline, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, indole ring, quinoline ring, acridine ring, carbazole ring, furan ring, thiophene ring, benzoxazole ring, benzothiazole ring, benzimid- azole ring, dibenzofuran ring, triazine ring, oxazole ring, oxadiazole ring, thiazole ring, thiadia- zole ring, triazole ring, imidazole ring, indolidine ring, imidazopyridine ring, 4-imidazo[1,2-a]ben- zimidazoyl, 5-benzimidazo[1,2-a]benzimidazoyl, and benzimidazolo[2,1-b][1,3]benzothiazolyl, with the residues of benzofuran ring, indole ring, benzothiophene ring, dibenzofuran ring, carba- zole ring, and dibenzothiophene ring being preferred, and the residues of benzofuran ring, 1- phenylindol ring, benzothiophene ring, dibenzofuran-1-yl group, dibenzofuran-3-yl group, diben- zofuran-2-yl group, dibenzofuran-4-yl group, 9-phenylcarbazole-3-yl group, 9-phenylcarbazole- 2-yl group, 9-phenylcarbazole-4-yl group, dibenzothiophene-2-yl group, and dibenzothiophene- 4-yl, dibenzothiophene-1-yl group, and dibenzothiophene-3-yl group being more preferred. The substituted or unsubstituted N-heteroaryl group having 5 to 30, preferably 5 to 18 ring at- oms, more preferably having from 5 to 13 ring atoms, is described as the substituted or unsub- stituted heteroaryl group mentioned above, wherein at least one of the ring atoms is nitrogen. Examples of the alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substi- tuted, linear or branched include methyl group, ethyl group, n-propyl group, isopropyl group, n- butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, isopentyl, neopentyl, 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, neopentyl group, 1-methylpentyl group, with methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group being preferred. Preferred are alkyl groups having 1 to 8 carbon atoms, more 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. Most preferred are methyl, isopropyl and t-butyl. Preferably, the alkyl group is unsubstituted, i.e. it does not comprise atoms other than C and H and does not comprise unsaturated or aromatic groups. However, the alkyl group is linear or branched. Examples of the alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted include those disclosed as alkyl groups wherein the hydrogen atoms thereof are partly or entirely substituted by halogen atoms. Preferred alkylhalide groups are fluoroalkyl groups having 1 to 20 carbon atoms including the alkyl groups mentioned above wherein the hydrogen atoms thereof are partly or entirely substituted by fluorine atoms, for example CF3. Examples of the alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or sub- stituted include ethene group, n-propene group, isopropene group, n-butene group, isobutene 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 pre- ferred. Preferred are alkenyl groups having 2 to 8 carbon atoms, more preferably 2 to 4 carbon atoms. Suitable examples for alkenyl groups having 2 to 8 carbon atoms respectively 2 to 4 car- bon atoms are mentioned before. Examples of the alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or sub- stituted 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. Preferred are alkynyl groups having 2 to 8 carbon atoms, more preferably 2 to 4 carbon atoms. Suitable examples for alkynyl groups having 2 to 8 carbon atoms respectively 2 to 4 carbon atoms are mentioned before. Examples of the cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cy- clooctyl group, and adamantyl group, with cyclopentyl group, and cyclohexyl group being pre- ferred. Preferred are cycloalkyl groups having 3 to 6 carbon atoms. Suitable examples for cyclo- alkyl groups having 3 to 6 carbon atoms are mentioned before. An example for an aralkyl group having from 7 to 30 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. The group OR30 is preferably a C1-20alkoxy group or a C6-18aryloxy group. Examples of an alkoxy group having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, include those having an al- kyl portion selected from the alkyl groups mentioned above. Examples of an aryloxy group hav- ing 6 to 18 ring carbon atoms include those having an aryl portion selected from the aryl groups mentioned above, for example -OPh. The group SR31 is preferably a C1-20alkylthio group or a C6-18arylthio group. Examples of an al- kylthio group having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, include those having an alkyl portion selected from the alkyl groups mentioned above. Examples of an arylthio group having 6 to 18 ring carbon atoms include those having an aryl portion selected from the aryl groups mentioned above, for example -SPh. The group SiR34R35R36 is preferably a C1-20alkyl and/or C6-18aryl substituted silyl group. Preferred examples of C1-20alkyl and/or C6-18aryl substituted silyl groups include alkylsilyl groups having 1 to 8 carbon atoms in each alkyl residue, preferably 1 to 4 carbon atoms, including trimethylsilyl propyldimethylsilyl group, dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutyl- silyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group, and arylsilyl groups hav- ing 6 to 18 ring carbon atoms in each aryl residue, preferably triphenylsilyl group, and alkyl/ar- ylsilyl groups, preferably phenyldimethylsilyl group, diphenylmethylsilyl group, and diphenylterti- arybutylsilyl group, with diphenyltertiarybutylsilyl group and t-butyldimethylsilyl group being pre- ferred. The group NR84R85 is an amino group, wherein R84 and R85 are described above. Preferably, R84 and R85 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; or a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted, preferably, R84 and R85 each independently represents an aryl group having from 6 to 18 ring carbon atoms which is unsubstituted or substituted; or a het- eroaryl group having from 5 to 18 ring atoms which is unsubstituted or substituted. The optional substituents preferably each independently represents an aryl group having from 6 to 18 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 18 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; halogen, CN; SiR34R35R36, SR31 or OR30; or two adjacent substituents together form a ring structure which is in turn unsubstituted or substi- tuted. More preferably, the optional substituents each independently represents an aryl group having from 6 to 18 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 18 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; halogen, SiR34R35R36 or CN; or two adjacent substituents together form a ring structure which is in turn unsubstituted or substi- tuted. Most preferably, the optional substituents each independently represents an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 6 ring carbon atoms which is unsubstituted or substituted; an aryl group having 6 to 13 ring car- bon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 13 ring at- oms which is unsubstituted or substituted; halogen, SiR34R35R36 or CN. R30, R31, R32, R33 , R34, R35 and R36 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted or a cycloalkyl group having from 3 to 20 ring car- bon atoms which is unsubstituted or substituted. 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. According to the present invention, at least one of R1, R2, R3 and R4, preferably at least one of R2 and R3, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; at least one of R5, R6, R7 and R8, preferably at least one of R6 and R7, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; and at least one of R21, R22 and R23 represents a group HAr. The compound of formula (I) therefore mandatorily comprises at least 3 substituents, i.e. at least one of R1, R2, R3 and R4 as a first substituent, at least one of R5, R6, R7 and R8 as a sec- ond substituent and at least one of R21, R22 and R23 as a third substituent. Preferably, the total number of substituents in the compound of formula (I) is 3, 4, 5, 6, 7 or 8, preferably 3, 4, 5, or 6, i.e. the remaining residues are hydrogen. The “carbon number of a to b” in the expression of “X group having a to b carbon atoms which is substituted or unsubstituted” 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 substituents mentioned above. An index of 0 in the definition in the formulae mentioned above and below means that a hydro- gen atom is present at the position defined by said index. Examples for ring structures formed by two adjacent substituents are shown below:
Figure imgf000015_0001
Figure imgf000016_0001
wherein X’ represents O, S or CR68R69; R42, R43, R44, R45, R46, R47, R48, R49, R50, R51, R52, R53, R54, R55, R56, R57, R58, R59, R60, R61, R62, R63, R64, R65, R66 and R67, R70, R71, R72, R73, R74, R75, R76, R77 and R78 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 alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or two adjacent residues together form a ring structure which is unsubstituted or substituted, wherein the dotted lines are bonding sites; R68 and R69 each independently represents 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 substituted or an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or R68 and R69 together form an aromatic ring structure having from 3 to 13 ring atoms which is un- substituted or substituted or an aliphatic ring structure having from 3 to 9 ring atoms which is unsubstituted or substituted; X’’ and Y’’ each independently represents O, CRcRd, S, BRe or NRe, Rc and Rd each independently represents C1 to C8 alkyl or substituted or unsubstituted C6 to C18 aryl, preferably C1 to C4 alkyl or substituted or unsubstituted C6 to C10 aryl, more preferably me- thyl or unsubstituted or substituted phenyl, Re represents C1 to C8 alkyl, preferably C1 to C4 alkyl, or substituted or unsubstituted C6 to C10 aryl, preferably unsubstituted or substituted phenyl, and the dotted lines are bonding sites. Preferred examples for ring structures formed by two adjacent substituents are the ring struc- tures (A), (D), (G) and (H), more preferred ring structures formed by two adjacent substituents are
Figure imgf000017_0001
The compounds of formula (I) In the compounds of formula (I): - At least one of R1, R2, R3 and R4, preferably at least one of R2 and R3, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cyclo- alkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R1, R2, R3 and R4, preferably R2 and R3 together form an alkyl ring which is unsubstituted or substituted. - At least one of R5, R6, R7 and R8, preferably at least one of R6 and R7, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cyclo- alkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R5, R6, R7 and R8, preferably R6 and R7 together form an alkyl ring which is unsubstituted or substituted. - At least one of R21, R22 and R23 represents a group HAr. At least one of R1, R2, R3 and R4, preferably at least one of R2 and R3, and at least one of R5, R6, R7 and R8, preferably at least one of R6 and R7, each independently represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adja- cent residues together form an alkyl ring which is unsubstituted or substituted Suitable and preferred alkyl groups having from 1 to 20 carbon atoms which are unsubstituted or substituted, and cycloalkyl groups having from 3 to 20 ring carbon atoms which are unsubsti- tuted or substituted are mentioned above. Preferably, at least one of R1, R2, R3 and R4, prefera- bly at least one of R2 and R3, and at least one of R5, R6, R7 and R8, preferably at least one of R6 and R7, each independently represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, more preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted or substituted, most preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted or substituted, further most preferably a methyl group or a t-butyl group. Further preferably, the alkyl group mentioned above is unsubstituted. However, it is linear or branched. Suitable and preferred alkyl rings which are unsubstituted or substituted are mentioned above. Preferably, two adjacent residues R1, R2, R3 and R4, preferably R2 and R3 and/or R5, R6, R7 and R8, preferably R6 and R7 together form a ring structure (G) or (H) mentioned above. More prefer- ably one of the following ring structures:
Figure imgf000018_0001
Preferably, exactly one of R1, R2, R3 and R4, preferably exactly one of R2 and R3, and exactly one of R5, R6, R7 and R8, preferably exactly one of R6 and R7, each independently represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted. Preferred alkyl groups and cycloalkyl groups are mentioned above; or two adjacent residues R1, R2, R3 and R4, preferably R2 and R3 together form an alkyl ring which is unsubstituted or substituted and/or two adjacent residues R5, R6, R7 and R8, preferably R6 and R7 together form an alkyl ring which is unsubstituted or substituted, wherein preferred alkyl rings form a ring structure (G) or (H) as mentioned above, preferably
Figure imgf000018_0002
Figure imgf000018_0003
At least one of R21, R22 and R23 represents a group HAr The group HAr is a group of formula (II)
Figure imgf000019_0001
R12, R13, R14, R15, R16, R17, R18 and R19 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36; NR84R85, or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted; one of R12, R13, R14, R15, R16, R17, R18 and R19 is a bonding site. X is O, S or CR25R26. Preferably, R12, R13, R14, R15, R16, R17, R18 and R19 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a het- eroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted, wherein suitable and preferred ring structures are mentioned above; one of R12, R13, R14, R15, R16, R17, R18 and R19 is a bonding site. More preferably, R12, R13, R14, R15, R16, R17, R18 and R19 each independently represents hydro- gen; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a or two adjacent residues together form a ring structure which is unsubstituted or substituted, wherein suitable and preferred ring structures are mentioned above; one of R12, R13, R14, R15, R16, R17, R18 and R19 is a bonding site. Most preferably, R12, R13, R14, R15, R16, R17, R18 and R19 each independently represents hydro- gen; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; one of R12, R13, R14, R15, R16, R17, R18 and R19 is a bonding site. Further most preferably, 0, 1 or 2 of R12, R13, R14, R15, R16, R17, R18 and R19 each independently represents hydrogen; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted and the remaining residues are H; one of R12, R13, R14, R15, R16, R17, R18 and R19 is a bonding site. Examples for suitable groups of formula (II) are:
Figure imgf000020_0001
wherein R14, R17, R18, R19, R25 and R26 are described above, and the dotted line is a bonding site. In a preferred embodiment, exactly one of R21, R22 and R23, preferably R22 represents a group HAr. In a further preferred embodiment R21 represents a group HAr. Preferred groups HAr are mentioned above. Preferably, R25, R26 each independently represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted, more preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted, most preferably methyl; or R25 and R26 together form ring structure which is unsubstituted or substituted. In one embodiment, R25 and R26 do not form together a ring structure which is unsubstituted or More preferably, R25, R26 each independently represents an alkyl group having from 1 to 20 car- bon atoms which is unsubstituted or substituted, preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted, more preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted, most preferably methyl; or an aryl group having from 6 to 30 ring carbon atoms, preferably from 6 to 18 ring carbon atoms, more preferably having from 6 to 13 ring carbon atoms which is unsubstituted or substituted, most preferably a phenyl group which is unsubstituted or substituted, further most preferably a phenyl group which is unsubstituted. The remaining groups R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R20, R21, R22, R23 and R24 The remaining groups R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R20, R21, R22, R23 and R24, i.e. the groups which are not mandatorily defined as alkyl groups having from 1 to 20 carbon atoms which are unsubstituted or substituted, and cycloalkyl groups having from 3 to 20 ring carbon atoms which are unsubstituted or substituted, or two adjacent residues together form an alkyl ring which is unsubstituted or substituted, and as a group HAr each independently represents hydrogen; each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsub- stituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substi- tuted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36, NR84R85, or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted, pref- erably an alkyl ring which is unsubstituted or substituted; Preferably, the remaining groups R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R20, R21, R22, R23 and R24 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsub- stituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubsti- tuted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubsti- tuted or substituted; or NR84R85; or two adjacent residues together form a ring structure which is unsubstituted or substituted, pref- erably an alkyl ring which is unsubstituted or substituted. More preferably, the remaining groups R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R20, R21, R22, R23 and R24 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or NR84R85; or two adjacent residues together form a ring structure which is unsubstituted or substituted, pref- erably an alkyl ring which is unsubstituted or substituted. Further more preferably, the remaining groups R1, R2, R3, R4, R5, R6, R7, R8, R20, R21, R22, R23 and R24 each independently represents hydrogen; and at least one of R9, R10 and R11, preferably R10 represents hydrogen, an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; NR84R85, or R9 and R10 and/or R10 and R11 together form a ring structure which is unsubstituted or substi- tuted, preferably an alkyl ring which is unsubstituted or substituted. Suitable ring structures are mentioned above. In a further embodiment, R1, R4, R5, R8, R9, R11, R20 and R24 are hydrogen; or R1, R4, R5, R8, R9 and R11 are hydrogen, and R20 and R24 each independently represents hydrogen or an aryl group having from 6 to 30 ring carbon atoms, preferably from 6 to 18 ring carbon atoms, more preferably having from 6 to 13 ring carbon atoms which is unsubstituted or substituted, most preferably phenyl which is unsub- stituted or substituted, further most preferably phenyl which is unsubstituted. L, n, Y L represents a divalent aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a divalent heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; a divalent alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a divalent cycloalkyl group having from 3 to 20 ring carbon atoms which is un- substituted or substituted; preferably, L represents a divalent aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; or a divalent heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; more preferably, L represents a divalent aryl group having from 6 to 24 ring carbon atoms which is unsubstituted or substituted, preferably 6 to 18 ring atoms, or a divalent heteroaryl group hav- ing from 5 to 24 ring atoms which is unsubstituted or substituted, preferably 5 to 18 ring atoms; further more preferably, L represents a phenylene group which is unsubstituted or substituted, a divalent naphthyl group which is unsubstituted or substituted, a divalent anthryl group which is unsubstituted or substituted, a divalent phenanthryl group which is unsubstituted or substituted, a divalent triphenylenyl group which is unsubstituted or substituted, a divalent 9,9-dimethyl fluo- rene group which is unsubstituted or substituted, a divalent 9,9-diphenyl fluorene group which is unsubstituted or substituted, or a divalent heteroaryl group having from 3 to 24 ring atoms which is unsubstituted or substituted, preferably 3 to 14 ring atoms; most preferably, L represents a phenylene group which is unsubstituted or substituted, e.g. a 1,2-phenylene group, a 1,3-phenylene group or a 1,4-phenylene group. n represents 0, 1, 2 or 3; preferably 0, 1 or 2; more preferably 0 or 1. In the case that n repre- sents 0, there is a direct bond between N and Y. In the case that n is 1, L is preferably a group of the following formula:
Figure imgf000023_0001
wherein R37, R38, R39, R40 and R41 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsub- stituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substi- tuted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36, NR84R85, or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted, pref- erably an alkyl ring which is unsubstituted or substituted or an aryl ring, e.g. naphthyl or anthryl, which is unsubstituted or substituted; wherein one of R37, R38, R39, R40 and R41, preferably R39 or R40, more preferably R39 is Y; and the dotted line is a bonding site. Y is a group HAr or RY. The group HAr is a group of formula (II) defined as described above. RY represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubsti- tuted or substituted; a N-heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or sub- stituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36, NR84R85, or halogen; or RY forms with an adjacent residue at L a ring which is unsubstituted or substituted. The adjacent residue at L is preferably one of the residues R37, R38, R39, R40 and R41 which is not Y. Preferably, RY represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a N-heteroaryl group having from 5 to 30 ring atoms which is un- substituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubsti- tuted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or RY forms with an adjacent residue at L, preferably one of the residues R37, R38, R39, R40 and R41 which is not Y, an alkyl ring which is unsubstituted or substituted. More preferably, RY represents hydrogen, an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, more preferably an alkyl group having from 1 to 8 carbon atoms which is unsubstituted or substituted, most preferably an alkyl group having from 1 to 4 carbon atoms which is unsubstituted or substituted, further most preferably a methyl group or a t-butyl group; further preferably, the alkyl group mentioned above is unsubstituted, however, it is linear or branched; or RY forms with an adjacent residue at L, preferably one of the residues R37, R38, R39, R40 and R41 which is not Y, an alkyl ring which is unsubstituted or substituted; or RY represents an aryl group having from 6 to 30 ring carbon atoms, preferably from 6 to 18 ring carbon atoms, more preferably having from 6 to 13 ring carbon atoms which is unsubstituted or substituted, most preferably phenyl which is unsubstituted or substituted, further most preferably phenyl which is unsubstituted. Suitable and preferred alkyl rings which are unsubstituted or substituted are mentioned above; more preferred alkyl rings are represented by ring structure (G) or (H) mentioned above, most
Figure imgf000025_0001
Preferably, one of R37, R38, R39, R40 and R41, preferably one of R39 and R40 , more preferably R39 represents RY; or two adjacent residues RY and one of R37, R38, R39, R40 and R41 which is not Y, preferably RY at the position of R39 and R40 together form an alkyl ring which is unsubstituted or substituted, wherein preferred alkyl rings form a ring structure (G) or (H) as mentioned above, preferably
Figure imgf000025_0002
and the remaining residues of R37, R38, R39, R40 and R41 are hydrogen. Preferably, in the case that Y is HAr, one of R37, R38, R39, R40 and R41, preferably R39 or R40, more preferably R39 is HAr, wherein suitable and preferred groups HAr are the same groups HAr as mentioned above. In the case that n is 2 or 3, the groups L may be the same or different. In this case, the group -(L)n- can be described as -L1-L2- in the case of n = 2 and – L1-L2- L3- in the case of n = 3. In this case (n = 2 or 3), L1 is the group farthest from N and L2 (in the case of n = 2) or L3 (in the case of n = 3) respectively are the groups closest to N. L1, L2 and L3 are defined in the same way as L. L1 is preferably defined as mentioned for L above for the case n = 1. L2 and L3 are preferably each independently phenyl groups which are unsubstituted or substi- tuted, more preferably 1,2-phenylene, 1,3-phenylene or 1,4 phenylene groups which are are un- substituted or substituted, most preferably 1,2-phenylene, 1,3-phenylene or 1,4 phenylene groups which are are unsubstituted, and further most preferably 1,3-phenylene or 1,4 phenylene groups which are are unsubstituted. Examples for groups Y–(L)n- are
Figure imgf000026_0002
wherein the residues and groups RY, R13 and X are described above and below. Preferred groups Y–(L)n- are:
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
More preferred groups Y-(L)n- are:
Figure imgf000031_0002
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Preferred compounds of formula (I) are shown in the following, wherein the residues and groups and indices are defined above:
Figure imgf000035_0002
More preferred compounds of formula (I) are the following compounds, wherein the residues, groups and indices are defined above
Figure imgf000036_0001
More preferably, in the compounds of formula (Ia), (Ib), (Iaa), (Iba), (Iab) and (Ibb): R1, R4, R5, R8, R9, R11, R20 and R24 are hydrogen; or R1, R4, R5, R8, R9 and R11 are hydrogen and R20 and R24 each independently represents hydrogen or an aryl group having from 6 to 30 ring carbon atoms; at least one of R2 and R3 represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, and the remaining residue R2 or R3 is hydrogen; or R2 and R3 together form an alkyl ring which is unsubstituted or substituted; at least one of R6 and R7 represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, and the remaining residue R6 or R7 is hydrogen; or R6 and R7 together form an alkyl ring which is unsubstituted or substituted; R10 represents hydrogen, an alkyl group having from 1 to 20 carbon atoms which is unsubsti- tuted or substituted, a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubsti- tuted or substituted, or NR84R85; or an aryl group having from 6 to 30 ring carbon atoms; RY represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substi- tuted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or sub- stituted, or RY forms with an adjacent residue at L an alkyl ring which is unsubstituted or substi- tuted; or RY represents hydrogen or an aryl group having from 6 to 30 ring carbon atoms; R84 and R85 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; L represents a phenylene group which is unsubstituted or substituted; and n is 0 or 1. Below, examples for compounds of formula (I) are given:
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
Figure imgf000074_0001
Figure imgf000075_0001
Preparation of the compounds of formula (I)
The compounds represented by formula (I) can be synthesized in accordance with the reactions conducted in the examples of the present application, and by using alternative reactions or raw materials suited to an intended product, in analogy to reactions and raw materials known in the art.
The compounds of formula (I) are for example prepared by the following steps:
(I) Addition of A-Li to the intermediate (III) to generate in situ the lithiated species;
(ii) Addition of BHal’3 to the lithiated intermediate (III), or addition of BOR* 3 to the lithiated in- termediate (III), whereby intermediate (IV) is obtained:
Figure imgf000075_0002
wherein A represents a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms which may be linear or branched, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon at- oms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, preferably, A rep- resents an unsubstituted alkyl group having 1 to 6 carbon atoms which may be linear or branched; Hal represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br and most preferably Br; Hal’ represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br and most preferably Br; one of R20, R21, R22, R23 and R24 in the intermediate (IV) is Hal’’; Hal’’ represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br and most preferably Cl; R* represents an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted cyclo- alkyl group having 3 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, substi- tuted by one or two unsubstituted alkyl groups having 1 to 8 carbon atoms, a unsubstituted alkoxy group having 1 to 8 carbon atoms; or two resudues R* are joined together to form a ring, e.g.
Figure imgf000076_0001
all other residues, groups and indices are as defined before; one example for a preferred intermediate (IV) is intermediate (IVa), wherein R22 is Hal’:
Figure imgf000076_0002
(i) Reaction of the halogen atom of intermediate (IV) with BQ2-HAr (V), whereby the com- pound of formula (I) is obtained
Figure imgf000077_0002
wherein one of R12, R13, R14, R15, R16, R17, R18 and R19 in BQ2-HAr (V) is -BQ2; Q is an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, substituted by one or two unsubstituted alkyl groups having 1 to 8 carbon atoms, a unsubstituted alkoxy group hav- ing 1 to 8 carbon atoms, a hydroxyl group, wherein two alkyl groups Q or two alkoxy groups Q together may form a five or six membered substituted or unsubstituted ring; catalyst: preferred catalysts are Pd catalysts; all other residues, groups and indices are as defined before. It is generally also possible to prepare the compounds of formula (I) by reaction of a compound of formula (IV), wherein one of R20, R21, R22, R23 and R24 in the intermediate (IV) is -BQ2 with a compound of formula
Figure imgf000077_0001
wherein one of R12 R13 R14 R15 R16 R17 R18 and R19 in BQ2HAr (V) is Hal’’ One example for a preferred intermediate BQ2-HAr (V) is intermediate (Va), wherein R14 is
Figure imgf000078_0002
Suitable Pd catalysts are for example Pd(0) complexes with bidentate ligands like dba (diben- zylideneacetone), or Pd(II) salts like PdCl2 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 triphenylphosphine, tri-ortho-tolyl phos- phine, tri-tertbutylphosphine, tricyclohexylphosphine, 2-Dicyclohexylphosphino-2',6'-dimethox- ybiphenyl (SPhos), 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos), or N-hetero- cyclic carbenes such as 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr), 1,3-Dimesitylim- idazol-2-ylidene (Imes). Josiphos:
Figure imgf000078_0001
