JP2010192719A - Organic electroluminescence element - Google Patents
Organic electroluminescence element Download PDFInfo
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- JP2010192719A JP2010192719A JP2009036065A JP2009036065A JP2010192719A JP 2010192719 A JP2010192719 A JP 2010192719A JP 2009036065 A JP2009036065 A JP 2009036065A JP 2009036065 A JP2009036065 A JP 2009036065A JP 2010192719 A JP2010192719 A JP 2010192719A
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- 238000005401 electroluminescence Methods 0.000 title claims description 6
- 238000002347 injection Methods 0.000 claims abstract description 13
- 239000007924 injection Substances 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000011368 organic material Substances 0.000 claims abstract description 4
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 12
- 229910000476 molybdenum oxide Inorganic materials 0.000 abstract description 6
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 abstract description 6
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- 239000010410 layer Substances 0.000 description 73
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- 238000000034 method Methods 0.000 description 15
- 239000000758 substrate Substances 0.000 description 13
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
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- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 3
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- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
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- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- MWMNLUGPPZOPJQ-UHFFFAOYSA-N 4-(4-aminophenyl)-3-naphthalen-1-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC2=CC=CC=C12 MWMNLUGPPZOPJQ-UHFFFAOYSA-N 0.000 description 1
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- DBRHADJEDWLNII-UHFFFAOYSA-N C1=CC=CC=2SC3=CC=CC=C3NC12.C1=NN=CC2=CC=CC=C12 Chemical compound C1=CC=CC=2SC3=CC=CC=C3NC12.C1=NN=CC2=CC=CC=C12 DBRHADJEDWLNII-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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Images
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- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
本発明は、マルチフォトンエミッション素子構造を備えた有機エレクトロルミネッセンス素子（以下、有機ＥＬ素子と略称する）に関する。 The present invention relates to an organic electroluminescence element (hereinafter abbreviated as an organic EL element) having a multi-photon emission element structure.
有機ＥＬ素子は、有機化合物を発光材料とする自己発光型素子であり、高速度での発光が可能であるため、動画の表示に好適であり、また、素子構造が簡単でディスプレイパネルの薄型化が可能である等の特性を有している。このような優れた特性を有していることから、有機ＥＬ素子は、携帯電話や車載用ディスプレイとして、日常生活において普及しつつある。
さらに、近年では、上記のような薄型面発光という特長を活かして、次世代の照明としても注目されている。
An organic EL element is a self-luminous element that uses an organic compound as a luminescent material, and can emit light at a high speed. Therefore, it is suitable for displaying moving images, and the element structure is simple and the display panel is thinned. It has the characteristic that it is possible. Due to such excellent characteristics, organic EL elements are becoming popular in daily life as mobile phones and in-vehicle displays.
Furthermore, in recent years, it has been attracting attention as a next-generation illumination, taking advantage of the above-described thin surface light emission.
前記有機ＥＬ素子は、実用性の向上および普及のため、高効率化および長寿命化を図ることが求められており、その一手法としてマルチフォトンエミッション（以下、ＭＰＥと略称する）素子構造が提案されている。
マルチフォトンエミッションとは、少なくとも一層の発光層を含む複数個の発光ユニットを、電荷発生層（ＣＧＬ；Charge Generation Layer）を介して直列に接続するように積層させた素子構造である（例えば、特許文献１参照）。このような素子構造によれば、１ユニット素子と同じ電流量で、複数の各発光層からの発光が同時に得られるため、発光ユニット（以下、ＥＬ−ｕｎｉｔともいう）の個数倍相当の電流効率および外部量子効率を得ることができる。
The organic EL element is required to have high efficiency and long life in order to improve practical use and spread, and a multi-photon emission (hereinafter abbreviated as MPE) element structure is proposed as one method. Has been.
Multi-photon emission is an element structure in which a plurality of light emitting units including at least one light emitting layer are stacked so as to be connected in series via a charge generation layer (CGL) (for example, a patent) Reference 1). According to such an element structure, light emission from a plurality of light emitting layers can be simultaneously obtained with the same amount of current as that of one unit element, so that the current efficiency equivalent to the number of light emitting units (hereinafter also referred to as EL-units). And external quantum efficiency can be obtained.
従来のＭＰＥ素子は、一般に、ＩＴＯ／ＥＬ−ｕｎｉｔ／Ｌｉ／Ａｌ／ＭｏＯ3／ＥＬ−ｕｎｉｔ／Ａｌのような層構成からなり、発光ユニット間の電荷発生層の一部にモリブデンが使用されている。 Conventional MPE devices generally have a layer structure such as ITO / EL-unit / Li / Al / MoO 3 / EL-unit / Al, and molybdenum is used as part of the charge generation layer between the light emitting units. Yes.
