CN112094169B - 有机电致发光材料及其应用 - Google Patents
有机电致发光材料及其应用 Download PDFInfo
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- CN112094169B CN112094169B CN201910524656.6A CN201910524656A CN112094169B CN 112094169 B CN112094169 B CN 112094169B CN 201910524656 A CN201910524656 A CN 201910524656A CN 112094169 B CN112094169 B CN 112094169B
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- terphenyl
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- organic electroluminescent
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- 239000000463 material Substances 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- -1 C3-C12 cycloalkyl Chemical group 0.000 claims abstract description 58
- 230000000903 blocking effect Effects 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 3
- 239000011669 selenium Substances 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 88
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 claims description 3
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960005544 indolocarbazole Drugs 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 abstract description 2
- 239000005062 Polybutadiene Substances 0.000 abstract description 2
- 125000001769 aryl amino group Chemical group 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 125000005241 heteroarylamino group Chemical group 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- 239000011368 organic material Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 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 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YKCZGQXLXXMGNR-UHFFFAOYSA-N (9,9-dimethylfluoren-4-yl)boronic acid Chemical compound C1=CC=C(B(O)O)C2=C1C(C)(C)C1=CC=CC=C12 YKCZGQXLXXMGNR-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- 125000002078 anthracen-1-yl 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 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 125000005580 triphenylene group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IYTJAIPZOZCSOM-UHFFFAOYSA-N 1-bromo-2-methylsulfanylnaphthalene Chemical compound CSC1=C(Br)C2=CC=CC=C2C=C1 IYTJAIPZOZCSOM-UHFFFAOYSA-N 0.000 description 1
- LEHBLKHJWCNXKQ-UHFFFAOYSA-N 1-bromo-2-nitronaphthalene Chemical compound C1=CC=CC2=C(Br)C([N+](=O)[O-])=CC=C21 LEHBLKHJWCNXKQ-UHFFFAOYSA-N 0.000 description 1
