WO2016072690A1 - Dispositif électronique organique et dispositif d'affichage utilisant une composition pour dispositif électronique organique - Google Patents
Dispositif électronique organique et dispositif d'affichage utilisant une composition pour dispositif électronique organique Download PDFInfo
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- WO2016072690A1 WO2016072690A1 PCT/KR2015/011687 KR2015011687W WO2016072690A1 WO 2016072690 A1 WO2016072690 A1 WO 2016072690A1 KR 2015011687 W KR2015011687 W KR 2015011687W WO 2016072690 A1 WO2016072690 A1 WO 2016072690A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 230000005525 hole transport Effects 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 239000011368 organic material Substances 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 6
- 229910052722 tritium Inorganic materials 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio 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
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 230000008676 import Effects 0.000 claims description 2
- 238000007641 inkjet printing Methods 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
- 230000015572 biosynthetic process Effects 0.000 description 91
- 238000003786 synthesis reaction Methods 0.000 description 91
- 239000010410 layer Substances 0.000 description 57
- 239000000047 product Substances 0.000 description 47
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 26
- 238000001308 synthesis method Methods 0.000 description 25
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- 0 CCCN(C*)C(C)C Chemical compound CCCN(C*)C(C)C 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 238000002347 injection Methods 0.000 description 11
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- 239000000463 material Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229960001866 silicon dioxide Drugs 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- -1 oxygen radical Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 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 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- KVVDWTUHHMYSBM-UHFFFAOYSA-N 2-bromo-7-iodo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=C(I)C=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 KVVDWTUHHMYSBM-UHFFFAOYSA-N 0.000 description 3
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- HPCKEAXEWARUIH-UHFFFAOYSA-N 1-bromo-3-(4-iodophenyl)benzene Chemical group BrC1=CC=CC(C=2C=CC(I)=CC=2)=C1 HPCKEAXEWARUIH-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-UHFFFAOYSA-N 0.000 description 2
- MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 2
- OGENPBMBOLTWLZ-UHFFFAOYSA-N Brc(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound Brc(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 OGENPBMBOLTWLZ-UHFFFAOYSA-N 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- JAUCIDPGGHZXRP-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1Nc(cc1)ccc1-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1Nc(cc1)ccc1-c1ccccc1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 2
