TWI765091B - 有機電致發光化合物及包括所述有機電致發光化合物之有機電致發光裝置 - Google Patents
有機電致發光化合物及包括所述有機電致發光化合物之有機電致發光裝置 Download PDFInfo
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- TWI765091B TWI765091B TW107131256A TW107131256A TWI765091B TW I765091 B TWI765091 B TW I765091B TW 107131256 A TW107131256 A TW 107131256A TW 107131256 A TW107131256 A TW 107131256A TW I765091 B TWI765091 B TW I765091B
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- substituted
- unsubstituted
- alkyl
- aryl
- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 94
- 239000000463 material Substances 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000005104 aryl silyl group Chemical group 0.000 claims description 32
- 125000001769 aryl amino group Chemical group 0.000 claims description 30
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- -1 cyano, carboxyl Chemical group 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 150000004982 aromatic amines Chemical class 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 1
- 229940035422 diphenylamine Drugs 0.000 claims 1
- 239000010410 layer Substances 0.000 description 120
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 230000005525 hole transport Effects 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 17
- 230000000903 blocking effect Effects 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000872 buffer Substances 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-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
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
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- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WYLIRYQDDKDHLT-UHFFFAOYSA-N CC1=CC=CC=C1C.CC1=CC=CC=C1C Chemical compound CC1=CC=CC=C1C.CC1=CC=CC=C1C WYLIRYQDDKDHLT-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 2
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
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- 230000001590 oxidative effect Effects 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
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- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 125000006017 1-propenyl group Chemical group 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- MHJUNMARMFAUBI-UHFFFAOYSA-N n-phenyliminobenzamide Chemical compound C=1C=CC=CC=1C(=O)N=NC1=CC=CC=C1 MHJUNMARMFAUBI-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- 238000000197 pyrolysis Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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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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Abstract
本揭示案涉及一種有機電致發光化合物及包括所述有機電致發光化合物之有機電致發光裝置。可藉由包括根據本揭示案之有機電致發光化合物來提供具有低驅動電壓及/或高發光效率及/或長壽命的有機電致發光裝置。
Description
本揭示案涉及一種可以用於有機電致發光裝置(OLED)領域中之有機電致發光化合物及包括所述有機電致發光化合物之有機發光裝置。
電致發光裝置(EL裝置)為具有提供更寬視角、更高對比率及更快響應時間之優點的自發光裝置。第一種有機EL裝置由Eastman Kodak開發,使用小的芳族二胺分子及鋁錯合物作為形成發光層之材料(參見《應用物理學快報(Appl. Phys. Lett.)》51, 913, 1987)。
有機電致發光裝置(OLED)藉由將電荷注入有機發光材料而將電能轉換為光,且通常包括陽極、陰極及在兩個電極之間形成的有機層。有機EL裝置之有機層視需要可由電洞注入層、電洞傳輸層、電洞輔助層、發光輔助層、電子阻擋層、發光層(含有主體及摻雜劑材料)、電子緩衝層、電洞阻擋層、電子傳輸層、電子注入層等構成。有機層中使用的材料可根據功能而分為電洞注入材料、電洞傳輸材料、電洞輔助材料、發光輔助材料、電子阻擋材料、發光材料、電子緩衝材料、電洞阻擋材料、電子傳輸材料、電子注入材料等。在有機EL裝置中,來自陽極之電洞及來自陰極之電子藉由電壓注入至發光層中,且藉由電洞及電子的複合產生具有高能量的激子。有機發光化合物利用能量移動至激發態,且當有機發光化合物自激發態返回至基態時自能量發光。
決定有機EL裝置發光效率的最重要因素為發光材料。發光材料需要具有以下特徵:高量子效率、高電子及電洞之移動程度,以及所形成之發光材料層的均勻性及穩定性。發光材料根據發光顏色分為藍色、綠色及紅色發光材料,且進一步包含黃色或橙色發光材料。此外,在功能態樣中,發光材料分為主體材料及摻雜劑材料。最近,緊迫的任務為開發具有高效率及長壽命之有機EL裝置。特別是,考慮到中型及大型OLED面板所需的EL特性,迫切需要開發優於習知材料之非常優異的發光材料。為此,較佳地,作為固體狀態及能量傳輸器中之解決方法,主體材料應具有高純度及適當的分子量,以便在真空下沈積。此外,要求主體材料具有實現熱穩定性之高玻璃轉移溫度及熱解溫度、實現長壽命之高電化學穩定性、非晶薄膜易於成形性、與相鄰層的良好黏合性,以及在層間不移動。
此外,需要開發在電洞傳輸層、緩衝層、電子傳輸層等中具有良好熱穩定性,且能夠改良有機電致發光裝置的效能,諸如驅動電壓、發光效率及壽命的材料。
需要解決的問題
本揭示案之目的為提供一種能夠首先生產具有低驅動電壓及/或高的發光效率及/或長壽命之有機電致發光裝置的有機電致發光化合物,其次,為提供包括有機電致發光化合物之電致發光裝置。問題的解決方案
作為解決上述技術問題的深入研究的結果,本發明人發現其中5員環及芳環與7員環稠合的雜環化合物可提供具有低驅動電壓及/或高發光效率及/或長壽命特性之有機電致發光裝置,使本發明完成。具有低玻璃轉移溫度(Tg)的化合物可減少薄膜內的電荷遷移率,且降低OLED裝置的效能。因此,儘管分子量相對低,本發明人已開發一種新穎有機電致發光化合物,其具有高Tg,因此可提供優異的形態穩定性。
更具體地,上述目的可利用由下式1表示之有機電致發光化合物來實現。--- (1) 其中, X1
表示N-L-(Ar)a
、S或O; L表示單鍵、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之(3至30員)伸雜芳基; Ar表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基、或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基; Y1
至Y12
各自獨立地表示N或CR1
; R1
各自獨立地表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基、或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基;或者可與相鄰的取代基鍵聯以形成經取代或未經取代之環;及 a表示1至4之整數,其中當a為2至4時,Ar中之每一者可相同或不同。本發明的效果
具有低驅動電壓及/或高發光效率及/或長壽命之有機電致發光裝置可藉由包括根據本發明之有機電致發光化合物製備。
在下文中,將詳細描述本揭示案。然而,以下描述旨在解釋本發明,並不意味著以任何方式限制本發明的範圍。
本揭示案中之術語「有機電致發光化合物」意謂可用於有機電致發光裝置中且若需要,可包括在構成有機電致發光裝置之任何層中的化合物。
本揭示案中之術語「有機電致發光材料」意謂可用於有機電致發光裝置中且可包括至少一種化合物之材料。若需要,有機電致發光材料可包括在構成有機電致發光裝置的任何層中。例如,有機電致發光材料可為電洞注入材料、電洞傳輸材料、電洞輔助材料、發光輔助材料、電子阻擋材料、發光材料、電子緩衝材料、電洞阻擋材料、電子傳輸材料、電子注入材料等。
由上式1表示之化合物將更詳細地描述如下。
在式1中,X1
表示N-L-(Ar)a
