CN108064258B - 有机发光器件 - Google Patents
有机发光器件 Download PDFInfo
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- CN108064258B CN108064258B CN201780002730.7A CN201780002730A CN108064258B CN 108064258 B CN108064258 B CN 108064258B CN 201780002730 A CN201780002730 A CN 201780002730A CN 108064258 B CN108064258 B CN 108064258B
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- light emitting
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- 150000001875 compounds Chemical class 0.000 claims description 103
- 239000000126 substance Substances 0.000 claims description 70
- 239000000463 material Substances 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 230000005525 hole transport Effects 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 229910052710 silicon Inorganic materials 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000002560 nitrile group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 199
- -1 triethylsilyl group Chemical group 0.000 description 51
- 238000002360 preparation method Methods 0.000 description 36
- 230000032258 transport Effects 0.000 description 25
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000011368 organic material Substances 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 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 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
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Abstract
本公开内容提供了具有改善的驱动电压、效率和寿命的有机发光器件。
Description
技术领域
相关申请的交叉引用
本申请要求于2016年9月6日向韩国知识产权局提交的韩国专利申请第10-2016-0114284号的权益,其公开内容通过引用整体并入本文。
本公开内容涉及具有改善的驱动电压、效率和寿命的有机发光器件。
背景技术
一般而言,有机发光现象是指通过使用有机材料将电能转换成光能的现象。利用有机发光现象的有机发光器件具有诸如视角宽、对比度优异、响应时间快、亮度、驱动电压和响应速度优异的特性,因此已进行了很多研究。
有机发光器件通常具有这样的结构,其包括阳极、阴极和介于阳极与阴极之间的有机材料层。有机材料层常常具有包含不同材料的多层结构以提高有机发光器件的效率和稳定性,例如,有机材料层可由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。在有机发光器件的结构中,如果在两个电极之间施加电压,则空穴从阳极注入有机材料层,并且电子从阴极注入有机材料层,当注入的空穴和电子彼此相遇时,形成激子,并且当激子再次落到基态时发光。
