JPWO2010018858A1 - 有機硫黄化合物およびその製造方法、並びにそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
有機硫黄化合物およびその製造方法、並びにそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- JPWO2010018858A1 JPWO2010018858A1 JP2010524752A JP2010524752A JPWO2010018858A1 JP WO2010018858 A1 JPWO2010018858 A1 JP WO2010018858A1 JP 2010524752 A JP2010524752 A JP 2010524752A JP 2010524752 A JP2010524752 A JP 2010524752A JP WO2010018858 A1 JPWO2010018858 A1 JP WO2010018858A1
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- aromatic hydrocarbon
- represent
- aromatic heterocyclic
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- 150000002898 organic sulfur compounds Chemical class 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 29
- 238000005401 electroluminescence Methods 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 39
- 230000000903 blocking effect Effects 0.000 claims abstract description 25
- -1 boronic acid ester Chemical class 0.000 claims description 42
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052786 argon Inorganic materials 0.000 claims description 8
- 125000002524 organometallic group Chemical group 0.000 claims description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- GBSUYGRWPMYWPG-UHFFFAOYSA-N CC(C)C1=CC=CC(C(C)C)=C1N(C=CN1C=2C(=CC=CC=2C(C)C)C(C)C)C1=[Au]C#CC1=CC=C(C(C)=O)C=C1 Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C=CN1C=2C(=CC=CC=2C(C)C)C(C)C)C1=[Au]C#CC1=CC=C(C(C)=O)C=C1 GBSUYGRWPMYWPG-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 63
- 239000010410 layer Substances 0.000 description 148
- 238000006243 chemical reaction Methods 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000007787 solid Substances 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 230000005525 hole transport Effects 0.000 description 26
- 101000927946 Homo sapiens LisH domain-containing protein ARMC9 Proteins 0.000 description 24
- 102100036882 LisH domain-containing protein ARMC9 Human genes 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 239000011521 glass Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000872 buffer Substances 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000010408 film Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 238000010898 silica gel chromatography Methods 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
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- 239000007983 Tris buffer Substances 0.000 description 13
