KR20090005038A - 안트라센 유도체를 포함하는 전기발광 디바이스 - Google Patents
안트라센 유도체를 포함하는 전기발광 디바이스 Download PDFInfo
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- KR20090005038A KR20090005038A KR1020087025895A KR20087025895A KR20090005038A KR 20090005038 A KR20090005038 A KR 20090005038A KR 1020087025895 A KR1020087025895 A KR 1020087025895A KR 20087025895 A KR20087025895 A KR 20087025895A KR 20090005038 A KR20090005038 A KR 20090005038A
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- South Korea
- Prior art keywords
- oled device
- anthracene
- group
- electron
- layer
- 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.)
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- 239000000463 material Substances 0.000 claims abstract description 139
- 125000003118 aryl group Chemical group 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 230000003647 oxidation Effects 0.000 claims abstract description 20
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 20
- 239000002019 doping agent Substances 0.000 claims abstract description 8
- -1 anthracene compound Chemical class 0.000 claims description 94
- 125000001424 substituent group Chemical group 0.000 claims description 49
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 6
- 150000003518 tetracenes Chemical class 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 150000005041 phenanthrolines Chemical class 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 127
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
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- 238000002347 injection Methods 0.000 description 18
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 17
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 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 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 5
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- SJWDHKSOZAKMFR-UHFFFAOYSA-N 2-(4-methoxyphenyl)anthracene Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1 SJWDHKSOZAKMFR-UHFFFAOYSA-N 0.000 description 4
- BCUFROSIPJDSDA-UHFFFAOYSA-N 9,10-dibromo-2-(4-methoxyphenyl)anthracene Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(Br)=C2C(C=CC=C2)=C2Br)C2=C1 BCUFROSIPJDSDA-UHFFFAOYSA-N 0.000 description 4
- 229930192334 Auxin Natural products 0.000 description 4
- 0 Cc1ccc(B(c2ccc(*)cc2)c2ccc(C=Cc(cc3)ccc3-c3ccc(C=Cc4ccc(*(c5ccc(*)cc5)c(cc5)ccc5N)cc4)cc3)cc2)cc1 Chemical compound Cc1ccc(B(c2ccc(*)cc2)c2ccc(C=Cc(cc3)ccc3-c3ccc(C=Cc4ccc(*(c5ccc(*)cc5)c(cc5)ccc5N)cc4)cc3)cc2)cc1 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002363 auxin Substances 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000002848 electrochemical method Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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
- 229960003540 oxyquinoline Drugs 0.000 description 4
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 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 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
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- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- LQRAULANJCQXAM-UHFFFAOYSA-N 1-n,5-n-dinaphthalen-1-yl-1-n,5-n-diphenylnaphthalene-1,5-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC(=C2C=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC2=CC=CC=C12 LQRAULANJCQXAM-UHFFFAOYSA-N 0.000 description 2
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- 125000000033 alkoxyamino group Chemical group 0.000 description 2
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical group C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 2
- UHVLDCDWBKWDDN-UHFFFAOYSA-N n-phenyl-n-[4-[4-(n-pyren-2-ylanilino)phenyl]phenyl]pyren-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC3=CC=CC4=CC=C(C2=C43)C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC4=CC=CC5=CC=C(C3=C54)C=2)C=C1 UHVLDCDWBKWDDN-UHFFFAOYSA-N 0.000 description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 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 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/412,602 US20070252517A1 (en) | 2006-04-27 | 2006-04-27 | Electroluminescent device including an anthracene derivative |
| US11/412,602 | 2006-04-27 |
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| KR20090005038A true KR20090005038A (ko) | 2009-01-12 |
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| Country | Link |
|---|---|
| US (1) | US20070252517A1 (enExample) |
| EP (1) | EP2013313A1 (enExample) |
| JP (1) | JP2009535813A (enExample) |
| KR (1) | KR20090005038A (enExample) |
| WO (1) | WO2007130259A1 (enExample) |
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| KR101384785B1 (ko) | 2006-06-01 | 2014-04-14 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광소자, 발광장치 및 전자기기 |
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| US9666826B2 (en) * | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| US20070252516A1 (en) * | 2006-04-27 | 2007-11-01 | Eastman Kodak Company | Electroluminescent devices including organic EIL layer |
| US7733009B2 (en) * | 2006-04-27 | 2010-06-08 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| US20070252515A1 (en) * | 2006-04-27 | 2007-11-01 | Eastman Kodak Company | Electroluminescent device including an anthracene derivative |
-
2006
- 2006-04-27 US US11/412,602 patent/US20070252517A1/en not_active Abandoned
-
2007
- 2007-04-13 WO PCT/US2007/009164 patent/WO2007130259A1/en not_active Ceased
- 2007-04-13 JP JP2009507713A patent/JP2009535813A/ja active Pending
- 2007-04-13 KR KR1020087025895A patent/KR20090005038A/ko not_active Ceased
- 2007-04-13 EP EP07755436A patent/EP2013313A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20070252517A1 (en) | 2007-11-01 |
| EP2013313A1 (en) | 2009-01-14 |
| JP2009535813A (ja) | 2009-10-01 |
| WO2007130259A1 (en) | 2007-11-15 |
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