JP5503124B2 - 芳香族化合物およびこれを含む有機膜を備えた有機発光素子並びにその製造方法 - Google Patents
芳香族化合物およびこれを含む有機膜を備えた有機発光素子並びにその製造方法 Download PDFInfo
- Publication number
- JP5503124B2 JP5503124B2 JP2008190784A JP2008190784A JP5503124B2 JP 5503124 B2 JP5503124 B2 JP 5503124B2 JP 2008190784 A JP2008190784 A JP 2008190784A JP 2008190784 A JP2008190784 A JP 2008190784A JP 5503124 B2 JP5503124 B2 JP 5503124B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- ring
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title description 12
- 150000002894 organic compounds Chemical class 0.000 title 1
- -1 cycloalkynyl group Chemical group 0.000 claims description 320
- 239000000126 substance Substances 0.000 claims description 71
- 238000002347 injection Methods 0.000 claims description 51
- 239000007924 injection Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 47
- 150000001491 aromatic compounds Chemical class 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 230000005525 hole transport Effects 0.000 claims description 23
- 125000003277 amino group Chemical group 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003828 azulenyl group Chemical group 0.000 claims description 5
- 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 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 5
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 229910052800 carbon group element Inorganic materials 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004986 diarylamino group Chemical group 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl 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 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 150000001454 anthracenes Chemical group 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 3
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 claims description 3
- 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 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 3
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- SQFPKRNUGBRTAR-UHFFFAOYSA-N acephenanthrylene Chemical group C1=CC(C=C2)=C3C2=CC2=CC=CC=C2C3=C1 SQFPKRNUGBRTAR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 150000001616 biphenylenes Chemical group 0.000 claims description 2
- 150000001846 chrysenes Chemical group 0.000 claims description 2
- 150000001882 coronenes Chemical group 0.000 claims description 2
- 150000002219 fluoranthenes Chemical group 0.000 claims description 2
- 150000002380 heptalenes Chemical group 0.000 claims description 2
- 150000002396 hexacenes Chemical group 0.000 claims description 2
- PKIFBGYEEVFWTJ-UHFFFAOYSA-N hexaphene Chemical class C1=CC=C2C=C3C4=CC5=CC6=CC=CC=C6C=C5C=C4C=CC3=CC2=C1 PKIFBGYEEVFWTJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- KJKJUXGEMYCCJN-UHFFFAOYSA-N parathiazine Chemical group C12=CC=CC=C2SC2=CC=CC=C2N1CCN1CCCC1 KJKJUXGEMYCCJN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002964 pentacenes Chemical group 0.000 claims description 2
- 150000002968 pentalenes Chemical group 0.000 claims description 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
