CN102712663A - 新的有机电致发光化合物和使用该化合物的有机电致发光设备 - Google Patents
新的有机电致发光化合物和使用该化合物的有机电致发光设备 Download PDFInfo
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- CN102712663A CN102712663A CN2010800349510A CN201080034951A CN102712663A CN 102712663 A CN102712663 A CN 102712663A CN 2010800349510 A CN2010800349510 A CN 2010800349510A CN 201080034951 A CN201080034951 A CN 201080034951A CN 102712663 A CN102712663 A CN 102712663A
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- alkyl
- aryl
- silyl
- heteroaryl
- condensed ring
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 71
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 43
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 34
- -1 aromatic amine compound Chemical class 0.000 claims description 32
- 239000010410 layer Substances 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 23
- 125000001118 alkylidene group Chemical group 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 22
- 238000005401 electroluminescence Methods 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000004450 alkenylene group Chemical group 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 230000014509 gene expression Effects 0.000 claims description 14
- 125000005936 piperidyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 7
- JTSFIVQMXUDGAB-UHFFFAOYSA-N 4-thiomorpholin-4-ylmorpholine Chemical compound C1COCCN1N1CCSCC1 JTSFIVQMXUDGAB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 21
- 150000001721 carbon Chemical group 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 11
- 238000000151 deposition Methods 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 238000007445 Chromatographic isolation Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000011097 chromatography purification Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000004646 arylidenes Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 239000013049 sediment Substances 0.000 description 4
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940126545 compound 53 Drugs 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
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- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
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- 125000004306 triazinyl group Chemical group 0.000 description 2
