WO2011110276A1 - Materialien für elektronische vorrichtungen - Google Patents
Materialien für elektronische vorrichtungen Download PDFInfo
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- WO2011110276A1 WO2011110276A1 PCT/EP2011/000706 EP2011000706W WO2011110276A1 WO 2011110276 A1 WO2011110276 A1 WO 2011110276A1 EP 2011000706 W EP2011000706 W EP 2011000706W WO 2011110276 A1 WO2011110276 A1 WO 2011110276A1
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- Prior art keywords
- substituted
- atoms
- formula
- aromatic
- radicals
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- 239000000463 material Substances 0.000 title description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 238000005092 sublimation method Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 239000002019 doping agent Substances 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 239000011159 matrix material Substances 0.000 claims description 29
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000005577 anthracene group Chemical group 0.000 claims description 21
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical group C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 19
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 125000004001 thioalkyl group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 64
- 150000003254 radicals Chemical class 0.000 description 52
- -1 2-anthracenyl Chemical group 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000004986 diarylamino group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000001454 anthracenes Chemical class 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- UXOSWMZHKZFJHD-UHFFFAOYSA-N anthracene-2,6-diamine Chemical class C1=C(N)C=CC2=CC3=CC(N)=CC=C3C=C21 UXOSWMZHKZFJHD-UHFFFAOYSA-N 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical class C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 2
- JUUZQMUWOVDZSD-UHFFFAOYSA-N 1h-imidazole;pyrazine Chemical compound C1=CNC=N1.C1=CN=CC=N1 JUUZQMUWOVDZSD-UHFFFAOYSA-N 0.000 description 2
- IGHOZKDBCCFNNC-UHFFFAOYSA-N 1h-imidazole;quinoxaline Chemical compound C1=CNC=N1.N1=CC=NC2=CC=CC=C21 IGHOZKDBCCFNNC-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- LKSIXPHOLPIQSE-UHFFFAOYSA-N 2,6-bis(n-(9,9-dimethylfluoren-2-yl)anilino)-4a,9a-dihydroanthracene-9,10-dione Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC=CC=1)C(C=C1)=CC(C(C2=CC=3)=O)C1C(=O)C2=CC=3N(C=1C=C2C(C)(C)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 LKSIXPHOLPIQSE-UHFFFAOYSA-N 0.000 description 2
- QSPPZWHVOAJOGJ-UHFFFAOYSA-N 2,6-dichloro-4a,9a-dihydroanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3C=C(Cl)C=CC3C(=O)C2=C1 QSPPZWHVOAJOGJ-UHFFFAOYSA-N 0.000 description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- RFTRFDMRINNTSI-UHFFFAOYSA-N 9,9-dimethyl-n-phenylfluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1NC1=CC=CC=C1 RFTRFDMRINNTSI-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- VVLCNWYWKSWJTG-UHFFFAOYSA-N anthracene-1,2-diamine Chemical compound C1=CC=CC2=CC3=C(N)C(N)=CC=C3C=C21 VVLCNWYWKSWJTG-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Chemical class 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 238000006478 transmetalation reaction Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/001—Pyrene dyes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- H—ELECTRICITY
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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
Definitions
- the invention relates to an organic electroluminescent device having an anode and a cathode and at least one arranged between the anode and cathode electroluminescent layer, which at least one compound of formula (I) and at least one
- Compound of formula (II) contains.
- the invention further relates to the preparation of the organic electroluminescent device according to the invention by means of sublimation and / or by application from solution and a mixture containing at least one compound of formula (I) and at least one compound of formula (II).
- Organic semiconductor materials such as the above compounds are being developed for a variety of electronic applications.
- OLEDs organic electroluminescent devices
- the structure of organic electroluminescent devices (OLEDs) in which these organic semiconductors are used as functional materials is described, for example, in US Pat. Nos. 4,539,507, 5,151,629, EP 0676461 and WO 98/27136.
- further improvements are needed before these devices can be used for high quality and durable displays, such as televisions.
- Electroluminescent devices still need to be improved.