- 150000002979 perylenes Chemical group 0.000 claims description 2
- 150000002985 phenalenes Chemical group 0.000 claims description 2
- 150000003039 picenes 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
- LNKHTYQPVMAJSF-UHFFFAOYSA-N pyranthrene Chemical group C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 LNKHTYQPVMAJSF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003217 pyrazoles Chemical group 0.000 claims description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- FMKFBRKHHLWKDB-UHFFFAOYSA-N rubicene Chemical group C12=CC=CC=C2C2=CC=CC3=C2C1=C1C=CC=C2C4=CC=CC=C4C3=C21 FMKFBRKHHLWKDB-UHFFFAOYSA-N 0.000 claims description 2
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 claims description 2
- 150000003536 tetrazoles Chemical group 0.000 claims description 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical group C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003852 triazoles Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000002467 indacenes Chemical group 0.000 claims 1
- 150000003220 pyrenes Chemical group 0.000 claims 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 126
- 238000000034 method Methods 0.000 description 61
- 239000000463 material Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 229940126214 compound 3 Drugs 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000004528 spin coating Methods 0.000 description 16
- 238000001771 vacuum deposition Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 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
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 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 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 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 4
- 238000007740 vapor deposition Methods 0.000 description 4
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 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 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- OJLABXSUFRIXFL-UHFFFAOYSA-N (2-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 OJLABXSUFRIXFL-UHFFFAOYSA-N 0.000 description 1
- PLVCYMZAEQRYHJ-UHFFFAOYSA-N (2-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Br PLVCYMZAEQRYHJ-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- 125000005923 1,2-dimethylpropyloxy group Chemical group 0.000 description 1
- CMIMBQIBIZZZHQ-UHFFFAOYSA-N 1-bromo-2-methylnaphthalene Chemical compound C1=CC=CC2=C(Br)C(C)=CC=C21 CMIMBQIBIZZZHQ-UHFFFAOYSA-N 0.000 description 1
- ZJMLAQRBTXWRIO-UHFFFAOYSA-N 1-bromo-8-(2-bromophenyl)naphthalene Chemical compound BrC1=CC=CC=C1C1=CC=CC2=CC=CC(Br)=C12 ZJMLAQRBTXWRIO-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006607 3,3-dimethylbutyloxy group Chemical group 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006032 3-methyl-3-butenyl group Chemical group 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
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- SLHKDOGTVUCXKX-UHFFFAOYSA-N 4,4'-biphenyldiboronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=C(B(O)O)C=C1 SLHKDOGTVUCXKX-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- 125000000439 4-methylpentoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 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