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- UKTSSJJZFVGTCG-UHFFFAOYSA-N (4-bromophenyl)-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=C(Br)C=C1 UKTSSJJZFVGTCG-UHFFFAOYSA-N 0.000 description 1
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- XAOMFUPJQYNDEG-LBPRGKRZSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-methylpropan-1-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(C(C)C)=O XAOMFUPJQYNDEG-LBPRGKRZSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
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- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
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- 125000000962 organic group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical class COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
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Abstract
提供了新的有机电致发光化合物和包含该化合物的有机电致发光器件。所述有机电致发光化合物在发射蓝光时具有高的发光效率以及优异的寿命。因此,它们可用于制造具有良好工作寿命的OLED。
Description
技术领域
本发明涉及新颖的有机电致发光化合物以及使用该化合物的有机电致发光器件和有机太阳能电池。更具体地,本发明涉及用作蓝色发光材料的新有机电致发光化合物以及包括该化合物作为掺杂剂的有机电致发光器件。
背景技术
在显示器件中,电致发光(EL)器件是优选的,因为它们作为自发显示器件提供宽视角、优异的对比度和快速响应速率。伊斯曼柯达公司(Eastman Kodak)在1987年首先开发了一种有机EL器件,该器件使用低分子量芳香族二胺和铝配合物作为形成电致发光层的物质[Appl.Phys.Lett.51,913,1987]。
在有机EL器件中,决定其性能(包括发光效率和工作寿命)最重要的因素是电致发光材料。电致发光材料的一些要求包括高固态电致发光量子产率、高电子和空穴迁移、真空沉积过程中的耐分解性、形成均匀薄膜的能力和稳定性。
有机电致发光材料一般可以大致分类为高分子量材料和低分子量材料。低分子量材料可分为金属配合物和不含金属的纯有机电致发光材料,这取决于分子结构。螯合配合物例如三(8-羟基喹啉合)铝配合物、香豆素衍生物、四苯基丁二烯衍生物、二苯乙烯基亚芳基衍生物、二唑衍生物等是已知的。据报道,使用这些材料可得到可见光区域内从蓝光到红光的有机电致发光,且可预计实现彩色显示器件。
对于蓝色电致发光材料,在出光兴产公司(Idemitsu Kosan)的DPVBi(化合物a)之后,已经商业化了许多材料。除了出光兴产公司的蓝色材料体系,柯达的二萘基蒽(dinaphthylanthracene)(化合物b)和四(叔丁基)苝(tetra(t-butyl)perylene)(化合物c)是已知的,但是需要进行更多的研究和开发。直到现在,出光兴产公司的二苯乙烯基化合物体系已知具有最佳的效率。其具有6lm/W的功率效率(power efficiency)和30000小时或更长的工作寿命。但是,由于色纯度随着工作时间下降,全彩显示器的工作寿命仅有数千小时。通常,如果电致发光波长稍微向更长的波长偏移的话,蓝色电致发光在发光效率方面是有优势的。但是,它就不能用于高品质的显示器,因为不能得到纯蓝色。因此,急需提高色纯度、效率和热稳定性的研究和开发。
发明内容
技术问题
本发明的发明人通过努力解决了上述问题。因此,它们已经发明了具有优异发光效率以及能够实现具有显著提高的工作寿命的有机电致发光器件的新电致发光化合物。
因此,本发明的目的在于提供一种发光效率和器件工作寿命相对现有掺杂材料得到改进且具有符合适当色坐标的优异骨架(backbone)的有机电致发光化合物,以解决上述问题。本发明的另一个目的是提供使用有机电致发光化合物作为电致发光材料的有机电致发光器件。
技术方案
在一个通常方面,本发明提供了一种由化学式1表示的有机电致发光化合物以及包括该化合物的有机电子器件。因为本发明的有机电致发光化合物具有良好的发光效率和优异的寿命性质,它可用于制造具有非常好工作寿命的OLED设备。
其中
R1到R3独立地表示(C1-C60)烷基、(C1-C60)烷氧基、(C6-C60)芳基、(C2-C60)杂芳基或(C3-C60)环烷基,或者R1、R2或R3通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接到Ar1形成稠环,且R1到R3的烷基、烷氧基、芳基、杂芳基或环烷基还可由选自(C1-C60)烷基、(C6-C60)芳基和(C2-C60)杂芳基的一个或多个取代基取代;
X1、X2、Y1和Y2独立地表示化学键、-(CR4R5)a-、-N(R6)-、-Si(R7)(R8)-、-O-、-S-、-Se-、-P(R9)-或-(R10)C=C(R11)-;
