TWI586677B - A boron compound for organic electroluminescent elements and an organic electroluminescent element - Google Patents
A boron compound for organic electroluminescent elements and an organic electroluminescent element Download PDFInfo
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- TWI586677B TWI586677B TW103106488A TW103106488A TWI586677B TW I586677 B TWI586677 B TW I586677B TW 103106488 A TW103106488 A TW 103106488A TW 103106488 A TW103106488 A TW 103106488A TW I586677 B TWI586677 B TW I586677B
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- 150000001639 boron compounds Chemical class 0.000 title claims description 38
- 239000010410 layer Substances 0.000 claims description 159
- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 239000000463 material Substances 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 57
- -1 decylamino group Chemical group 0.000 claims description 40
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 28
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 27
- 238000005401 electroluminescence Methods 0.000 claims description 25
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052796 boron Inorganic materials 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000004986 diarylamino group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 25
- 230000000903 blocking effect Effects 0.000 description 20
- 230000003111 delayed effect Effects 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 11
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 150000001454 anthracenes Chemical class 0.000 description 9
- 150000001716 carbazoles Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 150000004866 oxadiazoles Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 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
- 150000004696 coordination complex Chemical class 0.000 description 6
- 239000007772 electrode material Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- 150000008425 anthrones Chemical class 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000123 polythiophene Polymers 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 3
- 241000234282 Allium Species 0.000 description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- 239000012327 Ruthenium complex Substances 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 150000004984 aromatic diamines Chemical group 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 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
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- QSQIGGCOCHABAP-UHFFFAOYSA-N hexacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C21 QSQIGGCOCHABAP-UHFFFAOYSA-N 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- CDTRJYSYYSRJIL-UHFFFAOYSA-N indene Chemical compound C1=CC=C2C=C=CC2=C1 CDTRJYSYYSRJIL-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000001748 luminescence spectrum Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-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