- Another requirement for light-emitting organic compounds is a small difference between excitation and emission wavelength, which is also referred to as "Stokes shift".
- the green dopant materials known from the prior art show predominantly broad emission bands, resulting in a loss of efficiency and a
- Electroluminescent devices still a relatively high
- Diaminoanthracene introduced as dopants The matrix material also influences the emission characteristics of the dopant compound.
- WO 2007/021 17 describes green-light-emitting organic electroluminescent devices which contain 2,6-diaminoanthracenes as dopants. These are in the electroluminescent layer with derivatives of anthracene,
- Benz [a] anthracens or naphthacene combined.
- substituents phenyl, 2-naphthyl, 2-anthracenyl, 2-fluoro-phenyl, 1-pyrenyl, 2-fluorenyl, 4-biphenyl and 3-perylenyl groups are used in the anthracene derivatives.
- US 2008/0182129 A1 describes an organic electroluminescent device in whose light-emitting layer a 2-arylanthracene compound as matrix material and a further
- Anthracene compound is contained as a dopant.
- the light-emitting second anthracene compound is at least two positions with a
- the 2-arylanthracene compound may be substituted at the 9- and 10-positions with phenyl-1-naphthyl, 2-naphthyl, 4-biphenyl, perylenyl, fluoro-anthyl, and phenanthryl groups.
- Naphthalene, anthracene, phenanthrene or pyrene derivative used.
- the anthracene derivatives may be substituted in positions 9 and 10.
- Naphthyl, phenanthryl and p-terphenyl radicals are described as substituents.
- WO 2008/145239 are organic
- Electroluminescent devices described in the light-emitting layer Benzanthracenderivate are included as a matrix material, wherein as fluorescent dopants monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers and arylamines are called.
- fluorescent dopants monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers and arylamines are called.
- arylamines for example, aromatic
- Pyrenamines aromatic Pyrendiamine, aromatic Chrysenamine or aromatic Chrysendiamine can be used. Under a
- aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group.
- anthracene derivatives which each have a diarylamino group in the 9- and in the 10-position are disclosed explicitly for use as dopants.
- alternative functional materials for organic electroluminescent devices there is still a need for alternative functional materials for organic electroluminescent devices.
- combinations of materials or blends which can be used in the emissive layer of organic electroluminescent devices This is often a critical issue in improving properties such as lifetime, color purity and device efficiency.
- the invention relates to an organic electroluminescent device comprising an anode and a cathode and at least one arranged between the anode and cathode electroluminescent layer, characterized in that the electroluminescent layer at least one compound of formula (I)
- Anthracene and the Benzanthracenringsystems can be substituted with one radical R 3 and wherein furthermore applies to the symbols occurring:
- Ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
- Ar 2 is the same or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals, wherein two radicals Ar 1 , which to the same
- H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic Ring atoms which may be substituted by one or more non-aromatic radicals R 4 , or a combination of these systems, wherein two or more radicals R 1 , R 2 and R 3 may be linked together and form a ring or a ring system; is identical or different at each occurrence H, D, F or an aliphatic, aromatic and / or heteroaromatic organic radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by D or F; It can have two or more same or different
- Substituents R 4 also be linked together and form a ring or a ring system.
- free position on a chemical group means any atom which has at least one unoccupied bonding position in the structural formula of the group in question
- Anthracene and benzanthracene compound for example, all numbered positions are vacant positions within the meaning of this definition.
- benzanthracene ring system in formula (II) may be attached to the anthracene group via any one of positions 1, 2, 3, 4, 5 or 6, the bond is represented as a line through the
- the anthracene group may be bonded in one of the positions 1, 2, 3, 4, 5 or 6 of the benzanthracene group. According to the invention, the bond at one of the two positions 4 and 5 of the benzanthracene group is preferred.
- An aryl group in the sense of this invention contains 6 to 60 C atoms;
- a heteroaryl group contains 1 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 (annelated) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, carbazole, etc. understood.