在有机发光器件的领域,一直需要开发具有改善的驱动电压、效率和寿命的有机发光器件。
[现有技术文献]
[专利文献]
(专利文献1)韩国专利公开第10-2000-0051826号
发明内容
技术问题
本公开内容涉及具有改善的驱动电压、效率和寿命的有机发光器件。
技术方案
本公开内容提供了以下有机发光器件:
一种有机发光器件,包括第一电极、空穴传输层、第一发光层、第二发光层、电子传输层、和第二电极,
其中第一发光层包含1-1主体和1-2主体,
第二发光层包含2-1主体和2-2主体,
空穴传输层包含与1-1主体相同的材料,以及
1-2主体和2-1主体是相同的材料。
此外,本公开内容提供了有机发光器件,其还包括在第二发光层与电子传输层之间的第三发光层,其中第三发光层包含3-1主体和3-2主体,以及1-2主体、2-1主体和3-1主体是相同的材料。
有益效果
上述有机发光器件具有优异的驱动电压、效率和寿命。
附图说明
图1示出了有机发光器件的一个实例,其包括基底(1)、阳极(2)、空穴传输层(3)、第一发光层(4)、第二发光层(5)、电子传输层(6)和阴极(7)。
图2示出了有机发光器件的一个实例,其包括基底(1)、阳极(2)、空穴传输层(3)、第一发光层(4)、第二发光层(5)、第三发光层(8)、电子传输层(6)和阴极(7)。
具体实施方式
在下文中,将更详细地描述本公开内容以帮助理解本发明。
如本文中使用的,术语“经取代或未经取代的”意指取代有选自以下中的一个或更多个取代基:氘;卤素基团;腈基;硝基;羟基;羰基;酯基;酰亚胺基;胺基;氧化膦基团;烷氧基;芳氧基;烷基硫基;芳基硫基;烷基磺酰基;芳基磺酰基;甲硅烷基;硼基;烷基;环烷基;烯基;芳基;芳烷基;芳烯基;烷基芳基;烷基胺基;芳烷基胺基;杂芳基胺基;芳基胺基;芳基膦基;或含有N、O和S原子中的至少一者的杂环基或者未被取代,或者取代有所例示的取代基中的两个或更多个取代基连接的取代基或者未被取代。例如,术语“两个或更多个取代基连接的取代基”可为联苯基。也就是说,联苯基可为芳基,或者可解释为两个苯基连接的取代基。
在本公开内容中,羰基的碳原子数没有特别限制,但优选为1至40。具体地,羰基可为由以下结构表示的化合物,但不限于此。
在本公开内容中,酯基的氧可被具有1至25个碳原子的直链、支链或环状烷基,或者具有6至25个碳原子的芳基取代。具体地,酯基可为由以下结构表示的化合物,但不限于此。
在本公开内容中,酰亚胺基中的碳原子数没有特别限制,但优选为1至25。具体地,酰亚胺基可为由以下结构表示的化合物,但不限于此。
在本公开内容中,甲硅烷基具体包括三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但不限于此。
在本公开内容中,硼基具体包括三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基和苯基硼基等,但不限于此。
在本公开内容中,卤素基团的实例包括氟、氯、溴或碘。
在本公开内容中,烷基可以是直链或支链的,并且其碳原子数没有特别限制,但优选为1至40。根据一个实施方案,烷基具有1至20个碳原子。根据另一个实施方案,烷基具有1至10个碳原子。根据另一个实施方案,烷基具有1至6个碳原子。烷基的具体实例包括甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基等,但不限于此。
在本公开内容中,烯基可以是直链或支链的,并且其碳原子数没有特别限制,但优选为2至40。根据一个实施方案,烯基具有2至20个碳原子。根据另一个实施方案,烯基具有2至10个碳原子。根据另一个实施方案,烯基具有2至6个碳原子。其具体实例包括乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、基、苯乙烯基等,但不限于此。
在本公开内容中,环烷基没有特别限制,但其碳原子数优选为3至60。根据一个实施方案,环烷基具有3至30个碳原子。根据另一个实施方案,环烷基具有3至20个碳原子。根据另一个实施方案,环烷基具有3至6个碳原子。其具体实例包括环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等,但不限于此。
