JP6691598B2 - 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 - Google Patents
有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 Download PDFInfo
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- JP6691598B2 JP6691598B2 JP2018501983A JP2018501983A JP6691598B2 JP 6691598 B2 JP6691598 B2 JP 6691598B2 JP 2018501983 A JP2018501983 A JP 2018501983A JP 2018501983 A JP2018501983 A JP 2018501983A JP 6691598 B2 JP6691598 B2 JP 6691598B2
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- 150000001875 compounds Chemical class 0.000 title claims description 201
- 239000010410 layer Substances 0.000 claims description 210
- 125000003118 aryl group Chemical group 0.000 claims description 85
- 229910052698 phosphorus Inorganic materials 0.000 claims description 77
- 125000000623 heterocyclic group Chemical group 0.000 claims description 65
- 230000005525 hole transport Effects 0.000 claims description 50
- 125000005842 heteroatom Chemical group 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 229910052710 silicon Inorganic materials 0.000 claims description 40
- 125000001931 aliphatic group Chemical group 0.000 claims description 39
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 39
- 239000012044 organic layer Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 24
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 125000005567 fluorenylene group Chemical group 0.000 claims description 17
- 239000011368 organic material Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- -1 condensed ring group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 10
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 9
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000003618 dip coating Methods 0.000 claims description 2
- 238000007641 inkjet printing Methods 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 455
- 238000003786 synthesis reaction Methods 0.000 description 455
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 241
- 239000000047 product Substances 0.000 description 163
- 238000006243 chemical reaction Methods 0.000 description 104
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 78
- 239000000463 material Substances 0.000 description 51
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 41
- 230000000052 comparative effect Effects 0.000 description 40
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 40
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 40
- 239000000460 chlorine Substances 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000000741 silica gel Substances 0.000 description 25
- 229910002027 silica gel Inorganic materials 0.000 description 25
- 229960001866 silicon dioxide Drugs 0.000 description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 22
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 21
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 21
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 20
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000004305 biphenyl Substances 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 12
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 12
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 12
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 11
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 9
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 9
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 9
- 125000006757 (C2-C30) heterocyclic group Chemical group 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- GWOAJJWBCSUGHH-UHFFFAOYSA-N 1-bromo-4-(4-iodophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(I)C=C1 GWOAJJWBCSUGHH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 239000005416 organic matter Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000003413 spiro compounds Chemical class 0.000 description 6
- 101150075118 sub1 gene Proteins 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- UICAYKZNZSFYNU-UHFFFAOYSA-N 2,4-dichloro-[1]benzofuro[2,3-d]pyrimidine Chemical compound ClC=1N=C(C2=C(N1)OC1=C2C=CC=C1)Cl UICAYKZNZSFYNU-UHFFFAOYSA-N 0.000 description 5
- RKVFFIZXAPIGNC-UHFFFAOYSA-N 2,4-dichloro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound ClC=1N=C(C2=C(N1)SC1=C2C=CC=C1)Cl RKVFFIZXAPIGNC-UHFFFAOYSA-N 0.000 description 5
- BSWVSKQCYPFXJF-UHFFFAOYSA-N 2,4-dichloro-[1]benzothiolo[3,2-d]pyrimidine Chemical compound C1=CC=C2C3=NC(Cl)=NC(Cl)=C3SC2=C1 BSWVSKQCYPFXJF-UHFFFAOYSA-N 0.000 description 5
- LOXUVZPMEXKUEJ-UHFFFAOYSA-N 2-bromo-7-iodo-9,9-dimethylfluorene Chemical compound C1=C(I)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LOXUVZPMEXKUEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- PHHATHMJJOZFEK-UHFFFAOYSA-N 2,4-dichloro-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C2C3=NC(Cl)=NC(Cl)=C3OC2=C1 PHHATHMJJOZFEK-UHFFFAOYSA-N 0.000 description 4
- VECLPBKDHAALGQ-UHFFFAOYSA-N 3-bromo-9,9-dimethylfluorene Chemical compound BrC1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 VECLPBKDHAALGQ-UHFFFAOYSA-N 0.000 description 4
- UGFOTZLGPPWNPY-UHFFFAOYSA-N 7h-benzo[c]carbazole Chemical compound C1=CC=CC2=C3C4=CC=CC=C4NC3=CC=C21 UGFOTZLGPPWNPY-UHFFFAOYSA-N 0.000 description 4
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical compound C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 4
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 4
- 238000000429 assembly Methods 0.000 description 4
- 230000000712 assembly Effects 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WNXNWOBGPRKOJF-UHFFFAOYSA-N 2-bromo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 WNXNWOBGPRKOJF-UHFFFAOYSA-N 0.000 description 3
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 101150003085 Pdcl gene Proteins 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- AXVLLFWWMWDULG-UHFFFAOYSA-N 3-bromo-9,9-diphenylfluorene Chemical compound C=1C(Br)=CC=C2C=1C1=CC=CC=C1C2(C=1C=CC=CC=1)C1=CC=CC=C1 AXVLLFWWMWDULG-UHFFFAOYSA-N 0.000 description 2
- ROEOVWIEALGNLM-UHFFFAOYSA-N 5h-benzo[b]carbazole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4NC3=CC2=C1 ROEOVWIEALGNLM-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 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
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- HXITXNWTGFUOAU-RALIUCGRSA-N (2,3,4,5,6-pentadeuteriophenyl)boronic acid Chemical compound [2H]C1=C([2H])C([2H])=C(B(O)O)C([2H])=C1[2H] HXITXNWTGFUOAU-RALIUCGRSA-N 0.000 description 1
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
- ICQAKBYFBIWELX-UHFFFAOYSA-N (4-naphthalen-2-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=C(C=CC=C2)C2=C1 ICQAKBYFBIWELX-UHFFFAOYSA-N 0.000 description 1
- BSKLSKWOKGVQHF-UHFFFAOYSA-N (4-phenylnaphthalen-1-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=CC=C1C1=CC=CC=C1 BSKLSKWOKGVQHF-UHFFFAOYSA-N 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
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- 238000010295 mobile communication Methods 0.000 description 1
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- JYAVHXABZQYLTH-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 JYAVHXABZQYLTH-UHFFFAOYSA-N 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002560 nitrile group Chemical group 0.000 description 1
- MWIZGXJYCNZVDW-UHFFFAOYSA-N phenanthren-2-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3C=CC2=C1 MWIZGXJYCNZVDW-UHFFFAOYSA-N 0.000 description 1
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- FZEWPLIHPXGNTB-UHFFFAOYSA-N thianthren-1-ylboronic acid Chemical compound S1C2=CC=CC=C2SC2=C1C=CC=C2B(O)O FZEWPLIHPXGNTB-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Description
1515565805539_81
した。反応が終了すれば、CH2Cl2と水で抽出した後、有機層をMgSO4で乾燥させ、濃縮した後、生成された化合物をsilicagel column及び再結晶して生成物6.8g(収率:71%)を得た。
の基準輝度でマックサイエンス社で製造された寿命測定装置によってT95寿命を測定した。その測定結果は、下記表7の通りである。
の基準輝度でマックサイエンス社で製造された寿命測定装置によってT95寿命を測定した。その測定結果は、下記表8の通りである。
110:基板
120:第1電極
130:正孔注入層
140:正孔輸送層
141:バッファ層
150:発光層
151:発光補助層
160:電子輸送層
170:電子注入層
180:第2電極
[関連出願の相互参照]
本特許出願は、2015年7月10日に韓国に出願した特許出願番号第10-2015-0098090号に対して米国特許法119(a)条(35U.S.C§119(a))によって優先権を主張し、そのあらゆる内容は参考文献として本特許出願に併合される。なお、本特許出願は米国以外に国に対しても上記のような理由で優先権を主張すれば、その全内容は参考文献として本特許出願に組み込まれる。
Claims (14)
- 第1電極、有機物層と第2電極が順次積層された有機電気素子において、
前記有機物層は正孔輸送層、発光補助層、及び発光層を含み、
前記正孔輸送層及び前記発光補助層のうち少なくとも一方は、下記式1で表される化合物を含み、前記発光層は、下記式2で表される化合物を含む有機電気素子:
前記式1と式2において、
Ar1〜Ar3は、互いに独立して、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、C1−C50のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C30のアルコキシ基、C6−C30のアリールオキシル基、並びに−L’−N(Ra)(Rb)からなる群より選択され、Ar2とAr3は互いに結合して環を形成することができ、
L1はC6−C60のアリーレン基、フルオレニレン基、O、N、S、Si及びPからなる群より選ばれる少なくとも1つのヘテロ原子を含むC2−C60の2価のヘテロ環基、C3−C60の脂肪族環とC6−C60の芳香族環との2価の縮合環基、並びにC2−C60の2価の脂肪族炭化水素基からなる群より選択され、
R1、R2、R3〜R5、及びR7は互いに独立に、i)重水素、ハロゲン、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、C1−C50のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C30のアルコキシ基、C6−C30のアリールオキシル基、並びに−L’−N(Ra)(Rb)からなる群より選択されるか、又はii)隣り合う基同士で互いに結合して少なくとも1つの環を形成し、このとき、環を形成しない基はi)で定義されたとおりであり、
mは0〜4の整数であり、nは0〜3の整数であり、a、b、c、及びhは、互いに独立に、0〜4の整数であり、mが2以上の整数である場合には、複数のR1は互いに同じでも異なっていてもよく、nが2以上の整数である場合には、複数のR2は互いに同じでも異なっていてもよく、aが2以上の整数である場合には、複数のR3は互いに同じでも異なっていてもよく、bが2以上の整数である場合には、複数のR4は互いに同じでも異なっていてもよく、cが2以上の整数である場合には、複数のR5は互いに同じでも異なっていてもよく、hが2以上の整数である場合には、複数のR7は互いに同じでも異なっていてもよく、
R6は水素、C6−C60のアリール基、フルオレニル基、並びにO、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選択され、
X及びYは、互いに独立に、単結合、S、O、N(R’)、及びC(R’)(R”)からなる群より選択され、ここで、R’及びR”は、互いに独立に、水素、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基、並びにC1−C50のアルキル基からなる群より選択され、R’とR”は互いに結合して環を形成することができ、d及びeは、互いに独立に、0又は1の整数であり、ただしd+eは1又は2の整数であり、
Z1及びZ2は、互いに独立に、単結合、S、及びOからなる群より選択され、f及びgは、互いに独立に、0又は1の整数であり、ただし、f+gは1又は2の整数であり、
前記Ar1〜Ar3、R1〜R5及びR7の−L’−N(Ra)(Rb)において、−L’は単結合、C6−C60のアリーレン基、フルオレニレン基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、並びにO、N、S、Si及びPからなる群より選ばれた少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選択され、Ra及びRbは、互いに独立に、C6−C60のアリール基、フルオレニル基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、並びにO、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選択され、
前記Ar1〜Ar3、R1〜R7、R’、R”、L1、L’、Ra又はRbで表されるアリール基、ヘテロ環基、フルオレニル基、アルキル基、アルケニル基、縮合環基、アルコキシ基、アリールオキシル基、アリーレン基、フルオレニレン基、又は脂肪族炭化水素基は、それぞれ、互いに独立に、重水素、ハロゲン、シラン基、シロキサン基、ホウ素基、ゲルマニウム基、シアノ基、ニトロ基、C1−C20のアルキルチオ基、C1−C20のアルコキシ基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C6−C20のアリール基、重水素で置換されたC6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1つのヘテロ原子を含むC2−C20のヘテロ環基、C3−C20のシクロアルキル基、C7−C20のアリールアルキル基、C8−C20のアリールアルケニル基、アリールアミン基、並びにヘテロアリールアミン基からなる群より選択された1つ以上の置換基で更に置換されていてもよい。 - 前記式1で表される化合物は下記式3−1〜式3−3のうちのいずれか1つによって表される、請求項1に記載の有機電気素子:
前記式3−1〜3−3において、Ar1〜Ar3、R1、R2、m及びnは請求項1において定義されたものと同一である。 - 前記式2で表される化合物は下記式4〜式7のうちのいずれか1つによって表される、請求項1に記載の有機電気素子:
前記式4〜7において、R3〜R7、X、Y、Z1、Z2、a、b、c及びhは、請求項1において定義されたものと同一である。 - 前記式1で表される化合物は下記化合物のうちの1つである、請求項1に記載の有機電気素子。
- 前記式2で表される化合物は下記化合物のうちの1つである、請求項1に記載の有機電気素子。
- 前記発光補助層は、前記式1で表される化合物を含み、前記正孔輸送層は、下記式8で示される化合物を含む、請求項1に記載の有機電気素子:
前記式8において、
Ar4及びAr5は、互いに独立して、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、C1−C50のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C30のアルコキシ基、C6−C30のアリールオキシル基、並びに−L’−N(Ra)(Rb)からなる群より選ばれ、
Ar6は下記化学式8−1、式8−2及び式8−3のうちいずれか1つで表される基であり、
前記式8−1、式8−2及び式8−3において、
Ar7、Ar8及びAr9は、互いに独立して、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、C1−C50のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C30のアルコキシ基、C6−C30のアリールオキシル基、並びに−L’−N(Ra)(Rb)からなる群より選択され、
R8〜R10は互いに独立して、i)重水素、ハロゲン、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、C1−C50のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C30のアルコキシ基、C6−C30のアリールオキシル基、並びに−L’−N(Ra)(Rb)からなる群より選択されるか、又はii)隣り合う基同士で互いに結合して少なくとも1つの環を形成し、このとき、環を形成しない基はi)で定義されたとおりであり、
h、i及びjは、互いに独立して、0〜4の整数であり、hが2以上の整数である場合には、複数のR8は互いに同じでも異なっていてもよく、iが2以上の整数である場合には、複数のR9は互いに同じでも異なっていてもよく、jが2以上の整数である場合には、複数のR10は互いに同じでも異なっていてもよく、
L2は、単結合、C6−C60のアリーレン基、フルオレニレン基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、並びにO、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選択され、
L3及びL4は、互いに独立して、C6−C60のアリーレン基、フルオレニレン基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、並びにO、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選択され、
前記Ar4、Ar5、Ar7〜Ar9、R8〜R10の−L’−N(Ra)(Rb)において、L’は単結合、C6−C60のアリーレン基、フルオレニレン基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、並びにO、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選択され、Ra及びRbは互いに独立して、C6−C60のアリール基、フルオレニル基、C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基、C1−C50のアルキル基、並びにO、N、S、Si及びPから選ばれる少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選択され、
前記Ar4−Ar5、Ar7−Ar9、R8−R10、R’、R”、L2、L3、L’、Ra又はRbで表されるアリール基、ヘテロ環基、フルオレニル基、アルキル基、アルケニル基、縮合環基、アルコキシ基、アリールオキシル基、アリーレン基、フルオレニレン基、又は脂肪族炭化水素基は、それぞれ、重水素、ハロゲン、シラン基、シロキサン基、ホウ素基、ゲルマニウム基、シアノ基、ニトロ基、C1−C20のアルキルチオ基、C1−C20のアルコキシ基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C6−C20のアリール基、重水素で置換されたC6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1つのヘテロ原子を含むC2−C20のヘテロ環基、C3−C20のシクロアルキル基、C7−C20のアリールアルキル基、並びにC8−C20のアリールアルケニル基からなる群より選択された1つ以上の置換基で更に置換されていてもよい。 - 前記式8で表される化合物は下記化合物のうちの1つである、請求項6に記載の有機電気素子。
- 前記式1で示される化合物は1種の単独又は2種以上の混合物の形で前記正孔輸送層または発光補助層に含まれる、請求項1に記載の有機電気素子。
- 前記式2で示される化合物は1種の単独又は2種以上の混合物の形で前記発光層に含まれる、請求項1に記載の有機電気素子。
- 前記式1で示される化合物は1種の単独又は2種以上の混合物の形で前記発光補助層に含まれ、
前記式8で示される化合物は1種の単独又は2種以上の混合物の形で前記正孔輸送層に含まれる、請求項6に記載の有機電気素子。 - 前記第1電極と第2電極の一面のうちの前記有機物層と反対となる少なくとも一面に形成される光効率改善層を更に含む、請求項1に記載の有機電気素子。
- 前記有機物層はスピンコーティング工程、ノズルプリンティング工程、インクジェットプリンティング工程、スロットコーティング工程、ディップコーティング工程又はロールツーロール工程によって形成される、請求項1に記載の有機電気素子。
- 請求項1に記載の有機電気素子を含むディスプレイ装置;及び
前記ディスプレイ装置を駆動する制御部;を含む電子装置。 - 前記有機電気素子は、有機電気発光素子、有機太陽電池、有機感光体、有機トランジスタ、及び単色又は白色照明用素子のうち、少なくとも1つである、請求項13に記載の電子装置。
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