CN100518424C - organic electroluminescent element - Google Patents
organic electroluminescent element Download PDFInfo
- Publication number
- CN100518424C CN100518424C CNB2003801068764A CN200380106876A CN100518424C CN 100518424 C CN100518424 C CN 100518424C CN B2003801068764 A CNB2003801068764 A CN B2003801068764A CN 200380106876 A CN200380106876 A CN 200380106876A CN 100518424 C CN100518424 C CN 100518424C
- Authority
- CN
- China
- Prior art keywords
- base
- luminescent layer
- dopant
- organic electroluminescent
- electroluminescent device
- 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.)
- Expired - Lifetime
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- 239000000463 material Substances 0.000 claims abstract description 115
- 239000002019 doping agent Substances 0.000 claims abstract description 104
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 238000001228 spectrum Methods 0.000 claims description 19
- 241001597008 Nomeidae Species 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000005504 styryl group Chemical group 0.000 claims description 7
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical group C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 238000000295 emission spectrum Methods 0.000 abstract 2
- -1 diamine compound Chemical class 0.000 description 318
- 239000010410 layer Substances 0.000 description 303
- 239000002585 base Substances 0.000 description 278
- 238000000034 method Methods 0.000 description 55
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 38
- 125000001424 substituent group Chemical group 0.000 description 34
- 238000002347 injection Methods 0.000 description 31
- 239000007924 injection Substances 0.000 description 31
- 239000010408 film Substances 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000005755 formation reaction Methods 0.000 description 20
- 150000001721 carbon Chemical group 0.000 description 16
- 238000000151 deposition Methods 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 239000011630 iodine Substances 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 230000004888 barrier function Effects 0.000 description 12
- 230000008021 deposition Effects 0.000 description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 230000005684 electric field Effects 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- 150000001342 alkaline earth metals Chemical class 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 7
- 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 6
- 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 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- 230000001052 transient effect Effects 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 5
- 239000004411 aluminium Substances 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 5
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 150000002910 rare earth metals Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 description 4
- 150000008045 alkali metal halides Chemical class 0.000 description 4
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 229910052798 chalcogen Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 4
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 3
- 125000006083 1-bromoethyl group Chemical group 0.000 description 3
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 125000005999 2-bromoethyl group Chemical group 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000006278 bromobenzyl group Chemical group 0.000 description 3
- 125000005998 bromoethyl group Chemical group 0.000 description 3
- 125000005997 bromomethyl group Chemical group 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 150000002220 fluorenes Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 3
- 150000005235 imidazopyrazines Chemical class 0.000 description 3
- 125000006178 methyl benzyl group Chemical group 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
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 125000006502 nitrobenzyl group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000005581 pyrene group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 238000002366 time-of-flight method Methods 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 239000012212 insulator Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical class CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 2
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical compound C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- 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 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- DKQIZRNNADMWTR-UHFFFAOYSA-N 3-(2-aminophenyl)-1-phenylprop-2-en-1-one Chemical class NC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 DKQIZRNNADMWTR-UHFFFAOYSA-N 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- XZVNKEAPHZSYCJ-UHFFFAOYSA-N 4-[4-amino-4-(4-phenylphenyl)cyclohexa-1,5-dien-1-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=CCC(N)(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 XZVNKEAPHZSYCJ-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
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- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910017083 AlN Inorganic materials 0.000 description 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CCPAKNGVCSJPDN-UHFFFAOYSA-N C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=C(C=CC(=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C=CC1=CC=C(C=C1)N)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=C(C=CC(=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C=CC1=CC=C(C=C1)N)C1=CC=CC=C1 CCPAKNGVCSJPDN-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- HDDYZBALTSRZPD-UHFFFAOYSA-N NCC=1C=C(C=CC1)N(C1=CC=CC=C1)C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound NCC=1C=C(C=CC1)N(C1=CC=CC=C1)C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 HDDYZBALTSRZPD-UHFFFAOYSA-N 0.000 description 1
- 229910000574 NaK Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
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- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
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- 229910052793 cadmium Inorganic materials 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
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- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- PKIFBGYEEVFWTJ-UHFFFAOYSA-N hexaphene Chemical group C1=CC=C2C=C3C4=CC5=CC6=CC=CC=C6C=C5C=C4C=CC3=CC2=C1 PKIFBGYEEVFWTJ-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
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- 239000005355 lead glass Substances 0.000 description 1
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
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- VXPCQISYVPFYRK-UHFFFAOYSA-N profenamine hydrochloride Chemical compound Cl.C1=CC=C2N(CC(C)N(CC)CC)C3=CC=CC=C3SC2=C1 VXPCQISYVPFYRK-UHFFFAOYSA-N 0.000 description 1
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Abstract
An organic electroluminescent element comprising an anode, a first light-emitting layer containing at least a first host material and a first dopant, a second light-emitting layer containing at least a second host material and a second dopant, and a cathode in this order, characterized in thatComprises the following steps: energy gap E of first host materialgh1. Energy gap E of first dopantgd1. Energy gap E of the second host materialgh2 and energy gap E of the second dopantgd2 satisfies the following formula, and the emission intensity I1 of the emission maximum wavelength of the emission spectrum from the first light-emitting layer and the emission intensity I2 of the emission maximum wavelength of the emission spectrum from the second light-emitting layer satisfy the following formula. Egh1＞Egd1;Egh2＞Egd2;Egd1＞Egd2;I1＞3.5×I2。
Description
Technical field
The present invention relates to organic electroluminescent device, in more detail, relate to the organic electroluminescent device that luminescent layer is a two-layer structure.
Background technology
Utilize the electroluminescent cell (following electroluminescence is abbreviated as " EL ") of electroluminescence because self is luminous, therefore visual high, and owing to be complete solid-state components, therefore have the characteristics of resistance to impact excellence etc., therefore in various display unit, utilize it noticeable as light-emitting component.
In this EL element, exist the inorganic EL element of in luminescent material, using inorganic compound and the organic EL that uses organic compound, wherein particularly organic EL except can reducing applied voltage significantly, also can easily carry out panchromaticization, and consumption of electric power is little, it is luminous to carry out face, therefore it is developed as follow-on light-emitting component.
About the formation of organic EL, as shown in Figure 3, constitute by anode/luminescent layer/negative electrode substantially.
This organic EL 10 is clamping luminescent layer 14 between the pair of electrodes that is formed by anode 12 and negative electrode 13.The normally stacked multilayer of luminescent layer 14 forms.During extra electric field, inject electronics from negative electrode 13 sides, between to two electrodes 12,13 of this element 10 from anode 12 side injected holes.So electronics and hole be combination once more in luminescent layer 14, produce excited state, when excited state is got back to ground state, energy is emitted as light.
Fig. 4 has shown the energy diagram of the organic EL of Fig. 3.In Fig. 4, valence energy level EV0 (HOMO) and conduction energy level EC0 (LUMO) have been shown as the energy level of luminescent layer 14.From anode 12 side injected holes, inject electronics from negative electrode 13 sides, the combination and luminous luminescent layer 14 in of these holes and electronics.
As the basis, be provided with aptly therein that transfer layer or electron injecting layer are injected in the hole and the structure that forms is known has anode/hole for example to inject the structure that transfer layer/luminescent layer/electron injecting layer/negative electrode is injected in transfer layer/luminescent layer/negative electrode or anode/hole with said structure.
At this, luminescent layer also has following function simultaneously.
1. function of injecting: when extra electric field, can inject the function of electronics by negative electrode or electron injecting layer by anode or hole injection layer injected hole.
2. conveying function: the mobile function of electric charge (electronics and hole) that under the effect of electric field force, makes injection.
3. lighting function: provide electronics and the hole field of combination once more, luminous thereupon function.
In addition, the hole is injected transfer layer and is had by the anode injected hole, and carries the function in this hole to organic luminous layer, in addition, also exists the structure that hole injection layer/hole transporting layer is made respectively.Electron injecting layer has by negative electrode injection electronics, is transported to the function of organic luminous layer.
For making luminous stronger in the luminescent layer, the known technology that has trace to add fluorescence molecule (dopant).
Fig. 5 has shown the energy diagram of the organic EL that has added dopant.In the figure, ECh is the conduction energy level of matrix, and EVh is the valence energy level of matrix, and ECd is the conduction energy level of dopant, and EVd is the valence energy level of dopant.In addition, E
GhBe the energy level gap (ECh and EVh's is poor) of matrix, E
GdEnergy level gap (ECd and EVd's is poor) for dopant.
Dopant is accepted the energy of the matrix that excites efficiently, has improved luminous efficiency.
As making the method for luminous multicolor of organic EL, roughly be divided into following 3 kinds of methods.
The method that 1. will be divided into 3 coloured light and take out from white luminous employing redness, green and the 3 kinds of blue colour filters that organic EL sends.
2. will carry out colour switching and the method for multicolor by the fluorescence coating that the light that is arranged on luminescent layer takes out side to blue light from the blue-light-emitting that the blue EL element sends.
3. on same substrate, place blue, red, green luminescent layer side by side, carry out the method for multicolor.
In these methods, demand has high briliancy and long organic EL of life-span.For example 1. and in the method 2., wish in the luminous organic EL in the broadband (spectrum that width is wide) of carrying out bluish-green colour system or white, to exist especially for initial stage briliancy hundreds of nit, have the organic EL in life-span half-life more than several ten thousand hours.
With respect to this needs, various element formations is studied.
As a kind of method wherein, as described below, proposed to obtain the method for white or broad-band illumination by organic luminous layer is carried out multiple stratification.
1. organic luminous layer is made double-layer structure, with first luminescent layer of anode-side as the blue light-emitting layer that constitutes by the aluminium complex, with second luminescent layer of cathode side as the red light emitting layer that constitutes by the aluminium complex that contains the red fluorescence material, the method (for example with reference to No. 0643549 specification of European patent) that white light is taken out.
2. organic luminous layer is made double-layer structure, with first luminescent layer of anode-side as the blue light-emitting layer that constitutes by diphenylethyllene propine compounds, with second luminescent layer of cathode side as in the aluminium complex that sends green glow, adding the luminescent layer that the red fluorescence material forms, the method (for example with reference to No. 5503910 specification of United States Patent (USP)) that white light is taken out.
3. in the luminescent layer that the mixed layer of electron transport compound that is made of the aluminium complex and the cavity conveying compound that is made of diamine compound constitutes, make it contain cumarin and rubrene, obtain to have the luminous method (for example with reference to the international book that discloses No. 98/08360) of green composition and orange composition as dopant.
4. in the host material that constitutes by diphenylethyllene propine compounds,, form the method (for example opening flat 12-68057 communique) of two-layer luminescent layer with reference to the spy by the different fluorescent substance of colour system more than two kinds that mixes.
These prior aries are to make the dopant of a plurality of kinds luminous comparably, obtain the method for broad-band illumination or white, and the light that is sent by organic EL is mixed with various wavelength.
But, in having the organic EL of multilayer laminated structure, the arrowband that colorimetric purity is high (spectrum that width is narrow) luminous, and long organic EL of life-span still belongs to the unknown.
At above-mentioned problem, the object of the present invention is to provide that to carry out the high arrowband of colorimetric purity luminous, and long organic EL of life-span.
Summary of the invention
For addressing the above problem, the present inventor finds in the organic EL that has two-layer luminescent layer at least, by suppressing the luminous of second luminescent layer or when two-layer luminescent layer satisfies certain relation, in the life-span that can improve colorimetric purity and/or element, finishing the present invention thus.
According to the present invention, provide following organic electroluminescent device.
[1] a kind of organic electroluminescent device, its contain in the following order anode,
At least contain first host material and first dopant first luminescent layer,
At least contain second host material and second dopant second luminescent layer,
And negative electrode, it is characterized by:
The energy gap E of above-mentioned first host material
Gh1, the energy gap E of above-mentioned first dopant
Gd1, the energy gap E of above-mentioned second host material
Gh2 and the energy gap E of above-mentioned second dopant
Gd2 satisfy following formula,
And satisfy following formula from the luminous intensity I1 of the luminous very big wavelength of the luminescent spectrum of described first luminescent layer with from the luminous intensity I2 of the luminous very big wavelength of the luminescent spectrum of described second luminescent layer.
I1＞3.5×I2
[2] as the organic electroluminescent device of above-mentioned [1] record, it is characterized by the relation that satisfies I1＞5 * I2.
[3] as the organic electroluminescent device of above-mentioned [1] or [2] record, it is characterized by E
Gd2＞2.7eV.
[4] a kind of organic electroluminescent device, its contain in the following order anode,
At least contain first host material and first dopant first luminescent layer,
At least contain second host material and second dopant second luminescent layer,
And negative electrode, it is characterized by:
The energy gap E of above-mentioned first host material
Gh1, the energy gap E of above-mentioned first dopant
Gd1, the energy gap E of above-mentioned second host material
Gh2 and the energy gap E of above-mentioned second dopant
Gd2 satisfy following formula.
[5] as the organic electroluminescent device of each record of above-mentioned [1]～[4], it is characterized by in above-mentioned first luminescent layer, above-mentioned first dopant is 0.1-10mol% with respect to the ratio of above-mentioned first host material.
[6] as the organic electroluminescent device of each record of above-mentioned [1]～[5], it is characterized by in above-mentioned second luminescent layer, above-mentioned second dopant is 0.1-10mol% with respect to the ratio of above-mentioned second host material.
[7] as the organic electroluminescent device of each record of above-mentioned [1]～[6], at least one side who it is characterized by above-mentioned first or second host material is the compound of following general formula [1] expression.
[in the formula, Ar
1For the nucleus carbon atom number is 6～50 aromatic ring, X is a substituting group.
M is 1～5 integer, and n is 0～6 integer.When m 〉=2, Ar can be identical or different respectively.When n 〉=2, X can be identical or different respectively.]
[8] as the organic electroluminescent device of each record of above-mentioned [1]～[7], it is identical with above-mentioned second host material to it is characterized by above-mentioned first host material.
[9] as the organic electroluminescent device of each record of above-mentioned [1]～[8], at least one side who it is characterized by above-mentioned first or second dopant material is the compound of following general formula [2] expression.
[in the formula, Ar
2～Ar
4For replacing or unsubstituted nucleus carbon atom number is 6～50 aromatic group, replacement or unsubstituted styryl, p is 1～4 integer.P 〉=2 o'clock, Ar
3And Ar
4Can be identical or different respectively.]
[10] as the organic electroluminescent device of each record of above-mentioned [1]～[9], the thickness that it is characterized by above-mentioned first luminescent layer is more than the 10nm.
[11] as the organic electroluminescent device of each record of above-mentioned [1]～[10], the luminous intensity I2 that it is characterized by from the luminous very big wavelength of the luminescent spectrum of described second luminescent layer is I2=0.
[12] as the organic electroluminescent device of each record of above-mentioned [1]～[11], it is characterized by between described second luminescent layer and negative electrode electron injecting layer is set, the electron mobility of this electron injecting layer is 10
-4Cm
2/ more than (V second).
[13] as the organic electroluminescent device of above-mentioned [12] record, it is characterized by described electron injecting layer and contain the organic compound that constitutes by nitogen-contained heterocycle derivant.
[14] as the organic electroluminescent device of above-mentioned [13] record, it is characterized by the described organic compound that is made of nitogen-contained heterocycle derivant is Imidazopyrazines derivative and/or imdazole derivatives.
Description of drawings
Fig. 1 is the simple sectional view of organic EL of the present invention.
Fig. 2 is the energy diagram of organic EL of the present invention.
Fig. 3 is the simple sectional view of general organic EL.
Fig. 4 is the energy diagram of organic EL.
Fig. 5 is the energy diagram that has added the organic EL of dopant.
Embodiment
Below the present invention is described in detail.
First organic EL of the present invention, its contain in the following order anode, at least contain first luminescent layer of first host material and first dopant, contain second luminescent layer and the negative electrode of second host material and second dopant at least, it is characterized by the energy gap E of first host material
Gh1, the energy gap E of first dopant
Gd1, the energy gap E of second host material
GhThe energy gap E of 2 and second dopant
Gd2 satisfy following formula, and satisfy following formula from the luminous intensity I1 of the luminous very big wavelength of the luminescent spectrum of first luminescent layer with from the luminous intensity I2 of the luminous very big wavelength of the luminescent spectrum of second luminescent layer.
I1＞3.5×I2
Fig. 1 is the simple sectional view of organic EL of the present invention.
Organic EL has anode 2, first luminescent layer 3, second luminescent layer 4 and negative electrode 5 at least, and these layers are according to this sequential cascade.
Fig. 2 is the energy diagram of organic EL 1.
There is shown the energy level of anode 2, first luminescent layer 3, second luminescent layer 4 and negative electrode 5 at this energy.In addition, also show the energy gap E of first host material
Gh1, the energy gap E of first dopant
Gd1, the energy gap E of second host material
GhThe energy gap E of 2 and second dopant
Gd2.
At this so-called energy gap, be equivalent to the valence energy level of organic EL Material and the energy difference of conduction energy level, obtain by the absorption edge in the optical absorption spectra of this material usually.
As shown in Figure 2, in the present invention,, make luminescent layer become two-layer structure, mainly make the luminous structure of first luminescent layer 3 that contains the big dopant of energy gap thereby form by in different luminescent layer 3,4, mix respectively first dopant and second dopant.
Usually, contain in making one deck luminescent layer under the situation of two kinds of dopants, because the distance between these dopants is near, therefore energy takes place easily move, normally two kinds of dopants are luminous respectively, perhaps only are that the little side's of energy gap dopant is luminous.It is extremely difficult only making the big dopant of energy gap luminous.
But,, judge that because first luminescent layer 3 and second luminescent layer 4 are all luminous, the arrowband that therefore can not obtain the colorimetric purity rising is luminous if only make luminescent layer become double-layer structure from the example of prior art.
As one of its reason is to exist hole and electronics that the position problems of combination again takes place.Think be injected in the luminescent layer the hole because and the combination again of electronics, concentration reduces along with entering into negative electrode 5 sides, but a part arrive negative electrode 5 near.Therefore, also exist the recombination region territory near negative electrode 5 sides, this is to cause first luminescent layer 3 (luminescent layer that is present in anode 2 sides) and all luminous reason of second luminescent layer 4 (luminescent layer that is present in negative electrode 5 sides).
Therefore in the present invention, as suppressing it is the luminous method of luminescent layer that contains the little dopant of energy gap that makes the reason of colorimetric purity reduction, can form such structure: in anode 2 sides that join probability is high again first luminescent layer 3 is set, second luminescent layer 4 is set in negative electrode 5 sides that join probability is low again.Thus, can mainly make first luminescent layer 3 luminous, and make the luminous of second luminescent layer 4 become enough little.
In addition, in the present invention, preferably between second luminescent layer 4 and negative electrode 5 electron injecting layer is set, this electron injecting layer is 1 * 10 in electric field strength (E)
5～10
6Electron mobility in the electric field region of V/cm is 10
-4Cm
2/ more than (V second).
Electron injecting layer by setting has this electron mobility can more stably be set in light-emitting zone in first luminescent layer 3.Therefore, because that first luminescent layer 3 is had more is optionally luminous, it is luminous to obtain the better arrowband of colorimetric purity, and long lifetime significantly.
In addition, assay method as electron mobility, method that has Time of flight method (method of calculating by the mensuration of electric charge travel time in the organic membrane) or calculate by the voltage characteristic of spatial limitation electric current etc. [with reference to Electronic Process in Organic Crystals (M.Pope, C.E.Swenberg), Organic Molecular Solids (W.Jones)].
In this manual, calculate by Time of flight method.Particularly, be the time response (transient characteristic time) of the rayed of transient current produce by to(for) the structure determination of ITO/ organic layer (electron injecting layer etc.)/Al, calculate electron mobility by following formula.
Electron mobility=(organic bed thickness)
2/ (transient characteristic time electric field strength)
Generally, the material that the big material of energy gap and energy gap are little is compared, because long material of life-span half-life is few, therefore cause and be difficult to selected material, but,, prolonged in the life-span of organic EL although second luminescent layer works hardly for luminous by this formation.
In this organic EL 1, the energy gap (E of first host material
Gh1) energy gap (E of ratio first dopant
Gd1) big.Promptly satisfy E
Gh1＞E
Gd1 relation.
The energy gap E of preferred first dopant
Gd1 greater than 2.7eV.The dopant that the big dopant of general energy gap and energy gap are little is compared, life-span half-life of organic EL short more.Therefore the organic EL of the pure blue that uses in panchromatic is difficult to make its long lifetime especially, but the present invention is by adopting above-mentioned formation, and it is luminous to obtain extremely long pure blue of life-span.
Second luminescent layer contains second host material and second dopant at least.
The energy gap E of second host material
GhThe energy gap E of 2 to the second dopants
Gd2 is big.Promptly satisfy E
Gh2＞E
Gd2 relation.
The energy gap E of first dopant
GdThe energy gap E of 1 to the second dopant
Gd2 is big.Promptly satisfy E
Gd1＞E
Gd2 relation.
In addition, the energy gap E of preferred second dopant
Gd2 greater than 2.7eV, promptly satisfies E
GdThe relation of 2＞2.7eV.Thus, can make the high blue-light-emitting organic EL of colorimetric purity of panchromatic usefulness.
This organic EL is from the luminous intensity I1 of the luminous very big wavelength of the luminescent spectrum of the light of first luminescent layer and satisfy the relation of I1＞3.5 * I2 from the luminous intensity I2 of the luminous very big wavelength of the luminescent spectrum of the light of second luminescent layer.By satisfying this relation, the arrowband that can obtain high color purity is luminous.Preferred I1＞5 * I2, more preferably I1＞10 * I2, especially preferably the luminous intensity I2 from second luminescent layer is 0.
Like this, even under the luminous luminous situation of doing hardly to contribute of second luminescent layer, prolonged in the life-span of organic EL with respect to organic EL integral body.
The long-life material of material that general energy gap is more little is many more, easily material is selected.Therefore broad-band illumination or white luminously be easier to constitute the long-life element with the EL element ratio.
But broad-band illumination particularly blue-light-emitting is difficult to selected long-life material system, and the pure blue luminescent material that particularly is suitable for panchromatic purposes does not almost have report so far yet.The present invention is for carrying out the technology of long lifetime to hitherto known pure blue luminescent material.That is, this technology is by using known long-life material, make it in abutting connection with luminescent layer, and does one's utmost to control luminous from herein, EL element is carried out the technology of long lifetime.
Second organic EL of the present invention contain in the following order anode, at least contain first luminescent layer of first host material and first dopant, contain second luminescent layer and the negative electrode of second host material and second dopant at least, it is characterized by the energy gap E of first host material
Gh1, the energy gap E of first dopant
Gd1, the energy gap E of second host material
GhThe energy gap E of 2 and second dopant
Gd2 satisfy following formula.
That is, for basic formation, its organic EL with above-mentioned explanation is identical.
This organic EL satisfies E
Gd1＞E
GdThe relation of 2＞2.7eV.Owing to satisfy this relation, so they are different with above-mentioned organic EL, even first luminescent layer and second luminescent layer are all luminous, also are blue-light-emitting, therefore can obtain the high blue-light-emitting of colorimetric purity.
And, constitute by becoming this element, can be the same with first invention, make the organic EL long lifetime.
The host material that uses in first luminescent layer and second luminescent layer can use respectively as the known host material of long-life luminescent material, but preferably uses the host material of the material shown in the general formula [1] as luminescent material.
[in the formula, Ar
1For the nucleus carbon atom number is 6～50 aromatic ring, X is a substituting group.
M is 1～5 integer, and n is 0～6 integer.When m 〉=2, Ar
1Can be identical or different respectively.When n 〉=2, X can be identical or different respectively.]
As Ar
1Instantiation, can enumerate the adjacent inferior phenyl ring of phenyl ring, naphthalene nucleus, anthracene nucleus, connection, Azulene ring, acenaphthene ring, fluorenes ring, phenanthrene ring, fluoranthene ring, ア セ Off
ェNa Application ス リ レ Application ring, benzo [9,10] phenanthrene ring, pyrene ring,
Ring, aphthacene Huan, Pi Huan, perylene ring, pentaphene ring, pentacene ring, four phenylenes (tetraphenylene) ring, hexaphene ring, hexacene ring, rubicene ring, coronene ring, trinaphthylene ring etc.
Preferably, can exemplify out phenyl ring, naphthalene nucleus, anthracene nucleus, acenaphthene ring, fluorenes ring, phenanthrene ring, fluoranthene ring, benzo [9,10] phenanthrene ring, pyrene ring,
Huan, perylene ring, trinaphthylene ring etc.
Further preferably, can exemplify out phenyl ring, naphthalene nucleus, anthracene nucleus, fluorenes ring, phenanthrene ring, fluoranthene ring, pyrene ring,
Huan, perylene ring etc.
In addition, as the instantiation of X, can be and replace or unsubstituted nucleus carbon atom number is 6～50 aromatic series base, replacement or unsubstituted nuclear atom number are 5～50 aromatic heterocycle, replacement or unsubstituted carbon number are 1～50 alkyl, replacement or unsubstituted carbon number are 1～50 alkoxyl, replacement or unsubstituted carbon number are 1～50 aralkyl, replacement or unsubstituted nuclear atom number are 5～50 aryloxy group, replacement or unsubstituted nuclear atom number are 5～50 arylthio, replacement or unsubstituted carbon number are 1～50 carboxyl, replace or unsubstituted styryl, halogen radical, cyano group, nitro, hydroxyl etc.
As replacing or unsubstituted nucleus carbon atom number is the example of 6～50 aromatic series base, can enumerate phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 1-phenanthryl, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, 1-aphthacene base, 2-aphthacene base, 9-aphthacene base, the 1-pyrenyl, the 2-pyrenyl, the 4-pyrenyl, the 2-xenyl, the 3-xenyl, the 4-xenyl, para-terpheny-4-base, para-terpheny-3-base, para-terpheny-2-base, meta-terphenyl-4-base, meta-terphenyl-3-base, meta-terphenyl-2-base, o-tolyl, between tolyl, p-methylphenyl, to tert-butyl-phenyl, right-(2-phenyl propyl) phenyl, 3-methyl-2-naphthyl, 4-methyl isophthalic acid-naphthyl, 4-methyl isophthalic acid-anthryl, 4 '-methyl biphenyl; 4 "-the tert-butyl group-para-terpheny-4-base, the 2-fluorenyl, 9,9-dimethyl-2-fluorenyl, 3-fluoranthene base etc.
Preferably, can exemplify out phenyl, 1-naphthyl, 2-naphthyl, 9-anthryl, 1-aphthacene base, 2-aphthacene base, 9-aphthacene base, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-xenyl, 3-xenyl, 4-xenyl, o-tolyl, a tolyl, p-methylphenyl, to tert-butyl-phenyl, 2-fluorenyl, 9,9-dimethyl-2-fluorenyl, 3-fluoranthene base etc.
As replacing or unsubstituted nuclear atom number is the example of 5～50 aromatic heterocycle, can enumerate the 1-pyrrole radicals, the 2-pyrrole radicals, the 3-pyrrole radicals, pyrazinyl, the 2-pyridine radicals, the 3-pyridine radicals, the 4-pyridine radicals, the 1-indyl, the 2-indyl, the 3-indyl, the 4-indyl, the 5-indyl, the 6-indyl, the 7-indyl, the 1-isoindolyl, the 2-isoindolyl, the 3-isoindolyl, the 4-isoindolyl, the 5-isoindolyl, the 6-isoindolyl, the 7-isoindolyl, the 2-furyl, the 3-furyl, the 2-benzofuranyl, the 3-benzofuranyl, the 4-benzofuranyl, the 5-benzofuranyl, the 6-benzofuranyl, the 7-benzofuranyl, the 1-isobenzofuran-base, the 3-isobenzofuran-base, the 4-isobenzofuran-base, the 5-isobenzofuran-base, the 6-isobenzofuran-base, the 7-isobenzofuran-base, quinolyl, the 3-quinolyl, the 4-quinolyl, the 5-quinolyl, the 6-quinolyl, the 7-quinolyl, the 8-quinolyl, the 1-isoquinolyl, the 3-isoquinolyl, the 4-isoquinolyl, the 5-isoquinolyl, the 6-isoquinolyl, the 7-isoquinolyl, the 8-isoquinolyl, the 2-quinoxalinyl, the 5-quinoxalinyl, the 6-quinoxalinyl, the 1-carbazyl, the 2-carbazyl, the 3-carbazyl, the 4-carbazyl, the 9-carbazyl, the 1-phenanthridinyl, the 2-phenanthridinyl, the 3-phenanthridinyl, the 4-phenanthridinyl, the 6-phenanthridinyl, the 7-phenanthridinyl, the 8-phenanthridinyl, the 9-phenanthridinyl, the 10-phenanthridinyl, the 1-acridinyl, the 2-acridinyl, the 3-acridinyl, the 4-acridinyl, the 9-acridinyl, 1,7-phenanthroline-2-base, 1,7-phenanthroline-3-base, 1,7-phenanthroline-4-base, 1,7-phenanthroline-5-base, 1,7-phenanthroline-6-base, 1,7-phenanthroline-8-base, 1,7-phenanthroline-9-base, 1,7-phenanthroline-10-base, 1,8-phenanthroline-2-base, 1,8-phenanthroline-3-base, 1,8-phenanthroline-4-base, 1,8-phenanthroline-5-base, 1,8-phenanthroline-6-base, 1,8-phenanthroline-7-base, 1,8-phenanthroline-9-base, 1,8-phenanthroline-10-base, 1,9-phenanthroline-2-base, 1,9-phenanthroline-3-base, 1,9-phenanthroline-4-base, 1,9-phenanthroline-5-base, 1,9-phenanthroline-6-base, 1,9-phenanthroline-7-base, 1,9-phenanthroline-8-base, 1,9-phenanthroline-10-base, 1,10-phenanthroline-2-base, 1,10-phenanthroline-3-base, 1,10-phenanthroline-4-base, 1,10-phenanthroline-5-base, 2,9-phenanthroline-1-base, 2,9-phenanthroline-3-base, 2,9-phenanthroline-4-base, 2,9-phenanthroline-5-base, 2,9-phenanthroline-6-base, 2,9-phenanthroline-7-base, 2,9-phenanthroline-8-base, 2,9-phenanthroline-10-base, 2,8-phenanthroline-1-base, 2,8-phenanthroline-3-base, 2,8-phenanthroline-4-base, 2,8-phenanthroline-5-base, 2,8-phenanthroline-6-base, 2,8-phenanthroline-7-base, 2,8-phenanthroline-9-base, 2,8-phenanthroline-10-base, 2,7-phenanthroline-1-base, 2,7-phenanthroline-3-base, 2,7-phenanthroline-4-base, 2,7-phenanthroline-5-base, 2,7-phenanthroline-6-base, 2,7-phenanthroline-8-base, 2,7-phenanthroline-9-base, 2,7-phenanthroline-10-base, the 1-phenazinyl, the 2-phenazinyl, the 1-phenothiazinyl, the 2-phenothiazinyl, the 3-phenothiazinyl, the 4-phenothiazinyl, the lysivane base, the 1-phenoxazine group, the 2-phenoxazine group, the 3-phenoxazine group, the 4-phenoxazine group, the 10-phenoxazine group, the 2-oxazolyl, the 4-oxazolyl, the 5-oxazolyl, 2-oxadiazole base, 5-oxadiazole base, 3-furazan base, the 2-thienyl, the 3-thienyl, 2-methylpyrrole-1-base, 2-methylpyrrole-3-base, 2-methylpyrrole-4-base, 2-methylpyrrole-5-base, 3-methylpyrrole-1-base, 3-methylpyrrole-2-base, 3-methylpyrrole-4-base, 3-methylpyrrole-5-base, 2-tert-butyl group pyrroles-4-base, 3-(2-phenyl propyl) pyrroles-1-base, 2-methyl isophthalic acid-indyl, 4-methyl isophthalic acid-indyl, 2-methyl-3-indyl, 4-methyl-3-indyl, the 2-tert-butyl group-1-indyl, the 4-tert-butyl group-1-indyl, the 2-tert-butyl group-3-indyl, the 4-tert-butyl group-3-indyl etc.
As replacing or unsubstituted carbon number is the example of 1～50 alkyl, can enumerate methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl, methylol, the 1-hydroxyethyl, the 2-hydroxyethyl, 2-hydroxyl isobutyl group, 1, the 2-dihydroxy ethyl, 1,3-dihydroxy isopropyl, 2, the 3-dihydroxy tert-butyl group, 1,2,3-trihydroxy propyl group, chloromethyl, the 1-chloroethyl, the 2-chloroethyl, 2-chlorine isobutyl group, 1, the 2-Dichloroethyl, 1,3-two chloro isopropyls, 2, the 3-dichloro tert-butyl group, 1,2,3-three chloropropyls, bromomethyl, the 1-bromoethyl, the 2-bromoethyl, 2-bromine isobutyl group, 1,2-two bromoethyls, 1,3-dibromo isopropyl, 2, the 3-dibromo tert-butyl group, 1,2,3-three bromopropyls, iodomethyl, 1-iodine ethyl, 2-iodine ethyl, 2-iodine isobutyl group, 1,2-diiodo-ethyl, 1,3-diiodo-isopropyl, 2, the 3-diiodo-tert-butyl group, 1,2,3-triiodo propyl group, amino methyl, the 1-amino-ethyl, the 2-amino-ethyl, 2-aminoisobutyric base, 1, the 2-diamino ethyl, 1,3-diaminourea isopropyl, 2, the 3-diaminourea tert-butyl group, 1,2,3-triamido propyl group, cyano methyl, the 1-cyano ethyl, the 2-cyano ethyl, 2-cyano group isobutyl group, 1,2-dicyano ethyl, 1,3-dicyano isopropyl, 2, the 3-dicyano tert-butyl group, 1,2,3-tricyano propyl group, the nitro methyl, the 1-nitro-ethyl, the 2-nitro-ethyl, 2-nitro isobutyl group, 1,2-dinitro ethyl, 1,3-dinitro isopropyl, 2, the 3-dinitro tert-butyl group, 1,2,3-trinitro-propyl group, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, the 4-methylcyclohexyl, the 1-adamantyl, the 2-adamantyl, 1-norborneol alkyl, 2-norborneol alkyl etc.
Replace or unsubstituted carbon number to be 1～50 alkoxyl be-group that OY represents, example as Y, can enumerate methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, the 1-hydroxyethyl, the 2-hydroxyethyl, 2-hydroxyl isobutyl group, 1, the 2-dihydroxy ethyl, 1,3-dihydroxy isopropyl, 2, the 3-dihydroxy tert-butyl group, 1,2,3-trihydroxy propyl group, chloromethyl, the 1-chloroethyl, the 2-chloroethyl, 2-chlorine isobutyl group, 1, the 2-Dichloroethyl, 1,3-two chloro isopropyls, 2, the 3-dichloro tert-butyl group, 1,2,3-three chloropropyls, bromomethyl, the 1-bromoethyl, the 2-bromoethyl, 2-bromine isobutyl group, 1,2-two bromoethyls, 1,3-dibromo isopropyl, 2, the 3-dibromo tert-butyl group, 1,2,3-three bromopropyls, iodomethyl, 1-iodine ethyl, 2-iodine ethyl, 2-iodine isobutyl group, 1,2-diiodo-ethyl, 1,3-diiodo-isopropyl, 2, the 3-diiodo-tert-butyl group, 1,2,3-triiodo propyl group, amino methyl, the 1-amino-ethyl, the 2-amino-ethyl, 2-aminoisobutyric base, 1, the 2-diamino ethyl, 1,3-diaminourea isopropyl, 2, the 3-diaminourea tert-butyl group, 1,2,3-triamido propyl group, cyano methyl, the 1-cyano ethyl, the 2-cyano ethyl, 2-cyano group isobutyl group, 1,2-dicyano ethyl, 1,3-dicyano isopropyl, 2, the 3-dicyano tert-butyl group, 1,2,3-tricyano propyl group, the nitro methyl, the 1-nitro-ethyl, the 2-nitro-ethyl, 2-nitro isobutyl group, 1,2-dinitro ethyl, 1,3-dinitro isopropyl, 2, the 3-dinitro tert-butyl group, 1,2,3-trinitro-propyl group etc.
As replacing or unsubstituted carbon number is the example of 1～50 aralkyl, can enumerate benzyl, the 1-phenylethyl, the 2-phenylethyl, 1-propyloxy phenyl base, 2-propyloxy phenyl base, the phenyl tert-butyl group, the Alpha-Naphthyl methyl, 1-Alpha-Naphthyl ethyl, 2-Alpha-Naphthyl ethyl, 1-Alpha-Naphthyl isopropyl, 2-Alpha-Naphthyl isopropyl, the betanaphthyl methyl, 1-betanaphthyl ethyl, 2-betanaphthyl ethyl, 1-betanaphthyl isopropyl, 2-betanaphthyl isopropyl, 1-pyrrole radicals methyl, 2-(1-pyrrole radicals) ethyl, to methyl-benzyl, between methyl-benzyl, adjacent methyl-benzyl, p-chlorobenzyl, the m-chloro benzyl, o-chlorobenzyl, to bromobenzyl, between bromobenzyl, adjacent bromobenzyl, to the iodine benzyl, between the iodine benzyl, adjacent iodine benzyl, to hydroxybenzyl, between hydroxybenzyl, adjacent hydroxybenzyl, PAB, between aminobenzyl, adjacent aminobenzyl, to nitrobenzyl, between nitrobenzyl, adjacent nitrobenzyl, to the cyano group benzyl, between the cyano group benzyl, o-cyanobenzyl, 1-hydroxyl-2-propyloxy phenyl base, 1-chloro-2-propyloxy phenyl base etc.
Replacement or unsubstituted nuclear atom number are 5～50 aryloxy group usefulness-OY ' expression, example as Y ', can exemplify out phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 1-phenanthryl, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, 1-aphthacene base, 2-aphthacene base, 9-aphthacene base, the 1-pyrenyl, the 2-pyrenyl, the 4-pyrenyl, the 2-xenyl, the 3-xenyl, the 4-xenyl, para-terpheny-4-base, para-terpheny-3-base, para-terpheny-2-base, meta-terphenyl-4-base, meta-terphenyl-3-base, meta-terphenyl-2-base, o-tolyl, between tolyl, p-methylphenyl, to tert-butyl-phenyl, right-(2-phenyl propyl) phenyl, 3-methyl-2-naphthyl, 4-methyl isophthalic acid-naphthyl, 4-methyl isophthalic acid-anthryl, 4 '-methyl biphenyl; 4 "-tert-butyl group para-terpheny-4-base, the 2-pyrrole radicals, the 3-pyrrole radicals, pyrazinyl, the 2-pyridine radicals, the 3-pyridine radicals, the 4-pyridine radicals, the 2-indyl, the 3-indyl, the 4-indyl, the 5-indyl, the 6-indyl, the 7-indyl, the 1-isoindolyl, the 3-isoindolyl, the 4-isoindolyl, the 5-isoindolyl, the 6-isoindolyl, the 7-isoindolyl, the 2-furyl, the 3-furyl, the 2-benzofuranyl, the 3-benzofuranyl, the 4-benzofuranyl, the 5-benzofuranyl, the 6-benzofuranyl, the 7-benzofuranyl, the 1-isobenzofuran-base, the 3-isobenzofuran-base, the 4-isobenzofuran-base, the 5-isobenzofuran-base, the 6-isobenzofuran-base, the 7-isobenzofuran-base, the 2-quinolyl, the 3-quinolyl, the 4-quinolyl, the 5-quinolyl, the 6-quinolyl, the 7-quinolyl, the 8-quinolyl, the 1-isoquinolyl, the 3-isoquinolyl, the 4-isoquinolyl, the 5-isoquinolyl, the 6-isoquinolyl, the 7-isoquinolyl, the 8-isoquinolyl, the 2-quinoxalinyl, the 5-quinoxalinyl, the 6-quinoxalinyl, the 1-carbazyl, the 2-carbazyl, the 3-carbazyl, the 4-carbazyl, the 1-phenanthridinyl, the 2-phenanthridinyl, the 3-phenanthridinyl, the 4-phenanthridinyl, the 6-phenanthridinyl, the 7-phenanthridinyl, the 8-phenanthridinyl, the 9-phenanthridinyl, the 10-phenanthridinyl, the 1-acridinyl, the 2-acridinyl, the 3-acridinyl, the 4-acridinyl, the 9-acridinyl, 1,7-phenanthroline-2-base, 1,7-phenanthroline-3-base, 1,7-phenanthroline-4-base, 1,7-phenanthroline-5-base, 1,7-phenanthroline-6-base, 1,7-phenanthroline-8-base, 1,7-phenanthroline-9-base, 1,7-phenanthroline-10-base, 1,8-phenanthroline-2-base, 1,8-phenanthroline-3-base, 1,8-phenanthroline-4-base, 1,8-phenanthroline-5-base, 1,8-phenanthroline-6-base, 1,8-phenanthroline-7-base, 1,8-phenanthroline-9-base, 1,8-phenanthroline-10-base, 1,9-phenanthroline-2-base, 1,9-phenanthroline-3-base, 1,9-phenanthroline-4-base, 1,9-phenanthroline-5-base, 1,9-phenanthroline-6-base, 1,9-phenanthroline-7-base, 1,9-phenanthroline-8-base, 1,9-phenanthroline-10-base, 1,10-phenanthroline-2-base, 1,10-phenanthroline-3-base, 1,10-phenanthroline-4-base, 1,10-phenanthroline-5-base, 2,9-phenanthroline-1-base, 2,9-phenanthroline-3-base, 2,9-phenanthroline-4-base, 2,9-phenanthroline-5-base, 2,9-phenanthroline-6-base, 2,9-phenanthroline-7-base, 2,9-phenanthroline-8-base, 2,9-phenanthroline-10-base, 2,8-phenanthroline-1-base, 2,8-phenanthroline-3-base, 2,8-phenanthroline-4-base, 2,8-phenanthroline-5-base, 2,8-phenanthroline-6-base, 2,8-phenanthroline-7-base, 2,8-phenanthroline-9-base, 2,8-phenanthroline-10-base, 2,7-phenanthroline-1-base, 2,7-phenanthroline-3-base, 2,7-phenanthroline-4-base, 2,7-phenanthroline-5-base, 2,7-phenanthroline-6-base, 2,7-phenanthroline-8-base, 2,7-phenanthroline-9-base, 2,7-phenanthroline-10-base, the 1-phenazinyl, the 2-phenazinyl, the 1-phenothiazinyl, the 2-phenothiazinyl, the 3-phenothiazinyl, the 4-phenothiazinyl, the 1-phenoxazine group, the 2-phenoxazine group, the 3-phenoxazine group, the 4-phenoxazine group, the 2-oxazolyl, the 4-oxazolyl, the 5-oxazolyl, 2-oxadiazole base, 5-oxadiazole base, 3-furazan base, the 2-thienyl, the 3-thienyl, 2-methylpyrrole-1-base, 2-methylpyrrole-3-base, 2-methylpyrrole-4-base, 2-methylpyrrole-5-base, 3-methylpyrrole-1-base, 3-methylpyrrole-2-base, 3-methylpyrrole-4-base, 3-methylpyrrole-5-base, 2-tert-butyl group pyrroles-4-base, 3-(2-phenyl propyl) pyrroles-1-base, 2-methyl isophthalic acid-indyl, 4-methyl isophthalic acid-indyl, 2-methyl-3-indyl, 4-methyl-3-indyl, the 2-tert-butyl group-1-indyl, the 4-tert-butyl group-1-indyl, the 2-tert-butyl group-3-indyl, the 4-tert-butyl group-3-indyl etc.
Replace or unsubstituted nuclear atom number is 5～50 arylthio usefulness-SY " represent; as Y " example, can exemplify out phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 1-phenanthryl, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, 1-aphthacene base, 2-aphthacene base, 9-aphthacene base, the 1-pyrenyl, the 2-pyrenyl, the 4-pyrenyl, the 2-xenyl, the 3-xenyl, the 4-xenyl, para-terpheny-4-base, para-terpheny-3-base, para-terpheny-2-base, meta-terphenyl-4-base, meta-terphenyl-3-base, meta-terphenyl-2-base, o-tolyl, between tolyl, p-methylphenyl, to tert-butyl-phenyl, right-(2-phenyl propyl) phenyl, 3-methyl-2-naphthyl, 4-methyl isophthalic acid-naphthyl, 4-methyl isophthalic acid-anthryl, 4 '-methyl biphenyl; 4 "-tert-butyl group para-terpheny-4-base, the 2-pyrrole radicals, the 3-pyrrole radicals, pyrazinyl, the 2-pyridine radicals, the 3-pyridine radicals, the 4-pyridine radicals, the 2-indyl, the 3-indyl, the 4-indyl, the 5-indyl, the 6-indyl, the 7-indyl, the 1-isoindolyl, the 3-isoindolyl, the 4-isoindolyl, the 5-isoindolyl, the 6-isoindolyl, the 7-isoindolyl, the 2-furyl, the 3-furyl, the 2-benzofuranyl, the 3-benzofuranyl, the 4-benzofuranyl, the 5-benzofuranyl, the 6-benzofuranyl, the 7-benzofuranyl, the 1-isobenzofuran-base, the 3-isobenzofuran-base, the 4-isobenzofuran-base, the 5-isobenzofuran-base, the 6-isobenzofuran-base, the 7-isobenzofuran-base, the 2-quinolyl, the 3-quinolyl, the 4-quinolyl, the 5-quinolyl, the 6-quinolyl, the 7-quinolyl, the 8-quinolyl, the 1-isoquinolyl, the 3-isoquinolyl, the 4-isoquinolyl, the 5-isoquinolyl, the 6-isoquinolyl, the 7-isoquinolyl, the 8-isoquinolyl, the 2-quinoxalinyl, the 5-quinoxalinyl, the 6-quinoxalinyl, the 1-carbazyl, the 2-carbazyl, the 3-carbazyl, the 4-carbazyl, the 1-phenanthridinyl, the 2-phenanthridinyl, the 3-phenanthridinyl, the 4-phenanthridinyl, the 6-phenanthridinyl, the 7-phenanthridinyl, the 8-phenanthridinyl, the 9-phenanthridinyl, the 10-phenanthridinyl, the 1-acridinyl, the 2-acridinyl, the 3-acridinyl, the 4-acridinyl, the 9-acridinyl, 1,7-phenanthroline-2-base, 1,7-phenanthroline-3-base, 1,7-phenanthroline-4-base, 1,7-phenanthroline-5-base, 1,7-phenanthroline-6-base, 1,7-phenanthroline-8-base, 1,7-phenanthroline-9-base, 1,7-phenanthroline-10-base, 1,8-phenanthroline-2-base, 1,8-phenanthroline-3-base, 1,8-phenanthroline-4-base, 1,8-phenanthroline-5-base, 1,8-phenanthroline-6-base, 1,8-phenanthroline-7-base, 1,8-phenanthroline-9-base, 1,8-phenanthroline-10-base, 1,9-phenanthroline-2-base, 1,9-phenanthroline-3-base, 1,9-phenanthroline-4-base, 1,9-phenanthroline-5-base, 1,9-phenanthroline-6-base, 1,9-phenanthroline-7-base, 1,9-phenanthroline-8-base, 1,9-phenanthroline-10-base, 1,10-phenanthroline-2-base, 1,10-phenanthroline-3-base, 1,10-phenanthroline-4-base, 1,10-phenanthroline-5-base, 2,9-phenanthroline-1-base, 2,9-phenanthroline-3-base, 2,9-phenanthroline-4-base, 2,9-phenanthroline-5-base, 2,9-phenanthroline-6-base, 2,9-phenanthroline-7-base, 2,9-phenanthroline-8-base, 2,9-phenanthroline-10-base, 2,8-phenanthroline-1-base, 2,8-phenanthroline-3-base, 2,8-phenanthroline-4-base, 2,8-phenanthroline-5-base, 2,8-phenanthroline-6-base, 2,8-phenanthroline-7-base, 2,8-phenanthroline-9-base, 2,8-phenanthroline-10-base, 2,7-phenanthroline-1-base, 2,7-phenanthroline-3-base, 2,7-phenanthroline-4-base, 2,7-phenanthroline-5-base, 2,7-phenanthroline-6-base, 2,7-phenanthroline-8-base, 2,7-phenanthroline-9-base, 2,7-phenanthroline-10-base, the 1-phenazinyl, the 2-phenazinyl, the 1-phenothiazinyl, the 2-phenothiazinyl, the 3-phenothiazinyl, the 4-phenothiazinyl, the 1-phenoxazine group, the 2-phenoxazine group, the 3-phenoxazine group, the 4-phenoxazine group, the 2-oxazolyl, the 4-oxazolyl, the 5-oxazolyl, 2-oxadiazole base, 5-oxadiazole base, 3-furazan base, the 2-thienyl, the 3-thienyl, 2-methylpyrrole-1-base, 2-methylpyrrole-3-base, 2-methylpyrrole-4-base, 2-methylpyrrole-5-base, 3-methylpyrrole-1-base, 3-methylpyrrole-2-base, 3-methylpyrrole-4-base, 3-methylpyrrole-5-base, 2-tert-butyl group pyrroles-4-base, 3-(2-phenyl propyl) pyrroles-1-base, 2-methyl isophthalic acid-indyl, 4-methyl isophthalic acid-indyl, 2-methyl-3-indyl, 4-methyl-3-indyl, the 2-tert-butyl group-1-indyl, the 4-tert-butyl group-1-indyl, the 2-tert-butyl group-3-indyl, the 4-tert-butyl group-3-indyl etc.
Replace or unsubstituted carbon number to be 1～50 carboxyl represent with-COOZ, example as Z, can enumerate methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, the 1-hydroxyethyl, the 2-hydroxyethyl, 2-hydroxyl isobutyl group, 1, the 2-dihydroxy ethyl, 1,3-dihydroxy isopropyl, 2, the 3-dihydroxy tert-butyl group, 1,2,3-trihydroxy propyl group, chloromethyl, the 1-chloroethyl, the 2-chloroethyl, 2-chlorine isobutyl group, 1, the 2-Dichloroethyl, 1,3-two chloro isopropyls, 2, the 3-dichloro tert-butyl group, 1,2,3-three chloropropyls, bromomethyl, the 1-bromoethyl, the 2-bromoethyl, 2-bromine isobutyl group, 1,2-two bromoethyls, 1,3-dibromo isopropyl, 2, the 3-dibromo tert-butyl group, 1,2,3-three bromopropyls, iodomethyl, 1-iodine ethyl, 2-iodine ethyl, 2-iodine isobutyl group, 1,2-diiodo-ethyl, 1,3-diiodo-isopropyl, 2, the 3-diiodo-tert-butyl group, 1,2,3-triiodo propyl group, amino methyl, the 1-amino-ethyl, the 2-amino-ethyl, 2-aminoisobutyric base, 1, the 2-diamino ethyl, 1,3-diaminourea isopropyl, 2, the 3-diaminourea tert-butyl group, 1,2,3-triamido propyl group, cyano methyl, the 1-cyano ethyl, the 2-cyano ethyl, 2-cyano group isobutyl group, 1,2-dicyano ethyl, 1,3-dicyano isopropyl, 2, the 3-dicyano tert-butyl group, 1,2,3-tricyano propyl group, the nitro methyl, the 1-nitro-ethyl, the 2-nitro-ethyl, 2-nitro isobutyl group, 1,2-dinitro ethyl, 1,3-dinitro isopropyl, 2, the 3-dinitro tert-butyl group, 1,2,3-trinitro-propyl group etc.
As the example of replacement or unsubstituted styryl, can enumerate 2-phenyl-1-vinyl, 2,2-diphenyl-1-vinyl, 1,2,2-triphenyl-1-vinyl etc.
As the example of halogen radical, can enumerate fluorine, chlorine, bromine, iodine etc.
Preferred m is 1～2, and n is 0～4.
Below show the instantiation of the compound of general formula [1].
In organic EL of the present invention, in order to carry out evaporation easily, first host material and second host material can be identical materials.
The dopant that uses in first luminescent layer and second luminescent layer can use respectively as the known dopant of long-life luminescent material, preferably uses the dopant material of the material shown in the general formula [2] as luminescent material.
[in the formula, Ar
2-Ar
4For replacing or unsubstituted nucleus carbon atom number is 6～50 aromatic series base, replacement or unsubstituted styryl.P is 1～4 integer.P 〉=2 o'clock, Ar
3And Ar
4Can be identical or different respectively.]
As replacing or unsubstituted nucleus carbon atom number is the example of 6～50 aromatic series base, can enumerate phenyl, the 1-naphthyl, the 2-naphthyl, the 1-anthryl, the 2-anthryl, the 9-anthryl, the 1-phenanthryl, the 2-phenanthryl, the 3-phenanthryl, the 4-phenanthryl, the 9-phenanthryl, 1-aphthacene base, 2-aphthacene base, 9-aphthacene base, the 1-pyrenyl, the 2-pyrenyl, the 4-pyrenyl, the 2-xenyl, the 3-xenyl, the 4-xenyl, para-terpheny-4-base, para-terpheny-3-base, para-terpheny-2-base, meta-terphenyl-4-base, meta-terphenyl-3-base, meta-terphenyl-2-base, o-tolyl, between tolyl, p-methylphenyl, to tert-butyl-phenyl, right-(2-phenyl propyl) phenyl, 3-methyl-2-naphthyl, 4-methyl isophthalic acid-naphthyl, 4-methyl isophthalic acid-anthryl, 4 '-methyl biphenyl; 4 "-tert-butyl group para-terpheny-4-base, the 2-fluorenyl, 9,9-dimethyl-2-fluorenyl, 3-fluoranthene base etc.
Preferably, can enumerate phenyl, 1-naphthyl, 2-naphthyl, 9-phenanthryl, 1-aphthacene base, 2-aphthacene base, 9-aphthacene base, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-xenyl, 3-xenyl, 4-xenyl, o-tolyl, a tolyl, p-methylphenyl, to tert-butyl-phenyl, 2-fluorenyl, 9,9-dimethyl-2-fluorenyl, 3-fluoranthene base etc.
As the example of replacement or unsubstituted styryl, can enumerate 2-phenyl-1-vinyl, 2,2-diphenyl-1-vinyl, 1,2,2-triphenyl-1-vinyl etc.
Below show the instantiation of compound of general formula [2] and other and be suitable for examples of compounds as dopant.In addition, in formula, Me represents methyl, and Et represents ethyl.
Above-mentioned first dopant is preferably 0.1～10mol% with respect to the ratio of first host material, is preferably 1～10mol% especially.When less than 0.1mol%, can not obtain enough luminously, and when surpassing 10mol%, will cause the concentration delustring, luminous efficiency might descend.
In addition, above-mentioned second dopant is preferably 0.1～10mol% with respect to the ratio of second host material, is preferably 0.1～5mol% especially.
More than the preferred 10nm of the thickness of first luminescent layer, be preferably 10nm～40nm especially.When not enough 10nm, the hole of enough concentration will arrive second luminescent layer, and the light that makes second luminescent layer send surpasses the degree that institute must use, the possible variation of colorimetric purity.Therefore, can make first luminescent layer than the second luminous bed thickness.
The thickness of second luminescent layer cooperates modulation with first luminescent layer, but is preferably 10nm～40nm, is preferably 10nm～30nm especially.
As the formation method of luminescent layer, the known method of applicable for example vapour deposition method, spin-coating method, LB method etc.Luminescent layer is preferably the packing of molecules film especially.
Here so-called packing of molecules film refers to the film that forms from the material compound deposition of gas phase state, the perhaps film that forms from the material compound solidification of solution state or liquid phase state, this packing of molecules film usually can be by building up the different of structure, higher order structure with the film that is formed by the LB method (molecule built up film), and the difference of the function that perhaps causes is thus distinguished.
In addition, as disclosed open clear 57-51781 communique the spy in, after binding agent such as dissolving resin and material compound are made solution in solvent, make its filming, also can form luminescent layer by spin-coating method etc.
Below describe for the composed component beyond the formation of organic EL of the present invention and the luminescent layer.
In the scope of not damaging action effect of the present invention, other organic layer or inorganic layer can got involved between first luminescent layer and second luminescent layer, between anode and first luminescent layer or between second luminescent layer and the negative electrode.
As the structure of organic EL of the present invention, for example can enumerate
I) anode/first luminescent layer/second luminescent layer/negative electrode
Ii) anode/hole injection layer/first luminescent layer/second luminescent layer/negative electrode
Iii) anode/first luminescent layer/second luminescent layer/electron injecting layer/negative electrode
Iv) anode/hole injection layer/first luminescent layer/second luminescent layer/electron injecting layer/negative electrode
V) anode/organic semiconductor layer/first luminescent layer/second luminescent layer/negative electrode
Vi) anode/organic semiconductor layer/electronics barrier layer/first luminescent layer/second luminescent layer/negative electrode
Vii) anode/organic semiconductor layer/first luminescent layer/second luminescent layer/adhere to improving layer/negative electrode
Viii) anode/hole injection layer/hole transporting layer/first luminescent layer/second luminescent layer/electron injecting layer/negative electrode
Ix) anode/insulating barrier/first luminescent layer/second luminescent layer // insulating barrier/negative electrode
X) anode/inorganic semiconductor layer/insulating barrier/first luminescent layer/second luminescent layer/insulating barrier/negative electrode
Xi) anode/organic semiconductor layer/insulating barrier/first luminescent layer/second luminescent layer/insulating barrier/negative electrode
Xii) anode/insulating barrier/hole injection layer/hole transporting layer/first luminescent layer/second luminescent layer/insulating barrier/negative electrode
Xiii) structure of anode/insulating barrier/hole injection layer/hole transporting layer/first luminescent layer/second luminescent layer/electron injecting layer/negative electrode etc.
The wherein preferred usually structure of using viii).
(1) light-transmitting substrate
Organic EL of the present invention is made on light-transmitting substrate.At this so-called light-transmitting substrate is the substrate of supporting organic EL, and preferably its transmitance at the light of the visible region of 400～700nm is more than 50%, is level and smooth substrate.
Specifically can enumerate glass plate, polymer sheet etc.Can enumerate glass, lead glass, aluminum silicate glass, pyrex, barium pyrex, quartz of soda lime glass, baric, strontium etc. especially as glass plate.As polymer sheet, can enumerate Merlon, acrylic resin, PETG, polyethers thioether, polysulfones etc.
(2) anode
The anode of organic film EL element is being born the effect to hole transporting layer or luminescent layer injected hole, is effective when having the work function more than the 4.5eV.As the instantiation of the used anode material of the present invention, can use tin indium oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, copper etc.In addition, as negative electrode, in order in electron supplying layer or luminescent layer, to inject electronics, the preferred little material of work function.
Anode can form film by the method that these electrode substances is adopted vapour deposition method or sputtering method etc. and make.
Taking out from anode under the situation of the light send by luminescent layer like this, preferably making luminous transmitance with respect to anode greater than 10%.In addition, the film resistor of anode is preferably below hundreds of Ω/.The thickness of anode is different according to material, but is generally 10nm～1 μ m, preferably selects in the scope of 10～200nm.
(3) hole injection, transfer layer
The hole is injected, transfer layer is to help to the luminescent layer injected hole, and with the layer of cavity conveying to light-emitting zone, hole mobility is big, and the ionization energy is usually little, below 5.5eV.As the injection of this hole, transfer layer, preferably under low electric field strength, carry the material in hole to luminescent layer, more preferably the mobility in hole is for example adding 10
4～10
6During the electric field of V/cm, be at least 10
-4Cm
2/ (V second).
The hole is injected as forming, the material of transfer layer, as long as it has above-mentioned preferred character, it there is not special restriction, can perhaps select arbitrarily in the well known materials of from the hole injection layer of organic EL, using to use from the material of photoconductive material, habitually practising in the past as the charge transport material in hole.
As instantiation, can enumerate triazole derivative (with reference to No. 3112197 specifications of United States Patent (USP) etc.) oxadiazole derivative (with reference to No. 3189447 specification of United States Patent (USP) etc.), imdazole derivatives (the special public clear 37-16096 communique of reference etc.), poly-aromatic yl paraffin derivative is (with reference to No. 3615402 specifications of United States Patent (USP), No. 3820989 specifications of United States Patent (USP), No. 3542544 specifications of United States Patent (USP), special public clear 45-555 communique, special public clear 51-10983 communique, the spy opens clear 51-93224 communique, the spy opens clear 55-17105 communique, the spy opens clear 56-4148 communique, the spy opens clear 55-108667 communique, the spy opens clear 55-156953 communique, the spy opens clear 56-36656 communique etc.), pyrazoline derivative and pyrazolone derivative are (with reference to No. 3180729 specification of United States Patent (USP), No. 4278746 specification of United States Patent (USP), the spy opens clear 55-88064 communique, the spy opens clear 55-88065 communique, the spy opens clear 49-105537 communique, the spy opens clear 55-51086 communique, the spy opens clear 56-80051 communique, the spy opens clear 56-88141 communique, the spy opens clear 57-45545 communique, the spy opens clear 54-112637 communique, the spy opens clear 55-74546 communique etc.), phenylenediamine derivative is (with reference to No. 3615404 specification of United States Patent (USP), special public clear 51-10105 communique, special public clear 46-3712 communique, special public clear 47-25336 communique, the spy opens clear 54-53435 communique, the spy opens clear 54-110536 communique, the spy opens clear 54-119925 communique etc.), the arylamine derivative is (with reference to No. 3567450 specification of United States Patent (USP), No. 3180703 specification of United States Patent (USP), No. 3240597 specification of United States Patent (USP), No. 3658520 specification of United States Patent (USP), No. 4232103 specification of United States Patent (USP), No. 4175961 specification of United States Patent (USP), No. 4012376 specification of United States Patent (USP), special public clear 49-35702 communique, special public clear 39-27577 communique, the spy opens clear 55-144250 communique, the spy opens clear 56-119132 communique, the spy opens clear 56-22437 communique, only No. 1110518 specification of patent in west etc.), amino chalcone derivative (with reference to No. 3526501 specification of United States Patent (USP) etc.) the oxazole derivative (disclosed in No. 3257203 specification of United States Patent (USP) etc.) that replaces, styryl anthracene derivant (opening clear 56-46234 communique etc. with reference to the spy), fluorenone derivatives (opening clear 54-110837 communique etc. with reference to the spy), hydazone derivative is (with reference to No. 3717462 specification of United States Patent (USP), the spy opens clear 54-59143 communique, the spy opens clear 55-52063 communique, the spy opens clear 55-52064 communique, the spy opens clear 55-46760 communique, the spy opens clear 55-85495 communique, the spy opens clear 57-11350 communique, the spy opens clear 57-148749 communique, Te Kaiping 2-311591 communique etc.), stilbene derivative (is opened clear 61-210363 communique with reference to the spy, the spy opens clear 61-228451 communique, the spy opens clear 61-14642 communique, the spy opens clear 61-72255 communique, the spy opens clear 62-47646 communique, the spy opens clear 62-36674 communique, the spy opens clear 62-10652 communique, the spy opens clear 62-30255 communique, the spy opens clear 60-93455 communique, the spy opens clear 60-94462 communique, the spy opens clear 60-174749 communique, the spy opens clear 60-175052 communique etc.), silazane derivative (No. 4950950 specification of United States Patent (USP)), polysilanes (spy opens flat 2-204996 communique), phenyl amines copolymer (spy opens flat 2-282263 communique), disclosed electroconductive polymer oligomer (particularly thiophene oligomers) etc. in the Te Kaiping 1-211399 communique.
Material as hole injection layer, can use above-mentioned material, but preferably use porphyrin compound (opening in clear 63-2956965 communique etc. disclosed) the spy, aromatic uncle amine compound and styrylamine compound are (with reference to No. 4127412 specification of United States Patent (USP), the spy opens clear 53-27033 communique, the spy opens clear 54-58445 communique, the spy opens clear 54-149634 communique, the spy opens clear 54-64299 communique, the spy opens clear 55-79450 communique, the spy opens clear 55-144250 communique, the spy opens clear 56-119132 communique, the spy opens clear 61-295558 communique, the spy opens clear 61-98353 communique, the spy opens clear 63-295695 communique etc.), especially preferably use aromatic uncle amine compound.
In addition, that also can enumerate in No. the 5061569th, United States Patent (USP) record has 2 condensation aromatic rings in molecule, for example 4,4 '-two (N-(1-naphthyl)-N-phenyl amino) biphenyl (below be abbreviated as NPD), in addition, also can enumerate the spy open put down in writing in the flat 4-308688 communique 3 triphenylamine unit are connected into star-like 4,4 ', 4 "-three (N-(3-aminomethyl phenyl)-N-phenyl amino) triphenylamine (below be abbreviated as MTDATA) etc.
In addition, except as the two methine compounds of the above-mentioned aromatic series shown in the luminescent layer material, also the inorganic compound of p type Si, p type SiC etc. also can be used as the hole injection layer material.
The hole is injected, transfer layer can known methods such as vacuum vapour deposition, spin-coating method, casting method, LB method carry out filming formation by above-claimed cpd being adopted for example.As the hole inject, there is no particular restriction for the thickness of transfer layer, is generally 5nm～5 μ m.If this hole injection, transfer layer contain compound of the present invention in the cavity conveying region, it can be made of a kind of of above-mentioned material or the one deck that constitutes more than 2 kinds, and the hole that perhaps will inject with above-mentioned hole, the different types of compound of transfer layer constitutes is injected, the stacked formation of transfer layer.
In addition, organic semiconductor layer is to help to carry out the layer that the hole is injected or electronics injects to luminescent layer, and preferably it has 10
-10The conductivity that S/cm is above.As the material of this organic semiconductor layer, can use to contain thiophene oligomers or special open the disclosed conductivity oligomer that contains arylamine oligomer etc. in the flat 8-193191 communique, contain the conductivity dendritic of arylamine dendritic etc. etc.
(4) electron injecting layer
Electron injecting layer is the layer that helps to inject to luminescent layer electronics, and its electron mobility is big, and adhere to improving layer be by with this electron injecting layer in particularly negative electrode adhere to the layer that good material constitutes.
As the material that uses in the electron injecting layer, the metal complex or the nitogen-contained heterocycle derivant of preferred oxine and derivative thereof.
As the instantiation of the metal complex of above-mentioned oxine or derivatives thereof, can enumerate the metallo-chelate quinoline compound of the chelate that contains oxine (being generally oxine or oxine).
For example, the Alq that puts down in writing in the luminescent material item can be used as electron injecting layer.
On the other hand, as nitogen-contained heterocycle derivant, Cun Zai oxadiazole derivative etc.
Zuo Wei oxadiazole derivative can be enumerated the electrical conductivity compound of following general formula [3]～[5] expression.
[in the formula, Ar
5, Ar
6, Ar
7, Ar
9, Ar
10, Ar
13Expression replaces or unsubstituted aryl respectively, can be same to each other or different to each other respectively.In addition, Ar
8, Ar
11, Ar
13Expression replaces or unsubstituted arlydene, can be identical or different respectively.]
At this,, can enumerate phenyl, xenyl, anthryl, perylene base, pyrenyl as aryl.In addition, as arlydene, can enumerate phenylene, naphthylene, biphenylene, anthrylene, Ya perylene base, inferior pyrenyl etc.In addition, as substituting group, can enumerate carbon number and be 1～10 alkyl, carbon number and be 1～10 alkoxyl or cyano group etc.This electrical conductivity compound is preferably film formation property compound.
As the instantiation of above-mentioned electronic conductivity compound, can enumerate following compound.
In addition, as other nitogen-contained heterocycle derivant organic compound, can enumerate the compound of general formula [6] expression.
HAr-L
1-Ar
14-Ar
15 [6]
(in the formula, HAr is 3～40 nitrogen heterocyclic ring for having substituent carbon number, L
1For singly-bound, can to have substituent carbon number be 6～60 arlydene, can have substituent carbon number is that 3～60 inferior heteroaryl maybe can have substituent fluorenylidene, Ar
14For having substituent carbon number is 6～60 divalent aromatic hydrocarbyl, Ar
15It is 6～60 aryl or can to have substituent carbon number be 3～60 heteroaryl that expression can have substituent carbon number.)
The compound of above-mentioned formula [6] can be synthetic according to the method for record in the former 2003-004139 of spy number.
In the nitogen-contained heterocycle derivant organic compound of this general formula [6], preferred Imidazopyrazines derivative, imdazole derivatives.
As the Imidazopyrazines derivative, can enumerate the compound shown in the general formula [7].
(in the formula, A
1～A
3Be nitrogen-atoms or carbon atom, R is 6～60 aryl for having substituent carbon number, can have substituent carbon number is that 3～60 heteroaryl, carbon number are that 1～20 alkyl, carbon number are that 1～20 haloalkyl, carbon number are 1～20 alkoxyl, q is 0 to 5 integer, when q was a integer more than 2, a plurality of R can be same to each other or different to each other.In addition, also can mutually combine between adjacent a plurality of R bases, form replacement or unsubstituted carbon-ring type aliphat ring, perhaps form replacement or unsubstituted carbon-ring type aromatic ring.Ar
16Be 6～60 aryl for having substituent carbon number, can to have substituent carbon number be 3～60 heteroaryl, Ar
17For hydrogen atom, carbon number are that 1～20 alkyl, carbon number are that 1～20 haloalkyl, carbon number are 1～20 alkoxyl, can to have substituent carbon number be 6～60 aryl, can have substituent carbon number to be 3～60 heteroaryl (Ar
16, Ar
17In either party be 10～60 condensation cyclic group for having substituent carbon number, can to have substituent carbon number be 3～60 assorted condensation cyclic group).L
2, L
3To be respectively singly-bound, can to have substituent carbon number be 6～60 condensed ring, can have substituent carbon number is that 3～60 assorted condensed ring maybe can have substituent fluorenylidene).
The compound of above-mentioned [7] can be synthetic according to the method for record in the former 2003-005184 of spy number.
As imdazole derivatives, can enumerate the compound shown in general formula [8] or [9].
(in the formula, R
1For hydrogen atom, can to have substituent carbon number be 6～60 aryl, can have substituent pyridine radicals, can have substituent quinolyl, can have substituent carbon number is that maybe can to have substituent carbon number be 1～20 alkoxyl for 1～20 alkyl, r is 0～4 integer, R
2Be 6～60 aryl for having substituent carbon number, can have substituent pyridine radicals, can have substituent quinolyl, can have substituent carbon number be 1～20 alkyl maybe can to have substituent carbon number be 1～20 alkoxyl, R
3For hydrogen atom, can to have substituent carbon number be 6～60 aryl, can have substituent pyridine radicals, can have substituent quinolyl, can have substituent carbon number be 1～20 alkyl maybe can to have substituent carbon number be 1～20 alkoxyl, L
4Be 6～60 arlydene, can have substituent inferior pyridine radicals, can have substituent inferior quinolyl, can have substituent fluorenylidene, Ar for having substituent carbon number
18Expression can have substituent carbon number and be 6～60 arlydene, can have substituent inferior pyridine radicals, can have substituent inferior quinolyl, Ar
19It is 6～60 aryl that expression can have substituent carbon number, can have substituent pyridine radicals, can have substituent quinolyl, can have substituent carbon number is that maybe can to have substituent carbon number be 1～20 alkoxyl for 1～20 alkyl).
The compound of above-mentioned formula [8] can be synthetic according to the method for the former 2003-67847 of spy number record.
The instantiation of nitogen-contained heterocycle derivant organic compound is as follows.
In the present invention, electron injecting layer is 10 in electric field strength (E)
4～10
6In the zone of V/cm, the preferred electron mobility is 10
-4Cm
2/ more than (V second).By in electron injecting layer, using organic compound, can reduce the driving voltage of organic EL with this electron mobility.
In addition, owing to can make light-emitting zone move into place first luminescent layer in anode-side, can suppress the luminous of second luminescent layer thus, it is luminous therefore can to obtain the better arrowband of colorimetric purity, and makes efficient height, life-span long.
Therefore, particularly preferably in using the extra high compound of electron mobility, for example above-mentioned nitogen-contained heterocycle derivant organic compound, particularly Imidazopyrazines derivative and/or imdazole derivatives in the electron injecting layer.
In addition, above-claimed cpd can be as required forms electron injecting layer with the form of stacked, mixing etc.
In a preferred form of the invention, in the interface zone of the zone of conveying electronic or negative electrode and organic layer, there is the element that contains the reproducibility dopant.Be defined as the material that can reduce to the electron transport compound at this so-called reproducibility dopant.Therefore, if be material with certain reproducibility, can use various materials, preferred use for example is selected from least a material in the organic complex of organic complex, rare earth metal of the oxide of alkali metal, alkaline-earth metal, rare earth metal, alkali-metal oxide, alkali-metal halide, alkaline-earth metal, the halide of alkaline-earth metal, the oxide of rare earth metal or the halide of rare earth metal, alkali-metal organic complex, alkaline-earth metal.
In addition, more specifically, as preferred reproducibility dopant, be preferably selected from Na (work function: 2.36eV), K (work function: 2.28eV), Rb (work function: 2.16eV) and Cs (work function: at least a alkali metal 1.95eV), and Ca (work function: 2.9eV), Sr (work function: 2.0～2.5eV) and Ba (work function: the dopant of the work function of at least a alkaline-earth metal 2.52eV) below 2.9eV especially.Wherein, preferred reproducibility dopant is at least a alkali metal that is selected from K, Rb and Cs, and more preferably Rb or Cs most preferably are Cs.
These alkali-metal reducing powers are high especially, by adding more a spot of these metals to the electron injection region territory, can make glorious degrees raising and life-span lengthening in the organic EL.In addition,, preferably above-mentioned alkali metal more than 2 kinds is used in combination, is preferably the combination that contains Cs especially, for example the combination of Cs and Na, Cs and K, Cs and Rb or Cs and Na and K as the reproducibility dopant of work function below 2.9eV.Contain Cs by combination, can bring into play reducing power efficiently,, can make glorious degrees raising and life-span lengthening in the organic EL by in the electron injection region territory, adding.
In the present invention, the electron injecting layer that is made of insulator or semiconductor can further be set between negative electrode and organic layer.At this moment, can prevent effectively that electric current from leaking, and can improve the electronics injection.As this insulator, the preferred halid at least a metallic compound that is selected from alkali metal chalcogens thing, alkaline-earth metal chalcogenide, alkali-metal halide and alkaline-earth metal that uses.If electron injecting layer is made of these alkali metal chalcogens things etc., can further improve the electronics injection, therefore preferred aspect this.Particularly, as preferred alkali metal chalcogens thing, can enumerate for example Li
2O, LiO, Na
2S, Na
2Se and NaO as preferred alkaline-earth metal chalcogenide, can enumerate for example CaO, BaO, SrO, BeO, BaS and CaSe.In addition, as preferred alkali-metal halide, can enumerate for example LiF, NaF, KF, LiCl, KCl and NaCl etc.In addition, as the halide of preferred alkaline-earth metal, can enumerate for example CaF
2, BaF
2, SrF
2, MgF
2And BeF
2Halide beyond such fluoride and the fluoride.
In addition, electron supplying layer can be set.As the semiconductor that constitutes electron supplying layer, can enumerate the oxide that comprises at least a element that is selected from Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn, the independent a kind of or combination more than 2 kinds of nitride or nitrogen oxide etc.In addition, the inorganic compound of formation electron supplying layer is preferably micro-crystallization or amorphous insulating properties film.If electron supplying layer is made of these insulating properties films, can form the more film of homogeneous, therefore can reduce pixel defectives such as stain.In addition, as this inorganic compound, can enumerate the halide of above-mentioned alkali metal chalcogens thing, alkaline-earth metal chalcogenide, alkali-metal halide and alkaline-earth metal etc.
(5) negative electrode
As negative electrode, use the mixture of metal, alloy, electrical conductivity compound and these materials of work function little (4eV is following) negative electrode as electrode substance.As the instantiation of these electrode substances, can enumerate sodium, sodium-potassium-sodium alloy, magnesium, lithium, magnesium silver alloy, aluminium/aluminium oxide, aluminium lithium alloy, indium, rare earth metal etc.
This negative electrode can be made by these electrode substances being adopted methods such as evaporation or sputter form film.
At this, taking out under the situation of the light send from luminescent layer from negative electrode, preferably make luminous transmitance with respect to negative electrode greater than 10%.
In addition, be preferably below hundreds of Ω/ as the film resistor of negative electrode, thickness is generally 10nm～1 μ m, is preferably 50～200nm.
(6) insulating barrier
Therefore organic EL is easy to generate the picture element flaw that electric leakage or short circuit cause owing to extra electric field on ultrathin membrane.For preventing this phenomenon, preferably between pair of electrodes, insert the thin layer of insulating properties.
As the material that in insulating barrier, uses, can enumerate for example aluminium oxide, lithium fluoride, lithia, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcirm-fluoride, aluminium nitride, titanium oxide, silica, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium-oxide, vanadium oxide etc.
Can use the mixture or the sandwich of these materials.
By the material that exemplifies out more than adopting and method form anode, luminescent layer, as required hole injection layer and electron injecting layer as required, and further form negative electrode, can produce organic EL.In addition, also can from the negative electrode anode according to above-mentioned opposite sequentially built organic EL.
Below put down in writing the example of making of the organic EL of the structure that on light-transmitting substrate, sets gradually anode/hole injection layer/luminescent layer/electron injecting layer/negative electrode.
At first, adopt methods such as evaporation or sputter to form the film that is made of anode material on suitable permeability substrate, making its thickness is below the 1 μ m, preferably in the scope of 10～200nm, makes anode thus.
Secondly, on this anode, hole injection layer is set.The formation of hole injection layer can adopt methods such as aforesaid vacuum vapour deposition, spin-coating method, casting method, LB method to carry out, but obtains homogeneous membrane easily and be not easy to produce pin hole etc. from vacuum vapour deposition, and therefore preferred this method of employing forms.When forming hole injection layer by vacuum vapour deposition, its evaporation condition is because of the crystalline texture of employed compound (material of hole injection layer), required hole injection layer or integrated structure etc. is different again, but general preferred is 50～450 ℃ in the vapor deposition source temperature, and vacuum degree is 10
-7～10
-3Torr, evaporation rate are 0.01～50nm/ second, and substrate temperature is-50～300 ℃, and thickness is suitably to select in the scope of 5nm～5 μ m.
Secondly, when luminescent layer formation luminescent layer is set on hole injection layer, also can adopt required luminous organic material, methods such as employing vacuum vapour deposition, sputtering method, spin-coating method, casting method make organic luminescent material thin-filmization and form, because vacuum vapour deposition obtains homogeneous membrane easily, and be not easy to produce pin hole etc., therefore preferred this method of employing forms.When adopting vacuum vapour deposition to form luminescent layer, its evaporation condition is different because of employed compound, generally can select in the condition and range identical with hole injection layer.
Then, on this luminescent layer, electron injecting layer is set.The same with hole injection layer and luminescent layer, in order to obtain homogeneous membrane, preferably adopt vacuum vapour deposition to form.The evaporation condition can from the same condition and range of hole injection layer, luminescent layer in select.
Can obtain organic EL by stacked negative electrode at last.
Because negative electrode is made of metal, therefore can use vapour deposition method, sputtering method.But, the damage when avoiding making film, preferred vacuum vapour deposition for the organic matter layer that makes substrate.
So far the making of the organic EL of being put down in writing is preferably made from the anode to the negative electrode by once vacuumizing consistently.
The formation method of each layer of organic EL of the present invention is not particularly limited.Can use the formation method of existing known employing vacuum vapour deposition, spin-coating method etc.In addition, organic thin film layer can adopt the dip coating, spin-coating method, casting method, the rod that use vacuum vapour deposition, molecular beam vapour deposition method (MBE method) or be dissolved in the solution in the solvent to be coated with the known method formation of rubbing methods such as method, rolling method.
The thickness of each organic layer of organic EL of the present invention is not particularly limited, and general thickness is crossed when thin, is easy to generate the defective of pin hole etc., and is opposite when blocked up, needs high applied voltage, and deterioration of efficiency is therefore preferred usually in the scope of several nm to 1 μ m.
In addition, to the organic EL impressed DC voltage time, if make anode be+, negative electrode for-polarity add the voltage of 5～40V, may observe is luminous.And with opposite polarity applied voltage the time, electric current does not flow through, and does not produce luminous fully.Further when adding alternating voltage, only make anode be+, negative electrode for-polarity chron can observe the luminous of homogeneous.The AC wave shape that adds can be random waveform.
Organic EL of the present invention, it is luminous to carry out the high arrowband of colorimetric purity, excellent especially as the element of blue-light-emitting.And the life-span also improves.
[embodiment]
Below embodiments of the invention are elaborated, but the present invention is not subjected to the restriction of these embodiment.
In addition, the element of the character of the compound that uses in each embodiment and making is estimated in accordance with the following methods.
(1) energy gap: the absorption edge of the absorption spectrum from benzene is measured.Particularly, use commercially available visible ultraviolet spectrophotometer to measure absorption spectrum, the wavelength when its absorption spectrum begins to rise is calculated.
(2) briliancy: adopt and divide light emission brightness photometer (CS-1000, ミ ノ Le system) to measure.
(3) luminous intensity of luminous very big wavelength: under the condition same, make the monofilm of first luminescent layer and second luminescent layer respectively, use commercially available fluorescence determination device to measure the fluorescence spectrum of each monofilm with making EL element.From the fluorescence spectrum of first luminescent layer of gained, measure the fluorescence intensity Ia of first luminescent layer at the luminous very big wavelength a place of first luminescent layer.Equally, from the fluorescence spectrum of second luminescent layer of gained, measure the fluorescence intensity Ib of second luminescent layer at the luminous very big wavelength b place of second luminescent layer.
When the luminous very big wavelength of first luminescent layer and second luminescent layer fully separated, in the luminescent spectrum of EL element, luminous intensity Ia, the Ib at the wavelength place of a, b can be approximately I1, I2 respectively.
When the luminous maximum wave appearance mutual connection of first luminescent layer and second luminescent layer is near, the luminescent spectrum of EL element integral body can be assumed to from the luminescent spectrum of first luminescent layer and from the luminescent spectrum of second luminescent layer and.
Therefore, in the fluorescence spectrum of first luminescent layer of gained, measure fluorescence intensity I1a, the I1b of wavelength a, b.Equally, in the fluorescence spectrum of second luminescent layer of gained, measure fluorescence intensity I2a, the I2b of wavelength a, b.For I1, I2, following formula is set up.
Ia＝I1*I1a+I2*I2a
Ib＝I1*I1b+I2*I2b
By above-mentioned formula, obtain the ratio of I1, I2.
(4) luminous efficiency: calculate from current density value and the briliancy (100 nit) of using multitester measuring.
(5) C.I.E chromaticity coordinate: by similarly measuring acquisition with (2).
(6) life-span half-life: briliancy is 1000 nits, decides under the current condition in the early stage, and the element of sealing is measured.(room temperature)
(7) electron mobility: calculate according to Time of flight method.Particularly, for the formation of ITO/ organic layer (1～2 micron of electron injecting layer etc., bed thickness)/Al, measure because the time response (transient characteristic time) of the transient current that rayed produces is obtained electron mobility according to following formula.
Electron mobility=(organic bed thickness)
2/ (transient characteristic time electric field strength)
Below show the compound that uses in an embodiment.
The glass substrate that has ito transparent electrode (ジ オ マ テ that 25mm * 75mm * 1.1mm is thick in isopropyl alcohol
ィ ッNetwork company makes) carry out 5 minutes ultrasonic waves for cleaning, after this, carry out 30 minutes UV ozone clean.
The glass substrate that has transparent electrode lines after cleaning is installed on the substrate support of vacuum deposition apparatus, at first on the face that has formed the transparent electrode lines side to cover the mode of above-mentioned transparency electrode, forming thickness is the N of 60nm, N '-two (N, N '-diphenyl-4-aminophenyl)-N, N-diphenyl-4,4 '-diaminostilbene, 1 '-biphenyl film (below be abbreviated as " TPD232 film ").This TPD232 film performance is as the function of hole injection layer.
After TPD232 film film forming, forming thickness on the TPD232 film is the N of 20nm, N, N ', N '-four (4-xenyl)-benzidine layer (hereinafter referred to as " TBDB layer ").This film has the function as hole transporting layer.
To be that the mode of 1.0: 20 (weight ratio) is carried out evaporation according to the ratio of D1: H1 as the H1 of the host material of first luminescent layer with as the D1 of first dopant further, forming thickness be the layer (first dopant is about 5.4mol%) of 20nm.This layer has the function as first luminescent layer.
To be that the mode of 1.0: 20 (weight ratio) is carried out evaporation according to the ratio of D2: H1 as the H1 of the host material of second luminescent layer with as the D2 of second dopant further, forming thickness be the layer (second dopant is about 5.7mol%) of 20nm.This layer has the function as second luminescent layer.
Forming thickness on this film is the Alq film of 10nm.This layer has the function of electron injecting layer.
In addition, the electron mobility of Alq is 5 * 10
-6Cm
2/ (V second) (E=5 * 10
5V/cm).
After this, will be as Li (the Li source: サ エ ス グ of reproducibility dopant
ッ-company makes) and Alq carry out the binary evaporation, formation is as the Alq:Li film (thickness is 10nm) of electron injecting layer (negative electrode).Evaporation metal Al on this Alq:Li film forms metallic cathode, forms organic EL luminous element thus.
Except the thickness that makes first luminescent layer is that the ratio of 10nm, D1: H1 is 0.3: 10 (weight ratio), the thickness that makes second luminescent layer be the ratio of 30nm, D2: H1 be 1.4: 30 (weight ratio) in addition, according to making organic EL (first dopant is about 3.3mol%, and second dopant is about 5.3mol%) with embodiment 1 duplicate mode.
Except the thickness that makes first luminescent layer is that the ratio of 20nm, D1: H1 is 0.5: 20 (weight ratio), the thickness that makes second luminescent layer be the ratio of 20nm, D2: H1 be 1.0: 20 (weight ratio) in addition, according to making organic EL (first dopant is about 2.8mol%, and second dopant is about 5.7mol%) with embodiment 1 duplicate mode.
Except the thickness that makes first luminescent layer is 20nm, adopt D2 to replace D1, make D2: the ratio of H1 is 1.0: 20 (weight ratio), the thickness that makes second luminescent layer is 20nm, adopt D3 to replace D2, and the ratio that makes D3: H1 be 1.0: 20 (weight ratio) in addition, according to making organic EL (first dopant is about 5.7mol%, and second dopant is about 4.8mol%) with embodiment 1 duplicate mode.
Except the Alq that uses ETM-020 replacement formation electron injecting layer, according to making organic EL with embodiment 4 duplicate modes.
Wherein, the electron mobility of ETM-020 is 4 * 10
-4Cm
2/ (V second) (E=5 * 10
5V/cm).
Comparative example 1
Except the thickness that makes first luminescent layer is that the ratio of 20nm, D1: H1 is 1.0: 20 (weight ratio), the thickness that makes second luminescent layer is 20nm, does not use beyond the D2, according to making organic EL (first dopant is about 5.4mol%, and second dopant is 0mol%) with embodiment 1 duplicate mode.
Comparative example 2
Except the thickness that makes first luminescent layer is 20nm, use D2 to replace D1, make that the ratio of D2: H1 is 1.0: 20 (weight ratio), the thickness that makes second luminescent layer is 20nm, do not use beyond the D2, according to making organic EL (first dopant is about 5.7mol%, and second dopant is 0mol%) with embodiment 1 duplicate mode.
Comparative example 3
Except the thickness that makes first luminescent layer is 20nm, use D2 to replace D1, make D2: the ratio of H1 is 1.0: 20 (weight ratio), the thickness that makes second luminescent layer is 20nm, make D1: the ratio of H1 be 1.0: 20 (weight ratio) in addition, according to making organic EL (first dopant is about 5.7mol%, and second dopant is about 5.4mol%) with embodiment 1 duplicate mode.
Comparative example 4
Except the thickness that makes first luminescent layer is 20nm, use D3 to replace D1, make D3: the ratio of H1 is 1.0: 20 (weight ratio), the thickness that makes second luminescent layer is 20nm, do not use beyond the D2, according to making organic EL (first dopant is about 4.8mol%, and second dopant is 0mol%) with embodiment 1 duplicate mode.
Comparative example 5
Except the thickness that makes first luminescent layer is 20nm, use D3 to replace D1, make D3: the ratio of H1 is 1.0: 20 (weight ratio), make D2: the ratio of H1 be 1.0: 20 (weight ratio) in addition, according to making organic EL (first dopant is about 4.8mol%, and second dopant is about 5.7mol%) with embodiment 1 duplicate mode.
Comparative example 6
Except second luminescent layer is had the structure identical with first luminescent layer, make organic EL according to the mode the same with embodiment 5.
For the organic EL of making in embodiment 1～5 and the comparative example 1～6, measure ratio (I1/I2), initial stage luminous efficiency, C.I.E chromaticity coordinate and life-span half-life of luminous intensity (I2) of luminous very big wavelength of the luminescent spectrum of the luminous intensity (I1) of luminous very big wavelength of luminescent spectrum of formation, the first luminescent layer origin of the luminescent layer of each organic EL and the above-mentioned second luminescent layer origin.The result has been shown in the table 1.
Table 1
| First luminescent layer (Egh/Egd1) | Second luminescent layer (Egh/Egd2) | I1/ I2 | Luminous efficiency (cd/A) | The C.I.E chromaticity coordinate | Life-span half-life | |
| Embodiment 1 | H1/D1 (3.0eV/2.9eV) | H1/D2 (3.0eV/2.8eV) | 80/20 | 6.7 | 0.15，0.17 | 3,000 |
| Embodiment 2 | H1/D1 (3.0eV/2.9eV) | H1/D2 (3.0eV/2.8eV) | 55/45 | 7.4 | 0.15，0.20 | 3,500 |
| Embodiment 3 | H1/D1 (3.0eV/2.9eV) | H1/D2 (3.0eV/2.8eV) | 80/20 | 6.3 | 0.15，0.16 | 2,500 |
| Comparative example 1 | H1/D1 (3.0eV/2.9eV) | H1 (3.0eV) | 100/0 | 5.3 | 0.15，0.15 | 1,500 |
| Comparative example 2 | H1/D2 (3.0eV/2.8eV) | H1 (3.0eV) | 100/0 | 11.5 | 0.16，0.31 | 3,700 |
| Comparative example 3 | H1/D2 (3.0eV/2.8eV) | H1/D1 (3.0eV/2.9eV) | 100/0 | 11.9 | 0.16，0.30 | 2,900 |
| Embodiment 4 | H1/D2 (3.0eV/2.8eV) | H1/D3 (3.0eV/2.6eV) | 90/10 | 6.8 | 0.25，0.26 | 13,000 |
| Comparative example 4 | H1/D3 (3.0eV/2.6eV) | H1 (3.0eV) | 100/0 | 8.2 | 0.50，0.48 | 15,000 |
| Comparative example 5 | H1/D3 (3.0eV/2.6eV) | H1/D2 (3.0eV/2.8eV) | 100/0 | 8.3 | 0.49，0.48 | 14,000 |
| Embodiment 5 | H1/D2 (3.0eV/2.8eV) | H1/D3 (3.0eV/2.6eV) | 100/0 | 13.5 | 0.16，0.31 | 8,000 |
| Comparative example 6 | H1/D2 (3.0eV/2.8eV) | H1/D2 (3.0eV/2.8eV) | 100/0 | 10.0 | 0.16，0.31 | 1,500 |
As known from Table 1, only use the organic EL of the big dopant of energy gap, colorimetric purity is good, but luminous efficiency is low, and life-span half-life is short.On the contrary, only use the organic EL of the little dopant of energy gap, the luminous efficiency height, life-span half-life is long, but colorimetric purity is poor, is unsuitable for panchromatic purposes.
But organic EL of the present invention is compared with the situation of merely only using the big dopant of energy gap, and life-span and luminous efficiency all improve, and colorimetric purity also changes hardly, and therefore it is specially adapted to panchromatic purposes as can be known.
In addition, in embodiment 5 and comparative example 6, in electron injecting layer, used the high ETM-020 of electron mobility, therefore can only make first luminescent layer luminous (I2=0).In this case, satisfy important document of the present invention, can significantly improve life-span half-life, can make effect of the present invention definitely very big by the energy gap that makes first dopant and second dopant.
According to the present invention, can provide and carry out the organic EL that the high arrowband of colorimetric purity is luminous and the life-span is long.
Claims (24)
1. organic electroluminescent device, it contains in the following order
Anode,
At least contain first host material and first dopant first luminescent layer,
At least contain second host material and second dopant second luminescent layer,
And negative electrode, it is characterized by:
The energy gap E of described first host material
Gh1, the energy gap E of described first dopant
Gd1, the energy gap E of described second host material
Gh2 and the energy gap E of described second dopant
Gd2 satisfy following formula,
And satisfy following formula from the luminous intensity I1 of the luminous very big wavelength of the luminescent spectrum of described first luminescent layer with from the luminous intensity I2 of the luminous very big wavelength of the luminescent spectrum of described second luminescent layer:
E
gh1＞E
gd1
E
gh2＞E
gd2
E
gd1＞E
gd2
I1＞3.5×I2。
2. organic electroluminescent device as claimed in claim 1 is characterized by the relation that satisfies I1＞5 * I2.
3. organic electroluminescent device as claimed in claim 1 or 2 is characterized by E
Gd2＞2.7eV.
4. organic electroluminescent device as claimed in claim 1 is characterized by in described first luminescent layer, and described first dopant is 0.1～10mol% with respect to the ratio of described first host material.
5. organic electroluminescent device as claimed in claim 1 is characterized by in described second luminescent layer, and described second dopant is 0.1～10mol% with respect to the ratio of described second host material.
6. organic electroluminescent device as claimed in claim 1, at least one side who it is characterized by described first or second host material is the compound of following general formula [1] expression,
In the formula, Ar
1For the nucleus carbon atom number is 6～50 aromatic ring, X is a substituting group,
M is 1～5 integer, and n is 0～6 integer, when m 〉=2, and Ar
1Can be identical or different respectively, when n 〉=2, X can be identical or different respectively.
7. organic electroluminescent device as claimed in claim 1, it is identical with described second host material to it is characterized by described first host material.
8. organic electroluminescent device as claimed in claim 1, at least one side who it is characterized by described first or second dopant material is the compound of following general formula [2] expression,
In the formula, Ar
2～Ar
4For replacing or unsubstituted nucleus carbon atom number is 6～50 aromatic group, replacement or unsubstituted styryl, p is 1～4 integer, p 〉=2 o'clock, Ar
3And Ar
4Can be identical or different respectively.
9. organic electroluminescent device as claimed in claim 1, the thickness that it is characterized by described first luminescent layer is more than the 10nm.
10. organic electroluminescent device as claimed in claim 1, the luminous intensity I2 that it is characterized by from the luminous very big wavelength of the luminescent spectrum of described second luminescent layer is I2=0.
11. organic electroluminescent device as claimed in claim 1 is characterized by between described second luminescent layer and negative electrode electron injecting layer is set, the electron mobility of this electron injecting layer is 10
-4Cm
2/ more than (V second).
12. organic electroluminescent device as claimed in claim 11 is characterized by described electron injecting layer and contains nitogen-contained heterocycle derivant.
13. organic electroluminescent device as claimed in claim 12, it is characterized by described nitogen-contained heterocycle derivant is Imidazopyrazines derivative and/or imdazole derivatives.
14. an organic electroluminescent device, it contains in the following order
Anode,
At least contain first host material and first dopant first luminescent layer,
At least contain second host material and second dopant second luminescent layer,
And negative electrode, it is characterized by:
The energy gap E of described first host material
Gh1, the energy gap E of described first dopant
Gd1, the energy gap E of described second host material
Gh2 and the energy gap E of described second dopant
Gd2 satisfy following formula:
E
gh1＞E
gd1
E
gh2＞E
gd2
E
gd1＞E
gd2＞2.7eV。
15. organic electroluminescent device as claimed in claim 14 is characterized by in described first luminescent layer, described first dopant is 0.1～10mol% with respect to the ratio of described first host material.
16. organic electroluminescent device as claimed in claim 14 is characterized by in described second luminescent layer, described second dopant is 0.1～10mol% with respect to the ratio of described second host material.
17. organic electroluminescent device as claimed in claim 14, at least one side who it is characterized by described first or second host material is the compound of following general formula [1] expression,
In the formula, Ar
1For the nucleus carbon atom number is 6～50 aromatic ring, X is a substituting group,
M is 1～5 integer, and n is 0～6 integer, when m 〉=2, and Ar
1Can be identical or different respectively, when n 〉=2, X can be identical or different respectively.
18. organic electroluminescent device as claimed in claim 14, it is identical with described second host material to it is characterized by described first host material.
19. organic electroluminescent device as claimed in claim 14, at least one side who it is characterized by described first or second dopant material is the compound of following general formula [2] expression,
In the formula, Ar
2～Ar
4For replacing or unsubstituted nucleus carbon atom number is 6～50 aromatic group, replacement or unsubstituted styryl, p is 1～4 integer, p 〉=2 o'clock, Ar
3And Ar
4Can be identical or different respectively.
20. organic electroluminescent device as claimed in claim 14, the thickness that it is characterized by described first luminescent layer is more than the 10nm.
21. organic electroluminescent device as claimed in claim 14, the luminous intensity I2 that it is characterized by from the luminous very big wavelength of the luminescent spectrum of described second luminescent layer is I2=0.
22. organic electroluminescent device as claimed in claim 14 is characterized by between described second luminescent layer and negative electrode electron injecting layer is set, the electron mobility of this electron injecting layer is 10
-4Cm
2/ more than (V second).
23. organic electroluminescent device as claimed in claim 22 is characterized by described electron injecting layer and contains nitogen-contained heterocycle derivant.
24. organic electroluminescent device as claimed in claim 23, it is characterized by described nitogen-contained heterocycle derivant is Imidazopyrazines derivative and/or imdazole derivatives.
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| CN103682117B (en) * | 2013-12-31 | 2017-10-27 | 北京维信诺科技有限公司 | A kind of organic light emission lighting device |
| CN106856225B (en) | 2016-12-15 | 2019-10-15 | 上海天马有机发光显示技术有限公司 | A kind of organic light emitting display panel and device |
| CN110752307B (en) * | 2019-10-31 | 2022-11-15 | 昆山国显光电有限公司 | Light emitting device and display panel |
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| JP4631122B2 (en) * | 2000-02-21 | 2011-02-16 | Ｔｄｋ株式会社 | Organic EL device |
| JP4718025B2 (en) * | 2001-03-16 | 2011-07-06 | 保土谷化学工業株式会社 | Benzimidazole derivatives and organic electroluminescent devices |
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