WO2008149829A1 - 有機エレクトロルミネッセンス素子および該素子を用いた表示装置 - Google Patents
有機エレクトロルミネッセンス素子および該素子を用いた表示装置 Download PDFInfo
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- WO2008149829A1 WO2008149829A1 PCT/JP2008/060110 JP2008060110W WO2008149829A1 WO 2008149829 A1 WO2008149829 A1 WO 2008149829A1 JP 2008060110 W JP2008060110 W JP 2008060110W WO 2008149829 A1 WO2008149829 A1 WO 2008149829A1
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
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- 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
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
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- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
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- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
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- 125000006308 propyl amino group Chemical group 0.000 description 1
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- 239000005053 propyltrichlorosilane Substances 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- HLWCOIUDOLYBGD-UHFFFAOYSA-N trichloro(decyl)silane Chemical compound CCCCCCCCCC[Si](Cl)(Cl)Cl HLWCOIUDOLYBGD-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical group COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 description 1
- 229960001128 triprolidine Drugs 0.000 description 1
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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Definitions
- the present invention relates to an organic electoluminescence device (hereinafter sometimes referred to as an organic EL device) and a display device using the device.
- Organic EL devices are attracting attention as members for next-generation displays, for example, because they are characterized by the ability to easily emit light of many colors in addition to low voltage drive and high brightness.
- the organic EL device includes an anode, a cathode, and an organic layer having a light emitting layer.
- an organic layer hole transport made of poly (ethylene dioxythiophene) monopolystyrene sulfonic acid (hereinafter referred to as PED0T: PSS) is used. It is known to use organic layers with layers. Disclosure of the invention
- PED0T PSS is a strongly acidic water-soluble compound
- an alternative material is required from the viewpoint of manufacturing processes such as coating and film formation.
- an object of the present invention is to find the substitute material from the viewpoint of a manufacturing process such as coating and film formation, and to provide an organic electoluminescence device using the substitute material. That is, the present invention firstly
- An organic layer comprising at least two layers including
- At least one of the anode and the cathode is transparent or translucent
- the organic layer is provided between the anode and the cathode so as to be in contact with the anode, and at least a portion of the surface of the anode in contact with the organic layer is represented by the following general formula (1): (X) v — ! — M— R 1 (1)
- X is a group or atom that reacts with a group or atom existing on the surface of the anode to form a bond
- M is a group 4, 5, 6, 13, 13 in the periodic table
- R 15 independently represents an alkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, or an arylalkynyl group
- V represents an atom of M Show the price.
- a layer in contact with the anode constituting the organic layer contains the organic compound.
- An organic electoluminescence device is provided.
- a second aspect of the present invention provides a planar light source comprising the organic electoluminescence device.
- the present invention provides a segment display device comprising the organic electoluminescence device.
- the present invention provides a dot matrix display device comprising the organic electoluminescence element.
- the present invention provides a liquid crystal display device comprising a pack light composed of the organic electoluminescence element.
- halogen atoms fluorine atom, chlorine atom, bromine atom, and iodine atom are Illustrated.
- C m to C n indicates that the organic group described with this term has m to n carbon atoms.
- the alkyl group means an unsubstituted alkyl group and an alkyl group substituted with an octalogen atom, an amino group, a mercapto group or the like, and includes both a linear alkyl group and a cyclic alkyl group (cycloalkyl group).
- the alkyl group may have a branch.
- the number of carbon atoms in the alkyl group is usually about 1 to 20, preferably about 1 to 15 and more preferably about 1 to 10.
- Examples include methyl, ethyl, propyl, i-propyl, butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, cyclohexyl, Heptyl, Octyl, 2-Ethylhexyl, Nonyl, Decyl, 3,7-Dimethyloctyl, Lauryl, Trifluoromethyl, Pentafluoroethyl, Perfluorobutyl, Parf Fluorohexyl group, perfluorooctyl group, trifluoropropyl group, tride force fluoro-1,1,2,2-tetrahydrooctyl group, heptadecafluoro-1,1,2,2-tetrahydrodecyl group , Aminopropyl group, aminooctyl group, aminodecyl group, mercaptopropyl group, mercaptooctyl
- the C i ⁇ C 1 2 alkyl group for example, a methyl group, E Ji group, propyl group, i one propyl group, butyl group, i- butyl, s- butyl, t one-butyl group, a pentyl group, Examples include isoamyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group and the like.
- the alkoxy group means an unsubstituted alkoxy group and an alkoxy group substituted with a halogen atom, an alkoxy group or the like, and includes both a linear alkoxy group and a cyclic alkoxy group (cycloalkoxy group).
- the alkoxy group may have a branch.
- the number of carbon atoms of the alkoxy group is usually 1 to 20, preferably 1 to 15 and more preferably about 1 to 10.
- Examples include methoxy, ethoxy, and pro Pyroxy, i_propyloxy, butoxy, i-butoxy, t-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy Decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyl group, perfluorooctyl group , Methoxymethyloxy group, 2-methoxyethyloxy group and the like.
- Examples of the C 1 to C 12 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an i-propyloxy group, a butoxy group, an i-butoxy group, a t-butoxy group, a pentyloxy group, a hexyloxy group, Examples thereof include a cyclohexyloxy group, a heptyloxy group, an octyloxy group, a 21-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, and a lauryloxy group.
- the alkylthio group means an unsubstituted alkylthio group and an alkylthio group substituted with a halogen atom or the like, and includes both a linear alkylthio group and a cyclic alkylthio group (cycloalkylthio group).
- the alkylthio group may have a branch.
- the number of carbon atoms of the alkylthio group is usually about 1 to 20, preferably about 1 to 15 and more preferably about 1 to 10.
- Examples thereof include methylthio group, ethylthio group, propylthio group, i-propylthio group, butylthio group, i-butylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, Examples include 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, laurylthio group, and trifluoromethylthio group.
- Examples of the C 1 to C 2 alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an i-propylthio group, a butylthio group, an i-butylylthio group, a t-butylthio group, a pentylthio group, a hexylthio group, and a cyclohexyl group.
- Examples include xylthio group, heptylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, and laurylthio group.
- An aryl group is a remaining atomic group obtained by removing one hydrogen atom bonded to a carbon atom constituting an aromatic ring from an aromatic hydrocarbon, an unsubstituted aryl group, a halogen atom, an alkoxy group, an alkyl group. Means an aryl group substituted by, etc.
- the aryl group includes those having a condensed ring and those in which two or more independent benzene rings or condensed rings are bonded via a single bond or a divalent organic group, for example, an alkenylene group such as a vinylene group.
- the number of carbon atoms in the aryl group is usually about 6 to 60, preferably about 7 to 48, and more preferably about 7 to 30.
- a phenyl group As an aryl group, a phenyl group, a C 1 , a C 1 2 alkoxy phenyl group, a C 1 , a C 2 C alkyl alkyl group, a 1 naphthyl group, a 2 naphthyl group, a 1 anthracenyl group, a 2 anthracenyl group, Examples include 9-anthracenyl group and penfluorofluorophenyl group, and an alkoxyphenyl group and a C 1 ⁇ C 12 alkylphenyl group are preferable.
- alkoxyphenyl groups include methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, i-propyloxyphenyl group, butoxyphenyl group, i-butoxyphenyl group , T-butoxyphenyl group, pentyloxyphenyl group, hexyloxyphenyl group, cyclohexyloxyphenyl group, heptyloxyphenyl group, octyloxyphenyl group, 2-ethylhexyloxyphenyl Group, nonyloxyphenyl group, decyloxyphenyl group, 3,7-dimethyloctyloxyphenyl group, lauryloxyphenyl group, and the like.
- C 1 , ⁇ C 1 2 alkyl phenyl groups include methyl phenyl group, ethenyl phenyl group, dimethyl phenyl group, propyl phenyl group, mesityl group, methyl ethyl phenyl group, i-propyl phenyl group, butyl phenyl group, i Examples include monobutylphenyl group, t-butylphenyl group, pentylphenyl group, isoamylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group, and dodecylphenyl group.
- the aryloxy group means an unsubstituted aryloxy group and an aryloxy group substituted with a halogen atom, an alkoxy group, an alkyl group or the like.
- the number of carbon atoms in the aryloxy group is usually 6-60, preferably? ⁇ 48, more preferably about 7 ⁇ 30. Examples include phenoxy groups, C 1 , ⁇ C 1 2 alkoxy phenoxy groups, C 1 , ⁇ C 1, 2 alkyl phenoxy groups, 1-naphthyloxy groups, 2-naphthyloxy groups, pen fluorphenoxy groups, etc. , And.
- An alkoxyphenoxy group and a C 1 , to C 12 alkylphenoxy group are preferred.
- alkoxyphenoxy groups include methoxyphenoxy group, ethoxyphenoxy group, propyloxyphenoxy group, i-propyloxyphenoxy group, butoxyphenoxy group I-butoxyphenoxy group, t-butoxyphenoxy group, pentyloxyphenoxy group, hexyloxyphenoxy group, cyclohexoxyphenoxy group, heptyloxyphenoxy group, Octyloxyphenoxy group, 2-ethylhexyloxyphenoxy group, nonyloxyphenoxy group, decyloxyphenoxy group, 3,7-dimethyloctyloxyphenoxy group, lauryloxyf An enoxy group etc. are mentioned.
- Examples of 2 alkylphenoxy groups include methylphenoxy group, ethylphenoxy group, dimethylphenoxy group, propylphenoxy group, 1,3,5- 5-methylphenoxy group, methyl group Tylphenoxy group, i-propylphenoxy group, Butylphenoxy group, i-Butylphenoxy group, t-Butylphenoxy group, Pentylphenoxy group, Isoamylphenoxy group, Hexylphenoxy group, Heptylphenoxy group, Octylphenoxy group Ci group, nonylphenoxy group, decylphenoxy group, dodecylphenoxy group, etc.
- the allylthio group means an unsubstituted allylthio group and an allylthio group substituted with an octalogen atom, an alkoxy group, an alkyl group, etc.
- Base charcoal The number of elementary atoms is usually about 6 to 60, preferably about 7 to 48, and more preferably about 7 to 30. Examples include phenylene thio group, C, -C 12 Arukokishifue two thio group, C, ⁇ C, 2 alkyl phenylthio group, 1 one naphthylthio group, 2-Nafuchiruchi O group, penta full O Loftus et two Lucio Groups and the like.
- An arylalkyl group means an unsubstituted arylalkyl group and an arylalkyl group substituted with a halogen atom, an alkoxy group, an alkyl group or the like. Is the number of carbon atoms in the arylalkyl group normal? -60, preferably 7-48, more preferably about 7-30.
- Examples include phenylene Lou 1-2 alkyl group, 2 Arukokishifue two Roux C, ⁇ C, 2 alkyl group, C, -C I 2 Arukirufue two Roux C, -C, 2 alkyl group, 1 one Nafuchiru C, -C 12 alkyl group, 2 one Nafuchiru C, etc. -C twelve alkyl group.
- An arylalkoxy group means an unsubstituted aryloalkoxy group and an aryloalkoxy group substituted with a halogen atom, an alkoxy group, an alkyl group or the like.
- the number of carbon atoms in the arylalkoxy group is usually 7-60, preferably 7-48, more preferably? ⁇ 30 or so.
- Examples include phenylene Lou C, -C 12 alkoxy group, C, -C I2 Arukokishifue two routes to (12 alkoxy group, Ji alkylphenyl -. (:, ⁇ (:, 2 alkoxy groups, 1 -Naphthyl ( ⁇ ⁇ ji alkoxy group, 2-naphthyl- ⁇ ( 12 alkoxy group, etc.
- An arylalkylthio group is an unsubstituted arylalkylthio group, a halogen atom, an alkoxy group, an alkyl group, etc. This means a substituted arylalkylthio group
- the number of carbon atoms of the arylalkylthio group is usually 7 to 60, preferably 7 to 48, more preferably about 7 to 30.
- Examples thereof include phenyl-C , ⁇ C, 2 alkylthio group, c,, ⁇ c 12 alkoxy phenyl, alkyl thio group, C, ⁇ C, 2 alkylphenyl- C, ⁇ C, 2 alkylthio group, 1 naphthyl C, ⁇ C, 2 alkylthio group, 2-naphthyl ( ⁇ ⁇ . Alkylthio group etc. are mentioned.
- the arylalkenyl group is substituted with an unsubstituted arylene alkenyl group and a halogen atom, an alkoxy group, an alkyl group, etc. means ⁇ reel alkenyl group.
- the number of carbon atoms in ⁇ reel alkenyl group is usually 8 to 60, preferably 8 to 48, yo Ri preferably about 8-30.
- examples include phenylene Lou C 2 ⁇ C 12 alkenyl group, ⁇ Alkoxy phenyl C 2 ⁇ C 12 alkenyl group, C, ⁇ C 12 alkyl phenyl-C Z ⁇ C I2 alkenyl group, 1-naphthyl-C 2 ⁇ C 12 alkenyl group , 2-naphthyl - such as C 2 -C 12 alkenyl group, and ⁇ Ji alcohol Kishifueniru - C 2 -C 12 alkenyl group, C 2 -C 12 alkylphenyl - C 2 -C, 2 alkenyl groups are preferred.
- the C 2 -C 12 alkenyl group include a vinyl group, 1 one propenyl group, 2 one propenyl, 1-butenyl, 2-butenyl group, 1 one-pentenyl group, 2-Bae Nparu group, 1-hexenyl group, 2-hexenyl group, 1-octenyl group and the like can be mentioned.
- An arylalkynyl group means an unsubstituted allylalkynyl group and an allylalkynyl group substituted with a halogen atom, an alkoxy group, an alkyl group or the like.
- the number of carbon atoms of the aryl alkynyl group is usually 8 to 60, preferably 8 to 48, and more preferably about 8 to 30.
- Examples thereof include phenyl C 2 -C 12 alkynyl group, C 1, C 2 , 2 alkoxy phenyl C 2 C C, 2 alkynyl group, C C 1 C 2 alkyl phenyl C 2 C 12 Alkynyl groups, 1-naphthyl-c 2 to c 12 alkynyl groups, 2-naphthyl C 2 to C 12 alkynyl groups, and the like, and-( 12 alkoxyphenyl-C 2 -C !
- 2 alkynyl groups C, -C, A 2- alkyl phenyl C 2 -C, 2 alkynyl group is preferred.
- the C 2 -C 1 2 alkynyl group for example, Echiniru group, 1 one propynyl group, 2-Puropieru group, 1 Buchiniru group, 2 Bucheru group, 1 one-pentynyl, 2-pentynyl group, 1 one to hexynyl group, Examples include 2-hexynyl group and 1-octynyl group.
- the monovalent heterocyclic group is a remaining atomic group obtained by removing one hydrogen atom from a heterocyclic compound, and is a monovalent substituted with a substituent such as an unsubstituted monovalent heterocyclic group or an alkyl group.
- a heterocyclic group of The number of carbon atoms of the monovalent heterocyclic group is usually about 4 to 60, preferably about 4 to 30 and more preferably about 4 to 20 without including the number of carbon atoms of the substituent.
- the heterocyclic compound is an organic compound having a cyclic structure, and as an element constituting the ring, not only a carbon atom but also an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorus atom, a boron atom, An atom, selenium atom, tellurium atom, arsenic atom, etc.
- Monovalent heterocyclic groups include, for example, a cenyl group, C,
- -C 1 2 alkyl chain group a pyrrolyl group, a furyl group, a pyridyl group, (:> - (:, 2 ⁇ Rukirupirijiru group, pyridazinyl group, pyrimidyl group, pyrazinyl group, triazine two group, pyrrolidyl group, piperidyl group, A quinolyl group, an isoquinolyl group, etc. are mentioned, Among these, a cenyl group, C 1, C 2 , C 2 alkyl enyl group, pyridyl group, c 1 , c 1 2 alkyl pyridyl group are preferable.
- the amino group includes an unsubstituted amino group, an alkyl group, an aryl group, an arylalkyl group, and an amino group. It means an amino group (hereinafter referred to as a substituted amino group) substituted with 1 or 2 substituents selected from a monovalent heterocyclic group, which is further referred to as a secondary substituent (hereinafter referred to as a secondary substituent). In some cases, it may have a carbon atom of a substituted amino group.
- the number of atoms is usually 1 to 60, preferably 2 to 48, more preferably about 2 to 40, not including the number of carbon atoms of the secondary substituent.
- substituted amino group examples include a methylamino group, a dimethylamino group, an ethylamino group, a jetylamino group, a propylamino group, a dipropylamino group, an isopropylamino group, a diisopropylamino group, a ptylamino group, an isoptylamino group, an s-ptylamino group, t 1-ptylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexylamino group, noelamino group, decylamino group, 3,7-dimethyloctylamino group, dodecylamino group, cyclopentylamino group group, dicyclopentyl Rua amino group, Kishiruamino group cyclohexylene,
- Arukirufue two Lou C, -C 12 alkyl) amino group 1 one Nafuchiru C ⁇ C alkylamino group, such as 2- Nafuchiru ⁇ (12 alkylamino group silyl group,
- An unsubstituted silyl group and a silyl group substituted with 1, 2 or 3 substituents selected from an alkyl group, an aryl group, an arylalkyl group and a monovalent heterocyclic group hereinafter referred to as a substituted silyl group
- the substituent may have a secondary substituent
- the number of carbon atoms of the substituted silyl group does not include the number of carbon atoms of the secondary substituent, and is usually 1 to 60, preferably 3 to 48, more preferably about 3-40 .
- Examples of the substituted silyl group include a trimethylsilyl group, Toryechirushiri group, triprolidine building silyl group, tri - isopropyl silyl group, dimethyl chromatography isopropoxy Methyl pyrsilyl group, Jetyl-isopropyl silyl group, t-Ipylsilyldimethylmethylsilyl group, Octyldimethylsilyl group, 21-ethylhexyl dimethylsilyl group, Nonyldimethylsilyl group, Decyldimethylsilyl group, 3,7-dimethyl Octyl-dimethylsilyl group, dodecyldimethylsilyl group, phenyl-
- Examples include a butyl diphenylsilyl group and a dimethylphenylsilyl group.
- the acyl group means an unsubstituted acyl group and an acyl group substituted with an eight-rogen atom or the like.
- the number of carbon atoms of the isyl group is usually about 1 to 20, preferably about 2 to 18, and more preferably about 2 to 16.
- Examples of the acyl group include a formyl group, an acetyl group, a propionyl group, a petityl group, an isoptylyl group, a pivaloyl group, a benzoyl group, a trifluoroacetyl group, and a pentafluorobenzoyl group. It is possible.
- the acyloxy group means an unsubstituted acyloxy group and an acyloxy group substituted with a halogen atom or the like.
- the number of carbon atoms of the acyloxy group is usually about 1 to 20, preferably about 2 to 18, and more preferably about 2 to 16.
- As the acyloxy group for example, formyloxy group, acetoxy group, propionyloxy group, petityloxy group, isoptyryloxy group, pivaloyloxy group, benzoyloxy group, trifluoroacetyloxy group, pentafluorobenzoyl group Examples include a ruoxy group.
- the imine residue is at least one of the formula: H—N—C and the formula: one N ⁇ CH— It means a residue obtained by removing one hydrogen atom in this structure from an imine compound having the structure represented.
- an imine compound for example, a hydrogen atom bonded to a nitrogen atom in aldimine, ketimine, and aldimine is substituted with an alkyl group, an aryl group, an aryl alkyl group, an aryl alkenyl group, an aryl alkynyl group, or the like.
- the number of carbon atoms in the imine residue is usually about 2 to 20, preferably about 2 to 18, and more preferably about 2 to 16.
- a ring may be formed as an alkylene group having 2 to 18 carbon atoms, and examples of the imine residue include groups represented by the
- An amide group means an unsubstituted amide group or an amide group substituted with a halogen atom or the like.
- the number of carbon atoms in the amide group is usually about 2 to 20, preferably about 2 to 18, and more preferably about 2 to 16.
- the amide group examples include a formamide group, a acetoamide group, a propioamide group, a ptyramide group, a benzamide group, a trifluoroacetamide group, a penufluorene benzamide group, a diformamide group, a diacetoamide group, a dipropioamide group, a dibutyroamide group, Examples thereof include a dibenzamide group, a mid group, and a dipentafluorobensamide group.
- the acid imide group means a residue obtained by removing a hydrogen atom bonded to the nitrogen atom from an acid imide.
- the number of carbon atoms in the acid imide group is usually about 4 to 20, preferably about 4 to 18, and more preferably about 4 to 16.
- Examples of the acid imide group include the following groups.
- the force lpoxyl group is a force substituted with an unsubstituted carboxyl group and a substituent such as an alkyl group, an aryl group, an aryl alkyl group, or a monovalent heterocyclic group. It means a lupoxyl group (hereinafter referred to as a substituted carboxyl group).
- the substituent may have a secondary substituent.
- the number of carbon atoms of the substituted carboxyl group is usually 1 to 60, preferably 2 to 48, more preferably about 2 to 45 without including the number of carbon atoms of the secondary substituent.
- substituent lpoxyl group examples include a methoxycarbonyl group, a ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, an s-butoxycarbonyl group, a t-butoxycarbonyl group, and a pentylcarbonyl group.
- Xycarbonyl group hexyloxycarbonyl group, cyclohexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, 2-ethyl hexyloxycarbonyl group, nonyloxycarbonyl group Group, decyloxycarbonyl group, 3,7-dimethyloctyloxycarbonyl group, dodecyloxycarbonyl group, trifluoromethoxycarbonyl group A group, a penoxyfluoroethoxycarbonyl group, a perfluorooxycarbonyl group, a perfluorohexoxycarbonyl group, a perfluorooctylcarbonyl group, a phenoxycarbonyl group, a naphthoxycarbonyl group, Examples thereof include a pyridyloxy carbonyl group.
- the organic compound used for the treatment of the anode surface and added to Z or a layer in contact with the anode constituting the organic layer is represented by the following general formula (1):
- X is a group or atom that reacts with a group or atom existing on the surface of the anode to form a bond
- M is a group 4, 5, 6, 13 or 14 in the periodic table.
- R 15 independently represents an alkyl group, an aryl group, an aryl alkyl group, an aryl alkenyl group, or an aryl alkynyl group
- V represents the valence of M. Show.
- X is a group or atom that reacts with a group or atom present on the surface of the anode to form a bond. X can be appropriately selected depending on the group or atom present on the surface of the anode.
- examples of X include a hydroxyl group, a carboxyl group, an acyl group, an acyloxy group, and a halo force sulfonyl group (formula: one C (0) one Y (Wherein Y represents a halogen atom) means a group represented by the formula: —C (0) — a group represented by C 1 and a formula: one C (0) one Br A halogen atom, an alkoxy group, an aryloxy group, an aryloxy group, a phosphoric acid residue (a group represented by the formula: (HO) 2 P (O) — O—), a phosphate ester residue Group (formula: (R'O).
- a bond such as a covalent bond, a coordinate bond, or an ionic bond is formed between the organic compound represented by the general formula (1) and the anode. Is done.
- the anode a conductive inorganic oxide or metal thin film is generally used, and since the surface often has a hydroxyl group, X can be a group capable of reacting with a hydroxyl group or An atom such as a halogen atom, an alkoxy group, a phosphoric acid residue, or an amino group is preferred.
- X may directly react with a group or atom present on the surface of the anode, but may react indirectly with another substance.
- M is an atom of a metal element belonging to Group 4, Group 5, Group 6, Group 13, Group 14, or Group 15 of the Periodic Table.
- the metal element also includes metalloid elements such as boron, silicon, germanium, phosphorus, arsenic, antimony, and bismuth.
- M atoms of metal elements belonging to Group 4 such as titanium, zirconium and hafnium; atoms of metal elements belonging to Group 5 such as vanadium, niobium and tantalum; Group 6 such as chromium, molybdenum and tungsten Atoms of metal elements belonging to the group; atoms of metal elements belonging to the group 13 such as boron, aluminum, gallium, indium, thallium; atoms of metal elements belonging to the group 14 such as kaium, germanium, tin, lead; Atoms of metal elements belonging to Group 15 such as phosphorus, arsenic, antimony, bismuth, etc. It is.
- Group 4 such as titanium, zirconium and hafnium
- atoms of metal elements belonging to Group 5 such as vanadium, niobium and tantalum
- Group 6 such as chromium, molybdenum and tungsten Atoms of metal elements belonging to the group
- atoms of metal elements belonging to the group 13 such
- a gate atom, a zirconium atom, an aluminum atom, a boron atom, a phosphorus atom, a boron atom, a boron atom, a phosphorus atom, a boron atom, a boron atom, and a phosphorus atom are preferable.
- An atom is more preferable, and a silicon atom, a titanium atom, and a phosphorus atom are still more preferable.
- R 1 independently represents an alkyl group, an aryl group, an aryl alkyl group, an aryl alkenyl group, or an aryl alkynyl group.
- V represents the valence of M, and the value is known to those skilled in the art for each of the above metal elements.
- M is a key atom, titanium atom, zirconium atom, etc.
- V is 4
- M is boron, aluminum, etc.
- V is 3.
- a hydroxyl group is present on the surface of the anode, and the organic compound represented by the general formula (1) is represented by the following general formula (2):
- X is particularly preferably a halogen atom, an alkoxy group, a phosphoric acid residue, or an amino group.
- R 1 is particularly preferably an alkyl group or an aryl group.
- the organic compound represented by the general formula (1) is represented by the following general formula (4):
- A is independently a chlorine atom or a hydroxyl group
- B is an alkyl group having 2 to 10 carbon atoms.
- It is an organic compound represented by these. Examples of the organic compound represented by the general formula (1) are as follows.
- silane coupling agents examples include propyltrimethoxysilane, decyltrimethoxysilane, decyltrimethoxysilane,
- Octyltriethoxysilane tridecafluoro-1,1,2,2,2-tetraoctyltritrimethoxysilane, tridecafluoro-1,1,2,2-tetrahydrate, octyltrichlorosilane, trifluoropropyltrimethoxysilane, etc.
- the fluorinated alkylsilane can be mentioned. These silane coupling agents may be used alone or in combination of two or more. Of these, fluoroalkylsilane is preferred.
- titanium coupling agents examples include propyltrimethoxy titanium, octyl Trimethoxytitanium, Amaminopropyltrimethoxytitanium, Amaminodecyltrimethoxytitanium, Mercaptopropyltrimethoxytitanium, Mercaptooctyltrimethoxytitanium, Amaminopropyltriethoxytitanium, Mercaptoprobilt triethoxytitanium, Mercaptodecyltriethoxytitanium , Propyl trichrome mouth titanium, octyl trichrome mouth titanium, decyl trichrome mouth titanium, aminopropyl trichrome mouth titanium, mercaptopropyl triclo mouth titanium, mercaptooctyl trichrome mouth titanium, heptadecafluoro- 1,1,2,2-tetrahydrodecyltriethoxy titanium And heptadecafluoro
- titanium coupling agents may be used alone or in combination of two or more.
- a phosphonate ester compound ((R 1 0) 2 P ( ⁇ ) 1 R 1 ), acidic phosphonate compounds ((R 1 O) (HO) P (O) -R 1 ), phosphonate compounds ((HO) 2 P (O) — R 1 ), phosphonite compounds (( R 1 O) 2 P— R 1 ), acidic phosphonite compounds ((R 1 0) (HO) PR 1 ), phosphonite compounds ((HO) 2 PR 1 ) (in these 6 formulas: 1 is as described above.)) Can also be used.
- the organic EL device of the present invention at least a portion of the surface of the anode in contact with the organic layer is treated with the organic compound represented by the general formula (1) or a layer in contact with the anode constituting the organic layer Contains the organic compound, or at least a portion of the surface of the anode in contact with the organic layer is treated with the organic compound, and a layer in contact with the anode constituting the organic layer contains the organic compound.
- the organic compound is dissolved in a solvent, and obtained.
- the anode is immersed in a solution so that the group X (that is, the hydrophilic portion) in the organic compound reacts with the anode, and then the anode is separated from the solution, and the anode is added with a solvent that dissolves the organic compound.
- cleaning is mentioned.
- the solvent that dissolves the organic compound is not particularly limited as long as it does not react with the organic compound.
- solvent examples include chlorine-based solvents such as black mouth form, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, black mouth benzene and o-dichloro mouth benzene; ethers such as tetrahydrofuran and dioxane. Solvents; aromatic hydrocarbon solvents such as toluene and xylene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.
- chlorine-based solvents such as black mouth form, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, black mouth benzene and o-dichloro mouth benzene
- ethers such as tetrahydrofuran and dioxane.
- Aliphatic hydrocarbon solvents such as acetone, methylethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and cetyl cellosolve acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol Monoethyl ether, Ethylene Daricol monomethyl ether, Dimethyl Polyhydric alcohols and derivatives thereof such as xishane, propylene glycol, diethoxymethane, polyethylene glycol monoethyl ether, glycerin, 1,2-hexanediol; methanol, ethanol, propanol, isopropanol, cyclohexanol Examples thereof include alcohol solvents such as sulfoxide solvents such as dimethyl sulfoxide.
- the said solvent may be used individually by 1 type, or may use 2 or more types together.
- the concentration of the organic compound in a solution obtained by dissolving the organic compound represented by the general formula (1) in a solvent is not particularly limited, but if the concentration is low, the organic compound and the cathode Since the reaction may take a long time, it is not preferable. A high concentration is not preferable because the film forming property may be deteriorated due to aggregation of molecules of the organic compound. Accordingly, the concentration of the organic compound is preferably from 0.01 to 100 mm o 1/1, but is not limited to this range.
- the temperature at which the organic compound represented by the general formula (1) is reacted with the anode is not particularly limited, but is preferably in the range of 10 to 50 ° C.
- the time required for the reaction is not particularly limited, but generally it is preferably in the range of 1 minute to 24 hours.
- the polymer compound containing a repeating unit consisting of an aromatic amine skeleton in the main chain has 3 repeating units consisting of an aromatic amine skeleton with respect to all repeating units in the polymer compound. 0 mol% or more and 100 mol% or less, and is used for transporting holes in the organic layer, and particularly when the hole transport layer containing the polymer compound is in contact with the anode, It is also used to efficiently inject holes into the organic layer.
- the proportion of the repeating unit comprising an aromatic amine skeleton is 40 mol% or more and 100 mol% or less, preferably 50 mol% or more and 85 mol% or less, based on all repeating units in the polymer compound.
- the polymer compound includes a repeating unit composed of an aromatic amine skeleton and another repeating unit composed of a conjugated compound residue having an aromatic hydrocarbon ring and / or an aromatic heterocyclic ring.
- Aromatic amine copolymers are used.
- the repeating unit comprising the above aromatic amine skeleton the following formula (5):
- a r 1 A r 2 , A r 3 and A r 4 independently represent an arylene group or a divalent heterocyclic group.
- a r 5 , A r 6 and A r 7 are independently Represents an aryl group or a monovalent heterocyclic group, or A r 6 and A r 7 together represent a nitrogen atom to which A r 6 and A r 7 are bonded, instead of representing the above group. And may form a ring together with o and p independently represent 0 or 1.
- arylene groups include phenylene group, biphenylene group, terfenylene group, naphthalenediyl group, anthracenedyl group, phenanthrene group, pentadenyl group, indendyl group, Heptophane diyl group, indendezyl group, triphenyl diyl group, binaphthyl diyl group, phenyl naphthalene diyl group, stilbene diyl group, full orange diyl group, etc.
- divalent heterocyclic groups examples include pyridine-diyl group, diazaphenylene group Quinoline diyl group, quinoxaline diyl group, acrylidine diyl group, piperidyl diyl group, phenanthoxylin diyl group and the like.
- the aryl group usually has 6 to 60 carbon atoms, and examples thereof include a phenyl group.
- a monovalent heterocyclic group means an atomic group formed by removing one hydrogen atom from a heterocyclic compound, and examples thereof include a pyridyl group.
- the repeating unit represented by the formula (5) examples include a repeating unit represented by the following formula.
- the hydrogen atom on the aromatic hydrocarbon ring or aromatic heterocyclic ring is independently an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or 7 to 2 carbon atoms.
- 6 phenylalkyl groups, 7-26 phenyl alkoxy groups, phenyl groups, phenoxy groups, 7-26 alkyl group-substituted phenyl groups, carbon Substituted with an alkoxy group-substituted phenyl group having 7 to 26 atoms, an alkyl carbonyl group having 2 to 21 carbon atoms, a formyl group, an alkoxycarbonyl group having 2 to 21 carbon atoms, or a strong loxyl group.
- phenylalkyl group examples include those having usually 7 to 26 carbon atoms, preferably 11 to 21 and more preferably 14 to 18 carbon atoms, and examples thereof include phenylmethyl.
- phenylethyl group phenylpropyl group, phenylbutyl group, phenylpentyl group, phenylhexyl group, phenylheptyl group, phenyloctyl group, phenylnoel group, phenyldecyl group, and phenyldodecyl group.
- phenylalkoxy group examples include those having usually 7 to 26 carbon atoms, preferably 11 to 21 and more preferably 14 to 18 carbon atoms.
- examples thereof include phenyl Methoxy group, phenylethoxy group, phenylpropyloxy group, phenylbutoxy group, phenylpentyloxy group, phenylhexyloxy group, phenylheptyloxy group, phenyloctyloxy group, phenylnonyloxy group A phenyldecyloxy group, a phenyldecyloxy group, and the like.
- An alkyl group-substituted phenyl group is a group in which one or more hydrogen atoms on a phenyl group are substituted with an alkyl group having 1 to 20 carbon atoms, that is, a monoalkylphenyl group, a dialkylphenyl group, A trialkylphenyl group, a tetraalkylphenyl group, and a pen alkyl group.
- alkyl group-substituted phenyl group include those having usually 7 to 26 carbon atoms, preferably 11 to 21 and more preferably 14 to 18 carbon atoms.
- An alkoxy group-substituted phenyl group is a group in which one or more hydrogen atoms on a phenyl group are substituted with an alkoxy group having 1 to 20 carbon atoms, that is, a monoalkoxyphenyl group, a dialkoxyphenyl group, An alkoxyphenyl group, a tetraalkoxyphenyl group, and a pentaalkoxyphenyl group.
- Examples of the alkoxy group-substituted vinyl group include those having usually 7 to 26 carbon atoms, preferably 11 to 21 and more preferably 14 to 18 carbon atoms.
- alkylcarbonyl group examples include those having usually 2 to 21 carbon atoms, preferably 5 to 1.5 carbon atoms, more preferably 8 to 12 carbon atoms, and examples thereof include acetyl groups and propionyl groups.
- alkoxycarbonyl group examples include those having usually 2 to 21 carbon atoms, preferably 5 to 15 carbon atoms, more preferably 8 to 12 carbon atoms.
- Examples thereof include a methoxycarbonyl group, Ethoxycarbonyl group, propyloxy group, isopropyloxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl group, s-butoxycarbonyl group, t-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxy group Carbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, 3,7-dimethyloctyloxycarbonyl group, dodecyloxy group
- Examples thereof include a xycarbonyl group.
- the repeating units represented by the above formula (5) the following formula (6):
- R 3 , R 4 and R 5 are independently an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a phenylalkyl group having 7 to 26 carbon atoms, 7-26 phenyl alkoxy group, phenyl group, phenoxy group, carbon atom number?
- -26 alkyl group-substituted phenyl group, 7-26 alkoxy group-substituted phenyl group, 2-carbon atom number 21 represents an alkyl carbonyl group, a formyl group, an alkoxy carbonyl group having 2 to 21 carbon atoms, or a strong lpoxyl group, or R 3 and R 4 are combined together instead of the above groups.
- X and y are each independently an integer of 0 to 4, z is 1 or 2, and w is an integer of 0 to 5.
- R 3 , R 4 and R 5 In the case where a plurality of at least one kind is present, the plural groups present may be the same or different You can have me.
- the repeating unit represented by is preferable.
- Examples of the heterocyclic ring include a morpholine ring, a thiomorpholine ring, a pyrrole ring, a piperidine ring, and a piperazine ring.
- Examples of the repeating unit represented by the general formula (6) include repeating units represented by the following formulas (6—) to (6-10).
- R 6 represents an alkyl group having 1 to 20 carbon atoms, and w is an integer of 0 to 5. When a plurality of R 6 are present, they are the same or different. It is okay.)
- the terminal portion of the polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain has a polymerization active group as it is, and when used in the production of a device, the light emitting characteristics and lifetime of the resulting device are reduced. Since it may be lowered, it is preferably protected with a stable protecting group.
- the protecting group preferably has a conjugated bond continuous with the conjugated structure of the main chain.
- an aryl group or a monovalent heterocyclic group is bonded to the main chain via a carbon-carbon bond.
- Structure. Specific examples include substituents described in Chemical formula 10 of JP-A-9-45478.
- the polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain is represented by the following general formula (8) together with at least one repeating unit composed of the aromatic amine skeleton. It is preferable from the viewpoint of device characteristics such as maximum luminous efficiency and device lifetime that the main chain contains at least one type of repeating unit represented by
- Ar 8 represents an arylene group.
- the arylene group is a hydrogen atom bonded to a carbon atom constituting an aromatic ring from an aromatic hydrocarbon. It is the remaining atomic group excluding 2 and means an unsubstituted arylene group and a substituted arylene group.
- the arylene group includes those having a condensed ring, and those having two or more independent benzene rings or condensed rings bonded via a single bond or a divalent organic group, for example, an alkenylene group such as vinylene.
- the substituent atom and the substituent in the substituted arylene group are not particularly limited, but from the viewpoints of solubility, fluorescence characteristics, ease of synthesis, characteristics in the case of an element, etc.
- a cyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a strong loxyl group, a cyano group or a nitro group are preferred.
- the number of carbon atoms in the arylene group excluding the substituent is usually 6 to 60, preferably 6 to 20 and more preferably about 6 to 18.
- the total number of carbon atoms including the substituent of the arylene group is usually about 6 to 100, preferably about 6 to 80, and more preferably about 6 to 70.
- arylene groups include phenylene groups (for example, groups represented by the following general formulas:! To 3), naphthalene diyl groups (for example, groups represented by the following general formulas 4 to 13).
- Anthracene monozyl group for example, a group represented by the following general formula 14 to 19
- biphenyl group for example, a group represented by the following general formula 20 to 25
- terfenyl group for example, , A group represented by the following general formula 2 6 to 28, a fluorene-zyl group (for example, a group represented by the following general formula 3 6 to 38), a benzofluorene-zyl (for example, the following general formula 3 9 to 4 6), other divalent condensed polycyclic aromatic hydrocarbon groups (for example, groups represented by the following general formulas 29 to 35), and the like.
- R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkylthio group, an arylalkylthio group.
- a plurality of R may be the same or different.
- the repeating unit represented by the following general formula (9) is preferable from the viewpoint of the luminance half life of the organic electoluminescence element of the present invention.
- R 7 and R 8 may be the same or different and independently represent a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, Aryloxy group, arylalkylthio group, arylalkenyl group, arylalkynyl group, monovalent heterocyclic group, heterocyclicthio group, amino group, silyl group, acyl group, acyloxy group, imine residue , An amide group, an acid imide group, a strong lpoxyl group, a cyano group or a nitro group, h and i may be the same or different, and independently represent an integer of 0 to 3, and R 9 and.
- h and i are preferably 0 or 1, particularly preferably 0, from the viewpoint of ease of synthesis of the raw material monomer.
- R 9 and 1 ⁇ in the general formula (9). Is preferably an alkole group or aryl group from the viewpoint of ease of synthesis of the raw material monomer.
- Examples of the repeating unit represented by the general formula (9) include the repeating units represented by the following general formulas (9-1) to (9-8).
- the polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain preferably has a number average molecular weight of about 10 3 to 10 8 in terms of polystyrene, about 10 4 to about L 0 6 Is more preferable.
- “number average molecular weight” and “weight average molecular weight” in terms of polystyrene are determined using size exclusion chromatography (SEC) (manufactured by Shimadzu Corporation: LC-1 OAvp). The sample to be measured is dissolved in tetrahydrofuran to a concentration of about 0.5 wt%, and 50 L is injected into the SEC.
- SEC size exclusion chromatography
- tetrahydrofuran is used as the mobile phase of SEC, and it is allowed to flow at a flow rate of 0.6 mL / min.
- TSKgel Super HM-H manufactured by Tosohichi
- TSKgel SuperH2000 manufactured by Tosohichi
- a differential refractive index detector (manufactured by Shimadzu Corp .: RID-10A) is used as the detector.
- Examples of a method for synthesizing a polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain include a method of polymerizing from a monomer according to a desired polymer compound by a Suzuki coupling reaction, and a method of polymerizing by a Grignard reaction.
- the method of polymerizing by Suzuki coupling reaction the method of polymerizing by Grignard reaction, and the method of polymerizing by Ni (0) catalyst are preferable because the reaction control is easy.
- an alkali or a suitable catalyst can be added as appropriate to promote the reaction.
- These alkalis and appropriate catalysts may be selected according to the type of reaction, but those that are sufficiently soluble in the solvent used in the reaction are preferred.
- the alkali include inorganic bases such as potassium carbonate and sodium carbonate; organic bases such as triethylamine and tetraethylammonium hydroxide; and inorganic salts such as cesium fluoride.
- the catalyst examples include tetrakis (triphenylphosphine) palladium and palladium acetates.
- Purity of polymer compound containing repeating unit consisting of aromatic amine skeleton in main chain Since it affects the light emission characteristics of the device, it is preferable to polymerize the monomer before polymerization after purification by methods such as distillation, sublimation purification, and recrystallization, and after synthesis, reprecipitation purification, and fractionation by chromatography. It is preferable to perform a purification treatment such as the above.
- Examples of the solvent used in the reaction include saturated hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, and xylene; carbon tetrachloride, black mouth Form, Dichloromethane, Chlorobutane, Bromobutane, Black Pentan, Bromopentane, Black Hexane, Bromohexane, Chlorocyclohexane, Bromocyclohexane, etc., Rogenated saturated hydrocarbons; Black mouth benzene, Dichlorobenzene Halogenated aromatic hydrocarbons such as benzene, trichloromethane; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, and t-butyl alcohol; carboxylic acids such as formic acid, ace
- a crude polymer compound can be obtained by ordinary post-treatment such as quenching with water, extraction with an organic solvent, and distillation of the organic solvent. Further, as described above, the isolation and purification of the polymer compound can be performed by methods such as fractionation by chromatography and recrystallization. Examples of the synthesis method of the polymer compound include a compound represented by the following formula (1 0) alone, or a compound represented by the following formula (1 0) and the following formula (1 1). And a method of polymerizing the compound by the above-described method.
- X 1 to X 4 are independently a halogen atom, an alkylsulfo group, an arylsulfo group, an arylalkylsulfo group, or a boric acid ester residue.
- x ′ to x 4 are independently a halogen atom, an alkylsulfo group, an arylsulfo group. It is preferably an arylalkylsulfo group, a boric acid ester residue, or a boric acid residue.
- alkylsulfo group examples include a methanesulfo group, a ethanesulfo group, and a trifluoromethanesulfo group.
- arylsulfo groups examples include benzenesulfo groups and p-toluenesulfo groups.
- arylalkylsulfo groups examples include benzylsulfo groups.
- boric acid ester residue include a group represented by the following formula.
- Me represents a methyl group
- Et represents an ethyl group.
- sulfonium methyl group examples include groups represented by the following formulae.
- X represents a halogen atom
- Me represents a methyl group
- Ph represents a phenol.
- Examples of the phosphonium methyl group include groups represented by the following formulae.
- R 11 represents an alkyl group, an aryl group, or an aryl alkyl group.
- the monohalogenated methyl group include a methyl fluoride group, a methyl chloride group, a methyl bromide group, or a methyl iodide group. Illustrated.
- a hole transport layer containing a polymer compound containing a repeating unit composed of an aromatic amine amine skeleton in the main chain (hereinafter sometimes referred to as an aromatic amine polymer compound) is used.
- an aromatic amine polymer compound a polymer compound containing a repeating unit composed of an aromatic amine amine skeleton in the main chain
- aromatic amine polymer compound As a treatment for insolubilization, aromatic amine polymer compound Using an aromatic amine polymer compound having a soluble precursor or a soluble substituent, the precursor is converted into a polymer compound by heat treatment, or the solubility is lowered by decomposing the substituent.
- a method in which an aromatic amine polymer compound having a crosslinkable group in the molecule is used to cause a crosslinking reaction between the aromatic amine polymer compounds; and a crosslinking agent (heat, light) A method using a monomer or a macromer that causes a crosslinking reaction by an electron beam, etc .; an aromatic amine high molecular compound having no crosslinking group in the molecule and a crosslinking agent (a monomer that causes a crosslinking reaction by heat, light, electron beam, etc.) And the like, and the like.
- a polymer compound having a repeating unit composed of an aromatic amine skeleton in the main chain having a crosslinkable group in the molecule and if necessary, a crosslinking agent.
- the polymer compound containing a repeating unit comprising an aromatic amine skeleton in the main chain having a crosslinkable group in the molecule includes a repeating unit comprising an aromatic amine skeleton in the main chain having a crosslinkable group in the side chain.
- bridging groups include pinyl group, acetylene group, butenyl group, acryloyl group, acryloyloxy group, acrylamide group, methacryloyl group, methacryloyloxy group, methacrylamide group, vinyl ether group, A group having a vinylamino group, a silanol group, a crosslinkable group having a small ring (for example, a cyclopropyl group, a cyclobutyl group, an epoxy group, an oxetane group, a diketene group, an episulfide group, etc.), a lactone group, a lactam group, or a siloxane
- Examples include groups containing derivatives.
- combinations of groups capable of forming an ester bond or an amide bond can also be used.
- groups including a benzocyclobutane structure described in the W0 9/0 9 3 9 4 published specification are also exemplified.
- an acryloyloxy group or a methacryloyloxy group is particularly preferable.
- Such a polymer compound containing a repeating unit consisting of an aromatic amine skeleton in the main chain having a crosslinkable group in the molecule polymerizes a monomer having a corresponding crosslinkable group. Can be synthesized.
- examples of monofunctional monomers having an acryloyloxy group or a methacryloyloxy group include 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and the like.
- examples of bifunctional monomers having acryloyloxy or methacryloyloxy groups include 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol diacrylate, ethylene glycol Dimethacrylate, neopentyldalycol diacrylate, neopentyldalycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, 3-methylpentanediol diacrylate, 3-methylpentanediol dimethacrylate Etc.
- Examples of other polyfunctional monomers having an acryloyloxy group or a methacryloyloxy group include trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pen erythritol triacrylate, pentaerythritol trimethacrylate, pen Examples include erythritol tetraacrylate, pen erythritol tetramethacrylate, dipentaerythritol 1 ⁇ 1 pentene acrylate, dipentaerythritol pentamethacrylate, dipentyl erythritol hexaacrylate, dipentyl erythritol hexyl acrylate.
- the content of the crosslinkable group in the polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain having the crosslinkable group in the molecule is usually 0.1 to 30% by weight, Preferably it is 0.5 to 20% by weight, more preferably 1 to 10% by weight.
- the cross-linking agent include those having a polystyrene-equivalent weight average molecular weight of 200 or less and having two or more cross-linkable groups. Examples thereof include an acryloxy group or a methacryloyloxy group.
- bifunctional monomer having the above compounds other acryloyloxy groups or methacryloyloxy
- polyfunctional monomer having a silyl group examples include the above-mentioned compounds, rispenite erythritol octaacrylate (TPEA), and the like.
- TPEA rispenite erythritol octaacrylate
- crosslinking reaction of a polymer having a crosslinkable group or a crosslinking agent include reactions that occur by heating, irradiation with light, electron beam or the like. The reaction may be performed in the presence of a thermal polymerization initiator, a photopolymerization initiator, a thermal polymerization initiation assistant, a photopolymerization initiation assistant, or the like.
- the heating temperature is not particularly limited as long as it is lower than the temperature at which the characteristics are degraded by decomposition of the material, but is, for example, 50 ° C to 300 ° C, 100. C to 250 ° C is preferred.
- a thermal polymerization initiator that can be used in combination, those generally known as radical polymerization initiators can be used.
- 2, 2′-azobisi Azo compounds such as sobutyronitrile, 2,2, -azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile); benzoylperoxide, lauroyl And organic peroxides such as beloxide, t-butylperoxypivalate, 1,1,1bis (t-butylperoxy) cyclohexane; and hydrogen peroxide.
- the peroxide may be used together with a reducing agent to form a redox initiator.
- Each of these thermal polymerization initiators can be used alone or in combination of two or more.
- the reaction temperature when the thermal polymerization initiator is used in combination is, for example, 40 ° ( ⁇ 250 ° C, preferably 50 ° C to 200 ° C.
- ultraviolet light is 0.0 ImW.
- Irradiation with an irradiation intensity of / cm 2 or more is performed for 1 second to 3600 seconds, preferably 30 seconds to 600 seconds.
- the photopolymerization initiator include an active radical generator that generates an active radical when irradiated with light, and an acid generator that generates an acid.
- Examples of the active radical generator include a acetophenone photopolymerization initiator, a benzoin photopolymerization initiator, a benzophenone photopolymerization initiator, a thixanthone photopolymerization initiator, and a triazine photopolymerization initiator.
- Examples of the acid generator include compounds that generate an acid directly or indirectly upon irradiation with ultraviolet rays, far ultraviolet rays, electron beams, X-rays, and the like, for example, described in JP-A-4 1 1 6 3 5 52 Examples thereof include trihalomethyltriazine compounds and disulfone compounds described in JP-A No. 5 7 7 7 7. These photopolymerization initiators can be used alone or in combination of two or more.
- the light emitting layer is preferably formed between a cathode and a hole transport layer containing a polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain.
- a single molecule having functions such as a hole transport function, an electron transport function, a recombination function, and a light emission function may be used.
- Two or more types of molecules having the same or a plurality of types of molecules having the same function may be used in combination.
- the luminescent material may be a low molecule or a polymer.
- Examples of a method for forming a light emitting layer containing these include (co) evaporation and film formation from a solution. If the luminescent material is soluble in a solvent, a film-forming method from a solution can be used, and if it is evaporated in a vacuum, a vapor-depositing method can also be used.
- a vapor-depositing method As the luminescent material contained in the light emitting layer, “Organic EL Display” (Co-authored by Shizuo Tokito, Chiba Adachi, Hideyuki Murata, Ohm Co., Ltd., 2004, 1st edition, 1st edition) 1 7-48, The fluorescent materials or triplet light-emitting materials described on pages 83 to 99 and pages 101 to 120 can be used.
- low-molecular fluorescent materials include naphthalene derivatives, anthracene and derivatives thereof, perylene and derivatives thereof, polymethine series, xanthene. , Coumarin and cyanine dyes, metal complexes of 8-hydroxyquinoline, metal complexes of 8-hydroxyquinoline derivatives, aromatic amines, tetraphenyl oral pens and their derivatives, tetraphenylbutagen and its derivatives Etc. can be used. Specifically, for example, known ones such as those described in JP-A-57-51781 and JP-A-59-194393 can be used.
- triplet light-emitting complexes that are triplet light-emitting materials include Ir (ppy) 3 , Btp 2 Ir (acac), whose central metal is iridium, PtOEP whose central metal is platinum, and europium as the central metal.
- the light-emitting material used in the present invention may be a polymer compound, for example, any of an alternating copolymer, a random polymer, a block polymer, or a graft copolymer.
- a high molecular compound having an intermediate structure for example, a random copolymer having a blocking property may be used. From the standpoint of high charge transport performance and, as a result, high luminous efficiency, low driving voltage, and long life, random copolymers with block properties that are more blocky than complete random copolymers, block copolymers A coalescence or a graph copolymer is preferred.
- a polymer compound having a branched main chain and three or more terminal portions, and so-called dendrimers are also included.
- the main chain contains a repeating unit composed of the above aromatic amine skeleton.
- a polymer compound is preferred.
- the ratio of the repeating unit is 0.1 mol% or more and less than 30 mol% with respect to all repeating units in the high molecular compound. It is preferable. If it is less than 0.1 mol%, sufficient hole injection properties may not be obtained. If it is 30 mol% or more, light may not be emitted, but holes may reach the cathode as the counter electrode, resulting in a decrease in luminous efficiency.
- the ratio is 0.5 mol% or more and 10 mol% or less with respect to all the repeating units in the polymer compound, so that an organic electroluminescent device having higher luminous efficiency can be obtained.
- the repeating unit comprising the aromatic amine skeleton the repeating unit represented by the above formula (5) can be used.
- the organic EL device of the present invention when the luminescent material contains at least one repeating unit comprising the aromatic amine skeleton, at least one of the repeating units represented by the general formula (8) is mainly used together with this. Inclusion in the chain is preferable from the viewpoint of device characteristics such as maximum luminous efficiency and device lifetime.
- the definition, examples, etc. of the repeating unit represented by the general formula (8) are as described above.
- the light-emitting material used in the present invention is a polymer having a polystyrene-equivalent number average molecular weight of 1 X 10 3 to 1 X 1 0 8 from the viewpoint of lifetime characteristics of the organic electoluminescence device of the present invention. It is preferably a compound, more preferably a polymer compound having a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 to 1 ⁇ 10 6 .
- a repeating unit comprising an aromatic amine skeleton in the main chain examples thereof include the same methods as those exemplified for the method for synthesizing the polymer compound containing.
- the organic layer in the organic EL device of the present invention may further include an electron transport layer.
- well-known materials can be used as the material for the electron transport layer. Examples thereof include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyananthraquinodimethane and derivatives thereof, fluorenone derivatives, And enyldisyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, and polyfluorene and derivatives thereof.
- the organic EL device of the present invention at least a portion in contact with the organic layer on the surface of the anode is treated with the organic compound represented by the general formula (1) or a layer in contact with the anode constituting the organic layer.
- the organic compound represented by the general formula (1) a layer in contact with the anode constituting the organic layer.
- the organic layer between the hole-injecting electrode (referred to as the anode) and the electron-injecting electrode (referred to as the cathode) includes the hole injection layer, hole transport layer, light emitting layer, electron transport layer, and electron injection layer. It can be appropriately selected and laminated.
- Z indicates that the layers described on both sides of this symbol or layers and electrodes are stacked.
- the hole transport layer, the light emitting layer, and the electron transport layer may be one layer, or two or more layers having the same function may be stacked.
- Examples of materials that can be used in the organic layer in the organic electroluminescent device of the present invention include charge transporting materials and luminescent materials used in low molecular organic electroluminescent devices and high molecular organic electroluminescent devices. Is done.
- examples of light emission colors include intermediate colors and white.
- a material that emits light of three primary colors is preferably used for a full color element, and a material that emits light of white or intermediate color is preferably used for a planar light source.
- the total thickness of the organic layer varies depending on the material used, and may be adjusted so that the driving voltage, luminous efficiency, and device lifetime are appropriate. 30 nm to l « ⁇ , preferably It is 40 nm to 500 nm, and more preferably 60 nm to 400 nm.
- the thickness of each layer included in the organic layer is appropriately selected so that the light emission efficiency and the driving voltage are as desired, but is generally 5 nm to 200 nm.
- the thickness of the hole transport layer containing a polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain is exemplified by 10 to 300 nm, and preferably 20 to 150 nm. is there.
- the thickness of the light emitting layer that emits light by recombination of holes and electrons is exemplified by 5 to 300 nm, preferably 30 to 200 nm, and more preferably 40 to 150 nm.
- Examples of the thickness of the hole blocking layer include 5 to 50 nm, and preferably 10 to 30 nm.
- the thickness of the electron transport layer is exemplified by 10 to 100 nm, and preferably 20 to 80 nm.
- a method for forming these layers in addition to vacuum processes such as vacuum deposition, cluster one deposition, and molecular beam deposition, those that can form soluble emulsions are formed by the coating method or the printing method.
- a method is illustrated.
- a hole transport layer containing a polymer compound containing a repeating unit comprising an aromatic amine skeleton in the main chain a light emitting layer that emits light by recombination of holes and electrons, and an electron transport layer
- a method of forming a film from a solution is used.
- Examples of the method for forming a film from a solution include a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coat method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, Coating methods such as screen printing, flexographic printing, offset printing, inkjet printing, nozzle coating, and capillary coating can be used.
- a printing method such as a screen printing method, a flexographic printing method, an offset printing method, and an ink jet printing method is preferable because pattern formation and multicolor coating are easy.
- Ink is usually used for the method of forming a film from the above solution.
- This ink A polymer compound containing a repeating unit comprising an aromatic amine skeleton in the main chain and a solvent.
- the solvent is not particularly limited, but can dissolve or uniformly disperse components other than the solvent constituting the ink, that is, a polymer compound containing a repeating unit composed of an aromatic amine skeleton in the main chain, a luminescent material, and the like. I like things.
- the solvent include chlorine-based solvents such as black mouth form, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, black mouth benzene, and o-dichloro mouth benzene; ethers such as tetrahydrofuran and dioxane.
- Solvents aromatic hydrocarbon solvents such as toluene and xylene; aliphatics such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane Hydrocarbon solvents; cane solvents such as acetone, methyl ethyl ketone, cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosol acetate; ethylene glycol, ethylene glycol monobutyl ether , Ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, di Polyoxygen alcohols and their derivatives such as toxetane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexan
- the said solvent may be used individually by 1 type, or may use 2 or more types together.
- aromatic hydrocarbons from the viewpoints of high molecular weight compounds containing repeating units consisting of an aromatic amine skeleton in the main chain, solubility of luminescent materials, uniformity during film formation, viscosity characteristics, etc.
- Solvents aliphatic hydrocarbon solvents, ester solvents, ketone solvents are preferred, toluene, xylene, ethylbenzene, jetylbenzene, trimethylbenzene, n-propylbenzene, i-propylbenzene, n-butylbenzene, i Butylbenzene, s-butylbenzene, anisole, ethoxybenzene, 1-methylnaphthalene, cyclohexane, cyclohexanone, cyclohexyl Benzene, Bicyclohexyl, Cyclohexenylcyclohexanone, n_Hexylcyclohexane, n-Hexylcyclohexane, 2-Propylcyclohexanone, 21-Heptanone, 31-Heptanone, 4-Heptone Even non, 2-octanone, 2-nonanone, 2-decanone
- the ratio of the solvent in the ink is 1% by weight to 99.9% by weight with respect to the solute (that is, the total amount of the polymer compound containing a repeating unit having an aromatic amine skeleton in the main chain and the luminescent material). %, Preferably 60% to 99.5% by weight, and more preferably 80% to 99.0% by weight.
- the viscosity of the ink varies depending on the printing method, but in the case of ink that passes through the ejection device, such as the inkjet printing method, the viscosity is 1 at 25 ° C in order to prevent clogging and flight bending during ejection. It is preferably in the range of ⁇ 2 OmPa ⁇ s.
- an organic electroluminescence device can be constructed with a structure in which the light emitting layer is laminated with the charge injection layer or the charge transport layer.
- hole transporting materials, electron transporting materials, and light-emitting materials that are polymer compounds include WO 99/13692 publication specification, W099 no 48 160 publication specification, GB 2340304 A, WO 00/53656 published specification, WOO 1Z19834 published specification, WO 00/55927 published specification, GB23 48316, WO00 / 46321 published specification, WO 00/06665 published specification, WO 99/54943 published specification, WQ99Z54385 published specification , US 5777070, WO 98/06773 published specification, WO97Z05184 published Specification, WO 00/35987 published specification, WOO 0/53655 published specification, WO 01/34722 published specification, WO 99/24526 published specification, WO 00/22027 published specification, W00 / 22026 published Specification, WO 98/271 36 published specification, US 573636, WO 98 21262 published specification, US 5 741 921, WO 97/09394
- Po Illustrative examples are rearylene, derivatives and copolymers thereof, primary alkylene vinylene, derivatives and copolymers thereof, and (co) polymers of aromatic amines and derivatives thereof.
- the light emitting material and the charge transporting material may be used in combination with the light emitting material or charge transporting material for the low molecular weight organic electoluminescence device described above.
- the low molecular weight material and the polymer material can be used in combination.
- a metal complex having an organic ligand can be used in combination.
- a combination with a low-molecular fluorescent material or a phosphorescent material known as a so-called triplet light-emitting complex is effective.
- the central metal of the metal complex having an organic ligand that is a light-emitting material include aluminum, zinc, beryllium, iridium, platinum, gold, europium, and terbium.
- An insulating layer of 1 Onm or less may be provided in contact with the cathode. As a material of the insulating layer, W
- Metal fluorides, metal oxides, organic insulating materials, and the like Metal fluorides, metal oxides, organic insulating materials, and the like. Metal fluorides and metal oxides such as alkali metals or alkaline earth metals are preferable.
- a vacuum deposition method is exemplified as a method for forming the inorganic compound used for the insulating layer.
- the substrate for forming the organic electoluminescence device of the present invention may be any substrate as long as it does not change when forming each layer of the electrode, for example, a substrate of glass, plastic, polymer film, silicon or the like. Is done.
- the electrode closer to the substrate and the opposite electrode be transparent or translucent.
- transparent means that the ratio (transmittance) of transmitted light intensity to incident light intensity when light having a wavelength of 7500 to 400 nm passes through the electrode is 90% to 100%. It means that.
- “Semi-transparent” means that the transmittance is 40% or more and less than 90%.
- the anode side is preferably transparent or translucent.
- a conductive metal oxide, a translucent metal, or the like is used as the material of the anode. Specifically, indium oxide, zinc oxide, tin oxide, and their composites such as indium tin oxide (ITO), indium / zinc / oxide conductive glass (NESA, etc.), gold Platinum, silver, copper, and the like are used, and ITO, indium zinc oxide, and tin oxide are preferable.
- an organic transparent conductive film such as polyaniline and a derivative thereof, polythiophene and a derivative thereof may be used.
- the materials for the anode may be used singly or in combination of two or more.
- the film thickness of the anode can be appropriately selected in consideration of light transmittance and electrical conductivity, and is, for example, 10 nm to 10 m, preferably 20 nm to 1 m. More preferably, it is 50 nm to 500 nm. Examples of the method for producing the anode include vacuum deposition, sputtering, ion plating, and plating.
- the cathode material preferably has a low work function, for example, alkali metals such as lithium, sodium, potassium, rubidium, and cesium, beryllium, magnesium, calcium, strontium, and barium.
- Alkaline earth metals such as aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and two or more alloys thereof, or of them
- gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin's alloy, graphite, graphite intercalation compound, etc. are used.
- alloys include magnesium silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, calcium-aluminum alloy, and the like. I can get lost.
- the cathode may be a single layer or two or more layers. Further, the cathode material may be used alone or in combination of two or more.
- the thickness of the pole can be appropriately adjusted in consideration of electric conductivity and durability, for example, 10 nm to l 0 / m, preferably 20 nm to L: More preferably, it is 50 nm to 500 nm.
- a method such as the Nate method is used. Between the cathode and the organic layer, a layer made of a conductive polymer compound, a layer made of a metal oxide, a metal fluoride, an organic insulating material, etc. (usually a layer with an average film thickness of 2 nm or less) ) May be provided. After the cathode is fabricated, a protective layer for protecting the organic electoluminescence device may be attached.
- a protective layer and / or a protective cover in order to protect the device from the outside.
- a polymer compound, metal oxide, metal nitride, metal nitride oxide, metal fluoride, metal boride and the like can be used.
- a glass plate, a plastic plate having a low water permeability treatment on the surface, or the like can be used. Preferably used. If the space is maintained by using a spacer, it is easy to prevent the element from being damaged.
- the cathode can be prevented from being oxidized, and a manufacturing process can be performed by installing a desiccant such as barium oxide or calcium oxide in the space. This makes it easy to control the moisture adsorbed by the degrading of the element performance. Of these, it is preferable to take one or more of these measures.
- the organic electoluminescence device of the present invention can be used as a planar light source, a segment display device, a dot matrix display device, a pack light of a liquid crystal display device, and the like.
- the planar anode and cathode may be arranged so as to overlap each other.
- a mask provided with a pattern-like window on the surface of the planar light-emitting element is used.
- a method of installing a mask a method of forming an organic material layer of a non-light emitting portion extremely thick to make it substantially non-light emitting, and a method of forming either the anode or the cathode, or both electrodes in a pattern.
- a segment-type display element that can display numbers, letters, simple symbols, etc. by forming a pattern with any of these methods and arranging several electrodes independently to enable On ZO FF Is obtained.
- both the anode and the cathode may be formed in stripes and arranged so as to be orthogonal to each other. Partial color display and multi-color display are possible by coating different types of polymers with different emission colors or by using color filters or fluorescence conversion filters.
- the dot matrix element may be either passive drive or active drive combined with a thin film transistor using amorphous silicon or low-temperature polysilicon. These display elements can be used as display devices for computers, televisions, mobile terminals, mobile phones, car navigation systems, video camera viewfinders, and the like.
- planar light-emitting element is thin and self-luminous, and can be suitably used as a planar light source for 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 or display device.
- the obtained polymer compound A is obtained from the charged raw materials, using the following structural formula:
- repeating unit represented by the formula (1) has a 1: 1 (molar ratio).
- a glass substrate with an ITO film with a thickness of 150 nm was subjected to UV ozone treatment for 15 minutes by the sputtering method. Thereafter, the glass substrate is attached to a silane cut product made by F 1 uka. It was reacted with 1H, 1H, 2H, 2H-perfluorooctyltrichlorosilane. 1H, 1 H, 2H, 2 H—perfluorooctyltrichlorosilan 500 1 and 25 mi octane were mixed and the substrate was allowed to react by immersing in the solution for 22 hours.
- This glass substrate was spin-coated with the polymer compound A in a xylene solution to form a film having a thickness of 10 nm. Heat treatment was performed at 180 ° C. for 15 minutes on a hot plate. Next, the polymer compound B was spin-coated in the form of a xylene solution on the polymer compound A thus formed to form a film having a thickness of 75 nm. Thereafter, the solvent was removed by heating at 130 ° C for 60 minutes on a hot plate in a nitrogen atmosphere. The thin film thus prepared was introduced into a vacuum deposition machine, and an EL device was fabricated by depositing about 5 nm of metal palladium and then about 100 nm of aluminum as a cathode. Degree of vacuum metal vapor deposition was initiated after reaching below 1 X 10- 4 P a.
- the EL element obtained above was set to a drive current of 2 mA, then driven at a constant current, and the change in luminance over time was measured. As a result, the luminance dropped to 80% after 1.71 hours and halved after 4.3 hours.
- Example 1 was the same as Example 1 except that the glass substrate was not reacted with 1H, 1H, 2H, 2H-perfluorooctyltrichlorosilane, which is a silane coupling agent manufactured by F1uka. To produce organic-elect mouth luminescence elements did. When voltage was applied to the resulting device, blue light emission having a peak wavelength of 460 nm derived from polymer compound B was observed, and the light emission starting voltage at 1 cd / cm 2 was 6.4 V. The maximum luminous efficiency was 0.10 cd / A, and the current density at 9 V was 70 mAZcm 2 . When driving at a constant current at a current of 2 mA, the brightness dropped to 80% after 0.08 hours and halved after 1.3 hours.
- 1H, 1H, 2H, 2H-perfluorooctyltrichlorosilane which is a silane coupling agent manufactured by F1uka.
- Example 1 an organic electoluminescence device was produced in the same manner as in Example 1 except that the polymer compound A was not formed into a film.
- blue light emission having a peak wavelength of 460 nm derived from the polymer compound B was exhibited, and the light emission starting voltage at 1 cd / cm 2 was 3.4V.
- the maximum luminous efficiency was 2.72 c dZA, and the current density at 9 V was 242 mA / cm 2 .
- the brightness dropped to 80% after 0.38 hours and halved after 0.96 hours.
- Example 1 the polymer substrate A was produced without reacting the glass substrate with 1 H, 1H, 2H, 2 H-perfluorooctyltrichlorosilane, which is a silane coupling agent manufactured by F 1uka.
- An organic electroluminescence element was produced in the same manner as in Example 1 except that no film was formed.
- blue light emission having a peak wavelength of 460 nm derived from the polymer compound B was exhibited, and the light emission starting voltage at which 1 cdZcm 2 was obtained was 4.7 V.
- the maximum luminous efficiency was 1.44 cd / A, and the current density at 9 V was 88 mA / cm 2 .
- the brightness dropped to 80% after 0.01 hour and halved after 0.04 hour.
- a glass substrate with an ITO film with a thickness of 150 nm was subjected to UV ozone treatment for 15 minutes by the sputtering method. Thereafter, the glass substrate was reacted with 1 H, 1H, 2H, 2H-perfluorooctyltrichlorosilane, which is a silane coupling agent manufactured by F1uka.
- 1 H, 1H, 2H, 2H—perfluorooctyltrichlorosilane 50 1 and 25 ml of octane were mixed and reacted by immersing the substrate in the solution for 17 hours.
- This glass substrate was spin-coated with polymer compound A in the form of a xylene solution to form a film having a thickness of 20 nm. Heat treatment was performed on a hot plate at 180 ° C. for 60 minutes. Next, the polymer compound C was spin-coated in the form of a xylene solution on the film-formed polymer compound A to form a film having a thickness of 75 nm. Then, the solvent was removed by heating on a hot plate in a nitrogen atmosphere at 130 ° (: for 10 minutes. The thin film thus prepared was introduced into a vacuum deposition machine, and a metal barrier was formed to a thickness of about 5 nm as a cathode. to produce an EL element by depositing aluminum to a thickness of about 100 nm. in addition, to Hirakidai vapor deposition of metal after the degree of vacuum reached below 1 X 10- 4 P a.
- the current value of the EL device obtained above was set so that the drive current was 2 mA, and then the device was driven at a constant current, and the change in luminance over time was measured. As a result, the luminance decreased to 80% after 0.9 hours and halved after 6.8 hours.
- Example 2 an organic electroluminescent device was produced in the same manner as in Example 2 except that ⁇ 1 NPD manufactured by Aldrich Co. was formed by vacuum deposition instead of forming polymer compound A. The vacuum deposition of ⁇ -NPD was started after the degree of vacuum reached 5 XI 0_ 4 Pa or lower. When voltage was applied to the resulting device, blue light emission having a peak wavelength of 450 nm derived from polymer compound C was observed, and the light emission starting voltage at 1 cd / cm 2 was 3.4 V. The maximum luminous efficiency was 2.20 cd / A, and the current density at 9 V was 128 mAZcm 2 . When driven at a constant current at a current of 2 mA, the brightness dropped to 80% after 0.25 hours, and halved after 1.1 hours.
- Example 2 the polymer substrate A is formed without reacting the glass substrate with 1H, 1H, 2H, 2H-perfluorooctyltrichlorosilane, which is a silane coupling agent manufactured by F1uka. Instead, an organic electoluminescence device was produced in the same manner as in Example 2 except that ⁇ -NPD made by Aldrich was formed by vacuum deposition. When voltage was applied to the resulting device, blue light emission having a peak wavelength of 45 Onm derived from the polymer compound C was exhibited, and the light emission starting voltage at 1 cd / cm 2 was 5.8V. The maximum luminous efficiency current density at 0. 51 CDZA, 9V was 55 mAZcm 2. When driven at a constant current at a current of 2 mA, the brightness dropped to 80% after 0.06 hours and halved after 0.01 hours.
- a glass substrate with an ITO film with a thickness of 150 nm was subjected to UV ozone treatment for 15 minutes by the sputtering method. Thereafter, the glass substrate was reacted with 1H, 1H, 2H, 2H-perfluorooctyltrichlorosilane, which is a silane coupling agent manufactured by F 1 Uka.
- 1H, 1H, 2H, 2H—Perfluorooctyltrichlorosilane 500 1 and 25 ml of octane are mixed, and the substrate is immersed in the solution for 17 hours. It was made to react.
- polymer compound A in the xylene solution state is mixed with dipentaerythritol hexacrylate (Nippon Kayaku Co., Ltd., trade name ⁇ RAD DPHA) as a cross-linking agent to obtain a coating solution (polymer compound)
- the ratio of the cross-linking agent to the total of A and the cross-linking agent was 20% by weight.
- the polymer compound A was heat-treated on a hot plate for 180 and 60 minutes, and polymer compound A was crosslinked with dipentylerythritol hexacrylate to obtain a thin film comprising a crosslinked product of polymer compound A.
- polymer compound C was spin-coated in a xylene solution to form a film having a thickness of 75 nm. Then, the solvent was removed by heating on a hot plate in a nitrogen atmosphere for 130 minutes for 10 minutes.
- the thin film thus prepared was introduced into a vacuum evaporation machine, and metal EL was fabricated by depositing metal barium at about 5 nm and aluminum at about 100 nm as the cathode. The vacuum degree was initiated vapor deposition of metal after reaching below 1 X 10- 4 Pa. (EL element evaluation)
- the current value of the EL device obtained above was set so that the drive current would be 2 mA, then it was driven at a constant current, and the change in luminance over time was measured. As a result, the brightness decreased to 80% after 0.66 hours.
- Example 3 An organic electoluminescence device was produced in the same manner as in Example 3 except that the thickness of the coating solution was changed from 80 nm to 20 nm.
- the current value of the EL device obtained above was set so that the drive current would be 2 mA, then it was driven at a constant current, and the change in luminance over time was measured. As a result, the brightness dropped to 80% after 0.56 hours.
- the organic electoluminescence device of the present invention is easy to manufacture because it uses an alternative material of PED0T: PSS from the viewpoint of manufacturing processes such as coating and film formation.
- the organic electoluminescence device of the present invention usually has a long lifetime and also has a high luminous efficiency.
- the organic electoluminescence device of the present invention can be preferably used in devices such as a segment type display device and a dot matrix flat panel display. It can also be used as a curved or flat light source for backlight or illumination of liquid crystal displays.
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Abstract
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US12/601,946 US20100171104A1 (en) | 2007-05-30 | 2008-05-27 | Organic electroluminescence device and display using the device |
EP08753126A EP2173141A4 (en) | 2007-05-30 | 2008-05-27 | ORGANIC ELECTROLUMINESCENT DEVICE AND DISPLAY DEVICE USING THE DEVICE |
CN2008800214520A CN101682955B (zh) | 2007-05-30 | 2008-05-27 | 有机电致发光元件及使用该元件的显示装置 |
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US12004369B2 (en) | 2009-05-21 | 2024-06-04 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting device |
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JP2010278157A (ja) * | 2009-05-27 | 2010-12-09 | Sumitomo Chemical Co Ltd | 有機エレクトロルミネッセンス素子及びその製造方法 |
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- 2008-05-27 EP EP08753126A patent/EP2173141A4/en not_active Withdrawn
- 2008-05-27 KR KR1020097027021A patent/KR20100024961A/ko not_active Application Discontinuation
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- 2008-05-27 CN CN2008800214520A patent/CN101682955B/zh not_active Expired - Fee Related
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US20110207039A1 (en) * | 2010-02-23 | 2011-08-25 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor, process cartridge, image forming apparatus, cured film, and organic electroluminescent device |
US8859173B2 (en) * | 2010-02-23 | 2014-10-14 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor, process cartridge, image forming apparatus, cured film, and organic electroluminescent device |
Also Published As
Publication number | Publication date |
---|---|
CN101682955A (zh) | 2010-03-24 |
US20100171104A1 (en) | 2010-07-08 |
EP2173141A4 (en) | 2011-09-21 |
KR20100024961A (ko) | 2010-03-08 |
EP2173141A1 (en) | 2010-04-07 |
TW200910662A (en) | 2009-03-01 |
CN101682955B (zh) | 2013-03-13 |
JP5248910B2 (ja) | 2013-07-31 |
JP2009010343A (ja) | 2009-01-15 |
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