、S或O。
在式1,L表示單鍵、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之(3至30員)伸雜芳基;較佳地,可為單鍵、經取代或未經取代之(C6-C25)伸芳基、或經取代或未經取代之(5至25員)伸雜芳基;更佳地,可為單鍵、未取代之(C6-C18)伸芳基、或未取代之(5至18員)伸雜芳基,且伸雜芳基可包含至少一個氮。
在一個實施例中,在式1中,L可為單鍵、經取代或未經取代之伸苯基、經取代或未經取代之間伸聯苯基、經取代或未經取代之對伸聯苯基、經取代或未經取代之伸吡啶基、經取代或未經取代之伸嘧啶基、經取代或未經取代之伸三嗪基、經取代或未經取代之伸萘基、經取代或未經取代之伸喹唑啉基、或經取代或未經取代之伸喹喏啉基。
在式1,Ar表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基、或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基;較佳地,可為氫、經取代或未經取代之(C6-C25)芳基、經取代或未經取代之(5至25員)雜芳基、或經取代或未經取代之二(C6-C25)芳基胺基;更佳地,可為氫、經取代或未經取代之(C6-C18)芳基、經取代或未經取代之(5至18員)雜芳基、或經取代或未經取代之二(C6-C18)芳基胺基。
在一個實施例中,在式1中,Ar可為氫、經取代或未經取代之苯基、經取代或未經取代之間聯苯、經取代或未經取代之對聯苯、經取代或未經取代之萘基、經取代或未經取代之吡啶基、經取代或未經取代之嘧啶基、經取代或未經取代之三嗪基、經取代或未經取代之喹唑啉基、經取代或未經取代之喹喏啉基、經取代或未經取代之咔唑基、經取代或未經取代之二苯基胺基、或經取代或未經取代之茀基苯基胺基。
在式1,a表示1至4之整數,且當a為2至4時,Ar中之每一者可相同或不同,例如當a為2時,Ar可全部為苯基或各自可為苯基及萘基或苯基及茀基。
在式1中,Y1
至Y12
各自獨立地表示N或CR1
。根據本揭示案之一個實施例,Y1
至Y12
可全部為CR1
,且根據本揭示案之另一實施例,Y1
至Y12
中之至少一者可為N。
在式1中,R1
各自獨立地表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基、或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基;或可鍵聯至相鄰的取代基以形成經取代或未經取代之環,例如可鍵聯至相鄰取代基以形成經取代或未經取代之(C3-C30)單環或多環脂環或芳環、或其組合,其碳原子可經選自氮、氧及硫之至少一個雜原子置換;較佳地,可為氫、經取代或未經取代之(C1-C20)烷基、經取代或未經取代之(C6-C25)芳基、經取代或未經取代之(5至25員)雜芳基、或經取代或未經取代之二(C6-C25)芳基胺基;或可連接至相鄰取代基以形成經取代或未取代之(C3-C25)單環或多環芳環,其至少一個碳原子可經氮置換;更佳地,可為氫、經取代或未經取代之(C1-C10)烷基、經取代或未經取代之(C6-C18)芳基、經取代或未經取代之(5至18員)雜芳基、或經取代或未經取代之二(C6-C18)芳基胺基;或可連接至相鄰取代基以形成經取代或未取代之(C6-C18)單環或多環芳環,其至少一個碳原子可經氮置換。
在一個實施例中,在式1中,R1
各自獨立地可為氫、經取代或未經取代之甲基、經取代或未經取代之苯基、經取代或未經取代之間聯苯、經取代或未經取代之對聯苯、經取代或未經取代之萘基、經取代或未經取代之吡啶基、經取代或未經取代之嘧啶基、經取代或未經取代之三嗪基、經取代或未經取代之喹唑啉基、經取代或未經取代之喹喏啉基、或經取代或未經取代之苯基聯苯胺基。
根據本揭示案之一個實施例,在式1中,Y1
至Y12
中之兩個相鄰基團表示CR1
,且兩個相鄰的R1
可以彼此稠合以形成由下式2至5中之任一者表示的環。例如,式1化合物可含有下式2至5中之至少一個環。
在式4中,X表示N或CR2
。根據本揭示案之一個實施例,X可全部為CR2
,且根據本揭示案之另一實施例,X中之至少一者可為N。
R2
各自獨立地表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基、或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基,較佳地,可為經取代或未經取代之(C6-C25)芳基或經取代或未經取代之(5至25員)雜芳基,更佳地,可為未經取代之(C6-C18)芳基或未經取代之(5至18員)雜芳基。
在式5中,R3
表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之單或二(C1-C30)烷基胺基、經取代或未經取代之單或二(C6-C30)芳基胺基、或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基,較佳地,可為經取代或未經取代之(C6-C25)芳基或經取代或未經取代之(5至25員)雜芳基,更佳地,可為未經取代之(C6-C18)芳基或未經取代之(5至18員)雜芳基。例如,在式5中,R3
可為苯基。
在式1中,(伸)雜芳基各自獨立地含有選自B、N、O、S、Si及P之至少一個雜原子,較佳地,可含有選自N、O及S之至少一個雜原子,更佳地,可含有至少一個氮原子。