- NTEIZPBYXABJKN-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical group C1=CC(Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 NTEIZPBYXABJKN-UHFFFAOYSA-N 0.000 description 1
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 1
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- BLFDNIPIBSFUEL-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9h-carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC2=C1C1=CC=CC=C1N2 BLFDNIPIBSFUEL-UHFFFAOYSA-N 0.000 description 1
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 1
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- 101100069853 Caenorhabditis elegans hil-3 gene Proteins 0.000 description 1
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- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 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
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- DAUCSGSCDZOKLE-UHFFFAOYSA-N methyl 1-bromonaphthalene-2-carboxylate Chemical compound C1=CC=CC2=C(Br)C(C(=O)OC)=CC=C21 DAUCSGSCDZOKLE-UHFFFAOYSA-N 0.000 description 1
- 238000005232 molecular self-assembly Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 230000007704 transition Effects 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
- CGRJOQDFNTYSGH-UHFFFAOYSA-N tritylphosphane Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(P)C1=CC=CC=C1 CGRJOQDFNTYSGH-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
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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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- C07C211/54—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 two or three six-membered aromatic rings
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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Abstract
本发明涉及一种有机电致发光材料及其应用,该材料具有如下式(1)的结构:X和Y分别独立地选自氧、硫、硒、BRa、NRb、CRcRd、SiReRf、CRg=CRh或CRiRj‑CRkRl,且X和Y中至少有一个为CRcRd;Z1‑Z10各自独立地选自C或N;R1、R2、R3和R4分别独立地选自C1~C12的烷基、C3~C12的环烷基、C1~C12的烷氧基、卤素、氰基、硝基、羟基、硅烷基、氨基、取代或未取代的C6~C30的芳基氨基、取代或未取代的C3~C30的杂芳基氨基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种。本发明的化合物作为OLED器件中的发光主体材料或者用作空穴阻挡层材料时,表现出优异的器件性能和稳定性。本发明同时保护采用上述通式化合物的有机电致发光器件。
Description
技术领域
本发明涉及一种有机化合物,其可以用作有机电致发光材料;本发明还涉及该化合物在有机电致发光器件中的应用。
背景技术
近年来,基于有机材料的光电子器件已经变得越来越受欢迎。有机材料固有的柔性令其十分适合用于在柔性基板上制造,可根据需求设计、生产出美观而炫酷的光电子产品,获得相对于无机材料无以比拟的优势。此类有机光电子器件的示例包括有机发光二极管(OLED),有机场效应管,有机光伏打电池,有机传感器等。其中OLED发展尤其迅速,已经在信息显示领域取得商业上的成功。OLED可以提供高饱和度的红、绿、蓝三颜色,用其制成的全色显示装置无需额外的背光源,具有色彩炫丽,轻薄柔软等优点。
OLED器件核心为含有多种有机功能材料的薄膜结构。常见的功能化有机材料有:空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料,电子阻挡材料以及发光主体材料和发光客体(染料)等。通电时,电子和空穴被分别注入、传输到发光区域并在此复合,从而产生激子并发光。
人们已经开发出多种有机材料,结合各种奇特的器件结构,可以提升载流子迁移率、调控载流子平衡、突破电致发光效率、延缓器件衰减。出于量子力学的原因,常见的荧光发光体主要利用电子和空穴结合时产生的单线态激子发光,现在仍然广泛地应用于各种OLED产品中。有些金属络合物如铱络合物,可以同时利用三线态激子和单线态激子进行发光,被称为磷光发光体,其能量转换效率可以比传统的荧光发光体提升高达四倍。热激发延迟荧光(TADF)技术通过促进三线态激子朝单线态激子的转变,在不采用金属配合物的情况下,仍然可以有效地利用三线态激子而实现较高的发光效率。
随着OLED产品逐步进入市场,人们对这类产品的性能有越来越高的要求。当前使用的OLED材料和器件结构无法完全解决OLED产品效率、寿命、成本等各方面的问题。
发明内容
针对上述现有技术方案的缺陷,本发明提出一类可用于有机电致发光器件的有机化合物和使用该有机化合物的器件。
作为本发明的一个方面,提供一种新型化合物具有如下通式(1)所示的结构:
式(1)中,X和Y分别独立地选自氧、硫、硒、BRa、NRb、CRcRd、SiReRf、CRg=CRh或CRiRj-CRkRl,且X和Y中至少有一个为CRcRd;
Z1-Z10各自独立地选自C或N;
R1代表0~3个相同或不同的取代基,R2代表0~2个相同或不同的取代基,R3代表0~2个相同或不同的取代基,R4代表0~3个相同或不同的取代基,R1、R2、R3和R4分别独立地选自C1~C12的烷基、C3~C12的环烷基、C1~C12的烷氧基、卤素、氰基、硝基、羟基、硅烷基、氨基、取代或未取代的C6~C30的芳基氨基、取代或未取代的C3~C30的杂芳基氨基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;
Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、Ri、Rj、Rk和Rl分别独立地选自氢、C1~C12的烷基、C3~C12的环烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;
当上述基团存在取代基时,所述取代基分别独立地选自卤素、C1-C10的烷基、C3-C10的环烷基、C1-C6的烷氧基、C1-C6的硫代烷氧基、C1-C6羰基、C6~C30的芳基、C6~C30杂芳基中的一种或多种。
优选的,本发明所述化合物具有如下式(2)所示的结构:
式(2)中,X和Y、R1、R2、R3和R4的定义均与在式(1)中的定义相同。
进一步优选的,本发明所述化合物具有如下式(2-1)至式(2-12)所示的结构:
式(2-1)至式(2-12)中,R1、R2、R3和R4的定义以及Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、Ri、Rj、Rk和Rl的定义均与在式(1)中的定义相同。
再进一步优选的,本发明的式(1)、式(2)或式(2-1)至式(2-12)中所述的R1、R 2、R3和R4各自独立地选自取代或未取代的以下基团中的至少一种:甲基、乙基、正丙基、异丙基、正丁基、正己基、正辛基、异丁基、叔丁基、环戊基、环己基、环丙基、环丁基、环戊基、环己基、四氢呋喃、吡咯烷、四氢噻吩、苯基、联苯基、三联苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、菲基、茚基、1-芴基、2-芴基、3-芴基、4-芴基、9-芴基、荧蒽基、三亚苯基、苝基、基、2-联苯基、4-联苯基、对-三联苯基-4-基、对-三联苯基-3-基、对-三联苯基-2-基、间-三联苯基-4-基、间-三联苯基-3-基、间-三联苯基-2-基、9,9’-二甲基芴、9,9’-螺二芴、苯并芴、1-芘基、2-芘基、4-芘基、1-并四苯基、2-并四苯基、9-并四苯基、呋喃基、噻吩基、吡咯基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、吲哚基、二苯并呋喃基、二苯并噻吩基、9-苯基咔唑、9-萘基咔唑苯并咔唑、二苯并咔唑或吲哚并咔唑。
再进一步优选的,本发明的式(1)、式(2)或式(2-1)至式(2-12)中所述的Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、Ri、Rj、Rk和Rl分别独立地选自氢,或者各自独立地选自取代或未取代的以下基团中的至少一种:甲基、乙基、正丙基、异丙基、正丁基、正己基、正辛基、异丁基、叔丁基、环戊基、环己基、环丙基、环丁基、环戊基、环己基、苯基、联苯基、三联苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、菲基、茚基、1-芴基、2-芴基、3-芴基、4-芴基、9-芴基、荧蒽基、三亚苯基、苝基、基、2-联苯基、4-联苯基、对-三联苯基-4-基、对-三联苯基-3-基、对-三联苯基-2-基、间-三联苯基-4-基、间-三联苯基-3-基、间-三联苯基-2-基、9,9’-二甲基芴、9,9’-螺二芴、苯并芴、1-芘基、2-芘基、4-芘基、1-并四苯基、2-并四苯基、9-并四苯基、呋喃基、噻吩基、吡咯基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、吲哚基、二苯并呋喃基、二苯并噻吩基、9-苯基咔唑、9-萘基咔唑苯并咔唑、二苯并咔唑或吲哚并咔唑。
进一步优选地,本发明的化合物为如下化合物P1-P143中的任意一种:
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另一方面,本发明提供了如上所述的化合物在有机电致发光器件中的应用,本发明的化合物优选应用在有机电致发光器件中作为发光主体材料,相比现有技术中的化合物,能够进一步降低驱动电压、提高发光效率和延长使用寿命。此外,本发明的化合物还可用作空穴阻挡材料,提升器件的性能。
在本发明中,含有本发明所述化合物的有机层可以用作但不限于用在发光层、空穴阻挡层。此外,本发明的化合物还可以应用于有机电子器件中,所述有机电子元器件可举出例如有机电致发光器件、照明元件、有机薄膜晶体管、有机场效应晶体管、有机薄膜太阳能电池、信息标签、电子人工皮肤片材、片材型扫描器等大面积传感器、电子纸及有机EL面板等。
同时,本发明提供一种有机电致发光器件,包括第一电极、第二电极和***在所述第一电极和第二电极之间的一层或多层有机层,其中,所述有机层包含如上述通式(1)或通式(2)或具体结构式中任一所示的化合物。
具体而言,本发明提供了一种有机电致发光器件,包括基板,以及依次形成在所述基板上的阳极层、多个发光功能层和阴极层;所述的发光功能层包括空穴注入层、空穴传输层、发光层、电子阻挡层、电子传输层中的至少一个,其中,所述发光层或空穴阻挡层中的至少一个含有本发明上述通式或具体结构式中任一所示的化合物。
上述本发明化合物用作有机电致发光材料性能优异的具体原因尚不明确,推测可能是以下的原因:本发明化合物将具有良好电荷传输性能的萘环和芴整合在一起,创造出一个特别有利于分子自组装的刚性大环共轭体系,同时引入适当的取代基团;在这些结构的协同作用下,提升材料的电荷传输性能。需要进一步指出的是,芴类结构本身具有双极性(同时传输电子和空穴)的传输特征,它与此大环共轭体系的其他片段(如苯并呋喃、吲哚等)的有机结合,调控空穴和电子的传输特性。此外,刚性大环共轭体系上的取代基团,也可以进一步调节材料的HOMO/LUMO能级,以有效地调控空穴和电子在各层之间的注入与阻挡。所有这些,有利于达成载流子的传输平衡,从而提升OLED器件性能。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明中如下合成例中所用溶剂和试剂,例如芳基溴代物、2-溴-9,9’-二甲基芴、2-溴代二苯并呋喃、2-溴代二苯并噻吩、、4-溴联苯、[1,1’-双(二苯基膦)二茂铁]二氯化钯、三(二亚苄基丙酮)二钯、甲苯、石油醚、正己烷、二氯甲烷、丙酮、硫酸钠、乙酸乙酯、乙醇、三特丁基膦、叔丁基醇钾/钠等化学试剂,均可以从国内化工产品市场购买或定制,例如购买自国药集团试剂公司、Sigma-Aldrich公司、百灵威试剂公司,中间体M通过试剂公司定制。另外,本领域技术人员也可以通过公知方法合成。
在本发明中,对所述化合物的合成方法进行简要说明,所述化合物的代表性合成路径如下:
合成实施例
代表性合成路径1:
代表性合成路径2:
代表性合成路径3:
M1的合成
在氮气氛围下,将1-溴-2-硝基萘(25.21g,100mmol)、4-硼酸-9,9-二甲基芴(23.81g,100mmol)、四(三苯基膦)钯(1.15g,1mmol)、碳酸钾(27.6g,200mmol)、1,4-二氧六环600ml,蒸馏水200ml放入2L反应容器中,在100℃下回流反应12h。冷却至室温,合并浓缩有机相。利用柱色谱法进行分离得到中间体M1-1 29.47g。分子量计算值:365.43,实测值C/Z:365.4。
在氮气氛围下,将M1-1(29.23g,80mmol)、三苯基膦(52.46g,200mmol)、邻二氯苯300ml放入1L反应容器中,在180℃下回流反应12h。冷却至室温,合并浓缩有机相。利用柱色谱法进行分离得到中间体M1-2 20.00g。分子量计算值:333.43,实测值C/Z:333.4。