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 2
- 239000003451 thiazide diuretic agent Substances 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RGXAPHRWCPNLDR-UHFFFAOYSA-N 2-(2-phenylethenyl)-7H-purine Chemical class C(=Cc1ncc2[nH]cnc2n1)c1ccccc1 RGXAPHRWCPNLDR-UHFFFAOYSA-N 0.000 description 1
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- 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
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical class C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 description 1
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Classifications
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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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C09B57/00—Other synthetic dyes of known constitution
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- 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
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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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- H—ELECTRICITY
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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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- H—ELECTRICITY
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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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
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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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
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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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H—ELECTRICITY
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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
- H10K85/658—Organoboranes
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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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Description
本發明係關於新穎有機電致發光元件用硼化合物及使用此之有機電致發光元件者,詳細而言,關於對由有機化合物所構成之發光層施加電場而發出光之薄膜型裝置者。
一般而言,有機電致發光元件(以下,稱為有機EL元件)之最為簡單之構造係由發光層及挾持該層之一對之對向電極所構成。即,有機EL元件係利用對兩電極間施加電場時,由陰極注入電子,由陽極注入電洞,且此等於發光層中再結合,進而發出光之現象。
近年來逐漸開始開發使用有機薄膜之有機EL元件。尤其,為了提高發光效率,以提升由電極之載體注入效率為目的,而進行電極種類之最佳化,藉由開發在電極間將由芳香族二胺所構成之電洞輸送層與由8-羥基喹啉鋁錯合物(以下,稱為Alq3)所構成之發光層設置作為薄膜之元件,與過往之使用蒽等之單結晶之元件相比,發光效率受到大幅改善,故以邁向具有自體發光‧高速回應
性之特徵之高性能平板之實用化前進至今。
