JP5242612B2 - 新規な有機化合物を利用した有機発光素子 - Google Patents
新規な有機化合物を利用した有機発光素子 Download PDFInfo
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- JP5242612B2 JP5242612B2 JP2010049535A JP2010049535A JP5242612B2 JP 5242612 B2 JP5242612 B2 JP 5242612B2 JP 2010049535 A JP2010049535 A JP 2010049535A JP 2010049535 A JP2010049535 A JP 2010049535A JP 5242612 B2 JP5242612 B2 JP 5242612B2
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- 150000002894 organic compounds Chemical class 0.000 title description 2
- 239000010410 layer Substances 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 83
- 239000000126 substance Substances 0.000 claims description 46
- 239000011368 organic material Substances 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical group O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 150000003974 aralkylamines Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000005504 styryl group Chemical group 0.000 claims description 6
- WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical group C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 claims description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
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- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004151 quinonyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007924 injection Substances 0.000 description 51
- 238000002347 injection Methods 0.000 description 51
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- 125000001424 substituent group Chemical group 0.000 description 17
- -1 4-biphenylyl Chemical group 0.000 description 16
- 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 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
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- 238000004519 manufacturing process Methods 0.000 description 12
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- 230000000903 blocking effect Effects 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 229910052727 yttrium Inorganic materials 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- TWEGKOWCJNQSMS-UHFFFAOYSA-N 2-chloro-1h-perimidine Chemical compound C1=CC(NC(Cl)=N2)=C3C2=CC=CC3=C1 TWEGKOWCJNQSMS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005829 trimerization reaction Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Chemical group C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 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 description 3
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
