JP2007126403A - Dibenzothiophene derivative and organic electroluminescent device using the same - Google Patents
Dibenzothiophene derivative and organic electroluminescent device using the same Download PDFInfo
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 title claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 52
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 238000002347 injection Methods 0.000 claims description 22
- 239000007924 injection Substances 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000005401 siloxanyl group Chemical group 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 238000005401 electroluminescence Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 48
- HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 0 **c1c(**)c(*)c(*)c2c1[n]c1c2CC(*)=CC=I1 Chemical compound **c1c(**)c(*)c(*)c2c1[n]c1c2CC(*)=CC=I1 0.000 description 1
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N Cc1cc(C)cc(C)c1 Chemical compound Cc1cc(C)cc(C)c1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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Abstract
Description
本発明は、ジベンゾチオフェン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子に関するものである。 The present invention relates to dibenzothiophene derivatives and organic electroluminescence devices using the same.
有機エレクトロルミネッセンス素子（有機ＥＬ素子）は、ディスプレイや照明への応用の観点から活発に開発が進められている。有機ＥＬ素子の駆動原理は、以下のようなものである。すなわち、ホール注入電極及び電子注入電極からそれぞれホールと電子が注入され、これらが有機化合物からなる薄膜中を輸送され、発光層において再結合し励起状態が生じ、この励起状態から発光が得られる。発光層における発光材料としては、１重項状態から発光する蛍光発光材料や、３重項状態から発光する燐光発光材料が用いられている。燐光発光材料としては、イリジウムや白金などの重金属錯体が用いられており、発光材料として燐光発光材料を用いることにより、蛍光発光材料を用いた場合に比べ、高い効率の発光特性が理論上可能であることから、燐光発光材料を用いた有機ＥＬ素子について急速に開発が進められている。 Organic electroluminescence elements (organic EL elements) are being actively developed from the viewpoint of application to displays and lighting. The driving principle of the organic EL element is as follows. That is, holes and electrons are injected from the hole injection electrode and the electron injection electrode, respectively, and are transported through a thin film made of an organic compound, recombined in the light emitting layer to generate an excited state, and light emission is obtained from this excited state. As the light emitting material in the light emitting layer, a fluorescent light emitting material that emits light from a singlet state or a phosphorescent material that emits light from a triplet state is used. As the phosphorescent material, heavy metal complexes such as iridium and platinum are used, and by using the phosphorescent material as the light emitting material, light emission characteristics with higher efficiency are theoretically possible compared to the case of using a fluorescent material. For this reason, organic EL devices using phosphorescent materials are being rapidly developed.
燐光発光材料を用いた有機ＥＬ素子の発光層においては、ホスト材料に発光材料を添加することにより発光層を形成することが提案されており、ホスト材料としては、従来よりＣＢＰ（４，４′−Ｎ，Ｎ′−ジカルバゾール−ビフェニル）などのカルバゾール誘導体が主に提案されている。 In a light emitting layer of an organic EL element using a phosphorescent light emitting material, it has been proposed to form a light emitting layer by adding a light emitting material to a host material. As a host material, CBP (4, 4 'has been conventionally used. Carbazole derivatives such as -N, N'-dicarbazole-biphenyl) have been mainly proposed.
しかしながら、カルバゾール誘導体をホスト材料として用いた有機ＥＬ素子においては、駆動電圧が高く、消費電力を低減することができないという問題があった。 However, an organic EL element using a carbazole derivative as a host material has a problem that driving voltage is high and power consumption cannot be reduced.
また、カルバゾール誘導体は、その結晶性の高さから製膜安定性や高温駆動時における素子安定性に問題があった。 In addition, the carbazole derivative has a problem in film formation stability and device stability during high temperature driving because of its high crystallinity.
