JP3196230B2 - Organic electroluminescent device - Google Patents
Organic electroluminescent deviceInfo
- Publication number
- JP3196230B2 JP3196230B2 JP10754091A JP10754091A JP3196230B2 JP 3196230 B2 JP3196230 B2 JP 3196230B2 JP 10754091 A JP10754091 A JP 10754091A JP 10754091 A JP10754091 A JP 10754091A JP 3196230 B2 JP3196230 B2 JP 3196230B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- organic
- electroluminescent device
- layer
- transport layer
- 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
Links
- 238000002347 injection Methods 0.000 claims description 46
- 239000007924 injection Substances 0.000 claims description 46
- 239000000463 material Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 230000005684 electric field Effects 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001935 tetracenyl group Chemical class C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims 1
- 230000032258 transport Effects 0.000 description 43
- -1 polycyclic aromatic compound Chemical class 0.000 description 24
- 150000003518 tetracenes Chemical class 0.000 description 17
- 239000000758 substrate Substances 0.000 description 16
- 239000007850 fluorescent dye Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229960003540 oxyquinoline Drugs 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 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
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- SULWTXOWAFVWOY-PHEQNACWSA-N 2,3-bis[(E)-2-phenylethenyl]pyrazine Chemical class C=1C=CC=CC=1/C=C/C1=NC=CN=C1\C=C\C1=CC=CC=C1 SULWTXOWAFVWOY-PHEQNACWSA-N 0.000 description 1
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical class O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- OAIASDHEWOTKFL-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(4-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C)C=CC=1)C1=CC=CC=C1 OAIASDHEWOTKFL-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910001111 Fine metal Inorganic materials 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- CELAVSIYCCQNGG-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1CCCCC1)C1=CC=C(C)C=C1 CELAVSIYCCQNGG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical class C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は有機電界発光素子に関す
るものであり、詳しくは、有機化合物から成る正孔注入
輸送層と電子注入輸送層との組合せにより、電界をかけ
て光を放出する薄膜型デバイスに関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device, and more particularly, to a thin film which emits light by applying an electric field by a combination of a hole injection transport layer and an electron injection transport layer made of an organic compound. It concerns a type device.
【０００２】[0002]
【従来の技術】従来、薄膜型の電界発光素子としては、
無機材料のＩＩ−ＶＩ族化合物半導体であるＺｎＳ、Ｃ
ａＳ、ＳｒＳ等に、発光中心であるＭｎや希土類元素
（Ｅｕ、Ｃｅ、Ｔｂ、Ｓｍ等）をドープしたものが一般
的であるが、上記の無機材料から作製した電界発光素子
は、 交流駆動が必要（５０〜１０００Ｈｚ）、
駆動電圧が高い（〜２００Ｖ）、 フルカラー化が困
難（特に青色が問題）、 周辺駆動回路のコストが高
い、という問題点を有している。2. Description of the Related Art Conventionally, as a thin film type electroluminescent device,
ZnS, C which are II-VI compound semiconductors of inorganic materials
In general, aS, SrS, and the like are doped with Mn or a rare earth element (Eu, Ce, Tb, Sm, or the like) that is a light emission center. Required (50-1000Hz)
There are problems that the driving voltage is high (up to 200 V), it is difficult to achieve full color (particularly, blue is a problem), and the cost of the peripheral driving circuit is high.
【０００３】これに対して、近年、上記問題点の改良の
ため、有機材料を用いた電界発光素子の開発が行われる
ようになった。有機発光層材料としては以前から知られ
ていたアントラセンやピレン等の他に、シアニン色素
（J. Chem. Soc., Chem. Commun., ５５７頁、１９８５
年）、ピラゾリン（Mol. Crys. Liq. Cryst., １３５
巻、３５５頁、１９８６年）、ペリレン（Jpn. J. App
l. Phys., ２５巻、Ｌ７７３頁、１９８６年）、或い
は、クマリン系化合物やテトラフェニルブタジエン（特
開昭５７−５１７８１号公報）などが報告されており、
更に、発光効率を高めるために電極からのキャリアーの
注入効率の向上を目的として、電極種類の最適化や、正
孔注入輸送層と有機蛍光体からなる発光層を設ける工夫
（特開昭５７−５１７８１号公報、特開昭５９−１９４
３９３号公報、特開昭６３−２９５６９５号公報、App
l. Phys. Lett.,５１巻、９１３頁、１９８７年）等が
行われている。On the other hand, in recent years, an electroluminescent device using an organic material has been developed to improve the above problem. As organic luminescent layer materials, in addition to anthracene and pyrene which have been known for a long time, cyanine dyes (J. Chem. Soc., Chem. Commun., P. 557, 1985)
Years), pyrazoline (Mol. Crys. Liq. Cryst., 135
Volume, p. 355, 1986), Perylene (Jpn. J. App
l. Phys., 25, L773, 1986), or coumarin compounds and tetraphenylbutadiene (JP-A-57-51781).
Furthermore, in order to improve the efficiency of injecting carriers from the electrodes in order to enhance the luminous efficiency, the type of the electrodes is optimized, and a device for providing a hole injection / transport layer and a luminescent layer composed of an organic phosphor is disclosed (Japanese Patent Application Laid-Open No. Sho 57-57). No. 51781, JP-A-59-194.
393, JP-A-63-29569, App
l. Phys. Lett., 51, 913, 1987).
【０００４】また、素子の発光効率を向上させるととも
に発光色を変える目的で、８−ヒドロキシキノリンのア
ルミニウム錯体をホスト材料として、クマリン等のレー
ザ用蛍光色素をドープすること（J. Appl. Phys., ６５
巻、３６１０頁、１９８９年）も行われているが、ドー
プ量により発光波長が変わるので、ドープ量の厳密な制
御が必要とされるという不具合がある。Further, for the purpose of improving the luminous efficiency of the device and changing the luminescent color, a fluorescent dye for laser such as coumarin is doped using an aluminum complex of 8-hydroxyquinoline as a host material (J. Appl. Phys. , 65
Vol. 3610, 1989). However, since the emission wavelength changes depending on the doping amount, there is a problem that strict control of the doping amount is required.
【０００５】また、アントラセンをホスト材料として、
縮合多環芳香族化合物である下記構造式のペリレン（Ｎ
１）やナフタセン（Ｎ２）をドープして発光させること
も検討されてきているが（Ｊｐｎ．Ｊ．Ａｐｐｌ．Ｐｈ
ｙｓ．，１０巻、５２７頁、１９７１年；Ｍｏｌ．Ｃｒ
ｙｓｔ．Ｌｉｑ．Ｃｒｙｓｔ．，７２巻、１１３頁、１
９８１年；電子通信学会技術研究報告、ＯＭＥ８９−４
８、１９８９年）、駆動電圧が高く、発光輝度としては
低い値しか得られていない。Further, using anthracene as a host material,
A condensed polycyclic aromatic compound, perylene of the following structural formula (N
1) and doping with naphthacene (N2) to emit light have been studied (Jpn. J. Appl. Ph.
ys. , 10, 527, 1971; Mol. Cr
yst. Liq. Cryst. , 72, 113 pages, 1
981; IEICE Technical Report, OME89-4
8, 1989), the driving voltage is high, and only a low value is obtained as the light emission luminance.
【０００６】[0006]
【化２】 Embedded image
【０００７】[0007]
【化３】 Embedded image
【０００８】[0008]
【発明が解決しようとする課題】上記のように、これま
でに開示されている有機電界発光素子では、発光性能、
特に発光効率が未だ不十分であり、更なる改良検討が望
まれていた。As described above, in the organic electroluminescent devices disclosed so far, the luminous performance,
In particular, the luminous efficiency is still insufficient, and further improvement studies have been desired.
【０００９】本発明は上記従来の実状に鑑みてなされた
ものであり、高発光効率で駆動させることができる有機
電界発光素子を提供することを目的とする。The present invention has been made in view of the above-mentioned conventional situation, and has as its object to provide an organic electroluminescent device which can be driven with high luminous efficiency.
【００１０】[0010]
【課題を解決するための手段】本発明の有機電界発光素
子は、順次に、陽極、有機正孔注入輸送層、有機電子注
入輸送層及び陰極が積層されて成る有機電界発光素子に
おいて、有機正孔注入輸送層、或いは、有機正孔注入輸
送層及び有機電子注入輸送層が、下記一般式（Ｉ）で表
わされるナフタセン誘導体を含有することを特徴とす
る。According to the present invention, there is provided an organic electroluminescent device comprising an anode, an organic hole injecting / transporting layer, an organic electron injecting / transporting layer and a cathode which are sequentially laminated. Hole injection transport layer or organic hole injection transport
The transport layer and the organic electron injection / transport layer contain a naphthacene derivative represented by the following general formula (I).
【００１１】[0011]
【化４】 （式中、Ｒ１，Ｒ２，Ｒ３及びＲ４は水素原子、アルキ
ル基、アラルキル基、アルケニル基、アリル基、置換基
を有していても良い芳香族炭化水素環基又は芳香族複素
環基、ハロゲン原子、アミド基、アルコキシ基、アルコ
キシカルボニル基、ニトロ基、或いは置換基を有してい
ても良いアミノ基を表し、Ｒ １ 〜Ｒ ４ のうちの少なくと
も１つは、置換基を有していても良い芳香族炭化水素環
基又はハロゲン原子である。Ｒ５及びＲ６は水素原子、
ハロゲン原子、アルコキシ基、アルコキシカルボニル
基、又はアルキル基を示す。）Embedded image (Wherein R 1 , R 2 , R 3 and R 4 represent a hydrogen atom, an alkyl group, an aralkyl group, an alkenyl group, an allyl group, an aromatic hydrocarbon ring group which may have a substituent or an aromatic heterocyclic group) A ring group, a halogen atom, an amide group, an alkoxy group, an alkoxycarbonyl group, a nitro group, or an amino group which may have a substituent, and at least one of R 1 to R 4
One is an aromatic hydrocarbon ring which may have a substituent.
Group or a halogen atom. R 5 and R 6 are a hydrogen atom,
It represents a halogen atom, an alkoxy group, an alkoxycarbonyl group, or an alkyl group. )
【００１２】即ち、本発明者らは、高発光効率で駆動さ
せることができる有機電界発光素子について、鋭意検討
した結果、有機正孔注入輸送層、或いは、有機正孔注入
輸送層及び有機電子注入輸送層が特定の化合物を含有す
ることが好適であることを見出し、本発明を完成した。That is, the present inventors have made intensive studies on an organic electroluminescent device which can be driven with high luminous efficiency. As a result, an organic hole injecting / transporting layer or an organic hole injecting device was developed.
It has been found that the transport layer and the organic electron injection / transport layer preferably contain a specific compound, and the present invention has been completed.
【００１３】以下に、本発明の有機電界発光素子につい
て、図面を参照して詳細に説明する。Hereinafter, the organic electroluminescent device of the present invention will be described in detail with reference to the drawings.
【００１４】第１図は本発明の有機電界発光素子の構造
例を模式的に示す断面図であり、１は基板、２ａ、２ｂ
は導電層、３は有機正孔注入輸送層、４は有機電子注入
輸送層を各々表す。FIG. 1 is a cross-sectional view schematically showing an example of the structure of an organic electroluminescent device of the present invention, wherein 1 is a substrate, 2a, 2b
Represents a conductive layer, 3 represents an organic hole injecting and transporting layer, and 4 represents an organic electron injecting and transporting layer.
【００１５】基板１は本発明の有機電界発光素子の支持
体となるものであり、通常、石英やガラスの板、金属板
や金属箔、プラスチックフィルムやシートなどが用いら
れるが、これらのうち、ガラス板や、ポリエステル、ポ
リメチルメタアクリレート、ポリカーボネート、ポリス
ルホンなどの透明な合成樹脂基板が好ましい。The substrate 1 serves as a support for the organic electroluminescent device of the present invention. Usually, a quartz or glass plate, a metal plate or a metal foil, a plastic film or a sheet, or the like is used. A glass plate or a transparent synthetic resin substrate such as polyester, polymethyl methacrylate, polycarbonate, and polysulfone is preferable.
【００１６】基板１上には導電層２ａが設けられる。こ
の導電層２ａは、通常、アルミニウム、金、銀、ニッケ
ル、パラジウム、テルル等の金属、インジウム及び／又
はスズの酸化物などの金属酸化物やヨウ化銅、カーボン
ブラック、或いは、ポリ（３−メチルチオフェン）等の
導電性樹脂などにより構成される。On the substrate 1, a conductive layer 2a is provided. The conductive layer 2a is usually made of a metal such as aluminum, gold, silver, nickel, palladium, and tellurium, a metal oxide such as an oxide of indium and / or tin, copper iodide, carbon black, or poly (3- (Methylthiophene) and the like.
【００１７】第１図の例では、導電層２ａは陽極（アノ
ード）として正孔注入の役割を果たすものである。一
方、導電層２ｂは陰極（カソード）として有機電子注入
輸送層４に電子を注入する役割を果たす。導電層２ｂの
構成材料としては、前記導電層２ａの構成材料を用いる
ことが可能であるが、効率良く電子注入を行うには、仕
事関数の低い値をもつ金属が好ましく、例えば、スズ、
マグネシウム、インジウム、アルミニウム、銀等の適当
な金属又はそれらの合金が好適である。In the example shown in FIG. 1, the conductive layer 2a functions as an anode (anode) for injecting holes. On the other hand, the conductive layer 2b plays a role of injecting electrons into the organic electron injection / transport layer 4 as a cathode (cathode). As the constituent material of the conductive layer 2b, the constituent material of the conductive layer 2a can be used. However, for efficient electron injection, a metal having a low work function is preferable.
Suitable metals such as magnesium, indium, aluminum, silver and the like or alloys thereof are preferred.
【００１８】導電層２ａ、２ｂの形成は、通常、スパッ
タリング法、真空蒸着法などにより行われることが多い
が、銀などの金属微粒子或いはヨウ化銅、カーボンブラ
ック、導電性の金属酸化物微粒子、導電性樹脂微粉末な
どの場合には、これらの粉末を適当なバインダー樹脂溶
液に分散し、基板上に塗布することにより形成すること
もできる。更に、導電性樹脂の場合は電界重合により直
接基板上に薄膜を形成することもできる。なお、導電層
２ａ、２ｂは２以上の物質を積層してなる複合層であっ
ても良い。The conductive layers 2a and 2b are usually formed by a sputtering method, a vacuum deposition method, or the like. However, fine metal particles such as silver or copper iodide, carbon black, conductive metal oxide fine particles, In the case of a conductive resin fine powder or the like, these powders can also be formed by dispersing these powders in an appropriate binder resin solution and applying the powder on a substrate. Further, in the case of a conductive resin, a thin film can be formed directly on a substrate by electric field polymerization. Note that the conductive layers 2a and 2b may be composite layers formed by laminating two or more substances.
【００１９】導電層２ａの厚みは、必要とする透明性に
より異なるが、透明性が必要とされる場合は、可視光の
透過率が６０％以上、好ましくは８０％以上透過するこ
とが望ましく、この場合、厚みは、通常、５０〜１０，
０００Å、好ましくは１００〜５，０００Å程度であ
る。なお、導電層２ａが不透明で良い場合は、導電層２
ａの材質は基板１と同一でも良く、また、更には導電層
を前記導電層構成材料と異なる他の物質で積層すること
も可能である。一方、導電層２ｂの膜厚は、通常の場
合、導電層２ａの膜厚と同程度とされる。The thickness of the conductive layer 2a varies depending on the required transparency. If transparency is required, the transmittance of visible light is desirably 60% or more, preferably 80% or more. In this case, the thickness is usually 50 to 10,
000 °, preferably about 100 to 5,000 °. When the conductive layer 2a may be opaque, the conductive layer 2a
The material of a may be the same as that of the substrate 1, and furthermore, the conductive layer may be laminated with another material different from the conductive layer constituting material. On the other hand, the thickness of the conductive layer 2b is generally equal to the thickness of the conductive layer 2a.
【００２０】第１図には示していないが、この導電層２
ｂの上に更に基板１と同様の基板を設けることもでき
る。但し、導電層２ａと２ｂの少なくとも一方は透明性
の良いことが電界発光素子としては必要である。このこ
とから、導電層２ａと２ｂの少なくとも一方は、１００
〜５，０００Åの膜厚であることが好ましく、透明性の
良いことが望まれる。Although not shown in FIG. 1, this conductive layer 2
A substrate similar to the substrate 1 can be further provided on b. However, at least one of the conductive layers 2a and 2b needs to have good transparency as an electroluminescent element. From this, at least one of the conductive layers 2a and 2b
The thickness is preferably 5,000 to 5,000, and good transparency is desired.
【００２１】導電層２ａの上に設けられる有機正孔注入
輸送層３は、電界を与えられた電極間において、陽極か
らの正孔を効率良く有機電子注入輸送層４の方向に輸送
することができる化合物より形成されることが必要とさ
れる。従って、有機正孔注入輸送化合物としては、導電
層２ａからの正孔注入効率が高く、かつ、注入された正
孔を効率良く輸送することができる化合物であることが
必要である。そのためには、イオン化ポテンシャルが小
さく、しかも正孔移動度が大きく、更に安定性に優れ、
トラップとなる不純物が製造時や使用時に発生し難い化
合物であることが要求される。The organic hole injecting and transporting layer 3 provided on the conductive layer 2a can efficiently transport holes from the anode in the direction of the organic electron injecting and transporting layer 4 between the electrodes to which an electric field is applied. It needs to be formed from a compound that can. Therefore, the organic hole injection / transport compound needs to be a compound having a high hole injection efficiency from the conductive layer 2a and capable of efficiently transporting the injected holes. For this purpose, the ionization potential is small, the hole mobility is large, and the stability is excellent.
It is required that impurities serving as traps are compounds that hardly occur during production or use.
【００２２】このような正孔注入輸送化合物は、例え
ば、特開昭５９−１９４３９３号公報の第５〜６頁及び
米国特許第４１７５９６０号の第１３〜１４欄に解説さ
れるものなどが挙げられる。これら化合物の好ましい具
体例としては、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−（３
−メチルフェニル）−１，１’−ビフェニル−４，４’
−ジアミン：１，１’−ビス（４−ジ−ｐ−トリルアミ
ノフェニル）シクロヘキサン：４，４’−ビス（ジフェ
ニルアミノ）クワドロフェニルなどの芳香族アミン系化
合物が挙げられる。芳香族アミン系化合物以外では、特
開平２−３１１５９１号公報に示されるヒドラゾン化合
物が挙げられる。これらの芳香族アミン化合物又はヒド
ラゾン化合物は、単独で用いられるか、必要に応じて、
各々、混合物として用いても良い。Such hole injecting and transporting compounds include, for example, those described in JP-A-59-194393, pp. 5-6 and US Pat. No. 4,175,960, columns 13-14. . Preferred specific examples of these compounds include N, N'-diphenyl-N, N '-(3
-Methylphenyl) -1,1'-biphenyl-4,4 '
-Diamine: 1,1'-bis (4-di-p-tolylaminophenyl) cyclohexane: aromatic amine compounds such as 4,4'-bis (diphenylamino) quadrophenyl. In addition to the aromatic amine compounds, hydrazone compounds described in JP-A-2-311591 can be mentioned. These aromatic amine compounds or hydrazone compounds are used alone or, if necessary,
Each of them may be used as a mixture.
【００２３】有機正孔注入輸送層３の上に設けられる有
機電子注入輸送層４は、電界を与えられた電極間におい
て、陰極からの電子を効率良く有機正孔注入輸送層の方
向に輸送することができる化合物より形成されることが
必要とされる。従って、有機電子注入輸送化合物として
は、導電層２ｂからの電子注入効率が高く、かつ、注入
された電子を効率良く輸送することができる化合物であ
ることが必要である。そのためには、電子親和力が大き
く、しかも電子移動度が大きく、更に安定性に優れ、ト
ラップとなる不純物が製造時や使用時に発生し難い化合
物であることが要求される。The organic electron injecting and transporting layer 4 provided on the organic hole injecting and transporting layer 3 efficiently transports electrons from the cathode in the direction of the organic hole injecting and transporting layer between the electrodes to which an electric field is applied. It is required to be formed from a compound that can. Therefore, the organic electron injecting and transporting compound needs to be a compound having high electron injecting efficiency from the conductive layer 2b and capable of efficiently transporting the injected electrons. For this purpose, it is required that the compound has high electron affinity, high electron mobility, excellent stability, and hardly generates impurities serving as traps during production or use.
【００２４】このような条件を満たす材料としては、テ
トラフェニルブタジエンなどの芳香族化合物（特開昭５
７−５１７８１号公報）、８−ヒドロキシキノリンのア
ルミニウム錯体などの金属錯体（特開昭５９−１９４３
９３号公報）、シクロペンタジエン誘導体（特開平２−
２８９６７５号公報）、ペリノン誘導体（特開平２−２
８９６７６号公報）、オキサジアゾール誘導体（特開平
２−２１６７９１号公報）、ビススチリルベンゼン誘導
体（特開平１−２４５０８７号公報、同２−２２２４８
４号公報）、ペリレン誘導体（特開平２−１８９８９０
号公報、同３−７９１号公報）、クマリン化合物（特開
平２−１９１６９４号公報、同３−７９２号公報）、希
土類錯体（特開平１−２５６５８４号公報）、ジスチリ
ルピラジン誘導体（特開平２−２５２７９３号公報）な
どが挙げられる。これらの化合物を用いた場合は、有機
電子注入輸送層は電子を輸送する役割と、正孔と電子の
再結合の際に発光をもたらす役割を同時に果たす。Materials satisfying such conditions include aromatic compounds such as tetraphenylbutadiene (Japanese Patent Laid-Open No.
And metal complexes such as aluminum complexes of 8-hydroxyquinoline (JP-A-59-1943).
No. 93), cyclopentadiene derivatives (Japanese Unexamined Patent Publication No.
289675), perinone derivatives (JP-A 2-2)
No. 89676), oxadiazole derivatives (Japanese Patent Application Laid-Open No. 2-216991), and bisstyrylbenzene derivatives (Japanese Patent Application Laid-Open Nos. 1-245087 and 2-222448).
No. 4), perylene derivatives (JP-A-2-189890)
JP-A-3-7991), coumarin compounds (JP-A-2-191694 and JP-A-3-792), rare-earth complexes (JP-A-1-256584), and distyrylpyrazine derivatives (JP-A-2-19584). 252793). When these compounds are used, the organic electron injecting and transporting layer simultaneously plays a role of transporting electrons and a role of emitting light when holes and electrons recombine.
【００２５】本発明の有機電界発光素子においては、こ
のような材料よりなる有機正孔注入輸送層、或いは有機
正孔注入輸送層及び有機電子注入輸送層に前記一般式
（Ｉ）で表されるナフタセン誘導体を含有させるが、通
常の場合、前記一般式（Ｉ）で表されるナフタセン誘導
体は、有機正孔注入輸送層３と有機電子注入輸送層４の
界面近傍の領域にドープされる。ドープされる層は、有
機正孔注入輸送層３、或いは、有機正孔注入輸送層３及
び有機電子注入輸送層４であり、各層の一部分の領域で
あっても良い。例えば、第２図に示す如く、有機正孔注
入輸送層３の有機電子注入輸送層４側の界面近傍の層３
ａであっても良く、第３図に示す如く、有機電子注入輸
送層４（４ａ）と有機正孔注入輸送層３の有機電子注入
輸送層４側の界面近傍の層３ａの両方であっても良い
（第２図、第３図において、３ａ、４ａはドープされた
領域、３ｂ、４ｂはドープされていない領域であり、符
号１，２ａ，２ｂ，３，４は第１図におけると同じもの
をさす。）。上記ナフタセン誘導体がホスト材料に対し
てドープされる量は１０−３〜１０モル％が好ましい。
なお、ホスト材料とは、例えば、有機電子注入輸送層４
がその役割を果たす場合、前述の有機電子注入輸送化合
物が挙げられ、有機正孔注入輸送層３がホスト材料とし
ての役割を果たす場合、前述の芳香族アミン化合物やヒ
ドラゾン化合物が挙げられる。In the organic electroluminescent device of the present invention, an organic hole injection / transport layer made of such a material ,
The hole injecting and transporting layer and the organic electron injecting and transporting layer contain the naphthacene derivative represented by the general formula (I). In general, the naphthacene derivative represented by the general formula (I) contains an organic hole. The region near the interface between the injection transport layer 3 and the organic electron injection transport layer 4 is doped. The layer to be doped is the organic hole injection / transport layer 3 or the organic hole injection / transport layer 3
Fine Organic an electron injecting and transporting layer 4 may be a region of a portion of each layer. For example, as shown in FIG. 2, organic hole injection transport layer 3 of the organic electron injecting and transporting layer 4 side of the layer near the interface 3
3 , the organic electron injecting and transporting layer 4 (4a) and the layer 3a near the interface of the organic hole injecting and transporting layer 3 on the organic electron injecting and transporting layer 4 side, as shown in FIG. good (FIG. 2 also Oite in FIG. 3, 3a, 4a is doped regions, 3b, is 4b is a region that is not doped, in the code 1, 2a, 2b, Figure 1 is 3,4 The same thing as.). The doping amount of the naphthacene derivative with respect to the host material is preferably 10 −3 to 10 mol%.
The host material is, for example, the organic electron injection / transport layer 4
When the organic hole injecting and transporting layer 3 plays a role as a host material, the above-mentioned aromatic amine compounds and hydrazone compounds are exemplified.
【００２６】前記一般式（Ｉ）において、Ｒ１，Ｒ２，
Ｒ３及びＲ４としては、水素原子；メチル基、エチル基
等の炭素数１〜６のアルキル基；メトキシエチル基、エ
トキシエチル基等のアルコキシアルキル基；メトキシ−
エトキシエチル基、ｎ−ブトキシエトキシエチル基等の
アルコキシアルコキシアルキル基；フェニルオキシエチ
ル基、ナフチルオキシエチル基、ｐ−クロロフェニルオ
キシエチル基等のアリールオキシアルキル基；ベンジル
基、フェネチル基、ｐ−クロロベンジル基、ｐ−ニトロ
ベンジル基等のアリールアルキル基；シクロヘキシルメ
チル基、シクロヘキシルエチル基、シクロペンチルエチ
ル基等のシクロアルキルアルキル基；アリルオキシエチ
ル基、３−ブロモアリルオキシエチル基等のアルケニル
オキシアルキル基；シアノエチル基、シアノメチル基等
のシアノアルキル基；ヒドロキシエチル基、ヒドロキシ
メチル基等のヒドロキシアルキル基；テトラヒドロフリ
ル基、テトラヒドロフリルエチル基等のテトラヒドロフ
リルアルキル基等の置換又は非置換のアルキル基、アリ
ル基、２−クロロアリル基等の置換又は非置換のアルケ
ニル基；フェニル基、ｐ−メチルフェニル基、ナフチル
基、ｍ−メトキシフェニル基等の置換又は非置換のアリ
ール基；シクロヘキシル基、シクロペンチル基等のシク
ロアルキル基；塩素原子、臭素原子等のハロゲン原子；
アミド基；メトキシ基、エトキシ基等の炭素数１〜６の
アルコキシ基；メトキシカルボニル基、エトキシカルボ
ニル基等の炭素数１〜６のアルコキシカルボニル基；ニ
トロ基；置換基を有していても良いアミノ基が挙げられ
るが、好ましくは、置換又は非置換のアリール基、ハロ
ゲン原子、水素原子から選ばれる。なお、Ｒ １ 〜Ｒ ４ の
うちの少なくとも１つは、置換又は非置換のアリール基
のような置換基を有していても良い芳香族炭化水素環基
又はハロゲン原子である。 In the general formula (I), R 1 , R 2 ,
R 3 and R 4 each represent a hydrogen atom; an alkyl group having 1 to 6 carbon atoms such as a methyl group or an ethyl group; an alkoxyalkyl group such as a methoxyethyl group or an ethoxyethyl group;
Alkoxyalkoxyalkyl groups such as ethoxyethyl group and n-butoxyethoxyethyl group; aryloxyalkyl groups such as phenyloxyethyl group, naphthyloxyethyl group and p-chlorophenyloxyethyl group; benzyl group, phenethyl group and p-chlorobenzyl An arylalkyl group such as a p-nitrobenzyl group; a cycloalkylalkyl group such as a cyclohexylmethyl group, a cyclohexylethyl group or a cyclopentylethyl group; an alkenyloxyalkyl group such as an allyloxyethyl group or a 3-bromoallyloxyethyl group; Cyanoalkyl group such as cyanoethyl group and cyanomethyl group; hydroxyalkyl group such as hydroxyethyl group and hydroxymethyl group; tetrahydrofurylalkyl group such as tetrahydrofuryl group and tetrahydrofurylethyl group Substituted or unsubstituted alkenyl group such as substituted or unsubstituted alkyl group, allyl group, 2-chloroallyl group; substituted or unsubstituted aryl group such as phenyl group, p-methylphenyl group, naphthyl group, m-methoxyphenyl group Groups; cycloalkyl groups such as cyclohexyl group and cyclopentyl group; halogen atoms such as chlorine atom and bromine atom;
An amide group; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group; an alkoxycarbonyl group having 1 to 6 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group; a nitro group; An amino group is mentioned, and preferably, it is selected from a substituted or unsubstituted aryl group, a halogen atom and a hydrogen atom. Incidentally, the R 1 to R 4
At least one of which is a substituted or unsubstituted aryl group;
Aromatic hydrocarbon ring group which may have a substituent such as
Or a halogen atom.
【００２７】Ｒ５及びＲ６としては水素原子；塩素原
子、ハロゲン原子；メトキシ基、エトキシ基等の炭素数
１〜６のアルコキシ基；メトキシカルボニル基、エトキ
シカルボニル基等の炭素数１〜６のアルコキシカルボニ
ル基；メチル基、エチル基等の炭素数１〜６のアルキル
基；ベンジル基、フェネチル基、ｐ−クロロベンジル
基、ｐ−ニトロベンジル基等のアリールアルキル基；シ
クロヘキシルメチル基、シクロヘキシルエチル基、シク
ロペンチルエチル基等のシクロアルキルアルキル基；ア
リルオキシエチル基、３−ブロモアリルオキシエチル基
等のアルケニルオキシアルキル基；シクロペンチル基等
のシクロアルキル基が挙げられるが、好ましくは、水素
原子、炭素数１〜６のアルコキシ基、炭素数１〜６のア
ルキル基から選ばれる。R 5 and R 6 each represent a hydrogen atom; a chlorine atom, a halogen atom; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group or an ethoxy group; An alkoxycarbonyl group; an alkyl group having 1 to 6 carbon atoms such as a methyl group and an ethyl group; an arylalkyl group such as a benzyl group, a phenethyl group, a p-chlorobenzyl group and a p-nitrobenzyl group; a cyclohexylmethyl group and a cyclohexylethyl group A cycloalkylalkyl group such as a cyclopentylethyl group; an alkenyloxyalkyl group such as an allyloxyethyl group or a 3-bromoallyloxyethyl group; a cycloalkyl group such as a cyclopentyl group; Selected from an alkoxy group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms. .
【００２８】本発明に係るナフタセン誘導体の合成法
は、例えば、Ｃｏｐｍｔ．Ｒｅｎｄ．，２０７巻、５８
５頁（１９３８年）；同２４０巻、１１１３頁（１９５
５年）；同２３９巻、１１０１頁（１９５４年）；Ｂｕ
ｌｌ．Ｓｏｃ．Ｃｈｉｍ．Ｆｒａｎｃｅ，４１８頁（１
９４８年）；同１５５頁（１９５２年）；Ｃｏｍｐｔ．
Ｒｅｎｄ．，２３１巻、５頁（１９５０年）；同２４６
巻、６６１頁（１９５８年）；同２３７巻、６２１頁
（１９５３年）；同２３２巻、２２３３頁（１９５１
年）；Ｊ．Ｃｈｅｍ．Ｓｏｃ．，３１５１頁（１９５４
年）；Ａｎｎ，Ｃｈｉｍ．，４巻、３６５頁（１９５９
年）；Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ．，２９巻、
１３５９頁（１９８８年）等に示されている。The method for synthesizing the naphthacene derivative according to the present invention is described in, for example, Copmt. Rend. , 207, 58
5 (1938); ibid., 240, 1113 (195
5th); 239, 1101 (1954); Bu
ll. Soc. Chim. France, p. 418 (1
948); ibid. 155 (1952); Compt.
Rend. 231: 5, 1950; 246
, 661 (1958); 237, 621 (1953); 232, 2233 (1951).
Year); Chem. Soc. , P. 3151 (1954).
Year); Ann, Chim. , 4, 365 (1959).
Year); Tetrahedron Lett. , 29 volumes,
1359 (1988).
【００２９】前記一般式（Ｉ）で表されるナフタセン誘
導体の具体例を、以下の構造式（１）〜（１４）に示す
が、これらに限定するものではない。Specific examples of the naphthacene derivative represented by the general formula (I) are shown in the following structural formulas (1) to (14), but are not limited thereto.
【００３０】[0030]
【化５】 Embedded image
【００３１】[0031]
【化６】 Embedded image
【００３２】本発明において、有機正孔注入輸送層３及
び有機電子注入輸送層４は、例えば、塗布法或いは真空
蒸着法により前記導電層２ａ上に積層することにより形
成される。In the present invention, the organic hole injecting and transporting layer 3 and the organic electron injecting and transporting layer 4 are formed by, for example, laminating on the conductive layer 2a by a coating method or a vacuum evaporation method.
【００３３】塗布の場合は、有機正孔注入輸送化合物又
は有機電子注入輸送化合物と、前記一般式（Ｉ）で表さ
れるナフタセン誘導体、更に必要により、電子や正孔の
トラップや発光の消光剤とならないバインダー樹脂や、
レベリング剤等の塗布性改良剤などの添加剤を添加、溶
解した塗布溶液を調製し、スピンコート法などの方法に
より導電層２ａ又は有機正孔注入輸送層３上に塗布し、
乾燥して有機正孔注入輸送層３又は有機電子注入輸送層
４を形成する。バインダー樹脂としては、ポリカーボネ
ート、ポリアリレート、ポリエステル等が挙げられる。
バインダー樹脂は添加量が多いと電子移動度を低下させ
るので、少ない方が望ましく、塗布溶液に対して５０重
量％以下が好ましい。In the case of coating, an organic hole injecting / transporting compound or an organic electron injecting / transporting compound, a naphthacene derivative represented by the above general formula (I), and, if necessary, a trap for electrons and holes or a quencher for luminescence. Binder resin that does not become
Additives such as a coating agent such as a leveling agent are added and dissolved to prepare a coating solution, and applied on the conductive layer 2a or the organic hole injection transport layer 3 by a method such as spin coating,
After drying, the organic hole injection / transport layer 3 or the organic electron injection / transport layer 4 is formed. Examples of the binder resin include polycarbonate, polyarylate, and polyester.
If the amount of the binder resin is large, the electron mobility is reduced. Therefore, the amount of the binder resin is preferably small, and is preferably 50% by weight or less based on the coating solution.
【００３４】真空蒸着法の場合には、有機正孔注入輸送
材料又は有機電子注入輸送材料を真空容器内に設置され
たるつぼに入れ、前記一般式（Ｉ）で表されるナフタセ
ン誘導体を別のるつぼに入れ、真空容器内を適当な真空
ポンプで１０−６Ｔｏｒｒ程度にまで排気した後、各々
のるつぼを同時に加熱して内容物を蒸発させ、るつぼと
向き合って置かれた基板１に有機正孔注入輸送層３又は
更にその上に有機電子注入輸送層４上に層を形成する。
また、他の方法として、上記の材料を予め所定比で混合
したものを同一のるつぼを用いて蒸発させても良い。In the case of the vacuum evaporation method, an organic hole injecting and transporting material or an organic electron injecting and transporting material is placed in a crucible provided in a vacuum vessel, and the naphthacene derivative represented by the above general formula (I) is added to another crucible. After placing in a crucible and evacuating the inside of the vacuum vessel to about 10 −6 Torr with a suitable vacuum pump, each crucible is heated simultaneously to evaporate the contents, and the organic positive electrode is placed on the substrate 1 placed opposite to the crucible. A layer is formed on the hole injection transport layer 3 or on the organic electron injection transport layer 4 further thereon.
As another method, a mixture of the above materials at a predetermined ratio may be evaporated using the same crucible.
【００３５】このようにして形成される有機正孔注入輸
送層３の膜厚は、通常、１００〜３０００Å、好ましく
は３００〜１０００Åであり、また、有機電子注入輸送
層４の膜厚は、通常、１００〜２０００Å、好ましくは
３００〜１０００Åである。このような薄い膜を一様に
形成するためには、通常の場合、真空蒸着法が好適に用
いられる。The thickness of the organic hole injecting and transporting layer 3 thus formed is usually 100 to 3000 °, preferably 300 to 1000 °, and the thickness of the organic electron injecting and transporting layer 4 is usually , 100-2000 °, preferably 300-1000 °. In order to form such a thin film uniformly, a vacuum evaporation method is preferably used in a normal case.
【００３６】上記は、前記一般式（Ｉ）で表されるナフ
タセン誘導体をドープする場合の方法であるが、ドープ
を行なわない場合には、ナフタセン誘導体を用いずに、
同様にして形成することができる。The above method is for doping the naphthacene derivative represented by the general formula (I). When doping is not performed, the naphthacene derivative is used without using the naphthacene derivative.
It can be formed in a similar manner.
【００３７】また、有機電界発光素子の発光効率を更に
向上させるために、上述のようにしてドープされた有機
電子注入輸送層４の上に、第４図に示す如く、更に他の
有機電子注入輸送層５を積層することが考えられる。こ
の有機電子注入輸送層５に用いられる化合物には、陰極
からの電子注入が容易で、電子の輸送能力がさらに大き
いことが要求される。この様な有機電子注入輸送材料と
しては、化７に示す化合物などのジフェニルキノン誘導
体、化８に示す化合物などのペリレンテトラカルボン酸
誘導体（Jpn. J. Appl. Phys. ２７巻、Ｌ２６９頁、１
９８８年）、化９に示す化合物などのオキサジアゾール
誘導体（Appl. Phys. Lett. ５５巻、１４８９頁、１９
８９年）などが挙げられる。In order to further improve the luminous efficiency of the organic electroluminescent device, another organic electron injecting layer is formed on the organic electron injecting and transporting layer 4 doped as described above, as shown in FIG. Laminating the transport layer 5 is conceivable. The compound used for the organic electron injecting and transporting layer 5 is required to be capable of easily injecting electrons from the cathode and having a higher electron transporting ability. Such organic electron injecting and transporting materials include diphenylquinone derivatives such as the compound shown in Chemical formula 7, and perylenetetracarboxylic acid derivatives such as the compound shown in Chemical formula 8 (Jpn. J. Appl. Phys. 27, L269, 1
988), an oxadiazole derivative such as the compound shown in Chemical formula 9 (Appl. Phys. Lett. 55, 1489, 19).
1989).
【００３８】[0038]
【化７】 Embedded image
【００３９】[0039]
【化８】 Embedded image
【００４０】[0040]
【化９】 Embedded image
【００４１】このような有機電子注入輸送層５の膜厚
は、通常、１００〜２０００Å、好ましくは３００〜１
０００Åである。The thickness of the organic electron injecting and transporting layer 5 is usually 100 to 2000 °, preferably 300 to 1１.
000.
【００４２】なお、本発明においては第１図とは逆の構
造、即ち、基板上に導電層２ｂ、有機電子注入輸送層
４、有機正孔注入輸送層３、導電層２ａの順に積層する
構成を採用することも可能であり、既述した様に少なく
とも一方が透明性の高い２枚の基板の間に本発明の有機
電界発光素子を設けることも可能である。また、同様
に、第２図、第３図及び第４図についても、これらと逆
の構造に積層することも可能である。In the present invention, a structure opposite to that of FIG. 1, that is, a structure in which a conductive layer 2b, an organic electron injection / transport layer 4, an organic hole injection / transport layer 3, and a conductive layer 2a are stacked in this order on a substrate. It is also possible to employ the organic electroluminescent element of the present invention between two substrates, at least one of which has high transparency, as described above. Similarly, in FIGS. 2, 3 and 4, it is also possible to laminate the structure opposite to these.
【００４３】[0043]
【作用】有機電界発光素子の前述の有機正孔注入輸送層
或いは、有機正孔注入輸送層及び有機電子注入輸送層の
ドープ材料として、前記一般式（Ｉ）で表されるナフタ
セン誘導体を用いることにより、優れた発光特性をもた
らすことが可能とされる。The organic hole injecting and transporting layer of the organic electroluminescent device described above.
Alternatively, by using the naphthacene derivative represented by the general formula (I) as a doping material for the organic hole injecting and transporting layer and the organic electron injecting and transporting layer, excellent emission characteristics can be provided.
【００４４】ところで、有機電界発光素子の発光効率を
向上させるとともに発光色を変化させる目的で、８−ヒ
ドロキシキノリンのアルミニウム錯体をホスト材料とし
て、各種の蛍光色素をドープすることが行われている
（米国特許４，７６９，２９２号）。この方法の利点と
しては、 高効率の蛍光色素により発光効率が向上、
蛍光色素の選択により発光波長が可変、 濃度消
光を起こす蛍光色素も使用可能、 薄膜性のわるい蛍
光色素も使用可能、等が挙げられる。By the way, for the purpose of improving the luminous efficiency of the organic electroluminescent device and changing the luminescent color, various fluorescent dyes are doped with an aluminum complex of 8-hydroxyquinoline as a host material. U.S. Pat. No. 4,769,292). The advantage of this method is that the luminous efficiency is improved by the highly efficient fluorescent dye,
The emission wavelength can be varied by selecting the fluorescent dye, a fluorescent dye that causes concentration quenching can be used, and a fluorescent dye with poor thin film properties can be used.
【００４５】本発明の有機電界発光素子においては、陽
極と陰極から注入された正孔と電子が再結合してエキシ
トンが生成され、このエキシトンが拡散する領域に存在
する蛍光色素がエキシトンと衝突して励起されることに
より発光が起きると考えられる。正孔と電子が再結合す
る領域は、前記有機正孔注入輸送層３と有機電子注入輸
送層４の界面近傍と考えられる。従って、前期一般式
（Ｉ）で表されるナフタセン誘導体は、有機正孔注入輸
送層３と有機電子注入輸送層４との界面近傍の領域とす
るのが好ましい。In the organic electroluminescent device of the present invention, the holes and electrons injected from the anode and the cathode are recombined to generate excitons, and the fluorescent dye existing in the exciton diffusion region collides with the excitons. It is considered that light is emitted by the excitation. The region where holes and electrons recombine is considered to be near the interface between the organic hole injection / transport layer 3 and the organic electron injection / transport layer 4. Therefore, it is preferable that the naphthacene derivative represented by the general formula (I) be a region near the interface between the organic hole injection / transport layer 3 and the organic electron injection / transport layer 4.
【００４６】[0046]
【実施例】次に、実施例及び比較例を挙げて本発明を更
に具体的に説明するが、本発明はその要旨を超えない限
り、以下の実施例の記載に限定されるものではない。Next, the present invention will be described more specifically with reference to examples and comparative examples, but the present invention is not limited to the description of the following examples unless it exceeds the gist.
【００４７】実施例１ 第２図に示す構造の有機電界発光素子を以下の方法で作
製した。Example1 No.2An organic electroluminescent device having the structure shown in the figure was fabricated by the following method.
Made.
【００４８】ガラス基板上にインジウム・スズ酸化物
（ＩＴＯ）透明導電膜を１２００Å厚さに堆積したもの
を水洗し、更にイソプロピルアルコールで超音波洗浄し
た後、真空蒸着装置内に設置して、装置内の真空度が２
×１０−６Ｔｏｒｒ以下になるまで油拡散ポンプを用い
て排気した。有機正孔注入輸送層材料として、以下のヒ
ドラゾン化合物（Ｈ１）及び（Ｈ２）を、モル比で（Ｈ
１）：（Ｈ２）＝１：０．３で混合したものを、セラミ
ックるつぼに入れ、るつぼの周囲のタンタル線ヒーター
で加熱して真空容器中で蒸発させた。るつぼの温度は１
５０〜１７０℃の範囲で、蒸着時の真空度は７×１０
−７Ｔｏｒｒであった。有機正孔注入輸送層をこのよう
にして３００Åの膜厚で蒸着した。A transparent conductive film of indium tin oxide (ITO) deposited on a glass substrate to a thickness of 1200 mm was washed with water, further ultrasonically washed with isopropyl alcohol, and then installed in a vacuum evaporation apparatus. The degree of vacuum inside is 2
Evacuation was performed using an oil diffusion pump until the pressure became × 10 −6 Torr or less. The following hydrazone compounds (H1) and (H2) are used as organic hole injection / transport layer materials in a molar ratio of (H
1) :( H2) = 1: 0.3, the mixture was placed in a ceramic crucible, heated with a tantalum wire heater around the crucible, and evaporated in a vacuum vessel. Crucible temperature is 1
In the range of 50 to 170 ° C, the degree of vacuum during deposition is 7 × 10
-7 Torr. An organic hole injecting and transporting layer was thus deposited to a thickness of 300 °.
【００４９】次に前記化５で示されるナフタセン誘導体
（ルブレン）を、ヒドラゾン混合物とは異なるるつぼ
を用いて、ヒドラゾン混合物と同時に加熱して蒸着を行
った 。この様にして前記ナフタセン誘導体を８．０モ
ル％含有する有機正孔注入輸送層を２００Åの膜厚で蒸
着した。 Next, a naphthacene derivative represented by the above formula (5 )
(Rubrene) in a crucible different from the hydrazone mixture
And simultaneously heat the hydrazone mixture to perform evaporation.
Was . In this way, the above-mentioned naphthacene derivative was converted to 8.0
% Of the organic hole injecting and transporting layer containing
I wore it.
【００５０】[0050]
【化１０】 Embedded image
【００５１】次に、有機電子注入輸送層の材料として、
以下の構造式に示すアルミニウムの８−ヒドロキシキノ
リン錯体Ａｌ（Ｃ９Ｈ６ＮＯ）３ を加熱蒸着して、アル
ミニウムの８−ヒドロキシキノリン錯体のみからなる有
機電子注入輸送層を７２０Åの膜厚で蒸着した。 Next, as a material for the organic electron injection / transport layer,
An 8-hydroxyquinoline complex of aluminum represented by the following structural formula, Al (C 9 H 6 NO) 3, was heated and vapor-deposited,
Only consisting of an 8-hydroxyquinoline complex of minium
The electron injection and transport layer was deposited to a thickness of 720 °.
【００５２】[0052]
【化１１】 Embedded image
【００５３】最後にカソードとして、マグネシウムと銀
の合金電極を２元同時蒸着法によって膜厚１５００Åに
蒸着形成した。蒸着はモリブデンボートを用い、真空度
は８×１０−６Ｔｏｒｒで、蒸着時間は８分とし、その
結果、光沢のある膜が得られた。マグネシウムと銀の原
子比は１０：１〜２の範囲であった。Finally, as a cathode, an alloy electrode of magnesium and silver was vapor-deposited and formed to a thickness of 1500 ° by a binary simultaneous vapor deposition method. The deposition was performed using a molybdenum boat, the degree of vacuum was set to 8 × 10 −6 Torr, and the deposition time was set to 8 minutes. As a result, a glossy film was obtained. The atomic ratio of magnesium to silver was in the range of 10: 1 to 2.
【００５４】このようにして有機電界発光素子Ａを作製
した。Thus, an organic electroluminescent device A was manufactured.
【００５５】この有機電界発光素子ＡのＩＴＯ電極（ア
ノード）にプラス、マグネシウム・銀電極（カソード）
にマイナスの直流電圧を印加して測定した発光特性の結
果を表１に示す。なお、この素子Ａの発光スペクトルの
ピーク波長は５７０ｎｍで、黄色の一様な発光を示し
た。 A positive electrode was added to the ITO electrode (anode) and a magnesium / silver electrode (cathode) of the organic electroluminescent device A.
Table 1 shows the results of emission characteristics were measured boss by applying a negative DC voltage to. In addition, the peak wavelength of the emission spectrum of this device A was 570 nm, and yellow uniform light emission was exhibited.
【００５６】なお、表１において、Ｖｔｈは輝度が１ｃ
ｄ／ｍ２となる電圧である。In Table 1, Vth indicates a luminance of 1c.
d / m 2 .
【００５７】実施例２ 第３図に示す構造の有機電界発光素子を以下の方法で作
製した。 [0057]Example 2 An organic electroluminescent device having the structure shown in FIG. 3 was manufactured by the following method.
Made.
【００５８】実施例１と同様にして、洗浄したＩＴＯガ
ラス基板上に、前記ヒドラゾン混合物からなる有機正孔
注入輸送層を３００Åの膜厚で蒸着した。 In the same manner as in Example 1, the cleaned ITO
Organic holes comprising the hydrazone mixture on a glass substrate
The injection transport layer was deposited to a thickness of 300 °.
【００５９】次に、実施例１と同様にして、前期ナフタ
セン誘導体を８．０モル％含有する有機正孔注入輸送
層を２００Åの膜厚で蒸着した。 Next, in the same manner as in Example 1,
Organic hole injection transport containing 8.0 mol% of a cene derivative
The layer was deposited to a thickness of 200 °.
【００６０】次に、有機正孔注入輸送層の材料として、
アルミニウムの８−ヒドロキシキノリン錯体とドープす
る蛍光色素としてナフタセン誘導体を、各々、別々の
るつぼを用いて、同時に加熱して蒸着を行い、膜厚８４
０Åでナフタセン誘導体が上記錯体に対して３．９モ
ル％ドープされた有機電子注入輸送層を得た。 Next, as a material for the organic hole injection transport layer,
Doping with 8-hydroxyquinoline complex of aluminum
Naphthacene derivatives as fluorescent dyes
Using a crucible, heating is performed at the same time to perform vapor deposition.
At 0 °, the naphthacene derivative is 3.9 moles to the above complex.
% Of the organic electron injecting and transporting layer was obtained.
【００６１】最後に、実施例１と同様にして陰極を蒸着
して素子Ｂを得た。 Finally, a cathode was deposited in the same manner as in Example 1.
As a result, an element B was obtained.
【００６２】この素子Ｂの発光特性を表１に示す。この
素子Ｂの発光スペクトルのピーク波長は５７０ｎｍで、
黄色の一様な発光を示した。 Table 1 shows the emission characteristics of the device B. this
The peak wavelength of the emission spectrum of device B was 570 nm,
It showed a yellow uniform emission.
【００６３】比較例１ 有機正孔注入輸送層にナフタセンのドープを行なわな
い他は実施例１と同様にして有機電界発光素子Ｃを作製
した。この素子の発光特性の測定結果を表１に示す。こ
の素子Ｃの発光スペクトルのピーク波長は５３０ｎｍ
で、緑色の一様な発光を示した。Comparative Example 1 An organic electroluminescent device C was produced in the same manner as in Example 1 except that the organic hole injecting and transporting layer was not doped with naphthacene. Table 1 shows the measurement results of the light emission characteristics of this device. The peak wavelength of the emission spectrum of this device C is 530 nm.
, Showed uniform green light emission.
【００６４】[0064]
【表１】 [Table 1]
【００６５】[0065]
【発明の効果】以上詳述した通り、本発明の有機電界発
光素子によれば、陽極、有機正孔注入輸送層、有機電子
注入輸送層、陰極が基板上に順次設けられ、しかも、有
機正孔注入輸送層、或いは有機正孔注入輸送層及び有機
電子注入輸送層、もしくはその一部分に特定のナフタセ
ン誘導体をドープしているため、両極に電圧を印加した
場合、低い駆動電圧で実用上十分な輝度の発光を得るこ
とができ、長期間の保存後も初期の発光特性を維持でき
る。As described above in detail, according to the organic electroluminescent device of the present invention, an anode, an organic hole injecting and transporting layer, an organic electron injecting and transporting layer, and a cathode are sequentially provided on a substrate. Since the hole injection transport layer , or the organic hole injection transport layer and the organic electron injection transport layer, or a part thereof is doped with a specific naphthacene derivative, when a voltage is applied to both electrodes, a low drive voltage is sufficient for practical use. Bright light emission can be obtained, and the initial light emission characteristics can be maintained even after long-term storage.
【００６６】本発明の電界発光素子はフラットパネル・
ディスプレイ（例えば壁掛けテレビ）の分野や画発光体
としての特徴を生かした光源（例えば、複写機の光源、
液晶ディスプレイや計器類のバックライト光源）、表示
板、標識灯への応用が考えられ、その工業的有用性は極
めて大である。The electroluminescent device of the present invention has a flat panel structure.
Light source (for example, light source for copier,
It can be applied to liquid crystal displays and backlight sources for instruments, display boards, and marker lights, and its industrial utility is extremely large.
【図１】第１図は本発明の有機電界発光素子の一実施例
を示す断面図である。FIG. 1 is a sectional view showing an embodiment of the organic electroluminescent device of the present invention.
【図２】第２図は本発明の有機電界発光素子の他の実施
例を示す断面図である。FIG. 2 is a sectional view showing another embodiment of the organic electroluminescent device of the present invention.
【図３】第３図は本発明の有機電界発光素子の別の実施
例を示す断面図である。FIG. 3 is a sectional view showing another embodiment of the organic electroluminescent device of the present invention.
【図４】第４図は本発明の有機電界発光素子の更に別の
実施例を示す断面図である。FIG. 4 is a sectional view showing still another embodiment of the organic electroluminescent device of the present invention.
１ 基板 ２ａ，２ｂ 導電層 ３ 有機正孔注入輸送層 ４ 有機電子注入輸送層 DESCRIPTION OF SYMBOLS 1 Substrate 2a, 2b Conductive layer 3 Organic hole injection transport layer 4 Organic electron injection transport layer
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭61−37862（ＪＰ，Ａ) 特開 昭61−37861（ＪＰ，Ａ) 特開 昭61−37860（ＪＰ，Ａ) 特開 昭61−37859（ＪＰ，Ａ) 特開 昭61−37858（ＪＰ，Ａ) 特開 昭63−264692（ＪＰ，Ａ) 特開 平３−82174（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C09K 11/06 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-61-37862 (JP, A) JP-A-61-37861 (JP, A) JP-A-61-37860 (JP, A) JP-A-61-37860 37859 (JP, A) JP-A-61-37858 (JP, A) JP-A-63-264692 (JP, A) JP-A-3-82174 (JP, A) (58) Fields investigated (Int. 7 , DB name) C09K 11/06 CA (STN) REGISTRY (STN)
Claims (5)
機電子注入輸送層及び陰極が積層されて成る有機電界発
光素子において、有機正孔注入輸送層が、下記一般式
（Ｉ）で表わされるナフタセン誘導体を含有することを
特徴とする有機電界発光素子。 【化１】 （式中、Ｒ１，Ｒ２，Ｒ３及びＲ４は水素原子、アルキ
ル基、アラルキル基、アルケニル基、アリル基、置換基
を有していても良い芳香族炭化水素環基又は芳香族複素
環基、ハロゲン原子、アミド基、アルコキシ基、アルコ
キシカルボニル基、ニトロ基、或いは置換基を有してい
ても良いアミノ基を表し、Ｒ １ 〜Ｒ ４ のうちの少なくと
も１つは、置換基を有していても良い芳香族炭化水素環
基又はハロゲン原子である。Ｒ５及びＲ６は水素原子、
ハロゲン原子、アルコキシ基、アルコキシカルボニル
基、又はアルキル基を示す。）1. An organic electroluminescent device comprising an anode, an organic hole injecting and transporting layer, an organic electron injecting and transporting layer and a cathode sequentially laminated, wherein the organic hole injecting and transporting layer is represented by the following general formula (I). An organic electroluminescent device comprising a naphthacene derivative represented by the formula: Embedded image (Wherein R 1 , R 2 , R 3 and R 4 represent a hydrogen atom, an alkyl group, an aralkyl group, an alkenyl group, an allyl group, an aromatic hydrocarbon ring group which may have a substituent or an aromatic heterocyclic group) A ring group, a halogen atom, an amide group, an alkoxy group, an alkoxycarbonyl group, a nitro group, or an amino group which may have a substituent, and at least one of R 1 to R 4
One is an aromatic hydrocarbon ring which may have a substituent.
Group or a halogen atom. R 5 and R 6 are a hydrogen atom,
It represents a halogen atom, an alkoxy group, an alkoxycarbonyl group, or an alkyl group. )
表わされる化合物が有機正孔注入輸送層及び有機電子注
入輸送層に含有されていることを特徴とする有機電界発
光素子。2. The method according to claim 1, wherein
The compound represented is an organic hole injection transport layer and an organic electron injection
Organic electric field generation characterized by being contained in the in-transport layer
Optical element .
表わされる化合物が、有機正孔注入輸送層中の有機正孔
注入輸送化合物をホスト材料とし、該ホスト材料に対し
てドープされていることを特徴とする有機電界発光素
子。 3. The method according to claim 1, wherein
The compound represented is an organic hole in the organic hole injection transport layer.
The injection / transport compound is used as a host material, and the host material is
Organic electroluminescent element characterized by being doped
Child.
表わされる化合物が、有機正孔注入輸送層中の有機正孔
注入輸送化合物及び有機電子注入輸送層中の有機電子注
入輸送化合物をホスト材料とし、該ホスト材料に対して
ドープされていることを特徴とする有機電界発光素子。4. The method of claim 2, the compound represented by the general formula (I), an organic electron injecting and transporting organic hole injection transport compound及beauty organic electron injecting and transporting layer of organic hole injection transport layer An organic electroluminescent device comprising a compound as a host material and being doped with respect to the host material.
（Ｉ）で表わされる化合物のドープ量が、ホスト材料に
対して１０−３〜１０モル％であることを特徴とする有
機電界発光素子。5. The organic electroluminescent device according to claim 3 , wherein a doping amount of the compound represented by the general formula (I) is 10 −3 to 10 mol% with respect to a host material. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10754091A JP3196230B2 (en) | 1991-05-13 | 1991-05-13 | Organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10754091A JP3196230B2 (en) | 1991-05-13 | 1991-05-13 | Organic electroluminescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04335087A JPH04335087A (en) | 1992-11-24 |
| JP3196230B2 true JP3196230B2 (en) | 2001-08-06 |
Family
ID=14461781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10754091A Expired - Lifetime JP3196230B2 (en) | 1991-05-13 | 1991-05-13 | Organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3196230B2 (en) |
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| Publication number | Publication date |
|---|---|
| JPH04335087A (en) | 1992-11-24 |
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