WO2010054730A1 - Organische elektrolumineszenzvorrichtungen - Google Patents
Organische elektrolumineszenzvorrichtungen Download PDFInfo
- Publication number
- WO2010054730A1 WO2010054730A1 PCT/EP2009/007406 EP2009007406W WO2010054730A1 WO 2010054730 A1 WO2010054730 A1 WO 2010054730A1 EP 2009007406 W EP2009007406 W EP 2009007406W WO 2010054730 A1 WO2010054730 A1 WO 2010054730A1
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- WO
- WIPO (PCT)
- Prior art keywords
- formula
- group
- aromatic
- atoms
- substituted
- Prior art date
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- KNVVMNKJHCIPRV-UHFFFAOYSA-M lithium;3-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=CC=C2N=C(C([O-])=O)C(O)=CC2=C1 KNVVMNKJHCIPRV-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65844—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a five-membered ring which may be condensed with another ring system
-
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
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- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
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- 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
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- H10K2101/10—Triplet emission
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to organic electroluminescent devices and materials for use in organic
- Electroluminescent devices are Electroluminescent devices.
- OLEDs organic electroluminescent devices
- organic semiconductors organic semiconductors
- Organometallic complexes which exhibit phosphorescence instead of fluorescence are increasingly being used as emitting materials (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, A-6).
- organometallic compounds for quantum mechanical reasons, using organometallic compounds as phosphorescence emitters, an up to fourfold increase in energy and power efficiency is possible.
- the properties of phosphorescent OLEDs are not only determined by the triplet emitters used.
- the other materials used such as matrix materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials are of particular importance. Improvements to these materials can thus also lead to significant improvements in the OLED properties. For fluorescent OLEDs there is still room for improvement with these materials.
- ketones for example according to WO 04/093207 or according to the unpublished application DE 102008033943.1
- phosphine oxides eg according to WO 05/003253
- the object of the present invention is to provide compounds which are suitable for use in a fluorescent or phosphorescent OLED, in particular a phosphorescent OLED, for example as matrix material or as hole transport / electron blocking material or exciton blocking material or as electron transport or hole blocking material.
- a fluorescent or phosphorescent OLED in particular a phosphorescent OLED
- matrix material for example as matrix material or as hole transport / electron blocking material or exciton blocking material or as electron transport or hole blocking material.
- the present invention is an electronic device containing at least one compound according to the following formula (1),
- Z is the same or different at each occurrence, NR 2 , O or S;
- Ar is the same or different at each occurrence an aromatic or heteroaromatic ring system with 5 to 60 aromatic
- Ring atoms which may be substituted by one or more radicals R 1 ;
- Ar 1 is the same or different at each occurrence and is an aryl or heteroaryl group having 5 to 18 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
- X is the same or different CR 1 or N at each occurrence;
- L is a single bond or a bivalent, trivalent or tetravalent group
- Heteroaryloxy with 5 to 60 aromatic ring atoms, which with one or more R 3 may be substituted, or a combination of these systems, optionally two or more adjacent substituents R 1 may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more R 3 radicals ;
- an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 3 , or a combination of these systems;
- those R 1 and R 2 adjacent to one another in the 1, 2-position may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 3 radicals;
- R 3 is selected from the group consisting of H, D, F, CN, aliphatic hydrocarbon radical having 1 to 20 C atoms, aromatic or heteroaromatic ring system having 5 to 30 aromatic
- n is 1 to 10, preferably 1, 2, 3, 4, 5 or 6;
- m is 1 if L is a single bond or a divalent group, or 2 if L is a trivalent group, or 3 if L is a tetravalent group;
- q is the same or different 0 or 1 for each occurrence.
- An aryl group in the sense of this invention contains 6 to 60 C atoms;
- a heteroaryl group contains 2 to 60 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- aryl group or heteroaryl either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.
- aromatics linked to one another by single bond such as, for example, biphenyl, are not designated as aryl or heteroaryl group but as aromatic ring system.