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- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 229910052708 sodium Inorganic materials 0.000 description 3
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- 238000012546 transfer Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
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- VLVOJGBSVBEYHN-UHFFFAOYSA-N 2-chloro-1-iodoimidazole-4,5-dicarbonitrile Chemical compound ClC1=NC(C#N)=C(C#N)N1I VLVOJGBSVBEYHN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- CPHGOBGXZQKCKI-UHFFFAOYSA-N 4,5-diphenyl-1h-imidazole Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPHGOBGXZQKCKI-UHFFFAOYSA-N 0.000 description 2
- QVVZVWKGWGFUTA-UHFFFAOYSA-N 6-bromo-2-chloro-1h-benzimidazole Chemical compound BrC1=CC=C2NC(Cl)=NC2=C1 QVVZVWKGWGFUTA-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
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- 239000003599 detergent Substances 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 230000003139 buffering effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
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- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 238000010907 mechanical stirring Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- SNZXFRFQGXSSGN-UHFFFAOYSA-N phenylsulfanyloxysulfanylbenzene Chemical compound C=1C=CC=CC=1SOSC1=CC=CC=C1 SNZXFRFQGXSSGN-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
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Description
本発明者らは有機発光素子の耐久性及び/または效率性のために正孔注入、正孔輸送、正孔阻止、発光、電子輸送、電子注入、正極と正孔注入層との間の緩衝(buffer)役割のうちでいずれか一つ以上の役割を遂行することができる有機物質を下記化学式1で表示される環状の三量体(trimer)中心骨格(core)構造を利用して分子設計しようとする。
本発明は下記化学式1の化合物を提供する:
AはBまたはNであり、
XはNまたはCR0であり、ここでR0は水素(H)、ハロゲン原子、ニトリル基(CN)、ニトロ基(NO2)、ホルミル基、アセチル基、ベンゾイル基、アミド基、スチリル基、アセチレン基、キノリン基、キナゾリン基、フェナントロリン基、クプロイン基、アントラキノン基、ベンゾキノン基、キノン基、アクリジン基、置換または非置換のアルキル基、置換または非置換のアリール基、置換または非置換のアラルキル基、置換または非置換のアリールアミン基、置換または非置換のアルキルアミン基、置換または非置換のアラルキルアミン基、置換または非置換の異形環基で構成された群から選択されるものであり、
Y、Y'及びY''は環員としてA及びXを含む5員芳香族異形環または環員としてA及びXを含む6員芳香族異形環を含む置換または非置換芳香族複素環であり、Y、Y'及びY''は同一であるか相異であることができる。
以下で本発明に関して詳しく説明する。
本発明は前記化学式1の化合物を提供する。
化学式1で表示される化合物は環状の三量体(trimer)中心骨格(core)構造を含む有機物質として、前記三量体(trimer)を構成する各単位体(unit)自体の種類または前記単位体の置換基によって有機発光素子で正孔注入、正孔輸送、正孔阻止、発光、電子輸送、電子注入、正極と正孔注入層との間の緩衝(buffer)役割をすることができる。ここで、正極と正孔注入層との間の緩衝役割とは、正極と正孔注入層との間の界面の接触が良くないか、または正孔注入層に直接正孔注入がよくなされない時に必要である。正孔注入、正孔輸送、正孔阻止、発光、電子輸送、電子注入、正極と正孔注入層との間の緩衝(buffer)役割などをすることができる化合物らは多数公知されているし、概して置換または非置換された芳香族またはヘテロ芳香族基を含んでいる。
前記化学式1において、Xは窒素(N)であることが望ましい。
