JP5326568B2 - 発光素子材料および発光素子 - Google Patents
発光素子材料および発光素子 Download PDFInfo
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- JP5326568B2 JP5326568B2 JP2008516647A JP2008516647A JP5326568B2 JP 5326568 B2 JP5326568 B2 JP 5326568B2 JP 2008516647 A JP2008516647 A JP 2008516647A JP 2008516647 A JP2008516647 A JP 2008516647A JP 5326568 B2 JP5326568 B2 JP 5326568B2
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- light emitting
- emitting device
- aryl
- derivatives
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- 239000000463 material Substances 0.000 title claims abstract description 123
- -1 pyrene compound Chemical class 0.000 claims abstract description 42
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 23
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000000732 arylene group Chemical group 0.000 claims abstract description 11
- 125000005013 aryl ether group Chemical group 0.000 claims abstract description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 150000004832 aryl thioethers Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 239000002019 doping agent Substances 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 42
- 238000000746 purification Methods 0.000 description 34
- 230000032258 transport Effects 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 33
- 238000000859 sublimation Methods 0.000 description 30
- 230000008022 sublimation Effects 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 239000000758 substrate Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 16
- 239000011259 mixed solution Substances 0.000 description 15
- 239000010409 thin film Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000011521 glass Substances 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- 0 CC(C)(C)c1cccc(-c2ccc(cc3)c4c2ccc(c(-c2c5[o]c(cccc6)c6c5ccc2)c2)c4c3c2-c2cccc(C(C)(C)*)c2)c1 Chemical compound CC(C)(C)c1cccc(-c2ccc(cc3)c4c2ccc(c(-c2c5[o]c(cccc6)c6c5ccc2)c2)c4c3c2-c2cccc(C(C)(C)*)c2)c1 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 238000009792 diffusion process Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000010408 film Substances 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 238000001291 vacuum drying Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 238000010894 electron beam technology Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 150000004866 oxadiazoles Chemical class 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 5
- 235000019798 tripotassium phosphate Nutrition 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 150000003220 pyrenes Chemical class 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 3
- NSESELKUHFTIJN-UHFFFAOYSA-N 2-(4-dibenzofuran-4-ylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 NSESELKUHFTIJN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000005581 pyrene group Chemical group 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 2