在本文中,「(C1-C30)烷基」意謂構成鏈的具有1至30個碳原子的直鏈或分支鏈烷基,其中碳原子數較佳為1至20,更佳為1至10,且包含甲基、乙基、正丙基、異丙基、正丁基、異丁基及第三丁基等。「(C2-C30)烯基」意謂構成鏈的具有2至30個碳原子的直鏈或分支鏈烯基,其中碳原子數較佳為2至20,更佳為2至10,且包含乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等。「(C2-C30)炔基」意謂構成鏈的具有2至30個碳原子的直鏈或分支鏈炔基,其中碳原子數較佳為2至20,更佳為2至10,且包含乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等。「(C3-C30)環烷基」意謂具有3至30個環骨架碳原子的單環或多環烴,其中碳原子數較佳為3至20,更佳為3至7,且包含環丙基、環丁基、環戊基、環己基等。「(3至7員)雜環烷基」意謂具有3至7個環骨架原子,較佳5至7個環骨架原子,包含選自由B、N、O、S、Si及P,較佳O、S及N組成之群的至少一個雜原子的環烷基,且包含四氫呋喃、吡咯啶、硫雜環戊烷、四氫哌喃等。「(C6-C30)(伸)芳基」意謂衍生自具有6至30個環骨架碳原子之芳族烴的單環或稠環基團,其中環骨架碳原子之數目較佳為6至25,更佳為6至18,可為部分飽和的,且可包括螺環結構。芳基包含苯基、聯苯、聯三苯、萘基,聯萘、苯基萘基、萘基苯基、茀基、苯基茀基、苯并茀基、二苯并茀基、菲基、苯基菲基、蒽基、茚基、三伸苯基、芘基、并四苯基、苝基、屈基、稠四苯基、茀蒽基、螺茀基等。「(3至30員)(伸)雜芳基」意謂具有選自由B、N、O、S、Si及P組成之群的至少一個雜原子且具有3至30個,較佳5至25個,更佳5至18個環骨架原子的芳基;較佳具有1至4個雜原子,且可為單環,或與至少一個苯環稠合的稠環;可為部分飽和的。此外,(伸)雜芳基可為經由單鍵將至少一個雜芳基或芳基與雜芳基鍵聯而形成的基團;且可包含螺環結構。雜芳基包含單環環型雜芳基,諸如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋呫基、吡啶基、吡嗪基、嘧啶基、噠嗪基等,及稠環型雜芳基,諸如苯并呋喃基、苯并噻吩基、異苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異噁唑基、苯并噁唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、噌啉基、喹唑啉基、喹喏啉基、咔唑基、苯并咔唑基、啡噁嗪基、啡噻嗪基、啡啶基、苯并二氧雜環戊烯基、二氫吖啶基等。「鹵素」包含F、Cl、Br及I。
在本文中,「經取代或未取代之環」意謂經取代或未經取代之(C3-C30)單環或多環脂環或芳環、或其組合,較佳地,可為經取代或未經取代之(C5-C25)單環或多環脂環或芳環、或其組合,更佳地,可為經取代或未經取代之(C5-C18)單環或多環脂環或芳環、或其組合。
另外,表述“經取代或未經取代”中之“經取代”意謂某個官能基中之氫原子經另一個原子或另一個官能基,即取代基置換。式1之L、Ar及R1
中的經取代之(C1-C30)烷基、經取代之(C6-C30)(伸)芳基、經取代之(3至30員)(伸)雜芳基、經取代之(C3-C30)環烷基、經取代之(C1-C30)烷氧基、經取代之三(C1-C30)烷基矽烷基、經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基、經取代之三(C6-C30)芳基矽烷基、經取代之單或二(C1-C30)烷基胺基、經取代之單或二(C6-C30)芳基胺基、經取代之(C1-C30)烷基(C6-C30)芳基胺基及經取代之環的取代基各自獨立地為選自由氘、鹵素、氰基、羧基、硝基、羥基、(C1-C30)烷基、鹵基(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)環烷基、(C3-C30)環烯基、(3至7員)雜環烷基、(C6-C30)芳氧基、(C6-C30)芳硫基、(5至30員)雜芳基取代或未經取代之(C6-C30)芳基,二(C6-C30)芳基胺基取代或未經取代之(C6-C30)芳基、(C6-C30)芳基取代或未經取代之(5至30員)雜芳基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30)烷基二(C6-C30)芳基矽烷基、胺基、單或二(C1-C30)烷基胺基、(C1-C30)烷基取代或未經取代之單或二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧基羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼烷基、二(C1-C30)烷基硼烷基、(C1-C30)烷基(C6-C30)芳基硼烷基、(C6-C30)芳基(C1-C30)烷基及(C1-C30)烷基(C6-C30)芳基組成之群的至少一個;較佳地,可為二(C6-C25)芳基胺基取代或未經取代之(C6-C25)芳基、(C6-C25)芳基取代或未經取代之(5至25員)雜芳基、或二(C6-C30)芳基胺基;更佳地,可為二(C6-C18)芳基胺基取代或未經取代之(C6-C18)芳基、(C6-C18)芳基取代或未經取代之(5至18員)雜芳基、或二(C6-C18)芳基胺基,例如苯基;萘;咔唑;經一或多個苯基取代之吡啶、嘧啶或三嗪;經一或多個苯基取代之胺、經苯基及茀基取代之胺、經苯基及聯苯取代之胺、或經苯基及萘基取代之三嗪。
在反應方案1至3中,L、Ar、R1
及a如式1中所定義,且R2
至R12
如R1
中所定義。
本揭示案可提供包括式1之有機電致發光化合物的有機電致發光材料,及包括所述有機電致發光材料之有機電致發光裝置。