又,作為提升元件發光效率之嚐試,亦探討不使用螢光而改為使用磷光。以上述之設置有由芳香族二胺所構成之電洞輸送層與由Alq3所構成之發光層之元件為首之諸多元件係利用螢光發光者,但,藉由使用磷光發光,即藉由利用來自三重態激勵狀態之發光,在與使用先前螢光(一重態)之元件相比,則期望3~4倍程度之效率提升。為此目的,既有探討將香豆素衍生物或二苯甲酮衍生物作為發光層,但僅能取得極低之亮度。又,作為利用三重態狀態之嚐試,雖已有探討使用銪錯合物,但此亦無法達成高效率之發光。近年來進行眾多如專利文獻1中提出般之以發光之高效率化或長壽命化為目的,且以銥錯合物等之有機金屬錯合物為中心之磷光發光摻雜劑材料之研究。
[專利文獻1]日本特表2003-515897號公報
[專利文獻2]日本特開2001-313178號公報
[專利文獻3]日本特開平11-162650號公報
[專利文獻4]日本特開平11-176578號公報
[專利文獻5]WO2007/063754號公報
[專利文獻6]WO2008/149691號公報
[專利文獻7]KR10-2011-132721號公報
[專利文獻8]日本特開2011-71460號公報
為了取得高發光效率,與前述摻雜劑材料同時使用之主材料亦變得重要。作為主材料所提出之代表性者的,可舉出專利文獻2中介紹之咔唑化合物之4,4’-雙(9-咔唑基)聯苯(以下,稱為CBP)。CBP在將由參(2-苯基吡啶)銥錯合物(以下,稱為Ir(ppy)3)所代表之綠色磷光發光材料使用作為主材料使用時,在容易流動電洞但不易流動電子之特性上,造成電荷注入平衡崩塌,促使過剩之電洞流出至電子輸送層側,其結果係導致來自Ir(ppy)3之發光效率下降。
如前述般,為了在有機EL元件中取高發光效率,則必須要具有高三重態激發能,且在兩電荷(電洞‧電子)注入輸送特性上取得平衡之主材料。並且,希望同時具備電化學性安定、高耐熱性及優異非晶質安定性之化合物,進而要求更多之改良。
專利文獻3中揭示作為電洞輸送材料之具有二苯基胺基之吲哚咔唑化合物。專利文獻4中揭示作為電洞輸送材料之二苯基吲哚咔唑化合物。專利文獻5及6中揭示作為磷光主材料之於分子內含有2個吲哚咔唑基之化合物,使用此之有機EL元件之發光效率受到改善,且具有高驅動安定性。
專利文獻1~6中皆係揭示將具有吲哚咔唑骨架之化合物使用於有機EL元件中,但並未揭示於吲哚咔
唑骨架上具有含硼基之化合物。又,專利文獻7中教示連結2個吲哚咔唑基之取代基及於吲哚咔唑骨架上經各種取代基所取代之化合物,但並未教示、連結2個吲哚咔唑基之基或於吲哚咔唑骨架上具有含硼基之化合物。並且,專利文獻8中揭示作為連結3個吲哚咔唑基之基為具有含硼基之化合物,但並未教示連結2個吲哚咔唑基之基為具有含硼基之化合物。
為了將有機EL元件應用於平板顯示器等之顯示元件,改善元件之發光效率之同時亦必須充分確保低驅動電壓等之驅動時之安定性。本發明係有鑑於上述現狀,以提供具有高效率且驅動時之高亮度安定性之實用上有用之有機EL元件及適宜於此之化合物為目的。
本發明者等經過精心探討之結果,發現藉由將具有特定構造之吲哚咔唑骨架之化合物使用作為有機EL元件,即可顯現優特性,進而完成本發明。
本發明之有機電致發光元件用化合物為下述一般式(1)或(2)之任一式所表示者。
式中,L1係獨立表示選自取代或未取代之碳數6~18之芳香族烴基、取代或未取代之碳數3~17之芳香族雜環基、及該取代或未取代之芳香族烴基及芳香族雜環基之芳香族環2~6個連結所構成之連結芳香族基之2價或3價之基,連結芳香族基可為直鏈狀亦可為分枝狀,連結之芳香族環可為相同亦可為相異。又,於一分子中包含2個L1時,此等可為相同亦可為相異。
Z表示式(1a)所表示之含硼基。
A係獨立表示氫、氘、碳數1~12之烷基、碳數2~12之烯基、碳數2~12之炔基、碳數1~12之烷氧基、羥基、氯、溴、氟、取代或未取代之碳數6~18之芳香族烴基、或取代或未取代之碳數3~17之芳香族雜環基,A為烷基、烯基、炔基、烷氧基、芳香族烴基、或芳香族雜環基時,鄰接之此等基或此等基所具有之取代基亦可相互結合而形成環,此等環可為包含B之雜環,亦可為縮合環。
Y係獨立表示下述式(1b)所表示之吲哚咔唑基。
在此,環I係與鄰接環在任意位置進行縮合之式(1c)所表示之芳香族烴環,環II係與鄰接環在任意位置進行縮合之式(1d)所表示之雜環。L2係與上述L1中同義,但為c+1價之基。
Z係與一般式(2)之Z為同義,Z為複數存在時,分別可為相同亦可為相異。
R表示氘、碳數1~12之烷基、碳數7~19之芳烷基、碳數2~12之烯基、碳數2~12之炔基、氰基、碳數2~24之二烷基胺基、碳數6~36之二芳基胺基、碳數14~38之二芳烷基胺基、胺基、硝基、碳數2~12之醯基、碳數2~12之烷氧基羰基、羧基、碳數1~12之烷氧基、碳數1~12之烷基磺醯基、碳數1~12之鹵烷基、羥基、醯胺基、苯氧基、碳數1~12之烷硫基、取代或未取代之碳數6~18之芳香族烴基、取代或未取代之碳數3~17之芳香族
雜環基、或式(1a)所表示之含硼基。
j及m係分別獨立表示0~4之整數,n表示0~2之整數。
一般式(1)及(2)中,a及b表示0或1之整數,c表示0~5之整數。但,一般式(1)中,j+m+n+a+c≧1,一般式(2)中,j+m+n+b+c≧1,a+c或b+c為0時,至少一個R表示式(1a)所表示之含硼基。又,j、m、n、b及c為2以上時,複數之R及Z分別可為相同亦可為相異。
一般式(1)及(2)中,Y係可舉出如一般式(3)~(6)之任一式所表示之吲哚咔唑基。
一般式(1)及(2)中,A係分別獨立地可舉出如碳數1~12之烷基、取代或未取代之碳數6~18之芳香族烴基、或取代或未取代之碳數3~17之芳香族雜環基。又,作為L1及L2,可舉出如L1及L2之至少一者為具有縮環構造之基。
又,本發明為具有包含上述之有機電致發光元件用硼化合物之有機層之有機電致發光元件。
本發明之有機電致發光元件之其他態樣係為於上述有機電致發光元件中,包含有機電致發光元件用硼化合物之有機層係選自發光層、電洞輸送層、電洞注入層、電子輸送層及電子注入層之至少一層。並且,其他態樣係於上述有機電致發光元件中,包含有機電致發光元件
用硼化合物之有機層為發光層,該發光層係含有磷光發光性摻雜劑與該有機電致發光元件用化合物作為主材料。
本發明之有機電致發光元件用硼化合物係於分子內具有2個吲哚咔唑基與至少一個含硼基。含硼基係由於硼原子在其分子軌域上具有空軌域,故具有最低未佔軌域(LUMO)能量順位低,且縮小與陰極之價電子帶之能隙之特性,藉由將本發明之化合物使用於有機EL元件,可期待電荷之注入輸送性提升,且降低有機EL元件之電壓之效果。