在氮气氛围下,将M1-2(16.67g,50mmol)、氯化钠(58.44g,1000mmol)、三氯化铝(482.86g,2000mmol)、苯1000ml放入2L反应容器中,回流反应12h。冷却至室温,用NaHCO3饱和水溶液处理掉过量的AlCl3,合并浓缩有机相。利用柱色谱法进行分离得到中间体M15.87g。分子量计算值:365.43,实测值C/Z:331.42。
M2的合成
在氮气氛围下,将1-溴-2-萘甲酸甲酯(26.51g,100mmol)、咔唑-4-硼酸频那醇酯(29.32g,100mmol)、四(三苯基膦)钯(1.15g,1mmol)、碳酸钾(27.6g,200mmol)、1,4-二氧六环600ml,蒸馏水200ml放入2L反应容器中,在100℃下回流反应12h。冷却至室温,合并浓缩有机相。利用柱色谱法进行分离得到中间体M2-1 31.21g。分子量计算值:351.41,实测值C/Z:351.4。
在氮气氛围下,将M2-1(28.11g,80mmol)、四氢呋喃300ml放入1L反应容器中,降温至0℃,缓慢加入甲基溴化镁(58.92g,320mmol)。恢复至室温反应12h,加入饱和MH4Cl水溶液,搅拌15min,用乙酸乙酯萃取,并合并浓缩有机相。利用柱色谱法进行分离得到中间体M2-2 25.11g。分子量计算值:351.45,实测值C/Z:351.4。
在氮气氛围下,将M2-2(24.60g,70mmol)、二氯甲烷300ml放入1L反应容器中,降温至0℃,加入甲基磺酸(6.72g,70mmol)、反应12h。加水搅拌1h,萃取并合并浓缩有机相。利用柱色谱法进行分离得到中间体M2-3 16.91g。分子量计算值:333.43,实测值C/Z:333.4。
在氮气氛围下,将M1-2(16.67g,50mmol)、氯化钠(58.44g,1000mmol)、三氯化铝(482.86g,2000mmol)、苯1000ml放入2L反应容器中,回流反应12h。冷却至室温,用NaHCO3饱和水溶液处理掉过量的AlCl3,合并浓缩有机相。利用柱色谱法进行分离得到中间体M26.32g。分子量计算值:331.42,实测值C/Z:331.4。
合成例1:
P2的合成
在氮气氛围下,将M1(6.63g,20mmol)、4-溴-1,1'-联苯(4.66g,20mmol)、Pd2(dba)3(0.91g,1m mol)、s-phos(0.82g,2mmol),叔丁醇钠(3.84g,40mmol)、甲苯100ml放入250ml反应容器中,在110℃下回流反应12h。冷却至室温,合并浓缩有机相。利用柱色谱法进行分离得到P2 4.72g。分子量计算值:483.61,实测值C/Z:483.6。
合成例2:
P10的合成
在氮气氛围下,将M1(6.63g,20mmol)、2-氯-4-苯基喹唑啉(4.81g,20mmol)、碳酸铯(13.04g,40mmol)、DMF 100ml放入250ml反应容器中,回流反应12h。冷却至室温,合并浓缩有机相。利用柱色谱法进行分离得到P10 5.16g。分子量计算值:535.65,实测值C/Z:535.6。
合成例3:
P15的合成
在氮气氛围下,将2-氯-4-苯基喹唑啉(7.22g,30mmol)、4-氟苯硼酸(4.20g,30mmol)、四(三苯基膦)钯(0.69g,0.6mmol)、碳酸钾(16.56g,60mmol)、二氧六环100ml,蒸馏水30ml放入500ml反应容器中,在100℃下回流反应12h。冷却至室温,合并浓缩有机相。利用柱色谱法进行分离得到中间体瓶P15-18.04g。M:300.3。
将合成例2中的2-氯-4-苯基喹唑啉替换成P15-1,其他不变,得到P15。分子量计算值:611.75,实测值C/Z:611.8。
合成例4:
P16的合成
将合成例3中的2-氯-4-苯基喹唑啉替换成2-(4-氯苯基)-4,6-二苯基-1,3,5-三嗪,其他不变,得到P16。分子量计算值:638.77,实测值C/Z:638.8。
合成例5:
P56的合成
将合成例3中的M1替换成M2,其他不变,得到P56。分子量计算值:611.75,实测值C/Z:611.8。
合成例6:
P95的合成
将M2的合成中的咔唑-4-硼酸频那醇酯替换成二苯并呋喃-4-硼酸,其他不变,得到P95。分子量计算值:332.40,实测值C/Z:332.4。
合成例7:
P103的合成
在氮气氛围下,将(1-溴萘-2-基)(甲基)硫烷(25.20g,100mmol)、4-硼酸-9,9-二甲基芴(23.81g,100mmol)、四(三苯基膦)钯(1.15g,1mmol)、碳酸钾(27.6g,200mmol)、1,4-二氧六环600ml,蒸馏水200ml放入2L反应容器中,在100℃下回流反应12h。冷却至室温,合并浓缩有机相。利用柱色谱法进行分离得到中间体P103-1 31.74g。分子量计算值:366.52,实测值C/Z:366.5。
在氮气氛围下,将P103-1(29.32g,80mmol)、乙酸300ml放入1L反应容器中,将H2O2(8.16g,240mmol)溶于50ml乙酸,逐滴缓慢加入上述溶液,室温下反应8h。反应结束后,合并浓缩除掉乙酸。利用柱色谱法进行分离得到中间体P103-2 23.59g。分子量计算值:382.52,实测值C/Z:382.5。
在氮气氛围下,将P103-2(19.13g,50mmol)、三氟甲磺酸75ml放入500ml反应容器中,室温搅拌24h,加入40ml吡啶和5ml水,回流反应30min。恢复至室温,用二氯甲烷萃取并合并浓缩有机相。利用柱色谱法进行分离得到中间体P103-3 12.64g。分子量计算值:350.48,实测值C/Z:350.5。