- An aromatic ring system according to this invention contains 6 to 60
- a heteroaromatic ring system in the sense of this invention contains 2 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and
- Heteroatoms at least 5 results.
- the heteroatoms are preferably selected from N, O and / or S.
- An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups Heteroaryl groups by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as.
- a non-aromatic unit preferably less than 10% of the atoms other than H
- an sp 3 -hybridized C, N or O atom may be interrupted.
- systems such as fluorene, 9,9'-spirobifluorene, 9,9-diaryl fluorene, triarylamine, diaryl ether, stilbene, etc. as aromatic ring systems in terms of this
- an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may typically contain 1 to 40 or also 1 to 20 C atoms, and in which also individual H atoms or CH 2 - Groups may be substituted by the abovementioned groups, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-
- alkoxy group having 1 to 40 carbon atoms methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy understood.
- one or more H atoms can also be replaced by D, F, Cl, Br, I, CN or NO 2 , preferably F, Cl or CN, more preferably F or CN, particularly preferably CN.
- an aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms which may be substituted in each case with the above-mentioned radicals R 3 or a hydrocarbon radical and which may be linked via any position on the aromatic or heteroaromatic, are understood in particular groups derived are benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans indenofluorene, cis or trans indolocarbazole, truxene, isotruxene, spirotruxene,
- Diazaanthracene 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, Fluorubin, naphthyridine, azacarbazole, benzo-carboline, phenanthroline, 1, 2,3-triazole, 1, 2,4-triazole, benzotriazole, 1, 2,3-oxadiazole, 1, 2,4-oxadiazole, 1, 2, 5-oxadiazole, 1, 3,4-oxadiazole, 1, 2,3-thiadiazole, 1, 2,4-thiadiazole, 1, 2,5-thiadiazole, 1, 3,4-thiadiazole, 1, 3,5- Triazine, 1, 2,4-triazine, 1, 2,3-triazine
- Ar 1 is preferably the same or different each occurrence of an aryl or heteroaryl group having 5 to 14 aromatic ring atoms, especially preferably with 5 to 10 aromatic ring atoms, very particularly preferably with 6 aromatic ring atoms.
- aryl and heteroaryl groups are Ar 1 the same or different at each occurrence selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, furan, thiophene, pyrrole, naphthalene, phenanthrene, quinoline, isoquinoline, quinoxaline, indole, benzofuran, benzothiophene and carbazole.
- Preferred embodiments of the compounds of formula (1) above are the compounds of formulas (8) to (18),
- n stands, identically or differently for each occurrence, for NR 2 .
- the L symbol represents a single bond, 25 O, S, NR 2, an alkylene group having 1 to 10 carbon atoms, which with one or more radicals R 3 may be substituted, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic Ringaattoommeen which may be substituted with one or more R 3 radicals.
- a maximum of two symbols X in each cycle stand for N and the other symbols X stand the same or different for each occurrence for CR 1 .
- a symbol X is a maximum in each cycle is N and the "5 other symbols X are identical or different at each occurrence for CR 1 .
- all symbols X are the same or different at each occurrence for CR 1 .
- the group Ar represents an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, particularly preferably having 5 to 24 aromatic ring atoms. In this case, preferably none of the aryl or heteroaryl groups of the aromatic or heteroaromatic ring system contains more than 10 aromatic ring atoms.
- Preferred groups Ar are therefore composed of one or more of the groups benzene,
- Particularly preferred groups Ar are each composed of one or more groups benzene, pyridine, pyrimidine, pyridazine,
- Group Ar is triphenylene.
- Ar is selected from the group consisting of the units of the following
- the index q 0.
- the index n 1, 2, 3 or 4, particularly preferably 1, 2 or 3, very particularly preferably 1 or 2.
- the radical R 1 is the same or different at each occurrence selected from the group consisting of H, D 1 F, CN 1 N (R 3 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 20 C.