使用本發明之化合物之有機EL元件,對於發光層中之多種摻雜劑可實現最佳載體平衡,其結果係變得可提供發光特性受到大幅改善之有機EL元件。又,藉由於分子內具有2個吲哚咔唑基,而能設計成賦予溶解性提升機能之材料,且可賦予適宜於濕式製程之材料。並且,此化合物在氧化、還原、激發之各活性狀態下皆可使安定性提升,且同時具有良好非晶質特性,故可實現低驅動電壓且高耐久性之有機EL元件。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧電洞注入層
4‧‧‧電洞輸送層
5‧‧‧發光層
6‧‧‧電子輸送層
7‧‧‧陰極
[圖1]展示有機EL元件之一構造例之剖面圖。
[圖2]展示有機電致發光元件用硼化合物之1H-NMR圖。
本發明之有機EL元件用硼化合物係如前述一般式(1)或(2)所表示者。
一般式(1)、(2)中,L1表示選自取代或未取代之碳數6~18之芳香族烴基、取代或未取代之碳數3~17之芳香族雜環基、及此等基之芳香族環2~6個連結所構成之連結芳香族基之2價之基。連結芳香族基可為直鏈狀亦可為分枝狀,連結之芳香族環可為相同亦可為相異。又,2個L1可為相同亦可為相異。
作為L1係未取代之芳香族烴基、芳香族雜環基、或連結芳香族基時之具體例,可舉出如從苯、并環戊二烯、茚、萘、蒽、菲、吡咯、咪唑、吡唑、噻唑、噻吩、吡啶、吡嗪、嘧啶、噠嗪、三嗪、異吲哚、吲唑、嘌呤、苯并咪唑、吲嗪、苯并哌喃、苯并噁唑、異苯并呋喃、喹嗪、異喹啉、咪唑、萘啶、酞嗪、喹唑啉、喹喔啉、噌啉、喹啉、蝶啶、呸啶、啡啉、啡啶、吖啶、啡嗪、啡噻嗪、啡噁嗪、phenazasilane、二苯并二氧雜苯、咔啉、吲哚、吲哚并吲哚、咔唑、呋喃、苯并呋喃、異苯并呋喃、苯并噻唑、oxathrene、二苯并呋喃、噻吩、噻吨、噻蒽、吩噁嗪、噻茚、異苯并噻吩、并噻吩、萘并[2,3-b]噻吩(thiophanthrene)、二苯并噻吩等之芳香族化合物去除2或3個氫而生成之基,或從此等2~6個連結而成之芳香族化合物去除2或3個氫生成之基。
作為L1係具有取代基之芳香族烴基、具有取
代基之芳香族雜環基、或具有取代基之連結芳香族基時之取代基,則有氘、碳數1~12之烷基、碳數7~19之芳烷基、碳數2~12之烯基、碳數2~12之炔基、氰基、碳數2~24之二烷基胺基、碳數6~36之二芳基胺基、碳數14~38之二芳烷基胺基、胺基、硝基、醯基、碳數2~12之烷氧基羰基、羧基、碳數1~12之烷氧基、碳數1~12之烷基磺醯基、碳數1~12之鹵烷基、羥基、醯胺基、苯氧基、或碳數1~12之烷硫基。較佳為氘、碳數1~12之烷基、碳數7~19之芳烷基、碳數2~12之烯基、碳數2~12之炔基、碳數2~24之二烷基胺基、碳數6~36之二芳基胺基、碳數14~38之二芳烷基胺基、碳數2~12之醯基、碳數2~12之烷氧基羰基、碳數1~12之烷氧基、碳數1~12之烷基磺醯基、碳數1~12之鹵烷基、苯氧基、或碳數1~12之烷硫基。
在此,在L1為未取代之2或3價之連結芳香族基時,作為連結芳香族基,可舉出如從下述式(7)~(9)所示般之基去除2或3個氫而生成之基。
式(7)~(9)中,Ar1~Ar6表示未取代之單環或縮合環之芳香族環,可為相同亦可為相異。在此,與吲哚咔唑環之氮結合之基係以縮合環為佳。
作為L1係未取代之連結芳香族基時之具體例,例如可舉出從以下般基去除1~2個氫而生成之基。
式中,R’表示碳數6~18之芳香族烴基或碳數3~17之芳香族雜環基。此等之芳香族烴基或芳香族雜環基之具體例,除1價之基以外,其他係與上述L1中所說明者相同。
一般式(1)及(2)中,A表示氫、氘、碳數1~12之烷基、碳數2~12之烯基、碳數2~12之炔基、碳數1~12之烷氧基、羥基、氯、溴、氟、取代或未取代之碳數6~18之芳香族烴基、或取代或未取代之碳數3~17之芳香族雜環基。較佳為取代或未取代之碳數6~18之芳香族烴基、或取代或未取代之碳數3~17之芳香族雜環基。A為烷基、烯基、炔基、烷氧基、芳香族烴基、或芳香族雜環基時,鄰接之此等基或芳香族烴基、或芳香族雜環基所具有之取代基亦可相互結合而形成環,此等之環可為包含B之雜環,亦可為縮合環。
A為具有取代基之芳香族烴基或具有取代基之芳香族雜環基時之取代基,可舉出如氘、碳數1~12之烷基、碳數7~19之芳烷基、碳數2~12之烯基、碳數2~12之炔基、氰基、碳數2~24之二烷基胺基、碳數6~36之二芳基胺基、碳數14~38之二芳烷基胺基、胺基、硝基、醯基、碳數2~12之烷氧基羰基、羧基、碳數1~12之烷氧基、碳數1~12之烷基磺醯基、碳數1~12之鹵烷基、羥基、氯、溴、氟、醯胺基、苯氧基、碳數1~12之烷硫基、碳數6~18之芳香族烴基、或碳數3~17之芳香族雜環基。較佳之取代基為氘、碳數1~12之烷基、碳數7~19之芳烷基、碳數2~12之烯基、或碳數2~12之炔基、碳數6~18之芳香族烴基、或碳數3~17之芳香族雜環基。
一般式(1)、(2)中,Y表示上述式(1b)所表示之吲哚咔唑基。
式(1b)中,環I表示與鄰接環在任意位置進行縮合之式(1c)所表示之芳香族烴環,環II表示與鄰接環在任意位置進行縮合之式(1d)所表示之雜環。
式(1b)所表示之吲哚咔唑基具有吲哚咔唑骨架。此吲哚咔唑骨架中,式(1c)所表示之芳香族烴環係可與2個鄰接環在任意位置進行縮合,但亦有在構造上無法縮合之位置。式(1c)所表示之芳香族烴環係具有6個邊,但不會以鄰接之2個邊與2個鄰接環進行縮合。又,式(1d)所表示之雜環係可與2個鄰接環在任意位置進行縮合,但亦有在構造上無法縮合之位置。即,式(1d)所表示之雜環雖具有5個邊,但不會以鄰接之2個邊與2個鄰接環進行縮合,又,不會以包含氮原子之邊與鄰接環進行縮合。因此,吲哚咔唑骨架之種類受到限制。
式(1b)中,吲哚咔唑骨架係以以下構造所表示者為佳。由此等之例,即可理解吲哚咔唑骨架中之芳香族烴環及雜環之較佳縮合位置。
式(1d)中,L2為c+1價之基。除存有價數不一致之情況以外,其他係與一般式(2)之L1同義。在此,可與存在於分子內之其他之L1相同,亦可為相異。
一般式(1)及式(1d)中之Z為式(1a)所表示之含硼基。式(1a)中之A係與一般式(1)之A為同義,2個A可分別為相同亦可為相異。
式(1b)及式(1c)中,R係分別獨立表示氘、碳數1~12之烷基、碳數2~12之芳烷基、碳數2~12之烯基、碳數2~12之炔基、氰基、碳數2~24之二烷基胺基、碳數6~36之二芳基胺基、碳數14~38之二芳烷基胺基、胺基、硝基、碳數2~12之醯基、碳數2~12之烷氧基羰基、羧基、碳數1~12之烷氧基、碳數1~12之烷基磺醯