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在氮气氛围下,将P103-3(10.52g,30mmol)、氯化钠(35.06g,600mmol)、三氯化铝(289.68g,1200mmol)、苯1000ml放入2L反应容器中,回流反应12h。冷却至室温,用NaHCO3饱和水溶液处理掉过量的AlCl3,合并浓缩有机相。利用柱色谱法进行分离得到P103 5.01g。分子量计算值:348.46,实测值C/Z:348.5。
接下来,对本发明的有机电致发光器件的制备方法进行详细说明。
器件实施例
实施方式
OLED包括位于第一电极和第二电极,以及位于电极之间的有机材料层。该有机材料又可以分为多个区域。比如,该有机材料层可以包括空穴传输区、发光层、电子传输区。
在具体实施例中,在第一电极下方或者第二电极上方可以使用基板。基板均为具有机械强度、热稳定性、防水性、透明度优异的玻璃或聚合物材料。此外,作为显示器用的基板上也可以带有薄膜晶体管(TFT)。
第一电极可以通过在基板上溅射或者沉积用作第一电极的材料的方式来形成。当第一电极作为阳极时,可以采用铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等氧化物透明导电材料和它们的任意组合。第一电极作为阴极时,可以采用镁(Mg)、银(Ag)、铝(Al)、铝-锂(Al-Li)、钙(Ca)、镁-铟(Mg-In)、镁-银(Mg-Ag)等金属或合金以及它们之间的任意组合。
有机材料层可以通过真空热蒸镀、旋转涂敷、打印等方法形成于电极之上。用作有机材料层的化合物可以为有机小分子、有机大分子和聚合物,以及它们的组合。
空穴传输区位于阳极和发光层之间。空穴传输区可以为单层结构的空穴传输层(HTL),包括只含有一种化合物的单层空穴传输层和含有多种化合物的单层空穴传输层。空穴传输区也可以为包括空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)中的至少一层的多层结构。
空穴传输区的材料可以选自、但不限于酞菁衍生物如CuPc、导电聚合物或含导电掺杂剂的聚合物如聚苯撑乙烯、聚苯胺/十二烷基苯磺酸(Pani/DBSA)、聚(3,4-乙撑二氧噻吩)/聚(4-苯乙烯磺酸盐)(PEDOT/PSS)、聚苯胺/樟脑磺酸(Pani/CSA)、聚苯胺/聚(4-苯乙烯磺酸盐)(Pani/PSS)、芳香胺衍生物如下面HT-1至HT-34所示的化合物;或者其任意组合。
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空穴注入层位于阳极和空穴传输层之间。空穴注入层可以是单一化合物材料,也可以是多种化合物的组合。例如,空穴注入层可以采用上述HT-1至HT-34的一种或多种化合物,或者采用下述HI 1-HI3中的一种或多种化合物;也可以采用HT-1至HT-34的一种或多种化合物掺杂下述HI1-HI3中的一种或多种化合物。
发光层包括可以发射不同波长光谱的发光染料(即掺杂剂,dopant),还可以同时包括主体材料(Host)。发光层可以是发射红、绿、蓝等单一颜色的单色发光层。多种不同颜色的单色发光层可以按照像素图形进行平面排列,也可以堆叠在一起而形成彩色发光层。当不同颜色的发光层堆叠在一起时,它们可以彼此隔开,也可以彼此相连。发光层也可以是能同时发射红、绿、蓝等不同颜色的单一彩色发光层。
根据不同的技术,发光层材料可以采用荧光电致发光材料、磷光电致发光材料、热活化延迟荧光发光材料等不同的材料。在一个OLED器件中,可以采用单一的发光技术,也可以采用多种不同的发光技术的组合。这些按技术分类的不同发光材料可以发射同种颜色的光,也可以发射不同种颜色的光。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层主体材料选自、但不限于GPH-1至GPH-80中的一种或多种的组合。
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在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的GPD-1至GPD-47的一种或多种的组合。
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在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的RPD-1至RPD-28的一种或多种的组合。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的YPD-1—YPD-11的一种或多种的组合。
OLED有机材料层还可以包括发光层与阴极之间的电子传输区。电子传输区可以为单层结构的电子传输层(ETL),包括只含有一种化合物的单层电子传输层和含有多种化合物的单层电子传输层。电子传输区也可以为包括电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)中的至少一层的多层结构。