在本公开内容中,芳基没有特别限制,但优选具有6至60个碳原子,并且可为单环芳基或多环芳基。根据一个实施方案,芳基具有6至30个碳原子。根据一个实施方案,芳基具有6至20个碳原子。作为单环芳基,芳基可为苯基、联苯基、三联苯基等,但不限于此。多环芳基的实例包括萘基、蒽基、菲基、芘基、基、基和芴基等,但不限于此。
在本公开内容中,杂环基为包含O、N、Si和S中的至少一者作为杂原子的杂环基,其碳原子数没有特别限制,但优选为2至60。杂环基的实例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基、噻唑基、异唑基、二唑基、噻二唑基、苯并噻唑基、吩噻嗪基、二苯并呋喃基等,但不限于此。
在本公开内容中,芳烷基、芳烯基、烷基芳基和芳基胺基中的芳基与上述芳基的实例相同。在本公开内容中,芳烷基、烷基芳基和烷基胺基中的烷基与上述烷基的实例相同。在本公开内容中,杂芳基胺基中的杂芳基可以应用上述对杂环基的描述。在本公开内容中,芳烯基中的烯基与上述烯基的实例相同。在本公开内容中,可以应用上述对芳基的描述,不同之处在于亚芳基是二价基团。在本公开内容中,可以应用上述对杂环基的描述,不同之处在于亚杂芳基是二价基团。在本公开内容中,可以应用上述对芳基或环烷基的描述,不同之处在于烃环不是一价基团而是通过使两个取代基结合而形成的。在本公开内容中,可以应用上述对杂环基的描述,不同之处在于杂环不是一价基团而是通过使两个取代基结合而形成的。
本公开内容提供了以下有机发光器件:
一种有机发光器件,包括第一电极、空穴传输层、第一发光层、第二发光层、电子传输层、和第二电极,
其中第一发光层包含1-1主体和1-2主体,
第二发光层包含2-1主体和2-2主体,
空穴传输层包含与1-1主体相同的材料,以及
1-2主体和2-1主体是相同的材料。
根据本公开内容的有机发光器件的特征在于,其可以通过控制空穴传输层和发光层中包含的材料而控制层之间的能级来改善驱动电压、效率和寿命。
在下文中,将关于各个组件详细地描述本公开内容。
第一电极和第二电极
本公开内容中使用的第一电极和第二电极为用于有机发光器件的电极。例如,第一电极为阳极,第二电极为阴极,或者第一电极为阴极,第二电极为阳极。
作为阳极材料,通常优选使用具有大的功函数的材料,以使空穴可以顺利地注入有机材料层。阳极材料的具体实例包括:金属,例如钒、铬、铜、锌和金,或其合金;金属氧化物,例如锌氧化物、铟氧化物、铟锡氧化物(ITO)和铟锌氧化物(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDOT)、聚吡咯和聚苯胺;等等,但不限于此。
作为阴极材料,通常优选使用具有小的功函数的材料,以使电子可以容易地注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金;多层结构材料,例如LiF/Al或LiO2/Al;等等,但不限于此。
另外,还可在阳极上包括空穴注入层。空穴注入层由空穴注入材料制成,并且空穴注入材料优选为这样的化合物:其具有传输空穴的能力,在阳极具有空穴注入效应,对发光层或发光材料具有优异的空穴注入效应,防止发光层中产生的激子迁移至电子注入层或电子注入材料,并且具有优异的薄膜形成能力。
空穴注入材料的HOMO(最高占据分子轨道)优选在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖酮的有机材料、基于的有机材料、蒽醌、基于聚苯胺和聚噻吩的导电聚合物等,但不限于此。
另外,还可在第一电极与空穴传输层之间和/或在第二电极与电子传输层之间包括有机层。有机层也包括发光层。
空穴传输层、第一发光层、第二发光层
本公开内容的空穴传输层是接收来自形成在阳极中或其上的空穴注入层的空穴并将空穴传输至发光层的层。对于空穴传输材料,可以接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料、对空穴具有大的迁移率的材料是合适的。
特别地,在本公开内容的有机发光器件中,优选空穴传输层与第一发光层彼此接触,并且使用与第一发光层中包含的1-1主体相同的材料作为空穴传输材料。
