CN104583184A - 基质化合物和掺杂剂化合物的新颖组合及包含该组合的有机电致发光器件 - Google Patents
基质化合物和掺杂剂化合物的新颖组合及包含该组合的有机电致发光器件 Download PDFInfo
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- CN104583184A CN104583184A CN201380043768.0A CN201380043768A CN104583184A CN 104583184 A CN104583184 A CN 104583184A CN 201380043768 A CN201380043768 A CN 201380043768A CN 104583184 A CN104583184 A CN 104583184A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 133
- 239000002019 doping agent Substances 0.000 title claims abstract description 38
- 238000005401 electroluminescence Methods 0.000 title claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 239000011159 matrix material Substances 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims description 2
- 239000013110 organic ligand Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 29
- 239000000203 mixture Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- 239000010410 layer Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- -1 aromatic diamine small molecules Chemical class 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
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- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 CC1=C*(C(C=C(/C=C/C[C@]2N)C(C=CC3c4c5cccc4)=CC3C5c3ccccc3)=C)=C2C=*C2=CC=CCC2*1 Chemical compound CC1=C*(C(C=C(/C=C/C[C@]2N)C(C=CC3c4c5cccc4)=CC3C5c3ccccc3)=C)=C2C=*C2=CC=CCC2*1 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000005104 aryl silyl group Chemical group 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl 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
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- ZLSGUABVPXAURB-UHFFFAOYSA-N C=Bc1ccccc1[N+]([O-])=O Chemical compound C=Bc1ccccc1[N+]([O-])=O ZLSGUABVPXAURB-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
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- 101150003085 Pdcl gene Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- JXDJGUVZSMZRAV-UHFFFAOYSA-N [O-][N+](c1ccccc1-c1c2[s]c3ccccc3c2ccc1)=O Chemical compound [O-][N+](c1ccccc1-c1c2[s]c3ccccc3c2ccc1)=O JXDJGUVZSMZRAV-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
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- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 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
- 239000004327 boric acid Substances 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NPHLAWPEXYBGTP-UHFFFAOYSA-N c1ccc2[nH]c3ccc(c4ccccc4[s]4)c4c3c2c1 Chemical compound c1ccc2[nH]c3ccc(c4ccccc4[s]4)c4c3c2c1 NPHLAWPEXYBGTP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- ZLWLTDZLUVBSRJ-UHFFFAOYSA-K chembl2360149 Chemical compound [Na+].[Na+].[Na+].O=C1C(N=NC=2C=CC(=CC=2)S([O-])(=O)=O)=C(C(=O)[O-])NN1C1=CC=C(S([O-])(=O)=O)C=C1 ZLWLTDZLUVBSRJ-UHFFFAOYSA-K 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
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- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
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- 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 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
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- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
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Abstract
本发明涉及掺杂剂化合物和基质化合物的特定组合以及包括该特定组合的有机电致发光器件。本发明的有机电致发光器件相比包含常规发光材料的器件在较低驱动电压条件下提供较高的发光效率。
Description
技术领域
本发明涉及基质化合物和掺杂剂化合物的新颖组合以及包含该新颖组合的有机电致发光器件。
背景技术
电致发光(EL)器件是一种自发光器件,其优势在于相比LED提供了更宽的可视角、更高的对比度并具有更快速的响应时间。伊斯曼柯达公司(Eastman Kodak)通过使用芳族二胺小分子和铝配合物作为形成发光层的材料,最先开发了一种有机EL器件[Appl.Phys.Lett.51,913,1987]。
有机EL器件中决定发光效率的最重要的因素是发光材料。电致发光材料包括基质材料和用于功能性目的的掺杂剂材料。通常,已知具有极其优异电致发光特性的器件具有这样的结构,其中,基质用掺杂剂掺杂以形成电致发光层。目前,开发具有高效率和长寿命的有机EL器件正成为一项急迫的任务。具体地,考虑到中到大型OLED面板所需的电致发光性能,开发相比常规电致发光材料性能更优异的材料变得急迫。
迄今为止,荧光材料被广泛地用作发光材料。然而,从电致发光的机理来看,研制磷光材料是理论上将发光效率提高4倍的最好的方法之一。铱(III)络合物是众所周知的磷光物质的掺杂剂化合物,其包括二(2-(2'-苯并噻吩基)-吡啶根合-N,C3')(乙酰丙酮酸根合)铱[(acac)Ir(btp)2]、三(2-苯基吡啶)铱[Ir(ppy)3]和二(4,6-二氟苯基吡啶合-N,C2)吡啶甲酸根合(picolinato)铱〔Firpic〕,分别作为红色、绿色和蓝色材料。迄今为止,已知4,4'-N,N'-二咔唑-联苯(CBP)是最广泛用作磷光物质的基质材料。此外,空穴阻挡层使用浴铜灵(bathocuproine)(BCP)和二(2-甲基-8-羟基喹啉合(quinolinate))(4-苯基苯酚)铝(III)(BAlq)的高效有机EL器件也是已知的。但是,当使用包含常规掺杂剂和基质化合物的发光材料时,在功率效率、工作寿命和发光效率方面存在问题。
