JP5194649B2 - Light emitting device material and light emitting device - Google Patents
Light emitting device material and light emitting device Download PDFInfo
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- JP5194649B2 JP5194649B2 JP2007225260A JP2007225260A JP5194649B2 JP 5194649 B2 JP5194649 B2 JP 5194649B2 JP 2007225260 A JP2007225260 A JP 2007225260A JP 2007225260 A JP2007225260 A JP 2007225260A JP 5194649 B2 JP5194649 B2 JP 5194649B2
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- light emitting
- light
- derivatives
- emitting device
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[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
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical group N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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
- 239000002356 single layer Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 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
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Description
本発明は、蛍光色素や電荷輸送材として有用な発光素子材料およびこれを用いた発光素子に関する。本発明の発光素子は、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である。 The present invention relates to a light emitting device material useful as a fluorescent dye or a charge transport material, and a light emitting device using the same. The light-emitting element of the present invention can be used in the fields of display elements, flat panel displays, backlights, illumination, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like.
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発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、近年活発に行われている。この発光素子は、薄型で、低駆動電圧下で高輝度発光が可能であり、かつ、発光材料を選ぶことにより多色発光が可能なことが特徴であり、注目を集めている。 In recent years, research on organic thin-film light-emitting devices that emit light when electrons injected from a cathode and holes injected from an anode are recombined in an organic light-emitting body sandwiched between both electrodes has been actively conducted. This light-emitting element is characterized by being thin, capable of emitting high-luminance under a low driving voltage, and capable of emitting multicolor light by selecting a light-emitting material.
イーストマンコダック社のＣ．Ｗ．Ｔａｎｇらによって有機薄膜発光素子が高輝度に発光することが示されて以来、この技術について、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（合金）を順次設けたものであり、１０Ｖ程度の駆動電圧で１,０００ｃｄ／ｍ２の緑色発光が可能であった（非特許文献１参照）。 C. of Eastman Kodak Company W. Since Tang et al. Have shown that organic thin-film light-emitting elements emit light with high brightness, many research institutions have studied this technology. A typical structure of the organic thin-film light-emitting device presented by the Kodak research group is a hole-transporting diamine compound, a light-emitting layer of tris (8-quinolinolato) aluminum (III), and a cathode. As described above, Mg: Ag (alloy) was sequentially provided, and green light emission of 1,000 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の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 green luminescent materials is the most advanced. At present, intensive research is being conducted with the aim of improving the characteristics of red and blue luminescent materials.
有機薄膜発光素子における最大の課題の１つは、素子の発光効率と色純度の両立である。特に青色発光素子に関しては、発光効率が高く、色純度に優れた素子を提供する青色発光材料は少ない。例えば、青色ゲスト材料として、スチリルアミン誘導体（特許文献１参照）、ペリレン誘導体（特許文献２参照）、アントラセン誘導体（特許文献３参照）を用いる技術が開示されている。また、クリセン化合物として、クリセン構造とアミン構造が連結している芳香族アミン誘導体や（特許文献４参照）、少なくとも２つのクリセンが、少なくとも１つ以上のアリール基もしくは複素環基を介在させて結合されるクリセン化合物（特許文献５参照）を青色発光素子に用いる技術が開示されている。しかしながら、いずれも発光効率と色純度の両立が十分ではなかった。
そこで本発明は、かかる従来技術の問題を解決し、発光効率が高く、色純度に優れた発光素子を可能にする発光素子材料およびこれを用いた発光素子を提供することを目的とする。 SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to solve the problems of the prior art, and to provide a light emitting element material that enables a light emitting element with high luminous efficiency and excellent color purity, and a light emitting element using the same.
本発明は一般式（１）で表されるクリセン化合物を含有する発光素子材料である。 The present invention is a light emitting device material containing a chrysene compound represented by the general formula (1).
Ｒ１〜Ｒ１７はそれぞれ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、アミノ基、シリル基、並びに−Ｐ（＝Ｏ）Ｒ１８Ｒ１９ の中から選ばれる。Ｒ１８およびＲ１９は、アリール基およびヘテロアリール基の中から選ばれる。Ｒ ２ またはＲ ８ のうちいずれかｎ個は二環式ベンゾへテロ環との連結に使われる。ｎは１〜２の整数である。Ｘは酸素原子、硫黄原子、−ＮＲ２０−の中から選ばれる。Ｒ２０は水素、アルキル基、シクロアルキル基、複素環基、アリール基、ヘテロアリール基の中から選ばれる。 R 1 to R 17 may be the same as or different from each other, and are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether. group, an aryl group, a heteroaryl group, an amino group, a silyl group, and -P (= O) selected from the R 18 R 1 9. R 18 and R 19 are selected from aryl groups and heteroaryl groups. Either n of R 2 or R 8 is used for linking to a bicyclic benzoheterocycle. n is an integer of 1-2 . X is selected from an oxygen atom, a sulfur atom, and —NR 20 —. R 20 is selected from hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an aryl group, and a heteroaryl group .
本発明の発光素子材料は、発光素子等に利用可能な、発光性能の高い発光素子材料を提供できる。本発明によれば、発光効率が高く、色純度に優れた発光素子が得られる。 The light-emitting element material of the present invention can provide a light-emitting element material having high light-emitting performance that can be used for a light-emitting element or the like. According to the present invention, a light emitting device having high luminous efficiency and excellent color purity can be obtained.
本発明において用いる一般式（１）で表されるクリセン化合物について説明する。 The chrysene compound represented by the general formula (1) used in the present invention will be described.
Ｒ１〜Ｒ１７はそれぞれ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、アミノ基、シリル基、−Ｐ（＝Ｏ）Ｒ１８Ｒ１９、並びに隣接置換基との間に形成される環構造の中から選ばれる。Ｒ１８およびＲ１９は、アリール基およびヘテロアリール基の中から選ばれる。Ｒ１〜Ｒ１２のうちいずれかｎ個は二環式ベンゾへテロ環との連結に使われる。ｎは１〜４の整数である。Ｘは酸素原子、硫黄原子、−ＮＲ２０−の中から選ばれる。Ｒ２０は水素、アルキル基、シクロアルキル基、複素環基、アリール基、ヘテロアリール基の中から選ばれる。Ｒ２０はＲ１３と結合し環を形成していてもよい。 R 1 to R 17 may be the same as or different from each other, and are hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether. It is selected from a ring structure formed between a group, an aryl group, a heteroaryl group, an amino group, a silyl group, —P (═O) R 18 R 19 , and an adjacent substituent. R 18 and R 19 are selected from aryl groups and heteroaryl groups. Any n of R 1 to R 12 are used for linking to a bicyclic benzoheterocycle. n is an integer of 1-4. X is selected from an oxygen atom, a sulfur atom, and —NR 20 —. R 20 is selected from hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an aryl group, and a heteroaryl group. R 20 may combine with R 13 to form a ring.
