CN112055705A - 新的化合物和包含其的有机发光器件 - Google Patents
新的化合物和包含其的有机发光器件 Download PDFInfo
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- CN112055705A CN112055705A CN201980026299.9A CN201980026299A CN112055705A CN 112055705 A CN112055705 A CN 112055705A CN 201980026299 A CN201980026299 A CN 201980026299A CN 112055705 A CN112055705 A CN 112055705A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 104
- 239000000126 substance Substances 0.000 claims description 59
- -1 dimethylfluorenyl Chemical group 0.000 claims description 56
- 239000011368 organic material Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 description 123
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000000463 material Substances 0.000 description 37
- 238000002347 injection Methods 0.000 description 35
- 239000007924 injection Substances 0.000 description 35
- 238000002360 preparation method Methods 0.000 description 35
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 28
- 230000032258 transport Effects 0.000 description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 5
- 239000010405 anode material Substances 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 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
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 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
- 150000002739 metals Chemical class 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 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
- 239000001301 oxygen Substances 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 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
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 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
- 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
- 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
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
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- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
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- 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 1
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- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition 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
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
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Abstract
本公开内容提供了新的化合物和包含其的有机发光器件。
Description
技术领域
相关申请的交叉引用
本申请要求于2018年9月4日向韩国知识产权局提交的韩国专利申请第10-2018-0105513号的权益,其公开内容通过引用整体并入本文。
本公开内容涉及新的化合物和包含其的有机发光器件。
背景技术
通常,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宽视角,优异的对比度,快速的响应时间,优异的亮度、驱动电压和响应速度的特性,并因此进行了许多研究。
有机发光器件通常具有包括阳极、阴极和介于阳极与阴极之间的有机材料层的结构。有机材料层经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,有机材料层可以由空穴注入层、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中并且电子从阴极注入有机材料层中,当注入的空穴和电子彼此相遇时,形成激子,并且当激子再次落至基态时发光。
持续需要开发用于在如上所述的有机发光器件中使用的有机材料的新材料。
[现有技术文献]
[专利文献]
(专利文献0001)韩国专利公开第10-2000-0051826号
发明内容
技术问题
本公开内容的目的是提供新的化合物和包含其的有机发光器件。
技术方案
根据本公开内容的一个方面,提供了由以下化学式1表示的化合物:
[化学式1]
在化学式1中,
Q1和Q2各自独立地为C6-30芳族环;
a和b各自独立地为0至3的整数;
X为单键;CR3R4;SiR5R6;NR7;O;S;SO2;或由以下化学式2表示的取代基,
[化学式2]
R1至R7各自独立地为氢;氘;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C6-60芳基;经取代或未经取代的含有选自N、O和S中的一个或更多个杂原子的C5-60杂芳基;或者可以与相邻基团键合以形成环,
L1至L3各自独立地为单键;经取代或未经取代的C6-60亚芳基;或者经取代或未经取代的含有选自N、O和S中的任一个或更多个杂原子的C2-60亚杂芳基,以及
Ar1和Ar2各自独立地为经取代或未经取代的C6-60芳基;经取代或未经取代的含有选自N、O和S中的一个或更多个杂原子的C2-60杂芳基;经取代或未经取代的C1-30烷基甲硅烷基;或者经取代或未经取代的C5-30芳基甲硅烷基,条件是排除二苯基芴。
根据本公开内容的另一个方面,提供了有机发光器件,其包括:第一电极;与第一电极相对设置的第二电极;和设置在第一电极与第二电极之间的一个或更多个有机材料层,其中有机材料层中的一个或更多个层包含上述由化学式1表示的化合物。
有益效果
上述由化学式1表示的化合物可以用作有机发光器件的有机材料层的材料,并且可以在有机发光器件中改善效率,实现低驱动电压和/或改善寿命特性。特别地,由化学式1表示的化合物可以用作空穴注入材料、空穴传输材料、空穴注入和传输材料、发光材料、电子传输材料、或电子注入材料。
附图说明
图1示出了包括基底1、阳极2、发光层3和阴极4的有机发光器件的一个实例。
图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4的有机发光器件的一个实例。
具体实施方式
在下文中,将更详细地描述本公开内容的实施方案以帮助理解本发明。
本公开内容提供了由化学式1表示的化合物。
如本文所使用的,术语“经取代或未经取代的”意指未经取代或经选自以下的一个或更多个取代基取代:氘;卤素基团;腈基;硝基;羟基;羰基;酯基;酰亚胺基;氨基;氧化膦基;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;以及含有N、O和S原子中的至少一者的杂环基,或者未经取代或经以上例示的取代基中的两个或更多个取代基相连接的取代基取代。例如,“两个或更多个取代基相连接的取代基”可以为联苯基。即,联苯基可以为芳基,或者其也可以解释为两个苯基相连接的取代基。
在本公开内容中,羰基的碳数没有特别限制,但优选为1至40。具体地,羰基可以为具有以下结构式的化合物,但不限于此。
在本公开内容中,酯基可以具有其中酯基的氧可以被具有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的结构。具体地,酯基可以为具有以下结构式的化合物,但不限于此。
在本公开内容中,酰亚胺基的碳数没有特别限制,但优选为1至25。具体地,酰亚胺基可以为具有以下结构式的化合物,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,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,烷基可以为直链或支链,并且其碳数没有特别限制,但优选为1至40。根据一个实施方案,烷基的碳数为1至20。根据另一个实施方案,烷基的碳数为1至10。根据另一个实施方案,烷基的碳数为1至6。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,烯基可以为直链或支链,并且其碳数没有特别限制,但优选为2至40。根据一个实施方案,烯基的碳数为2至20。根据另一个实施方案,烯基的碳数为2至10。根据又一个实施方案,烯基的碳数为2至6。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、茋基、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,但其碳数优选为3至60。根据一个实施方案,环烷基的碳数为3至30。根据另一个实施方案,环烷基的碳数为3至20。根据又一个实施方案,环烷基的碳数为3至6。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,但其碳数优选为6至60,并且其可以为单环芳基或多环芳基。根据一个实施方案,芳基的碳数为6至30。根据一个实施方案,芳基的碳数为6至20。作为单环芳基,芳基可以为苯基、联苯基、三联苯基等,但不限于此。多环芳基包括萘基、蒽基、菲基、芘基、苝基、基、芴基等,但不限于此。