基、碳數1~12之鹵烷基、羥基、醯胺基、苯氧基、碳數1~12之烷硫基、取代或未取代之碳數6~18之芳香族烴基、取代或未取代之碳數3~17之芳香族雜環基、或式(1d)所表示之含硼基。較佳為氘、碳數1~12之烷基、碳數3~10之環烷基、取代或未取代之碳數6~12之芳香族烴基、取代或未取代之碳數3~12之芳香族雜環基、或式(1d)所表示之含硼基。R為具有取代基之芳香族烴基或具有取代基之芳香族雜環基時之取代基,係與L1為具有取代基之芳香族烴基或具有取代基之芳香族雜環基時之取代基相同。
式(1b)~(1c)中,j及m係分別獨立表示0~4之整數,n表示0~2之整數。
一般式(1)、(2)、式(1b)~(1d)中,a及b表示0或1之整數,c表示0~5之整數。在此,j+m+n+(a或b)+c≧1,較佳為j+m+n+(a或b)+c=1。
又,a+c或b+c為0時,至少一個R表示式(1d)所表示之含硼基。j、m、n及b為2以上時,複數之R及Z可分別為相同亦可為相異。
式(1d)中,除L2為c+1價之基以外,其他與一般式(1)、(2)之L1為同義。一般式(1)、(2)及式(1d)中,L1及L2係以至少一個具有縮環構造者為佳,以L1及L2之任一者具有縮環構造者為較佳。
作為式(1b)所表示之吲哚咔唑基之較佳
例,有一般式(3)~(6)之任一式所表示之吲哚咔唑基。一般式(3)~(6)中,與一般式(1)、(2)、式(1b)~(1d)共通之記號係具有相同意義。又,一般式(1)~(6)、式(1b)~(1d)中,在未特別界定時,共通之記號具有相同意義。
作為式(1b)所表示之吲哚咔唑基所包含之吲哚咔唑骨架,係以式(IC-1)~(IC-4)之任一式所表示之骨架為較佳者。式(1b)係包含式(IC-1)~(IC-4)所表示之骨架之概念,能以式(1b)所表示之吲哚咔唑基所代表說明此等式。
式(1b)所表示之吲哚咔唑基可思考為如式(IC-1)~(IC-4)之形態所表示般之母骨架,此等係可因應目的之化合物構造而選擇,使用公知之手法進行合成。
例如,式(IC-1)所表示之吲哚咔唑骨架係可參考Synlett,2005,No.1,p42-48中揭示之合成例,藉由以下之反應式而合成。
又,式(IC-3)所表示之吲哚咔唑骨架係可參考Archiv der Pharmazie(Weinheim,Germany)1987,320(3),p280-2中揭示之合成例,藉由以下之反應式進行
合成。
一般式(1)或(2)所表示之硼化合物係經由L1而2個吲哚咔唑基(Y)鍵結於硼上,1個或2個A具有鍵結於硼之構造。以下例示一般式(1)或(2)所表示之硼化合物之具體例,但本發明之有機電致發光元件用硼化合物並非係受限於此等。
上述一般式(1)或(2)所表示之硼化合物具有2個吲哚咔唑構造與硼,較佳之硼化合物為具有1個
硼與2個吲哚咔唑基者。藉由使此硼化合物(以下,亦稱為本發明之化合物)被包含於基板上層合陽極、複數有機層及陰極而成之有機EL元件之至少一個有機層中,而可賦予優異有機EL元件。作為含有之有機層,適宜為發光層、電洞輸送層、電子輸送層、電洞阻止層或電子阻止層。在此,使用於發光層時,除可使用作為含有螢光發光、延遲螢光發光或磷光發光性之摻雜劑之發光層之主材料以外,亦可將本發明之化合物使用作為發出螢光及延遲螢光之有機發光材料。本發明之化合物係以被含有作為含有磷光發光摻雜劑之發光層之主材料為特佳。
其次,說明關於本發明之有機EL元件。
本發明之有機EL元件係在層合於基板上之陽極與陰極之間具有含有至少一個發光層之有機層,且至少一有機層包含上述硼化合物。在發光層中一同包含磷光發光摻雜劑與本發明之有機EL元件用化合物則較為有利。
其次,參照圖式同時說明關於本發明之有機EL元件之構造,但本發明之有機EL元件之構造並非係受到圖示而有所任何限定者。
圖1為展示本發明所使用之一般性有機EL元件之構造例之剖面圖,1表示基板、2表示陽極、3表示電洞注入層、4表示電洞輸送層、5表示發光層、6表示電子輸送層、7表示陰極。本發明之有機EL元件中亦可具有與發光層鄰接之激子阻止層,又,發光層與電洞注入層之間亦可具有電子阻止層。激子阻止層可插入於發光層
之陽極側、陰極側之任一者,亦可同時插入於兩者。本發明之有機EL元件中,雖係以基板、陽極、發光層及陰極為必須之層,但必須之層以外之層係亦可具有電洞注入輸送層、電子注入輸送層,並且係以在發光層與電子注入輸送層之間具有電洞阻止層為宜。尚且,電洞注入輸送層係意指電洞注入層與電洞輸送層之任一者或兩者,電子注入輸送層係意指電子注入層與電子輸送層之任一者或兩者。
尚且,亦可為與圖1相反之構造,即,亦可於基板1上依序層合陰極7、電子輸送層6、發光層5、電洞輸送層4、陽極2,於此情況因應需要亦可追加層,或予以省略。
本發明之有機EL元件係被支撐於基板上為佳。此基板並無特別限制,只要係自以往慣用於有機EL元件中者即可,可使用例如由玻璃、透明塑膠、石英等所構成者。
作為有機EL元件中之陽極,較佳可使用將功函數大之(4eV以上)金屬、合金、導電性化合物及此等混合物作為電極物質者。此般電極物質之具體例可舉出如Au等之金屬、CuI、銦錫氧化物(ITO)、SnO2、ZnO等之導電性透明材料。又,亦可使用IDIXO(In2O3-ZnO)等可製成非晶質且透明導電膜之材料。陽極係可使此等電極物
質藉由蒸鍍或濺鍍等之方法,形成薄膜,並以光微影術形成所欲形狀之圖型,或在不強烈需要圖型精度時(100μm以上程度),於上述電極物質之蒸鍍或濺鍍時,經由所欲形狀之遮罩形成圖型亦可。或,在使用如有機導電性化合物般之能塗布之物質時,亦可使用印刷方式、塗覆方式等濕式成膜法。在從此陽極取出發光時,穿透率係以設成大於10%為理想,且作為陽極之薄膜電阻係以數百Ω/□以下為佳。並且,膜厚雖係根據材料而不同,通常為10~1000nm,較佳選自10~200nm之範圍內。
另一方面,陰極係使用將功函數小之(4eV以下)金屬(稱為電子注入性金屬)、合金、導電性化合物及此等混合物作為電極物質者。此般電極物質之具體例可舉出如,鈉、鈉-鉀合金、鎂、鋰、鎂/銅混合物、鎂/銀混合物、鎂/鋁混合物、鎂/銦混合物、鋁/氧化鋁(Al2O3)混合物、銦、鋰/鋁混合物、稀土類金屬等。此等之中,由電子注入性及對氧化等之耐久性之觀點,以電子注入性金屬與比此之功函數值還大且安定金屬之第二金屬之混合物,例如、鎂/銀混合物、鎂/鋁混合物、鎂/銦混合物、鋁/氧化鋁(Al2O3)混合物、鋰/鋁混合物、鋁等為適宜。陰極係藉由使電極物質藉由蒸鍍或濺鍍等之方法形成薄膜,即可製成。又,陰極之薄膜電阻係以數百Ω/□以下為佳,膜厚通常為10nm~5μm,較佳選自50~200nm之範圍
