JP2016000724A - 複素環化合物、発光素子、発光装置、電子機器、および照明装置 - Google Patents
複素環化合物、発光素子、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP2016000724A JP2016000724A JP2015100795A JP2015100795A JP2016000724A JP 2016000724 A JP2016000724 A JP 2016000724A JP 2015100795 A JP2015100795 A JP 2015100795A JP 2015100795 A JP2015100795 A JP 2015100795A JP 2016000724 A JP2016000724 A JP 2016000724A
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- heterocyclic compound
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 76
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 229910052799 carbon Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000000732 arylene group Chemical group 0.000 claims abstract description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- -1 2-fluorenyl group Chemical group 0.000 claims description 38
- 239000000758 substrate Substances 0.000 claims description 30
- 150000002894 organic compounds Chemical class 0.000 claims description 20
- 150000001721 carbon Chemical class 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 172
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- 125000005595 acetylacetonate group Chemical group 0.000 description 8
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- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 4
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 3
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- SUFKFXIFMLKZTD-UHFFFAOYSA-N [Tb+3].N1=CC=CC2=CC=C3C=CC=NC3=C12 Chemical compound [Tb+3].N1=CC=CC2=CC=C3C=CC=NC3=C12 SUFKFXIFMLKZTD-UHFFFAOYSA-N 0.000 description 1
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- 125000005264 aryl amine group Chemical group 0.000 description 1
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- 238000005452 bending Methods 0.000 description 1
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- 230000002457 bidirectional effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- HTJWUNNIRKDDIV-UHFFFAOYSA-N bis(1-adamantyl)-butylphosphane Chemical compound C1C(C2)CC(C3)CC2CC13P(CCCC)C1(C2)CC(C3)CC2CC3C1 HTJWUNNIRKDDIV-UHFFFAOYSA-N 0.000 description 1
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- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
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- JRUYYVYCSJCVMP-UHFFFAOYSA-N coumarin 30 Chemical compound C1=CC=C2N(C)C(C=3C4=CC=C(C=C4OC(=O)C=3)N(CC)CC)=NC2=C1 JRUYYVYCSJCVMP-UHFFFAOYSA-N 0.000 description 1
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- 239000003822 epoxy resin Substances 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 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
- 229910052746 lanthanum Inorganic materials 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
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- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
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- AJNJGJDDJIBTBP-UHFFFAOYSA-N n-(9,10-diphenylanthracen-2-yl)-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AJNJGJDDJIBTBP-UHFFFAOYSA-N 0.000 description 1
- RVHDEFQSXAYURV-UHFFFAOYSA-N n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)C=C1 RVHDEFQSXAYURV-UHFFFAOYSA-N 0.000 description 1
- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- 229960000286 proflavine Drugs 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
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Abstract
【解決手段】本発明の一態様は、一般式(G1)で表される複素環化合物。
(但し、一般式(G1)中、A1およびA2は、窒素または水素と結合する炭素を表し、A1およびA2の少なくとも一方は窒素を表す。また、Arは、置換もしくは無置換の炭素数6〜18のアリーレン基を表し、Bは、置換もしくは無置換のフルオレニル基を表す。また、R1は、水素、炭素数1〜6のアルキル基、炭素数6〜13のアリール基のいずれかを表す。)
【選択図】なし
Description
(但し、一般式(G1)中、A1およびA2は、窒素または水素と結合する炭素を表し、A1およびA2の少なくとも一方は窒素を表す。また、Arは、置換もしくは無置換の炭素数6〜18のアリーレン基を表し、Bは、置換もしくは無置換のフルオレニル基を表す。また、R1は、水素、炭素数1〜6のアルキル基、炭素数6〜13のアリール基のいずれかを表す。)
(但し、一般式(α)中、R11〜R19は、それぞれ独立に、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基を表す。)
(但し、一般式(β)中、R17およびR18は、それぞれ独立に、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基を表す。)
本実施の形態では、本発明の一態様である複素環化合物について説明する。なお、本発明の一態様である複素環化合物は、複素環骨格(ピリミジン骨格、またはトリアジン骨格)とフルオレン骨格とが、アリーレン基を介して結合した構造を有する化合物である。
(但し、一般式(G1)中、A1およびA2は、窒素または水素と結合する炭素を表し、A1およびA2の少なくとも一方は窒素を表す。また、Arは、置換もしくは無置換の炭素数6〜18のアリーレン基を表し、Bは、置換もしくは無置換のフルオレニル基を表す。また、R1は、水素、炭素数1〜6のアルキル基、炭素数6〜13のアリール基のいずれかを表す。)
(但し、一般式(α)中、R11〜R19は、それぞれ独立に、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基を表す。)
(但し、一般式(β)中、R17およびR18は、それぞれ独立に、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基を表す。)
一般式(G1)で表される複素環化合物は、以下のような簡便な合成スキームにより合成できる。例えば、下記スキーム(a)に示すように、ピリミジンまたはトリアジン誘導体のハロゲン化合物(A1)とフルオレン誘導体で置換されたアリールボロン酸化合物(A2)とを反応させることにより得られる。
本実施の形態では、本発明の一態様である複素環化合物をEL材料として用いることができる発光素子の一態様について図1を用いて説明する。
フェニル)ベンズオキサゾラト]亜鉛(略称:Zn(BOX)2)、ビス[2−(2−ヒドロキシフェニル)ベンゾチアゾラト]亜鉛(略称:Zn(BTZ)2)などの金属錯体を用いることができる。また、2−(4−ビフェニリル)−5−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾール(略称:PBD)、1,3−ビス[5−(p−tert−ブチルフェニル)−1,3,4−オキサジアゾール−2−イル]ベンゼン(略称:OXD−7)、3−(4’−tert−ブチルフェニル)−4−フェニル−5−(4’’−ビフェニル)−1,2,4−トリアゾール(略称:TAZ)、3−(4−tert−ブチルフェニル)−4−(4−エチルフェニル)−5−(4−ビフェニリル)−1,2,4−トリアゾール(略称:p−EtTAZ)、バソフェナントロリン(略称:BPhen)、バソキュプロイン(略称:BCP)、4,4’−ビス(5−メチルベンゾオキサゾール−2−イル)スチルベン(略称:BzOs)などの複素芳香族化合物も用いることができる。また、ポリ(2,5−ピリジンジイル)(略称:PPy)、ポリ[(9,9−ジヘキシルフルオレン−2,7−ジイル)−co−(ピリジン−3,5−ジイル)](略称:PF−Py)、ポリ[(9,9−ジオクチルフルオレン−2,7−ジイル)−co−(2,2’−ビピリジン−6,6’−ジイル)](略称:PF−BPy)のような高分子化合物を用いることもできる。ここに述べた物質は、主に1×10−6cm2/Vs以上の電子移動度を有する物質である。なお、正孔よりも電子の輸送性の高い物質であれば、上記以外の物質を電子輸送層114として用いてもよい。また、実施の形態1で示した本発明の一態様である複素環化合物を用いることもできる。
本実施の形態では、本発明の一態様である複素環化合物をEL材料としてEL層に用い、電荷発生層を挟んでEL層を複数有する構造の発光素子(以下、タンデム型発光素子という)について説明する。
本実施の形態では、本発明の一態様である複素環化合物をEL層に用いた発光素子を有する発光装置について説明する。
本実施の形態では、本発明の一態様である発光装置を適用して完成させた様々な電子機器の一例について、図4、図5を用いて説明する。
本実施の形態では、本発明の一態様である発光装置を適用した照明装置の一例について、図6を用いて説明する。
本実施例では、本発明の一態様である複素環化合物、4,6−ビス[3−(9,9−ジメチルフルオレン−2−イル)フェニル]ピリミジン(略称:4,6mFP2Pm)(構造式(100))の合成方法について説明する。なお、4,6mFP2Pmの構造を以下に示す。
まず、9,9−ジメチルフルオレン−2−ボロン酸ピナコールエステル7.8g(24mmol)、3−ブロモヨードベンゼン6.2g(22mmol)、炭酸ナトリウム5.0g(47mmol)、トルエン100mL、エタノール10mLを300mL三口フラスコに入れ、フラスコ内を窒素置換した。この混合物に、テトラキス(トリフェニルホスフィン)パラジウム(0)(略称:Pd(PPh3)4)0.42g(0.36mmol)を加え、80℃で10時間加熱撹拌した。得られた混合物に水を加え、再び水層をトルエンで抽出した。
2−(3−ブロモフェニル)−9,9−ジメチルフルオレン4.8g(14mmol)を300mL三口フラスコに入れ、フラスコ内を窒素置換した後、テトラヒドロフラン(THF)70mLを加え、−78℃で撹拌した。この混合溶液に、n−ブチルリチウム(1.58mol/Lヘキサン溶液)10mL(15mmol)を滴下し、−78℃で1.5時間撹拌した。この混合溶液に、ホウ酸トリメチル1.8mL(16mmol)を滴下し、20℃に昇温しながら18時間撹拌した。所定時間経過後、この混合溶液に1mol/L塩酸100mLを加え、室温で撹拌した。これにより、水層と有機層を含む混合溶液を得た。
3−(9,9−ジメチルフルオレン−2−イル)フェニルボロン酸1.9g(6.1mmol)、4,6−ジクロロピリミジン0.36g(2.4mmol)、炭酸ナトリウム1.3g(12mmol)、1,3−ジメチル−3,4,5,6−テトラヒドロ−2(1H)ピリミジノン(DMPU)25mL、水15mLを100mL丸底フラスコに入れフラスコ内をアルゴン置換した。この混合物にビス(トリフェニルホスフィン)パラジウム(II)ジクロリド17mg(0.020mmol)を加え、150℃、100Wの条件でマイクロ波を1時間照射して反応させた。
本実施例では、本発明の一態様である複素環化合物、4,6−ビス{3−[3−(9,9−ジメチルフルオレン−2−イル)フェニル]フェニル}ピリミジン(略称:4,6mFBP2Pm)(構造式(109))の合成方法について説明する。なお、4,6mFBP2Pmの構造を以下に示す。
3L三口フラスコに2−(3−ブロモフェニル)−9,9−ジメチルフルオレン130g(0.37mol)、4,4,4’,4’,5,5,5’,5’−オクタメチル−2,2’−ビ−1,3,2−ジオキサボロラン103g(0.41mol)、酢酸カリウム109g(1.1mol)、N,N−ジメチルホルムアミド(DMF)1.2Lを加えた。この混合物を、減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物に、酢酸パラジウム(II)2.5g(0.011mol)を加えた。この混合物を窒素気流下、100℃で5時間撹拌した。所定時間経過後、この混合物をろ紙上にセライト、アルミナの順に積層して吸引ろ過し、得られたろ液を濃縮して油状物を得た。この固体をエタノールで再結晶したところ、褐色固体118g、収率81%で得た。
100mL三口フラスコに4,6−ビス(3−クロロフェニル)ピリミジン1.0g(3.3mmol)、2−[3−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)フェニル]−9,9−ジメチルフルオレン2.9g(7.3mmol)、t−ブタノール0.70g(9.9mmol)、リン酸三カリウム5.6g(11mmol)、1,4−ジオキサン22mL加えた。この混合物を、減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物に、酢酸パラジウム(II)22mg(1.0mmol)、ジ(1−アダマンチル)−n−ブチルホスフィン(別名:cataCXium(登録商標) A 、Aldrich製)(略称:cataCXium)71g(2.0mmol)を加えた。
まず、ガラス製の基板800上に酸化珪素を含むインジウム錫酸化物(ITO−2)をスパッタリング法により成膜し、陽極として機能する第1の電極801を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
作製した発光素子1の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
本実施例で作製した発光素子2および発光素子3の素子構造を表3に示す。なお、発光素子2および発光素子3の第1の電極には、酸化珪素を含むインジウム錫酸化物(ITO−3)を用いてスパッタリング法により成膜し、形成した。また、発光素子3の正孔輸送層には、9−フェニル−9H−3−(9−フェニル−9H−カルバゾール−3−イル)カルバゾール(略称:PCCP)を用いた。また、発光素子2および発光素子3の発光層には、実施例2で合成した4,6mFBP2Pmを用いた。
作製した発光素子2および発光素子3の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
102 EL層
103 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
201 第1の電極
202(1) 第1のEL層
202(2) 第2のEL層
202(n−1) 第(n−1)のEL層
202(n) 第(n)のEL層
204 第2の電極
205 電荷発生層
205(1) 第1の電荷発生層
205(2) 第2の電荷発生層
205(n−2) 第(n−2)の電荷発生層
205(n−1) 第(n−1)の電荷発生層
301 素子基板
302 画素部
303 駆動回路部(ソース線駆動回路)
304a、304b 駆動回路部(ゲート線駆動回路)
305 シール材
306 封止基板
307 配線
308 FPC(フレキシブルプリントサーキット)
309 FET
310 FET
311 スイッチング用FET
312 電流制御用FET
313 第1の電極(陽極)
314 絶縁物
315 EL層
316 第2の電極(陰極)
317 発光素子
318 空間
800 基板
801 第1の電極
802 EL層
803 第2の電極
811 正孔注入層
812 正孔輸送層
813 発光層
814 電子輸送層
815 電子注入層
7100 テレビジョン装置
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7302 筐体
7304 表示パネル
7305 時刻を表すアイコン
7306 その他のアイコン
7311 操作ボタン
7312 操作ボタン
7313 接続端子
7321 バンド
7322 留め金
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作用ボタン
7404 外部接続部
7405 スピーカ
7406 マイク
7407 カメラ
8001 照明装置
8002 照明装置
8003 照明装置
8004 照明装置
9310 携帯情報端末
9311 表示パネル
9312 表示領域
9313 ヒンジ
9315 筐体
Claims (13)
- 一般式(G1)で表される複素環化合物。
(一般式(G1)中、A1およびA2は、窒素または水素と結合する炭素を表し、A1およびA2の少なくとも一方は窒素を表す。また、Arは、置換もしくは無置換の炭素数6〜18のアリーレン基を表し、Bは、置換もしくは無置換のフルオレニル基を表す。また、R1は、水素、炭素数1〜6のアルキル基、炭素数6〜13のアリール基のいずれかを表す。) - 請求項1において、
前記一般式(G1)中のBは、置換もしくは無置換の2−フルオレニル基である複素環化合物。 - 請求項1または請求項2において、
前記一般式(G1)中のBは、下記一般式(α)で表される複素環化合物。
(一般式(α)中、R11〜R19は、それぞれ独立に、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基を表す。) - 請求項1または請求項2において、
前記一般式(G1)中のBは、下記一般式(β)で表される複素環化合物。
(一般式(β)中、R17およびR18は、それぞれ独立に、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基を表す。) - 構造式(100)で表される複素環化合物。
- 構造式(109)で表される複素環化合物。
- 請求項1乃至請求項6のいずれか一に記載の複素環化合物を用いた発光素子。
- 一対の電極間にEL層を有し、
前記EL層は、請求項1乃至請求項6のいずれか一に記載の複素環化合物を有する発光素子。 - 一対の電極間にEL層を有し、
前記EL層は、発光層を有し、
前記発光層は、請求項1乃至請求項6のいずれか一に記載の複素環化合物を有する発光素子。 - 一対の電極間にEL層を有し、
前記EL層は、発光層を有し、
前記発光層は、3種以上の有機化合物を有し、
前記3種以上の有機化合物のうちの一は、
請求項1乃至請求項6のいずれか一に記載の複素環化合物である発光素子。 - 請求項7乃至請求項10のいずれか一に記載の発光素子と、
トランジスタ、または、基板と、
を有する発光装置。 - 請求項11に記載の発光装置と、
マイク、カメラ、操作用ボタン、外部接続部、または、スピーカと、
を有する電子機器。 - 請求項11に記載の発光装置と、
筐体、カバー、または、支持台を有する照明装置。
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CN105085409A (zh) | 2015-11-25 |
CN114039017A (zh) | 2022-02-11 |
JP2019186571A (ja) | 2019-10-24 |
JP7008666B2 (ja) | 2022-02-10 |
US10770660B2 (en) | 2020-09-08 |
JP2021052209A (ja) | 2021-04-01 |
JP7035158B2 (ja) | 2022-03-14 |
US20180198073A1 (en) | 2018-07-12 |
KR102509231B1 (ko) | 2023-03-10 |
US9923149B2 (en) | 2018-03-20 |
US20150340622A1 (en) | 2015-11-26 |
KR20150135097A (ko) | 2015-12-02 |
KR102457008B1 (ko) | 2022-10-19 |
JP6557056B2 (ja) | 2019-08-07 |
CN113549016A (zh) | 2021-10-26 |
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