なお、特許文献２に、下記（化１）に示す１，４，５，８，９，１２−ヘキサアザトリフェニレンヘキサカルボニトリル（以下、ＨＡＴ（ＣＮ）6またはＨＡＴＣＮと略称する）を含む層を有する有機発光素子が開示されているが、これらは、ＨＡＴＣＮをＭＰＥ素子における電荷発生層として採用するものではない。
しかしながら、遷移金属であるモリブデン酸化物は、融点が非常に高く、高温（蒸着源温度６００℃以上）での成膜を余儀なくされ、発光層等の他の有機層およびプロセスの効率化に悪影響を与えていた。 However, molybdenum oxide, which is a transition metal, has a very high melting point, which necessitates film formation at a high temperature (evaporation source temperature of 600 ° C. or higher), and adversely affects the efficiency of other organic layers such as a light-emitting layer and the process. Was giving.
本発明は、上記技術的課題を解決するためになされたものであり、上記のようなＭＰＥ素子において、電荷発生層にモリブデン酸化物に代わる材料を採用し、かつ、より高効率で発光が得られる層構成を備えた有機ＥＬ素子を提供することを目的とするものである。 The present invention has been made to solve the above technical problem, and in the MPE element as described above, a material replacing the molybdenum oxide is used for the charge generation layer, and light emission can be obtained with higher efficiency. An object of the present invention is to provide an organic EL device having a layer structure.
本発明に係る有機ＥＬ素子は、一対の電極間に、少なくとも１層の発光層を含む発光ユニットを複数個備え、前記各発光ユニットが電荷発生層によって仕切られたＭＰＥ構造の有機ＥＬ素子であって、前記電荷発生層が少なくとも下記一般式（１）で表される化合物を含む有機材料で構成され、前記電荷発生層と前記発光ユニットとの間にアルカリ金属化合物を含む電子注入層が設けられていることを特徴とする。 The organic EL device according to the present invention is an organic EL device having an MPE structure in which a plurality of light emitting units including at least one light emitting layer are provided between a pair of electrodes, and each of the light emitting units is partitioned by a charge generation layer. The charge generation layer is made of an organic material containing at least a compound represented by the following general formula (1), and an electron injection layer containing an alkali metal compound is provided between the charge generation layer and the light emitting unit. It is characterized by.
前記一般式（１）中、Ｒは、それぞれ独立に、水素、ハロゲン基、炭素数１〜１２のアルキル基、アルコキシ基、アルキルアミノ基、アルキルシリル基、アリール基、アリールアミノ基、複素環基、エステル基、アミド基、ニトロ基およびニトリル基からなる群の中から選ばれた置換基である。隣接するＲは互いに結合して、環状構造を形成していてもよい。
このような化合物を電荷発生層に用いることにより、モリブデン酸化物を用いなくても、高効率で発光する有機ＥＬ素子を構成することができる。
In the general formula (1), each R independently represents hydrogen, a halogen group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group, an alkylamino group, an alkylsilyl group, an aryl group, an arylamino group, or a heterocyclic group. , A substituent selected from the group consisting of an ester group, an amide group, a nitro group and a nitrile group. Adjacent Rs may be bonded to each other to form a cyclic structure.
By using such a compound for the charge generation layer, an organic EL element that emits light with high efficiency can be configured without using molybdenum oxide.
本発明に係る有機ＥＬ素子によれば、ＭＰＥ素子構造において、電荷発生層にモリブデン酸化物に代わる材料を採用し、かつ、より高効率で発光が得られる層構成を備えた有機ＥＬ素子を提供することが可能となる。
したがって、本発明に係る有機エレクトロルミネッセンス素子は、近年、より優れた色再現性が求められるＯＡコンピュータ用や壁掛けテレビ用のフラットパネル・ディスプレイ、さらに、照明機器、複写機の光源、液晶ディスプレイや計器類のバックライト光源等の面発光体としての特徴を活かした光源、表示板、標識灯への応用が期待される。
The organic EL element according to the present invention provides an organic EL element that employs a material in place of molybdenum oxide for the charge generation layer in the MPE element structure and has a layer structure that can emit light with higher efficiency. It becomes possible to do.
Therefore, the organic electroluminescence device according to the present invention is a flat panel display for OA computers and wall-mounted televisions, which have recently been required to have better color reproducibility, as well as lighting equipment, light sources for copying machines, liquid crystal displays and instruments. Applications to light sources, display boards, and marker lamps that take advantage of the characteristics of surface light emitters, such as other types of backlight light sources, are expected.