- An aryl or heteroaryl group which may be substituted in each case by the abovementioned radicals and which may be linked via any position on the aromatic or heteroaromatic compounds is understood in particular to mean groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, Dihydropyrenes, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, Indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine,
- Phenanthridine benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyrimididazole, pyrazine imidazole, quinoxaline imidazole, oxazole, Benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole,
- An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
- a heteroaromatic ring system in the context of this invention contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
- 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 a non-aromatic moiety (preferably less than 0% of the atoms other than H), e.g. As an sp 3 - hybridized C, N or O atom, may be connected.
- systems such as 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl group or linked by a silyl group.
- alkoxy or thioalkyl 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, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n -propylthio, i -propylthio , n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthi
- a preferred embodiment of the invention corresponds to
- CR 4 C (R 4 ) 2 , CN, NO 2l Si (R) 3 , B (OR 4 ) 2 , OSO 2 R 4 , OH, COOR 4 , CON (R) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or a
- R 5 on each occurrence is identical or different and is H, D, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms. Most preferably, R 5 is H. It is further preferred according to the invention that in the compound of formula (II) the bond between the Benzanthracenoli and the anthracene group in the 4- or in the 5-position of
- Benzanthracene group is present. This corresponds to compounds of the formulas (11-1) and (II-2),
- the compound of formula (II) is substituted in positions 7 and 12 of the Benzanthracenringsystems with a radical R 3 and in all other free positions of the
- Benzanthracene ring system is substituted with a hydrogen atom.
- aromatic ring atoms which may be substituted by one or more R radicals.
- A is the same or different on each occurrence selected from an aryl or heteroaryl group having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R 1 .
- A is the same or different on each occurrence, an aryl group having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R 1 .
- A is the same or different at each occurrence selected from the following groups
- Ar 1 is the same or different at each occurrence selected from an aromatic or
- Ar 1 is more preferably the same or differently selected on each occurrence from an aromatic ring system having 6 to 20
- aromatic ring atoms which may be substituted by one or more radicals R 1 , wherein two radicals Ar 1 , which to the same
- the groups Ar 1 bound to the same nitrogen atom are not identical.
- each time Ar 1 is the same or different selected from the following groups
- Ar 2 is the same or different selected on each occurrence of an aromatic or
- heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R 1 .
- Ar 2 is the same or different selected from the following groups at each occurrence
- Formula (II) represent all radicals R 3 are hydrogen atoms.
- Embodiments for the groups A, Ar 1 and Ar 2 in formula (I) and (II) and the preferred linking pattern of the benzanthracene group and the anthracene group in formula (II) occur in combination with each other.
- the compounds of the formula (I) used in the organic electroluminescent device according to the invention and the compounds of the formula (II) used can be prepared by processes known to the person skilled in the art.
- 4-bromobenz [a] anthracene can be prepared according to Badgar et al., J. Chem. Soc. 1949, 799, 5-bromobenz [a] anthracene can be obtained according to Newman et al., J. Org. Chem. 1982, 47 (15), 2837.
- Both the benzanthracene group and the anthracene group may be substituted with R 3 radicals as shown above. Instead of
- Bromine derivatives other halogen derivatives can be used, preferably iodine derivatives.
- Dialkyl-2,6-diaminoanthracenes are presented (Scheme 4). In this way, a variety of different alkyl derivatives of 2,6-diaminoanthracenes can be prepared.
- R alkyl
- the invention further provides mixtures comprising at least one compound of the formula (I)
- Anthracene and the Benzanthracenringsystems can be substituted with one radical R 3 and wherein furthermore applies to the symbols occurring:
- Ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
- Ar 1 , Ar 2 is identical or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic Ring atoms which may be substituted by one or more radicals R 1 , wherein two radicals Ar 1 , which to the same
- H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 4 , or a combination of these
- R 1 , R 2 and R 3 may be linked together and form a ring or a ring system; is identical or different at each occurrence H, D, F or an aliphatic, aromatic and / or heteroaromatic organic radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by D or F; It can have two or more same or different Substituents R 4 also be linked together and form a ring or a ring system.