- the radical R 1 is the same or different at each occurrence selected from the group consisting of H, D, CN, F, a straight-chain alkyl group having 1 to 10 carbon atoms, more preferably having 1 to 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, more preferably having 3 to 6 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, more preferably having 2 to 4 carbon atoms, each having one or more radicals R 3 may be substituted, wherein one or more HI atoms may be replaced by D, an aromatic or heteroaromatic ring system having 5 to 12 aromatic ring atoms, each of which may be substituted by one or more R 3 radicals, or a combination of these systems, optionally two or more adjacent substituents R can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system substituted by one or more R 3 substituents can be tuiert
- R 2 is the same or different selected on each occurrence from the group consisting of a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each with a or several radicals R 3 may be substituted, wherein one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, each of which may be substituted with one or more R 3 radicals, or a combination of these systems;
- those R 1 and R 2 adjacent to one another in the 1, 2-position may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 3 radicals.
- R 2 is the same or different selected on each occurrence from the group consisting of an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted in each case with one or more radicals R 3 .
- R 2 is phenyl, naphthyl, biphenyl or terphenyl, which in each case may be substituted by one or more radicals R 3 , in particular phenyl or biphenyl, which in each case has one or more substituents R 1 may be substituted, but preferably unsubstituted
- Ar 1 is the same or different at each occurrence for an aryl or heteroaryl group having 5 to 14 aromatic ring atoms, more preferably having 5 to 10 aromatic ring atoms, especially
- OK preferably with 6 aromatic ring atoms
- Z is the same or different every occurrence of NR 2 , if it is not
- X stands for CR 1 or N, with a maximum of two symbols X representing N, preferably a maximum of one symbol X;
- Ar is the same or different and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, particularly preferably having 5 to 24 aromatic ring atoms; preferably any of the aryl or heteroaryl groups of the aromatic or heteroaromatic ring system containing more than 10 aromatic 5 ring atoms;
- n is 1, 2, 3 or 4, preferably 1, 2 or 3. 10
- R 1 is identical or different at each occurrence selected from the group consisting of H, D, F, CN, N (R 3 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or one
- Ring system having 5 to 30 aromatic ring atoms, each of which may be substituted by one or more radicals R 3 , an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms which may be substituted by one or more radicals R 3 , or a combination of these systems where optionally two or more
- substituents R can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R 3 ;
- R is the same or different at each occurrence selected from the
- those R 1 and R 2 adjacent to one another in the 1, 2-position may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 3 radicals.
- Ar 1 is identical or different at each occurrence selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, furan, thiophene, pyrrole, naphthalene, quinoline, isoquinoline,
- Z is the same or different at each occurrence of NR 2 if it does not form with A or B a ring according to formula (7);
- X is the same or different every occurrence CR 1 ;
- Ar is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which is composed of one or more of the groups benzene, pyridine, pyrimidine, pyridazine,
- n is 1 or 2;
- R 1 is identical or different at each occurrence selected from the group consisting of H, D 1 F, CN, a straight-chain alkyl group having 1 to 10 carbon atoms, preferably having 1 to 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 C atoms, particularly preferably having 3 to 5 C atoms, or an alkenyl group having 2 to 10 C atoms, preferably having 2 to 4 C atoms, which may each be substituted by one or more radicals R 3 , wherein one or more H atoms may be replaced by D, an aromatic or heteroaromatic ring system having from 5 to 12 aromatic ring atoms, each of which may be substituted with one or more R 3 radicals, and a combination of these systems optionally having two or more adjacent ones
- Substituents R 1 may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or
- R 2 is the same or different at each occurrence selected from the group consisting of an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more R 3 radicals.
- suitable substituents are in particular also long alkyl groups, for example having 5 to 10 C atoms, or substituted or unsubstituted oligoarylene groups.
- Suitable oligoarylene groups are, for example, terphenyl, in particular meta-terphenyl, branched terphenyl, meta-quarterphenyl or branched quarterphenyl.
- Examples of preferred compounds according to the above-listed embodiments or compounds, as they can be preferably used in organic electronic devices, are the compounds of the following structures (1) to (274).
- an electronic device is understood to mean a device which contains at least one layer which contains at least one organic compound.
- the component may also contain inorganic materials or even layers which are completely composed of inorganic materials.
- the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting emissive electrochemical cells (LECs), organic laser diodes (O-lasers) and "organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4), but preferably organic electroluminescent devices (OLEDs) 1 particularly preferably phosphorescent
- the organic electroluminescent device includes cathode, anode and at least one emitting layer. In addition to these layers, they may also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers and / or charge generation layers (charge generation layers). Likewise, interlayer may be introduced between two emitting layers which, for example, have an exciton-blocking function. It should be noted, however, that not necessarily each of these layers must be present. In this case, the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers. If several emission layers are present, they preferably have a total of several emission maxima between
- various emitting compounds are used which can fluoresce or phosphoresce. Particular preference is given to three-layer systems, the three layers exhibiting blue, green and orange or red emission (for the basic structure see, for example, WO 05/011013).
- an organic electroluminescent device comprising a compound according to formula (1) or formula (8) to (18) as matrix material for fluorescent or phosphorescent emitters, in particular for phosphorescent emitters, and / or in a hole blocking layer and / or in an electron transport layer and or in an electron-blocking or exciton-blocking layer and / or in a hole-transport layer.
- a compound according to formula (1) or formula (8) to (18) as matrix material for fluorescent or phosphorescent emitters, in particular for phosphorescent emitters, and / or in a hole blocking layer and / or in an electron transport layer and or in an electron-blocking or exciton-blocking layer and / or in a hole-transport layer.
- the compound according to formula (1) or formula (8) to (18) is used as matrix material for a fluorescent or phosphorescent compound in an emitting layer.
- the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers, wherein at least one emitting layer comprises at least one compound according to the invention as
- Layer is used, it is preferably used in combination with one or more phosphorescent materials (triplet emitter).
- phosphorescence is understood as meaning the luminescence from an excited state with a higher spin multiplicity, ie a spin state> 1, in particular from an excited triplet state.
- spin multiplicity ie a spin state> 1
- the mixture of the compound according to formula (1) or (8) to (18) and the emitting compound contains between 99 and 1% by volume, preferably between 98 and 10% by volume, more preferably between 97 and 60% by volume .-%, in particular between 95 and 80 vol .-% of the compound according to formula (1) or (8) to (18) based on the total mixture of
- the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, more preferably between 3 and 40% by volume, in particular between 5 and 20% by volume of the emitter, based on the total mixture Emitter and matrix material.
- a further preferred embodiment of the present invention is the use of the compound according to formula (1) or formula (8) to (18) as matrix material for a phosphorescent emitter in combination with another matrix material.
- Particularly suitable matrix materials which can be used in combination with the compounds according to formula (1) or formula (8) to (18) are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, eg. B.
- WO 08/086851 disclosed carbazole derivatives, indolocarbazole derivatives, e.g. B. according to WO 07/063754 or WO 08/056746, Azacarbazolderivate, z. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, for. B. according to WO 07/137725, silanes, z. B. according to WO 05/111172, azaborole or boronic esters, for. B. according to WO 06/117052, triazine derivatives, z.
- Suitable phosphorescent compounds are, in particular, compounds which, with suitable excitation, emit light, preferably in the visible range, and also at least one
- Preferred phosphorescence emitters are compounds comprising copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium,
- Examples of the emitters described above can be found in the applications WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373 and US 2005 / 0258742 are taken.
- all are suitable phosphorescent complexes, as used in the prior art for phosphorescent OLEDs and as those skilled in the art of organic electroluminescence known, and the skilled artisan can use other phosphorescent complexes without inventive step.
- the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, ie. H. the emissive
- Layer directly adjoins the hole injection layer or the anode, and / or the emissive layer directly adjoins the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 05/053051. Furthermore, it is possible to have a
- Metal complex that is the same or similar to the metal complex in the emitting layer, to be used directly adjacent to the emitting layer as Lochtransport- or Lochinjetechnischsmaterial such. As described in WO 09/030981.