以下、本発明について、図面を参照して、より詳細に説明する。
図１に、本発明に係る有機ＥＬ素子の層構成の概要を示す。
図１に示すように、本発明に係る有機ＥＬ素子は、陽極１と陰極５の一対の電極間に、少なくとも１層の発光層を含む発光ユニット２を複数個備え、前記各発光ユニット２が電荷発生層４によって仕切られたＭＰＥ素子構造の有機ＥＬ素子である。そして、前記電荷発生層４が少なくとも前記一般式（１）表される化合物を含む有機材料で構成され、前記電荷発生層４と前記発光ユニット２との間にアルカリ金属化合物を含む電子注入層３が設けられているものである。
このような構成とすることにより、電荷発生層の少なくとも一部に含まれる前記一般式（１）表される化合物は、隣接する発光ユニットの正孔輸送性材料（例えば、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ビス（１−ナフチル）−１，１’−ビフェニル−４，４’−ジアミン（以下、α−ＮＰＤと略称する））等により、優れた電荷発生層として機能する。さらに、他方の発光ユニットに隣接する層として、電子注入層としての機能を有するアルカリ金属化合物（例えば、ＬｉＦ／Ａｌ）を用いることにより、双方の組み合わせによって、モリブデン酸化物等を用いた従来の電荷発生層を用いた場合と同等以上の高効率での発光を得ることができる。
また、電荷発生層を有するＭＰＥ素子構造であっても、低温プロセスでの素子の製造が可能となり、プロセス中の有機層へのダメージを低減することができる。
Hereinafter, the present invention will be described in more detail with reference to the drawings.
In FIG. 1, the outline | summary of the layer structure of the organic EL element which concerns on this invention is shown.
As shown in FIG. 1, the organic EL device according to the present invention includes a plurality of
With such a configuration, the compound represented by the general formula (1) contained in at least a part of the charge generation layer is a hole transporting material (for example, N, N′-diphenyl) of an adjacent light emitting unit. -N, N′-bis (1-naphthyl) -1,1′-biphenyl-4,4′-diamine (hereinafter abbreviated as α-NPD)) and the like function as an excellent charge generation layer. Furthermore, by using an alkali metal compound (for example, LiF / Al) having a function as an electron injection layer as a layer adjacent to the other light emitting unit, a conventional charge using molybdenum oxide or the like can be obtained by combining both. It is possible to obtain light emission with high efficiency equal to or higher than that when the generation layer is used.
Further, even with an MPE element structure having a charge generation layer, it is possible to manufacture an element by a low temperature process, and to reduce damage to the organic layer during the process.
本発明に係る有機ＥＬ素子において、各発光ユニットを仕切る電荷発生層に用いられる化合物は、前記一般式（１）で表されるように、１，４，５，８，９，１２−ヘキサアザトリフェニレン（以下、ＨＡＴと略称する）を母骨格とする化合物であり、前記一般式（１）において、Ｒは、それぞれ独立に、水素、ハロゲン基、炭素数１〜１２のアルキル基、アルコキシ基、アルキルアミノ基、アルキルシリル基、アリール基、アリールアミノ基、複素環基、エステル基、アミド基、ニトロ基およびニトリル基からなる群の中から選ばれた置換基である。また、隣接するＲは互いに結合して、環状構造を形成していてもよい。 In the organic EL device according to the present invention, the compound used in the charge generation layer partitioning each light emitting unit is 1, 4, 5, 8, 9, 12-hexaaza as represented by the general formula (1). A compound having triphenylene (hereinafter abbreviated as HAT) as a mother skeleton, and in the general formula (1), each R independently represents hydrogen, a halogen group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group, The substituent is selected from the group consisting of an alkylamino group, an alkylsilyl group, an aryl group, an arylamino group, a heterocyclic group, an ester group, an amide group, a nitro group, and a nitrile group. Further, adjacent Rs may be bonded to each other to form a cyclic structure.
上記置換基のうち、ハロゲン基とは、フッ素、塩素、臭素およびヨウ素のいずれかを示す。
アルキル基とは、例えば、メチル基、エチル基、プロピル基、ブチル基等の飽和脂肪族炭化水素基を示し、炭素数は１〜１２であり、直鎖状であっても分岐鎖状であってもよい。
アルコキシ基とは、例えば、メトキシ基等のエーテル結合を介した飽和脂肪族炭化水素基を示し、直鎖状であっても分岐鎖状であってもよい。
アルキルアミノ基は、例えば、ジメチルアミノ基、ジエチルアミノ基等の窒素原子を介した脂肪族炭化水素基を示して、直鎖状であっても分岐状であってもよい。
アルキルシリル基とは、例えば、トリメチルシリル基等のケイ素化合物基を示す。
アリール基は、例えば、フェニル基、ナフチル基、アントラニル基等の芳香族炭化水素基を示し、無置換であっても置換されていてもよい。
アリールアミノ基は、例えば、ジフェニルアミノ基、ジトリルアミノ基等の窒素原子を介した芳香族炭化水素基を示し、無置換であっても置換されていてもよい。
複素環基は、炭素以外に、窒素、酸素または酸素のいずれかを環構成元素として含む基を示す。例えば、トリアジン、オキサゾール、オキサジアゾール、チアゾール、チアジアゾール、フラン、フラザン、チオフェン、ピラン、ピロール、ピラゾール、イミダゾール、イミダゾリジン、イミダゾリン、クマロン、クロメン、インドール、インドリン、イソクマロン、シンノリン、キナゾリン、キノキサリン、フタラジン、フェノチアジン、アクリジン、フェナンソリジン、キノリン、イソキノリン、ナフチリジン、ピリジン、ピリミジン、トリアゾール、カルバゾール等が挙げられ、無置換であっても置換されていてもよい。
Among the above substituents, the halogen group means any of fluorine, chlorine, bromine and iodine.