有機電致發光材料可僅由本發明之有機電致發光化合物組成,或可進一步包括一般在有機電致發光材料中使用的習知材料。
本發明之由式1表示的有機電致發光化合物可包括在電洞傳輸層(HTL)、發光層(EML)、電子緩衝層(沈積裝置中在電子層與發光層之間沈積的化合物)及電子傳輸層(ETL)等,較佳在發光層中。
同時,根據本揭示案之有機電致發光裝置可包括第一電極;第二電極;及在第一及第二電極之間的至少一個有機層。有機層可包括至少一種式1之有機電致發光化合物。此外,有機層可進一步包括選自由基於芳胺之化合物及基於苯乙烯基芳胺之化合物組成之群的至少一種化合物。此外,有機層可進一步包括選自由元素週期表中第1族之金屬、第2族之金屬、第4週期之過渡金屬、第5週期之過渡金屬、鑭系元素及d-過渡元素之有機金屬組成之群的至少一種金屬、或至少一種包括所述金屬之錯合物。
第一及第二電極中之一者可為陽極,且另一者可為陰極。有機層可包括發光層,且可進一步包括選自電洞注入層、電洞傳輸層、電洞輔助層、發光輔助層、電子傳輸層、電子注入層、中間層、電洞阻擋層、電子阻擋層及電子緩衝層中之至少一層。
可在陽極與發光層之間使用電洞注入層、電洞傳輸層、電子阻擋層或其組合。電洞注入層可為多層,以便降低自陽極至電洞傳輸層或電子阻擋層的電洞注入勢壘(或電洞注入電壓),其中多層中之每一層可同時使用兩種化合物。電子阻擋層可置於電洞傳輸層(或電洞注入層)與發光層之間,且可藉由阻擋電子自發光層溢出而將激子限制於發光層內,以防止發光洩漏。電洞傳輸層或電子阻擋層亦可由多層形成,其中多層中之每一層可使用多種化合物。
可在發光層與陰極之間使用電子緩衝層、電洞阻擋層、電子傳輸層或電子注入層、或其組合。電子緩衝層可為多層以便控制電子的注入,增強發光層與電子注入層之間的界面特性,其中多層中之每一層可同時使用兩種化合物。電洞阻擋層或電子傳輸層亦可由多層形成,且每層可使用多種化合物。
發光輔助層可置於陽極與發光層之間,或置於陰極與發光層之間。當發光輔助層置於陽極與發光層之間時,其可用於促進電洞注入及/或電洞傳輸,或用於防止電子溢出。當發光輔助層置於陰極與發光層之間時,其可用於促進電子注入及/或電子傳輸,或用於防止電洞溢出。另外,電洞輔助層可置於電洞傳輸層(或電洞注入層)與發光層之間,且可有效地促進或阻擋電洞傳輸速率(或電洞注入速率),從而使得能夠控制電荷平衡。當有機電致發光裝置包含兩個或更多個電洞傳輸層時,另外包含之電洞傳輸層可用作電洞輔助層或電子阻擋層。發光輔助層、電洞輔助層或電子阻擋層可具有提高有機電致發光裝置的效率及/或壽命的效果。
在本發明之有機電致發光裝置中,較佳地,選自硫族化物層、金屬鹵化物層及金屬氧化物層之至少一個層(下文中,「表面層」)可置於一對電極之至少一個內表面上。具體地,矽及鋁之硫族化物(包含氧化物)層較佳地置於發光介質層的陽極表面上,且金屬鹵化物層或金屬氧化物層較佳地置於發光介質層的陰極表面上。可藉由表面層獲得有機電致發光裝置的操作穩定性。較佳地,硫族化物包含SiOX
(1≤X≤2)、AlOX
(1≤X≤1.5)、SiON、SiAlON等;金屬鹵化物包含LiF、MgF2
、CaF2
、稀土金屬氟化物等;金屬氧化物包含Cs2
O、Li2
O、MgO、SrO、BaO、CaO等。
另外,在本發明之有機電致發光裝置中,電子傳輸化合物及還原性摻雜劑之混合區域,或電洞傳輸化合物及氧化性摻雜劑之混合區域可置於一對電極的至少一個表面上。在此情況下,電子傳輸化合物還原成陰離子,因此變得更容易將電子自混合區域注入及傳輸至電致發光介質。此外,電洞傳輸化合物氧化成陽離子,因此變得更容易將電洞自混合區域注入及傳輸至發光介質。較佳地,氧化性摻雜劑包含各種路易斯酸及受體化合物,還原性摻雜劑包含鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬及其混合物。還原性摻雜劑層可用作電荷產生層,以製備具有兩個或更多個發光層且發射白光的有機電致發光裝置。
由式1表示之本揭示案之化合物可包括在發光層中。當用於發光層時,可包括式1之有機電致發光化合物作為主體材料。較佳地,發光層可進一步包括至少一種摻雜劑。若需要,可進一步包括除了本揭示案之由式1表示的有機電致發光化合物之外的化合物作為第二主體材料。在本文中,第一主體材料與第二主體材料之重量比在1:99至99:1的範圍內。任何已知的磷光主體均可用作第二主體材料。
包括在本揭示案之有機電致發光裝置中的摻雜劑較佳為至少一種磷光摻雜劑。包括在本揭示案之有機電致發光裝置中的磷光摻雜劑材料不受特別限制,但可較佳選自銥(Ir)、鋨(Os)、銅(Cu)及鉑(Pt)之金屬化錯合化合物,更佳選自銥(Ir)、鋨(Os)、銅(Cu)及鉑(Pt)之鄰位金屬化錯合化合物,甚至更佳鄰位金屬化之銥錯合化合物。
根據本發明包括在有機電致發光裝置中之摻雜劑可使用選自由下式101至104表示之化合物中之至少一種,但不限於此。其中, L選自以下結構:---(結構1)---(結構2) R100
、R134
及R135
各自獨立地表示氫、氘、經取代或未經取代之(C1-C30)烷基、或經取代或未經取代之(C3-C30)環烷基; R101
至R109
及R111
至R123
各自獨立地表示氫、氘、鹵素、未經取代或經氘或鹵素取代之(C1-C30)烷基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C6-C30)芳基、氰基或經取代或未經取代之(C1-C30)烷氧基,其中R106
至R109
可與相鄰的R106
至R109
鍵聯以形成經取代或未經取代之稠環,例如未經取代或經烷基取代之茀、未經取代或經烷基取代之二苯并噻吩、或未經取代或經烷基取代之二苯并呋喃;且R120