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- OXAPHTWFEWINHC-UHFFFAOYSA-N 1-(4-methylphenyl)pyrene Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=C2)C3=C4C2=CC=CC4=CC=C13 OXAPHTWFEWINHC-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MQNDWBDMDCOJJJ-UHFFFAOYSA-N 1-bromo-6-(4-methylphenyl)pyrene Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=C2)C3=C4C2=C(Br)C=CC4=CC=C13 MQNDWBDMDCOJJJ-UHFFFAOYSA-N 0.000 description 2
- UHPILNVIPDIPLG-UHFFFAOYSA-N 1-bromo-6-phenylpyrene Chemical compound C1=CC(C2=C34)=CC=C4C(Br)=CC=C3C=CC2=C1C1=CC=CC=C1 UHPILNVIPDIPLG-UHFFFAOYSA-N 0.000 description 2
- ZNFFNDGZOFVOSY-UHFFFAOYSA-N 1-bromo-7-tert-butyl-3-phenylpyrene Chemical compound C12=C3C=4C=CC1=CC(C(C)(C)C)=CC2=CC=C3C(Br)=CC=4C1=CC=CC=C1 ZNFFNDGZOFVOSY-UHFFFAOYSA-N 0.000 description 2
- RDPLDMAQCSKQAP-UHFFFAOYSA-N 1-bromo-7-tert-butylpyrene Chemical compound C1=CC(Br)=C2C=CC3=CC(C(C)(C)C)=CC4=CC=C1C2=C43 RDPLDMAQCSKQAP-UHFFFAOYSA-N 0.000 description 2
- XBYPYLBHOCRFSC-UHFFFAOYSA-N 1-bromo-8-phenylpyrene Chemical compound C12=C3C4=CC=C1C(Br)=CC=C2C=CC3=CC=C4C1=CC=CC=C1 XBYPYLBHOCRFSC-UHFFFAOYSA-N 0.000 description 2
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 2
- QRVQUBKLRBKFCG-UHFFFAOYSA-N 1-phenylpyrene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2)C3=C4C2=CC=CC4=CC=C13 QRVQUBKLRBKFCG-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- AYMGBIYWAZRPJY-UHFFFAOYSA-N 2-tert-butylpyrene Chemical compound C1=CC=C2C=CC3=CC(C(C)(C)C)=CC4=CC=C1C2=C43 AYMGBIYWAZRPJY-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- DKYHXVMLDCZITL-UHFFFAOYSA-N 7-tert-butyl-1-phenylpyrene Chemical compound C12=C3C=4C=CC1=CC(C(C)(C)C)=CC2=CC=C3C=CC=4C1=CC=CC=C1 DKYHXVMLDCZITL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- IJOBMDYMHCHXMZ-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1-c(c1ccc2cc3)ccc(cc4)c1c2c4c3-c(cc1)ccc1-c1c2[o]c3cc(-c4c(ccc(c5c(cc6)cc7)c6-c6c(C)cccc6)c5c7c(-c(cc5)ccc5-c5cccc6c5[o]c5ccccc65)c4)ccc3c2ccc1 Chemical compound CC(C)(C)c(cc1)ccc1-c(c1ccc2cc3)ccc(cc4)c1c2c4c3-c(cc1)ccc1-c1c2[o]c3cc(-c4c(ccc(c5c(cc6)cc7)c6-c6c(C)cccc6)c5c7c(-c(cc5)ccc5-c5cccc6c5[o]c5ccccc65)c4)ccc3c2ccc1 IJOBMDYMHCHXMZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- IFWCMHLBDWQEFI-UHFFFAOYSA-N Cc(cc1)ccc1-c(cc1)c(cc2)c3c1ccc1c3c2ccc1-c(cc1)ccc1-c1c2[o]c3ccccc3c2ccc1 Chemical compound Cc(cc1)ccc1-c(cc1)c(cc2)c3c1ccc1c3c2ccc1-c(cc1)ccc1-c1c2[o]c3ccccc3c2ccc1 IFWCMHLBDWQEFI-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical group N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound 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 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C07D405/02—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
- C07D405/10—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 carbon chain containing aromatic rings
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- H10K50/00—Organic light-emitting devices
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Description
化合物[22]の合成
1−ブロモピレン45g、4−メチルフェニルボロン酸21.7g、リン酸三カリウム34g、テトラブチルアンモニウムブロミド10.3g、酢酸パラジウム0.71gとジメチルホルムアミド1.6l(リットル)の混合溶液を窒素気流下、120℃で5時間加熱撹拌した。室温に冷却した後、水1.6lを注入し、室温で0.5時間撹拌した。析出した固体をろ取し、水200mlで2回洗浄した。得られた固体をジクロロメタン500mlに溶解し、硫酸マグネシウムで乾燥後、セライトを用いてろ過した。ろ液をエバポレートし、残さをメタノール200mlで2回洗浄し、析出した固体をろ取した。真空乾燥した後、1−(4−メチルフェニル)ピレン40gを得た。
1H−NMR(CDCl3(d=ppm)):2.52(s, 3H), 7.38-8.37(m, 23H)。
化合物[7]の合成
4−[4−(4,4,5,5−テトラメチル−[1,3,2]ジオキサボロラン−2−イル)フェニル]ジベンゾフランの代わりに3−(4,4,5,5−テトラメチル−[1,3,2]ジオキサボロラン−2−イル)ジベンゾフランを用いた以外は合成例1と同様の方法で合成し、淡黄色結晶を得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた淡黄色結晶が化合物[7]であることが確認された。
1H−NMR(CDCl3(d=ppm)):2.52(s, 3H), 7.38-7.66(m, 8H), 7.86(s, 1H) , 7.98-8.26(m, 10H)。
化合物[28]の合成
4−メチルフェニルボロン酸の代わりに2−ナフタレンボロン酸を用いた以外は合成例1と同様の方法で合成し、淡黄色結晶を得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた淡黄色結晶が化合物[28]であることが確認された。
1H−NMR(CDCl3(d=ppm)):7.37-8.39(m, 26H)。
化合物[36]の合成
4−メチルフェニルボロン酸の代わりに4−ビフェニルボロン酸を用いた以外は合成例1と同様の方法で合成し、淡黄色結晶を得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた淡黄色結晶が化合物[36]であることが確認された。
1H−NMR(CDCl3(d=ppm)):7.37-8.39(m, 28H)。
化合物[132]の合成
ピレン4.1g、t−ブチルクロリド2gとジクロロメタン33mlの混合溶液を窒素気流下、0℃に冷やし、塩化アルミニウム2.7gを加えた。この混合溶液を室温で3時間撹拌した後、水30mlを注入し、ジクロロメタン30mlで抽出した。有機層を水20mlで2回洗浄し、硫酸マグネシウムで乾燥後、エバポレートした。シリカゲルカラムクロマトグラフィーにより精製し、真空乾燥した後、2−t−ブチルピレン3g(含有率65%)を得た。
1H−NMR(CDCl3(d=ppm)):1.60(s, 9H), 7.35-8.36(m, 23H)。
化合物[140]の合成
フェニルボロン酸の代わりに2−ナフタレンボロン酸を用いた以外は合成例5と同様の方法で合成し、白色結晶を得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた白色結晶が化合物[140]であることが確認された。
1H−NMR(CDCl3(d=ppm)):1.61(s, 9H), 7.24-8.38(m, 25H)。
化合物[124]の合成
フェニルボロン酸の代わりに4−ジベンゾフランボロン酸、4−[4−(4,4,5,5−テトラメチル−[1,3,2]ジオキサボロラン−2−イル)フェニル]ジベンゾフランの代わりに4−ジベンゾフランボロン酸を用いた以外は合成例5と同様の方法で合成し、白色結晶を得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた白色結晶が化合物[124]であることが確認された。
1H−NMR(CDCl3(d=ppm)):1.60(s, 9H), 7.31-7.77(m, 10H), 7.98-8.31(m, 11H)。
化合物[138]の合成
フェニルボロン酸の代わりに4−ビフェニルボロン酸を用いた以外は合成例5と同様の方法で合成し、白色結晶を得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた白色結晶が化合物[138]であることが確認された。
1H−NMR(CDCl3(d=ppm)):1.61(s, 9H), 7.37-8.38(m, 27H)。
化合物[163]の合成
4−[4−(4,4,5,5−テトラメチル−[1,3,2]ジオキサボロラン−2−イル)フェニル]ジベンゾフランの代わりに2−[4−(4,4,5,5−テトラメチル−[1,3,2]ジオキサボロラン−2−イル)フェニル]ジベンゾフランを用いた以外は合成例1と同様の方法で合成し、淡黄色結晶を得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた淡黄色結晶が化合物[163]であることが確認された。
1H−NMR(CDCl3(d=ppm)):2.52(s, 3H), 7.38-8.31(m, 23H)。
化合物[21]の合成
1−ブロモピレン9.4g、フェニルボロン酸4.5g、炭酸セシウム13g、(トリ−t−ブチルホスフィン)テトラフルオロホウ酸塩348mg、ビス(ジベンジリデンアセトン)パラジウム(0)575mgと1,4−ジオキサン33mlの混合溶液を窒素気流下、100℃で3時間加熱撹拌した。溶液を室温に冷却した後、セライトを用いてろ過した。ろ液をエバポレートし、濃縮物をシリカゲルカラムクロマトグラフィーにより精製し、真空乾燥した後、1−フェニルピレン7.8gを得た。
1H−NMR(CDCl3(d=ppm)):7.38-8.38(m, 24H)。
30×40mmのガラス基板(旭硝子(株)製、15Ω/□、電子ビーム蒸着品)上にITO導電膜をガラス基板中央部分に150nmの厚さで30×13mmの大きさに形成し陽極とした。陽極が形成された基板を “セミコクリン(登録商標)56”(フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールで15分間超音波洗浄してから熱メタノールに15分間浸漬させて乾燥させた。素子を作製する直前にこの基板を1時間UV−オゾン処理し、さらに真空蒸着装置内に設置して、装置内の真空度が5×10−5Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として、銅フタロシアニンを10nm、正孔輸送材料として、4,4’−ビス(N−(1−ナフチル)−N−フェニルアミノ)ビフェニルを50nm蒸着した。次に、発光材料として、ホスト材料として、化合物[22]を、またドーパント材料として下記式に示すD−1をドープ濃度が5%になるように35nmの厚さに蒸着した。次に、電子輸送材料として、下記式に示すE−1を20nmの厚さに積層した。以上で形成した有機層上に、リチウムを0.5nmの厚さに蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニターの表示値である。この発光素子を10mA/cm2で直流駆動したところ、発光効率6.6lm/Wの高効率青色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は6400時間であった。
ホスト材料として表1に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。各実施例の結果は表1に示した。
ホスト材料として下記式に示すH−1を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率3.0lm/Wの青色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、400時間で輝度半減した。
ホスト材料として表1に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。各比較例の結果は表1に示した。なお表1のH−2、H−3、H−4、H−5、H−6、H−7は下記式で表される化合物である。
ドーパント材料として下記式に示すD−2をドープ濃度が2%となるように用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率4.7lm/Wの高効率青色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は4500時間であった。
ホスト材料およびドーパント材料として表2に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。各実施例の結果は表2に示した。なお表2のD−3、D−4、D−5、D−6、D−7、D−8は下記式で表される化合物である。
電子輸送材料として下記式で表されるE−2を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率3.3lm/Wの高効率青色発光が得られた。この発光素子を10mA/cm2で直流駆動したところ、輝度半減時間は3200時間であった。
ホスト材料および電子輸送材料として表3に記載した材料を用いた以外は、実施例1と同様にして発光素子を作製した。各実施例の結果は表3に示した。なお表2のE−3、E−4、E−5、E−6、E−7は下記式で表される化合物である。
ドーパント材料を用いなかったこと以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率1.2lm/Wの青色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は3500時間であった。
ホスト材料として化合物[132]を用いた以外は、実施例32と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率0.9lm/Wの青色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は3300時間であった。
ドーパント材料として下記に示すD−9をドープ濃度が5%となるように用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率6.0lm/Wの高効率緑色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は5000時間であった。
ドーパント材料として表4に記載した材料を用いた以外は、実施例34と同様にして発光素子を作製した。各実施例の結果は表4に示した。なお表4のD−10、D−11は下記式で表される化合物である。
ホスト材料として化合物[132]を用いた以外は、実施例34と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率5.6lm/Wの高効率緑色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は4900時間であった。
発光材料として、ホスト材料として化合物[22]を、ドーパント材料としてD−1をドープ濃度が5%になるように5nmの厚さに蒸着したのち、さらに発光材料として、ホスト材料として化合物[22]を、ドーパント材料として下記に示すD−12をドープ濃度が1%になるように30nmの厚さに積層した以外は、実施例1と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率7.0lm/Wの高効率白色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は7100時間であった。
ホスト材料として化合物[132]を用いた以外は、実施例38と同様にして発光素子を作製した。この発光素子を10mA/cm2で直流駆動したところ、発光効率6.6lm/Wの高効率白色発光が得られた。この発光素子を10mA/cm2の直流で連続駆動したところ、輝度半減時間は6100時間であった。
30×40mmのガラス基板(旭硝子(株)製、15Ω/□、電子ビーム蒸着品)上にITO導電膜をガラス基板中央部分に150nmの厚さで30×13mmの大きさに形成し陽極とした。陽極が形成された基板をアセトン、“セミコクリン(登録商標)56”(フルウチ化学(株)製)で各々15分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールで15分間超音波洗浄してから熱メタノールに15分間浸漬させて乾燥させた。この基板を素子を作製する直前に1時間UV−オゾン処理し、さらに真空蒸着装置内に設置して、装置内の真空度が5×10−4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料として4,4’−ビス(N−(m−トリル)−N−フェニルアミノ)ビフェニルを150nm蒸着した。次に、ホスト材料として化合物[22]を、またドーパント材料としてD−1をドープ濃度が5%になるように35nmの厚さに蒸着した。次に、電子輸送材料として、E−1を20nmの厚さに積層した。ここで言う膜厚は、水晶発振式膜厚モニターの表示値である。次に、厚さ50μmのコバール板にウエットエッチングによって16本の250μm開口部(残り幅50μm、300μmピッチに相当)を設けたマスクを、真空中でITOストライプに直交するようにマスク交換し、マスクとITO基板が密着するように裏面から磁石で固定した。そしてリチウムを0.5nm有機層にドーピングした後、アルミニウムを200nm蒸着して32×16ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
Claims (5)
- 一般式(1)で表されるピレン化合物を含有することを特徴とする発光素子材料。
(A)R 3 およびR 5 の少なくとも一つがアリール基またはヘテロアリール基である。
(B)R 3 およびR 5 が水素、R 4 がアルキル基、R 8 がアリール基またはヘテロアリール基である。) - Xがアリーレン基であることを特徴とする請求項1記載の発光素子材料。
- 陽極と陰極の間に少なくとも発光層が存在し、電気エネルギーにより発光する発光素子であって、発光素子が請求項1または2記載の発光素子材料を含有することを特徴とする発光素子。
- 発光層がホスト材料とドーパント材料を有し、一般式(1)で表される発光素子材料がホスト材料であることを特徴とする請求項3記載の発光素子。
- 発光層と陰極の間に少なくとも電子輸送層が存在し、電子輸送層が、電子受容性窒素を含み、さらに炭素、水素、窒素、酸素、ケイ素、リンの中から選ばれる元素で構成されるヘテロアリール環構造を有する化合物を含有することを特徴とする請求項3記載の発光素子。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019505091A (ja) * | 2016-04-28 | 2019-02-21 | エルジー・ケム・リミテッド | 有機発光素子 |
US11723268B2 (en) | 2016-04-28 | 2023-08-08 | Lg Chem, Ltd. | Organic light-emitting element |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130079658A (ko) * | 2005-09-08 | 2013-07-10 | 도레이 카부시키가이샤 | 발광 소자 재료 및 발광 소자 |
US8114530B2 (en) * | 2007-07-10 | 2012-02-14 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device utilizing the same |
CN102084514A (zh) | 2008-07-01 | 2011-06-01 | 东丽株式会社 | 发光元件 |
JP2010150235A (ja) * | 2008-11-27 | 2010-07-08 | Canon Inc | 化合物の製造方法 |
KR101195655B1 (ko) | 2009-03-30 | 2012-10-30 | 도레이 카부시키가이샤 | 발광 소자 재료 및 발광 소자 |
US8431250B2 (en) | 2009-04-24 | 2013-04-30 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescent element comprising the same |
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KR101912675B1 (ko) * | 2010-10-04 | 2018-10-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 복합 재료, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
KR101950363B1 (ko) * | 2010-10-29 | 2019-02-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 페난트렌 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
US20120234392A1 (en) * | 2011-03-17 | 2012-09-20 | Semiconductor Energy Laboratory Co., Ltd. | Photoelectric conversion device |
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US20140027754A1 (en) | 2011-06-15 | 2014-01-30 | Toray Industries, Inc. | Light emitting device material and light emitting device |
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KR101918953B1 (ko) | 2012-03-06 | 2018-11-16 | 삼성디스플레이 주식회사 | 아민계 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 유기 발광 장치 |
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EP3182478B1 (en) * | 2015-12-18 | 2018-11-28 | Novaled GmbH | Electron injection layer for an organic light-emitting diode (oled) |
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CN111848413B (zh) * | 2020-07-27 | 2022-07-15 | 山东理工大学 | 一类沿短轴修饰的芘基衍生物及其制备方法和应用 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004096945A1 (ja) * | 2003-05-01 | 2004-11-11 | Fujitsu Limited | 1,3,6,8−四置換ピレン化合物、有機el素子及び有機elディスプレイ |
WO2006128800A1 (en) * | 2005-05-30 | 2006-12-07 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
JP2007077094A (ja) * | 2005-09-15 | 2007-03-29 | Mitsui Chemicals Inc | 芳香族化合物、該芳香族化合物を含有する有機電界発光素子 |
JP2007169581A (ja) * | 2005-11-25 | 2007-07-05 | Toray Ind Inc | 発光素子材料および発光素子 |
JP2007238500A (ja) * | 2006-03-08 | 2007-09-20 | Mitsui Chemicals Inc | アントラセン化合物および該化合物を含有する有機電界発光素子 |
JP4830750B2 (ja) * | 2006-09-21 | 2011-12-07 | 東レ株式会社 | 発光素子材料および発光素子 |
JP5029013B2 (ja) * | 2005-09-08 | 2012-09-19 | 東レ株式会社 | 発光素子材料および発光素子 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4429438B2 (ja) | 1999-01-19 | 2010-03-10 | 出光興産株式会社 | アミノ化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2002063988A (ja) | 2000-08-22 | 2002-02-28 | Toray Ind Inc | 発光素子 |
JP2004075567A (ja) | 2002-08-12 | 2004-03-11 | Idemitsu Kosan Co Ltd | オリゴアリーレン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
TW593624B (en) | 2002-10-16 | 2004-06-21 | Univ Tsinghua | Aromatic compounds and organic LED |
KR20050109940A (ko) * | 2003-02-14 | 2005-11-22 | 이데미쓰 고산 가부시키가이샤 | 복소 다환계 화합물, 이를 이용한 색소, 안료 또는 염료,색변환 재료 조성물 및 색변환막 |
JP2006176494A (ja) * | 2004-11-25 | 2006-07-06 | Kyoto Univ | ピレン系化合物及びこれを用いた発光トランジスタ素子及びエレクトロルミネッセンス素子 |
TWI312804B (en) * | 2005-04-01 | 2009-08-01 | Tetrahedron Technology Corporatio | Triazine compounds |
US20090278115A1 (en) * | 2005-07-11 | 2009-11-12 | Idemitsu Kosan Co., Ltd. | Nitrogen-containing heterocyclic derivative and organic electroluminescence element using the same |
-
2008
- 2008-02-28 KR KR1020097016682A patent/KR101475309B1/ko active IP Right Grant
- 2008-02-28 CN CN200880007460XA patent/CN101627102B/zh active Active
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- 2008-02-28 US US12/529,829 patent/US7989802B2/en active Active
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004096945A1 (ja) * | 2003-05-01 | 2004-11-11 | Fujitsu Limited | 1,3,6,8−四置換ピレン化合物、有機el素子及び有機elディスプレイ |
WO2006128800A1 (en) * | 2005-05-30 | 2006-12-07 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
JP5029013B2 (ja) * | 2005-09-08 | 2012-09-19 | 東レ株式会社 | 発光素子材料および発光素子 |
JP2007077094A (ja) * | 2005-09-15 | 2007-03-29 | Mitsui Chemicals Inc | 芳香族化合物、該芳香族化合物を含有する有機電界発光素子 |
JP2007169581A (ja) * | 2005-11-25 | 2007-07-05 | Toray Ind Inc | 発光素子材料および発光素子 |
JP2007238500A (ja) * | 2006-03-08 | 2007-09-20 | Mitsui Chemicals Inc | アントラセン化合物および該化合物を含有する有機電界発光素子 |
JP4830750B2 (ja) * | 2006-09-21 | 2011-12-07 | 東レ株式会社 | 発光素子材料および発光素子 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019505091A (ja) * | 2016-04-28 | 2019-02-21 | エルジー・ケム・リミテッド | 有機発光素子 |
US11723268B2 (en) | 2016-04-28 | 2023-08-08 | Lg Chem, Ltd. | Organic light-emitting element |
US12082498B2 (en) | 2016-04-28 | 2024-09-03 | Lg Chem, Ltd. | Organic light-emitting element |
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