- A is the same or different at each occurrence from the following groups
- the proportion of the compound of the formula (II) is between 50.0 and 99.9% by weight,
- the proportion of the compound of formula (I) is preferably between 0.1 and 50.0 wt .-%, more preferably between 0.5 and 20.0 wt .-% and most preferably between 1.0 and 10.0 wt .-%.
- the mixtures listed above are inventively in
- the compound of the formula (I) is preferably used as dopant and the compound of the formula (II) is preferably used as matrix material in the electroluminescent layer of an organic electroluminescent device.
- a matrix material is understood in a system of matrix and dopant that component which is present in the system in the higher proportion.
- the matrix material is understood to be that component whose proportion is the highest in the mixture.
- mixtures according to the invention may additionally be contained in further layers of the organic electroluminescent device, for example in a hole transport layer,
- Electron transport layer or interlayer Electron transport layer or interlayer.
- Another object of the invention are formulations containing a mixture as defined above and at least one solvent, preferably an organic solvent.
- the organic electroluminescent device may contain further layers. These are, for example, selected from in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, intermediate layers
- the organic electroluminescent devices according to the invention are preferably fluorescent organic electroluminescent devices. It can also be about
- the devices according to the invention can contain both fluorescent electroluminescent layers and phosphorescent electroluminescent layers.
- the organic electroluminescent device contains several
- electroluminescent layers wherein at least one
- electroluminescent layer at least one compound according to formula (I) and at least one compound according to formula (II).
- these emission layers have a total of several emission maxima between 380 nm and 750 nm, so that total white emission results, that is, in the emitting layers different emitting compounds are used, which can fluoresce or phosphoresce and the blue or yellow or orange or red light emit.
- three-layer systems that is to say systems having three emitting layers, one of these layers being characterized by those disclosed in US Pat
- Organic electroluminescent device according to the invention arranged electroluminescent layer is formed, which layer preferably emits green light. In addition to this layer can then be arranged a layer which shows blue or orange or red emission.
- Electroluminescent device is described for example in WO 05/01 1013.
- Examples of preferred hole transport materials that can be used in a hole transport or hole injection layer in the electroluminescent device according to the invention are indenofluorenamines and derivatives (for example according to WO 06/22630 or WO 06/100896), which are described in EP 166 888 disclosed amine derivatives, Hexaazatriphenylenderivate (eg., According to WO 01/049806), amine derivatives with condensed aromatics (eg., According to US 5,061,569), disclosed in WO 95/09147 amine derivatives, Monobenzoindenofluorenamine (for example, according to WO 08 / 006449) or dibenzoindenofluoreneamines (eg according to WO 07/140847).
- indenofluorenamines and derivatives for example according to WO 06/22630 or WO 06/100896
- EP 166 888 disclosed amine derivatives, Hexaazatriphenylenderivate (eg., According to WO 01
- hole transport and hole injection materials are derivatives of the above-depicted compounds, as described in JP 2001/226331, EP 676461, EP 650955, WO 01/049806, US 4780536, WO 98/30071, EP 891 121, EP 1661888, JP 2006/253445, EP 650955, WO 06/073054 and US 5061569 are disclosed.
- Suitable hole transport or hole injection materials are, for example, the materials listed in the following table.
- organic electroluminescent devices preferably the compound of formula (I) as a dopant and the compound of formula (II) preferably used as a matrix.
- organic electroluminescent devices according to the invention may contain, in addition to the compounds of the formula (I), further
- Preferred dopants are selected from the class of monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers and arylamines.
- a monostyrylamine is understood as meaning a compound which contains a substituted or unsubstituted styryl group and at least one, preferably aromatic, amine.
- a distyrylamine is understood as meaning a compound which contains two substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
- a tristyrylamine is understood as meaning a compound which contains three substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
- a tetrastyrylamine is meant a compound containing four substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
- the styryl groups are particularly preferably silibene, which may also be further substituted.
- An arylamine or an aromatic amine in the context of this invention is understood as meaning a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. At least one of these is preferred aromatic or heteroaromatic ring systems a fused ring system, more preferably having at least 14 aromatic ring atoms.