至R123
可與相鄰的R120
至R123
鍵聯以形成經取代或未經取代之稠環,例如未經取代或經選自烷基、芳基、芳烷基及烷芳基中之至少一者取代的喹啉; R124
至R133
及R136
至R139
各自獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、或經取代或未經取代之(C6-C30)芳基,其中R124
至R127
可與相鄰的R124
至R127
鍵聯以形成經取代或未經取代之稠環,例如未經取代或經烷基取代之茀、未經取代或經烷基取代之二苯并噻吩、或未經取代或經烷基取代之二苯并呋喃; X表示CR11
R12
、O或S; R11
及R12
各自獨立地表示經取代或未經取代之(C1-C10)烷基、或經取代或未經取代之(C6-C30)芳基; R201
至R211
各自獨立地表示氫、氘、鹵素、未經取代或經氘或鹵素取代之(C1-C30)烷基、經取代或未經取代之(C3-C30)環烷基、或未經取代或經烷基或氘取代之(C6-C30)芳基,其中R208
至R211
可與相鄰的R208
至R211
鍵聯以形成經取代或未經取代之稠環,例如未經取代或經烷基取代之茀、未經取代或經烷基取代之二苯并噻吩、或未經取代或經烷基取代之二苯并呋喃; f及g各自獨立地表示1至3之整數;其中若f或g為2或更大的整數,則各R100
可相同或不同;及 s表示1至3之整數。
本揭示案之有機電致發光裝置的每層的形成可使用乾式成膜方法,諸如真空蒸發、濺射、電漿、離子電鍍方法等,以及濕式成膜方法,諸如噴墨印刷、噴嘴印刷、狹縫塗佈、旋塗、浸塗、流塗方法等中之一者,但不限於此。本揭示案的摻雜劑及主體化合物可共蒸發或混合蒸發,但不限於此。
當使用濕式成膜方法時,可藉由將形成各層的材料溶解或擴散至任何適合的溶劑諸如乙醇、氯仿、四氫呋喃、二噁烷等中來形成薄膜。溶劑可為可溶解或擴散形成各層的材料,且在成膜能力方面沒有問題的任何溶劑。
共沈積為將兩種或更多種異構體材料放入各個坩堝源中,同時向兩個單元施加電流以蒸發材料並進行混合沈積的混合沈積方法;且混合沈積為在沈積之前將兩種或更多種異構體材料混合在一個坩堝源中,然後將電流施加至一個單元以蒸發材料的混合沈積方法。
此外,本揭示案之有機電致發光裝置可用於製造諸如智慧型電話、平板電腦、筆記本電腦、PC、TV或用於車輛之顯示裝置的顯示裝置,或諸如室外或室內照明的照明裝置。
在下文中,為了詳細地理解本揭示案,將參考本揭示案之代表性化合物詳細解釋根據本揭示案之有機電致發光化合物的製備方法及其性質。然而,本揭示案不受以下實例的限制。實例 1 :化合物 C-8 的製備 化合物1-1的製備
將1H-吲哚-2-甲醛(50g,344mmol),二甲基亞砜( 29.3mL , 413mmol ),溴化氫( 22.4mL , 413mmol)和1,300mL乙酸乙酯加入燒瓶中並溶解, 然後將混合物在60℃下攪拌2小時。反應完成後,有機層用乙酸乙酯萃取。用硫酸鎂移除殘留的水分且乾燥,並藉由管柱層析純化所得產物,得到化合物1-1
(42.2 g,產率:55%)。 化合物1-2的製備
將化合物1-1(42.2 g,188 mmol)、2-溴苯基硼酸(45.4 g,226 mmol)、四(三苯基膦)鈀(0)(10.9 g,9.4 mmol)、碳酸鈉(50 g,471 mmol)、940 mL甲苯及235 mL水添加至燒瓶中且溶解,隨後將混合物回流4小時。反應完成後,有機層用乙酸乙酯萃取。用硫酸鎂移除殘留的水分且乾燥,並藉由管柱層析純化所得產物,得到化合物1-2
(42 g,產率:74%)。 化合物1-3的製備
將化合物1-2(42 g,299 mmol)、2-氯苯基硼酸(26.2 g,168 mmol)、四(三苯基膦)鈀(0)(8.1 g,7 mmol)、碳酸鈉(37 g,350 mmol)、700 mL甲苯、170 mL乙醇及170 mL水添加至燒瓶中且溶解,隨後將混合物回流20小時。反應完成後,有機層用乙酸乙酯萃取。用硫酸鎂移除殘留的水分且乾燥,並藉由管柱層析純化所得產物,得到化合物1-3
(36.5 g,產率:78%)。 化合物1-4的製備
將化合物1-3(10 g,30 mmol)、乙二醇(16.8 mL,300 mmol)、對甲苯磺酸水合物(57 mg,0.3 mmol)及170 mL甲苯添加至燒瓶中且溶解,並將混合物回流20小時。反應完成後,有機層用乙酸乙酯萃取。用硫酸鎂移除殘留的水分且乾燥,並藉由管柱層析純化所得產物,得到化合物1-4
(20 g,產率:88%)。 化合物1-5的製備
將化合物1-4(10 g,26 mmol)、乙酸鈀(II)(0.29 g,1.3 mmol)、四氟硼酸三環己基膦(979 mg,2.6 mmol)、碳酸銫(17.3 g,53 mmol)及130 mL 1,2-二甲基苯(鄰二甲苯)添加至燒瓶中且溶解,隨後將混合物回流1小時。反應完成後,有機層用乙酸乙酯萃取。用硫酸鎂移除殘留的水分且乾燥,並藉由管柱層析純化所得產物,得到化合物1-5
(7.7 g,產率:85%)。 化合物1-6的製備
將化合物1-5(17.2 g,50.7 mmol)、75 mL三氟甲磺酸及200 mL氯仿添加至燒瓶中且溶解,隨後將混合物在室溫下攪拌24小時。反應完成後,用碳酸氫鈉中和後,用乙酸乙酯萃取有機層。用硫酸鎂移除殘留的水分且乾燥,並藉由管柱層析純化所得產物,得到化合物1-6
(10 g,產率:74%)。 化合物C-8的製備
