TWI408209B - Organic electroluminescent element materials and organic electroluminescent devices using the same - Google Patents
Organic electroluminescent element materials and organic electroluminescent devices using the same Download PDFInfo
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- TWI408209B TWI408209B TW096119810A TW96119810A TWI408209B TW I408209 B TWI408209 B TW I408209B TW 096119810 A TW096119810 A TW 096119810A TW 96119810 A TW96119810 A TW 96119810A TW I408209 B TWI408209 B TW I408209B
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- 239000000463 material Substances 0.000 title claims description 103
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 238000005401 electroluminescence Methods 0.000 claims abstract description 23
- 239000010409 thin film Substances 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims description 131
- 125000004432 carbon atom Chemical group C* 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 23
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 230000004888 barrier function Effects 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 150000003974 aralkylamines Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 229910052734 helium Inorganic materials 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical group [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 230000007547 defect Effects 0.000 abstract description 8
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- -1 tris(8-quinolinol) aluminum Chemical compound 0.000 description 324
- 239000010410 layer Substances 0.000 description 128
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 238000000434 field desorption mass spectrometry Methods 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 18
- 230000032258 transport Effects 0.000 description 17
- 238000005259 measurement Methods 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000007740 vapor deposition Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 10
- 229910052707 ruthenium Inorganic materials 0.000 description 10
- 239000012267 brine Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 238000000859 sublimation Methods 0.000 description 7
- 230000008022 sublimation Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 239000012327 Ruthenium complex Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 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 5
- 230000002950 deficient Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 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 4
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- XIPZIJBBZXOVGJ-UHFFFAOYSA-N ClC(C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl)CCCCCCCC Chemical compound ClC(C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl)CCCCCCCC XIPZIJBBZXOVGJ-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 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
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910018068 Li 2 O Inorganic materials 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- OPTDDWCXQQYKGU-UHFFFAOYSA-N diphenyldichloromethane Chemical compound C=1C=CC=CC=1C(Cl)(Cl)C1=CC=CC=C1 OPTDDWCXQQYKGU-UHFFFAOYSA-N 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 208000027386 essential tremor 1 Diseases 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 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
- 239000011368 organic material Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- YCEZZDNWLVQCRU-UHFFFAOYSA-N 1,2-diaminoethyl Chemical group N[CH]CN YCEZZDNWLVQCRU-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- HIHYAKDOWUFGBK-UHFFFAOYSA-N 1,3-dibromo-5-phenylbenzene Chemical group BrC1=CC(Br)=CC(C=2C=CC=CC=2)=C1 HIHYAKDOWUFGBK-UHFFFAOYSA-N 0.000 description 2
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 125000006083 1-bromoethyl group Chemical group 0.000 description 2