Ar1和Ar2独立地表示化学键、(C6-C60)亚芳基或包含一个或多个选自N、O、S和Se的杂原子的(C2-C60)亚杂芳基;
Ar3和Ar4独立地表示(C1-C60)烷基、(C6-C60)芳基、(C2-C60)杂芳基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、单-、二-或三-(C15-C60)螺环、包含一个或多个选自N、O和S的杂原子的(C10-C60)杂螺环基、金刚烷基或或者Ar3和Ar4通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成稠环,所述亚烷基的碳原子由O、S、NR24或SiR25R26取代;
R4到R11独立地表示氢、氘、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、吗啉代(morpholino)、硫代吗啉代(thiomorpholino)、哌啶基(piperidino)、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、(C7-C60)二环烷基、金刚烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基,或者R4和R5、R7和R8或者R10和R11可独立地通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成螺环或稠环;
R21到R26独立地表示氢、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、吗啉代、硫代吗啉代、哌啶基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、金刚烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基,或者R25和R26可独立地通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成螺环或稠环;
Ar1和Ar2的亚芳基或杂亚芳基,Ar3和Ar4的烷基、芳基、杂芳基、杂环烷基、环烷基、螺环基、杂螺环基或金刚烷基,Ar3和Ar4通过有或没有稠环的亚烷基或亚烯基连接形成的稠环,以及R4到R11、R21到R26的烷基、烷氧基、杂环烷基、环烷基、二环烷基、金刚烷基、芳基、杂芳基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基还可由选自下述取代基的一个或多个取代基取代:(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、哌啶基、吗啉代、硫代吗啉代、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基(C6-C60)芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基;以及
a表示1-4的整数。
在本发明中,包含“(C1-C60)烷基”的取代基可具有1-60个碳原子,优选1-20个碳原子,更优选1-10个碳原子。包含“(C6-C60)芳基”的取代基可具有6-60个碳原子,优选6-20个碳原子,更优选6-12个碳原子。包含“(C3-C60)杂芳基”的取代基可具有3-60个碳原子,优选4-20个碳原子,更优选4-12个碳原子。包含“(C3-C60)环烷基”的取代基可具有3-60个碳原子,优选3-20个碳原子,更优选3-7个碳原子。包含“(C2-C60)烯基或炔基”的取代基可具有2-60个碳原子,优选2-20个碳原子,更优选2-10个碳原子。
在本发明中,“烷基”包括直链或支链的饱和伯烃基,其仅由碳和氢原子组成,或其组合,且“烷氧基”表示-O-烷基,其中烷基与上述相同。
在本发明中,“芳基”表示通过从芳香烃除去一个氢原子得到的有机基团,可包括4-到7-元、优选5-或6-元的单环或稠环。具体例子包括苯基、萘基、联苯基(biphenyl)、蒽基、茚基、芴基、菲基(phenanthryl)、苯并[9,10]菲基(triphenylenyl)、芘基、苝基(perylenyl)、基(chrysenyl)、并四苯基(naphthacenyl)、荧蒽基(fluoranthenyl)等,但不限于此。
在本发明中,“杂芳基”表示包含1-4个选自N、O和S的杂原子作为芳环骨架原子、其他芳环骨架原子为碳的芳基。它可以是与苯环缩合得到的5-或6-元单环杂芳基或多环杂芳基,且可部分饱和。另外,所述杂芳基包括通过化学键连接的超过一个杂芳基。所述杂芳基包括二价芳基,其中环中的杂原子可被氧化或季铵化形成例如N-氧化物或季铵盐。具体的例子包括单环杂芳基例如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异唑基、唑基、二唑基、三嗪基、四嗪基、三唑基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等;多环杂芳基例如苯并呋咱基(benzofuranyl)、苯并噻吩基、异苯并呋喃基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异唑基、苯并唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基(cinnolinyl)、喹唑啉基、喹喔啉基(quinoxalinyl)、咔唑基、菲啶基(phenanthridinyl)、苯并间二氧杂环戊烯基(benzodioxolyl)等;及其N-氧化物(例如吡啶基N-氧化物、喹啉基N-氧化物等);及其季铵盐等,但并不限于此。