, wherein R and R’ are generally substituted or unsubstituted phenyl. It is generally possible to change the sequence of steps (i) and (ii) in the process mentioned above, i.e. to carry out the addition of BQ2-HAr (equivalent to step (ii)) first and to carry out the borylation of the obtained intermediate (equivalent to step (i)) subsequently. Suitable reaction conditions are known by a person skilled in the art. Reaction steps for obtain- ing intermediates (III), (IV) and (V) are shown in the examples of the present application. Details of all reaction steps and process conditions are mentioned in the examples of the pre- sent application. 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. According to another aspect of the invention, the following organic electroluminescence device 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). According to another aspect of the invention an organic electroluminescence device is provided, wherein the light emitting layer comprises at least one compound of formula (I). According to another aspect of the invention an organic electroluminescence device is provided, wherein the light emitting layer comprises at least one compound of formula (I) as a dopant ma- terial and an anthracene compound as a host material. According to another aspect of the invention an electronic equipment provided with the organic electroluminescence device according to the present invention is provided. According to another aspect of the invention an emitter material is provided comprising at least one compound of formula (I). According to another aspect of the invention a light emitting layer is provided comprising at least one host and at least one dopant, wherein the dopant comprises at least one compound of for- mula (I). According to another aspect of the invention the use of a compound of formula (I) according to the present invention in an organic electroluminescence device is provided. In one embodiment, the organic EL device comprises a hole-transporting layer between the an- ode and the emitting layer. In one embodiment, the organic EL device comprises an electron-transporting layer between the cathode and the emitting layer. In the present specification, regarding 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. For example, if two or more organic layers are present between the emitting layer 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. Similarly, regarding 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. For example, if two or more organic layers are present between the emitting layer and the cath- ode, 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. By the presence of a compound of formula (I) in the organic EL device, preferably in the emitting layer, organic EL devices characterized by high external quantum efficiencies (EQE) and long lifetimes are pro- vided. According to another aspect of the invention, an emitting layer of the organic electrolumines- cence device is provided which comprises at least one compound of formula (I). Preferably, the emitting layer comprises at least one emitting material (dopant material) and at least one host material, wherein the emitting material is at least one compound of formula (I). In one embodiment, 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(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3- yl)-1 ,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1 ,3,5-triazine) and/or TST (2,4,6-tris(9,9'- spirobifluorene-2-yl)- 1,3,5-triazine). 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. More preferably, the organic electroluminescence device according to the present invention 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. Preferably, the at least one host is at least one substituted or unsubstituted anthracene compound. In a further preferred embodiment, the organic electroluminescence device according to the pre- sent invention 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. Preferably, the at least one host is at least one substituted or unsubstituted anthracene compound. According to another aspect of the invention, an emitting layer of the organic electrolumines- cence device is provided 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):
Figure imgf000081_0001
wherein one or more pairs of two or more adjacent R101 to R110 may form a substituted or unsubstituted, saturated or unsaturated ring; R101 to R110 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 substituted or unsubstituted cycloal- kyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group in- cluding 1 to 50 carbon atoms, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms Si(R121)(R122)(R123) C(=O)R124 COOR125, -N(R126)(R127), a halogen atom, a cyano group, a nitro group, a substituted or unsub- stituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted monova- lent heterocyclic group including 5 to 50 ring atoms, or a group represented by the following for- mula (31); R121 to R127 are independently a hydrogen atom, a substituted or unsubstituted alkyl group in- cluding 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when each of R121 to R127 is present in plural, each of the plural R121 to R127 may be the same or different; provided that at least one of R101 to R110 that do not form the substituted or unsubstituted, satu- rated or unsaturated ring is a group represented by the following formula (31). If two or more groups represented by the formula (31) are present, each of these groups may be the same or different; -L101-Ar101 (31) wherein in the formula (31), L101 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; Ar101 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. Specific examples of each substituent, substituents for “substituted or unsubstituted” and the halogen atom in the compound (10) are the same as those mentioned above. An explanation will be given on “one or more pairs of two or more adjacent R101 to R110 may form a substituted or unsubstituted, saturated or unsaturated ring”. The “one pair of two or more adjacent R101 to R110” is a combination of R101 and R102, R102 and R103, R103 and R104, R105 and R106, R106 and R107, R107 and R108, R108 and R109, R101 and R102 and R103 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 R101 and R102 form a ring, for example, a ring formed by a carbon atom with which R101 is bonded, a carbon atom with which R102 is bonded and one or more arbitrary elements. Specifically, when a ring is formed by R101 and R102, when an unsaturated ring is formed by a carbon atom with which R101 is bonded, a carbon atom with R102 is bonded and four carbon atoms, the ring formed by R101 and R102 is a benzene ring. The “arbitrary element” is preferably a C element, a N element, an O element or a 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. For example, R101 and R102 may form a ring, and simultaneously, R105 and R106 may form a ring. In this case, the compound represented by the formula (10) is a compound represented by the following formula (10A), for example:
Figure imgf000083_0001
In one embodiment, R101 to R110 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). Preferably, R101 to R110 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, R101 to R110 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 R109 and R110 is a group represented by the formula (31). Further most preferably, R109 and R110 are independently a group represented by the formula (31). In one embodiment, the compound (10) is a compound represented by the following formula (10-1):
Figure imgf000084_0003
wherein in the formula (10-1), R101 to R108, L101 and Ar101 are as defined in the formula (10). In one embodiment, the compound (10) is a compound represented by the following formula (10-2):
Figure imgf000084_0002
wherein in the formula (10-2), R101, R103 to R108, L101 and Ar101 are as defined in the formula (10). In one embodiment, the compound (10) is a compound represented by the following formula (10-3):
Figure imgf000084_0001
wherein in the formula (10-3), R101A to R108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; L101A is a single bond or a substituted or unsubstituted arylene group including 6 to 30 ring car- bon atoms, and the two L101As may be the same or different; Ar101A is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and the two Ar101As may be the same or different. In one embodiment, the compound (10) is a compound represented by the following formula (10-4):
Figure imgf000085_0001
wherein in the formula (10-4), L101 and Ar101 are as defined in the formula (10); R101A to R108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; X11 is O, S, or N(R61’); R61’ 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 R62’ to R69’ is an atomic bonding that is bonded with L101; one or more pairs of adjacent R62’ to R69’ that are not bonded with L101 may be bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring; and R62’ to R69’ that are not bonded with L101 and do not form the substituted or unsubstituted, satu- rated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted al- kyl group including 1 to 50 carbon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. In one embodiment, the compound (10) is a compound represented by the following formula (10-4A):
Figure imgf000086_0001
( ) wherein in the formula (10-4A), L101 and Ar101 are as defined in the formula (10); R101A to R108A are independently a hydrogen atom or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; X11 is O, S or N(R61); R61 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 R62A to R69A may form a substituted or unsubsti- tuted, saturated or unsaturated ring, and adjacent two of R62A to R69A form a ring represented by the following formula (10-4A-1); and R62A to R69A that do not form a substituted or unsubstituted, saturated or unsaturated ring are in- dependently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 car- bon atoms or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
Figure imgf000086_0002
wherein in the formula (10-4A-1), each of the two atomic bondings * is bonded with adjacent two of R62A to R69A; one of R70’ to R73’ is an atomic bonding that is bonded with L101; and R70’ to R73’ that are not bonded with L101 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. In one embodiment, the compound (10) is a compound represented by the following formula (10-6):
Figure imgf000087_0001
(10-6) wherein in the formula (10-6), L101 and Ar101 are as defined in the formula (10); R101A to R108A are as defined in the formula (10-4); R66’ to R69’ are as defined in the formula (10-4); and X12 is O or S. In one embodiment, the compound represented by the formula (10-6) is a compound repre- sented by the following formula (10-6H):
Figure imgf000087_0002
(10-6H) wherein in the formula (10-6H), L101 and Ar101 are as defined in the formula (10); R66’ to R69’ are as defined in the formula (10-4); and X12 is O or S. In one embodiment, the compound represented by the formulae (10-6) and (10-6H) is a com- pound represented by the following formula (10-6Ha):
Figure imgf000088_0001
(10-6Ha) wherein in the formula (10-6Ha), L101 and Ar101 are as defined in the formula (10); and X12 is O or S. In one embodiment, 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):
Figure imgf000088_0002
wherein in the formula (10-6Ha-1) and (10-6Ha-2), L101 and Ar101 are as defined in the formula (10); and X12 is O or S. In one embodiment, the compound (10) is a compound represented by the following formula (10-7):
Figure imgf000088_0003
(10-7) wherein in the formula (10-7), R101A to R108A are as defined in the formula (10-4); X11 is as defined in the formula (10-4); and R62’ to R69’ are as defined in the formula (10-4), provided that any one pair of R66’ and R67’, R67’ and R68’, and R68’ and R69’ are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring. In one embodiment, the compound (10) is a compound represented by the following formula (10-7H):
Figure imgf000089_0001
wherein in the formula (10-7H), L101 and Ar101 are as defined in the formula (10); X11 is as defined in the formula (10-4); and R62’ to R69’ are as defined in the formula (10-4), provided that any one pair of R66’ and R67’, R67’ and R68’, and R68’ and R69’ are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring. In one embodiment, the compound (10) is a compound represented by the following formula (10-8):
Figure imgf000089_0002
R101A to R108A are as defined in the formula (10-4); X12 is O or S; and R66’ to R69’ are as defined in the formula (10-4), provided that any one pair of R66’ and R67’, R67’ and R68’, as well as R68’ and R69’ are bonded with each other to form a substituted or unsubsti- tuted, saturated or unsaturated ring. In one embodiment, the compound represented by the formula (10-8) is a compound repre- sented by the following formula (10-8H):
Figure imgf000090_0001
In the formula (10-8H), L101 and Ar101 are as defined in the formula (10). R66’ to R69’ are as defined in the formula (10-4), provided that any one pair of R66’ and R67’, R67’ and R68’, as well as R68’ and R69’ are bonded with each other to form a substituted or unsubsti- tuted, saturated or unsaturated ring. Any one pair of R66’ and R67’, R67’ and R68’, as well as R68’ and R69’ may preferably be bonded with each other to form an unsubstituted benzene ring; and X12 is O or S. In one embodiment, as for the compound represented by the formula (10-7), (10-8) or (10-8H), any one pair of R66’ and R67’, R67’ and R68’, as well as R68’ and R69’ are bonded with each other to form a ring represented by the following formula (10-8-1) or (10-8-2), and R66’ to R69’ 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.
Figure imgf000090_0002
(10-8-1) (10-8-2) wherein in the formulae (10-8-1) and (10-8-2), the two atomic bondings * are independently bonded with one pair of R66’ and R67’, R67’ and R68’, or R68’ and R69’; R80 to R83 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 X13 is O or S. In one embodiment, the compound (10) is a compound represented by the following formula (10-9):
Figure imgf000091_0001
(10-9) wherein in the formula (10-9), L101 and Ar101 are as defined in the formula (10); R101A to R108A are as defined in the formula (10-4); R66’ to R69’ are as defined in the formula (10-4), provided that R66’ and R67’, R67’ and R68’, as well as R68’ and R69’ are not bonded with each other and do not form a substituted or unsubstituted, saturated or unsaturated ring; and X12 is O or S. In one embodiment, the compound (10) is selected from the group consisting of compounds represented by the following formulae (10-10-1) to (10-10-4).
Figure imgf000091_0002
Figure imgf000092_0001
In the formulae (10-10-1H) to (10-10-4H), L101A and Ar101A are as defined in the formula (10-3). In one embodiment, in the compound represented by the formula (10-1), at least one Ar101 is a monovalent group having a structure represented by the following formula (50).
Figure imgf000092_0002
In the formula (50), X151 is O, S, or C(R161)(R162). One of R151 to R160 is a single bond which bonds with L101. One or more sets of adjacent two or more of R151 to R154 and one or more sets of adjacent two or more of R155 to R160, which are not a single bond which bonds with L101, 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. R161 and R162 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. R161 and R162 which do not form the substituted or unsubstituted, saturated or unsaturated ring, and R151 to R160 which are not a single bond which bonds with L101 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 unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, -Si(R121)(R122)(R123), -C(=O)R124, -COOR125, -N(R126)(R127), a halo- gen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group includ- ing 5 to 50 ring atoms. Ar101, 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 L101 in the formula (50) is not particularly limited. In one embodiment, one of R151 to R160 in the formula (50) is a single bond which bonds with L101. In one embodiment, Ar101 is a monovalent group represented by the following formula (50-R152),
Figure imgf000093_0001
In the formulas (50-R152), (50-R153), (50-R154), (50-R157), and (50-R158), X151, R151 to R160 are as defined in the formula (50). * is a single bond which bonds with L101. As for the compound represented by the formula (10), the following compounds can be given as specific examples. The compound represented by the formula (10) is not limited to these spe- cific examples. In the following specific examples, "D" represents a deuterium atom.
Figure imgf000094_0001
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
Figure imgf000105_0001
Figure imgf000106_0001
Figure imgf000107_0001