- RULVBMDEPWAFIN-UHFFFAOYSA-N 6,12-dibromochrysene Chemical compound C1=CC=C2C(Br)=CC3=C(C=CC=C4)C4=C(Br)C=C3C2=C1 RULVBMDEPWAFIN-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 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
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- GRADOOOISCPIDG-UHFFFAOYSA-N buta-1,3-diyne Chemical group [C]#CC#C GRADOOOISCPIDG-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 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
- 239000003054 catalyst Substances 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RFBZWPFBCXBBJS-UHFFFAOYSA-N ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1B1OC(C)(C)C(C)(C)O1 RFBZWPFBCXBBJS-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 125000003427 indacenyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical group CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 125000005033 thiopyranyl group Chemical group 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
-
- 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
-
- 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
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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
-
- 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
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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]
- H10K50/18—Carrier blocking layers
-
- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
下記反応式1〜3の合成経路によって化合物3を合成した。
テトラヒドロフラン(THF)(110ml)に9,10−ジブロモアントラセン 9.1g(27.2mmol)を溶かした。次いで、中間体A 7.5g(27.2mmol)、テトラキストリフェニルホスフィンパラジウム(Pd(PPh3)4) 1.57g(1.4mmol)および炭酸カリウム(K2CO3)1.5g(109mmol)をそれぞれトルエン55mlおよび水55mlに溶解させて添加し、24時間還流させた。反応が完結した後、溶媒を蒸発させて除去した。次いで、酢酸エチル500mlおよび水500mlをそれぞれ添加して洗浄した後、有機層を回収して無水硫酸マグネシウムで乾燥させた。次いで、シリカゲルクロマトグラフィで分離して、前記反応式1中の中間体Bで表される化合物を2.9g(収率26%)得た。なお、中間体Aは、エチル2−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ベンゾエート(ethyl 2−(4,4,5,5−tetramethyl−1,3,2−dioxaborolan−2−yl)benzoate)であり、例えばAldrich社から入手することができる。
THF(48ml)に中間体B 2.0g(4.9mmol)を溶かした。次いで、4,4’−ビフェニルジボロン酸409g(2.5mmol)、テトラキストリフェニルホスフィンパラジウム(Pd(PPh3)4) 290mg(0.25mmol)および炭酸カリウム(K2CO3) 3.4mg(24.7mmol)をそれぞれトルエン12mlおよび水12.5mlに溶解させて添加し、24時間還流させた。反応が完結した後、溶媒を蒸発させて除去した。次いで、酢酸エチル200mlおよび水200mlをそれぞれ添加して洗浄した後、有機層を回収して無水硫酸マグネシウムで乾燥させた。次いで、シリカゲルクロマトグラフィで分離して、前記反応式2中の中間体Cで表される化合物を1.4g(収率77%)得た。
THF(4ml)に中間体C 129mg(0.2mmol)を溶かした後、メチル臭化マグネシウム(MeMgBr 3.0M、0.3ml)を添加して温度を70℃に上げた後、1時間攪拌した。反応が完結した後、水10mlと酢酸エチルとを10mlをそれぞれ添加して洗浄した後、有機層を回収して無水硫酸マグネシウムで乾燥させた。有機層を減圧条件で乾燥させた後、これから得られた固体を塩化メチレン4mlに溶かした後、三フッ化ホウ素−ジエチルエーテル錯体0.2mlを添加して30分間攪拌した。メタノール1mlを添加して反応を終結させた後、塩化メチレン10mlと水10mlとをそれぞれ添加して洗浄した後、有機層を回収して無水硫酸マグネシウムで乾燥させた。次いで、シリカゲルクロマトグラフィで分離して化合物3を100mg(収率75%)得た。
下記反応式4の合成経路によって化合物10を合成した。
下記反応式5〜7の合成経路によって化合物13を合成した。
下記反応式8および9の合成経路によって化合物26を合成した。