当如本公开内容的有机发光器件中设置多个发光层时,设置在阳极侧上的第一发光层应充当用于将空穴注入第二发光层的空穴传输层。为了使空穴迁移至第二发光层,应没有任何损耗地传输来自阳极的空穴。为此,构成第一发光层的主体的材料之一优选由与空穴传输层中包含的材料相同的材料组成。在这种情况下,可以减小空穴传输层与第一发光层之间的界面电阻,可以更容易地将空穴引入第一发光层,并且可以增加传输至第二发光层的空穴的量,从而整体地提高有机发光器件的发光效率并防止驱动电压增加。此外,通过使用具有优异空穴传输特性的材料作为第一发光层的主体之一,可以提高第一发光层自身的空穴传输特性。此外,由于提供足够量的空穴用于通过第一发光层的掺杂剂进行空穴捕获,因此可以提供提高第一发光层和第二发光层中的发光效率所需的足够的空穴。
作为空穴传输材料和1-1主体,可以使用由以下化学式1表示的化合物:
[化学式1]
在化学式1中,
R1和R2各自独立地为氢;氘;卤素;腈基;硝基;胺基;经取代或未经取代的C1-60烷基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂环基,
L1和L2各自独立地为键、或者经取代或未经取代的C6-60亚芳基,以及
Ar1和Ar2各自独立地为经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂芳基。
优选地,R1和R2各自独立地为经取代或未经取代的C1-60烷基,并且更优选为甲基。
优选地,L1和L2各自独立地为键或亚苯基。
优选地,由化学式1表示的化合物可为选自以下中的任一者:
由化学式1表示的化合物可如以下反应式1中进行制备:
[反应式1]
(在反应式1中,R1、R2、L1、L2、Ar1和Ar2与化学式1中限定的相同)
具体地,由化学式1表示的化合物可通过包括使由化学式1-1表示的化合物与由化学式1-2表示的化合物反应的步骤的方法来制备。制备方法将在以下实施例中更具体地描述。
或者,作为空穴传输材料和1-1主体,可以使用由以下化学式1'表示的化合物:
[化学式1']
在化学式1'中,
R3和R4各自独立地为氢;氘;卤素;腈基;硝基;胺基;经取代或未经取代的C1-60烷基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂环基,
L3为键、或者经取代或未经取代的C6-60亚芳基,以及
Ar3和Ar4各自独立地为经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂芳基。
优选地,R3和R4为氢。
优选地,L3为亚联苯基。
优选地,Ar3和Ar4为联苯基。
优选地,由化学式1'表示的化合物可为以下化合物:
该化合物的制备方法将在以下实施例中更具体地描述。
另外,除了空穴传输材料与第一发光层中包含的1-1主体相同之外,第一发光层中包含的1-2主体与第二发光层中包含的2-1主体相同。也就是说,空穴传输层、第一发光层和第二发光层依次层合,并且第一发光层中包含的1-2主体和第二发光层中包含的2-1主体使用相同的材料。
如上所述,由于第一发光层包含与空穴传输层相同的材料,因此可以将空穴充分地供应至第一发光层。然而,为了提高有机发光器件的整体发光效率,电子应该通过第二发光层容易地进入第一发光层。为此,通过包含与第二发光层的主体相同且与第一发光层的空穴传输层不同的材料,可以适当地调节第一发光层中的电子与空穴之间的平衡以提高发光效率。此外,当电子从第二发光层注入第一发光层时,电子迁移通过相同的材料,使得第一发光层与第二发光层之间的界面电阻减小,并且可以降低驱动电压。
作为1-2主体,可以使用由以下化学式2表示的化合物:
[化学式2]
在化学式2中,
Ar5和Ar6各自独立地为经取代或未经取代的C6-60芳基。
优选地,由化学式2表示化合物可为选自以下中的任一者:
由化学式2表示的化合物可如以下反应式2中进行制备:
[反应式2]
(在反应式2中,Ar3和Ar4与化学式2中限定的相同)
具体地,由化学式2表示的化合物可通过包括使由化学式2'表示的化合物与由化学式2"表示的化合物反应的步骤的方法来制备。制备方法将在以下实施例中更具体地描述。
如上所述,第一发光层包含两种主体,并且主体中的一种与空穴传输层的材料相同,另一种与第二发光层相同。
