JP2014533435A - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP2014533435A JP2014533435A JP2014539252A JP2014539252A JP2014533435A JP 2014533435 A JP2014533435 A JP 2014533435A JP 2014539252 A JP2014539252 A JP 2014539252A JP 2014539252 A JP2014539252 A JP 2014539252A JP 2014533435 A JP2014533435 A JP 2014533435A
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- 238000005401 electroluminescence Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims description 139
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 239000011159 matrix material Substances 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- -1 NR 2 Inorganic materials 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 17
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 150000003951 lactams Chemical group 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- 238000006664 bond formation reaction Methods 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims description 3
- 229960005544 indolocarbazole Drugs 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 238000007689 inspection Methods 0.000 claims description 2
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical group N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 230000005518 electrochemistry Effects 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000463 material Substances 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 0 O=C(C(*=*CCC1)=C1C1=C2****1)N2I Chemical compound O=C(C(*=*CCC1)=C1C1=C2****1)N2I 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000008569 process Effects 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 10
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 238000004587 chromatography analysis Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000012286 potassium permanganate Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- NTTRIFCMSRYTIK-UHFFFAOYSA-N 2-phenyl-5-(4-phenylphenyl)-6h-phenanthridine Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C2=CC=CC=C2CN1C(C=C1)=CC=C1C1=CC=CC=C1 NTTRIFCMSRYTIK-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- FYPGEEHQXMFSIJ-UHFFFAOYSA-N 10-[(2-bromophenyl)methyl]-9,9-dimethylacridine Chemical compound C12=CC=CC=C2C(C)(C)C2=CC=CC=C2N1CC1=CC=CC=C1Br FYPGEEHQXMFSIJ-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-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
- OEMYZFFUEMRORO-UHFFFAOYSA-N 2,9-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1,4,6,8,11,13,15-heptaene-3,10-dione Chemical compound C1=CC=C2C(=O)N=C3C4=C2C1=NC(=O)C4=CC=C3 OEMYZFFUEMRORO-UHFFFAOYSA-N 0.000 description 2
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 2
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- XZESMTFIRRDELY-UHFFFAOYSA-N 5-(4-bromophenyl)phenanthridin-6-one Chemical compound C1=CC(Br)=CC=C1N1C(=O)C2=CC=CC=C2C2=CC=CC=C21 XZESMTFIRRDELY-UHFFFAOYSA-N 0.000 description 2
- KCAVAHMVCQPJFI-UHFFFAOYSA-N 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]phenanthridin-6-one Chemical compound C12=CC=CC=C2C2=CC=CC=C2C(=O)N1C(C=1)=CC=CC=1C(N=1)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 KCAVAHMVCQPJFI-UHFFFAOYSA-N 0.000 description 2
- KPBSJEPTQQYBES-UHFFFAOYSA-N 5-phenyl-6h-phenanthridine Chemical compound C12=CC=CC=C2C2=CC=CC=C2CN1C1=CC=CC=C1 KPBSJEPTQQYBES-UHFFFAOYSA-N 0.000 description 2