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- 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 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 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 2
- 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 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
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- 229960005286 carbaryl Drugs 0.000 description 1
- 150000001716 carbazoles Chemical group 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- CSLSCVHILGCSTE-UHFFFAOYSA-N dibenzothiophen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3SC2=C1 CSLSCVHILGCSTE-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002541 furyl group Chemical group 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LNIGFYSAOIMZNA-UHFFFAOYSA-N n,n-dimethylbenzenecarboximidamide Chemical compound CN(C)C(=N)C1=CC=CC=C1 LNIGFYSAOIMZNA-UHFFFAOYSA-N 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical group C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- KELCFVWDYYCEOQ-UHFFFAOYSA-N phenanthridin-1-ol Chemical compound C1=CC=CC2=C3C(O)=CC=CC3=NC=C21 KELCFVWDYYCEOQ-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000005381 potential energy Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical group [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical group C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Description
本發明係關於有機電致發光元件用材料及使用其之有機電致發光元件，尤其是關於發光效率高，無像素缺陷，耐熱性優異，長壽命之有機電致發光元件及實現其之有機電致發光元件用材料。
有機電致發光元件(以下，電致發光簡稱為EL)，係藉由電場之外加，藉由自陽極注入之電洞與自陰極注入之電子之再結合能量，利用螢光性物質之發光原理的自發光元件者。自伊士曼．柯達公司之C.W.Tang等人所提出層合型元件所致低電壓驅動有機EL元件之報告(C.W.Tang,S.A.Vanslyke，應用物理論壇(Applied Physics Letters)，51卷，913頁，1987年等)發表以來，關於使有機材料作為構成材料之有機EL元件的研究正盛行著。Tang等人，係使三(8－喹啉酚根)鋁在發光層，將三苯基二胺衍生物使用於電洞輸送層。在層合構造之優點方面，可例舉對發光層之電洞注入效率提高者，將陰極所注入之電子予以阻塞藉由再結合使生成之激發子生成效率提高者，使發光層內生成之激發子閉鎖者等。如該例之方式，在有機EL元件之元件構造方面，有電洞輸送(注入)層，電子輸送發光層之2層型，或電洞輸送(注入)層，發光層，電子輸送(注入)層之3層型等為周知。在此等層合型構造元件，為提高所注入之電洞與電子之再結合效率，故對元件構造或形成方法下極大的工夫。
有機EL元件之發光材料方面有三(8－喹啉酚根)鋁錯合物等鉗合錯合物，香豆素衍生物，四苯基丁二烯衍生物，雙苯乙烯基伸芳基衍生物，噁二唑衍生物等發光材料為周知，由該等可獲得自藍色至紅色為止之可視區域之發光則有報告被發表，而可期待彩色顯示元件之實現(例如，專利文獻1，專利文獻2，專利文獻3等)。
又，近年來，在有機EL元件之發光層除了螢光材料以外，亦有利用磷光材料者被提案出(參照例如，非專利文獻1，非專利文獻2)。如此，在有機EL元件之發光層中利用有機磷光材料之激發狀態之一重態狀態與三重態狀態，可達成高度發光效率。吾人認為在有機EL元件內在電子與電洞再結合之際因旋轉多重度之差異使得一重態激發子與三重態激發予以1：3之比率產生，故吾人認為在使用磷光性發光材料時，與僅使用螢光之元件比較可達成3~4倍之發光效率。
此種有機EL元件中，為使3重態之激發狀態或3重態之激發子不致消光則使用以陽極，電洞輸送層，有機發光層，電子輸送層(電洞阻止層)，電子輸送層，陰極之順序使層層合之構成，而在有機發光層則有使用主材料與磷光發光性之化合物(例如，專利文獻4~8)。在此有記載具有二苯并呋喃，二苯并噻吩骨架之主材料。但是，與其他咔唑基骨架比較在元件性能並無顯示優越性，即使在矽，鍺原子之組合中亦無任何記載。
又，在專利文獻9及10，雖有記載芳基甲矽烷基等具有取代基之化合物，但並無本發明般之化合物群之記載，在可廣泛保持3重態之能量間隙等，有機EL元件用材料，尤其是作為藍色系磷光元件用材料為有用的效果亦無記載。
進而，在專利文獻11~18，有記載芳基矽烷，芳基鍺烷(germane)系化合物，作為藍色系磷光元件之主材料雖有實施例之記載，但關於本發明般之化合物群則無記載，效果亦不明。
專利文獻1：日本特開平8－239655號公報專利文獻2：日本特開平7－138561號公報專利文獻3：日本特開平3－200889號公報專利文獻4：國際公開WO05/101912號公報專利文獻5：日本特開平5－109485號公報專利文獻6：日本特開2004－002351號公報專利文獻7：國際公開WO04/096945號公報專利文獻8：日本特開2002－308837號公報專利文獻9：日本特開2003－138251號公報專利文獻10二日本特開2000－351966號公報專利文獻11：國際公開WO04/095598號公報專利文獻12：US2004－209115號公報專利文獻13：日本特開2004－103463號公報專利文獻14：日本特開2005－183303號公報專利文獻15：日本特開2005－317275號公報專利文獻16：日本特開2004－200104號公報專利文獻17：日本特開2005－310672號公報專利文獻18：日本特開2005－306864號公報
非專利文獻1：D.F.O'Brien and M.A.Baldo et al."Improved energy transfering electrophosphorescent devices" Applied Physics letters Vol.74 No.3,pp442－444,January 18,1999非專利文獻2：M.A.Baldo et al."Very high－efficiency green organic light－emitting devices based on electrophosphorescence" Applied Physics letters Vol.75 No.1,pp4－6,July 5,1999
本發明係為解決前述課題而完成者，其目的在於提供一種，發光效率高，無像素缺陷，耐熱性優異，長壽命之有機EL元件及實現該等之有機EL元件用材料。
本發明人等為達成該目的經一再重覆戮力研究，結果首先發現將下述一般式(1)或(2)所記載之化合物作為有機EL元件材料使用，而可獲得無像素缺陷，高效率，高耐熱且長壽命之有機EL元件，因而得以本發明來解決。
亦即，本發明係提供一種下述一般式(1)或(2)所示之化合物所成有機EL元件用材料。
本發明係提供一種下述一般式(1)所示之化合物所成有機電致發光元件用材料。
X係硫原子，氧原子，SiRa
Rb
所示之取代矽原子或GeRc
Rd
所示之取代鍺原子，Ra
，Rb
，Rc
及Rd
係，各自獨立示，可具有取代基之碳數1~40之烷基或可具有取代基之碳數6~20之芳基。]
X，L及Z同一般式(1)，Y同一般式(1)之Y1
~Y3
。n為1~4之整數。]
又，本發明係提供一種，在陰極與陽極間夾持至少具有發光層一層或複數層所成有機薄膜層之有機EL元件中，該有機薄膜層之至少一層含有該有機EL元件用材料之有機EL元件。
在使用本發明一般式(1)或(2)所示之化合物所成有機EL元件用材料時，可獲得發光效率高，無像素缺陷，耐熱性優異，且壽命長的有機EL元件。
本發明之有機EL元件用材料係由下述一般式(1)或(2)所示之化合物所成。
首先，就一般式(1)所示之化合物加以說明。
一般式(1)中，R1
~R8
係各自獨立，示氫原子，鹵原子，可具有取代基之碳數1~40之烷基，可具有取代基之碳數3~20之雜環基，可具有取代基之碳數1~40之烷氧基，可具有取代基之碳數6~40之非縮合芳基，可具有取代基之碳數6~12之縮合芳基，可具有取代基之碳數6~20之芳氧基，可具有取代基之碳數7~20之芳烷基，可具有取代基之碳數2~40之鏈烯基，可具有取代基之1~40之烷基胺基，可具有取代基之碳數7~60之芳烷胺基，可具有取代基之碳數3~20之烷基甲矽烷基，可具有取代基之碳數8~40之芳基甲矽烷基，可具有取代基之碳數8~40之芳烷甲矽烷基，可具有取代基之碳數3~20之烷基鍺基，可具有取代基之碳數8~4o之芳基鍺基，可具有取代基之碳數8~40之芳烷鍺基，可具有取代基之碳數7~40之酮芳基，可具有取代基之碳數1~40之鹵化烷基，氰基或下述一般式(a)所示之構造，R1
~R8
中至少一個係下述一般式(a)所示構造。
該鹵原子方面，可例舉例如氟，氯，溴，碘等。
該烷基方面，可例舉例如甲基，乙基，丙基，異丙基，正丁基，二級丁基，異丁基，三級丁基，正戊基，正己基，正庚基，正辛基，正壬基，正癸基，正十一基，正十二基，正十三基，正十四基，正十五基，正十六基，正十七基，正十八基，新戊基，1－甲基戊基，2－甲基戊基，1－戊基己基，1－丁基戊基，1－庚基辛基，3－甲基戊基，羥基甲基，1－羥基乙基，2－羥基乙基，2－羥基異丁基，1,2－二羥基乙基，1,3－二羥基異丙基，2,3－二羥基－三級丁基，1,2,3－三羥基丙基，氯甲基，1－氯乙基，2－氯乙基，2－氯異丁基，1,2－二氯乙基，1,3－二氯異丙基，2,3－二氯－三級丁基，1,2,3－三氯丙基，溴甲基，1－溴乙基，2－溴乙基，2－溴異丁基，1,2－二溴乙基，1,3－二溴異丙基，2,3－二溴－三級丁基，1,2,3－三溴丙基，碘甲基，1－碘乙基，2－碘乙基，2－碘異丁基，1,2－二碘乙基，1,3－二碘異丙基，2,3－二碘－三級丁基，1,2,3－三碘丙基，胺基甲基，1－胺基乙基，2－胺基乙基，2－胺基異丁基，1,2－二胺基乙基，1,3－二胺基異丙基，2,3－二胺基－三級丁基，1,2,3－三胺基丙基，氰甲基，1－氰乙基，2－氰乙基，2－氰異丁基，1,2－二氰乙基，1,3－二氰異丙基，2,3－二氰－三級丁基，1,2,3－三氰丙基，硝基甲基，1－硝基乙基，2－硝基乙基，1,2－二硝基乙基，2,3－二硝基－三級丁基，1,2,3－三硝基丙基，環戊基，環己基，環辛基，3,5－四甲基環己基等。
該等中較佳為甲基，乙基，丙基，異丙基，正丁基，二級丁基，異丁基，三級丁基，正戊基，正己基基，正庚基，正辛基，正壬基，正癸基基，正十一基基，正十二基，正十三基，正十四基，正十五基，正十六基，正十七基，正十八基，新戊基，1－甲基戊基，1－戊基己基，1－丁基戊基，1－庚基辛基，環己基，環辛基，3,5－四甲基環己基。
該雜環基方面，可例舉例如1－吡咯基，2－吡咯基，3－吡咯基，吡嗪基，2－吡啶基，1－咪唑基，2－咪唑基，1－吡唑基，1－吲哚嗪(indolizinyl)基，2－吲哚嗪基，3－吲哚嗪基，5－吲哚嗪基，6－吲哚嗪基，7－吲哚嗪基，8－吲哚嗪基，2－咪唑并吡啶基，3－咪唑并吡啶基，5－咪唑并吡啶基，6－咪唑并吡啶基，7－咪唑并吡啶基，8－咪唑并吡啶基，3－吡啶基，4－吡啶基，1－吲哚基，2－吲哚基，3－吲哚基，4－吲哚基，5－吲哚基，6－吲哚基，7－吲哚基，1－異吲哚基，2－異吲哚基，3－異吲哚基，4－異吲哚基，5－異吲哚基，6－異吲哚基，7－異吲哚基，2－呋喃基，3－呋喃基，2－苯并呋喃基，3－苯并呋喃基，4－苯并呋喃基，5－苯并呋喃基，6－苯并呋喃基，7－苯并呋喃基，1－異苯并呋喃基，3－異苯并呋喃基，4－異苯并呋喃基，5－異苯并呋喃基，6－異苯并呋喃基，7－異苯并呋喃基，2－喹啉基，3－喹啉基，4－喹啉基，5－喹啉基，6－喹啉基，7－喹啉基，8－喹啉基，1－異喹啉基，3－異喹啉基，4－異喹啉基，5－異喹啉基，6－異喹啉基，7－異喹啉基，8－異喹啉基，2－喹喔啉基，5－喹喔啉基，6－喹喔啉基，1－咔唑基，2－咔唑基，3－咔唑基，4－咔唑基，9－咔唑基，β－咔啉(carboline)－1－基，β－咔啉－3－基，β－咔啉－4－基，β－咔啉－5－基，β咔啉－6－基，β－咔啉－7－基，β－咔啉－6－基，β－咔啉－9－基，1－菲啶基，2－菲啶基，3－菲啶基，4－菲啶基，6－菲啶基，7－菲啶基，8－菲啶基，9－菲啶基，10－菲啶基，1－吖啶基，2－吖啶基，3－吖啶基，4－吖啶基，9－吖啶基，1,7－菲繞啉－2－基，1,7－菲繞啉－3－基，1,7－菲繞啉－4－基，1,7－菲繞啉－5－基，1,7－菲繞啉－6－基，1,7－菲繞啉－8－基，1,7－菲繞啉－9－基，1,7－菲繞啉－10－基，1,8－菲繞啉－2－基，1,8－菲繞啉－3－基，1,8－菲繞啉－4－基，1,8－菲繞啉－5－基，1,8－菲繞啉－6－基，1,8－菲繞啉－7－基，1,8－菲繞啉－9－基，1,8－菲繞啉－10－基，1,9－菲繞啉－2－基，1,9－菲繞啉－3－基，1,9－菲繞啉－4－基，1,9－菲繞啉－5－基，1,9－菲繞啉－6－基，1,9－菲繞啉－7－基，1,9－菲繞啉－8－基，1,9－菲繞啉－10－基，1,10－菲繞啉－2－基，1,10－菲繞啉－3－基，1,10－菲繞啉－4－基，1,10－菲繞啉－5－基，2,9－菲繞啉－1－基，2,9－菲繞啉－3－基，2,9－菲繞啉－4－基，2,9－菲繞啉－5－基，2,9－菲繞啉－6－基，2,9－菲繞啉－7－基，2,9－菲繞啉－8－基，2,9－菲繞啉－10－基，2,8－菲繞啉－1－基，2,8－菲繞啉－3－基，2,8－菲繞啉－4－基，2,8－菲繞啉－5－基，2,8－菲繞啉－6－基，2,8－菲繞啉－7－基，2,8－菲繞啉－9－基，2,8－菲繞啉－10－基，2,7－菲繞啉－1－基，2,7－菲繞啉－3－基，2,7－菲繞啉－4－基，2,7－菲繞啉－5－基，2,7－菲繞啉－6－基，2,7－菲繞啉－8－基，2,7－菲繞啉－9－基，2,7－菲繞啉－10－基，1－吩嗪基，2－吩嗪基，1－啡噻基，2－啡噻基，3－啡噻基，4－啡噻基，10－啡噻基，1－吩噁嗪基，2－吩噁嗪基，3－吩噁嗪基，4－吩噁嗪基，10－吩噁嗪基，2－噁唑基，4－噁唑基，5－噁唑基，2－噁二唑基，5－噁二唑基，3－呋咱基，2－噻吩基，3－噻吩基，2－甲基吡咯－1－基，2－甲基吡咯－3－基，2－甲基吡咯－4－基，2－甲基吡咯－5－基，3－甲基吡咯－1－基，3－甲基吡咯－2－基，3－甲基吡咯－4－基，3－甲基吡咯－5－基，2－三級丁基吡咯－4－基，3－(2－苯基丙基)吡咯－1－基，2－甲基－1－吲哚基，4－甲基－1－吲哚基，2－甲基－3－吲哚基，4－甲基－3－吲哚基，2－三級丁基1－吲哚基，4－三級丁基1－吲哚基，2－三級丁基3－吲哚基，4－三級丁基3－吲哚基，1－二苯并呋喃基，2－二苯并呋喃基，3－二苯并呋喃基，4－二苯并呋喃基，1－二苯并噻吩基，2－二苯并噻吩基，3－二苯并噻吩基，4－二苯并噻吩基，1－矽烷基芴基，2－矽烷基芴基，3－矽烷基芴基，4－矽烷基芴基，1－鍺烷基芴基，2－鍺烷基芴基，3－鍺烷基芴基，4－鍺烷基芴基等。
該等中較佳為2－吡啶基，1－吲哚嗪基，2－吲哚嗪基，3－吲哚嗪基，5－吲哚嗪基，6－吲哚嗪基，7－吲哚嗪基，8－明哚嗪基，2－咪唑并吡啶基，3－咪唑并吡啶基，5－咪唑并吡啶基，6－咪唑并吡啶基，7－咪唑并吡啶基，8－咪唑并吡啶基，3－吡啶基，4－吡啶基，1－吲哚基，2－吲哚基，3－吲哚基，4－吲哚基，5－吲哚基，6－吲哚基，7－吲哚基，1－異吲哚基，2－異吲哚基，3－異吲哚基，4－異吲哚基，5－異吲哚基，6－異吲哚基，7－異吲哚基，1－咔唑基，2－咔唑基，3－咔唑基，4－咔唑基，9－咔唑基，1－二苯并呋喃基，2－二苯并呋喃基，3－二苯并呋喃基，4－二苯并呋喃基，1－二苯并噻吩基，2－二苯并噻吩基，3－二苯并噻吩基，4－二苯并噻吩基，1－矽烷基芴基，2－矽烷基芴基，3－矽烷基芴基，4－矽烷基芴基，1－鍺烷基芴基，2－鍺烷基芴基，3－鍺烷基芴基，4－鍺烷基芴基。
該烷氧基係以－OY所示之基，Y之具體例方面，可例舉與以該烷基所說明者相同之物，較佳之例亦同。
該非縮合芳基方面，可例舉例如苯基，2－聯苯基，3－聯苯基，4－聯苯基，對聯三苯基－4－基，對聯三苯基－3－基，對聯三苯基－2－基，間聯三苯基－4－基，間聯三苯基－3－基，間聯三苯基－2－基，鄰甲苯基，間甲苯基，對甲苯基，對三級丁基苯基，對(2－苯基丙基)苯基，4'－甲基聯苯基，4"－三級丁基－對聯三苯基－4－基，鄰異丙苯(cumenyl)基，間異丙苯基，對異丙苯基，2,3－甲苄基(xylyl)，3,4－甲苄基，2,5－甲苄基，基(mesityl)，間四分之一(quarter－)聯三苯基等。
該等中較佳為苯基，2－聯苯基，3－聯苯基，4－聯苯基，間聯三苯基－4－基，間聯三苯基－3－基，間聯三苯基－2－基，對甲苯基，3,4－甲苄基，間四分之一聯三苯基－2－基。
該縮合芳基之例方面，可例舉1－萘基，2－萘基。
該芳氧基係以－OAr表示之基，Ar之具體例方面，可例舉以與該非縮合芳基所說明者相同之物，較佳之例亦同。
該芳烷基方面，可例舉例如苄基，1－苯基乙基，2－苯基乙基，1－苯基異丙基，2－苯基異丙基，苯基－三級丁基，α－萘基甲基，1－α－萘基乙基，2－α－萘基乙基，1－α－萘基異丙基，2－α－萘基異丙基，β－萘基甲基，1－β－萘基乙基，2－β－萘基乙基，1－β－萘基異丙基，2－β－萘基異丙基，1－吡咯甲基，2－(1－吡咯)乙基，對甲基苄基，間甲基苄基，鄰甲基苄基，對氯苄基，間氯苄基，鄰氯苄基，對溴苄基，間溴苄基，鄰溴苄基，對碘苄基，間碘苄基，鄰碘苄基，對羥基苄基，間羥基苄基，鄰羥基苄基，對胺基苄基，間胺基苄基，鄰胺基苄基，對硝基苄基，間硝基苄基，鄰硝基苄基，對氰苄基，間氰苄基，鄰氰苄基，1－羥基－2－苯基異丙基，1－氯－2－苯基異丙基等。
該等中較佳為，苄基，對氰苄基，間氰苄基，鄰氰苄基，1－苯基乙基，2－苯基乙基，1－苯基異丙基，2－苯基異丙基。
該鏈烯基方面，可例舉例如乙烯基，烯丙基，1－丁烯基，2－丁烯基，3－丁烯基，1,3－丁二烯基，1－甲基乙烯基，苯乙烯基，2,2－二苯基乙烯基，1,2－二苯基乙烯基，1－甲基烯丙基，1,1－二甲基烯丙基，2－甲基烯丙基，1－苯基烯丙基，2－苯基烯丙基，3－苯基烯丙基，3,3－二苯基烯丙基，1,2－二甲基烯丙基，1－苯基－1－丁烯基，3－苯基－1－丁烯基等，較佳為，苯乙烯基，2,2－二苯基乙烯基，1,2－二苯基乙烯基等。
該烷基胺基，及可具有取代基之碳數7~60之芳烷胺基，係以－NQ1
Q2
表示，Q1
及Q2
之具體例方面，可例舉各自獨立，與該烷基，該芳基，該芳烷基所說明者相同之物，較佳之例亦同。
該烷基甲矽烷基方面，可例舉例如三甲基甲矽烷基，三乙基甲矽烷基，三級丁基二甲基甲矽烷基，乙烯二甲基甲矽烷基，丙基二甲基甲矽烷基等。該芳基甲矽烷基方面，可例舉例如三苯基甲矽烷基，三聯苯基甲矽烷基，二－聯三苯基－苯基甲矽烷基，苯基二甲基甲矽烷基，三級丁基二苯基甲矽烷基等。
該芳烷甲矽烷基方面，可例舉例如，三苄基甲矽烷基，苄基二甲基甲矽烷基，三級丁基二苄基甲矽烷基等。
該烷基鍺基方面，可例舉例如三甲基鍺基，三乙基鍺基，三級丁基二甲基鍺基，乙烯二甲基鍺基，丙基二甲基鍺基等。
該芳基鍺基方面，可例舉例如三苯基鍺基，三聯苯基鍺基，二－聯三苯基－苯基鍺基，苯基二甲基鍺基，三級丁基二苯基鍺基等。
該芳烷鍺基方面，可例舉例如三苄基鍺基，苄基二甲基鍺基，三級丁基二苄基鍺基等。
該酮芳基係以－COAr2
表示，Ar2
之具體例方面，可例舉與該芳基所說明者相同之物，較佳之例亦同。
該鹵化烷基方面，可例舉例如使該烷基之至少一個氫原子以鹵原子取代之物，較佳之例亦同。
一般式(1)中，X示硫原子，氧原子，以SiRa
Rb
所示之取代矽原子或以GeRc
Rd
所示之取代鍺原子，Ra
，Rb
，Rc
及Rd
係各自獨立，示可具有取代基之碳數1~40之烷基或可具有取代基之碳數6~20之芳基。
Ra
，Rb
，Rc
及Rd
之烷基方面，可例舉與該R1
~R8
之烷基相同之物，較佳為甲基，乙基，丙基及丁基。
Ra
，Rb
，Rc
及Rd
之碳數6~20之芳基方面，可例舉與該R1
~R8
之非縮合芳基相同之物，較佳為苯基，對甲苯基，4－聯苯基。
又，一般式(a)為下述構造。
一般式(a)中，L係單鍵或可具有取代基之碳數1~10之烷撐基，可具有取代基之碳數6~40之非縮合伸芳基，可具有取代基之碳數6~12之縮合伸芳基，可具有取代基之2價碳數3~40之芳香族雜環基。
L之烷撐基方面，可例舉以該R1
~R8
說明之烷基之例作為2價基者，以亞甲基，乙烯基，丙烯基，丁烯基，2價環己烷基，2價金剛烷基，2價降烯基(norbornene)為佳。
L之非縮合伸芳基方面，可例舉以該R1
~R8
說明之非縮合芳基之例作為2價基者，而以伸苯基，對聯伸苯基，間聯伸苯基，鄰聯伸苯基，鄰聯伸三苯基，間聯伸三苯基，對聯伸三苯基之2價基為佳。
L之縮合伸芳基方面，可例舉萘等之2價残基。
L之芳香族雜環基方面，可例舉吡啶，吡嗪，喹啉，嘧啶，三，噻吩，silole，苯并呋喃，苯并噻吩，二苯并呋喃，二苯并噻吩，咔唑，喹啉，呋喃，吡咯，咪唑，吡唑，異噻唑，異噁唑，異喹啉，喹唑啉，喹嗪(quinolizine)，喹喔啉，噌啉，苯并咪唑，咪唑并吡啶，萘叉(naphthylidene)，1,2－苯并異噁唑，苯并噁唑，苯并噻唑，唑并(oxazolo－)吡啶，異噻唑并(isothiazolo－)吡啶，以苯并噻吩基骨架為母骨架之2價残基，以吡啶，吡嗪，喹啉，嘧啶，噻吩，silole，二苯并呋喃，二苯并噻吩，咪唑并吡啶，苯并咪唑骨架為母骨架之2價基為佳。
一般式(a)中，Y1
~Y3
係各自獨立，示可具有取代基之碳數1~10之烷基，可具有取代基之碳數6~20之芳基，可具有取代基之碳數6~30之芳香族雜環基。
Y1
~Y3
之烷基方面，可例舉與該R1
~R8
相同之例。
Y1
~Y3
之芳基方面，可例舉與該R1
~R8
之非縮合芳基及縮合芳基相同之例。
Y1
~Y3
之芳香族雜環基方面，可例舉例如呋喃基，噻吩基，吡咯基，咪唑基，吡唑基，異噻唑基，異唑基，吡啶基，嘧啶基，喹啉基，異喹啉基，喹唑啉基，喹嗪基，喹喔啉基，噌啉基，苯并咪唑基，咪唑并吡啶基，苯并呋喃基，萘叉(naphthylidinyl)基，1,2－苯并異唑基，苯并噁唑基，苯并噻唑基，唑并(oxazolo－)吡啶基，異噻唑并(isothiazolo－)吡啶基，苯并噻吩基等。
一般式(a)中，Z為矽原子或鍺原子。
接著，就一般式(2)所示之化合物加以說明。
一般式(2)中，R11
~R14
及R係各自獨立，示氫原子，鹵原子，可具有取代基之碳數1~40之烷基，可具有取代基之碳數3~20之雜環基，可具有取代基之碳數1~40之烷氧基，可具有取代基之碳數6~40之非縮合芳基，可具有取代基之碳數6~12之縮合芳基，可具有取代基之碳數6~20之芳氧基，可具有取代基之碳數7~20之芳烷基，可具有取代基之碳數2~40之鏈烯基，可具有取代基之1~40之烷基胺基，可具有取代基之碳數7~60之芳烷胺基，可具有取代基之碳數3~20之烷基甲矽烷基，可具有取代基之碳數8~40之芳基甲矽烷基，可具有取代基之碳數8~40之芳烷甲矽烷基，可具有取代基之碳數3~20之烷基鍺基，可具有取代基之碳數8~40之芳基鍺基，可具有取代基之碳數8~40之芳烷鍺基，可具有取代基之碳數7~40之酮芳基，可具有取代基之碳數1~40之鹵化烷基或氰基。
該等各基之具體例方面，可例舉與一般式(1)之R1
~R8
說明之物相同之例。
一般式(2)中，X，L及Z同一般式(1)，Y與一般式(1)之Y1
~Y3
同，具體例及較佳之例亦同。
一般式(2)中，n為1~4之整數，若為2~3時則成為適當的分子量，因可充分滿足昇華性，熱穩定性之兩者故佳。
該一般式(2)所示之化合物，若為下述一般式(3)或(4)所示之化合物時則因製造容易故佳。
一般式(3)及(4)中，R11
~R17
與一般式(2)之R11
~R14
及R同，具體例及較佳之例亦同。又，L，X，Z，Y及n亦同。
一般式(1)~(4)所示各基之取代基方面，可例舉例如烷基(甲基，乙基，丙基，異丙基，正丁基，二級丁基，異丁基，三級丁基，正戊基，正己基基，正庚基，正辛基，羥基甲基，1－羥基乙基，2－羥基乙基，2－羥基異丁基，1,2－二羥基乙基，1,3－二羥基異丙基，2,3－二羥基－三級丁基，1,2,3－三羥基丙基，氯甲基，1－氯乙基，2－氯乙基，2－氯異丁基，1,2－二氯乙基，1,3－二氯異丙基，2,3－二氯－三級丁基，1,2,3－三氯丙基，溴甲基，1－溴乙基，2－溴乙基，2－溴異丁基，1,2－二溴乙基，1,3－二溴異丙基，2,3－二溴三級丁基，1,2,3－三溴丙基，碘甲基，1－碘乙基，2－碘乙基，2－碘異丁基，1,2－二碘乙基，1,3－二碘異丙基，2,3－二碘三級丁基，1,2,3－三碘丙基，胺基甲基，1－胺基乙基，2－胺基乙基，2－胺基異丁基，1,2－二胺基乙基，1,3－二胺基異丙基，2,3－二胺基－三級丁基，1,2,3－三胺基丙基，氰甲基，1－氰乙基，2－氰乙基，2－氰異丁基，1,2－二氰乙基，1,3－二氰異丙基，2,3－二氰－三級丁基，1,2,3－三氰丙基，硝基甲基，1－硝基乙基，2－硝基乙基，2－硝基異丁基，1,2－二硝基乙基，1,3－二硝基異丙基，2,3－二硝基－三級丁基，1,2,3－三硝基丙基，環丙基，環丁基，環戊基，環己基，4－甲基環己基，1－金剛烷基，2－金剛烷基，1－正基，2－正基等)，碳數1~6之烷氧基(乙氧基，甲氧基，異丙氧基，正丙氧基，二級丁氧基，三級丁氧基，戊氧基，己氧基，環戊氧基，環己氧基等)，核原子數5~40之芳基，以核原子數5~40之芳基取代之胺基，具有核原子數5~40之芳基之酯基，具有碳數1~6之烷基之酯基，氰基，硝基，鹵原子等。
本發明之一般式(1)~(4)之任一種所示之化合物所成有機EL元件用材料之具體例係如以下所示，然而並非限定於該等例示化合物。
本發明之有機EL元件用材料，若為含於有機EL元件之發光層之主材料時，則佳。
接著，就本發明之有機EL元件加以說明。
本發明之有機EL元件係，在陰極與陽極間夾持至少具有發光層一層或複數層所成有機薄膜層之有機EL元件中，該有機薄膜層之至少一層含有本發明之有機EL元件用材料。
多層型之有機EL元件之構造方面，可例舉例如，將陽極/電洞輸送層(電洞注入層)/發光層/陰極，陽極/發光層/電子輸送層(電子注入層)/陰極，陽極/電洞輸送層(電洞注入層)/發光層/電子輸送層(電子注入層)/陰極，陽極/電洞輸送層(電洞注入層)/發光層/電洞障壁層/電子輸送層(電子注入層)/陰極，等之多層構成所層合者。
本發明之有機EL元件中，該發光層以含有本發明之有機EL元件用材料作為主材料為佳。又，該發光層係由主材料與磷光性之發光材料所成，該主材料以該有機EL元件用材料為佳。
磷光性之發光材料方面，在磷光量子收率高，發光元件之外部量子效率可更為提高之點而言，以含有銥(Ir),鋨(Os)或鉑(Pt)金屬之化合物為佳，以銥錯合物，鋨錯合物，鉑錯合物等金屬錯合物進而為佳，其中以銥錯合物及鉑錯合物較佳，正金屬化銥錯合物最佳。正金屬化金屬錯合物之進而為佳之形態方面，可例舉以下所示銥錯合物。
又，本發明之有機EL元件，該發光層含有主材料與磷光性之發光材料，該磷光性之發光材料若為具有金屬-碳烯(carbene)碳鍵結之發光材料則為佳。
進而，該發光層以含有最高發光亮度之波長500nm以下之藍色系金屬錯合物為佳，此種藍色系金屬錯合物方面，可例舉例如前述之K-1，K-2，K-3，K-10，K-11，K-12，K-15，K-16及K-17等。
本發明之有機EL元件，具有電洞輸送層(電洞注入層)，該電洞輸送層(電洞注入層)以含有本發明之有機EL元件用材料為佳，本發明之有機EL元件具有電子輸送層(電子注入層)及/或電洞障壁層，該電子輸送層(電子注入層)及/或電洞障壁層以含有本發明之有機EL元件用材料為佳。
電洞注入層係為了自陽極使電洞有效率地注入於有機EL元件內而設之層，可自陽極使電洞和緩地注入於層內，藉此可使驅動電壓降下，而可抑制驅動所致載體平衡(carrier balance)之變化。電洞注入層所使用之材料方面，一般係使用近於陽極金屬之功函數的具有游離電位能量之化合物。可例舉例如芳基胺化合物，銅，銥等各種金屬錯合物，或六氮雜三伸苯基衍生物等。
電洞輸送層係具有，將來自陽極所注入之電洞予以輸送，到達發光層之機能的層。藉由設置電洞輸送層，可在發光層使電洞與電子有效率的再結合，使發光效率提高。因此，在電洞輸送層所使用之材料，則有要求對發光層可有效率地使電洞傳導之機能。一般電洞輸送層所使用之材料方面係使用芳基胺系材料。一般電場強度之乘以二分之一之值在300~800(V/cm)1/2
之範圍可獲得具有10－5
cm2
/Vs以上之電洞移動度之材料為佳。在電洞注入層或電洞輸送層含有本發明之有機EL元件用材料為佳。
電洞障壁層係為使電子與電洞在發光層內效率良好的再結合，而設置於發光層與陰極間之層。在電洞障壁層，係使用以發光層材料之第一氧化電位為大的物質，藉此可防止對電子輸送層之電洞注入。在使用於電洞障壁層之材料方面，可例舉例如專利第2673261號公報記載之電洞阻止層用材料。
電子輸送層，係擔任自陰極所注入之電子予以輸送，到達發光層之機能的層。藉由電子輸送層之設置，在發光層使電洞與電子有效率地再結合，而可提高發光效率者。為有效率的使EL發光，則有必要在發光層有效率的使電子傳導。電子輸送層所使用之材料方面，一般係使用含氮系芳香族化合物材料，或silole化合物等氮以外之雜化合物，或鋁，鎵等之金屬錯合物，或縮合芳香族烴等一般所使用者。此種材料之電子移動度，一般係電場強度之乘以二分之一之值在300~800(V/cm)1/2
之範圍為10－6
cm2
/Vs以上。電子輸送材料方面，可例舉後述之材料為佳。在電子輸送層或電洞障壁層以含有本發明之有機EL元件用材料為佳。
電子注入層係自陰極至有機EL元件內使電子有效率的注入而設置之層。藉由電子注入層之設置，因可自陰極使電子和緩的注入，故可使驅動電壓降下，可抑制驅動所致載體平衡之變化。在構成電子注入層之材料方面，可恰當例舉後述之材料。
本發明之有機EL元件，係在陰極與有機薄膜層之界面區域添加還原性摻雜劑所成者為佳。
該還原性摻雜劑方面，可例舉選自鹼金屬，鹼金屬錯合物，鹼金屬化合物，鹼土類金屬，鹼土類金屬錯合物，鹼土類金屬化合物，稀土類金屬，稀土類金屬錯合物，及稀土類金屬化合物等之至少一種。
該鹼金屬方面，可例舉Na(功函數2.36eV)，K(功函數2.28eV)，Rb(功函數2.16eV)，Cs(功函數1.95eV)等，以功函數2.9eV以下之者特佳。該等中較佳為K，Rb，Cs，進而較佳為Rb或Cs，最佳為Cs。
該鹼土類金屬方面，可例舉Ca(功函數2.9eV)，Sr(功函數：2.0~2.5eV)，Ba(功函數2.52eV)等，以功函數2.9eV以下者特佳。
該稀土類金屬方面，可例舉Sc，Y，Ce，Tb，Yb等，以功函數2.9eV以下者特佳。
以上之金屬中較佳之金屬，尤以還原能力高，對電子注入域之比較少量之添加，可使有機EL元件中發光亮度提高或長壽命化之該鹼金屬化合物方面，可例舉Li2
O，Cs2
O，K2
O等之鹼氧化物，LiF，NaF，CsF，KF等之鹼鹵化物等，以LiF，Li2
O，NaF之鹼氧化物或鹼氟化物為佳。
該鹼土類金屬化合物方面，可例舉BaO，SrO，CaO及混合該等之Bax
Sr1－x
O(0<x<1)，或Bax
Ca1－x
O(0<x<1)等，而以BaO，SrO，CaO為佳。
該稀土類金屬化合物方面，可例舉YbF3
，ScF3
，ScO3
，Y2
O3
，Ce2
O3
，GdF3
，TbF3
等，以YbF3
，ScF3
，TbF3
為佳。
該鹼金屬錯合物，鹼土類金屬錯合物，稀土類金屬錯合物方面，在各金屬離子方面，若為含有鹼金屬離子，鹼土類金屬離子，稀土類金屬離子之至少一種則並無特別限定。又，在配位基以喹啉酚，苯并喹啉酚，吖啶醇(acridinol)，啡啶醇(phenanthridinol)，羥基苯基噁唑，羥基苯基噻唑，羥基二芳基噁二唑，羥基二芳基噻二唑，羥基苯基吡啶，羥基苯基苯并咪唑，羥基苯并三唑，羥基全硼氫化物(full－borane)，聯二吡啶基，菲繞啉，酞菁，卟啉，環戊二烯，β－二酮類，甲亞胺類，及該等之衍生物等為佳，但並非限定於該等。
還原性摻雜劑之添加形態方面，可例舉在該界面區域形成層狀或島狀為佳。形成方法方面，藉由電阻加熱蒸鍍法使還原性摻雜劑一面蒸鍍，一面使形成界面區域之發光材料或為電子注入材料之有機物同時蒸鍍，在有機物中使還原性摻雜劑分散之方法為佳。分散濃度方面以莫耳比為有機物：還原性摻雜劑＝100：1~1：100，較佳為5：1~1：5。
在將還原性摻雜劑形成為層狀之情形，將為界面之有機層之發光材料或電子注入材料形成層狀後，使還原性摻雜劑單獨以電阻加熱蒸鍍法予以蒸鍍，較佳為以層之厚度0.1~15nm形成。
在將還原性摻雜劑形成為島狀之情形，將為界面有機層之發光材料或電子注入材料形成為島狀後，使還原性摻雜劑單獨以電阻加熱蒸鍍法進行蒸鍍，較佳為以島之厚度0.05~1nm形成。
又，在本發明之有機EL元件中，在主成分與還原性摻雜劑之比率方面，以莫耳比主成分：還原性摻雜劑＝5：1~1：5為佳，以2：1~1：2進而為佳。
本發明之有機EL元件，係在該發光層與陰極之間具有電子注入層，該電子注入層含有以含氮環衍生物為主成分時，因與陰極之密接性被提高之分子骨架變多故佳。
在使用於該電子注入層之電子輸送材料方面，以使用分子內含有雜原子1個以上之芳香族雜環化合物為佳，尤其是以含氮環衍生物為佳。
在此含氮環衍生物方面，以例如一般式(A)所示之物為佳。
R2
~R7
係各自獨立，示氫原子，鹵原子，氧基，胺基，或碳數1~40之烴基，該等可具有取代基。
此鹵原子之例方面，可例舉與前述同樣之物。又，具有取代基之胺基之例方面，可例舉與該烷基胺基，芳基胺基，芳烷胺基相同之物。
碳數1~40之烴基方面，可例舉取代或者無取代之烷基，鏈烯基，環烷基，烷氧基，芳基，雜環基，芳烷基，芳氧基，烷氧羰基等。此烷基，鏈烯基，環烷基，烷氧基，芳基，雜環基，芳烷基，芳氧基之例方面，可例舉與該等同樣之物，烷氧羰基係以－COOY'表示，Y'之例方面可例舉與該烷基同樣之物。
M係鋁(Al)，鎵(Ga)或銦(In)，以In為佳。
一般式(A)之L，係下述一般式(A')或(A")所示之基。
一般式(A')及(A")之R8
~R12
及Rl3
~R27
所示之碳數1~40之烴基方面，可例舉與該R2
~R7
之具體例相同之物。
又，該R8
~R12
及R13
~R27
之互為鄰接之基在形成環狀構造情形之2價基方面，可例舉四亞甲基，五亞甲基，亞己基，二苯基甲烷－2,2'－二基，二苯基乙烷－3,3'－二基，二苯基丙烷－4,4'－二基等。
一般式(A)所示之含氮環之金屬鉗合錯合物之具體例係如以下所示，但並非限定於該等之例示化合物。
該含氮環衍生物方面，以含氮5員環衍生物為佳，含氮5員環方面，可例舉咪唑環，三唑環，四唑環，噁二唑環，噻二唑環，氧雜三唑環，噻三唑環等，含氮5員環衍生物方面，則有苯并咪唑環，苯并三唑環，吡啶并咪唑環，嘧啶并咪唑環，嗒并咪唑環，特佳為，下述一般式(B)所示之物。
一般式(B)中，LB
示二價以上之鍵聯基，例如碳，矽，氮，硼，氧，硫，金屬(例如鋇，鈹)，芳香族烴環，芳香族雜環等，該等中以碳原子，氮原子，矽原子，硼原子，氧原子，硫原子，芳基，芳香族雜環基為佳，以碳原子，矽原子，芳基，芳香族雜環基進而為佳。
LB
之芳基及芳香族雜環基可具有取代基，取代基方面較佳為烷基，鏈烯基，炔基，芳基，胺基，烷氧基，芳氧基，醯基，烷氧羰基，芳氧羰基，醯基氧基，醯基胺基，烷氧羰胺基，芳氧羰胺基，磺醯胺基，胺磺醯基，胺甲醯基，烷基硫基，芳基硫基，磺醯基，鹵原子，氰基，芳香族雜環基，更佳為烷基，芳基，烷氧基，芳氧基，鹵原子，氰基，芳香族雜環基，進而較佳為烷基，芳基，烷氧基，芳氧基，芳香族雜環基，特佳為烷基，芳基，烷氧基，芳香族雜環基。
LB
之具體例方面，可舉以下所示者。
一般式(B)中XB2
示－O－，－S－或＝N－RB2
。RB2
示氫原子，脂肪族烴基，芳基或雜環基。
RB2
之脂肪族烴基，有直鏈，分支鏈或環狀之烷基(較佳為碳數1~20，更佳為碳數1~12，特佳為碳數1~8之烷基，可例舉例如甲基，乙基，異丙基，三級丁基，正辛基，正癸基，正十六基，環丙基，環戊基，環己基等。)，鏈烯基(較佳為碳數2~20，更佳為碳數2~12，特佳為碳數2~8之鏈烯基，例如，乙烯，烯丙基，2－丁烯基，3－戊烯基等。)，炔基(較佳為碳數2~20，更佳為碳數2~12，特佳為碳數2~8之炔基，例如，炔丙基(propargyl)，3－戊炔基(pentynyl)等。)，以烷基為佳。
RB2
之芳基係單環或縮合環，較佳為碳數6~30，更佳為碳數6~20，進而較佳為碳數6~12之芳基，例如，苯基，2－甲基苯基，3－甲基苯基，4－甲基苯基，2－甲氧基苯基，3－三氟甲基苯基，五氟苯基，1－萘基，2－萘基等。
RB2
之雜環基係單環或縮合環，較佳為碳數1~20，更佳為碳數1~12，進而較佳為碳數2~10之雜環基，較佳為含氮原子，氧原子，硫原子，硒原子之至少一個之芳香族雜環基。此雜環基之例方面，可例舉例如吡咯啶，哌啶，六氫吡，嗎啉，噻吩，和吩(selenophene)，呋喃，吡咯，咪唑，吡唑，吡啶，吡嗪，嗒，嘧啶，三唑，三，吲哚，吲唑，嘌呤，噻唑啉，噻唑，噻二唑，噁唑啉，噁唑，噁二唑，喹啉，異喹啉，酞(phthalazine)，萘叉(naphthylidene)，喹喔啉，喹唑啉，噌啉，喋啶，吖啶，菲繞啉，啡啉(phenazine)，四唑，苯并咪唑，苯并噁唑，苯并噻唑，苯并三唑，四氧雜(tetrazaindene)茚，咔唑，吖庚因等，較佳為，呋喃，噻吩，吡啶，吡嗪，嘧啶，嗒，三，喹啉，酞(phthalazine)，萘叉(naphthylidene)，喹喔啉，喹唑啉，更佳為呋喃，噻吩，吡啶，喹啉，進而較佳為喹啉。
RB2
所示之脂肪族烴基，芳基及雜環基可具有取代基，取代基方面係與以該LB
所示基之取代基所例舉者相同，又恰當的取代基亦同。
RB2
方面較佳為脂肪族烴基，芳基或雜環基，更佳為脂肪族烴基(較佳為碳數6~30，更佳為碳數6~20，進而較佳為碳數6~12之物)或芳基，進而較佳為脂肪族烴基(較佳為碳數1~20，更佳為碳數1~12，進而較佳為碳數2~10之物)。
XB2
方面較佳為－O－，＝N－RB2
，更佳為＝N－RB2
，特佳為＝N－RB2
。
ZB2
示為形成芳香族環而為必要的原子群。ZB2
所形成之芳香族環可為芳香族烴環，芳香族雜環之任一種，具體例方面，可例舉例如苯環，吡啶環，吡嗪環，嘧啶環，嗒環，三環，吡咯環，呋喃環，噻吩環，和吩(selenophene)環，tellurophene環：，咪唑環，噻唑環，selenazole環，tellurazole環，噻二唑環，噁二唑環，吡唑環等，較佳為苯環，吡啶環，吡嗪環，嘧啶環，嗒環，更佳為苯環，吡啶環，吡嗪環，進而較佳為苯環，吡啶環，特佳為吡啶環。
ZB2
所形成之芳香族環，進而與其他環形成縮合環亦可，亦可具有取代基。取代基方面則與以該LB
所示基之取代基所例舉者相同，較佳為烷基，鏈烯基，炔基，芳基，胺基，烷氧基，芳氧基，醯基，烷氧羰基，芳氧羰基，醯基氧基，醯基胺基，烷氧羰胺基，芳氧羰胺基，磺醯胺基，胺磺醯基，胺甲醯基，烷基硫基，芳基硫基，磺醯基，鹵原子，氰基，雜環基，更佳為烷基，芳基，烷氧基，芳氧基，鹵原子，氰基，雜環基，進而較佳為烷基，芳基，烷氧基，芳氧基，芳香族雜環基，特佳為烷基，芳基，烷氧基，芳香族雜環基。
nB2
係1~4之整數，以2~3為佳。
該一般式(B)所示之含氮5員環衍生物中，進而較佳為下述一般式(B')所示者為佳。
一般式(B')中，RB71
，RB72
及RB73
在各自一般式(B)中與RB2
同，又恰當的範圍亦同。
ZB71
，ZB72
及ZB73
，各自在一般式(B)中與ZB2
同，又恰當的範圍亦同。
LB71
，LB72
及LB73
各表鍵聯基，在一般式(B)中可例舉LB
之例為二價者及單鍵，較佳為單鍵，二價芳香族烴環基，二價芳香族雜環基，及該等組合所成鍵聯，更佳為單鍵。LB71
，LB72
及LB73
可具有取代基，取代基方面與該一般式(B)中以LB
所示基之取代基所舉者同，又恰當之取代基亦同。
Y示氮原子，1,3,5－苯三基或2,4,6－三三基。1,3,5－苯三基可在2,4,6－位具有取代基，取代基方面，可例舉例如烷基，芳香族烴環基，鹵原子等。
一般式(B)或(B')所示之含氮5員環衍生物之具體例係如以下所示，但並非限定於該等例示化合物。
在構成電子注入層及電子輸送層之化合物方面，除了本發明之有機EL元件用材料之外，可例舉具有電子缺乏性含氮5員環或電子缺乏性含氮6員環骨架，與取代或無取代之吲哚骨架，取代或無取代之咔唑骨架，取代或無取代之氮雜咔唑骨架予以組合之構造的化合物等。又，恰當的電子缺乏性含氮5員環或電子缺乏性含氮6員環骨架方面，可例舉吡啶，嘧啶，吡嗪，三，三唑，噁二唑，吡唑，咪唑，喹喔啉，吡咯骨架及該等互為縮合之苯并咪唑，咪唑并吡啶等之分子骨架。該等組合中較佳為吡啶，嘧啶，吡嗪，三骨架，與咔唑，吲哚，氮雜咔唑，喹喔啉骨架。前述骨架可被取代亦可不被取代。
電子輸送性化合物之具體例係如以下所示。
電子注入層及電子輸送層，可為該材料之1種或2種以上所成單層構造，亦可為同一組成或異種組成之複數層所成多層構造。
該等以π電子缺乏性含氮雜環基為佳。
又，該電子注入層之構成成分方面，除了該含氮環衍生物之外之無機化合物方面，以使用絕緣體或半導體為佳。電子注入層若為以絕緣體或半導體所構成，則可有效地防止電流之漏出，可使電子注入性提高。
此種絕緣體方面，以使用選自鹼金屬硫化物(chalcogenide)，鹼土類金屬硫化物，鹼金屬之鹵化物及鹼土類金屬之鹵化物所成群之至少一個金屬化合物為佳。電子注入層若為以該等鹼金屬硫化物等所構成的話，就可使電子注入性進而提高之點為佳。具體而言，恰當的鹼金屬硫化物方面，可例舉例如Li2
O，K2
O，Na2
S，Na2
Se及Na2
O，恰當的鹼土類金屬硫化物方面，可例舉例如CaO，BaO，SrO，BeO，BaS及CaSe。又，恰當的鹼金屬之鹵化物方面，可例舉例如LiF，NaF，KF，LiCl，KCl及NaCl等。又，恰當的鹼土類金屬之鹵化物方面，可例舉例如CaF2
，BaF2
，SrF2
，MgF2
及BeF2
等之氟化物，或氟化物以外之鹵化物。
又，半導體方面，可例舉含有Ba，Ca，Sr，Yb，Al，Ga，In，Li，Na，Cd，Mg，Si，Ta，Sb及Zn之至少一個元素之氧化物，氮化物或氧化氮化物等之一種，單獨或二種以上之組合。又，構成電子注入層之無機化合物，以微結晶或非晶質之絕緣性薄膜為佳。電子注入層若為以該等絕緣性薄膜所構成，則為了形成更為均質的薄膜，則可使黑點(dark spot)等像素缺陷減少。此外，此種無機化合物方面，可例舉該鹼金屬硫化物，鹼土類金屬硫化物，鹼金屬之鹵化物及鹼土類金屬之鹵化物等。
又，本發明中電子注入層可含有前述還原性摻雜劑。
本發明中，有機EL元件之陽極，係擔任使電洞注入於電洞輸送層或發光層之任務，以具有4.5eV以上之功函數者為有效。本發明所使用之陽極材料之具體例方面，可適用氧化銦錫合金(ITO)，氧化錫(NESA)，金，銀，鉑，銅等。又陰極方面，以在電子注入層或發光層注入電子為目的，以功函數小的材料為佳。陰極材料並無特別限定，具體言之可使用銦，鋁，鎂，鎂－銦合金，鎂－鋁合金，鋁－鋰合金，鋁－鈧－鋰合金，鎂－銀合金等。
本發明有機EL元件之各層形成方法並無特別限定。可使用周知之真空蒸鍍法，旋轉塗佈法等所致形成方法。使用於本發明之有機EL元件之，含有該一般式(1)或(2)所示之化合物之有機薄膜層，可以真空蒸鍍法，分子線蒸鍍法(MBE法)或溶解於溶劑之溶液之浸漬法，旋轉塗佈法，鑄塑法，棒塗佈法，輥塗佈法等塗佈法所致周知之方法來形成。
本發明有機EL元件之各有機層之膜厚並無特別限定，一般膜厚過薄時易於產生針孔等缺陷，相反地過厚時高度外加電壓為必要，因效率惡化，通常以數nm至1μm之範圍為佳。
接著，使用實施例進而詳細說明本發明。
藉由下述合成路徑來合成化合物A－2。
裝入4－二苯并呋喃硼酸3.12g，1－溴－3－碘苯4.07g，四個－三苯基膦鈀(0)0.33g，2M碳酸鈉水溶液25g，二甲氧基乙烷70ml於燒瓶，在氬氛圍下，經8小時加熱回流。以薄層層析術(TLC)確認反應完成後，添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂乾燥有機層後，過濾並濃縮，獲得黃色油狀物質。以柱色譜精製後，獲得4.13g之白色固體(收率89%，中間體A)。關於此物質，進行FD－MS(場解吸質量光譜(Field Desorption Massspetrum)分析)測定，結果如以下所示。
FD－MS：calcd C18
H11
BrO 323.18,found 323
接著將中間體A全量裝入燒瓶，在氬氛圍下，添加脫水二乙基醚40ml，脫水四氫呋喃30ml一邊攪拌一邊溶解，以MeOH－乾冰浴冷卻至－60℃，在該處將1.6M正丁基鋰己烷溶液10ml以注射器滴下。經15分攪拌後，將使二氯二苯基矽烷1.35ml溶解於脫水四氫呋喃10ml之溶液滴下。升溫至5℃後以TLC確認反應完成，添加飽和氯化銨水溶液使反應完成。添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂使溶液乾燥後，過濾並濃縮，獲得無色油狀物質。以柱色譜精製後，獲得白色固體。使其以己烷再度洗淨，乾燥之，獲得化合物A－2 2.42g(收率56%)。就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcdC48
H32
O2
Si 668.85,found 668
所得之化合物A－2在320℃，1.3×10－3
Torr進行昇華精製用於蒸鍍。
高速液體層析術(HPLC)純度為99.5%。
以下述合成路徑來合成化合物B－1。
將2－二苯并噻吩硼酸3.3g，1－溴－3－碘苯4.0g，四個三苯基膦鈀(0)0.31g，2M碳酸鈉水溶液25ml，二甲氧基乙烷70ml裝入燒瓶，在氬氛圍下，經9小時加熱回流。以TLC確認反應完成後，添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂乾燥有機層後，過濾並濃縮，獲得黃色油狀物質。以柱色譜精製後，獲得3.96g之白色固體(收率83%，中間體B)。就此物質，進行FD－MS測定結果如以下所示。
FD－MS：calcd C18
H11
BrS 339.25,found 339
將中間體B 3.96g裝入燒瓶，在氬氛圍下添加脫水四氫呋喃40ml一邊攪拌一邊溶解，以MeOH－乾冰浴冷卻至－70℃，對此將1.6M正丁基鋰己烷溶液8ml以注射器滴下。經15分攪拌後，將二氯二苯基矽烷1.35ml溶解於脫水四氫呋喃10ml之溶液滴下。升溫至5℃後以TLC確認反應完成，添加飽和氯化銨水溶液使反應完成。添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂使溶液乾燥後，過濾並濃縮，獲得無色油狀物質。以柱色譜精製後，獲得白色固體。使其以己烷經3次洗淨，乾燥之，獲得化合物B－1 2.49g(收率68%)。就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcd C48
H32
S2
Si 700.98,found 700
所得之化合物B－1於310℃，5.0×10－6
Torr進行昇華精製用於蒸鍍。HPLC純度為99.3%。
以下述之合成路徑來合成化合物B－2。
將4－二苯并噻吩硼酸3.3g，1－溴－3－碘苯4.0g，四個三苯基膦鈀(0)0.31g，2M碳酸鈉水溶液25ml，二甲氧基乙烷70ml裝入燒瓶，在氬氛圍下，經9小時加熱回流。以TLC確認反應完成後，添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂乾燥有機層後，過濾並濃縮，獲得黃色油狀物質。以柱色譜精製後，獲得4.2g之白色固體(收率88%，中間體C)。就此物質，進行FD－MS測定之結果如以下所示。
FD－MS：calcd C18
H11
BrS 339.25,found 339
將中間體C 4.0g裝入燒瓶，在氬氛圍下，添加脫水四氫呋喃40ml予以一邊攪拌一邊溶解，以MeOH－乾冰浴冷卻至－70℃，對此將1.6M正丁基鋰己烷溶液8ml以注射器滴下。經15分攪拌後，將二氯二苯基矽烷1.4ml溶解於脫水四氫呋喃10ml之溶液予以滴下。升溫至5℃後以TLC確認反應完成，添加飽和氯化銨水溶液使反應完成。添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂使溶液乾燥後，過濾並濃縮，獲得無色油狀物質。
以柱色譜精製後，獲得白色固體。使其以己烷經3次洗淨，乾燥之，獲得化合物B－2 2.52g(收率69%)。就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcd C48
H32
S2
Si 700.98,found 700
所得之化合物B－2以310℃，5.5×10－6
T0rr昇華精製使用於蒸鍍。HPLC純度為99.3%。
以下述之合成路徑來合成化合物C－2。
將中間體A 2.48g裝入燒瓶，在氬氛圍下，添加脫水四氫呋喃30ml一邊攪拌一邊溶解，以MeOH－乾冰浴冷卻至－60℃，對此使1.6M正丁基鋰己烷溶液5ml以注射器滴下。經15分攪拌後，將二苯基二氯鍺烷1.0g溶解於脫水四氫呋喃13ml之溶液予以滴下。升溫至5℃後以TLC確認反應完成，添加飽和氯化銨水溶液來完成反應。添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂使溶液乾燥後，過濾並濃縮，獲得無色油狀物質。以柱色譜精製後，獲得白色固體。使其以己烷再度洗淨，乾燥之，獲得化合物C－2 1.61g(收率67%)，就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcd C48
H32
O2
Ge 713.41,found 713
所得之化合物C－2以340℃，1.9×10－3
Torr昇華精製而用於蒸鍍。
HPLC純度為99.7%。
以下述之合成路徑來合成化合物C－7。
將3,5－二溴聯苯基3.08g裝入燒瓶在氬氛圍下，添加脫水二乙基醚40ml一邊攪拌一邊溶解，以MeOH－乾冰浴冷卻至－60℃，對此將1.6M正丁基鋰己烷溶液6.2ml以注射器滴下。升溫至－10℃為止後，冷卻至－40℃將二苯基二氯鍺烷1.36g溶解於脫水二乙基醚10ml之溶液予以滴下。升溫至－10℃為止後以TLC確認反應完成，添加飽和氯化銨水溶液使反應完成。添加二氯甲烷，以水洗淨後，使有機層分離，以硫酸鎂使溶液乾燥後，過濾並濃縮，獲得黃色油狀物質。以柱色譜精製後，獲得白色固體。使其以己烷再度洗淨，乾燥之，獲得中間體D 2.85g(收率90%)。就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcd C36
H26
Br2
Ge 691.01,found 691
將中間體D全量2.85g,4－二苯并呋喃硼酸1.85g，四個－三苯基膦鈀(0)0.19g，2M碳酸鈉水溶液19g，二甲氧基乙烷50ml裝入燒瓶，在氬氛圍下，經9小時加熱回流。以TLC確認反應完成後，添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂乾燥有機層後，過濾並濃縮，獲得橙色油狀物質。以柱色譜精製後，可獲得2.86g之白色固體之化合物C－7(收率80%)。就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcd C60
H40
GeO2
865.60,found 865
所得之化合物C－7以360℃，3.7×10－6
Torr進行昇華精製用於蒸鍍。
HPLC純度為99.1%。
以下述之合成路徑來合成化合物D－2。
將中間體C 2.57g裝入燒瓶，在氬氛圍下，添加脫水四氫呋喃30ml一邊攪拌一邊溶解，以MeOH－乾冰浴冷卻至－70℃，對此使1.6M正丁基鋰己烷溶液5ml以注射器滴下。經15分攪拌後，將二氯二苯基鍺烷1.0g溶解於脫水四氫呋喃15ml之溶液予以滴下。在升溫至－12℃後以TLC確認反應完成，添加飽和氯化銨水溶液使反應完成。添加二氯甲烷，以水洗淨後，使有機層分離，以硫酸鎂使溶液乾燥後，過濾並濃縮，獲得淡黃色油狀物質。以柱色譜精製後，獲得白色固體。使其以己烷經2次洗淨，乾燥之，獲得化合物D－2 1.97g(收率79%)。就此物質，進行FD－MS測定之結果如以下所示。
FD－MS：calcd C48
H32
S2
Ge 745.54,found 745
所得之化合物D－2以320℃，7.7×10－6
Torr進行昇華精製用於蒸鍍。
HPLC純度為99.8%。
以下述之合成路徑來合成化合物A－7。
將3,5－二溴聯苯基3.0g裝入燒瓶，在氬氛圍下，添加脫水二乙基醚40ml一邊攪拌一邊溶解，以MeOH－乾冰浴冷卻至－70℃，對此將1.6M正丁基鋰己烷溶液6.0ml以注射器滴下。在升溫至－10℃後，冷卻至－40℃將二苯基二氯矽烷0.92g溶解於脫水二乙基醚10ml之溶液予以滴下。在升溫至0℃後以TLC確認反應完成，添加飽和氯化銨水溶液使反應完成，添加二氯甲烷，以水洗淨後，使有機層分離，以硫酸鎂使溶液乾燥後，過濾並濃縮，獲得黃色油狀物質。以柱色譜精製後，獲得白色固體。使其以己烷再度洗淨，乾燥之，獲得中間體E 1.64g(收率58%)。就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcd C36
H26
Br2
Si 646.46,found 646
將中間體E全量1.64g，4－二苯并呋喃硼酸1.07g，四個－三苯基膦鈀(0)0.12g，2M碳酸鈉水溶液10g，二甲氧基乙烷40ml裝入燒瓶，在氬氛圍下，經8小時加熱回流。以TLC確認反應完成後，添加二氯甲烷，以水，飽和食鹽水洗淨後，使有機層分離，以硫酸鎂乾燥有機層後，過濾並濃縮，獲得黃色油狀物質。以柱色譜精製後，獲得1.87g之白色固體A－7(收率90%)。就此物質，進行FD－MS測定，結果如以下所示。
FD－MS：calcd C60
H40
SiO2
821.04,found 821
化合物A－7係以350℃，6.1×10－6
Torr昇華精製用於蒸鍍。HPLC純度為99.3%。
此外，合成實施例1~7中用於FD－MS之測定之裝置及測定條件如以下所示。
<FD－MS測定>裝置：HX110(日本電子公司製)條件：加速電壓8kV掃瞄範圍m/z＝50~1500發射種：碳發射電流：0mA→2mA/分→40mA(保持10分)
將附有25mm×75mm×1.1mm厚ITO透明電極之玻璃基板(Geomatic公司製)在異丙基醇中進行超音波洗淨5分鐘後，進行UV臭氧洗淨30分鐘。將洗淨後附有透明電極線之玻璃基板安裝於真空蒸鍍裝置之基板保持架，首先在形成透明電極線側的面上，以覆蓋該透明電極之方式使膜厚95nm之下述材料HTM成膜。此HTM膜係作為電洞注入輸送層來作用。進而，在電洞注入輸送層上以膜厚30nm，主材料係將合成例1所得之化合物A－2與上述錯合物K－1藉由電阻加熱進行共蒸鍍成膜。錯合物K－1之濃度為7重量%。此膜係以發光層來作用。持續在此發光層上，將下述材料ETM1以膜厚25nm，進而，在此ETM1上將下述材料ETM2進行5nm層合成膜。此ETM1層，ETM2層各自係以電子輸送層，電子注入層來作用。其後，將LiF作為電子注入性電極(陰極)以成膜速度1/min形成膜厚1nm。在此LiF層上使金屬AI蒸鍍，使金屬陰極形成膜厚150nm來製作有機EL元件。
(有機EL元件之發光性能評價)將以上方式製作之有機EL元件以直流電流驅動予以發光進行通電試驗，測定發光波長(λ)，亮度(L)，電流密度(J)，來求得電流效率(L/J)。其結果如表1所示。又，關於壽命，則測定初期亮度1500cd/m2
衰減一半之時間，以比較例1為100之相對值如表1所示。
在實施例1中，主材料係使用表1之合成例2~7所得之主材料，以替代化合物A－2以外，其他則同樣地來製作有機EL元件。關於所得之各自有機EL元件，與實施例1同，進行通電試驗及壽命之測定。該等結果如表1所示。
實施例1中，主材料係使用，國際公開WO2004/095598號公報，日本特開2005－310672號公報，日本特開2005－306864號公報及日本特開2005－317275號公報各自記載之下述比較化合物1~4，以替代化合物A－2以外，其他則同樣地來製作有機EL元件。就所得之各自有機EL元件，與實施例1同樣地進行通電試驗及壽命之測定。該等結果如表1所示。
如表1所示，與實施例所用之主材料比較，比較例所用之主材料均顯示電流效率低的值，電壓亦高，壽命減短。
如以上之詳細說明，利用本發明之一般式(1)或(2)所示之化合物所成有機EL元件用材料時，可獲得發光效率高，並無像素缺陷，耐熱性優異，且壽命長的有機EL元件。
因此，本發明之有機EL元件，作為各種電子機器之光源等極為有用。
Claims (12)
- 一種有機電致發光元件用材料，其係由下述一般式(2)所示之化合物所構成，
- 如申請專利範圍第1項之有機電致發光元件用材料，其係由下述一般式(3)或(4)所示之化合物所構成；
- 一種有機電致發光元件，其為在陰極與陽極間夾持有至少具有發光層之由一層或複數層所構成的有機薄膜層之有機電致發光元件，其特徵為，該有機薄膜層之至少一 層係含有如申請專利範圍第1項或第2項之有機電致發光元件用材料。
- 如申請專利範圍第3項之有機電致發光元件，其中該發光層係含有該有機電致發光元件用材料作為主材料。
- 如申請專利範圍第3項之有機電致發光元件，其中該發光層含有主材料與磷光性之發光材料，該主材料為該有機電致發光元件用材料。
- 如申請專利範圍第3項之有機電致發光元件，其中該發光層含有主材料與磷光性之發光材料，該磷光性之發光材料係含有銥(Ir)、鋨(0s)或鉑(Pt)金屬之化合物。
- 如申請專利範圍第3項之有機電致發光元件，其中該發光層係含有主材料與磷光性之發光材料，該磷光性之發光材料為具有金屬-碳烯(carbene)碳鍵結之發光材料。
- 如申請專利範圍第3項之有機電致發光元件，其中該發光層係含有最高發光亮度之波長為500nm以下之藍色系金屬錯合物。
- 如申請專利範圍第3項之有機電致發光元件，其中在該發光層與陰極之間具有電子注入層，該電子注入層含有含氮環衍生物作為主成分者。
- 如申請專利範圍第3項之有機電致發光元件，其中該有機電致發光元件具有電洞輸送層，該電洞輸送層含有該有機電致發光元件用材料。
- 如申請專利範圍第3項之有機電致發光元件，其中該有機電致發光元件具有電子輸送層及/或電洞障壁層，該電子輸送層及/或電洞障壁層，含有該有機電致發光元件用材料。
- 如申請專利範圍第3項之有機電致發光元件，其中在陰極與有機薄膜層之界面區域添加還原性摻雜劑所成者。
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- 2007-05-29 JP JP2008520508A patent/JP5081821B2/ja not_active Expired - Fee Related
- 2007-05-29 EP EP07744340.6A patent/EP2034538B1/en not_active Not-in-force
- 2007-05-29 US US12/303,199 patent/US8563145B2/en active Active
- 2007-05-29 WO PCT/JP2007/060921 patent/WO2007142083A1/ja not_active Ceased
- 2007-06-01 TW TW096119810A patent/TWI408209B/zh not_active IP Right Cessation
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2013
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20090016684A (ko) | 2009-02-17 |
| EP2034538A4 (en) | 2010-12-29 |
| JPWO2007142083A1 (ja) | 2009-10-22 |
| EP2034538B1 (en) | 2013-10-09 |
| EP2034538A1 (en) | 2009-03-11 |
| US20090224658A1 (en) | 2009-09-10 |
| CN101461074B (zh) | 2011-06-15 |
| JP5081821B2 (ja) | 2012-11-28 |
| TW200806776A (en) | 2008-02-01 |
| US20140021461A1 (en) | 2014-01-23 |
| US8563145B2 (en) | 2013-10-22 |
| CN101461074A (zh) | 2009-06-17 |
| WO2007142083A1 (ja) | 2007-12-13 |
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