前記化合物3、13、10および26のUV吸収スペクトルおよび発光(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3をトルエンで0.2mMの濃度になるよう溶解させ、島津製作所社製UV−350スペクトロメーターを利用してUV吸収スペクトルを測定した。これを化合物10、13および26について化合物3と同様に測定した。一方、化合物3をトルエンに10mM濃度になるように溶解させて、キセノンランプ付きのISC PC1スペクトロフルオロメーターを利用して、発光スペクトルを測定した。これを化合物10、13および26について化合物3と同様に測定した。その結果を下記の表5に示す。特に、化合物3のUV吸収スペクトルおよび発光スペクトルは図2に示した。また、化合物3のガラス転移温度Tgは、174℃であった。
化合物3を発光層のドーパントとして使用し、ADNを発光層のホストとして使用して、次のような構造を持つOLEDを製作した:ITO/α−NPD(75nm)/化合物3(5質量%)+ADN(35nm)/Alq3(18nm)/LiF(1nm)/Al(200nm)。
実施例1のうち、化合物3の代わりに化合物10を使用した点を除いては、実施例1のOLEDの製造方法と同様の方法によりOLEDを製作した。これをサンプル2とした。
実施例1のうち、化合物3の代わりに化合物13を使用した点を除いては、実施例1のOLEDの製造方法と同様の方法によりOLEDを製作した。これをサンプル3とした。
実施例1のうち、化合物3の代わりに化合物26を使用した点を除いては、実施例1のOLEDの製造方法と同様の方法によりOLEDを製作した。これをサンプル4とした。
実施例1のうち、化合物3の代わりに下記化合物27を使用した点を除いては、前記実施例1のOLEDの製造方法と同様の方法を利用してOLEDを製作した。これをサンプルAとする。
サンプル1〜4およびAに対して、PR650Spectroscan測定装置を使用して、駆動電圧、輝度、効率をそれぞれ評価し、その結果を下記の表2に示した。特に、サンプル1の電圧−効率グラフは図3に示した。
12 正孔注入層、
13 正孔輸送層、
14 発光層、
15 正孔阻止層
16 電子輸送層、
18 電子注入層、
20 第2電極。
Claims (11)
- 下記化学式1で表される芳香族化合物:
Bは、置換若しくは非置換のC1〜C60アルキレン基、置換若しくは非置換のC5〜C60シクロアルキレン基、置換若しくは非置換のC5〜C60ヘテロシクロアルキレン基、置換若しくは非置換のC6〜C60アリーレン基、置換若しくは非置換のC2〜C60ヘテロアリーレン基、−N(Z1)−で表される2価の基、この際、Z1は、水素原子、置換若しくは非置換のC1〜C60アルキル基、置換若しくは非置換のC6〜C60アリール基であり、
nは、1〜10の整数であり、nが2以上の場合にはBは互いに同一でも異なってもよく、
M1およびM2は互いに独立して、下記化学式2で表される化合物から誘導された末端基であり:
Xは14族元素であり、
R1、R2、R3、R4、R5、R6、R7、R21およびR22は互いに独立して、水素原子、ハロゲン原子、シアノ基、アミノ基、ニトロ基、ヒドロキシル基、置換または非置換のC1〜C60アルキル基、置換または非置換のC1〜C60アルコキシ基、置換または非置換のC2〜C60アルケニル基、置換または非置換のC2〜C60アルキニル基、置換または非置換のC5〜C60シクロアルキル基、置換または非置換のC5〜C60シクロアルケニル基、置換または非置換のC5−C60シクロアルキニル基、置換または非置換のC6〜C60アリール基、置換または非置換のC2〜C60ヘテロアリール基、置換または非置換のC6〜C60モノアリールアミノ基、置換または非置換のC6〜C60ジアリールアミノ基、置換または非置換のC1〜C60モノアルキルアミノ基、置換または非置換のC1〜C60ジアルキルアミノ基、置換または非置換のC6〜C60モノアリールシリル基、置換または非置換のC6〜C60ジアリールシリル基、置換または非置換のC6〜C60トリアリールシリル基、置換または非置換のC1〜C60モノアルキルシリル基、置換または非置換のC1〜C60ジアルキルシリル基、および、置換または非置換のC1〜C60トリアルキルシリル基のいずれかであり、前記R 2 、R3、R4、R5、R6、およびR7、R21およびR22のうち、2つ以上は互いに結合または縮合して、置換若しくは非置換のC6〜C60芳香族環または置換若しくは非置換のC6〜C60芳香族複素環を形成でき、
A1は、置換若しくは非置換のC6〜C60芳香族環または置換若しくは非置換のC6〜C60芳香族複素環である。 - 前記Bで用いられるアルキレン基、シクロアルキレン基、ヘテロシクロアルキレン基、アリーレン基およびヘテロアリーレン基、並びに、前記R1、R2、R3、R4、R5、R6、R7、R21およびR22のアルキル基、アルコキシ基、アルケニル基、アルキニル基、シクロアルキル基、シクロアルケニル基、シクロアルキニル基、アリール基およびヘテロアリール基の置換基は、フッ素原子、;塩素原子;臭素原子;シアノ基;ニトロ基;アミノ基;水酸基;非置換の、または、C1〜C60アルコキシ基、フッ素原子、塩素原子、臭素原子、シアノ基、ニトロ基、アミノ基若しくは水酸基で置換されたC1〜C60アルキル基;非置換の、または、C1〜C60アルキル基、C1〜C60アルコキシ基、フッ素原子、塩素原子、臭素原子、シアノ基、ニトロ基、アミノ基若しくは水酸基で置換されたC5〜C60シクロアルキル基;非置換の、または、C1〜C60アルキル基、C1〜C60アルコキシ基、フッ素原子、塩素原子、臭素原子、シアノ基、ニトロ基、アミノ基若しくは水酸基で置換されたC6〜C60アリール基;および非置換の、またはC1〜C60アルキル基、C1〜C60アルコキシ基、フッ素原子、塩素原子、臭素原子、シアノ基、ニトロ基、アミノ基若しくは水酸基で置換されたC2〜C60ヘテロアリール基からなる群から選択された一つ以上であることを特徴とする請求項1に記載の芳香族化合物。
- 前記Bは、置換若しくは非置換のC1〜C10アルキレン基、置換若しくは非置換のC5〜C22シクロアルキレン基、置換若しくは非置換のC5〜C22ヘテロシクロアルキレン基、置換若しくは非置換のC6〜C22アリーレン基、置換若しくは非置換のC2〜C22ヘテロアリーレン基、または−N(Z1)−で表される2価の基であり、この際、Z1は、水素原子、置換若しくは非置換のC1〜C10アルキル基、置換若しくは非置換のC6〜C22アリール基であることを特徴とする請求項1または2に記載の芳香族化合物。
- 前記Xは、炭素原子、ケイ素原子またはゲルマニウム原子であることを特徴とする請求項1〜3のいずれか一項に記載の芳香族化合物。