- the emitting layer may be fluorescent or phosphorescent.
- the compound when used as an electron transport material, it may be preferred if it is doped, for example with alkali metal complexes, such as. B. Liq (lithium hydroxyquinolinate).
- the compound according to formula (1) or (8) to (18) is used in a hole blocking layer. Under a hole blocking layer becomes a
- the compound of the formula (1) or (8) to (18) is used in a hole transport layer or in an electron blocking layer or exciton blocking layer.
- organic electroluminescent device characterized in that one or more layers with a
- Sublimation method to be coated The materials in vacuum sublimation are at an initial pressure less than 10 "5 mbar, preferably less than 10 'deposited 6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 -7 mbar.
- an organic electroluminescent device characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
- the materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
- OVJP Organic Vapor Jet Printing
- the materials are applied directly through a nozzle and thus structured (for example, BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
- an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
- flexographic printing or offset printing but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing (ink jet printing), are produced.
- LITI Light Induced Thermal Imaging, thermal transfer printing
- inkjet printing ink jet printing
- soluble compounds are necessary, which are obtained for example by suitable substitution.
- the invention therefore relates to compounds according to formula (1 '),
- A-B and D-E are the same or different at each occurrence
- the dashed bond represents the bond to Z
- Ar is the same or different at each occurrence an aromatic or heteroaromatic ring system with 5 to 60 aromatic
- Ring atoms which may be substituted by one or more radicals R 1 ;
- Ar 1 is the same or different at each occurrence and is an aryl or heteroaryl group having 5 to 16 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
- X is the same or different CR 1 or N at each occurrence;
- L is a single bond or a bivalent, trivalent or tetravalent group
- Heteroaryloxy with 5 to 60 aromatic ring atoms, which with one or more R 3 may be substituted, or a combination of these systems, optionally two or more adjacent substituents R 1 may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more R 3 radicals ;
- those R 1 and R 2 adjacent to one another in the 1, 2-position may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 3 radicals;
- R 3 is selected from the group consisting of H 1 D, F, CN, aliphatic hydrocarbon radical having 1 to 20 C atoms, aromatic or heteroaromatic ring system having 5 to 30 aromatic
- n is 1 to 10, preferably 1, 2, 3, 4, 5 or 6;
- m is 1 if L is a single bond or a divalent group, or 2 if L is a trivalent group, or 3 if L is a tetravalent group;
- q is the same or different 0 or 1 at each occurrence
- the invention furthermore relates to compounds of the formula (39) and their use in electronic devices and electronic devices, in particular organic electroluminescent devices comprising these compounds:
- Another object of the present invention is a process for the preparation of the compounds of the invention listed above by reacting an ortho-diamino-substituted aromatic, wherein the amino groups are unsubstituted or preferably monosubstituted, with an aromatic phosphonic acid chloride derivative or an aromatic Oligophosphonklarechloridderivat.
- the compounds according to the invention described above in particular compounds which are substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or by reactive, polymerizable groups, such as olefins or oxetanes, can be used as Monomers for generating corresponding oligomers, dendrimers or polymers find use.
- the oligomerization or polymerization takes place preferably via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible to crosslink the polymers via such groups.
- the 5 polymers according to the invention can be used as crosslinked or uncrosslinked
- the invention therefore further oligomers, polymers or dendrimers containing one or more of the compounds of the invention listed above, wherein one or more bonds of the inventive compound to the polymer, oligomer or dendrimer are present. Depending on the linkage of the compound according to the invention, this therefore forms a side chain of the oligomer or polymer or is linked in the main chain.
- -I C or dendrimers may be conjugated, partially conjugated or non-conjugated.
- the oligomers or polymers may be linear, branched or dendritic.
- the repeat units of the compounds according to the invention in oligomers, dendrimers and polymers have the same preferences as described above. 20
- the monomers according to the invention are homopolymerized or copolymerized with further monomers. Preference is given to homopolymers or copolymers in which the units of the formula (1) or (8) to (18) or (39) are from 0.01 to 99.9
- Suitable and preferred comonomers which form the polymer backbone are selected from fluorenes (for example according to EP 842208 or WO 00/22026), spirobifluorenes (for example according to EP 707020, EP 894107 or WO 06/061181), para- phenylenes (z. B. 3 0 according WO 92/18552) WO, carbazoles (for. example, according 04/070772 or
- WO 04/113468 thiophenes (for example according to EP 1028136), dihydrophenanthrenes (for example according to WO 05/014689), cis- and trans-indeno-fluorenes (for example according to WO 04/041901 or WO 04/113412), ketones (for example according to WO 05/040302), phenanthrenes (for example according to US Pat
- the polymers, oligomers and dendrimers may also contain other units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.
- the polymers may either be copolymerized or mixed in as a blend containing triplet emitters. Especially the combination of units according to the formulas (1) or (8) to (18) with triplet emitters leads to particularly good results.
- the symbols used have the meanings given above and r stands for an integer between 2 and 1,000,000. These compounds, oligomers and polymers are also the subject of the present invention. The above-mentioned preferences apply to the symbols listed in formulas (37) and (38).
- the group Ar 1 is the same or different at each occurrence selected from 1, 2,4,5-linked benzene or 1,2,3,4-linked benzene.
- the compounds of the formula (1) or (1 ') can also be further functionalized and thus converted to extended structures.
- the compounds of the formula (1) or (V) can also be bound directly to phosphorescent metal complexes or else to other metal complexes.
- the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished by the following surprising advantages over the prior art:
- the compounds of the invention or compounds of formula (1) or formula (8) to (18), used as a matrix material for fluorescent or phosphorescent emitters lead to very high efficiencies and to long lifetimes. This applies in particular if the compounds are used as matrix material for a phosphorescent emitter. Significantly better efficiencies, in particular power efficiencies, and lifetimes are obtained than with the use of structurally similar phosphine oxides as matrix materials.
- the compounds of the invention or compounds of the formula (1) or (8) to (18) are not only suitable as a matrix for green and red phosphorescent compounds, but in particular also for blue phosphorescent compounds.
- the compounds of the invention have high thermal stability.
- Electroluminescent devices lead to high efficiencies and steep current-voltage curves with low threshold voltages.
- the synthesis is carried out according to the general procedure according to Example 2 from 56.6 g (240 mmol) of 1, 2-dibromobenzene and 54 ml (505 mmol) of o-toluidine.
- the precipitated solid is recrystallized from toluene / acetonitrile (5: 1) and the residue is washed with MeOH. This gives 68 g (237 mmol) of a crystalline solid.
- the total yield is 90%.
- the synthesis is carried out according to the general procedure according to Example 2 from 63.3 g (240 mmol) of 1,2-dibromo-4,5-dimethylbenzene and 54 ml (505 mmol) of p-toluidine.
- the precipitated solid is from toluene / acetonitrile
- the synthesis is carried out according to the general procedure according to Example 2 from 56.6 g (240 mmol) of 1, 2-dibromobenzene and 85.4 g (505 mmol) of 4-amine biphenyl.
- the precipitated solid is extracted from toluene / acetonitrile (5: 1). recrystallized and the residue washed with MeOH. This gives 78 g (189 mmol) of a crystalline solid.
- the total yield is 80%.
- the synthesis is carried out according to the general procedure according to Example 2 from 63.3 g (240 mmol) of 1,2-dibromo-4,5-dimethylbenzene and 85.4 g (505 mmol) of 4-aminobiphenyl.
- the precipitated solid is recrystallized from toluene / acetonitrile (5: 1) and the residue is washed with MeOH. This gives 80.3 g (182 mmol) of a crystalline solid. The total yield is 76%.
- the synthesis is carried out according to the general procedure according to Example 2 from 56.6 g (240 mmol) of 1, 2-dibromo-benzene and 47.5 g (505 mmol) of 4-aminopyridine.
- the precipitated solid is recrystallized from toluene / acetonitrile (5: 1) and the residue is washed with MeOH. This gives 46.2 g (176 mmol) of a crystalline solid.
- the total yield is 73%.
- inventive OLEDs and OLEDs according to the prior art is carried out according to a general method according to WO 04/058911, which is adapted to the circumstances described here (layer thickness variation, materials used).
- the OLEDs have the following layer structure: substrate / hole transport layer (HTL) / optional intermediate layer (IL) / electron blocking layer (EBL) / emission layer (EML) / optional
- HBL Hole blocking layer
- ETL electron transport layer
- Electron injection layer (EIL) and finally a cathode.
- Cathode is formed by a 100 nm thick aluminum layer.
- the exact structure of the OLEDs is shown in Table 1.
- the materials used to make the OLEDs are shown in Table 3.
- the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is admixed to the matrix material or the matrix materials by co-evaporation in a specific volume fraction.
- the electron transport layer may consist of a mixture of two materials. The OLEDs are characterized by default.
- the life is defined as the time after which the luminance has dropped from a certain starting luminous density I 0 to a certain proportion.
- the term LD80 means that the said lifetime is the time at which the luminance has fallen to 0.8 I 0 (to 80%), ie of z. B. 4000 cd / m 2 to 3200 cd / m 2 .
- the compounds according to the invention can be used inter alia as matrix materials (host materials, host materials) for phosphorescent dopants.
- matrix materials host materials, host materials
- the compounds of the invention H3, H4, H5, H6 and H7 are used.
- the compounds H1, H2 and H8 are used.
- OLEDs with the green-emitting dopant TEG 1, the blue-emitting dopant TEB 1 and the red-emitting dopant TER 1 are shown. The results of the OLEDs are in
- the compounds according to the invention show the greatest progress (comparison of Ex. 35-37 with Ex. 44-48).
- the corresponding matrix materials H3, H4, H5, H6 and H7 comparable operating voltages as in the use of H2 according to the prior art, but the current efficiency can be significantly increased.
- the improvement is between about 25% (example 45 and example 36) up to about 50% (example 48 and example 37), which gives correspondingly improved performance efficiencies.
- Matrix materials a very significant improvement in the life.
- the diamines listed below can be prepared from the corresponding dibromoaromatic compounds by reaction with the corresponding o-phenylenediamine analogously to Example 51.
- diazaphospholes listed below can be prepared from the corresponding diamino aromatics by reaction with the corresponding phosphonous chloride analogously to Example 55.
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Abstract
Description
Claims
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CN200980125117.XA CN102076813B (zh) | 2008-11-11 | 2009-10-15 | 有机电致发光器件 |
EP09736571.2A EP2344607B1 (de) | 2008-11-11 | 2009-10-15 | Organische elektrolumineszenzvorrichtungen |
US13/001,731 US8865321B2 (en) | 2008-11-11 | 2009-10-15 | Organic electroluminescent devices |
JP2011535023A JP5701766B2 (ja) | 2008-11-11 | 2009-10-15 | 有機エレクトロルミネセント素子 |
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DE102009022858A DE102009022858A1 (de) | 2009-05-27 | 2009-05-27 | Organische Elektrolumineszenzvorrichtungen |
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Also Published As
Publication number | Publication date |
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CN102076813A (zh) | 2011-05-25 |
TWI466893B (zh) | 2015-01-01 |
CN102076813B (zh) | 2016-05-18 |
JP5701766B2 (ja) | 2015-04-15 |
KR20110097612A (ko) | 2011-08-31 |
KR101763422B1 (ko) | 2017-07-31 |
US8865321B2 (en) | 2014-10-21 |
EP2344607A1 (de) | 2011-07-20 |
US20110201778A1 (en) | 2011-08-18 |
EP2344607B1 (de) | 2013-04-10 |
KR20100053454A (ko) | 2010-05-20 |
JP2012508202A (ja) | 2012-04-05 |
TW201033227A (en) | 2010-09-16 |
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