內。尚且,為了使發光之光穿透,有機EL元件之陽極或陰極之任一者若為透明或半透明,則發光亮度提升且恰好有利。
又,於陰極上將上述金屬製成1~20nm之膜厚後,藉由於其上製作陽極之說明中例舉之導電性透明材料,而可製成透明或半透明之陰極,藉由應用此即可製成陽極與陰極之兩者皆具有穿透性之元件。
發光層係為藉由分別從陽極及陰極所注入之電洞及電子之再結合而生成激子後進行發光之層,發光層中係以包含有機發光材料與主材料為理想。
發光層為螢光發光層時,發光層中雖亦可單獨使用螢光發光材料,但以將螢光發光材料使用作為螢光發光摻雜劑並與主材料為佳。
作為發光層中之螢光發光材料,可使用本發明之硼化合物,但螢光發光材料係如多數之專利文獻等中所已知般,亦可選自此等。例如可舉出苯并噁唑衍生物、苯并噻唑衍生物、苯并咪唑衍生物、苯乙烯基苯衍生物、聚苯基衍生物、二苯基丁二烯衍生物、四苯基丁二烯衍生物、萘二甲醯亞胺衍生物、香豆素衍生物、縮合芳香族化合物、苝酮(perynone)衍生物、噁二唑(oxadiazole)衍生物、噁嗪(oxazine)衍生物、醛連氮(aldazine)衍生物、Pyraridine衍生物、環戊二烯衍生物、雙苯乙烯基
蒽衍生物、喹吖啶酮衍生物、吡咯并吡啶衍生物、噻二唑并吡啶(thidiazolopyridine)衍生物、苯乙烯基胺衍生物、二酮吡咯並吡咯衍生物、芳香族二次甲基化合物、8-喹啉醇衍生物之金屬錯合物或pyrromethene衍生物之金屬錯合物、稀土類錯合物、遷移金屬錯合物所代表之各種金屬錯合物等、聚噻吩、聚苯、聚苯并乙烯(polyphenylene vinylene)等之聚合物化合物、有機矽烷衍生物等。較佳可舉出如縮合芳香族化合物、苯乙烯基化合物、二酮吡咯並吡咯化合物、噁嗪化合物、pyrromethene金屬錯合物、遷移金屬錯合物、或鑭系元素錯合物,更佳可舉出如稠四苯、芘、屈(chrysene)、聯三伸苯、苯并[c]菲、苯并[a]蒽、稠五苯、苝、熒(Fluoranthene)、苊并熒(Acenaphthofluoranthene)、二苯并[a,j]蒽、二苯并[a,h]蒽、苯并[a]稠四苯、並六苯(Hexacene)、蒽嵌蒽(Anthanthren)、萘并[2,1-f]異喹啉、α-萘非啶、菲并噁唑(phenanthrooxazole)、喹啉并[6,5-f]喹啉、苯并萘并[2,3-b]噻吩(benzothiophanthrene)等。此等亦可具有烷基、芳基、芳香族雜環基、或二芳基胺基作為取代基。
作為發光層中之螢光主材料,可使用本發明之硼化合物,但螢光主材料係如多數之專利文獻等中所已知般,亦可選自此等。例如可使用,萘、蒽、菲、芘、屈、稠四苯、聯三伸苯、苝、熒、茀、茚等之具有縮合芳基環之化合物或其衍生物、N,N’-二萘基-N,N’-二苯基-4,4’-二苯基-1,1’-二胺等之芳香族胺衍生物、以參(8-羥
基喹啉)鋁(III)為首之金屬螯合化類奧辛化合物(metal chelated oxinoid compound)、二苯乙烯基苯衍生物等之雙苯乙烯基衍生物、四苯基丁二烯衍生物、茚衍生物、香豆素衍生物、噁二唑衍生物、吡咯并吡啶衍生物、苝酮衍生物、環戊二烯衍生物、吡咯并吡咯衍生物、噻二唑并吡啶衍生物、二苯并呋喃衍生物、咔唑衍生物、吲哚咔唑衍生物、三嗪衍生物,聚合物系則如聚苯并乙烯衍生物、聚對亞苯衍生物、聚茀衍生物、聚乙烯咔唑衍生物、聚噻吩衍生物等,但並非係受到特別限定者。
在將前述螢光發光材料使用作為螢光發光摻雜劑且包含主材料時,螢光發光摻雜劑在發光層中所含有之量為0.01~20重量%,較佳在0.1~10重量%之範圍內為宜。
通常有機EL元件係從陽極、陰極之兩電極對發光物質注入電荷而生成激發狀態之發光物質進而使其發光。在電荷注入型之有機EL元件之情況,一般認為所生成之激子之中,被激發至一重態激發狀態者為25%,剩餘75%為被激發至三重態激發狀態者。如Advanced Materials 2009,21,4802-4806.所示般,已知特定之螢光發光物質藉由系間交差等向三重態激發狀態遷移能量後,因三重態-三重態消滅或熱能之吸收,在一重態激發狀態下反系間交差而放射螢光,進而可發現熱活性化延遲螢光。於本發明之有機EL元件中亦可能發現延遲螢光。此時,亦可包含螢光發光及延遲螢光發光之兩者。但,發光之一
部或部分可具有來自主材料之發光。
發光層為延遲螢光發光層時,發光層雖亦可單獨使用遲延發光材料,但係以將延遲螢光材料使用作為延遲螢光發光摻雜劑且混合主材料為佳。
作為發光層中之延遲螢光發光材料,可使用本發明之硼化合物,亦可選自公知之延遲螢光發光材料。例如,可舉出錫錯合物、吲哚咔唑衍生物、銅錯合物、咔唑衍生物等。具體地可舉出如以下之非專利文獻、專利文獻中記載之化合物,但並非受限於此等化合物者。
Adv.Mater.2009,21,4802-4806、Appl.Phys.Lett.98,083302(2011)、日本特開2011-213643號公報、及J.Am.Chem.Soc.2012,134,14706-14709。
遲延發光材料之具體例係如下述,但並非係受限於下述化合物者。
將前述延遲螢光發光材料使用作為延遲螢光發光摻雜劑且混合主材料時,延遲螢光發光摻雜劑在發光層中所被含有之量為在0.01~50重量%,較佳在0.1~20重量%,更佳在0.01~10%之範圍為宜。
作為發光層中之延遲螢光主材料,可使用本發明之硼化合物,但亦可選自硼以外之化合物。例如,可使用萘、蒽、菲、芘、屈、稠四苯、聯三伸苯、苝、熒、茀、茚等之具有縮合芳基環之化合物或其衍生物、N,N’-二萘基-N,N’-二苯基-4,4’-二苯基-1,1’-二胺等之芳香族胺衍生物、以參(8-羥基喹啉)鋁(III)為首之金屬螯合化類奧辛化合物、二苯乙烯基苯衍生物等之雙苯乙烯基衍生
物、四苯基丁二烯衍生物、茚衍生物、香豆素衍生物、噁二唑衍生物、吡咯并吡啶衍生物、苝酮衍生物、環戊二烯衍生物、吡咯并吡咯衍生物、噻二唑并吡啶衍生物、二苯并呋喃衍生物、咔唑衍生物、吲哚咔唑衍生物、三嗪衍生物,聚合物系則有聚苯并乙烯衍生物、聚對亞苯衍生物、聚茀衍生物、聚乙烯咔唑衍生物則有聚噻吩衍生物、芳基矽烷衍生物等,但並非係受限於此等者。