- 前記A1は、置換または非置換のベンゼン環、置換または非置換のペンタレン環、置換または非置換のインデン環、置換または非置換のナフタレン環、置換または非置換のアズレン環、置換または非置換のヘプタレン環、置換または非置換のビフェニレン環、置換または非置換のインダセン環、置換または非置換のアセナフチレン環、置換または非置換のフルオレン環、置換または非置換のフェナレン環、置換または非置換のフェナントレン環、置換または非置換のアントラセン環、置換または非置換のフルオランテン環、置換または非置換のアセフェナントリレン環、置換または非置換のアセアントリレン環、置換または非置換のトリフェニレン環、置換または非置換のピレン環、置換または非置換のクリセン環、置換または非置換のナフタセン環、置換または非置換のピセン環、置換または非置換のペリレン環、置換または非置換のペンタフェン環、置換または非置換のペンタセン環、置換または非置換のテトラフェニレン環、置換または非置換のヘキサフェン環、置換または非置換のヘキサセン環、置換または非置換のルビセン環、置換または非置換のコロネン環、置換または非置換のピラントレン環、置換または非置換のオバレン環、置換または非置換のチオフェン環、置換または非置換のインドール環、置換または非置換のフラン環、置換または非置換のベンゾチオフェン環、置換または非置換のパラチアジン環、置換または非置換のベンゾフラン環、置換または非置換のピロール環、置換または非置換のピラゾール環、置換または非置換のイミダゾール環、置換または非置換のイミダゾリン環、置換または非置換のオキサゾール環、置換または非置換のチアゾール環、置換または非置換のトリアゾール環、置換または非置換のテトラゾール環、置換または非置換のオキサジアゾール環、置換または非置換のピリジン環、置換または非置換のピリダジン環、置換または非置換のピラジン環、置換または非置換のピリミジン環、置換または非置換のベンズイミダゾール環、置換または非置換のキノリン環、置換または非置換のフェノチアジン環、および置換または非置換のチアントレン環のいずれかであることを特徴とする請求項1〜4のいずれか一項に記載の芳香族化合物。
- 前記R1、R2、R3、R4、R5、R6、R7、R21およびR22は、互いに独立して、水素原子、C1〜C60アルキル基、C2〜C60アルケニル基、C2〜C60アルキニル基、C5〜C60シクロアルキル基、C5〜C60シクロアルケニル基、C5〜C60シクロアルキニル基、フェニル基、ビフェニル基、ペンタレニル基、インデニル基、ナフチル基、ビフェニレニル基、アントラセニル基、アズレニル基、ヘプタレニル基、アセナフチレニル基、フェナレニル基、フルオレニル基、メチルアントリル基、フェナントレニル基、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、ヘプタフェニル基、ヘプタセニル基、ピラントレニル基、オバレニル基、カルバゾリル基、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、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、モルホリニル基、ジ(C6〜C60アリール)アミノ基、トリ(C6〜C60アリール)シリル基、ジフェニルアミノフェニル基、ジトリルアミノフェニル基およびこれらの誘導体基からなる群から選択されたことを特徴とする請求項1〜5のいずれか一項に記載の芳香族化合物。
- 前記化学式2で表される化合物が、下記化学式2a、2bまたは2cであることを特徴とする請求項1〜6のいずれか一項に記載の芳香族化合物:
Xは14族元素であり、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R21およびR22は、互いに独立して、水素原子、ハロゲン原子、シアノ基、アミノ基、ニトロ基、ヒドロキシル基、置換または非置換のC1〜C60アルキル基、置換または非置換のC1〜C60アルコキシ基、置換または非置換のC2〜C60アルケニル基、置換または非置換のC2〜C60アルキニル基、置換または非置換のC5〜C60シクロアルキル基、置換または非置換のC5〜C60シクロアルケニル基、置換または非置換のC5〜C60シクロアルキニル基、置換または非置換のC6〜C60アリール基、置換または非置換のC2〜C60ヘテロアリール基、置換または非置換のC6〜C60モノアリールアミノ基、置換または非置換のC6〜C60ジアリールアミノ基、置換または非置換のC1〜C60モノアルキルアミノ基、置換または非置換のC1〜C60ジアルキルアミノ基、置換または非置換のC6〜C60モノアリールシリル基、置換または非置換のC6〜C60ジアリールシリル基、置換または非置換のC6〜C60トリアリールシリル基、置換または非置換のC1〜C60アルキルシリル基、置換または非置換のC1〜C60ジアルキルシリル基、および、置換または非置換のC1〜C60トリアルキルシリル基のいずれかであり、前記R 2 、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R21およびR22のうち、2つ以上は互いに結合または縮合して、置換若しくは非置換のC6〜C60芳香族環または置換若しくは非置換のC6〜C60芳香族複素環を形成していてもよい。 - 前記化学式2で表される化合物から誘導された末端基は、下記化学式4で表される基からなる群から選択される少なくとも1つであることを特徴とする請求項1〜7のいずれか一項に記載の芳香族化合物:
- 下記化合物からなる群から選択される少なくとも1つであることを特徴とする請求項1〜8のいずれか一項に記載の芳香族化合物:
- 第1電極と、
第2電極と、
前記第1電極と前記第2電極との間に請求項1〜9のいずれか一項に記載の芳香族化合物を含む有機膜と、
を備えた有機発光素子。 - 前記有機膜は、発光層、正孔注入層、正孔輸送層、正孔阻止層または電子輸送層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。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020070074126A KR101453872B1 (ko) | 2007-07-24 | 2007-07-24 | 방향족 화합물 및 이를 포함한 유기막을 구비한 유기 발광소자 |
KR10-2007-0074126 | 2007-07-24 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009062362A JP2009062362A (ja) | 2009-03-26 |
JP2009062362A5 JP2009062362A5 (ja) | 2011-09-08 |
JP5503124B2 true JP5503124B2 (ja) | 2014-05-28 |
Family
ID=40294676
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008190784A Expired - Fee Related JP5503124B2 (ja) | 2007-07-24 | 2008-07-24 | 芳香族化合物およびこれを含む有機膜を備えた有機発光素子並びにその製造方法 |
Country Status (3)
Country | Link |
---|---|
US (1) | US20090026930A1 (ja) |
JP (1) | JP5503124B2 (ja) |
KR (1) | KR101453872B1 (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008280331A (ja) * | 2007-04-11 | 2008-11-20 | Chisso Corp | ジベンゾフェナレン化合物、発光素子用材料及びそれを用いた有機電界発光素子 |
JP5473600B2 (ja) * | 2007-07-07 | 2014-04-16 | 出光興産株式会社 | クリセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US9153790B2 (en) * | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
KR101324785B1 (ko) * | 2011-02-22 | 2013-10-31 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
KR102050484B1 (ko) | 2013-03-04 | 2019-12-02 | 삼성디스플레이 주식회사 | 안트라센 유도체 및 이를 포함하는 유기전계발광소자 |
KR102107106B1 (ko) | 2013-05-09 | 2020-05-07 | 삼성디스플레이 주식회사 | 스티릴계 화합물 및 이를 포함한 유기 발광 소자 |
US9425416B2 (en) | 2013-06-07 | 2016-08-23 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
KR102269131B1 (ko) | 2013-07-01 | 2021-06-25 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
KR101627754B1 (ko) | 2013-07-11 | 2016-06-07 | 제일모직 주식회사 | 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치 |
KR102191990B1 (ko) | 2013-09-10 | 2020-12-17 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102291490B1 (ko) * | 2013-12-12 | 2021-08-23 | 삼성디스플레이 주식회사 | 아민계 화합물 및 이를 포함한 유기 발광 소자 |
US10062850B2 (en) * | 2013-12-12 | 2018-08-28 | Samsung Display Co., Ltd. | Amine-based compounds and organic light-emitting devices comprising the same |
KR102220425B1 (ko) * | 2014-03-10 | 2021-02-26 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
KR20150132795A (ko) | 2014-05-16 | 2015-11-26 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102261640B1 (ko) | 2014-05-19 | 2021-06-08 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102360091B1 (ko) | 2014-12-31 | 2022-02-09 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102343145B1 (ko) | 2015-01-12 | 2021-12-27 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102642200B1 (ko) | 2016-01-25 | 2024-03-05 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102577003B1 (ko) | 2016-06-03 | 2023-09-12 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102090364B1 (ko) * | 2017-04-10 | 2020-03-17 | 주식회사 엘지화학 | 안트라센 유도체 및 이를 이용한 유기 발광 소자 |
CN107698490B (zh) * | 2017-09-04 | 2020-12-22 | 奥来德(上海)光电材料科技有限公司 | 一种有机发光化合物及其制备方法和应用 |
CN112397675B (zh) * | 2020-11-18 | 2022-07-22 | 合肥维信诺科技有限公司 | 显示面板制备方法及显示面板 |
KR102625596B1 (ko) * | 2021-06-07 | 2024-01-18 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4356429A (en) * | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
KR100577179B1 (ko) * | 2001-10-30 | 2006-05-10 | 엘지전자 주식회사 | 유기 전계 발광 소자 |
JP4127095B2 (ja) * | 2003-03-27 | 2008-07-30 | セイコーエプソン株式会社 | 半導体装置の製造方法 |
JP4280617B2 (ja) * | 2003-12-11 | 2009-06-17 | キヤノン株式会社 | 有機発光素子 |
JP4533015B2 (ja) * | 2004-06-15 | 2010-08-25 | キヤノン株式会社 | 化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2006011879A1 (en) | 2004-06-30 | 2006-02-02 | Eastman Kodak Company | Process for forming an aromatic amine compound |
KR100700430B1 (ko) * | 2005-01-04 | 2007-03-27 | 네오뷰코오롱 주식회사 | 안트라센계 유기 발광 화합물 및 이를 포함하는 유기 발광다이오드 |
JP4865258B2 (ja) | 2005-06-21 | 2012-02-01 | キヤノン株式会社 | 1,8−ナフチリジン化合物及びそれを用いた有機発光素子 |
KR100788254B1 (ko) | 2005-08-16 | 2007-12-27 | (주)그라쎌 | 녹색 발광 화합물 및 이를 발광재료로서 채용하고 있는발광소자 |