- ZTUXLWBGCHWARM-UHFFFAOYSA-N 5-phenylphenanthridin-6-one Chemical compound C12=CC=CC=C2C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 ZTUXLWBGCHWARM-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 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
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- RZFVLEJOHSLEFR-UHFFFAOYSA-N phenanthridone Chemical compound C1=CC=C2C(O)=NC3=CC=CC=C3C2=C1 RZFVLEJOHSLEFR-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229960002429 proline Drugs 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 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
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- 238000001931 thermography Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229910000083 tin tetrahydride Inorganic materials 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
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation 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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- 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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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- 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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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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Abstract
Description
本発明の目的は、蛍光もしくは燐光OLED、特に、燐光OLEDにおける、たとえば、マトリックス材料としてまたは正孔輸送/電子ブロック材料としてまたは励起子ブロック材料として、電子輸送もしくは正孔ブロック材料としての使用に適している化合物を提供することである。特に、緑色-、赤色-および随意に青色-燐光OLEDに適するマトリックス材料を提供することが本発明の目的である。
Arは、出現毎に同一であるか異なり、1以上の基Rにより置換されてよい5〜13個の芳香族環原子を有するアリールもしくはヘテロアリール基であり;
Ar1は、1以上の基Rにより置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まない5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Yは、-C(=O)N(Ar1)-、-C(=O)-O-、-CR1=CR1-、-CR1=N-、C(R1)2、NR1、O、S、C(=O)、C(=S)、C(=NR1)、C(=C(R1)2)、Si(R1)2、BR1、PR1、P(=O)(R1)、SOまたはSO2であり;
R、R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar2)2、N(R2)2、C(=O)Ar2、C(=O)R2、P(=O)(Ar2)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、C=O、C=S、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれらの構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rもしくは2個以上の隣接する置換基R1は、一以上の置換基R2により置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まないモノ環状あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;Ar1上の基Rは、さらに、Ar上の基Rとともに脂肪族環構造をさらに形成してもよく;ただし、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基は、基RもしくはR1の環形成によっては形成されず;
Ar2は、出現毎に同一であるか異なり、1以上の非芳香族基R2により置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まない5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;同じN原子もしくはP原子に結合する二個の基Ar2は、単結合またはN(R2)、C(R2)2もしくはOから選ばれるブリッジにより互いにブリッジしてもよく;
R2は、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上のH原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよく、ここで、2個以上の隣接する置換基R2は、モノ-あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を互いに形成してもよく;
nは、出現毎に同一であるか異なり、0または1であり、ここで、n=0は、基Yが存在せず、代わって置換基Rが結合するか、または基Arのヘテロ原子は、Yが式(1)中で結合するAr上の位置に存在することを意味し;
ただし、ArもしくはAr1上の基は、ラクタム基を含まない。
Xは、出現毎に同一であるか異なり、CRもしくはNであるか、または、式(2)もしくは式(6)中の二個の隣接する基Xは、以下の式(9)もしくは(10)の基であり、
Vは、NR、OまたはSである。
Arは、出現毎に同一であるか異なり、1以上の基Rにより置換されてよい5〜13個の芳香族環原子を有するアリールもしくはヘテロアリール基であり;
