KR20100012808A - 전자 소자용 화합물 - Google Patents
전자 소자용 화합물 Download PDFInfo
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- KR20100012808A KR20100012808A KR1020090057711A KR20090057711A KR20100012808A KR 20100012808 A KR20100012808 A KR 20100012808A KR 1020090057711 A KR1020090057711 A KR 1020090057711A KR 20090057711 A KR20090057711 A KR 20090057711A KR 20100012808 A KR20100012808 A KR 20100012808A
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- KR
- South Korea
- Prior art keywords
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- group
- compound
- aromatic
- substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 114
- 125000003118 aryl group Chemical group 0.000 claims abstract description 93
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 33
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims abstract description 10
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 50
- 239000000463 material Substances 0.000 claims description 45
- -1 NR 3 Inorganic materials 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 27
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 26
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 239000000412 dendrimer Substances 0.000 claims description 18
- 229920000736 dendritic polymer Polymers 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 150000007942 carboxylates Chemical group 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- KHNYNFUTFKJLDD-UHFFFAOYSA-N Benzo[j]fluoranthene Chemical compound C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005577 anthracene group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 2
- RAASUWZPTOJQAY-UHFFFAOYSA-N Dibenz[a,c]anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C3=CC=CC=C3C2=C1 RAASUWZPTOJQAY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 235000012054 meals Nutrition 0.000 claims description 2
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 238000005401 electroluminescence Methods 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 150000003254 radicals Chemical group 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000006872 improvement Effects 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 125000005504 styryl group Chemical group 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000004986 diarylamino group Chemical group 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical group C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- ULWORHXYSIFJLN-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)-2-naphthalen-1-yl-5-pyren-1-ylphenyl]propan-2-ol Chemical compound C1=CC=C2C(C3=CC(=C(C=4C5=CC=C6C=CC=C7C=CC(C5=C76)=CC=4)C=C3C(C)(O)C)C(C)(C)O)=CC=CC2=C1 ULWORHXYSIFJLN-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- HUOFGNUAVGKVDA-UHFFFAOYSA-N diethyl 2-chloro-5-naphthalen-1-ylbenzene-1,4-dicarboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(C=2C3=CC=CC=C3C=CC=2)=C1C(=O)OCC HUOFGNUAVGKVDA-UHFFFAOYSA-N 0.000 description 2
