JP2006306870A - アミノスチリル化合物、その製造方法及びそれを備えた有機発光素子 - Google Patents
アミノスチリル化合物、その製造方法及びそれを備えた有機発光素子 Download PDFInfo
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- JP2006306870A JP2006306870A JP2006110119A JP2006110119A JP2006306870A JP 2006306870 A JP2006306870 A JP 2006306870A JP 2006110119 A JP2006110119 A JP 2006110119A JP 2006110119 A JP2006110119 A JP 2006110119A JP 2006306870 A JP2006306870 A JP 2006306870A
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- -1 Aminostyryl compound Chemical class 0.000 title claims abstract description 115
- 150000001875 compounds Chemical class 0.000 title claims abstract description 70
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 238000002347 injection Methods 0.000 claims description 54
- 239000007924 injection Substances 0.000 claims description 54
- 230000005525 hole transport Effects 0.000 claims description 22
- 230000000903 blocking effect Effects 0.000 claims description 16
- 239000002019 doping agent Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000006267 biphenyl group Chemical group 0.000 claims description 6
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 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 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 125000003828 azulenyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 claims description 4
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000005059 halophenyl group Chemical group 0.000 claims description 4
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 claims description 4
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 4
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000003824 heptacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC7=CC=CC=C7C=C6C=C5C=C4C=C3C=C12)* 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 113
- 230000015572 biosynthetic process Effects 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 18
- 238000004528 spin coating Methods 0.000 description 14
- 229940126062 Compound A Drugs 0.000 description 13
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 11
- 238000001771 vacuum deposition Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 229940125773 compound 10 Drugs 0.000 description 5
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000000103 photoluminescence spectrum Methods 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
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- 238000002411 thermogravimetry Methods 0.000 description 3
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 2
- 0 C*1C=CCC*1 Chemical compound C*1C=CCC*1 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- AIPRAPZUGUTQKX-UHFFFAOYSA-N diethoxyphosphorylmethylbenzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1 AIPRAPZUGUTQKX-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
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- 239000002184 metal Substances 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- MBYOBTPZNDJPCC-UHFFFAOYSA-N (4-phenylphenoxy)boronic acid Chemical compound C1=CC(OB(O)O)=CC=C1C1=CC=CC=C1 MBYOBTPZNDJPCC-UHFFFAOYSA-N 0.000 description 1
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 1
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
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- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 229910052771 Terbium Inorganic materials 0.000 description 1
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- YNCYPMUJDDXIRH-UHFFFAOYSA-N benzo[b]thiophene-2-boronic acid Chemical compound C1=CC=C2SC(B(O)O)=CC2=C1 YNCYPMUJDDXIRH-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- CFSPJNSHRWOAEJ-UHFFFAOYSA-N cyclohexyl(propoxy)borinic acid Chemical compound CCCOB(O)C1CCCCC1 CFSPJNSHRWOAEJ-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- VCJZTATVUDMNLU-UHFFFAOYSA-N dibromomethylbenzene Chemical compound BrC(Br)C1=CC=CC=C1 VCJZTATVUDMNLU-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical compound OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
Description
Ar1及びAr2は、互いに独立して置換または非置換のC6−C30のアリール基、置換または非置換のC2−C30のヘテロアリール基であり、
R1、R2、R3、R4、R5、R6、R7及びR8は、互いに独立して水素原子、置換または非置換のC1−C20のアルキル基または置換または非置換のC1−C20アルコキシ基であり;
nは、1〜3の整数であり、
Lは、置換または非置換のC6−C30のアリール基、置換または非置換のC2−C30のヘテロアリール基、C5−C20のシクロアルキル基またはC5−C30のヘテロシクロアルキル基である
前記本発明の課題を解決するために、本発明の第2態様は、下記化学式1aで表される化合物及び下記化学式1bで表される化合物を反応させて、下記化学式1cで表される化合物を形成する工程と、前記化学式1cで表される化合物及び化学式:L−Qで表される化合物を反応させて、下記化学式1で表される化合物を形成する工程と、を含むアミノスチリル化合物の製造方法を提供する。
ベンジルホスホン酸ジエチルエステル(4.39mmol,1g)をテトラヒドロフラン(100ml)溶媒に溶解させた後、水素化ナトリウム(6.57mmol,0.157g)を添加して50℃で1時間反応させた後、4−(N,N−ジフェニルアミノ)ベンズアルデヒド(3.66mmol,1g)を滴下して、70℃で一日間反応させた後、エタノール(20ml)を添加して真空で乾燥させた後、塩化メチレン(200ml)を添加した。これから集められた有機層を水(50ml)で2回洗浄し、無水硫酸マグネシウムを入れて乾燥させた後、濾過して溶媒部分のみを乾燥させた。その後、シリカゲルカラムクロマトグラフィーで精製して、下記化学式で表される比較化合物A(収率78%)を得た。
下記反応式の反応経路によって化合物2を合成した。
4−臭化ブロモベンジル(12mmol,3g)をP(OCH2CH3)3(18mmol,4.5g)と混合して、185℃で6時間攪拌した。常温まで冷却させて粗生成物を得た後、シリカゲルカラムクロマトグラフィーで分離精製して3.13g(収率85%)の中間体Bを得た。