- DZRDATNLTUIPAY-UHFFFAOYSA-N c(cc1)ccc1Nc(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 Chemical compound c(cc1)ccc1Nc(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 DZRDATNLTUIPAY-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- XAOMFUPJQYNDEG-LBPRGKRZSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-methylpropan-1-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(C(C)C)=O XAOMFUPJQYNDEG-LBPRGKRZSA-N 0.000 description 1
- VXZCZCODBREKPY-UHFFFAOYSA-N 1-bromo-4-(3-iodophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC(I)=C1 VXZCZCODBREKPY-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- OKDQJGCCMJHSQF-UHFFFAOYSA-N 2'-bromo-7'-iodo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC(I)=CC=C1C1=CC=C(Br)C=C12 OKDQJGCCMJHSQF-UHFFFAOYSA-N 0.000 description 1
- QFBDMDNYRZVSMF-UHFFFAOYSA-N 2-(4-bromophenyl)-9,9-diphenylfluorene Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2C(=CC=CC=2)C2(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 QFBDMDNYRZVSMF-UHFFFAOYSA-N 0.000 description 1
- ALXCEAWHEVDVHS-UHFFFAOYSA-N 2-(4-bromophenyl)dibenzofuran Chemical compound C1=CC(Br)=CC=C1C1=CC=C(OC=2C3=CC=CC=2)C3=C1 ALXCEAWHEVDVHS-UHFFFAOYSA-N 0.000 description 1
- FGJDRITYPHJFOH-UHFFFAOYSA-N 2-bromo-1-nitro-4-phenylbenzene Chemical group C1=C(Br)C([N+](=O)[O-])=CC=C1C1=CC=CC=C1 FGJDRITYPHJFOH-UHFFFAOYSA-N 0.000 description 1
- SBABEHDRJFHMEU-UHFFFAOYSA-N 2-bromo-1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(Br)C=CC2=C1 SBABEHDRJFHMEU-UHFFFAOYSA-N 0.000 description 1
- KRQFZBUWIOZDMP-UHFFFAOYSA-N 2-bromo-3-nitronaphthalene Chemical compound C1=CC=C2C=C(Br)C([N+](=O)[O-])=CC2=C1 KRQFZBUWIOZDMP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AZFABGHLDGJASW-UHFFFAOYSA-N 3-bromodibenzofuran Chemical compound C1=CC=C2C3=CC=C(Br)C=C3OC2=C1 AZFABGHLDGJASW-UHFFFAOYSA-N 0.000 description 1
- JVHWZEWMZMHZFN-UHFFFAOYSA-N 4-(3-bromophenyl)dibenzothiophene Chemical compound BrC1=CC=CC(C=2C3=C(C4=CC=CC=C4S3)C=CC=2)=C1 JVHWZEWMZMHZFN-UHFFFAOYSA-N 0.000 description 1
- GIWPFBXOJOXJBN-UHFFFAOYSA-N 4-dibenzofuran-2-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(OC=2C3=CC=CC=2)C3=C1 GIWPFBXOJOXJBN-UHFFFAOYSA-N 0.000 description 1
- WLTWDKFFRPIRCA-UHFFFAOYSA-N 4-dibenzothiophen-2-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(SC=2C3=CC=CC=2)C3=C1 WLTWDKFFRPIRCA-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-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
- RLIHNBGCJAAFJD-UHFFFAOYSA-N 9-bromo-15-iodo-12-thiapentacyclo[11.8.0.02,11.03,8.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene Chemical compound BrC1=CC=2SC3=C(C=2C=2C=CC=CC1=2)C1=CC=CC=C1C(=C3)I RLIHNBGCJAAFJD-UHFFFAOYSA-N 0.000 description 1
- PEGNPIUDNVSNGF-UHFFFAOYSA-N BrC1=C(C=C(C=C1)C=1C=CC2=C(SC3=C2C=CC=C3)C=1)[N+](=O)[O-] Chemical compound BrC1=C(C=C(C=C1)C=1C=CC2=C(SC3=C2C=CC=C3)C=1)[N+](=O)[O-] PEGNPIUDNVSNGF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- BUQWXYXOVCCNJT-UHFFFAOYSA-N C(C1c2ccccc2-c2c1cccc2)c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1[o]c1c2CCC=C1)c1ccc2[o]c(cccc3)c3c2c1 Chemical compound C(C1c2ccccc2-c2c1cccc2)c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1[o]c1c2CCC=C1)c1ccc2[o]c(cccc3)c3c2c1 BUQWXYXOVCCNJT-UHFFFAOYSA-N 0.000 description 1
- IYGSBGWWWNFMNT-UHFFFAOYSA-N C1(=CC=CC=C1)N1C2=CC=CC=C2C=2C=CC(=CC1=2)C1=CC=C(N)C=C1 Chemical compound C1(=CC=CC=C1)N1C2=CC=CC=C2C=2C=CC(=CC1=2)C1=CC=C(N)C=C1 IYGSBGWWWNFMNT-UHFFFAOYSA-N 0.000 description 1
- WBXRTYKCUPAUOW-UHFFFAOYSA-N CC(C)(c1c2)c3cc(-[n]4c5ccccc5c5c4cccc5)ccc3-c1ccc2N(c(cc1)ccc1-c1ccccc1)c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 Chemical compound CC(C)(c1c2)c3cc(-[n]4c5ccccc5c5c4cccc5)ccc3-c1ccc2N(c(cc1)ccc1-c1ccccc1)c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 WBXRTYKCUPAUOW-UHFFFAOYSA-N 0.000 description 1
- HWIYIZDPBPVEEE-UHFFFAOYSA-N CC(C1)C=Cc(c2c3C=CCC2)c1[n]3-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound CC(C1)C=Cc(c2c3C=CCC2)c1[n]3-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 HWIYIZDPBPVEEE-UHFFFAOYSA-N 0.000 description 1
- PQTPRGAOOBHNNL-UHFFFAOYSA-N CC1(C)c(cc(cc2)Br)c2-c(cc2)c1cc2-[n]1c2ccccc2c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)Br)c2-c(cc2)c1cc2-[n]1c2ccccc2c2c1cccc2 PQTPRGAOOBHNNL-UHFFFAOYSA-N 0.000 description 1
- CWTHAPSQHMGCAN-UHFFFAOYSA-N CC1(C)c2cc(cccc3)c3cc2-c2c1ccc(N(c(cc1)ccc1-c(cc1)ccc1-[n]1c3ccc(cccc4)c4c3c3c1ccc1c3cccc1)c1cc(-c3ccncc3)cc3c1[s]c1c3cccc1)c2 Chemical compound CC1(C)c2cc(cccc3)c3cc2-c2c1ccc(N(c(cc1)ccc1-c(cc1)ccc1-[n]1c3ccc(cccc4)c4c3c3c1ccc1c3cccc1)c1cc(-c3ccncc3)cc3c1[s]c1c3cccc1)c2 CWTHAPSQHMGCAN-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N CC[n]1c2ccccc2c2ccccc12 Chemical compound CC[n]1c2ccccc2c2ccccc12 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NAFKMUWLIYQHHI-UHFFFAOYSA-N I[n]1c2ccccc2c2c1cccc2 Chemical compound I[n]1c2ccccc2c2c1cccc2 NAFKMUWLIYQHHI-UHFFFAOYSA-N 0.000 description 1
- LAUAYLCGWGFIMK-UHFFFAOYSA-N N[IH]N([IH][AlH2])[IH][IH][Al]=[IH] Chemical compound N[IH]N([IH][AlH2])[IH][IH][Al]=[IH] LAUAYLCGWGFIMK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 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 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- JJZCMNWGDBAGHE-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1[o]c1ccccc21)c1ccc2[s]c(cccc3)c3c2c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1[o]c1ccccc21)c1ccc2[s]c(cccc3)c3c2c1 JJZCMNWGDBAGHE-UHFFFAOYSA-N 0.000 description 1
- ALTHUPNZFBOVTL-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1N(c1ccc(c2ccccc2[o]2)c2c1)c1ccc(c(cccc2)c2[s]2)c2c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1N(c1ccc(c2ccccc2[o]2)c2c1)c1ccc(c(cccc2)c2[s]2)c2c1 ALTHUPNZFBOVTL-UHFFFAOYSA-N 0.000 description 1
- CNJQQLKVISROGE-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc(C23c4ccccc4-c4c2cccc4)c1-c1c3cccc1)c(cc1)cc2c1[s]c1ccccc21 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc(C23c4ccccc4-c4c2cccc4)c1-c1c3cccc1)c(cc1)cc2c1[s]c1ccccc21 CNJQQLKVISROGE-UHFFFAOYSA-N 0.000 description 1
- YOUNGCKXIMWJEV-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n](c1c2c(cccc3)c3cc1)c1c2c2ccccc2cc1)c1cccc(-c(cccc2)c2-c(cc2)cc(cc3)c2c(c2c(cccc4)c4ccc22)c3[n]2-c(cc2)ccc2-c(cc2)ccc2N(c2cccc(-c3c4[s]c(cccc5)c5c4ccc3)c2)c2c(cccc3)c3ccc2)c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n](c1c2c(cccc3)c3cc1)c1c2c2ccccc2cc1)c1cccc(-c(cccc2)c2-c(cc2)cc(cc3)c2c(c2c(cccc4)c4ccc22)c3[n]2-c(cc2)ccc2-c(cc2)ccc2N(c2cccc(-c3c4[s]c(cccc5)c5c4ccc3)c2)c2c(cccc3)c3ccc2)c1 YOUNGCKXIMWJEV-UHFFFAOYSA-N 0.000 description 1
- SWTKZXWNEZJKNY-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1Nc(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1Nc(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 SWTKZXWNEZJKNY-UHFFFAOYSA-N 0.000 description 1
- OXFLCTUIVKIUAC-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(Nc2ccc3[o]c(cccc4)c4c3c2)c1 Chemical compound c(cc1)ccc1-c1cccc(Nc2ccc3[o]c(cccc4)c4c3c2)c1 OXFLCTUIVKIUAC-UHFFFAOYSA-N 0.000 description 1
- ZZIGDAKJJOMVDI-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccc(cccc3)c3c2c2c1ccc1c2cccc1)c1cccc(-c2ncc3[o]c(cccc4)c4c3c2)c1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccc(cccc3)c3c2c2c1ccc1c2cccc1)c1cccc(-c2ncc3[o]c(cccc4)c4c3c2)c1 ZZIGDAKJJOMVDI-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- OCVXZQOKBHXGRU-UHFFFAOYSA-N iodine(1+) Chemical compound [I+] OCVXZQOKBHXGRU-UHFFFAOYSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/875—Arrangements for extracting light from the devices
-
- 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
- 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
- H10K50/15—Hole transporting layers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
La présente invention porte sur un dispositif électronique organique et un dispositif d'affichage et un dispositif électronique les comprenant, le dispositif électronique organique comprenant, en tant que couche de transport de trous, une composition formée à partir d'au moins deux composés qui ont des structures différentes les unes des autres, ce qui leur permet d'avoir un rendement d'émission de lumière prédéfini accru et une stabilité accrue ainsi qu'une durée de vie prolongée.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140151984A KR102329806B1 (ko) | 2014-11-04 | 2014-11-04 | 유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자 |
| KR10-2014-0151984 | 2014-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2016072690A1 true WO2016072690A1 (fr) | 2016-05-12 |
Family
ID=55909358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2015/011687 WO2016072690A1 (fr) | 2014-11-04 | 2015-11-03 | Dispositif électronique organique et dispositif d'affichage utilisant une composition pour dispositif électronique organique |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102329806B1 (fr) |
| WO (1) | WO2016072690A1 (fr) |
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| WO2018164239A1 (fr) | 2017-03-08 | 2018-09-13 | 出光興産株式会社 | Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique, et appareil électronique |
| CN110382488B (zh) * | 2017-03-08 | 2023-11-03 | 出光兴产株式会社 | 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
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| CN110498765B (zh) * | 2018-05-17 | 2022-09-02 | 北京鼎材科技有限公司 | 化合物、有机电致发光材料和有机电致发光器件 |
| CN110498765A (zh) * | 2018-05-17 | 2019-11-26 | 北京鼎材科技有限公司 | 化合物、有机电致发光材料和有机电致发光器件 |
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| CN114728947A (zh) * | 2020-02-13 | 2022-07-08 | 株式会社Lg化学 | 新型化合物及利用其的有机发光器件 |
| US11678569B2 (en) | 2020-03-31 | 2023-06-13 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| WO2022250028A1 (fr) * | 2021-05-27 | 2022-12-01 | 出光興産株式会社 | Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique |
| CN114790184A (zh) * | 2022-06-22 | 2022-07-26 | 吉林奥来德光电材料股份有限公司 | 一种发光辅助材料及其制备方法、发光器件、发光装置 |
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| Publication number | Publication date |
|---|---|
| KR20160052136A (ko) | 2016-05-12 |
| KR102329806B1 (ko) | 2021-11-22 |
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