JP5432106B2 - 高分子及びこれを含む有機発光素子 - Google Patents
高分子及びこれを含む有機発光素子 Download PDFInfo
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- JP5432106B2 JP5432106B2 JP2010228733A JP2010228733A JP5432106B2 JP 5432106 B2 JP5432106 B2 JP 5432106B2 JP 2010228733 A JP2010228733 A JP 2010228733A JP 2010228733 A JP2010228733 A JP 2010228733A JP 5432106 B2 JP5432106 B2 JP 5432106B2
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- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HJDKCHUESYFUMG-UHFFFAOYSA-N cycloocta-1,5-diene;nickel Chemical compound [Ni].C1CC=CCCC=C1 HJDKCHUESYFUMG-UHFFFAOYSA-N 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003824 heptacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC7=CC=CC=C7C=C6C=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 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
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YPJRZWDWVBNDIW-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-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
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 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
Classifications
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- C—CHEMISTRY; METALLURGY
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0683—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0688—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polyquinolines
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0683—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0694—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring, e.g. polyquinoxalines
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- 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
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
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- C08G2261/50—Physical properties
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
下記反応式2によって化合物(e)(フェノキサジンダイマー)を合成した。
4−ブロモフェノール50g(0.29mole)をアセトン(500mL)に溶解させた後。ここにK2CO3 48.4g(0.35mole)を添加した。次いで、前記混合物に1−ブロモオクタン73.3g(0.38mole)を添加して24時間還流させた。前記反応が完了した後、水:CHCl3=2:1体積比溶液で抽出してK2CO3を除去した。これにより収得した有機層をMgSO4で乾燥させた後、濃縮させ、ヘキサンを溶離液として使用してシリカゲルカラムクロマトグラフィーを実施した。ここで得た溶出液を減圧蒸留して未反応1−ブロモオクタンを除去して化合物(a)80g(収率:96%)を収得した。
前記化合物(a)18g(64mmol)、フェノキサジン10g(54mmol)、ナトリウムtert−ブトキシド7.4g(77mmol)、Pd2(dba)3[(Tris(dibenzylidineacetone)dipalladium(0))]0.61g(1.1mmol)、及びトリ(tert−ブチル)ホスフィン0.22g(1.1mmol)をキシレン250mLに溶解させた後、80℃で12時間反応させた。前記反応が完了した後、反応混合物を室温まで冷却させて、蒸溜水200mlを添加してキシレン:水=1:1(体積比)で抽出した。これより収得した有機層をMgSO4で乾燥させた後、濃縮して、トルエン:ヘキサン=1:2(体積比)を溶離液として使用してシリカゲルカラムクロマトグラフィーを実施した。ここで得た溶出液を濃縮、乾燥させて18.5g(収率:88%)の化合物(b)を収得した。
前記化合物(b)5g(13mmol)をCHCl3 150mLに溶解させた後、0℃に維持しつつ、化合物(b)に対して臭素1当量をゆっくりと添加した。薄膜クロマトグラフィー(TLC)によって出発物質がなくなったことを確認した後に、前記混合物に臭素添加を中止し、反応混合物を10分間攪拌後、反応を停止させた。前記反応混合物に少量のアセトンを添加して臭素をケンチングした後に水:CHCl3=2:1(体積比)を使用して抽出を実施した。収得した有機層をMgSO4で乾燥させた後、濃縮させて、MeOHで再沈殿させることによって6g(収率:85%)の化合物(c)を得た。化合物(c)の構造を1H−NMRを通じて確認した。その結果を以下に示す。
1H−NMR(300MHz、CDCl3):δ0.91(m、6H)、δ1.45(m、8H)、δ1.82(m、1H)、δ3.89(d、2H)、δ5.82(d、2H)、δ6.5〜7.5(m、9H)
シュレンクフラスコ(Schlenk flask)内部を数回真空化、窒素還流させて水分を完全に除去した後、ビス1,5−シクロオクタジエンニッケル880mg(3.2mmol)とビピリダル(bipyridal)500mg(3.2mmol)をグローブボックス(glovebox)内に投入した後、さらに数回フラスコ内部を真空化、窒素還流させた。次いで、窒素気流下で無水ジメチルフラン(DMF)10mlと1,5−シクロオクタジエン(COD)346mg(3.2mmol)、及び無水トルエン10mlを添加した。80℃で30分間攪拌させた後、前記化合物(c)0.746g(0.16mmol)をトルエン10mlに希釈して添加した。次いで、器壁に付いている物質をいずれも洗浄しつつ、トルエン10mlを添加した後、80℃で2時間攪拌させた。攪拌が完了した後、前記反応液の温度を60℃に降温した後、HCl:アセトン:メタノール=1:1:2溶液に注いで沈殿を形成させた。沈殿物をクロロホルムに溶解させた後、有機層をMgSO4で乾燥させた後、濃縮して、トルエン:ヘキサン=3:7(体積比)を溶離液として使用してシリカゲルカラムクロマトグラフィーを実施した。ここで得た溶出液を濃縮、乾燥させて0.5gの化合物(d)を収得した。化合物(d)の構造を1H−NMRを通じて確認した。その結果を以下に示す。
1H−NMR(300MHz、CDCl3):δ0.93(12H)、δ1.48(16H)、δ1.80(2H)、δ3.92(4H)、δ5.85(4H)、δ6.3〜7.7(18H)
前記化合物(d)0.5g(0.647mmol)をCHCl3に溶かした後、0℃に維持しつつ、臭素2.1当量をゆっくりと添加した。反応混合物を10分間攪拌後、反応を停止させた。前記反応混合物に少量のアセトンを添加して、臭素をケンチングした後、水:クロロホルム=2:1(体積比)を使用して抽出した。これにより収得した有機層を無水マグネシウムスルフェートで乾燥させた後、濃縮させて、メタノールに再沈殿させることによって580mg(収率:96%)の化合物(e)を得た。化合物(e)の構造を1H−NMRを通じて確認した。その結果を以下に示す。
1H NMR(300MHz、CDCl3)δ0.93(12H)、δ1.48(16H)、δ1.80(2H)、δ3.92(4H)、δ5.92(4H)、δ6.2〜7.9(18H)
下記反応式3によって高分子1を合成した。
下記反応式4によって高分子2を合成した。
下記反応式5によって高分子3を合成した。
アノードとしては、コーニング(Corning)15Ω/cm2(1200Å)ITOガラス基板を50mm×50mm×0.7mmの大きさに切って、イソプロピルアルコールと純水中で各5分間超音波洗浄した後、30分間UVオゾン洗浄して使用した。次いで、前記ITO膜上に伝導性バッファ層としてPEDOT:PSS(H.C.Stark社のAI4083)を約600の厚さにコーティングした後、200℃で約20分間熱処理した。次いで、前記合成例2で製造された高分子1(5mg)をトルエン1mlに溶解させて高分子溶液を収得し、この高分子溶液は、スピンコーティングの前に0.2μmフィルターでろ過した。これを前記伝導性バッファ層上にスピンコーティングして、200℃で10分間熱処理して正孔輸送層を形成した。前記正孔輸送層の厚さは、前記高分子溶液の濃度とスピン速度とを調節することによって、約300Åになるように調節した。前記正孔輸送層の上部に、DSA(燐光ホスト)及びTBPe(ドープ剤、3重量%)を真空蒸着して300Åの厚さの発光層を形成した。その後、前記発光層の上部にAlq3を真空蒸着して200Å厚さの電子輸送層を形成した。前記電子輸送層の上部にLiF80ÅとAl3000Åを順次に真空蒸着して、LiF/Al電極を形成して、有機発光素子を製作した。この際、蒸着時の膜の厚さ及び膜の成長速度は、クリスタルセンサーを用いた。
前記実施例1において、正孔輸送層形成のために高分子1を使用する代わりに、前記合成例3の高分子2を使用したという点を除いては、前記実施例1と同じ方法で有機発光素子を製作した。
前記実施例1において、正孔輸送層形成のために高分子1を使用する代わりに、前記合成例4の高分子3を使用したという点を除いては、前記実施例1と同じ方法で有機発光素子を製作した。
前記実施例1において、正孔輸送層を形成せず、伝導性バッファ層上に発光層を形成したという点を除いては、前記実施例1と同じ方法で有機発光素子を製作した。
前記実施例1において、正孔輸送層形成のために高分子1を使用する代わりに、下記高分子Aを使用したという点を除いては、前記実施例1と同じ方法で有機発光素子を製作した。高分子AをGPCで分析した結果、重量平均分子量(Mw)は58,000であり、多分散度は2.7であった。
前記実施例1、実施例2、実施例3、比較例1、及び比較例2の有機発光素子について、輝度(cd/m2)、及び効率(cd/A)及び寿命をPR650(Spectroscan)Source Measurement Unitを用いて測定し、その結果を下記表1に示した。寿命は初期輝度100cd/m2が半減する時間を測定することによって評価した。
Claims (19)
- 下記化学式1で表示される高分子。
Ar1は、互いに独立して、−(Q1)n−の化学式で表示され、前記Q1は置換または非置換のC5−C30アリーレン基、置換または非置換のC4−C30ヘテロアリーレン基、置換または非置換のC2−C30アルケニレン基及び化学式−N(Z1)−で表示される基からなる群から選択され、前記nは、1〜10の整数であり、−(Q1)n−のうち、n個のQ1は互いに同一であるか異なり、
X1及びX2は、互いに独立して、−O−、−S−、−N(Z2)−及び−C(Z3)(Z4)−からなる群から選択され、
前記R1、R2、Z1、Z2、Z3、及びZ4は、互いに独立して、水素、置換または非置換のC1−C30アルキル基、置換または非置換のC2−C30アルケニル基、置換または非置換のC2−C30アルキニル基、置換または非置換のC1−C30アルコキシ基、置換または非置換のC3−C12シクロアルキル基、置換または非置換のC3−C12シクロヘテロアルキル基、置換または非置換のC5−C30アリール基及び置換または非置換のC4−C30ヘテロアリール基からなる群から選択され、
a及びbは、互いに独立して、0.01〜0.99の実数であるが、a+b=1である。 - 前記Q1が、置換または非置換のC5−C14アリーレン基、置換または非置換のC4−C14ヘテロアリーレン基、置換または非置換のC2−C10アルケニレン基、及び化学式−N(Z1)−で表示される基からなる群から選択される、請求項1に記載の高分子。
- 前記Q1が、C2−C10アルケニレン基及び下記化学式2a〜2xからなる群から選択される、請求項1または2に記載の高分子。
前記化学式中、
T1〜T4は、互いに独立して、水素、ハロゲン原子、シアノ基、ヒドロキシル基、C1−C10アルキル基、C1−C10アルコキシ基、C2−C10アルケニル基、C5−C14アリール基、C4−C14ヘテロアリール基、及び−N(Z5)(Z6)で表示される基からなる群から選択され、
p、q、r及びsは、互いに独立して、1〜4の整数であり、
Z5及びZ6は、互いに独立して、水素、ハロゲン原子、シアノ基、ヒドロキシル基、C1−C10アルキル基、C1−C10アルコキシ基、C2−C10アルケニル基、C5−C14アリール基、及びC4−C14ヘテロアリール基からなる群から選択され、
−(T1)pのうち、p個のT1は互いに同一であるか異なり、−(T2)qのうち、q個のT2は互いに同一であるか異なり、−(T3)rのうち、r個のT3は互いに同一であるか異なり、−(T4)sのうち、s個のT4は互いに同一であるか異なる。 - 前記T1〜T4は、互いに独立して、水素、C1−C10アルキル基、C1−C10アルコキシ基、フェニル基、ナフチル基、及び−N(Z5)(Z6)で表示される基からなる群から選択され、前記Z5及びZ6は、互いに独立して、水素、C1−C10アルキル基、C1−C10アルコキシ基、フェニル基、及びナフチル基からなる群から選択される、請求項3に記載の高分子。
- 前記nは、1、2、3、4、5、または6である、請求項1〜4のいずれか1項に記載の高分子。
- 前記Ar1が、互いに独立して、下記化学式2a〜2x及び3a〜3lからなる群から選択される、請求項1〜5のいずれか1項に記載の高分子。
T1〜T4は、互いに独立して、水素、ハロゲン原子、シアノ基、ヒドロキシル基、C1−C10アルキル基、C1−C10アルコキシ基、C2−C10アルケニル基、C5−C14アリール基、C4−C14ヘテロアリール基、及び−N(Z5)(Z6)で表示される基からなる群から選択され、
Z5及びZ6は、互いに独立して、水素、ハロゲン原子、シアノ基、ヒドロキシル基、C1−C10アルキル基、C1−C10アルコキシ基、C2−C10アルケニル基、C5−C14アリール基、及びC4−C14ヘテロアリール基からなる群から選択され、
p、q、r及びsは、互いに独立して、1〜4の整数であり、
−(T1)pのうち、p個のT1は互いに同一であるか異なり、−(T2)qのうち、q個のT2は互いに同一であるか異なり、−(T3)rのうち、r個のT3は互いに同一であるか異なり、−(T4)sのうち、s個のT4は互いに同一であるか異なる。 - 前記Ar1が、下記化学式2dで表示され、且つ、下記化学式2dのうち、T1及びT2は水素であり、T3及びT4が互いに独立して水素、C1−C10アルキル基及びC1−C10アルコキシ基からなる群から選択される、請求項1〜6のいずれか1項に記載の高分子。
- 前記Ar1が、下記化学式2eで表示され、且つ、下記化学式2eのうち、T1及びT2は水素であり、T3及びT4が互いに独立して水素、C1−C10アルキル基及びC1−C10アルコキシ基からなる群から選択される、請求項1〜7のいずれか1項に記載の高分子。
- 前記X1及びX2が、−O−である、請求項1〜8のいずれか1項に記載の高分子。
- 前記R1及びR2が、互いに独立して、C5−C14アリール基;C4−C14ヘテロアリール基;ハロゲン原子、ヒドロキシル基、シアノ基、C1−C10アルキル基、C1−C10アルコキシ基及びC5−C14アリール基からなる群から選択された1つ以上の置換基で置換されたC5−C14アリール基;及びハロゲン原子、ヒドロキシル基、シアノ基、C1−C10アルキル基、C1−C10アルコキシ基及びC5−C14アリール基からなる群から選択された1つ以上の置換基で置換されたC5−C14ヘテロアリール基;からなる群から選択される、請求項1〜9のいずれか1項に記載の高分子。
- 前記R1及びR2が、下記化学式4aで表示される、請求項1〜10のいずれか1項に記載の高分子。
- 前記化学式1中、a及びbは、互いに独立して、0.3〜0.7の実数である、請求項1〜11のいずれか1項に記載の高分子。
- 下記化学式6または7で表示される、請求項1〜12のいずれか1項に記載の高分子。
- 10,000〜200,000の重量平均分子量(Mw)を有する、請求項1〜13のいずれか1項に記載の高分子。
- 1.5〜5の多分散度(PDI)を有する、請求項1〜14のいずれか1項に記載の高分子。
- 請求項1〜15のいずれか1項に記載の高分子からなる、有機発光素子用の正孔輸送物質。
- 基板と、第1電極と、第2電極と、前記第1電極と前記第2電極との間に請求項1〜15のいずれか1項に記載の高分子を含む第1層と、を備える、有機発光素子。
- 前記第1層が、正孔輸送層である、請求項17に記載の有機発光素子。
- 前記第1電極と前記第2電極との間に伝導性バッファ層、正孔注入層、正孔輸送層、発光層、正孔阻止層、電子輸送層及び電子注入層からなる群から選択された1つ以上の層をさらに備える、請求項17に記載の有機発光素子。
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KR101202340B1 (ko) * | 2005-01-21 | 2012-11-16 | 삼성디스플레이 주식회사 | 청색 발광 화합물 및 이를 채용한 유기 전계 발광 소자 |
WO2007043495A1 (ja) * | 2005-10-07 | 2007-04-19 | Sumitomo Chemical Company, Limited | 共重合体およびそれを用いた高分子発光素子 |
KR101243918B1 (ko) * | 2006-01-03 | 2013-03-14 | 삼성디스플레이 주식회사 | 청색 발광 고분자, 그 제조방법 및 이를 채용한 유기 전계발광 소자 |
KR101328972B1 (ko) | 2006-01-26 | 2013-11-13 | 삼성디스플레이 주식회사 | 전계발광 고분자 및 이를 이용한 유기 전계발광 소자 |
KR101288304B1 (ko) * | 2006-01-27 | 2013-07-18 | 삼성디스플레이 주식회사 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
KR101223720B1 (ko) | 2006-06-05 | 2013-01-17 | 삼성디스플레이 주식회사 | 고분자 화합물 및 이를 이용한 유기 발광 소자 |
JP5407122B2 (ja) * | 2006-08-01 | 2014-02-05 | 住友化学株式会社 | 高分子化合物および高分子発光素子 |
JP5251043B2 (ja) * | 2006-09-13 | 2013-07-31 | 住友化学株式会社 | 高分子化合物および高分子発光素子 |
WO2008032720A1 (fr) * | 2006-09-13 | 2008-03-20 | Sumitomo Chemical Company, Limited | Composé polymère et dispositif polymère émettant de la lumière |
-
2009
- 2009-10-09 KR KR1020090096394A patent/KR101137386B1/ko active IP Right Grant
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2010
- 2010-09-30 US US12/895,374 patent/US8987709B2/en active Active
- 2010-10-04 EP EP10186431A patent/EP2308911A3/en not_active Withdrawn
- 2010-10-08 JP JP2010228733A patent/JP5432106B2/ja active Active
- 2010-10-09 CN CN201010503410.XA patent/CN102040728B/zh active Active
Also Published As
Publication number | Publication date |
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KR20110039109A (ko) | 2011-04-15 |
CN102040728A (zh) | 2011-05-04 |
US20110084254A1 (en) | 2011-04-14 |
US8987709B2 (en) | 2015-03-24 |
CN102040728B (zh) | 2016-02-17 |
EP2308911A2 (en) | 2011-04-13 |
JP2011080066A (ja) | 2011-04-21 |
EP2308911A3 (en) | 2012-02-01 |
KR101137386B1 (ko) | 2012-04-20 |
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