此外,除2-1主体之外,本公开内容的第二发光层还可包含一种主体,即2-2主体。作为2-2主体,可以使用由以下化学式3表示的化合物:
[化学式3]
在化学式3中,
L4为键;经取代或未经取代的C6-60亚芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60亚杂芳基,
Ar7和Ar8各自独立地为经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂芳基,以及
Ar9为含有至少一个N的经取代或未经取代的C2-60杂芳基。
优选地,L4为亚苯基或二苯并呋喃二基。
优选地,Ar7和Ar8为苯基。
优选地,Ar9为选自以下中的任一者:
优选地,由化学式3表示的化合物可为选自以下中的任一者:
该化合物的制备方法将在以下实施例中更具体地描述。
同时,第一发光层优选为红色发光层。为此,第一发光层优选包含红色磷光掺杂剂。红色磷光掺杂剂没有特别限制,只要其为用于有机发光器件的红色磷光掺杂剂即可。例如,第一发光层还可包含由下式4表示的化合物:
[化学式4]
在化学式4中,
n1为1或2,
R5至R8各自独立地为氢;经取代或未经取代的C1-60烷基;或者经取代或未经取代的C6-60芳基,前提条件是R5至R8中的一者或更多者为含有4个或更多个碳的支化烷基,以及
X-Y为辅助配体。
优选地,n1为2。
优选地,R5为异丁基。优选地,R6为氢。优选地,R7和R8为甲基。
优选地,X-Y为乙酰丙酮化物。
优选地,由化学式4表示的化合物可为以下化合物:
另外,第二发光层优选为黄绿色发光层。为此,第二发光层优选包含黄绿色磷光掺杂剂。黄绿色磷光掺杂剂没有特别限制,只要其为用于有机发光器件的黄绿色磷光掺杂剂即可。例如,第二发光层还可包含由下式5表示的化合物:
[化学式5]
在化学式5中,
n2为1或2,
a为0至4的整数,以及
Ar10和Ar11各自独立地为经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂芳基。
优选地,n2为2。
优选地,a为0。
优选地,Ar10和Ar11各自独立地为苯基。
优选地,由化学式5表示化合物可为以下化合物:
第三发光层
本公开内容的有机发光器件还可包括第三发光层。优选地,本公开内容的有机发光器件可具有空穴传输层、第一发光层、第二发光层和第三发光依次层合的结构。
特别地,第三发光层包含3-1主体和3-2主体。此外,对于1-2主体、2-1主体和3-1主体,使用相同的材料。
在第二发光层周围,第一发光层应具有注入空穴的作用,并且第三发光层应具有注入电子的作用。如上所述,第一发光层包含与空穴传输层中包含的材料相同的在空穴传输方面优异的材料。此外,由于第一发光层离阴极最远,因此第三发光层优选包含与第二发光层相同的材料以便顺利地提供电子。由于第二发光层比第一发光层更靠近阴极,因此其需要良好地传输电子,但可以通过包含具有双极特性的材料来调节电荷平衡以提高效率。此外,由于在两个或更多个发光层中包含相同的材料,因此还具有通过减小发光层之间的界面电阻降低驱动电压的效果。
此外,除3-1主体之外,本公开内容的第三发光层还可包含一种主体,即3-2主体。作为3-2主体,可以使用由以下化学式3表示的化合物。
3-2主体可使用由以下化学式3表示的化合物。
[化学式3]
在化学式3中,
L4为键;经取代或未经取代的C6-60亚芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60亚杂芳基,
Ar7和Ar8各自独立地为经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂芳基,以及
Ar9为含有至少一个N的经取代或未经取代的C2-60杂芳基。
优选地,L4为亚苯基或二苯并呋喃二基。
优选地,Ar7和Ar8为苯基。
优选地,Ar9为选自以下中的任一者:
优选地,由化学式3表示的化合物可为选自以下中的任一者:
该化合物的制备方法将在以下实施例中更具体地描述。
同时,第三发光层优选为绿色发光层。为此,第三发光层优选包含绿色磷光掺杂剂。绿色磷光掺杂剂没有特别限制,只要其为用于有机发光器件的绿色磷光掺杂剂即可。例如,第三发光层还可包含由以下化学式6表示的化合物
[化学式6]
在化学式6中,
n3为1或2,以及
R8至R11各自独立地为氢;氘;卤素;腈基;硝基;胺基;经取代或未经取代的C1-60烷基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;或者含有O、N、Si和S中的至少一者的经取代或未经取代的C2-60杂环基。
优选地,n3为1。
优选地,R8至R11各自独立地为氢或CD3。
优选地,R8为氢,并且R9至R11为CD3。
优选地,由化学式6表示化合物可为以下化合物:
电子传输层
本公开内容的电子传输材料是接收来自形成在阴极中或其上的电子注入层的电子并将电子传输至发光层的层。对于电子传输材料,可以良好地接收来自阴极的电子并将电子传输至发光层的材料、对电子具有大的迁移率的材料是合适的。
电子传输材料的具体实例包括8-羟基喹啉Al配合物、包含Alq3的配合物、有机自由基化合物、羟基黄酮-金属配合物等,但不限于此。电子传输层可以与如根据现有技术使用的预先期望的阴极材料一起使用。特别地,适当的阴极材料的实例为具有小的功函数的一般材料,后接铝层或银层。其具体实例包括铯、钡、钙、镱和钐,并且每种情况都后接铝层或银层。
电子注入层
本公开内容的有机发光器件还可包括在电子传输层与阴极之间的电子注入层。电子注入层是注入来自电极的电子的层,并且优选为这样的化合物:其具有传输电子的能力,具有从阴极注入电子的效应,对发光层或发光材料具有优异的电子注入效应,防止发光层中产生的激子迁移至空穴注入层,并且具有优异的薄膜形成能力。
金属配合物化合物的实例包括8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但不限于此。有机发光器件
根据本公开内容的有机发光器件的结构在图1中示出。图1示出了有机发光器件的一个实例,其包括基底(1)、阳极(2)、空穴传输层(3)、第一发光层(4)、第二发光层(5)、电子传输层(6)和阴极(7)。
此外,根据本公开内容的有机发光器件的另一种结构在图2中示出。图2示出了有机发光器件的一个实例,其包括基底(1)、阳极(2)、空穴传输层(3)、第一发光层(4)、第二发光层(5)、第三发光层(8)、电子传输层(6)和阴极(7)。
根据本公开内容的有机发光器件可通过依次层合上述组件来制造。在这种情况下,有机发光器件可通过以下过程来制造:通过使用PVD(物理气相沉积)法(例如溅射法或电子束蒸发方法)在基底上沉积金属、具有导电性的金属氧化物或其合金以形成阳极,在阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机材料层,然后在有机材料层上沉积可以用作阴极的材料。除了这样的方法之外,有机发光器件还可通过在基底上依次沉积阴极材料、有机材料层和阳极材料来制造。此外,发光层可通过溶液涂覆法以及真空沉积法使用主体和掺杂剂形成。在此,溶液涂覆法意指旋涂、浸涂、刮涂、喷墨印刷、丝网印刷、喷涂法、辊涂等,但不限于此。
除了这样的方法之外,有机发光器件还可通过在基底上依次沉积阴极材料、有机材料层和阳极材料来制造(国际公开WO 2003/012890)。然而,制造方法不限于此。
同时,根据所使用的材料,根据本公开内容的有机发光器件可为前侧发光型、后侧发光型或双侧发光型。
在下文中,为了更好的理解提供了优选实施例。然而,这些实施例仅用于举例说明的目的,并且本发明不旨在受这些实施例限制。
制备例1
1)化合物1-1的制备
向脱气的甲苯(500mL)中添加由A表示的化合物(144mmol)、由B表示的化合物(111mmol)、三叔丁基膦(4.4mmol)、乙酸钯(1.1mmol)和叔丁醇钠(166mmol),并在回流下将混合物加热2小时。将反应混合物冷却至室温,用甲苯增量并通过硅藻土过滤。在真空下使滤液蒸发,并使残余物从乙酸乙酯/庚烷中结晶。从索氏萃取器(Soxhlet extractor)(甲苯)中萃取粗产物,并在真空下通过升华纯化。
MS:[M+H]+=676
在下文中,以与化合物1-1的制备相同的方式制备以下化合物,不同之处在于将由A表示的化合物和由B表示的化合物改变成对应于待制备的化合物结构。
2)化合物1-7的制备
MS:[M+H]+=604
3)化合物1-8的制备
MS:[M+H]+=604
4)化合物1-13的制备
向THF中添加由A'表示的化合物(46.6mmol)、由B'表示的化合物(51.3mmol)、碳酸钾(139.8mmol)和四(三苯基膦)钯(0)(0.9mmol),并将混合物回流18小时。在反应完成之后,除去水层,用硫酸镁干燥有机层,并在减压下对滤液进行蒸馏。将所得的固体溶解在氯仿(100ml)中,向其中添加乙酸乙酯(100ml),然后再结晶并干燥。
MS:[M+H]+=639
制备例2
1)化合物2-1的制备
将由C表示的化合物(50mmol)、由D表示的化合物(55mmol)、K2CO3(100mmol)和Pd(PPh3)4与THF(200mL)和H2O(100mL)混合,然后搅拌并回流约20小时。在将反应混合物冷却至室温之后,除去水层,并对有机层进行蒸发。将残余物溶解在甲苯中并用水洗涤。在除去水层之后,对有机层进行蒸发,并使用硅胶使残余物经受柱色谱。
MS:[M+H]+=561
在下文中,以与化合物2-1的制备相同的方式制备以下化合物,不同之处在于将由C表示的化合物和由D表示的化合物改变成对应于待制备的化合物结构。
2)化合物2-2的制备
MS:[M+H]+=535
3)化合物2-3的制备
MS:[M+H]+=637
4)化合物2-4的制备
MS:[M+H]+=611
5)化合物2-5的制备
MS:[M+H]+=637
6)化合物2-10的制备
MS:[M+H]+=637
7)化合物2-11的制备
MS:[M+H]+=637
8)化合物2-12的制备
MS:[M+H]+=585
9)化合物2-13的制备
MS:[M+H]+=585
10)化合物2-23的制备
MS:[M+H]+=535
11)化合物2-30的制备
MS:[M+H]+=561
制备例3
1)化合物3-1的制备
将由E表示的化合物(156mmol)、由F表示的化合物(172mmol)、碳酸钠(340mmol)与乙二醇二胺醚(1000mL)和水(280mL)混合。在其中添加四(三苯基膦)钯(0)(1.5mmol),并在回流下将混合物加热16小时。在将反应混合物冷却至室温之后,分离有机相,通过硅胶过滤,用200mL水洗涤三次,随后进行蒸发。在甲苯/庚烷(1:2)下使用硅胶柱色谱法将产物纯化,并在真空下进行升华。
MS:[M+H]+=641
2)化合物3-2的制备
将由G表示的化合物(67mmol)、由H表示的化合物(74mmol)和19.3g NaOtBu与1000mL对二甲苯混合。然后向悬浮体中添加Pd(OAc)2(1.34mmol)和1M三-叔丁基膦溶液(1mL)。在回流下将反应混合物加热16小时。在将反应混合物冷却至室温之后,向其中添加二氯甲烷,分离有机相,用200mL水洗涤三次,然后进行蒸发。用热甲苯萃取残余物,从甲苯中再结晶,最后在真空下进行升华。
MS:[M+H]+=591
实施例1
将其上以150nm的厚度施加有ITO(氧化铟锡)薄膜的玻璃基底放入其中溶解有清洁剂的蒸馏水中并通过超声波进行洗涤。使用的清洁剂为从Fisher Co.商购的产品,蒸馏水为通过使用从Millipore Co.商购的过滤器过滤两次的蒸馏水。将ITO洗涤30分钟,然后通过使用蒸馏水重复进行两次超声波洗涤10分钟。在用蒸馏水洗涤完成之后,使用异丙醇、丙酮和甲醇溶剂进行超声波洗涤。然后将玻璃基底干燥,并传输至等离子体洗涤器。使用氧等离子体洗涤基底5分钟,并传输至真空蒸发器。然后在真空下在以上准备的ITO透明电极上热沉积以下HI-1化合物至50nm的厚度以形成空穴注入层。
此外,在真空下热沉积制备例1-1中制备的化合物以形成厚度为100nm的空穴传输层。然后在真空下同时沉积作为主体的制备例1-1和2-1中制备的化合物(重量比为7:3)以及作为掺杂剂的以下RD化合物(基于主体为2重量%)以形成厚度为150nm的第一发光层。在真空下同时沉积作为主体的制备例2-1和3-2中制备的化合物(重量比为3:7)以及作为掺杂剂的以下YGD化合物(基于主体为10重量%)以形成厚度为300nm的第二发光层。然后在真空下同时沉积作为主体的制备例2-1和3-2中制备的化合物(重量比为3:7)以及作为掺杂剂的以下GD化合物(基于主体为5重量%)以形成厚度为100nm的第三发光层。
此外,在真空下沉积以下ET2化合物以形成厚度为250nm的电子传输层。然后在真空下沉积以下ET1化合物(锂掺杂量为2%)以形成厚度为100nm的电子注入层。此外,沉积铝以形成阴极,从而制备有机发光器件。
实施例2至23和比较例1至8
以与实施例1相同的方式制备有机发光器件,不同之处在于使用下表1和表2中描述的化合物作为空穴传输层、第一发光层、第二发光层和第三发光层。在表1和表2中,各材料意指制备例的编号,并且括号中的值意指重量%。
同时,表2中的RH意指使用以下化合物。
[表1]
[表2]
实验例1
向实施例1至23和比较例1至8中制备的有机发光器件施加电流以获得下表3和表4中所示的结果。
[表3]
[表4]
实施例24
将其上以150nm的厚度施加有ITO(氧化铟锡)薄膜的玻璃基底放入其中溶解有清洁剂的蒸馏水中并通过超声波进行洗涤。使用的清洁剂为从Fisher Co.商购的产品,蒸馏水为通过使用从Millipore Co.商购的过滤器过滤两次的蒸馏水。将ITO洗涤30分钟,然后通过使用蒸馏水重复进行两次超声波洗涤10分钟。在用蒸馏水洗涤完成之后,使用异丙醇、丙酮和甲醇溶剂进行超声波洗涤。然后将玻璃基底干燥,并传输至等离子体洗涤器。使用氧等离子体洗涤基底5分钟,然后传输至真空蒸发器。在真空下在以上准备的ITO透明电极上热沉积HI-1化合物至50nm的厚度以形成空穴注入层。
在真空下热沉积制备例1-1中制备的化合物以形成厚度为100nm的空穴传输层。然后在真空下同时沉积作为主体的制备例1-1和2-1中制备的化合物(重量比为7:3)以及作为掺杂剂的RD化合物(基于主体为2重量%)以形成厚度为100nm的第一发光层。在真空下同时沉积作为主体的制备例2-1和3-2中制备的化合物(重量比为3:7)以及作为掺杂剂的YGD化合物(基于主体为10重量%)以形厚度为400nm的第二发光层。
此外,在真空下沉积ET2化合物以形成厚度为250nm的电子传输层。然后在真空下沉积ET1化合物(锂掺杂量为2%)以形成厚度为100nm的电子注入层。此外,沉积铝以形成阴极,从而制备有机发光器件。
实施例25至43和比较例9至16
以与实施例24相同的方式制备有机发光器件,不同之处在于使用下表5和表6中描述的化合物作为空穴传输层、第一发光层和第二发光层。在表5和表6中,各材料意指制备例的编号,并且括号中的值意指重量%。
[表5]
[表6]
实验例2
向实施例24至43和比较例9至16中制备的有机发光器件施加电流以获得下表7和表8中所示的结果。
[表7]
[表8]
[附图标记]
1:基底 2:阳极
3:空穴传输层 4:第一发光层
5:第二发光层 6:电子传输层
7:阴极 8:阳极
Claims (14)
1.一种有机发光器件,包括:
第一电极;
空穴传输层;
第一发光层;
第二发光层;
电子传输层;
在所述第二发光层与所述电子传输层之间的第三发光层;和
第二电极,
其中所述第一发光层包含1-1主体和1-2主体,
所述第二发光层包含2-1主体和2-2主体,
所述第三发光层包含3-1主体和3-2主体,
所述空穴传输层包含与所述1-1主体相同的材料,以及
所述1-2主体、所述2-1主体和所述3-1主体是相同的材料。
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Publication number | Publication date |
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US11223017B2 (en) | 2022-01-11 |
JP2018531480A (ja) | 2018-10-25 |
US20190006590A1 (en) | 2019-01-03 |
KR101744248B1 (ko) | 2017-06-07 |
CN108064258A (zh) | 2018-05-22 |
TWI640115B (zh) | 2018-11-01 |
EP3336159A4 (en) | 2018-10-10 |
WO2018048074A1 (ko) | 2018-03-15 |
EP3336159A1 (en) | 2018-06-20 |
EP3336159B1 (en) | 2019-08-28 |
TW201813155A (zh) | 2018-04-01 |
JP6598173B2 (ja) | 2019-10-30 |
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