これらの置換基のうち、アルキル基とは、例えば、メチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基などの飽和脂肪族炭化水素基を示し、これは置換基を有していても有していなくてもよい。置換されている場合の追加の置換基には特に制限は無く、例えば、アルキル基、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、以下の記載にも共通する。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以上２０以下、より好ましくは１以上８以下の範囲である。 Among these substituents, the alkyl group is, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, or a tert-butyl group. This may or may not have a substituent. There is no restriction | limiting in particular in the additional substituent in the case of being substituted, For example, an alkyl group, an aryl group, heteroaryl group etc. can be mentioned, This point is common also in the following description. The number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 and more preferably 1 to 8 from the viewpoint of availability and cost.
シクロアルキル基とは、例えば、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、これは置換基を有していても有していなくてもよい。アルキル基部分の炭素数は特に限定されないが、通常、３以上２０以下の範囲である。 The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may or may not have a substituent. Although carbon number of an alkyl group part is not specifically limited, Usually, it is the range of 3-20.
複素環基とは、例えば、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示し、これは置換基を有していても有していなくてもよい。複素環基の炭素数は特に限定されないが、通常、２以上２０以下の範囲である。 The heterocyclic group refers to an aliphatic ring having atoms other than carbon, such as a pyran ring, a piperidine ring, and a cyclic amide, in the ring, which may or may not have a substituent. . Although carbon number of a heterocyclic group is not specifically limited, Usually, it is the range of 2-20.
アルケニル基とは、例えば、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、これは置換基を有していても有していなくてもよい。アルケニル基の炭素数は特に限定されないが、通常、２以上２０以下の範囲である。 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 or may not have a substituent. Although carbon number of an alkenyl group is not specifically limited, Usually, it is the range of 2-20.
シクロアルケニル基とは、例えば、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、これは置換基を有していても有していなくてもよい。 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 have a substituent. You don't have to.
アルキニル基とは、例えば、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、これは置換基を有していても有していなくてもよい。アルキニル基の炭素数は特に限定されないが、通常、２以上２０以下の範囲である。 An alkynyl group shows the unsaturated aliphatic hydrocarbon group containing triple bonds, such as an ethynyl group, for example, and may or may not have a substituent. Although carbon number of an alkynyl group is not specifically limited, Usually, it is the range of 2-20.
アルコキシ基とは、例えば、メトキシ基、エトキシ基、プロポキシ基などのエーテル結合を介して脂肪族炭化水素基が結合した官能基を示し、この脂肪族炭化水素基は置換基を有していても有していなくてもよい。アルコキシ基の炭素数は特に限定されないが、通常、１以上２０以下の範囲である。 The alkoxy group refers to, for example, a functional group having an aliphatic hydrocarbon group bonded through an ether bond such as a methoxy group, an ethoxy group, or a propoxy group, and the aliphatic hydrocarbon group may have a substituent. It may not have. Although carbon number of an alkoxy group is not specifically limited, Usually, it is the range of 1-20.
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。アルキルチオ基の炭化水素基は置換基を有していても有していなくてもよい。アルキルチオ基の炭素数は特に限定されないが、通常、１以上２０以下の範囲である。 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. The hydrocarbon group of the alkylthio group may or may not have a substituent. Although carbon number of an alkylthio group is not specifically limited, Usually, it is the range of 1-20.
アリールエーテル基とは、例えば、フェノキシ基など、エーテル結合を介した芳香族炭化水素基が結合した官能基を示し、芳香族炭化水素基は置換基を有していても有していなくてもよい。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以上４０以下の範囲である。 An aryl ether group refers to a functional group to which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may or may not have a substituent. Good. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.
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。アリールエーテル基における芳香族炭化水素基は置換基を有していても有していなくてもよい。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以上４０以下の範囲である。 An aryl thioether group is one in which the oxygen atom of the ether bond of the aryl ether group is substituted with a sulfur atom. The aromatic hydrocarbon group in the aryl ether group may or may not have a substituent. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.
アリール基とは、例えば、フェニル基、ナフチル基、ビフェニル基、アントラセニル基、フェナントリル基、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かまわない。アリール基の炭素数は特に限定されないが、通常、６以上４０以下の範囲である。 The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, an anthracenyl group, a phenanthryl group, a terphenyl group, or 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.
ヘテロアリール基とは、フラニル基、チオフェニル基、ピロリル基、ベンゾフラニル基、ベンゾチオフェニル基、インドリル基、ピリジル基、キノリニル基などの炭素以外の原子を一個または複数個環内に有する環状芳香族基を示し、これは置換基を有していても有していなくてもよい。ヘテロアリール基の炭素数は特に限定されないが、通常好ましくは、２以上３０以下の範囲である。 A heteroaryl group is a cyclic aromatic group having one or more atoms other than carbon such as furanyl group, thiophenyl group, pyrrolyl group, benzofuranyl group, benzothiophenyl group, indolyl group, pyridyl group, quinolinyl group in the ring. This may or may not have a substituent. Although carbon number of a heteroaryl group is not specifically limited, Usually, it is 2 or more and 30 or less range.
アミノ基、シアノ基、−Ｐ(＝Ｏ)Ｒ１８Ｒ１９は、置換基を有していても有していなくてもよい。置換基としては例えば上記のようなアルキル基、シクロアルキル基、アリール基、ヘテロアリール基などが挙げられる。 The amino group, cyano group, and -P (= O) R 18 R 19 may or may not have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group as described above.
Ｒ１８およびＲ１９は、アリール基およびヘテロアリール基の中から選ばれる基である。 R 18 and R 19 are groups selected from aryl groups and heteroaryl groups.
シリル基とは、例えば、トリメチルシリル基などのケイ素原子への結合を有する官能基を示し、これは置換基を有していても有していなくてもよい。シリル基の炭素数は特に限定されないが、通常好ましくは、３以上２０以下の範囲である。また、ケイ素数は、通常好ましくは、１以上６以下の範囲である。 A silyl group refers to, for example, a functional group having a bond to a silicon atom, such as a trimethylsilyl group, which may or may not have a substituent. Although carbon number of a silyl group is not specifically limited, Usually, it is the range of 3-20. The number of silicon is usually preferably in the range of 1 or more and 6 or less.
また、任意の隣接する２置換基（例えば一般式（１）のＲ１とＲ２）が互いに結合して、共役または非共役の縮合環を形成していてもよい。縮合環の構成元素としては、炭素以外にも窒素、酸素、硫黄、リンおよびケイ素から選ばれる元素を含んでいてもよい。また、縮合環がさらに別の環と縮合してもよい。 Moreover, arbitrary adjacent 2 substituents (for example, R 1 and R 2 in the general formula (1)) may be bonded to each other to form a conjugated or non-conjugated condensed ring. As a constituent element of the condensed ring, an element selected from nitrogen, oxygen, sulfur, phosphorus, and silicon may be included in addition to carbon. Further, the condensed ring may be further condensed with another ring.
一般式（１）で表されるクリセン化合物は、分子中にクリセン骨格および１〜４個の二環式ベンゾヘテロ環を有する。ここで本発明において二環式ベンゾヘテロ環とは、電子供与性縮合芳香族であるベンゾフラン環（Ｘが酸素原子の場合）、ベンゾチオフェン環（Ｘが硫黄原子の場合）またはインドール環（Ｘが−ＮＲ２０−の場合）をいう。このような二環式ベンゾへテロ環を１〜４個有することによって、クリセン化合物の蛍光量子収率が優れるので好ましい。中でも、二環式ベンゾへテロ環の数が１〜２個の範囲であると、高色純度の青色発光が得られるため、さらに好ましい。なお、クリセン化合物中に含まれる二環式ベンゾヘテロ環は、１種類であってもよいし、複数種が含まれていてもよい。 The chrysene compound represented by the general formula (1) has a chrysene skeleton and 1 to 4 bicyclic benzoheterocycles in the molecule. Here, in the present invention, the bicyclic benzoheterocycle means an electron-donating condensed aromatic benzofuran ring (when X is an oxygen atom), a benzothiophene ring (when X is a sulfur atom) or an indole ring (where X is −). NR 20 - refers to the case). Having 1 to 4 such bicyclic benzoheterocycles is preferable because the fluorescence quantum yield of the chrysene compound is excellent. Among them, it is more preferable that the number of bicyclic benzoheterocycles is in the range of 1 to 2 since high-purity blue light emission can be obtained. In addition, the bicyclic benzoheterocycle contained in a chrysene compound may be one type, and multiple types may be contained.
Ｒ１〜Ｒ１２のうちいずれかｎ個は二環式ベンゾヘテロ環との連結に使われるが、原料の入手性や合成の容易さの点およびさらに蛍光量子収率や色純度が優れる点から、Ｒ２またはＲ８のうち少なくとも１つが二環式ベンゾヘテロ環との連結に用いられることが好ましい。 Any one of R 1 to R 12 is used for linking with a bicyclic benzoheterocycle, but from the viewpoint of availability of raw materials, ease of synthesis, and further excellent fluorescence quantum yield and color purity, It is preferred that at least one of R 2 or R 8 is used for linking with a bicyclic benzoheterocycle.
さらに、一般式（１）のＸが酸素原子であると、より高い蛍光量子収率が得られるため好ましい。 Furthermore, it is preferable that X in the general formula (1) is an oxygen atom because a higher fluorescence quantum yield is obtained.
一般式（１）で表されるクリセン化合物は、蛍光量子収率が高く、色純度に優れているため、発光素子材料として用いることにより、発光効率が高く、かつ色純度が優れた発光素子が可能となる。 The chrysene compound represented by the general formula (1) has a high fluorescence quantum yield and excellent color purity. Therefore, when used as a light emitting device material, a light emitting device having high luminous efficiency and excellent color purity can be obtained. It becomes possible.
上記のようなクリセン化合物として、特に限定されるものではないが、具体的には以下のような例が挙げられる。 Although it does not specifically limit as said chrysene compound, Specifically, the following examples are mentioned.
一般式（１）で表されるクリセン化合物の合成には、公知の方法を使用することができる。クリセン骨格へ、ベンゾフラニル基、ベンゾチオフェニル基またはインドリル基を導入する方法は、例えば、パラジウムやニッケル触媒下でのハロゲン化クリセン誘導体とベンゾフラニル金属錯体、ベンゾチオフェニル金属錯体またはインドリル金属錯体とのカップリング反応を用いる方法、パラジウムやニッケル触媒下でのクリセニル金属錯体とハロゲン化ベンゾフラン誘導体、ハロゲン化ベンゾチオフェン誘導体またはハロゲン化インドール誘導体とのカップリング反応を用いる方法などが挙げられるが、これらに限定されるものではない。 A known method can be used for the synthesis of the chrysene compound represented by the general formula (1). A method for introducing a benzofuranyl group, a benzothiophenyl group, or an indolyl group into a chrysene skeleton is, for example, a cup of a halogenated chrysene derivative and a benzofuranyl metal complex, a benzothiophenyl metal complex, or an indolyl metal complex under a palladium or nickel catalyst. Examples include a method using a ring reaction, a method using a coupling reaction between a chrysenyl metal complex and a halogenated benzofuran derivative, a halogenated benzothiophene derivative, or a halogenated indole derivative under a palladium or nickel catalyst, but are not limited thereto. It is not something.
次に、本発明における発光素子の実施形態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、陽極、陰極、および該陽極と該陰極の間に存在する有機層を有し、該有機層は少なくとも発光層を含み、該発光層が電気エネルギーにより発光する。 Next, embodiments of the light-emitting element in the present invention will be described in detail with examples. The light-emitting element of the present invention includes an anode, a cathode, and an organic layer present between the anode and the cathode. The organic layer includes at least a light-emitting layer, and the light-emitting layer emits light by electric energy.
有機層は、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、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、複数層のいずれでもよい。正孔輸送層および電子輸送層が複数層をからなる場合、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、正孔注入材料は正孔輸送材料に、電子注入材料は電子輸送材料にそれぞれ含まれる。 The organic layer is composed of only the light-emitting layer, and 1) a hole transport layer / light-emitting layer / electron transport layer, 2) a light-emitting layer / electron transport layer, and 3) a hole transport layer / light-emitting layer. Is mentioned. Each of the 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 on the side in contact with the electrode may be referred to as the hole injection layer and the electron injection layer, respectively. The hole transport material and the electron injection material are included in the electron transport material, respectively.
本発明の発光素子は、一般式（１）で表されるクリセン化合物を含む発光素子材料が有機層に含まれる。ここで、発光素子材料とは、発光素子における発光に関与している化合物を指すものであり、自ら発光するもの、およびその発光を助けるもののいずれかに該当する。具体的には、正孔輸送材料、発光材料および電子輸送材料などが発光素子材料に該当する。 In the light emitting device of the present invention, a light emitting device material containing a chrysene compound represented by the general formula (1) is included in the organic layer. Here, the light emitting element material refers to a compound that participates in light emission in the light emitting element, and corresponds to either one that emits light by itself or one that assists in the light emission. Specifically, a hole transport material, a light emitting material, an electron transport material, and the like correspond to the light emitting element material.
本発明の発光素子材料は、正孔輸送材料や電子輸送材料として用いてもよいが、高い発光性能を有することから発光材料として好適に用いられる。また、本発明の発光素子材料は、青色領域に強い発光を示すことから、青色発光材料として好適に用いられるが、緑色〜赤色発光素子や白色発光素子用の材料としても用いることができる。白色発光素子は、異なる発光色の材料を複数積層することで得られる。具体的には、水色発光材料と橙色発光材料の２層積層系、青色発光材料と緑色発光材料と赤色発光材料の３層積層系が挙げられる。本発明の発光素子材料は、青色発光材料として好適に用いられるため、その他の異なる発光材料として、例えば、２，３，５，６−１Ｈ，４Ｈ−テトラヒドロ−９−（２’−ベンゾチアゾリル）キノリジノ［９，９ａ，１−ｇｈ］クマリンなどの緑色発光材料、１，３，５，７−テトラ（４−ｔ−ブチルフェニル）−８−フェニル−４，４−ジフルオロ−４−ボラ−３ａ，４ａ−ジアザ−ｓ−インダセンなどの赤色発光材料との３層積層をすることにより、白色発光素子を得ることができる。 The light emitting device material of the present invention may be used as a hole transport material or an electron transport material, but is preferably used as a light emitting material because of its high light emission performance. The light-emitting element material of the present invention is preferably used as a blue light-emitting material because it exhibits strong light emission in the blue region, but can also be used as a material for green to red light-emitting elements and white light-emitting elements. A white light emitting element is obtained by laminating a plurality of materials having different emission colors. Specifically, a two-layer laminated system of a light blue light emitting material and an orange light emitting material, and a three-layer laminated system of a blue light emitting material, a green light emitting material, and a red light emitting material can be given. Since the light emitting device material of the present invention is suitably used as a blue light emitting material, other different light emitting materials include, for example, 2,3,5,6-1H, 4H-tetrahydro-9- (2′-benzothiazolyl) quinolizino. Green light-emitting materials such as [9,9a, 1-gh] coumarin, 1,3,5,7-tetra (4-t-butylphenyl) -8-phenyl-4,4-difluoro-4-bora-3a, A white light emitting element can be obtained by laminating three layers with a red light emitting material such as 4a-diaza-s-indacene.
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い。陽極の材料としては、例えば、酸化錫、酸化インジウム、酸化亜鉛インジウム、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 is not particularly limited as long as it can efficiently inject holes into the organic layer, but a material having a relatively large work function is preferably used. Examples of the material for the anode include conductive metal oxides such as tin oxide, indium oxide, indium zinc oxide, and indium tin oxide (ITO), metals such as gold, silver, and chromium, copper iodide, and copper sulfide. Examples include inorganic conductive materials, 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.
陽極の抵抗は、発光素子の発光に十分な電流が供給できればよいが、発光素子の消費電力の点からは低抵抗であることが望ましい。例えば、抵抗が３００Ω／□以下であれば電極として機能するが、現在では１０Ω／□程度のＩＴＯ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。陽極の厚みは抵抗値に合わせて任意に選ぶことができるが、通常１００〜３００ｎｍの間で用いられることが多い。 The resistance of the anode is not limited as long as a current sufficient for light emission of the light emitting element can be supplied, but it is desirable that the resistance be low from the viewpoint of power consumption of the light emitting element. For example, if the resistance is 300Ω / □ or less, it functions as an electrode. However, since it is now possible to supply an ITO substrate of about 10Ω / □, it is possible to use a low resistance product of 100Ω / □ or less. Particularly desirable. The thickness of the anode 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、陽極を基板上に形成することが好ましい。基板は、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。陽極の形成方法は、特に制限されず、例えば、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を用いることができる。 In order to maintain the mechanical strength of the light emitting element, it is preferable to form the anode on the 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. The glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass, but soda lime glass with a barrier coat such as SiO 2 is also available on the market. 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 method for forming the anode is not particularly limited, and for example, an electron beam method, a sputtering method, a chemical reaction method, or the like can be used.
陰極に用いられる材料は、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、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、セシウム、カルシウムおよびマグネシウムならびに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、セシウム、カルシウム、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いため、有機層に微量（真空蒸着の膜厚計表示で１ｎｍ以下）のリチウムやマグネシウムをドーピングして安定性の高い電極を得る方法が好ましい例として挙げることができる。また、フッ化リチウムのような無機塩の使用も可能である。さらに、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、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、ポリ塩化ビニル、炭化水素系高分子化合物などの有機高分子化合物を積層することが、好ましい例として挙げられる。陰極の形成方法は、特に制限されず、例えば、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を用いることができる。 The material used for the cathode is not particularly limited as long as it can efficiently inject electrons into the organic layer, but platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium, sodium, potassium , Cesium, calcium and magnesium, and alloys thereof. Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, since these low work function metals are generally unstable in the atmosphere, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less in the thickness gauge display of vacuum deposition) to stabilize the organic layer. A preferred example is a method for obtaining a high electrode. Also, an inorganic salt such as lithium fluoride can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, polyvinyl chloride Lamination of organic polymer compounds such as hydrocarbon polymer compounds is a preferred example. The method for forming the cathode is not particularly limited, and for example, resistance heating, electron beam, sputtering, ion plating and coating can be used.
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または混合する方法、もしくは、正孔輸送材料と高分子結着剤の混合物を用いる方法により形成される。また、正孔輸送材料に塩化鉄（III）のような無機塩を添加して正孔輸送層を形成してもよい。正孔輸送材料は、薄膜を形成でき、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ない。例えば、４，４’−ビス（Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ）ビフェニル、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニル、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）などのビス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、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、ポリマー系では前記単量体を側鎖に有するポリカーボネートやスチレン誘導体、ポリチオフェン、ポリアニリン、ポリフルオレン、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。 The hole transport layer is formed by a method of laminating or mixing one or more hole transport materials or a method using a mixture of a hole transport material and a polymer binder. Alternatively, the hole transport layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole transport material. The hole transport material is not particularly limited as long as it is a compound capable of forming a thin film, injecting holes from the anode, and further transporting holes. For example, 4,4′-bis (N- (3-methylphenyl) -N-phenylamino) biphenyl, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl, 4,4 Triphenylamine derivatives such as', 4 "-tris (3-methylphenyl (phenyl) amino) triphenylamine, biscarbazole derivatives such as bis (N-allylcarbazole) or bis (N-alkylcarbazole), pyrazoline derivatives, Heterocyclic compounds such as stilbene compounds, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives, in the case of polymers, polycarbonates or styrene derivatives, polythiophene, polyaniline having the above monomers in the side chain , Polyfluorene, poly Such alkenyl carbazole and polysilane are preferred.
発光層は、ホスト材料とドーパント材料との混合物であっても、ホスト材料単独であっても、いずれでもよい。ホスト材料とドーパント材料は、それぞれ一種類であっても、複数の組み合わせであってもよい。ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれでもよい。ドーパント材料はホスト材料と積層されていても、ホスト材料中に分散されていても、いずれでもよい。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、ホスト材料とドーパント材料の合計に対して２０重量％以下が好ましく、さらに好ましくは１０重量％以下である。ドーピング方法は、ドーパント材料をホスト材料との共蒸着法によって形成してもよいし、ホスト材料とドーパント材料を予め混合してから蒸着しても良い。本発明において発光素子材料として用いられるクリセン化合物はホスト材料として用いてもよいが、蛍光量子収率が高いことから、ドーパント材料として好適に用いられる。 The light emitting layer may be a mixture of a host material and a dopant material or a host material alone. Each of the host material and the dopant material may be one kind or a plurality of combinations. The dopant material may be included in the entire host material or may be partially included. The dopant material may be either laminated with the host material or dispersed in the host material. If the amount of the dopant material is too large, a concentration quenching phenomenon occurs, so that the amount is preferably 20% by weight or less, more preferably 10% by weight or less, based on the total of the host material and the dopant material. As a doping method, the dopant material may be formed by a co-evaporation method with the host material, or the host material and the dopant material may be mixed in advance before the deposition. The chrysene compound used as the light-emitting element material in the present invention may be used as a host material, but is preferably used as a dopant material because of its high fluorescence quantum yield.
本発明に用いられるクリセン化合物のイオン化ポテンシャルは、特に限定されないが、好ましくは４．５ｅＶ以上７．０ｅＶ以下であり、より好ましくは５．４ｅＶ以上６．４ｅＶ以下である。なお、イオン化ポテンシャルの絶対値は測定方法により異なる場合がある。本発明のイオン化ポテンシャルは、大気雰囲気型紫外線光電子分析装置（ＡＣ−１、理研機器（株）製）を用いて、ＩＴＯガラス基板上に３０ｎｍ〜１００ｎｍの厚さに蒸着した薄膜を測定した値である。 The ionization potential of the chrysene compound used in the present invention is not particularly limited, but is preferably 4.5 eV or more and 7.0 eV or less, and more preferably 5.4 eV or more and 6.4 eV or less. Note that the absolute value of the ionization potential may vary depending on the measurement method. The ionization potential of the present invention is a value obtained by measuring a thin film deposited to a thickness of 30 nm to 100 nm on an ITO glass substrate using an atmospheric type ultraviolet photoelectron analyzer (AC-1, manufactured by Riken Kikai Co., Ltd.). is there.
ドーパント材料は、一般式（１）で表されるクリセン化合物一種のみを用いても、複数のクリセン化合物を混合して用いてもよい。また、その他のドーパント材料の一種類以上を一般式（１）で表されるクリセン化合物と混合して用いてもよい。混合しうるドーパント材料としては、ナフタレン、アントラセン、クリセン、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（例えば２−（ベンゾチアゾール−２−イル）−９，１０−ジフェニルアントラセンや５，６，１１，１２−テトラフェニルナフタセンなど）、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、４，４’−ビス（２−（４−ジフェニルアミノフェニル）エテニル）ビフェニル、４，４’−ビス（Ｎ−（スチルベン−４−イル）−Ｎ−フェニルアミノ）スチルベンなどの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、ピロメテン誘導体、ジケトピロロ［３，４−ｃ］ピロール誘導体、２，３，５，６−１Ｈ，４Ｈ−テトラヒドロ−９−（２’−ベンゾチアゾリル）キノリジノ［９，９ａ，１−ｇｈ］クマリンなどのクマリン誘導体、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。 As the dopant material, only one chrysene compound represented by the general formula (1) may be used, or a plurality of chrysene compounds may be mixed and used. One or more other dopant materials may be mixed with the chrysene compound represented by the general formula (1). As dopant materials that can be mixed, compounds having an aryl ring such as naphthalene, anthracene, chrysene, phenanthrene, pyrene, triphenylene, perylene, fluorene, and indene and derivatives thereof (for example, 2- (benzothiazol-2-yl) -9, 10-diphenylanthracene, 5,6,11,12-tetraphenylnaphthacene, etc.), furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9′-spirobisilafluorene, benzothiophene, benzofuran, indole, Compounds having heteroaryl rings such as dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene, and derivatives thereof, distyrylbenzene derivatives, , 4′-bis (2- (4-diphenylaminophenyl) ethenyl) biphenyl, 4,4′-bis (N- (stilben-4-yl) -N-phenylamino) stilbene, and other aminostyryl derivatives, aromatic Acetylene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, pyromethene derivatives, diketopyrrolo [3,4-c] pyrrole derivatives, 2,3,5,6-1H, 4H-tetrahydro-9- (2′-benzothiazolyl) Coumarin derivatives such as quinolidino [9,9a, 1-gh] coumarin, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole and their metal complexes and N, N′-diphenyl-N, N '-Di (3-methylphenyl)- And aromatic amine derivatives typified by 4'-diphenyl-1,1'-diamine.
発光材料に含有されるホスト材料は、特に限定されないが、アントラセンやピレンなどの縮合アリール環を有する化合物やその誘導体、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、ピロロピロール誘導体、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、ポリチオフェン誘導体などが好適に用いられる。中でも、電子供与性または中性置換基を有する縮合芳香環誘導体をホストとして用いると、本発明のクリセン化合物が有する高発光効率の効果がより顕著になるため、好ましい。具体的には、アントラセン化合物、ピレン化合物およびジスチリルベンゼン誘導体から選ばれた化合物をホスト材料として用いると、本発明のクリセン化合物と組み合わせた際により高効率となり、好ましい。 The host material contained in the light-emitting material is not particularly limited, but is a compound having a condensed aryl ring such as anthracene or pyrene or a derivative thereof, N, N′-dinaphthyl-N, N′-diphenyl-4,4′-diphenyl Aromatic amine derivatives such as -1,1'-diamine, 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, pyrrolopyrrole derivatives, in polymer systems, polyphenylene vinylene derivatives, polyparaphenylene derivatives, poly Fluorene derivatives, polyvinylcarbazole derivatives, and polythiophene derivatives are suitably used. Among them, it is preferable to use a condensed aromatic ring derivative having an electron donating property or a neutral substituent as a host because the effect of high luminous efficiency of the chrysene compound of the present invention becomes more remarkable. Specifically, it is preferable to use a compound selected from an anthracene compound, a pyrene compound, and a distyrylbenzene derivative as a host material because it becomes more efficient when combined with the chrysene compound of the present invention.
電子輸送層は、陰極から電子が注入され、さらに電子を輸送する層である。電子輸送層には、電子注入効率が高く、かつ、注入された電子を効率良く輸送することが望まれる。そのため電子輸送層は、電子親和力が大きく、電子移動度が大きく、安定性に優れ、かつ、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構成されることが望ましい。しかしながら、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ならば、電子輸送能力がそれ程高くない材料で構成されていても、発光効率を向上させる効果は電子輸送能力が高い材料で構成されている場合と同等となる。 The electron transport layer is a layer in which electrons are injected from the cathode and further transports electrons. The electron transport layer is desired to have high electron injection efficiency and efficiently transport injected electrons. Therefore, it is desirable that the electron transport layer is made of a material having a high electron affinity, a high electron mobility, excellent stability, and impurities that are traps are less likely to be generated during manufacture and use. However, considering the transport balance between holes and electrons, if the electron transport layer mainly plays a role of effectively preventing the holes from the anode from recombining and flowing to the cathode side, the electron transport Even if it is made of a material that does not have a high capability, the effect of improving the luminous efficiency is equivalent to that of a material that has a high electron transport capability.
電子輸送層に用いられる電子輸送材料は、特に限定されないが、ナフタレン、アントラセンなどの縮合アリール環を有する化合物やその誘導体、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が挙げられる。駆動電圧を低減できることから、電子輸送材料は、炭素、水素、窒素、酸素、ケイ素およびリンの中から選ばれる元素で構成され、電子受容性窒素を含むヘテロアリール環構造を有する化合物を用いることが好ましい。 The electron transport material used for the electron transport layer is not particularly limited, but is a compound having a condensed aryl ring such as naphthalene or anthracene or a derivative thereof, or a styryl-based fragrance represented by 4,4′-bis (diphenylethenyl) biphenyl. Ring derivatives, perylene derivatives, 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 hydroxy Examples include hydroxyazole complexes such as phenyloxazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes. Since the driving voltage can be reduced, the electron transport material is composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon and phosphorus, and a compound having a heteroaryl ring structure containing electron-accepting nitrogen is used. preferable.
電子受容性窒素とは、隣接原子との間に多重結合を形成している窒素原子を表す。窒素原子が高い電子陰性度を有することから、該多重結合は電子受容的な性質を有し、電子輸送能に優れ、電子輸送層に用いることで発光素子の駆動電圧を低減できる。それゆえ、電子受容性窒素を含むヘテロアリール環は、高い電子親和性を有する。電子受容性窒素を含むヘテロアリール環としては、例えば、ピリジン環、ピラジン環、ピリミジン環、キノリン環、キノキサリン環、ナフチリジン環、ピリミドピリミジン環、ベンゾキノリン環、フェナントロリン環、イミダゾール環、オキサゾール環、オキサジアゾール環、トリアゾール環、チアゾール環、チアジアゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、ベンズイミダゾール環、フェナンスロイミダゾール環などが挙げられる。 The electron-accepting nitrogen represents a nitrogen atom that forms a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond has an electron-accepting property, has an excellent electron transporting ability, and can be used for an electron transporting layer to reduce the driving voltage of the light emitting element. Therefore, heteroaryl rings containing electron-accepting nitrogen have a high electron affinity. Examples of the heteroaryl ring containing an electron-accepting nitrogen include, for example, a pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, Examples thereof include an oxadiazole ring, a triazole ring, a thiazole ring, a thiadiazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthrimidazole ring.
これらのヘテロアリール環構造を有する化合物としては、例えば、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、イミダゾピリジン誘導体、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、２，５−ビス（６’−（２’，２”−ビピリジル））−１，１−ジメチル−３，４−ジフェニルシロールなどのビピリジン誘導体、１，３−ビス（４’−（２，２’：６’２”−ターピリジニル））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、電子輸送能の点から好ましく用いられる。さらに、１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼン、２，７−ビス（１，１０−フェナントロリン−９−イル）ナフタレン、１，３−ビス（２−フェニル−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二量体、および２，５−ビス（６’−（２’，２”−ビピリジル））−１，１−ジメチル−３，４−ジフェニルシロールなどのビピリジン二量体は、一般式（１）で表されるクリセン化合物を含む発光層と組み合わせた際の発光効率向上効果が著しく高く、特に好ましい例として挙げられる。 Examples of these compounds having a heteroaryl ring structure include benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoins. Preferred compounds include quinoline derivatives, imidazopyridine derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives and naphthyridine derivatives. 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 ′ A benzoquinoline derivative such as bis (benzo [h] quinolin-2-yl) -9,9′-spirobifluorene, 2,5-bis (6 ′-(2 ′, 2 ″ -bipyridyl))-1, Bipyridine derivatives such as 1-dimethyl-3,4-diphenylsilole, 1,3-bis (4 ′-(2,2 ′: 6′2 ″ -ta Terpyridine derivatives such as pyridinyl)) benzene, naphthyridine derivatives such as bis (1-naphthyl) -4- (1,8-naphthyridin-2-yl) phenylphosphine oxide are preferably used from the viewpoint of electron transporting capability. Furthermore, 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,7-bis (1,10-phenanthroline-9-yl) naphthalene, 1,3-bis (2-phenyl-1, Phenanthroline dimers such as 10-phenanthroline-9-yl) benzene, 2,5-bis (6 ′-(2 ′, 2 ″ -bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, etc. This bipyridine dimer has a remarkably high luminous efficiency improvement effect when combined with a light emitting layer containing a chrysene compound represented by the general formula (1), and is particularly preferable.
上記電子輸送材料は単独でも用いられるが、上記電子輸送材料の２種以上を混合して用いたり、その他の電子輸送材料の一種以上を上記の電子輸送材料に混合して用いても構わない。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、特に限定されないが、好ましくは５．８ｅＶ以上８．０ｅＶ以下であり、より好ましくは６．０ｅＶ以上７．５ｅＶ以下である。 The electron transport material may be used alone, but two or more of the electron transport materials may be mixed and used, or one or more of the other electron transport materials may be mixed with the electron transport material. 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 and 8.0 eV or less, and more preferably 6.0 eV or more and 7.5 eV or less.
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、インクジェット法、印刷法、レーザー誘起熱転写法など特に限定されないが、通常は、素子特性の点から抵抗加熱蒸着または電子ビーム蒸着が好ましい。 The method of forming each of the above layers 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, ink jet method, printing method, laser induced thermal transfer method, etc. From this point, resistance heating vapor deposition or electron beam vapor deposition is preferable.
有機層の厚みは、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、電子輸送層および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 organic 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機能を有する。ここで電気エネルギーとしては主に直流電流が使用されるが、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選ばれることが好ましい。 The light-emitting element of the present invention has a function of converting electrical energy into light. Here, a direct current is mainly used as the electric energy, but a pulse current or an alternating current can also be used. The current value and the voltage value are not particularly limited, but are preferably selected so that 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.
マトリクス方式では、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、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、緑および青の画素を並べて表示させる。カラー表示の場合、その配列方式は、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は、線順次駆動およびアクティブマトリクスのどちらでもよい。線順次駆動は、発光素子の構造が簡単であるが、動作特性を考慮した場合、アクティブマトリクスの方が優れる場合がある。駆動方法は、用途によって使い分ける。 In the matrix method, pixels for display are two-dimensionally arranged such as a lattice shape or a mosaic shape, and characters and images are displayed 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 the case of color display, there are typically a delta type and a stripe type. The matrix driving method may be either line sequential driving or active matrix. In the line sequential drive, the structure of the light emitting element is simple, but the active matrix may be superior in consideration of operation characteristics. The driving method is properly used depending on the application.
セグメント方式とは、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、このパターンの配置によって決められた領域を発光させる方式である。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。 The segment method is a method in which a pattern is formed so as to display predetermined information, and an area determined by the arrangement of the pattern 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, etc. 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、中でも薄型化が検討されているパソコン用途のバックライトに、本発明の発光素子は好ましく用いられる。本発明の発光素子により、従来のものより薄型で軽量なバックライトを提供できる。 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, the light-emitting element of the present invention is preferably used for a backlight for liquid crystal display devices, especially for personal computers for which thinning is being studied. The light-emitting element of the present invention can provide a backlight that is thinner and lighter than conventional ones.
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ない。なお、下記の各実施例にある化合物の番号は上の化学式に記載した化合物の番号を指す。また構造分析に関する評価方法を下記に示す。 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 described in the above chemical formula. The evaluation method for structural analysis is shown below.
１Ｈ−ＮＭＲは超伝導ＦＴＮＭＲ ＥＸ−２７０（日本電子（株）製）を用い、重クロロホルム溶液にて測定を行った。 1 H-NMR was measured with a deuterated chloroform solution using superconducting FTNMR EX-270 (manufactured by JEOL Ltd.).
ＨＰＬＣは、高速液体クロマトグラフ ＬＣ−１０（（株）島津製作所製）を用い、０．１ｇ／Ｌのクロロホルム溶液にて測定した。カラムの展開溶媒としては、０．１％リン酸水溶液とアセトニトリルの混合溶液を用いた。 HPLC was measured with a 0.1 g / L chloroform solution using a high performance liquid chromatograph LC-10 (manufactured by Shimadzu Corporation). As a developing solvent for the column, a mixed solution of 0.1% phosphoric acid aqueous solution and acetonitrile was used.
合成例１（化合物[２９]の合成方法）
クリセン１．２ｇ、Ｎ−ブロモスクシンイミド２．２ｇとジメチルホルムアミド５２ｍｌの混合溶液を窒素気流下、室温で１１時間撹拌した。溶液に水５０ｍｌを注入し、析出物をろ過した。ろ別した固体を水５０ｍｌ、メタノール５０ｍｌでそれぞれ洗浄した後、真空乾燥して、６，１２−ジブロモクリセン１．４ｇを乳白色粉末として得た。
Synthesis Example 1 (Synthesis Method of Compound [29])
A mixed solution of 1.2 g of chrysene, 2.2 g of N-bromosuccinimide and 52 ml of dimethylformamide was stirred at room temperature for 11 hours under a nitrogen stream. 50 ml of water was poured into the solution, and the precipitate was filtered. The solid filtered off was washed with 50 ml of water and 50 ml of methanol, respectively, and then vacuum-dried to obtain 1.4 g of 6,12-dibromochrysene as a milky white powder.
次に、６，１２−ジブロモクリセン１．４ｇ、２−ベンゾフランボロン酸１．９ｇ、リン酸三カリウム４．９ｇ、ＰｄＣｌ２（ｄｐｐｆ）・ＣＨ２Ｃｌ２１７６ｍｇと脱気したジメチルホルムアミド３６ｍｌとの混合溶液を窒素気流下、１００℃で３時間加熱撹拌した。溶液を室温に冷却した後、水３０ｍｌを注入し、ろ過した。得られた固体をメタノール３０ｍｌで洗浄した後、トルエンから再結晶し、真空乾燥した後、黄色結晶１．１ｇを得た。得られた粉末の１Ｈ−ＮＭＲ分析結果は次の通りであり、上記で得られた黄色結晶が化合物［２９］であることが確認された。
１Ｈ−ＮＭＲ（ＣＤＣl３（d=ppm））：7.27-7.44(m, 6H), 7.68-7.84(m, 8H), 8.61-8.65(m, 2H), 8.96(m, 2H), 9.16(s, 2H)。
Next, 1.4 g of 6,12-dibromochrysene, 1.9 g of 2-benzofuranboronic acid, 4.9 g of tripotassium phosphate, 176 mg of PdCl 2 (dppf) · CH 2 Cl 2 and 36 ml of degassed dimethylformamide The mixed solution was heated and stirred at 100 ° C. for 3 hours under a nitrogen stream. After the solution was cooled to room temperature, 30 ml of water was poured and filtered. The obtained solid was washed with 30 ml of methanol, recrystallized from toluene, and vacuum dried to obtain 1.1 g of yellow crystals. The results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the yellow crystals obtained above were the compound [29].
1 H-NMR (CDCl 3 (d = ppm)): 7.27-7.44 (m, 6H), 7.68-7.84 (m, 8H), 8.61-8.65 (m, 2H), 8.96 (m, 2H), 9.16 ( s, 2H).
なお、この化合物［２９］は、油拡散ポンプを用いて１×１０−３Ｐａの圧力下、約２６０℃で昇華精製を行ってから発光素子材料として使用した。ＨＰＬＣ純度（測定波長２５４ｎｍにおける面積％）は昇華精製前が９９．６％、昇華精製後が９９．８％であった。 This compound [29] was used as a light emitting device material after sublimation purification at about 260 ° C. under a pressure of 1 × 10 −3 Pa using an oil diffusion pump. The HPLC purity (area% at a measurement wavelength of 254 nm) was 99.6% before sublimation purification and 99.8% after sublimation purification.
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に切断し、ＩＴＯ導電膜をフォトリソグラフィー法によりパターン加工して、発光部分および電極引き出し部分を作製した。得られた基板をアセトン、“セミコクリン５６”（フルウチ化学（株）製）で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。素子を作製する直前にこの基板を１時間ＵＶ−オゾン処理し、さらに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、銅フタロシアニンを１０ｎｍ、正孔輸送材料として、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニルを５０ｎｍ蒸着した。次に、発光材料として、ホスト材料として下記式に示すＨ−１を、またドーパント材料として化合物[２９]をドープ濃度が２％になるように３５ｎｍの厚さに蒸着した。次に、電子輸送材料として、下記式に示すＥ−１を２０ｎｍの厚さに積層した。以上で形成した有機層上に、フッ化リチウムを０．５ｎｍの厚さに蒸着した後、アルミニウムを１０００ｎｍ蒸着して陰極とし、５×５ｍｍ角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニターの表示値である。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率３．３ｌｍ／Ｗの高効率発光と、C.I.E色度座標で（０．１５，０．１６）と高色純度の青色発光が得られた。
Example 1
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, electron beam vapor-deposited product) on which an ITO transparent conductive film is deposited to 150 nm is cut to 30 × 40 mm, and the ITO conductive film is patterned by a photolithography method to produce a light emitting portion And the electrode extraction part was produced. The obtained substrate was ultrasonically cleaned with acetone, “Semicocrine 56” (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes and dried. Immediately before the device was fabricated, this substrate was subjected to UV-ozone treatment for 1 hour, further placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −5 Pa or less. By the resistance heating method, first, copper phthalocyanine was deposited as a hole injecting material at 10 nm, and 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl was deposited as a hole transporting material at 50 nm. Next, H-1 represented by the following formula as a host material and a compound [29] as a dopant material were vapor-deposited to a thickness of 35 nm so as to have a doping concentration of 2%. Next, as an electron transport material, E-1 represented by the following formula was laminated to a thickness of 20 nm. On the organic layer formed as described above, lithium fluoride was vapor-deposited to a thickness of 0.5 nm, and then aluminum was vapor-deposited with a thickness of 1000 nm to form a 5 × 5 mm square device. The film thickness referred to here is a display value of a crystal oscillation type film thickness monitor. When this light-emitting element was DC-driven at 10 mA / cm 2 , high-efficiency light emission with a luminous efficiency of 3.3 lm / W and blue light emission with high color purity (0.15, 0.16) in CIE chromaticity coordinates were obtained. It was.
比較例１
ドーパント材料として下記式に示すＤ−１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。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、１．６ｌｍ／Ｗの発光効率と、C.I.E色度座標で（０．１５，０．１８）の青色発光が得られた。
Comparative Example 1
A light emitting device was produced in the same manner as in Example 1 except that D-1 shown in the following formula was used as the dopant material. When this light emitting device was DC-driven at 10 mA / cm 2 , a light emission efficiency of 1.6 lm / W and blue light emission of (0.15, 0.18) in CIE chromaticity coordinates were obtained.
比較例２
ドーパント材料として下記式に示すＤ−２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。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、３．３ｌｍ／Ｗの発光効率と、C.I.E色度座標で（０．１８，０．３８）の青緑色発光が得られた。
Comparative Example 2
A light emitting device was produced in the same manner as in Example 1 except that D-2 shown by the following formula was used as the dopant material. When this light emitting device was DC-driven at 10 mA / cm 2 , emission efficiency of 3.3 lm / W and blue-green light emission of (0.18, 0.38) in CIE chromaticity coordinates were obtained.
比較例３
ドーパント材料として下記式に示すＤ−３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。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率１．８ｌｍ／Ｗの発光効率と、C.I.E色度座標で（０．１５，０．１５）と高色純度の青色発光が得られた。
Comparative Example 3
A light emitting device was produced in the same manner as in Example 1 except that D-3 represented by the following formula was used as the dopant material. When this light emitting device was DC driven at 10 mA / cm 2 , a light emission efficiency of 1.8 lm / W and a blue light emission with high color purity of (0.15, 0.15) in CIE chromaticity coordinates were obtained. It was.
比較例４
ドーパント材料として下記式に示すＤ−４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。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率１．７ｌｍ／Ｗの発光効率と、C.I.E色度座標で（０．１５，０．２０）の青色発光が得られた。
Comparative Example 4
A light emitting device was produced in the same manner as in Example 1 except that D-4 represented by the following formula was used as the dopant material. When this light emitting device was DC-driven at 10 mA / cm 2 , a light emission efficiency of 1.7 lm / W and a blue light emission of (0.15, 0.20) in CIE chromaticity coordinates were obtained.
実施例２
ホスト材料として下記式に示すＨ−２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。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率３．５ｌｍ／Ｗの発光効率と、C.I.E色度座標で（０．１５，０．１６）と高色純度の青色発光が得られた。
Example 2
A light-emitting element was fabricated in the same manner as in Example 1 except that H-2 shown by the following formula was used as the host material. When this light emitting device was DC-driven at 10 mA / cm 2 , a light emission efficiency of 3.5 lm / W and a blue light emission with a high color purity of (0.15, 0.16) in CIE chromaticity coordinates were obtained. It was.
実施例３
ホスト材料としてＨ−２、ドーパント材料として化合物[２９]、電子輸送材料としてＥ−２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。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率２．４ｌｍ／Ｗの発光効率と、C.I.E色度座標で（０．１５，０．１６）と高色純度の青色発光が得られた。
Example 3
A light emitting device was produced in the same manner as in Example 1 except that H-2 was used as the host material, Compound [29] was used as the dopant material, and E-2 was used as the electron transport material. When this light emitting device was DC-driven at 10 mA / cm 2 , a light emission efficiency of 2.4 lm / W and a blue light emission with a high color purity of (0.15, 0.16) in CIE chromaticity coordinates were obtained. It was.
実施例４
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に切断し、フォトリソグラフィー法によって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５６”（商品名、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、まず正孔輸送材料として４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニルを１５０ｎｍ蒸着した。次に、ホスト材料としてＨ−１を、またドーパント材料として化合物［２９］をドープ濃度が２％になるように３５ｎｍの厚さに蒸着した。次に、電子輸送材料としてＥ−１を２０ｎｍの厚さに積層した。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。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。そしてフッ化リチウムを０．５ｎｍ蒸着した後、アルミニウムを２００ｎｍ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 4
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 a 300 μm pitch (remaining width 270 μm) × 32 pieces is obtained by photolithography. Patterned into stripes. 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 cleaned with acetone and “Semicocrine 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, respectively, and then washed with ultrapure 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 became 5 × 10 −4 Pa or less. First, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl was deposited as a hole transport material by a resistance heating method to a thickness of 150 nm. Next, H-1 as a host material and compound [29] as a dopant material were deposited to a thickness of 35 nm so that the doping concentration was 2%. Next, E-1 was laminated to a thickness of 20 nm as an electron transport material. The film thickness referred to here is a crystal oscillation type film thickness monitor display value. Next, the mask provided with 16 250 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) by wet etching on a 50 μm thick Kovar plate was replaced with a mask so as to be orthogonal to the ITO stripe in vacuum, It fixed with the magnet from the back surface so that a mask and an ITO board | substrate might closely_contact | adhere. Then, after 0.5 nm of lithium fluoride was deposited, 200 nm of aluminum was deposited to prepare a 32 × 16 dot matrix element. When this element was driven in matrix, characters could be displayed without crosstalk.
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