在本公开内容中,杂环基为包含O、N、P、Si和S中的一者或更多者作为杂原子的杂环基,并且其碳数没有特别限制,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、***基、吡啶基、联吡啶基、嘧啶基、三嗪基、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、异唑基、噻二唑基、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,杂芳基胺中的杂芳基可以应用上述杂环基的描述。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,可以应用上述芳基的描述,不同之处在于亚芳基为二价基团。在本公开内容中,可以应用上述杂环基的描述,不同之处在于亚杂芳基为二价基团。在本公开内容中,可以应用上述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相结合而形成的。在本公开内容中,可以应用上述杂环基的描述,不同之处在于杂环不是一价基团而是通过使两个取代基相结合而形成的。
在化学式1中,优选地,Q1和Q2可以各自独立地为苯环或萘环,并且更优选地,Q1和Q2二者均可以为苯环。
优选地,化学式1可以由以下化学式1-1至1-7表示。
[化学式1-1]
[化学式1-2]
[化学式1-3]
[化学式1-4]
[化学式1-5]
[化学式1-6]
[化学式1-7]
在化学式1-1至1-7中,
a、b、R1、R2、L1至L3、Ar1和Ar2与以上定义的相同。
优选地,a和b二者均可以为0。
优选地,L1至L3可以各自独立地为单键;亚苯基;或亚联苯基。
优选地,Ar1和Ar2可以各自独立地为苯基、联苯基、三联苯基、萘基、二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、或三苯基甲硅烷基。
例如,化合物可以选自:
同时,由化学式1表示的化合物可以通过以下化学方案1或2中所示的方法来制备。
[反应方案1]
[反应方案2]
在化学方案1或2中,T为卤素,优选地为溴、或氯,其他取代基的定义与以上描述的相同。
具体地,由化学式1表示的化合物经由通过Suzuki偶联反应使起始材料偶联来制备。这样的Suzuki偶联反应优选在钯催化剂和碱的存在下进行,并且用于Suzuki偶联反应的反应性基团可以如本领域中已知的来修改。以上制备方法可以在下文描述的制备例中进一步体现。
在本发明的另一个实施方案中,提供了包含上述由化学式1表示的化合物的有机发光器件。作为一个实例,提供了这样的有机发光器件,其包括第一电极;与第一电极相对设置的第二电极;和设置在第一电极与第二电极之间的一个或更多个有机材料层,其中有机材料层中的一个或更多个层包含由化学式1表示的化合物。
通常,在金刚烷的情况下,由于其三维尺寸和刚度,其具有优异的升华特性和化学结构稳定性,因此其表现出优异的热稳定性。因此,由化学式1表示的化合物通过引入金刚烷的庞大且刚性的结构而具有优异的升华特性和化学结构稳定性,并因此具有优异的热稳定性。因此,当制造包含由化学式1表示的化合物的有机发光器件时,可以改善效率和寿命。
本公开内容的有机发光器件的有机材料层可以具有单层结构,或者其可以具有其中堆叠有两个或更多个有机材料层的多层结构。例如,本公开内容的有机发光器件可以具有包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等作为有机材料层的结构。然而,有机发光器件的结构不限于此,并且其可以包括较少数量的有机材料层。
此外,有机材料层可以包括空穴注入层、空穴传输层、或用于同时进行空穴注入和传输的层,其中空穴注入层、空穴传输层、或用于同时进行空穴注入和传输的层可以包含由化学式1表示的化合物。
此外,有机材料层可以包括发光层,其中发光层可以包含由化学式1表示的化合物。
此外,有机材料层可以包括电子传输层或电子注入层,其中电子传输层或电子注入层可以包含由化学式1表示的化合物。
此外,电子传输层、电子注入层、或用于同时进行电子传输和电子注入的层可以包含由化学式1表示的化合物。
此外,有机材料层可以包括发光层和电子传输层,其中电子传输层可以包含由化学式1表示的化合物。
此外,根据本公开内容的有机发光器件可以为其中阳极、一个或更多个有机材料层和阴极顺序地堆叠在基底上的正常型有机发光器件。此外,根据本公开内容的有机发光器件可以为其中阴极、一个或更多个有机材料层和阳极顺序地堆叠在基底上的倒置型有机发光器件。例如,图1和图2中示出了根据本公开内容的一个实施方案的有机发光器件的结构。
图1示出了包括基底1、阳极2、发光层3和阴极4的有机发光器件的一个实例。在这样的结构中,由化学式1表示的化合物可以包含在发光层中。
图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4的有机发光器件的一个实例。在这样的结构中,由化学式1表示的化合物可以包含在空穴注入层、空穴传输层、发光层和电子传输层中的一个或更多个层中。