- AUWAVTOWGKXNNK-UHFFFAOYSA-N diethyl 2-chloro-5-pyren-1-ylbenzene-1,4-dicarboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)=C1C(=O)OCC AUWAVTOWGKXNNK-UHFFFAOYSA-N 0.000 description 2
- WHFLYJCKDUDLBK-UHFFFAOYSA-N diethyl 2-naphthalen-1-yl-5-pyren-1-ylbenzene-1,4-dicarboxylate Chemical compound C1=C2C(C=3C=C(C(=CC=3C(=O)OCC)C=3C4=CC=CC=C4C=CC=3)C(=O)OCC)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WHFLYJCKDUDLBK-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
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- 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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Abstract
Description
Claims (19)
- 화학식 (1)의 화합물:[화학식 1][식 중, 사용된 기호 및 지수에 하기의 정의가 적용됨:Ar1, Ar2, Ar3 은 각각의 경우, 동일 또는 상이하게, 하나 이상의 라디칼 R1로 치환될 수 있는, 5 내지 30개 방향족 고리 원자를 가지는 아릴 또는 헤테로아릴기이고, 단 Ar2는 안트라센, 나프타센 또는 펜타센을 나타내지 않고;X 는 각각의 경우, 동일 또는 상이하게, BR2, C(R2)2, Si(R2)2, C=O, C=NR2, C=C(R2)2, O, S, S=O, SO2, NR2, PR2, P(=O)R2 및 P(=S)R2에서 선택되는 기이고;R1, R2 는 각각의 경우, 동일 또는 상이하게, H, D, F, Cl, Br, I, N(Ar4)2, C(=O)Ar4, P(=O)(Ar4)2, S(=O)Ar4, S(=O)2Ar4, CR2=CR2Ar4, CHO, CR3=C(R3)2, CN, NO2, Si(R3)3, B(OR3)2, B(R3)2, B(N(R3)2)2, OSO2R3, 1 내지 40개 탄소 원자를 가지는 직쇄형 알킬, 알콕시 또는 티오알콕시기, 또는 2 내지 40개 탄소 원자를 가지는 직쇄형 알케닐, 알키닐기, 또는 3 내지 40개 탄소 원자를 가지는 분지형 또는 환형 알킬, 알케닐, 알키닐, 알콕시 또는 티오알콕시기이고, 각각은 하나 이상의 라디칼 R3에 의해 치환될 수 있으며, 각각의 경우 하나 이상의 비인접한 CH2기가 R3C=CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C=O, C=S, C=Se, C=NR3, P(=O)R3, SO, SO2, NR3, O, S 또는 CONR3으로 대체될 수 있고, 하나 이상의 H 원자가 F, Cl, Br, I, CN 또는 NO2, 또는 5 내지 60개 방향족 고리 원자를 가지는 방향족 또는 헤테로방향족 고리계로 대체될 수 있는데, 각각의 경우 하나 이상의 라디칼 R3 또는 이러한 계의 조합으로 치환될 수 있고; 여기서의 둘 이상의 치환기 R1 또는 R2는 또한 다른 하나와 함께 단일환- 또는 다중환, 지방족 또는 방향족 고리계를 형성할 수 있고;R3 은 각각의 경우, 동일 또는 상이하게, H, D 또는 1 내지 20개 탄소 원자를 가지는 지방족 또는 방향족 탄화수소 라디칼이고;Ar4 는 각각의 경우, 동일 또는 상이하게, 5 내지 30개 방향족 고리 원자를 가지는 방향족 또는 헤테로방향족 고리계이고, 이는 하나 이상의 비방향족 라디칼 R1 로 치환될 수 있고; 동일 질소 또는 인 원자 상의 두개의 라디칼 Ar 은 서로 단일 결합 또는 브릿지 X 에 의해 또한 연결될 수 있으며;m, n은 0 또는 1이고, 단 m + n = 1이고;p는 1, 2, 3, 4, 5 또는 6 이고;여기서 Ar1, Ar2 및 X는 함께 5원 고리 또는 6원 고리를 형성하고, Ar2, Ar3 및 X는 함께 5원 고리 또는 6원 고리를 형성하고, 단 화학식 (1)의 화합물에서의 모든 기호 X는 5원 고리 중에서 결합하거나 또는 화학식 (1)의 화합물에서의 모든 기호 X는 6원 고리 중에서 결합하고;Ar1, Ar2 및 Ar3기에서의 모든 π-전자의 합이 p = 1인 경우 28 이상이고, p = 2인 경우 합이 34 이상이며, p = 3인 경우 합이 40 이상이고, p = 4인 경우 46 이상이고, p = 5인 경우 합이 52 이상이며, p = 6인 경우 합이 58 이상인 것을 특징으로 함];단, 하기 화합물은 본 발명에서 제외됨:
- 제 1 항에 있어서, p = 1, 2 또는 3 이고, Ar1, Ar2 및 Ar3기에서의 모든 π-전자의 합이 p = 1인 경우 28 내지 50이고, p = 2인 경우 34 내지 56이고, p = 3인 경우 40 내지 62인 것을 특징으로 하는 화합물.
- 제 1 항에 있어서, 기호 Ar1, Ar2 및 Ar3이 각각의 경우 동일 또는 상이하게, 5 내지 22개 방향족 고리 원자를 가지는 아릴 또는 헤테로아릴기를 나타내며, 벤젠, 나프탈렌, 안트라센, 페난트렌, 플루오르안텐, 나프타센, 벤즈안트라센, 크리센, 피렌, 벤조플루오르안텐, 트리페닐렌, 페릴렌, 디벤즈안트라센, 벤조피렌, 피센, 펜타센, 펜타펜, 피리딘, 피라진, 피리미딘, 피리다진, 퀴놀린, 이소퀴놀린, 페난트롤린, 아크리딘에서 선택되는 것을 특징으로 하는 화합물.
- 제 1 항에 있어서, Ar1, Ar2 및 Ar3기 중 하나 이상이 4개 이상의 축합 고리, 즉 16개 이상의 π-전자를 가지는 것을 특징으로 하는 화합물.