本発明者は、特定の構造を有するジベンゾチオフェン誘導体が、発光層のホスト材料などの電子輸送性材料として優れていることを見出し、本発明を完成するに至った。特許文献１及び特許文献２においては、ジベンゾチオフェン誘導体を有機ＥＬ素子の材料として用いることが開示されているが、これらの文献において用いられているジベンゾチオフェン誘導体は、ジベンゾチオフェン骨格にカルバゾールあるいはアミン置換基が導入されたものであり、本発明のジベンゾチオフェン誘導体のような優れた特性が得られるものではない。
The present inventor has found that a dibenzothiophene derivative having a specific structure is excellent as an electron transporting material such as a host material of a light emitting layer, and has completed the present invention.
また、これらの文献においては、電荷輸送材料や、１重項ドーパントのホスト材料として検討されており、燐光発光材料のホスト材料としての検討はなされていない。
本発明の目的は、有機ＥＬ素子の発光層のホスト材料などの電子輸送性材料として用いて駆動電圧を低減することができ、発光効率を向上させることができるジベンゾチオフェン誘導体及びそれらを用いた有機ＥＬ素子を提供することにある。 An object of the present invention is to use a dibenzothiophene derivative capable of reducing driving voltage and improving luminous efficiency by using it as an electron transporting material such as a host material of a light emitting layer of an organic EL element, and an organic material using them. The object is to provide an EL element.
本発明のジベンゾチオフェン誘導体は、以下の一般式（１）で表されることを特徴としている。 The dibenzothiophene derivative of the present invention is represented by the following general formula (1).
（ここでＲ１〜Ｒ１８は、それぞれ同じであっても異なっていてもよく、水素、アルキル基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アリール基、アラルキル基、アリールオキシ基、アリールチオ基、ヘテロ環基、アミノ基、アシル基、カルボニル基、カルボキシル基、カルバモイル基、アルコキシカルボニル基、アリールオキシカルボニル基、アシルオキシ基、アシルアミノ基、ヒドロキシル基、イミノ基、シアノ基、ニトロ基、ハロゲン基、スルホニル基、シリル基、シロキサニル基のうちのいずれかを表し、これらの基は置換されたものであってもよい。また、隣接した置換基との間で環が形成されていてもよい。） (Wherein R 1 to R 18 may be the same as or different from each other, hydrogen, alkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, aryl group, aralkyl group, aryloxy group, Arylthio group, heterocyclic group, amino group, acyl group, carbonyl group, carboxyl group, carbamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, hydroxyl group, imino group, cyano group, nitro group, halogen Represents any one of a group, a sulfonyl group, a silyl group, and a siloxanyl group, and these groups may be substituted, or a ring may be formed between adjacent substituents. .)
本発明のジベンゾチオフェン誘導体は、電子輸送性を有する化合物であり、有機ＥＬ素子における発光層のホスト材料、及び電子輸送性材料として用いることができる。本発明のジベンゾチオフェン誘導体を用いることにより、従来のＣＢＰなどの電子輸送性材料に比べ、発光効率を向上させることができ、駆動電圧を低減させることができる。従って、消費電力を低減することができる。 The dibenzothiophene derivative of the present invention is a compound having an electron transporting property, and can be used as a host material and an electron transporting material for a light emitting layer in an organic EL device. By using the dibenzothiophene derivative of the present invention, light emission efficiency can be improved and driving voltage can be reduced as compared with conventional electron transporting materials such as CBP. Therefore, power consumption can be reduced.
また、本発明のジベンゾチオフェン誘導体を用いることにより、素子の連続駆動における輝度半減期を長くすることができる。従って、素子の駆動安定性を向上させることができる。 Further, by using the dibenzothiophene derivative of the present invention, the luminance half-life in continuous driving of the element can be extended. Therefore, the driving stability of the element can be improved.
本発明のジベンゾチオフェン誘導体は、上記のように電子輸送性を有するものであるので、発光層におけるホスト材料、ホール阻止層、電子輸送層、電子注入層などの有機化合物層に用いることができる。 Since the dibenzothiophene derivative of the present invention has an electron transport property as described above, it can be used for organic compound layers such as a host material, a hole blocking layer, an electron transport layer, and an electron injection layer in a light emitting layer.
本発明のジベンゾチオフェン誘導体においては、カルバゾールなどにおける窒素原子に比べ重い原子である硫黄原子を含むジベンゾチオフェン（ジフェニルスルフィド）の構造を有している。一般的に重い原子が近傍に存在すると、励起過程において３重項励起状態への遷移が誘発されることが知られている（重原子効果）。本発明におけるジベンゾチオフェン誘導体においては、重原子である硫黄原子が導入されているので、発光層のホスト材料として用いた場合に、燐光発光材料の３重項励起状態からの発光である燐光発光の効率を向上させることができると考えられる。従って、本発明のジベンゾチオフェン誘導体は、燐光発光材料を用いた発光層におけるホスト材料として用いた場合により有効な効果が得られる。 The dibenzothiophene derivative of the present invention has a dibenzothiophene (diphenyl sulfide) structure containing a sulfur atom that is heavier than a nitrogen atom in carbazole or the like. In general, it is known that when a heavy atom is present in the vicinity, a transition to a triplet excited state is induced in the excitation process (heavy atom effect). In the dibenzothiophene derivative in the present invention, a sulfur atom which is a heavy atom is introduced. Therefore, when used as a host material of the light emitting layer, phosphorescence emission which is light emission from a triplet excited state of the phosphorescent light emitting material is performed. It is thought that efficiency can be improved. Therefore, the dibenzothiophene derivative of the present invention provides a more effective effect when used as a host material in a light emitting layer using a phosphorescent light emitting material.
また、本発明のジベンゾチオフェン誘導体においては、ベンゼン環のメタ位、すなわち１位、３位、及び５位のいずれかにベンゾチアゾール環が複数導入されている。このような骨格の化合物は、良好なアモルファス性を有することが知られている。従って、本発明のジベンゾチオフェン誘導体は、製膜した際の安定性に優れている。実施例において作製したジベンゾチオフェン誘導体は、熱分析により明確なガラス転移点が確認されておらず、良好な融解型の熱特性を有するものであることがわかっている。 In the dibenzothiophene derivative of the present invention, a plurality of benzothiazole rings are introduced at any of the meta positions of the benzene ring, that is, the 1-position, 3-position, and 5-position. Such a skeleton compound is known to have good amorphous properties. Therefore, the dibenzothiophene derivative of the present invention is excellent in stability when formed into a film. The dibenzothiophene derivatives produced in the examples have no clear glass transition point confirmed by thermal analysis and are known to have good melting-type thermal characteristics.
本発明の限定された局面におけるジベンゾチオフェン誘導体は、以下の一般式（２）で表されることを特徴としている。 The dibenzothiophene derivative in a limited aspect of the present invention is characterized by being represented by the following general formula (2).
（ここでＲ１〜Ｒ１４及びＲ１９〜Ｒ２５は、それぞれ同じであっても異なっていてもよく、水素、アルキル基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アリール基、アラルキル基、アリールオキシ基、アリールチオ基、ヘテロ環基、アミノ基、アシル基、カルボニル基、カルボキシル基、カルバモイル基、アルコキシカルボニル基、アリールオキシカルボニル基、アシルオキシ基、アシルアミノ基、ヒドロキシル基、イミノ基、シアノ基、ニトロ基、ハロゲン基、スルホニル基、シリル基、シロキサニル基のうちのいずれかを表し、これらの基は置換されたものであってもよい。また、隣接した置換基との間で環が形成されていてもよい。） (Wherein R 1 to R 14 and R 19 to R 25 may be the same as or different from each other, hydrogen, alkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, aryl group, aralkyl. Group, aryloxy group, arylthio group, heterocyclic group, amino group, acyl group, carbonyl group, carboxyl group, carbamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, hydroxyl group, imino group, cyano Represents any one of a group, a nitro group, a halogen group, a sulfonyl group, a silyl group, and a siloxanyl group, and these groups may be substituted, and a ring is formed between adjacent substituents. (It may be formed.)
本発明のさらに限定された局面におけるジベンゾチオフェン誘導体は、以下の一般式（３）で表されることを特徴としている。 The dibenzothiophene derivative in a further limited aspect of the present invention is characterized by being represented by the following general formula (3).
（ここでＲ１、Ｒ１２及びＲ２３は、それぞれ同じであっても異なっていてもよく、水素、アルキル基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アリール基、アラルキル基、アリールオキシ基、アリールチオ基、ヘテロ環基、アミノ基、アシル基、カルボニル基、カルボキシル基、カルバモイル基、アルコキシカルボニル基、アリールオキシカルボニル基、アシルオキシ基、アシルアミノ基、ヒドロキシル基、イミノ基、シアノ基、ニトロ基、ハロゲン基、スルホニル基、シリル基、シロキサニル基のうちのいずれかを表し、これらの基は置換されたものであってもよい。また、隣接した置換基との間で環が形成されていてもよい。） (Wherein R 1 , R 12 and R 23 may be the same as or different from each other, hydrogen, alkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, aryl group, aralkyl group, aryl Oxy group, arylthio group, heterocyclic group, amino group, acyl group, carbonyl group, carboxyl group, carbamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, hydroxyl group, imino group, cyano group, nitro Represents any one of a group, a halogen group, a sulfonyl group, a silyl group, and a siloxanyl group, and these groups may be substituted, and a ring is formed between adjacent substituents. May be.)
本発明の有機ＥＬ素子は、ホール注入電極と電子注入電極の間に、発光層を含む有機化合物層が設けられた有機ＥＬ素子であり、有機化合物層に上記本発明のジベンゾチオフェン誘導体が含有されていることを特徴としている。 The organic EL device of the present invention is an organic EL device in which an organic compound layer including a light emitting layer is provided between a hole injection electrode and an electron injection electrode, and the organic compound layer contains the dibenzothiophene derivative of the present invention. It is characterized by having.
本発明における有機ＥＬ素子において、上記本発明のジベンゾチオフェン誘導体は、発光層を含む有機化合物層のいずれかに含有されていればよい。 In the organic EL device of the present invention, the dibenzothiophene derivative of the present invention may be contained in any one of the organic compound layers including the light emitting layer.
発光層がホスト材料と発光材料から形成される場合、本発明のジベンゾチオフェン誘導体は、ホスト材料として発光層に含有されていることが好ましい。また、発光材料は３重項状態から発光する燐光発光材料であることが好ましい。本発明のジベンゾチオフェン誘導体を発光層のホスト材料として用いることにより、発光材料の燐光発光の効率を向上させるとこができ、駆動電圧を低減し、消費電力を低くすることができる。 When the light emitting layer is formed from a host material and a light emitting material, the dibenzothiophene derivative of the present invention is preferably contained in the light emitting layer as a host material. The light-emitting material is preferably a phosphorescent material that emits light from a triplet state. By using the dibenzothiophene derivative of the present invention as the host material of the light emitting layer, the phosphorescence efficiency of the light emitting material can be improved, the driving voltage can be reduced, and the power consumption can be reduced.
本発明のジベンゾチオフェン誘導体を、有機ＥＬ素子の有機化合物層に用いることにより、有機ＥＬ素子の発光効率を向上させ、駆動電圧を低減させることができる。従って、消費電力を低減化させることができる。また、素子の連続駆動における輝度半減期を長くすることができ、素子の駆動安定性を高めることができる。 By using the dibenzothiophene derivative of the present invention for the organic compound layer of the organic EL element, the light emission efficiency of the organic EL element can be improved and the driving voltage can be reduced. Therefore, power consumption can be reduced. Further, the luminance half-life in continuous driving of the element can be increased, and the driving stability of the element can be improved.
また、本発明の有機ＥＬ素子は、上記本発明のジベンゾチオフェン誘導体を用いるものであるので、高い発光効率を示し、駆動電圧及び消費電力の低い有機ＥＬ素子とすることができる。 Moreover, since the organic EL element of this invention uses the dibenzothiophene derivative of the said invention, it can be set as an organic EL element which shows high luminous efficiency and low drive voltage and power consumption.
以下、本発明を実施例により具体的に説明するが、本発明は以下の実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to a following example.
（実施例１）
〔ベンゾチオフェン誘導体１の合成〕
以下の反応式に従い、以下に示す構造のベンゾチオフェン誘導体１（化合物１）を合成した。
Example 1
[Synthesis of benzothiophene derivative 1]
A benzothiophene derivative 1 (compound 1) having the following structure was synthesized according to the following reaction formula.
具体的には以下のようにしてベンゾチオフェン誘導体１を合成した。
Specifically,
環流管を備えた２００ｍＬ三つ口フラスコ内において、４−ジベンゾチオフェンボロン酸２．２８ｇ（１０．０ｍｍｏｌ）、１，３，５−トリブロモベンゼン３１４ｍｇ（１．０ｍｍｏｌ）を加え、セプタムキャップで密閉し窒素置換した後、ＴＨＦ（テトラヒドロフラン）３０ｍＬを加えた。この溶液に３０ｍＬのＴＨＦに溶解させたテトラキス（トリフェニルホスフィン）パラジウム１２５ｍｇを加え、さらに２Ｎ炭酸カリウム水溶液１０ｍＬを加えて窒素フロー中攪拌しながら７０℃で８時間還流させた。 In a 200 mL three-necked flask equipped with a reflux tube, 2.28 g (10.0 mmol) of 4-dibenzothiopheneboronic acid and 314 mg (1.0 mmol) of 1,3,5-tribromobenzene were added and sealed with a septum cap. After substituting with nitrogen, 30 mL of THF (tetrahydrofuran) was added. To this solution, 125 mg of tetrakis (triphenylphosphine) palladium dissolved in 30 mL of THF was added, and further 10 mL of 2N potassium carbonate aqueous solution was added and refluxed at 70 ° C. for 8 hours with stirring in a nitrogen flow.
反応後、分液ロートにて反応溶液の水層を水洗し、有機層を濃縮した。残渣をトルエン／ヘキサン混合液（１：２）に溶かしてアルミナカラムに通し、粗精製を行った。トルエン／ヘキサンからの再結晶を２度行い、目的物（白色固体）を３８０ｍｇ（収率６０％）得た。 After the reaction, the aqueous layer of the reaction solution was washed with a separatory funnel, and the organic layer was concentrated. The residue was dissolved in a toluene / hexane mixture (1: 2) and passed through an alumina column for rough purification. Recrystallization from toluene / hexane was performed twice to obtain 380 mg (yield 60%) of the desired product (white solid).
得られたベンゾチオフェン誘導体１のＮＭＲスペクトルデータは以下の通りである。
The NMR spectrum data of the obtained
１Ｈ−ＮＭＲ（４００ＭＨｚ，ＴＨＦ−ｄ６）：δ １０．２０−１０．１４（ｍ，９Ｈ），９．７９−９．７４（ｍ，３Ｈ），９．６５（ｄｄ，３Ｈ，Ｊ＝８．０，１．２Ｈｚ），９．５２（ｔ，３Ｈ，Ｊ＝８．０Ｈｚ），９．３７−９．３０（ｍ，６Ｈ）
ベンゾチオフェン誘導体のＩＲスペクトルは図２に示す通りであり、ピーク波数は以下の通りである。
ＩＲスペクトルのピーク波数（ＫＢｒ法，ｃｍ−１）：３０５８，３０４１，１５８９，１５６９，１４４０，１３７５，１３０１，１２４５，１１０３，１０４５，８８３，７９８，７５２
1 H-NMR (400 MHz, THF-d 6 ): δ 10.20-10.14 (m, 9H), 9.79-9.74 (m, 3H), 9.65 (dd, 3H, J = 8.0, 1.2 Hz), 9.52 (t, 3H, J = 8.0 Hz), 9.37-9.30 (m, 6H)
The IR spectrum of the benzothiophene derivative is as shown in FIG. 2, and the peak wave number is as follows.
Peak wave number of IR spectrum (KBr method, cm −1 ): 3058, 3041, 1589, 1569, 1440, 1375, 1301, 1245, 1103, 1045, 883, 798, 752
〔有機ＥＬ素子の作製〕
図１に示す有機ＥＬ素子を作製した。
[Production of organic EL elements]
The organic EL element shown in FIG. 1 was produced.
図１に示すように、ガラス基板からなる基板１の上に、インジウム−錫酸化物（ＩＴＯ）からなるホール注入電極（陽極）２を形成し、その上にフッ化炭素（ＣＦｘ）からなるホール注入層３（厚み１ｎｍ）を形成した。ホール注入層３の上に、ＮＰＢからなるホール輸送層４（厚み５０ｎｍ）を形成した。ホール輸送層４の上に、上記のようにして合成したベンゾチオフェン誘導体１をホスト材料として用い、Ｉｒ（ｐｐｙ）３からなる燐光発光材料をドーパント材料として含有した発光層５（厚み４２ｎｍ）を形成した。ドーパント材料は、ホスト材料に対して６．５重量％となるように含有させた。
As shown in FIG. 1, a hole injection electrode (anode) 2 made of indium-tin oxide (ITO) is formed on a
発光層５の上に、ＢＡｌｑからなるホール阻止層（励起子阻止層）６（厚み１０ｎｍ）を形成した。ホール阻止層６の上に、Ａｌｑからなる電子輸送・注入層７（厚み２０ｎｍ）及び、フッ化リチウム（厚み１ｎｍ）とアルミニウム（厚み２００ｎｍ）を積層した構造の電子注入電極８を形成し、有機ＥＬ素子を作製した。
A hole blocking layer (exciton blocking layer) 6 (thickness 10 nm) made of BAlq was formed on the light emitting layer 5. On the hole blocking layer 6, an electron transport / injection layer 7 (thickness 20 nm) made of Alq and an
上記構造の有機ＥＬ素子において、各層は具体的には以下のようにして作製した。まず、ガラス基板上にインジウム−錫酸化物（ＩＴＯ）が形成された基板をイソプロピルアルコールで５分間超音波洗浄を２回行い、Ｏ２プラズマ処理を行った。次に、上記ＩＴＯからなるホール注入電極２の上に、ホール注入層３をフッ化炭素膜形成装置により製膜し、続いて真空蒸着装置内に入れ、ホール輸送層４、発光層５、ホール阻止層６、電子輸送・注入層７、及び電子注入電極８の順に真空蒸着法により各層を積層した。発光層５は、ベンゾチオフェン誘導体１とＩｒ（ｐｐｙ）３とを同時に加熱して蒸着する共蒸着法で形成した。蒸着は、いずれも真空度１×１０−６Ｔｏｒｒ、基板温度制御無しの条件下で行った。ＮＰＢは、Ｎ，Ｎ′−ジ（ナフタセン−１−イル）−Ｎ，Ｎ′−ジフェニルベンジジンであり、以下の構造を有している。
In the organic EL device having the above structure, each layer was specifically produced as follows. First, a substrate in which indium-tin oxide (ITO) was formed on a glass substrate was subjected to ultrasonic cleaning twice with isopropyl alcohol for 5 minutes, and O 2 plasma treatment was performed. Next, a
Ｉｒ（ｐｐｙ）３は、トリス（２−フェニルピリジン）イリジウム（III）であり、以下の構造を有している。 Ir (ppy) 3 is tris (2-phenylpyridine) iridium (III) and has the following structure.
ＢＡｌｑは、ビス（２−メチル−８−キノリノラト）−４−フェニルフェノラトアルミニウム（III）であり、以下の構造を有している。 BAlq is bis (2-methyl-8-quinolinolato) -4-phenylphenolato aluminum (III) and has the following structure.
Ａｌｑは、トリス−（８−キノリラト）アルミニウム（III）であり、以下の構造を有している。 Alq is tris- (8-quinolinato) aluminum (III) and has the following structure.
〔有機ＥＬ素子の評価〕
上記のようにして作製した有機ＥＬ素子の駆動電圧及び輝度半減期を測定した。具体的には、上記有機ＥＬ素子のホール注入電極をプラス、電子注入電極をマイナスにバイアスして、電圧を印加し、発光特性を測定した。その結果、ピーク波長５１２ｎｍのＩｒ（ｐｐｙ）３の発光に基づく緑色発光が観測された。
[Evaluation of organic EL elements]
The driving voltage and luminance half-life of the organic EL device produced as described above were measured. Specifically, the hole injection electrode of the organic EL element was biased positively and the electron injection electrode was negatively biased, a voltage was applied, and the light emission characteristics were measured. As a result, green light emission based on Ir (ppy) 3 light emission with a peak wavelength of 512 nm was observed.
初期特性は電流密度２ｍＡ／ｃｍ２において、電流効率３９．４ｃｄ／Ａであり、パワー（電力）効率２１．３ｌｍ／Ｗであった。また、１０ｍＡ／ｃｍ２における駆動電圧は６．８Ｖであった。 The initial characteristics were a current efficiency of 39.4 cd / A and a power (power) efficiency of 21.3 lm / W at a current density of 2 mA / cm 2 . The driving voltage at 10 mA / cm 2 was 6.8V.
この素子を、３０００ｃｄ／ｍ２で連続駆動させた際の輝度半減期は４８５時間であった。 When this element was continuously driven at 3000 cd / m 2 , the luminance half-life was 485 hours.
（比較例）
発光層のホスト材料として、ベンゾチオフェン誘導体１に代えて、ＣＢＰを用いる以外は、上記実施例と同様にして有機ＥＬ素子を作製した。なお、ＣＢＰは以下の構造を有している。
(Comparative example)
An organic EL device was produced in the same manner as in the above example except that CBP was used instead of the
この有機ＥＬ素子について、上記と同様に評価したところ、ピーク波長５１２ｎｍのＩｒ（ｐｐｙ）３の発光に基づく緑色発光が観測された。初期特性は電流密度２ｍＡ／ｃｍ２において、電流効率２７．８ｃｄ／Ａであり、パワー（電力）効率１５．０ｌｍ／Ｗであった。また、１０ｍＡ／ｃｍ２における駆動電圧は７．０Ｖであった。この素子を３０００ｃｄ／ｍ２で連続駆動させた際の輝度半減期は４００時間であった。 When this organic EL element was evaluated in the same manner as described above, green light emission based on Ir (ppy) 3 light emission having a peak wavelength of 512 nm was observed. The initial characteristics were a current efficiency of 27.8 cd / A at a current density of 2 mA / cm 2 and a power (power) efficiency of 15.0 lm / W. The driving voltage at 10 mA / cm 2 was 7.0V. The luminance half-life when this device was continuously driven at 3000 cd / m 2 was 400 hours.
以上の結果から明らかなように、発光層のホスト材料として、本発明に従うベンゾチオフェン誘導体１を用いた実施例の有機ＥＬ素子は、ホスト材料としてＣＢＰを用いた比較例に比べ、発光効率が高く、駆動電圧が低減されることがわかる。また、連続駆動させた際の輝度半減期が長くなり、素子の駆動安定性を高め、長寿命化を図ることができることがわかる。
As is clear from the above results, the organic EL element of the example using the
１…基板
２…ホール注入電極
３…ホール注入層
４…ホール輸送層
５…発光層
６…ホール阻止層
７…電子輸送・注入層
８…電子注入電極
DESCRIPTION OF
Claims (8)
前記有機化合物層に請求項１〜４のいずれか１項に記載のジベンゾチオフェン誘導体が含有されていることを特徴とする有機エレクトロルミネッセンス素子。 In an organic electroluminescence device in which an organic compound layer including a light emitting layer is provided between a hole injection electrode and an electron injection electrode,
An organic electroluminescence device, wherein the organic compound layer contains the dibenzothiophene derivative according to any one of claims 1 to 4.
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