前記化学式1において、Y、Y’、Y”に結合された置換基でアルキル基が含まれる場合、アルキル基の長さは化学式1の化合物が正孔注入、正孔輸送、正孔阻止、発光、電子輸送、電子注入、正極と正孔注入層との間の緩衝(buffer)役割を遂行するにおいて、大きく影響を及ぼさない。電子素子で吸光または発光は作用化合物の共役長さ(conjugation length)によって影響を受けることができる。しかし、化合物中に含まれているアルキル基の長さは化合物の共役長さには影響を及ぼさないから化合物の波長や素子の特性には直接的に影響を及ぼさないで、単に、付随的に化合物の有機発光素子への適用方法、例えば、真空蒸着法または溶液塗布法の適用に影響を及ぼすことができる。よって、化学式1の構造に含まれることができるアルキル基の長さは特別に制限されない。
A及びXは前記化学式1での定義のようであり、
R1ないしR6はお互いに同一であるか、または相異なものであり、それぞれ水素、ハロゲン原子、ニトリル基(CN)、ニトロ基(NO2)、ホルミル基、アセチル基、ベンゾイル基、アミド基、スチリル基、アセチレン基、キノリン基、キナゾリン基、フェナントロリン基、クプロイン基、アントラキノン基、ベンゾキノン基、キノン基、アクリジン基、置換または非置換のアルキル基、置換または非置換のアリール基、置換または非置換のアラルキル基、置換または非置換のアリールアミン基、置換または非置換のアルキルアミン基、置換または非置換のアラルキルアミン基、置換または非置換の異形環基で構成された群から選択されて、ここで前記R1とR2、R3とR4及びR5とR6はお互いに縮合環を形成することができる。
A及びXは前記化学式1での定義のようであり、
R1ないしR18はお互いに同一であるか、または相異なものであり、前記化学式2でのR1ないしR6の定義のようであり、ここでR1ないしR18はそれぞれお互いに接した置換基と縮合環を形成することができる。
化学式1-1の化合物の合成(2-クロロベンゾイミダゾールの三量体化)
前記化合物の分析結果は次のようである。
融点391-393℃;1H NMR(500MHz、DMSO-d6)8.51(d、3H)、7.96(d、3H)、7.59(m、6H);MS[M+1]348
化学式1-5の化合物の合成(1-ヨード-2-クロロ-4、5-ジシアノ−イミダゾールの三量体化)
前記化合物の分析結果は次のようである。
純度99.6%と、融点>400℃;13C NMR(400MHz、DMSO-d6、ppm)135.0、123.2、110.3、106.5、106.2
前記化合物の分析結果は次のようである。
純度99.6%;融点361-363℃;1H NMR(400MHz、DMSO-d6)7.60-7.64(m、5H)、7.23-7.16(m、5H);MS[M+1]+655、[M]-654
メタノール25mLに出発物質である2-クロロベンゾイミダゾール(0.763g、5mmol)がとけている混合物に臭素/メタノール(0.26mL/5mL)溶液をゆっくり滴加した。そして、この反応混合物を5時間の間室温で撹拌した。反応程度をHPLCで確認後、水25mLを注いで室温で18時間撹拌した。この時、生成された沈殿物を濾過して中性になるまで、冷たい水で何回洗滌した後これをメタノール/水(1:1)溶液で再結晶して白色の前記化学式4aの化合物(0.6g、52.0%)を得た。
前記化合物の分析結果は次のようである。
融点228-230℃;1H NMR(400MHz、DMSO-d6)7.73(s、1H)、7.49-7.47(d、1H)、7.39-7.36(d、1H);MS[M+1]+231
出発物質である5-ブロモ-2-クロロベンゾイミダゾール1.1g(4.7mmole)を50mL長いフラスコ内に入れて、あらかじめ230℃で加熱されたオイルバスに入れた。この時、前記出発物質がとけながら直ちに、再び固体に変わる時に塩酸ガスが発生する。ガス放出が止めると、反応混合物を室温まで冷却した後に、生成された固体化合物をニトロベンゼンで再結晶した。これを濾過してエタノール、エーテルで順に洗った後、真空乾燥してアイボリー色の前記化学式4bで表示される化合物(0.43g、収率47%)を得た。
前記化合物の分析結果は次のようである。
融点354℃;MS[M+1]583(isomer)
メシチレン(mesitylene)10mLと前記化学式4bの化合物(0.4g、0.68mmol)の混合溶液、Pd2(dba)3 50mg(0.005mmol)、P(t-Bu)3 17mg(0.081mmol)及びNa(t-OBu)0.28g(3mmol)を冷却機が連結された50mL丸い底のフラスコ内に順に入れて120℃で5時間反応させた。これを室温まで冷凍させた後、トルエン20mLと水30mLを入れて層分離して有機層をMgSO4で乾燥して減圧蒸溜ですべての溶媒をとり除いた後、管クロマトグラフィーで分離してエタノールで洗滌して白色の化学式1-12の化合物(200mg、30%)を得た。
融点≧350℃;1H NMR(500MHz、DMSO-d6)8.27-8.15(m、1H)、8.09-7.74(m、3H)、7.63-7.16(m、8H)、6.97-6.86(m、3H);MS[M+1]1000
精製された1、8-ジアミノ−ナフタレン(1.7g、10.7mmol)を薄い塩酸溶液(0.5N)30mLに入れた後、加熱して完全にとかした。ここに試案化ナトリウム(0.7g10.7mmol)水溶液10mLをゆっくり加えた結果、赤い色の沈澱が生じた。これを1時間加熱後に冷却して沈殿物を濾過してエーテルで洗滌後に真空乾燥して、薄い赤色が漂う白色固体である2-ペリミジノン(perimidinone)(5a)(1.12g、6.1mmol、収率57%)を得た。得られたこの固体を塩化ホスホリル(POCl3)10mLに入れた後に加熱して3時間還流させた。過量で入れられた 塩化ホスホリルは、真空蒸溜によってとり除いて残されたものを水に分散させた後、2Nアンモニア水溶液で中和させた結果、黄色の沈殿物が生じたし、これを濾過して濾過物をTHFとヘキサン溶媒に再沈殿して濾過した後、濾過物を真空乾燥した結果、明るい黄色の2-クロロペリミジン(0.6g、2.9mmol、収率50%)を得ることができた。