在本发明中,“螺环”表示其中两个环仅共享一个原子(sp3碳)的烃基。两个环共享的原子称为螺原子(“螺”是表示螺旋的希腊语),且可以是碳或硅。并且,“杂螺环基”表示由碳原子和一个或多个选自N、S和O的杂原子组成的螺环,条件在于所述杂原子并不互相相邻。
本发明的有机电致发光化合物包括化学式(2)表示的化合物:
其中R1到R3、X1、X2、Y1、Y2和Ar1到Ar4与化学式1中的定义相同。
R1到R3可独立地表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二烷基、十六烷基、苄基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基、异戊氧基、正己氧基、正庚氧基、苯基、甲苯基、丁基苯基、萘基、联苯基、芴基、菲基、蒽基、荧蒽基(fluoranthenyl)、苯并[9,10]菲基(triphenylenyl)、芘基、基(chrysenyl)、并四苯基(naphthacenyl)、苝基(perylenyl)、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、哌嗪基、嘧啶基、哒嗪基、喹啉基、三嗪基、苯并呋喃基、苯并噻吩基、吡唑基、吲哚基、咔唑基、噻唑基、唑基、苯并噻唑基、苯并唑基、菲咯啉基(phenanthrolinyl)、环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基或环癸基,或者R1、R2或R3可通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基与Ar1连接形成稠环。
其中
R4到R10独立地表示氢、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、吗啉代、硫代吗啉代、哌啶基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、(C7-C60)二环烷基、金刚烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基,或者R4和R5、R7和R8或者R10和R11可独立地通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成螺环或稠环;以及
R4到R11的烷基、烷氧基、杂环烷基、环烷基、二环烷基、金刚烷基、芳基、杂芳基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基还可由选自下述取代基的一个或多个取代基取代:(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、哌啶基、吗啉代、硫代吗啉代、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基(C6-C60)芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基。
Ar1到Ar2可独立地表示化学键或选自下述结构的亚芳基或亚杂芳基,但不限于:
其中
R31到R36独立地表示氢、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、哌啶基、吗啉代、硫代吗啉代、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、(C6-C60)芳基(C1-C60)烷基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基。
更具体地,Ar1和Ar2可独立地表示化学键、或选自下述结构的亚芳基或亚杂芳基,但不限于:
并且,Ar3和Ar4可独立地表示(C1-C60)烷基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、金刚烷基、或选自下述结构的芳基或杂芳基。Ar3和Ar4可通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成稠环,且所述亚烷基的碳原子可用O、S、NR24或SiR25R26取代。Ar3和Ar4的烷基、芳基、杂芳基、杂环烷基、环烷基、螺环基、杂螺环基或金刚烷基,Ar3和Ar4通过有或没有稠环的亚烷基或亚烯基连接形成的稠环还可由选自下述取代基的一个或多个取代基取代:(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、哌啶基、吗啉代、硫代吗啉代、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基(C6-C60)芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基。
在上述结构中,
R42到R52独立地表示氢、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、哌啶基、吗啉代、硫代吗啉代、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基(C6-C60)芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基,R44和R45可通过有或没有稠环的(C3-C60)亚烷基或(C3-C60)亚烯基连接形成脂环或者单环或多环芳环;以及