本发明的一方面,电子传输层材料可以选自、但不限于以下所罗列的ET-1至ET-57的一种或多种的组合。
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器件中还可以包括位于电子传输层与阴极之间的电子注入层,电子注入层材料包括但不限于以下罗列的一种或多种的组合。
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
本发明中有机电致发光器件制备过程如下:
实施例1
本实施例中有机电致发光器件制备过程如下:
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至<1×10-5Pa,在上述阳极层膜上按先后顺序真空热蒸镀10nm的HT-4:HI-3(97/3,w/w)混合物作为空穴注入层,60nm的化合物HT-4作为空穴传输层,40nm的本发明的化合物P2:RPD-8(100:3,w/w)二元混合物作为发光层,25nm的化合物ET-46:ET-57(50/50,w/w)混合物作为电子传输层,1nm的LiF作为电子注入层,150nm的金属铝作为阴极。所有有机层和LiF的蒸镀总速率控制在0.1nm/秒,金属电极的蒸镀速率控制在1nm/秒。
实施例2
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为化合物P10作为发光层材料。
实施例3
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为化合物P15作为发光层材料。
实施例4
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为化合物P16作为发光层材料。
实施例5
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为化合物P56作为发光层材料。
实施例6
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为化合物P95作为发光层材料。
实施例7
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为化合物P103作为发光层材料。
对比例1
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为现有技术中的化合物D1作为发光层材料。
对比例2
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为现有技术中的化合物D2作为发光层材料。
对比例3
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物P2替换为现有技术中的化合物D3作为发光层材料。
本发明对比例所采用的化合物结构式如下:
针对由上述过程制备的各个有机电致发光器件进行如下性能测定:
在同样亮度下,使用数字源表及亮度计测定实施例1-7以及对比例1-3中制备得到的有机电致发光器件的驱动电压和电流效率以及器件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光器件的亮度达到3000cd/m2时的电压即驱动电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率;LT95的寿命测试如下:使用亮度计在10000cd/m2亮度下,保持恒定的电流,测量有机电致发光器件的亮度降为9500cd/m2的时间,单位为小时。有机电致发光器件性能见下表1和表2。
表1:
由表1可见,采用本发明的化合物P2、P95和P103所相应制备的器件实施例1、6和7与采用现有技术中结构与本发明化合物结构相近的材料D1所制备的器件对比例1相比,采用本发明化合物的器件的在电压、电流效率和寿命方面都有更好的表现。
表2:
由表2可见,采用本发明的化合物P10、P15、P16和P56所相应制备的器件实施例2、3、4和5与采用现有技术中结构与本发明化合物结构相近的材料D2和D3所分别制备的器件对比例2和对比例3相比,采用本发明化合物的器件的在电流效率和寿命方面都有显著的优异效果。
以上结果表明,本发明的新型有机材料用于有机电致发光器件,可以有效的降低起降电压,提高电流效率,是性能良好的红光主体材料。
实施例8
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至<1×10-5Pa,在上述阳极层膜上按先后顺序真空热蒸镀10nm的HT-4:HIL-3(97/3,w/w)混合物作为空穴注入层,60nm的化合物HT-4作为空穴传输层,40nm的化合物GPH-62:RPD-8(100:3,w/w)二元混合物作为发光层,5nm的本发明的化合物P15作为空穴阻挡层,25nm的化合物ET-46:ET-57(50/50,w/w)混合物作为电子传输层,1nm的LiF作为电子注入层,150nm的金属铝作为阴极。所有有机层和LiF的蒸镀总速率控制在0.1nm/秒,金属电极的蒸镀速率控制在1nm/秒。
实施例9
