JP2006310538A - Light-emitting element - Google Patents
Light-emitting element Download PDFInfo
- Publication number
- JP2006310538A JP2006310538A JP2005131247A JP2005131247A JP2006310538A JP 2006310538 A JP2006310538 A JP 2006310538A JP 2005131247 A JP2005131247 A JP 2005131247A JP 2005131247 A JP2005131247 A JP 2005131247A JP 2006310538 A JP2006310538 A JP 2006310538A
- Authority
- JP
- Japan
- Prior art keywords
- group
- aryl
- derivatives
- light emitting
- heteroaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims description 96
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 229910052757 nitrogen Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- -1 alkylseleno group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 12
- NKHUXLDXYURVLX-UHFFFAOYSA-N 2h-pyrrolo[3,4-c]pyrrole-4,6-dione Chemical class N1C=C2C(=O)NC(=O)C2=C1 NKHUXLDXYURVLX-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000005401 siloxanyl group Chemical group 0.000 claims description 11
- 125000005013 aryl ether group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 150000004832 aryl thioethers Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
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- 125000003172 aldehyde group Chemical group 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
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- 239000011651 chromium Substances 0.000 claims description 5
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- 239000011701 zinc Substances 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
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- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
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- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
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- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 150000001893 coumarin derivatives Chemical class 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- KXMKGOPUYUWQHC-UHFFFAOYSA-N 2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C=4C=CC=C(C=4)C=4N=C5C6=NC=CC=C6C=CC5=CC=4)=CC=C3C=CC2=C1 KXMKGOPUYUWQHC-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
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- 238000010549 co-Evaporation Methods 0.000 description 3
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- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- GNXPUXGOQIHJLJ-UHFFFAOYSA-N thiadiazolo[4,5-b]pyridine Chemical compound C1=CN=C2N=NSC2=C1 GNXPUXGOQIHJLJ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 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
- 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
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
Abstract
Description
本発明は、電気エネルギーを光に変換できる発光素子であって、表示素子、フラットパネルディスプレイ、バックライト、照明、インテリア、標識、看板、電子写真機および光信号発生器などの分野に利用可能な発光素子に関する。 The present invention is a light emitting element capable of converting electrical energy into light, and can be used in the fields of display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like. The present invention relates to a light emitting element.
陰極から注入された電子と陽極から注入された正孔が両極に挟まれた有機蛍光体内で再結合する際に発光するという有機薄膜発光素子の研究が活発に行われている。この発光素子は、薄型でかつ低駆動電圧下での高輝度発光と、発光材料を選ぶことによる多色発光が特徴である。 Researches on organic thin-film light-emitting elements that emit light when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between both electrodes are actively conducted. This light emitting element is thin and has high luminance light emission under a low driving voltage, and multicolor light emission by selecting a light emitting material.
この研究は、コダック社のＣ．Ｗ．Ｔａｎｇらによって有機薄膜素子が高輝度に発光することが示されて以来、多くの研究機関が検討を行っている。コダック社の研究グループが提示した有機薄膜発光素子の代表的な構成は、ＩＴＯガラス基板上に正孔輸送性のジアミン化合物、発光層であるトリス（８−キノリノラート）アルミニウム（III）、そして陰極としてＭｇ：Ａｇを順次設けたものであり、１０Ｖ程度の駆動電圧で１０００ｃｄ／ｍ２の緑色発光が可能であった（非特許文献１参照）。 This study was conducted by C.D. W. Since Tang et al. Have shown that organic thin film elements emit light with high brightness, many research institutions have studied. The representative structure of the organic thin film light emitting device presented by the Kodak research group is a hole transporting diamine compound on an ITO glass substrate, tris (8-quinolinolato) aluminum (III) as a light emitting layer, and a cathode. Mg: Ag was sequentially provided, and green light emission of 1000 cd / m 2 was possible with a driving voltage of about 10 V (see Non-Patent Document 1).
また、有機薄膜発光素子は、発光層に種々の蛍光材料を用いることにより、多様な発光色を得ることが可能であることから、ディスプレイなどへの実用化研究が盛んである。三原色の発光材料の中では緑色発光材料の研究が最も進んでおり、現在は赤色発光材料と青色発光材料において、特性向上を目指して鋭意研究がなされている。 In addition, organic thin-film light-emitting elements can be obtained in various emission colors by using various fluorescent materials for the light-emitting layer, and therefore, researches for practical application to displays and the like are actively conducted. Among the three primary color luminescent materials, research on the green luminescent material is the most advanced, and at present, intensive research is being conducted to improve the characteristics of the red and blue luminescent materials.
赤色発光を得る手法として、ホスト材料の中に微量の赤色発光材料をドーパント材料として混入させる方法が広く検討されており、ホスト材料であるＡｌｑ３に微量の４−（ジシアノメチレン）−２−ｔｅｒｔ−ブチル−６−（１，１，７，７−テトラメチルジュロリジル−９−エニル）−４Ｈ−ピラン（ＤＣＪＴＢ）を混入した赤色発光材料（特許文献１参照）が知られている。また、高効率・高色純度の赤色発光を得る手段として、ホスト材料としてジケトピロロ［３，４−ｃ］ピロール誘導体を、ドーパント材料としてピロメテン骨格を有する化合物もしくは金属錯体のような発光ピーク波長が５８０ｎｍ以上７２０ｎｍ以下の有機蛍光物質を組み合わせたもの（特許文献２〜４参照）がある。
しかしながら従来の赤色発光素子では、高効率・高色純度の赤色発光が得られるものの、長寿命の赤色発光を実現することは困難であった。本発明は、従来にない長寿命を有し、かつ高効率・高色純度発光を有する赤色発光素子を提供することを目的とする。 However, with the conventional red light emitting device, red light emission with high efficiency and high color purity can be obtained, but it has been difficult to achieve long life red light emission. An object of the present invention is to provide a red light-emitting element having an unprecedented long life and having high efficiency and high color purity light emission.
すなわち本発明は、陽極と陰極の間に少なくとも発光層が存在し、電気エネルギーにより発光する素子であって、発光層が少なくとも一般式（１）または（４）に示すジケトピロロ［３，４−ｃ］ピロール誘導体と蛍光ピーク波長が５８０ｎｍ以上７２０ｎｍ以下の有機蛍光物質を含有することを特徴とする発光素子である。 That is, the present invention is an element in which at least a light emitting layer exists between an anode and a cathode and emits light by electric energy, and the light emitting layer is at least diketopyrrolo represented by the general formula (1) or (4) [3,4-c. A light-emitting element comprising a pyrrole derivative and an organic fluorescent material having a fluorescence peak wavelength of 580 nm to 720 nm.
｛Ｒ１およびＲ２は同じでも異なっていてもよく、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、アリール基、ヘテロアリール基、シリル基、シロキサニル基、または一般式（２）で表される有機基の中から選ばれ、 {R 1 and R 2 may be the same or different, and alkyl group, cycloalkyl group, heterocyclic group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, aryl group, heteroaryl group, silyl group, siloxanyl A group, or an organic group represented by the general formula (2),
(Ｒ３およびＲ４は同じでも異なっていてもよく、アルキル基、フェニル基から選ばれ、Ａｒ３はアリール基の中から選ばれる。ｍは０〜４の整数を表す。）
Ａｒ１は一般式（３）で表される有機基より選ばれ、
(R 3 and R 4 may be the same or different and are selected from an alkyl group and a phenyl group, and Ar 3 is selected from an aryl group. M represents an integer of 0 to 4.)
Ar 1 is selected from organic groups represented by the general formula (3),
（Ｒ５〜Ｒ１１は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環もしくは脂肪族環の中から選ばれる。Ｘは炭素または窒素であるが、窒素の場合には上記Ｒ８は存在しない。）Ａｒ２はＡｒ１と異なっており、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロアリール基の中から選ばれる。｝ (R 5 to R 11 may be the same or different, and are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group. Group, aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group And X is carbon or nitrogen, but in the case of nitrogen, the above R 8 is not present.) Ar 2 is different from Ar 1, a substituted or unsubstituted aryl group, substituted if It is selected from the unsubstituted heteroaryl group. }
（Ｒ１およびＲ２は同じでも異なっていてもよく、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、アリール基、ヘテロアリール基、シリル基、シロキサニル基、または一般式（２）で表される有機基の中から選ばれ、Ａｒ４およびＡｒ５は同じでも異なっていてもよく、一般式（３）で表される有機基より選ばれ、Ａｒ６はアリール鎖、ヘテロアリール鎖から選ばれる。） (R 1 and R 2 may be the same or different, and alkyl group, cycloalkyl group, heterocyclic group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, aryl group, heteroaryl group, silyl group, siloxanyl. Group, or an organic group represented by the general formula (2), Ar 4 and Ar 5 may be the same or different, and are selected from the organic group represented by the general formula (3), Ar 6 is selected from an aryl chain and a heteroaryl chain.)
本発明によれば、長寿命発光が可能で、高効率・高色純度を有する赤色発光素子が得られる。 According to the present invention, it is possible to obtain a red light-emitting element that can emit light with a long lifetime and has high efficiency and high color purity.
本発明における発光素子について例をあげて詳細に説明する。本発明の発光素子は、少なくとも陽極と陰極、およびそれら陽極と陰極の間に介在する発光層を含む有機層とで構成されている。 The light-emitting element in the present invention will be described in detail with examples. The light emitting device of the present invention is composed of at least an anode and a cathode, and an organic layer including a light emitting layer interposed between the anode and the cathode.
本発明で用いられる陽極は、正孔を有機層に効率よく注入できる材料であれば特に限定されないが、比較的仕事関数の大きい材料を用いるのが好ましく、例えば、酸化錫、酸化インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、あるいは金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、ポリチオフェン、ポリピロールおよびポリアニリンなどの導電性ポリマーなどが挙げられる。これらの電極材料は、単独で用いてもよいが、複数の材料を積層または混合して用いてもよい。 The anode used in the present invention is not particularly limited as long as it is a material capable of efficiently injecting holes into the organic layer. However, it is preferable to use a material having a relatively large work function, for example, tin oxide, indium oxide, tin oxide. Examples thereof include conductive metal oxides such as indium (ITO), metals such as gold, silver and chromium, inorganic conductive materials such as copper iodide and copper sulfide, and conductive polymers such as polythiophene, polypyrrole and polyaniline. These electrode materials may be used alone, or a plurality of materials may be laminated or mixed.
電極の抵抗は、発光素子の発光に十分な電流が供給できればよく、発光素子の消費電力の観点からは低抵抗であることが望ましい。例えば、３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、現在では１０Ω／□程度の基板の供給も可能になっていることから、１００Ω／□以下の低抵抗品を使用することが特に望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。 The resistance of the electrode is not limited as long as a current sufficient for light emission of the light-emitting element can be supplied, and is preferably low from the viewpoint of power consumption of the light-emitting element. For example, an ITO substrate of 300Ω / □ or less will function as a device electrode, but since it is now possible to supply a substrate of about 10Ω / □, use a low-resistance product of 100Ω / □ or less. Is particularly desirable. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.
また、発光素子の機械的強度を保つために、発光素子を基板上に形成することが好ましい。基板としては、ソーダガラスや無アルカリガラスなどのガラス基板が好適に用いられる。ガラス基板の厚みは、機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ２などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することもできる。さらに、陽極が安定に機能するのであれば、基板はガラスである必要はなく、例えば、プラスチック基板上に陽極を形成しても良い。ＩＴＯ膜形成方法は、電子線ビーム法、スパッタリング法および化学反応法など特に制限を受けるものではない。 In order to maintain the mechanical strength of the light emitting element, the light emitting element is preferably formed over a substrate. As the substrate, a glass substrate such as soda glass or non-alkali glass is preferably used. As the thickness of the glass substrate, it is sufficient that the thickness is sufficient to maintain the mechanical strength. As for the material of the glass, non-alkali glass is preferable because it is better that there are fewer ions eluted from the glass. However, soda lime glass with a barrier coat such as SiO 2 is also commercially available, and this can be used. it can. Furthermore, if the anode functions stably, the substrate does not have to be glass. For example, the anode may be formed on a plastic substrate. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, and a chemical reaction method.
本発明で用いられる陰極に用いられる材料としては、電子を有機層に効率良く注入できる物質であれば特に限定されないが、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、カルシウム、セシウム、マグネシウムおよびこれらの合金などが挙げられる。電子注入効率をあげて素子特性を向上させるためには、リチウム、ナトリウム、カリウム、カルシウム、セシウム、マグネシウムまたはこれら低仕事関数金属を含む合金が有効である。しかしながら、これらの低仕事関数金属は、一般に大気中で不安定であることが多く、例えば、有機層に微量のリチウムやマグネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドーピングして安定性の高い電極を使用する方法が好ましい例として挙げることができる。また、フッ化リチウム、酸化リチウムのような無機塩の使用も可能である。更に、電極保護のために白金、金、銀、銅、鉄、錫、アルミニウムおよびインジウムなどの金属、またはこれら金属を用いた合金、そしてシリカ、チタニアおよび窒化ケイ素などの無機物、ポリビニルアルコール、塩化ビニル、炭化水素系高分子化合物などを積層することが、好ましい例として挙げられる。これらの電極の作製法は、抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティングおよびコーティングなど、導通を取ることができれば特に制限されない。 The material used for the cathode used in the present invention is not particularly limited as long as it can efficiently inject electrons into the organic layer, but generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, Examples thereof include chromium, lithium, sodium, potassium, calcium, cesium, magnesium, and alloys thereof. Lithium, sodium, potassium, calcium, cesium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less in the vacuum vapor deposition thickness meter display) to be stable. A method using a high electrode can be cited as a preferred example. Also, inorganic salts such as lithium fluoride and lithium oxide can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam, sputtering, ion plating, and coating.
有機層の一部である発光層とは実際に発光が行われる層であり、本発明の発光層は、一般式（１）または（４）で示されるジケトピロロ［３，４−ｃ］ピロール誘導体を含む。 The light emitting layer that is part of the organic layer is a layer that actually emits light, and the light emitting layer of the present invention is a diketopyrrolo [3,4-c] pyrrole derivative represented by the general formula (1) or (4). including.
Ｒ１およびＲ２は同じでも異なっていてもよく、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、アリール基、ヘテロアリール基、シリル基、シロキサニル基または、一般式（２）で表される有機基の中から選ばれ、 R 1 and R 2 may be the same or different and are an alkyl group, a cycloalkyl group, a heterocyclic group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a silyl group, and a siloxanyl group. Or, it is selected from organic groups represented by the general formula (2),
Ｒ３およびＲ４は同じでも異なっていてもよく、アルキル基、フェニル基から選ばれ、Ａｒ３はアリール基の中から選ばれる。ｍは０〜４の整数を表す。
Ａｒ１は一般式（３）で表される有機基より選ばれ、
R 3 and R 4 may be the same or different and are selected from an alkyl group and a phenyl group, and Ar 3 is selected from an aryl group. m represents an integer of 0 to 4.
Ar 1 is selected from organic groups represented by the general formula (3),
Ｒ５〜Ｒ１１は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環もしくは脂肪族環の中から選ばれる。Ｘは炭素または窒素であるが、窒素の場合には上記Ｒ８は存在しない。）Ａｒ２はＡｒ１と異なっており、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロアリール基の中から選ばれる。 R 5 to R 11 may be the same or different, and are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group. , Aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group , A siloxanyl group, a condensed ring formed between adjacent substituents or an aliphatic ring. X is carbon or nitrogen, but in the case of nitrogen, the above R 8 does not exist. ) Ar 2 is different from Ar 1 and is selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group.
Ｒ１およびＲ２は同じでも異なっていてもよく、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、アリール基、ヘテロアリール基、シリル基、シロキサニル基または、一般式（２）で表される有機基の中から選ばれ、Ａｒ４およびＡｒ５は同じでも異なっていてもよく、一般式（３）で表される有機基より選ばれ、Ａｒ６はアリール鎖、ヘテロアリール鎖から選ばれる。 R 1 and R 2 may be the same or different and are an alkyl group, a cycloalkyl group, a heterocyclic group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a silyl group, and a siloxanyl group. Or, it is selected from the organic groups represented by the general formula (2), Ar 4 and Ar 5 may be the same or different, are selected from the organic groups represented by the general formula (3), and Ar 6 Is selected from an aryl chain and a heteroaryl chain.
有機材料を発光層に用いた発光素子では、安定した発光を得るために、発光層を構成する有機材料がアモルファス状態の薄膜を形成することが望まれる。連続駆動時の輝度低下原因の一つとして、駆動時の発熱等によりそのアモルファス状態が変化することが知られている。特に平面性・対称性が高い構造を有する有機材料では、熱による結晶化が進行しやすく、安定なアモルファス状態を維持することが困難な場合が多い。 In a light emitting element using an organic material for a light emitting layer, in order to obtain stable light emission, it is desired that an organic material constituting the light emitting layer forms an amorphous thin film. As one of the causes of luminance reduction during continuous driving, it is known that the amorphous state changes due to heat generation during driving. In particular, in an organic material having a structure with high planarity and symmetry, crystallization by heat is likely to proceed, and it is often difficult to maintain a stable amorphous state.
本発明の一般式（１）で表されるジケトピロロ［３，４−ｃ］ピロール誘導体は、Ａｒ１とＡｒ２が異なる置換基を有することにより、分子構造が非対称型になり、発光層を形成する際に安定なアモルファス状態を得ることが可能となり、長寿命の発光が得られるようになる。また、Ａｒ１に一般式（３）で示される置換基を導入することで、平面性の高いジケトピロロ［３，４−ｃ］ピロール骨格に対してねじれの関係でＡｒ１が導入されることになり、分子全体の平面性も低くなる。さらに、平面性が低くなることで、薄膜形成時の濃度消光を抑制でき、高効率発光を得ることも可能となる。 In the diketopyrrolo [3,4-c] pyrrole derivative represented by the general formula (1) of the present invention, Ar 1 and Ar 2 have different substituents, whereby the molecular structure becomes asymmetric and forms a light emitting layer. In this case, a stable amorphous state can be obtained, and light emission with a long lifetime can be obtained. Further, by introducing a substituent represented by Ar 1 in the general formula (3), that Ar 1 is introduced at a twisted relationship to the plane highly diketopyrrolo [3,4-c] pyrrole skeletons Therefore, the planarity of the whole molecule is also lowered. Furthermore, since the flatness is lowered, concentration quenching during the formation of the thin film can be suppressed, and high-efficiency light emission can be obtained.
一般式（３）の中でも、Ｒ５〜Ｒ１１のうち少なくとも一つがアルキル基もしくはアルコキシ基もしくはアミノ基で置換されているか、隣接置換基との間に縮合環を形成しているものが、より分子構造がかさ高くなり、安定なアモルファス状態を形成する観点からより好ましい。さらに、合成の容易さの観点から、Ｒ９の位置がメチル基もしくはメトキシ基もしくはジフェニルアミノ基が置換されたもの、あるいはＲ９およびＲ１０の間でピリジン環もしくはベンゼン環が縮合したものを特に好ましい例として挙げることができる。 Among the general formula (3), at least one of R 5 to R 11 is substituted with an alkyl group, an alkoxy group or an amino group, or a condensed ring is formed between adjacent substituents. It is more preferable from the viewpoint of increasing the molecular structure and forming a stable amorphous state. Furthermore, from the viewpoint of ease of synthesis, those in which the position of R 9 is substituted with a methyl group, a methoxy group or a diphenylamino group, or those in which a pyridine ring or a benzene ring is condensed between R 9 and R 10 are particularly preferred. It can be mentioned as a preferred example.
また、一般式（４）で表されるジケトピロロ［３，４−ｃ］ピロール誘導体は、ピロール骨格をＡｒ６で連結することにより分子が全体として嵩高い構造となるため、安定なアモルファス膜を得ることが可能となり、さらに一般式（１）の誘導体と同様、一般式（３）で表される置換基を有するため高効率発光を得ることも可能となる。 In addition, the diketopyrrolo [3,4-c] pyrrole derivative represented by the general formula (4) has a bulky structure as a whole by connecting the pyrrole skeleton with Ar 6 , so that a stable amorphous film is obtained. Furthermore, as with the derivative of the general formula (1), since it has a substituent represented by the general formula (3), it is possible to obtain highly efficient light emission.
これらの置換基のうち、アルキル基とは、メチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもよい。置換されている場合の置換基には特に制限は無く、例えば、アルコキシ基、アルケニル基、アリール基、ヘテロアリール基等を挙げることができ、この点は、特にことわりがない限り、以下に説明する他の置換基についても同様である。また、アルキル基の炭素数は特に限定されないが、入手の容易性やコストの点から、通常、１〜２０の範囲である。 Among these substituents, the alkyl group represents a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. The substituent in the case of being substituted is not particularly limited, and examples thereof include an alkoxy group, an alkenyl group, an aryl group, a heteroaryl group, and the like, and this point will be described below unless otherwise specified. The same applies to other substituents. Further, the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.
また、シクロアルキル基とは、シクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどの飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもよい。 The cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl and the like, which may be unsubstituted or substituted.
また、複素環基とは、ピラン環、ピペリジン環、環状アミドなどの炭素以外の原子を環内に有する脂肪族環を有する基を示し、これは無置換でも置換されていてもよい。複素環基の炭素数は特に限定されないが、通常、２〜２０の範囲である。 The heterocyclic group refers to a group having an aliphatic ring having atoms other than carbon in the ring, such as a pyran ring, a piperidine ring, and a cyclic amide, which may be unsubstituted or substituted. Although carbon number of a heterocyclic group is not specifically limited, Usually, it is the range of 2-20.
また、アラルキル基とは、例えばベンジル基、フェニルエチル基などの脂肪族炭化水素を介した芳香族炭化水素基を示し、これは無置換でも置換されていてもよい。アラルキル基の炭素数に特に制限はないが、通常、７〜２４の範囲である。 Moreover, an aralkyl group shows the aromatic hydrocarbon group via aliphatic hydrocarbons, such as a benzyl group and a phenylethyl group, for example, and this may be unsubstituted or substituted. Although there is no restriction | limiting in particular in carbon number of an aralkyl group, Usually, it is the range of 7-24.
また、アルケニル基とは、ビニル基、アリル基、ブタジエニル基などの二重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもよい。アルケニル基の炭素数は特に限定されないが、通常、２〜２０の範囲である。 Moreover, an alkenyl group shows the unsaturated aliphatic hydrocarbon group containing double bonds, such as a vinyl group, an allyl group, and a butadienyl group, and this may be unsubstituted or substituted. Although carbon number of an alkenyl group is not specifically limited, Usually, it is the range of 2-20.
また、シクロアルケニル基とは、シクロペンテニル基、シクロペンタジエニル基、シクロヘキセニル基などの二重結合を含む不飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもよい。 The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, which may be unsubstituted or substituted. .
また、アルキニル基とは、エチニル基などの三重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもよい。アルキニル基の炭素数は特に限定されないが、通常、２〜２０の範囲である。 Moreover, an alkynyl group shows the unsaturated aliphatic hydrocarbon group containing triple bonds, such as an ethynyl group, and this may be unsubstituted or substituted. Although carbon number of an alkynyl group is not specifically limited, Usually, it is the range of 2-20.
また、アリール基とは、フェニル基、ナフチル基、ビフェニル基、フェナンスリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基を示す。アリール基は、無置換でも置換されていてもよい。アリール基の炭素数は特に限定されないが、通常、６〜４０の範囲である。 Moreover, an aryl group shows aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, a pyrenyl group. The aryl group may be unsubstituted or substituted. Although carbon number of an aryl group is not specifically limited, Usually, it is the range of 6-40.
また、ヘテロアリール基とは、フラニル基、チオフェニル基、オキサゾリル基、ピリジル基、キノリニル基、フェナントロリル基、カルバゾリル基などの炭素以外の原子を環内に有する芳香族基を示し、これは無置換でも置換されていてもよい。ヘテロアリール基の炭素数は特に限定されないが、通常、２〜３０の範囲である。 The heteroaryl group refers to an aromatic group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a phenanthryl group, or a carbazolyl group, which may be unsubstituted. May be substituted. Although carbon number of a heteroaryl group is not specifically limited, Usually, it is the range of 2-30.
また、シリル基とは、例えば、トリメチルシリル基などのケイ素化合物基を示し、これは無置換でも置換されていてもよい。シリル基の炭素数は特に限定されないが、通常、３〜２０の範囲である。また、ケイ素数は、通常、１〜６である。 Moreover, a silyl group shows silicon compound groups, such as a trimethylsilyl group, for example, and this may be unsubstituted or substituted. Although carbon number of a silyl group is not specifically limited, Usually, it is the range of 3-20. Moreover, the number of silicon is 1-6 normally.
また、シロキサニル基とは、トリメチルシロキサニル基などのエーテル結合を介したケイ素化合物基を示し、これは無置換でも置換されていてもよい。シリル基の炭素数は特に限定されないが、通常、３〜２０の範囲である。また、ケイ素数は、通常、１〜６である。 The siloxanyl group refers to a silicon compound group through an ether bond such as a trimethylsiloxanyl group, which may be unsubstituted or substituted. Although carbon number of a silyl group is not specifically limited, Usually, it is the range of 3-20. Moreover, the number of silicon is 1-6 normally.
また、隣接置換基との間に形成される縮合環もしくは脂肪族環とは、例えばＲ９とＲ１０のような隣接する置換基間で共役または非共役の環を形成するものである。そして、これらの環は環内構造に窒素、酸素、硫黄原子を含んでいても良いし、さらに別の環と縮合していても良い。 The condensed ring or aliphatic ring formed between adjacent substituents is a ring that forms a conjugated or non-conjugated ring between adjacent substituents such as R 9 and R 10 . These rings may contain nitrogen, oxygen and sulfur atoms in the ring structure, or may be condensed with another ring.
また、アルコキシ基とは、メトキシ基などのエーテル結合を介した脂肪族炭化水素基を示し、脂肪族炭化水素基は無置換でも置換されていてもよい。アルコキシ基の炭素数は特に限定されないが、通常、１〜２０の範囲である。 The alkoxy group means an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an alkoxy group is not specifically limited, Usually, it is the range of 1-20.
また、アルキルチオ基とは、アルコキシ基のエーテル結合の酸素原子が硫黄原子に置換されたものである。 The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
また、アリールエーテル基とは、フェノキシ基などのエーテル結合を介した芳香族炭化水素基を示し、芳香族炭化水素基は無置換でも置換されていてもよい。アリールエーテル基の炭素数は特に限定されないが、通常、６〜４０の範囲である。 The aryl ether group refers to an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.
また、アリールチオエーテル基とは、アリールエーテル基のエーテル結合の酸素原子が硫黄原子に置換されたものである。
ハロゲンとは、フッ素、塩素、臭素、ヨウ素を示す。カルボニル基、エステル基、カルバモイル基、アミノ基、ホスフィンオキサイド基は、無置換でも置換されていてもよく、これら置換基はさらに置換されていてもよい。
The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom.
Halogen is fluorine, chlorine, bromine or iodine. The carbonyl group, ester group, carbamoyl group, amino group, and phosphine oxide group may be unsubstituted or substituted, and these substituents may be further substituted.
アリール鎖とはフェニル鎖、ナフチル鎖、ビフェニル鎖、フェナンスリル鎖、ターフェニル鎖などの芳香族炭化水素鎖を示し、無置換でも置換されていてもよい。ヘテロアリール鎖とはフラニル鎖、チオフェニル鎖、オキサゾリル鎖、ピリジル鎖、キノリニル鎖、フェナントロリル鎖、カルバゾリル鎖などの炭素以外の原子を環内に有する芳香族鎖を示し、これは無置換でも置換されていてもよい。 The aryl chain refers to an aromatic hydrocarbon chain such as a phenyl chain, a naphthyl chain, a biphenyl chain, a phenanthryl chain, and a terphenyl chain, which may be unsubstituted or substituted. A heteroaryl chain is an aromatic chain having atoms other than carbon, such as furanyl chain, thiophenyl chain, oxazolyl chain, pyridyl chain, quinolinyl chain, phenanthroyl chain, carbazolyl chain, which are unsubstituted or substituted. May be.
一般式（１）で表される化合物の具体例として、以下のような化合物が挙げられる。 Specific examples of the compound represented by the general formula (1) include the following compounds.
一般式（４）で表される化合物の具体例として、以下のような化合物が挙げられる。 Specific examples of the compound represented by the general formula (4) include the following compounds.
本発明のジケトピロロ［３，４−ｃ］ピロール誘導体は蛍光性であり、一般にその蛍光量子収率が０．３以上（トルエンあるいはＤＭＦ中）あるいはモル吸光係数が５０００以上の値を有する。 The diketopyrrolo [3,4-c] pyrrole derivative of the present invention is fluorescent and generally has a fluorescence quantum yield of 0.3 or more (in toluene or DMF) or a molar extinction coefficient of 5000 or more.
本発明では赤色発光を得るために発光層に前記ジケトピロロ［３，４−ｃ］ピロール誘導体とともに蛍光ピーク波長が５８０ｎｍ以上７２０ｎｍ以下の有機蛍光物質が用いられるが、具体的には従来から知られている、テリレンなどの芳香族炭化水素の縮合環誘導体、ピリジノチアジアゾールやピラゾロピリジン、ジケトピロロピロールなどの縮合複素環誘導体、ビス（ジイソプロピルフェニル）ペリレンテトラカルボン酸イミドなどのナフタルイミド誘導体、ペリノン誘導体、アセチルアセトンやベンゾイルアセトンとフェナントロリンなどを配位子とするＥｕ錯体などの希土類錯体、４−（ジシアノメチレン）−２−メチル−６−（ｐ−ジメチルアミノスチリル）−４Ｈ−ピランやその類縁体、マグネシウムフタロシアニン、アルミニウムクロロフタロシアニンなどの金属フタロシアニン誘導体、亜鉛ポルフィリンなどの金属ポルフィリン誘導体、チオフェン誘導体、ピロール誘導体、ローダミン化合物、デアザフラビン誘導体、クマリン誘導体、オキサジン化合物、フェノキサジン誘導体、フェノキサゾン誘導体、キナクリドン誘導体、ベンゾチオキサンテンやその類縁体、ジシアノエテニルアレーン誘導体などを用いることが出来るが、特にこれらに限定されるものではない。 In the present invention, an organic fluorescent material having a fluorescence peak wavelength of 580 nm or more and 720 nm or less is used together with the diketopyrrolo [3,4-c] pyrrole derivative in the light emitting layer in order to obtain red light emission. Condensed ring derivatives of aromatic hydrocarbons such as terylene, condensed heterocyclic derivatives such as pyridinothiadiazole, pyrazolopyridine, diketopyrrolopyrrole, naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone Derivatives, rare earth complexes such as Eu complexes with acetylacetone, benzoylacetone and phenanthroline as ligands, 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs , Magnesium phthalocyanine, aluminum Metal phthalocyanine derivatives such as chlorophthalocyanine, metal porphyrin derivatives such as zinc porphyrin, thiophene derivatives, pyrrole derivatives, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, oxazine compounds, phenoxazine derivatives, phenoxazone derivatives, quinacridone derivatives, benzothioxanthene and related compounds , Dicyanoethenylarene derivatives and the like can be used, but are not particularly limited thereto.
優れた色純度特性を持つ赤色発光を得るために、前記有機蛍光物質の中でも一般式（５）に示すピロメテン骨格を有する化合物もしくはその金属錯体を好適に用いることができる。 In order to obtain red light emission having excellent color purity characteristics, among the organic fluorescent materials, a compound having a pyromethene skeleton represented by the general formula (5) or a metal complex thereof can be preferably used.
Ｒ１２〜Ｒ１８のうち少なくとも一つはアリール基、ヘテロアリール基を含むかあるいは隣接置換基との間に縮合環を形成し、残りは水素、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アルキルセレノ基、アリールエーテル基、アリールチオエーテル基、アリールセレノエーテル基、アリール基、ヘテロアリール基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環もしくは脂肪族環の中から選ばれる。Ｙは炭素または窒素であるが、窒素の場合には上記Ｒ１８は存在しない。金属錯体の金属は、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛、白金から選ばれる少なくとも一種である。 At least one of R 12 to R 18 contains an aryl group, a heteroaryl group, or forms a condensed ring with an adjacent substituent, and the rest are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, aralkyl Group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, alkylseleno group, arylether group, arylthioether group, arylselenoether group, aryl group, heteroaryl group, halogen, haloalkane , Haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, condensed ring formed between adjacent substituents or aliphatic Selected from the ring. Y is carbon or nitrogen, but in the case of nitrogen, the above R 18 does not exist. The metal of the metal complex is at least one selected from boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum.
これらの置換基については上述したものと同じである。一般式（５）で示された化合物は金属錯体を形成してもよく、そのときに用いられる好ましい金属は、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛、白金から選ばれる少なくとも一種である。これらの金属は、いずれもピロメテン骨格を有する化合物に対して安定な配位状態を取ることが可能なものであり、配位することにより蛍光ピーク波長の半値幅が狭くなり、高色純度発光が可能となる。またこれら金属錯体の中でさらに好ましいのは、一般式（６）に表される金属錯体である。 These substituents are the same as those described above. The compound represented by the general formula (5) may form a metal complex, and preferred metals used at that time are selected from boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum. Is at least one kind. All of these metals can take a stable coordination state with respect to a compound having a pyromethene skeleton. By coordination, the half-value width of the fluorescence peak wavelength is narrowed, and light emission with high color purity is achieved. It becomes possible. Further, among these metal complexes, the metal complex represented by the general formula (6) is more preferable.
高効率発光を得るためには、蛍光量子収率が高いものがより好ましく、ピロメテン骨格を有する化合物の金属錯体として、一般式（６）で表される化合物をより好適に用いることができる。 In order to obtain high-efficiency light emission, those having a high fluorescence quantum yield are more preferable, and the compound represented by the general formula (6) can be more suitably used as a metal complex of a compound having a pyromethene skeleton.
Ｒ１９〜Ｒ２５のうち少なくとも一つはアリール基、ヘテロアリール基を含むかあるいは隣接置換基との間に縮合環を形成し、残りは水素、アルキル基、シクロアルキル基、複素環基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アルキルセレノ基、アリールエーテル基、アリールチオエーテル基、アリールセレノエーテル基、アリール基、ヘテロアリール基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環もしくは脂肪族環の中から選ばれる。Ｒ２６およびＲ２７は同じでも異なっていてもよく、ハロゲン、水素、アルキル基、アルコキシ基、アリール基、ヘテロアリール基から選ばれる。Ｙは炭素または窒素であるが、窒素の場合には上記Ｒ２５は存在しない。これらの置換基の説明は上述したものと同じである。 At least one of R 19 to R 25 contains an aryl group, a heteroaryl group, or forms a condensed ring with an adjacent substituent, and the rest are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, aralkyl Group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, alkylseleno group, arylether group, arylthioether group, arylselenoether group, aryl group, heteroaryl group, halogen, haloalkane , Haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, condensed ring formed between adjacent substituents or aliphatic Selected from the ring. R 26 and R 27 may be the same or different and are selected from halogen, hydrogen, an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Y is carbon or nitrogen, but in the case of nitrogen, the above R 25 does not exist. The explanation of these substituents is the same as described above.
さらなる高効率発光を得るためには、濃度消光が抑制された一般式（７）で表される化合物をより好適に用いることができる。 In order to obtain further high-efficiency light emission, the compound represented by the general formula (7) in which concentration quenching is suppressed can be used more suitably.
ここで、Ｒ２８およびＲ２９は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、ハロゲン、シアノ基、カルボニル基、エステル基、カルバモイル基、アミノ基、シリル基、ホスフィンオキサイド基の中から選ばれる。Ｒ３０およびＲ３１は同じでも異なっていてもよく、ハロゲン、水素、アルキル基、アルコキシ基、アリール基、ヘテロアリール基から選ばれる。Ａｒ７〜Ａｒ１１はアリール基もしくはヘテロアリール基を表す。Ｙは炭素または窒素であるが、窒素の場合には上記Ａｒ１１は存在しない。これらの置換基の説明は上述したものと同じである。 Here, R 28 and R 29 may be the same or different, and are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, The arylthioether group, aryl group, heteroaryl group, halogen, cyano group, carbonyl group, ester group, carbamoyl group, amino group, silyl group, and phosphine oxide group are selected. R 30 and R 31 may be the same or different and are selected from halogen, hydrogen, an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Ar 7 to Ar 11 represent an aryl group or a heteroaryl group. Y is carbon or nitrogen, but in the case of nitrogen, Ar 11 does not exist. The explanation of these substituents is the same as described above.
一般式（６）で表される化合物の具体例として、以下のような化合物が挙げられる。 Specific examples of the compound represented by the general formula (6) include the following compounds.
発光層は単一層でも複数層からなってもどちらでもよく、それぞれ発光材料（ホスト材料、ドーパント材料）により形成される。ホスト材料とドーパント材料は、それぞれ一種類を用いてもよく、またそれぞれ複数の組み合わせで用いてもよい。ドーパント材料はホスト材料の全体に含まれていてもよく、また部分的に含まれていてもよい。ドーパント材料の導入は積層されていてもよく、また層内に分散されていてもよい。 The light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting material (host material, dopant material). One kind of host material and one dopant material may be used, or a plurality of combinations may be used. The dopant material may be included in the entire host material or may be partially included. The introduction of the dopant material may be laminated, or may be dispersed in the layer.
ドーパント材料の量は、多すぎると濃度消光現象が起きるため、ホスト材料に対して２０重量％以下で用いることが好ましく、さらに好ましくは１０重量％以下である。ドーピング方法としては、ホスト材料との共蒸着法によって形成することができるが、ホスト材料と予め混合してから同時に蒸着しても良い。本発明で用いられるジケトピロロ［３，４−ｃ］ピロール誘導体は、溶液状態での蛍光量子収率が高いことからドーパント材料として用いても良いが、固体状態での蛍光強度も強いことから、ホスト材料として好適に用いられる。一方のピロメテン化合物は、固体状態でも蛍光を有することから、ホスト材料として用いても良いが、溶液状態での蛍光量子収率が極めて高いことや、発光スペクトルの半値幅が小さく、高色純度発光が可能なことからドーパント材料として好適に用いられる。 If the amount of the dopant material is too large, a concentration quenching phenomenon occurs, so that it is preferably used at 20% by weight or less, more preferably 10% by weight or less with respect to the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited. The diketopyrrolo [3,4-c] pyrrole derivative used in the present invention may be used as a dopant material because of its high fluorescence quantum yield in the solution state, but since the fluorescence intensity in the solid state is also strong, the host It is suitably used as a material. One pyromethene compound, which has fluorescence even in the solid state, may be used as a host material. However, the fluorescence quantum yield in the solution state is extremely high, the half width of the emission spectrum is small, and high color purity light emission. Can be suitably used as a dopant material.
本発明で用いられる好ましいホスト材料としては、ジケトピロロ［３，４−ｃ］ピロール誘導体一種のみに限る必要はなく、複数のジケトピロロ［３，４−ｃ］ピロール誘導体を混合して用いたり、既知のホスト材料の一種類以上をジケトピロロ［３，４−ｃ］ピロール誘導体と混合して用いてもよい。以前から発光体として知られていたアントラセン、フェナンスレン、ピレン、テトラセンなどの縮合環誘導体、Ｎ，Ｎ’−ジナフチル−Ｎ，Ｎ’−ジフェニル−４，４’−ジフェニル−１，１’−ジアミンなどの芳香族アミン誘導体、トリス（８−キノリナート）アルミニウム（III）をはじめとする金属キレート化オキシノイド化合物、ジスチリルベンゼン誘導体などのビススチリル誘導体、テトラフェニルブタジエン誘導体、インデン誘導体、クマリン誘導体、オキサジアゾール誘導体、ピロロピリジン誘導体、ペリノン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、カルバゾール誘導体、ポリマー系では、ポリフェニレンビニレン誘導体、ポリパラフェニレン誘導体、ポリフルオレン誘導体、ポリビニルカルバゾール誘導体そして、ポリチオフェン誘導体が好適に用いられる。 The preferred host material used in the present invention is not limited to a single diketopyrrolo [3,4-c] pyrrole derivative, and a mixture of a plurality of diketopyrrolo [3,4-c] pyrrole derivatives may be used. One or more kinds of host materials may be mixed with a diketopyrrolo [3,4-c] pyrrole derivative and used. Fused ring derivatives such as anthracene, phenanthrene, pyrene and tetracene, which have been known as light emitters, N, N′-dinaphthyl-N, N′-diphenyl-4,4′-diphenyl-1,1′-diamine, etc. Aromatic amine derivatives, metal chelated oxinoid compounds such as tris (8-quinolinato) aluminum (III), bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives , Pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, carbazole derivatives, in the polymer system, polyphenylene vinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives Body And, polythiophene derivatives are suitably used.
好ましいドーパント材料としては、ピロメテン化合物一種のみに限る必要はなく、複数のピロメテン化合物を混合して用いたり、既知のドーパント材料の一種類以上をピロメテン化合物と混合して用いても良い。従来から知られているナフタレン、アントラセン、フェナンスレン、ピレン、トリフェニレン、ペリレン、フルオレン、インデンなどのアリール環を有する化合物やその誘導体、フラン、ピロール、チオフェン、シロール、９−シラフルオレン、９，９’−スピロビシラフルオレン、ベンゾチオフェン、ベンゾフラン、インドール、ジベンゾチオフェン、ジベンゾフラン、イミダゾピリジン、フェナントロリン、ピラジン、ナフチリジン、キノキサリン、ピロロピリジン、チオキサンテンなどのヘテロアリール環を有する化合物やその誘導体、ジスチリルベンゼン誘導体、アミノスチリル誘導体、芳香族アセチレン誘導体、テトラフェニルブタジエン誘導体、スチルベン誘導体、アルダジン誘導体、クマリン誘導体、イミダゾール、チアゾール、チアジアゾール、カルバゾール、オキサゾール、オキサジアゾール、トリアゾールなどのアゾール誘導体およびその金属錯体およびＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミンに代表される芳香族アミン誘導体などが挙げられるが、これに限定されるものではない。 The preferred dopant material is not limited to a single pyromethene compound, and a plurality of pyromethene compounds may be mixed and used, or one or more known dopant materials may be mixed with a pyromethene compound. Conventionally known compounds having an aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene and derivatives thereof, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9′- Compounds having heteroaryl rings such as spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene, derivatives thereof, distyrylbenzene derivatives, Aminostyryl derivatives, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazoles, thiazoles Azole derivatives such as thiadiazole, carbazole, oxazole, oxadiazole, triazole and metal complexes thereof, and N, N′-diphenyl-N, N′-di (3-methylphenyl) -4,4′-diphenyl-1, An aromatic amine derivative typified by 1′-diamine is exemplified, but the invention is not limited thereto.
本発明の発光素子は陽極と陰極の間に少なくとも発光層が存在するが、発光層のみからなる構成の他に、１）正孔輸送層／発光層／電子輸送層および、２）発光層／電子輸送層、３）正孔輸送層／発光層などの積層構成が挙げられる。また、上記各層は、それぞれ単一層であってもよいし、複数層であってもよい。正孔輸送層および電子輸送層が複数層からなる場合、電極に接する側の層をそれぞれ正孔注入層および電子注入層と呼ぶことがあるが、以下の説明では正孔注入層は正孔輸送層に、電子注入層は電子輸送層にそれぞれ含まれる。 In the light emitting device of the present invention, at least a light emitting layer exists between the anode and the cathode. In addition to the constitution consisting of only the light emitting layer, 1) hole transport layer / light emitting layer / electron transport layer and 2) light emitting layer / Examples thereof include a laminated structure such as an electron transport layer and 3) a hole transport layer / a light emitting layer. Each of the above layers may be a single layer or a plurality of layers. When the hole transport layer and the electron transport layer are composed of a plurality of layers, the layers in contact with the electrodes may be referred to as a hole injection layer and an electron injection layer, respectively. The electron injection layer is included in each of the layers.
正孔輸送層は、正孔輸送材料の一種または二種以上を積層、混合するか、正孔輸送材料と高分子結着剤の混合物により形成される。正孔輸送材料としては、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミン、Ｎ，Ｎ’−ジナフチル−Ｎ，Ｎ’−ジフェニル−４，４’−ジフェニル−１，１’−ジアミン、４，４’，４”−トリス（３−メチルフェニル（フェニル）アミノ）トリフェニルアミンなどのトリフェニルアミン誘導体、ビス（Ｎ−アリルカルバゾール）またはビス（Ｎ−アルキルカルバゾール）などのカルバゾール誘導体、ピラゾリン誘導体、スチルベン系化合物、ヒドラゾン系化合物、ベンゾフラン誘導体やチオフェン誘導体、オキサジアゾール誘導体、フタロシアニン誘導体、ポルフィリン誘導体などの複素環化合物、ポリマー系ではトリフェニルアミン等の前記誘導体を側鎖に有するポリカーボネートやスチレン誘導体、ポリビニルカルバゾールおよびポリシランなどが好ましいが、発光素子の作製に必要な薄膜を形成し、陽極から正孔が注入できて、さらに正孔を輸送できる化合物であれば特に限定されるものではない。 The hole transport layer is formed by laminating and mixing one or more hole transport materials or a mixture of the hole transport material and the polymer binder. As the hole transport material, N, N′-diphenyl-N, N′-di (3-methylphenyl) -4,4′-diphenyl-1,1′-diamine, N, N′-dinaphthyl-N, Triphenylamine derivatives such as N′-diphenyl-4,4′-diphenyl-1,1′-diamine, 4,4 ′, 4 ″ -tris (3-methylphenyl (phenyl) amino) triphenylamine, bis ( Heterocyclic compounds such as carbazole derivatives such as N-allylcarbazole) or bis (N-alkylcarbazole), pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives In the polymer system, a polycarbonate having the above-mentioned derivative such as triphenylamine in the side chain And styrene derivatives, polyvinyl carbazole, and polysilane are preferable, but the compound is particularly limited as long as it is a compound that can form a thin film necessary for manufacturing a light emitting device, inject holes from the anode, and further transport holes. is not.
本発明において電子輸送層とは、陰極から電子が注入され、さらに電子を輸送する層であり、電子注入効率が高く、注入された電子を効率良く輸送することが望ましい。そのため電子輸送層に用いられる材料は、電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であることが要求される。ただし、正孔と電子の輸送バランスを考えた場合に、電子輸送層が陽極からの正孔が再結合せずに陰極側へ流れるのを効率よく阻止できる役割を主に果たす場合には、電子輸送能力がそれ程高くなくても、発光効率を向上させる効果は電子輸送能力が高い材料と同等に有する。したがって、本発明における電子輸送層は、正孔の移動を効率よく阻止できる正孔阻止層も同義のものとして含まれる。 In the present invention, the electron transport layer is a layer in which electrons are injected from the cathode and further transports electrons, and it is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. Therefore, the material used for the electron transport layer is required to be a substance having a high electron affinity, a high electron mobility, excellent stability, and a trapping impurity that is unlikely to be generated during manufacture and use. However, when considering the transport balance between holes and electrons, the electron transport layer mainly plays the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination. Even if the transport capability is not so high, the effect of improving the light emission efficiency is equivalent to that of a material having a high electron transport capability. Therefore, the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.
電子輸送層に用いられる電子輸送材料としては、ナフタレン、アントラセンなどの縮合環系芳香環誘導体、４，４’−ビス（ジフェニルエテニル）ビフェニルに代表されるスチリル系芳香環誘導体、ペリレン誘導体、ペリノン誘導体、クマリン誘導体、ナフタルイミド誘導体、アントラキノンやジフェノキノンなどのキノン誘導体、リンオキサイド誘導体、カルバゾール誘導体およびインドール誘導体、トリス（８−キノリノラート）アルミニウム（III）などのキノリノール錯体やヒドロキシフェニルオキサゾール錯体などのヒドロキシアゾール錯体、アゾメチン錯体、トロポロン金属錯体およびフラボノール金属錯体、電子受容性窒素を有するヘテロアリール環からなる化合物などが挙げられる。中でも、駆動電圧の低下や、耐久性の向上の観点から、電子受容性窒素を有するヘテロアリール環を有する化合物が、好適に用いられる。さらにヘテロアリール環を有する化合物が炭素、水素、窒素、酸素、ケイ素、リンからなる群の中から選ばれる元素で構成されると、駆動電圧が著しく低下するため好ましい。 Examples of the electron transport material used for the electron transport layer include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, perylene derivatives, and perinone. Derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives, quinolinol complexes such as tris (8-quinolinolato) aluminum (III), and hydroxyazoles such as hydroxyphenyl oxazole complexes Examples include complexes, azomethine complexes, tropolone metal complexes and flavonol metal complexes, and compounds composed of heteroaryl rings having electron-accepting nitrogen. Among these, compounds having a heteroaryl ring having electron-accepting nitrogen are preferably used from the viewpoint of lowering driving voltage and improving durability. Furthermore, it is preferable that the compound having a heteroaryl ring is composed of an element selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, silicon and phosphorus because the driving voltage is remarkably lowered.
電子受容性窒素を有するヘテロアリール環を有し、かつ炭素、水素、窒素、酸素、ケイ素、リンからなる群の中から選ばれる元素で構成される化合物としては、ベンズイミダゾール誘導体、ベンズオキサゾール誘導体、ベンズチアゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体、ピラジン誘導体、フェナントロリン誘導体、キノキサリン誘導体、キノリン誘導体、ベンゾキノリン誘導体、ビピリジンやターピリジンなどのオリゴピリジン誘導体、キノキサリン誘導体およびナフチリジン誘導体などが好ましい化合物として挙げられる。中でも、トリス（Ｎ−フェニルベンズイミダゾール−２−イル）ベンゼンなどのイミダゾール誘導体、１，３−ビス［（４−ｔｅｒｔ−ブチルフェニル）１，３，４−オキサジアゾリル］フェニレンなどのオキサジアゾール誘導体、Ｎ−ナフチル−２，５−ジフェニル−１，３，４−トリアゾールなどのトリアゾール誘導体、バソクプロインや１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンなどのフェナントロリン誘導体、２，２’−ビス（ベンゾ［ｈ］キノリン−２−イル）−９，９’−スピロビフルオレンなどのベンゾキノリン誘導体、１，３−ビス（２，６−ジピリジルピリジン−４−イル）ベンゼンなどのターピリジン誘導体、ビス（１−ナフチル）−４−（１，８−ナフチリジン−２−イル）フェニルホスフィンオキサイドなどのナフチリジン誘導体が、電子輸送能の観点から好ましく用いられる。 As a compound having a heteroaryl ring having an electron-accepting nitrogen and composed of an element selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus, a benzimidazole derivative, a benzoxazole derivative, Preferred compounds include benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives, and naphthyridine derivatives. Can be mentioned. Among them, imidazole derivatives such as tris (N-phenylbenzimidazol-2-yl) benzene, oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) 1,3,4-oxadiazolyl] phenylene, Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproine and 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,2 ′ Benzoquinoline derivatives such as bis (benzo [h] quinolin-2-yl) -9,9′-spirobifluorene, terpyridine derivatives such as 1,3-bis (2,6-dipyridylpyridin-4-yl) benzene Bis (1-naphthyl) -4- (1,8-naphthyridin-2-yl) phenylphosphite Naphthyridine derivatives such as oxide are preferably used from the viewpoint of electron transporting capability.
これらの電子輸送材料は単独でも用いられるが、異なる電子輸送材料と混合して使用しても構わない。また、アルカリ金属やアルカリ土類金属などの金属と混合して用いることも可能である。電子輸送層のイオン化ポテンシャルは、特に限定されるものではないが、好ましくは５．８ｅＶ以上、より好ましくは６ｅＶ以上である。５．８ｅＶ以上であれば、発光層内の正孔を効率よく閉じこめ、電子と正孔の再結合確率を向上させることができる。 These electron transport materials are used alone, but may be used in combination with different electron transport materials. It is also possible to use a mixture with a metal such as an alkali metal or an alkaline earth metal. The ionization potential of the electron transport layer is not particularly limited, but is preferably 5.8 eV or more, more preferably 6 eV or more. If it is 5.8 eV or more, the hole in a light emitting layer can be confined efficiently and the recombination probability of an electron and a hole can be improved.
発光素子を構成する上記各層の形成方法は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、コーティング法など特に限定されるものではないが、通常は、抵抗加熱蒸着または電子ビーム蒸着が特性面で好ましい。 The method for forming each layer constituting the light-emitting element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, etc., but resistance heating vapor deposition or electron beam vapor deposition is usually a characteristic. In terms of surface.
層の厚みは、発光物質の抵抗値にもよるので限定することはできないが、１〜１０００ｎｍの間から選ばれる。発光層、電子輸送層、正孔輸送層の膜厚はそれぞれ、好ましくは１ｎｍ以上２００ｎｍ以下であり、さらに好ましくは５ｎｍ以上１００ｎｍ以下である。 The thickness of the layer depends on the resistance value of the luminescent material and cannot be limited, but is selected from 1 to 1000 nm. The film thicknesses of the light emitting layer, the electron transport layer, and the hole transport layer are each preferably 1 nm to 200 nm, and more preferably 5 nm to 100 nm.
本発明の発光素子は、電気エネルギーを光に変換できる発光素子である。ここに電気エネルギーとは主に直流電流を指すが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力や寿命を考慮すると、できるだけ低いエネルギーで最大の輝度が得られるようにする。 The light-emitting element of the present invention is a light-emitting element that can convert electrical energy into light. Here, the electric energy mainly indicates a direct current, but a pulse current or an alternating current can also be used. The current value and the voltage value are not particularly limited, but the maximum luminance can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the element.
本発明の発光素子は、例えば、マトリクスおよび／またはセグメント方式で表示するディスプレイとして好適に用いられる。 The light emitting device of the present invention is suitably used as a display for displaying in a matrix and / or segment system, for example.
本発明におけるマトリクスとは、表示のための画素が格子状やモザイク状など二次元的に配置されたものをいい、画素の集合で文字や画像を表示する。画素の形状やサイズは用途によって決まる。例えば、パソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられ、また、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法としては、線順次駆動方法やアクティブマトリクスのどちらでもよい。線順次駆動は構造が簡単であり、動作特性を考慮した場合、アクティブマトリクスの方が用いる材料に負担をかけず、長寿命のディスプレイが得られる点で優れる場合があるので、これも用途によって使い分ければ良い。 The matrix in the present invention refers to a pixel in which pixels for display are two-dimensionally arranged such as a lattice shape or a mosaic shape, and displays a character or an image by a set of pixels. The shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become. In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential drive has a simple structure, and considering the operating characteristics, the active matrix may be superior in terms of obtaining a long-life display without imposing a burden on the material used. Just do it.
本発明におけるセグメント方式（タイプ）とは、予め決められた情報を表示するようにパターンを形成し、決められた領域を発光させることになる。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示および自動車のパネル表示などが挙げられる。そして、マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。 In the segment system (type) in the present invention, a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned. The matrix display and the segment display may coexist in the same panel.
本発明の発光素子は、各種機器等のバックライトとしても好ましく用いられる。バックライトは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ装置、自動車パネル、表示板および標識などに使用される。特に、液晶表示装置、中でも薄型化が課題となっているパソコン用途のバックライトには、薄型、軽量の特性を有する本発明の発光素子を好適に用いることができる。 The light emitting device of the present invention is also preferably used as a backlight for various devices. The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like. In particular, a light-emitting element of the present invention having thin and lightweight characteristics can be suitably used for a liquid crystal display device, particularly a backlight for a personal computer for which thinning is an issue.
以下、実施例をあげて本発明を説明するが、本発明はこれらの実施例によって限定されるものではない。なお、下記の各実施例にある化合物の番号は上記の具体的に列挙した化合物の番号を指すものである。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not limited by these Examples. In addition, the number of the compound in each following Example points out the number of the compound specifically enumerated above.
実施例１
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、エッチングを行った。得られた基板をアセトン、セミコクリン（登録商標）５６（フルウチ化学（株）製）で各々１５分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０−５Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として銅フタロシアニン（ＣｕＰｃ）を１０ｎｍ蒸着した。次に、正孔輸送材料としてＮ，Ｎ’−ジナフチル−Ｎ，Ｎ’−ジフェニル−１，１’−ジフェニル−４，４’−ジアミン（ＮＰＤ）を５０ｎｍの厚さに蒸着し、正孔輸送層を形成した。次にホスト材料として化合物（Ａ−１）を、ドーパント材料として９−ジエチルアミノ−５Ｈ−ベンゾ（ａ）フェノキサジン−５−オン（ジクロロメタン溶液中の蛍光ピーク波長は６１０ｎｍ）を用いて、ドーパント材料の濃度が１ｗｔ％になるように４０ｎｍの厚さに共蒸着して発光層を形成し、１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンを３５ｎｍの厚さに蒸着して電子輸送層を形成した。電子輸送材料のイオン化ポテンシャルは６．１０ｅＶである（大気雰囲気型紫外線光電子分析装置（ＡＣ−１：理研計器（株））を用いて薄膜状態で測定）。次にフッ化リチウムを０．５ｎｍドーピングした後、アルミニウムを１５０ｎｍ蒸着して陰極を形成し、５×５ｍｍ角の素子を作製した。この発光素子からは、発光ピーク波長６０９ｎｍ、スペクトル半値幅７１ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は２．０ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 1
A glass substrate on which an ITO transparent conductive film was deposited to a thickness of 150 nm (Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporated product) was cut into 30 × 40 mm and etched. The obtained substrate was ultrasonically washed with acetone and Semicocrine (registered trademark) 56 (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, respectively, and then washed with ultra pure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes and dried. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus was 5 × 10 −5 Pa or less. First, copper phthalocyanine (CuPc) was vapor-deposited to a thickness of 10 nm as a hole injection material by a resistance heating method. Next, as a hole transport material, N, N′-dinaphthyl-N, N′-diphenyl-1,1′-diphenyl-4,4′-diamine (NPD) is vapor-deposited to a thickness of 50 nm, and hole transport is performed. A layer was formed. Next, using the compound (A-1) as the host material and 9-diethylamino-5H-benzo (a) phenoxazin-5-one (the fluorescence peak wavelength in the dichloromethane solution is 610 nm) as the dopant material, A light emitting layer is formed by co-evaporation to a thickness of 40 nm so that the concentration is 1 wt%, and 1,3-bis (1,10-phenanthroline-9-yl) benzene is deposited to a thickness of 35 nm to form electrons. A transport layer was formed. The ionization potential of the electron transport material is 6.10 eV (measured in a thin film state using an atmospheric-type ultraviolet photoelectron analyzer (AC-1: Riken Keiki Co., Ltd.)). Next, after doping 0.5 nm of lithium fluoride, 150 nm of aluminum was deposited to form a cathode, and a 5 × 5 mm square device was fabricated. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 609 nm and a spectral half width of 71 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 2.0 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例２
ドーパント材料として４−（ジシアノメチレン）−２−メチル−６−（１，１，７，７−テトラメチルジュロリジル−９−エニル）−４Ｈ−ピラン（ジクロロメタン溶液中の蛍光ピーク波長は６２５ｎｍ）を用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６０９ｎｍ、スペクトル半値幅８８ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は３．０ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 2
4- (Dicyanomethylene) -2-methyl-6- (1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (fluorescent peak wavelength in dichloromethane solution is 625 nm) as dopant material A light emitting device was produced in the same manner as in Example 1 except that was used. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 609 nm and a spectral half width of 88 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 3.0 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例３
ドーパント材料として化合物（Ｂ−３１）（ジクロロメタン溶液中の蛍光ピーク波長は６２９ｎｍ）を用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６３６ｎｍ、スペクトル半値幅３３ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は１．５ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 3
A light emitting device was produced in the same manner as in Example 1 except that the compound (B-31) (fluorescence peak wavelength in dichloromethane solution was 629 nm) was used as the dopant material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 636 nm and a spectral half width of 33 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 1.5 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例４
ドーパント材料として化合物（Ｂ−１）（ジクロロメタン溶液中の蛍光ピーク波長は６０５ｎｍ）を用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は４．０ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 4
A light emitting device was produced in the same manner as in Example 1 except that the compound (B-1) (fluorescence peak wavelength in dichloromethane solution was 605 nm) was used as the dopant material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 4.0 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
比較例１
ホスト材料として１，４−ジケト−２，５−ジメチル−３，６−ジフェニルピロロ［３，４−ｃ］ピロールを用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６０９ｎｍ、スペクトル半値幅５２ｎｍのドーパント材料に基づく赤色発光が得られたが、１０ｍＡ／ｃｍ２時の発光効率は２．０ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は２５％であった。
Comparative Example 1
A light emitting device was produced in the same manner as in Example 1 except that 1,4-diketo-2,5-dimethyl-3,6-diphenylpyrrolo [3,4-c] pyrrole was used as the host material. From this light-emitting element, red light emission based on a dopant material having an emission peak wavelength of 609 nm and a spectral half width of 52 nm was obtained, but the light emission efficiency at 10 mA / cm 2 was 2.0 cd / A. In addition, the luminance retention rate after 500 hours of continuous lighting of this element was 25%.
比較例２
ホスト材料として１，４−ジケト−２，５−ビス（３，５−ジメチルベンジル）−３，６−ビス（４−メチルフェニル）ピロロ［３，４−ｃ］ピロールを用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６０９ｎｍ、スペクトル半値幅５２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は４．０ｃｄ／Ａであった。しかしながら、この素子の５００時間連続点灯後の輝度保持率は３５％であった。
Comparative Example 2
Examples except that 1,4-diketo-2,5-bis (3,5-dimethylbenzyl) -3,6-bis (4-methylphenyl) pyrrolo [3,4-c] pyrrole was used as the host material In the same manner as in Example 1, a light emitting device was manufactured. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 609 nm and a spectral half width of 52 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 4.0 cd / A. However, the luminance retention rate after 500 hours of continuous lighting of this element was 35%.
比較例３
ホスト材料として１，４−ジケト−２，５−３，５−ジメチル−３，６−ビス（４−メチルナフタレン−１−イル）ピロロ［３，４−ｃ］ピロールを用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６０９ｎｍ、スペクトル半値幅５２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は４．０ｃｄ／Ａであった。しかしながら、この素子の５００時間連続点灯後の輝度保持率は６０％であった。
Comparative Example 3
Examples except that 1,4-diketo-2,5-3,5-dimethyl-3,6-bis (4-methylnaphthalen-1-yl) pyrrolo [3,4-c] pyrrole was used as the host material In the same manner as in Example 1, a light emitting device was manufactured. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 609 nm and a spectral half width of 52 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 4.0 cd / A. However, the luminance retention rate of this device after continuous lighting for 500 hours was 60%.
実施例５
ドーパント材料として化合物（Ｂ−３９）（ジクロロメタン溶液中の蛍光ピーク波長は６１３ｎｍ）を用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１８ｎｍ、スペクトル半値幅４８ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は５．０ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 5
A light emitting device was produced in the same manner as in Example 1 except that the compound (B-39) (fluorescence peak wavelength in dichloromethane solution was 613 nm) was used as the dopant material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 618 nm and a spectral half width of 48 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 5.0 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例６
ドーパント材料として化合物（Ｂ−５１）（ジクロロメタン溶液中の蛍光ピーク波長は６０９ｎｍ）を用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は６．０ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 6
A light emitting device was produced in the same manner as in Example 1 except that the compound (B-51) (fluorescence peak wavelength in dichloromethane solution was 609 nm) was used as the dopant material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 6.0 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例７
ホスト材料として化合物（Ａ−２）を用いた以外は実施例６と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は３．８ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 7
A light emitting device was produced in the same manner as in Example 6 except that the compound (A-2) was used as the host material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 3.8 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例８
ホスト材料として化合物（Ａ−４）を用いた以外は実施例６と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は６．０ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 8
A light emitting device was produced in the same manner as in Example 6 except that the compound (A-4) was used as the host material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 6.0 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例９
ホスト材料として化合物（Ａ−７）を用いた以外は実施例６と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は３．５ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は９０％であった。
Example 9
A light emitting device was produced in the same manner as in Example 6 except that the compound (A-7) was used as the host material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 3.5 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 90%.
実施例１０
ホスト材料として化合物（Ａ−２１）を用いた以外は実施例６と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は４．２ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８０％であった。
Example 10
A light-emitting element was fabricated in the same manner as in Example 6 except that the compound (A-21) was used as the host material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 4.2 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 80%.
実施例１１
電子輸送材料として下記に示すＥＴＭ１を用いた以外は実施例６と同様にして発光素子を作製した。ＥＴＭ１のイオン化ポテンシャルは５．９９ｅＶである。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は５．５ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８０％であった。
Example 11
A light emitting device was produced in the same manner as in Example 6 except that ETM1 shown below was used as the electron transporting material. The ionization potential of ETM1 is 5.99 eV. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 5.5 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 80%.
実施例１２
電子輸送材料として下記に示すＥＴＭ２を用いた以外は実施例６と同様にして発光素子を作製した。ＥＴＭ２のイオン化ポテンシャルは６．０７ｅＶである。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は５．７ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 12
A light emitting device was produced in the same manner as in Example 6 except that ETM2 shown below was used as the electron transport material. The ionization potential of ETM2 is 6.07 eV. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 5.7 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例１３
電子輸送材料として下記に示すＥＴＭ３用いた以外は実施例６と同様にして発光素子を作製した。ＥＴＭ３のイオン化ポテンシャルは６．０７ｅＶである。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は６．２／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 13
A light emitting device was produced in the same manner as in Example 6 except that ETM3 shown below was used as the electron transport material. The ionization potential of ETM3 is 6.07 eV. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 6.2 / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例１４
ホスト材料として化合物（Ａ−１０）を用いた以外は実施例１３と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長６１７ｎｍ、スペクトル半値幅４２ｎｍのドーパント材料に基づく赤色発光が得られ、１０ｍＡ／ｃｍ２時の発光効率は６．５ｃｄ／Ａであった。また、この素子の５００時間連続点灯後の輝度保持率は８５％であった。
Example 14
A light emitting device was produced in the same manner as in Example 13 except that the compound (A-10) was used as the host material. From this light emitting element, red light emission based on a dopant material having an emission peak wavelength of 617 nm and a spectral half width of 42 nm was obtained, and the light emission efficiency at 10 mA / cm 2 was 6.5 cd / A. In addition, the luminance retention rate after continuous lighting for 500 hours of this element was 85%.
実施例１５
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子社製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、フォトリソグラフィ法によって３００μｍピッチ（残り幅２７０μｍ）×３２本のストライプ状にパターン加工した。ＩＴＯストライプの長辺方向片側は外部との電気的接続を容易にするために１．２７ｍｍピッチ（開口部幅８００μｍ）まで広げてある。得られた基板をアセトン、セミコクリン（登録商標）５６（フルウチ化学（株）製）で各々１５分間超音波洗浄してから、超純水で洗浄した。続いてイソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０−４Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料としてＣｕＰｃを１０ｎｍ蒸着した。次に、正孔輸送材料としてＮＰＤを５０ｎｍの厚さに蒸着し、正孔輸送層を形成した。次にホスト材料として化合物（Ａ−１）を、ドーパント材料として化合物（Ｂ−３５）を用いて、ドーパント材料の濃度が１ｗｔ％になるように４０ｎｍの厚さに共蒸着して発光層を形成し、１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンを３５ｎｍの厚さに蒸着して電子輸送層を形成した。次に厚さ５０μｍのコバール板にウエットエッチングによって１６本の２５０μｍの開口部（残り幅５０μｍ、３００μｍピッチに相当）を設けたマスクを、真空中でＩＴＯストライプに直交するようにマスク交換し、マスクとＩＴＯ基板が密着するように裏面から磁石で固定した。そしてマグネシウムを５０ｎｍ、アルミニウムを１５０ｎｍ蒸着して３２×１６ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
Example 15
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporation product) on which an ITO transparent conductive film is deposited to 150 nm is cut into 30 × 40 mm, and 300 μm pitch (remaining width 270 μm) × 32 stripes by photolithography. Pattern processed. One side of the ITO stripe in the long side direction is expanded to a pitch of 1.27 mm (opening width 800 μm) in order to facilitate electrical connection with the outside. The obtained substrate was ultrasonically washed with acetone and Semicocrine (registered trademark) 56 (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, respectively, and then washed with ultra pure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. First, CuPc was vapor-deposited as a hole injection material by 10 nm by a resistance heating method. Next, NPD was vapor-deposited as a hole transport material to a thickness of 50 nm to form a hole transport layer. Next, using compound (A-1) as the host material and compound (B-35) as the dopant material, a light emitting layer is formed by co-evaporation to a thickness of 40 nm so that the concentration of the dopant material is 1 wt%. Then, 1,3-bis (1,10-phenanthroline-9-yl) benzene was evaporated to a thickness of 35 nm to form an electron transport layer. Next, a mask having 16 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) formed by wet etching on a 50 μm thick Kovar plate was replaced by a mask so as to be orthogonal to the ITO stripe in a vacuum. And it fixed with the magnet from the back so that an ITO board | substrate might closely_contact | adhere. Magnesium was deposited with a thickness of 50 nm and aluminum was deposited with a thickness of 150 nm to produce a 32 × 16 dot matrix element. When this element was driven in matrix, characters could be displayed without crosstalk.
Claims (2)
Ａｒ１は一般式（３）で表される有機基より選ばれ、
Ar 1 is selected from organic groups represented by the general formula (3),
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| JPWO2021039205A1 (en) * | 2019-08-29 | 2021-03-04 |
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| US9209412B2 (en) | 2011-09-02 | 2015-12-08 | Basf Se | Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers |
| JP2015228460A (en) * | 2014-06-02 | 2015-12-17 | セイコーエプソン株式会社 | Light-emitting device, electronic apparatus and inspection method |
| US10367148B2 (en) | 2014-06-02 | 2019-07-30 | Seiko Epson Corporation | Light-emitting device, electronic apparatus, and inspection method |
| JPWO2021039205A1 (en) * | 2019-08-29 | 2021-03-04 | ||
| WO2021039205A1 (en) * | 2019-08-29 | 2021-03-04 | 富士フイルム株式会社 | Composition, film, near-infrared cut-off filter, pattern formation method, laminate, solid-state imaging element, infrared sensor, image display device, camera module and compound |
| CN114269556A (en) * | 2019-08-29 | 2022-04-01 | 富士胶片株式会社 | Composition, film, near-infrared cut filter, pattern formation method, laminate, solid-state imaging element, infrared sensor, image display device, camera module, and compound |
| JP7237166B2 (en) | 2019-08-29 | 2023-03-10 | 富士フイルム株式会社 | Composition, film, near-infrared cut filter, pattern forming method, laminate, solid-state imaging device, infrared sensor, image display device, camera module, and compound |
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