將化合物1-6(4 g,15 mmol)、2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪(5.8 g,15 mmol)、三(二亞芐基丙酮)二鈀(0)(0.54 g,0.6 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.6 g,1.5 mmol)、第三丁醇鈉(3.6 g,37 mmol)及100 mL 1,2-二甲基苯(鄰二甲苯)添加至燒瓶中且溶解,隨後將混合物回流24小時。反應完成後,真空蒸餾後用乙酸乙酯萃取有機層。用硫酸鎂移除殘留的水分且乾燥,並藉由管柱層析純化所得產物,得到化合物C-8
(6.0 g,產率:70%)。
在下文中,將描述包括本揭示案之主體化合物的有機電致發光裝置的製備方法及其發光特性,以便詳細地理解本發明。[ 裝置實例 1] 藉由沈積根據本揭示案之化合物作 為 主體來製備有機電致發光裝置
製造不根據本揭示案之OLED裝置。在用於OLED(GEOMATEC CO., LTD., Japan)之玻璃基板上的透明電極氧化銦錫(ITO)薄膜(10Ω/sq)依次用丙酮、異丙醇及蒸餾水進行超音波清洗,隨後儲存在異丙醇中。接下來,將ITO基板安裝在真空氣相沈積設備的基板支架上。將化合物HI-1
引入真空氣相沈積設備之單元中,隨後將設備室中之壓力控制在10-6
托。此後,向單元施加電流以蒸發引入的材料,從而在ITO基板上形成厚度為80 nm之第一電洞注入層。隨後將化合物HI-2
引入真空氣相沈積設備之另一單元中,且向所述單元施加電流以蒸發引入的材料,從而在第一電洞注入層上形成厚度為5 nm之第二電洞注入層。接下來,將化合物HT-1
引入真空氣相沈積設備之另一單元中。此後,向單元施加電流以蒸發引入的材料,從而在第二電洞注入層上形成厚度為10 nm之第一電洞傳輸層。隨後將化合物HT-2
引入真空氣相沈積設備之另一單元中,且向所述單元施加電流以蒸發引入的材料,從而在第一電洞傳輸層上形成厚度為60 nm之第二電洞傳輸層。在形成電洞注入層及電洞傳輸層之後,接著如下沈積發光層。將作為主體之化合物C-8
引入真空氣相沈積設備之一個單元中,且將作為摻雜劑之化合物D-71
引入所述設備之另一單元中。兩種材料以不同的速率蒸發,摻雜劑按主體及摻雜劑之總重量計以3 wt%之摻雜量沈積,從而在第二電洞傳輸層上形成厚度為40 nm之發光層。接下來,作為電子傳輸材料,將化合物ETL-1
引入一個單元中,且作為電子注入材料,將化合物ETL-1
及EIL-1
引入另一單元中,以1:1之比率蒸發且沈積,從而在發光層上形成厚度為30 nm之電子傳輸層。接下來,將化合物EIL-1
沈積於電子傳輸層上作為厚度為2 nm之電子注入層,且藉由另一真空氣相沈積設備在電子注入層上沈積厚度為80 nm之Al陰極。
結果,確認在3.0 V電壓下之效率為23.8 cd/A;此外,確認1000 cd/m2
之紅色發射。此外,在5,000尼特之亮度下,發光自100%減少至90%所需的最短時間為9小時。[ 比較例 1] 製備包括習知化合物作為主體的有機電致發光裝置
除了作為發光層之主體的化合物X
之外,以與裝置實例1中相同的方式製造OLED裝置。
結果,確認在9.2 V電壓下之效率為9.2 cd/A;此外,確認1000 cd/m2
之紅色發射。此外,在5,000尼特之亮度下,發光自100%減少至90%所需的最短時間為0.9小時。
自以上裝置實例1及比較例1,可確認使用根據本揭示案之有機電致發光化合物作為發光材料的OLED裝置具有比使用習知發光材料的OLED裝置好得多的驅動壽命。
亦即,當使用根據本揭示案之有機電致發光化合物時,有機電致發光化合物可由於發射相同亮度之光所用的電壓低而在降低功耗方面為有利的。此外,其具有在主要使用OLED面板之便攜式顯示裝置中增加電池使用時間的優點。
Claims (10)
- 一種有機電致發光化合物,其由下式1表示:
- 如申請專利範圍第1項所述之有機電致發光化合物,其中L、Ar及R1中的所述經取代之(C1-C30)烷基、所述經取代之(C6-C30)(伸)芳基、所述經取代之3至30員)(伸)雜芳基、所述經取代之(C3-C30)環烷基、所述經取代之(C1-C30)烷氧基、所述經取代之三(C1-C30)烷基矽烷基、所述經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、所述經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基、所述經取代之三(C6-C30)芳基矽烷基、所述經取代之單或二(C1-C30)烷基胺基、所述經取代之單或二(C6-C30)芳基胺基、所述經取代之(C1-C30)烷基(C6-C30)芳基胺基及所述經取代之環中的取代基各自獨立地為選自由氘、鹵素、氰基、羧基、硝基、羥基、(C1-C30)烷基、鹵基(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)環烷基、(C3-C30)環烯基、(3至7員)雜環烷基、(C6-C30)芳氧基、(C6-C30)芳硫基、(C6-C30)芳基取代或未經取代之(5至30員)雜芳基、(5至30員)雜芳基取代或未經取代之(C6-C30)芳基、二(C6-C30)芳基胺基取代或未經取代之(C6-C30)芳基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30)烷基二(C6-C30)芳基矽烷基、胺基、單或二(C1-C30)烷基胺基、(C1-C30)烷基取代或未經取代之單或二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧基羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼烷基、二(C1-C30)烷基硼烷基、(C1-C30)烷基(C6-C30)芳基硼烷基、(C6-C30)芳基(C1-C30)烷基及(C1-C30)烷基(C6-C30)芳基組成之群中之至少一者。
- 如申請專利範圍第1項所述之有機電致發光化合物,其中L表示單鍵、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之(3至30員)伸雜芳基;Ar表示氫、氘、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之 (3至30員)雜芳基、或經取代或未經取代之二(C6-C30)芳基胺基;R1各自獨立地表示氫、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(3至30員)雜芳基、或經取代或未經取代之二(C6-C30)芳基胺基;或可與相鄰的取代基鍵聯以形成經取代或未經取代之(C3-C30)單環或多環芳環,其至少一個碳原子可經氮置換;其中L、Ar及R1中的所述經取代之(C6-C30)(伸)芳基、所述經取代之3至30員)(伸)雜芳基、所述經取代之二(C6-C30)芳基胺基的取代基各自獨立地為選自由氘、(5至30員)雜芳基取代或未經取代之(C6-C30)芳基、(C6-C30)芳基取代或未經取代之(5至30員)雜芳基、胺基、單或二(C1-C30)烷基胺基、(C1-C30)烷基取代或未經取代之單或二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基組成之群中之至少一者。
- 如申請專利範圍第1項所述之有機電致發光化合物,其中L表示單鍵、經取代或未經取代之伸苯基、經取代或未經取代之間伸聯苯基、經取代或未經取代之對伸聯苯基、經取代或未經取代之伸吡啶基、經取代或未經取代之伸嘧啶基、經取代或未經取代之伸三嗪基、經取代或未經取代之伸萘基、經取代或未經取代之伸喹唑啉基、或經取代或未經取代之伸喹喏啉;Ar表示氫、經取代或未經取代之苯基、經取代或未經取代之萘基、經取代或未經取代之間聯苯、經取代或未經取代之對聯苯、經取代或未經取代之三嗪基、經取代或未經取代之吡啶基、經取代或未經取代之嘧啶基、經取代或未經取代之喹唑啉基、經取代或未經取代之喹喏啉基、經取代或未經取代之咔唑基、經取代或未經取代之二苯基胺基、或經取代或未經取代之茀基苯基胺基。
- 如申請專利範圍第1項所述之有機電致發光化合物,其中Y3至Y12中之兩個相鄰基團表示CR1,Y3至Y12中之兩個相鄰的R1彼此稠合以形成由下式2至5中之任一者表示的環,且所述式1化合物含有下列環中之至少一者:
- 一種有機電致發光材料,其包括如申請專利範圍第1項所述之有機電致發光化合物。
- 一種有機電致發光裝置,其包括如申請專利範圍第1項所述之有機電致發光化合物。
- 如申請專利範圍第8項所述之有機電致發光裝置,其中所述有機電致發光化合物被包含在發光層中。
- 一種顯示裝置,其包括如申請專利範圍第1項所述之有機電致發光化合物。
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KR102613183B1 (ko) * | 2017-02-28 | 2023-12-14 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
TWI764984B (zh) * | 2017-02-28 | 2022-05-21 | 南韓商羅門哈斯電子材料韓國公司 | 有機電致發光化合物及包含其之有機電致發光裝置 |
KR102690159B1 (ko) * | 2017-02-28 | 2024-08-01 | 듀폰스페셜티머터리얼스코리아 유한회사 | 유기 전계 발광 소자 |
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2018
- 2018-06-28 KR KR1020180074578A patent/KR102158472B1/ko active IP Right Grant
- 2018-08-22 US US16/641,284 patent/US11584719B2/en active Active
- 2018-08-22 CN CN201880062103.7A patent/CN111133078A/zh active Pending
- 2018-09-06 TW TW107131256A patent/TWI765091B/zh active
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KR20150121337A (ko) * | 2014-04-18 | 2015-10-29 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
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TW201918540A (zh) | 2019-05-16 |
US20200207712A1 (en) | 2020-07-02 |
KR102158472B1 (ko) | 2020-09-23 |
US11584719B2 (en) | 2023-02-21 |
KR20190035475A (ko) | 2019-04-03 |
CN111133078A (zh) | 2020-05-08 |
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