この化合物の分析結果は次のようである。
2-ペリミジノン(perimidinone)(5a):1H NMR(400MHz、DMSO-d6)、10.06(s、2H)、7.21(t、J=7.6Hz、2H)、7.10(d、J=8.4Hz、2H)、6.51(d、J=7.6Hz、2H)
2-クロロペリミジン(5b):1H NMR(400MHz、DMSO-d6)、11.35(s、1H)、7.20 - 7.08(m、4H)、6.60(d、J=6.4Hz、1H)、6.38(d、J=6.8Hz、1H)
窒素雰囲気下で2-クロロペリミジン(0.73g、3.6mmol)を機械撹拌を取り揃えたフラスコに入れて熱を210度まで加えて溶融させて10分間撹拌させた結果、濃い赤色を帯びた。ここにニトロベンゼン20mL程度入れて1時間程度撹拌した後、冷却して沈澱物を濾過した。濾過物をニトロベンゼン、飽和された炭酸ナトリウム水溶液、水、エタノール、THF順で充分に洗滌後に真空乾燥して赤色固体0.57g(収率32%)を得た。
この化合物の分析結果は次のようである。
1H NMR(400MHz、DMSO-d6)、7.52−7.28(m、12H)、6.94−6.80(m、6H);MS(M+HCl+H)535
(有機発光素子の製造)
ITO(インジウムスズ酸化物)が1500Åの厚さで薄膜コーティングされたガラス基板を洗剤をとかした蒸溜水に入れて超音波で30分間洗滌して、引き継いで蒸溜水で超音波洗滌を2回10分間進行した。洗剤としては、フィッシャー社(Fishcher Co。)の製品を使ったし、蒸溜水としては、ミリフォア社(Millipore Co。)製品のフィルターで2回濾過された蒸溜水を使った。蒸溜水の洗滌が終わった後、イソプロピルアルコール、アセトン、メタノールなどの溶剤を順次に利用して超音波洗滌をして、乾燥させた後、プラズマ洗浄機に移送させた。引き継いで、窒素プラズマを利用して前記基板を5分間洗浄した後、真空蒸着機で基板を移送させた。
発光層上に前記の化学式1-1の化合物の代りに既存に電子注入及び輸送役割をするものとして知られているAlq3を200Åの厚さで真空蒸着して電子注入及び輸送層を形成したことを除き、前記実施例1と等しい方法で有機発光素子を製造した。
実施例1のような方法で準備したITO透明電極上に前記化学式4で表示されるヘキサニトリルヘキサアザトリフェニレンを500Åの厚さで熱真空蒸着して、正孔注入層を形成した。その上に正孔を輸送する物質として、製造例4で製造した化学式1-12の化合物を200Åの厚さで真空蒸着した後、その上に発光層の役割をする前記化学式5の化合物(Alq3)を300Åの厚さで真空蒸着した。発光層上に下記化学式6の化合物を200Åの厚さで真空蒸着して電子注入及び輸送層を形成した。前記電子注入及び輸送層上に順次に10Åの厚さのふっ化リチウム(LiF)と2500Åの厚さのアルミニウムを蒸着して負極を形成した。前記の過程で有機物の蒸着速度は1Å/secを維持したし、ふっ化リチウム及びアルミニウムの蒸着速度はそれぞれ0.2Å/秒及び3〜7Å/秒を維持した。
正孔注入層上に前記化学式1-12の化合物の代りに既存に正孔輸送物質として知られたNPBを200Åの厚さで真空蒸着して、正孔輸送層を形成したことを除き、前記実施例2と等しい方法で有機発光素子を製造した。
102 正極
103 正孔注入層
104 正孔輸送層
105 発光層
108 正孔阻止層
106 電子輸送層
107 負極
Claims (2)
- 第1電極、1層以上でなされた有機物層及び第2電極を順次に積層された形態で含む有機発光素子であって、前記有機物層のうちで少なくとも一層は下記化学式2の化合物1種以上を含むことを特徴とする、有機発光素子。
AはNであり、
XはNであり、
R1ないしR6はお互いに同一であるか、または相異なものであり、それぞれ水素原子(H)、ハロゲン原子、ニトリル基(CN)、ニトロ基(NO2)、ホルミル基、アセチル基、ベンゾイル基、アミド基、スチリル基、アセチレン基、キノリン基、キナゾリン基、フェナントロリン基、クプロイン基、アントラキノン基、ベンゾキノン基、キノン基、アクリジン基、置換または非置換のアルキル基、置換または非置換のアリール基、置換または非置換のアラルキル基、置換または非置換のアリールアミン基、置換または非置換のアルキルアミン基、置換または非置換のアラルキルアミン基、置換または非置換の複素環基で構成された群から選択される。
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US20050123800A1 (en) | 2005-06-09 |
CN101841005A (zh) | 2010-09-22 |
KR20050037378A (ko) | 2005-04-21 |
US7455917B2 (en) | 2008-11-25 |
TW200527959A (en) | 2005-08-16 |
CN101841005B (zh) | 2012-04-25 |
KR100591022B1 (ko) | 2006-06-22 |
JP5372867B2 (ja) | 2013-12-18 |
JP2007512233A (ja) | 2007-05-17 |
CN1863891A (zh) | 2006-11-15 |
EP1680479A4 (en) | 2010-08-11 |
JP2010199592A (ja) | 2010-09-09 |
TWI246356B (en) | 2005-12-21 |
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