韩国专利申请公开KR2007080438A公开了Ir(ppy)3结构(其是常规掺杂剂化合物)上引入烷基或芳基的铱络合物作为包含在有机电致发光器件的发光材料中的掺杂剂化合物。但是,上述文献并没有揭示与基质化合物的优选组合,也不能解决发光效率等的问题。
本发明的发明人发现掺杂剂化合物和基质化合物的特定组合可适合制造具有高色纯度、高发光和长寿命的有机EL器件。
发明内容
待解决的问题
本发明的目的在于提供新的掺杂剂/基质组合以及包含该组合的有机电致发光器件,其在较低工作电压的情况下提供了优异的发光效率。
解决问题的方法
为了达到上述目的,本发明提供了一种或多种下式1表示的掺杂剂化合物和一种或多种下式2表示的基质化合物的组合:
其中,
L是有机配体;
R1到R9各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C3-C30)环烷基、取代或未取代的(C1-C30)烷氧基、取代或未取代的(C6-C30)芳基或取代或未取代的3元到30元杂芳基;
R表示氢、卤素、取代或未取代的(C1-C30)烷基或取代或未取代的(C3-C30)环烷基;
a表示1-3的整数;当a是大于或等于2的整数时,每个R是相同的或不同的;以及
n表示1-3的整数;
A–D–C ----------(2)
其中,
D表示单键、取代或未取代的(C3-C30)环亚烷基、取代或未取代的(C6-C30)亚芳基、或取代或未取代的5元至30元杂亚芳基;
A由下式3或4表示:
其中,
-*表示与D连接的位置;
X表示NR10、O、S或CR11R12;
Ar1-Ar4各自独立地表示氢、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的5-30元杂芳基、取代或未取代的(C3-C30)环烷基、-NR13R14、-SiR15R16R17、-SR18或-OR19;和
R10-R19各自独立地表示氢,取代或未取代的(C1-C30)烷基,或者取代或未取代的(C6-C30)芳基;
C由下式5表示:
其中,
-*表示与D连接的位置;
Y和Z各自独立地表示CH或N;
E环表示取代或未取代的苯环,或者不存在;
Ar5和Ar6各自独立地表示氢、取代或未取代的(C6-C30)芳基、取代或未取代的5-30元杂芳基、取代或未取代的(C6-C30)环烷基、-NR21R22、-SiR23R24R25、-SR26或-OR27;和
R21-R27各自独立地表示氢,取代或未取代的(C1-C30)烷基,取代或未取代的(C6-C30)芳基,或者取代或未取代的5-30元杂芳基。
发明的有益效果
本发明的有机电致发光器件包含掺杂剂化合物和基质化合物的特定组合,相比包含常规发光材料的器件在较低驱动电压条件下提供较高的发光效率。
本发明实施方式
下面将详细描述本发明。但是,以下描述是用于解释本发明,而不是为了以任意方式限制本发明的范围。
本发明涉及包含一种或多种下式1表示的掺杂剂化合物和一种或多种下式2表示的基质化合物的有机电致发光器件。
式1表示的掺杂剂化合物优选由式6或7表示:
其中R,R1-R9,L,n和a如式1所定义的。
在式1、6和7中,L选自下述结构,但不限于此:
其中R201-R211各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、或取代或未取代的(C3-C30)环烷基。
在式1、6和7中,R和R1-R9优选各自独立地表示氢、卤素、取代或未取代的(C1-C10)烷基、或取代或未取代的(C3-C10)环烷基,且更优选地各自独立地表示氢、卤素、未取代的(C1-C6)烷基、被(C1-C6)烷基取代的(C1-C6)烷基、未取代的(C3-C7)环烷基或被(C1-C6)烷基取代的(C3-C7)环烷基。
式1的代表性化合物包括以下化合物,但不限于此:
在式2中,D优选表示单键,或选自下组:
其中,-*表示与C连接的位置,表示与A连接的位置。
在式2中,A由式3或4表示,其中X优选表示NR10,O,S或CR11R12,R10-R12优选各自独立地表示(C1-C6)烷基或(C6-C12)芳基。Ar1-Ar4优选各自独立地表示氢;未取代的(C1-C10)烷基或被(C1-C6)烷基取代的(C1-C10)烷基;未取代的(C6-C15)芳基,或被(C1-C6)烷基或(C6-C12)芳基取代的(C6-C15)芳基;未取代的或被(C1-C6)烷基或(C6-C12)芳基取代的5-15元杂芳基;或-SiR15R16R17,其中R15-R17优选各自独立地表示(C1-C6)烷基。
在式2中,A优选自下组:
在式2中,C由式5表示,其中E环表示未取代的或被(C6-C12)芳基取代的苯环,或者不存在E环,Ar5和Ar6优选各自独立地表示氢、取代或未取代的(C6-C20)芳基、取代或未取代的5-20元杂芳基、或者-SiR23R24R25,R23-R25各自独立地表示(C6-C12)芳基。
取代的芳基以及取代的杂芳基的取代基各自独立地优选是选自下组的至少一种:卤素,(C1-C6)烷基,(C3-C7)环烷基,未取代的或被(C1-C6)烷基取代的(C6-C12)芳基,未取代的或被(C6-C12)芳基取代的5-15元杂芳基,三(C6-C12)芳基甲硅烷基,以及(C1-C6)烷基二(C6-C12)芳基甲硅烷基。
在式2中,C优选自下组:
在本文中,烷基包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基等;烷氧基包括甲氧基、乙氧基、正丙氧基、异丙氧基等;环烷基包括环丙基、环丁基、环戊基、环己基等;芳基包括苯基、联苯基、三联苯基、萘基、芴基、菲基、蒽基、茚基、苯并菲基、芘基、并四苯基(tetracenyl)、二萘嵌苯基、屈基、萘并萘基(naphthacenyl)、荧蒽基等。
在本文中,(亚)杂芳基包含至少一个选自B、N、O、S、P(=O)、Si和P的杂原子;其是单环或与至少一个苯环稠合的稠环;其可以是部分饱和的;其可以将至少一个杂芳基或芳基基团与杂芳基通过单键连接形成;包括单环型杂芳基,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、异噁唑基、噁唑基、噁二唑基、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;以及稠环型杂芳基,如苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、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、喹唑啉基、喹喔啉基、咔唑基、吩噁嗪基、菲啶基、苯并间二氧杂环戊烯基等。此外,“卤素”包括F、Cl、Br和I。
本文所用术语“取代或未取代的”中的“取代”指的是某个官能团中的氢原子被另一个原子或基团(即取代基)代替。
上述式中取代的烷基、取代的(亚)芳基、取代的杂(亚)芳基、取代的环(亚)烷基和取代的烷氧基的取代基各自独立地优选是至少一种选自下组的基团:氘、卤素、未取代的或被卤素取代的(C1-C30)烷基、(C6-C30)芳基、未取代的或被(C6-C30)芳基取代的3-至30-元杂芳基、5-至7-元杂环烷基、与至少一个(C6-C30)芳环稠合的5-至7-元杂环烷基、(C3-C30)环烷基、与至少一个(C6-C30)芳环稠合的(C6-C30)环烷基、RaRbRcSi-、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、-NRdRe、-BRfRg、-PRhRi、-P(=O)RjRk、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、RlW-、RmC(=O)-、RmC(=O)O-、羧基、硝基和羟基,其中Ra至Rl各自独立地表示(C1-C30)烷基、(C6-C30)芳基或3-至30-元杂芳基,或与相邻取代基连接以形成单环或多环的5元到30元脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子代替,W表示S或O,以及Rm表示(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳基或(C6-C30)芳氧基。
式2的代表性化合物包括以下化合物,但不限于此:
式1表示的化合物可根据下述反应流程1制备,但不限于此。另外,改良合成方法对于本领域普通技术人员来说都是显而易见的。
[反应流程1]
其中L,R,R1-R9,n和a如式1所定义的。
特别地,所述有机电致发光器件包括第一电极、第二电极以及所述第一电极和第二电极之间的至少一层有机层。所述有机层包括发光层,所述发光层包含一种或多种式1所示掺杂剂化合物和一种或多种式2所示基质化合物的组合。
所述发光层是指发射光的层,其可以是单层或者两层或更多的层层合的多层。除了发出光,所述发光层也可以注入/转移电子/空穴。掺杂浓度(即掺杂剂化合物相对于基质化合物的比例)优选小于20重量%。
本发明的另一个实施方式提供了一种或多种式1表示的掺杂剂化合物和一种或多种式2表示的基质化合物的基质/掺杂剂组合,以及包含该基质/掺杂剂组合的有机EL器件。
本发明的另一个实施方式提供了由一种或多种式1表示的掺杂剂化合物和一种或多种式2表示的基质化合物的组合构成的有机层。所述有机层包括多个层。所述掺杂剂化合物和所述基质化合物可以包含在同一层中,或者包含在不同层中。此外,本发明提供了包含所述有机层的有机EL器件。
在本发明的有机电致发光器件中,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可设置在一对电极中的至少一个表面上。在这种情况下,电子传输化合物被还原成阴离子,这样电子从混合区注入并传输到电致发光介质中变得更加容易。此外,空穴传输化合物被氧化成阳离子,从而空穴从混合区注入并传输到电致发光介质中变得更加容易。优选地,所述氧化性掺杂剂包括各种路易斯酸和受体化合物;所述还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属及其混合物。可以采用还原性掺杂剂层作为电荷产生层来制备具有两层或更多层电致发光层并发射白光的电致发光器件。
下文中,结合以下实施例详细地解释了所述化合物、该化合物的制备方法、以及器件的发光性质。但是,这些仅仅用于举例描述本发明的实施方式,所以本发明的范围并不限于此。
实施例1:化合物D-5的制备
化合物5-1的制备
向甲苯(100mL)、乙醇(50mL)和H2O(50mL)的混合溶剂中加入4-联苯基硼酸(12g,64mmol)、2-溴-3-甲基吡啶(10g,58mmol)、PdCl2(PPh3)2(1.2g,1.7mmol)和Na2CO3(10g,94mmol)之后,混合物在120℃搅拌4小时。然后,反应混合物用乙酸乙酯(EA)/H2O萃取(work up),用MgSO4去除水分,再减压蒸馏剩余产物。接着,产物用二氯甲烷(MC):己烷(Hex)通过柱层析纯化得到14g(70%)白色固体化合物5-1。
化合物5-2的制备
向2-乙氧基乙醇(120mL)和H2O(40mL)的混合溶剂中加入化合物5-1(10g,41mmol)和IrCl3·xH2O(5g,17mmol)后,混合物在120℃回流搅拌24小时。完成反应后,混合物用H2O/MeOH/Hex洗涤,并干燥得到化合物5-210g(75%)。
化合物5-3的制备
向2-乙氧基乙醇(120mL)加入化合物5-2(10g,7.0mmol),2,4-戊二酮(pentanedion)(1.4g,14mmol)和Na2CO3(3.7g,34.7mmol)后,混合物在110℃搅拌12小时。完成反应后,形成的固体用H2O/MeOH/Hex洗涤。充分干燥后,产物用CHCl3溶解并用MC/Hex通过柱层析纯化得到化合物5-37.5g(68%)。
化合物D-5的制备
向化合物5-3(5g,6.25mmol)和化合物5-1(3.1g,12.4mmol)的混合物中加入甘油后,混合物回流搅拌16小时。反应后,对形成的固体进行过滤,用H2O/MeOH/Hex洗涤并干燥。充分干燥后,产物用CHCl3溶解并用MC/Hex通过柱层析纯化得到化合物D-53.8g(64%)。
实施例2:化合物D-9的制备
化合物9-1的制备
向甲苯(100mL)和乙醇(400mL)的混合溶剂中加入3-联苯基硼酸(35g,174mmol)、2-溴-4-甲基吡啶(20g,116mmol)、Pd(PPh3)4(4g,3.5mmol)和2M K2CO3(200mL,400mmol)之后,混合物在100℃搅拌3小时。然后,反应混合物用EA/H2O萃取(work up),用MgSO4去除水分,再减压蒸馏剩余产物。接着,产物用MC/Hex通过柱层析纯化得到18g(63%)白色固体化合物9-1。
化合物9-2的制备
向2-乙氧基乙醇(100mL)和H2O(37mL)的混合溶剂中加入化合物9-1(7.6g,31mmol)和IrCl3·xH2O(4.2g,14mmol)后,混合物在130℃搅拌24小时。反应完成后,混合物冷却到室温,用水和MeOH洗涤,并干燥得到化合物9-28g(80%)。
化合物9-3的制备
向2-乙氧基乙醇(80mL)加入化合物9-2(7g,5mmol),2,4-戊二酮(pentanedion)(1.5g,15mmol)和Na2CO3(1.6g,15mmol)后,反应在110℃进行3小时。反应完成之后,用柱色谱对形成的固体进行纯化,得到化合物9-3(5g,70%)。
化合物D-9的制备
向化合物9-3(4g,5mmol)和化合物9-1(2.5g,10mmol)的混合物中加入甘油后,混合物在220℃回流搅拌24小时。反应完成之后,用柱色谱对形成的固体进行纯化,得到化合物D-9(4g,80%)。
实施例3:化合物D-28的制备
按照与实施例2的化合物9-1到化合物9-3的合成方法相同的方法制备化学28-1到化合物28-3。
化合物D-28的制备
向化合物28-3(4.5g,5.2mmol)和化合物28-1(3.0g,10.4mmol)的混合物中加入甘油后,混合物回流搅拌16小时。反应后,对形成的固体进行过滤,用H2O/MeOH/Hex洗涤并干燥。充分干燥后,产物用CHCl3溶解并用MC/Hex通过柱层析纯化得到化合物D-281.8g(33%)。
实施例1-3中制备的掺杂剂化合物的详细数据以及使用实施例1-3容易制备的掺杂剂化合物如下表1所示。
[表1]
化合物 | 产率(%) | UV光谱(nm) | PL光谱(nm) | 熔点(℃) |
D-2 | 63 | 322 | 540 | 310 |
D-5 | 64 | 326 | 534 | 高于400 |
D-9 | 80 | 286 | 513 | 高于400 |
D-10 | 56 | 269 | 517 | 389 |
D-14 | 23 | 324 | 510 | 335 |
D-18 | 68 | 294 | 515 | 350 |
D-28 | 27 | 296 | 511.94 | 高于400 |
实施例4:化合物C-11的制备
化合物C-11-1的制备
将1-溴-2-硝基苯(85g,0.42mol),二苯并[b,d]噻吩-4-基硼酸(80g,0.35mol),Pd(PPh3)4(20g,0.018mol),K2CO3(116g,1.0mol),甲苯(1700mL),乙醇(440mL)和H2O(440mL)在圆底烧瓶中混合之后,在120℃搅拌该混合物12小时。反应完成之后,用乙酸乙酯萃取混合物,用MgSO4干燥有机层。接着,过滤剩余产物,减压下除去溶剂,通过柱将剩余的产物分离以得到白色固体化合物C-11-1(93g,87%)。
化合物C-11-2的制备
将化合物C-11-1(88g,0.29mol),1,2-二氯苯(960mL,0.4M)和亚磷酸三乙酯(960mL)在无水条件下在圆底烧瓶中混合之后,将该混合物在90℃搅拌12小时。反应完成后,蒸馏混合物除去亚磷酸三乙酯,通过柱将剩余的产物分离,得到白色固体化合物C-11-2(40g,70%)。
化合物C-11-3的制备
将9H-咔唑(30g,0.18mol)、1.3-二溴苯(85g,0.36mol)、CuI(34g,0.18mol)、K3PO4(114g,0.54mol)和甲苯(1200ml)在圆底烧瓶中混合之后,将混合物在120℃搅拌10分钟。然后,向混合物中加入乙二胺(24mL,0.36mol),在120℃搅拌混合物12小时。反应完成之后,用乙酸乙酯(EA)萃取混合物,用MgSO4干燥有机层。接着,过滤剩余产物,减压下除去溶剂,通过柱将剩余的产物分离以得到白色固体化合物C-11-3(30g,52%)。
化合物C-11-4的制备
在四氢呋喃(THF)中溶解化合物C-11-325g(80.85mmol)之后,将正丁基锂(42mL,105.10mmol,在乙烷中浓度为2.5M)于-78℃缓慢加入到混合物中。1小时后,向该混合物加入硼酸三甲酯(14.42mL,129.3mmol)。然后,在室温下搅拌该混合物12小时,在该混合物中加入蒸馏水。接着,用EA萃取混合物,用MgSO4干燥,减压蒸馏,用MC和己烷重结晶,得到化合物C-11-4(15g,58%)。
化合物C-11-5的制备
将化合物C-11-4(20g,72.96mmol)、2,4-二氯嘧啶(9.8g,80.25mmol)、Pd(PPh3)4(2.28g,2.18mmol)、K2CO3(2M,80mL),甲苯(150ML)和乙醇(50mL)加入烧瓶中后,所述混合物回流搅拌5小时。接着,混合物冷却到室温,向混合物中加入蒸馏水。接着,用EA萃取混合物,用MgSO4干燥,减压蒸馏,用EA和甲醇重结晶,得到化合物C-11-5(9.8g,80%)。
化合物C-11的制备
将NaH(0.9g,60%,20mmol)和二甲基甲酰胺(DMF,50mL)在500mL圆底烧瓶中在无水条件下混合后,将化合物C-11-2(4.69g,17mmol)溶解在DMF(20mL)中,加入包含NaH的圆底烧瓶中。将混合物搅拌1小时后,将化合物C-11-5(6.1g,17mmol)溶于DMF(100mL),并添加到包含化合物C-11-2的烧瓶中。将混合物搅拌12小时后,过滤黄色固体,重结晶,得到化合物C-113g(30%)。
实施例5:化合物C-38的制备
化合物C-38-1的制备
在甲苯(900mL)、EtOH(200mL)和纯化水(300mL)的混合溶剂中加入1-溴-2-硝基苯(50g,248毫摩尔)、二苯并噻吩-4-硼酸(62g,272毫摩尔)、K2CO3(85g,619毫摩尔)和Pd(PPh3)4(14g,12.4毫摩尔)后,回流搅拌该混合物1天。反应完成后,将该混合物冷却至室温,用蒸馏水和EA进行萃取。随后,将该有机层减压蒸馏,然后通过柱用MC/Hex进行分离,得到化合物C-38-1(60g,80%)。
化合物C-38-2的制备
将P(OEt)3(1L)加入化合物C-38-1(130g,426mmol)后,将该混合物在150℃搅拌1天。反应完成后,所述混合物减压浓缩,用MC进行萃取,浓缩有机层。接着,通过柱用MC/Hex分离所得产物,得到化合物C-38-2(46g,40%)。
化合物C-38-3的制备
将POCl3缓慢滴加到苯胺(15mL,169mmol)和丙二酸(25g,492mmol)的混合物中后,将该混合物回流搅拌1天。将反应混合物缓慢加入到冰水后,用5M NaOH中和该混合物。随后,用蒸馏水和MC萃取所得固体,有机层减压蒸馏,然后通过柱用MC/Hex进行分离,得到化合物C-38-3(17g,53%)。
化合物C-38-4的制备
将1,2-二氯苯加入化合物C-38-2(6.2g,31.4mmol),化合物C-38-3(8.6g,31.4mmol),CuI(12g,63mmol),Cs2CO3(31g,95mmol)和反式-1,2-二氨基环己烷的混合物中后,将混合物回流搅拌1天。反应完成后,所述混合物减压浓缩,用MC进行萃取,浓缩有机层。接着,通过柱用MC/Hex分离所得产物,得到化合物C-38-4(7.4g,55%)。
化合物C-38的制备
在甲苯(100mL)、EtOH(15mL)和纯化水(20mL)的混合溶剂中加入化合物C-38-4(6.8g,15.6mmol),4-联苯基硼酸(6.2g,31毫摩尔)、K2CO3(5.4g,38.9毫摩尔)和Pd(PPh3)4(1.8g,1.6毫摩尔)后,回流搅拌该混合物1天。反应完成后,将该混合物冷却至室温,用蒸馏水和MC进行萃取。随后,将该有机层减压蒸馏,然后通过柱用MC/Hex进行分离,得到化合物C-38(3.5g,41%)。
实施例4和5中制备的基质化合物的详细数据以及使用实施例4和5容易制备的基质化合物如下表2所示。
[表2]
器件实施例1:使用本发明有机电致发光化合物制造OLED器件
使用本发明的发光材料制造了OLED器件。用三氯乙烯、丙酮、乙醇和蒸馏水依次对用于有机发光二极管(OLED)器件的玻璃基材上的透明电极氧化铟锡(ITO)薄膜(15Ω/平方)(韩国三星康宁公司(Samsung Corning))进行超声清洗,然后储存在异丙醇中。接着,将ITO基材安装在真空气相沉积设备的基材夹具(holder)上。将N1,N1’-([1,1’-联苯]-4,4’-二基)二(N1-(萘-1-基)-N4,N4-二苯基苯-1,4-二胺)引入所述真空气相沉积设备的室中,然后对所述设备的室压进行控制以达到10-6托。接着,向小室施加电流以蒸发上述引入的物质,从而在ITO基材上形成厚度为60nm的空穴注入层。然后,将N,N’-二(4-联苯基)-N,N’-二(4-联苯基)-4,4’-二氨基苯引入所述真空气相沉积设备的另一个小室中,通过向该小室施加电流以进行蒸发,从而在所述空穴注入层上形成厚度为20nm的空穴传输层。之后,将化合物C-11引入真空气相沉积设备的一个小室中作为基质材料,并将化合物D-9引入另一个小室中作为掺杂剂。将两种材料以不同的速率进行蒸发,并以15重量%(以基质材料和掺杂剂的总重量为基准计)的掺杂量进行沉积,从而在空穴传输层上形成厚度为30nm的发光层。然后,将2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑引入一个小室中,并将8-羟基喹啉合锂(lithium quinolate)引入另一个小室中。将两种材料以相同的速率进行蒸发,并分别以50重量%的掺杂量进行沉积,从而在发光层上形成厚度为30nm的电子传输层。然后,在电子传输层上沉积了厚度为2nm的8-羟基喹啉合锂作为电子注入层之后,通过另一真空气相沉积设备在电子注入层上沉积厚度为150nm的Al阴极。从而,制备了OLED器件。制备OLED器件所用的所有材料,在使用前通过在10-6托条件下的真空升华进行纯化。
制备的OLED器件在5.0V的驱动电压下发射出亮度为5030cd/m2的绿光且电流密度为13.97mA/cm2。
器件实施例2:使用本发明有机电致发光化合物制造OLED器件
用与器件实施例1同样的方式制备OLED器件,不同之处在于使用化合物C-17作为基质,使用化合物D-28作为发光材料的掺杂剂。
制备的OLED器件在3.2V的驱动电压下发射出亮度为2060cd/m2的绿光且电流密度为4.63mA/cm2。
比较例1:使用常规有机电致发光材料制造OLED器件
使用与器件实施例1相同的方法制备OLED器件,不同之处在于使用4,4'-N,N'-二咔唑-联苯作为基质材料,使用化合物Ir(ppy)3作为掺杂剂,以在空穴传输层上形成厚度为30nm的发光层;并且通过沉积二(2-甲基-8-羟基喹啉合(quinolinato))4-苯基苯酚铝(III)形成厚度为10nm的空穴阻挡层。
制备的OLED器件在7.5V的驱动电压下发射出亮度为3000cd/m2的绿光且电流密度为9.8mA/cm2。
如上所示,本发明的有机EL器件所含有的发光材料包含掺杂剂和基质化合物的特定组合,相比使用常规发光材料的器件在较低驱动电压条件下提供改善的发光效率。这是因为通过将烷基和芳基引入到作为常用掺杂剂化合物的Ir(ppy)3结构上控制了能隙。通过该方法,本发明的基质化合物的能隙相比常规基质化合物与本发明的掺杂剂化合物更好的结合,最终本发明的有机EL器件提供了优异的发光效率。
Claims (9)
1.一种或多种下式1表示的掺杂剂化合物和一种或多种下式2表示的基质化合物的组合:
其中,
L是有机配体;
R1到R9各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C3-C30)环烷基、取代或未取代的(C1-C30)烷氧基、取代或未取代的(C6-C30)芳基或取代或未取代的3元到30元杂芳基;
R表示氢、卤素、取代或未取代的(C1-C30)烷基或取代或未取代的(C3-C30)环烷基;
a表示1-3的整数;当a是大于或等于2的整数时,每个R是相同的或不同的;以及
n表示1-3的整数;
A–D–C ----------(2)
其中,
D表示单键、取代或未取代的(C3-C30)环亚烷基、取代或未取代的(C6-C30)亚芳基、或取代或未取代的5元至30元杂亚芳基;
A由下式3或4表示:
其中,
-*表示与D连接的位置;
X表示NR10、O、S或CR11R12;
Ar1-Ar4各自独立地表示氢、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的5-30元杂芳基、取代或未取代的(C3-C30)环烷基、-NR13R14、-SiR15R16R17、-SR18或-OR19;和
R10-R19各自独立地表示氢,取代或未取代的(C1-C30)烷基,或者取代或未取代的(C6-C30)芳基;
C由下式5表示:
其中,
-*表示与D连接的位置;
Y和Z各自独立的表示CH或N;
E环表示取代或未取代的苯环,或者不存在;
Ar5和Ar6各自独立地表示氢、取代或未取代的(C6-C30)芳基、取代或未取代的5-30元杂芳基、取代或未取代的(C6-C30)环烷基、-NR21R22、-SiR23R24R25、-SR26或-OR27;和
R21-R27各自独立地表示氢,取代或未取代的(C1-C30)烷基,取代或未取代的(C6-C30)芳基,或者取代或未取代的5-30元杂芳基。
2.如权利要求1所述的组合,其特征在于,由式1表示的化合物由下式6或7表示:
其中R,R1-R9,L,n和a如权利要求1所定义。
3.如权利要求1所述的组合,其特征在于,式1中的L选自下组:
其中R201-R211各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、或取代或未取代的(C3-C30)环烷基。
4.如权利要求1所述的组合,其特征在于,式2中的D是单键或选自下组:
其中,-*表示与C连接的位置,表示与A连接的位置。
5.如权利要求1所述的组合,其特征在于,式2中的A选自下组:
6.如权利要求1所述的组合,其特征在于,式2中的C选自下组:
7.如权利要求1所述的组合,其特征在于,由式1表示的化合物选自下组:
8.如权利要求1所述的组合,其特征在于,由式2表示的化合物选自下组:
9.一种包含权利要求1所述的组合的有机电致发光器件。
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CN114031609A (zh) * | 2021-12-14 | 2022-02-11 | 北京燕化集联光电技术有限公司 | 一种含咔唑及喹唑啉类结构化合物及其应用 |
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WO2015174738A1 (en) * | 2014-05-14 | 2015-11-19 | Rohm And Haas Electronic Materials Korea Ltd. | Multi-component host material and organic electroluminescent device comprising the same |
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