US20120305908A1 - Organic electroluminescence device and display - Google Patents
Organic electroluminescence device and display Download PDFInfo
- Publication number
- US20120305908A1 US20120305908A1 US13/585,132 US201213585132A US2012305908A1 US 20120305908 A1 US20120305908 A1 US 20120305908A1 US 201213585132 A US201213585132 A US 201213585132A US 2012305908 A1 US2012305908 A1 US 2012305908A1
- Authority
- US
- United States
- Prior art keywords
- group
- substituted
- unsubstituted
- carbon atoms
- formula
- 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.)
- Abandoned
Links
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 94
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 36
- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical group C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 claims abstract description 31
- 239000002019 doping agent Substances 0.000 claims abstract description 29
- 125000001935 tetracenyl group Chemical class C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims abstract description 28
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 129
- -1 dibenzoanthracene Chemical compound 0.000 claims description 123
- 125000003118 aryl group Chemical group 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000003277 amino group Chemical group 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000005493 quinolyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 125000003172 aldehyde group Chemical group 0.000 claims description 9
- 125000005013 aryl ether group Chemical group 0.000 claims description 9
- 150000004832 aryl thioethers Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000004185 ester group Chemical group 0.000 claims description 9
- 125000005401 siloxanyl group Chemical group 0.000 claims description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005567 fluorenylene group Chemical group 0.000 claims description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005551 pyridylene group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229960000956 coumarin Drugs 0.000 claims description 3
- 235000001671 coumarin Nutrition 0.000 claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 claims description 2
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 2
- KHNYNFUTFKJLDD-UHFFFAOYSA-N Benzo[j]fluoranthene Chemical compound C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- JNTHRSHGARDABO-UHFFFAOYSA-N dibenzo[a,l]pyrene Chemical compound C1=CC=CC2=C3C4=CC=CC=C4C=C(C=C4)C3=C3C4=CC=CC3=C21 JNTHRSHGARDABO-UHFFFAOYSA-N 0.000 claims description 2
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229930003944 flavone Natural products 0.000 claims description 2
- 150000002212 flavone derivatives Chemical class 0.000 claims description 2
- 235000011949 flavones Nutrition 0.000 claims description 2
- VLUUZERMKSSBKW-UHFFFAOYSA-N hexacyclo[14.7.1.02,15.03,12.06,11.020,24]tetracosa-1(23),2(15),3(12),4,6,8,10,13,16,18,20(24),21-dodecaene Chemical compound C1=CC(C2=C3C=CC=4C(C3=CC=C22)=CC=CC=4)=C3C2=CC=CC3=C1 VLUUZERMKSSBKW-UHFFFAOYSA-N 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 2
- 229950000688 phenothiazine Drugs 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 150000003518 tetracenes Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 55
- 239000010410 layer Substances 0.000 description 223
- 238000004020 luminiscence type Methods 0.000 description 43
- 230000002829 reductive effect Effects 0.000 description 20
- 0 CC1=C(C)C(C)=C2C(C)=C3C(C)=C4C(C)=C(C)C(C)=C(C)C4=C(C)C3=C(C)C2=C1C.[15*]C1=C([16*])C([17*])=N/C1=C(/[21*])C1=C([20*])C([19*])=C([18*])N1 Chemical compound CC1=C(C)C(C)=C2C(C)=C3C(C)=C4C(C)=C(C)C(C)=C(C)C4=C(C)C3=C(C)C2=C1C.[15*]C1=C([16*])C([17*])=N/C1=C(/[21*])C1=C([20*])C([19*])=C([18*])N1 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 229910052783 alkali metal Inorganic materials 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000010408 film Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 239000010409 thin film Substances 0.000 description 14
- 150000001340 alkali metals Chemical class 0.000 description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 238000001771 vacuum deposition Methods 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 229910052792 caesium Inorganic materials 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000001725 pyrenyl group Chemical group 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 230000037230 mobility Effects 0.000 description 5
- 229960003540 oxyquinoline Drugs 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 150000002910 rare earth metals Chemical class 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 230000032258 transport Effects 0.000 description 5
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical group C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 125000005133 alkynyloxy group Chemical group 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- 125000000707 boryl group Chemical group B* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 2
- 229910001634 calcium fluoride Inorganic materials 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000012212 insulator Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 2
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005548 pyrenylene group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000003967 siloles Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 125000003944 tolyl group Chemical group 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 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910017083 AlN Inorganic materials 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QCEOSYBXVSOSET-UHFFFAOYSA-N C.C.CNC(C)COC Chemical compound C.C.CNC(C)COC QCEOSYBXVSOSET-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K C1=CC2=CC=CC3=C2N(=C1)[Al]12(OC4=CC=CC5=CC=CN1=C54)(O3)O/C1=C/C=C\C3=C1N2=CC=C3 Chemical compound C1=CC2=CC=CC3=C2N(=C1)[Al]12(OC4=CC=CC5=CC=CN1=C54)(O3)O/C1=C/C=C\C3=C1N2=CC=C3 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- HPQUISQBRAIEGK-UHFFFAOYSA-N C1=CC=C(C(C2=CC=CC=C2)=C(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C(C3=CC=CC=C3)=C(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(C4=CC=CC=C4)C4=CC=CC=C4C(C4=CC=CC=C4)=C23)C=C1.C1=CC=C(C2=C3C(C4=CC5=CC=CC=C5C=C4)=C4C=CC=CC4=C(C4=CC5=CC=CC=C5C=C4)C3=C(C3=CC=CC=C3)C3=CC=CC=C32)C=C1.C1=CC=C(C2=C3C(C4=CC=C(N(C5=CC=CC=C5)C5=CC=CC=C5)C=C4)=C4C=CC=CC4=C(C4=CC=C(N(C5=CC=CC=C5)C5=CC=CC=C5)C=C4)C3=C(C3=CC=CC=C3)C3=CC=CC=C32)C=C1 Chemical compound C1=CC=C(C(C2=CC=CC=C2)=C(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C(C3=CC=CC=C3)=C(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(C4=CC=CC=C4)C4=CC=CC=C4C(C4=CC=CC=C4)=C23)C=C1.C1=CC=C(C2=C3C(C4=CC5=CC=CC=C5C=C4)=C4C=CC=CC4=C(C4=CC5=CC=CC=C5C=C4)C3=C(C3=CC=CC=C3)C3=CC=CC=C32)C=C1.C1=CC=C(C2=C3C(C4=CC=C(N(C5=CC=CC=C5)C5=CC=CC=C5)C=C4)=C4C=CC=CC4=C(C4=CC=C(N(C5=CC=CC=C5)C5=CC=CC=C5)C=C4)C3=C(C3=CC=CC=C3)C3=CC=CC=C32)C=C1 HPQUISQBRAIEGK-UHFFFAOYSA-N 0.000 description 1
- KPZCRMHRSCQGTK-UHFFFAOYSA-N C1=CC=C(C2=C3C=CC=CC3=C(C3=CC=CC=C3)C3=C(C4=CC=CC=C4)C4=CC=CC=C4C(C4=CC=CC=C4)=C23)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC6=CC=CC=C6C=C5)C5=CC=CC=C5C(C5=CC=C6C=CC=CC6=C5)=C34)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC=C(C6=CC=CC=C6)C=C5)C5=CC=CC=C5C(C5=CC=C(C6=CC=CC=C6)C=C5)=C34)C=C2)C=C1 Chemical compound C1=CC=C(C2=C3C=CC=CC3=C(C3=CC=CC=C3)C3=C(C4=CC=CC=C4)C4=CC=CC=C4C(C4=CC=CC=C4)=C23)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC6=CC=CC=C6C=C5)C5=CC=CC=C5C(C5=CC=C6C=CC=CC6=C5)=C34)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC=C(C6=CC=CC=C6)C=C5)C5=CC=CC=C5C(C5=CC=C(C6=CC=CC=C6)C=C5)=C34)C=C2)C=C1 KPZCRMHRSCQGTK-UHFFFAOYSA-N 0.000 description 1
- VCPVYFHDNCSQEV-UHFFFAOYSA-N C1=CC=C(C2=C3C=CC=CC3=C(C3=CC=CC=C3)C3=C(C4=CC=CC=C4)C4=CC=CC=C4C(C4=CC=CC=C4)=C23)C=C1.CC1=CC=C(C2=C(C3=CC=CC=C3)C(C)=C3C(C4=CC=CC=C4)=C4C(C)=C(C5=CC=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1 Chemical compound C1=CC=C(C2=C3C=CC=CC3=C(C3=CC=CC=C3)C3=C(C4=CC=CC=C4)C4=CC=CC=C4C(C4=CC=CC=C4)=C23)C=C1.CC1=CC=C(C2=C(C3=CC=CC=C3)C(C)=C3C(C4=CC=CC=C4)=C4C(C)=C(C5=CC=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1 VCPVYFHDNCSQEV-UHFFFAOYSA-N 0.000 description 1
- AVCYLMDFKLYQJM-UHFFFAOYSA-N C1=CC=C(C2=CC=C(C3=C4C(C5=CC=C(C6=CC=CC=C6C6=CC=CC=C6)C=C5)=C5C=CC=CC5=C(C5=CC=C(C6=C(C7=CC=CC=C7)C=CC=C6)C=C5)C4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC=CC=C5)C5=CC(C6=CC=CC=C6)=C(C6=CC=CC=C6)C=C5C(C5=CC=CC=C5)=C34)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=CC=C(C4=C5C=CC=CC5=C(C5=CC=C(C6=CC=C(C7=CC=CC=C7)C=C6)C=C5)C5=C(C6=CC=C(C7=CC=CC=C7)C=C6)C6=CC=CC=C6C(C6=CC=C(C7=CC=CC=C7)C=C6)=C45)C=C3)C=C2)C=C1 Chemical compound C1=CC=C(C2=CC=C(C3=C4C(C5=CC=C(C6=CC=CC=C6C6=CC=CC=C6)C=C5)=C5C=CC=CC5=C(C5=CC=C(C6=C(C7=CC=CC=C7)C=CC=C6)C=C5)C4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC=CC=C5)C5=CC(C6=CC=CC=C6)=C(C6=CC=CC=C6)C=C5C(C5=CC=CC=C5)=C34)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=CC=C(C4=C5C=CC=CC5=C(C5=CC=C(C6=CC=C(C7=CC=CC=C7)C=C6)C=C5)C5=C(C6=CC=C(C7=CC=CC=C7)C=C6)C6=CC=CC=C6C(C6=CC=C(C7=CC=CC=C7)C=C6)=C45)C=C3)C=C2)C=C1 AVCYLMDFKLYQJM-UHFFFAOYSA-N 0.000 description 1
- GSLOMNDFUIQEQW-UHFFFAOYSA-N C1=CC=C(C2=CC=C(C3=C4C(C5=CC=CC=C5)=C5C=CC=CC5=C(C5=CC=CC=C5)C4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=C(C5=CC=CC=C5)C=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC=CC=C5)C5=CC=CC=C5C(C5=CC=CC=C5)=C34)C(C3=CC=CC=C3)=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=C(C5=CC=CC=C5)C=C(C5=CC=CC=C5)C=C4)C4=CC5=CC=CC=C5C=C43)C(C3=CC=CC=C3)=C2)C=C1 Chemical compound C1=CC=C(C2=CC=C(C3=C4C(C5=CC=CC=C5)=C5C=CC=CC5=C(C5=CC=CC=C5)C4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=C(C5=CC=CC=C5)C=C(C5=CC=CC=C5)C=C4)C4=C(C5=CC=CC=C5)C5=CC=CC=C5C(C5=CC=CC=C5)=C34)C(C3=CC=CC=C3)=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C(C4=C(C5=CC=CC=C5)C=C(C5=CC=CC=C5)C=C4)C4=CC5=CC=CC=C5C=C43)C(C3=CC=CC=C3)=C2)C=C1 GSLOMNDFUIQEQW-UHFFFAOYSA-N 0.000 description 1
- SBIHFZWWHPXEFQ-UHFFFAOYSA-N C1=CC=C(C2=CC=C(C3=C4C=C5C=CC=CC5=CC4=C(C4=C(C5=CC=CC=C5)C=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C(C3=CC=CC=C3)=C2)C=C1 Chemical compound C1=CC=C(C2=CC=C(C3=C4C=C5C=CC=CC5=CC4=C(C4=C(C5=CC=CC=C5)C=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C(C3=CC=CC=C3)=C2)C=C1 SBIHFZWWHPXEFQ-UHFFFAOYSA-N 0.000 description 1
- FJCDTHMWPZHRIM-UHFFFAOYSA-N C1=CC=C(C2=CC=C(C3=C4C=C5C=CC=CC5=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1 Chemical compound C1=CC=C(C2=CC=C(C3=C4C=C5C=CC=CC5=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1 FJCDTHMWPZHRIM-UHFFFAOYSA-N 0.000 description 1
- RPVKHOYSGFGZSH-UHFFFAOYSA-N C1=CC=C(C2=CC=C(C3=C4C=C5C=CC=CC5=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=CC=C(C4=C5C=CC=CC5=C(C5=CC=C(C6=CC=C(C7=CC=CC=C7)C=C6)C=C5)C5=C(C6=CC=CC=C6)C6=CC=CC=C6C(C6=CC=CC=C6)=C45)C=C3)C=C2)C=C1.C1=CC=C(C2=CC=CC=C2C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=C(C6=CC=CC=C6)C=CC=C5)C=C4)C4=C(C5=CC=CC=C5)C5=CC=CC=C5C(C5=CC=CC=C5)=C34)C=C2)C=C1 Chemical compound C1=CC=C(C2=CC=C(C3=C4C=C5C=CC=CC5=CC4=C(C4=CC=C(C5=CC=CC=C5)C=C4)C4=CC=CC=C43)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=CC=C(C4=C5C=CC=CC5=C(C5=CC=C(C6=CC=C(C7=CC=CC=C7)C=C6)C=C5)C5=C(C6=CC=CC=C6)C6=CC=CC=C6C(C6=CC=CC=C6)=C45)C=C3)C=C2)C=C1.C1=CC=C(C2=CC=CC=C2C2=CC=C(C3=C4C=CC=CC4=C(C4=CC=C(C5=C(C6=CC=CC=C6)C=CC=C5)C=C4)C4=C(C5=CC=CC=C5)C5=CC=CC=C5C(C5=CC=CC=C5)=C34)C=C2)C=C1 RPVKHOYSGFGZSH-UHFFFAOYSA-N 0.000 description 1
- BLFYVWGNANEYAJ-UHFFFAOYSA-N C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=C(C5=CC=C(C6=NN=C(C7=CC=C(C8=CC=CC=C8)C=C7)O6)C=C5)C=C4)O3)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=C(OC5=CC=C(C6=NN=C(C7=CC=C(C8=CC=CC=C8)C=C7)O6)C=C5)C=C4)O3)C=C2)C=C1.CC(C)(C)C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=C(C5=CC=C(C6=NN=C(C7=CC=C(C8=CC=C(C(C)(C)C)C=C8)C=C7)O6)C=C5)C=C4)O3)C=C2)C=C1.CC(C)(C)C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=CC=C4)O3)C=C2)C=C1.CC1=CC(C2=CC(C)=C(C3=NN=C(C4=C5C=CC=CC5=CC=C4)O3)C=C2)=CC=C1C1=NN=C(C2=CC=CC3=C2C=CC=C3)O1 Chemical compound C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=C(C5=CC=C(C6=NN=C(C7=CC=C(C8=CC=CC=C8)C=C7)O6)C=C5)C=C4)O3)C=C2)C=C1.C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=C(OC5=CC=C(C6=NN=C(C7=CC=C(C8=CC=CC=C8)C=C7)O6)C=C5)C=C4)O3)C=C2)C=C1.CC(C)(C)C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=C(C5=CC=C(C6=NN=C(C7=CC=C(C8=CC=C(C(C)(C)C)C=C8)C=C7)O6)C=C5)C=C4)O3)C=C2)C=C1.CC(C)(C)C1=CC=C(C2=CC=C(C3=NN=C(C4=CC=CC=C4)O3)C=C2)C=C1.CC1=CC(C2=CC(C)=C(C3=NN=C(C4=C5C=CC=CC5=CC=C4)O3)C=C2)=CC=C1C1=NN=C(C2=CC=CC3=C2C=CC=C3)O1 BLFYVWGNANEYAJ-UHFFFAOYSA-N 0.000 description 1
- PHBJYIUTTPNUBD-UHFFFAOYSA-N C1=CC=C(C2=NC3=C(C=CC=C3)N2C2=CC=C(C3=C4C=CC=CC4=C(C4=CC5=C(C=CC=C5)C=C4)C4=C3C=CC=C4)C=C2)C=C1 Chemical compound C1=CC=C(C2=NC3=C(C=CC=C3)N2C2=CC=C(C3=C4C=CC=CC4=C(C4=CC5=C(C=CC=C5)C=C4)C4=C3C=CC=C4)C=C2)C=C1 PHBJYIUTTPNUBD-UHFFFAOYSA-N 0.000 description 1
- JXOUADPUMDUUHT-UHFFFAOYSA-N CC(=O)OC1=C(C2=C3C=CC(C4=C(C)OC5=C4C=CC=C5)=N3B(F)(F)N3C(C4=C(C)OC5=C4C=CC=C5)=CC=C23)C=CC=C1.FB1(F)N2C(=CC=C2C2=CC=C(C3=CC=CC=C3)C=C2)C=C2C=CC(C3=CC=C(C4=CC=CC=C4)C=C3)=N21.FB1(F)N2C(C3=C4C=CC=CC4=C4C=CC=CC4=C3)=CC(C3=CC4=C(C=CC=C4)C4=C3C=CC=C4)=C2C=C2C(C3=C4C=CC=CC4=C4C=CC=CC4=C3)=CC(C3=CC4=C(C=CC=C4)C4=C3C=CC=C4)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2N=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21 Chemical compound CC(=O)OC1=C(C2=C3C=CC(C4=C(C)OC5=C4C=CC=C5)=N3B(F)(F)N3C(C4=C(C)OC5=C4C=CC=C5)=CC=C23)C=CC=C1.FB1(F)N2C(=CC=C2C2=CC=C(C3=CC=CC=C3)C=C2)C=C2C=CC(C3=CC=C(C4=CC=CC=C4)C=C3)=N21.FB1(F)N2C(C3=C4C=CC=CC4=C4C=CC=CC4=C3)=CC(C3=CC4=C(C=CC=C4)C4=C3C=CC=C4)=C2C=C2C(C3=C4C=CC=CC4=C4C=CC=CC4=C3)=CC(C3=CC4=C(C=CC=C4)C4=C3C=CC=C4)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2N=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21 JXOUADPUMDUUHT-UHFFFAOYSA-N 0.000 description 1
- CAZBXLIDLQYUGQ-UHFFFAOYSA-N CC(C)(C)C1=CC=C(C2=C3C4=C(C=CC=C4)C=CC3=C3C=C4C5=C(C6=C(C=CC=C6)C=C5)C(C5=CC=C(C(C)(C)C)C=C5)=N4B(F)(F)N32)C=C1.CN1C(=O)C2=C(C3=CC=C(C4=CC=C5C=C6C=CC(C7=CC=C(C8=C9C(=O)N(C)C(C%10=CC=CC=C%10)=C9C(=O)N8C)C=C7)=N6B(F)(F)N54)C=C3)N(C)C(=O)C2=C1C1=CC=CC=C1.COC1=CC=C(C2=C3C4=C(C=CC=C4)C=CC3=C3C=C4C5=C(C6=C(C=CC=C6)C=C5)C(C5=CC=C(OC)C=C5)=N4B(F)(F)N32)C=C1.FB1(F)N2C(=C3C4=C(C=CC=C4)C=CC3=C2C2=CC=CC=C2)C=C2C3=C(C=CC4=C3C=CC=C4)C(C3=CC=CC=C3)=N21.FB1(F)N2C(=C3C=CC4=C(C=CC=C4)C3=C2C2=CC=NC=C2)C=C2C3=C(C4=C(C=CC=C4)C=C3)C(C3=CC=NC=C3)=N21 Chemical compound CC(C)(C)C1=CC=C(C2=C3C4=C(C=CC=C4)C=CC3=C3C=C4C5=C(C6=C(C=CC=C6)C=C5)C(C5=CC=C(C(C)(C)C)C=C5)=N4B(F)(F)N32)C=C1.CN1C(=O)C2=C(C3=CC=C(C4=CC=C5C=C6C=CC(C7=CC=C(C8=C9C(=O)N(C)C(C%10=CC=CC=C%10)=C9C(=O)N8C)C=C7)=N6B(F)(F)N54)C=C3)N(C)C(=O)C2=C1C1=CC=CC=C1.COC1=CC=C(C2=C3C4=C(C=CC=C4)C=CC3=C3C=C4C5=C(C6=C(C=CC=C6)C=C5)C(C5=CC=C(OC)C=C5)=N4B(F)(F)N32)C=C1.FB1(F)N2C(=C3C4=C(C=CC=C4)C=CC3=C2C2=CC=CC=C2)C=C2C3=C(C=CC4=C3C=CC=C4)C(C3=CC=CC=C3)=N21.FB1(F)N2C(=C3C=CC4=C(C=CC=C4)C3=C2C2=CC=NC=C2)C=C2C3=C(C4=C(C=CC=C4)C=C3)C(C3=CC=NC=C3)=N21 CAZBXLIDLQYUGQ-UHFFFAOYSA-N 0.000 description 1
- LQTRJSBBZVQIRM-UHFFFAOYSA-N CC.CC.CN(C)C1=CC=C(C2=CC=C(N(C)C)C=C2)C=C1 Chemical compound CC.CC.CN(C)C1=CC=C(C2=CC=C(N(C)C)C=C2)C=C1 LQTRJSBBZVQIRM-UHFFFAOYSA-N 0.000 description 1
- DVHRSKHJXVSBSZ-UHFFFAOYSA-N CC1=C(C)C(C)=C(C2=C3C(C)=C(C)C(C)=C(C)C3=C(C3=C(C)C(C)=C(C)C(C)=C3C)C3=C2C(C)=C2C(C)=C(C)C(C)=C(C)C2=C3C)C(C)=C1C Chemical compound CC1=C(C)C(C)=C(C2=C3C(C)=C(C)C(C)=C(C)C3=C(C3=C(C)C(C)=C(C)C(C)=C3C)C3=C2C(C)=C2C(C)=C(C)C(C)=C(C)C2=C3C)C(C)=C1C DVHRSKHJXVSBSZ-UHFFFAOYSA-N 0.000 description 1
- OWYBEMJVGUEIDP-UHFFFAOYSA-N CC1=C(C)C=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=C3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=N3B(F)(F)N3C(C4=CC=C(C)C=C4)=C4C=CC=CC4=C23)C=C1.CC1=CC=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=CC(C2=CC(C3=CC=CC=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=C(C)C=CC(C)=C4)N2B3(F)F)=C1 Chemical compound CC1=C(C)C=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=C3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=N3B(F)(F)N3C(C4=CC=C(C)C=C4)=C4C=CC=CC4=C23)C=C1.CC1=CC=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=CC(C2=CC(C3=CC=CC=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=C(C)C=CC(C)=C4)N2B3(F)F)=C1 OWYBEMJVGUEIDP-UHFFFAOYSA-N 0.000 description 1
- URCOQFRYOVZQOL-UHFFFAOYSA-N CC1=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=CC=C1.CC1=CC(C)=CC(C2=N3C(=C(C4=CC=CC=C4)C4=C5C=CC=CC5=C(C5=C(C)C=C(C)C=C5C)N4B3(F)F)C(C3=CC=CC=C3)=C2)=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=C(C)C(C)=CC4=C(C4=C(C)C=C(C)C=C4C)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 Chemical compound CC1=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=CC=C1.CC1=CC(C)=CC(C2=N3C(=C(C4=CC=CC=C4)C4=C5C=CC=CC5=C(C5=C(C)C=C(C)C=C5C)N4B3(F)F)C(C3=CC=CC=C3)=C2)=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=C(C)C(C)=CC4=C(C4=C(C)C=C(C)C=C4C)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 URCOQFRYOVZQOL-UHFFFAOYSA-N 0.000 description 1
- DECMDVPDLRKYQB-UHFFFAOYSA-N CC1=C(C2=CC=CC=C2)C(C2=CC=CC=C2)=N2C1=C(C1=CC=C(C(C)(C)C)C=C1)C1=C(C)C(C3=CC=CC=C3)=C(C3=CC=CC=C3)N1B2(F)F Chemical compound CC1=C(C2=CC=CC=C2)C(C2=CC=CC=C2)=N2C1=C(C1=CC=C(C(C)(C)C)C=C1)C1=C(C)C(C3=CC=CC=C3)=C(C3=CC=CC=C3)N1B2(F)F DECMDVPDLRKYQB-UHFFFAOYSA-N 0.000 description 1
- NHCAMHYIYGLGHA-UHFFFAOYSA-N CC1=C(C2=CC=CC=C2)C(C2=CC=CC=C2)=N2C1=C(C1=CC=C(C(C)(C)C)C=C1)C1=C(C)C(C3=CC=CC=C3)=C(C3=CC=CC=C3)N1B2(F)F.CC1=CC=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC(C)=CC=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C Chemical compound CC1=C(C2=CC=CC=C2)C(C2=CC=CC=C2)=N2C1=C(C1=CC=C(C(C)(C)C)C=C1)C1=C(C)C(C3=CC=CC=C3)=C(C3=CC=CC=C3)N1B2(F)F.CC1=CC=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC(C)=CC=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C NHCAMHYIYGLGHA-UHFFFAOYSA-N 0.000 description 1
- WJEVXMURJBSSNS-UHFFFAOYSA-N CC1=C2C3=C(C=CC=C3)C(C)=N2B(F)(F)N2C(C)=C3C=CC=CC3=C12.CC1=C2C=CC=CC2=C2C(C3=CC=CC=C3)=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N12.CC1=CC2=C(C=C1C)C(C)=N1C2=C(C)C2=C3C=C(C)C(C)=CC3=C(C)N2B1(F)F.CC1=CC=C(C2=C3C=CC=CC3=C3N=C4C(C5=CC(C)=CC(C)=C5)=CC(C5=CC(C)=CC(C)=C5)=N4B(F)(F)N32)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=CC(C)=CC(C)=C4)N3B(F)(F)N2=C1C Chemical compound CC1=C2C3=C(C=CC=C3)C(C)=N2B(F)(F)N2C(C)=C3C=CC=CC3=C12.CC1=C2C=CC=CC2=C2C(C3=CC=CC=C3)=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N12.CC1=CC2=C(C=C1C)C(C)=N1C2=C(C)C2=C3C=C(C)C(C)=CC3=C(C)N2B1(F)F.CC1=CC=C(C2=C3C=CC=CC3=C3N=C4C(C5=CC(C)=CC(C)=C5)=CC(C5=CC(C)=CC(C)=C5)=N4B(F)(F)N32)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=CC(C)=CC(C)=C4)N3B(F)(F)N2=C1C WJEVXMURJBSSNS-UHFFFAOYSA-N 0.000 description 1
- AABHCMJTJNYEMN-UHFFFAOYSA-N CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C(C)=C1 Chemical compound CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C(C)=C1 AABHCMJTJNYEMN-UHFFFAOYSA-N 0.000 description 1
- CJLDXRIPIZMEPU-UHFFFAOYSA-N CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C(C)=C1.CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C(C)=C1.CC1=CC=C(C2=C(C3=CC=CC=C3)C(C)=C3C(C4=CC=CC=C4)=C4C(C)=C(C5=CC=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1 Chemical compound CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C(C)=C1.CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C(C)=C1.CC1=CC=C(C2=C(C3=CC=CC=C3)C(C)=C3C(C4=CC=CC=C4)=C4C(C)=C(C5=CC=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1 CJLDXRIPIZMEPU-UHFFFAOYSA-N 0.000 description 1