根据本公开内容的有机发光器件可以通过本领域已知的材料和方法来制造,不同之处在于有机材料层中的一个或更多个层包含由化学式1表示的化合物。此外,当有机发光器件包括复数个有机材料层时,有机材料层可以由相同材料或不同材料形成。
例如,根据本公开内容的有机发光器件可以通过在基底上顺序地堆叠第一电极、有机材料层和第二电极来制造。在这种情况下,有机发光器件可以通过如下来制造:使用PVD(物理气相沉积)法例如溅射法或电子束蒸镀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,有机发光器件可以通过在基底上顺序地沉积阴极材料、有机材料层和阳极材料来制造。
此外,在制造有机发光器件时,由化学式1表示的化合物可以通过溶液涂覆法以及真空沉积法形成为有机材料层。在此,溶液涂覆法意指旋涂、浸涂、刮涂、喷墨印刷、丝网印刷、喷洒法、辊涂等,但不限于此。
除了这样的方法之外,有机发光器件可以通过在基底上顺序地沉积阴极材料、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。
作为一个实例,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功函数的材料使得空穴可以顺利地注入有机材料层中。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,例如氧化锌、氧化铟、氧化铟锡(ITO)、和氧化铟锌(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功函数的材料使得电子可以容易地注入有机材料层中。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。
空穴注入层是用于注入来自电极的空穴的层,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,因此具有在阳极中的空穴注入效应以及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移动至电子注入层或电子注入材料,并且还具有优异的薄膜形成能力。优选空穴注入材料的HOMO(最高占据分子轨道)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、基于喹吖啶酮的有机材料、基于苝的有机材料、蒽醌、基于聚苯胺和基于聚噻吩的导电化合物等,但不限于此。
空穴传输层是接收来自空穴注入层的空穴并将空穴传输至发光层的层。空穴传输材料适当地为具有大的空穴迁移率的材料,其可以接收来自阳极或空穴注入层的空穴并将空穴转移至发光层。其具体实例包括基于芳基胺的有机材料、导电化合物、同时存在共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
发光材料优选为这样的材料:其可以接收分别从空穴传输层和电子传输层传输的空穴和电子,并且使空穴与电子结合以发出可见光区域内的光,并且对荧光或磷光具有良好的量子效率。发光材料的具体实例包括8-羟基-喹啉铝配合物(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并唑、基于苯并噻唑和基于苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基)(PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。
发光层可以包含主体材料和掺杂剂材料。主体材料可以为稠合芳族环衍生物、含杂环的化合物等。稠合芳族环衍生物的具体实例包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等。含杂环的化合物的实例包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,但不限于此。
掺杂剂材料的实例包括芳族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体地,芳族胺衍生物为经取代或未经取代的具有芳基氨基的稠合芳族环衍生物,并且其实例包括具有芳基氨基的芘、蒽、二茚并芘等。苯乙烯基胺化合物为其中经取代或未经取代的芳基胺中取代有至少一个芳基乙烯基的化合物,其中选自芳基、甲硅烷基、烷基、环烷基和芳基氨基的一个或两个或更多个取代基为经取代或未经取代的。其具体实例包括苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺等,但不限于此。此外,金属配合物包括铱配合物、铂配合物等,但不限于此。
电子传输层是接收来自电子注入层的电子并将电子传输至发光层的层,并且电子传输材料适当地为可以很好地接收来自阴极的电子并将电子转移至发光层,并且具有大的电子迁移率的材料。电子传输材料的具体实例包括:8-羟基喹啉的A1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相关技术使用的任何期望的阴极材料一起使用。特别地,阴极材料的合适的实例为具有小功函数的典型材料,后接铝层或银层。其具体实例包括铯、钡、钙、镱和钐,在每种情况下都后接铝层或银层。
