JP6821959B2 - Manufacturing method of organic EL element - Google Patents
Manufacturing method of organic EL element Download PDFInfo
- Publication number
- JP6821959B2 JP6821959B2 JP2016115085A JP2016115085A JP6821959B2 JP 6821959 B2 JP6821959 B2 JP 6821959B2 JP 2016115085 A JP2016115085 A JP 2016115085A JP 2016115085 A JP2016115085 A JP 2016115085A JP 6821959 B2 JP6821959 B2 JP 6821959B2
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- Prior art keywords
- organic
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- forming
- derivatives
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- 238000004519 manufacturing process Methods 0.000 title claims description 43
- 239000000463 material Substances 0.000 claims description 105
- 239000010410 layer Substances 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 54
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 45
- 239000002346 layers by function Substances 0.000 claims description 38
- 238000007789 sealing Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 12
- 238000002347 injection Methods 0.000 description 46
- 239000007924 injection Substances 0.000 description 46
- 230000005525 hole transport Effects 0.000 description 22
- -1 dimethylboryl Chemical group 0.000 description 16
- 230000001186 cumulative effect Effects 0.000 description 14
- 230000008569 process Effects 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 229920002098 polyfluorene Polymers 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229920000265 Polyparaphenylene Polymers 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000010304 firing Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000002605 large molecules Chemical class 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000011254 layer-forming composition Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000123 polythiophene Polymers 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 229960000956 coumarin Drugs 0.000 description 3
- 235000001671 coumarin Nutrition 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- 229910000846 In alloy Inorganic materials 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000007611 bar coating method Methods 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- 229910003472 fullerene Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- SHXCHSNZIGEBFL-UHFFFAOYSA-N 1,3-benzothiazole;zinc Chemical compound [Zn].C1=CC=C2SC=NC2=C1 SHXCHSNZIGEBFL-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- ZMLPKJYZRQZLDA-UHFFFAOYSA-N 1-(2-phenylethenyl)-4-[4-(2-phenylethenyl)phenyl]benzene Chemical group C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZMLPKJYZRQZLDA-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
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- AJWRRBADQOOFSF-UHFFFAOYSA-N C1=CC=C2OC([Zn])=NC2=C1 Chemical compound C1=CC=C2OC([Zn])=NC2=C1 AJWRRBADQOOFSF-UHFFFAOYSA-N 0.000 description 1
- UXYHZIYEDDINQH-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=C1 Chemical compound C1=CNC2=C3C=NN=C3C=CC2=C1 UXYHZIYEDDINQH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CRZQGDNQQAALAY-UHFFFAOYSA-N Me ester-Phenylacetic acid Natural products COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229920000292 Polyquinoline Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
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- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
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- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 239000010931 gold Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
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- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
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- 229910003437 indium oxide Inorganic materials 0.000 description 1
- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 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
- 239000011229 interlayer Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound 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
- FIZIRKROSLGMPL-UHFFFAOYSA-N phenoxazin-1-one Chemical compound C1=CC=C2N=C3C(=O)C=CC=C3OC2=C1 FIZIRKROSLGMPL-UHFFFAOYSA-N 0.000 description 1
- UOMHBFAJZRZNQD-UHFFFAOYSA-N phenoxazone Natural products C1=CC=C2OC3=CC(=O)C=CC3=NC2=C1 UOMHBFAJZRZNQD-UHFFFAOYSA-N 0.000 description 1
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- 238000007747 plating Methods 0.000 description 1
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- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
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- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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- Electroluminescent Light Sources (AREA)
Description
本発明は、有機ＥＬ素子の製造方法に関する。 The present invention relates to a method for manufacturing an organic EL device.
有機エレクトロルミネッセンス素子（以下、「有機ＥＬ素子」と言う。）は、発光効率が高く、駆動電圧が低いことから、ディスプレイ及び照明の用途に好適に使用することが可能である。有機ＥＬ素子は、陽極と陰極と、該陽極及び該陰極間に配置される発光層とを含み、該陽極及び該陰極からそれぞれ注入される正孔及び電子が、該発光層において結合することによって発光する。 An organic electroluminescence element (hereinafter referred to as an "organic EL element") has high luminous efficiency and a low drive voltage, and therefore can be suitably used for display and lighting applications. The organic EL element includes an anode and a cathode, and a light emitting layer arranged between the anode and the cathode, and holes and electrons injected from the anode and the cathode, respectively, are combined in the light emitting layer. It emits light.
有機ＥＬ素子には、製造方法が容易で、素子の大面積化が容易な塗布法によって発光層等の有機層を形成できるという利点がある。有機ＥＬ素子の有機層を形成する際の環境に関しては、有機層の成膜工程を、硫黄酸化物濃度が２．２μｇ／ｍ3以下、窒素酸化物濃度が３．１μｇ／ｍ3以下、二酸化炭素濃度が０．７μｇ／ｍ3以下で製造する有機ＥＬ素子の製造方法が提案されている（特許文献１）。 The organic EL device has an advantage that an organic layer such as a light emitting layer can be formed by a coating method that is easy to manufacture and can easily increase the area of the device. Regarding the environment for forming the organic layer of the organic EL element, the process of forming the organic layer is as follows: sulfur oxide concentration is 2.2 μg / m 3 or less, nitrogen oxide concentration is 3.1 μg / m 3 or less, and dioxide. A method for producing an organic EL element having a carbon concentration of 0.7 μg / m 3 or less has been proposed (Patent Document 1).
しかし、上記の製造方法により製造された有機ＥＬ素子は、必ずしも発光寿命が十分ではなかった。
そこで、本発明は、発光寿命が優れる有機ＥＬ素子の製造方法を提供することを目的とする。
However, the organic EL device manufactured by the above manufacturing method does not always have a sufficient light emission life.
Therefore, an object of the present invention is to provide a method for manufacturing an organic EL element having an excellent light emitting life.
本発明は、以下の[１]〜[５]を提供する。
［１］
陽極と、陰極と、陽極と陰極の間に設けられた少なくとも１層の有機機能層と、封止層とを有する有機ＥＬ素子の製造方法であって、
陽極を形成する工程と、陰極を形成する工程と、少なくとも１層の有機機能層を形成する工程と、封止層を形成する工程とを含み、
少なくとも１層の有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子が曝露されるプロピレングリコール−１−モノメチルエーテル−２−アセテート（以下、「ＰＧＭＥＡ」と言う。）の平均濃度：Ａ（ｐｐｍ）と、曝露時間：Ｂ（秒）とが、式（１−１）を満たす、有機ＥＬ素子の製造方法。
０≦Ａ×Ｂ＜９ （１−１）
［２］
Ａが、式（２−１）を満たす、［１］に記載の有機ＥＬ素子の製造方法。
０≦Ａ＜１ （２−１）
［３］
Ｂが、式（３−１）を満たす、［１］又は［２］に記載の有機ＥＬ素子の製造方法。
０≦Ｂ≦８６４００ （３−１）
［４］
少なくとも１層の有機機能層を形成する工程が、有機機能材料と有機溶媒とを含有する組成物を用いて、塗布法により成膜される工程を含む、［１］〜［３］のいずれか１項に記載の有機ＥＬ素子の製造方法。
［５］
少なくとも１層の有機機能層が高分子化合物を含む［１］〜［４］のいずれか１項に記載の有機ＥＬ素子の製造方法。
The present invention provides the following [1] to [5].
[1]
A method for manufacturing an organic EL device having an anode, a cathode, at least one organic functional layer provided between the anode and the cathode, and a sealing layer.
It includes a step of forming an anode, a step of forming a cathode, a step of forming at least one organic functional layer, and a step of forming a sealing layer.
Propylene glycol-1-monomethyl ether-2-acetate (hereinafter referred to as propylene glycol-1-monomethyl ether-2-acetate) to which the organic EL device being manufactured is exposed from the start of the step of forming at least one organic functional layer to the end of the step of forming the sealing layer. , "PGMEA"), a method for producing an organic EL device, wherein the average concentration: A (ppm) and the exposure time: B (seconds) satisfy the formula (1-1).
0 ≦ A × B <9 (1-1)
[2]
The method for manufacturing an organic EL device according to [1], wherein A satisfies the formula (2-1).
0 ≦ A <1 (2-1)
[3]
The method for producing an organic EL device according to [1] or [2], wherein B satisfies the formula (3-1).
0 ≦ B ≦ 86400 (3-1)
[4]
Any of [1] to [3], wherein the step of forming at least one organic functional layer includes a step of forming a film by a coating method using a composition containing an organic functional material and an organic solvent. The method for manufacturing an organic EL element according to item 1.
[5]
The method for producing an organic EL device according to any one of [1] to [4], wherein at least one organic functional layer contains a polymer compound.
本発明によれば、発光寿命が優れる有機ＥＬ素子の製造方法を提供することができる。 According to the present invention, it is possible to provide a method for manufacturing an organic EL element having an excellent light emitting life.
以下、本発明の好ましい実施形態について説明する。 Hereinafter, preferred embodiments of the present invention will be described.
＜共通する用語の説明＞
本明細書で共通して用いられる用語は、特記しない限り、以下の意味である。
<Explanation of common terms>
Unless otherwise specified, the terms commonly used in the present specification have the following meanings.
「高分子化合物」とは、分子量分布を有し、ポリスチレン換算の数平均分子量が１×103〜１×108である重合体を意味する。 The “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 × 10 3 to 1 × 10 8 .
高分子化合物は、ブロック共重合体、ランダム共重合体、交互共重合体、グラフト共重合体のいずれであってもよいし、その他の態様であってもよい。 The polymer compound may be a block copolymer, a random copolymer, an alternate copolymer, a graft copolymer, or any other embodiment.
「低分子化合物」とは、分子量分布を有さず、分子量が１×104以下の化合物を意味する。 By "low molecular compound" does not have a molecular weight distribution, molecular weight means a 1 × 10 4 or less of the compound.
「架橋基」とは、加熱処理（焼成）、紫外線照射処理、ラジカル反応等に供することにより、新たな結合を生成することが可能な基であり、好ましくは、式(B-1)-(B-17)のいずれかで表される基である。これらの基は、置換基を有していてもよい。 The "crosslinked group" is a group capable of forming a new bond by being subjected to heat treatment (baking), ultraviolet irradiation treatment, radical reaction, etc., and is preferably the formula (B-1)-(. It is a radical represented by any of B-17). These groups may have substituents.
「製造中の有機ＥＬ素子が曝露される」とは、該有機ＥＬ素子の外に存在する気体に曝露されることを意味する。 "The organic EL device being manufactured is exposed" means that it is exposed to a gas existing outside the organic EL device.
「少なくとも１層の有機機能層を形成する工程の開始時」とは、最初の有機機能層を形成する工程の開始時を意味する。 “At the start of the step of forming at least one organic functional layer” means the start of the step of forming the first organic functional layer.
「ｐｐｍ」は、体積基準である。 "Ppm" is a volume basis.
＜有機ＥＬ素子の製造方法＞
本発明の製造方法は、
陽極と、陰極と、陽極と陰極の間に設けられた少なくとも１層の有機機能層と、封止層とを有する有機ＥＬ素子の製造方法であって、
陽極を形成する工程と、陰極を形成する工程と、少なくとも１層の有機機能層を形成する工程と、封止層を形成する工程とを含み、
少なくとも１層の有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子が曝露されるＰＧＭＥＡの平均濃度：Ａ（ｐｐｍ）と、曝露時間：Ｂ（秒）とが、前記式（１−１）を満たす、有機ＥＬ素子の製造方法である。
<Manufacturing method of organic EL element>
The manufacturing method of the present invention
A method for manufacturing an organic EL device having an anode, a cathode, at least one organic functional layer provided between the anode and the cathode, and a sealing layer.
It includes a step of forming an anode, a step of forming a cathode, a step of forming at least one organic functional layer, and a step of forming a sealing layer.
The average concentration of PGMEA to which the organic EL device being manufactured is exposed from the start of the step of forming at least one organic functional layer to the end of the step of forming the sealing layer: A (ppm) and the exposure time. : B (seconds) is a method for manufacturing an organic EL device that satisfies the above formula (1-1).
有機ＥＬ素子が複数の有機機能層を有する場合、ＰＧＭＥＡの平均濃度Ａと曝露時間Ｂとの積Ａ×Ｂは、各有機機能層を形成する工程で製造中の有機ＥＬ素子が曝露されるＰＧＭＥＡの平均濃度ａ（ｐｐｍ）と、曝露時間ｂ（秒）の積の総和からも算出できる。 When the organic EL element has a plurality of organic functional layers, the product A × B of the average concentration A of PGMEA and the exposure time B is PGMEA to which the organic EL element being manufactured is exposed in the step of forming each organic functional layer. It can also be calculated from the sum of the products of the average concentration a (ppm) and the exposure time b (seconds).
Ａ×Ｂは、良好な素子寿命を保持できるので、式（１−２）を満たすことが好ましく、式（１−３）を満たすことがより好ましい。また、Ａ×Ｂは、発光効率を考慮すると、４以上であることが好ましい。
０≦Ａ×Ｂ＜８．５ （１−２）
０≦Ａ×Ｂ＜７ （１−３）
Since A × B can maintain a good element life, it is preferable to satisfy the formula (1-2), and it is more preferable to satisfy the formula (1-3). Further, A × B is preferably 4 or more in consideration of luminous efficiency.
0 ≦ A × B <8.5 (1-2)
0 ≦ A × B <7 (1-3)
少なくとも１層の有機機能層を形成する工程は、通常、成膜段階、乾燥段階、待機段階、焼成段階、及び、冷却段階を含む。これらのうち、乾燥段階、待機段階、焼成段階、及び、冷却段階は、不要である場合には省略することができる。
成膜段階とは、真空蒸着法又は塗布法を用いて、有機機能材料、又は、有機機能材料と有機溶媒とを含有する組成物で、膜を形成する段階である。
乾燥段階とは、成膜段階を塗布法により行った場合に、必要に応じて有機溶媒を除去する段階である。乾燥段階は、膜形状を平坦にするために、真空中で行うことが好ましい。
待機段階とは、次の段階に移るまでに製造中の有機ＥＬ素子が保持される段階である。待機段階は、短時間であることが好ましい。
焼成段階とは、有機機能材料が架橋基を有する場合に、該架橋基を架橋させるため、又は、乾燥段階に残留した有機溶媒、若しくは、有機機能層中の水分を除去する段階である。焼成段階は、有機機能材料の酸化を防ぐため、不活性ガス雰囲気下で行うことが好ましい。
冷却段階とは、焼成した製造中の有機ＥＬ素子を、室温まで戻す段階である。冷却段階は、水分の吸着を防ぐため、水分濃度が１ｐｐｍ以下の乾燥環境で行うことが好ましい。
The step of forming at least one organic functional layer usually includes a film forming step, a drying step, a waiting step, a firing step, and a cooling step. Of these, the drying step, the waiting step, the firing step, and the cooling step can be omitted if unnecessary.
The film forming step is a step of forming a film with an organic functional material or a composition containing an organic functional material and an organic solvent by using a vacuum vapor deposition method or a coating method.
The drying step is a step of removing the organic solvent, if necessary, when the film forming step is performed by the coating method. The drying step is preferably carried out in vacuum in order to flatten the film shape.
The standby stage is a stage in which the organic EL element being manufactured is held before moving to the next stage. The waiting stage is preferably short.
The firing step is a step of removing the water content in the organic solvent or the organic functional layer remaining in the drying step or for cross-linking the cross-linking group when the organic functional material has a cross-linking group. The firing step is preferably carried out in an inert gas atmosphere in order to prevent oxidation of the organic functional material.
The cooling stage is a stage in which the fired organic EL element being manufactured is returned to room temperature. The cooling step is preferably performed in a dry environment having a water concentration of 1 ppm or less in order to prevent adsorption of water.
Ａは、良好な素子寿命を保持できるので、前記式（２−１）を満たすことが好ましく、式（２−２）を満たすことがより好ましく、式（２−３）を満たすことが更に好ましい。
０≦Ａ＜０．５ （２−２）
０≦Ａ＜０．１ （２−３）
Since A can maintain a good element life, it is preferable to satisfy the above formula (2-1), more preferably to satisfy the formula (2-2), and further preferably to satisfy the formula (2-3). ..
0 ≤ A <0.5 (2-2)
0 ≦ A <0.1 (2-3)
Ｂは、良好な素子寿命を保持できるので、前記式（３−１）を満たすことが好ましく、式（３−２）を満たすことがより好ましく、式（３−３）を満たすことが更に好ましい。
０≦Ｂ＜４３２００ （３−２）
０≦Ｂ＜１８０００ （３−３）
Since B can maintain a good element life, it is preferable to satisfy the above formula (3-1), more preferably to satisfy the formula (3-2), and further preferably to satisfy the formula (3-3). ..
0 ≦ B <43200 (3-2)
0 ≤ B <18000 (3-3)
本発明の製造方法において、少なくとも１層の有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までは、ＰＧＭＥＡの平均濃度が低い環境下で行われる。こうした環境は、いかなる方法で準備してもよいが、少なくとも１層の有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までは、外気取り入れ口に除去フィルターを設置した室内環境下で行うことが好ましい。 In the production method of the present invention, from the start of the step of forming at least one organic functional layer to the end of the step of forming the sealing layer, the process is carried out in an environment where the average concentration of PGMEA is low. Such an environment may be prepared by any method, but a removal filter is installed at the outside air intake port from the start of the process of forming at least one organic functional layer to the end of the process of forming the sealing layer. It is preferable to carry out in an indoor environment.
除去フィルターとしては、例えば、活性炭を用いたケミカルフィルター、触媒を用いたケミカルフィルター等のケミカルフィルターが挙げられ、ＰＧＭＥＡの平均濃度をより低減することができるので、活性炭を用いたケミカルフィルターが好ましい。 Examples of the removal filter include a chemical filter using activated carbon, a chemical filter using a catalyst, and the like, and since the average concentration of PGMEA can be further reduced, a chemical filter using activated carbon is preferable.
ＰＧＭＥＡの平均濃度は、例えば、日本レイシステムズ社製のＶＯＣモニターを用いて測定することができる。 The average concentration of PGMEA can be measured, for example, using a VOC monitor manufactured by Nippon Ray Systems Co., Ltd.
＜有機ＥＬ素子の層構成＞
本発明の製造方法により製造される有機ＥＬ素子は、陽極、陰極、少なくとも１層の有機機能層、及び、封止層を有している。
<Layer structure of organic EL element>
The organic EL device manufactured by the manufacturing method of the present invention has an anode, a cathode, at least one organic functional layer, and a sealing layer.
有機機能層は、陽極及び陰極に電流を流すことにより、又は、電圧を印加することにより、正孔又は電子を注入輸送し、発光することが可能な材料を含有する層である。有機機能層に用いられる材料としては、電流を流すことにより、又は、電圧を印加することによって、正孔又は電子を注入輸送し、発光することが可能な材料であればよく、有機機能材料が好ましい。 The organic functional layer is a layer containing a material capable of injecting and transporting holes or electrons and emitting light by passing an electric current through the anode and the cathode or by applying a voltage. The material used for the organic functional layer may be any material capable of injecting and transporting holes or electrons and emitting light by passing an electric current or applying a voltage. preferable.
有機機能材料としては、公知の材料を用いることができ、例えば、ジスチリルビフェニル系材料、ジメシチルボリル系材料、スチルベン系材料、ジピリリルジシアノベンゼン材料、ベンズオキサゾール系材料、ジスチリル系材料、カルバゾール系材料、ジベンゾクリセン系材料、アリールアミン系材料、ピレン置換オリゴチオフェン系材料、ＰＰＶオリゴマー系材料、カルバゾール系材料、ポリフルオレン系材料が挙げられる。 As the organic functional material, known materials can be used, for example, distyrylbiphenyl-based material, dimethylboryl-based material, stelvene-based material, dipyrrylyl dicyanobenzene material, benzoxazole-based material, distyryl-based material, carbazole-based material. , Dibenzoglycene-based material, arylamine-based material, pyrene-substituted oligothiophene-based material, PPV oligomer-based material, carbazole-based material, polyfluorene-based material.
有機機能層の形成は、有機機能材料と有機溶媒を含有する組成物を用いて、塗布法により形成されることが好ましい。塗布法としては、例えば、スピンコート法、キャスティング法、マイクログラビアコート法、グラビアコート法、バーコート法、ロールコート法、ワイヤーバーコート法、ディップコート法、スプレーコート法、スクリーン印刷法、フレキソ印刷法、オフセット印刷法、インクジェット印刷法、キャピラリ−コート法、ノズルコート法が挙げられ、スピンコート法、ノズルコート法、及び、インクジェット印刷法が好ましい。 The formation of the organic functional layer is preferably formed by a coating method using a composition containing an organic functional material and an organic solvent. Examples of the coating method include spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, and flexo printing. A method, an offset printing method, an inkjet printing method, a capillary coating method, and a nozzle coating method are mentioned, and a spin coating method, a nozzle coating method, and an inkjet printing method are preferable.
組成物の粘度は、塗布法の種類によって調整すればよいが、インクジェット印刷法等のインクが吐出装置を経由する印刷法に適用する場合には、吐出時の目づまりと飛行曲がりを防止するために、好ましくは２５℃において１〜２０mPa・sである。 The viscosity of the composition may be adjusted according to the type of coating method, but when the ink is applied to a printing method such as an inkjet printing method via an ejection device, in order to prevent clogging and flight bending during ejection. In addition, it is preferably 1 to 20 mPa · s at 25 ° C.
組成物に含有される有機溶媒は、該組成物中の固形分を溶解又は均一に分散できる溶媒が好ましい。有機溶媒としては、例えば、1,2-ジクロロエタン、1,1,2-トリクロロエタン、クロロベンゼン、o-ジクロロベンゼン等の塩素系溶媒；テトラヒドロフラン、ジオキサン、アニソール、4-メチルアニソール等のエーテル系溶媒；トルエン、キシレン、メシチレン、エチルベンゼン、n-ヘキシルベンゼン、シクロヘキシルベンゼン等の芳香族炭化水素系溶媒；シクロヘキサン、メチルシクロヘキサン、n-ペンタン、n-ヘキサン、n-へプタン、n-オクタン、n-ノナン、n-デカン、n-ドデカン、ビシクロヘキシル等の脂肪族炭化水素系溶媒；アセトン、メチルエチルケトン、シクロヘキサノン、アセトフェノン等のケトン系溶媒；酢酸エチル、酢酸ブチル、エチルセルソルブアセテート、安息香酸メチル、酢酸フェニル等のエステル系溶媒；エチレングリコール、グリセリン、1,2-ヘキサンジオール等の多価アルコール系溶媒；イソプロピルアルコール、シクロヘキサノール等のアルコール系溶媒；ジメチルスルホキシド等のスルホキシド系溶媒；N,N-ジメチルホルムアミド等のアミド系溶媒が挙げられる。溶媒は、一種単独で用いても二種以上を併用してもよい。 The organic solvent contained in the composition is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the composition. Examples of the organic solvent include chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole; toluene. , Xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene and other aromatic hydrocarbon solvents; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptan, n-octane, n-nonane, n -Adipose hydrocarbon solvents such as decane, n-dodecane and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone and acetophenone; ethyl acetate, butyl acetate, ethyl cellsolve acetate, methyl benzoate, phenyl acetate and the like Ester solvent; Polyhydric alcohol solvent such as ethylene glycol, glycerin, 1,2-hexanediol; Alcohol solvent such as isopropyl alcohol and cyclohexanol; Sulfoxide solvent such as dimethyl sulfoxide; N, N-dimethylformamide and the like Examples include amide-based solvents. The solvent may be used alone or in combination of two or more.
有機機能層としては、例えば、正孔輸送層、正孔注入層、電子輸送層、電子注入層及び発光層が挙げられる。
正孔輸送層、正孔注入層、電子輸送層、電子注入層及び発光層は、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料及び発光材料をそれぞれ含有し、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料及び発光材料を用いてそれぞれ形成することができる。
Examples of the organic functional layer include a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and a light emitting layer.
The hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer and the light emitting layer contain a hole transport material, a hole injection material, an electron transport material, an electron injection material and a light emitting material, respectively, and perform hole transport. It can be formed using a material, a hole injection material, an electron transport material, an electron injection material, and a light emitting material, respectively.
積層する層の順番、数及び厚さは、本発明の製造方法により製造される有機ＥＬ素子の発光寿命を勘案して調整すればよい。 The order, number, and thickness of the layers to be laminated may be adjusted in consideration of the light emitting life of the organic EL element manufactured by the manufacturing method of the present invention.
正孔輸送層、正孔注入層、電子輸送層、電子注入層及び発光層の厚さは、通常、それぞれ、１ｎｍ〜10μｍである。 The thickness of the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer and the light emitting layer is usually 1 nm to 10 μm, respectively.
本発明の製造方法により製造される有機ＥＬ素子は、正孔注入性及び正孔輸送性の観点からは、陽極と発光層との間に、正孔注入層及び正孔輸送層の少なくとも１層を有することが好ましく、電子注入性及び電子輸送性の観点からは、陰極と発光層の間に、電子注入層及び電子輸送層の少なくとも１層を有することが好ましい。 The organic EL element manufactured by the manufacturing method of the present invention has at least one of a hole injection layer and a hole transport layer between the anode and the light emitting layer from the viewpoint of hole injection property and hole transport property. From the viewpoint of electron injection property and electron transport property, it is preferable to have at least one layer of the electron injection layer and the electron transport layer between the cathode and the light emitting layer.
本発明の製造方法により製造される有機ＥＬ素子において、正孔輸送層、正孔注入層、電子輸送層、電子注入層及び発光層の形成方法としては、低分子化合物を用いる場合、例えば、粉末からの真空蒸着法、溶液又は溶融状態からの成膜による方法が挙げられ、高分子化合物を用いる場合、例えば、溶液又は溶融状態からの成膜による方法が挙げられる。 When a low molecular weight compound is used as a method for forming the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer and the light emitting layer in the organic EL device manufactured by the production method of the present invention, for example, powder. A method of forming a film from a solution or a molten state can be mentioned, and a method of forming a film from a solution or a molten state can be mentioned when a polymer compound is used.
正孔輸送層、正孔注入層、電子輸送層、電子注入層及び発光層は、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料及び発光層をそれぞれ含有する組成物を用いて、塗布法により形成することができる。塗布法としては、例えば、上述した有機機能層の形成における塗布法と同様のものが挙げられる。また、該組成物に含有される有機溶媒としては、例えば、上述した有機機能層の形成における組成物に含有される有機溶媒と同様のものが挙げられる。 For the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer and the light emitting layer, a composition containing the hole transport material, the hole injection material, the electron transport material, the electron injection material and the light emitting layer is used. It can be formed by a coating method. Examples of the coating method include the same coating method as in the above-mentioned formation of the organic functional layer. Further, as the organic solvent contained in the composition, for example, the same as the organic solvent contained in the composition in the formation of the organic functional layer described above can be mentioned.
組成物において、有機溶媒の配合量は、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料及び発光材料100重量部に対して、通常、1000〜100000重量部であり、好ましくは2000〜20000重量部である。 In the composition, the blending amount of the organic solvent is usually 1000 to 10000 parts by weight, preferably 1000 to 10000 parts by weight, based on 100 parts by weight of the hole transport material, the hole injection material, the electron transport material, the electron injection material and the light emitting material. 2000 to 20000 parts by weight.
正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料及び発光材料は、本発明の有機ＥＬ素子の製造方法において、各々、正孔輸送層、正孔注入層、電子輸送層、電子注入層及び発光層に隣接する層の形成時に使用される溶媒に溶解する場合、該溶媒に該材料が溶解することを回避するために、該材料が架橋基を有することが好ましい。架橋基を有する材料を用いて各層を形成した後、該架橋基を架橋させることにより、該層を不溶化させることができる。 The hole transport material, the hole injection material, the electron transport material, the electron injection material and the light emitting material are the hole transport layer, the hole injection layer, the electron transport layer and the electrons, respectively, in the method for manufacturing the organic EL device of the present invention. When dissolved in the solvent used in the formation of the injection layer and the layer adjacent to the light emitting layer, it is preferable that the material has a cross-linking group in order to prevent the material from being dissolved in the solvent. After forming each layer using a material having a cross-linking group, the layer can be insolubilized by cross-linking the cross-linking group.
各層を架橋させるための加熱の温度は、通常、25〜300℃であり、本発明の製造方法により製造される有機ＥＬ素子の発光寿命が優れるので、好ましくは50〜250℃であり、より好ましくは150〜200℃である。 The heating temperature for cross-linking each layer is usually 25 to 300 ° C., and the emission life of the organic EL device manufactured by the production method of the present invention is excellent, so it is preferably 50 to 250 ° C., more preferably. Is 150-200 ° C.
各層を架橋させるための光照射に用いられる光の種類は、例えば、紫外光、近紫外光、可視光である。 The types of light used for light irradiation for cross-linking each layer are, for example, ultraviolet light, near-ultraviolet light, and visible light.
［基板/電極（材料）］
本発明の製造方法により製造される有機ＥＬ素子は、通常、基板を有する。この基板は、電極を形成することができ、かつ、有機機能層を形成する際に化学的に変化しない基板であればよく、例えば、ガラス、プラスチック、シリコン等の材料からなる基板である。
[Substrate / Electrode (Material)]
The organic EL device manufactured by the manufacturing method of the present invention usually has a substrate. The substrate may be any substrate that can form electrodes and does not chemically change when the organic functional layer is formed, and is, for example, a substrate made of a material such as glass, plastic, or silicon.
陽極の材料としては、例えば、導電性の金属酸化物、半透明の金属が挙げられ、好ましくは、酸化インジウム、酸化亜鉛、酸化スズ；インジウム・スズ・オキサイド(ITO)、インジウム・亜鉛・オキサイド等の導電性化合物；銀とパラジウムと銅との複合体(APC)；NESA、金、白金、銀、銅である。 Examples of the material of the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide and the like. Conductive compounds; composites of silver, palladium and copper (APC); NESA, gold, platinum, silver, copper.
陰極の材料としては、例えば、リチウム、ナトリウム、カリウム、ルビジウム、セシウム、ベリリウム、マグネシウム、カルシウム、ストロンチウム、バリウム、アルミニウム、亜鉛、インジウム等の金属；それらのうち２種以上の合金；それらのうち１種以上と、銀、銅、マンガン、チタン、コバルト、ニッケル、タングステン、錫のうち１種以上との合金；並びに、グラファイト及びグラファイト層間化合物が挙げられる。合金としては、例えば、マグネシウム−銀合金、マグネシウム−インジウム合金、マグネシウム−アルミニウム合金、インジウム−銀合金、リチウム−アルミニウム合金、リチウム−マグネシウム合金、リチウム−インジウム合金、カルシウム−アルミニウム合金が挙げられる。 As the material of the cathode, for example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more alloys among them; one of them. Alloys of more than one species with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten and tin; as well as graphite and graphite interlayer compounds. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.
陽極及び陰極は、各々、２層以上の積層構造としてもよい。 The anode and cathode may each have a laminated structure of two or more layers.
本発明の製造方法により製造される有機ＥＬ素子において、陽極及び陰極の少なくとも一方は、通常、透明又は半透明であるが、陽極が透明又は半透明であることが好ましい。 In the organic EL device manufactured by the manufacturing method of the present invention, at least one of the anode and the cathode is usually transparent or translucent, but it is preferable that the anode is transparent or translucent.
陽極及び陰極の形成方法としては、例えば、真空蒸着法、スパッタリング法、イオンプレーティング法、メッキ法及びラミネート法が挙げられる。 Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method and a laminating method.
［発光層（発光材料）］
発光材料は、通常、主として蛍光又はりん光を発光する有機化合物(低分子化合物及び高分子化合物)と、これを補助するドーパントとから形成される。発光材料としては、例えば、色素系材料、金属錯体系材料、高分子系材料が挙げられる。
[Light emitting layer (light emitting material)]
The luminescent material is usually formed mainly of an organic compound (low molecular weight compound and high molecular weight compound) that emits fluorescence or phosphorescence, and a dopant that assists the organic compound. Examples of the light emitting material include dye-based materials, metal complex-based materials, and polymer-based materials.
色素系材料としては、例えば、シクロペンダミン及びその誘導体、テトラフェニルブタジエン及びその誘導体、トリフェニルアミン及びその誘導体、オキサジアゾール及びその誘導体、ピラゾロキノリン及びその誘導体、ジスチリルベンゼン及びその誘導体、ジスチリルアリーレン及びその誘導体、ピロール及びその誘導体、チオフェン環化合物、ピリジン環化合物、ペリノン及びその誘導体、ペリレン及びその誘導体、オリゴチオフェン及びその誘導体、オキサジアゾールダイマー、ピラゾリンダイマーが挙げられる。 Examples of the dye-based material include cyclopendamine and its derivatives, tetraphenylbutadiene and its derivatives, triphenylamine and its derivatives, oxadiazol and its derivatives, pyrazoloquinolin and its derivatives, distyrylbenzene and its derivatives, and the like. Examples thereof include distyrylarylene and its derivatives, pyrrole and its derivatives, thiophene ring compounds, pyridine ring compounds, perinone and its derivatives, perylene and its derivatives, oligothiophene and its derivatives, oxaziazole dimer and pyrazoline dimer.
金属錯体系材料としては、例えば、アルミニウムキノリノール錯体、ベンゾキノリノールベリリウム錯体、ベンゾオキサゾリル亜鉛錯体、ベンゾチアゾール亜鉛錯体、アゾメチル亜鉛錯体、ポルフィリン亜鉛錯体、ユーロピウム錯体等、中心金属に、Al、Zn、Be等又はTb、Eu、Dy等の希土類金属を有し、配位子にオキサジアゾール、チアジアゾール、フェニルピリジン、フェニルベンゾイミダゾール、キノリン構造等を有する金属錯体を挙げることができる。 Examples of the metal complex-based material include aluminum quinolinol complex, benzoquinolinol berylium complex, benzooxazolyl zinc complex, benzothiazole zinc complex, azomethylzinc complex, porphyrin zinc complex, europium complex and the like, and Al, Zn, etc. Examples thereof include metal complexes having rare earth metals such as Be and Tb, Eu and Dy, and having oxadiazole, thiadiazol, phenylpyridine, phenylbenzimidazole, quinoline structure and the like as ligands.
高分子系材料としては、例えば、ポリパラフェニレンビニレン及びその誘導体、ポリチオフェン及びその誘導体、ポリパラフェニレン及びその誘導体、ポリシラン及びその誘導体、ポリアセチレン及びその誘導体、ポリフルオレン及びその誘導体、ポリビニルカルバゾール及びその誘導体、上記色素系材料又は金属錯体系材料を高分子化した化合物が挙げられる。 Examples of the polymer-based material include polyparaphenylene vinylene and its derivatives, polythiophene and its derivatives, polyparaphenylene and its derivatives, polysilane and its derivatives, polyacetylene and its derivatives, polyfluorene and its derivatives, polyvinylcarbazole and its derivatives. , A compound obtained by polymerizing the above dye-based material or metal complex-based material.
発光材料のうち、青色発光材料としては、例えば、ジスチリルアリーレン及びその誘導体、オキサジアゾール及びその誘導体、並びに、これらの重合体；ポリビニルカルバゾール及びその誘導体、ポリパラフェニレン及びその誘導体、ポリフルオレン及びその誘導体が挙げられ、ポリビニルカルバゾール及びその誘導体、ポリパラフェニレン及びその誘導体、ポリフルオレン及びその誘導体が好ましい。 Among the luminescent materials, the blue luminescent materials include, for example, distyrylarylene and its derivatives, oxadiazole and its derivatives, and polymers thereof; polyvinylcarbazole and its derivatives, polyparaphenylene and its derivatives, polyfluorene and Examples thereof include polyvinylcarbazole and its derivatives, polyparaphenylene and its derivatives, and polyfluorene and its derivatives are preferable.
発光材料のうち、緑色発光材料としては、例えば、キナクリドン及びその誘導体、クマリン及びその誘導体、並びに、これらの重合体；ポリパラフェニレンビニレン及びその誘導体、ポリフルオレン及びその誘導体が挙げられ、ポリパラフェニレンビニレン及びその誘導体、ポリフルオレン及びその誘導体が好ましい。 Among the luminescent materials, examples of the green luminescent material include quinacridone and its derivatives, coumarin and its derivatives, and polymers thereof; polyparaphenylene vinylene and its derivatives, polyfluorene and its derivatives, and polyparaphenylene. Vinylene and its derivatives, polyfluorene and its derivatives are preferred.
発光材料のうち、赤色発光材料としては、例えば、クマリン及びその誘導体、チオフェン環化合物、並びに、これらの重合体；ポリパラフェニレンビニレン及びその誘導体、ポリチオフェン及びその誘導体、ポリフルオレン及びその誘導体が挙げられ、ポリパラフェニレンビニレン及びその誘導体、ポリチオフェン及びその誘導体、ポリフルオレン及びその誘導体が好ましい。 Among the luminescent materials, examples of the red luminescent material include coumarin and its derivatives, thiophene ring compounds, and polymers thereof; polyparaphenylene vinylene and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives. , Polyparaphenylene vinylene and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives are preferred.
発光効率の向上、発光波長の変化等の目的で、発光層中にドーパントを添加することができる。ドーパントとしては、例えば、ペリレン及びその誘導体、クマリン及びその誘導体、ルブレン及びその誘導体、キナクリドン及びその誘導体、スクアリウム及びその誘導体、ポルフィリン及びその誘導体、スチリル系色素、テトラセン及びその誘導体、ピラゾロン及びその誘導体、デカシクレン、フェノキサゾンが挙げられる。 Dopants can be added to the light emitting layer for the purpose of improving the light emitting efficiency, changing the light emitting wavelength, and the like. Examples of the dopant include perylene and its derivatives, coumarin and its derivatives, rubrene and its derivatives, quinacridone and its derivatives, squalium and its derivatives, porphyrin and its derivatives, styryl dyes, tetracene and its derivatives, pyrazolone and its derivatives. Examples include decasiclen and phenoxazone.
発光材料は、１種単独で用いても２種以上を併用してもよい。 The luminescent material may be used alone or in combination of two or more.
［正孔輸送層（正孔輸送材料）］
正孔輸送材料は、低分子化合物と高分子化合物とに分類され、好ましくは高分子化合物である。正孔輸送材料は、架橋基を有していてもよい。
[Hole transport layer (hole transport material)]
The hole transporting material is classified into a low molecular weight compound and a high molecular weight compound, and is preferably a high molecular weight compound. The hole transport material may have a cross-linking group.
高分子化合物としては、例えば、ポリビニルカルバゾール及びその誘導体；側鎖又は主鎖に芳香族アミン構造を有するポリアリーレン及びその誘導体が挙げられる。高分子化合物は、電子受容性部位が結合された化合物でもよい。電子受容性部位としては、例えば、フラーレン、テトラフルオロテトラシアノキノジメタン、テトラシアノエチレン、トリニトロフルオレノンが挙げられ、好ましくはフラーレンである。 Examples of the polymer compound include polyvinylcarbazole and its derivatives; polyarylene having an aromatic amine structure in its side chain or main chain and its derivatives. The polymer compound may be a compound to which an electron accepting site is bound. Examples of the electron-accepting site include fullerenes, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, and fullerenes are preferable.
正孔輸送材料は、１種単独で用いても２種以上を併用してもよい。 The hole transporting material may be used alone or in combination of two or more.
［電子輸送層（電子輸送材料）］
電子輸送材料は、低分子化合物と高分子化合物とに分類される。電子輸送材料は、架橋基を有していてもよい。
[Electron transport layer (electron transport material)]
Electron transport materials are classified into low molecular weight compounds and high molecular weight compounds. The electron transport material may have a cross-linking group.
低分子化合物としては、例えば、8-ヒドロキシキノリンを配位子とする金属錯体、オキサジアゾール、アントラキノジメタン、ベンゾキノン、ナフトキノン、アントラキノン、テトラシアノアントラキノジメタン、フルオレノン、ジフェニルジシアノエチレン及びジフェノキノン、並びに、これらの誘導体が挙げられる。 Examples of low molecular weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinone dimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinone dimethane, fluorenone, diphenyldicyanoethylene and diphenoquinone. , And these derivatives.
高分子化合物としては、例えば、ポリフェニレン、ポリフルオレン、及び、これらの誘導体が挙げられる。高分子化合物は、金属でドープされていてもよい。 Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymeric compound may be doped with a metal.
電子輸送材料は、１種単独で用いても２種以上を併用してもよい。 The electron transport material may be used alone or in combination of two or more.
［正孔注入材料及び電子注入材料］
正孔注入材料及び電子注入材料は、各々、低分子化合物と高分子化合物とに分類される。正孔注入材料及び電子注入材料は、架橋基を有していてもよい。
[Hole injection material and electron injection material]
The hole injection material and the electron injection material are classified into low molecular weight compounds and high molecular weight compounds, respectively. The hole injection material and the electron injection material may have a cross-linking group.
低分子化合物としては、例えば、銅フタロシアニン等の金属フタロシアニン；カーボン；モリブデン、タングステン等の金属酸化物；フッ化リチウム、フッ化ナトリウム、フッ化セシウム、フッ化カリウム等の金属フッ化物が挙げられる。 Examples of the low molecular weight compound include metal phthalocyanines such as copper phthalocyanines; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride and potassium fluoride.
高分子化合物としては、例えば、ポリアニリン、ポリチオフェン、ポリピロール、ポリフェニレンビニレン、ポリチエニレンビニレン、ポリキノリン及びポリキノキサリン、並びに、これらの誘導体；芳香族アミン構造を主鎖又は側鎖に含む重合体等の導電性高分子が挙げられる。 Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductivity of polymers containing an aromatic amine structure in the main chain or side chain. Examples include polypolymers.
組成物において、正孔注入材料及び電子注入材料の含有量は、各々、正孔注入材料100重量部に対して、通常、１〜100重量部であり、好ましくは５〜100重量部である。 In the composition, the contents of the hole injection material and the electron injection material are usually 1 to 100 parts by weight, preferably 5 to 100 parts by weight, based on 100 parts by weight of the hole injection material.
正孔注入材料及び電子注入材料は、各々、１種単独で用いても２種以上を併用してもよい。 The hole injection material and the electron injection material may be used alone or in combination of two or more.
正孔注入材料又は電子注入材料が導電性高分子を含む場合、導電性高分子の電気伝導度は、好ましくは、１×10-5S/cm〜１×103S/cmである。導電性高分子の電気伝導度をかかる範囲とするために、導電性高分子に適量のイオンをドープすることができる。 When the hole injection material or the electron injection material contains a conductive polymer, the electric conductivity of the conductive polymer is preferably 1 × 10 -5 S / cm to 1 × 10 3 S / cm. In order to keep the electric conductivity of the conductive polymer within such a range, an appropriate amount of ions can be doped into the conductive polymer.
ドープするイオンの種類は、正孔注入材料であればアニオン、電子注入材料であればカチオンである。アニオンとしては、例えば、ポリスチレンスルホン酸イオン、アルキルベンゼンスルホン酸イオン、樟脳スルホン酸イオンが挙げられる。カチオンとしては、例えば、リチウムイオン、ナトリウムイオン、カリウムイオン、テトラブチルアンモニウムイオンが挙げられる。 The type of ion to be doped is an anion in the case of a hole injection material and a cation in the case of an electron injection material. Examples of the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion. Examples of the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.
ドープするイオンは、１種単独で用いても２種以上を併用してもよい。 The type of ion to be doped may be used alone or in combination of two or more.
［封止層（材料）］
封止層は、水分及び酸素ガスに対してバリア性を有するものであればよいが、封止層の一形態としては、有機ＥＬ素子が有する陽極、陰極、及び、少なくとも１層の有機機能層が、窒素ガス、アルゴンガス等の不活性ガスが充填された状態で、ガラス、プラスチック、シリコン等の材料からなる基板により密封されたものが挙げられる。封止層の他の一形態としては、有機ＥＬ素子が有する陽極、陰極、及び、少なくとも１層の有機機能層が、有機化合物からなる絶縁層又は無機化合物からなる絶縁層を介して、ガラス、プラスチック、シリコン等の材料からなる基板により密封されたものが挙げられる。有機化合物からなる絶縁層の材料としては、例えば、熱可塑性樹脂、光架橋性樹脂が挙げられる。無機化合物からなる絶縁層の材料としては、例えば、金属酸化物、金属窒化物が挙げられる。
[Encapsulation layer (material)]
The sealing layer may have a barrier property against water and oxygen gas, but one form of the sealing layer is an anode and a cathode of the organic EL element, and at least one organic functional layer. However, a state in which an inert gas such as nitrogen gas or argon gas is filled and sealed with a substrate made of a material such as glass, plastic or silicon can be mentioned. As another form of the sealing layer, the anode and cathode of the organic EL element, and at least one organic functional layer are made of glass via an insulating layer made of an organic compound or an insulating layer made of an inorganic compound. Examples thereof include those sealed by a substrate made of a material such as plastic or silicon. Examples of the material of the insulating layer made of an organic compound include a thermoplastic resin and a photocrosslinkable resin. Examples of the material of the insulating layer made of an inorganic compound include metal oxides and metal nitrides.
封止層には、乾燥剤が配置されていてもよいし、乾燥剤が内部に含まれていてもよい。 A desiccant may be arranged on the sealing layer, or a desiccant may be contained therein.
封止層は、通常、陽極、陰極、少なくとも一層の有機機能層を形成した後、最後に形成する。 The sealing layer is usually formed at the end after forming an anode, a cathode, and at least one organic functional layer.
＜有機ＥＬ素子の用途＞
有機ＥＬ素子を用いて面状の発光を得るためには、面状の陽極と陰極が重なり合うように配置すればよい。パターン状の発光を得るためには、面状の有機ＥＬ素子の表面にパターン状の窓を設けたマスクを設置する方法、非発光部にしたい層を極端に厚く形成し実質的に非発光とする方法、陽極若しくは陰極、又は両方の電極をパターン状に形成する方法がある。これらのいずれかの方法でパターンを形成し、いくつかの電極を独立にＯＮ／ＯＦＦできるように配置することにより、数字、文字等を表示できるセグメントタイプの表示装置が得られる。ドットマトリックス表示装置とするためには、陽極と陰極を共にストライプ状に形成して直交するように配置すればよい。複数の種類の発光色の異なる高分子化合物を塗り分ける方法、カラーフィルター又は蛍光変換フィルターを用いる方法により、部分カラー表示、マルチカラー表示が可能となる。ドットマトリックス表示装置は、パッシブ駆動も可能であるし、ＴＦＴ等と組み合わせてアクティブ駆動も可能である。これらの表示装置は、コンピュータ、テレビ、携帯端末等のディスプレイに用いることができる。面状の有機ＥＬ素子は、液晶表示装置のバックライト用の面状光源、又は、面状の照明用光源として好適に用いることができる。フレキシブルな基板を用いれば、曲面状の光源及び表示装置としても使用できる。
<Use of organic EL elements>
In order to obtain planar light emission using the organic EL element, the planar anode and cathode may be arranged so as to overlap each other. In order to obtain patterned light emission, a method of installing a mask having a patterned window on the surface of a planar organic EL element, or forming a layer to be a non-light emitting part extremely thick to make it substantially non-light emitting. There is a method of forming an anode or a cathode, or both electrodes in a pattern. By forming a pattern by any of these methods and arranging several electrodes so that they can be turned ON / OFF independently, a segment type display device capable of displaying numbers, characters, etc. can be obtained. In order to use the dot matrix display device, both the anode and the cathode may be formed in a striped shape and arranged so as to be orthogonal to each other. Partial color display and multi-color display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method of using a color filter or a fluorescence conversion filter. The dot matrix display device can be passively driven, or can be actively driven in combination with a TFT or the like. These display devices can be used for displays such as computers, televisions, and mobile terminals. The planar organic EL element can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can also be used as a curved light source and display device.
以下、実施例によって本発明を詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to these Examples.
＜実施例１＞
以下の工程は、ケミカルガード（ニチアス社製、型番：ＷＡＶＥ−ＨＡA）を用いて準備した空間で行った。
<Example 1>
The following steps were performed in a space prepared using a chemical guard (manufactured by Nichias Corporation, model number: WAVE-HAA).
（陽極及び正孔注入層の形成）
ガラス基板に、スパッタ法により４５ｎｍの厚さでＩＴＯ膜を付けることにより陽極を形成した。この基板を、有機溶媒、アルカリ洗剤、及び、超純水で洗浄し、約８０℃の温風で約４時間乾燥させた。次に、ＩＴＯ膜が形成された面に対して、ＵＶ−Ｏ3装置を用いてＵＶ−Ｏ3処理を約１５分間行った。ＩＴＯ膜上に、正孔注入材料を含む組成物を滴下し、スピンコート法によって２８秒間処理することにより、３５ｎｍの厚さの膜を形成した。ホットプレート上で、８０℃で４分間乾燥させ、３５分間の待機時間の後、更に、２３０℃で１５分間加熱し、次いで１０分間冷却し、正孔注入層を形成した。
正孔注入層を形成する工程において、ＰＧＭＥＡに製造中の有機ＥＬ素子が曝露される積算曝露量は、０ｐｐｍ・ｓeｃであった。
(Formation of anode and hole injection layer)
An anode was formed by attaching an ITO film to a glass substrate to a thickness of 45 nm by a sputtering method. The substrate was washed with an organic solvent, an alkaline detergent, and ultrapure water, and dried with warm air at about 80 ° C. for about 4 hours. Next, with respect to the plane ITO film is formed, a UV-O 3 treatment was carried out for about 15 minutes using a UV-O 3 apparatus. A composition containing a hole injection material was dropped onto the ITO film and treated by a spin coating method for 28 seconds to form a film having a thickness of 35 nm. On a hot plate, dried at 80 ° C. for 4 minutes, after a waiting time of 35 minutes, further heated at 230 ° C. for 15 minutes and then cooled for 10 minutes to form a hole injection layer.
In the step of forming the hole injection layer, the cumulative exposure amount of the organic EL device being manufactured to PGMEA was 0 ppm · sec.
（正孔輸送層の形成）
キシレンに正孔輸送材料を混合し、固形分濃度（正孔輸送材料）が０．６重量％の正孔輸送層形成用組成物を得た。この正孔輸送層形成用組成物を用いてスピンコート法によって、正孔注入層上に滴下した正孔輸送層形成用組成物を１３秒間処理することにより、２０ｎｍの厚さで成膜した。８分間の待機時間の後、窒素ガス雰囲気下、１８０℃で６０分間焼成した後、室温まで自然冷却し、正孔輸送層を形成した。
正孔輸送層を形成する工程において、ＰＧＭＥＡに製造中の有機ＥＬ素子が曝露される積算曝露量は、０ｐｐｍ・ｓeｃであった。
(Formation of hole transport layer)
A hole transporting material was mixed with xylene to obtain a composition for forming a hole transporting layer having a solid content concentration (hole transporting material) of 0.6% by weight. Using this hole transport layer forming composition, the hole transport layer forming composition dropped onto the hole injection layer was treated for 13 seconds by a spin coating method to form a film having a thickness of 20 nm. After a waiting time of 8 minutes, it was calcined at 180 ° C. for 60 minutes in a nitrogen gas atmosphere, and then naturally cooled to room temperature to form a hole transport layer.
In the step of forming the hole transport layer, the cumulative exposure amount of the organic EL device being manufactured to PGMEA was 0 ppm · sec.
（発光層の形成）
キシレンに発光性共役高分子化合物を混合し、固形分濃度（発光性共役高分子化合物）が１．３重量％の発光層形成用組成物を得た。この発光層形成用組成物を用いてスピンコート法により、正孔輸送層上に滴下した発光層形成用組成物を３４秒間処理することにより、６０ｎｍの厚さで成膜した。その後、３０分間待機した。次いで、窒素ガス雰囲気下、１５０℃で１０分間焼成した後、窒素ガス雰囲気下で室温まで自然冷却し、発光層を形成した。発光層を形成する工程において、製造中の有機ＥＬ素子がＰＧＭＥＡに曝露された積算曝露量は、０ｐｐｍ・ｓeｃであった。
(Formation of light emitting layer)
A luminescent conjugated polymer compound was mixed with xylene to obtain a composition for forming a luminescent layer having a solid content concentration (luminescent conjugated polymer compound) of 1.3% by weight. Using this light emitting layer forming composition, the light emitting layer forming composition dropped onto the hole transport layer was treated for 34 seconds by a spin coating method to form a film having a thickness of 60 nm. Then, it waited for 30 minutes. Then, after firing at 150 ° C. for 10 minutes in a nitrogen gas atmosphere, it was naturally cooled to room temperature in a nitrogen gas atmosphere to form a light emitting layer. In the step of forming the light emitting layer, the cumulative exposure amount of the organic EL device being manufactured to PGMEA was 0 ppm · sec.
（陰極の形成）
発光層を形成した製造中の有機ＥＬ素子を蒸着機内に置いて、１．０×１０-4Ｐａ以下となるまで減圧した後、発光層の上に、陰極として、フッ化ナトリウムを約３ｎｍ、次いで、アルミニウムを約１００ｎｍ蒸着した。その後、窒素ガス雰囲気下、ガラス基板を用いて封止層を形成することにより、有機ＥＬ素子１を作製した。陰極の形成及び封止に要した時間は、４５００秒であった。
(Cathode formation)
The organic EL element under production on which the light emitting layer is formed is placed in a vapor deposition machine, and the pressure is reduced to 1.0 × 10 -4 Pa or less. Then, sodium fluoride is placed on the light emitting layer as a cathode at about 3 nm. Next, aluminum was deposited at about 100 nm. Then, the organic EL element 1 was manufactured by forming a sealing layer using a glass substrate in a nitrogen gas atmosphere. The time required to form and seal the cathode was 4500 seconds.
以上のとおり、有機ＥＬ素子１の製造中、有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子がＰＧＭＥＡに曝露された積算曝露量Ａ×Ｂは、０ｐｐｍ・ｓeｃであった。ＰＧＭＥＡの平均濃度Ａは０ｐｐｍであり、曝露時間Ｂは６１９５秒であった。 As described above, during the production of the organic EL element 1, the cumulative exposure amount of the organic EL element being manufactured from the start of the process of forming the organic functional layer to the end of the process of forming the sealing layer is exposed to PGMEA. A × B was 0 ppm · sec. The average concentration A of PGMEA was 0 ppm and the exposure time B was 6195 seconds.
有機ＥＬ素子１に電圧を印加したところ、青色のＥＬ発光が観測された。初期輝度が１０００ｃｄ／ｍ2となるように電流値を設定後、定電流で駆動させ、初期輝度が５％低下する寿命（以下、「ＬＴ９５」と言う。）を測定したところ、２９．９時間であった。 When a voltage was applied to the organic EL element 1, blue EL light emission was observed. After setting the current value so that the initial brightness is 1000 cd / m 2 , it is driven by a constant current, and the life (hereinafter referred to as "LT95") in which the initial brightness is reduced by 5% is measured and found to be 29.9 hours. Met.
＜実施例２＞
実施例１において、発光層を成膜した製造中の有機ＥＬ素子がＰＧＭＥＡ濃度を制御した雰囲気でＰＧＭＥＡに曝露された積算曝露量が、６．７ｐｐｍ・ｓeｃとなるようにＰＧＭＥＡに曝露させた以外は実施例１と同様にして、有機ＥＬ素子を作製した（以下、「有機ＥＬ素子２」と言う。）。ＰＧＭＥＡの平均濃度は０．６１ｐｐｍであり、曝露時間は１１秒であった。ＰＧＭＥＡ濃度は、日本レイシステムズ社製のVOCモニター（型番：ｐｐｂレイ３０００）を用いて測定した。
<Example 2>
In Example 1, except that the organic EL device in production on which the light emitting layer was formed was exposed to PGMEA so that the cumulative exposure amount exposed to PGMEA in an atmosphere in which the PGMEA concentration was controlled was 6.7 ppm · sec. Made an organic EL element in the same manner as in Example 1 (hereinafter, referred to as "organic EL element 2"). The average concentration of PGMEA was 0.61 ppm and the exposure time was 11 seconds. The PGMEA concentration was measured using a VOC monitor (model number: ppb ray 3000) manufactured by Nippon Ray Systems Co., Ltd.
以上のとおり、有機ＥＬ素子２の製造中、有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子がＰＧＭＥＡに曝露された積算曝露量Ａ×Ｂは、６．７ｐｐｍ・ｓeｃであった。ＰＧＭＥＡの平均濃度Ａは０．００１０８ｐｐｍであり、曝露時間Ｂは６２０６秒であった。 As described above, during the production of the organic EL element 2, the cumulative exposure amount of the organic EL element being manufactured from the start of the process of forming the organic functional layer to the end of the process of forming the sealing layer is exposed to PGMEA. A × B was 6.7 ppm · sec. The average concentration A of PGMEA was 0.00108 ppm and the exposure time B was 6206 seconds.
有機ＥＬ素子２に電圧を印加したところ、青色のＥＬ発光が観測された。初期輝度が１０００ｃｄ／ｍ2となるように電流値を設定後、定電流で駆動させ、ＬＴ９５を測定したところ、２９．５時間であった。 When a voltage was applied to the organic EL element 2, blue EL light emission was observed. After setting the current value so that the initial brightness was 1000 cd / m 2 , it was driven by a constant current and the LT95 was measured. It was 29.5 hours.
＜実施例３＞
実施例１において、発光層を成膜した製造中の有機ＥＬ素子がＰＧＭＥＡ濃度を制御した雰囲気でＰＧＭＥＡに曝露された積算曝露量が、８．４ｐｐｍ・ｓeｃとなるようにＰＧＭＥＡに曝露させた以外は実施例１と同様にして、有機ＥＬ素子を作製した（以下、「有機ＥＬ素子３」と言う。）。ＰＧＭＥＡの平均濃度は０．４２ｐｐｍであり、曝露時間は２０秒であった。
<Example 3>
In Example 1, except that the organic EL device in production on which the light emitting layer was formed was exposed to PGMEA so that the cumulative exposure amount exposed to PGMEA in an atmosphere in which the PGMEA concentration was controlled was 8.4 ppm · sec. Made an organic EL element in the same manner as in Example 1 (hereinafter, referred to as "organic EL element 3"). The average concentration of PGMEA was 0.42 ppm and the exposure time was 20 seconds.
以上のとおり、有機ＥＬ素子３の製造中、有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子がＰＧＭＥＡに曝露された積算曝露量Ａ×Ｂは、８．４ｐｐｍ・ｓeｃであった。ＰＧＭＥＡの平均濃度Ａは０．００１３５ｐｐｍであり、曝露時間Ｂは６２１５秒であった。 As described above, during the production of the organic EL element 3, the cumulative exposure amount of the organic EL element being manufactured from the start of the step of forming the organic functional layer to the end of the step of forming the sealing layer is exposed to PGMEA. A × B was 8.4 ppm · sec. The average concentration A of PGMEA was 0.00135 ppm and the exposure time B was 6215 seconds.
有機ＥＬ素子３に電圧を印加したところ、青色のＥＬ発光が観測された。初期輝度が１０００ｃｄ／ｍ2となるように電流値を設定後、定電流で駆動させ、ＬＴ９５を測定したところ、２９．８時間であった。 When a voltage was applied to the organic EL element 3, blue EL light emission was observed. After setting the current value so that the initial brightness was 1000 cd / m 2 , it was driven by a constant current and the LT95 was measured. It was 29.8 hours.
＜比較例１＞
実施例１において、発光層を成膜した製造中の有機ＥＬ素子がＰＧＭＥＡ濃度を制御した雰囲気でＰＧＭＥＡに曝露された積算曝露量が、２０ｐｐｍ・ｓeｃとなるようにＰＧＭＥＡに曝露させた以外は実施例１と同様にして、有機ＥＬ素子を作製した（以下、「有機ＥＬ素子Ｃ１」と言う。）。ＰＧＭＥＡの平均濃度は０．５５ｐｐｍであり、曝露時間は３６秒であった。
<Comparative example 1>
In Example 1, the organic EL device being manufactured having the light emitting layer formed was exposed to PGMEA so that the cumulative exposure amount exposed to PGMEA in an atmosphere in which the PGMEA concentration was controlled was 20 ppm · sec. An organic EL element was produced in the same manner as in Example 1 (hereinafter, referred to as "organic EL element C1"). The average concentration of PGMEA was 0.55 ppm and the exposure time was 36 seconds.
以上のとおり、有機ＥＬ素子Ｃ１の製造中、有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子がＰＧＭＥＡに曝露された積算曝露量Ａ×Ｂは、２０ｐｐｍ・ｓeｃであった。ＰＧＭＥＡの平均濃度Ａは０．００３２１ｐｐｍであり、曝露時間Ｂは６２３１秒であった。 As described above, during the production of the organic EL element C1, the cumulative exposure amount of the organic EL element being manufactured from the start of the process of forming the organic functional layer to the end of the process of forming the sealing layer is exposed to PGMEA. A × B was 20 ppm · sec. The average concentration A of PGMEA was 0.00321 ppm and the exposure time B was 6231 seconds.
有機ＥＬ素子Ｃ１に電圧を印加したところ、青色のＥＬ発光が観測された。初期輝度が１０００ｃｄ／ｍ2となるように電流値を設定後、定電流で駆動させ、ＬＴ９５を測定したところ、２５．２時間であった。 When a voltage was applied to the organic EL element C1, blue EL light emission was observed. After setting the current value so that the initial brightness was 1000 cd / m 2 , it was driven by a constant current and the LT95 was measured. It was 25.2 hours.
＜比較例２＞
実施例１において、発光層を成膜した製造中の有機ＥＬ素子がＰＧＭＥＡ濃度を制御した雰囲気でＰＧＭＥＡに曝露された積算曝露量が、４０ｐｐｍ・ｓeｃとなるようにＰＧＭＥＡに曝露させた以外は実施例１と同様にして、有機ＥＬ素子を作製した（以下、「有機ＥＬ素子Ｃ２」と言う。）。ＰＧＭＥＡの平均濃度は０．７３ｐｐｍであり、曝露時間は５５秒であった。
<Comparative example 2>
In Example 1, the organic EL device being manufactured having the light emitting layer formed was exposed to PGMEA in an atmosphere in which the concentration of PGMEA was controlled so that the cumulative exposure amount was 40 ppm · sec. An organic EL element was produced in the same manner as in Example 1 (hereinafter, referred to as "organic EL element C2"). The average concentration of PGMEA was 0.73 ppm and the exposure time was 55 seconds.
以上のとおり、有機ＥＬ素子Ｃ２の製造中、有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子がＰＧＭＥＡに曝露された積算曝露量Ａ×Ｂは、４０ｐｐｍ・ｓeｃであった。ＰＧＭＥＡの平均濃度Ａは０．００６４０ｐｐｍであり、曝露時間Ｂは６２５０秒であった。 As described above, during the production of the organic EL element C2, the cumulative exposure amount of the organic EL element being manufactured from the start of the process of forming the organic functional layer to the end of the process of forming the sealing layer is exposed to PGMEA. A × B was 40 ppm · sec. The average concentration A of PGMEA was 0.00640 ppm and the exposure time B was 6250 seconds.
有機ＥＬ素子Ｃ２に電圧を印加したところ、青色のＥＬ発光が観測された。初期輝度が１０００ｃｄ／ｍ2となるように電流値を設定後、定電流で駆動させ、ＬＴ９５を測定したところ、２４．１時間であった。 When a voltage was applied to the organic EL element C2, blue EL light emission was observed. After setting the current value so that the initial brightness was 1000 cd / m 2 , it was driven by a constant current and the LT95 was measured. It was 24.1 hours.
＜比較例３＞
実施例１において、発光層を成膜した製造中の有機ＥＬ素子がＰＧＭＥＡ濃度を制御した雰囲気でＰＧＭＥＡに曝露された積算曝露量が、１１３ｐｐｍ・ｓeｃとなるようにＰＧＭＥＡに曝露させた以外は実施例１と同様にして、有機ＥＬ素子を作製した（以下、「有機ＥＬ素子Ｃ３」と言う。）。ＰＧＭＥＡの平均濃度は１．２５ｐｐｍであり、曝露時間は９０秒であった。
<Comparative example 3>
In Example 1, the organic EL device in production having a light emitting layer formed on the film was exposed to PGMEA in an atmosphere in which the concentration of PGMEA was controlled, except that the cumulative exposure amount was 113 ppm · sec. An organic EL element was produced in the same manner as in Example 1 (hereinafter, referred to as "organic EL element C3"). The average concentration of PGMEA was 1.25 ppm and the exposure time was 90 seconds.
以上のとおり、有機ＥＬ素子Ｃ３の製造中、有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子がＰＧＭＥＡに曝露された積算曝露量Ａ×Ｂは、１１３ｐｐｍ・ｓeｃであった。ＰＧＭＥＡの平均濃度Ａは０．０１７９８ｐｐｍであり、曝露時間Ｂは６２８５秒であった。 As described above, during the production of the organic EL element C3, the cumulative exposure amount of the organic EL element being manufactured from the start of the process of forming the organic functional layer to the end of the process of forming the sealing layer is exposed to PGMEA. A × B was 113 ppm · sec. The average concentration A of PGMEA was 0.01798 ppm and the exposure time B was 6285 seconds.
有機ＥＬ素子Ｃ３に電圧を印加したところ、青色のＥＬ発光が観測された。初期輝度が１０００ｃｄ／ｍ2となるように電流値を設定後、定電流で駆動させ、ＬＴ９５を測定したところ、２４．２時間であった。 When a voltage was applied to the organic EL element C3, blue EL light emission was observed. After setting the current value so that the initial brightness was 1000 cd / m 2 , it was driven by a constant current and the LT95 was measured. It was 24.2 hours.
Claims (6)
陽極を形成する工程と、陰極を形成する工程と、少なくとも１層の有機機能層を形成する工程と、封止層を形成する工程とを含み、
少なくとも１層の有機機能層を形成する工程の開始時から封止層を形成する工程の終了時までに製造中の有機ＥＬ素子が曝露されるプロピレングリコール−１−モノメチルエーテル−２−アセテートの平均濃度：Ａ（ｐｐｍ）と、曝露時間：Ｂ（秒）とが、式（１−１）を満たす、有機ＥＬ素子の製造方法。
０≦Ａ×Ｂ＜９ （１−１）
A method for manufacturing an organic EL device having an anode, a cathode, at least one organic functional layer provided between the anode and the cathode, and a sealing layer.
It includes a step of forming an anode, a step of forming a cathode, a step of forming at least one organic functional layer, and a step of forming a sealing layer.
The average of propylene glycol-1-monomethyl ether-2-acetate to which the organic EL element being manufactured is exposed from the start of the step of forming at least one organic functional layer to the end of the step of forming the sealing layer. A method for producing an organic EL element, wherein the concentration: A (ppm) and the exposure time: B (seconds) satisfy the formula (1-1).
0 ≦ A × B <9 (1-1)
０≦Ａ＜１ （２−１）
The method for manufacturing an organic EL device according to claim 1, wherein A satisfies the formula (2-1).
0 ≦ A <1 (2-1)
０≦Ｂ≦８６４００ （３−１）
The method for producing an organic EL device according to claim 1 or 2, wherein B satisfies the formula (3-1).
0 ≦ B ≦ 86400 (3-1)
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