- LKSIFYWHRLEXGR-UHFFFAOYSA-N CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C(C)=C1 Chemical compound CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C(C)=C1 LKSIFYWHRLEXGR-UHFFFAOYSA-N 0.000 description 1
- SBULKGYOAJUCPR-UHFFFAOYSA-N CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C(C)=C1.CC1=CC=C(C2=C3C=CC(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC(C)=C(C)C=C4)N3B(F)(F)N2=C1C Chemical compound CC1=CC(C)=C(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C(C)=C1.CC1=CC=C(C2=C3C=CC(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC(C)=C(C)C=C4)N3B(F)(F)N2=C1C SBULKGYOAJUCPR-UHFFFAOYSA-N 0.000 description 1
- XKFMITGHHHUMDI-UHFFFAOYSA-N CC1=CC(C)=CC(C2=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N3C(C)=C4C=CC=CC4=C23)=C1.CC1=CC2=C(C(C)=C1C)C1=C(C)C3=C4C(C)=C(C)C(C)=C(C)C4=C(C)N3B(F)(F)N1=C2C.CC1=CC2=C(C=C1)C1=C(C)C3=C4C=CC(C)=CC4=C(C)N3B(F)(F)N1=C2C.CC1=CC=C(C2=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N3C(C)=C4C=CC=CC4=C23)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3N=C4C(C5=CC(C)=CC(C)=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=C(C)C(C)=CC=C4)N3B(F)(F)N2=C1C Chemical compound CC1=CC(C)=CC(C2=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N3C(C)=C4C=CC=CC4=C23)=C1.CC1=CC2=C(C(C)=C1C)C1=C(C)C3=C4C(C)=C(C)C(C)=C(C)C4=C(C)N3B(F)(F)N1=C2C.CC1=CC2=C(C=C1)C1=C(C)C3=C4C=CC(C)=CC4=C(C)N3B(F)(F)N1=C2C.CC1=CC=C(C2=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N3C(C)=C4C=CC=CC4=C23)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3N=C4C(C5=CC(C)=CC(C)=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=C(C)C(C)=CC=C4)N3B(F)(F)N2=C1C XKFMITGHHHUMDI-UHFFFAOYSA-N 0.000 description 1
- VMAOQDKIFZZMEA-UHFFFAOYSA-N CC1=CC(C)=CC(C2=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N3C(C)=C4C=CC=CC4=C23)=C1.CC1=CC2=C(C=C1)C1=C(C3=CC=CC=C3)C3=C4C=CC(C)=CC4=C(C4=CC=C(C)C(C)=C4)N3B(F)(F)N1=C2C1=CC=C(C)C(C)=C1.CC1=CC2=C3N=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N3C(C3=CC=CC=C3)=C2C=C1C.CC1=CC=C(C2=C3C=C(C)C=CC3=C3C=C4C5=C(C=C(C)C=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C Chemical compound CC1=CC(C)=CC(C2=C3C4=C(C=CC=C4)C(C)=N3B(F)(F)N3C(C)=C4C=CC=CC4=C23)=C1.CC1=CC2=C(C=C1)C1=C(C3=CC=CC=C3)C3=C4C=CC(C)=CC4=C(C4=CC=C(C)C(C)=C4)N3B(F)(F)N1=C2C1=CC=C(C)C(C)=C1.CC1=CC2=C3N=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N3C(C3=CC=CC=C3)=C2C=C1C.CC1=CC=C(C2=C3C=C(C)C=CC3=C3C=C4C5=C(C=C(C)C=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C VMAOQDKIFZZMEA-UHFFFAOYSA-N 0.000 description 1
- WIAGEPLEIFJBPF-UHFFFAOYSA-N CC1=CC(C)=CC(C2=C3C4=C(C=CC=C4)C=CC3=C3C=C4C5=C(C6=C(C=CC=C6)C=C5)C(C5=CC(C)=CC(C)=C5)=N4B(F)(F)N32)=C1.CC1=CC=CC=C1C1=N2C(=CC3=C4C=CC5=C(C=CC=C5)C4=C(C4=C(C)C=CC=C4)N3B2(F)F)C2=C1C1=C(C=CC=C1)C=C2.COC1=CC=C(C2=CC(C3=CC=C(OC)C=C3)=N3C2=CC2=C(C4=CC=C(CO)C=C4)C=C(C4=CC=C(CO)C=C4)N2B3(F)F)C=C1.CSC1=CC=C(C2=CC(C3=CC=C(SC)C=C3)=N3C2=CC2=C(C4=CC=C(CS)C=C4)C=C(C4=CC=C(CS)C=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC4=C(C=CC=C4)C3=C2C2=C3C=CC=CC3=CC=C2)C=C2C3=C(C4=C(C=CC=C4)C=C3)C(C3=CC=CC4=C3C=CC=C4)=N21 Chemical compound CC1=CC(C)=CC(C2=C3C4=C(C=CC=C4)C=CC3=C3C=C4C5=C(C6=C(C=CC=C6)C=C5)C(C5=CC(C)=CC(C)=C5)=N4B(F)(F)N32)=C1.CC1=CC=CC=C1C1=N2C(=CC3=C4C=CC5=C(C=CC=C5)C4=C(C4=C(C)C=CC=C4)N3B2(F)F)C2=C1C1=C(C=CC=C1)C=C2.COC1=CC=C(C2=CC(C3=CC=C(OC)C=C3)=N3C2=CC2=C(C4=CC=C(CO)C=C4)C=C(C4=CC=C(CO)C=C4)N2B3(F)F)C=C1.CSC1=CC=C(C2=CC(C3=CC=C(SC)C=C3)=N3C2=CC2=C(C4=CC=C(CS)C=C4)C=C(C4=CC=C(CS)C=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC4=C(C=CC=C4)C3=C2C2=C3C=CC=CC3=CC=C2)C=C2C3=C(C4=C(C=CC=C4)C=C3)C(C3=CC=CC4=C3C=CC=C4)=N21 WIAGEPLEIFJBPF-UHFFFAOYSA-N 0.000 description 1
- NKZRTKXYBALWCU-UHFFFAOYSA-N CC1=CC(C)=CC(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)=C1.CC1=CC(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)=CC(C)=C1C.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1C.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C4C=C(C)C=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 Chemical compound CC1=CC(C)=CC(C2=C3C=C(C)C(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)=C1.CC1=CC(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)=CC(C)=C1C.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1C.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C4C=C(C)C=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 NKZRTKXYBALWCU-UHFFFAOYSA-N 0.000 description 1
- ZUFPNTVXDWKARW-UHFFFAOYSA-N CC1=CC(C)=CC(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)=C1.CC1=CC2=C(C=C1C)C(C1=CC=CC=C1)=N1C2=C(C2=CC=CC=C2)C2=C3C=C(C)C(C)=CC3=C(C3=CC=CC=C3)N2B1(F)F.CC1=CC2=C(C=C1C)C(C1=CC=CC=C1)=N1C2=CC2=C3C=C(C)C(C)=CC3=C(C3=CC=CC=C3)N2B1(F)F.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21 Chemical compound CC1=CC(C)=CC(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)=C1.CC1=CC2=C(C=C1C)C(C1=CC=CC=C1)=N1C2=C(C2=CC=CC=C2)C2=C3C=C(C)C(C)=CC3=C(C3=CC=CC=C3)N2B1(F)F.CC1=CC2=C(C=C1C)C(C1=CC=CC=C1)=N1C2=CC2=C3C=C(C)C(C)=CC3=C(C3=CC=CC=C3)N2B1(F)F.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21 ZUFPNTVXDWKARW-UHFFFAOYSA-N 0.000 description 1
- BUHSOICXOOVUCC-UHFFFAOYSA-N CC1=CC(C)=CC(C2=CC(C3=CC(C)=CC(C)=C3)=N3C2=CC2=C(C4=CC(C)=CC(C)=C4)C=C(C4=CC(C)=CC(C)=C4)N2B3(F)F)=C1.CC1=CC=C(C2=C3C=C4C(C5=C6C=CC=CC6=C(C)C=C5)=CC(C5=CC=C(C)C6=C5C=CC=C6)=N4B(F)(F)N3C(C3=C4C=CC=CC4=C(C)C=C3)=C2)C2=C1C=CC=C2.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=C3C=C4C=CC(C5=CN=CO5)=N4B(F)(F)N23)C=C1.CCCCCCC1=CC=C(C2=CC(C3=CC=C(CCCCCC)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C(C4=CC=C(CCCCCC)C=C4)C=C(C4=CC=C(CCCCCC)C=C4)N2B3(F)F)C=C1 Chemical compound CC1=CC(C)=CC(C2=CC(C3=CC(C)=CC(C)=C3)=N3C2=CC2=C(C4=CC(C)=CC(C)=C4)C=C(C4=CC(C)=CC(C)=C4)N2B3(F)F)=C1.CC1=CC=C(C2=C3C=C4C(C5=C6C=CC=CC6=C(C)C=C5)=CC(C5=CC=C(C)C6=C5C=CC=C6)=N4B(F)(F)N3C(C3=C4C=CC=CC4=C(C)C=C3)=C2)C2=C1C=CC=C2.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=C3C=C4C=CC(C5=CN=CO5)=N4B(F)(F)N23)C=C1.CCCCCCC1=CC=C(C2=CC(C3=CC=C(CCCCCC)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C(C4=CC=C(CCCCCC)C=C4)C=C(C4=CC=C(CCCCCC)C=C4)N2B3(F)F)C=C1 BUHSOICXOOVUCC-UHFFFAOYSA-N 0.000 description 1
- SPIOORFBIAVRQL-UHFFFAOYSA-N CC1=CC(C)=CC(C2=CC(C3=CC=CC=C3)=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC(C)=CC(C)=C5)=N4B(F)(F)N23)=C1.CC1=CC(C)=CC(C2=CC(C3=CC=CC=C3)=N3C2=CC2=C(C4=CC(C)=CC(C)=C4)C=C(C4=CC=CC=C4)N2B3(F)F)=C1.CC1=CC2=C(C=C1)C1=C(C3=CC=CC=C3)C3=C4C=CC(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N1=C2C1=CC=CC=C1.CC1=CC2=C(C=C1)C1=CC3=C4C=CC(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N1=C2C1=CC=CC=C1.CC1=CC2=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N3C(C3=CC=CC=C3)=C2C=C1C Chemical compound CC1=CC(C)=CC(C2=CC(C3=CC=CC=C3)=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC(C)=CC(C)=C5)=N4B(F)(F)N23)=C1.CC1=CC(C)=CC(C2=CC(C3=CC=CC=C3)=N3C2=CC2=C(C4=CC(C)=CC(C)=C4)C=C(C4=CC=CC=C4)N2B3(F)F)=C1.CC1=CC2=C(C=C1)C1=C(C3=CC=CC=C3)C3=C4C=CC(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N1=C2C1=CC=CC=C1.CC1=CC2=C(C=C1)C1=CC3=C4C=CC(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N1=C2C1=CC=CC=C1.CC1=CC2=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N3C(C3=CC=CC=C3)=C2C=C1C SPIOORFBIAVRQL-UHFFFAOYSA-N 0.000 description 1
- MGUJKGIXOYZSEV-UHFFFAOYSA-N CC1=CC(C)=CC(C2=CC(C3=CC=CC=C3)=N3C2=NC2=C(C4=CC(C)=CC(C)=C4)C=C(C4=CC=CC=C4)N2B3(F)F)=C1.CC1=CC2=C(C=C1)C1=NC3=C4C=CC(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N1=C2C1=CC=CC=C1.CC1=CC=C(C2=C3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=N3B(F)(F)N3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=C23)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=NC2=C4C=CC=CC4=C(C4=CC=CC=C4)N2B3(F)F)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=CC(C)=C(C)C(C)=C4)N3B(F)(F)N2=C1C Chemical compound CC1=CC(C)=CC(C2=CC(C3=CC=CC=C3)=N3C2=NC2=C(C4=CC(C)=CC(C)=C4)C=C(C4=CC=CC=C4)N2B3(F)F)=C1.CC1=CC2=C(C=C1)C1=NC3=C4C=CC(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N1=C2C1=CC=CC=C1.CC1=CC=C(C2=C3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=N3B(F)(F)N3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=C23)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=NC2=C4C=CC=CC4=C(C4=CC=CC=C4)N2B3(F)F)C=C1.CCC1=C(C)C2=NC3=C4C=CC=CC4=C(C4=CC(C)=C(C)C(C)=C4)N3B(F)(F)N2=C1C MGUJKGIXOYZSEV-UHFFFAOYSA-N 0.000 description 1
- OVFXIHGXNXYUKF-UHFFFAOYSA-N CC1=CC(C2=C3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=N3B(F)(F)N3C(C4=C(C)C=C(C)C=C4C)=C4C=CC=CC4=C23)=CC=C1.CC1=CC=C(C2=C3C=CC(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C5=C(C=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1 Chemical compound CC1=CC(C2=C3C(C4=CC=CC=C4)=CC(C4=CC=CC=C4)=N3B(F)(F)N3C(C4=C(C)C=C(C)C=C4C)=C4C=CC=CC4=C23)=CC=C1.CC1=CC=C(C2=C3C=CC(C)=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C5=C(C=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1 OVFXIHGXNXYUKF-UHFFFAOYSA-N 0.000 description 1
- VDWAGUGVTXNLNS-UHFFFAOYSA-N CC1=CC2=C(C=C1C)C(C1=CC=CC=C1)=N1C2=NC2=C3C=C(C)C(C)=CC3=C(C3=CC=CC=C3)N2B1(F)F.CC1=CC=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=C(C2=CC=CC=C2)C2=C(C4=CC=C(C)C=C4)C=C(C4=CC=CC=C4)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=NC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=CC=C4)N2B3(F)F)C=C1 Chemical compound CC1=CC2=C(C=C1C)C(C1=CC=CC=C1)=N1C2=NC2=C3C=C(C)C(C)=CC3=C(C3=CC=CC=C3)N2B1(F)F.CC1=CC=C(C2=C3C=C(C)C(C)=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=C(C2=CC=CC=C2)C2=C(C4=CC=C(C)C=C4)C=C(C4=CC=CC=C4)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=NC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=CC=C4)N2B3(F)F)C=C1 VDWAGUGVTXNLNS-UHFFFAOYSA-N 0.000 description 1
- VTJNMUJBQWHLIB-UHFFFAOYSA-N CC1=CC=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC=CC3=C2C2=CC=CC=C2)N=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C(C2=CC=CC=C2)=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2N=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21 Chemical compound CC1=CC=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC=CC3=C2C2=CC=CC=C2)N=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C(C2=CC=CC=C2)=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2N=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21 VTJNMUJBQWHLIB-UHFFFAOYSA-N 0.000 description 1
- PBDJVTOYPPASAY-UHFFFAOYSA-N CC1=CC=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C5=C(C=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=CC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=CC=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC=CC3=C2C2=CC=CC=C2)C=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=C3C=CC=CC3=C2C(C2=CC=CC=C2)=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21 Chemical compound CC1=CC=C(C2=C3C=CC=CC3=C3C(C4=CC=CC=C4)=C4C5=C(C=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=CC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=CC=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC=CC3=C2C2=CC=CC=C2)C=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=C3C=CC=CC3=C2C(C2=CC=CC=C2)=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21 PBDJVTOYPPASAY-UHFFFAOYSA-N 0.000 description 1
- IKYPEFNOEXYTLW-UHFFFAOYSA-N CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC(C)=CC(C)=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=C(C)C=C(C)C=C5C)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=CC2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 Chemical compound CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC(C)=CC(C)=C5)=CC(C5=CC=CC=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=C3C=CC=CC3=C3C=C4C(C5=CC=CC=C5)=CC(C5=C(C)C=C(C)C=C5C)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=N3C2=CC2=C4C=CC=CC4=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 IKYPEFNOEXYTLW-UHFFFAOYSA-N 0.000 description 1
- NERXCHHRXGHJJR-UHFFFAOYSA-N CC1=CC=C(C2=C3C=CC=CC3=C3N=C4C5=C(C=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=CC=C4)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=C3N=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1 Chemical compound CC1=CC=C(C2=C3C=CC=CC3=C3N=C4C5=C(C=CC=C5)C(C5=CC=C(C)C=C5)=N4B(F)(F)N32)C=C1.CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C4C=CC=CC4=C(C4=CC=CC=C4)N2B3(F)F)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=C3C(C4=CC=CC=C4)=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1.CC1=CC=C(C2=CC(C3=CC=CC=C3)=C3N=C4C(C5=CC=CC=C5)=CC(C5=CC=C(C)C=C5)=N4B(F)(F)N23)C=C1 NERXCHHRXGHJJR-UHFFFAOYSA-N 0.000 description 1
- DLRUTDQKCQLCEG-UHFFFAOYSA-N CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 Chemical compound CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1 DLRUTDQKCQLCEG-UHFFFAOYSA-N 0.000 description 1
- AINKAPGYUGEOEX-UHFFFAOYSA-N CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC4=C(C=CC=C4)C3=C2C2=CC=CC=C2)C=C2C3=C(C4=C(C=CC=C4)C=C3)C(C3=CC=CC=C3)=N21.FB1(F)N2C(=C3C=CC=CC3=C2C2=C3C=CC=CC3=C3C=CC=CC3=C2)C=C2C3=C(C=CC=C3)C(C3=CC4=C(C=CC=C4)C4=C3C=CC=C4)=N21.FB1(F)N2C(=C3C=CC=CC3=C2C2=C3C=CC=CC3=CC=C2)C=C2C3=C(C=CC=C3)C(C3=CC=CC4=C3C=CC=C4)=N21.FB1(F)N2C(=C3C=CC=CC3=C2C2=CC=CC=C2)C=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21 Chemical compound CC1=CC=C(C2=CC(C3=CC=C(C)C=C3)=N3C2=CC2=C(C4=CC=C(C)C=C4)C=C(C4=CC=C(C)C=C4)N2B3(F)F)C=C1.FB1(F)N2C(=C3C=CC4=C(C=CC=C4)C3=C2C2=CC=CC=C2)C=C2C3=C(C4=C(C=CC=C4)C=C3)C(C3=CC=CC=C3)=N21.FB1(F)N2C(=C3C=CC=CC3=C2C2=C3C=CC=CC3=C3C=CC=CC3=C2)C=C2C3=C(C=CC=C3)C(C3=CC4=C(C=CC=C4)C4=C3C=CC=C4)=N21.FB1(F)N2C(=C3C=CC=CC3=C2C2=C3C=CC=CC3=CC=C2)C=C2C3=C(C=CC=C3)C(C3=CC=CC4=C3C=CC=C4)=N21.FB1(F)N2C(=C3C=CC=CC3=C2C2=CC=CC=C2)C=C2C3=C(C=CC=C3)C(C3=CC=CC=C3)=N21 AINKAPGYUGEOEX-UHFFFAOYSA-N 0.000 description 1
- YVSMRTOGMKSFCA-UHFFFAOYSA-N CC1=NN=C(C)O1.CC1=NN=C(CC2=NN=C(C)O2)O1.CC1=NN=C(COCC2=NN=C(C)O2)O1 Chemical compound CC1=NN=C(C)O1.CC1=NN=C(CC2=NN=C(C)O2)O1.CC1=NN=C(COCC2=NN=C(C)O2)O1 YVSMRTOGMKSFCA-UHFFFAOYSA-N 0.000 description 1
- FPOVEDKHVUVCHA-VPKGJNAPSA-N CC1=NOC(C)=C1/C=C/C1=CC=C2C=C3C=CC(/C=C/C4=CC=CC=C4)=N3B(F)(F)N21.FB1(F)N2C(=CC=C2C2=C3C=CC=CC3=CC=C2)C=C2C=CC(C3=CC=CS3)=N21.FB1(F)N2C(C3=CC4=C(C=CC=C4)C=C3)=CC(C3=CC=C4C=CC=CC4=C3)=C2C=C2C(C3=CC4=C(C=CC=C4)C=C3)=CC(C3=CC=C4C=CC=CC4=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(/C=C/C3=CC=CC4=C3C=CC=C4)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CC=CN3)=N21 Chemical compound CC1=NOC(C)=C1/C=C/C1=CC=C2C=C3C=CC(/C=C/C4=CC=CC=C4)=N3B(F)(F)N21.FB1(F)N2C(=CC=C2C2=C3C=CC=CC3=CC=C2)C=C2C=CC(C3=CC=CS3)=N21.FB1(F)N2C(C3=CC4=C(C=CC=C4)C=C3)=CC(C3=CC=C4C=CC=CC4=C3)=C2C=C2C(C3=CC4=C(C=CC=C4)C=C3)=CC(C3=CC=C4C=CC=CC4=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(/C=C/C3=CC=CC4=C3C=CC=C4)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CC=CN3)=N21 FPOVEDKHVUVCHA-VPKGJNAPSA-N 0.000 description 1
- YEURFAPKMGNSJH-UHFFFAOYSA-N CCC1=C(C)C2=CC3=C4C=C(C)C(C)=CC4=C(C4=CC(C)=CC(C)=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=C(C)C(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=C(C)C=CC4=C(C4=CC=C(C)C=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=C(C)C=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=C(C)C=C(C)C=C4C)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC(C)=CC(C)=C4)N3B(F)(F)N2=C1C Chemical compound CCC1=C(C)C2=CC3=C4C=C(C)C(C)=CC4=C(C4=CC(C)=CC(C)=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=C(C)C(C)=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=C(C)C=CC4=C(C4=CC=C(C)C=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=C(C)C=CC4=C(C4=CC=CC=C4)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=C(C)C=C(C)C=C4C)N3B(F)(F)N2=C1C.CCC1=C(C)C2=CC3=C4C=CC=CC4=C(C4=CC(C)=CC(C)=C4)N3B(F)(F)N2=C1C YEURFAPKMGNSJH-UHFFFAOYSA-N 0.000 description 1
- QRQVCUXELYLCTD-UHFFFAOYSA-N CCCCCCC1=CC=C(C2=CC(C3=CC=C(CCCCCC)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C(C4=CC=C(CCCCCC)C=C4)C=C(C4=CC=C(CCCCCC)C=C4)N2B3(F)F)C=C1 Chemical compound CCCCCCC1=CC=C(C2=CC(C3=CC=C(CCCCCC)C=C3)=N3C2=C(C2=CC=CC=C2)C2=C(C4=CC=C(CCCCCC)C=C4)C=C(C4=CC=C(CCCCCC)C=C4)N2B3(F)F)C=C1 QRQVCUXELYLCTD-UHFFFAOYSA-N 0.000 description 1
- XCZXGTMEAKBVPV-UHFFFAOYSA-N C[Ga](C)C Chemical compound C[Ga](C)C XCZXGTMEAKBVPV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ATCRCYQOMFNDRP-WXGKVSOISA-N FB1(F)N2C(=CC=C2/C=C/C2=CC=CC=C2)C=C2C=CC(/C=C/C3=CC=CC=C3)=N21.FB1(F)N2C(=CC=C2C2=CC=CN2)C=C2C=CC(C3=CC=CN3)=N21.FB1(F)N2C(=CC=C2C2=CC=CS2)C=C2C=CC(C3=CC=CS3)=N21.FB1(F)N2C(=CC=C2C2=CN=CO2)C=C2C=CC(C3=CN=CO3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CC4=C(C=CC=C4)S3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=NC4=C(C=CC=C4)O3)=N21 Chemical compound FB1(F)N2C(=CC=C2/C=C/C2=CC=CC=C2)C=C2C=CC(/C=C/C3=CC=CC=C3)=N21.FB1(F)N2C(=CC=C2C2=CC=CN2)C=C2C=CC(C3=CC=CN3)=N21.FB1(F)N2C(=CC=C2C2=CC=CS2)C=C2C=CC(C3=CC=CS3)=N21.FB1(F)N2C(=CC=C2C2=CN=CO2)C=C2C=CC(C3=CN=CO3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CC4=C(C=CC=C4)S3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=NC4=C(C=CC=C4)O3)=N21 ATCRCYQOMFNDRP-WXGKVSOISA-N 0.000 description 1
- IRPCXBSMQZUNAE-NCAGBYRDSA-N FB1(F)N2C(C3=C4C=CC=CC4=CC=C3)=CC(C3=CC=CC4=C3C=CC=C4)=C2C=C2C(C3=C4C=CC=CC4=CC=C3)=CC(C3=CC=CC4=C3C=CC=C4)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(/C=C/C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CC=CS3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CN=CO3)=N21 Chemical compound FB1(F)N2C(C3=C4C=CC=CC4=CC=C3)=CC(C3=CC=CC4=C3C=CC=C4)=C2C=C2C(C3=C4C=CC=CC4=CC=C3)=CC(C3=CC=CC4=C3C=CC=C4)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(/C=C/C3=CC=CC=C3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CC=CS3)=N21.FB1(F)N2C(C3=CC=CC=C3)=CC(C3=CC=CC=C3)=C2C=C2C=CC(C3=CN=CO3)=N21 IRPCXBSMQZUNAE-NCAGBYRDSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- UIFONGQSVSRGRO-ATWNPGLXSA-N [C-]#[N+]/C(C#N)=C1\C=C(/C=C/C2=CC3=C4C(=C2)C(C)(C)CCN4CCC3(C)C)OC(C(C)(C)C)=C1 Chemical compound [C-]#[N+]/C(C#N)=C1\C=C(/C=C/C2=CC3=C4C(=C2)C(C)(C)CCN4CCC3(C)C)OC(C(C)(C)C)=C1 UIFONGQSVSRGRO-ATWNPGLXSA-N 0.000 description 1
- KJNGJIPPQOFCSK-UHFFFAOYSA-N [H][Sr][H] Chemical compound [H][Sr][H] KJNGJIPPQOFCSK-UHFFFAOYSA-N 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 239000005354 aluminosilicate glass Substances 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- BIOPPFDHKHWJIA-UHFFFAOYSA-N anthracene-9,10-dinitrile Chemical class C1=CC=C2C(C#N)=C(C=CC=C3)C3=C(C#N)C2=C1 BIOPPFDHKHWJIA-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- JZKFIPKXQBZXMW-UHFFFAOYSA-L beryllium difluoride Chemical compound F[Be]F JZKFIPKXQBZXMW-UHFFFAOYSA-L 0.000 description 1
- 229910001633 beryllium fluoride Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 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
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N caesium oxide Chemical compound [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 229910001942 caesium oxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000005584 chrysenylene group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010893 electron trap Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 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 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005563 perylenylene group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 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
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 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
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/62—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing four rings
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
Definitions
- the present invention relates to an organic electroluminescence device (organic EL device) and a display that use a naphthacene derivative and a compound having a pyrromethene skeleton or a metal complex of the compound together.
- Organic electroluminescence (EL) devices have been known.
- Organic EL devices formed from organic materials have been vigorously studied since a report on a low voltage-driven organic EL device formed by laminating layers was made by C. W. Tang et al. of Eastman Kodak Company (see Document 1: Applied Physics Letters, vol. 51, page 913, by C. W. Tang and S. A. Vanslyke, 1987).
- an emitting material used for an organic EL device are a chelate complex such as a tris(8-quinolinol)aluminum (Alq) complex, a coumarin complex, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, an oxadiazole derivative or the like.
- Alq tris(8-quinolinol)aluminum
- coumarin complex e.g., a tris(8-quinolinol)aluminum (Alq) complex
- a coumarin complex e.g., a tris(8-quinolinol)aluminum (Alq) complex
- a coumarin complex e.g., a tris(8-quinolinol)aluminum (Alq) complex
- a coumarin complex e.g., a tris(8-quinolinol)aluminum (Alq) complex
- Document 5 JP-A-08-311442 has recently disclosed a red-emitting device whose emitting layer is added with a naphthacene derivative or a pentacene derivative.
- the red-emitting device is excellent in purity of red color, the red-emitting device requires voltage of 11V to be applied, and time lapsed until the luminescent intensity decreases to half is approximately 150 hours, i.e., the performance of the device is insufficient.
- Document 6 JP-A-03-162481 discloses a device whose emitting layer is added with a dicyanomethylene (DCM)-based compound. However, the device exhibits insufficient purity of red color.
- DCM dicyanomethylene
- Document 7 JP-A-2001-81451 discloses a red-emitting device whose emitting layer is added with an amine-based aromatic compound. However, although the emitting device exhibits excellent CIE (Commission Internationale d'Eclairage) chromaticity (0.64, 0.33) and chromatic purity, the device requires high voltage for driving.
- Document 8 WO/01/23497
- Document 9 JP-A-2003-40845 disclose devices in which an amine-based aromatic compound and an Alq compound are used for the emitting layer. However, although emitting red light, the device exhibits low efficiency and short lifetime.
- JP-A-2003-81924 discloses devices in which an amine-based aromatic compound and DPVDPAN are used for the emitting layer. However, high-efficient one of the devices emits orange light while red-emitting one of the devices exhibits low efficiency.
- JP-A-2001-307885 discloses a device in which a dicyanoanthracene derivative and an indenoperylene derivative are used for the emitting layer while a metal complex is used for the electron transporting layer.
- the device emits light of red orange color.
- JP-A-2003-338377 discloses a device in which a fluoranthene derivative and an indenoperylene derivative are used for the emitting layer while a fluoranthene derivative is used for the electron transporting layer.
- the device does not exhibit practically-applicable efficiency.
- An object of the present invention is to provide an practically-applicable organic EL device and a practically-applicable display excellent in efficiency, lifetime and chromatic purity.
- an organic EL device exhibits longer lifetime and higher efficiency by using a naphthacene derivative and a compound having a pyrromethene skeleton or a metal complex of the compound in at least one layer of organic compound layers of the organic EL device, and reached the present invention.
- An organic electroluminescence device includes: a cathode; an anode; and an emitting layer provided between the cathode and the anode, in which the emitting layer comprises a host and a dopant, the host is a naphthacene derivative represented by a formula (1) as follows, and the dopant is a compound having a pyrromethene skeleton represented by a formula (2) as follows or a metal complex of the compound.
- Q 10 , Q 20 , Q 30 , Q 40 , Q 50 , Q 60 , Q 70 , Q 80 , Q 110 , Q 120 , Q 130 and Q 140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group
- R 15 to R 21 is a substitute having an aromatic ring or forms a condensed ring together with an adjacent substituent while the rest of R 15 to R 21 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, a haloalkane, a haloalkene, a haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or
- R 15 to R 21 each may form a condensed ring or an aliphatic ring with an adjacent substituent (the groups listed above each have 1 to 20 carbon atoms).
- R 15 to R 21 may be mutually the same or different and may be substituted or unsubstituted.
- X represents a carbon atom or a nitrogen atom on a condition that R 21 above does not exist when X represents a nitrogen atom.
- a metal in the metal complex is at least one metal selected from a group consisting of boron, beryllium, magnesium, chrome, iron, cobalt, nickel, copper, zinc and platinum.
- the metal in the metal complex is particularly preferably boron.
- the substituted or unsubstituted alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, further preferably an alkyl group having 1 to 5 carbon atoms.
- the alkyl group may be linear or branched.
- the alkyl group may be a primary alkyl group, a secondary alkyl group or a tertiary alkyl group.
- alkyl group are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group and an n-decyl group.
- the substituted or unsubstituted aryl group is preferably an aryl group having 6 to carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms.
- the aryl group are a phenyl group, a phenylphenyl group (4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group), a naphthylphenyl group (4-(1-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group), a naphthyl group (1-naphthyl group, 2-naphthyl group), a phenylnaphthyl group (6-phenyl-2-naphthyl group, 4-phenyl-1-naphthyl group), a naphthylnaphthyl group (6-naphthyl-2-naphthyl group
- the amino group may be an amino group, a substituted or unsubstituted monoalkyl-aryl group having 1 to 20 carbon atoms, a substituted or unsubstituted dialkyl-aryl group having 1 to 20 carbon atoms, a substituted or unsubstituted monoaryl-aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted bisaryl-aryl group having 6 to 30 carbon atoms.
- Examples of the amino group are a dimethylamino group, a diethylamino group, a diphenylamino group, a ditolylamino group and a dixylylamino group.
- the substituted or unsubstituted alkoxy group is preferably an alkoxy group having 1 to 20 carbon atoms, examples of which are a methoxy group, an ethoxy group and a propoxy group.
- the substituted or unsubstituted alkylthio group is preferably an alkylthio group having 1 to 20 carbon atoms, examples of which are a methylthio group and an ethylthio group.
- the substituted or unsubstituted aryloxy group is preferably an aryloxy group having 6 to 30 carbon atoms, an example of which is a phenoxy group.
- the substituted or unsubstituted aryloxythio group is preferably an aryloxythio group having 6 to 30 carbon atoms, an example of which is a phenylthio group.
- the substituted or unsubstituted alkenyl group is preferably an alkenyl group having 1 to 20 carbon atoms, examples of which are a vinyl group and a propenyl group.
- the substituted or unsubstituted aralkyl group is preferably an aralkyl group having 7 to 30 carbon atoms, an example of which is a benzyl group.
- the substituted or unsubstituted heterocyclic group is preferably a heterocyclic group having 5 to 30 carbon atoms, examples of which are a pyridyl group, a furyl group, a thienyl group, a pyrazyl group, a pyrimidyl group and a quinolyl group.
- the emitting layer contains the host formed of a naphthacene derivative and the dopant formed of a compound having a pyrromethene skeleton or a metal complex of the compound, the organic EL device having practically-applicable efficiency and lifetime can be realized.
- the compound having the pyrromethene skeleton represented by the formula (2) or the metal complex of the compound is a metal complex having a pyrromethene skeleton represented by a formula (2-1) as follows.
- R 22 to R 28 is a substitute having an aromatic ring or forms a condensed aromatic ring together with an adjacent substituent while the rest of R 22 to R 28 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a silox
- R 22 to R 28 each may form a condensed ring or an aliphatic ring with an adjacent substituent.
- R 22 to R 28 may be mutually the same or different and may be substituted or unsubstituted.
- R 29 and R 30 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group.
- X represents a carbon atom or a nitrogen atom on a condition that R 28 above does not exist when X represents a nitrogen atom.
- At least one of R 22 to R 28 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a substituent having an aromatic ring.
- At least one of R 22 to R 28 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a condensed aromatic ring together with an adjacent substituent.
- At least one of R 22 to R 24 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a substituted or unsubstituted condensed aromatic ring together with an adjacent substituent and/or at least one of R 25 to R 27 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a substituted or unsubstituted condensed aromatic ring together with an adjacent substituent.
- the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a metal complex having a pyrromethene skeleton represented by a formula (2-2) as follows.
- R 31 to R 39 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group.
- R 31 to R 39 may be mutually the same or different and may be substituted or unsubstituted.
- R 40 and R 41 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group.
- X represents a carbon atom or a nitrogen atom on a condition that R 39 above does not exist when X represents a nitrogen atom.
- the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a metal complex having a pyrromethene skeleton represented by a formula (2-3) as follows.
- R 42 to R 52 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group.
- R 42 to R 52 may be mutually the same or different and may be substituted or unsubstituted.
- R 53 and R 54 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group.
- X represents a carbon atom or a nitrogen atom on a condition that R 52 above does not exist when X represents a nitrogen atom.
- At least one of Q 10 , Q 20 , Q 30 and Q 40 in the naphthacene derivative represented by the formula (1) is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- the naphthacene derivative represented by the formula (1) is a naphthacene derivative represented by a formula (3) as follows.
- Q 10 , Q 21 to Q 25 , Q 31 to Q 35 , Q 40 to Q 80 and Q 110 to Q 140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
- Q 10 , Q 21 to Q 25 , Q 31 to Q 35 , Q 40 to Q 80 and Q 110 to Q 140 may be mutually the same or different.
- Adjacent two or more of Q 21 to Q 25 and Q 31 to Q 35 may be mutually bonded to form a cyclic structure.
- At least one of Q 21 , Q 25 , Q 31 an Q 35 in the naphthacene derivative represented by the formula (3) represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
- the naphthacene derivative represented by the formula (3) has a substituent in at least one ortho position of two benzene rings bonded to naphthacene.
- a steric hindrance is caused between the introduced substituent(s) and the naphthacene skeleton.
- the steric hindrance directs the introduced substituent(s) to face in an out-of-plane direction of the naphthacene skeleton. Then, the substituent(s) directed in the out-of-plane direction prevents association of naphthacene derivatives with each other.
- Q 21 , Q 25 , Q 31 and Q 35 When two or more of Q 21 , Q 25 , Q 31 and Q 35 are substituents, the substituents may be mutually the same or different. In addition, adjacent two or more of Q 21 to Q 25 and Q 31 to Q 35 may be mutually bonded to form a cyclic structure.
- substituent is a substituted or unsubstituted phenyl group.
- Two or more of the ortho positions of the two benzene rings bonded to naphthacene are preferably substituted.
- At least one of Q 21 and Q 25 in the naphthacene derivative represented by the formula (3) represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group while at least one of Q 31 and Q 35 in the naphthacene derivative represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
- the dopant is contained in the emitting layer at a doping concentration of 0.1 to 10 mass %. It is more preferable that the dopant is contained in the emitting layer at a doping concentration of 0.5 to 2.0 mass %.
- the organic EL device further includes an electron transporting layer provided between the cathode and the anode, in which the electron transporting layer comprises a compound represented by a formula (4) as follows.
- A represents a substituted or unsubstituted condensed aromatic hydrocarbon group having three or more rings
- B represents a substituted or unsubstituted heterocyclic group.
- m and n each represent an integer in a range of 1 to 6.
- a in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from a group consisting of anthracene, phenanthrene, naphthacene, pyrene, chrysene, benzoanthracene, pentacene, dibenzoanthracene, benzopyrene, fluorene, benzofluorene, fluoranthene, benzofluoranthene, naphthofluoranthene, dibenzofluorene, dibenzopyrene and dibenzofluoranthene.
- B in the compound represented by the formula (4) is a nitrogen-containing heterocyclic group.
- B in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from a group consisting of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, acridine, imidazopyridine, imidazopyrimidine, phenanthroline, pyrazole, imidazole and benzoimidazole.
- the compound represented by the formula (4) is a benzoimidazole derivative represented by a formula (5) or a formula (6) as follows.
- R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;
- p represents an integer in a range of 1 to 4;
- R 11 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms;
- R 12 represents a hydrogen atom, a substituted or unsubsti
- At least one of R, R 11 , R 12 , L and Ar 1 corresponds to A in the compound represented by the formula (4) and is a condensed aromatic hydrocarbon group having three or more rings.
- the emitting layer emits light of orange to red.
- a display according to another aspect of the present invention includes the above-described organic electroluminescence device.
- the display since the display is formed from the above-described organic electroluminescence device, the display can exhibit high efficiency, long lifetime and excellent chromatic purity.
- the present invention can provide a practically-applicable organic EL device that exhibits high efficiency, long life and excellent chromatic purity.
- the organic EL device can exhibit higher efficiency. Specifically, with the arrangement according to the present invention, generation of exciters in the electron transporting layer can be prevented, thereby providing a highly chromatically-pure organic EL device whose micro emission from the electron transporting layer is further reduced In addition, for the same reason(s), the lifetime of the device can be prolonged.
- FIG. 1 shows a first embodiment of an organic EL device according to the present invention.
- anode/emitting layer/electron transporting layer/cathode (2) anode/hole transporting layer/emitting layer/electron transporting layer/cathode (3) anode/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/cathode (4) anode/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/cathode (5) anode/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/cathode ( FIG.
- anode/insulating layer/hole transporting layer/emitting layer/electron transporting layer/cathode (7) anode/hole transporting layer/emitting layer/electron transporting layer/insulating layer/cathode (8) anode/insulating layer/hole transporting layer/emitting layer/electron transporting layer/insulating layer/cathode (9) anode/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/insulating layer/cathode (10) anode/insulating layer/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/cathode (11) anode/insulating layer/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/insulating layer/cathode
- the arrangement (2), (3), (4), (5), (8), (9) or (11) is typically preferable.
- the organic EL device includes an anode, a cathode and a single-layered or plural-layered organic layer including an emitting layer. At least one layer of the organic layer contains a host formed of a naphthacene derivative and a dopant formed of a compound having a pyrromethene skeleton or a metal complex of the compound.
- the organic EL device 1 includes an anode 20 , a hole injecting layer 30 , a hole transporting layer 40 , an emitting layer 50 , an electron transporting layer 60 , an electron injecting layer 70 and a cathode 80 , which are all laminated on a substrate 10 in this order.
- the hole injecting layer 30 , the hole transporting layer 40 , the emitting layer 50 , the electron transporting layer 60 and the electron injecting layer 70 correspond to the organic layer interposed between the cathode 80 and the anode 20 .
- At least one of the above layers contains a host material formed of a naphthacene derivative and a dopant material formed of a compound having a pyrromethene skeleton or a metal complex of the compound.
- the emitting layer contains a naphthacene derivative and a compound having a pyrromethene skeleton or a metal complex of the compound.
- the organic EL device When the organic EL device is to emit light through the substrate (i.e., when the organic EL device is bottom-emission type), the organic EL device according to the present invention is manufactured on a light-transmissive substrate.
- the light-transmissive plate, which supports the organic EL device is preferably a smoothly-shaped substrate that transmits 50% or more of light in a visible region of 400 nm to 700 nm.
- the light-transmissive plate is exemplarily a glass plate, a polymer plate or the like.
- the glass plate such materials as soda-lime glass, barium/strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like can be used.
- the polymer plate such materials as polycarbonate, acryl, polyethylene terephthalate, polyether sulfide, polysulfone and the like can be used.
- the light-transmissive plate may be a TFT substrate on which a TFT (thin film transistor) for driving is formed.
- the light-transmissive plate is required to be provided with a light reflector, an exemplary material of which is a metal such as aluminum.
- the anode of the organic EL device is used for injecting holes into the hole transporting layer or the emitting layer. It is effective that the anode includes a work function of 4.5 eV or more.
- Exemplary materials for the anode are indium-tin oxide (ITO), tin oxide (NESA), indium zinc oxide alloy (IZO), gold, silver, platinum and copper.
- One of the above materials may be singularly used, or alloys formed by mixing the above materials and materials formed by adding other element(s) to the above material(s) may be suitably selected as the material of the anode.
- the anode may be made by forming a thin film from the above electrode materials through methods such as vapor deposition and sputtering.
- the anode When the organic EL device is bottom-emission type, the anode preferably transmits more than 10% of light emitted by the emitting layer. Sheet resistance of the anode is preferably several hundreds ⁇ /square or lower. Although depending on the material of the anode, thickness of the anode is typically in a range of 10 nm to 1 ⁇ m, and preferably in a range of 10 to 200 nm.
- the emitting layer of the organic EL device has functions described below. Specifically, the emitting layer has:
- injecting function a function for accepting, when an electrical field is applied, the holes injected by the anode or the hole injecting/transporting layer, or the electrons injected by the cathode or the electron injecting/transporting layer;
- transporting function a function for transporting injected electric charges (the electrons and the holes) by the force of the electrical field; and
- emitting function a function for providing a condition for recombination of the electrons and the holes to emit light.
- the emitting layer preferably transports at least either one of the electric charges.
- the emitting layer is preferably a molecular deposit film.
- the molecular deposit film means a thin film formed by depositing a material compound in gas phase or a film formed by solidifying a material compound in a solution state or in liquid phase.
- the molecular deposit film is generally distinguished from a thin film formed by the LB method (molecular accumulation film) by differences in aggregation structures, higher order structures and functional differences arising therefrom.
- the emitting layer can be formed from a thin film formed by spin coating or the like, the thin film being formed from a solution prepared by dissolving a binder (e.g. a resin) and a material compound in a solvent.
- a binder e.g. a resin
- the emitting layer of the present invention contains a host and a dopant.
- the emitting layer is preferably doped with a dopant material at a doping concentration of 0.1 to 10 mass %, more preferably 0.5 to 2.0 mass %.
- the emitting layer preferably emits light of orange to red.
- the host is a naphthacene derivative represented by the above formula (1).
- Q 10 , Q 20 , Q 30 , Q 40 , Q 50 , Q 60 , Q 70 , Q 80 , Q 110 , Q 120 , Q 130 and Q 140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group
- Q 10 , Q 20 , Q 30 and Q 40 are each preferably selected from a group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group and a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms. More preferably, Q 10 to Q 40 are aryl groups. Particularly, a structure where Q 10 and Q 40 are hydrogen atoms while Q 20 and Q 30 are the above substituents is also preferable.
- Q 10 and Q 40 are the same while Q 20 and Q 30 are the same is preferable, Q 10 to Q 40 may be mutually different.
- Q 50 , Q 60 , Q 70 and Q 80 are each preferably selected from a group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms and a substituted or unsubstituted heterocyclic group.
- Q 50 to Q 80 are each a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- Q 50 to Q 80 may be mutually different.
- Q 10 , Q 120 , Q 130 and Q 140 are each preferably a hydrogen atom.
- the alkyl group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 may be substituted or unsubstituted, or may be linear or branched.
- Preferable examples of the alkyl group are a methyl group, an ethyl group, a (n, i)-propyl group, a (n, i, sec, tert)-butyl group, and (n, i, neo, tert)-pentyl group.
- the aryl group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 may monocyclic or polycyclic, or may be of a condensed-ring structure or of a ring-assembly structure.
- the aryl group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 may be substituted or unsubstituted.
- the aryl group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 is preferably a phenyl group, an (o-, m-, p-) tolyl group, a pyrenyl group, a perylenyl group, a coronenyl group, a (1-, and 2-) naphthyl group, an anthryl group, a (o-, m-, p-) biphenyl group, a taphenyl group and a phenanthryl group.
- amino group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 10 to Q 140 may be substituted or unsubstituted, the amino group(s) is preferably substituted and may be an alkylamino group, an arylamino group, an aralkylamino group or the like.
- the above amino groups each preferably contain fatty series having 1 to 6 carbon atoms in total and/or an aromatic carbon ring having 1 to 4 rings.
- Examples of such an amino group are a dimethylamino group, a diethylamino group, an abutyl-amino group, a diphenylamino group, a ditolylamino group, a bis-diphenylamino group and a bis-naphtylamino group.
- the heterocyclic group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 may be substituted or unsubstituted.
- the heterocyclic group(s) are a five- or six-membered aromatic heterocyclic group containing O, N and S as heteroatoms and a condensed polycyclic aromatic group having 2 to 20 carbon atoms.
- the aromatic heterocyclic group and the condensed polycyclic aromatic heterocyclic group are a thienyl group, a furyl group, a pyronyl group, a pyridyl group, a quinolyl group and a quinoxalyl group.
- Examples of the substituted or unsubstituted alkenyl group(s) having 1 to 20 carbon atoms represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 are a (1- and 2-) phenylalkenyl group, a (1,2- and 2,2-) diphenylalkenyl group and a (1,2,2-)triphenylalkenyl group that are each substituted by at least one phenyl group.
- Each of the above examples may be unsubstituted.
- the alkoxy group(s) or the alkylthio group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 may be substituted or unsubstituted.
- the alkoxy group(s) or the alkylthio group(s) preferably contains the above-described alkyl group.
- the aryloxy group(s) or the arylthio group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 may be substituted or unsubstituted.
- the aryloxy group(s) or the arylthio group(s) preferably has an aryl group.
- An example of the aryloxy group(s) is an (o-, m-, p-) phenoxy group while an example of the arylthio group(s) is an (o-, m-, p-) phenylthio group.
- the aralkyl group(s) represented by Q 10 to Q 40 , Q 50 to Q 80 and Q 110 to Q 140 may be substituted or unsubstituted, examples of which are a benzyl group and a phenethyl group.
- At least two of the substituents contained, particularly, in Q 10 to Q 40 are each preferably an aryl group, an amino group, a heterocyclic group, an alkenyl group or an aryloxy group, more preferably an aryl group.
- the same as described in relation to Q 10 to Q 40 applies to the aryl group, the amino group, the heterocyclic group and the alkenyl group.
- Q 10 to Q 40 , Q 50 to Q 80 , and Q 110 to Q 140 are substituted, at least two, particularly, of Q 10 to Q 40 each preferably contain the above substituent.
- the substitution positions are not subject to any specific limitations.
- the substitution positions may be any one of meta, para and ortho positions.
- At least one of Q 10 to Q 80 is preferably a substituted or unsubstituted aryl group. More preferably, at least one of Q 10 to Q 40 is a substituted or unsubstituted aryl group.
- the naphthacene derivative is more preferably represented by the above formula (3).
- Q 10 , Q 21 to Q 25 , Q 31 to Q 35 Q 40 to Q 80 and Q 110 to Q 140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
- Q 10 , Q 21 to Q 25 , Q 31 to Q 35 , Q 40 to Q 80 and Q 110 to Q 140 may be mutually the same or different. Adjacent two or more of Q 21 to Q 25 and Q 31 to Q 35 may be mutually bonded to form a cyclic structure.
- Q 21 to Q 25 and Q 31 to Q 35 are each preferably selected from a group consisting of a hydrogen group, an aryl group, an amino group, a heterocyclic group, an aryloxy group and an alkenyl group, more preferably an aryl group.
- at least one of Q 21 to Q 25 and Q 31 to Q 35 is preferably substituted by an aryl group, an amino group, a heterocyclic group or an aryloxy group, more preferably by an aryl group. Adjacent two or more of the above may form a condensed ring.
- the same as described in relation to Q 10 to Q 40 applies to preferable examples of the aryl group, the amino group, the heterocyclic group and the alkenyl group.
- Q 21 to Q 25 and Q 31 to Q 35 are the same is preferable, Q 21 to Q 25 may be different from Q 31 to Q 35 .
- the amino group for substituting Q 21 to Q 25 and Q 31 to Q 35 are an alkylamino group, an arylamino group and an aralkylamino group.
- the above amino groups each preferably contain fatty series having 1 to 6 carbon atoms in total and/or an aromatic carbon ring having 1 to 4 rings.
- Examples of such an amino group are a dimethylamino group, a diethylamino group, an abutyl-amino group, a diphenylamino group, a ditolylamino group, a bis-diphenylamino group and a bis-naphtylamino group.
- Examples of the condensed ring formed as above are indene, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, quinoxaline, phenazine, acridine, indole, carbazole, phenoxazine, phenothiazine, benzothiazole, benzothiophen, benzofuran, acridone, benzoimidazole, coumarin and flavone.
- Q 10 , Q 40 and Q 110 to Q 140 are each particularly preferably a hydrogen atom.
- the dopant is a compound having the pyrromethene skeleton represented by the formula (2) or a metal complex of the compound.
- the compound having the pyrromethene skeleton represented by the formula (2) or the metal complex of the compound is preferably a compound having a pyrromethene skeleton represented by the following formula (2-1) or a metal complex of the compound.
- R 22 to R 28 is a substitute having an aromatic ring or forms a condensed aromatic ring together with an adjacent substituent while the rest of R 22 to R 28 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a silox
- R 22 to R 28 each may form a condensed ring or an aliphatic ring with an adjacent substituent.
- R 22 to R 28 may be mutually the same or different and may be substituted or unsubstituted.
- R 29 and R 30 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group.
- X represents a carbon atom or a nitrogen atom on a condition that R 28 above does not exist when X represents a nitrogen atom.
- the condensed aromatic ring(s) is preferably formed by a pair of R 22 and R 23 , a pair of R 23 and R 24 , a pair of R 25 and R 26 and/or a pair of R 26 and R 27 .
- the condensed aromatic ring(s) is particularly preferably formed by the pair of R 22 and R 23 and/or the pair of R 26 and R 27 .
- Examples of the condensed aromatic ring(s) are a benzo ring and a naphtho ring.
- the compound having the pyrromethene skeleton represented by the formula (2) or the metal complex of the compound is preferably a compound having a pyrromethene skeleton represented by the following formula (2-2) or a metal complex of the compound.
- R 31 to R 39 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group.
- R 31 to R 39 may be mutually the same or different and may be substituted or unsubstituted.
- R 40 and R 41 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group.
- X represents a carbon atom or a nitrogen atom on a condition that R 39 above does not exist when X represents a nitrogen atom.
- the compound having the pyrromethene skeleton represented by the formula (2-1) or the metal complex of the compound is preferably a metal complex having a pyrromethene skeleton represented by the following formula (2-3).
- R 42 to R 52 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group.
- R 42 to R 52 may be mutually the same or different and may be substituted or unsubstituted.
- R 53 and R 54 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group.
- X represents a carbon atom or a nitrogen atom on a condition that R 52 above does not exist when X represents a nitrogen atom.
- Q 10 to Q 140 and R 15 to R 54 may be substituted or unsubstituted, a substituent for each of which is preferably an alkyl group, an aryl group or an alkoxy group.
- the alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, further preferably an alkyl group having 1 to 5 carbon atoms.
- the alkyl group may be linear or branched.
- the alkyl group may be a primary alkyl group, a secondary alkyl group or a tertiary alkyl group.
- alkyl group are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group and an n-decyl group.
- the aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms.
- Examples of the aryl group are a phenyl group, a tolyl group, a xylyl group, a phenylphenyl group (4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group), a naphthylphenyl group, a naphthyl group (1-naphthyl group, 2-naphthyl group), a phenylnaphthyl group, a naphthylnaphthyl group, a taphenyl group, an anthranil group, a phenantyl group, a pyrenyl group and a chrysenyl group.
- the hole transporting layer helps injection of the holes into the emitting layer and transports the holes to an emitting region, in which the hole mobility is large and the energy of ionization is typically small (5.5 eV or smaller).
- a material of the hole transporting layer is preferably such a material that transports the holes to the emitting layer with a low field intensity, and more preferably such a material that transports the holes with the hole mobility of at least 10 ⁇ 4 cm 2 /V*sec when the exemplary electrical field of 10 4 to 10 6 V/cm is applied.
- a material for the hole transporting layer is not specifically limited as long as the material has the above preferable characteristics. Any materials conventionally used for transporting charges of the holes in photoconducting materials or any materials publicly known to be applicable to the hole transporting layers of the EL devices may be used.
- Examples of the material are a triazole derivative (see, for instance, the specification of U.S. Pat. No. 3,112,197), an oxadiazole derivative (see, for instance, the specification of U.S. Pat. No. 3,189,447), an imidazole derivative (see, for instance, the publication of JP-B-37-16096), a polyarylalkane derivative (see, for instance, the specifications of U.S. Pat. No. 3,615,402, No. 3,820,989 and No.
- a material represented by the following formula (7) may be used.
- Q 1 and Q 2 each represent a portion having at least one tertiary amine while G represents a linking group.
- More preferable material is an amine derivative represented by the following formula (8).
- Ar 21 to Ar 24 each represent a substituted or unsubstituted aromatic ring having 6 to 50 carbon atoms forming the ring or a substituted or unsubstituted heteroaromatic ring having 5 to 50 atoms forming the ring.
- R 21 and R 22 each represent a substituent while s and t each represent an integer in a range of 0 to 4.
- Ar 21 and Ar 22 may be bonded together to form a cyclic structure while Ar 23 and Ar 24 may also be bonded together to form a cyclic structure.
- R 21 and R 22 may also be bonded together to form a cyclic structure.
- the substituent for Ar 21 to Ar 24 each, and R 21 and R 22 are selected from a group consisting of a substituted or unsubstituted aromatic ring having 6 to 50 carbon atoms forming the ring, a substituted or unsubstituted heteroaromatic ring having 5 to 50 atoms forming the ring, an alkyl group having 1 to 50 carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylaryl group having 1 to 50 carbon atoms, an aralkyl group having 1 to 50 carbon atoms, a styryl group, an amino group substituted by an aromatic ring having 6 to 50 carbon atoms forming the ring or by a heteroaromatic ring having 5 to 50 atoms forming the ring, an aromatic ring having 6 to 50 carbon atoms forming the ring substituted by an amino group substituted by an aromatic ring having 6 to 50 carbon atoms forming the ring or by a heteroaromatic ring having 5 to
- a hole injecting layer may be provided in addition to the hole transporting layer.
- the above materials for the hole transporting layer can be used as the materials of the hole injecting layer, preferable examples of which are a porphyrin compound (disclosed in JP-A-63-295695), an aromatic tertiary amine compound and a styrylamine compound (see, for instance, the specification of U.S. Pat. No.
- NPD 4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl
- MTDATA 4,4′,4′′-tris(N-3-methylphenyl-N-phenylamino)triphenylamine
- a nitrogen-containing heterocyclic derivative represented by the following formula (9), which is disclosed in Japanese Patent No. 03571977, may be used.
- R 1 to R 6 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
- R 1 to R 6 may be mutually the same or different.
- a pair of R 1 and R 2 , a pair of R 3 and R 4 or a pair of R 5 and R 6 may form a condensed ring(s).
- a pair of R 1 and R 6 , a pair of R 2 and R 3 or a pair of R 4 and R 5 may form a condensed ring(s).
- R1 to R6 each represent a substituent, a preferable example of which is an electron-attracting group such as a cyano group, a nitro group, a sulfonyl group, a carbonyl group, a trifluoromethyl group and halogen.
- inorganic compounds such as p-type Si and p-type SiC can be used as the material of the hole injecting layer.
- the hole injecting layer and the hole transporting layer can be formed by forming thin films from the compounds listed above by known methods such as vacuum deposition, spin coating, casting and the LB method.
- the thickness of the hole injecting layer and the hole transporting layer is not particularly limited, the thickness is typically in the range from 5 nm to 5 ⁇ m.
- the hole injecting layer and the hole transporting layer may be formed by a single layer formed of at least one of the above materials as long as the hole injecting layer and the hole transporting layer contains the above compound(s) in the hole transporting region.
- the hole injecting layer and the hole transporting layer may be formed by laminating layers respectively formed of a different material.
- an organic semiconductor layer which is a part of the hole transporting layer, aids the injection of the holes or the electrons into the emitting layer.
- the organic semiconductor layer preferably has electric conductivity of 10 ⁇ 10 S/cm or more.
- Examples of a material for the organic semiconductor layer are a conductive oligomer such as a thiophene-containing oligomer or an arylamine-containing oligomer (disclosed in JP-A-08-193191), and a conductive dendrimer such as an arylamine-containing dendrimer.
- the electron transporting layer which aids injection of the electrons into the emitting layer, has a high electron mobility.
- the thickness of the electron transporting layer is suitably selected from the range of several nanometers to several micrometers. However, especially when the thickness of the electron transporting layer is large, the electron mobility, in order to prevent voltage from rising, is preferably at least 10 ⁇ 5 cm 2 /Vs or higher with the electrical field of 10 4 to 10 6 V/cm applied.
- the electron transporting layer preferably contains a compound represented by any one of the following formulae (4), (5) and (6).
- R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms while p represents an integer in a range of 1 to 4.
- aryl group having 6 to 60 carbon atoms are a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-ta-phenyl-4-yl group, p-ta-phenyl-3-yl group, p-ta-phenyl-2-yl group, m-ta-phenyl-4-yl group, m-ta-phenyl group, m
- More preferable examples thereof are a phenyl group, naphthyl group, biphenyl group, anthracenyl group, phenanthryl group, pyrenyl group, crycenyl group, fluoranthenyl group and fluorenyl group.
- alkyl group having 1 to 20 carbon atoms are a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group,
- the alkoxy group having 1 to 20 carbon atoms is a group represented by —OY′′′.
- Y′′′ are the same as those of the above alkyl group.
- Examples of the substituent for the aryl group, the pyridyl group, the quinolyl group, the alkyl group or the alkoxy group are a substituted or unsubstituted aryl group having 6 to 50 carbon atoms forming the ring, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 atoms forming the ring, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 atoms forming the ring, a substituted or unsubstituted arylthio group having 5 to 50 atoms forming the ring, a substituted or unsubstituted carboxyl group having 1 to 50 carbon atoms
- p represents an integer in a range of 1 to 4.
- p is any one of 1 to 3, more preferably 1 or 2.
- R preferably represents a hydrogen atom.
- R 11 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms. Examples of each group and substituent are the same as R.
- R 12 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Examples of each group and substituent are the same as R.
- L represents a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted quinolinylene group, or a substituted or unsubstituted fluorenylene group.
- arylene group having 6 to 60 carbon atoms are divalent substituents formed by further removing one hydrogen atom from the substituents listed in the description of the aryl group having 6 to 60 carbon atoms. More preferable examples thereof are a phenylene group, naphthylene group, biphenylene group, anthracenylene group, phenantolylene group, pyrenylene group, chrysenylene group, fluoranthenylene group and fluorenylene group.
- Examples of the substituent for each of the arylene group, the pyridinylene group, the quinolinylene group or the fluorenylene group are the same as R.
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms (preferably, 6 to 30 carbon atoms), a substituted or unsubstituted pyridyl group or a substituted or unsubstituted quinolyl group.
- Examples of the substituent for each of the aryl group having 6 to 60 carbon atoms, the aryl group, the pyridyl group or the quinolyl group are the same as R.
- R represents a hydrogen atom
- R 11 represents an aryl group
- L represents an arylene group having 6 to 30 carbon atoms (preferably, 6 to 20 carbon atoms)
- Ar 1 represents an aryl group having 6 to 30 carbon atoms.
- R represents a hydrogen atom
- R 12 represents an aryl group
- L represents an arylene group having 6 to 30 carbon atoms (preferably, 6 to 20 carbon atoms)
- Ar 1 represents an aryl group having 6 to 30 carbon atoms.
- the material of the electron transporting layer is not limited thereto.
- Compounds containing 8-hydroxyquinoline, a metal complex of its derivative, or a nitrogen-containing heterocycle may be preferably applicable to the electron transporting layer.
- 8-hydroxyquinoline or the metal complex of its derivative is a metal chelate oxinoid compound containing a chelate of oxine (typically 8-quinolinol or 8-hydroxyquinoline).
- a metal chelate oxinoid compound containing a chelate of oxine typically 8-quinolinol or 8-hydroxyquinoline.
- an Alq complex having Al as its central metal can be used for the electron transporting layer.
- examples of the oxadiazole derivative are electron transporting compounds represented by the following general formulae.
- Ar 321 , Ar 322 , Ar 323 , Ar 325 , Ar 326 and Ar 329 each represent a substituted or unsubstituted aryl group, which may be mutually the same or different.
- Ar 324 , Ar 327 and Ar 328 each represent a substituted or unsubstituted arylene group, which may be mutually the same or different.
- Examples of the aryl group are a phenyl group, a biphenyl group, an anthranil group, a perylenyl group, and a pyrenyl group.
- Examples of the arylene group are a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a perylenylene group and a pyrenylene group.
- the substituent therefor are an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a cyano group.
- the electron transporting compounds are preferably compounds that exhibit favorable performance in forming a thin film.
- Examples of the electron transporting compounds are as follows.
- Me represents a methyl group while Bu represents a butyl group.
- a silacyclopentadiene derivative represented by the following formula (disclosed in JP-A-09-087616) is also preferably applicable to the electron transporting layer.
- X 351 and Y 351 may each represent a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle, or X 351 and Y 351 may be bonded together to form a saturated or unsaturated ring.
- R 351 to R 354 may each represent hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an azo group, an alkylcarbonyloxy group, an arylcarbonyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyl group, a sulfonyl group, a sulfanyl group, a silyl group, a carbamoyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, a nitro group, a formyl group, a
- a silacyclopentadiene derivative represented by the following formula (disclosed in JP-A-09-194487) is also preferably applicable to the electron transporting layer.
- X 361 and Y 361 may each represent a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle, or X 361 and Y 361 may be bonded together to form a saturated or unsaturated ring.
- R 361 to R 364 may each represent hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an azo group, an alkylcarbonyloxy group, an arylcarbonyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyl group, a sulfonyl group, a sulfanyl group, a silyl group, a carbamoyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, a nitro group, a formyl group, a
- R 361 and R 364 are phenyl groups
- neither X 361 nor Y 361 is an alkyl group or a phenyl group.
- R 361 and R 364 are thienyl groups
- X 361 and Y 361 are each a univalent hydrocarbon group provided that neither R 362 nor R 363 is an alkyl group, an aryl group or an alkenyl group, or that R 362 and R 363 are not bonded together to form an aliphatic ring group.
- R 361 and R 364 are silyl groups
- none of R 362 , R 363 , X 361 and Y 361 is a univalent hydrocarbon group having 1 to 6 carbon atoms or a hydrogen atom.
- R 361 and R 362 are of a condensed benzene-ring structure
- neither of X 361 nor Y 361 is an alkyl group or a phenyl group.
- a borane derivative represented by the following formula (disclosed in JP-A1-2000-040586) is also preferably applicable to the electron transporting layer.
- R 371 to R 378 and Z 372 each represent a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amino group, a substituted boryl group, an alkoxy group or an aryloxy group;
- X 371 , Y 371 and Z 371 each represent a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amino group, an alkoxy group or an aryloxy group;
- substituent groups of Z 371 and Z 372 may be bonded to form a condensed ring; and
- n represents an integer in a range of 1 to 3, where when n is equal to or larger than 2, Z 371 does not have to be the same.
- n is 1; X 371 , Y 371 and R 372 are the methyl groups; and R 378 is the hydrogen atom or the substituted boryl group, or when: n is 3; and Z 371 is the methyl group.
- a compound represented by the following formula (disclosed in JP-A-10-088121) is also preferably applicable to the electron transporting layer.
- Q 381 and Q 382 each represent a ligand shown by the formula below.
- L 381 represents a ligand which may be a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or L 381 represents a ligand represented by —OR 391 (R 391 representing a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group) or a ligand represented by —O—Ga-Q 391 (Q 392 ) (Q 391 and Q 392 being the same as Q 381 and Q 382 ).
- rings A 401 and A 402 are bonded together to form a substituted or unsubstituted aryl ring or a heterocycle.
- substituent groups of the ring A 401 and the ring A 402 that form the ligands in the formula above are: halogen atoms such as chlorine, bromine, iodine and fluorine; substituted or unsubstituted alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group and a trichloromethyl group; substituted or unsubstituted aryl groups such as a phenyl group, a naphthyl group a 3-methylphenyl group, a 3-methoxyphenyl group, a 3-fluorophenyl group, a 3-trichloromethylphenyl group, a 3-trifluoromethyl
- the organic EL device As a preferred embodiment of the organic EL device according to the present invention, there is known a device containing a reductive dopant at a boundary between a region transporting the electrons or the cathode and an organic layer.
- the reductive dopant is defined as a substance capable of reducing an electron transporting compound.
- various substances having a certain level of reducibility can be used, preferable examples of which are at least one substance selected from a group consisting of: alkali metal, alkali earth metal, rare earth metal, an oxide of the alkali metal, a halogenide of the alkali metal, an oxide of the alkali earth metal, a halogenide of the alkali earth metal, an oxide of the rare earth metal, a halogenide of the rare earth metal, an organic complex of the alkali metal, an organic complex of the alkali earth metal and an organic complex of the rare earth metal.
- the reductive dopant is preferably a substance(s) having the work function of 2.9 eV or lower, which is exemplified by at least one alkali metal selected from a group consisting of Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1.95 eV) or at least one alkali earth metal selected from a group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV) and Ba (work function: 2.52 eV).
- the reductive dopant is more preferably at least one alkali metal selected from a group consisting of K, Rb and Cs, among which Rb and Cs are even more preferable and Cs is the most preferable.
- alkali metals have particularly high reducibility, so that addition of a relatively small amount of these alkali metals to an electron injecting zone can enhance luminescence intensity and lifecycle of the organic electroluminescence device.
- the reductive dopant having the work function of 2.9 eV or lower a combination of two or more of these alkali metals is also preferable, and a combination including Cs is particularly preferable (e.g.
- combinations of Cs and Na, Cs and K, Cs and Rb or Cs, Na and K can effectively exert the reducibility, so that the addition of such reductive dopant to the electron injecting zone can enhance the luminescence intensity and the lifecycle of the organic electroluminescence device.
- an electron injecting layer formed from an insulator or a semiconductor may be provided between the cathode and the organic layer.
- the insulator it is preferable to use at least one metal compound selected from a group consisting of an alkali metal chalcogenide, an alkali earth metal chalcogenide, a halogenide of alkali metal and a halogenide of alkali earth metal.
- preferable examples of the alkali metal chalcogenide are Li 2 O, LiO, Na 2 S, Na 2 Se and NaO, while preferable example of the alkali earth metal chalcogenide are CaO, BaO, SrO, BeO, BaS and CaSe.
- Preferable examples of the halogenide of the alkali metal are LiF, NaF, KF, LiCl, KCl and NaCl.
- Preferable examples of the halogenide of the alkali earth metal are fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halogenides other than the fluoride.
- Examples of the semiconductor for forming the electron injecting layer are one of or a combination of two or more of an oxide, a nitride or an oxidized nitride containing at least one element selected from a group consisting of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn.
- An inorganic compound for forming the electron injecting layer is preferably a microcrystalline or amorphous semiconductor film. When the electron injecting layer is formed of such semiconductor film, more uniform thin film can be formed, thereby reducing pixel defects such as a dark spot.
- Examples of such an inorganic compound are the above-described alkali metal chalcogenide, alkali earth metal chalcogenide, halogenide of the alkali metal and halogenide of the alkali earth metal.
- a material whose work function is small (4 eV or lower) is used as an electrode material for the cathode, examples of the material being metals, alloys, electrically conductive compounds and mixtures thereof.
- the electrode material are sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-silver alloy, aluminium/aluminium oxide, an aluminium-lithium alloy, indium, rare earth metal and the like.
- the cathode is made by forming a thin film from the electrode material by vapor deposition and sputtering.
- the cathode When the organic EL device is top-emission type, the cathode preferably transmits more than 10% of light emitted by the emitting layer.
- the sheet resistance as the cathode is preferably several hundreds ⁇ /square or lower, and the thickness of the film is typically in a range from 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
- Examples of a material used for the insulating layer are aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, cesium fluoride, cesium carbonate, aluminium nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like.
- Mixtures or laminates thereof may also be used.
- the organic EL device can be manufactured by forming the anode, the emitting layer and the cathode (in addition to the above, forming the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer as necessary) from the materials listed above by the above-described formation methods.
- the organic EL device can also be manufactured by forming the above elements in the inverse order of the above, namely from the cathode to the anode.
- the following is a manufacturing example of the organic EL device in which the anode, the hole transporting layer, the emitting layer, the electron transporting layer and the cathode are sequentially formed on the light-transmissive substrate.
- a thin film is formed of the anode material on a suitable light-transmissive substrate by vapor deposition or sputtering such that the thickness of the thin film is 1 m or smaller, preferably in a range from 10 nm to 200 nm, thereby forming the anode.
- the hole transporting layer is formed on the formed anode.
- the hole transporting layer may be formed by a method such as vacuum deposition, spin coating, casting and the LB method as described above, among which vacuum deposition is preferable in forming the hole transporting layer because the method can easily form homogeneous films and can prevent generation of pin holes.
- conditions for conducting vacuum deposition depend on the compounds to be used (i.e., the material of the hole transporting layer), a crystal structure of the targeted hole transporting layer, and a recombination structure of the targeted hole transporting layer.
- conditions are preferably set so as to satisfy deposition-source temperature of 50 to 450 degrees C., vacuum of 10 ⁇ 7 to 10 ⁇ 3 torr, deposition speed of 0.01 to 50 nm/second, substrate temperature of ⁇ 50 to 300 degrees C., film thickness of 5 nm to ⁇ m.
- the emitting layer is formed on the hole transporting layer.
- the emitting layer may also be formed of a desirable material by a method such as vacuum deposition, sputtering, spin coating and casting, among which vacuum deposition is preferable in forming the emitting layer because the method can easily form homogeneous films and can prevent generation of pin holes.
- deposition conditions for forming the emitting layer can be generally set in the same manner as the hole transporting layer although the deposition conditions may vary depending on compounds used for forming the emitting layer.
- the electron transporting layer is formed on the emitting layer.
- the electron transporting layer is also preferably formed by vacuum deposition so as to form a homogeneous film. Deposition conditions for forming the electron transporting layer can be set in the same manner as the hole transporting layer and the emitting layer.
- the cathode is laminated thereon.
- the cathode can be formed from a metal by a method such as vapor deposition and sputtering. In order to protect the organic layers deposited under the cathode from being damaged, the vacuum deposition is preferable.
- the above-described organic EL device is preferably manufactured such that all layers from the anode to the cathode are formed in one vacuuming.
- each layer of the organic EL device is not particularly limited. Conventionally-known methods such as vacuum deposition, molecular-beam deposition, spin coating, dipping, casting, bar coating and roll coating are applicable to forming the layers.
- each organic layer of the organic EL device is not particularly limited, the thickness is generally preferably in a range of several nanometers to 1 ⁇ m because excessively-thinned film likely entails defects such as a pin hole while excessively-thickened film requires high voltage to be applied and deteriorates efficiency.
- the light-emission can be observed by applying a voltage of 3 to 40V with the anode having the positive polarity and the cathode having the negative polarity.
- the voltage is applied with the inversed polarity, no current flows, so that no light is emitted.
- an alternating voltage is applied, the uniform light-emission can be observed only when the anode has the positive polarity and the cathode has the negative polarity.
- a waveform of the alternating current to be applied may be suitably selected.
- a 130 nm-thick transparent electrode formed of indium tin oxide was formed on a glass substrate having a size of 25 mm by 75 mm by 0.7 mm. After the transparent substrate was ultrasonically cleaned in isopropyl alcohol for five minutes, the substrate was further cleaned with UV (ultraviolet) ozone for thirty minutes, and then the substrate was mounted on a vapor deposition apparatus.
- N,N′-bis[4-(N,N-diphenylamino)phenyl-1-yl]-N,N′-diphenyl-4,4′-benzidine was deposited on the substrate to form a 60 nm-thick hole injecting layer, and subsequently N,N′-bis[4′- ⁇ N-(naphthyl-1-yl)-N-phenyl ⁇ aminobiphenyl-4-yl]-N-phenylamine was deposited thereon to form a 10 nm-thick hole transporting layer.
- the organic EL device was manufactured by the above-described manner.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.7 V to emit red light having a luminescence intensity of 711 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.11 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half (i.e., time until half-life) was 1,800 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (A-2) was used in place of the compound (A-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 720 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.20 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 2,000 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (A-3) was used in place of the compound (A-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 737 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.37 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 3,200 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-2) was used in place of the compound (B-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 698 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 6.98 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 1,900 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-3) was used in place of the compound (B-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 710 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.10 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 1,500 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-4) was used in place of the compound (B-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.7 V to emit red light having a luminescence intensity of 676 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 6.76 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 1,600 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (C-2) was used in place of the compound (C-1) for forming the electron transporting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 5.6 V to emit red light having a luminescence intensity of 564 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.64, 0.34), and efficiency of the device was 5.64 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 1,000 hours.
- An organic EL device was manufactured in the same manner as in Example 7 except that the following compound (C-2) was used in place of the compound (A-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 6.1 V to emit red light having a luminescence intensity of 434 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.63, 0.35), and efficiency of the device was 4.34 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 500 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-5) was used in place of the compound (B-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.7 V to emit red light having a luminescence intensity of 385 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.64, 0.37), and efficiency of the device was 3.85 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 700 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (C-2) was used in place of the compound (A-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 5.2 V to emit red light having a luminescence intensity of 451 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.65, 0.33), and efficiency of the device was 4.51 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 600 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-6) was used in place of the compound (B-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.4 V to emit red light having a luminescence intensity of 1,081 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.65, 0.34), and efficiency of the device was 10.81 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 3,500 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-7) was used in place of the compound (B-1) for forming the emitting layer.
- the organic EL device When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.5 V to emit red light having a luminescence intensity of 852 cd/m 2 at a current density of 10 mA/cm 2 , a trichromatic coordinate of the emitted light was (0.67, 0.33), and efficiency of the device was 8.52 cd/A.
- a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m 2 , time elapsed until the luminescence intensity was reduced by half was 3,300 hours.
- Example 7 in which the compound (A-1) was used as the host, is more excellent in drive voltage, luminescence intensity, chromaticity and time until half-life.
- a combination of the compound (A-1) and the compound (B-1) as the combination of the host and the dopant is more excellent than a combination of the compound (C-2), a general host material, and the compound (B-1).
- Example 1 to 6 and Comparatives 2 and 3 the compound (C-1) was used as the electron transporting layer.
- the compound (B-5) was used as the dopant in Comparative 2 while the compound (C-2) was used as the host in Comparative 3.
- the combination of the host and the dopant according to the present invention was used in Examples 1 to 6.
- the combination of the host and the dopant according to the present invention is excellent in terms of drive voltage, luminescence intensity, chromaticity, luminous efficiency and time until half-life.
- the combination of the host material and the dopant material according to the present invention is excellent in terms of drive voltage, luminescence intensity, chromaticity, efficiency and time until half-life.
- Example 7 It is understood from a comparison between Examples 1 to 6 and Example 7 that, by using such a material as represented by the compound (C-1) according to the present invention for the electron transporting material, the device can exhibit excellent performance in terms of drive voltage, luminescence intensity, chromaticity, efficiency, time until half-time and the like.
- the emitting region is typically preferably located within the emitting layer in the organic EL device.
- an emitting material for emitting red light tends to cause electron traps because an energy gap of the dopant is small. Accordingly, the electrons injected into the emitting layer from the electron transporting layer tend to be trapped in the dopant located adjacent to the electron transporting layer, thereby moving the emitting region toward the electron transporting layer.
- Example 7 the chromaticity was shifted toward green, and the compound (C-2) emitted light. It can be deduced from the above with respect to Example 7 that the holes were more strongly injected into the emitting layer than the electrons, and that many of the holes penetrated the emitting layer to reach the electron transporting layer, thereby generating exciters in the compound (C-2) forming the electron transporting layer. In addition, since the compound (C-2) emitted light, the time elapsed until the lifetime of the organic EL device was reduced by half is short.
- the electron transporting material according to the present invention is excellent in transporting electrons.
- the electron transporting layer formed of such an electron transporting material can strongly inject the electrons into the emitting layer, thereby preventing the holes from penetrating the emitting layer to reach the electron transporting layer.
- the organic EL device according to the present invention can emit light of high chromaticity with high efficiency while preventing generation of exciters in the electron transporting layer, and lifetime of the entire device is long.
- the electron transporting material can exhibit above-described excellent effects and advantages.
- Example 3 Lifetime of Example 3 is much longer than those of Examples 1 and 2 because the compound A-3 was used for the host in Example 3. It has been revealed from the above that substituent(s) in ortho position(s) of benzene rings bonded to the naphthacene skeleton prevents molecular association, thereby contributing to longer lifetime.
- the present invention is not limited to the above examples, but includes modifications and improvements made within a scope where an object of the present invention can be achieved.
- ruburene which is an example of the host material of Example 1
- the compounds used in the other Examples may be substituted or unsubstituted.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In an organic electroluminescence device including a cathode and an anode, at least an emitting layer and an electron transporting layer are provided between the cathode and the anode. The emitting layer contains a host material formed of a naphthacene derivative represented by the following formula (1) and a dopant material formed of a compound having a pyrromethene skeleton represented by the following formula (2) or a metal complex of the compound. The electron transporting layer is preferably a benzoimidazole derivative.
Description
- 1. Field of the Invention
- The present invention relates to an organic electroluminescence device (organic EL device) and a display that use a naphthacene derivative and a compound having a pyrromethene skeleton or a metal complex of the compound together.
- 2. Description of Related Art
- Organic electroluminescence (EL) devices have been known. Organic EL devices formed from organic materials have been vigorously studied since a report on a low voltage-driven organic EL device formed by laminating layers was made by C. W. Tang et al. of Eastman Kodak Company (see Document 1: Applied Physics Letters, vol. 51, page 913, by C. W. Tang and S. A. Vanslyke, 1987).
- Known examples of an emitting material used for an organic EL device are a chelate complex such as a tris(8-quinolinol)aluminum (Alq) complex, a coumarin complex, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, an oxadiazole derivative or the like. These emitting materials, which have been reported to emit blue to red light in a visible region, are expected to be applied to color-display devices (e.g., Document 2: JP-A-08-239655, Document 3: JP-A-07-138561, Document 4: JP-A-03-200889 and the like). However, luminous efficiency and lifetime of such a device has been so insufficient that the device has not been practically applicable. While a full color display requires three primary colors of blue, green and red, among them, a red-emitting device with high efficiency has been demanded.
- For instance, Document 5 (JP-A-08-311442) has recently disclosed a red-emitting device whose emitting layer is added with a naphthacene derivative or a pentacene derivative. However, although the red-emitting device is excellent in purity of red color, the red-emitting device requires voltage of 11V to be applied, and time lapsed until the luminescent intensity decreases to half is approximately 150 hours, i.e., the performance of the device is insufficient. Document 6 (JP-A-03-162481) discloses a device whose emitting layer is added with a dicyanomethylene (DCM)-based compound. However, the device exhibits insufficient purity of red color. Document 7 (JP-A-2001-81451) discloses a red-emitting device whose emitting layer is added with an amine-based aromatic compound. However, although the emitting device exhibits excellent CIE (Commission Internationale d'Eclairage) chromaticity (0.64, 0.33) and chromatic purity, the device requires high voltage for driving. Document 8 (WO/01/23497) and Document 9 (JP-A-2003-40845) disclose devices in which an amine-based aromatic compound and an Alq compound are used for the emitting layer. However, although emitting red light, the device exhibits low efficiency and short lifetime.
- Document 10 (JP-A-2003-81924) discloses devices in which an amine-based aromatic compound and DPVDPAN are used for the emitting layer. However, high-efficient one of the devices emits orange light while red-emitting one of the devices exhibits low efficiency.
- Document 11 (JP-A-2001-307885) discloses a device in which a dicyanoanthracene derivative and an indenoperylene derivative are used for the emitting layer while a metal complex is used for the electron transporting layer. However, the device emits light of red orange color.
- Document 12 (JP-A-2003-338377) discloses a device in which a fluoranthene derivative and an indenoperylene derivative are used for the emitting layer while a fluoranthene derivative is used for the electron transporting layer. However, the device does not exhibit practically-applicable efficiency.
- An object of the present invention is to provide an practically-applicable organic EL device and a practically-applicable display excellent in efficiency, lifetime and chromatic purity.
- After conducting concentrated studies in order to achieve such an object, the inventors have found that an organic EL device exhibits longer lifetime and higher efficiency by using a naphthacene derivative and a compound having a pyrromethene skeleton or a metal complex of the compound in at least one layer of organic compound layers of the organic EL device, and reached the present invention.
- An organic electroluminescence device according to an aspect of the present invention includes: a cathode; an anode; and an emitting layer provided between the cathode and the anode, in which the emitting layer comprises a host and a dopant, the host is a naphthacene derivative represented by a formula (1) as follows, and the dopant is a compound having a pyrromethene skeleton represented by a formula (2) as follows or a metal complex of the compound.
- In the formula (1), Q10, Q20, Q30, Q40, Q50, Q60, Q70, Q80, Q110, Q120, Q130 and Q140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group. Q10, Q20, Q30, Q40, Q50, Q60, Q70, Q80, Q110, Q120, Q130 and Q140 may be mutually the same or different.
- In the formula (2), at least one of R15 to R21 is a substitute having an aromatic ring or forms a condensed ring together with an adjacent substituent while the rest of R15 to R21 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, a haloalkane, a haloalkene, a haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group. The rest of R15 to R21 each may form a condensed ring or an aliphatic ring with an adjacent substituent (the groups listed above each have 1 to 20 carbon atoms). R15 to R21 may be mutually the same or different and may be substituted or unsubstituted. X represents a carbon atom or a nitrogen atom on a condition that R21 above does not exist when X represents a nitrogen atom. A metal in the metal complex is at least one metal selected from a group consisting of boron, beryllium, magnesium, chrome, iron, cobalt, nickel, copper, zinc and platinum.
- The metal in the metal complex is particularly preferably boron.
- The substituted or unsubstituted alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, further preferably an alkyl group having 1 to 5 carbon atoms. The alkyl group may be linear or branched. The alkyl group may be a primary alkyl group, a secondary alkyl group or a tertiary alkyl group.
- Preferable examples of the alkyl group are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group and an n-decyl group.
- The substituted or unsubstituted aryl group is preferably an aryl group having 6 to carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms. Examples of the aryl group are a phenyl group, a phenylphenyl group (4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group), a naphthylphenyl group (4-(1-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group), a naphthyl group (1-naphthyl group, 2-naphthyl group), a phenylnaphthyl group (6-phenyl-2-naphthyl group, 4-phenyl-1-naphthyl group), a naphthylnaphthyl group (6-naphthyl-2-naphthyl group, 4-naphthyl-1-naphthyl group), an anthranil group, a phenantyl group, a pyrenyl group and a chrysenyl group.
- The amino group may be an amino group, a substituted or unsubstituted monoalkyl-aryl group having 1 to 20 carbon atoms, a substituted or unsubstituted dialkyl-aryl group having 1 to 20 carbon atoms, a substituted or unsubstituted monoaryl-aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted bisaryl-aryl group having 6 to 30 carbon atoms. Examples of the amino group are a dimethylamino group, a diethylamino group, a diphenylamino group, a ditolylamino group and a dixylylamino group.
- The substituted or unsubstituted alkoxy group is preferably an alkoxy group having 1 to 20 carbon atoms, examples of which are a methoxy group, an ethoxy group and a propoxy group.
- The substituted or unsubstituted alkylthio group is preferably an alkylthio group having 1 to 20 carbon atoms, examples of which are a methylthio group and an ethylthio group.
- The substituted or unsubstituted aryloxy group is preferably an aryloxy group having 6 to 30 carbon atoms, an example of which is a phenoxy group.
- The substituted or unsubstituted aryloxythio group is preferably an aryloxythio group having 6 to 30 carbon atoms, an example of which is a phenylthio group.
- The substituted or unsubstituted alkenyl group is preferably an alkenyl group having 1 to 20 carbon atoms, examples of which are a vinyl group and a propenyl group.
- The substituted or unsubstituted aralkyl group is preferably an aralkyl group having 7 to 30 carbon atoms, an example of which is a benzyl group.
- The substituted or unsubstituted heterocyclic group is preferably a heterocyclic group having 5 to 30 carbon atoms, examples of which are a pyridyl group, a furyl group, a thienyl group, a pyrazyl group, a pyrimidyl group and a quinolyl group.
- According to the aspect of the present invention, since the emitting layer contains the host formed of a naphthacene derivative and the dopant formed of a compound having a pyrromethene skeleton or a metal complex of the compound, the organic EL device having practically-applicable efficiency and lifetime can be realized.
- According to the aspect of the present invention, it is preferable that the compound having the pyrromethene skeleton represented by the formula (2) or the metal complex of the compound is a metal complex having a pyrromethene skeleton represented by a formula (2-1) as follows.
- In the formula (2-1), at least one of R22 to R28 is a substitute having an aromatic ring or forms a condensed aromatic ring together with an adjacent substituent while the rest of R22 to R28 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group. The rest of R22 to R28 each may form a condensed ring or an aliphatic ring with an adjacent substituent. R22 to R28 may be mutually the same or different and may be substituted or unsubstituted. R29 and R30 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group. X represents a carbon atom or a nitrogen atom on a condition that R28 above does not exist when X represents a nitrogen atom.
- According to the aspect of the present invention, it is preferable that at least one of R22 to R28 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a substituent having an aromatic ring.
- According to the aspect of the present invention, it is preferable that at least one of R22 to R28 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a condensed aromatic ring together with an adjacent substituent.
- According to the aspect of the present invention, it is preferable that at least one of R22 to R24 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a substituted or unsubstituted condensed aromatic ring together with an adjacent substituent and/or at least one of R25 to R27 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a substituted or unsubstituted condensed aromatic ring together with an adjacent substituent.
- According to the aspect of the present invention, it is preferable that the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a metal complex having a pyrromethene skeleton represented by a formula (2-2) as follows.
- In the formula (2-2), R31 to R39 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group. R31 to R39 may be mutually the same or different and may be substituted or unsubstituted. R40 and R41 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group. X represents a carbon atom or a nitrogen atom on a condition that R39 above does not exist when X represents a nitrogen atom.
- According to the aspect of the present invention, it is preferable that the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a metal complex having a pyrromethene skeleton represented by a formula (2-3) as follows.
- In the formula (2-3), R42 to R52 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group. R42 to R52 may be mutually the same or different and may be substituted or unsubstituted. R53 and R54 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group. X represents a carbon atom or a nitrogen atom on a condition that R52 above does not exist when X represents a nitrogen atom.
- According to the aspect of the present invention, it is preferable that at least one of Q10, Q20, Q30 and Q40 in the naphthacene derivative represented by the formula (1) is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- According to the aspect of the present invention, it is preferable that the naphthacene derivative represented by the formula (1) is a naphthacene derivative represented by a formula (3) as follows.
- In the formula (3), Q10, Q21 to Q25, Q31 to Q35, Q40 to Q80 and Q110 to Q140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group. Q10, Q21 to Q25, Q31 to Q35, Q40 to Q80 and Q110 to Q140 may be mutually the same or different.
- Adjacent two or more of Q21 to Q25 and Q31 to Q35 may be mutually bonded to form a cyclic structure.
- According to the aspect of the present invention, it is preferable that at least one of Q21, Q25, Q31 an Q35 in the naphthacene derivative represented by the formula (3) represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
- According to the above structure, the naphthacene derivative represented by the formula (3) has a substituent in at least one ortho position of two benzene rings bonded to naphthacene.
- By introducing substituent(s) to ortho position(s) of the two benzene rings bonded to naphthacene, a steric hindrance is caused between the introduced substituent(s) and the naphthacene skeleton. The steric hindrance directs the introduced substituent(s) to face in an out-of-plane direction of the naphthacene skeleton. Then, the substituent(s) directed in the out-of-plane direction prevents association of naphthacene derivatives with each other.
- When two or more of Q21, Q25, Q31 and Q35 are substituents, the substituents may be mutually the same or different. In addition, adjacent two or more of Q21 to Q25 and Q31 to Q35 may be mutually bonded to form a cyclic structure.
- An example of the substituent is a substituted or unsubstituted phenyl group.
- Two or more of the ortho positions of the two benzene rings bonded to naphthacene are preferably substituted.
- According to the aspect of the present invention, it is preferable that at least one of Q21 and Q25 in the naphthacene derivative represented by the formula (3) represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group while at least one of Q31 and Q35 in the naphthacene derivative represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
- According to the aspect of the present invention, it is preferable that the dopant is contained in the emitting layer at a doping concentration of 0.1 to 10 mass %. It is more preferable that the dopant is contained in the emitting layer at a doping concentration of 0.5 to 2.0 mass %.
- According to the aspect of the present invention, it is preferable that the organic EL device further includes an electron transporting layer provided between the cathode and the anode, in which the electron transporting layer comprises a compound represented by a formula (4) as follows.
-
(A)m-(B)n (4) - In the formula, A represents a substituted or unsubstituted condensed aromatic hydrocarbon group having three or more rings, and B represents a substituted or unsubstituted heterocyclic group. In addition, m and n each represent an integer in a range of 1 to 6.
- According to the aspect of the present invention, it is preferable that A in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from a group consisting of anthracene, phenanthrene, naphthacene, pyrene, chrysene, benzoanthracene, pentacene, dibenzoanthracene, benzopyrene, fluorene, benzofluorene, fluoranthene, benzofluoranthene, naphthofluoranthene, dibenzofluorene, dibenzopyrene and dibenzofluoranthene.
- According to the aspect of the present invention, it is preferable that B in the compound represented by the formula (4) is a nitrogen-containing heterocyclic group.
- According to the aspect of the present invention, it is preferable that B in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from a group consisting of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, acridine, imidazopyridine, imidazopyrimidine, phenanthroline, pyrazole, imidazole and benzoimidazole.
- According to the aspect of the present invention, it is preferable that the compound represented by the formula (4) is a benzoimidazole derivative represented by a formula (5) or a formula (6) as follows.
- In the formulae: R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; p represents an integer in a range of 1 to 4; R11 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms; R12 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; L represents a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted quinolinylene group or a substituted or unsubstituted fluorenylene group; and Ar1 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group or a substituted or unsubstituted quinolyl group.
- At least one of R, R11, R12, L and Ar1 corresponds to A in the compound represented by the formula (4) and is a condensed aromatic hydrocarbon group having three or more rings.
- According to the aspect of the present invention, it is preferable that the emitting layer emits light of orange to red.
- A display according to another aspect of the present invention includes the above-described organic electroluminescence device.
- According to the above arrangement, since the display is formed from the above-described organic electroluminescence device, the display can exhibit high efficiency, long lifetime and excellent chromatic purity.
- The present invention can provide a practically-applicable organic EL device that exhibits high efficiency, long life and excellent chromatic purity.
- In addition, according to the present invention, by selecting a suitable compound for the materials of the electron transporting layer and the emitting layer, the organic EL device can exhibit higher efficiency. Specifically, with the arrangement according to the present invention, generation of exciters in the electron transporting layer can be prevented, thereby providing a highly chromatically-pure organic EL device whose micro emission from the electron transporting layer is further reduced In addition, for the same reason(s), the lifetime of the device can be prolonged.
-
FIG. 1 shows a first embodiment of an organic EL device according to the present invention. - Representative exemplary arrangements of an organic EL device usable in the present invention will be described below. As a matter of course, the present invention is not limited thereto.
- (1) anode/emitting layer/electron transporting layer/cathode
(2) anode/hole transporting layer/emitting layer/electron transporting layer/cathode
(3) anode/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/cathode
(4) anode/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/cathode
(5) anode/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/cathode (FIG. 1 )
(6) anode/insulating layer/hole transporting layer/emitting layer/electron transporting layer/cathode
(7) anode/hole transporting layer/emitting layer/electron transporting layer/insulating layer/cathode
(8) anode/insulating layer/hole transporting layer/emitting layer/electron transporting layer/insulating layer/cathode
(9) anode/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/insulating layer/cathode
(10) anode/insulating layer/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/cathode
(11) anode/insulating layer/hole injecting layer/hole transporting layer/emitting layer/electron transporting layer/electron injecting layer/insulating layer/cathode - Among the above, the arrangement (2), (3), (4), (5), (8), (9) or (11) is typically preferable.
- The organic EL device according to the present invention includes an anode, a cathode and a single-layered or plural-layered organic layer including an emitting layer. At least one layer of the organic layer contains a host formed of a naphthacene derivative and a dopant formed of a compound having a pyrromethene skeleton or a metal complex of the compound.
- An exemplary arrangement of the organic EL device according to the present invention is shown in
FIG. 1 . InFIG. 1 , the organic EL device 1 includes ananode 20, ahole injecting layer 30, ahole transporting layer 40, an emittinglayer 50, anelectron transporting layer 60, anelectron injecting layer 70 and acathode 80, which are all laminated on asubstrate 10 in this order. Thehole injecting layer 30, thehole transporting layer 40, the emittinglayer 50, theelectron transporting layer 60 and theelectron injecting layer 70 correspond to the organic layer interposed between thecathode 80 and theanode 20. At least one of the above layers contains a host material formed of a naphthacene derivative and a dopant material formed of a compound having a pyrromethene skeleton or a metal complex of the compound. Preferably, the emitting layer contains a naphthacene derivative and a compound having a pyrromethene skeleton or a metal complex of the compound. - Functions or the like of the layers of the organic EL device will be described below.
- When the organic EL device is to emit light through the substrate (i.e., when the organic EL device is bottom-emission type), the organic EL device according to the present invention is manufactured on a light-transmissive substrate. The light-transmissive plate, which supports the organic EL device, is preferably a smoothly-shaped substrate that transmits 50% or more of light in a visible region of 400 nm to 700 nm.
- The light-transmissive plate is exemplarily a glass plate, a polymer plate or the like. For the glass plate, such materials as soda-lime glass, barium/strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like can be used. For the polymer plate, such materials as polycarbonate, acryl, polyethylene terephthalate, polyether sulfide, polysulfone and the like can be used. In addition, the light-transmissive plate may be a TFT substrate on which a TFT (thin film transistor) for driving is formed.
- On the other hand, when the organic EL device is to emit light from its top portion (i.e., when the organic EL device is top-emission type), the light-transmissive plate is required to be provided with a light reflector, an exemplary material of which is a metal such as aluminum.
- The anode of the organic EL device is used for injecting holes into the hole transporting layer or the emitting layer. It is effective that the anode includes a work function of 4.5 eV or more. Exemplary materials for the anode are indium-tin oxide (ITO), tin oxide (NESA), indium zinc oxide alloy (IZO), gold, silver, platinum and copper.
- One of the above materials may be singularly used, or alloys formed by mixing the above materials and materials formed by adding other element(s) to the above material(s) may be suitably selected as the material of the anode.
- The anode may be made by forming a thin film from the above electrode materials through methods such as vapor deposition and sputtering.
- When the organic EL device is bottom-emission type, the anode preferably transmits more than 10% of light emitted by the emitting layer. Sheet resistance of the anode is preferably several hundreds Ω/square or lower. Although depending on the material of the anode, thickness of the anode is typically in a range of 10 nm to 1 μm, and preferably in a range of 10 to 200 nm.
- The emitting layer of the organic EL device has functions described below. Specifically, the emitting layer has:
- (i) injecting function: a function for accepting, when an electrical field is applied, the holes injected by the anode or the hole injecting/transporting layer, or the electrons injected by the cathode or the electron injecting/transporting layer;
(ii) transporting function: a function for transporting injected electric charges (the electrons and the holes) by the force of the electrical field; and
(iii) emitting function; a function for providing a condition for recombination of the electrons and the holes to emit light. - Although injectability of the holes may differ from that of the electrons and transporting capabilities represented by mobilities of the holes and the electrons may differ from each other, the emitting layer preferably transports at least either one of the electric charges.
- As a method to form the emitting layer, known methods such as vapor deposition, spin coating and an LB (Langmuir Blodgett) method may be employed. The emitting layer is preferably a molecular deposit film.
- The molecular deposit film means a thin film formed by depositing a material compound in gas phase or a film formed by solidifying a material compound in a solution state or in liquid phase. The molecular deposit film is generally distinguished from a thin film formed by the LB method (molecular accumulation film) by differences in aggregation structures, higher order structures and functional differences arising therefrom.
- As disclosed in JP-A-57-51781, the emitting layer can be formed from a thin film formed by spin coating or the like, the thin film being formed from a solution prepared by dissolving a binder (e.g. a resin) and a material compound in a solvent.
- The emitting layer of the present invention contains a host and a dopant.
- The emitting layer is preferably doped with a dopant material at a doping concentration of 0.1 to 10 mass %, more preferably 0.5 to 2.0 mass %.
- The emitting layer preferably emits light of orange to red.
- The host is a naphthacene derivative represented by the above formula (1).
- In the formula (1), Q10, Q20, Q30, Q40, Q50, Q60, Q70, Q80, Q110, Q120, Q130 and Q140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group. Q10, Q20, Q30, Q40, Q50, Q60, Q70, Q80, Q110, Q120, Q130 and Q140 may be mutually the same or different.
- In the above formula (1), Q10, Q20, Q30 and Q40 (collectively referred to as Q10 to Q40) are each preferably selected from a group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group and a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms. More preferably, Q10 to Q40 are aryl groups. Particularly, a structure where Q10 and Q40 are hydrogen atoms while Q20 and Q30 are the above substituents is also preferable.
- In addition, although a structure where Q10 and Q40 are the same while Q20 and Q30 are the same is preferable, Q10 to Q40 may be mutually different.
- In the above formula, Q50, Q60, Q70 and Q80 (collectively referred to as Q50 to Q80) are each preferably selected from a group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms and a substituted or unsubstituted heterocyclic group. More preferably, Q50 to Q80 are each a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. In addition, although a structure where Q50 and Q60 are the same while Q70 and Q80 are the same is preferable, Q50 to Q80 may be mutually different. Q10, Q120, Q130 and Q140 (collectively referred to as Q110 to Q140) are each preferably a hydrogen atom.
- The alkyl group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 may be substituted or unsubstituted, or may be linear or branched. Preferable examples of the alkyl group are a methyl group, an ethyl group, a (n, i)-propyl group, a (n, i, sec, tert)-butyl group, and (n, i, neo, tert)-pentyl group.
- The aryl group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 may monocyclic or polycyclic, or may be of a condensed-ring structure or of a ring-assembly structure. The aryl group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 may be substituted or unsubstituted. The aryl group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 is preferably a phenyl group, an (o-, m-, p-) tolyl group, a pyrenyl group, a perylenyl group, a coronenyl group, a (1-, and 2-) naphthyl group, an anthryl group, a (o-, m-, p-) biphenyl group, a taphenyl group and a phenanthryl group.
- Although the amino group(s) represented by Q10 to Q40, Q50 to Q80 and Q10 to Q140 may be substituted or unsubstituted, the amino group(s) is preferably substituted and may be an alkylamino group, an arylamino group, an aralkylamino group or the like. The above amino groups each preferably contain fatty series having 1 to 6 carbon atoms in total and/or an aromatic carbon ring having 1 to 4 rings. Examples of such an amino group are a dimethylamino group, a diethylamino group, an abutyl-amino group, a diphenylamino group, a ditolylamino group, a bis-diphenylamino group and a bis-naphtylamino group.
- The heterocyclic group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 may be substituted or unsubstituted. Examples of the heterocyclic group(s) are a five- or six-membered aromatic heterocyclic group containing O, N and S as heteroatoms and a condensed polycyclic aromatic group having 2 to 20 carbon atoms. Examples of the aromatic heterocyclic group and the condensed polycyclic aromatic heterocyclic group are a thienyl group, a furyl group, a pyronyl group, a pyridyl group, a quinolyl group and a quinoxalyl group.
- Preferable Examples of the substituted or unsubstituted alkenyl group(s) having 1 to 20 carbon atoms represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 are a (1- and 2-) phenylalkenyl group, a (1,2- and 2,2-) diphenylalkenyl group and a (1,2,2-)triphenylalkenyl group that are each substituted by at least one phenyl group. Each of the above examples may be unsubstituted.
- The alkoxy group(s) or the alkylthio group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 may be substituted or unsubstituted. The alkoxy group(s) or the alkylthio group(s) preferably contains the above-described alkyl group.
- The aryloxy group(s) or the arylthio group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 may be substituted or unsubstituted. The aryloxy group(s) or the arylthio group(s) preferably has an aryl group. An example of the aryloxy group(s) is an (o-, m-, p-) phenoxy group while an example of the arylthio group(s) is an (o-, m-, p-) phenylthio group.
- The aralkyl group(s) represented by Q10 to Q40, Q50 to Q80 and Q110 to Q140 may be substituted or unsubstituted, examples of which are a benzyl group and a phenethyl group.
- When Q10 to Q40, Q50 to Q80, and Q110 to Q140 are substituted, at least two of the substituents contained, particularly, in Q10 to Q40 are each preferably an aryl group, an amino group, a heterocyclic group, an alkenyl group or an aryloxy group, more preferably an aryl group. The same as described in relation to Q10 to Q40 applies to the aryl group, the amino group, the heterocyclic group and the alkenyl group.
- Two or more of the above substituents may form a condensed ring. The above substituents may be further substituted, preferable substituents for which are the same as in the above description.
- When Q10 to Q40, Q50 to Q80, and Q110 to Q140 are substituted, at least two, particularly, of Q10 to Q40 each preferably contain the above substituent. The substitution positions are not subject to any specific limitations. When Q10 to Q40 contains phenyl, the substitution positions may be any one of meta, para and ortho positions.
- In the above formula (1), at least one of Q10 to Q80 is preferably a substituted or unsubstituted aryl group. More preferably, at least one of Q10 to Q40 is a substituted or unsubstituted aryl group.
- Specifically, the naphthacene derivative is more preferably represented by the above formula (3).
- In the formula (3), Q10, Q21 to Q25, Q31 to Q35 Q40 to Q80 and Q110 to Q140 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group. Q10, Q21 to Q25, Q31 to Q35, Q40 to Q80 and Q110 to Q140 may be mutually the same or different. Adjacent two or more of Q21 to Q25 and Q31 to Q35 may be mutually bonded to form a cyclic structure.
- The same as described in relation to Q10 and the like of the formula (1) applies to examples of these groups.
- In the formula (3), Q21 to Q25 and Q31 to Q35 are each preferably selected from a group consisting of a hydrogen group, an aryl group, an amino group, a heterocyclic group, an aryloxy group and an alkenyl group, more preferably an aryl group. In addition, at least one of Q21 to Q25 and Q31 to Q35 is preferably substituted by an aryl group, an amino group, a heterocyclic group or an aryloxy group, more preferably by an aryl group. Adjacent two or more of the above may form a condensed ring. The same as described in relation to Q10 to Q40 applies to preferable examples of the aryl group, the amino group, the heterocyclic group and the alkenyl group.
- In addition, although a structure where Q21 to Q25 and Q31 to Q35 are the same is preferable, Q21 to Q25 may be different from Q31 to Q35. Examples of the amino group for substituting Q21 to Q25 and Q31 to Q35 are an alkylamino group, an arylamino group and an aralkylamino group. The above amino groups each preferably contain fatty series having 1 to 6 carbon atoms in total and/or an aromatic carbon ring having 1 to 4 rings. Examples of such an amino group are a dimethylamino group, a diethylamino group, an abutyl-amino group, a diphenylamino group, a ditolylamino group, a bis-diphenylamino group and a bis-naphtylamino group.
- Examples of the condensed ring formed as above are indene, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, quinoxaline, phenazine, acridine, indole, carbazole, phenoxazine, phenothiazine, benzothiazole, benzothiophen, benzofuran, acridone, benzoimidazole, coumarin and flavone.
- Q10, Q40 and Q110 to Q140 are each particularly preferably a hydrogen atom.
- Examples of the aromatic compound represented by the general formula (1) according to the present invention will be shown below. However, the present invention is not limited to the exemplary compounds shown below.
- The dopant is a compound having the pyrromethene skeleton represented by the formula (2) or a metal complex of the compound.
- The compound having the pyrromethene skeleton represented by the formula (2) or the metal complex of the compound is preferably a compound having a pyrromethene skeleton represented by the following formula (2-1) or a metal complex of the compound.
- In the formula (2-1), at least one of R22 to R28 is a substitute having an aromatic ring or forms a condensed aromatic ring together with an adjacent substituent while the rest of R22 to R28 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group. The rest of R22 to R28 each may form a condensed ring or an aliphatic ring with an adjacent substituent. R22 to R28 may be mutually the same or different and may be substituted or unsubstituted. R29 and R30 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group. X represents a carbon atom or a nitrogen atom on a condition that R28 above does not exist when X represents a nitrogen atom.
- When one or more of R22 to R28 forms a condensed aromatic ring(s) together with adjacent substituent(s), the condensed aromatic ring(s) is preferably formed by a pair of R22 and R23, a pair of R23 and R24, a pair of R25 and R26 and/or a pair of R26 and R27. The condensed aromatic ring(s) is particularly preferably formed by the pair of R22 and R23 and/or the pair of R26 and R27. Examples of the condensed aromatic ring(s) are a benzo ring and a naphtho ring.
- The compound having the pyrromethene skeleton represented by the formula (2) or the metal complex of the compound is preferably a compound having a pyrromethene skeleton represented by the following formula (2-2) or a metal complex of the compound.
- In the formula (2-2), R31 to R39 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group. R31 to R39 may be mutually the same or different and may be substituted or unsubstituted. R40 and R41 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group. X represents a carbon atom or a nitrogen atom on a condition that R39 above does not exist when X represents a nitrogen atom.
- According to the present invention, the compound having the pyrromethene skeleton represented by the formula (2-1) or the metal complex of the compound is preferably a metal complex having a pyrromethene skeleton represented by the following formula (2-3).
- In the formula (2-3), R42 to R52 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group. R42 to R52 may be mutually the same or different and may be substituted or unsubstituted. R53 and R54 may be mutually the same or different and each are selected from a group consisting of halogen, a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group. X represents a carbon atom or a nitrogen atom on a condition that R52 above does not exist when X represents a nitrogen atom.
- Examples of the aromatic compound represented by the general formula (2) according to the present invention will be shown below. However, the present invention is not limited to the exemplary compounds shown below.
- In the above formulae, Q10 to Q140 and R15 to R54 may be substituted or unsubstituted, a substituent for each of which is preferably an alkyl group, an aryl group or an alkoxy group.
- The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, further preferably an alkyl group having 1 to 5 carbon atoms. The alkyl group may be linear or branched. The alkyl group may be a primary alkyl group, a secondary alkyl group or a tertiary alkyl group.
- Preferable examples of the alkyl group are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group and an n-decyl group.
- The aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms. Examples of the aryl group are a phenyl group, a tolyl group, a xylyl group, a phenylphenyl group (4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group), a naphthylphenyl group, a naphthyl group (1-naphthyl group, 2-naphthyl group), a phenylnaphthyl group, a naphthylnaphthyl group, a taphenyl group, an anthranil group, a phenantyl group, a pyrenyl group and a chrysenyl group.
- The hole transporting layer helps injection of the holes into the emitting layer and transports the holes to an emitting region, in which the hole mobility is large and the energy of ionization is typically small (5.5 eV or smaller). A material of the hole transporting layer is preferably such a material that transports the holes to the emitting layer with a low field intensity, and more preferably such a material that transports the holes with the hole mobility of at least 10−4 cm2/V*sec when the exemplary electrical field of 104 to 106 V/cm is applied.
- A material for the hole transporting layer is not specifically limited as long as the material has the above preferable characteristics. Any materials conventionally used for transporting charges of the holes in photoconducting materials or any materials publicly known to be applicable to the hole transporting layers of the EL devices may be used.
- Examples of the material are a triazole derivative (see, for instance, the specification of U.S. Pat. No. 3,112,197), an oxadiazole derivative (see, for instance, the specification of U.S. Pat. No. 3,189,447), an imidazole derivative (see, for instance, the publication of JP-B-37-16096), a polyarylalkane derivative (see, for instance, the specifications of U.S. Pat. No. 3,615,402, No. 3,820,989 and No. 3,542,544 and the publications of JP-B-45-555, JP-B-51-10983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148, JP-A-55-108667, JP-A-55-156953, and JP-A-56-36656), a pyrazoline derivative and a pyrazolone derivative (see, for instance, the specifications of U.S. Pat. No. 3,180,729 and No. 4,278,746 and the publications of JP-A-55-88064, JP-A-55-88065, JP-49-105537, JP-A-55-51086, JP-A-56-80051, JP-A-56-88141, JP-A-57-45545, JP-A-54-112637 and JP-A-55-74546, a phenylenediamine derivative (see, for instance, the specification of U.S. Pat. No. 3,615,404 and the publications of JP-B-51-10105, JP-B-46-3712, JP-B-47-25336 and JP-A-54-119925), an arylamine derivative (see, for instance, the specifications of U.S. Pat. No. 3,567,450, No. 3,240,597, No. 3,658,520, No. 4,232,103, No. 4,175,961 and No. 4,012,376 and the publications of JP-B-49-35702, JP-B-39-27577, JP-A-55-144250, JP-A-56-119132 and JP-A-56-22437 and the specification of West Germany Patent No. 1,110,518), an amino-substituted chalcone derivative (see, for instance, the specification of U.S. Pat. No. 3,526,501), an oxazole derivative (disclosed in, for instance, the specification of U.S. Pat. No. 3,257,203), a styrylanthracene derivative (see, for instance, the publication of JP-A-56-46234), a fluorenone derivative (see, for instance, the publication of JP-A-54-110837), a hydrazone derivative (see, for instance, the specification of U.S. Pat. No. 3,717,462 and the publications of JP-A-54-59143, JP-A-55-52063, JP-A-55-52064, JP-A-55-46760, JP-A-57-11350, JP-A-57-148749 and JP-A-2-311591), a stilbene derivative (see, for instance, the publications of JP-A-61-210363, JP-A-61-228451, JP-A-61-14642, JP-A-61-72255, JP-A-62-47646, JP-A-62-36674, JP-A-62-10652, JP-A-62-30255, JP-A-60-93455, JP-A-60-94462, JP-A-60-174749 and JP-A-60-175052), a silazane derivative (see the specification of U.S. Pat. No. 4,950,950), a polysilane type (see the publication of JP-A-2-204996), an aniline-based copolymer (see the publication of JP-A-02-282263), and a conductive high-molecular oligomer (particularly, thiophene oligomer).
- Preferably, a material represented by the following formula (7) may be used.
-
Q1-G-Q2 (7) - In the formula (7), Q1 and Q2 each represent a portion having at least one tertiary amine while G represents a linking group.
- More preferable material is an amine derivative represented by the following formula (8).
- In the above formula (8), Ar21 to Ar24 each represent a substituted or unsubstituted aromatic ring having 6 to 50 carbon atoms forming the ring or a substituted or unsubstituted heteroaromatic ring having 5 to 50 atoms forming the ring. R21 and R22 each represent a substituent while s and t each represent an integer in a range of 0 to 4.
- Ar21 and Ar22 may be bonded together to form a cyclic structure while Ar23 and Ar24 may also be bonded together to form a cyclic structure. R21 and R22 may also be bonded together to form a cyclic structure.
- The substituent for Ar21 to Ar24 each, and R21 and R22 are selected from a group consisting of a substituted or unsubstituted aromatic ring having 6 to 50 carbon atoms forming the ring, a substituted or unsubstituted heteroaromatic ring having 5 to 50 atoms forming the ring, an alkyl group having 1 to 50 carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylaryl group having 1 to 50 carbon atoms, an aralkyl group having 1 to 50 carbon atoms, a styryl group, an amino group substituted by an aromatic ring having 6 to 50 carbon atoms forming the ring or by a heteroaromatic ring having 5 to 50 atoms forming the ring, an aromatic ring having 6 to 50 carbon atoms forming the ring substituted by an amino group substituted by an aromatic ring having 6 to 50 carbon atoms forming the ring or by a heteroaromatic ring having 5 to 50 atoms forming the ring, and a heteroaromatic ring having 5 to 50 atoms forming the ring substituted by an amino group substituted by an aromatic ring having 6 to 50 carbon atoms forming the ring or by a heteroaromatic ring having 5 to 50 atoms forming the ring.
- In order to aid the injection of the holes, a hole injecting layer may be provided in addition to the hole transporting layer. The above materials for the hole transporting layer can be used as the materials of the hole injecting layer, preferable examples of which are a porphyrin compound (disclosed in JP-A-63-295695), an aromatic tertiary amine compound and a styrylamine compound (see, for instance, the specification of U.S. Pat. No. 4,127,412, JP-A-53-27033, JP-A-54-58445, JP-A-55-79450, JP-A-55-144250, JP-A-56-119132, JP-A-61-29558, JP-A-61-98353 and JP-A-63-295695). Among these, use of an aromatic tertiary amine compound is particularly preferable.
- In addition, 4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (hereinafter, abbreviated as NPD) having in the molecule two condensed aromatic rings disclosed in U.S. Pat. Nos. 5,061,569, 4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (hereinafter, abbreviated as MTDATA) in which three triphenylamine units disclosed in JP-A-04-30868 are bonded in a starbust form and the like may also be used.
- As another example, a nitrogen-containing heterocyclic derivative represented by the following formula (9), which is disclosed in Japanese Patent No. 03571977, may be used.
- In the formula (9), R1 to R6 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group. R1 to R6 may be mutually the same or different. A pair of R1 and R2, a pair of R3 and R4 or a pair of R5 and R6 may form a condensed ring(s). Alternatively, a pair of R1 and R6, a pair of R2 and R3 or a pair of R4 and R5 may form a condensed ring(s).
- As another example, a compound represented by the following formula (10), which is disclosed in US 2004/113547A1, may be used.
- In the formula (10), R1 to R6 each represent a substituent, a preferable example of which is an electron-attracting group such as a cyano group, a nitro group, a sulfonyl group, a carbonyl group, a trifluoromethyl group and halogen.
- In addition to aromatic dimethylidyne-based compounds, inorganic compounds such as p-type Si and p-type SiC can be used as the material of the hole injecting layer.
- The hole injecting layer and the hole transporting layer can be formed by forming thin films from the compounds listed above by known methods such as vacuum deposition, spin coating, casting and the LB method. Although the thickness of the hole injecting layer and the hole transporting layer is not particularly limited, the thickness is typically in the range from 5 nm to 5 μm. The hole injecting layer and the hole transporting layer may be formed by a single layer formed of at least one of the above materials as long as the hole injecting layer and the hole transporting layer contains the above compound(s) in the hole transporting region. Alternatively, the hole injecting layer and the hole transporting layer may be formed by laminating layers respectively formed of a different material.
- In addition, an organic semiconductor layer, which is a part of the hole transporting layer, aids the injection of the holes or the electrons into the emitting layer. The organic semiconductor layer preferably has electric conductivity of 10−10 S/cm or more. Examples of a material for the organic semiconductor layer are a conductive oligomer such as a thiophene-containing oligomer or an arylamine-containing oligomer (disclosed in JP-A-08-193191), and a conductive dendrimer such as an arylamine-containing dendrimer.
- The electron transporting layer, which aids injection of the electrons into the emitting layer, has a high electron mobility. The thickness of the electron transporting layer is suitably selected from the range of several nanometers to several micrometers. However, especially when the thickness of the electron transporting layer is large, the electron mobility, in order to prevent voltage from rising, is preferably at least 10−5 cm2/Vs or higher with the electrical field of 104 to 106 V/cm applied.
- The electron transporting layer preferably contains a compound represented by any one of the following formulae (4), (5) and (6).
- In the formulae (5) and (6), R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms while p represents an integer in a range of 1 to 4.
- Preferable examples of the aryl group having 6 to 60 carbon atoms are a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-ta-phenyl-4-yl group, p-ta-phenyl-3-yl group, p-ta-phenyl-2-yl group, m-ta-phenyl-4-yl group, m-ta-phenyl-3-yl group, m-ta-phenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4″-t-butyl-p-ta-phenyl-4-yl group, fluoranthenyl group and fluorenyl group. More preferable examples thereof are a phenyl group, naphthyl group, biphenyl group, anthracenyl group, phenanthryl group, pyrenyl group, crycenyl group, fluoranthenyl group and fluorenyl group.
- Preferable examples of the alkyl group having 1 to 20 carbon atoms are a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobuthyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
- The alkoxy group having 1 to 20 carbon atoms is a group represented by —OY′″. Examples of Y′″ are the same as those of the above alkyl group.
- Examples of the substituent for the aryl group, the pyridyl group, the quinolyl group, the alkyl group or the alkoxy group are a substituted or unsubstituted aryl group having 6 to 50 carbon atoms forming the ring, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 atoms forming the ring, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 atoms forming the ring, a substituted or unsubstituted arylthio group having 5 to 50 atoms forming the ring, a substituted or unsubstituted carboxyl group having 1 to 50 carbon atoms, a halogen group, a cyano group, a nitro group and a hydroxyl group.
- In the formulae (5) and (6), p represents an integer in a range of 1 to 4. Preferably, p is any one of 1 to 3, more preferably 1 or 2.
- R preferably represents a hydrogen atom.
- R11 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms. Examples of each group and substituent are the same as R.
- R12 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Examples of each group and substituent are the same as R.
- L represents a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted quinolinylene group, or a substituted or unsubstituted fluorenylene group.
- Preferable examples of the arylene group having 6 to 60 carbon atoms are divalent substituents formed by further removing one hydrogen atom from the substituents listed in the description of the aryl group having 6 to 60 carbon atoms. More preferable examples thereof are a phenylene group, naphthylene group, biphenylene group, anthracenylene group, phenantolylene group, pyrenylene group, chrysenylene group, fluoranthenylene group and fluorenylene group.
- Examples of the substituent for each of the arylene group, the pyridinylene group, the quinolinylene group or the fluorenylene group are the same as R.
- Ar1 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms (preferably, 6 to 30 carbon atoms), a substituted or unsubstituted pyridyl group or a substituted or unsubstituted quinolyl group.
- Examples of the substituent for each of the aryl group having 6 to 60 carbon atoms, the aryl group, the pyridyl group or the quinolyl group are the same as R.
- Preferably in the benzoimidazole derivative represented by the formula (5): R represents a hydrogen atom; R11 represents an aryl group; L represents an arylene group having 6 to 30 carbon atoms (preferably, 6 to 20 carbon atoms); and Ar1 represents an aryl group having 6 to 30 carbon atoms.
- Preferably in the benzoimidazole derivative represented by the formula (6): R represents a hydrogen atom; R12 represents an aryl group; L represents an arylene group having 6 to 30 carbon atoms (preferably, 6 to 20 carbon atoms); and Ar1 represents an aryl group having 6 to 30 carbon atoms.
- Although the compound(s) represented by the formulae (4), (5) and (6) are preferably applicable to the electron transporting layer, the material of the electron transporting layer is not limited thereto. Compounds containing 8-hydroxyquinoline, a metal complex of its derivative, or a nitrogen-containing heterocycle may be preferably applicable to the electron transporting layer.
- An example of the 8-hydroxyquinoline or the metal complex of its derivative is a metal chelate oxinoid compound containing a chelate of oxine (typically 8-quinolinol or 8-hydroxyquinoline). For example, an Alq complex having Al as its central metal can be used for the electron transporting layer.
- On the other hand, examples of the oxadiazole derivative are electron transporting compounds represented by the following general formulae.
- In the formulae, Ar321, Ar322, Ar323, Ar325, Ar326 and Ar329 each represent a substituted or unsubstituted aryl group, which may be mutually the same or different. Ar324, Ar327 and Ar328 each represent a substituted or unsubstituted arylene group, which may be mutually the same or different.
- Examples of the aryl group are a phenyl group, a biphenyl group, an anthranil group, a perylenyl group, and a pyrenyl group. Examples of the arylene group are a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a perylenylene group and a pyrenylene group. Examples of the substituent therefor are an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or a cyano group. The electron transporting compounds are preferably compounds that exhibit favorable performance in forming a thin film.
- Examples of the electron transporting compounds are as follows.
- Me represents a methyl group while Bu represents a butyl group.
- A silacyclopentadiene derivative represented by the following formula (disclosed in JP-A-09-087616) is also preferably applicable to the electron transporting layer.
- In the formula, X351 and Y351 may each represent a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle, or X351 and Y351 may be bonded together to form a saturated or unsaturated ring. R351 to R354 may each represent hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an azo group, an alkylcarbonyloxy group, an arylcarbonyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyl group, a sulfonyl group, a sulfanyl group, a silyl group, a carbamoyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, a nitro group, a formyl group, a nitroso group, a formyloxy group, an isocyano group, a cyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group or cyano group, or an adjacent set of R351 to R354 may be condensed to form a substituted or unsubstituted ring.
- A silacyclopentadiene derivative represented by the following formula (disclosed in JP-A-09-194487) is also preferably applicable to the electron transporting layer.
- In the formula, X361 and Y361 may each represent a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle, or X361 and Y361 may be bonded together to form a saturated or unsaturated ring. R361 to R364 may each represent hydrogen, halogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an azo group, an alkylcarbonyloxy group, an arylcarbonyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyl group, a sulfonyl group, a sulfanyl group, a silyl group, a carbamoyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, a nitro group, a formyl group, a nitroso group, a formyloxy group, an isocyano group, a cyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group or cyano group, or an adjacent set of R361 to R364 may be condensed to form a substituted or unsubstituted ring. However, when R361 and R364 are phenyl groups, neither X361 nor Y361 is an alkyl group or a phenyl group. When R361 and R364 are thienyl groups, X361 and Y361 are each a univalent hydrocarbon group provided that neither R362 nor R363 is an alkyl group, an aryl group or an alkenyl group, or that R362 and R363 are not bonded together to form an aliphatic ring group. When R361 and R364 are silyl groups, none of R362, R363, X361 and Y361 is a univalent hydrocarbon group having 1 to 6 carbon atoms or a hydrogen atom. When R361 and R362 are of a condensed benzene-ring structure, neither of X361 nor Y361 is an alkyl group or a phenyl group.
- A borane derivative represented by the following formula (disclosed in JP-A1-2000-040586) is also preferably applicable to the electron transporting layer.
- In the formula, R371 to R378 and Z372 each represent a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amino group, a substituted boryl group, an alkoxy group or an aryloxy group; X371, Y371 and Z371 each represent a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amino group, an alkoxy group or an aryloxy group; substituent groups of Z371 and Z372 may be bonded to form a condensed ring; and n represents an integer in a range of 1 to 3, where when n is equal to or larger than 2, Z371 does not have to be the same. However, the above does not apply when: n is 1; X371, Y371 and R372 are the methyl groups; and R378 is the hydrogen atom or the substituted boryl group, or when: n is 3; and Z371 is the methyl group.
- A compound represented by the following formula (disclosed in JP-A-10-088121) is also preferably applicable to the electron transporting layer.
- In this formula, Q381 and Q382 each represent a ligand shown by the formula below. L381 represents a ligand which may be a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or L381 represents a ligand represented by —OR391 (R391 representing a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group) or a ligand represented by —O—Ga-Q391 (Q392) (Q391 and Q392 being the same as Q381 and Q382).
- In the above formula, rings A401 and A402 are bonded together to form a substituted or unsubstituted aryl ring or a heterocycle.
- Examples of the substituent groups of the ring A401 and the ring A402 that form the ligands in the formula above are: halogen atoms such as chlorine, bromine, iodine and fluorine; substituted or unsubstituted alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group and a trichloromethyl group; substituted or unsubstituted aryl groups such as a phenyl group, a naphthyl group a 3-methylphenyl group, a 3-methoxyphenyl group, a 3-fluorophenyl group, a 3-trichloromethylphenyl group, a 3-trifluoromethylphenyl group and a 3-nitrophenyl group; substituted or unsubstituted alkoxy groups such as a methoxy group, a n-butoxy group, a tert-butoxy group, a trichloromethoxy group, a trifluoroethoxy group, a pentafluoropropoxy group, a 2,2,3,3-tetrafluoropropoxy group, a 1,1,1,3,3,3-hexafluoro-2-propoxy group and a 6-(perfluorohethyl)hexyloxy group; substituted or unsubstituted aryloxy groups such as a phenoxy group, a p-nitrophenoxy group, a p-tert-butylphenoxy group, a 3-fluorophenoxy group, a pentafluorophenyl group and a 3-trifluoromethylphenoxy group; substituted or unsubstituted alkylthio groups such as a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group and a trifluoromethylthio group; substituted or unsubstituted arylthio groups such as a phenylthio group, a p-nitrophenylthio group, a p-tert-butylphenylthio group, a 3-fluorophenylthio group, a pentafluorophenylthio group and a 3-trifluoromethylphenylthio group; mono- or disubstituted amino groups such as a cyano group, a nitro group, an amino group, a methylamino group, a diethylamino group, an ethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group and a diphenylamino group; acylamino groups such as a bis(acetoxymethyl)amino group, a bis(acetoxyethyl)amino group, a bis(acetoxypropyl)amino group and a bis(acetoxybutyl)amino group; a hydroxyl group; a siloxy group; an acyl group; carbamoyl groups such as a methylcarbamoyl group, a dimethylcarbamoyl group, an ethylcarbamoyl group, a diethylcarbamoyl group, a propylcarbamoyl group, a butylcarbamoyl group, and a phenylcarbamoyl group; a carboxylic acid group; a sulfonic acid group; an imide group; cycloalkyl groups such as a cyclopentane group and a cyclohexyl group; aryl groups such as a phenyl group, a naphthyl group, a biphenyl group, an anthranil group, a phenanthryl group, a fluorenyl group and a pyrenyl group; and heterocyclic groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolinyl group, a quinolyl group, an acridinyl group, a pyrrolidinyl group, a dioxanyl group, a piperidinyl group, a morpholidinyl group, a piperazinyl group, a carbazolyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group and a benzoimidazolyl group. In addition, the substituent groups listed above may be bonded together to form a 6-membered aryl ring or a heterocycle.
- As a preferred embodiment of the organic EL device according to the present invention, there is known a device containing a reductive dopant at a boundary between a region transporting the electrons or the cathode and an organic layer. The reductive dopant is defined as a substance capable of reducing an electron transporting compound. Thus, various substances having a certain level of reducibility can be used, preferable examples of which are at least one substance selected from a group consisting of: alkali metal, alkali earth metal, rare earth metal, an oxide of the alkali metal, a halogenide of the alkali metal, an oxide of the alkali earth metal, a halogenide of the alkali earth metal, an oxide of the rare earth metal, a halogenide of the rare earth metal, an organic complex of the alkali metal, an organic complex of the alkali earth metal and an organic complex of the rare earth metal.
- Specifically, the reductive dopant is preferably a substance(s) having the work function of 2.9 eV or lower, which is exemplified by at least one alkali metal selected from a group consisting of Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1.95 eV) or at least one alkali earth metal selected from a group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV) and Ba (work function: 2.52 eV). Among these, the reductive dopant is more preferably at least one alkali metal selected from a group consisting of K, Rb and Cs, among which Rb and Cs are even more preferable and Cs is the most preferable. These alkali metals have particularly high reducibility, so that addition of a relatively small amount of these alkali metals to an electron injecting zone can enhance luminescence intensity and lifecycle of the organic electroluminescence device. In addition, as the reductive dopant having the work function of 2.9 eV or lower, a combination of two or more of these alkali metals is also preferable, and a combination including Cs is particularly preferable (e.g. combinations of Cs and Na, Cs and K, Cs and Rb or Cs, Na and K). The combinations including Cs can effectively exert the reducibility, so that the addition of such reductive dopant to the electron injecting zone can enhance the luminescence intensity and the lifecycle of the organic electroluminescence device.
- According to the present invention, an electron injecting layer formed from an insulator or a semiconductor may be provided between the cathode and the organic layer. With the arrangement, leak of electric current can be effectively prevented and the electron injecting capability can be enhanced. As the insulator, it is preferable to use at least one metal compound selected from a group consisting of an alkali metal chalcogenide, an alkali earth metal chalcogenide, a halogenide of alkali metal and a halogenide of alkali earth metal. By forming the electron injecting layer from the alkali metal chalcogenide or the like, the electron injecting capability can preferably be further enhanced. Specifically, preferable examples of the alkali metal chalcogenide are Li2O, LiO, Na2 S, Na2 Se and NaO, while preferable example of the alkali earth metal chalcogenide are CaO, BaO, SrO, BeO, BaS and CaSe. Preferable examples of the halogenide of the alkali metal are LiF, NaF, KF, LiCl, KCl and NaCl. Preferable examples of the halogenide of the alkali earth metal are fluorides such as CaF2, BaF2, SrF2, MgF2 and BeF2, and halogenides other than the fluoride.
- Examples of the semiconductor for forming the electron injecting layer are one of or a combination of two or more of an oxide, a nitride or an oxidized nitride containing at least one element selected from a group consisting of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn. An inorganic compound for forming the electron injecting layer is preferably a microcrystalline or amorphous semiconductor film. When the electron injecting layer is formed of such semiconductor film, more uniform thin film can be formed, thereby reducing pixel defects such as a dark spot. Examples of such an inorganic compound are the above-described alkali metal chalcogenide, alkali earth metal chalcogenide, halogenide of the alkali metal and halogenide of the alkali earth metal.
- In order to inject the electrons into the electron injecting and transporting layers or the emitting layer, a material whose work function is small (4 eV or lower) is used as an electrode material for the cathode, examples of the material being metals, alloys, electrically conductive compounds and mixtures thereof. Examples of the electrode material are sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-silver alloy, aluminium/aluminium oxide, an aluminium-lithium alloy, indium, rare earth metal and the like.
- The cathode is made by forming a thin film from the electrode material by vapor deposition and sputtering.
- When the organic EL device is top-emission type, the cathode preferably transmits more than 10% of light emitted by the emitting layer.
- The sheet resistance as the cathode is preferably several hundreds Ω/square or lower, and the thickness of the film is typically in a range from 10 nm to 1 μm, preferably 50 to 200 nm.
- Since the electrical field is applied to ultra thin films in the organic electroluminescence device, pixel defects resulted from leak or short circuit are likely to occur. In order to prevent such defects, it is preferable to interpose an insulating thin film layer between a pair of electrodes.
- Examples of a material used for the insulating layer are aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, cesium fluoride, cesium carbonate, aluminium nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like.
- Mixtures or laminates thereof may also be used.
- The organic EL device can be manufactured by forming the anode, the emitting layer and the cathode (in addition to the above, forming the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer as necessary) from the materials listed above by the above-described formation methods. The organic EL device can also be manufactured by forming the above elements in the inverse order of the above, namely from the cathode to the anode.
- The following is a manufacturing example of the organic EL device in which the anode, the hole transporting layer, the emitting layer, the electron transporting layer and the cathode are sequentially formed on the light-transmissive substrate.
- A thin film is formed of the anode material on a suitable light-transmissive substrate by vapor deposition or sputtering such that the thickness of the thin film is 1 m or smaller, preferably in a range from 10 nm to 200 nm, thereby forming the anode. Then, the hole transporting layer is formed on the formed anode. The hole transporting layer may be formed by a method such as vacuum deposition, spin coating, casting and the LB method as described above, among which vacuum deposition is preferable in forming the hole transporting layer because the method can easily form homogeneous films and can prevent generation of pin holes. When the hole transporting layer is formed by vacuum deposition, conditions for conducting vacuum deposition depend on the compounds to be used (i.e., the material of the hole transporting layer), a crystal structure of the targeted hole transporting layer, and a recombination structure of the targeted hole transporting layer. Generally, conditions are preferably set so as to satisfy deposition-source temperature of 50 to 450 degrees C., vacuum of 10−7 to 10−3 torr, deposition speed of 0.01 to 50 nm/second, substrate temperature of −50 to 300 degrees C., film thickness of 5 nm to μm.
- Then, the emitting layer is formed on the hole transporting layer. The emitting layer may also be formed of a desirable material by a method such as vacuum deposition, sputtering, spin coating and casting, among which vacuum deposition is preferable in forming the emitting layer because the method can easily form homogeneous films and can prevent generation of pin holes. When the emitting layer is formed by vacuum deposition, deposition conditions for forming the emitting layer can be generally set in the same manner as the hole transporting layer although the deposition conditions may vary depending on compounds used for forming the emitting layer.
- Next, the electron transporting layer is formed on the emitting layer. As with the hole transporting layer and the emitting layer, the electron transporting layer is also preferably formed by vacuum deposition so as to form a homogeneous film. Deposition conditions for forming the electron transporting layer can be set in the same manner as the hole transporting layer and the emitting layer.
- Lastly, the cathode is laminated thereon.
- The cathode can be formed from a metal by a method such as vapor deposition and sputtering. In order to protect the organic layers deposited under the cathode from being damaged, the vacuum deposition is preferable.
- The above-described organic EL device is preferably manufactured such that all layers from the anode to the cathode are formed in one vacuuming.
- The methods for forming each layer of the organic EL device are not particularly limited. Conventionally-known methods such as vacuum deposition, molecular-beam deposition, spin coating, dipping, casting, bar coating and roll coating are applicable to forming the layers.
- Although the thickness of each organic layer of the organic EL device is not particularly limited, the thickness is generally preferably in a range of several nanometers to 1 μm because excessively-thinned film likely entails defects such as a pin hole while excessively-thickened film requires high voltage to be applied and deteriorates efficiency.
- When a voltage is applied to the organic EL device, the light-emission can be observed by applying a voltage of 3 to 40V with the anode having the positive polarity and the cathode having the negative polarity. When the voltage is applied with the inversed polarity, no current flows, so that no light is emitted. When an alternating voltage is applied, the uniform light-emission can be observed only when the anode has the positive polarity and the cathode has the negative polarity. A waveform of the alternating current to be applied may be suitably selected.
- Next, the present invention will be further described in detail by exemplifying Examples. However, the present invention is not limited to such Examples.
- A 130 nm-thick transparent electrode formed of indium tin oxide was formed on a glass substrate having a size of 25 mm by 75 mm by 0.7 mm. After the transparent substrate was ultrasonically cleaned in isopropyl alcohol for five minutes, the substrate was further cleaned with UV (ultraviolet) ozone for thirty minutes, and then the substrate was mounted on a vapor deposition apparatus.
- Initially, N,N′-bis[4-(N,N-diphenylamino)phenyl-1-yl]-N,N′-diphenyl-4,4′-benzidine was deposited on the substrate to form a 60 nm-thick hole injecting layer, and subsequently N,N′-bis[4′-{N-(naphthyl-1-yl)-N-phenyl}aminobiphenyl-4-yl]-N-phenylamine was deposited thereon to form a 10 nm-thick hole transporting layer. Then, the following compound (A-1), a naphthacene derivative, and the following compound (B-1), a compound having a pyrromethene skeleton, were simultaneously deposited thereon by weight ratio of 40 to 0.4 (=0.99 wt %) to form a 40 nm-thick emitting layer.
- Next, the following compound (C-1) was deposited thereon to form a 30 nm-thick electron transporting layer.
- After 0.5 nm-thick lithium fluoride was subsequently deposited thereon, 150 nm-thick aluminum was deposited further thereon. The layer of aluminum/lithium fluoride served as the cathode. The organic EL device was manufactured by the above-described manner.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.7 V to emit red light having a luminescence intensity of 711 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.11 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half (i.e., time until half-life) was 1,800 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (A-2) was used in place of the compound (A-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 720 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.20 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 2,000 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (A-3) was used in place of the compound (A-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 737 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.37 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 3,200 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-2) was used in place of the compound (B-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 698 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 6.98 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 1,900 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-3) was used in place of the compound (B-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.8 V to emit red light having a luminescence intensity of 710 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 7.10 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 1,500 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-4) was used in place of the compound (B-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.7 V to emit red light having a luminescence intensity of 676 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.66, 0.33), and efficiency of the device was 6.76 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 1,600 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (C-2) was used in place of the compound (C-1) for forming the electron transporting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 5.6 V to emit red light having a luminescence intensity of 564 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.64, 0.34), and efficiency of the device was 5.64 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 1,000 hours.
- An organic EL device was manufactured in the same manner as in Example 7 except that the following compound (C-2) was used in place of the compound (A-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 6.1 V to emit red light having a luminescence intensity of 434 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.63, 0.35), and efficiency of the device was 4.34 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 500 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-5) was used in place of the compound (B-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.7 V to emit red light having a luminescence intensity of 385 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.64, 0.37), and efficiency of the device was 3.85 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 700 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (C-2) was used in place of the compound (A-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 5.2 V to emit red light having a luminescence intensity of 451 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.65, 0.33), and efficiency of the device was 4.51 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 600 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-6) was used in place of the compound (B-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.4 V to emit red light having a luminescence intensity of 1,081 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.65, 0.34), and efficiency of the device was 10.81 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 3,500 hours.
- An organic EL device was manufactured in the same manner as in Example 1 except that the following compound (B-7) was used in place of the compound (B-1) for forming the emitting layer.
- When a current test was conducted on the obtained device, the organic EL device was driven by a voltage of 4.5 V to emit red light having a luminescence intensity of 852 cd/m2 at a current density of 10 mA/cm2, a trichromatic coordinate of the emitted light was (0.67, 0.33), and efficiency of the device was 8.52 cd/A. In addition, when a continuous direct-current test was conducted with the initial luminescence intensity set at 5,000 cd/m2, time elapsed until the luminescence intensity was reduced by half was 3,300 hours.
-
TABLE 1 time Drive luminescence Luminous until Voltage intensity trichromatic Efficiency half- (V) (cd/m2) coordinate (cd/A) life (hr) Example 1 4.7 711 (0.66, 0.33) 7.11 1,800 Example 2 4.8 720 (0.66, 0.33) 7.20 2,000 Example 3 4.8 737 (0.66, 0.33) 7.37 3,200 Example 4 4.8 698 (0.66, 0.33) 6.98 1,900 Example 5 4.8 710 (0.66, 0.33) 7.10 1,500 Example 6 4.7 676 (0.66, 0.33) 6.76 1,600 Example 7 5.6 564 (0.64, 0.34) 5.64 1,000 Compar- 6.1 434 (0.63, 0.35) 4.34 500 ative 1 Compar- 4.7 385 (0.64, 0.37) 3.85 700 ative 2 Compar- 5.2 451 (0.65, 0.33) 4.51 600 ative 3 Example 8 4.4 1,081 (0.65, 0.34) 10.81 3,500 Example 9 4.5 852 (0.67, 0.33) 8.52 3,300 - It is understood from a comparison between Example 7 and Comparative 1 that Example 7, in which the compound (A-1) was used as the host, is more excellent in drive voltage, luminescence intensity, chromaticity and time until half-life.
- In other words, a combination of the compound (A-1) and the compound (B-1) as the combination of the host and the dopant is more excellent than a combination of the compound (C-2), a general host material, and the compound (B-1).
- In Examples 1 to 6 and Comparatives 2 and 3, the compound (C-1) was used as the electron transporting layer. The compound (B-5) was used as the dopant in Comparative 2 while the compound (C-2) was used as the host in Comparative 3. In contrast, the combination of the host and the dopant according to the present invention was used in Examples 1 to 6.
- Consequently, the combination of the host and the dopant according to the present invention is excellent in terms of drive voltage, luminescence intensity, chromaticity, luminous efficiency and time until half-life.
- In other words, irrespective of what compound is used for forming the electron transporting layer, the combination of the host material and the dopant material according to the present invention is excellent in terms of drive voltage, luminescence intensity, chromaticity, efficiency and time until half-life.
- It is understood from a comparison between Examples 1 to 6 and Example 7 that, by using such a material as represented by the compound (C-1) according to the present invention for the electron transporting material, the device can exhibit excellent performance in terms of drive voltage, luminescence intensity, chromaticity, efficiency, time until half-time and the like.
- The emitting region is typically preferably located within the emitting layer in the organic EL device.
- On the other hand, an emitting material for emitting red light tends to cause electron traps because an energy gap of the dopant is small. Accordingly, the electrons injected into the emitting layer from the electron transporting layer tend to be trapped in the dopant located adjacent to the electron transporting layer, thereby moving the emitting region toward the electron transporting layer.
- In Example 7, the chromaticity was shifted toward green, and the compound (C-2) emitted light. It can be deduced from the above with respect to Example 7 that the holes were more strongly injected into the emitting layer than the electrons, and that many of the holes penetrated the emitting layer to reach the electron transporting layer, thereby generating exciters in the compound (C-2) forming the electron transporting layer. In addition, since the compound (C-2) emitted light, the time elapsed until the lifetime of the organic EL device was reduced by half is short.
- In this respect, the electron transporting material according to the present invention, a representative example of which is the compound (C-1), is excellent in transporting electrons. The electron transporting layer formed of such an electron transporting material can strongly inject the electrons into the emitting layer, thereby preventing the holes from penetrating the emitting layer to reach the electron transporting layer.
- In other words, the organic EL device according to the present invention can emit light of high chromaticity with high efficiency while preventing generation of exciters in the electron transporting layer, and lifetime of the entire device is long.
- In addition, when a naphthacene derivative and a compound having pyrromethene skeleton or the like are respectively used for the host and the dopant, the electron transporting material can exhibit above-described excellent effects and advantages.
- Lifetime of Example 3 is much longer than those of Examples 1 and 2 because the compound A-3 was used for the host in Example 3. It has been revealed from the above that substituent(s) in ortho position(s) of benzene rings bonded to the naphthacene skeleton prevents molecular association, thereby contributing to longer lifetime.
- The present invention is not limited to the above examples, but includes modifications and improvements made within a scope where an object of the present invention can be achieved.
- For instance, ruburene, which is an example of the host material of Example 1, may be substituted or unsubstituted. In addition, the compounds used in the other Examples may be substituted or unsubstituted.
- The priority application Number JP2007-061091 upon which this patent application is based is hereby incorporated by reference.
Claims (18)
1-20. (canceled)
21. An organic electroluminescence device, comprising:
a cathode;
an anode; and
an emitting layer provided between the cathode and the anode, wherein
the emitting layer comprises a host and a dopant,
the host is a naphthacene derivative represented by a formula (1) as follows, and
the dopant is a compound having a pyrromethene skeleton represented by a formula (2) as follows or a metal complex of the compound,
in the formula (1), Q10, Q40, Q50, Q60, Q70, Q80, Q110, Q120, Q130 and Q140 each representing a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group, Q10, Q40, Q50, Q60, Q70, Q80, Q110, Q120, Q130 and Q140 being allowed to be mutually the same or different,
Q20 and Q30 in the formula (1) each representing a substituted or unsubstituted heterocylic group, Q20 and Q30 being allowed to be mutually the same or different,
in the formula (2): at least one of R15 to R21 being a substitute containing an aromatic ring or forming a condensed ring with an adjacent substituent while the rest of R15 to R21 each representing a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, a halogen, a haloalkane, a haloalkene, a haloalkyne, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group, the rest of R5 to R21 each being allowed to form a condensed ring or an aliphatic ring with an adjacent substituent, the groups listed above each having 1 to 20 carbon atoms, R15 to R21 being allowed to be mutually the same or different and being allowed to be substituted or unsubstituted; X representing a carbon atom or a nitrogen atom on a condition that R21 above does not exist when X represents a nitrogen atom; and a metal in the metal complex is at least one metal selected from the group consisting of boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc and platinum.
22. The organic electroluminescence device according to claim 21 , wherein
the substituted or unsubstituted heterocyclic group represented by Q20 and Q30 is a condensed polycyclic aromatic heterocyclic group having 2 to 20 carbon atoms.
23. The organic electroluminescence device according to claim 21 , wherein
the heterocyclic group represented by Q20 and Q30 comprises a substituent, the substituent forming a condensed ring, and
the condensed ring is substituted or unsubstituted.
24. The organic electroluminescence device according to claim 21 , wherein
the substituted or unsubstituted heterocyclic group represented by Q20 and Q30 is at least one substituted or unsubstituted condensed polycyclic aromatic heterocyclic group selected from the group consisting of quinoline, isoquinoline, quinoxaline, phenazine, acridine, indole, carbazole, phenoxazine, phenothiazine, benzothiazole, benzothiophen, benzofuran, acridone, benzoimidazole, coumarin and flavone.
25. The organic electroluminescence device according to claim 21 , wherein
the metal complex represented by the formula (2) is a metal complex having a pyrromethene skeleton represented by a formula (2-1) as follows,
where: at least one of R22 to R28 is a substituent having an aromatic ring or forms a condensed aromatic ring together with an adjacent substituent while the rest of R22 to R28 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heterocyclic group, halogen, haloalkene, haloalkene, haloalkyne, a cyan group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group, the rest of R22 to R28 each being allowed to form a condensed ring or an aliphatic ring with an adjacent substituent, R22 to R28 being allowed to be mutually the same or different and being allowed to be substituted or unsubstituted; R29 and R30 are allowed to be mutually the same or different and each are selected from the group consisting of halogen, a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and a substituted or unsubstituted heterocyclic group; and X representing a carbon atom or a nitrogen atom on a condition that R21 above does not exist when X represents a nitrogen atom.
26. The organic electroluminescence device according to claim 25 , wherein
at least one of R22 to R28 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) is a substituent having an aromatic ring.
27. The organic electroluminescence device according to claim 25 , wherein
at least one of R22 to R28 in the metal complex having the pyrromethene skeleton represented by the formula (2-1) forms a condensed aromatic ring together with an adjacent substituent.
28. The organic electroluminescence device according to claim 21 , wherein
at least one of Q10 and Q40 in the naphthacene derivative represented by the formula (1) is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
29. The organic electroluminescence device according to claim 21 , wherein
the dopant is contained in the emitting layer at a doping concentration of 0.1 to 10 mass %.
30. The organic electroluminescence device according to claim 29 , wherein
the dopant is contained in the emitting layer at a doping concentration of 0.5 to 2 mass %.
31. The organic electroluminescence device according to claim 21 , further comprising:
an electron transporting layer provided between the cathode and the anode, wherein the electron transporting layer comprises a compound represented by a formula (4) as follows,
(A)m-(B)n (4)
(A)m-(B)n (4)
where: A represents a substituted or unsubstituted condensed aromatic hydrocarbon group having three or more rings; B represents a substituted or unsubstituted heterocyclic group; and m and n each represent an integer in a range of 1 to 6.
32. The organic electroluminescence device according to claim 31 , wherein
A in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from the group consisting of anthracene, phenanthrene, naphthacene, pyrene, chrysene, benzoanthracene, pentacene, dibenzoanthracene, benzopyrene, fluorene, benzofluorene, fluoranthene, benzofluoranthene, naphthofluoranthene, dibenzofluorene, dibenzopyrene and dibenzofluoranthene.
33. The organic electroluminescence device according to claim 31 , wherein
B in the compound represented by the formula (4) is a nitrogen-containing heterocyclic group.
34. The organic electroluminescence device according to claim 33 , wherein
B in the compound represented by the formula (4) has a skeleton in its molecule, the skeleton selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, acridine, imidazopyridine, imidazopyrimidine, phenanthroline, pyrazole, imidazole and benzoimidazole.
35. The organic electroluminescence device according to claim 34 ,
wherein the compound represented by the formula (4) is a benzoimidazole derivative represented by a formula (5) or a formula (6) as follows,
where: R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; p represents an integer in a range of 1 to 4; R11 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms; R12 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; L represents a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted quinolinylene group or a substituted or unsubstituted fluorenylene group; and Ar1 represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group or a substituted or unsubstituted quinolyl group, at least one of R, R11, R12, L and Ar1 corresponding to A in the compound represented by the formula (4) and being a condensed aromatic hydrocarbon group having three or more rings.
36. The organic electroluminescence device according to claim 21 , wherein
the emitting layer emits light of orange to red.
37. A display, comprising the organic electroluminescence device according to claim 21 .
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/585,132 US20120305908A1 (en) | 2007-03-09 | 2012-08-14 | Organic electroluminescence device and display |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007-061091 | 2007-03-09 | ||
JP2007061091 | 2007-03-09 | ||
US12/044,436 US8278819B2 (en) | 2007-03-09 | 2008-03-07 | Organic electroluminescence device and display |
US13/585,132 US20120305908A1 (en) | 2007-03-09 | 2012-08-14 | Organic electroluminescence device and display |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/044,436 Continuation US8278819B2 (en) | 2007-03-09 | 2008-03-07 | Organic electroluminescence device and display |
Publications (1)
Publication Number | Publication Date |
---|---|
US20120305908A1 true US20120305908A1 (en) | 2012-12-06 |
Family
ID=39759489
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/044,436 Active 2030-09-28 US8278819B2 (en) | 2007-03-09 | 2008-03-07 | Organic electroluminescence device and display |
US13/585,132 Abandoned US20120305908A1 (en) | 2007-03-09 | 2012-08-14 | Organic electroluminescence device and display |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/044,436 Active 2030-09-28 US8278819B2 (en) | 2007-03-09 | 2008-03-07 | Organic electroluminescence device and display |
Country Status (7)
Country | Link |
---|---|
US (2) | US8278819B2 (en) |
EP (1) | EP2128910B1 (en) |
JP (2) | JP5336352B2 (en) |
KR (1) | KR101397219B1 (en) |
CN (1) | CN101689612B (en) |
TW (1) | TW200907014A (en) |
WO (1) | WO2008111554A1 (en) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2008047744A1 (en) * | 2006-10-16 | 2010-02-25 | 東レ株式会社 | Light emitting element |
US8278819B2 (en) * | 2007-03-09 | 2012-10-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and display |
EP2208772B1 (en) * | 2007-11-02 | 2016-01-06 | Toray Industries, Inc. | Luminescent-element material and luminescent element |
JP2009146886A (en) * | 2007-11-22 | 2009-07-02 | Tohoku Univ | Organic el element, organic el display device, and its manufacturing method |
US20110226992A1 (en) * | 2008-09-19 | 2011-09-22 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent material compositions |
JP2010092960A (en) * | 2008-10-06 | 2010-04-22 | Sony Corp | Organic electroluminescent device and display apparatus |
JP5408124B2 (en) * | 2009-01-23 | 2014-02-05 | 東レ株式会社 | Light emitting device material and light emitting device |
KR101153910B1 (en) * | 2010-02-19 | 2012-06-07 | 덕산하이메탈(주) | Chemical Comprising Indole Derivatives and Organic Electronic Element using the same, Terminal thereof |
CN105409020A (en) * | 2012-05-15 | 2016-03-16 | 密歇根大学董事会 | Dipyrrin based materials for photovoltaics, compounds capable of undergoing symmetry breaking intramolecular charge transfer in a polarizing medium and organic photovoltaic devices comprising the same |
WO2014010611A1 (en) * | 2012-07-13 | 2014-01-16 | 出光興産株式会社 | Organic electroluminescence element and electronic apparatus |
KR20150131807A (en) * | 2014-05-16 | 2015-11-25 | 에스케이케미칼주식회사 | Dye comprising pyrromethene boron complex compound |
KR20150131825A (en) * | 2014-05-16 | 2015-11-25 | 에스케이케미칼주식회사 | Dye comprising pyrromethene boron complex compound |
JP5833201B2 (en) * | 2014-08-21 | 2015-12-16 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENCE ELEMENT ITS MANUFACTURING METHOD, LIGHTING DEVICE, AND DISPLAY DEVICE |
JP6923837B2 (en) * | 2015-06-29 | 2021-08-25 | 国立研究開発法人理化学研究所 | Method for high polarization of nuclear spin by dynamic nuclear polarization using soluble pentacene |
WO2018101129A1 (en) * | 2016-11-30 | 2018-06-07 | 東レ株式会社 | Pyrromethene-boron complex, color conversion composition, color conversion film, light source unit, display, and illumination device |
KR20180077834A (en) * | 2016-12-29 | 2018-07-09 | 엘지디스플레이 주식회사 | Electroluminescent Display Device |
JP6670776B2 (en) * | 2017-03-02 | 2020-03-25 | 富士フイルム株式会社 | Emissive resin composition for wavelength conversion, wavelength conversion member, wavelength conversion unit, and light emitting element |
US10497738B2 (en) * | 2018-04-20 | 2019-12-03 | Omnivision Technologies, Inc. | First photon correlated time-of-flight sensor |
US11029397B2 (en) * | 2018-04-20 | 2021-06-08 | Omnivision Technologies, Inc. | Correlated time-of-flight sensor |
JP7325731B2 (en) | 2018-08-23 | 2023-08-15 | 国立大学法人九州大学 | organic electroluminescence element |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8278819B2 (en) * | 2007-03-09 | 2012-10-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and display |
Family Cites Families (112)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU35193A1 (en) | 1956-06-04 | |||
LU35237A1 (en) | 1956-06-27 | |||
US3180729A (en) | 1956-12-22 | 1965-04-27 | Azoplate Corp | Material for electrophotographic reproduction |
BE581861A (en) | 1958-08-20 | |||
US3240597A (en) | 1961-08-21 | 1966-03-15 | Eastman Kodak Co | Photoconducting polymers for preparing electrophotographic materials |
JPS463712B1 (en) | 1966-04-14 | 1971-01-29 | ||
US3526501A (en) | 1967-02-03 | 1970-09-01 | Eastman Kodak Co | 4-diarylamino-substituted chalcone containing photoconductive compositions for use in electrophotography |
US3542544A (en) | 1967-04-03 | 1970-11-24 | Eastman Kodak Co | Photoconductive elements containing organic photoconductors of the triarylalkane and tetraarylmethane types |
US3658520A (en) | 1968-02-20 | 1972-04-25 | Eastman Kodak Co | Photoconductive elements containing as photoconductors triarylamines substituted by active hydrogen-containing groups |
US3567450A (en) | 1968-02-20 | 1971-03-02 | Eastman Kodak Co | Photoconductive elements containing substituted triarylamine photoconductors |
US3615404A (en) | 1968-04-25 | 1971-10-26 | Scott Paper Co | 1 3-phenylenediamine containing photoconductive materials |
CA917980A (en) | 1969-06-20 | 1973-01-02 | J. Fox Charles | Alkylaminoaromatic organic photoconductors |
US3717462A (en) | 1969-07-28 | 1973-02-20 | Canon Kk | Heat treatment of an electrophotographic photosensitive member |
BE756375A (en) | 1969-09-30 | 1971-03-01 | Eastman Kodak Co | NEW PHOTOCONDUCTIVE COMPOSITION AND PRODUCT CONTAINING IT FOR USE IN ELECTROPHOTOGRAPHY |
BE756943A (en) | 1969-10-01 | 1971-03-16 | Eastman Kodak Co | NEW PHOTOCONDUCTIVE COMPOSITIONS AND PRODUCTS CONTAINING THEM, USED IN PARTICULAR IN ELECTROPHOTOGRAPHY |
JPS4725336B1 (en) | 1969-11-26 | 1972-07-11 | ||
JPS5110983B2 (en) | 1971-09-10 | 1976-04-08 | ||
GB1413352A (en) | 1972-02-09 | 1975-11-12 | Scott Paper Co | Electrophotographic material |
US3837851A (en) | 1973-01-15 | 1974-09-24 | Ibm | Photoconductor overcoated with triarylpyrazoline charge transport layer |
GB1505409A (en) | 1974-12-20 | 1978-03-30 | Eastman Kodak Co | Photoconductive compositions |
US4127412A (en) | 1975-12-09 | 1978-11-28 | Eastman Kodak Company | Photoconductive compositions and elements |
US4012376A (en) | 1975-12-29 | 1977-03-15 | Eastman Kodak Company | Photosensitive colorant materials |
CA1104866A (en) | 1976-08-23 | 1981-07-14 | Milan Stolka | Imaging member containing a substituted n,n,n',n',- tetraphenyl-[1,1'-biphenyl]-4,4'-diamine in the chargge transport layer |
US4175961A (en) | 1976-12-22 | 1979-11-27 | Eastman Kodak Company | Multi-active photoconductive elements |
US4123269A (en) | 1977-09-29 | 1978-10-31 | Xerox Corporation | Electrostatographic photosensitive device comprising hole injecting and hole transport layers |
US4150987A (en) | 1977-10-17 | 1979-04-24 | International Business Machines Corporation | Hydrazone containing charge transport element and photoconductive process of using same |
JPS54112637A (en) | 1978-02-06 | 1979-09-03 | Ricoh Co Ltd | Electrophotographic photoreceptor |
JPS54110837A (en) | 1978-02-17 | 1979-08-30 | Ricoh Co Ltd | Electrophotographic photoreceptor |
JPS54119925A (en) | 1978-03-10 | 1979-09-18 | Ricoh Co Ltd | Photosensitive material for electrophotography |
JPS6028342B2 (en) | 1978-06-21 | 1985-07-04 | コニカ株式会社 | electrophotographic photoreceptor |
JPS6060052B2 (en) | 1978-07-21 | 1985-12-27 | コニカ株式会社 | electrophotographic photoreceptor |
JPS5551086A (en) | 1978-09-04 | 1980-04-14 | Copyer Co Ltd | Novel pyrazoline compound, its preparation, and electrophotographic photosensitive substance comprising it |
JPS5546760A (en) | 1978-09-29 | 1980-04-02 | Ricoh Co Ltd | Electrophotographic photoreceptor |
JPS5552063A (en) | 1978-10-13 | 1980-04-16 | Ricoh Co Ltd | Electrophotographic receptor |
JPS5552064A (en) | 1978-10-13 | 1980-04-16 | Ricoh Co Ltd | Electrophotographic receptor |
JPS5574546A (en) | 1978-11-30 | 1980-06-05 | Ricoh Co Ltd | Electrophotographic photoreceptor |
US4306008A (en) | 1978-12-04 | 1981-12-15 | Xerox Corporation | Imaging system with a diamine charge transport material in a polycarbonate resin |
JPS5588064A (en) | 1978-12-05 | 1980-07-03 | Konishiroku Photo Ind Co Ltd | Electrophotographic receptor |
JPS5588065A (en) | 1978-12-12 | 1980-07-03 | Konishiroku Photo Ind Co Ltd | Electrophotographic receptor |
JPS55108667A (en) | 1979-02-13 | 1980-08-21 | Ricoh Co Ltd | Electrophotographic receptor |
US4233384A (en) | 1979-04-30 | 1980-11-11 | Xerox Corporation | Imaging system using novel charge transport layer |
JPS6035058B2 (en) | 1979-05-17 | 1985-08-12 | 三菱製紙株式会社 | Organic photo-semiconductor electrophotographic materials |
JPS564148A (en) | 1979-06-21 | 1981-01-17 | Konishiroku Photo Ind Co Ltd | Electrophotographic receptor |
JPS5622437A (en) | 1979-08-01 | 1981-03-03 | Ricoh Co Ltd | Electrophotographic receptor |
US4232103A (en) | 1979-08-27 | 1980-11-04 | Xerox Corporation | Phenyl benzotriazole stabilized photosensitive device |
JPS5636656A (en) | 1979-09-03 | 1981-04-09 | Mitsubishi Paper Mills Ltd | Electrophotographic material |
JPS5646234A (en) | 1979-09-21 | 1981-04-27 | Ricoh Co Ltd | Electrophotographic receptor |
US4273846A (en) | 1979-11-23 | 1981-06-16 | Xerox Corporation | Imaging member having a charge transport layer of a terphenyl diamine and a polycarbonate resin |
JPS5680051A (en) | 1979-12-04 | 1981-07-01 | Ricoh Co Ltd | Electrophotographic receptor |
JPS5688141A (en) | 1979-12-20 | 1981-07-17 | Konishiroku Photo Ind Co Ltd | Electrophotographic receptor |
JPS6034099B2 (en) | 1980-06-24 | 1985-08-07 | 富士写真フイルム株式会社 | electrophotographic photoreceptor |
US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
JPS6059590B2 (en) | 1980-09-03 | 1985-12-25 | 三菱製紙株式会社 | electrophotographic photoreceptor |
JPS57148749A (en) | 1981-03-11 | 1982-09-14 | Fuji Photo Film Co Ltd | Electrophotographic receptor |
US4539507A (en) * | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
JPS6094462A (en) | 1983-10-28 | 1985-05-27 | Ricoh Co Ltd | Stilbene derivative and production thereof |
JPS6093455A (en) | 1983-10-28 | 1985-05-25 | Fuji Xerox Co Ltd | Developer for electrophotography |
JPS60175052A (en) | 1984-02-21 | 1985-09-09 | Ricoh Co Ltd | Electrophotographic sensitive body |
JPS60174749A (en) | 1984-02-21 | 1985-09-09 | Ricoh Co Ltd | Styryl compound and preparation thereof |
JPS6114642A (en) | 1984-06-29 | 1986-01-22 | Konishiroku Photo Ind Co Ltd | Electrophotographic sensitive body |
JPS6129558A (en) | 1984-07-20 | 1986-02-10 | Nec Corp | Controller for density of printing of thermal printer |
JPS6172255A (en) | 1984-09-14 | 1986-04-14 | Konishiroku Photo Ind Co Ltd | Electrophotographic sensitive body |
US4665000A (en) | 1984-10-19 | 1987-05-12 | Xerox Corporation | Photoresponsive devices containing aromatic ether hole transport layers |
JPS61210363A (en) | 1985-03-15 | 1986-09-18 | Canon Inc | Electrophotographic sensitive body |
JPS61228451A (en) | 1985-04-03 | 1986-10-11 | Canon Inc | Electrophotographic sensitive body |
JPS6210652A (en) | 1985-07-08 | 1987-01-19 | Minolta Camera Co Ltd | Photosensitive body |
JPS6230255A (en) | 1985-07-31 | 1987-02-09 | Minolta Camera Co Ltd | Electrophotographic sensitive body |
JPS6236674A (en) | 1985-08-05 | 1987-02-17 | Fuji Photo Film Co Ltd | Electrophotographic sensitive body |
JPS6247646A (en) | 1985-08-27 | 1987-03-02 | Konishiroku Photo Ind Co Ltd | Photosensitive body |
US4720432A (en) | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
JPH02282263A (en) | 1988-12-09 | 1990-11-19 | Nippon Oil Co Ltd | Hole transferring material |
JP2727620B2 (en) | 1989-02-01 | 1998-03-11 | 日本電気株式会社 | Organic thin film EL device |
US5653713A (en) | 1989-04-24 | 1997-08-05 | Michelson; Gary Karlin | Surgical rongeur |
US4950950A (en) | 1989-05-18 | 1990-08-21 | Eastman Kodak Company | Electroluminescent device with silazane-containing luminescent zone |
JPH02311591A (en) | 1989-05-25 | 1990-12-27 | Mitsubishi Kasei Corp | Organic electroluminescent element |
JP2897138B2 (en) | 1989-06-30 | 1999-05-31 | 株式会社リコー | EL device |
JPH03162481A (en) | 1989-11-20 | 1991-07-12 | Pioneer Electron Corp | Electroluminescent element |
JPH0430868A (en) | 1990-05-28 | 1992-02-03 | Naoyuki Omatoi | Golf simulator |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
JPH07138561A (en) | 1993-11-17 | 1995-05-30 | Idemitsu Kosan Co Ltd | Organic electroluminescent element |
JP3306735B2 (en) | 1995-01-19 | 2002-07-24 | 出光興産株式会社 | Organic electroluminescent device and organic thin film |
JP3724833B2 (en) | 1995-03-06 | 2005-12-07 | 出光興産株式会社 | Organic electroluminescence device |
JP3712760B2 (en) | 1995-05-17 | 2005-11-02 | Tdk株式会社 | Organic EL device |
JP3677850B2 (en) | 1996-01-12 | 2005-08-03 | チッソ株式会社 | Silacyclopentadiene derivative |
JP2918150B2 (en) | 1995-07-17 | 1999-07-12 | チッソ株式会社 | Organic electroluminescent device using silacyclopentadiene derivative |
JP2982699B2 (en) | 1995-08-04 | 1999-11-29 | 東洋インキ製造株式会社 | Material for forming electron injection layer of multilayer organic electroluminescence device |
JP3716096B2 (en) | 1998-04-02 | 2005-11-16 | 三菱重工業株式会社 | Pulverized coal separator |
JP2000040586A (en) | 1998-07-21 | 2000-02-08 | Tdk Corp | Organic el element module |
JP3539628B2 (en) | 1999-09-17 | 2004-07-07 | 富士写真フイルム株式会社 | Light emitting device material, light emitting device and amine compound using the same |
DE60034105T2 (en) | 1999-09-30 | 2007-07-12 | Idemitsu Kosan Co. Ltd. | ELECTROLUMINESCENT, ORGANIC DEVICE |
JP3571977B2 (en) | 1999-11-12 | 2004-09-29 | キヤノン株式会社 | Organic light emitting device |
US7560175B2 (en) | 1999-12-31 | 2009-07-14 | Lg Chem, Ltd. | Electroluminescent devices with low work function anode |
JP4085574B2 (en) | 2000-01-06 | 2008-05-14 | 東レ株式会社 | Light emitting element |
JP3688207B2 (en) | 2000-02-18 | 2005-08-24 | 三星エスディアイ株式会社 | Organic EL device and organic EL display |
JP4024009B2 (en) * | 2000-04-21 | 2007-12-19 | Tdk株式会社 | Organic EL device |
TW565604B (en) * | 2001-04-25 | 2003-12-11 | Toray Industries | Pyrromethene metal complex, material of luminescent element using it and luminescent element |
JP4061969B2 (en) | 2001-05-28 | 2008-03-19 | 東レ株式会社 | Light emitting element |
JP4885381B2 (en) | 2001-07-23 | 2012-02-29 | 一般財団法人石油エネルギー技術センター | Novel aromatic compound and organic electroluminescence device using the same |
JP4860849B2 (en) | 2001-09-14 | 2012-01-25 | 一般財団法人石油エネルギー技術センター | Novel aromatic compound having amino group and organic electroluminescence device using the same |
JP4299028B2 (en) | 2002-03-11 | 2009-07-22 | Tdk株式会社 | Organic EL device |
JP2004311030A (en) | 2002-06-03 | 2004-11-04 | Mitsubishi Chemicals Corp | Organic electroluminescent element |
JP2004200162A (en) | 2002-12-05 | 2004-07-15 | Toray Ind Inc | Light emitting element |
CN101503393B (en) * | 2003-03-13 | 2015-08-19 | 出光兴产株式会社 | Nitrogen-containing heterocyclic derivative and organic electroluminescent element using same |
JP2005154534A (en) | 2003-11-25 | 2005-06-16 | Toray Ind Inc | Light emitting device material and light emitting device using the same |
US6885026B1 (en) | 2004-01-30 | 2005-04-26 | Eastman Kodak Company | Organic element for electroluminescent devices |
US7300709B2 (en) * | 2004-03-31 | 2007-11-27 | Eastman Kodak Company | Organic element for electroluminescent devices |
US7504163B2 (en) | 2004-07-12 | 2009-03-17 | Eastman Kodak Company | Hole-trapping materials for improved OLED efficiency |
JP2006073809A (en) * | 2004-09-02 | 2006-03-16 | Nippon Kayaku Co Ltd | Light emitting element |
JP2006245172A (en) | 2005-03-02 | 2006-09-14 | Toray Ind Inc | Light emitting element |
WO2007105448A1 (en) | 2006-02-28 | 2007-09-20 | Idemitsu Kosan Co., Ltd. | Naphthacene derivative and organic electroluminescent device using same |
JPWO2008047744A1 (en) | 2006-10-16 | 2010-02-25 | 東レ株式会社 | Light emitting element |
TW201035079A (en) * | 2009-02-27 | 2010-10-01 | Idemitsu Kosan Co | Pyrromethene-boron complex compounds and organic electro- luminescent elements using same |
-
2008
- 2008-03-07 US US12/044,436 patent/US8278819B2/en active Active
- 2008-03-10 EP EP08721707.1A patent/EP2128910B1/en active Active
- 2008-03-10 WO PCT/JP2008/054291 patent/WO2008111554A1/en active Application Filing
- 2008-03-10 JP JP2009504044A patent/JP5336352B2/en not_active Expired - Fee Related
- 2008-03-10 KR KR1020097020970A patent/KR101397219B1/en active IP Right Grant
- 2008-03-10 TW TW097108330A patent/TW200907014A/en unknown
- 2008-03-10 CN CN200880007661XA patent/CN101689612B/en active Active
-
2012
- 2012-08-14 US US13/585,132 patent/US20120305908A1/en not_active Abandoned
-
2013
- 2013-04-18 JP JP2013087718A patent/JP5647291B2/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8278819B2 (en) * | 2007-03-09 | 2012-10-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and display |
Also Published As
Publication number | Publication date |
---|---|
US8278819B2 (en) | 2012-10-02 |
JP5336352B2 (en) | 2013-11-06 |
JP5647291B2 (en) | 2014-12-24 |
EP2128910A4 (en) | 2011-04-20 |
KR101397219B1 (en) | 2014-05-20 |
US20080254319A1 (en) | 2008-10-16 |
CN101689612B (en) | 2013-08-14 |
EP2128910B1 (en) | 2016-03-09 |
TW200907014A (en) | 2009-02-16 |
JPWO2008111554A1 (en) | 2010-06-24 |
KR20100015424A (en) | 2010-02-12 |
EP2128910A1 (en) | 2009-12-02 |
CN101689612A (en) | 2010-03-31 |
JP2013179326A (en) | 2013-09-09 |
WO2008111554A1 (en) | 2008-09-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8278819B2 (en) | Organic electroluminescence device and display | |
US8044222B2 (en) | Aromatic amine derivatives and organic electroluminescent device using same | |
US7425654B2 (en) | Aromatic triamine compound and organic electroluminescence device using the same | |
US20180040828A1 (en) | Organic electroluminescent device using aryl amine derivative containing heterocycle | |
JP5374486B2 (en) | Organic electroluminescence device | |
US20100039027A1 (en) | Organic electroluminescence device | |
US20080091025A1 (en) | Aromatic amine derivative and organic electroluminescence device using the same | |
US20090066239A1 (en) | Aromatic amine derivative and organic electroluminescent device using same | |
US20070063638A1 (en) | White color organic electroluminescence device | |
US20090167161A1 (en) | Aromatic amine derivatives and organic electroluminescence device using the same | |
US20070145888A1 (en) | Aromatic amine derivatives and organic electroluminescence device using the same | |
US20120302793A1 (en) | Aromatic amine derivative and organic electroluminescent device using same | |
US20080007160A1 (en) | Organic electroluminescent device using fluoranthene derivative and indenoperylene derivative | |
US20060217572A1 (en) | Aromatic amine derivative and organic electroluminescence device employing the same | |
US20070222373A1 (en) | Naphthacene derivative and organic electroluminescent device using the same | |
JPWO2009081857A1 (en) | Organic electroluminescence device | |
JP2007186461A (en) | Aromatic amine derivative and organic electroluminescent element using the same | |
JP2009188136A (en) | Organic el element and display device | |
US20080241588A1 (en) | Organic electroluminescence device and display |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |