JP2006328037A - Binaphthyl derivative, host material and hole transport material each made therefrom, and organic el device using the hole transport material - Google Patents
Binaphthyl derivative, host material and hole transport material each made therefrom, and organic el device using the hole transport material Download PDFInfo
- Publication number
- JP2006328037A JP2006328037A JP2005212187A JP2005212187A JP2006328037A JP 2006328037 A JP2006328037 A JP 2006328037A JP 2005212187 A JP2005212187 A JP 2005212187A JP 2005212187 A JP2005212187 A JP 2005212187A JP 2006328037 A JP2006328037 A JP 2006328037A
- Authority
- JP
- Japan
- Prior art keywords
- group
- binaphthyl derivative
- hole transport
- organic
- binaphthyl
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 89
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 230000005525 hole transport Effects 0.000 title claims abstract description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims 1
- TXKUKWYVFCPPGA-UHFFFAOYSA-N 4-(3-anilino-2-methoxynaphthalen-1-yl)-3-methoxy-n-phenylnaphthalen-2-amine Chemical group C1=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=C(NC=3C=CC=CC=3)C=2OC)C(OC)=C1NC1=CC=CC=C1 TXKUKWYVFCPPGA-UHFFFAOYSA-N 0.000 abstract description 2
- 0 *C(C(Cc1c2cccc1)N(c1c(*)cccc1)c1ccccc1*)=C2c1c(cccc2)c2cc(N2c3c(*)cccc3)c1*C1C=C(*)C2=CC1 Chemical compound *C(C(Cc1c2cccc1)N(c1c(*)cccc1)c1ccccc1*)=C2c1c(cccc2)c2cc(N2c3c(*)cccc3)c1*C1C=C(*)C2=CC1 0.000 description 28
- 239000010410 layer Substances 0.000 description 26
- -1 nobiphenyl Chemical group 0.000 description 21
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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 20
- 239000002904 solvent Substances 0.000 description 18
- 238000007740 vapor deposition Methods 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- NSABRUJKERBGOU-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 NSABRUJKERBGOU-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000000151 deposition Methods 0.000 description 11
- 230000008021 deposition Effects 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BJAADAKPADTRCH-UHFFFAOYSA-N 2-methoxy-1-(2-methoxynaphthalen-1-yl)naphthalene Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OC)=C(OC)C=CC2=C1 BJAADAKPADTRCH-UHFFFAOYSA-N 0.000 description 3
- DFTUKDIMHCCQIT-UHFFFAOYSA-N 3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC(Br)=C3OC)=C(OC)C(Br)=CC2=C1 DFTUKDIMHCCQIT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 125000003828 azulenyl group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- ZRXVCYGHAUGABY-UHFFFAOYSA-O tris(4-bromophenyl)azanium Chemical compound C1=CC(Br)=CC=C1[NH+](C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 ZRXVCYGHAUGABY-UHFFFAOYSA-O 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- QMFVLQXRHBTDSH-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C QMFVLQXRHBTDSH-UHFFFAOYSA-N 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- CZAVPKZCPBVPDJ-UHFFFAOYSA-N 1,2-bis[2-(2-phenylphenyl)phenyl]benzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 CZAVPKZCPBVPDJ-UHFFFAOYSA-N 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- UTXIFKBYNJRJPH-UHFFFAOYSA-N 1-(2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-5,6,7,8-tetrahydronaphthalen-2-ol Chemical group C1CCCC2=C1C=CC(O)=C2C1=C2CCCCC2=CC=C1O UTXIFKBYNJRJPH-UHFFFAOYSA-N 0.000 description 1
- IERDDDBDINUYCD-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)phenyl]phenyl]-9h-carbazole Chemical group C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 IERDDDBDINUYCD-UHFFFAOYSA-N 0.000 description 1
- GKEGJNRVJZBCOX-UHFFFAOYSA-N 1-phenyl-2-[2-[2-[2-[2-(2-phenylphenyl)phenyl]phenyl]phenyl]phenyl]benzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 GKEGJNRVJZBCOX-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- CLJLIUPVJYTDBY-UHFFFAOYSA-N 3-methoxy-4-[2-methoxy-3-(2-methylanilino)-5,6,7,8-tetrahydronaphthalen-1-yl]-N-(2-methylphenyl)-5,6,7,8-tetrahydronaphthalen-2-amine Chemical group CC1=CC=CC=C1NC2=C(C(=C3CCCCC3=C2)C4=C5CCCCC5=CC(=C4OC)NC6=CC=CC=C6C)OC CLJLIUPVJYTDBY-UHFFFAOYSA-N 0.000 description 1
- IWZMLKAQOIEKSM-UHFFFAOYSA-N 3-methoxy-4-[2-methoxy-3-(2-methylanilino)naphthalen-1-yl]-N-(2-methylphenyl)naphthalen-2-amine Chemical group CC1=CC=CC=C1NC2=CC3=CC=CC=C3C(=C2OC)C4=C(C(=CC5=CC=CC=C54)NC6=CC=CC=C6C)OC IWZMLKAQOIEKSM-UHFFFAOYSA-N 0.000 description 1
- BAWSNNMGXOOZLV-UHFFFAOYSA-N 7-bromo-5-(3-bromo-2-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl)-6-methoxy-1,2,3,4-tetrahydronaphthalene Chemical group C1CCCC2=CC(Br)=C(OC)C(C3=C4CCCCC4=CC(Br)=C3OC)=C21 BAWSNNMGXOOZLV-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- QLMVMZUEXHJYMD-UHFFFAOYSA-N CC(C)(c1ccccc1-c1c2)c1ccc2N(c1cccc(C)c1)c1c(C)c(-c2c(C)c(N(c3cc(-c4c(C5(C)C)cccc4)c5cc3)c3cccc(C)c3)cc3ccccc23)c(cccc2)c2c1 Chemical compound CC(C)(c1ccccc1-c1c2)c1ccc2N(c1cccc(C)c1)c1c(C)c(-c2c(C)c(N(c3cc(-c4c(C5(C)C)cccc4)c5cc3)c3cccc(C)c3)cc3ccccc23)c(cccc2)c2c1 QLMVMZUEXHJYMD-UHFFFAOYSA-N 0.000 description 1
- MBUGIRQAHIDGPM-UHFFFAOYSA-N CCc(cccc1)c1N(c1cc2ccccc2c(-c2c(cccc3)c3cc(N(c3c(CC)cccc3)c3c(CC)cccc3)c2CC)c1)c1c(CC)cccc1 Chemical compound CCc(cccc1)c1N(c1cc2ccccc2c(-c2c(cccc3)c3cc(N(c3c(CC)cccc3)c3c(CC)cccc3)c2CC)c1)c1c(CC)cccc1 MBUGIRQAHIDGPM-UHFFFAOYSA-N 0.000 description 1
- YNIRQDJPOVHBAM-UHFFFAOYSA-N Cc(c(-c1c(C)c(-[n]2c3cc4ccccc4cc3c3cc(cccc4)c4cc23)cc2ccccc12)c(cccc1)c1c1)c1-[n]1c2cc(cccc3)c3cc2c2cc3ccccc3cc12 Chemical compound Cc(c(-c1c(C)c(-[n]2c3cc4ccccc4cc3c3cc(cccc4)c4cc23)cc2ccccc12)c(cccc1)c1c1)c1-[n]1c2cc(cccc3)c3cc2c2cc3ccccc3cc12 YNIRQDJPOVHBAM-UHFFFAOYSA-N 0.000 description 1
- ONJFSICGYSJEBZ-UHFFFAOYSA-N Cc(c(-c1c(C)c(-[n]2c3cc4ccccc4cc3c3ccccc23)cc2ccccc12)c(cccc1)c1c1)c1-[n]1c2cc3ccccc3cc2c2c1cccc2 Chemical compound Cc(c(-c1c(C)c(-[n]2c3cc4ccccc4cc3c3ccccc23)cc2ccccc12)c(cccc1)c1c1)c1-[n]1c2cc3ccccc3cc2c2c1cccc2 ONJFSICGYSJEBZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VFUDMQLBKNMONU-UHFFFAOYSA-N c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 230000000052 comparative effect Effects 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
- 230000009849 deactivation Effects 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000003824 heptacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC7=CC=CC=C7C=C6C=C5C=C4C=C3C=C12)* 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
- 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
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- WOSISLOTWLGNKT-UHFFFAOYSA-L iron(2+);dichloride;hexahydrate Chemical compound O.O.O.O.O.O.Cl[Fe]Cl WOSISLOTWLGNKT-UHFFFAOYSA-L 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl 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])[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
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001420 pyrrolonyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
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Abstract
Description
本発明は、新規なビナフチル誘導体、それよりなるホスト材料、ホール輸送材料およびそれを用いた有機ＥＬ素子に関する。 The present invention relates to a novel binaphthyl derivative, a host material comprising the same, a hole transport material, and an organic EL device using the same.
有機ＥＬの実用化に向けた研究開発が、国内外の電気メーカーや材料メーカーなどが中心になって進められている。液晶表示素子や発光ダイオードなどの既に世間に知られているディスプレイなどと、互角に渡り歩いていくには消費電力の低減および素子の長寿命化が必須の課題としてあげられている。
そこで、この問題を解決する目的で、近年リン光材料による有機ＥＬ素子の検討が成されている。
リン光材料は従来の蛍光材料と異なり、三重項励起状態を使用することができるため量子効率が非常に高く、エネルギー失活がほとんどなく内部発光量子収率でほぼ１００％に達する材料である。
しかしこのリン光材料は、濃度消光を起こしやすいため蛍光材料同様にホスト材料との併用が必要になってくる。
高効率発光を得るためには、輸送材料やホスト材料の最適化を図らないといけないが、リン光材料は蛍光材料とは異なり三重項エネルギーを完全に閉じこめないと満足な効果が得られない。特に青色の材料に関してはエネルギーレベルが非常に高い。そのためこれまで使用していたα−ＮＰＤでは十分なエネルギーの閉じこめができない。これまでこの青色リン光エネルギーを閉じ込めることができるワイドギャップ化された輸送材料やホスト材料が無く、青色リン光材料の開発を妨げる一つの要因になっていた。
Research and development for the practical application of organic EL is being promoted mainly by domestic and foreign electric and material manufacturers. Reducing power consumption and prolonging the life of the elements are indispensable issues for walking alongside displays that are already known to the public such as liquid crystal display elements and light emitting diodes.
Therefore, in order to solve this problem, an organic EL element using a phosphorescent material has recently been studied.
Unlike conventional fluorescent materials, phosphorescent materials can use triplet excited states, so that quantum efficiency is very high, energy deactivation is hardly caused, and the internal emission quantum yield reaches almost 100%.
However, since this phosphorescent material easily causes concentration quenching, it is necessary to use it together with a host material in the same manner as a fluorescent material.
In order to obtain high-efficiency light emission, it is necessary to optimize transport materials and host materials, but unlike phosphor materials, phosphorescent materials cannot obtain satisfactory effects unless triplet energy is completely confined. Especially for blue materials, the energy level is very high. Therefore, the α-NPD that has been used so far cannot confine sufficient energy. Until now, there was no wide-gap transport material or host material capable of confining this blue phosphorescent energy, which was one factor hindering the development of blue phosphorescent materials.
本発明の第１の目的は、新規なリン光材料に適したワイドギャップなホール輸送層を形成するための新規なビナフチル誘導体を提供する点にある。
本発明の第２の目的は、新規なビナフチル誘導体よりなるホスト材料、ホール輸送材料、およびこれを用いた新規な有機ＥＬ素子を提供する点にある。
A first object of the present invention is to provide a novel binaphthyl derivative for forming a wide-gap hole transport layer suitable for a novel phosphorescent material.
The second object of the present invention is to provide a host material comprising a novel binaphthyl derivative, a hole transport material, and a novel organic EL device using the same.
本発明の第１は、下記一般式（１）
で示されるビナフチル誘導体に関する。
本発明の第２は、一般式（１）におけるＱ１とＱ２のうちの少なくともいずれか一方およびＱ３とＱ４のうち少なくともいずれか一方が、Ａｒ１とＡｒ２が一体になったヘテロアリール基である請求項１記載のビナフチル誘導体に関する。
本発明の第３は、前記ヘテロアリール基が、下記式（２）
で示されるカルバゾリル基である請求項２記載のビナフチル誘導体に関する。
本発明の第４は、３．１ｅＶを越える広いエネルギーギャップを有するものである請求項１〜３いずれか記載のビナフチル誘導体に関する。
本発明の第５は、請求項１〜４いずれか記載のビナフチル誘導体よりなることを特徴とするホスト材料に関する。
本発明の第６は、請求項１〜４いずれか記載のビナフチル誘導体よりなることを特徴とするホール輸送材料に関する。
本発明の第７は、請求項１〜４いずれか記載のビナフチル誘導体を用いたことを特徴とする有機ＥＬ素子に関する。
本発明の第８は、請求項１〜４いずれか記載のビナフチル誘導体を発光層またはホール輸送層に用いたことを特徴とする有機ＥＬ素子に関する。
本発明の第９は、発光材料として燐光材料を用いた請求項７または８記載の有機ＥＬ素子に関する。
本発明の第１０は、その発光ピーク波長が４８０ｎｍよりも短波長の青色発光を示す燐光材料を発光材料として用いた請求項９記載の有機ＥＬ素子に関する。
The first of the present invention is the following general formula (1)
It relates to the binaphthyl derivative shown by these.
In the second aspect of the present invention, at least one of Q 1 and Q 2 and at least one of Q 3 and Q 4 in the general formula (1) are heterogeneous in which Ar 1 and Ar 2 are integrated. The binaphthyl derivative according to claim 1, which is an aryl group.
In a third aspect of the present invention, the heteroaryl group has the following formula (2):
The binaphthyl derivative according to
A fourth aspect of the present invention relates to the binaphthyl derivative according to any one of claims 1 to 3, which has a wide energy gap exceeding 3.1 eV.
5th of this invention is related with the host material characterized by consisting of the binaphthyl derivative in any one of Claims 1-4.
6th of this invention is related with the hole transport material which consists of a binaphthyl derivative in any one of Claims 1-4.
A seventh aspect of the present invention relates to an organic EL device using the binaphthyl derivative according to any one of claims 1 to 4.
The eighth of the present invention relates to an organic EL device characterized in that the binaphthyl derivative according to any one of claims 1 to 4 is used for a light emitting layer or a hole transport layer.
A ninth aspect of the present invention relates to the organic EL element according to
The tenth aspect of the present invention relates to the organic EL element according to claim 9, wherein a phosphorescent material that emits blue light having an emission peak wavelength shorter than 480 nm is used as a light emitting material.
前記、Ａｒ１、Ａｒ２、Ｒ１〜Ｒ２およびＲ２０〜Ｒ２７におけるアリール基としては、置換基を有することもある１環または多環構造のいずれのものであってもよい。具体例を挙げるとフェニル、ビフェニル、ターフェニル、クオーターフェニル、クウィンクフェニル、セスキフェニル、セプチフェニル、オクチフェニル、ノビフェニル、デシフェニル、ナフチル、アズレニル、アントラニル、フェナンソレニル、ナフタセニル、クリセニル、ペンタレニル、インデニル、アズレニル、ヘプタデニル、ビフェニレル、ａｓ−インダセニル、ｓ−インダセニル、アセナフチレニル、フルオレニル、フェナレニル、フルオラセニル、アセフェナンソラレニル、アセアンソリレニル、トリフェニレル、ピレニル、プレイアデニル、ピセニル、ペリレニル、ペンタフェニル、ペンタセニル、テトラフェニレニル、ヘキサフェニル、ヘキサアセニル、ルビセニル、コロネリル、トリナフチレニル、ヘキサフェニル、ヘキサアセニル、ルビセニル、コロネリル、トリナフテレニル、ヘプタフェニル、ヘプタセニル、ピランセニル、オバレニルなどを挙げることができる。 The aryl group in Ar 1 , Ar 2 , R 1 to R 2 and R 20 to R 27 may be a monocyclic or polycyclic structure that may have a substituent. Specific examples include phenyl, biphenyl, terphenyl, quarterphenyl, quinckphenyl, sesquiphenyl, septiphenyl, octiphenyl, nobiphenyl, decylphenyl, naphthyl, azulenyl, anthranyl, phenanthrenyl, naphthacenyl, chrysenyl, pentarenyl, indenyl, azulenyl, Heptadenyl, biphenylyl, as-indacenyl, s-indacenyl, acenaphthylenyl, fluorenyl, phenalenyl, fluoracenyl, acephenanthrarenyl, aceanthrylenyl, triphenylyl, pyrenyl, preadenyl, picenyl, perylenyl, pentaphenyl, pentaphenyl, tetraphenylenyl Nyl, hexaphenyl, hexaacenyl, ruvicenyl, coronyl, trinaphthylenyl, hexaphenyl, hex It Aseniru, rubicenyl, coronenyl, Torinafutereniru, heptaphenyl, heptacenyl, Piranseniru, and ovalenyl.
前記、Ａｒ１、Ａｒ２、Ｒ１〜Ｒ２およびＲ２０〜Ｒ２７におけるヘテロアリール基としては、置換基を有することもある各種へテロアリール基であり、１環または多環構造のいずれのものであってもよい。具体例を挙げると、フラニル、ピロロニル、３−ピロロニル、ピラゾリル、イミダゾリル、オキサゾリル、チアゾリル、１，２，３−オキサジアゾリル、トリアゾリル、ピラニル、ピリジニル、ピリダジニル、ピリミジニル、ピラジニル、１,３，５−トリアジニル、ベンゾフラニル、インドリル、ベンゾ〔ｂ〕チオフェニル、ベンゾイミダゾリル、ベンゾチアゾリル、プリニル、キノリニル、イソキノリニル、シンノリニル、キノキサリニル、カルバゾリル、アクリジニル、１，１０−フェントレニルなどを挙げることができる。 The heteroaryl groups in Ar 1 , Ar 2 , R 1 to R 2 and R 20 to R 27 are various heteroaryl groups that may have a substituent, and are either monocyclic or polycyclic structures. It may be. Specific examples include furanyl, pyrrolonyl, 3-pyrrolonyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, 1,2,3-oxadiazolyl, triazolyl, pyranyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, Examples thereof include benzofuranyl, indolyl, benzo [b] thiophenyl, benzimidazolyl, benzothiazolyl, purinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinoxalinyl, carbazolyl, acridinyl, 1,10-fentrenyl and the like.
また、Ａｒ１とＡｒ２が結合した場合の形としてはＡｒ１とＡｒ２が結合しているＮ原子も含めてその構造例を示すと
勿論これらの環構造においても必要に応じて置換基を有する場合も含んでいる。
In addition, when Ar 1 and Ar 2 are bonded, the structure example including the N atom to which Ar 1 and Ar 2 are bonded is shown.
Of course, these ring structures include cases where they have substituents as necessary.
前記Ｒ１〜Ｒ２およびＲ２０〜Ｒ２７におけるアルキル基としては、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、ノニル、デシル、ウンデシル、ドデシル、トリデシル、テトラデシル、ペンタデシル、ヘキサデシル、ヘプタデシル、オクタデシル、ノナデシル、エイコシルなどを挙げることができる。これらについては直鎖でも枝分かれでも構わない。 Examples of the alkyl group in R 1 to R 2 and R 20 to R 27 include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, Examples include heptadecyl, octadecyl, nonadecyl, eicosyl and the like. These may be linear or branched.
前記Ｒ１〜Ｒ２およびＲ２０〜Ｒ２７におけるアルコキシ基としては、メトキシ、エトキシ、プロポキシ、ブトキシ、ペントキシ、ヘキシロキシ、ヘプチロキシ、オクトキシ、ノニロキシ、デシロキシ、フンデシロシキシ、ドデシロキシ、トリデシロキシ、テトラデシロキシ、ペンタデシロキシ、ヘキサデシロキシ、ヘプタデシロキシ、オクタデシロキシ、ノナデシロキシ、エイコシロキシなどを挙げることができる。これらについては直鎖でも枝分かれでも構わない。Ｒ１〜Ｒ２のアルコキシカルボニル基におけるアルコキシ部分は前記アルコキシ基と同様である。 Examples of the alkoxy group in R 1 to R 2 and R 20 to R 27 include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, heptyloxy, octoxy, nonyloxy, decyloxy, decyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentade Examples include siloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, eicosiloxy and the like. These may be linear or branched. The alkoxy moiety in the alkoxycarbonyl group of R 1 to R 2 is the same as the alkoxy group.
前記Ｒ１〜Ｒ２およびＲ２０〜Ｒ２７におけるハロゲンとしては、いずれのハロゲンでもよい。 The halogen in R 1 to R 2 and R 20 to R 27 may be any halogen.
前記アリールオキシ基、アリールオキシカルボニル基におけるアリール部分は前記アリール基と同様であり、ヘテロアリールオキシ基、ヘテロアリールオキシカルボニル基におけるヘテロアリール部分はヘテロアリール基と同様であり、アリール基、アリーロキシ基、ヘテロアリール基、ヘテロアリールオキシ基、アリールオキシカルボニル基、ヘテロアリーロキシカルボニル基における置換基としては、アルキル基、アルコキシル基、アルコキシカルボニル基、アリールオキシカルボニル基およびハロゲンをあげることができ、アルキル基やアルコキシ基としては前述のものを例示することができ、アルコキシカルボニル基につくアルキルグループやアリールオキシカルボニル基につくアリールグループについても同様に前述のものを例示することができる。
また、アルキル基やアルコキシ基における置換基としては、エステル基やハロゲンを挙げることができる。
The aryl moiety in the aryloxy group and aryloxycarbonyl group is the same as the aryl group, the heteroaryl moiety in the heteroaryloxy group and heteroaryloxycarbonyl group is the same as the heteroaryl group, and the aryl group, aryloxy group, Examples of the substituent in the heteroaryl group, heteroaryloxy group, aryloxycarbonyl group, and heteroaryloxycarbonyl group include an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, and a halogen. The above-mentioned thing can be illustrated as an alkoxy group, The above-mentioned thing is similarly illustrated about the alkyl group attached to an alkoxycarbonyl group, and the aryl group attached to an aryloxycarbonyl group. Rukoto can.
In addition, examples of the substituent in the alkyl group or alkoxy group include an ester group and a halogen.
本発明化合物の代表的な合成方法の１例を下記に示す。Ｒ１〜Ｒ２およびＡｒ１、Ａｒ２は前記のとおりである。
また、本発明の化合物の例を下記に示す。 Examples of the compound of the present invention are shown below.
多くの発光材料は濃度消光を起こしやすくこのため効率の低下を起こしやすい。リン光材料もこの例外でなく、高効率化を維持するめには発光材料よりもエネルギーレベルの大きな材料（すなわちホスト材料）の中に分散させて使用する必要がある。
ホスト材料に求められる特性としては、均一なアモルファス膜になることやキャリアーの輸送能力があること等が挙げられる。
特に青色リン光材料に使用されるホスト材料としてはリン光材料の三重項エネルギーが他の緑や赤に比べて大きいため、これまで使用されているようなホスト材料では十分な青色の効率を達成するのが困難であり、ワイドギャップ化させる必要がある。
すなわちリン光ゲスト材料よりも大きな三重項エネルギーを有していること（ワイドギャップ化）の必要である。
今回のホスト材料としての本発明化合物はこの点に着目し合成を行ったものである。ホスト材料に混ぜられるゲスト化合物の量はおよそ４％から８％程度が理想的とされている。また、その膜厚は、４０ｎｍ〜６０ｎｍ位が適当とされている。
Many light-emitting materials tend to cause concentration quenching, and thus easily reduce efficiency. The phosphorescent material is no exception. To maintain high efficiency, it is necessary to use the phosphorescent material dispersed in a material having a higher energy level than the light emitting material (that is, a host material).
Properties required for the host material include a uniform amorphous film and a carrier transport capability.
Especially as a host material used for blue phosphorescent materials, the triplet energy of phosphorescent materials is larger than other green and red, so that the host materials used so far achieve sufficient blue efficiency. It is difficult to do so, and it is necessary to make a wide gap.
That is, it is necessary to have a triplet energy larger than that of the phosphorescent guest material (wide gap formation).
The compound of the present invention as the host material was synthesized by paying attention to this point. The amount of the guest compound mixed with the host material is ideally about 4% to 8%. The film thickness is suitably about 40 to 60 nm.
ホスト材料については、あくまでもゲスト材料（例えばこの場合ではリン光材料であるが）にホスト内で発生させた励起子を与え、ゲスト材料を発光に導くのが本来の目的である。しかしホスト内にゲスト分子が存在しない場合、ホスト内で生成した励起子同士はホスト内で再結合を起こしホスト材料が発光を起こす。このためホスト材料が発光材料として機能することになる。もしホストの中で発生した励起子がホストの膜を突き抜けてホスト層の外へ出るような場合、良好な励起子移動が起こらないためゲスト材料が発光しなくなる。
このためホスト材料が良好な発光材料であることは、ホスト−ゲスト効果の一つの基本だと考えられる。
このビナフチル化合物については、その３位にトリアリールアミン骨格を有しているためホール輸送機能を持つ。このためこの材料は、ホール輸送層に使用することが可能である。
As for the host material, the original purpose is to provide the guest material (for example, a phosphorescent material in this case) with excitons generated in the host and to guide the guest material to light emission. However, when there is no guest molecule in the host, excitons generated in the host recombine in the host and the host material emits light. For this reason, the host material functions as a light emitting material. If excitons generated in the host penetrate the host film and go out of the host layer, the exciton migration does not occur and the guest material does not emit light.
Therefore, it is considered that one of the host-guest effects is that the host material is a good light-emitting material.
Since this binaphthyl compound has a triarylamine skeleton at the 3-position, it has a hole transport function. For this reason, this material can be used for the hole transport layer.
請求項９についてみると、本発明化合物のビナフチル骨格は広いエネルギーレベルを持つ化合物であり、大きな三重項エネルギーを有しているため、青色リン光材料から赤色リン光材料にかけてのゲスト材料であるリン光材料に対して使用できるホスト材料である。 As for claim 9, since the binaphthyl skeleton of the compound of the present invention is a compound having a wide energy level and has a large triplet energy, phosphorous which is a guest material from a blue phosphorescent material to a red phosphorescent material. It is a host material that can be used for optical materials.
現在既存のホスト材料としてＣＢＰ（４,４′−ジカルバゾリル−１,１′−ビフェニル）があるが、この化合物の三重項エネルギーが青色のリン光材料に対して十分ではないため満足のできるリン光発光を得ることができなかった。しかし今回開発した新規ビナフチル誘導体に関しては、材料のねじれが大きいため十分な三重項エネルギーをもっており、多大なエネルギーが必要な４８０ｎｍより短波長な青色リン光材料を組み合わせてみると、有機ＥＬ素子としても良好な結果が得られる。 Currently, there is CBP (4,4'-dicarbazolyl-1,1'-biphenyl) as an existing host material, but the phosphorescence is satisfactory because the triplet energy of this compound is not sufficient for blue phosphorescent materials. Luminescence could not be obtained. However, the new binaphthyl derivative developed this time has sufficient triplet energy due to the large twist of the material, and when combined with a blue phosphorescent material having a wavelength shorter than 480 nm, which requires a lot of energy, it can be used as an organic EL device. Good results are obtained.
バッファー層とは一般に注入層のことをさしているが、その中には、電荷注入層やホール注入層も含まれている。
電荷注入層は、電極（ＩＴＯ電極、Ａｌ電極）からそれぞれホールと電子を有機材料に効率よく注入する役目を持っている。
The buffer layer generally refers to an injection layer, which includes a charge injection layer and a hole injection layer.
The charge injection layer has a role of efficiently injecting holes and electrons from the electrodes (ITO electrode, Al electrode) to the organic material.
（１）新規なビナフチル誘導体を提供することができた。
（２）この新規なビナフチル誘導体をホール輸送材料として使用して、リン光材料を含有する有機ＥＬ素子を作成したところ、従来に使用されているホール輸送層にα−ＮＰＤを用いた有機ＥＬ素子に比べ最大で約１．３倍の効率向上が認められた〔例えば、図５において、輝度が１０２の場合の視感効率はα−ＮＰＤの値（◇印）、３ＤＴＡ２ＭＢＮの値（△印）の方が１．３倍位高い位置にある〕。すなわち、本発明の新規ビナフチル誘導体はα−ＮＰＤの代換品として極めてすぐれたものであり、この分野の材料の豊富化に貢献するものである。
（３）本発明のビナフチル誘導体のエネルギーギャップ（ビナフチル化合物のＨＯＭＯ値からＬＵＭＯ値を引いた値）を測定したところ、３．４ｅＶであり、α−ＮＰＤの３．１ｅＶに比べてワイドギャップ化が図られており、大きなエネルギーを必要とする青色リン光材料を駆動させるためにも適応でき、これまで懸念されていた有機ＥＬ素子の高効率化、低消費電力化に貢献できる。いいかえれば、α−ＮＰＤのエネルギーギャップでは青色リン光材料を充分発光させることができなかったが、本発明の化合物をホスト材料とすることにより、青色リン光材料を発光させることができた。
(1) A novel binaphthyl derivative could be provided.
(2) Using this novel binaphthyl derivative as a hole transporting material, an organic EL device containing a phosphorescent material was prepared. As a result, an organic EL device using α-NPD in a conventionally used hole transporting layer maximum efficiency improved by about 1.3 times in was observed [for example, in FIG. 5, the value of luminous efficiency alpha-NPD if the luminance is 10 2 compared to (◇ symbol), the value of 3DTA2MBN (△ mark ) Is about 1.3 times higher]. That is, the novel binaphthyl derivative of the present invention is an excellent substitute for α-NPD, and contributes to the enrichment of materials in this field.
(3) The energy gap of the binaphthyl derivative of the present invention (the value obtained by subtracting the LUMO value from the HOMO value of the binaphthyl compound) was measured to be 3.4 eV, which is a wider gap than that of α-NPD of 3.1 eV. The present invention can be adapted to drive a blue phosphorescent material that requires a large amount of energy, and can contribute to higher efficiency and lower power consumption of organic EL elements that have been feared so far. In other words, although the blue phosphorescent material could not emit light sufficiently with the energy gap of α-NPD, the blue phosphorescent material could emit light by using the compound of the present invention as a host material.
以下、実施例を挙げて本発明を説明するが、本発明はこれにより何ら限定されるものではない。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not limited at all by this.
実施例１
（１）１，１′−ビ−２−ナフトール〔１，１′−Ｂｉ−２−Ｎａｐｈｔｈｏｌ（ＢＩＮＯＬ）〕の合成
(1) Synthesis of 1,1′-bi-2-naphthol [1,1′-Bi-2-Naphthol (BINOL)]
（２）２，２′−ジメトキシ−１，１′−ビナフチル〔２，２′−Ｄｉｍｅｔｈｏｘｙ−１，１′−ｂｉｎａｐｈｔｈｙｌ（２ＭＢＮ）〕の合成
（３）３，３′−ジブロモ−２，２′−ジメトキシ−１，１′−ビナフチル
〔３，３′−Ｄｉｂｒｏｍｏ−２，２′−ｄｉｍｅｔｈｏｘｙ−１，１′−ｂｉｎａｐｈｔｈｙｌ（３Ｂ２ＭＢＮ）〕の合成
（４）３，３′−ジフェニルアミノ−２，２′−ジメトキシ−１，１′−ビナフチル
〔３，３′−Ｄｉｐｈｅｎｙｌａｍｉｎｏ−２，２′−ｄｉｍｅｔｈｏｘｙ−１，１′−ｂｉｎａｐｈｔｈｙｌ（３ＤＰＡ２ＭＢＮ）〕の合成
実施例２
（１）３，３′−ジトリルアミノ−２，２′−ジメトキシ−１，１′−ビナフチル（３ＤＴＡ２ＭＢＮ）の合成
(1) Synthesis of 3,3′-ditolylamino-2,2′-dimethoxy-1,1′-binaphthyl (3DTA2MBN)
実施例３
（１）５，５′，６，６′，７，７′，８，８′−オクタヒドロ−２，２′−ジメトキシ−１，１′−ビナフチル（５，５′，６，６′，７，７′，８，８′−ｏｃｔａｈｙｄｒｏ−２，２′−ｄｉｍｅｔｈｏｘｙ−１，１′−ｂｉｎａｐｈｔｈｙｌ）（Ｈ８−２ＭＢＮ）の合成
(1) 5,5 ′, 6,6 ′, 7,7 ′, 8,8′-octahydro-2,2′-dimethoxy-1,1′-binaphthyl (5,5 ′, 6,6 ′, 7 , 7 ', 8,8'-octahydro- 2,2'-dimethoxy-1,1'-binaphthyl) synthesis of (H 8 -2MBN)
（２）３，３′−ジブロモ−５，５′，６，６′，７，７′，８，８′−オクタヒドロ−２，２′−ジメトキシ−１，１′−ビナフチル
（３，３′−Ｄｉｂｒｏｍｏ−５，５′，６，６′，７，７′，８，８′−ｏｃｔａｈｙｄｒｏ−２，２′−ｄｉｍｅｔｈｏｘｙ−１，１′−ｂｉｎａｐｈｔｈｙｌ）（Ｈ８−３Ｂ２ＭＢＮ）の合成
（３）３，３′−ジトルイルアミノ−５，５′，６，６′，７，７′，８，８′−オクタヒドロ−２，２′−ジメトキシ−１，１′−ビナフチル
〔３，３′−Ｄｉｔｏｌｙｌａｍｉｎｏ−５，５′，６，６′，７，７′，８，８′−ｏｃｔａｈｙｄｒｏ−２，２′−ｄｉｍｅｔｈｏｘｙ−１，１′−ｂｉｎａｐｈｔｈｙｌ〕（Ｈ８−３ＤＴＡ２ＭＢＮ）の合成
実施例４
ビナフチル誘導体よりなる各種のホール輸送材料を用いバッファー層を導入した下記構成の緑色リン光素子を作製し、α−ＮＰＤとの比較をおこなった。
デバイス１：〔ＩＴＯ／ＴＰＤＰＥＳ：ＴＢＰＡＨ（２００Å）／３ＤＰＡ２ＭＢＮ（実施例１）（２００Å）／ＣＢＰ：７ｗｔ％Ｉｒ（ｐｐｙ）３（３００Å）／ＢＣＰ（１００Å）／Ａｌｑ３（２００Å）／ＬｉＦ（５Å）／Ａｌ〕
デバイス２：〔ＩＴＯ／ＴＰＤＰＥＳ：ＴＢＰＡＨ（２００Å）／３ＤＴＡ２ＭＢＮ（実施例２）（２００Å）／ＣＢＰ：７ｗｔ％Ｉｒ（ｐｐｙ）３（３００Å）／ＢＣＰ（１００Å）／Ａｌｑ３（２００Å）／ＬｉＦ（５Å）／Ａｌ〕
デバイス３：〔ＩＴＯ／ＴＰＤＰＥＳ：ＴＢＰＡＨ（２００Å）／Ｈ８−３ＤＴＡ２ＭＢＮ（実施例３）（２００Å）／ＣＢＰ：７ｗｔ％Ｉｒ（ｐｐｙ）３（３００Å）／ＢＣＰ（１００Å）／Ａｌｑ３（２００Å）／ＬｉＦ（５Å）／Ａｌ〕
デバイス４：〔ＩＴＯ／ＴＰＤＰＥＳ：ＴＢＰＡＨ（２００Å）／α−ＮＰＤ（２００Å）／ＣＢＰ：７ｗｔ％Ｉｒ（ｐｐｙ）３（３００Å）／ＢＣＰ（１００Å）／Ａｌｑ３（２００Å）／ＬｉＦ（５Å）／Ａｌ〕
Example 4
A green phosphorescent device having the following constitution in which a buffer layer was introduced using various hole transport materials made of a binaphthyl derivative was prepared and compared with α-NPD.
Device 1: [ITO / TPDPES: TBPAH (200Å) / 3DPA2MBN (Example 1) (200Å) / CBP: 7 wt% Ir (ppy) 3 (300Å) / BCP (100Å) / Alq 3 (200Å) / LiF (5Å) ) / Al]
Device 2: [ITO / TPDPES: TBPAH (200Å) / 3DTA2MBN (Example 2) (200Å) / CBP: 7 wt% Ir (ppy) 3 (300Å) / BCP (100Å) / Alq 3 (200Å) / LiF (5Å) ) / Al]
Device 3: [ITO / TPDPES: TBPAH (200 Å) / H 8 -3DTA2MBN (Example 3) (200 Å) / CBP: 7 wt% Ir (ppy) 3 (300 Å) / BCP (100 Å) / Alq 3 (200 Å) / LiF (5cm) / Al]
Device 4: [ITO / TPDPES: TBPAH (200 Å) / α-NPD (200 Å) / CBP: 7 wt% Ir (ppy) 3 (300 Å) / BCP (100 Å) / Alq 3 (200 Å) / LiF (5 Å) / Al ]
デバイス１〜３は、本発明の有機ＥＬ素子であり、
デバイス４は比較例の有機ＥＬ素子である。
また、前記素子構成中のＴＰＤＰＥＳ、ＴＢＰＡＨ、α−ＮＰＤ、Ｉｒ（ｐｐｙ）３、ＢＣＰ、ＣＢＰ、Ａｌｑ３は下記のとおりである。
ＴＰＤＰＥＳは、ポリ〔オキシ−１，４−フェニレンスルホニル−１，４−フェニレンオキシ−１，４−フェニレン（フェニルイミノ）（１，１′−ビフェニル）−４，４′−ジイル（フェニルイミノ）−１，４−フェニレン〕{ｐｏｌｙ〔ｏｘｙ−１，４−ｐｈｅｎｙｌｅｎｓｕｌｆｏｎｙｌ−１,４−ｐｈｅｎｙｌｅｎｅｏｘｙ−１，４−ｐｈｅｎｙｌｅｎｅ)（ｐｈｅｎｙｌｉｍｉｎｏ）（１，１′−ｂｉｐｈｅｎｙｌ）−４，４′−ｄｉｙｌ（ｐｈｅｎｙｌｉｍｉｎｏ）−１，４−ｐｈｅｎｙｌｅｎｅ〕}（９ＣＩ）（ＣＡ ＩＮＤＥＸ ＮＡＭＥ）の略称である。
ＴＢＰＡＨはトリス（４−ブロモフェニル）アミニウム ヘキサクロロアンチモネート〔Ｔｒｉｓ（４−ｂｒｏｍｏｐｈｅｎｙｌ）ａｍｉｎｉｕｍ ｈｅｘａｃｈｌｏｒｏａｎｔｉｍｏｎａｔｅ〕である。
α−ＮＰＤ〔Ｎ，Ｎ′−ジフェニル−Ｎ，Ｎ′−ジ（１−ナフチル）ベンジジン〕
Further, TPDPES, TBPAH, α-NPD, Ir (ppy) 3 , BCP, CBP, and Alq 3 in the device structure are as follows.
TPDPES is a poly [oxy-1,4-phenylenesulfonyl-1,4-phenyleneoxy-1,4-phenylene (phenylimino) (1,1'-biphenyl) -4,4'-diyl (phenylimino)- 1,4-phenylene] {poly [oxy-1,4-phenylsulfonyl-1,4-phenylene-1,4-phenylene) (phenylimino) (1,1′-biphenyl) -4,4′-diyl (phenylimino) -1,4-phenylene]} (9CI) (CA INDEX NAME).
TBPAH is tris (4-bromophenyl) aminium hexachloroantimonate [Tris (4-bromophenyl) aminium hexachloroantimonate].
α-NPD [N, N′-diphenyl-N, N′-di (1-naphthyl) benzidine]
各有機ＥＬ素子の各層は下記のとおりの役目を果たすものである。
ＩＴＯ：陽極
ＴＰＤＰＥＳ：ＴＢＰＡＨ：ホール注入層（バッファー層）
３ＤＰＡ２ＭＢＮ，３ＤＴＡ２ＭＢＮ，Ｈ８−３ＤＴＡ２ＭＢＮ，α−ＮＰＤ
：ホール輸送層
ＣＢＰ：７ｗｔ％Ｉｒ（ｐｐｙ）３：発光層
ＢＣＰ：ホールブロック層
Ａｌｑ３：電子輸送層
ＬｉＦ：電子注入層
Ａｌ：背面電極
Each layer of each organic EL element fulfills the following role.
ITO: anode TPDPES: TBPAH: hole injection layer (buffer layer)
3DPA2MBN, 3DTA2MBN, H 8 -3DTA2MBN, α-NPD
: Hole transport layer CBP: 7 wt% Ir (ppy) 3 : light emitting layer BCP: hole block layer Alq 3 : electron transport layer LiF: electron injection layer Al: back electrode
（１）デバイス１の製造条件
ＴＰＤＰＥＳ／１０ｗｔ％ＴＢＰＡＨ ｉｎ １，２−ジクロロエタン
：スピンコート（１５００ｒｐｍ，１０ｓｅｃ）
３ＤＰＡ２ＭＢＮ：真空度４．４×１０−６ｔｏｒｒ，蒸着速度３−４Å／ｓｅｃ
Ｉｒ（ｐｐｙ）３：真空度３．９×１０−６ｔｏｒｒ，蒸着速度３５Å／１００ｓｅｃ
ＣＢＰ：真空度３．６×１０−６ｔｏｒｒ，蒸着速度５Å／ｓｅｃ
ＢＣＰ：真空度３．６×１０−６ｔｏｒｒ，蒸着速度２−３Å／ｓｅｃ
Ａｌｑ３：真空度４．５×１０−６ｔｏｒｒ，蒸着速度３−４Å／ｓｅｃ
ＬｉＦ：真空度１．８×１０−５ｔｏｒｒ，蒸着速度２Å／ｓｅｃ
Ａｌ：真空度３．０×１０−５ｔｏｒｒ，蒸着速度１０−１１Å／ｓｅｃ
(1) Manufacturing conditions of device 1 TPDPES / 10 wt% TBPAH in 1,2-dichloroethane
: Spin coating (1500 rpm, 10 sec)
3DPA2MBN: Degree of vacuum 4.4 × 10 −6 torr, deposition rate 3-4 Å / sec
Ir (ppy) 3 : Degree of vacuum 3.9 × 10 −6 torr, vapor deposition rate 35 Å / 100 sec
CBP: Degree of vacuum 3.6 × 10 −6 torr,
BCP: Degree of vacuum 3.6 × 10 −6 torr, deposition rate 2-3 Å / sec
Alq 3 : Degree of vacuum 4.5 × 10 −6 torr, vapor deposition rate 3-4 Å / sec
LiF: Degree of vacuum 1.8 × 10 −5 torr,
Al: Degree of vacuum 3.0 × 10 −5 torr,
（２）デバイス２の製造条件
ＴＰＤＰＥＳ／１０ｗｔ％ＴＢＰＡＨ ｉｎ １，２−ジクロロエタン
：スピンコート（１５００ｒｐｍ，１０ｓｅｃ）
３ＤＴＡ２ＭＢＮ：真空度５．２×１０−６ｔｏｒｒ，蒸着速度３−４Å／ｓｅｃ
Ｉｒ（ｐｐｙ）３：真空度４．５×１０−６ｔｏｒｒ，蒸着速度３５Å／１００ｓｅｃ
ＣＢＰ：真空度４．５×１０−６ｔｏｒｒ，蒸着速度４−５Å／ｓｅｃ
ＢＣＰ：真空度４．１×１０−６ｔｏｒｒ，蒸着速度３−４Å／ｓｅｃ
Ａｌｑ３：真空度５．２×１０−６ｔｏｒｒ，蒸着速度３−４Å／ｓｅｃ
ＬｉＦ：真空度１．７×１０−５ｔｏｒｒ，蒸着速度１−２Å／ｓｅｃ
Ａｌ：真空度３．０×１０−５ｔｏｒｒ，蒸着速度１０−１１Å／ｓｅｃ
(2) Manufacturing condition of
: Spin coating (1500 rpm, 10 sec)
3DTA2MBN: Degree of vacuum 5.2 × 10 −6 torr, vapor deposition rate 3-4 Å / sec
Ir (ppy) 3 : Degree of vacuum 4.5 × 10 −6 torr, deposition rate 35 Å / 100 sec
CBP: Degree of vacuum 4.5 × 10 −6 torr, deposition rate 4-5 Å / sec
BCP: Degree of vacuum 4.1 × 10 −6 torr, deposition rate 3-4 Å / sec
Alq 3 : Degree of vacuum 5.2 × 10 −6 torr, vapor deposition rate 3-4 Å / sec
LiF: degree of vacuum 1.7 × 10 −5 torr, vapor deposition rate 1-2 Å / sec
Al: Degree of vacuum 3.0 × 10 −5 torr,
（３）デバイス３の製造条件
ＴＰＤＰＥＳ／１０ｗｔ％ＴＢＰＡＨ ｉｎ １，２−ジクロロエタン
：スピンコート（１５００ｒｐｍ，１０ｓｅｃ）
Ｈ８−３ＤＴＡ２ＭＢＮ：真空度５．６×１０−６ｔｏｒｒ，蒸着速度２−３Å／ｓｅｃ
Ｉｒ（ｐｐｙ）３：真空度５．０×１０−６ｔｏｒｒ，蒸着速度３５Å／１００ｓｅｃ
ＣＢＰ：真空度５．０×１０−６ｔｏｒｒ，蒸着速度４−５Å／ｓｅｃ
ＢＣＰ：真空度４．７×１０−６ｔｏｒｒ，蒸着速度３Å／ｓｅｃ
Ａｌｑ３：真空度５．０×１０−６ｔｏｒｒ，蒸着速度３Å／ｓｅｃ
ＬｉＦ：真空度２．０×１０−５ｔｏｒｒ，蒸着速度２Å／ｓｅｃ
Ａｌ：真空度２．５×１０−５ｔｏｒｒ，蒸着速度１０−１１Å／ｓｅｃ
(3) Manufacturing conditions of device 3 TPDPES / 10 wt% TBPAH in 1,2-dichloroethane
: Spin coating (1500 rpm, 10 sec)
H 8 -3DTA2MBN: Degree of vacuum 5.6 × 10 −6 torr, vapor deposition rate 2-3 Å / sec
Ir (ppy) 3 : Degree of vacuum 5.0 × 10 −6 torr, vapor deposition rate 35 Å / 100 sec
CBP: Degree of vacuum 5.0 × 10 −6 torr, deposition rate 4-5 Å / sec
BCP: Degree of vacuum 4.7 × 10 −6 torr, deposition rate 3 Å / sec
Alq 3 : degree of vacuum 5.0 × 10 −6 torr, vapor deposition rate 3 Å / sec
LiF: Degree of vacuum 2.0 × 10 −5 torr,
Al: degree of vacuum 2.5 × 10 −5 torr,
（４）デバイス４の製造条件
ＴＰＤＰＥＳ／１０ｗｔ％ＴＢＰＡＨ ｉｎ １，２−ジクロロエタン
：スピンコート（１５００ｒｐｍ，１０ｓｅｃ）
α−ＮＰＤ：真空度４．３×１０−６ｔｏｒｒ，蒸着速度２Å／ｓｅｃ
Ｉｒ（ｐｐｙ）３：真空度３．８×１０−６ｔｏｒｒ，蒸着速度３５Å／１００ｓｅｃ
ＣＢＰ：真空度３．８×１０−６ｔｏｒｒ，蒸着速度５Å／ｓｅｃ
ＢＣＰ：真空度３．５×１０−６ｔｏｒｒ，蒸着速度２−３Å／ｓｅｃ
Ａｌｑ３：真空度３．９×１０−６ｔｏｒｒ，蒸着速度３−４Å／ｓｅｃ