- 제 1 항에 있어서, 기호 X가 각각의 경우 동일 또는 상이하게, B(R2), C(R2)2, Si(R2)2, O, S 또는 N(R2)로 이루어지는 군에서 선택되는 것을 특징으로 하는 화합물.
- 제 1 항에 있어서, 기호 R1이 각각의 경우 동일 또는 상이하게, H, D, F, Si(R3)3, 1 내지 10개 탄소 원자를 가지는 직쇄형 알킬 또는 알콕시기, 또는 3 내지 10개 탄소 원자를 가지는 분지형 또는 환형 알킬 또는 알콕시기에서 선택되며, 각각은 하나 이상의 라디칼 R3에 의해 치환될 수 있고, 여기서 각각의 경우 하나 이상의 비인접한 CH2 기가 R3C=CR3 또는 O에 의해 대체될 수 있고, 하나 이상의 H 원자가 F, 또는 5 내지 40개 방향족 고리 원자를 가지는 방향족 또는 헤테로방향족 고리계 또는 상기 계의 조합에 의해 대체될 수 있고; 여기서 둘 이상의 치환기 R1이 또한 서로 함께 단일환- 또는 다중환, 지방족 또는 방향족 고리계를 형성할 수 있는 것 을 특징으로 하는 화합물.
- 제 1 항에 있어서, 기호 R2가 각각의 경우 동일 또는 상이하게, H, 1 내지 10개 탄소 원자를 가지는 직쇄형 알킬기 또는 3 내지 10개 탄소 원자를 가지는 분지형 또는 환형 알킬기에서 선택되고, 여기서 각각의 경우 하나 이상의 비인접한 CH2 기가 -R2C=CR2- 또는 -O- 에 의해 대체될 수 있고, 하나 이상의 H 원자가 F, 또는 5 내지 16개 방향족 고리 원자를 가지는 1가 아릴 또는 헤테로아릴기에 의해 대체될 수 있으며, 이는 하나 이상의 비방향족 라디칼 R2에 의해 치환될 수 있고; 동일한 X기에서 결합하는 두 라디칼 R2가 또한 서로 함께 고리계를 형성할 수 있는 것을 특징으로 하는 화합물.
- 하나 이상의 라디칼 R1 및/또는 R2 는 중합체 또는 덴드리머로의 결합을 나타내는 제 1 항 내지 제 10 항 중 어느 한 항에 따른 하나 이상의 화합물을 포함하는 올리고머, 중합체 또는 덴드리머.
- 하기의 반응 단계를 포함하는, 제 1 항 내지 제 10 항 중 어느 한 항에 따른 화합물의 제조 방법:a) 적절히 치환된 Ar1, Ar2 및 Ar3 를 커플링시키는 단계, 여기서, 적절한 치환기는 카르복실레이트기일 수 있음; 및b) 브릿지 X 의 도입을 위해 치환기를 고리화하는 단계.
- 제 1 항 내지 제 10 항 중 어느 한 항에 있어서, 전자 소자에 사용되는 화합물.
- 하나의 유기층이 제 1 항 내지 제 10 항 중 어느 한 항에 따른 하나 이상의 화합물 또는 제 11 항에 따른 올리고머, 중합체 또는 덴드리머를 포함하는 것을 특징으로 하는, 유기 전계 발광 소자(OLED, PLED), 유기 전계 효과 트랜지스터(O-FET), 유기 박막 트랜지스터(O-TFT), 유기 발광 트랜지스터(O-LET), 유기 집적 회로(O-IC), 유기 태양 전지(O-SC), 유기 전계 퀀치 소자(O-FQD), 발광 전기화학 전지(LEC), 유기 광수용기 또는 유기 레이저 다이오드(O-레이저)에서 선택되는 유기 전자 소자.
- 제 14 항에 있어서, 제 1 항 내지 제 10 항 중 어느 한 항에 따른 화합물 또는 제 11 항에 따른 올리고머, 중합체 또는 덴드리머가 발광층에서의 발광 물질 또는 호스트 물질로서, 또는 정공 수송 또는 정공 주입층에서의 정공 수송 또는 정공 주입 물질로서, 또는 전자 수송층에서의 전자-수송 물질로서 사용되는 것을 특징으 로 하는 유기 전계 발광 소자.
- 제 14 항에 있어서, 제 1 항 내지 제 10 항 중 어느 한 항에 따른 화합물, 또는 제 11 항에 따른 올리고머, 중합체 또는 덴드리머가 호스트 물질과 조합되어 발광층에서의 발광 물질로서 사용되고, 상기 호스트 물질은 올리고아릴렌의 부류, 축합된 방향족기를 함유하는 올리고아릴렌, 안트라센, 올리고아릴렌비닐렌, 다각형 금속 착물, 정공 전도 화합물, 전자 전도 화합물, 케톤, 포스핀 옥사이드, 설폭사이드, 보론산 유도체, 벤즈안트라센 또는 하기 화학식 (138)의 화합물에서 선택되는 것을 특징으로 하는 유기 전계 발광 소자.[화학식 138]Ar4-(Ar5)p-Ar6[식 중,Ar4, Ar5, Ar6은 각각의 경우 동일 또는 상이하게, 5 내지 30개 방향족 고리 원자를 가지는 아릴 또는 헤테로아릴기이고, 이는 하나 이상의 라디칼 R1에 의해 치환될 수 있으며, R1 및 p는 제 1 항에 기재된 바와 동일한 의미를 가지고; Ar4, Ar5 및 Ar6에서의 π-전자의 합은 p = 1인 경우 30 이상이고, p = 2인 경우 36 이상이고, p = 3인 경우 42 이상임].
- 제 1 항 내지 제 10 항 중 어느 한 항에 따른 하나 이상의 화합물, 또는 제 11 항에 따른 올리고머, 중합체 또는 덴드리머를 포함하는 용액 또는 제형물.
- 제 2 항에 있어서, Ar1, Ar2 및 Ar3기에서의 모든 π-전자의 합이 p = 1인 경우 28 내지 46이고, p = 2인 경우 34 내지 52이고, p = 3인 경우 40 내지 58인 것을 특징으로 하는 화합물.
- 제 11 항에 있어서, 전자 소자에 사용되는 올리고머, 중합체 또는 덴드리머.
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- 2009-05-20 EP EP09776634.9A patent/EP2303814B1/de active Active
- 2009-05-20 US US13/001,818 patent/US9051233B2/en active Active
- 2009-05-22 EP EP09776642.2A patent/EP2303815B1/de active Active
- 2009-05-22 WO PCT/EP2009/003660 patent/WO2010012330A1/de active Application Filing
- 2009-05-22 JP JP2011520337A patent/JP5710479B2/ja active Active
- 2009-05-22 US US13/001,823 patent/US9090532B2/en active Active
- 2009-05-22 CN CN200980125133.9A patent/CN102076641B/zh active Active
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- 2009-05-25 TW TW098117307A patent/TWI478896B/zh active
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CN102076640B (zh) | 2015-06-17 |
US9090532B2 (en) | 2015-07-28 |
JP2011529614A (ja) | 2011-12-08 |
WO2010012328A1 (de) | 2010-02-04 |
US10074807B2 (en) | 2018-09-11 |
TWI478896B (zh) | 2015-04-01 |
JP5710479B2 (ja) | 2015-04-30 |
KR20100012781A (ko) | 2010-02-08 |
WO2010012330A1 (de) | 2010-02-04 |
CN102076640A (zh) | 2011-05-25 |
KR101104661B1 (ko) | 2012-01-13 |
KR101633135B1 (ko) | 2016-06-23 |
CN102076641B (zh) | 2015-02-18 |
US9051233B2 (en) | 2015-06-09 |
CN102076641A (zh) | 2011-05-25 |
US20150228905A1 (en) | 2015-08-13 |
US20110114889A1 (en) | 2011-05-19 |
EP2303815A1 (de) | 2011-04-06 |
DE102008035413A1 (de) | 2010-02-04 |
EP2303814B1 (de) | 2018-12-12 |
EP2303814A1 (de) | 2011-04-06 |
TW201012777A (en) | 2010-04-01 |
US20110108821A1 (en) | 2011-05-12 |
EP2303815B1 (de) | 2013-06-26 |
JP2011529455A (ja) | 2011-12-08 |
TW201012897A (en) | 2010-04-01 |
JP5726734B2 (ja) | 2015-06-03 |
KR20110050588A (ko) | 2011-05-16 |
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