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000011259 mixed solution Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000002955 isolation Methods 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229910000160 potassium phosphate Inorganic materials 0.000 description 9
- 235000011009 potassium phosphates Nutrition 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- WMKGGPCROCCUDY-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one Chemical compound C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WMKGGPCROCCUDY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- IBHGHNFGHAWRIK-UHFFFAOYSA-N 1,3-dichloro-5-(3,5-dichlorophenyl)sulfonylbenzene Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 IBHGHNFGHAWRIK-UHFFFAOYSA-N 0.000 description 5
- WRXIPCQPHZMXOO-UHFFFAOYSA-N 3,5-dichlorobenzenethiol Chemical compound SC1=CC(Cl)=CC(Cl)=C1 WRXIPCQPHZMXOO-UHFFFAOYSA-N 0.000 description 5
- WNIVWYCXZAGCIC-UHFFFAOYSA-N 3-[3-(3,5-dipyridin-3-ylphenyl)sulfonyl-5-pyridin-3-ylphenyl]pyridine Chemical compound C=1C(C=2C=NC=CC=2)=CC(C=2C=NC=CC=2)=CC=1S(=O)(=O)C(C=1)=CC(C=2C=NC=CC=2)=CC=1C1=CC=CN=C1 WNIVWYCXZAGCIC-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- 125000000101 thioether group Chemical group 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group 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 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 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 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 4
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- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
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- SUFKDKVEYSCWSK-UHFFFAOYSA-N 1-[3,5-bis(3-methylphenyl)phenyl]sulfonyl-3,5-bis(3-methylphenyl)benzene Chemical compound CC1=CC=CC(C=2C=C(C=C(C=2)C=2C=C(C)C=CC=2)S(=O)(=O)C=2C=C(C=C(C=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SUFKDKVEYSCWSK-UHFFFAOYSA-N 0.000 description 3
- IOMRHSGLZAIFFG-UHFFFAOYSA-N 1-[3,5-bis(4-methylphenyl)phenyl]sulfonyl-3,5-bis(4-methylphenyl)benzene Chemical compound C1=CC(C)=CC=C1C1=CC(C=2C=CC(C)=CC=2)=CC(S(=O)(=O)C=2C=C(C=C(C=2)C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C1 IOMRHSGLZAIFFG-UHFFFAOYSA-N 0.000 description 3
- JYJKHXKJEGJOPV-UHFFFAOYSA-N 1-chloro-3,5-diphenylbenzene Chemical compound C=1C(Cl)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JYJKHXKJEGJOPV-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
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- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
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- 125000003944 tolyl group Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