b表示1-5的整数。
更具体地,Ar3和Ar4可独立地表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二烷基、十六烷基、苄基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、环十二烷基、吗啉基、硫代吗啉基或金刚烷基,或者可选自下述结构,但不限于:
其中R61到R63独立地表示氢、(C1-C60)烷基或(C6-C60)芳基,或者R61和R62通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成稠环。
本发明的有机电致发光化合物可以为以下化合物,但不限于此:
本发明的有机电致发光化合物可根据下述方案1制备:
方案1
其中X1、X2、Y1、Y2、R1到R3和Ar1到Ar4与化学式1中的定义相同。
在一个通常方面中,本发明提供了一种有机电致发光设备,所述设备包括:第一电极;第二电极;和插入所述第一电极和第二电极之间的一层或多层有机层,所述有机层包括一种或多种化学式1表示的有机电致发光化合物。
所述有机层可包括化学式1表示的一种或多种有机电致发光化合物作为电致发光掺杂剂,且可包含一种或多种基质。用于本发明有机电致发光设备中的基质并没有特别限制,但可选自化学式3或4表示的化合物。化学式(3)或(4)表示的基质化合物的具体结构的例子参见韩国专利申请10-2008-0060393中的<162>到<210>,但不限于此。
(Ar11)c-L1-(Ar12)d(3)
(Ar13)e-L2-(Ar14)f(4)
其中
L1表示(C6-C60)亚芳基或(C4-C60)亚杂芳基;
L2表示亚蒽基;
Ar11到Ar14各自表示氢、(C1-C60)烷基、(C1-C60)烷氧基、卤素、(C4-C60)杂芳基、(C5-C60)环烷基和(C6-C60)芳基,所述Ar11到Ar14的环烷基、芳基或杂芳基还可由选自下述取代基的一个或多个取代基取代:由一个或多个取代基(所述取代基选自(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、(C3-C60)环烷基、卤素、氰基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基)取代或未取代的(C6-C60)芳基或(C4-C60)杂芳基、卤素取代或未取代的(C1-C60)烷基、(C1-C60)烷氧基、(C3-C60)环烷基、卤素、氰基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基;以及
c,d,e和f独立地是0-4的整数。
所述电致发光层是发生电致发光的层,可由单层或者两层或多层形成。当使用本发明的基质-掺杂剂体系时,本发明的电致发光基质可明显提高电致发光效率。所述掺杂浓度可以是0.5-10重量%。当与现有的其它基质材料相比时,本发明的电致发光基质可提供优异的空穴和电子传导性,以及非常优异的稳定性和明显提高的电致发光效率和工作寿命。
因此,当选择化学式(3)或(4)表示的化合物作为电致发光基质,可明显补偿本发明化学式(1)表示的有机电致发光化合物的电缺陷。
在本发明的有机电子器件中,除了化学式1表示的有机电致发光化合物以外,所述有机层还可同时包括一种或多种选自芳胺和苯乙烯基芳胺化合物的化合物。所述芳胺化合物或苯乙烯基芳胺化合物的例子参见韩国专利申请10-2008-0060393中的<212>到<224>,但不限于此。
此外,在本发明的有机电子器件中,除了化学式1表示的有机电致发光化合物以外,所述有机层还可包括一种或多种选自元素周期表第1族、第2族的有机金属、第四周期和第五周期过渡金属、镧系金属和d-过渡元素的金属。所述有机层可包括电致发光层和电荷产生层。
可实现具有独立发光模式的像素结构的有机电致发光设备,其中同时平行图案化(patt ern)包含本发明化学式(1)的有机电致发光化合物作为一个或多个子像素的有机电致发光器件,所述子像素包含一种或多种选自Ir、Pt、Pd、Rh、Re、Os、Tl、Pb、Bi、In、Sn、Sb、Te、Au和Ag的金属。
另外,除了所述有机电致发光化合物,所述有机层还可同时包括一种或多种发射蓝光、红光或绿光的有机电致发光层,以实现发射白光的有机电致发光器件。
在本发明的有机电致发光器件中,也优选在所制备的电极对的至少一个表面上设置电子传输化合物和还原性掺杂剂的混合区,或者空穴传输化合物和氧化性掺杂剂的混合区。因此,由于电子传输化合物还原成阴离子,从而促进电子从混合区注入以及传输到电致发光介质。另外,由于空穴传输化合物氧化形成阳离子,从而促进空穴从混合区注入和传输到电致发光介质。优选的氧化性掺杂剂包括各种路易斯酸和受体化合物。还原性掺杂剂的优选实例包括碱金属、碱金属化合物、碱土金属、稀土金属及其混合物。
有益效果
因为本发明的有机电致发光化合物具有良好的蓝色发光效率和优异的寿命性质,它可用于制造具有非常好工作寿命的OLED设备。
发明实施方式
本发明进一步描述了本发明的有机电致发光化合物、制备该化合物的工艺以及使用该化合物的设备的电致发光性质。但是,这些实施例仅仅是为了阐述的目的,而不是为了限制本发明的范围。
[制备例1]制备化合物4
制备化合物(A)
将1-溴-4-(三甲基甲硅烷基)苯(25g,0.10mol)加入到1-球形(bulb)烧瓶,且建立氩气气氛。加入四氢呋喃(500mL)后,所述混合物于-78℃搅拌10分钟。逐滴加入正丁基锂(在己烷中2.5M,43.6mL,0.10mol)后,混合物于-78℃搅拌1小时30分钟。然后,于-78℃加入硼酸三甲酯(13.6mL,0.11mol)。于-78℃搅拌30分钟后,混合物于室温搅拌4小时。反应完成后,使用蒸馏水和乙酸乙酯进行萃取。用MgSO4干燥有机层,使用旋转蒸发器除去溶剂。使用己烷和乙酸乙酯作为洗脱剂通过柱层析分离纯化合物A(18g,85%)。
化合物B的制备
将2,7-二溴-9,9’-二甲基芴(30g,0.078mol)、化合物A(15.3g,0.078mol)和四(三苯基膦)钯(2.73g,0.23mmol)加入到2-球形(bulb)烧瓶。搅拌同时加入甲苯后,加入2M碳酸钾和乙醇。于100℃回流5小时后,当反应完成时将混合物冷却到室温。接着,用蒸馏水和乙酸乙酯萃取后,用MgSO4干燥有机层,使用旋转蒸发器除去溶剂。使用己烷和乙酸乙酯作为洗脱剂通过柱层析分离纯化合物B(22g,62%)。
化合物C的制备
将化合物B(22g,0.048mol)加入到单颈RBF中,且建立氮气气氛。加入四氢呋喃后,所述混合物于-78℃搅拌10分钟。逐滴加入正丁基锂(在己烷中2.5M,29.3mL,0.073mol)后,混合物于-78℃搅拌1小时。接着,加入DMF(5.6mL,0.073mmol)且搅拌10分钟后,混合物于室温搅拌4小时。反应完成后,加入HCl(2.5mL),且使用蒸馏水和乙酸乙酯于室温进行萃取。用MgSO4干燥有机层,使用旋转蒸发器除去溶剂。使用己烷和乙酸乙酯作为洗脱剂通过柱层析分离纯化合物C(17g,87%)。
制备化合物D
将化合物C(17g,0.042mol)、NaBH4(6.4g,0.17mol)和乙醇(350mL)加入到2-球形烧瓶中。于78℃回流3小时后,反应完成时,混合物倒入填充有冰的烧杯中。冰熔融后,用乙酸乙酯进行萃取。用MgSO4干燥有机层,使用旋转蒸发器除去溶剂。使用己烷和乙酸乙酯作为洗脱剂通过柱层析分离纯化合物D(16g,94%)。
制备化合物E
将化合物D(16g,0.039mol)和亚磷酸三乙酯(20mL,0.119mol)加入到1-球形烧瓶中。加入碘(10.1g,0.039mol)且搅拌30分钟后,混合物于室温搅拌12小时。反应完成后,使用真空升华器除去亚磷酸酯,且使用蒸馏水和乙酸乙酯进行萃取。用MgSO4干燥有机层,使用旋转蒸发器除去溶剂。使用己烷和乙酸乙酯作为洗脱剂通过柱层析分离纯化合物E(14g,67%)。
化合物(4)的制备
将7-(二苯基氨基)-9,9-二乙基-9H-芴-2-醛(11.2g,0.026mol)和化合物E(14g,0.026mol)加入到1-球形烧瓶中,且建立氩气气氛。加入THF(400mL)且于0℃搅拌10分钟后,缓慢加入叔丁醇钾(26.8mL,0.032mol)。于0℃搅拌10分钟后,混合物于室温再搅拌3小时。反应完成后,使用真空升华器除去亚磷酸酯,且使用蒸馏水和乙酸乙酯进行萃取。用MgSO4干燥有机层,使用旋转蒸发器除去溶剂。使用己烷和乙酸乙酯作为洗脱剂通过柱层析分离纯化合物4(18.5g,88%)。
1H NMR(CDCl3,200MHz)δ=0.25(9H,s),0.9(12H,m),1.91(8H,m),6.58-6.63(5H,m),6.75-6.81(3H,m),6.95(2H,m),7.2(4H,m),7.46(2H,m),7.54(2H,m),7.62-7.63(2H,m),7.71-7.77(5H,m),7.87-7.93(3H,m)。
[制备例2]制备化合物53
制备化合物F
2,5-二溴吡啶(25g,0.10mol)和氯三甲基硅烷(22.9g,0.21mol)加入到1-球形烧瓶中,并建立氩气气氛。加入甲苯(500mL)后,所述混合物于-78℃搅拌10分钟。逐滴加入正丁基锂(在己烷中2.5M,50mL,0.12mol)且混合物于-78℃搅拌1小时30分钟后,混合物再于室温搅拌4小时。反应完成后,使用蒸馏水和乙酸乙酯进行萃取。用MgSO4干燥有机层,使用旋转蒸发器除去溶剂。使用己烷和乙酸乙酯作为洗脱剂通过柱层析分离纯化合物F(13g,54%)。
化合物(53)的制备
根据制备例1的方法由中间体化合物F制备纯化合物53(17.7g,84%)。
1H NMR(CDCl3,200MHz)δ=-0.33(9H,m),0.9(12H,m),1.91(8H,m),6.58-6.81(8H,m),6.95(2H,m),7.2(4H,m),7.54-7.93(12H,m),8.79(1H,m)。
根据制备例1-2的方法制备化合物1-52。所制得的有机电致发光化合物的1H NMR和MS/FAB数据列在表1中。
表1
[实施例1-11]使用本发明的有机电致发光化合物制备OLED设备
使用本发明的电致发光材料制造了OLED装置。首先,将由玻璃制成的用于OLED的透明电极ITO薄膜(15Ω/□)(购自三星康宁公司(Samsung-Corning))依次用三氯乙烯、丙酮、乙醇和蒸馏水进行超声清洗,并在使用之前储存在异丙醇中。然后,将ITO基片装在真空气相沉积设备的基片夹(folder)中,将4,4’,4″-三(N,N-(2-萘基)-苯基氨基)三苯胺(2-TNATA)置于真空气相沉积设备的小室(cell)中,然后,排气,使室内真空度最高达到10-6托。接着,通过向所述小室施加电流以蒸发2-TNATA,在ITO基材上形成60nm厚的空穴注入层。
接着,向真空沉积设备的另一个小室中加入N,N’-二(α-萘基)-N,N’-二苯基-4,4’-二胺(NPB),通过向所述小室施加电流蒸发NPB,以在所述空穴注入层上沉积20nm厚的空穴传输层。