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,具有注入来自阴极的电子的效应和将电子注入发光层或发光材料的优异效应,防止由发光层产生的激子移动至空穴注入层,并且还具有优异的薄膜形成能力。电子注入层的具体实例包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、***、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等,及其衍生物;金属配合物化合物;含氮5元环衍生物等,但不限于此。
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。
根据所使用的材料,根据本公开内容的有机发光器件可以为前侧发射型、后侧发射型、或双侧发射型。
此外,除了有机发光器件之外,由化学式1表示的化合物还可以包含在有机太阳能电池或有机晶体管中。
在以下实施例中将详细地描述由化学式1表示的化合物和包含其的有机发光器件的制备。然而,这些实施例仅出于说明性目的而提出,并不旨在限制本公开内容的范围。
[制备例]
制备例1:化合物1的制备
将10g(1当量)化合物A-1和10.0g(1当量)化合物B-1添加到甲苯(150mL)中。向其中添加6.0g(2当量)叔丁醇钠和0.08g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到14.5g化合物1(产率:77%)。
MS:[M+H]+=606
制备例2:化合物2的制备
将10g(1当量)化合物A-1和10.0g(1当量)化合物B-2添加到甲苯(150mL)中。向其中添加6.0g(2当量)叔丁醇钠和0.08g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到12.3g化合物2(产率:65%)。
MS:[M+H]+=606
制备例3:化合物3的制备
将10g(1当量)化合物A-2和11.3g(1当量)化合物B-3添加到甲苯(150mL)中。向其中添加6.0g(2当量)叔丁醇钠和0.08g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到14.3g化合物3(产率:71%)。
MS:[M+H]+=646
制备例4:化合物4的制备
将10g(1当量)化合物A-3和12.8g(1当量)化合物B-4添加到甲苯(150mL)中。向其中添加6.0g(2当量)叔丁醇钠和0.08g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到16.8g化合物4(产率:78%)。
MS:[M+H]+=692
制备例5:化合物5的制备
将10g(1当量)化合物A-4和8.3g(1当量)化合物B-5添加到四氢呋喃(150mL)中。向其中添加2M碳酸钾水溶液(100mL)和0.08g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流5小时。在将反应温度降低至室温并使反应完成之后,将碳酸钾溶液除去以过滤白色固体。将过滤的固体用四氢呋喃洗涤两次并用乙酸乙酯洗涤两次以得到14.0g化合物5(产率:70%)。
MS:[M+H]+=672
制备例6:化合物6的制备
将10g(1当量)化合物A-5和11.9g(1当量)化合物B-6添加到甲苯(150mL)中。向其中添加5.7g(2当量)叔丁醇钠和0.08g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到16.5g化合物6(产率:79%)。
MS:[M+H]+=702
制备例7:化合物7的制备
将10g(1当量)化合物A-6和11.9g(1当量)化合物B-7添加到甲苯(150mL)中。向其中添加4.7g(2当量)叔丁醇钠和0.06g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到12.8g化合物7(产率:68%)。
MS:[M+H]+=772
制备例8:化合物8的制备
将10g(1当量)化合物A-7和12.3g(1当量)化合物B-8添加到甲苯(150mL)中。向其中添加4.7g(2当量)叔丁醇钠和0.06g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到16.0g化合物8(产率:75%)。
MS:[M+H]+=878
制备例9:化合物9的制备
将10g(1当量)化合物A-8和12.8g(1当量)化合物B-9添加到四氢呋喃(150mL)中。向其中添加2M碳酸钾水溶液(100mL)和0.07g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流5小时。在将反应温度降低至室温并使反应完成之后,将碳酸钾溶液除去以过滤白色固体。将过滤的固体用四氢呋喃洗涤两次并用乙酸乙酯洗涤两次以得到14.2g化合物9(产率:69%)。
MS:[M+H]+=749
制备例10:化合物10的制备
将10g(1当量)化合物A-9和10.6g(1当量)化合物B-10添加到甲苯(150mL)中。向其中添加5.3g(2当量)叔丁醇钠和0.07g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到15.1g化合物10(产率:77%)。
MS:[M+H]+=711
制备例11:化合物11的制备
将10g(1当量)化合物A-10和10.0g(1当量)化合物B-11添加到甲苯(150mL)中。向其中添加3.9g(2当量)叔丁醇钠和0.05g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到11.7g化合物11(产率:61%)。
MS:[M+H]+=938
制备例12:化合物12的制备