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- QHBZMSRWWIZMHN-UHFFFAOYSA-N 1-[4-(3,5-diphenylphenyl)sulfonylphenyl]sulfonyl-3,5-diphenylbenzene Chemical compound C=1C(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=CC=1S(=O)(=O)C(C=C1)=CC=C1S(=O)(=O)C(C=1)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 QHBZMSRWWIZMHN-UHFFFAOYSA-N 0.000 description 2
- WFXNFQBADKGFLF-UHFFFAOYSA-N 1-[4-[4-(3,5-diphenylphenyl)phenyl]sulfonylphenyl]-3,5-diphenylbenzene Chemical compound C=1C=C(C=2C=C(C=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1S(=O)(=O)C(C=C1)=CC=C1C(C=1)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 WFXNFQBADKGFLF-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
- VQYDFPFSXHGHOD-UHFFFAOYSA-N 2-[4-(1,10-phenanthrolin-2-yl)phenyl]-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C4=CC=C(C=C4)C4=CC=C5C=CC=6C(C5=N4)=NC=CC=6)=CC=C3C=CC2=C1 VQYDFPFSXHGHOD-UHFFFAOYSA-N 0.000 description 2
- ONKCIMOQGCARHN-UHFFFAOYSA-N 3-methyl-n-[4-[4-(3-methylanilino)phenyl]phenyl]aniline Chemical compound CC1=CC=CC(NC=2C=CC(=CC=2)C=2C=CC(NC=3C=C(C)C=CC=3)=CC=2)=C1 ONKCIMOQGCARHN-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
Description
Aは、−S−、−S(O)−または−S(O)2−を表し、
Z1およびZ4は、互いに独立して、置換基を有していてもよい3価の芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、
Z2およびZ3は、互いに独立して、置換基を有していてもよい2価の芳香族炭化水素基または芳香族複素環基を表し、
Ar1、Ar2、Ar3およびAr4は、互いに独立して、置換基を有していてもよい芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、および
nは、0または1であり、2つのnは同一でも異なっていてもよい。)
または、
一般式(b1):
X、X1〜X4はハロゲン、好ましくはCl、BrおよびIから選ばれ、Xは好ましくはCl、BrおよびIであり、X1〜X4は好ましくはClまたはBrを示し、
PおよびP1は、PまたはP1を含む化合物がボロン酸、ボロン酸エステル、または有機金属試薬であるように選択される脱離性の基である。
(ii)出発原料の式(c3)においてAが−S−である化合物を選択して式(c1)(A=−S−)の化合物を合成し、ここで−S−を−S(O)2−に変換して式(c1)(A=−S(O)2−)の化合物を合成し、次に経路に従って式(a1)(A=−S(O)2−)を合成する;または
(iii)出発原料の式(c3)においてAが−S−である化合物を選択して式(c1)(A=−S−)の化合物を合成し、次いで式(a1)(A=−S−)の化合物を合成し、ここで−S−を−S(O)2−に変換して式(a1)(A=−S(O)2−)の化合物を合成する。
X、X1、X2はハロゲン、好ましくはCl、BrおよびIから選ばれ、ここで、m個のXは、同一でも、互いに異なっていてもよく、Xは好ましくはBrまたはIであり、X1およびX2は、好ましくはClまたはBrであり、より好ましくはClである。
(ii)出発原料の式(d3)においてAが−S−である化合物を選択して式(d1)(A=−S−)の化合物を合成し、ここで−S−を−S(O)2−に変換して式(d1)(A=−S(O)2−)の化合物を合成し、次に経路に従って式(b1)(A=−S(O)2−)を合成する;または
(iii)出発原料の式(d3)においてAが−S−である化合物を選択して式(d1)(A=−S−)の化合物を合成し、次いで式(b1)(A=−S−)の化合物を合成し、ここで−S−を−S(O)2−に変換して式(b1)(A=−S(O)2−)の化合物を合成する。
次に本発明の有機エレクトロルミネッセンス素子について説明する。本発明の有機EL素子は、本発明の有機硫黄化合物が、所定の層において使用される以外、公知の材料を使用することができる。
−−ビス(4−(m−ターフェニル−5’−イル)フェニル)スルホンの合成−−
標題化合物を、次のスキームに従って合成した。
1H−NMR(CDCl3,δ(ppm));7.34〜7.56(12H,m)、7.60〜7.92(18H,m)、8.04〜8.14(4H,m)
−−(ビス(m−ターフェニル−5’−イル)スルホンの合成−−
標題化合物を、次のスキームに従って合成した。
1H−NMR(CDCl3,δ(ppm));7.36〜7.53(12H,m)、7.58〜7.70(8H,m)、7.93〜8.00(2H,m)、8.10〜8.23(4H,m)
(3,5−ジフェニルクロロベンゼンの合成)
標題化合物を、次のスキームに従って合成した。
(2−(m−ターフェニル-5’−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボランの合成)
標題化合物を次のスキームに従って合成した。
(ビス(3,5−ジクロロフェニル)スルフィドの合成)
標題化合物を、次のスキームに従って合成した。
(ビス(3,5−ジクロロフェニル)スルホンの合成)
次のスキームに従って標題化合物を合成した。
EI−MS;354(M)、356(M+2)、358(M+4)
(3,5−ジクロロフェニル−3’,5’−ジブロモフェニルスルフィドの合成)
標題化合物を、次のスキームに従って合成した。
(3,5−ジクロロフェニル−3’,5’−ジブロモフェニルスルホンの合成)
標題化合物を次のスキームに従って合成した。
(ビス(3,5−ジ−m−トリルフェニル)スルホンの合成)
標題化合物を、次のスキームに従って合成した。
1H−NMR(CDCl3,δ(ppm));2.39(12H,s)、7.12〜7.50(16H,m)、7.88〜8.00(2H,m)、8.08〜8.20(4H,m)
(ビス(3,5−ジ−p−トリルフェニル)スルホン)の合成)
標題化合物を、次のスキームに従って合成した。
1H−NMR(CDCl3,δ(ppm));2.39(12H,s)、7.20〜7.34(8H,m)、7.46〜7.58(8H,m)、7.86〜7.98(2H,m)、8.08〜8.20(4H,m)
(ビス(3,5−ジ−o−トリルフェニル)スルホン)の合成)
標題化合物を、次のスキームに従って合成した。
1H−NMR(CDCl3,δ(ppm));2.30(12H,s)、7.20〜7.38(16H,m)、7.46〜7.58(2H,m)、7.85〜7.98(4H,m)
(ビス(3,5−ジ−3−ピリジルフェニル)スルホン)の合成)
標題化合物を次のスキームに従って合成した。
1H−NMR(CDCl3,δ(ppm));7.32〜7.50(4H,m)、7.84〜8.02(6H,m)、8.14〜8.28(4H,m)、8.58〜8.72(4H,m)、8.76〜8.92(4H,m)
(ビス(3,5−ジ−4−ピリジルフェニル)スルホン)の合成)
標題化合物を次のスキームに従って合成した。
1H−NMR(CDCl3,δ(ppm));7.45〜7.60(8H,m)、8.00〜8.10(2H,m)、8.24〜8.34(4H,m)、8.66〜8.82(8H,m)
1,3−ビス(3’,5’−ジクロロフェニルチオ)ベンゼンの合成
1,4−ビス(3’,5’−ジクロロフェニルチオ)ベンゼンの合成
1,3−ビス(3’,5’−ジクロロフェニルスルホニル)ベンゼンの合成
1,3−ビス(3’,5’−ジフェニルフェニルスルホニル)ベンゼンの合成
1H−NMR(CDCl3、δ(ppm));8.64(1H,s)、8.25〜7.90(8H,m)、7.75〜7.20(21H,m)
1,4−ビス(3’,5’−ジクロロフェニルスルホニル)ベンゼンの合成
1,4−ビス(3’,5’−ジフェニルフェニルスルホニル)ベンゼンの合成
1H−NMR(CDCl3、δ(ppm));8.18〜8.02(8H,m)、8.00〜7.95(2H,m)、7.68〜7.35(20H,m)
図1に示すように、基板側から、透明基板1、陽極2、バッファ層3、ホール輸送層4、発光層5、ホール阻止層6、電子輸送層7および陰極8の各層を備える有機EL素子を以下の方法により作製した。
BTPS:ビス(m−ターフェニル−5’−イル)スルホン;実施例2で合成したものを使用した。
BTPPS:ビス(4−(m−ターフェニル−5’−イル)フェニル)スルホン;実施例1で合成したものを使用した。
Optoelectronics Technology社(以下、e−Ray社という)製)=98.7:1.3を膜厚20nmで成膜し、さらにEB43(e−Ray社製):EB52(e−Ray社製)を膜厚30nmで成膜して形成した。発光層5の上に、ビス(2−メチル−8−キノリノラート)(p−フェニルフェノラート)アルミニウム(BAlq)を膜厚5nmで成膜し、ホール阻止層6を形成した。
陽極2: ITO(110nm)、
バッファ層3: NS21:MoO3(10nm、80:20)/NS21:MoO3=(20nm、90:10)、
ホール輸送層4: NS21(5nm)、
発光層5: NS21:EY52(20nm、98.7:1.3)/EB43:EB52(30nm、98.8:1.2)、
ホール阻止層6: BAlq(5nm)、
電子輸送層7: BTPS(17nm)/BTPS:Liq(10nm、74:26)、
陰極8: Al(100nm)
である。
素子製造1において、ホール阻止層のBAlqをBTPSとし、電子輸送層中で使用したBTPSに代えて1,4−ジ(1,10−フェナントロリン−2−イル)ベンゼン(DPB)を使用した以外は素子製造例1と同様に素子を作製した。
陽極2: ITO(110nm)、
バッファ層3: NS21:MoO3(10nm、80:20)/NS21:MoO3=(20nm、90:10)、
ホール輸送層4: NS21(5nm)、
発光層5: NS21:EY52(20nm、98.7:1.3)/EB43:EB52(30nm、98.8:1.2)、
ホール阻止層6: BTPS(5nm)、
電子輸送層7: DPB(14nm)/DPB:Liq(10nm、74:26)、
陰極8: Al(100nm)
である。
素子製造例1において、BTPSの代わりにBTPPSを使用した以外は素子製造例1と同様に素子を作成した。
陽極2: ITO(110nm)、
バッファ層3: NS21:MoO3(10nm、80:20)/NS21:MoO3=(20nm、90:10)、
ホール輸送層4: NS21(5nm)、
発光層5: NS21:EY52(20nm、98.7:1.3)/EB43:EB52(30nm、98.8:1.2)、
ホール阻止層6: BAlq(5nm)、
電子輸送層7: BTPPS(17nm)/BTPPS:Liq(10nm、74:26)、
陰極8: Al(100nm)
素子製造例2において、BTPSをBTPPSにした以外は素子製造例2と同様にして素子を作成した。
陽極2: ITO(110nm)、
バッファ層3: NS21:MoO3(10nm、80:20)/NS21:MoO3=(20nm、90:10)、
ホール輸送層4: NS21(5nm)、
発光層5: NS21:EY52(20nm、98.7:1.3)/EB43:EB52(30nm、98.8:1.2)、
ホール阻止層6: BTPPS(5nm)、
電子輸送層7: DPB(14nm)/DPB:Liq(10nm、74:26)、
陰極8: Al(100nm)
図2に示すように、基板側から透明基板11、陽極12、バッファ層13、ホール輸送層14、発光層15、電子輸送層16および陰極17の各層を備える有機EL素子を、素子製造例1と同様にして作製した。
陽極12:ITO(110nm)、
バッファ層13:NS21:MoO3(10nm、80:20)/NS21:MoO3=(20nm、90:10)、
ホール輸送層14:3DTAPBP(20nm)、
発光層15:4−アセチルフェニルエチニル[1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン]金:BTPS(10nm、80:20)、
電子輸送層16:BmPyPB(50nm)/Liq(0.5nm)、
陰極17:Al(100nm)
図2に示す各層を備える有機EL素子を、素子製造例1と同様にして作製した。
陽極12: ITO(110nm)、
バッファ層13: NS21:MoO3(20nm、80:20)、
ホール輸送層14: 3DTAPBP(20nm)、
発光層15: FIrpic:BTPS(4.5nm、20:80)/PQ2Ir(dpm):BTPS(1.0nm、5:95)/FIrpic:BTPS(4.5nm、80:20)、
電子輸送層16: BmPyPB(25nm)/KLET03(47nm)/Liq(1.0nm)、
陰極17: Al(100nm)
素子製造例6においてBTPSをBTPPSに変えた以外は同様にして、下記のように簡略化して示した層構成の素子を作成した。
陽極12: ITO(110nm)、
バッファ層13: NS21:MoO3(20nm、80:20)、
ホール輸送層14: 3DTAPBP(20nm)、
発光層15: FIrpic:BTPPS(4.5nm、20:80)/PQ2Ir(dpm):BTPPS(1.0nm、5:95)/FIrpic:BTPPS(4.5nm、80:20)、
電子輸送層16: BmPyPB(25nm)/KLET03(47nm)/Liq(1.0nm)、
陰極17: Al(100nm)
2 陽極
3 バッファ層
4 ホール輸送層
5 発光層
6 ホール阻止層
7 電子輸送層
8 陰極
11 透明基板
12 陽極
13 バッファ層
14 ホール輸送層
15 発光層
16 電子輸送層
17 陰極
Claims (11)
- 一般式(a1):
Aは、−S−、−S(O)−または−S(O)2−を表し、
Z1およびZ4は、互いに独立して、置換基を有していてもよい3価の芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、
Z2およびZ3は、互いに独立して、置換基を有していてもよい2価の芳香族炭化水素基または芳香族複素環基を表し、
Ar1、Ar2、Ar3およびAr4は、互いに独立して、置換基を有していてもよい芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、および
nは、0または1であり、2つのnは同一でも異なっていてもよい。)
または、
一般式(b1):
Aは、−S−、−S(O)−または−S(O)2−を表し、
Z5は、置換基を有していてもよい3価の芳香族炭化水素基または芳香族複素環基を表し、
Arは、置換基を有していてもよいm価の芳香族炭化水素基または芳香族複素環基を表し、
Ar1およびAr2は、互いに独立して前記一般式(a1)について定義された意味を表し、
mは、2または3であり、
但し、式中にそれぞれm個存在するA、Z5、Ar1、およびAr2は、そのm個の基が互いに同一でも異なっていてもよい。)
で示される有機硫黄化合物。 - 一般式(a1):
Aは、−S−、−S(O)−または−S(O)2−を表し、
Z1およびZ4、互いに独立して、置換基を有していてもよい3価の芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、
Z2およびZ3は、互いに独立して、置換基を有していてもよい2価の芳香族炭化水素基または芳香族複素環基を表し、
Ar1、Ar2、Ar3およびAr4は、互いに独立して、置換基を有していてもよい芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、および
nは、0または1であり、2つのnは同一でも異なっていてもよい。)
で示される化合物の製造方法であって、
一般式(c1):
A、Z1、Z4、Z2、Z3およびnは前記一般式(a1)について定義された意味を表し、
X1、X2、X3およびX4は、互いに独立してハロゲンを表す。)
で示される化合物と、
式Ar1P、Ar2P、Ar3PおよびAr4P
(式中、Ar1、Ar2、Ar3およびAr4は、前記一般式(a1)で定義された意味を表し、Pは、Pを含む化合物がボロン酸、ボロン酸エステル、または有機金属試薬であるように選択される脱離性の基である。)
で示される化合物を反応させることを特徴とする一般式(a1)で示される化合物の製造方法。 - 一般式(a1):
Aは、−S−、−S(O)−または−S(O)2−を表し、
Z1およびZ4、互いに独立して、置換基を有していてもよい3価の芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、
Z2およびZ3は、互いに独立して、置換基を有していてもよい2価の芳香族炭化水素基または芳香族複素環基を表し、
Ar1、Ar2、Ar3およびAr4は、互いに独立して、置換基を有していてもよい芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、および
nは、0または1であり、2つのnは同一でも異なっていてもよい。)
で示される化合物の製造方法であって、
一般式(c4):
A、Z2、Z3およびnは前記一般式(a1)で定義された意味を示し、
Xはハロゲンを表し、2つのXは同一でも異なっていてもよい。)
で示される化合物と、
一般式(c5i)および(c5ii):
Ar1、Ar2、Ar3、Ar4、Z1およびZ4は、前記一般式(a1)で定義された意味を表し、
Pは、Pを含む化合物がボロン酸、ボロン酸エステル、または有機金属試薬であるように選択される脱離性の基である。)
で示される化合物を反応させることを特徴とする一般式(a1)で示される化合物の製造方法。 - 一般式(b1):
Aは、−S−、−S(O)−または−S(O)2−を表し、
Z5は、置換基を有していてもよい3価の芳香族炭化水素基または芳香族複素環基を表し、
Arは、置換基を有していてもよいm価の芳香族炭化水素基または芳香族複素環基を表し、
Ar1およびAr2は、互いに独立して、置換基を有していてもよい芳香族炭化水素基またはカルバゾリル基を除く芳香族複素環基を表し、
mは、2または3であり、
但し、式中にそれぞれm個存在するA、Z5、Ar1、およびAr2は、そのm個の基が互いに同一でも異なっていてもよい。)
で示される化合物の製造方法であって、
一般式(d1):
X1およびX2は、互いに独立してハロゲンを表す。)
で示される化合物と、
式Ar1PおよびAr2P
(式中、Ar1およびAr2は、前記一般式(b1)で定義された意味を表し、Pは、Pを含む化合物がボロン酸、ボロン酸エステル、または有機金属試薬であるように選択される脱離性の基である。)
で示される化合物を反応させることを特徴とする一般式(b1)で示される化合物の製造方法。 - 請求項1〜4のいずれかに記載の有機硫黄化合物を含有することを特徴とする有機エレクトロルミネッセンス素子。
- 電子輸送層、ホール阻止層および発光層から選ばれる少なくとも1つの層に、請求項1〜4のいずれかに記載の有機硫黄化合物を含有することを特徴とする請求項8記載の有機エレクトロルミネッセンス素子。
- 発光層に4−アセチルフェニルエチニル[1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン]金を含む請求項9記載の有機エレクトロルミネッセンス素子。
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JP2012059962A (ja) * | 2010-09-09 | 2012-03-22 | Nippon Seiki Co Ltd | 有機el素子 |
JP5889030B2 (ja) * | 2011-02-14 | 2016-03-22 | 旭化成イーマテリアルズ株式会社 | 多環式芳香族化合物の製造方法 |
CN102394276B (zh) * | 2011-11-25 | 2014-08-27 | 中国科学院长春应用化学研究所 | 红色有机电致发光器件及其制备方法 |
JP6468579B2 (ja) * | 2013-05-10 | 2019-02-13 | 国立大学法人山形大学 | 青色有機エレクトロルミネッセンス素子 |
CN104177285A (zh) * | 2013-05-28 | 2014-12-03 | 海洋王照明科技股份有限公司 | 双极性蓝光磷光主体材料及其制备方法和有机电致发光器件 |
CN103694152A (zh) * | 2013-12-20 | 2014-04-02 | 华南理工大学 | 含多甲基取代苯基悬垂侧基的二氟苯砜化合物及合成方法 |
CN104370837A (zh) * | 2014-11-10 | 2015-02-25 | 天津师范大学 | 硫醚双三唑化合物及其制备方法与应用 |
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JP2004331588A (ja) * | 2003-05-08 | 2004-11-25 | Mitsubishi Chemicals Corp | ピラゾール系化合物、電荷輸送材料、有機電界発光素子材料及び有機電界発光素子 |
WO2005009979A1 (ja) * | 2003-07-28 | 2005-02-03 | Semiconductor Energy Laboratory Co., Ltd. | キノキサリン誘導体及びそれを用いた発光素子 |
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EP2332907A1 (en) | 2011-06-15 |
US8597799B2 (en) | 2013-12-03 |
KR20110043744A (ko) | 2011-04-27 |
CN102186813A (zh) | 2011-09-14 |
CN102186813B (zh) | 2014-12-24 |
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