ベンジルホスホン酸ジエチルエステルの代わりに中間体Bを使用する以外には、比較合成例1と同じ方法で中間体Cを合成及び精製して前記中間体C(収率75%)を得た。
前記中間体C(2.35mmol,1g)、1−ナフタレンボロン酸(2.81mmol,0.48g)、テトラキス(トリフェニルホスフィン)パラジウム(0.12mmol,0.135g)、K2CO3(3.53mmol,0.49g)をトルエン(100mL)及び水(10ml)に溶解させた後、還流温度で48時間攪拌した。常温まで冷却させた後、ジエチルエーテル(100ml)を添加して水(50mL)で2回洗浄し、有機層を集めて無水硫酸マグネシウムで乾燥させた後、溶媒を蒸発させて粗生成物を得た後、シリカゲルカラムクロマトグラフィーで分離精製して0.7g(収率63%)の化合物2を得た。
下記反応式の反応経路によって化合物3を合成した。
下記反応式の反応経路によって化合物4を合成した。
下記反応式の反応経路によって化合物5を合成した。
下記反応式の反応経路によって化合物6を合成した。
下記反応式の反応経路によって化合物7を合成した。
下記反応式の反応経路によって化合物8を合成した。
下記反応式の反応経路によって化合物9を合成した。
下記反応式の反応経路によって化合物10を合成した。
前記化合物2〜10の熱安定性を各化合物のTg(ガラス転移温度)及びTm(融点)を測定することによって評価した。Tg及びTmは、TGA(熱重量分析:Thermo Gravimetric Analysis)及びDSC(示差走査熱量測定:Differential Scanning Calorimetry)を利用した熱分析(N2雰囲気、温度区間:常温〜600℃(10℃/min)−TGA、常温〜400℃−DSC、パン型:使い捨てのAlパン中のPtパン Pan(TGA)、使い捨てのAlパン(DSC))を行って測定した。その結果を下記表1に示す。
比較化合物A及び化合物2〜10の吸収スペクトル及びPL(photoluminescence)スペクトルを評価することによって、各化合物の発光特性を評価した。まず、化合物2をトルエンで0.2mMの濃度に希釈し、島津UV−350スペクトロメーターを利用して吸収スペクトルを測定した。これを化合物3〜10及び比較化合物Aに対して繰り返した。一方、化合物2をトルエンで10mMの濃度に希釈し、キセノンランプが装着されているISC PC1スペクトロフルオロメーターを利用してPLスペクトルを測定した。これを化合物3〜10及び比較化合物Aに対して繰り返した。その結果を下記表2に示す。
比較化合物A及び化合物2〜10のそれぞれとPVKとを混合した混合物でフィルムを形成して、前記フィルムの吸収スペクトル、PLスペクトル及び量子収率を評価した。
比較化合物Aを発光層のドーパントとして使用して、次のような構造を有するOLEDを製作した:ITO/PEDOT−PSS(500Å)/比較化合物A_PVK(480Å)/TAZ(200Å)/LiF(10Å)/Al(2000Å)。
発光層の形成のために、比較化合物Aの代わりに前記合成例1〜合成例9で合成した化合物2〜化合物10をそれぞれ使用した点を除いては、前記比較実施例1と同じ方法でOLEDを製作した。これを各々サンプル2〜サンプル10という。
比較サンプルA及びサンプル2〜サンプル10に対して、PR650(Spectroscan)Source Measurement Unit.を利用して駆動電圧、色純度、効率及び外部量子収率をそれぞれ評価した。
Claims (14)
- 前記アルキル基、アルコキシ基、アリール基、ヘテロアリール基、シクロアルキル基及びヘテロシクロアルキル基の置換基は、−F、−Cl、−Br、−CN、−NO2、−OH;非置換または−F、−Cl、−Br、−CN、−NO2もしくは−OHに置換のC1−C20のアルキル基;非置換または−F、−Cl、−Br、−CN、−NO2または−OHに置換のC1−C20のアルコキシ基;非置換または−F、−Cl、−Br、−CN、−NO2もしくは−OHに置換のC6−C30のアリール基;非置換または−F、−Cl、−Br、−CN、−NO2または−OHに置換のC2−C30のヘテロアリール基;非置換または−F、−Cl、−Br、−CN、−NO2もしくは−OHに置換のC5−C20のシクロアルキル基;及び非置換または−F、−Cl、−Br、−CN、−NO2もしくは−OHに置換のC5−C30のヘテロシクロアルキル基からなる群から選択された一以上であることを特徴とする請求項1に記載のアミノスチリル化合物。
- Ar1及びAr2は、互いに独立して、フェニル基、C1−C10のアルキルフェニル基、C1−C10のアルコキシフェニル基、ハロフェニル基、シアノフェニル基、ジシアノフェニル基、トリフルオロメトキシフェニル基、o−,m−,またはp−トリル基、o−,m−,またはp−クメニル基、メシチル基、フェノキシフェニル基、(α,α−ジメチルベンゼン)フェニル基、(N,N’−ジメチル)アミノフェニル基、(N,N’−ジフェニル)アミノフェニル基、(C1−C10アルキルシクロヘキシル)フェニル基、(アントリル)フェニル基、ビフェニル基、C1−C10アルキルビフェニル基、C1−C10アルコキシビフェニル基、ペンタレニル基、インデニル基、ナフチル基、C1−C10アルキルナフチル基、C1−C10アルコキシナフチル基、ハロナフチル基、シアノナフチル基、ビフェニレニル基、C1−C10アルキルビフェニレニル基、C1−C10アルコキシビフェニレニル基、アントリル基、アズレニル基、へプタレニル基、アセナフチレニル基、フェナレニル基、フルオレニル基、アントラキノリル基、メチルアントリル基、フェナントリル基、トリフェニレニル基、ピレニル基、クリセニル基、エチルクリセニル基、ピセニル基、ペリレニル基、クロロペリレニル基、ペンタフェニル基、ペンタセニル基、テトラフェニレニル基、ヘキサフェニル基、ヘキサセニル基、ルビセニル基、コロネニル基、トリナフチレニル基、へプタフェニル基、へプタセニル基、ピラントレニル基、オバレニル基、カルバゾリル基、C1−10アルキルカルバゾリル基、チオフェニル基、インドリル基、プリニル基、ベンズイミダゾリル基、キノリニル基、ベンゾチオフェニル基、パラチアジニル基、ピロリル基、ピラゾリル基、イミダゾリル基、イミダゾリニル基、オキサゾリル基、チアゾリル基、トリアゾリル基、テトラゾリル基、オキサジアゾリル基、ピリジニル基、ピリダジニル基、ピリミジニル基、ピラジニル基及びチアントレニル基からなる群から選択されたことを特徴とする請求項1または2に記載のアミノスチリル化合物。
- nは、1または2であることを特徴とする請求項1〜3のいずれか1項に記載のアミノスチリル化合物。
- Lは、フェニル基、C1−C10のアルキルフェニル基、C1−C10のアルコキシフェニル基、ハロフェニル基、シアノフェニル基、ジシアノフェニル基、トリフルオロメトキシフェニル基、o−,m−,またはp−トリル基、o−,m−,またはp−クメニル基、メシチル基、フェノキシフェニル基、(α,α−ジメチルベンゼン)フェニル基、(N,N’−ジメチル)アミノフェニル基、(N,N’−ジフェニル)アミノフェニル基、(C1−C10アルキルシクロヘキシル)フェニル基、(アントリル)フェニル基、ビフェニル基、C1−C10アルキルビフェニル基、C1−C10アルコキシビフェニル基、ペンタレニル基、インデニル基、ナフチル基、C1−C10アルキルナフチル基、C1−C10アルコキシナフチル基、ハロナフチル基、シアノナフチル基、ビフェニレニル基、C1−C10アルキルビフェニレニル基、C1−C10アルコキシビフェニレニル基、アントリル基、アズレニル基、へプタレニル基、アセナフチレニル基、フェナレニル基、フルオレニル基、アントラキノリル基、メチルアントリル基、フェナントリル基、トリフェニレニル基、ピレニル基、クリセニル基、エチルクリセニル基、ピセニル基、ペリレニル基、クロロペリレニル基、ペンタフェニル基、ペンタセニル基、テトラフェニレニル基、ヘキサフェニル基、ヘキサセニル基、ルビセニル基、コロネニル基、トリナフチレニル基、へプタフェニル基、へプタセニル基、ピラントレニル基、オバレニル基、カルバゾリル基、C1−C10アルキルカルバゾリル基、チオフェニル基、インドリル基、プリニル基、ベンズイミダゾリル基、キノリニル基、ベンゾチオフェニル基、パラチアジニル基、ピロリル基、ピラゾリル基、イミダゾリル基、イミダゾリニル基、オキサゾリル基、チアゾリル基、トリアゾリル基、テトラゾリル基、オキサジアゾリル基、ピリジニル基、ピリダジニル基、ピリミジニル基、ピラジニル基、チアントレニル基、シクロペンチル基、シクロヘキシル基、C1−C10アルキルシクロヘキシル基、C1−C10アルコキシシクロヘキシル基、オキシラニル基、ピロリジニル基、ピラゾリジニル基、イミダゾリジニル基、ピペリジニル基、ピペラジニル基及びモルホリニル基からなる群から選択されたことを特徴とする請求項1〜4の何れか1項に記載のアミノスチリル化合物。
- 下記化学式1aで表される化合物及び下記化学式1bで表される化合物を反応させて、下記化学式1cで表される化合物を形成する工程と、
前記化学式1cで表される化合物及び化学式:L−Qで表される化合物を反応させて、下記化学式1で表されるアミノスチリル化合物を形成する工程と、
を含むアミノスチリル化合物の製造方法:
Ar1及びAr2は、互いに独立して、置換または非置換のC6−C30のアリール基、置換または非置換のC2−C30のヘテロアリール基であり、
R1、R2、R3、R4、R5、R6、R7及びR8は、互いに独立して水素原子、置換または非置換のC1−C20のアルキル基または置換または非置換のC1−C20のアルコキシ基であり;
nは、1〜3の整数であり、
Lは、置換または非置換のC6−C30のアリール基、置換または非置換のC2−C30のヘテロアリール基、C5−C20のシクロアルキル基またはC5−C30のヘテロシクロアルキル基であり、
Haは、ハロゲン原子であり、
Qは、ホウ素含有基である。 - 第1電極と、第2電極と、前記第1電極及び前記第2電極の間にある有機膜と、を含む有機発光素子であって、前記有機膜は、請求項1〜6のいずれか1項に記載のアミノスチリル化合物を含むことを特徴とする有機発光素子。
- 前記有機膜は、発光層または正孔輸送層の少なくとも一以上であることを特徴とする請求項10に記載の有機発光素子。
- 前記第1電極と第2電極との間に、発光層と、正孔注入層、正孔輸送層、電子阻止層、正孔阻止層、電子輸送層及び電子注入層からなる群から選択された一以上の層とを含むことを特徴とする請求項10または請求項11に記載の有機発光素子。
- 前記素子は、(1)第1電極/正孔注入層/発光層/電子輸送層/電子注入層/第2電極、(2)第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/第2電極または(3)第1電極/正孔注入層/正孔輸送層/発光層/正孔阻止層/電子輸送層/電子注入層/第2電極の構造を有することを特徴とする請求項12に記載の有機発光素子。
- 前記発光層は、赤色、緑色、青色または白色を含む燐光及び赤色、緑色、青色または白色を含む蛍光ドーパントからなる群から選択された一以上を含むことを特徴とする請求項11〜13のいずれか1項に記載の有機発光素子。
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