Ar1は、1以上の基Rにより置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まない5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Yは、-C(=O)N(Ar1)-、-C(=O)-O-、-CR1=CR1-、-CR1=N-、C(R1)2、NR1、O、S、C(=O)、C(=S)、C(=NR1)、C(=C(R1)2)、Si(R1)2、BR1、PR1、P(=O)(R1)、SOまたはSO2であり;
R、R1は、出現毎に同一であるか異なり、H、D、F、I、N(Ar2)2、C(=O)Ar2、C(=O)R2、P(=O)(Ar2)2、1〜40個のC原子を有する直鎖アルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、C=O、C=S、C=NR2、P(=O)(R2)、SO、SO2、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれらの構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rもしくは2個以上の隣接する置換基R1は、一以上の置換基R2により置換されてよいモノ環状あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;Ar1上の基Rは、Ar上の基Rと共に脂肪族環構造をさらに形成してもよく;ただし、互いに直接縮合する二個を超えるアリール基を有するアリールもしくはヘテロアリール基は、基RもしくはR1の環形成によっては形成されず;
Ar2は、出現毎に同一であるか異なり、1以上の非芳香族基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;同じN原子もしくはP原子に結合する二個の基Ar2は、単結合またはN(R2)、C(R2)2もしくはOから選ばれるブリッジにより互いにブリッジしてもよく;
R2は、H、D、F、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上のH原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよく、ここで、2個以上の隣接する置換基R3は、モノ-あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を互いに形成してもよく;
nは、出現毎に同一であるか異なり、0または1であり、ここで、n=1は、基Yが存在せず、代わって置換基Rが結合するか、または基Arのヘテロ原子は、Yが式(1)中で結合するAr上の位置に存在することを意味し;
ただし、ArもしくはAr1上の基は、ラクタム基を含まず、
以下の化合物は、本発明から除外される。
対応するラクタムへの酸化を伴う
a)ラクタムの窒素原子とAr1との間の結合形成;または
b)アミドの窒素原子とArとの間の結合形成;または
c)アミド基を介して互いに結合する二個の基Arとの間の結合形成;または
d)メチレンアミン基を介して互いに結合する二個の基Arとの間の結合形成。
以下の合成は、他に断らない限り、保護雰囲気下で行われる。出発材料は、アルドリッチ(ALDRICH)またはABCR(酢酸パラジウム(II)、トリ-o-トリルホスフィン、無機物、溶媒)から購入することができる。文献公知の出発物質の場合の番号は、CAS番号である。
本発明によるOLEDと先行技術によるOLEDが、WO 2004/058911にしたがう一般的プロセスにより製造されるが、ここに記載される状況(層の厚さの変化、材料)に適合される。
化合物9gを電子輸送層で使用するならば、4.3Vという低い駆動電圧と8%をやや超える非常に良好な量子効率が得られ、先行技術にしたがう化合物LaDi1の使用に関して、これらの値は、顕著により劣る(例V2とE5)。
緑色ドーパントTEG1と組合わせた一重項マトリックス材料としての本発明の材料の使用に関して、3.3Vという非常に低い駆動電圧と16.4%までの非常に良好な外部量子効率が得られる(例E10とE11)。
Claims (13)
- 式(1)の化合物を含む電子素子。
Arは、出現毎に同一であるか異なり、1以上の基Rにより置換されてよい5〜13個の芳香族環原子を有するアリールもしくはヘテロアリール基であり;
Ar1は、1以上の基Rにより置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まない、5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Yは、-C(=O)N(Ar1)-、-C(=O)-O-、-CR1=CR1-、-CR1=N-、C(R1)2、NR1、O、S、C(=O)、C(=S)、C(=NR1)、C(=C(R1)2)、Si(R1)2、BR1、PR1、P(=O)(R1)、SOまたはSO2であり;
R、R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar2)2、N(R2)2、C(=O)Ar2、C(=O)R2、P(=O)(Ar2)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、C=O、C=S、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれら構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rもしくは2個以上の隣接する置換基R1は、一以上の置換基R2により置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まない、モノ環状あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;Ar1上の基Rは、さらに、Ar上の基Rとともに脂肪族環構造をさらに形成してもよく;ただし、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基は、基RもしくはR1の環形成によっては形成されず;
Ar2は、出現毎に同一であるか異なり、1以上の非芳香族基R2により置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まない、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;同じN原子もしくはP原子に結合する二個の基Ar2は、単結合またはN(R2)、C(R2)2もしくはOから選ばれるブリッジにより互いにブリッジしてもよく;
R2は、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上のH原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよく、ここで、2個以上の隣接する置換基R2は、モノ-あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を互いに形成してもよく;
nは、出現毎に同一であるか異なり、0または1であり、ここで、n=0は、基Yが存在せず、代わって置換基Rが結合するか、または基Arのヘテロ原子が、Yが式(1)中で結合するAr上の位置に存在することを意味し;
ただし、ArもしくはAr1上の基は、ラクタム基を含まない。) - 有機エレクトロルミネッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機太陽電池、有機染料増感性太陽電池、有機光学検査器、有機光受容器、有機電場消光素子、発光電子化学電池、有機レーザーダイオード(O-laser)および「有機プラスモン発光素子」より成る群から選ばれる、請求項1記載の電子素子。
- Arは、出現毎に同一であるか異なり、それぞれ1以上の基Rにより置換されてよい6個の芳香族環原子を有するアリールもしくはヘテロアリール基または5個の芳香族環原子を有するヘテロアリール基であり;ここで、二個の置換基Rは、さらなる環構造を互いに形成してもよいことを特徴とする、請求項1または2記載の電子素子。
- n=0に対するArは、以下の式(2)〜(5)の基から選ばれ、n=1に対するArは、以下の式(6)〜(8)の基から選ばれ、ただし、n=1に対しては、少なくとも一つのArは、式(6)の基であることを特徴とする、請求項1〜3何れか1項記載の電子素子。
Xは、出現毎に同一であるか異なり、CRもしくはNであるか、または、式(2)もしくは式(6)中の二個の隣接する基Xは、以下の式(9)もしくは(10)の基であり、
Vは、NR、OまたはSである。) - 全ての基Xは、出現毎に同一であるか異なり、CRであることを特徴とする、請求項4または請求項5記載の電子素子。
- Ar1は、ベンゼン、オルト-、メタ-もしくはパラ-ビフェニル、オルト-、メタ-、パラ-もしくは分岐テルフェニル、直鎖もしくは分岐クアテルフェニル、フルオレン、スピロビフルオレン、カルバゾール、ジベンゾチオフェン、ジベンゾフラン、1,3,5-トリアジン、ピリジン、ピリミジン、インデノカルバゾール、架橋カルバゾールもしくはインドロカルバゾールまたは二もしくは三個のこれらの基の組み合わせから選ばれ、これらの基は、それぞれ1以上の基Rにより置換されてよいことを特徴とする、請求項1〜7何れか1項記載の電子素子。
- Rは、出現毎に同一であるか異なり、H、D、F、CN、N(Ar2)2、C(=O)Ar2、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜10個のC原子を有するアルケニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、DまたはFで置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜30個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基より成る群から選ばれることを特徴とする、請求項1〜8何れか1項記載の電子素子。
- 式(1)の化合物が、蛍光もしくは燐光エミッターのためのマトリックス材料としておよび/また正孔ブロック層中でおよび/または電子輸送中でおよび/または電子ブロック層もしくは励起子ブロック層中でおよび/または正孔輸送層中でおよび/または光学的アウトカップリング層中で使用されることを特徴とする、請求項1〜9何れか1項記載の電子素子:
- 式(1')の化合物。
Arは、出現毎に同一であるか異なり、1以上の基Rにより置換されてよい5〜13個の芳香族環原子を有するアリールもしくはヘテロアリール基であり;
Ar1は、1以上の基Rにより置換されてよく、互いに直接縮合する二個を超える芳香族六員環を有するアリールもしくはヘテロアリール基を含まない、5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Yは、-C(=O)N(Ar1)-、-C(=O)-O-、-CR1=CR1-、-CR1=N-、C(R1)2、NR1、O、S、C(=O)、C(=S)、C(=NR1)、C(=C(R1)2)、Si(R1)2、BR1、PR1、P(=O)(R1)、SOまたはSO2であり;
R、R1は、出現毎に同一であるか異なり、H、D、F、I、N(Ar2)2、C(=O)Ar2、C(=O)R2、P(=O)(Ar2)2、1〜40個のC原子を有する直鎖アルキル基、3〜40個のC原子を有する分岐あるいは環状アルキル基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、C=O、C=S、C=NR2、P(=O)(R2)、SO、SO2、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれらの構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rもしくは2個以上の隣接する置換基R1は、一以上の置換基R2により置換されてよいモノ環状あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;Ar1上の基Rは、Ar上の基Rと共に脂肪族環構造をさらに形成してもよく;ただし、互いに直接縮合する二個を超えるアリール基を有するアリールもしくはヘテロアリール基は、基RもしくはR1の環形成によっては形成されず;
Ar2は、出現毎に同一であるか異なり、1以上の非芳香族基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、同じN原子もしくはP原子に結合する二個の基Ar2は、単結合またはN(R2)、C(R2)2もしくはOから選ばれるブリッジにより互いにブリッジしてもよく;
R2は、H、D、F、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造より成る群から選ばれ、ここで、1以上のH原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよく、ここで、2個以上の隣接する置換基R3は、モノ-あるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を互いに形成してもよく;
nは、出現毎に同一であるか異なり、0または1であり、ここで、n=1は、基Yが存在せず、代わって置換基Rが結合するか、または基Arのヘテロ原子が、Yが式(1)中で結合するAr上の位置に存在することを意味し;
ただし、ArもしくはAr1上の基は、ラクタム基を含まず、
以下の化合物は、本発明から除外される。
- 以下を含む式(1')の化合物の製造方法:
対応するラクタムへの酸化を伴う
a)ラクタムの窒素原子とAr1との間の結合形成;または
b)アミドの窒素原子とArとの間の結合形成;または
c)アミド基を介して互いに結合する二個の基Arとの間の結合形成;または
d)メチレンアミン基を介して互いに結合する二個の基Arとの間の結合形成。 - 請求項11記載の化合物の、電子素子、特に、有機エレクトロルミネッセンス素子での使用。
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KR20140097275A (ko) | 2014-08-06 |
US20140249308A1 (en) | 2014-09-04 |
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CN104024371B (zh) | 2015-11-25 |
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EP2773721B1 (de) | 2015-11-25 |
US9337430B2 (en) | 2016-05-10 |
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