本实施例中有机电致发光器件制备过程与实施例8中相同,区别仅在于将化合物P15替换为化合物P16作为空穴阻挡层材料。
实施例10
本实施例中有机电致发光器件制备过程与实施例8中相同,区别仅在于将化合物P15替换为化合物P56作为空穴阻挡层材料。
对比例4
本实施例中有机电致发光器件制备过程与实施例8中相同,区别仅在于将化合物P15替换为化合物D2作为空穴阻挡层材料。
对比例5
本实施例中有机电致发光器件制备过程与实施例8中相同,区别仅在于将化合物P15替换为化合物D3作为空穴阻挡层材料。
对由上述过程制备的有机电致发光器件进行如下性能测定:
在同样亮度下,使用数字源表及亮度计测定实施例8-10及对比例4-5中制备得到的有机电致发光器件的驱动电压和电流效率以及器件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光器件的亮度达到3000cd/m2时的电压即驱动电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率;LT95的寿命测试如下:使用亮度计在10000cd/m2亮度下,保持恒定的电流,测量有机电致发光器件的亮度降为9500cd/m2的时间,单位为小时。
表3:
化合物编号 | HBL材料 | 要求亮度cd/m2 | 电压V | 电流效率cd/A | LT95(h) |
对比例4 | D2 | 3000.00 | 4.60 | 14.5 | 64 |
对比例5 | D3 | 3000.00 | 4.67 | 13.8 | 58 |
实施例8 | P15 | 3000.00 | 4.48 | 16.2 | 92 |
实施例9 | P16 | 3000.00 | 4.53 | 15.9 | 78 |
实施例10 | P56 | 3000.00 | 4.55 | 15.6 | 82 |
由表3可见,采用本发明的化合物P15、P16和P56所相应制备的器件实施例8、9和10与采用现有技术中结构与本发明化合物结构相近的材料D2和D3所分别制备的器件对比例4和对比例5相比,采用本发明化合物的器件的在电流效率和寿命方面都有显著的优异效果。
以上结果表明,本发明的新型有机材料用于有机电致发光器件,可以有效提高电流效率和寿命,是性能良好的空穴阻挡层材料。
尽管结合实施例对本发明进行了说明,但本发明并不局限于上述实施例,应当理解,在本发明构思的引导下,本领域技术人员可进行各种修改和改进,所附权利要求概括了本发明的范围。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (6)
1.一种通式化合物,如下式(2)所示:
式(2)中,X选自氧、硫、硒、NRb或CRcRd,Y为CRcRd或者为氧,且X和Y中至少有一个为CRcRd;
R1代表0~3个相同或不同的取代基,R2代表0~2个相同或不同的取代基,R3代表0~2个相同或不同的取代基,R4代表0~3个相同或不同的取代基,R1、R2、R3和R4分别独立地选自C1~C12的烷基;
Rb选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;
Rc、Rd分别独立地选自C1~C12的烷基;
当上述基团存在取代基时,所述取代基分别独立地选自C1-C10的烷基、C6~C30的芳基、C6~C30杂芳基中的一种。
2.根据权利要求1所述的通式化合物,其中所述的R1、R2、R3和R4各自独立地选自以下基团中的至少一种:甲基、乙基、正丙基、异丙基、正丁基、正己基、正辛基、异丁基或叔丁基。
3.根据权利要求1-2中任一所述的通式化合物,其中所述的Rb选自取代或未取代的以下基团中的一种:苯基、联苯基、三联苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、菲基、茚基、1-芴基、2-芴基、3-芴基、4-芴基、9-芴基、荧蒽基、三亚苯基、苝基、基、2-联苯基、4-联苯基、对-三联苯基-4-基、对-三联苯基-3-基、对-三联苯基-2-基、间-三联苯基-4-基、间-三联苯基-3-基、间-三联苯基-2-基、9,9’-二甲基芴、9,9’-螺二芴、苯并芴、1-芘基、2-芘基、4-芘基、1-并四苯基、2-并四苯基、9-并四苯基、呋喃基、噻吩基、吡咯基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、吲哚基、二苯并呋喃基、二苯并噻吩基、9-苯基咔唑、9-萘基咔唑苯并咔唑、二苯并咔唑或吲哚并咔唑;
Rc、Rd各自独立地选自以下基团中的一种:甲基、乙基、正丙基、异丙基、正丁基、正己基、正辛基、异丁基、叔丁基;
当上述基团存在取代基时,所述取代基分别独立地选自C1-C10的烷基、C6~C30的芳基、C6~C30杂芳基中的一种。
4.根据权利要求1所述的通式化合物,选自下述具体结构化合物:
5.权利要求1-4中任一所述的化合物的应用,所述应用为在有机电致发光器件中作为发光层材料或空穴阻挡层材料。
6.一种有机电致发光器件,该器件包括第一电极、第二电极和***所述第一电极和第二电极之间的一层或多层有机层,其特征在于,所述有机层中包括至少一种由权利要求1-4中任一所述的化合物。
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