将10g(1当量)化合物A-11和9.3g(1当量)化合物B-12添加到甲苯(150mL)中。向其中添加3.9g(2当量)叔丁醇钠和0.05g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到12.6g化合物12(产率:68%)。
MS:[M+H]+=902
制备例13:化合物13的制备
将10g(1当量)化合物A-12和10.4g(1当量)化合物B-13添加到甲苯(150mL)中。向其中添加4.0g(2当量)叔丁醇钠和0.05g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到15.9g化合物13(产率:81%)。
MS:[M+H]+=953
制备例14:化合物14的制备
将10g(1当量)化合物A-13和9.3g(1当量)化合物B-14添加到甲苯(150mL)中。向其中添加4.0g(2当量)叔丁醇钠和0.05g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到14.3g化合物14(产率:77%)。
MS:[M+H]+=901
制备例15:化合物15的制备
将10g(1当量)化合物A-14和12.0g(1当量)化合物B-15添加到甲苯(150mL)中。向其中添加5.0g(2当量)叔丁醇钠和0.07g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到15.1g化合物15(产率:72%)。
MS:[M+H]+=810
制备例16:化合物16的制备
将10g(1当量)化合物A-15和12.0g(1当量)化合物B-16添加到甲苯(150mL)中。向其中添加5.0g(2当量)叔丁醇钠和0.07g(0.005当量)双(三叔丁基膦)钯(0),然后搅拌并回流2小时。将混合物冷却至室温,然后过滤以得到固体。使所得固体从氯仿和乙醇中重结晶以得到15.3g化合物16(产率:68%)。
MS:[M+H]+=811
[实验例]
<实验例1>
将其上涂覆有厚度为的ITO(氧化铟锡)作为薄膜的玻璃基底放入其中溶解有清洁剂的蒸馏水中,并进行超声清洗。此时,使用由Fischer Co.制造的产品作为清洁剂,作为蒸馏水,使用利用由Millipore Co.制造的过滤器过滤两次的蒸馏水。在将ITO清洗30分钟之后,使用蒸馏水重复两次超声清洗10分钟。在用蒸馏水清洗完成之后,用异丙醇、丙酮和甲醇溶剂对基底进行超声清洗,干燥,然后转移至等离子体清洗器。此外,使用氧等离子体将基底清洗5分钟,然后转移至真空沉积器。
<实验例2至16>
以与实验例1中相同的方式制造有机发光器件,不同之处在于使用下表1中示出的化合物代替实验例1中的化合物。
<比较例1至6>
以与实验例1中相同的方式制造有机发光器件,不同之处在于使用下表1中示出的化合物代替实验例1中的化合物。下表1中使用的化合物HT-01至HT-06如下:
对于实验例和比较例中使用各化合物作为空穴传输层制造的有机发光器件,在10mA/cm2的电流密度下测量驱动电压和发光效率,以及在20mA/cm2的电流密度下测量亮度降低至初始亮度的98%所需的时间(LT98),并且结果示于下表1中。
[表1]
如表1所示,确定当使用本公开内容的化合物作为空穴传输层材料时,与比较例相比,其表现出优异的效率和寿命。这被认为是由于通过在核中引入金刚烷结构而提高了由化学式1表示的化合物的化学结构稳定性。
附图标记
1:基底 2:阳极
3:发光层 4:阴极
5:空穴注入层 6:空穴传输层
7:发光层 8:电子传输层
Claims (8)
1.一种由以下化学式1表示的化合物:
[化学式1]
在所述化学式1中,
Q1和Q2各自独立地为C6-30芳族环;
a和b各自独立地为0至3的整数;
X为单键;CR3R4;SiR5R6;NR7;O;S;SO2;或由以下化学式2表示的取代基,
[化学式2]
R1至R7各自独立地为氢;氘;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C6-60芳基;经取代或未经取代的含有选自N、O和S中的一个或更多个杂原子的C5-60杂芳基;或者可以与相邻基团键合以形成环,
L1至L3各自独立地为单键;经取代或未经取代的C6-60亚芳基;或者经取代或未经取代的含有选自N、O和S中的任一个或更多个杂原子的C2-60亚杂芳基,以及
Ar1和Ar2各自独立地为经取代或未经取代的C6-60芳基;经取代或未经取代的含有选自N、O和S中的一个或更多个杂原子的C2-60杂芳基;经取代或未经取代的C1-30烷基甲硅烷基;或者经取代或未经取代的C5-30芳基甲硅烷基,条件是排除二苯基芴。
2.根据权利要求1所述的化合物,
其中Q1和Q2各自独立地为苯环或萘环。
4.根据权利要求1所述的化合物,
其中a和b二者均为0。
5.根据权利要求1所述的化合物,
其中L1至L3独立地为单键;亚苯基;或亚联苯基。
6.根据权利要求1所述的化合物,
其中Ar1和Ar2各自独立地为苯基、联苯基、三联苯基、萘基、二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、或三苯基甲硅烷基。
8.一种有机发光器件,包括:第一电极;与所述第一电极相对设置的第二电极;和设置在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中所述有机材料层中的一个或更多个层包含根据权利要求1至7中任一项所述的化合物。
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