在發光層為磷光發光層之情況,發光層包含磷光發光摻雜劑與主材料。作為磷光發光摻雜劑材料,以含有包含選自釕、銠、鈀、銀、錸、鋨、銥、鉑及金之至少一個金屬之有機金屬錯合物為宜。具體地可舉出如以下之專利公報類中記載之化合物,但並非受限於此等化合物。
WO2009/073245號公報、WO2009/046266號公報、WO2007/095118號公報、WO2008/156879號公報、WO2008/140657號公報、US2008/261076號公報等。
作為較佳之磷光發光摻雜劑,可舉出如具有Ir等之貴金屬元素作為中心金屬之Ir(ppy)3等之錯合物類、Ir(bt)2‧acac3等之錯合物類、PtOEt3等之錯合物類。此等錯合物類之具體例係如以所下,但並非係受限於下述之化合物。
前述磷光發光摻雜劑在發光層中所被含有之量在2~40重量%,較佳在5~30重量%之範圍內為宜。
在發光層為磷光發光層之情況,發光層中之主材料係以使用前述一般式(1)所表示之硼化合物為佳。但,將該硼化合物使用於發光層以外之其他任意之有機層時,發光層所使用之材料亦可為硼化合物以外之其他主材料。又,亦可併用硼化合物與其他主材料。並且,亦可併用複數種類公知之主材料而使用。
作為能使用之公知之主體化合物,係以具有電洞輸送能、電子輸送能,且防止發光之長波長化,並且具有高玻璃轉移溫度之化合物為佳。
此般其他主材料係已由多數之專利文獻等所周知,故可選自該等文獻。主材料之具體例並非係受到特別限定者,可舉出如吲哚衍生物、咔唑衍生物、三唑衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基烷衍生物、吡唑啉衍生物、吡唑啉酮衍生物、苯二胺衍生物、芳基胺衍生物、胺基取代查酮衍生物、苯乙烯基蒽衍生物、茀酮衍生物、腙衍生物、茋衍生物、矽氮烷衍生物、芳香族第三胺化合物、苯乙烯基胺化合物、芳香族二次甲基系化合物、卟啉系化合物、蔥醌二甲烷(Anthraquinodimethane)衍生物、蔥酮衍生物、二苯基醌衍生物、噻喃二氧化物(Thiopyrandioxide)衍生物、萘苝等之雜環四羧酸酐、酞菁衍生物、以8-喹啉醇衍生物之金屬錯合物或金屬酞菁、苯并噁唑或苯并噻唑衍生物之
金屬錯合物所代表之各種金屬錯合物、聚矽烷系化合物、聚(N-乙烯咔唑)衍生物、苯胺系共聚物、噻吩寡聚物、聚噻吩衍生物、聚苯衍生物、聚苯并乙烯衍生物、聚茀衍生物等之高分子化合物等。
發光層可為螢光發光層、延遲螢光發光層或磷光發光層之任一者,但以磷光發光層為佳。
注入層係指為了降低驅動電壓或提高發光亮度而設置於電極與有機層間之層,具有電洞注入層與電子注入層,亦可使其存在陽極與發光層或電洞輸送層之間、及陰極與發光層或電子輸送層之間。注入層係可因應需要而設置。
電洞阻止層在廣義下係具有電子輸送層之機能,由具有輸送電子之機能且輸送電洞之能力為顯著小之電洞阻止材料所構成,藉由輸送電子並同時阻止電洞而可提升電子與電洞之再結合機率。
電洞阻止層中係以使用本發明之硼化合物為佳,但將硼化合物使用於其他任一有機層時,亦可使用公知之電洞阻止層材料。又,作為電洞阻止層材料,亦可因應需要而使用後述之電子輸送層之材料。
電子阻止層為具有輸送電洞並同時阻止電子到達電洞輸送層之功用,由具有輸送電洞之機能且輸送電子之能力為顯著小之電子阻止材料所構成,藉由輸送電洞並同時阻止電子而可提升電子與電洞之再結合機率。
電子阻止層之材料係可使用本發明之硼化合物,但作為其他材料,亦可因應需要使用後述之電洞輸送層之材料。電子阻止層之膜厚較佳為3~100nm,更佳為5~30nm。
激子阻止層係指用以阻止於發光層內因電洞與電子之再結合所產生之激子擴散至電荷輸送層之層,藉由插入本層,變得能有效地將激子封閉於發光層內,進而可使元件之發光效率提升。激子阻止層係可插入於與發光層鄰接之陽極側、陰極側之任一側,亦能同時插入於兩者。
激子阻止層之材料係可使用本發明之硼化合物,但作為其他材料,例如,可舉出1,3-二咔唑基苯(mCP),或雙(2-甲基-8-羥基喹啉)-4-苯基酚鋁(III)(BAlq)。
電洞輸送層係由具有輸送電洞之機能之電洞輸送材料所構成,電洞輸送層係可設置單層或複數層。
電洞輸送材料為具有電洞之注入或輸送、電
子之障壁性之任一性質者,可為有機物、無機物之任一者。電洞輸送層中係以使用一般式(1)所表示之硼化合物為佳,但亦可使用選自過往公知之化合物之中之任意者。作為能使用之公知之電洞輸送材料,例如可舉出三唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基烷衍生物、吡唑啉衍生物及吡唑啉酮衍生物、苯二胺生物、芳基胺衍生物、胺基取代查酮衍生物、噁唑衍生物、苯乙烯基蒽衍生物、茀酮衍生物、腙衍生物、茋衍生物、矽氮烷衍生物、苯胺系共聚物,及導電性高分子寡聚物、尤其係噻吩寡聚物等,以使用卟啉化合物、芳香族第3級胺化合物及苯乙烯基胺化合物為佳,以使用芳香族第3級胺化合物為更佳。
電子輸送層係由具有輸送電子之機能之材料所構成,電子輸送層可設置單層或複數層。
作為電子輸送材料(亦有兼具電洞阻止材料之情況),只要具有將從陰極所注入之電子傳達至發光層之機能即可。電子輸送層中係以使用本發明之一般式(1)所表示之材料為佳,可使用選自過往公知之化合物之中之任意者,例如可舉出硝基取代茀衍生物、二苯基醌衍生物、噻喃二氧化物衍生物、碳二醯亞胺、亞茀基甲烷衍生物、蔥醌二甲烷及蔥酮衍生物、噁二唑衍生物等。並且,上述噁二唑衍生物中噁二唑環之氧原子被硫原子所取
代之噻二唑衍生物,具有周知作為電子吸引基之喹喔啉環之喹喔啉衍生物亦可使用作為電子輸送材料。並且,亦可使用對此等材料導入高分子鏈之高分子材料,或將此等材料作為高分子之主鏈之高分子材料。
以下,根據實施例更詳細地說明本發明,但本發明當然地並非係受到此等實施例所限定者,在不超出其要旨之範圍內,皆可在各種之形態下實施。
依據以下所示之路徑合成磷光發光元件用材料之硼化合物。尚且,化合物編號係對應於上述例示化合物所附加之編號。
在氮環境下,添加化合物(A)10.00g(0.0390mol)、三溴苯6.14g(0.0195mol)、碘化銅0.74g、三磷酸鉀24.84g、1,4-二噁烷500ml,在室溫下攪
拌幾小時。添加反-1,2-環己烷二胺1.34g,在110℃下攪拌9小時。使該反應溶液冷卻至室溫,過濾後進行濃縮。藉由以矽膠管柱層析純化取得之殘渣,而取得白色固體之中間體(B)3.00g(0.00451mol、收率12%)。