DE112006003090T5 (de) * | 2005-11-11 | 2008-09-25 | Sumitomo Chemical Co. Ltd. | Konjugierte Polymerverbindung und polymere lichtemittierende Vorrichtung unter deren Verwendung |
-
2007
- 2007-07-24 KR KR1020070074126A patent/KR101453872B1/ko active IP Right Grant
-
2008
- 2008-03-28 US US12/078,334 patent/US20090026930A1/en not_active Abandoned
- 2008-07-24 JP JP2008190784A patent/JP5503124B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR101453872B1 (ko) | 2014-10-23 |
JP2009062362A (ja) | 2009-03-26 |
US20090026930A1 (en) | 2009-01-29 |
KR20090010763A (ko) | 2009-01-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5503124B2 (ja) | 芳香族化合物およびこれを含む有機膜を備えた有機発光素子並びにその製造方法 | |
JP5363710B2 (ja) | 有機発光性化合物およびこれを備えた有機電界発光素子 | |
JP4620079B2 (ja) | シラニルアミン系化合物、その製造方法及びそれを含む有機膜を備えた有機発光素子 | |
JP5518308B2 (ja) | フェニルフェノキサジン系化合物またはフェニルフェノチアジン系化合物およびこれを利用した有機電界発光素子 | |
JP5557984B2 (ja) | 燐光単位および蛍光単位を含む発光高分子ならびにこれを含む有機発光素子 | |
JP5449643B2 (ja) | オルガノシロキサン化合物及びこれを含む有機発光素子 | |
KR101462535B1 (ko) | 인덴 유도체 화합물 및 이를 이용한 유기 발광 소자 | |
JP5160046B2 (ja) | 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 | |
JP2007084828A (ja) | 有機発光化合物及びこれを備えた有機発光素子 | |
JP5937795B2 (ja) | デンドリマー及びこれを用いた有機発光素子 | |
JP2008133277A (ja) | イミダゾピリジン系化合物、及びこれを含んだ有機膜を具備した有機発光素子 | |
JP2013035839A (ja) | カルバゾール系化合物及び有機発光素子 | |
KR20140035692A (ko) | 포스핀 옥사이드계 화합물 및 이를 포함한 유기 발광 소자 | |
JP2011080066A (ja) | 高分子及びこれを含む有機発光素子 | |
JP4787277B2 (ja) | イミダゾピリミジン系化合物及びそれを含む有機膜を備えた有機発光素子 | |
JP5873265B2 (ja) | デンドリマー及びこれを用いた有機発光素子 | |
KR20070034430A (ko) | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 | |
JP7329324B2 (ja) | 化合物、組成物、液状組成物、有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子 | |
KR20140102088A (ko) | 유기금속 착체 및 이를 포함한 유기 발광 소자 | |
KR20090098588A (ko) | 신규한 유기 화합물 및 이를 이용한 유기 발광 소자 | |
JP2007314530A (ja) | ジアリールエテン系誘導体、これを使用して製造された有機電界発光素子及び該有機電界発光素子の製造方法 | |
JP2015127375A (ja) | フルオレン−トリフェニルアミン共重合体、組成物、液状組成物、薄膜、素子、面状光源装置及び表示装置 | |
CN115521242A (zh) | 有机化合物和电子元件及电子装置 | |
JP5306583B2 (ja) | シクロヘキサン誘導体、その製造方法、及びそれを具備した有機発光素子 | |
JP7359545B2 (ja) | 化合物、それを含む組成物、および該組成物を含む有機エレクトロルミネッセンス素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20100203 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20100304 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20100308 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110722 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110722 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120614 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20120912 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121107 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20121213 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130625 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130627 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130924 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140218 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140314 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5503124 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |