JP2001006877A - Light-emitting device - Google Patents
Light-emitting deviceInfo
- Publication number
- JP2001006877A JP2001006877A JP11174058A JP17405899A JP2001006877A JP 2001006877 A JP2001006877 A JP 2001006877A JP 11174058 A JP11174058 A JP 11174058A JP 17405899 A JP17405899 A JP 17405899A JP 2001006877 A JP2001006877 A JP 2001006877A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- emitting device
- light emitting
- light
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
- 125000005504 styryl group Chemical group 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 54
- -1 haloalkene Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 11
- 125000005013 aryl ether group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 125000003172 aldehyde group Chemical group 0.000 claims description 9
- 150000001350 alkyl halides Chemical class 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000004185 ester group Chemical group 0.000 claims description 9
- 125000005401 siloxanyl group Chemical group 0.000 claims description 9
- 150000004832 aryl thioethers Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- MCZUXEWWARACSP-UHFFFAOYSA-N 1-ethynylnaphthalene Chemical compound C1=CC=C2C(C#C)=CC=CC2=C1 MCZUXEWWARACSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 239000000975 dye Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 150000002739 metals Chemical class 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
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- 239000010409 thin film Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 150000004775 coumarins Chemical class 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- 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 4
- 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 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000004506 ultrasonic cleaning Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 150000004867 thiadiazoles Chemical class 0.000 description 3
- 150000003577 thiophenes Chemical class 0.000 description 3
- NGQSLSMAEVWNPU-UHFFFAOYSA-N 1,2-bis(2-phenylethenyl)benzene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1C=CC1=CC=CC=C1 NGQSLSMAEVWNPU-UHFFFAOYSA-N 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- VXKRQGLKRZZWBL-UHFFFAOYSA-N 1-[3,5-bis(2-bromoacetyl)phenyl]-2-bromoethanone Chemical compound BrCC(=O)C1=CC(C(=O)CBr)=CC(C(=O)CBr)=C1 VXKRQGLKRZZWBL-UHFFFAOYSA-N 0.000 description 2
- KIIGPNDJMVHUSL-UHFFFAOYSA-N 1-phenyl-2-benzofuran Chemical compound C=12C=CC=CC2=COC=1C1=CC=CC=C1 KIIGPNDJMVHUSL-UHFFFAOYSA-N 0.000 description 2
- TWZYORZPYCRVAX-UHFFFAOYSA-N 2-(2h-thiopyran-1-ylidene)propanedinitrile Chemical compound N#CC(C#N)=S1CC=CC=C1 TWZYORZPYCRVAX-UHFFFAOYSA-N 0.000 description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical class C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical compound N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 2
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
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- 239000000460 chlorine Substances 0.000 description 2
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- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-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
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- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
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- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
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- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
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- 239000011591 potassium Substances 0.000 description 2
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- RSTDIKJOEIERRN-UHFFFAOYSA-N pyreno[4,5-c][1,2,5]thiadiazole Chemical class C1=CC=C2C3=NSN=C3C3=CC=CC4=CC=C1C2=C43 RSTDIKJOEIERRN-UHFFFAOYSA-N 0.000 description 2
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 2
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- LBIUMLHTGBTILM-UHFFFAOYSA-N 1,3-bis(2-methylphenyl)-2-benzofuran Chemical compound CC1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C(=CC=CC=2)C)O1 LBIUMLHTGBTILM-UHFFFAOYSA-N 0.000 description 1
- JGOKQJGYALJSMZ-UHFFFAOYSA-N 1,3-bis[2-(trifluoromethyl)phenyl]-2-benzofuran Chemical compound FC(F)(F)C1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C(=CC=CC=2)C(F)(F)F)O1 JGOKQJGYALJSMZ-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- HSOAIPRTHLEQFI-UHFFFAOYSA-N 1-(3,5-diacetylphenyl)ethanone Chemical compound CC(=O)C1=CC(C(C)=O)=CC(C(C)=O)=C1 HSOAIPRTHLEQFI-UHFFFAOYSA-N 0.000 description 1
- UIWLITBBFICQKW-UHFFFAOYSA-N 1h-benzo[h]quinolin-2-one Chemical compound C1=CC=C2C3=NC(O)=CC=C3C=CC2=C1 UIWLITBBFICQKW-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- GZEYLLPOQRZUDF-UHFFFAOYSA-N 7-(dimethylamino)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(N(C)C)=CC=C21 GZEYLLPOQRZUDF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GHBQLFWTMLRYKN-UHFFFAOYSA-N 9-prop-2-enylcarbazole Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3C2=C1 GHBQLFWTMLRYKN-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GBRZYXPQVIYGCB-UHFFFAOYSA-M [Al+3].N1=C(C=CC=C1)[O-].CC1(NC2=CC=CC=C2C=C1)[O-].CC1(NC2=CC=CC=C2C=C1)[O-] Chemical compound [Al+3].N1=C(C=CC=C1)[O-].CC1(NC2=CC=CC=C2C=C1)[O-].CC1(NC2=CC=CC=C2C=C1)[O-] GBRZYXPQVIYGCB-UHFFFAOYSA-M 0.000 description 1
- 239000000999 acridine dye Substances 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004883 computer application Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- JNTHRSHGARDABO-UHFFFAOYSA-N dibenzo[a,l]pyrene Chemical class C1=CC=CC2=C3C4=CC=CC=C4C=C(C=C4)C3=C3C4=CC=CC3=C21 JNTHRSHGARDABO-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical class C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- LIIALPBMIOVAHH-UHFFFAOYSA-N herniarin Chemical class C1=CC(=O)OC2=CC(OC)=CC=C21 LIIALPBMIOVAHH-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910000833 kovar Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- PKXXWDSLPQQAPX-UHFFFAOYSA-N naphthopyrene Chemical compound C1=CC2=C3C4=CC=CC=C4C=CC3=C(C=CC=C3C=C4)C3=C2C4=C1 PKXXWDSLPQQAPX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 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
- 238000000206 photolithography Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000001022 rhodamine dye Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、電気エネルギーを
光に変換できる素子であって、表示素子、フラットパネ
ルディスプレイ、バックライト、照明、インテリア、標
識、看板、電子写真機、光信号発生器などの分野に利用
可能な発光素子に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an element capable of converting electric energy into light, and relates to a display element, a flat panel display, a backlight, lighting, an interior, a sign, a sign, an electrophotographic device, an optical signal generator, and the like. The present invention relates to a light emitting element that can be used in the field of (1).
【０００２】[0002]
【従来の技術】陰極から注入された電子と陽極から注入
された正孔が両極に挟まれた有機蛍光体内で再結合する
際に発光するという有機積層薄膜発光素子の研究が近年
活発に行われている。この素子は、薄型、低駆動電圧下
での高輝度発光、蛍光材料を選ぶことによる多色発光が
特徴であり注目を集めている。2. Description of the Related Art In recent years, studies have been actively conducted on organic laminated thin-film light emitting devices in which electrons injected from a cathode and holes injected from an anode emit light when they recombine in an organic phosphor sandwiched between both electrodes. ing. This device has attracted attention because it is thin, emits light with high luminance under a low driving voltage, and emits multicolor light by selecting a fluorescent material.
【０００３】この研究は、コダック社のＣ．Ｗ．Ｔａｎ
ｇらが有機積層薄膜素子が高輝度に発光することを示し
て以来（Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１（１２）
２１，ｐ．９１３，１９８７）、多くの研究機関が検討
を行っている。コダック社の研究グループが提示した有
機積層薄膜発光素子の代表的な構成は、ＩＴＯガラス基
板上に正孔輸送性のジアミン化合物、発光層である８−
ヒドロキシキノリンアルミニウム、そして陰極としてＭ
ｇ：Ａｇを順次設けたものであり、１０Ｖ程度の駆動電
圧で１０００ｃｄ／ｍ2の緑色発光が可能であった。現
在の有機積層薄膜発光素子は、上記の素子構成要素の他
に電子輸送層を設けているものなど構成を変えているも
のもあるが、基本的にはコダック社の構成を踏襲してい
る。[0003] This study was carried out by Kodak Corporation. W. Tan
g. et al. showed that the organic laminated thin film element emits light with high luminance (Appl. Phys. Lett. 51 (12)
21, p. 913, 1987), and many research institutions are conducting studies. A typical configuration of an organic laminated thin film light emitting device presented by a research group of Kodak Company is a diamine compound having a hole transporting property and a light emitting layer on an ITO glass substrate.
Aluminum hydroxyquinoline and M as cathode
g: Ag was sequentially provided, and green light emission of 1000 cd / m 2 was possible at a driving voltage of about 10 V. The present organic laminated thin-film light-emitting device has a different configuration, such as a device provided with an electron transport layer in addition to the above-described device components, but basically follows the configuration of Kodak Company.
【０００４】発光層はホスト材料のみや、ホスト材料に
ゲスト材料をドーピングして構成される。三原色の発光
材料の中では緑色発光材料の研究が最も進んでおり、現
在は赤色発光材料と青色発光材料において、特性向上を
目指して鋭意研究がなされている。特に青色発光におい
て、耐久性に優れ十分な輝度と色純度特性を示すものが
望まれている。[0004] The light emitting layer is composed of a host material alone or a host material doped with a guest material. Among the three primary color light-emitting materials, research on a green light-emitting material is the most advanced, and at present, earnest research is being conducted on red light-emitting materials and blue light-emitting materials with the aim of improving characteristics. Particularly, in blue light emission, a material having excellent durability and sufficient luminance and color purity characteristics is desired.
【０００５】ホスト材料としては、トリス（８−キノリ
ノラト）アルミニウムを始めとするキノリノール誘導体
の金属錯体、ベンゾキノリノールの金属錯体、ベンズオ
キサゾール誘導体、ベンゾチアゾール誘導体、チアジア
ゾール誘導体、チオフェン誘導体などがあげられる。Examples of the host material include metal complexes of quinolinol derivatives such as tris (8-quinolinolato) aluminum, metal complexes of benzoquinolinol, benzoxazole derivatives, benzothiazole derivatives, thiadiazole derivatives, and thiophene derivatives.
【０００６】青色発光用のホスト材料としては、キノリ
ノール誘導体と異なる配位子を組み合わせた金属錯体、
ベンゾイミダゾール誘導体などがあげられ、ビススチリ
ルベンゼン誘導体（特開平４−１１７４８５号公報）な
どは比較的良い特性を示すが、特に色純度が十分ではな
い。As a host material for emitting blue light, a metal complex obtained by combining a quinolinol derivative with a different ligand,
Examples include benzimidazole derivatives, and bisstyrylbenzene derivatives (Japanese Patent Application Laid-Open No. 4-117485) have relatively good characteristics, but the color purity is not particularly sufficient.
【０００７】一方、ゲスト材料としてのドーパント材料
には、レーザー染料として有用であることが知られてい
る、７−ジメチルアミノ−４−メチルクマリンを始めと
する蛍光性クマリン染料、ジシアノメチレンピラン染
料、ジシアノメチレンチオピラン染料、ポリメチン染
料、シアニン染料、オキソベンズアンスラセン染料、キ
サンテン染料、ローダミン染料、フルオレセイン染料、
ピリリウム染料、カルボスチリル染料、ペリレン染料、
アクリジン染料、ビス（スチリル）ベンゼン染料、ピレ
ン染料、オキサジン染料、フェニレンオキサイド染料、
ペリレン、テトラセン、ペンタセン、キナクリドン化合
物、キナゾリン化合物、ピロロピリジン化合物、フロピ
リジン化合物、１，２，５−チアジアゾロピレン誘導
体、ペリノン誘導体、ピロロピロール化合物、スクアリ
リウム化合物、ビオラントロン化合物、フェナジン誘導
体、アクリドン化合物、ジアザフラビン誘導体などが知
られている。On the other hand, as a dopant material as a guest material, a fluorescent coumarin dye such as 7-dimethylamino-4-methylcoumarin, a dicyanomethylenepyran dye, which is known to be useful as a laser dye, Dicyanomethylenethiopyran dye, polymethine dye, cyanine dye, oxobenzanthracene dye, xanthene dye, rhodamine dye, fluorescein dye,
Pyrylium dye, carbostyril dye, perylene dye,
Acridine dye, bis (styryl) benzene dye, pyrene dye, oxazine dye, phenylene oxide dye,
Perylene, tetracene, pentacene, quinacridone compound, quinazoline compound, pyrrolopyridine compound, furopyridine compound, 1,2,5-thiadiazolopyrene derivative, perinone derivative, pyrrolopyrrole compound, squarylium compound, biolanthrone compound, phenazine derivative, acridone compound, diazaflavin Derivatives and the like are known.
【０００８】[0008]
【発明が解決しようとする課題】しかし、従来技術に用
いられる発光材料（ホスト材料、ドーパント材料）に
は、発光効率が低く消費電力が高いものや、化合物の耐
久性が低く素子寿命の短いものが多かった。また、フル
カラーディスプレイとして赤色、緑色、青色の三原色発
光が求められているが、赤色、青色発光においては、発
光波長を満足させるものは少なく、発光ピークの幅も広
く色純度が良いものは少ない。中でも青色発光におい
て、耐久性に優れ十分な輝度と色純度特性を示すものが
必要とされている。However, the luminescent materials (host materials and dopant materials) used in the prior art include those having low luminous efficiency and high power consumption, and those having low durability of the compound and short element life. There were many. In addition, red, green, and blue light emission of three primary colors is required as a full-color display. However, in red and blue light emission, few light emission wavelengths are satisfied, and few light emission peaks have a wide emission peak width and good color purity. In particular, for blue light emission, a material having excellent durability and sufficient luminance and color purity characteristics is required.
【０００９】本発明は、かかる従来技術の問題を解決
し、発光効率が高く、高輝度で色純度に優れた発光素子
を提供することを目的とするものである。An object of the present invention is to solve the problems of the prior art and to provide a light emitting device having high luminous efficiency, high luminance and excellent color purity.
【００１０】[0010]
【課題を解決するための手段】本発明は、陽極と陰極の
間に発光を司る物質が存在し、電気エネルギーにより発
光する素子において、該素子がイミダゾピリジン骨格を
有する化合物を含むことを特徴とする発光素子である。According to the present invention, there is provided an element which emits light by electric energy, wherein a substance having light emission exists between an anode and a cathode, wherein the element contains a compound having an imidazopyridine skeleton. Light emitting element.
【００１１】[0011]
【発明の実施の形態】本発明において陽極は、光を取り
出すために透明であれば酸化錫、酸化インジウム、酸化
錫インジウム（ＩＴＯ）などの導電性金属酸化物、ある
いは金、銀、クロムなどの金属、ヨウ化銅、硫化銅など
の無機導電性物質、ポリチオフェン、ポリピロール、ポ
リアニリンなどの導電性ポリマなど特に限定されるもの
でないが、ＩＴＯガラスやネサガラスを用いることが特
に望ましい。透明電極の抵抗は素子の発光に十分な電流
が供給できればよいので限定されないが、素子の消費電
力の観点からは低抵抗であることが望ましい。例えば３
００Ω／□以下のＩＴＯ基板であれば素子電極として機
能するが、現在では１０Ω／□程度の基板の供給も可能
になっていることから、低抵抗品を使用することが特に
望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ
事ができるが、通常１００〜３００ｎｍの間で用いられ
ることが多い。また、ガラス基板はソーダライムガラ
ス、無アルカリガラスなどが用いられ、また厚みも機械
的強度を保つのに十分な厚みがあればよいので、０．５
ｍｍ以上あれば十分である。ガラスの材質については、
ガラスからの溶出イオンが少ない方がよいので無アルカ
リガラスの方が好ましいが、ＳｉＯ2などのバリアコー
トを施したソーダライムガラスも市販されているのでこ
れを使用できる。ＩＴＯ膜形成方法は、電子線ビーム
法、スパッタリング法、化学反応法など特に制限を受け
るものではない。DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, the anode is made of a conductive metal oxide such as tin oxide, indium oxide, indium tin oxide (ITO) or a metal such as gold, silver or chromium if it is transparent to extract light. Although not particularly limited, such as metals, inorganic conductive substances such as copper iodide and copper sulfide, and conductive polymers such as polythiophene, polypyrrole, and polyaniline, it is particularly preferable to use ITO glass or Nesa glass. The resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the element can be supplied, but is preferably low from the viewpoint of power consumption of the element. For example, 3
Although an ITO substrate having a resistance of 00 Ω / □ or less functions as an element electrode, a substrate having a resistance of about 10 Ω / □ can be supplied at present. The thickness of the ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of usually 100 to 300 nm. Further, the glass substrate is made of soda lime glass, non-alkali glass, or the like, and the thickness only needs to be sufficient to maintain the mechanical strength.
mm or more is sufficient. For the glass material,
Alkali-free glass is preferred because less ions elute from the glass is preferred, but soda-lime glass with a barrier coat such as SiO 2 is also commercially available and can be used. The method of forming the ITO film is not particularly limited, such as an electron beam method, a sputtering method, and a chemical reaction method.
【００１２】陰極は、電子を本有機物層に効率良く注入
できる物質であれば特に限定されないが、一般に白金、
金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウ
ム、クロム、リチウム、ナトリウム、カリウム、カルシ
ウム、マグネシウムなどがあげられるが、電子注入効率
をあげて素子特性を向上させるためにはリチウム、ナト
リウム、カリウム、カルシウム、マグネシウムまたはこ
れら低仕事関数金属を含む合金が有効である。しかし、
これらの低仕事関数金属は、一般に大気中で不安定であ
ることが多く、例えば、有機層に微量のリチウムやマグ
ネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドー
ピングして安定性の高い電極を使用する方法が好ましい
例として挙げることができるが、フッ化リチウムのよう
な無機塩の使用も可能であることから特にこれらに限定
されるものではない。更に電極保護のために白金、金、
銀、銅、鉄、錫、アルミニウム、インジウムなどの金
属、またはこれら金属を用いた合金、そしてシリカ、チ
タニア、窒化ケイ素などの無機物、ポリビニルアルコー
ル、塩化ビニル、炭化水素系高分子などを積層すること
が好ましい例として挙げられる。これらの電極の作製法
も抵抗加熱、電子線ビーム、スパッタリング、イオンプ
レーティング、コーティングなど導通を取ることができ
れば特に制限されない。The cathode is not particularly limited as long as it can efficiently inject electrons into the organic material layer.
Gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium, sodium, potassium, calcium, magnesium, etc., and lithium, sodium for improving the electron injection efficiency and improving the device characteristics , Potassium, calcium, magnesium or alloys containing these low work function metals are effective. But,
These low work function metals are generally unstable in the air in many cases. For example, an organic layer is doped with a very small amount of lithium or magnesium (1 nm or less as indicated by a film thickness gauge by vacuum deposition) to have high stability. Although a method using an electrode can be mentioned as a preferable example, it is not particularly limited because an inorganic salt such as lithium fluoride can be used. In addition, platinum, gold,
Lamination of metals such as silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymers. Are preferred examples. The method for producing these electrodes is not particularly limited, as long as electrical conduction such as resistance heating, electron beam, sputtering, ion plating, and coating can be achieved.
【００１３】発光を司る物質とは、１）正孔輸送層／発
光層、２）正孔輸送層／発光層／電子輸送層、３）発光
層／電子輸送層、そして、４）以上の組合わせ物質を一
層に混合した形態のいずれであってもよい。即ち、素子
構成としては、上記１）〜３）の多層積層構造の他に
４）のように発光材料単独または発光材料と正孔輸送材
料や電子輸送材料を含む層を一層設けるだけでもよい。The substances that control light emission include 1) a hole transport layer / a light emitting layer, 2) a hole transport layer / a light emitting layer / an electron transport layer, 3) a light emitting layer / an electron transport layer, and 4) a combination of the above. Any of the forms in which the combined substances are mixed together may be used. That is, as the element configuration, in addition to the multilayer laminated structure of the above 1) to 3), a single layer of a luminescent material alone or a layer containing a luminescent material and a hole transporting material or an electron transporting material may be provided as in 4).
【００１４】正孔輸送層は正孔輸送性物質単独または二
種類以上の物質を積層、混合するか正孔輸送性物質と高
分子結着剤の混合物により形成され、正孔輸送性物質と
してはＴＰＤ、ｍ−ＭＴＤＡＴＡ、α−ＮＰＤなどのト
リフェニルアミン類、ビス（Ｎ−アリルカルバゾール）
またはビス（Ｎ−アルキルカルバゾール）類、ピラゾリ
ン誘導体、スチルベン系化合物、ヒドラゾン系化合物、
オキサジアゾール誘導体やフタロシアニン誘導体、ポル
フィリン誘導体に代表される複素環化合物、ポリマー系
では前記単量体を側鎖に有するポリカーボネートやスチ
レン誘導体、ポリビニルカルバゾール、ポリシランなど
が好ましいが、素子作製に必要な薄膜を形成し、陽極か
ら正孔が注入できて、さらに正孔を輸送できる化合物で
あれば特に限定されるものではない。The hole transporting layer is formed by a hole transporting substance alone or by laminating and mixing two or more kinds of substances or by a mixture of a hole transporting substance and a polymer binder. Triphenylamines such as TPD, m-MTDATA, α-NPD, bis (N-allylcarbazole)
Or bis (N-alkylcarbazole) s, pyrazoline derivatives, stilbene compounds, hydrazone compounds,
Oxadiazole derivatives, phthalocyanine derivatives, heterocyclic compounds typified by porphyrin derivatives, and in polymer systems, polycarbonates and styrene derivatives having the above monomers in side chains, polyvinylcarbazole, polysilane, etc. are preferred, but thin films required for device fabrication are preferred. Is not particularly limited as long as it is a compound capable of injecting holes from the anode and transporting holes.
【００１５】発光材料はホスト材料のみでも、ホスト材
料とドーパント材料の組み合わせでも、いずれであって
もよい。また、ドーパント材料はホスト材料の全体に含
まれていても、部分的に含まれていても、いずれであっ
てもよい。ドーパント材料は積層されていても、分散さ
れていても、いずれであってもよい。The light emitting material may be either a host material alone or a combination of a host material and a dopant material. In addition, the dopant material may be included in the entire host material, partially, or may be included. The dopant material may be stacked, dispersed, or the like.
【００１６】本発明における発光材料はイミダゾピリジ
ン骨格を有する化合物を含有する。イミダゾピリジン骨
格を有する化合物の中でも下記一般式（１）あるいは一
般式（２）で表される化合物が好ましい。The luminescent material of the present invention contains a compound having an imidazopyridine skeleton. Among the compounds having an imidazopyridine skeleton, a compound represented by the following general formula (1) or (2) is preferable.
【００１７】[0017]
【化６】 Embedded image
【００１８】（ここでＲ1〜Ｒ6はそれぞれ同じでも異な
っていてもよく、結合、水素、アルキル基、シクロアル
キル基、アラルキル基、アルケニル基、シクロアルケニ
ル基、アルコキシ基、アルキルチオ基、アリールエーテ
ル基、アリールチオエーテル基、アリール基、複素環
基、ハロゲン、シアノ基、アルデヒド基、カルボニル
基、カルボキシル基、エステル基、カルバモイル基、ア
ミノ基、ニトロ基、シリル基、シロキサニル基、隣接置
換基との間に形成される環構造の中から選ばれる。）(Wherein R 1 to R 6 may be the same or different and each represents a bond, hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an aryl ether Group, arylthioether group, aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, and adjacent substituent It is selected from the ring structures formed between them.)
【００１９】[0019]
【化７】 Embedded image
【００２０】（ここでＲ7〜Ｒ12はそれぞれ同じでも異
なっていてもよく、結合、水素、アルキル基、シクロア
ルキル基、アラルキル基、アルケニル基、シクロアルケ
ニル基、アルコキシ基、アルキルチオ基、アリールエー
テル基、アリールチオエーテル基、アリール基、複素環
基、ハロゲン、ハロアルカン、ハロアルケン、シアノ
基、アルデヒド基、カルボニル基、カルボキシル基、エ
ステル基、カルバモイル基、アミノ基、ニトロ基、シリ
ル基、シロキサニル基、隣接置換基との間に形成される
環構造の中から選ばれる。） これらの置換基の説明のうち、結合とはその位置で複数
個のイミダゾピリジン骨格と連結されていることを意味
する。この場合、複数個のイミダゾピリジンは直接連結
されていても構わないし、ある結合単位を介して連結さ
れていても構わない。アルキル基とは例えばメチル基、
エチル基、プロピル基、ブチル基などの飽和脂肪族炭化
水素基を示し、これは無置換でも置換されていてもかま
わない。また、シクロアルキル基とは例えばシクロプロ
ピル、シクロヘキシル、ノルボルニル、アダマンチルな
どの飽和脂環式炭化水素基を示し、これは無置換でも置
換されていてもかまわない。また、アラルキル基とは例
えばベンジル基、フェニルエチル基などの脂肪族炭化水
素を介した芳香族炭化水素基を示し、脂肪族炭化水素と
芳香族炭化水素はいずれも無置換でも置換されていても
かまわない。また、アルケニル基とは例えばビニル基、
アリル基、ブタジエニル基などの二重結合を含む不飽和
脂肪族炭化水素基を示し、これは無置換でも置換されて
いてもかまわない。また、シクロアルケニル基とは例え
ばシクロペンテニル基、シクロペンタジエニル基、シク
ロヘキセン基などの二重結合を含む不飽和脂環式炭化水
素基を示し、これは無置換でも置換されていてもかまわ
ない。また、アルコキシ基とは例えばメトキシ基などの
エーテル結合を介した脂肪族炭化水素基を示し、脂肪族
炭化水素基は無置換でも置換されていてもかまわない。
また、アルキルチオ基とはアルコキシ基のエーテル結合
の酸素原子が硫黄原子に置換されたものである。また、
アリールエーテル基とは例えばフェノキシ基などのエー
テル結合を介した芳香族炭化水素基を示し、芳香族炭化
水素基は無置換でも置換されていてもかまわない。ま
た、アリールチオエーテル基とはアリールエーテル基の
エーテル結合の酸素原子が硫黄原子に置換されたもので
ある。また、アリール基とは例えばフェニル基、ナフチ
ル基、ビフェニル基、フェナントリル基、ターフェニル
基、ピレニル基などの芳香族炭化水素基を示し、これは
無置換でも置換されていてもかまわない。また、複素環
基とは例えばフリル基、チエニル基、オキサゾリル基、
ピリジル基、キノリル基、カルバゾリル基などの炭素以
外の原子を有する環状構造基を示し、これは無置換でも
置換されていてもかまわない。ハロゲンとはフッ素、塩
素、臭素、ヨウ素を示す。ハロアルカン、ハロアルケ
ン、ハロアルキンとは例えばトリフルオロメチル基など
の、前述のアルキル基、アルケニル基、アルキニル基の
一部あるいは全部が、前述のハロゲンで置換されたもの
を示し、残りの部分は無置換でも置換されていてもかま
わない。アルデヒド基、カルボニル基、エステル基、カ
ルバモイル基、アミノ基には脂肪族炭化水素、脂環式炭
化水素、芳香族炭化水素、複素環などで置換されたもの
も含み、さらに脂肪族炭化水素、脂環式炭化水素、芳香
族炭化水素、複素環は無置換でも置換されていてもかま
わない。シリル基とは例えばトリメチルシリル基などの
ケイ素化合物基を示し、これは無置換でも置換されてい
てもかまわない。シロキサニル基とは例えばトリメチル
シロキサニル基などのエーテル結合を介したケイ素化合
物基を示し、これは無置換でも置換されていてもかまわ
ない。隣接置換基との間に形成される環構造は無置換で
も置換されていてもかまわない。(Wherein R 7 to R 12 may be the same or different and each represents a bond, hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an aryl ether Group, arylthioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, adjacent It is selected from the ring structures formed between the substituents.) In the description of these substituents, the bond means that the imidazopyridine skeleton is linked at that position to a plurality of imidazopyridine skeletons. In this case, a plurality of imidazopyridines may be directly linked, or may be linked via a certain bonding unit. The alkyl group is, for example, a methyl group,
It represents a saturated aliphatic hydrocarbon group such as an ethyl group, a propyl group and a butyl group, which may be unsubstituted or substituted. The cycloalkyl group is, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted. The aralkyl group refers to an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group and a phenylethyl group, and the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. I don't care. The alkenyl group is, for example, a vinyl group,
It represents an unsaturated aliphatic hydrocarbon group containing a double bond such as an allyl group or a butadienyl group, which may be unsubstituted or substituted. The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexene group, which may be unsubstituted or substituted. . The alkoxy group refers to an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted.
The alkylthio group is obtained by substituting the oxygen atom of the ether bond of the alkoxy group with a sulfur atom. Also,
The aryl ether group indicates an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. Further, the arylthioether group is a group in which an oxygen atom of an ether bond of the arylether group is substituted with a sulfur atom. The aryl group refers to, for example, an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a pyrenyl group, which may be unsubstituted or substituted. Further, the heterocyclic group is, for example, a furyl group, a thienyl group, an oxazolyl group,
It represents a cyclic structural group having an atom other than carbon, such as a pyridyl group, a quinolyl group, and a carbazolyl group, which may be unsubstituted or substituted. Halogen refers to fluorine, chlorine, bromine and iodine. Haloalkanes, haloalkenes, and haloalkynes are those in which some or all of the aforementioned alkyl, alkenyl, and alkynyl groups, such as trifluoromethyl, have been substituted with the aforementioned halogens, and the rest are unsubstituted. It may be replaced. Aldehyde groups, carbonyl groups, ester groups, carbamoyl groups, and amino groups include those substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like. The cyclic hydrocarbon, aromatic hydrocarbon and heterocyclic ring may be unsubstituted or substituted. The silyl group means a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group, which may be unsubstituted or substituted. The ring structure formed between adjacent substituents may be unsubstituted or substituted.
【００２１】本発明における一般式（１）および一般式
（２）のイミダゾピリジン骨格を有する化合物の中で
は、適当なピーク波長の青色蛍光が得られることから一
般式（１）のＲ1〜Ｒ6のうち、あるいは一般式（２）の
Ｒ7〜Ｒ12のうち少なくとも一つは下記一般式（３）で
示される二重結合を含有する化合物が好適に用いられ
る。[0021] R 1 to R in formula (1) in the present invention and the general formula (2) Among the compounds having an imidazopyridine skeleton of the general formula since the blue phosphor suitable peak wavelength is obtained (1) of the six, or at least one of R 7 to R 12 in the general formula (2) is a compound containing a double bond represented by the following general formula (3) is preferably used.
【００２２】[0022]
【化８】 Embedded image
【００２３】（Ｒ13、Ｒ14、およびＲ15はそれぞれ同じ
でも異なっていても良く、水素、アルキル、シクロアル
キル、アラルキル、アルケニル、シクロアルケニル、ア
ルコキシ、アルキルチオ、アミノ、アルキルアミノ、ハ
ロゲン、ハロアルカン、シアノ、ニトロ、カルボキシ
ル、アリール、ベンジル、スチリル、エチニルナフタレ
ン、エチニルアントラセン、エチニルチオフェン、シン
ナミル、ベンジリデン、アシル、エステル、ホルミル基
から選ばれる。） これらの置換基の説明については、上述したものと同様
である。(R 13 , R 14 and R 15 may be the same or different and each represents hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkoxy, alkylthio, amino, alkylamino, halogen, haloalkane, Selected from cyano, nitro, carboxyl, aryl, benzyl, styryl, ethynylnaphthalene, ethynylanthracene, ethynylthiophene, cinnamyl, benzylidene, acyl, ester, and formyl groups.) The description of these substituents is the same as described above. It is.
【００２４】また、一般式（１）および一般式（２）の
イミダゾピリジン骨格を有する化合物の中では、熱的安
定性が得られることからイミダゾピリジン骨格を複数個
有する化合物が好ましく、分子を分岐状に修飾すること
が容易であることから下記一般式（４）および一般式
（５）で表される化合物がより好ましい。Further, among the compounds having an imidazopyridine skeleton represented by the general formulas (1) and (2), a compound having a plurality of imidazopyridine skeletons is preferable since thermal stability can be obtained. Compounds represented by the following general formulas (4) and (5) are more preferable because they can be easily modified into a shape.
【００２５】[0025]
【化９】 Embedded image
【００２６】（ここでＲ16〜Ｒ20はそれぞれ同じでも異
なっていてもよく、水素、アルキル基、シクロアルキル
基、アラルキル基、アルケニル基、シクロアルケニル
基、アルコキシ基、アルキルチオ基、アリールエーテル
基、アリールチオエーテル基、アリール基、複素環基、
ハロゲン、ハロアルカン、ハロアルケン、シアノ基、ア
ルデヒド基、カルボニル基、カルボキシル基、エステル
基、カルバモイル基、アミノ基、ニトロ基、シリル基、
シロキサニル基、隣接置換基との間に形成される環構造
の中から選ばれる。ｎは２以上の整数であり、Ｘ１は複
数のイミダゾピリジン骨格を共役的または非共役的に互
いに結合させる結合単位である。）(Wherein R 16 to R 20 may be the same or different and each represents hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an aryl ether group, Arylthioether group, aryl group, heterocyclic group,
Halogen, haloalkane, haloalkene, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group,
It is selected from a siloxanyl group and a ring structure formed between adjacent substituents. n is an integer of 2 or more, and X1 is a binding unit that binds a plurality of imidazopyridine skeletons to each other conjugated or non-conjugated. )
【００２７】[0027]
【化１０】 Embedded image
【００２８】（ここでＲ21〜Ｒ25はそれぞれ同じでも異
なっていてもよく、水素、アルキル基、シクロアルキル
基、アラルキル基、アルケニル基、シクロアルケニル
基、アルコキシ基、アルキルチオ基、アリールエーテル
基、アリールチオエーテル基、アリール基、複素環基、
ハロゲン、ハロアルカン、ハロアルケン、シアノ基、ア
ルデヒド基、カルボニル基、カルボキシル基、エステル
基、カルバモイル基、アミノ基、ニトロ基、シリル基、
シロキサニル基、隣接置換基との間に形成される環構造
の中から選ばれる。ｎは２以上の整数であり、Ｘ２は複
数のイミダゾピリジン骨格を共役的または非共役的に互
いに結合させる結合単位である。） これらの置換基の説明のうち、Ｒ16〜Ｒ20およびＲ21〜
Ｒ25に関しては上述したものと同様である。結合単位で
あるＸは単結合、二重結合、アルキル、シクロアルキ
ル、アリール、複素環、エーテルあるいはチオエーテル
からなり、これらは無置換でも置換されていてもかまわ
ないし、これらを単独あるいは組み合わせて用いてもか
まわない。(Wherein R 21 to R 25 may be the same or different and each represents hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an aryl ether group, Arylthioether group, aryl group, heterocyclic group,
Halogen, haloalkane, haloalkene, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group,
It is selected from a siloxanyl group and a ring structure formed between adjacent substituents. n is an integer of 2 or more, and X2 is a binding unit that binds a plurality of imidazopyridine skeletons to each other conjugated or non-conjugated. In the description of these substituents, R 16 to R 20 and R 21 to
R 25 is the same as described above. X, which is a bonding unit, is a single bond, a double bond, an alkyl, a cycloalkyl, an aryl, a heterocyclic ring, an ether or a thioether, which may be unsubstituted or substituted, and may be used alone or in combination. It doesn't matter.
【００２９】さらに、本発明における化合物を用いて高
輝度発光を得るには、キャリヤ輸送能が高い化合物を用
いるのが好ましい。そこで、前記イミダゾピリジン骨格
を複数個有する化合物としては、結合単位中に芳香環を
含んでいる化合物がより好ましい。ここでいう芳香環と
は置換または無置換の芳香族炭化水素あるいは芳香複素
環を意味し、これらを単独あるいは組合せて用いてもか
まわない。Further, in order to obtain high luminance emission using the compound of the present invention, it is preferable to use a compound having a high carrier transporting ability. Therefore, as the compound having a plurality of imidazopyridine skeletons, a compound containing an aromatic ring in the bonding unit is more preferable. The aromatic ring as used herein means a substituted or unsubstituted aromatic hydrocarbon or aromatic heterocyclic ring, and these may be used alone or in combination.
【００３０】上記のイミダゾピリジン骨格を有する化合
物として、具体的には下記のような構造があげられる。The compound having an imidazopyridine skeleton specifically has the following structure.
【００３１】[0031]
【化１１】 Embedded image
【００３２】[0032]
【化１２】 Embedded image
【００３３】[0033]
【化１３】 Embedded image
【００３４】[0034]
【化１４】 Embedded image
【００３５】[0035]
【化１５】 Embedded image
【００３６】[0036]
【化１６】 Embedded image
【００３７】[0037]
【化１７】 Embedded image
【００３８】[0038]
【化１８】 Embedded image
【００３９】[0039]
【化１９】 Embedded image
【００４０】[0040]
【化２０】 Embedded image
【００４１】[0041]
【化２１】 Embedded image
【００４２】イミダゾピリジン骨格を有する化合物はド
ーパント材料として用いてもホスト材料として用いても
かまわない。The compound having an imidazopyridine skeleton may be used as a dopant material or a host material.
【００４３】発光材料のホスト材料はイミダゾピリジン
骨格を有する化合物一種のみに限る必要はなく、複数の
該化合物を混合して用いたり、既知のホスト材料の一種
類以上を該化合物と混合して用いてもよい。既知のホス
ト材料としては特に限定されるものではないが、以前か
ら発光体として知られていたフェナンスレン、ピレン、
ペリレン、クリセンなどの縮合環誘導体、トリス（８−
キノリノラト）アルミニウムを始めとするキノリノール
誘導体の金属錯体、ベンズアゾール誘導体およびその金
属錯体、キノリノール誘導体と異なる配位子を組み合わ
せた金属錯体、オキサジアゾール誘導体およびその金属
錯体、チアジアゾール誘導体、スチルベン誘導体、チオ
フェン誘導体、テトラフェニルブタジエン誘導体、シク
ロペンタジエン誘導体、ビススチリルアントラセン誘導
体やジスチリルベンゼン誘導体などのビススチリル誘導
体、クマリン誘導体、ピロロピリジン誘導体、ピロロピ
ロール誘導体、ペリノン誘導体、チアジアゾロピリジン
誘導体、ポリマー系では、ポリフェニレンビニレン誘導
体、ポリパラフェニレン誘導体、そして、ポリチオフェ
ン誘導体などが使用できる。The host material of the light emitting material is not limited to one kind of the compound having an imidazopyridine skeleton. A plurality of such compounds may be used as a mixture, or one or more known host materials may be used as a mixture with the compound. You may. The known host material is not particularly limited, but phenanthrene, pyrene, which has long been known as a luminous body,
Fused ring derivatives such as perylene and chrysene; tris (8-
Metal complexes of quinolinol derivatives including quinolinolato) aluminum, benzazole derivatives and their metal complexes, metal complexes combining quinolinol derivatives with different ligands, oxadiazole derivatives and their metal complexes, thiadiazole derivatives, stilbene derivatives, thiophenes Derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, coumarin derivatives, pyrrolopyridine derivatives, pyrrolopyrrole derivatives, perinone derivatives, thiadiazolopyridine derivatives, and polyphenylene in the polymer system. Vinylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives can be used.
【００４４】発光材料に添加するドーパント材料は、特
に限定されるものではないが、イミダゾピリジン骨格を
有する化合物以外の具体的なものとしては、従来から知
られている、アントラセン、ピレン、テトラセン、ペン
タセン、ペリレン、ナフトピレン、ジベンゾピレンなど
の縮合環誘導体、アゾール誘導体およびその金属錯体、
トリアゾール誘導体およびその金属錯体、ベンズアゾー
ル誘導体及びその金属錯体、ベンズトリアゾール誘導体
およびその金属錯体、オキサジアゾール誘導体およびそ
の金属錯体、チアジアゾール誘導体およびその金属錯
体、ピラゾリン誘導体、スチルベン誘導体、チオフェン
誘導体、テトラフェニルブタジエン誘導体、シクロペン
タジエン誘導体、ビススチリルアントラセン誘導体やジ
スチリルベンゼン誘導体などのビススチリル誘導体、ジ
アザインダセン誘導体、フラン誘導体、ベンゾフラン誘
導体、フェニルイソベンゾフラン、ジメシチルイソベン
ゾフラン、ジ（２−メチルフェニル）イソベンゾフラ
ン、ジ（２−トリフルオロメチルフェニル）イソベンゾ
フラン、フェニルイソベンゾフランなどのイソベンゾフ
ラン誘導体、ジベンゾフラン誘導体、７−ジアルキルア
ミノクマリン誘導体、７−ピペリジノクマリン誘導体、
７−ヒドロキシクマリン誘導体、７−メトキシクマリン
誘導体、７−アセトキシクマリン誘導体、３−ベンズチ
アゾリルクマリン誘導体、３−ベンズイミダゾリルクマ
リン誘導体、３−ベンズオキサゾリルクマリン誘導体な
どのクマリン誘導体、ジシアノメチレンピラン誘導体、
ジシアノメチレンチオピラン誘導体、ポリメチン誘導
体、シアニン誘導体、オキソベンズアンスラセン誘導
体、キサンテン誘導体、ローダミン誘導体、フルオレセ
イン誘導体、ピリリウム誘導体、カルボスチリル誘導
体、アクリジン誘導体、ビス（スチリル）ベンゼン誘導
体、オキサジン誘導体、フェニレンオキサイド誘導体、
キナクリドン誘導体、キナゾリン誘導体、ピロロピリジ
ン誘導体、フロピリジン誘導体、１，２，５−チアジア
ゾロピレン誘導体、ペリノン誘導体、ピロロピロール誘
導体、スクアリリウム誘導体、ビオラントロン誘導体、
フェナジン誘導体、アクリドン誘導体、ジアザフラビン
誘導体などがそのまま使用できるが、特にイソベンゾフ
ラン誘導体が好適に用いられる。The dopant material to be added to the luminescent material is not particularly limited, but specific examples other than the compound having an imidazopyridine skeleton include conventionally known anthracene, pyrene, tetracene, and pentacene. , Perylene, naphthopyrene, fused ring derivatives such as dibenzopyrene, azole derivatives and metal complexes thereof,
Triazole derivative and its metal complex, benzazole derivative and its metal complex, benztriazole derivative and its metal complex, oxadiazole derivative and its metal complex, thiadiazole derivative and its metal complex, pyrazoline derivative, stilbene derivative, thiophene derivative, tetraphenyl Bisstyryl derivatives such as butadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives, diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di (2-methylphenyl) isobenzofuran, Isobenzofuran derivatives such as di (2-trifluoromethylphenyl) isobenzofuran and phenylisobenzofuran, dibenzo Run derivatives, 7-dialkylamino coumarin derivatives, 7-piperidinocarbonyl coumarin derivatives,
Coumarin derivatives such as 7-hydroxycoumarin derivative, 7-methoxycoumarin derivative, 7-acetoxycoumarin derivative, 3-benzthiazolyl coumarin derivative, 3-benzimidazolyl coumarin derivative, 3-benzoxazolyl coumarin derivative, dicyanomethylenepyran Derivatives,
Dicyanomethylenethiopyran derivative, polymethine derivative, cyanine derivative, oxobenzanthracene derivative, xanthene derivative, rhodamine derivative, fluorescein derivative, pyrylium derivative, carbostyril derivative, acridine derivative, bis (styryl) benzene derivative, oxazine derivative, phenylene oxide derivative ,
Quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, biolanthrone derivatives,
Although a phenazine derivative, an acridone derivative, a diazaflavin derivative and the like can be used as they are, an isobenzofuran derivative is particularly preferably used.
【００４５】本発明における電子輸送性材料としては、
電界を与えられた電極間において負極からの電子を効率
良く輸送することが必要で、電子注入効率が高く、注入
された電子を効率良く輸送することが望ましい。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、さらに安定性に優れ、トラップとなる不純物が製造
時および使用時に発生しにくい物質であることが要求さ
れる。このような条件を満たす物質として、８−ヒドロ
キシキノリンアルミニウムに代表されるキノリノール誘
導体金属錯体、トロポロン金属錯体、フラボノール金属
錯体、ペリレン誘導体、ペリノン誘導体、ナフタレン、
クマリン誘導体、オキサジアゾール誘導体、アルダジン
誘導体、ビススチリル誘導体、ピラジン誘導体、フェナ
ントロリン誘導体などがあるが特に限定されるものでは
ない。本発明におけるイミダゾピリジン骨格を有する化
合物も電子輸送能を有することから、電子輸送材料とし
ても用いることができる。これらの電子輸送材料は単独
でも用いられるが、異なる電子輸送材料と積層または混
合して使用しても構わない。As the electron transporting material in the present invention,
It is necessary to efficiently transport electrons from the negative electrode between the electrodes to which an electric field is applied, and it is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is required that the material has a high electron affinity, a high electron mobility, a high stability, and a small amount of impurities serving as traps during production and use. Materials satisfying such conditions include quinolinol derivative metal complexes represented by 8-hydroxyquinoline aluminum, tropolone metal complexes, flavonol metal complexes, perylene derivatives, perinone derivatives, naphthalene,
There are coumarin derivatives, oxadiazole derivatives, aldazine derivatives, bisstyryl derivatives, pyrazine derivatives, phenanthroline derivatives, and the like, but are not particularly limited. Since the compound having an imidazopyridine skeleton according to the invention also has an electron transporting ability, it can be used as an electron transporting material. These electron transporting materials may be used alone or may be laminated or mixed with different electron transporting materials.
【００４６】以上の正孔輸送層、発光層、電子輸送層に
用いられる材料は単独で各層を形成することができる
が、高分子結着剤としてポリ塩化ビニル、ポリカーボネ
ート、ポリスチレン、ポリ（Ｎ−ビニルカルバゾー
ル）、ポリメチルメタクリレート、ポリブチルメタクリ
レート、ポリエステル、ポリスルフォン、ポリフェニレ
ンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン
樹脂、フェノキシ樹脂、ポリアミド、エチルセルロー
ス、酢酸ビニル、ＡＢＳ樹脂、ポリウレタン樹脂などの
溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石
油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステ
ル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂
などの硬化性樹脂などに分散させて用いることも可能で
ある。The above materials used for the hole transporting layer, the light emitting layer and the electron transporting layer can be used alone to form the respective layers. As the polymer binder, polyvinyl chloride, polycarbonate, polystyrene, poly (N- (Vinyl carbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane resin, and other solvent-soluble resins. It can also be used by dispersing it in a curable resin such as a phenol resin, a xylene resin, a petroleum resin, a urea resin, a melamine resin, an unsaturated polyester resin, an alkyd resin, an epoxy resin, or a silicone resin.
【００４７】本発明における発光を司る物質の形成方法
は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング
法、分子積層法、コーティング法など特に限定されるも
のではないが、通常は、抵抗加熱蒸着、電子ビーム蒸着
が特性面で好ましい。層の厚みは発光を司る物質の抵抗
値にもよるので限定できないが、１０〜１０００ｎｍの
間から選ばれる。The method for forming the substance which controls light emission in the present invention is not particularly limited, such as resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, and coating. Beam evaporation is preferred in terms of properties. The thickness of the layer depends on the resistance of the substance that controls light emission and cannot be limited, but is selected from the range of 10 to 1000 nm.
【００４８】本発明における電気エネルギーとは主に直
流電流を指すが、パルス電流や交流電流を用いることも
可能である。電流値および電圧値は特に制限はないが、
素子の消費電力、寿命を考慮すると、できるだけ低いエ
ネルギーで最大の輝度が得られるようにするべきであ
る。The electric energy in the present invention mainly refers to a direct current, but it is also possible to use a pulse current or an alternating current. The current value and voltage value are not particularly limited,
In consideration of the power consumption and life of the device, it is necessary to obtain the maximum brightness with the lowest possible energy.
【００４９】本発明の発光素子はマトリクスまたはセグ
メント方式、あるいはその両者を組み合わせることによ
って表示するディスプレイを構成することが好ましい。
本発明におけるマトリクスとは、表示のための画素が格
子状に配置されたものをいい、画素の集合で文字や画像
を表示する。画素の形状、サイズは用途によって決ま
る。例えばパソコン、モニター、テレビの画像および文
字表示には、通常、一辺が３００μｍ以下の四角形の画
素が用いられるし、表示パネルのような大型ディスプレ
イの場合は、一辺がｍｍオーダーの画素を用いることに
なる。モノクロ表示の場合は、同じ色の画素を配列すれ
ばよいが、カラー表示の場合には赤、緑、青の画素を並
べて表示させる。この場合典型的にはデルタタイプとス
トライプタイプがある。尚、本発明における発光素子
は、赤、緑、青色発光が可能であるので、前記表示方法
を用いれば、マルチカラーまたはフルカラー表示もでき
る。そして、このマトリクスの駆動方法としては、線順
次駆動方法やアクティブマトリックスのどちらでもよ
い。線順次駆動の方が構造が簡単という利点があるが、
動作特性を考慮するとアクティブマトリックスの方が優
れる場合があるので、これも用途により使い分けること
が必要である。The light-emitting device of the present invention preferably constitutes a display for displaying by a matrix or segment system or a combination of both.
The matrix in the present invention refers to a matrix in which pixels for display are arranged in a lattice, and displays a character or an image by a set of pixels. The shape and size of the pixel depend on the application. For example, for the display of images and characters on personal computers, monitors, televisions, and the like, generally square pixels with a side of 300 μm or less are used, and in the case of a large display such as a display panel, pixels with a side on the order of mm are used. Become. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, red, green and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. Note that the light-emitting element of the present invention can emit red, green, and blue light, so that multi-color or full-color display can be performed by using the display method. The matrix may be driven by either a line-sequential driving method or an active matrix. Line-sequential drive has the advantage of a simpler structure,
In consideration of the operation characteristics, the active matrix is sometimes superior, so it is necessary to use the active matrix properly depending on the application.
【００５０】また、本発明におけるセグメントタイプと
は、予め決められた情報を表示するようにパターンを形
成し、決められた領域を発光させることを意味する。例
えば、デジタル時計や温度計における時刻や温度表示、
オーディオ機器や電磁調理器などの動作状態表示、自動
車のパネル表示などがあげられる。そして、前記マトリ
クス表示とセグメント表示は同じパネルの中に共存して
いてもよい。The segment type in the present invention means that a pattern is formed so as to display predetermined information and a predetermined area emits light. For example, the time and temperature display on a digital clock or thermometer,
Examples of the display include an operation state display of an audio device and an electromagnetic cooker, and a panel display of an automobile. The matrix display and the segment display may coexist in the same panel.
【００５１】本発明の発光素子はバックライトとしても
好ましく用いられる。バックライトは、主に自発光しな
い表示装置の視認性を向上させる目的に使用され、液晶
表示装置、時計、オーディオ装置、自動車パネル、表示
板、標識などに使用される。特に液晶表示装置、中でも
薄型化が課題となっているパソコン用途のバックライト
としては、従来方式のものが蛍光灯や導光板からなって
いるため薄型化が困難であることを考えると、本発明に
おける発光素子を用いたバックライトは薄型、軽量が特
徴になる。The light emitting device of the present invention is also preferably used as a backlight. The backlight is mainly used for improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like. In particular, as for the backlight for liquid crystal display devices, particularly for personal computer applications where thinning is an issue, the present invention is considered to be difficult because the conventional type is made of a fluorescent lamp or a light guide plate, and it is difficult to make it thin. The backlight using the light emitting element in the above is characterized by being thin and lightweight.
【００５２】[0052]
【実施例】以下、実施例および比較例をあげて本発明を
説明するが、本発明はこれらの例によって限定されるも
のではない。The present invention will be described below with reference to examples and comparative examples, but the present invention is not limited to these examples.
【００５３】実施例１ ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板
（旭硝子社製、１５Ω／□、電子ビーム蒸着品）を３０
×４０ｍｍに切断、エッチングを行った。得られた基板
をアセトン、セミコクリン５６で各々１５分間超音波洗
浄してから、超純水で洗浄した。続いてイソプロピルア
ルコールで１５分間超音波洗浄してから熱メタノールに
１５分間浸漬させて乾燥させた。この基板を素子を作製
する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内
に設置して、装置内の真空度が５×１０-5Ｐａ以下にな
るまで排気した。抵抗加熱法によって、まず正孔輸送材
料として４，４’−ビス（Ｎ−（ｍ−トリル）−Ｎ−フ
ェニルアミノ）ビフェニル（ＴＰＤ）を６５ｎｍ蒸着し
た。次に発光材料として、下記に示されるＥＭ１を１５
ｎｍの厚さに積層した。次に電子輸送材料として、２，
９−ジメチル−４，７−ジフェニル−１，１０−フェナ
ントロリンを３５ｎｍの厚さに積層し、引き続き金属リ
チウムを微量ドーピングした（膜厚換算０．５ｎｍ）。
最後に、銀を１５０ｎｍ蒸着して陰極とし、５×５ｍｍ
角の素子を作製した。ここで言う膜厚は表面粗さ計での
測定値で補正した水晶発振式膜厚モニター表示値であ
る。この発光素子からは、ピーク波長：４３０ｎｍの良
好な青色発光が得られた。Example 1 A glass substrate (15 Ω / □, electron beam vapor-deposited product, manufactured by Asahi Glass Co., Ltd.) on which an ITO transparent conductive film was deposited to a thickness of 150 nm
The wafer was cut into a size of 40 mm and etched. The obtained substrate was subjected to ultrasonic cleaning with acetone and semicocrine 56 for 15 minutes each, and then with ultrapure water. Subsequently, the substrate was subjected to ultrasonic cleaning with isopropyl alcohol for 15 minutes, immersed in hot methanol for 15 minutes, and dried. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the element, placed in a vacuum evaporation apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −5 Pa or less. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl (TPD) was deposited as a hole transporting material by a resistance heating method to a thickness of 65 nm. Next, as a light emitting material, EM1 shown below was added to 15
It was laminated to a thickness of nm. Next, as electron transport materials,
9-Dimethyl-4,7-diphenyl-1,10-phenanthroline was laminated to a thickness of 35 nm, and then a small amount of metallic lithium was doped (0.5 nm in film thickness conversion).
Finally, silver was deposited to a thickness of 150 nm to form a cathode, 5 × 5 mm
A corner element was produced. The film thickness referred to here is a value displayed on a crystal oscillation type film thickness monitor corrected by a value measured by a surface roughness meter. From this light emitting device, good blue light emission with a peak wavelength of 430 nm was obtained.
【００５４】[0054]
【化２２】 Embedded image
【００５５】実施例２ ホスト材料として下記に示されるＥＭ２を用いた他は実
施例１と全く同様にして発光素子を作製した。この発光
素子からは、ピーク波長：４５０ｎｍの良好な青色発光
が得られた。Example 2 A light emitting device was manufactured in exactly the same manner as in Example 1 except that EM2 shown below was used as a host material. From this light emitting device, good blue light emission with a peak wavelength of 450 nm was obtained.
【００５６】[0056]
【化２３】 Embedded image
【００５７】参考例１ ＥＭ３の合成 ３００ｍｌの三つ口フラスコに２２．４ｇの臭化銅(II)
を加え５０ｍｌの酢酸エチルを注ぎ、還流状態になるま
で加温した。続いて、５０ｍｌの四塩化炭素に４．１ｇ
の１，３，５−トリアセチルベンゼンを加えたものを注
ぎ、激しく攪拌した。反応終了後、放冷、沈殿物をろ別
した。得られたろ液を活性炭処理により脱色を行った
後、溶媒を除去し、水およびメタノールで洗浄した。得
られた固体をシリカゲルカラム処理し、１，３，５−ト
リス（ブロモアセチル）ベンゼンを得た。次に、３００
ｍｌの三つ口フラスコに６０℃に加温したポリリン酸５
０ｍｌを注ぎ、窒素下に保った。続いて、２．０ｇの
１，３，５−トリス（ブロモアセチル）ベンゼンおよび
２．３ｇの１−アミノイソキノリンを加えて、１２０〜
１５０℃の間で加熱攪拌した。反応終了後、反応溶液を
水に注ぎ、水酸化ナトリウムを用いて中和し、析出物を
濾別、減圧乾燥により褐色粉末を得た。この粉末は、シ
リカゲルカラム処理を行い、下記に示した化合物ＥＭ３
を得た。本化合物は３００ｎｍの励起光を照射すると４
５０ｎｍにピークを有する蛍光が観察された。Reference Example 1 Synthesis of EM3 22.4 g of copper (II) bromide was placed in a 300 ml three-necked flask.
Was added, 50 ml of ethyl acetate was poured, and the mixture was heated until a reflux state was reached. Subsequently, 4.1 g was added to 50 ml of carbon tetrachloride.
Of 1,3,5-triacetylbenzene was added and stirred vigorously. After the completion of the reaction, the mixture was allowed to cool and the precipitate was separated by filtration. After the obtained filtrate was decolorized by activated carbon treatment, the solvent was removed, and the filtrate was washed with water and methanol. The obtained solid was subjected to silica gel column treatment to obtain 1,3,5-tris (bromoacetyl) benzene. Next, 300
polyphosphoric acid 5 heated to 60 ° C. in a 3-ml three-necked flask
0 ml was poured and kept under nitrogen. Subsequently, 2.0 g of 1,3,5-tris (bromoacetyl) benzene and 2.3 g of 1-aminoisoquinoline were added, and
The mixture was heated and stirred at 150 ° C. After completion of the reaction, the reaction solution was poured into water, neutralized with sodium hydroxide, and the precipitate was separated by filtration and dried under reduced pressure to obtain a brown powder. This powder was subjected to silica gel column treatment to give the compound EM3 shown below.
I got This compound emits 4 when irradiated with 300 nm excitation light.
Fluorescence with a peak at 50 nm was observed.
【００５８】[0058]
【化２４】 Embedded image
【００５９】実施例３ ホスト材料として上記に示されるＥＭ３を用いた他は実
施例１と全く同様にして発光素子を作製した。この発光
素子からは、輝度：１０００カンデラ／平方メートル以
上、ピーク波長：４６０ｎｍの良好な青色発光が得られ
た。Example 3 A light emitting device was manufactured in exactly the same manner as in Example 1 except that EM3 shown above was used as a host material. From this light emitting device, good blue light emission having a luminance of 1000 candela / m 2 or more and a peak wavelength of 460 nm was obtained.
【００６０】参考例２ ＥＭ４の合成 ３００ｍｌの三つ口フラスコに２−（アミノメチル）ピ
リジン６．５ｇおよびトリメシン酸クロリド５．０ｇを
加え、６０ｍｌのピリジンおよび１２０ｍｌのベンゼン
を注ぎ、窒素下６０〜７０℃で加温攪拌した。２時間攪
拌後、反応溶液を５００ｍｌの水に注ぎ、ジクロロメタ
ンを加えた後有機層を抽出、溶媒除去を行い、白色粉末
を得た。次に、３００ｍｌの三つ口フラスコに６０℃に
加温したポリリン酸５０ｍｌを注ぎ、窒素下に保った。
続いて、先に得られた白色粉末３．０ｇ加えて、１２０
〜１５０℃の間で加熱攪拌した。反応終了後、反応溶液
を水に注ぎ、水酸化ナトリウムを用いて中和し、析出物
を濾別、減圧乾燥により褐色粉末を得た。この粉末は、
シリカゲルカラム処理を行い、下記に示した化合物ＥＭ
４を得た。本化合物は３００ｎｍの励起光を照射すると
４８０ｎｍにピークを有する蛍光が観察された。Reference Example 2 Synthesis of EM4 To a 300 ml three-necked flask, 6.5 g of 2- (aminomethyl) pyridine and 5.0 g of trimesic acid chloride were added, and 60 ml of pyridine and 120 ml of benzene were poured. The mixture was heated and stirred at 70 ° C. After stirring for 2 hours, the reaction solution was poured into 500 ml of water, dichloromethane was added, and then the organic layer was extracted and the solvent was removed to obtain a white powder. Next, 50 ml of polyphosphoric acid heated to 60 ° C. was poured into a 300 ml three-necked flask and kept under nitrogen.
Subsequently, 3.0 g of the previously obtained white powder was added, and
The mixture was heated and stirred at １５０150 ° C. After completion of the reaction, the reaction solution was poured into water, neutralized with sodium hydroxide, and the precipitate was separated by filtration and dried under reduced pressure to obtain a brown powder. This powder is
The silica gel column treatment was performed to obtain the compound EM shown below.
4 was obtained. When this compound was irradiated with 300 nm excitation light, fluorescence having a peak at 480 nm was observed.
【００６１】[0061]
【化２５】 Embedded image
【００６２】実施例４ ホスト材料として上記に示されるＥＭ４を用いた他は実
施例１と全く同様にして発光素子を作製した。この発光
素子からは、輝度：３０００カンデラ／平方メートル以
上、ピーク波長：４８０ｎｍの良好な青色発光が得られ
た。Example 4 A light emitting device was manufactured in exactly the same manner as in Example 1 except that EM4 shown above was used as a host material. From this light emitting device, good blue light emission having a luminance of 3000 candela / m 2 or more and a peak wavelength of 480 nm was obtained.
【００６３】比較例１ ホスト材料として実施例１で用いたＥＭ１の代わりにビ
ス（２−メチルキノリノラート）（２−ピリジノラー
ト）アルミニウム（III）を用いた以外は実施例１と全
く同様にして発光素子を作製した。この発光素子から
は、輝度：１０００カンデラ／平方メートル以上の発光
が得られたが、ピーク波長：５１０ｎｍの青緑色発光し
か得られなかった。Comparative Example 1 The procedure of Example 1 was repeated except that bis (2-methylquinolinolate) (2-pyridinolate) aluminum (III) was used instead of EM1 used in Example 1 as a host material. A light-emitting element was manufactured. The light-emitting device emitted light with a luminance of 1000 candela / square meter or more, but emitted only blue-green light with a peak wavelength of 510 nm.
【００６４】実施例５ ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板
（旭硝子社製、１５Ω／□、電子ビーム蒸着品）を３０
×４０ｍｍに切断、フォトリソグラフィ法によって３０
０μｍピッチ（残り幅２７０μｍ）×３２本のストライ
プ状にパターン加工した。ＩＴＯストライプの長辺方向
片側は外部との電気的接続を容易にするために１．２７
ｍｍピッチ（開口部幅８００μｍ）まで広げてある。得
られた基板をアセトン、セミコクリン５６で各々１５分
間超音波洗浄してから、超純水で洗浄した。続いてイソ
プロピルアルコールで１５分間超音波洗浄してから熱メ
タノールに１５分間浸漬させて乾燥させた。この基板を
素子を作製する直前に１時間ＵＶ−オゾン処理し、真空
蒸着装置内に設置して、装置内の真空度が５×１０-4Ｐ
ａ以下になるまで排気した。抵抗加熱法によって、まず
正孔輸送層として、ＴＰＤを５０ｎｍ蒸着し、発光層と
して、実施例３で用いたＥＭ３を１５ｎｍの厚さに、そ
して電子輸送層として、２，９−ジメチル−４，７−ジ
フェニル−１，１０−フェナントロリンを３５ｎｍの厚
さに蒸着した。ここで言う膜厚は表面粗さ計での測定値
で補正した水晶発振式膜厚モニター表示値である。次に
厚さ５０μｍのコバール板にウエットエッチングによっ
て１６本の２５０μｍの開口部（残り幅５０μｍ、３０
０μｍピッチに相当）を設けたマスクを、真空中でＩＴ
Ｏストライプに直交するようにマスク交換し、マスクと
ＩＴＯ基板が密着するように裏面から磁石で固定した。
そして金属リチウムを微量ドーピング（膜厚換算０．５
ｎｍ）した後、アルミニウムを１５０ｎｍ蒸着して３２
×１６ドットマトリクス素子を作製した。本素子をマト
リクス駆動させたところ、クロストークなく文字表示で
きた。Example 5 A glass substrate (15 Ω / □, electron beam vapor-deposited product, manufactured by Asahi Glass Co., Ltd.) on which an ITO transparent conductive film was deposited to a thickness of 150 nm
Cut to × 40mm, 30 by photolithography
The pattern was processed into a stripe pattern of 0 μm pitch (remaining width 270 μm) × 32 stripes. One side of the long side of the ITO stripe is 1.27 to facilitate electrical connection with the outside.
mm pitch (800 μm opening width). The obtained substrate was subjected to ultrasonic cleaning with acetone and semicocrine 56 for 15 minutes each, and then with ultrapure water. Subsequently, the substrate was subjected to ultrasonic cleaning with isopropyl alcohol for 15 minutes, immersed in hot methanol for 15 minutes, and dried. This substrate was subjected to UV-ozone treatment for one hour immediately before producing the element, and was placed in a vacuum evaporation apparatus, and the degree of vacuum in the apparatus was 5 × 10 -4 P
The gas was exhausted until the pressure became equal to or less than a. First, 50 nm of TPD was deposited as a hole transport layer by a resistance heating method, EM3 used in Example 3 was formed to a thickness of 15 nm as a light emitting layer, and 2,9-dimethyl-4, 7-Diphenyl-1,10-phenanthroline was deposited to a thickness of 35 nm. The film thickness referred to here is a value displayed on a crystal oscillation type film thickness monitor corrected by a value measured by a surface roughness meter. Next, 16 openings of 250 μm (remaining width 50 μm, 30 μm) were wet-etched into a 50 μm-thick Kovar plate.
A mask provided with a pitch of 0 μm) is placed in an IT
The mask was replaced so as to be orthogonal to the O stripe, and the mask and the ITO substrate were fixed with magnets from the back so that the ITO substrate was in close contact with the mask.
And doping with a small amount of metallic lithium (film thickness conversion 0.5
nm) and then depositing aluminum to a thickness of 150 nm to 32 nm.
A × 16 dot matrix element was manufactured. When this device was driven in a matrix, characters could be displayed without crosstalk.
【００６５】[0065]
【発明の効果】本発明は、発光効率が高く、高輝度で色
純度に優れた発光素子を提供できるものである。該発光
素子は、特に青色発光に対して有効なものである。According to the present invention, it is possible to provide a light emitting device having high luminous efficiency, high luminance and excellent color purity. The light emitting element is particularly effective for emitting blue light.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｃ０７Ｄ 471/04 １０８ Ｃ０７Ｄ 471/04 １０８Ｅ １０８Ｑ １０８Ｘ １０８Ａ Ｆターム(参考） 3K007 AB02 AB03 AB04 AB17 BA06 CA01 CB01 DA00 DB03 EB00 FA01 4C065 AA03 BB06 CC01 DD02 EE02 HH02 JJ03 PP03 PP07 PP09 PP18 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) C07D 471/04 108 C07D 471/04 108E 108Q 108X 108A F-term (Reference) 3K007 AB02 AB03 AB04 AB17 BA06 CA01 CB01 DA00 DB03 EB00 FA01 4C065 AA03 BB06 CC01 DD02 EE02 HH02 JJ03 PP03 PP07 PP09 PP18
Claims (12)
し、電気エネルギーにより発光する素子において、該素
子がイミダゾピリジン骨格を有する化合物を含むことを
特徴とする発光素子。1. A light-emitting element in which a substance which emits light exists between an anode and a cathode and which emits light by electric energy, wherein the element contains a compound having an imidazopyridine skeleton.
記一般式（１）で表されることを特徴とする請求項１記
載の発光素子。 【化１】 （ここでＲ1〜Ｒ6はそれぞれ同じでも異なっていてもよ
く、結合、水素、アルキル基、シクロアルキル基、アラ
ルキル基、アルケニル基、シクロアルケニル基、アルコ
キシ基、アルキルチオ基、アリールエーテル基、アリー
ルチオエーテル基、アリール基、複素環基、ハロゲン、
シアノ基、アルデヒド基、カルボニル基、カルボキシル
基、エステル基、カルバモイル基、アミノ基、ニトロ
基、シリル基、シロキサニル基、隣接置換基との間に形
成される環構造の中から選ばれる。）2. The light emitting device according to claim 1, wherein the compound having an imidazopyridine skeleton is represented by the following general formula (1). Embedded image (Wherein R 1 to R 6 may be the same or different, and each represents a bond, hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl Thioether group, aryl group, heterocyclic group, halogen,
It is selected from a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxanyl group, and a ring structure formed between adjacent substituents. )
記一般式（２）で表されることを特徴とする請求項１記
載の発光素子。 【化２】 （ここでＲ7〜Ｒ12はそれぞれ同じでも異なっていても
よく、結合、水素、アルキル基、シクロアルキル基、ア
ラルキル基、アルケニル基、シクロアルケニル基、アル
コキシ基、アルキルチオ基、アリールエーテル基、アリ
ールチオエーテル基、アリール基、複素環基、ハロゲ
ン、ハロアルカン、ハロアルケン、シアノ基、アルデヒ
ド基、カルボニル基、カルボキシル基、エステル基、カ
ルバモイル基、アミノ基、ニトロ基、シリル基、シロキ
サニル基、隣接置換基との間に形成される環構造の中か
ら選ばれる。）3. The light emitting device according to claim 1, wherein the compound having an imidazopyridine skeleton is represented by the following general formula (2). Embedded image (Here, R 7 to R 12 may be the same or different, and each represents a bond, hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an arylether group, an aryl group. Thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, adjacent substituent and Selected from the ring structures formed between them.)
おいて、Ｒ1〜Ｒ6のうち、少なくとも１つは下記一般式
（３）で示されることを特徴とする発光素子。 【化３】 （Ｒ13、Ｒ14、およびＲ15はそれぞれ同じでも異なって
いても良く、水素、アルキル、シクロアルキル、アラル
キル、アルケニル、シクロアルケニル、アルコキシ、ア
ルキルチオ、アミノ、アルキルアミノ、ハロゲン、ハロ
アルカン、シアノ、ニトロ、カルボキシル、アリール、
ベンジル、スチリル、エチニルナフタレン、エチニルア
ントラセン、エチニルチオフェン、シンナミル、ベンジ
リデン、アシル、エステル、ホルミル基から選ばれ
る。）In R 1 to R 6 of 4. The method of claim 2 formula wherein (1), of the R 1 to R 6, at least one light-emitting, characterized in that the general formula (3) element. Embedded image (R 13 , R 14 and R 15 may be the same or different and each represents hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkoxy, alkylthio, amino, alkylamino, halogen, haloalkane, cyano, nitro , Carboxyl, aryl,
It is selected from benzyl, styryl, ethynylnaphthalene, ethynylanthracene, ethynylthiophene, cinnamyl, benzylidene, acyl, ester, and formyl groups. )
において、Ｒ7〜Ｒ12のうち、少なくとも１つは上記一
般式（３）で表されることを特徴とする発光素子。5. R 7 to R 12 of the formula (2) according to claim 3.
, Wherein at least one of R 7 to R 12 is represented by the general formula (3).
し、電気エネルギーにより発光する素子において、該素
子がイミダゾピリジン骨格を複数個有する化合物を含む
ことを特徴とする請求項１〜３のいずれか記載の発光素
子。6. An element which emits light by electric energy, wherein a substance which emits light exists between the anode and the cathode, wherein the element contains a compound having a plurality of imidazopyridine skeletons. The light-emitting device according to any one of the above.
物が下記一般式（４）で表されることを特徴とする請求
項６記載の発光素子。 【化４】 （ここでＲ16〜Ｒ20はそれぞれ同じでも異なっていても
よく、水素、アルキル基、シクロアルキル基、アラルキ
ル基、アルケニル基、シクロアルケニル基、アルコキシ
基、アルキルチオ基、アリールエーテル基、アリールチ
オエーテル基、アリール基、複素環基、ハロゲン、ハロ
アルカン、ハロアルケン、シアノ基、アルデヒド基、カ
ルボニル基、カルボキシル基、エステル基、カルバモイ
ル基、アミノ基、ニトロ基、シリル基、シロキサニル
基、隣接置換基との間に形成される環構造の中から選ば
れる。ｎは２以上の整数であり、Ｘ１は複数のイミダゾ
ピリジン骨格を共役的または非共役的に互いに結合させ
る結合単位である。）7. The light emitting device according to claim 6, wherein the compound having a plurality of imidazopyridine skeletons is represented by the following general formula (4). Embedded image (Here, R 16 to R 20 may be the same or different, and each represents a hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group. , Aryl group, heterocyclic group, halogen, haloalkane, haloalkene, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, between adjacent substituents And n is an integer of 2 or more, and X1 is a binding unit that couples a plurality of imidazopyridine skeletons conjugately or non-conjugatedly.)
物が下記一般式（５）で表されることを特徴とする請求
項６記載の発光素子。 【化５】 （ここでＲ21〜Ｒ25はそれぞれ同じでも異なっていても
よく、水素、アルキル基、シクロアルキル基、アラルキ
ル基、アルケニル基、シクロアルケニル基、アルコキシ
基、アルキルチオ基、アリールエーテル基、アリールチ
オエーテル基、アリール基、複素環基、ハロゲン、ハロ
アルカン、ハロアルケン、シアノ基、アルデヒド基、カ
ルボニル基、カルボキシル基、エステル基、カルバモイ
ル基、アミノ基、ニトロ基、シリル基、シロキサニル
基、隣接置換基との間に形成される環構造の中から選ば
れる。ｎは２以上の整数であり、Ｘ２は複数のイミダゾ
ピリジン骨格を共役的または非共役的に互いに結合させ
る結合単位である。）8. The light emitting device according to claim 6, wherein the compound having a plurality of imidazopyridine skeletons is represented by the following general formula (5). Embedded image (Here, R 21 to R 25 may be the same or different, and each represents a hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group. , Aryl group, heterocyclic group, halogen, haloalkane, haloalkene, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, between adjacent substituents And n is an integer of 2 or more, and X2 is a binding unit that couples a plurality of imidazopyridine skeletons conjugated or non-conjugated to each other.)
で示した結合単位が芳香環を含むことを特徴とする請求
項７または８記載の発光素子。9. X1 of the general formula (4) and X2 of the general formula (5)
9. The light-emitting device according to claim 7, wherein the bonding unit represented by the formula (1) contains an aromatic ring.
とする請求項１〜９のいずれか記載の発光素子。10. The light emitting device according to claim 1, wherein said compound is a light emitting material.
特徴とする請求項１〜９のいずれか記載の発光素子。11. The light emitting device according to claim 1, wherein said compound is an electron transport material.
グメント方式によって表示するディスプレイを構成する
ことを特徴とする請求項１０または１１記載の発光素
子。12. The light emitting device according to claim 10, wherein the light emitting device constitutes a display for displaying by a matrix and / or segment method.
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|---|---|---|---|
| JP17405899A JP4032566B2 (en) | 1999-06-21 | 1999-06-21 | Light emitting element |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17405899A JP4032566B2 (en) | 1999-06-21 | 1999-06-21 | Light emitting element |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001006877A true JP2001006877A (en) | 2001-01-12 |
| JP2001006877A5 JP2001006877A5 (en) | 2006-08-03 |
| JP4032566B2 JP4032566B2 (en) | 2008-01-16 |
Family
ID=15971893
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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| Country | Link |
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| CN114316285A (en) * | 2021-11-30 | 2022-04-12 | 中国科学院福建物质结构研究所 | Inorganic-organic hybrid compound crystal KCuIL and preparation method and application thereof |
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