- Preferred examples thereof are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.
- aromatic anthracene amine is meant a compound in which a diarylamino group is bonded directly to an anthracene group.
- aromatic anthracenediamine is meant a compound in which two diarylamino groups are bonded directly to an anthracene group.
- Aromatic pyrenamine Aromatic pyrenamine
- Pyrene diamines, chrysenamines and chrysenediamines are defined analogously thereto, the diarylamino groups on the pyrene preferably being bonded in the 1-position or in the 1, 6-position.
- dopants are selected from indenofluorenamines or -diamines, for example according to WO 06/122630, benzoindenofluoreneamines or -diamines, for example according to WO 08/006449, and dibenzoindenofluorenamines or -diamines, for example according to WO
- dopants from the class of styrylamines are substituted or unsubstituted tristilbenamines or the dopants described in WO 06/000388, WO 06/058737, WO 06/000389, WO 07/065549 and WO 07/115610. Further preferred are those in
- WO 10/012328 disclosed condensed hydrocarbons.
- organic electroluminescent devices according to the invention may contain, in addition to the compounds of the formula (II)
- Suitable matrix materials are materials of various substance classes.
- Preferred matrix materials are selected from the classes of the oligoarylenes (eg 2,2 ', 7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligoarylenes containing condensed aromatic groups, the oligoarylenevinylenes (eg DPVBi or spiro -DPVBi according to EP 676461), the polypodal metal complexes (eg according to WO 04/081017), the hole-conducting compounds (eg.
- the electron-conducting compounds in particular ketones, phosphine oxides, sulfoxides, etc. (for example according to WO 05/084081 and WO 05/084082), the atropisomers (for example according to WO 06/048268), the boronic acid derivatives (for example according to WO 06 / 117052) or the benzanthracenes (eg according to WO 08/145239).
- Preferred matrix materials are furthermore selected from the classes of the oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides. Preferred matrix materials are further than the invention
- an oligoarylene is to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another.
- Suitable electron transport or electron injection materials that can be used in the electroluminescent device according to the invention are, for example, the materials listed in the following table. Further suitable electron transport and electron injection materials are, for example, AlQ 3 , BAIQ, LiQ and LiF.
- low work function metals, metal alloys or multilayer structures of various metals are preferable, such as
- Alkaline earth metals alkali metals, main group metals or lanthanides (eg Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Furthermore, are suitable
- an alloy of magnesium and silver In multilayer structures, it is also possible, in addition to the metals mentioned, to use further metals which have a relatively high work function, such as, for example, As Ag or Al, which then usually combinations of metals, such as Ca / Ag or Ba / Ag are used. It may also be preferred to introduce between a metallic cathode and the organic semiconductor a thin intermediate layer of a material with a high dielectric constant. Suitable examples of these are alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (eg LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 , etc.). Furthermore, lithium quinolinate (LiQ) can be used for this purpose.
- the layer thickness of this layer is preferably between 0.5 and 5 nm.
- the anode high workfunction materials are preferred.
- the anode has a work function greater than 4.5 eV. Vacuum up.
- metals with a high redox potential such as Ag, Pt or Au, are suitable for this purpose.
- metal / metal oxide electrodes eg Al / Ni / NiO x , Al / PtO x
- at least one of the electrodes must be transparent to either the irradiation of the organic material (organic
- a preferred construction uses a transparent anode.
- Preferred anode materials are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is furthermore given to conductive, doped organic materials, in particular conductive doped polymers.
- the device is structured accordingly (depending on the application), contacted and finally sealed, since the life of the devices according to the invention is shortened in the presence of water and / or air.
- Organic electroluminescent device characterized in that one or more layers are coated by a sublimation process.
- the materials in vacuum sublimation are "evaporated 6 mbar.
- the initial pressure is even lower, for example less than 10" at an initial pressure less than 10 -5 mbar, preferably 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.
- any printing process such.
- screen printing flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, Thermal transfer printing) or ink jet printing (ink jet printing).
- LITI Light Induced Thermal Imaging, Thermal transfer printing
- ink jet printing ink jet printing
- the electronic devices of the present invention can be used in displays, as light sources in lighting applications, and as light sources in medical and / or cosmetic applications (e.g., light therapy).
- the compounds used as dopant compounds according to formula (I) have minimal rotational degrees of freedom only a small Stokes shift and thus narrow emission bands.
- Electroluminescent devices high color purity and high power efficiency of the devices can be achieved.
- Matrix compounds 9- (Naphth-2-yl) -10- (benz [a] anthracen-4-yl) anthracene and 9- (phenyl) -10- (benz [a] anthracen-4-yl) anthracene are in the application WO 2008/145239 discloses.
- the OLEDs are produced by a general process according to WO 04/058911. These are glass slides with structured
- ITO Indium-tin oxide coated to a thickness of 150 nm, are used as substrates.
- PEDOT poly (3,4-ethylenedioxy-2,5-thiophene)
- H. C. Starck Goslar
- the OLEDs have the following layer sequence: Substrate / PEDOT,
- the emission layer always consists of one
- Matrix material (host) and a dopant (dopant), which is added to the matrix material by co-evaporation.
- dopant a dopant which is added to the matrix material by co-evaporation.
- the compound H1 is used, each of which doped with one of the dopants D1 to D3.
- the OLEDs show green
- the electroluminescence spectra the current efficiency (measured in cd / A), the power efficiency (measured in Im / W) and the external quantum efficiency (EQE, measured in percent) as a function of the brightness, are calculated from current-voltage brightness Characteristic curves (IUL characteristics) as well as the service life.
- the lifetime is defined as the time after which the initial brightness of 25,000 cd / m 2 has fallen to half.
- Examples 1 to 12 are shown.
- the compounds D2-D5 are used as dopants in combination with the matrix materials H2 and H4.
- the dopant D1 is used in combination with the matrix materials H1-H4.
- Table 2 therefore lists data on components with optimized concentration ratios.
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
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JP2012556399A JP5752716B2 (ja) | 2010-03-09 | 2011-02-15 | 電子デバイス用材料 |
US13/583,404 US10273404B2 (en) | 2010-03-09 | 2011-02-15 | Materials for electronic devices |
DE112011100832.5T DE112011100832B4 (de) | 2010-03-09 | 2011-02-15 | Mischung enthaltend Materialien für elektronische Vorrichtungen, Formulierung die Mischung enthaltend, organische Elektrolumineszenzvorrichtung und Verfahren zur Herstellung einer organischen Elektrolumineszenzvorrichtung |
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DE102010010631A DE102010010631A1 (de) | 2010-03-09 | 2010-03-09 | Materialien für elektronische Vorrichtungen |
DE102010010631.3 | 2010-03-09 |
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JP (1) | JP5752716B2 (de) |
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US11937498B2 (en) | 2018-05-31 | 2024-03-19 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, light-emitting device, light-emitting apparatus, electronic apparatus, and lighting apparatus |
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JP2014177442A (ja) * | 2013-03-15 | 2014-09-25 | Idemitsu Kosan Co Ltd | ジアミノアントラセン誘導体及び有機エレクトロルミネッセンス素子 |
KR20210090178A (ko) | 2018-11-08 | 2021-07-19 | 이데미쓰 고산 가부시키가이샤 | 신규 화합물, 그것을 이용한 유기 일렉트로루미네센스 소자 및 전자 기기 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US11937498B2 (en) | 2018-05-31 | 2024-03-19 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, light-emitting device, light-emitting apparatus, electronic apparatus, and lighting apparatus |
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DE112011100832A5 (de) | 2013-01-03 |
JP5752716B2 (ja) | 2015-07-22 |
US10273404B2 (en) | 2019-04-30 |
US20120326602A1 (en) | 2012-12-27 |
DE102010010631A1 (de) | 2011-09-15 |
DE112011100832B4 (de) | 2022-06-30 |
JP2013521670A (ja) | 2013-06-10 |
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