ＬｉＦ：真空度１．７×１０−５ｔｏｒｒ，蒸着速度１−２Å／ｓｅｃ
Ａｌ：真空度３．０×１０−５ｔｏｒｒ，蒸着速度１０−１１Å／ｓｅｃ
(4) Manufacturing condition of
: Spin coating (1500 rpm, 10 sec)
α-NPD: Degree of vacuum 4.3 × 10 −6 torr,
Ir (ppy) 3 : Degree of vacuum 3.8 × 10 −6 torr, vapor deposition rate 35 Å / 100 sec
CBP: Degree of vacuum 3.8 × 10 −6 torr,
BCP: Degree of vacuum 3.5 × 10 −6 torr, deposition rate 2-3 Å / sec
Alq 3 : Degree of vacuum 3.9 × 10 −6 torr, vapor deposition rate 3-4 Å / sec
LiF: degree of vacuum 1.7 × 10 −5 torr, vapor deposition rate 1-2 Å / sec
Al: Degree of vacuum 3.0 × 10 −5 torr,
すなわち、１００ｃｄ／ｍ２当りの電力効率の項をみてもα−ＮＰＤは３２．８（ｌｍ／Ｗ）であるのに対し、３ＤＴＡ２ＭＢＮは３９．０（ｌｍ／Ｗ）、Ｈ８−３ＤＴＡ２ＭＢＮは３７．０（ｌｍ／Ｗ）であり、これらはα−ＮＰＤを超えている。
That is, α-NPD is 32.8 (lm / W) in terms of power efficiency per 100 cd / m 2 , whereas 3DTA2MBN is 39.0 (lm / W) and H 8 -3DTA2MBN is 37. 0.0 (lm / W), which exceeds α-NPD.
各素子の電流の入りやすさはα−ＮＰＤと３ＤＴＡ２ＭＢＮはほぼ同等であり、以下Ｈ８−３ＤＴＡ２ＭＢＮ、３ＤＰＡ２ＭＢＮの順であった。３ＤＴＡ２ＭＢＮおよびＨ８−３ＤＴＡ２ＭＢＮを用いた素子はα−ＮＰＤを用いた素子にくらべ効率が高いことがわかる。 The easiness of input of current in each element was almost the same between α-NPD and 3DTA2MBN, and in the order of H 8 -3DTA2MBN and 3DPA2MBN. It can be seen that the device using 3DTA2MBN and H 8 -3DTA2MBN has higher efficiency than the device using α-NPD.
ビナフチル誘導体よりなるホール輸送材料を用いた緑色リン光素子はバッファー層を導入しない場合、ホール輸送層にα−ＮＰＤを用いた場合よりも電流が入っていかず高電圧駆動し、効率も低いことがわかっている。これはビナフチル系ホール輸送材料のホール注入性が低いためであると考えられる。そこでバッファー層を導入し同様にα−ＮＰＤとの比較をおこなったところ、３ＤＴＡ２ＭＢＮとＨ８−３ＤＴＡ２ＭＢＮにおいてα−ＮＰＤよりも効率が向上した。このことからこれらの材料がＩｒ（ｐｐｙ）３の発光にもとづく三重項励起子の移動を効率的に抑制しているものと考えられる。さらに３ＤＴＡ２ＭＢＮはＮＰＤ並みに電流が入っていっており、ホール注入性は低いもののα−ＮＰＤと同等のホール輸送性を有していると考えられる。またホール輸送性は各材料のイオン化ポテンシャルの順と一致しており、３ＤＴＡ２ＭＢＮ＞Ｈ８−３ＤＴＡ２ＭＢＮ＞３ＤＰＡ２ＭＢＮであることがわかった。３ＤＴＡ２ＭＢＮと３ＤＰＡ２ＭＢＮの比較よりアリールアミン系ではジフェニルアミンよりもジトリルアミンを有する方がホール輸送性を有していると言える。 When a green phosphorescent device using a hole transport material made of a binaphthyl derivative is not introduced with a buffer layer, it is driven at a higher voltage and has a lower efficiency than the case where α-NPD is used for the hole transport layer know. This is considered to be because the hole injection property of the binaphthyl-based hole transport material is low. Therefore, when a buffer layer was introduced and compared with α-NPD in the same manner, the efficiency of 3DTA2MBN and H 8 -3DTA2MBN was improved as compared with α-NPD. From this, it is considered that these materials efficiently suppress the movement of triplet excitons based on the emission of Ir (ppy) 3 . Further, 3DTA2MBN contains a current similar to that of NPD, and although it has a low hole injection property, it is considered to have a hole transport property equivalent to that of α-NPD. The hole transporting are consistent with the order of the ionization potential of the material was found to be 3DTA2MBN> H 8 -3DTA2MBN> 3DPA2MBN. From the comparison of 3DTA2MBN and 3DPA2MBN, it can be said that the arylamine system has a hole transporting property rather than diphenylamine.
Claims (10)
で示されるビナフチル誘導体。 The following general formula (1)
A binaphthyl derivative represented by:
で示されるカルバゾリル基である請求項２記載のビナフチル誘導体。 The heteroaryl group has the following formula (2)
The binaphthyl derivative according to claim 2, which is a carbazolyl group represented by the formula:
The organic EL device according to claim 9, wherein a phosphorescent material exhibiting blue light emission whose emission peak wavelength is shorter than 480 nm is used as a light emitting material.
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