形成空穴注入层和空穴输运层后,在其上面形成电致发光层,具体如下。DNA(实施例1-4)、化合物H-78(实施例5-8)或化合物H-89(实施例9-11)置于真空沉积设备的小室内作为基质,且本发明的有机电致发光化合物置于另一个小室内作为掺杂剂。两种材料以100∶1的速率气相沉积以在所述空穴传输层上沉积30nm厚的电致发光层。
之后,气相沉积20nm厚的三(8-羟基喹啉)合-铝(III)(Alq)作为电子传输层,且气相沉积1-2nm厚的喹啉合锂(Liq)作为电子注入层。然后,采用另一个真空气相沉积设备,气相沉积150纳米厚的Al阴极,制造OLED。
用于OLED的每种化合物通过于10-6托真空升华进行纯化。
[比较例1]使用现有电致发光材料制造OLED器件
如实施例1相同的方法形成空穴注入层和空穴传输层后,将发蓝光的DNA置于真空沉积设备的另一个小室内作为基质,且化合物A置于再一个小室内。两种材料以100∶1的速率气相沉积以在所述空穴传输层上沉积30nm厚的电致发光层。
然后,按照与实施例1相同的方式形成电子传输层和电子注入层后,使用另一台真空沉积设备气相沉积150nm厚的Al阴极,以制造OLED。
在1000cd/m2的条件下测量实施例1和比较例1制造的OLED器件的发光效率。结果列于表2。
表2
如表2所示,本发明的有机电致发光化合物相比现有电致发光化合物提供了纯的蓝色。特别地,化合物47提供了纯的蓝色,同时显示出与现有电致发光材料相当的效率。如所述,本发明的有机电致发光化合物可用作蓝色发光材料,以在有机电致发光显示器中提供接近NTSC标准的颜色。
Claims (8)
1.一种化学式(1)表示的有机电致发光化合物:
其中
R1到R3独立地表示(C1-C60)烷基、(C1-C60)烷氧基、(C6-C60)芳基、(C2-C60)杂芳基或(C3-C60)环烷基,或者R1、R2或R3通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接到Ar1形成稠环,且R1到R3的烷基、烷氧基、芳基、杂芳基或环烷基还可由选自(C1-C60)烷基、(C6-C60)芳基和(C2-C60)杂芳基的一个或多个取代基取代;
X1、X2、Y1和Y2独立地表示化学键、-(CR4R5)a-、-N(R6)-、-Si(R7)(R8)-、-O-、-S-、-Se-、-P(R9)-或-(R10)C=C(R11)-;
Ar1和Ar2独立地表示化学键、(C6-C60)亚芳基或包含一个或多个选自N、O、S和Se的杂原子的(C2-C60)杂亚芳基;
Ar3和Ar4独立地表示(C1-C60)烷基、(C6-C60)芳基、(C2-C60)杂芳基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、单-、二-或三-(C15-C60)螺环、包含一个或多个选自N、O和S的杂原子的(C10-C60)杂螺环基、金刚烷基或或者Ar3和Ar4通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成稠环,所述亚烷基的碳原子可由O、S、NR24或SiR25R26取代;
R4到R11独立地表示氢、氘、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、吗啉代、硫代吗啉代、哌啶基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、(C7-C60)二环烷基、金刚烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基,或者R4和R5、R7和R8或者R10和R11可独立地通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成螺环或稠环;
R21到R26独立地表示氢、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、吗啉代、硫代吗啉代、哌啶基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、金刚烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基,或者R25和R26可独立地通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成螺环或稠环;
Ar1和Ar2的亚芳基或杂亚芳基,Ar3和Ar4的烷基、芳基、杂芳基、杂环烷基、环烷基、螺环基、杂螺环基或金刚烷基,Ar3和Ar4通过有或没有稠环的亚烷基或亚烯基连接形成的稠环,以及R4到R11、R21到R26的烷基、烷氧基、杂环烷基、环烷基、二环烷基、金刚烷基、芳基、杂芳基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基还可由选自下述取代基的一个或多个取代基取代:(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、哌啶基、吗啉代、硫代吗啉代、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基(C6-C60)芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基;以及
a表示1-4的整数。
其中
R4到R10独立地表示氢、(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、吗啉代、硫代吗啉代、哌啶基、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、(C7-C60)二环烷基、金刚烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基或三(C6-C60)芳基甲硅烷基,或者R4和R5、R7和R8或者R10和R11可独立地通过有或没有稠环的(C3-C12)亚烷基或(C3-C12)亚烯基连接形成螺环或稠环;以及
R4到R11的烷基、烷氧基、杂环烷基、环烷基、二环烷基、金刚烷基、芳基、杂芳基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基还可由选自下述取代基的一个或多个取代基取代:(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、哌啶基、吗啉代、硫代吗啉代、包含一个或多个选自N、O和S的杂原子的5-或6-元杂环烷基、(C3-C60)环烷基、卤素、氰基、(C6-C60)芳基、(C2-C60)杂芳基、(C6-C60)芳基(C1-C60)烷基、(C1-C60)烷基(C6-C60)芳基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基。
4.一种有机电致发光器件,所述器件包括权利要求1-3中任一项所述的有机电致发光化合物。
5.如权利要求4所述的有机电致发光器件,所述器件由以下部分组成:第一电极;第二电极;以及插入所述第一电极和第二电极之间的至少一层有机层,其中所述有机层包含一种或多种权利要求1-3中任一项所述的有机电致发光化合物,和一种或多种选自化学式(3)或(4)表示的基质:
(Ar11)c-L1-(Ar12)d(3)
(Ar13)e-L2-(Ar14)f(4)
其中
L1表示(C6-C60)亚芳基或(C4-C60)亚杂芳基;
L2表示亚蒽基;
Ar11到Ar14各自表示氢、(C1-C60)烷基、(C1-C60)烷氧基、卤素、(C4-C60)杂芳基、(C5-C60)环烷基和(C6-C60)芳基,所述Ar11到Ar14的环烷基、芳基或杂芳基还可由选自下述取代基的一个或多个取代基取代:由一个或多个取代基(所述取代基选自(C1-C60)烷基、卤代(C1-C60)烷基、(C1-C60)烷氧基、(C3-C60)环烷基、卤素、氰基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基)取代或未取代的(C6-C60)芳基或(C4-C60)杂芳基、卤素取代或未取代的(C1-C60)烷基、(C1-C60)烷氧基、(C3-C60)环烷基、卤素、氰基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基(C6-C60)芳基甲硅烷基和三(C6-C60)芳基甲硅烷基;以及
c,d,e和f独立地是0-4的整数。
6.如权利要求5所述的有机电致发光器件,其特征在于,所述有机层还包含一种或多种选自芳胺化合物和苯乙烯基芳胺化合物的化合物,或选自元素周期表的第1族、第2族的有机金属、第四周期和第五周期的过渡金属、镧系金属和d-过渡元素的一种或多种金属。
7.如权利要求5所述的有机电致发光器件,其特征在于,所述有机层包括电致发光层和电荷产生层。
8.如权利要求5所述的有机电致发光器件,其特征在于,所述有机电致发光器件发射白光,因为所述有机层同时包括一层或多层发射蓝光、红光或绿光的有机电致发光层。
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KR10-2009-0048715 | 2009-06-02 | ||
PCT/KR2010/003456 WO2010140801A1 (en) | 2009-06-02 | 2010-05-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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KR (1) | KR20100130059A (zh) |
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WO2012137568A1 (ja) * | 2011-04-05 | 2012-10-11 | 株式会社Adeka | 新規化合物及び光電変換素子 |
US8652656B2 (en) * | 2011-11-14 | 2014-02-18 | Universal Display Corporation | Triphenylene silane hosts |
KR101952707B1 (ko) | 2012-01-03 | 2019-06-03 | 삼성디스플레이 주식회사 | 신규한 화합물 및 이를 포함한 유기발광 소자 |
WO2015114102A1 (en) * | 2014-02-03 | 2015-08-06 | Basf Se | Silyl substituted azadibenzofurans and azadibenzothiophenes |
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JP2012528852A (ja) | 2012-11-15 |
WO2010140801A1 (en) | 2010-12-09 |
KR20100130059A (ko) | 2010-12-10 |
JP5651689B2 (ja) | 2015-01-14 |
TW201107450A (en) | 2011-03-01 |
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