In the case that 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, wherein preferred hosts are mentioned above, preferably the at least one compound represented by formula (10) 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. Alternatively, 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. The organic EL device according to one aspect of the invention may be, for example, a fluores- cent or phosphorescent monochromatic light emitting device or a fluorescent/phosphorescent hybrid white light emitting device. Preferably, 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. In addition, 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. In this case, for example, 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. As the simple type organic EL device, 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. (a) (Hole-injecting layer/) Hole-transporting layer/Fluorescent emitting layer (/Electron- transport- ing layer/Electron-injecting layer) (b) (Hole-injecting layer/) Hole-transporting layer/Phosphorescent emitting layer (/Electron-trans- porting layer/Electron-injecting layer) (c) (Hole-injecting layer/) Hole-transporting layer/First fluorescent emitting layer/Second fluores- cent emitting layer (/Electron-transporting layer/Electron-injecting layer) (d) (Hole-injecting layer/) Hole-transporting layer/First phosphorescent layer/Second phospho- rescent layer (/Electron-transporting layer/Electron-injecting layer) (e) (Hole-injecting layer/) Hole-transporting layer/Phosphorescent emitting layer/Spacing layer /Fluorescent emitting layer (/Electron-transporting layer/Electron-injecting layer) (f) (Hole-injecting layer/) Hole-transporting layer/First phosphorescent emitting layer/Second phosphorescent emitting layer/Spacing layer/Fluorescent emitting layer (/Electron-transporting layer/Electron-injecting layer) (g) (Hole-injecting layer/) Hole-transporting layer/First phosphorescent layer/Spacing layer/ Sec- ond phosphorescent emitting layer/Spacing layer/Fluorescent emitting layer (/Electron-trans- porting layer / Electron-injecting layer) (h) (Hole-injecting layer/) Hole-transporting layer/Phosphorescent emitting layer/Spacing layer/First fluorescent emitting layer/Second fluorescent emitting layer (/Electron-transporting Layer/Electron-injecting Layer) (i) (Hole-injecting layer/) Hole-transporting layer/Electron-blocking layer/Fluorescent emitting layer (/Electron-transporting layer/Electron-injecting layer) (j) (Hole-injecting layer/) Hole-transporting layer/Electron-blocking layer/Phosphorescent emit- ting layer (/Electron-transporting layer /Electron-injecting layer) (k) (Hole-injecting layer/) Hole-transporting layer/Exciton-blocking layer/Fluorescent emitting layer (/Electron-transporting layer/Electron-injecting layer) (l) (Hole-injecting layer/) Hole-transporting layer/Exciton-blocking layer/Phosphorescent emitting layer (/Electron-transporting layer/Electron-injecting layer) (m) (Hole-injecting layer/) First hole-transporting Layer/Second hole-transporting Layer/ Fluores- cent emitting layer (/Electron-transporting layer/electron-injecting Layer) (n) (Hole-injecting layer/) First hole-transporting layer/Second hole-transporting layer/ Fluores- cent emitting layer (/First electron-transporting layer/Second electron-transporting layer /Elec- tron-injection layer) (o) (Hole-injecting layer/) First hole-transporting layer /Second hole-transporting layer/Phospho- rescent emitting layer (/Electron-transporting layer /Electron-injecting Layer) (p) (Hole-injecting layer/) First hole-transporting layer/Second hole-transporting layer /Phospho- rescent emitting layer (/First electron-transporting Layer/Second electron-transporting layer /Electron-injecting layer) (q) (Hole-injecting layer/) Hole-transporting layer/Fluorescent emitting layer/Hole-blocking layer (/Electron-transporting layer/Electron-injecting layer) (r) (Hole-injecting layer /) Hole-transporting layer/Phosphorescent emitting layer/ Hole-blocking layer (/ Electron-transport layer/ Electron-injecting layer) (s) (Hole-injecting layer/) Hole-transporting layer/Fluorescent emitting layer /Exciton-blocking layer (/Electron-transporting layer/Electron-injecting layer) (t) (Hole-injecting layer/) Hole-transporting layer/Phosphorescent emitting layer /Exciton- block- ing layer (/Electron-transporting layer/Electron-injecting layer) The layer structure of the organic EL device according to one aspect of the invention is not lim- ited to the examples mentioned above. For example, 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. For example, 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. 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. As a representative device configuration of a tandem type organic EL device, for example, 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. Hereinbelow, an explanation will be made on function, materials, etc. of each layer constituting the organic EL device described in the present specification. (Substrate) 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. As a substrate, a flexible substrate can be used. The flexible substrate means a substrate that can be bent (flexible), and examples thereof include a plastic substrate and the like. Specific examples of 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. Also, an inorganic vapor deposited film can be used. (Anode) As 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. In addition, it is also possi- ble to use gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (e.g. titanium oxide). The anode is normally formed by depositing these materials on the substrate by a sputtering method. For example, 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. Further, 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. As other methods for forming the anode, 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. (Hole-transporting layer) / (Hole-injecting layer) 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. Specific examples for acceptor materials are, quinone compounds with one or more electron withdrawing groups, such as F4TCNQ (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. 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. Specific examples for compounds for the hole transporting layer are represented by the general formula (H),
Figure imgf000113_0002
wherein Ar1’ to Ar3’ 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 Ar1’ to Ar3’ may be bonded to each other to form a ring structure, such as a carbazole ring structure, or a acridane ring structure. Preferably, at least one of Ar1’ to Ar3’ have additional one aryl or heterocyclic amine substituent, more preferably Ar1’ has an additional aryl amino substituent, at the case of that it is preferable that Ar1’ represents substituted or unsubstituted biphenylene group, substituted or unsubstituted fluorenylene group. Specific examples for the hole transport material are
Figure imgf000113_0001
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. It is preferred that 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. (Emitting layer) 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. For example, a fluorescent emitting compound (fluorescent dopant), a phosphorescent emitting compound (phosphorescent dopant) or the like can be used. 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. Further, 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. Preferably, 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. In some literatures, a dopant material is called a guest material, an emitter or an emitting material. In some literatures, 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. In the present specification, 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 same can be applied to the fluorescent host. In one embodiment, it is preferred that 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- further, it is preferred that the compound (I) be contained in the emitting layer as a blue fluores- cent dopant. In one embodiment, no specific restrictions are imposed on the content of the compound (I) as the dopant material in the emitting layer. In respect of sufficient emission and concentration quenching, the content 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. 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. As the boron-containing compound, a pyrromethene compound, a triphenylborane compound or the like can be given. 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. Specifically, 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- bazole-3-yl)triphenylamine (abbreviation: PCBAPA) or the like can be given. As a green fluorescent dopant, an aromatic amine compound or the like can be given, for exam- ple. Specifically, 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 (abbre- viation: 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), N-[9,10-bis(1,1’-biphenyl-2-yl)]-N-[4-(9H-carbazole-9- yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene- 9-amine (abbreviation: DPhAPhA) or the like can be given, for example. As a red fluorescent dopant, a tetracene compound, a diamine compound or the like can be 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. (Phosphorescent dopant) As a phosphorescent dopant, a phosphorescent emitting heavy metal complex and a phospho- rescent emitting rare earth metal complex can be given. As 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. Examples of rare earth metal complexes include terbium complexes, europium complexes and the like. Specifically, 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 can be given. These rare earth metal complexes are preferable as phosphorescent dopants since rare earth metal ions emit light due to electronic transition between different multiplicity. As a blue phosphorescent dopant, an iridium complex, an osmium complex, a platinum com- plex, or the like can be given, for example. Specifically, 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) or the like can be given. As a green phosphorescent dopant, an iridium complex or the like can be given, for example. Specifically, 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. As a red phosphorescent dopant, an iridium complex, a platinum complex, a terbium complex, a europium complex or the like can be given. Specifically, bis[2-(2’-benzo[4,5-α]thienyl)pyridinato- N,C3’]iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato- N,C2’)iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4- fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octae- thyl-21H,23H-porphyrin platinum(II) (abbreviation PtOEP) or the like can be given. As mentioned above, the emitting layer preferably comprises at least one compound (I) as a do- pant. (Host material) As 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 triarylamine compounds and fused polycyclic aromatic amine compounds can be given, for example. Plural types of host materials can be used in combination. As a fluorescent host, a compound having a higher singlet energy level than a fluorescent do- pant is preferable. For example, a heterocyclic compound, a fused aromatic compound or the like can be given. As 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. In the case that compound (I) is employed as at least one dopant material, 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. As a phosphorescent host, a compound having a higher triplet energy level as compared with a phosphorescent dopant is preferable. For example, a metal complex, a heterocyclic compound, a fused aromatic compound or the like can be given. Among these, an indole compound, a car- bazole 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. (Electron-transporting layer) / (Electron-injecting layer) 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. When the electron-transporting layer is formed of plural layers, 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. According to one embodiment, it is preferred that 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. According to one embodiment, it is preferred that 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. Here, the electron-donat- ing dopant means one having a metal with a work function of 3.8 eV or less. As specific exam- ples thereof, 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. As 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. Examples of the alkali metal compound include an alkali oxide such as Li2O, Cs2O or K2O, and an alkali halide such as LiF, NaF, CsF and KF. Among them, LiF, Li2O and NaF are preferable. Examples of the alkaline earth metal compound 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. Examples of the rare earth metal compound include YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3 and TbF3. Among these, YbF3, ScF3 and TbF3 are preferable. 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. Meanwhile, preferred examples of the ligand 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, β-diketones, and azomethines. Regarding the addition form of the electron-donating dopant, it is preferred that the electron-do- nating dopant be formed in a shape of a layer or an island in the interfacial region. A preferred 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. In a case where 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. After that, 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. In a case where 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. After that, 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. As the electron-transporting material used in the electron- transporting layer other than a compound of the formula (I), an aromatic heterocyclic compound having one or more hetero atoms in the molecule may preferably be used. In particular, a nitro- gen-containing heterocyclic compound is preferable. According to one embodiment, it is preferable that the electron-transporting layer comprises a nitrogen-containing heterocyclic metal chelate. According to the other embodiment, it is preferable that the electron-transporting layer compri- ses a substituted or unsubstituted nitrogen containing heterocyclic compound. Specific exam- ples of preferred heterocyclic compounds for the electron-transporting layer are, 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- midazophenanthridine compounds, benzimidzobenzimidazole compounds, preferably benzimid- azole compounds, imidazopyridine compounds or benzimidazophenanthridine compounds. According to another embodiment, it is preferable the electron-transporting layer comprises a phosphine oxide compound represented as Arp1Arp2ArP3P=O. 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. According to another embodiment, it is preferable that the electron-transporting layer comprises aromatic hydrocarbon compounds. Specific examples of preferred 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. (Cathode) For the cathode, 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. Specific examples of 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. Further, in the case of using a silver paste or the like, a coating method, an inkjet method, or the like can be employed. Moreover, 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. (Spacing 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 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. 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. As the material used for the spacing layer, the same materials as those used in the above-mentioned hole-transporting layer can be given. (Electron-blocking layer, hole-blocking layer, exciton-blocking layer) 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. In order to improve hole block- ing capability, 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. In order to improve triplet block capability, a material having a high triplet level is preferably used. (Method for forming a layer) The method for forming each layer of the organic EL device of the invention is not particularly limited unless otherwise specified. 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. (Film thickness) 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. If the film thickness is too large, a high driving voltage is required to be applied, leading to a lowering in efficiency. In this respect, the film thickness is preferably 0.1 nm to 10 μm, and more preferably 5 nm to 0.2 μm. (Electronic apparatus (electronic equipment)) The present invention further relates to an electronic equipment (electronic apparatus) compris- ing the organic electroluminescence device according to the present application. Examples of 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. EXAMPLES Next, the invention will be explained in more detail in accordance with the following synthesis examples, examples, and comparative examples, which should not be construed as limiting the scope of the invention. The percentages and ratios mentioned in the examples below – unless stated otherwise – are % by weight and weight ratios. I Synthesis Examples All experiments are carried out in protective gas atmosphere. Compound 1 Intermediate 1
Figure imgf000122_0001
Intermediate 1 In a 1 L degassed 3-necked round bottom flask was added 1,2-dibromo-3-iodo-5-methylben- zene (35.1g, 93 mmol), bis(4-(tert-butyl)phenyl)amine (25 g, 89 mmol), Tris(dibenzylideneace- tone)dipalladium(0) (1.66 g, 1.78 mmol), (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphos- phane) (4.2g, 7.1 mmol) and sodium tert-butoxide (12.3 g, 124 mmol). Toluene (500 mL) was then added and the reaction heated under an atmosphere of nitrogen at an oil bath temperature of 130°C for 16 hours. The reaction was then allowed to cool to room temperature and the mix- ture filtered over hyflo. The mother liquor was washed with aqueous saturated sodium hy- drogencarbonate, water and then saturated aqueous sodium chloride and dried over magne- sium sulphate. The solution was then filtered over a pad of silica flushing through with toluene. The solvent was removed under reduced pressure. The crude product was triturated with 2-pro- panol. The precipitate thus formed was then recrystallised from toluene-2-propanol to give the target product (27.4 g, 58% yield) as a white solid which was characterized by by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C27H31Br2N = 527, mass found=528 (M+1) Intermediate 2
Figure imgf000123_0001
The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 1 in place of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneacetone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 2 (63 % yield) was characterized by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C43H48BrClN2 = 706, mass found= 707 (M+1) Intermediate 3
Figure imgf000123_0002
Intermediate 2 Intermediate 3 Intermediate 2 (4 g, 5.65 mmol) dissolved in tButyl-benzene (100 ml) and cooled in a water-ice bath at 0°C under N2. tert-butyllithium (5.95 ml, 11.30 mmol) was added dropwise via a syringe and the resulting reaction mixture was allowed to warm to room temperautre. After 2 hours, lithi- ation of Intermediate 2 was complete. The reaction mixture was cooled at -30°C and then boron tribromide (1M solution in heptane, 1.869 ml, 19.77 mmol) was added dropwise. Upon complete addition, the reaction was allowed to warm to room temperature. Di-isopropylethylamine (4.93 ml, 28.2 mmol) was then added to the reaction and the mixture was heated at an oil bath tem- perature of 165°C for 2 hours. Upon cooling to room temperature, the reaction was quenched by the addition of saturated aqueous ammonium chloride. The organic phase was separated and subsequently washed with saturated aqueous sodium hydrogen carbonate, water and then saturated aqueous sodium chloride and dried over magnesium sulphate and solvent evaporated under reduced pressure. The crude reaction product was then purified by chromatography on silica with a gradien elution of 100% heptane to 10% dichloromethane in heptane. Intermediate 3(0.85g, 23% yield) was isolated as a yellow solid and characterized by by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESIMS: calcd for C43H46BClN2 = 636 mass found = 637 (M+1) Compound 1
Figure imgf000124_0001
Intermediate 3 Compound 1 Intermediate 3 (0.65 g, 1 mmol) was combined with dibenzo[b,d]furan-3-ylboronic acid (0.32 g, 1.5 mmol), palladium(II) acetate (5.7 mg, 0.026 mmol), dicyclohexyl[2′,4′,6′-tris(propan-2-yl)[1,1′ -biphenyl]-2-yl]phosphane (49 mg, 0.1 mmol) and caesium carbonate (0.83 g, 2.55 mmol) were combined in a pre-dried schlenk flask and degassed under N2. Toluene (6mL), EtOH (2.25 mL) and water (2.25 mL) were then added and the reaction heated at an oil bath temperature of 100°C overnight under an atmosphere of N2. The reaction was cooled to room temperature and diluted with toluene and washed sequentially with aqueous saturated sodium hydrogen car- bonate, water and aqueous saturated sodium chloride, dried over magnesium suphate and the solution filtered directly over silica gel washing through with toluene. The solvent was evapo- rated under reduced pressure and the crude residue was stirred in acetone at room temperature for 1 hour. Compound 1 was isolated by filtration (0.7g, 89% yield) and was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wave- length (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C55H53BN2O= 768, mass found= 769 (M+1) UV(PhMe) λonset: 458nm FL(PhMe, λex=400nm) λmax: 455nm Compound 2
Figure imgf000124_0002
The procedure for the synthesis of Intermediate 1 was repeated except for using 3-(tert- butyl)-N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and tri-tert-bu- tylphosphonium tetrafluoroborate in place of (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 4 (75% yield) was characterised by APCI-MS (At- mospheric pressure chemical ionisation). The results are shown below. APCI-MS: calcd. for C39H39BrCl2N2 = 684, mass found=685 (M+1).
Figure imgf000125_0001
The procedure for the synthesis of Intermediate 3 was repeated except for using intermediate 4 in place of Intermediate 2. The obtained Intermediate 5 (34 % yield) was characterized by APCI- MS (Atmospheric pressure chemical ionisation). The results are shown below. APCI-MS: calcd. for C39H37BCl2N2= 614, mass found= 615 (M+1)
Figure imgf000125_0002
Intermediate 5 Compound 2 The procedure for the synthesis of Compound 1 was repeated except for using Intermediate 5 in place of Intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid in place of dibenzo[b,d]furan- 3-ylboronic acid. The obtained Compound 2 (91%) was characterized by by ESI-MS (elec- trospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C63H51BN2O2 = 878, mass found= 879 (M+1) UV(PhMe) λonset: 449nm FL(PhMe, λex=400nm) λmax: 446nm Compound 3
Figure imgf000126_0001
The procedure for the synthesis of Intermediate 4 was repeated except for using 4-(tert-butyl)- N-(4-chlorophenyl)aniline in place of 3-(tert-butyl)-N-(4-chlorophenyl)aniline. The obtained Inter- mediate 6 (88%) was characterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C39H39BrCl2N2 = 684, mass found= 685 (M+1)
Figure imgf000126_0002
The procedure for the synthesis of Intermediate 3 was repeated except for using intermediate 6 in place of Intermediate 2. The obtained Intermediate 7 (34 % yield) was characterized by APCI- MS (Atmospheric pressure chemical ionisation). The results are shown below. APCI-MS: calcd. for C39H37BCl2N2= 614, mass found= 615 (M+1)
Figure imgf000126_0003
Intermediate 7 Compound 3 The procedure for the synthesis of Compound 1 was repeated except for using Intermediate 7 in place of Intermediate 3. The obtained Compound 3 (73%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene The results are shown below ESI-MS: calcd. for C63H51BN2O2 = 878, mass found= 879 (M+1) UV(PhMe) λonset: 458nm FL(PhMe, λex=400nm) λmax: 454nm Compound 4
Figure imgf000127_0001
Intermediate 8 The procedure for the synthesis of Intermediate 1 was repeated except for using 1,2-dibromo-5- (tert-butyl)-3-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained Inter- mediate 8 (78%) was characterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C30H37Br2N = 569, mass found= 570 (M+1)
Figure imgf000127_0002
Intermediate 8 Intermediate 9 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 8 in place of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneacetone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 9 (72 % yield) was characterized by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C46H54BrClN2 = 748, mass found= 749 (M+1)
Figure imgf000128_0001
The procedure for the synthesis of Intermediate 3 was repeated except for using intermediate 9 in place of Intermediate 2. The obtained Intermediate 10 (34 % yield) was characterized by ESI- MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C46H52BClN2 = 678, mass found= 679 (M+1)
Figure imgf000128_0002
The procedure for the synthesis of Compound 1 was repeated except for using Intermediate 10 in place of Intermediate 3. The obtained Compound 4 (92%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C58H59BN2O = 810, mass found= 811 (M+1) UV(PhMe) λonset: 463nm FL(PhMe, λex=400nm) λmax: 459nm Compound 5
Figure imgf000128_0003
Intermediate 8 Intermediate 11 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 8 in place of 1,2-dibromo-3-iodo-5-methylbenzene, 3-(tert-butyl)-N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneacetone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 11 (73 % yield) was characterized by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C46H54BrClN2 = 748, mass found= 749 (M+1)
Figure imgf000129_0001
The procedure for the synthesis of Intermediate 3 was repeated except for using intermediate 11 in place of Intermediate 2. The obtained Intermediate 12 (42% yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C46H52BClN2 = 678, mass found= 679 (M+1)
Figure imgf000129_0002
Intermediate 12 Compound 5 The procedure for the synthesis of Compound 1 was repeated except for using Intermediate 12 in place of Intermediate 3. The obtained Compound 5 (92%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C58H59BN2O = 810, mass found= 811 (M+1) UV(PhMe) λonset: 456nm FL(PhMe, λex=400nm) λmax: 454nm Compound 6
Figure imgf000130_0001
Intermediate 3 Compound 6 The procedure for the synthesis of compound 1 was repeated except for using dibenzo[b,d]fu- ran-4-ylboronic acid in place of dibenzo[b,d]furan-3-ylboronic acid. Compound 6 (62% yield) was characterised by ESI-MS (electrospray ionisation mass spectrometry), maximum ultravio- let absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wave- length (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C55H53BN2O= 768, mass found= 769 (M+1) UV(PhMe) λonset: 458nm FL(PhMe, λex=400nm) λmax: 455nm Compound 7
Figure imgf000130_0002
Intermediate 3 Compound 7 The procedure for the synthesis of compound 1 was repeated except for using dibenzo[b,d]thio- phen-4-ylboronic acid in place of dibenzo[b,d]furan-3-ylboronic acid. Compound 7 (82% yield) was characterised by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C55H53BN2S= 784, mass found= 785 (M+1) UV(PhMe) λonset: 458nm FL(PhMe, λex=400nm) λmax: 454nm Compound 8
Figure imgf000131_0001
Intermediate 13 4-chloroaniline (10.5g, 82 mmol) was combined with 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetra- hydronaphthalene (20g, 75 mmol) in toluene (250 mL) in a 500 mL 3-neck round bottom flask and degassed with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (0.68g, 0.75 mmol), 9,9- Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (1.7g, 3 mmol) and sodium tert-butoxide (10 g, 105 mmol) were then added. The reaction mixture was heated at an oil bath temperature of 120°C for 2 hours. The reaction mixture was then cooled to room temperature and the insolu- ble precipitate was removed by filtration over a pad of celite. The mother liquor was then washed sequentially with 2M aqueous hydrogen chloride solution, water and then saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate and filtered over a pad of silica flushing through with toluene. The solvent was evaporated under reduced pres- sure and the crude residue was dissolved in hot 2-propanol. The fine preciptiate that was formed was removed by filtration and discarded. The solvent was evaporated under reduced pressure and the intermediate 13 was purified by recrystallisation from hexanes. Intermediate 13 (17 g, 72.4% yield) was isolated as a white solid which was characterized by by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C20H24ClN = 313, mass found=314 (M+1)
Figure imgf000131_0002
Intermediate 13 Intermediate 14 In a degassed 500ml three neck round bottomed flask was added 1,2-dibromo-3-iodo-5- methylbenzene (7.4g, 19.6 mmol), Intermediate 13 (12.3g, 39.2 mmol), bis(tri-tert-bu- tylphosphoranyl)palladium (0.4g, 0.78 mmol) and sodium tert-butoxide (5.3g, 54.9 mmol). Tol- uene (200mL) was added and the reaction mixture was heated at an oil bath temperature of 115°C for 3 hours. The reaction was cooled to room temperature and filtered over a pad of celite, washing through with toluene. The mother liquor was then washed sequentially with chloride. The organic phase was dried over MgSO4 and the solvent was evaporated. The crude product was recrystallised from 2-propanol. Intermediate 14 (10.5g, 67.4% yield) was thus isolated and charaterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C47H51BrCl2N2= 792, mass found=793 (M+1).
Figure imgf000132_0001
Intermediate 14 Intermediate 15 Intermediate 14 (9.5 g, 11.9 mmol) dissolved in tButyl-benzene (200 ml) and cooled in a water- ice bath at 0°C under N2. Sec-butyllithium (1.4M solution in cyclohexane, 12.8 ml, 17.9 mmol) was added dropwise via a syringe and the resulting reaction mixture was allowed to warm to room temperature. After 2 hours, lithiation of Intermediate 14 was complete. The reaction mix- ture was cooled at -30°C and then boron tribromide (1M solution in heptane, 17.9 ml, 17.9 mmol) was added dropwise. Upon complete addition, the reaction was allowed to warm to room temperature. The reaction was then heated at an oil bath temperature of 140°C for 2 hours. The reaction was cooled to room temperature and di-isopropylethylamine (4.2 ml, 23.9 mmol) was then added and the mixture allowed to stir at room temperature for 1 hour. The reaction was then quenched by the addition of 10% aqueous sodium acetate and toluene was added to dis- solve any residual precipitate. The organic phase was separated and sequentially washed with saturated aqueous sodium hydrogen carbonate, water and then saturated aqueous sodium chloride and dried over magnesium sulphate. The solvent was concentrated to 50mL under re- duced pressure and the crude product was precipitated by the addition of ethanol. Purification could be achieved by recrystallisation from xylene – 2-propanol mixture. Intermediate 15 (3.2g, 37% yield) was isolated as a yellow solid and characterized by by ESI-MS (electrospray ionisa- tion mass spectrometry). The results are shown below. ESI-MS: calcd. for C47H49BCl2N2= 722, mass found= 723 (M+1)
Figure imgf000132_0002
Intermediate 15 Compound 8 To a 250 mL degassed 3 necked round bottom flask was added Intermediate 15 (3.2g, 4.46 mmol), dibenzo[b,d]furan-4-ylboronic acid (3.8g, 17.8 mmol), palladium(II)acetate (0.1g, 0.44 mmol), [2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl] (0.43g, 0.89 mmol) and cesium carbonate (5.82, 17.8 mmol) followed by toluene (80mL), ethanol (15mL) and water (15mL). The resulting reaction mixture was heated at an oil bath temperature of 100°C overnight under an atomosphere of nitrogen. The reaction mixture was then allowed to cool to room temperature and diluted with ethanol (50mL). The insoluble material was collected by filtration. The filter cake was then dissolved with dichloromethane and filtered over a pad of silica, flushing through with dichloromethane. The solvent was then evaporated to give the desired compound. The ob- tained Compound 8 (84%) was characterized by by ESI-MS (electrospray ionisation mass spec- trometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maxi- mum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C71H63BN2O2 = 986, mass found= 987 (M+1) UV(PhMe) λonset: 457nm FL(PhMe, λex=400nm) λmax: 456nm Compound 9
Figure imgf000133_0001
Intermediate 5 Compound 9 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 5 in place of Intermediate 15 and 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro- lane in place of dibenzo[b,d]furan-4-ylboronic acid. The obtained Compound 9 (97%) was char- acterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet ab- sorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C63H51BN2O2 = 878, mass found= 879 (M+1) UV(PhMe) λonset: 447nm FL(PhMe, λex=400nm) λmax: 445nm Compound 10
Figure imgf000133_0002
Intermediate 5 Compound 10 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 5 in place of Intermediate 15 and 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-diox- aborolane in place of dibenzo[b,d]furan-4-ylboronic acid. The obtained Compound 10 (88%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultravi- olet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wave- length (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C69H63BN2= 931, mass found= 932 (M+1) UV(PhMe) λonset: 446nm FL(PhMe, λex=400nm) λmax: 445nm Compound 11
Figure imgf000134_0001
The procedure for the synthesis of Intermediate 14 was repeated except for using 1,2-dibromo- 5-(tert-butyl)-3-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene and N-(4-chloro- phenyl)aniline in place of Intermediate 13. The obtained Intermediate 16 (71% yield) was char- acterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C42H45BrCl2N2 = 726, mass found=727 (M+1).
Figure imgf000134_0002
The procedure for the synthesis of Intermediate 15 was repeated except for using Intermediate 16 in place of Intermediate 14 and n-butyl lithium in place of sec-butyl lithium. The obtained In- termediate 17 (33 % yield) was characterized by ESI-MS (electrospray ionisation mass spec- trometry) The results are shown below ESI-MS: calcd. for C42H43BCl2N2 = 656, mass found= 657 (M+1)
Figure imgf000135_0001
Intermediate 17 Compound 11 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 17 in place of Intermediate 15. The obtained Compound 11 (95%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C66H57BN2O2 = 920, mass found= 921 (M+1) UV(PhMe) λonset: 454nm FL(PhMe, λex=400nm) λmax: 449nm
Figure imgf000135_0002
Intermediate 17 Compound 12 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 17 in place of Intermediate 15 and 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro- lane in place of dibenzo[b,d]furan-4-ylboronic acid. The obtained Compound 12 (82%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C66H57BN2O2 = 920, mass found= 921 (M+1) UV(PhMe) λonset: 454nm FL(PhMe, λex=400nm) λmax: 449nm Compound 13
Figure imgf000136_0001
Intermediate 17 Compound 13 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 17 in place of Intermediate 15 and 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-diox- aborolane in place of dibenzo[b,d]furan-4-ylboronic acid. The obtained Compound 13 (82%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultravi- olet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wave- length (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C72H69BN2 = 973, mass found= 974 (M+1) UV(PhMe) λonset: 453nm FL(PhMe, λex=400nm) λmax: 449nm Compound 14
Figure imgf000136_0002
Intermediate 18 The procedure for the synthesis of Intermediate 13 was repeated except for using 2-bromo-4- (tert-butyl)aniline in place of 4-chloroaniline and 1-chloro-4-iodobenzene in place of 6-bromo- 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene. The obtained Intermediate 18 (82%) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C16H17BrClN = 337, mass found= 338 (M+1)
Figure imgf000136_0003
Intermediate 19 To a 250 mL 3-necked round bottom flask was added trifluoroacetic acid (46.3 ml, 601 mmol), dichloromethane (30 ml) and 1-bromo-4-(tert-butyl)benzene (16.27 ml, 94 mmol). The reaction mixture was cooled in a water-ice bath and N-iodosuccinimide (25.3g, 113 mmol) was added portionwise. Upon complete addition of the N-iodosuccinimide, the ice-water bath was re- moved and the reaction was allowed to continue at room temperature for 6 hours. The reac- tion was then cooled again in a water-ice bath and N-iodosuccinimide (16.9g, 75 mmol) was added portionwise to the reaction followed by trifluoromethane sulfonic acid (12.5mL, 141mmol) and the reaction was allowed to continue overnight coming slowly to room tempera- ture. A further portion of N-iodosuccinimide (2.5g, 11.1 mmol) was added and the reaction al- lowed to continue for another 4 hours. The reaction mixture was then quenched by slowly pouring over ice cold 30% aqueous sodium hydroxide solution while stirring.10% aqueous so- dium thiosulfate (250mL) was then added. The crude product was then extracted with di- chloromethane. The solvent was evaporated and the crude product was recrystallised from ethyl acetate-methanol mixure. Intermediate 19 (38.4g, 88%) was characterised by 1H NMR (270MHz, CD2Cl2) 7.90ppm (2H, s); 1.30ppm (9H, s).
Figure imgf000137_0001
Intermediate 19 Intermediate 18 Intermediate 20 The procedure for the synthesis of Intermediate 1 was repeated except for using Intermediate 19 in place of 1,2-dibromo-3-iodo-5-methylbenzene and Intermediate 18 in place of bis(4- (tert-butyl)phenyl)amine and xylene in place of toluene. The obtained Intermediate 20 (63% yield) was characterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C26H27Br2ClIN = 673, mass found= 674 (M+1)
Figure imgf000137_0002
Intermediate 20 Intermediate 18 Intermediate 21 The procedure for the synthesis of Intermediate 1 was repeated except for using Intermediate 20 in place of 1,2-dibromo-3-iodo-5-methylbenzene and Intermediate 18 in place of bis(4- (tert-butyl)phenyl)amine and xylene in place of toluene. The obtained Intermediate 21 (44% yield) was characterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C42H43Br3Cl2N2 = 882, mass found= 883 (M+1)
Figure imgf000138_0001
Intermediate 21 (4.9g, 5.6mmol) was dissolved tert-butylbenzene (50mL) in a 100 mL 3 neck round bottom flask under nitrogen and cooled to <10°C in a water-ice bath. Secondary-butyl- lithium (12mL, 16.8 mmol, 1.4M in cyclohexane) was added and the reaction mixture was al- lowed to warm to room temperature and continued for 1 hour. The reaction was then cooled to 0°C in a water-ice bath and trimethoxyborane (2.86mL, 25.2 mmol) was added slowly. Upon complete addtion, the reaction was allowed to warm to room temperature and then heated at an oil bath temperature of 100°C and continued at this temperature for 4 hours. The reaction was then allowed to cool to room temperature. The preciptiate that was formed was collected by filtration and washed with water and then ethanol. Purification by recrystallisation from tolu- ene allowed the isolation of Intermediate 22 (2.95g, 80%) as a yellow solid and was character- ised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C42H43BCl2N2 = 656, mass found= 657 (M+1)
Figure imgf000138_0002
Intermediate 22 Compound 14 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 22 in place of Intermediate 15. The obtained Compound 14 (88%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C66H57BN2O2 = 920, mass found= 921 (M+1) UV(PhMe) λonset: 462nm FL(PhMe, λex=400nm) λmax: 458nm Compound 15
Figure imgf000139_0001
The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 22 in place of Intermediate 15 and 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-diox- aborolane in place of dibenzo[b,d]furan-4-ylboronic acid. The obtained Compound 15 (97%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultravi- olet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wave- length (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C72H69BN2 = 973, mass found= 973 (M) UV(PhMe) λonset: 461nm FL(PhMe, λex=400nm) λmax: 458nm Compound 16
Figure imgf000139_0002
Intermediate 1 Intermediate 13 Intermediate 23 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 1 in place of 1,2-dibromo-3-iodo-5-methylbenzene, Intermediate 13 in place of bis(4-(tert-bu- tyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneace- tone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The ob- tained Intermediate 23 (60 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C47H54BrClN2 = 762, mass found= 763 (M+1)
Figure imgf000140_0001
Intermediate 23 Intermediate 24 The procedure for the synthesis of Intermediate 15 was repeated except for using intermedi- ate 23 in place of Intermediate 14. The obtained Intermediate 24 (18 % yield) was character- ized by ESI-MS (Electrospray ionisation). The results are shown below. ESI-MS: calcd. for C47H52BClN2 = 691, mass found= 692 (M+1)
Figure imgf000140_0002
The procedure for the synthesis of compound 1 was repeated except for using Intermediate 24 in place of Intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid in place of dibenzo[b,d]furan- 3-ylboronic acid. Compound 16 (94% yield) was characterised by ESI-MS (electrospray ionisa- tion mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in tolu- ene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The re- sults are shown below. ESI-MS: calcd. for C59H59BN2O= 823, mass found= 724 (M+1) UV(PhMe) λonset: 459nm FL(PhMe, λex=400nm) λmax: 455nm Compound 17
Figure imgf000141_0001
Intermediate 25 The procedure of the synthesis of Intermediate 1 was repeated except for using, 3-(tert-butyl)- N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine. The obtained Intermediate 25 (69 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C23H22Br2ClN = 508, mass found= 509 (M+1)
Figure imgf000141_0002
Intermediate 25 Intermediate 26 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 25 in place of 1,2-dibromo-3-iodo-5-methylbenzene, 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-[1,1'-bi- phenyl]-2-amine in place of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)pal- ladium in place of tris(dibenzylideneacetone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5- diyl)bis(diphenylphosphane). The obtained Intermediate 26 (46 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C49H52BrClN2 = 784, mass found= 785 (M+1)
Figure imgf000141_0003
Intermediate 26 Intermediate 27 The procedure for the synthesis of Intermediate 15 was repeated except for using intermediate 26 in place of Intermediate 14. The obtained Intermediate 27 (19 % yield) was characterized by ESI-MS (Electrospray pressure chemical ionisation). The results are shown below.
Figure imgf000142_0001
Intermediate 27 Compound 17 The procedure for the synthesis of compound 1 was repeated except for using intermediate 27 in place of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid in place of dibenzo[b,d]furan- 3-ylboronic acid. Compound 17 (82% yield) was characterised by ESI-MS (electrospray ionisa- tion mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in tolu- ene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The re- sults are shown below. ESI-MS: calcd. for C61H57BN2O= 845, mass found= 846 (M+1) UV(PhMe) λonset: 457nm FL(PhMe, λex=400nm) λmax: 456nm
Figure imgf000142_0002
Intermediate 28 The procedure of the synthesis of Intermediate 1 was repeated except for using, 3-(tert-butyl)- N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-5-(tert-bu- tyl)-3-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained Intermediate 28 (62 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C26H28Br2ClN = 550, mass found= 550 (M+)
Figure imgf000143_0001
The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 28 in place of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneacetone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 29 (60 % yield) was characterized by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C42H45BrCl2N2 = 729, mass found= 729 (M+)
Figure imgf000143_0002
The procedure for the synthesis of Intermediate 15 was repeated except for using intermediate 29 in place of Intermediate 14. The obtained Intermediate 30 (30 % yield) was characterized by ESI-MS (Electrospray ionisation). The results are shown below. ESI-MS: calcd. for C42H43BCl2N2 = 657, mass found= 658 (M+1)
Figure imgf000143_0003
The procedure for the synthesis of compound 8 was repeated except for using intermediate 30 in place of intermediate 15. Compound 18 (82% yield) was characterised by ESI-MS (elec- λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C66H57BN2O2= 921, mass found= 922 (M+1) UV(PhMe) λonset: 456nm FL(PhMe, λex=400nm) λmax: 454nm Compound 19
Figure imgf000144_0001
The procedure for the synthesis of Intermediate 14 was repeated except for using 1,2-dibromo- 5-(tert-butyl)-3-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene and 3-(tert-butyl)- N-(3-chlorophenyl)aniline in place of Intermediate 13. The obtained Intermediate 31 (81% yield) was characterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C42H45BrCl2N2 = 728, mass found=729 (M+1).
Figure imgf000144_0002
The procedure for the synthesis of Intermediate 15 was repeated except for using Intermediate 31 in place of Intermediate 14 and n-butyl lithium in place of sec-butyl lithium. The obtained In- termediate 32 (21 % yield) was characterized by ESI-MS (electrospray ionisation mass spec- trometry). The results are shown below. ESI-MS: calcd. for C42H43BCl2N2 = 657, mass found= 657 (M+)
Figure imgf000145_0001
Intermediate 32 Compound 19 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 32 in place of Intermediate 15. The obtained Compound 19 (85%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C66H57BN2O2 = 920, mass found= 921 (M+1) UV(PhMe) λonset: 451nm FL(PhMe, λex=400nm) λmax: 449nm Compound 20
Figure imgf000145_0002
Intermediate 33 The procedure for the synthesis of Intermediate 13 was repeated except for using 5-bromo-2- chloro-1,3-dimethylbenzene in place of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphtha- lene and 3-(tert-butyl)aniline in place of 4-chloroaniline. The obtained Intermediate 33 (93% yield) was characterised by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below.
Figure imgf000145_0003
Intermediate 33 Intermediate 34 The procedure for the synthesis of Intermediate 14 was repeated except for using 2-bromo-1,3- diiodo-5-methylbenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene and intermediate 33 in place of Intermediate 13. The obtained Intermediate 34 (64% yield) was characterised by ESI- MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C43H47BrCl2N2 = 743, mass found=743 (M+).
Figure imgf000146_0001
Intermediate 34 Intermediate 35 The procedure for the synthesis of Intermediate 15 was repeated except for using Intermediate 34 in place of Intermediate 14. The obtained Intermediate 35 (18 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C43H45BCl2N2 = 670, mass found= 671 (M+1)
Figure imgf000146_0002
The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 35 in place of Intermediate 15 and dibenzo[b,d]furan-3-ylboronic acid in place of dibenzo[b,d]furan- 4-ylboronic acid. The obtained Compound 20 (70%) was characterized by by ESI-MS (elec- trospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C67H59BN2O2 = 935, mass found= 936 (M+1) UV(PhMe) λonset: 450nm FL(PhMe, λex=400nm) λmax: 447nm (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C70H65BN2O2 = 977, mass found= 978 (M+1) UV(PhMe) λonset: 450nm FL(PhMe λex=400nm) λmax: 446nm Compound 21
Figure imgf000147_0001
The procedure of the synthesis of Intermediate 1 was repeated except for using, 3-(tert-butyl)- N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine. The obtained Intermediate 36 (92 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C23H22Br2ClN = 507, mass found= 507 (M+)
Figure imgf000147_0002
Intermediate 36 Intermediate 37 The procedure for the synthesis of Intermediate 13 was repeated except for using 5,5,8,8-tetra- methyl-5,6,7,8-tetrahydronaphthalen-2-amine in place of 4-chloroaniline and Intermediate 36 in place of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene and (2,2’-bis(diphe- nylphosphino)-1,1’-binaphthyl) in place of 9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 37 (54% yield) was characterised by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C37H42BrClN2 = 630, mass found= 631 (M+1).
Figure imgf000147_0003
Intermediate 37 Intermediate 38 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 37 in place of bis(4-(tert-butyl)phenyl)amine and 1-bromo-4-(tert-butyl)-2-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained Intermediate 38 (65 % yield) was character- ized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C47H53Br2ClN2 = 841, mass found= 841 (M+)
Figure imgf000148_0001
Intermediate 38 Intermediate 39 Intermediate 38 (6.3g, 7.26 mmol) was dissolved in tert-butyl benzene and degassed under ni- trogen. The solution was cooled to -15°C in an salt-ice bath and tertiaty butyl lithium (15.3L, 29.1 mmol, 1.7M in hexanes) was added. Upon complete addition, the reaction was warmed to room temperature for 1.5 hours. Trimethoxy borane (2.4mL, 21.8 mmol) was then added and the reaction allowed to continue at room temperature. After 2 hours, the reaction was cooled at - 65°C in an acetone-dry ice bath. Boron tribromide (4.1mL, 43.6 mmol) was then added and the reaction allowed to continue overnight coming slowly to room temerpature. Di-isopropyl ethyl amine (11.4mL, 65.4 mmol) was then added and the reaction was allowed to continue for a fur- ther 4 hours. The reaction was then diluted with ethanol (300mL) and the yellow solid (1.1g, 21.9% yield) was collected by filtration and used without further purification. The obtained Inter- mediate 39 was characterized by ESI-MS (electrospray ionisation mass spectrometry). The re- sults are shown below. ESI-MS: calcd. for C47H52BClN2 = 691, mass found= 692 (M+1)
Figure imgf000148_0002
Intermediate 39 Compound 21 The procedure for the synthesis of Compound 1 was repeated except for using Intermediate 39 in place of Intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid in place of dibenzo[b,d]furan- 3-ylboronic acid. The obtained Compound 21 (31%) was characterized by by ESI-MS (elec- trospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C59H59BN2O = 823, mass found= 824 (M+1) UV(PhMe) λonset: 450nm FL(PhMe, λex=400nm) λmax: 447nm
Figure imgf000149_0001
Intermediate 13Intermediate 28
Figure imgf000149_0002
The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 28 in place of 1,2-dibromo-3-iodo-5-methylbenzene, Intermediate 13 in place of bis(4-(tert-bu- tyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneace- tone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The ob- tained Intermediate 40 (78 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C46H51BrCl2N2 = 782, mass found= 793 (M+1)
Figure imgf000149_0003
The procedure for the synthesis of Intermediate 15 was repeated except for using Intermediate 40 in place of Intermediate 14. The obtained Intermediate 41 (29 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C46H49BCl2N2 = 711, mass found= 711 (M+1)
Figure imgf000150_0001
The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 41 in place of Intermediate 15. The obtained Compound 22 (91%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C70H63BN2O2 = 975, mass found= 975 (M+) UV(PhMe) λonset: 456nm FL(PhMe, λex=400nm) λmax: 457nm
Figure imgf000150_0002
Intermediate 42 The procedure for the synthesis of Intermediate 14 was repeated except for using 1,2-dibromo- 3-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene and 3-(tert-butyl)-N-(4-chloro- phenyl)aniline in place of Intermediate 13. The obtained Intermediate 42 (82% yield) was char- acterised by ESI-MS (Electrospray ionisation). The results are shown below. ESI-MS: calcd. for C38H37BrCl2N2 = 672, mass found=673 (M+1).
Figure imgf000150_0003
Intermediate 42 Intermediate 43 The procedure for the synthesis of Intermediate 15 was repeated except for using intermediate 42 in place of Intermediate 14. The obtained Intermediate 43 (35 % yield) was characterized by ESI-MS (Electrospray ionisation). The results are shown below. ESI-MS: calcd. for C38H35BCl2N2 = 601, mass found= 602 (M+1)
Figure imgf000151_0001
Intermediate 43 Compound 23 The procedure for the synthesis of Compound 8 was repeated except for using Intermediate 43 in place of Intermediate 15. The obtained Compound 23 (97%) was characterized by by ESI-MS (electrospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C62H49BN2O2 = 865, mass found= 866 (M+1) UV(PhMe) λonset: 452nm FL(PhMe, λex=400nm) λmax: 448nm Compound 24
Figure imgf000151_0002
Intermediate 44 The procedure of the synthesis of Intermediate 1 was repeated except for using, 3-(tert-butyl)- N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-3-iodoben- zene in place of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained Intermediate 44 (91 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C22H20Br2ClN = 494, mass found= 494 (M+)
Figure imgf000152_0001
The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 44 in place of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline in place of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneacetone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 45 (72 % yield) was characterized by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C38H37BrCl2N2 = 672, mass found= 672 (M+)
Figure imgf000152_0002
Intermediate 45 Intermediate 46 The procedure for the synthesis of Intermediate 15 was repeated except for using intermediate 45 in place of Intermediate 14. The obtained Intermediate 46 (35 % yield) was characterized by ESI-MS (Electrospray ionisation). The results are shown below. ESI-MS: calcd. for C38H35BCl2N2 = 601, mass found= 602 (M+1)
Figure imgf000152_0003
The procedure for the synthesis of compound 8 was repeated except for using intermediate 46 in place of intermediate 15. Compound 24 (96% yield) was characterised by ESI-MS (elec- trospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C62H49BN2O2 = 865, mass found= 866 (M+1) UV(PhMe) λonset: 452nm FL(PhMe, λex=400nm) λmax: 448nm Compound 25
Figure imgf000153_0001
Intermediate 47 The procedure of the synthesis of Intermediate 1 was repeated except for using 4- (dibenzo[b,d]furan-4-yl)aniline in place of bis(4-(tert-butyl)phenyl)amine and 1-bromo-4-(tert-bu- tyl)-2-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene and (2,2′-bis(diphe- nylphosphino)-1,1′-binaphthyl) in place of (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphe- nylphosphane). The obtained Intermediate 47 (97 % yield) was characterized by ESI-MS (elec- trospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C28H24BrNO = 469, mass found= 470 (M+1).
Figure imgf000153_0002
The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 47 in place of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-5-(tert-butyl)-3-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained Intermediate 48 (94 % yield) was charac- terized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C38H34Br3NO = 757, mass found= 758 (M+1).
Figure imgf000154_0001
Intermediate 48 Intermediate 49 The procedure of the synthesis of Intermediate 1 was repeated except for using 9,9-dimethyl- 9H-fluoren-2-amine in place of bis(4-(tert-butyl)phenyl)amine and Intermediate 48 in place of 1,2-dibromo-3-iodo-5-methylbenzene and (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) in place of (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 49 (73 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The re- sults are shown below. ESI-MS: calcd. for C53H48Br2N2O = 886, mass found= 887 (M+1).
Figure imgf000154_0002
Intermediate 49 Intermediate 50 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 49 in place of bis(4-(tert-butyl)phenyl)amine and 1-bromo-4-(tert-butyl)-2-iodobenzene in place of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained Intermediate 50 (89 % yield) was character- ized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C53H48Br2N2O = 1074, mass found= 1075 (M+1).
Figure imgf000154_0003
Intermediate 50 Compound 25 The procedure of the synthesis of Intermediate 22 was repeated except for using Intermediate 50 in place of Intermediate 21. Compound 25 (72% yield) was characterised by ESI-MS (elec- trospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C63H59BN2O= 871, mass found= 872 (M+1) UV(PhMe) λonset: 454nm FL(PhMe, λex=400nm) λmax: 451nm Compound 26 Intermediate 44 Intermediate 51 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 44 in place of 1,2-dibromo-3-iodo-5-methylbenzene, N-(4-(tert-butyl)phenyl)-[1,1':3',1''-terphenyl]- 4'-amine in place of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5- diyl)bis(diphenylphosphane). The obtained Intermediate 51 (72 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C50H46BrClN2 = 788, mass found= 788 (M+) Intermediate 51 Intermediate 52 The procedure for the synthesis of Intermediate 15 was repeated except for using intermediate 51 in place of Intermediate 14. The obtained Intermediate 52 (33 % yield) was characterized by ESI-MS: calcd. for C50H44BClN2 = 718, mass found= 719 (M+1)
Figure imgf000156_0001
Intermediate 52 Compound 26 The procedure for the synthesis of compound 1 was repeated except for using intermediate 52 in place of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid in place of dibenzo[b,d]furan- 3-ylboronic acid. Compound 26 (92% yield) was characterised by ESI-MS (electrospray ionisa- tion mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in tolu- ene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The re- sults are shown below. ESI-MS: calcd. for C58H43BN2O = 794, mass found= 795 (M+1) UV(PhMe) λonset: 457nm FL(PhMe, λex=400nm) λmax: 454nm Comparative Compound 2
Figure imgf000156_0002
Intermediate 53 The procedure of the synthesis of Intermediate 1 was repeated except for using, diphenyl amine in place of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-3-iodobenzene in place of 1,2-di- bromo-3-iodo-5-methylbenzene. The obtained Intermediate 53 (49 % yield) was characterized by ESI-MS (electrospray ionisation mass spectrometry). The results are shown below. ESI-MS: calcd. for C18H13Br2N = 403, mass found= 403 (M+)
Figure imgf000156_0003
Intermediate 53 Intermediate 54 The procedure of the synthesis of Intermediate 1 was repeated except for using Intermediate 53 in place of 1,2-dibromo-3-iodo-5-methylbenzene, 4-chloro-N-phenylaniline in place of bis(4-(tert- butyl)phenyl)amine and bis(tri-tert-butylphosphoranyl)palladium in place of tris(dibenzyli- deneacetone)dipalladium(0) and (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 54 (55 % yield) was characterized by ESI-MS (electrospray ionisa- tion mass spectrometry). The results are shown below. ESI-MS: calcd. for C30H22BrClN2 = 526, mass found= 526 (M+)
Figure imgf000157_0001
The procedure for the synthesis of Intermediate 3 was repeated except for using intermediate 54 in place of Intermediate 2 and secondary butyl lithium in place of tertiary butyl lithium. The obtained Intermediate 55 (20 % yield) was characterized by ESI-MS (Electrospray ionisation). The results are shown below. ESI-MS: calcd. for C30H20BClN2 = 455, mass found= 456 (M+1)
Figure imgf000157_0002
Intermediate 55 Comparative Compound 2 The procedure for the synthesis of compound 1 was repeated except for using intermediate 55 in place of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid in place of dibenzo[b,d]furan- 3-ylboronic acid. Comparative Compound 2 (81% yield) was characterised by ESI-MS (elec- trospray ionisation mass spectrometry), maximum ultraviolet absorption wavelength (UV(PhMe) λonset) in toluene, and maximum fluorescence wavelength (FL(PhMe, λex=330nm) λmax) in toluene. The results are shown below. ESI-MS: calcd. for C42H27BN2O= 586, mass found= 587 (M+1) UV(PhMe) λonset: 457nm FL(PhMe, λex=400nm) λmax: 452nm Device (invented compound as emitter/dopant) Preparation and Evaluation of Organic EL Devices The organic EL devices were prepared and evaluated as follows: Application Example 1 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 Å/sec at about 10-6 -10-8 mbar. As a hole injection layer, 10 nm-thick mixture of Compound HT-1 and 3% by weight of compound HI was applied. Then 80 nm-thick of compound HT-1 and 10 nm of Compound HT-2 were applied as hole-transporting layer 1 and hole-transporting layer 2, respectively. Subsequently, a mixture of 2% by weight of an emitter Compound 1 and 98% by weight of host Compound BH-1 was applied to form a 25 nm-thick fluorescent emitting layer. On the emitting layer, 10 nm-thick Compound ET-1 was applied as an hole-blocking layer and 15 nm of Compound ET-2 as electron-transporting layer. Finally, 1 nm-thick LiF was deposited as an electron-injection layer and 50 nm-thick Al was then deposited as a cathode to complete the de- vice. The device was sealed with a glass lid and a getter in an inert nitrogen atmosphere with less than 1 ppm of water and oxygen. To characterize the OLED, electroluminescence (EL) spectra were recorded at various currents and voltages. EL peak maximum and Full Width at Half Maxi- mum (FWHM) were recorded at 10 mA/cm2. In addition, the current-voltage characteristic were measured in combination with the luminance to determine luminous efficiency and external quan- tum efficiency (EQE). Driving voltage (Voltage) was given at a current density of 10mA/cm2. Life- time of OLED device was measured as a decay of the luminance at constant current density of 50 mA/cm2 to 95% of its initial value. The device results are shown in Table 1.
Figure imgf000158_0001
Compound HI Compound HT-1
Figure imgf000159_0001
Application Example 2 Application example 1 was repeated except for using Compound 2 in place of Compound 1 in the emitter layer. The device result is shown in Table 1.
Figure imgf000159_0002
Compound 2 Comparative Application Example 1 Application example 1 was repeated except for using Comparative Compound 1 in place of Com- pound 1 in the emitter layer. The device result is shown in Table 1.
Figure imgf000160_0001
Comparative Compound 1 Table 1
Figure imgf000160_0003
1) Device lifetime measured at a current density of 50 mA/cm2 up to 95% of the initial lumi- nance (at 50mA/cm2), relative to the device lifetime of Comparative Example 1 using the following formula:
Figure imgf000160_0002
These results demonstrate that the lifetime (LT95) is improved in the case that the inventive com- pounds are used instead of the Comparative Compounds as the fluorescent emitting material. Application Example 3 Application Example 1 was repeated except for using the Compound 4 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 4 Application Example 1 was repeated except for using the Compound 5 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 5 Application Example 1 was repeated except for using the Compound 6 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 6 Application Example 1 was repeated except for using the Compound 7 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 7 Application Example 1 was repeated except for using the Compound 8 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 8 Application Example 1 was repeated except for using the Compound 11 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 9 Application Example 1 was repeated except for using the Compound 12 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 10 Application Example 1 was repeated except for using the Compound 13 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 11 Application Example 1 was repeated except for using the Compound 14 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 12 Application Example 1 was repeated except for using the Compound 15 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 13 Application Example 1 was repeated except for using the Compound 16 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 14 Application Example 1 was repeated except for using the Compound 17 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 15 Application Example 1 was repeated except for using the Compound 18 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 16 Application Example 1 was repeated except for using the Compound 19 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 17 Application Example 1 was repeated except for using the Compound 21 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 18 Application Example 1 was repeated except for using the Compound 23 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 19 Application Example 1 was repeated except for using the Compound 24 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 20 Application Example 1 was repeated except for using the Compound 25 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Application Example 21 Application Example 1 was repeated except for using the Compound 26 in place of Compound 1 in the emitter layer. The device results are shown in Table 2. Comparative Application Example 2 Application Example 1 was repeated except for using the Comparative Compound 2 in place of Compound 1 in the emitter layer. The device results are shown in Table 2.
Figure imgf000163_0001
Figure imgf000164_0001
Figure imgf000165_0001
Table 2: Results of the application examples
Figure imgf000166_0001
2) EQE of the device measured at a current density of 10 mA/cm2 relative to the EQE of Comparative Example 2 calculated using the following formula
Figure imgf000167_0001
3) device lifetime measured at a current density of 50 mA/cm2 up to 95% of the initial lumi- nance (at 50mA/cm2), relative to the device lifetime of Comparative Example 2 calcu- lated using the following formula
Figure imgf000167_0002
These results demonstrate that the lifetime and/or efficiency is improved in the case that the in- ventive compounds are used instead of the Comparative Compound 2 as the fluorescent emitting material.