於氮環境下,添加中間體(B)3.00g(0.00451mol)、碘苯110.41g(0.5412mol)、銅1.89g、及碳酸鉀6.86g,在180℃下攪拌5小時。使該反應溶液冷卻至室溫,過濾後進行濃縮。藉由以矽膠管柱層析純化取得之殘渣,而取得白色固體之化合物(C)3.50g(0.00428mol、收率95%)。
於氮環境下,添加中間體(C)3.50g(0.00428mol)、THF 50ml,冷卻至-60℃。添加1.59M n-BuLi 3.2ml,在-60℃下攪拌30分後,添加二基氟硼烷5.000g(0.0186mol),在室溫下攪拌22小時。其後,去除溶劑,以矽膠管柱層析使取得之殘渣再結晶進行純化而取得黃色固體之化合物B14 1.86g(0.00188mol、收率44%)。
APCI-TOFMS m/z 988[M+1]、1H-NMR測量結果(測量溶劑:C6D6)係如圖2所示。
於形成有由膜厚110nm之ITO所構成之陽極之玻璃基板上,以真空蒸鍍法在真空度4.0×10-5Pa下使各薄膜層合。首先,於ITO上以25nm之厚度形成銅酞菁(CuPC)。其次,以40nm之厚度使4,4’-雙[N-(1-萘基)-N-苯基胺基]聯苯(NPB)形成作為電洞輸送層。其次,於電洞輸送層上,從相異之蒸鍍源,使作為主材料之化合物(B14),與作為磷光發光摻雜劑之參(2-苯基吡
啶)銥(III)(Ir(ppy)3)進行共蒸鍍,而以40nm之厚度形成發光層。發光層中之Ir(ppy)3之濃度為10.0wt%。其次,以20nm之厚度使參(8-羥基喹啉)鋁(III)(Alq3)形成作為電子輸送層。並且,於電子輸送層上,以1.0nm之厚度形成氟化鋰(LiF)作為電子注入層。最後,於電子注入層上以70nm之厚度形成鋁(Al)作為電極,製成有機EL元件。
將取得之有機EL元件連接於外部電源並施加直流電壓時,且確認到具有如表1般之發光特性。於表1中,亮度、電壓及發光效率係表示在20mA/cm2下之值。元件發光光譜之最大波長為520nm,得知取得來自Ir(ppy)3之發光。
與合成例1同樣地施行而合成化合物A8、A15、A24、B5、B6、B24、C8、D37、E25、F28及F32。
除實施例1之發光層之主材料係取代化合物B14而改為使用化合物A8、A15、A24、B5、B6、B24、C8、D37、E25、F28及F32以外,其他係與實施例1同樣地實行而製成有機EL元件。各別之元件發光光譜之最大波長為520nm,得知取得來自Ir(ppy)3之發光。各自之發光特性係如表1所示。
除發光層之主材料係使用CBP以外,其他與實施例1同樣地實行而製成有機EL元件。
除發光層之主材料係使用下述化合物Ho-1以外,與實施例1同樣地實行而製成有機EL元件。
比較例1、比較例2中製成之有機EL元件之元件發光光譜之最大波長皆為520nm,得知取得來自Ir(ppy)3之發光。作為主材料使用之化合物及各別之發光特性係如表1所示。
從表1可得知,在相對於磷光主體係使用一般周知之CBP時,使用本發明之硼化合物之有機EL元件展示低驅動電壓且良好之發光特性。又,得知在與使用3個吲哚咔唑基係經由硼取代基而連結之化合物Ho-1相比時,本發明展示良好之發光特性。從以上可明白得知使用上述硼化合物之有機EL元件之優越性。
本發明之有機EL元件在發光特性、驅動電壓
以及耐久性上皆為可滿足實用上之等級,在平板顯示器(行動電話顯示元件、車上用顯示元件、OA電腦顯示元件或電視等)、活用作為面發光體之特徵之光源(照明、影印機之光源、液晶顯示器或計器類之背光光源)、顯示板或標識燈等之應用上,其係技術性價值為龐大者。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧電洞注入層
4‧‧‧電洞輸送層
5‧‧‧發光層
6‧‧‧電子輸送層
7‧‧‧陰極
Claims (7)
- 一種有機電致發光元件用硼化合物,其係下述一般式(1)或(2)所表示者;
- 如請求項1之有機電致發光元件用硼化合物,其中於一般式(1)及(2)中,Y為一般式(3)~(6)之任一式所表示之吲哚咔唑基;
- 如請求項1之有機電致發光元件用硼化合物,其中A係分別獨立為碳數1~12之烷基、取代或未取代之碳數6~18之芳香族烴基、或取代或未取代之碳數3~17之芳香族雜環基。
- 如請求項1之有機電致發光元件用硼化合物,其中L1及L2之至少一者為具有縮環構造之基。
- 一種有機電致發光元件,其係具有包含如請求項1~4中任一項之有機電致發光元件用硼化合物之有機層。
- 如請求項5之有機電致發光元件,其中包含有機電致發光元件用硼化合物之有機層為選自發光層、電洞輸送層、電洞注入層、電子輸送層及電子注入層之至少一層。
- 如請求項5之有機電致發光元件,其中包含有機電致發光元件用硼化合物之有機層為發光層,該發光層係含有磷光發光性摻雜劑與該有機電致發光元件用化合物作為主材料。
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US10892425B1 (en) * | 2017-03-03 | 2021-01-12 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
WO2019053067A1 (en) * | 2017-09-13 | 2019-03-21 | Cynora Gmbh | ORGANIC MOLECULES, IN PARTICULAR FOR USE IN OPTOELECTRONIC DEVICES |
US11706977B2 (en) | 2018-01-11 | 2023-07-18 | Samsung Electronics Co., Ltd. | Heterocyclic compound, composition including the same, and organic light-emitting device including the heterocyclic compound |
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CN110492010B (zh) * | 2018-05-15 | 2022-01-07 | 上海和辉光电股份有限公司 | 一种有机电致发光器 |
CN116675709A (zh) * | 2022-02-21 | 2023-09-01 | 华为技术有限公司 | 含硼化合物、发光器件和显示装置 |
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