Claims

Claims 1. A compound represented by formula (I)
Figure imgf000168_0001
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R20, R21, R22, R23 and R24 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsub- stituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsub- stituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsub- stituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubsti- tuted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is un- substituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is un- substituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is un- substituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36, NR84R85, or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted, preferably an alkyl ring which is unsubstituted or substituted; wherein at least one of R1, R2, R3 and R4, preferably at least one of R2 and R3, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cyclo- alkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R1, R2, R3 and R4, preferably R2 and R3 together form an alkyl ring which is unsubstituted or substituted; at least one of R5, R6, R7 and R8, preferably at least one of R6 and R7, represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cyclo- alkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or two adjacent residues R5, R6, R7 and R8, preferably R6 and R7 together form an alkyl ring which is unsubstituted or substituted; and at least one of R21, R22 and R23 represents a group HAr; Y represents a group HAr or RY wherein RY represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is un- substituted or substituted; a N-heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is un- substituted or substituted; an alkylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36, NR84R85, or halogen; or RY forms with an adjacent residue at L a ring which is unsubstituted or substituted; and HAr represents a group of formula (II)
Figure imgf000169_0001
wherein R12, R13, R14, R15, R16, R17, R18 and R19 each independently represents hydrogen; an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a het- eroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an aralkyl group having from 7 to 30 carbon atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an al- kylhalide group having from 1 to 20 carbon atoms which is unsubstituted or substituted; an alkenyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; an alkynyl group having from 2 to 20 carbon atoms which is unsubstituted or substituted; a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substi- tuted; CN; NO2; OR30; SR31; C(=O)R32; COOR33; SiR34R35R36; NR84R85, or halogen; or two adjacent residues together form a ring structure which is unsubstituted or substituted; one of R12, R13, R14, R15, R16, R17, R18 and R19 is a bonding site; X is O, S or CR25R26; L represents a divalent aryl group having from 6 to 30 ring carbon atoms which is unsub- stituted or substituted; a divalent heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; a divalent alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted; or a divalent cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted;; R30, R31, R32, R33 , R34, R35 and R36 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted or a cycloalkyl group hav- ing from 3 to 20 ring carbon atoms which is unsubstituted or substituted; R25, R26 each independently represents an aryl group having from 6 to 30 ring carbon at- oms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring at- oms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon at- oms which is unsubstituted or substituted or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or R25 and R26 together form a ring structure which is unsubstituted or substituted; R84 and R85 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; an alkyl group having from 1 to 20 carbon at- oms which is unsubstituted or substituted or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted; or together form a ring structure which is unsubstituted or substituted; n represents 0,1, 2 or 3; preferably 0, 1 or 2; more preferably 0 or 1.
2. The compound according to claim 1, wherein at least one of R2 and R3 represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cyclo- alkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or R2 and R3 together form a ring structure which is unsubstituted or substituted, preferably an alkyl ring which is unsubstituted or substituted.
3. The compound according to claim 1 or 2, wherein at least one of R6 and R7 represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substi- tuted, or R6 and R7 together form a ring structure which is unsubstituted or substituted, preferably an alkyl ring which is unsubstituted or substituted.
4. The compound according to any one of claims 1 to 3, wherein at least one of R9, R10 and R11, preferably R10 represents hydrogen, an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; NR84R85, or R9 and R10 and/or R10 and R11 together form a ring structure which is unsubstituted or sub- stituted, preferably an alkyl ring which is unsubstituted or substituted.
5. The compound according to any one of claims 1 to 4, wherein R22 is HAr or wherein R21 is HAr
6. The compound according to any one of claims 1 to 5, wherein n is 0 or 1.
7. The compound according to any one of claims 1 to 6, wherein the compound is repre- sented by one of the following formulae
Figure imgf000171_0001
8. The compound according to any one of claims 1 to 7, wherein R1, R4, R5, R8, R9, R11, R20 and R24 are hydrogen; or R1, R4, R5, R8, R9 and R11 are hydrogen and R20 and R24 each independently represents hydrogen or an aryl group having from 6 to 30 ring carbon at- oms.
9. The compound according to any one of claims 1 to 8, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R11 do not represent an amino group NR84R85.
10. The compound according to any one of claims 1 to 9, wherein the compound is repre- sented by one of the following formulae
Figure imgf000172_0001
wherein R1, R4, R5, R8, R9, R11, R20 and R24 are hydrogen; or R1, R4, R5, R8, R9 and R11 are hydro- gen and R20 and R24 each independently represents hydrogen or an aryl group having from 6 to 30 ring carbon atoms; at least one of R2 and R3 represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, and the remaining residue R2 or R3 is hydro- gen; or R2 and R3 together form an alkyl ring which is unsubstituted or substituted; at least one of R6 and R7 represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, and the remaining residue R6 or R7 is hydro- gen; or R6 and R7 together form an alkyl ring which is unsubstituted or substituted; R10 represents hydrogen, an alkyl group having from 1 to 20 carbon atoms which is un- substituted or substituted, a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubstituted or substituted, or NR84R85; or an aryl group having from 6 to 30 ring car- bon atoms; RY represents an alkyl group having from 1 to 20 carbon atoms which is unsubstituted or substituted, or a cycloalkyl group having from 3 to 20 ring carbon atoms which is unsubsti- tuted or substituted, or RY forms with an adjacent at L an alkyl ring which is unsubstituted or substituted; or RY represents hydrogen or an aryl group having from 6 to 30 ring carbon atoms; R84 and R85 each independently represents an aryl group having from 6 to 30 ring carbon atoms which is unsubstituted or substituted; a heteroaryl group having from 5 to 30 ring atoms which is unsubstituted or substituted; L represents a phenylene group which is unsubstituted or substituted; and n is 0 or 1.
11. A material, preferably an emitter material, for an organic electroluminescence device, comprising at least one compound according to any one of claims 1 to 10.
12. An organic electroluminescence device comprising at least one compound according to any one of claims 1 to 10.
13. The organic electroluminescence device according to claim 12, comprising a cathode, an anode and one or more organic thin film layers comprising an emitting layer disposed be- tween the cathode and the anode, wherein at least one layer of the organic thin film layers comprises at least one compound according to any one of claims 1 to 10.
14. The organic electroluminescence device according to claim 13, wherein the light emitting layer comprises at least one compound according to any one of claims 1 to 10.
15. The organic electroluminescence device according to claim 14, wherein the light emitting layer comprises at least one host and at least one dopant, wherein the dopant comprises at least one compound according to any one of claims 1 to 10.
16. The organic electroluminescence device according to claim 15, wherein the host com- prises at least one substituted or unsubstituted fused aromatic hydrocarbon compound and/or at least one substituted or unsubstituted anthracene compound.
17. The organic electroluminescence device according to claim 16, wherein the anthracene compound is represented by the following formula (10):
Figure imgf000174_0001
wherein one or more pairs of two or more adjacent R101 to R110 may form a substituted or unsubsti- tuted, saturated or unsaturated ring; R101 to R110 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 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 car- bon 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 unsub- stituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted al- kylene group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, -Si(R121)(R122)(R123), -C(=O)R124, -COOR125, -N(R126)(R127), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, or a group represented by the following formula (31); R121 to R127 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring to 50 ring atoms; when each of R121 to R127 is present in plural, each of the plural R121 to R127 may be the same or different; provided that at least one of R101 to R110 that do not form the substituted or unsubstituted, saturated or unsaturated ring is a group represented by the following formula (31). If two or more groups represented by the formula (31) are present, each of these groups may be the same or different; -L101-Ar101 (31) wherein in the formula (31), L101 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; Ar101 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
18. An electronic equipment comprising the organic electroluminescence device according to any one of claims 12 to 17.
19. A light emitting layer comprising at least one host and at least one dopant, wherein the do- pant comprises at least one compound according to any one of claims 1 to 10.
20. Use of a compound of formula (I) according to any one of claims 1 to 10 in an organic electroluminescence device.
PCT/IB2023/057218 2022-07-14 2023-07-14 Compound and an organic electroluminescence device comprising the compound WO2024013709A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22184974 2022-07-14
EP22184974.8 2022-07-14

Publications (1)

Publication Number Publication Date
WO2024013709A1 true WO2024013709A1 (en) 2024-01-18

Family

ID=82608056

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2023/057218 WO2024013709A1 (en) 2022-07-14 2023-07-14 Compound and an organic electroluminescence device comprising the compound

Country Status (1)

Country Link
WO (1) WO2024013709A1 (en)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190127529A (en) 2018-12-19 2019-11-13 머티어리얼사이언스 주식회사 Organic electroluminescent device
US20200176679A1 (en) 2017-05-22 2020-06-04 Material Science Co., Ltd. Organic compound and organic electroluminescent device comprising the same
US20210062078A1 (en) 2017-12-28 2021-03-04 Idemitsu Kosan Co.,Ltd. Novel compound and organic electroluminescence device
US20210066599A1 (en) 2017-12-28 2021-03-04 Idemitsu Kosan Co.,Ltd. Novel compound and organic electroluminescence device
WO2021049889A1 (en) 2019-09-10 2021-03-18 주식회사 엘지화학 Compound and organic light-emitting device comprising same
WO2021223688A1 (en) 2020-05-08 2021-11-11 陕西莱特光电材料股份有限公司 Organic compound, use, and organic electroluminescent device and electronic apparatus using same
US20220093874A1 (en) 2020-09-18 2022-03-24 Samsung Display Co., Ltd. Light emitting device and polycyclic compound for light emitting device

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200176679A1 (en) 2017-05-22 2020-06-04 Material Science Co., Ltd. Organic compound and organic electroluminescent device comprising the same
US20210062078A1 (en) 2017-12-28 2021-03-04 Idemitsu Kosan Co.,Ltd. Novel compound and organic electroluminescence device
US20210066599A1 (en) 2017-12-28 2021-03-04 Idemitsu Kosan Co.,Ltd. Novel compound and organic electroluminescence device
US20220020925A1 (en) 2017-12-28 2022-01-20 Idemitsu Kosan Co.,Ltd. Novel compound and organic electroluminescence device
KR20190127529A (en) 2018-12-19 2019-11-13 머티어리얼사이언스 주식회사 Organic electroluminescent device
WO2021049889A1 (en) 2019-09-10 2021-03-18 주식회사 엘지화학 Compound and organic light-emitting device comprising same
WO2021223688A1 (en) 2020-05-08 2021-11-11 陕西莱特光电材料股份有限公司 Organic compound, use, and organic electroluminescent device and electronic apparatus using same
US20220093874A1 (en) 2020-09-18 2022-03-24 Samsung Display Co., Ltd. Light emitting device and polycyclic compound for light emitting device

Similar Documents

Publication Publication Date Title
KR102515298B1 (en) Light emitting device, display including the same, lighting device and sensor
WO2020217229A1 (en) Polycyclic compound and an organic electroluminescence device comprising the polycyclic compound or the composition
KR102245875B1 (en) Material for organic electroluminescent elements, organic electroluminescent element using same, and electronic device
US20230137925A1 (en) Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound
KR101838833B1 (en) Condensed fluoranthene compound, material for organic electroluminescent element using this compound, organic electroluminescent element using this material, and electronic device
KR20150086095A (en) Organic light-emitting Devices
JPWO2014087657A1 (en) Aromatic amine derivative and organic electroluminescence device
KR20170057729A (en) Nitrile based compound and organic light emitting device comprising the same
JPWO2014148047A1 (en) Amine compound having hetero-fused ring and organic electroluminescence device using the same
US20230416278A1 (en) Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound
US20240043453A1 (en) Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound
WO2024013709A1 (en) Compound and an organic electroluminescence device comprising the compound
KR20200092875A (en) Compound and organic light emitting device comprising the same
EP4215535A1 (en) Compound and an organic electroluminescence device comprising the compound
KR20210062766A (en) Organic electroluminescence device and amine compound for organic electroluminescence device
EP4379018A1 (en) Compound and an organic electroluminescence device comprising the compound
EP4151697A1 (en) Compound and an organic electroluminescence device comprising the compound
US20240244972A1 (en) Compound and an organic electroluminescence device comprising the compound
KR20200067663A (en) Organic luminescent compound and organic electroluminescent device including the same
EP3865486A1 (en) Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound
WO2023228005A1 (en) Compound and an organic electroluminescence device comprising the compound
EP4124619A1 (en) Compound, material for an organic electroluminescence device and an organic electroluminescence device comprising the compound
EP4140994A1 (en) Compound, material for an organic electroluminescence device and an organic electroluminescence device comprising the compound
WO2024043018A1 (en) Organic el element, display device, and lighting device
WO2021132733A1 (en) Polycyclic compound, material for an organic electroluminescence device and an organic electroluminescence device comprising the polycyclic compound

Legal Events

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

Ref document number: 23748605

Country of ref document: EP

Kind code of ref document: A1