The alkyl group refers to, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group. The alkyl group has 1 to 12 carbon atoms and may be linear or branched. May be.
The alkoxy group represents, for example, a saturated aliphatic hydrocarbon group via an ether bond such as a methoxy group, and may be linear or branched.
The alkylamino group represents, for example, an aliphatic hydrocarbon group via a nitrogen atom such as a dimethylamino group or a diethylamino group, and may be linear or branched.
The alkylsilyl group refers to a silicon compound group such as a trimethylsilyl group.
The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, and an anthranyl group, and may be unsubstituted or substituted.
The arylamino group represents an aromatic hydrocarbon group via a nitrogen atom such as a diphenylamino group or a ditolylamino group, and may be unsubstituted or substituted.
The heterocyclic group represents a group containing any one of nitrogen, oxygen and oxygen as a ring constituent element in addition to carbon. For example, triazine, oxazole, oxadiazole, thiazole, thiadiazole, furan, furazane, thiophene, pyran, pyrrole, pyrazole, imidazole, imidazolidine, imidazoline, coumarone, chromene, indole, indoline, isocoumarone, cinnoline, quinazoline, quinoxaline, phthalazine Phenothiazine, acridine, phenanthridine, quinoline, isoquinoline, naphthyridine, pyridine, pyrimidine, triazole, carbazole and the like, which may be unsubstituted or substituted.
上記一般式（１）で表わされる化合物のうち、Ｒがニトリル基である上記（化１）に示す１，４，５，８，９，１２−ヘキサアザトリフェニレンヘキサカルボニトリル（ＨＡＴＣＮ）が、特に好適に用いることができる。 Among the compounds represented by the general formula (1), 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile (HATCN) represented by the above (Chemical Formula 1) in which R is a nitrile group is particularly preferable. It can be used suitably.
また、前記電子注入層に用いられるアルカリ金属化合物には、アルカリ金属ハロゲン化物およびアルカリ土類金属ハロゲン化物の群の中から選択される少なくとも一つの金属化合物を用いることが好ましい。
前記アルカリ金属ハロゲン化物としては、フッ化リチウム、フッ化ナトリウム、フッ化カリウム、フッ化セシウム、塩化リチウム等が挙げられる。
また、前記アルカリ土類金属ハロゲン化物としては、フッ化マグネシウム、フッ化カルシウム、フッ化バリウム、フッ化ストロンチウム等が挙げられる。
The alkali metal compound used for the electron injection layer is preferably at least one metal compound selected from the group of alkali metal halides and alkaline earth metal halides.
Examples of the alkali metal halide include lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, and lithium chloride.
Examples of the alkaline earth metal halide include magnesium fluoride, calcium fluoride, barium fluoride, and strontium fluoride.
本発明に係る有機ＥＬ素子の具体的な素子構成としては、例えば、発光ユニットが２個の場合は、ＩＴＯ／ＥＬ−ｕｎｉｔ／ＬｉＦ／Ａｌ／ＨＡＴ／ＥＬ−ｕｎｉｔ／Ａｌ、発光ユニットが３個以上の場合は、ＩＴＯ／ＥＬ−ｕｎｉｔ／ＬｉＦ／Ａｌ／ＨＡＴ／ＥＬ−ｕｎｉｔ／……／ＬｉＦ／Ａｌ／ＨＡＴ／ＥＬ−ｕｎｉｔ／Ａｌ等の層構成が挙げられる。 As a specific element configuration of the organic EL element according to the present invention, for example, when there are two light emitting units, ITO / EL-unit / LiF / Al / HAT / EL-unit / Al, three light emitting units are provided. In the above case, a layer structure such as ITO / EL-unit / LiF / Al / HAT / EL-unit /... / LiF / Al / HAT / EL-unit / Al can be used.
各発光ユニット自体の層構成は、特に限定されるものではないが、少なくとも１層の発光層を含むものであり、それ以外には、正孔輸送層、電子輸送層を含む層構成とすることができ、また、正孔注入層、正孔輸送発光層、電子注入層、電子輸送発光層等をも含む公知の層構成とすることもできる。例えば、１個の発光ユニットを、正孔注入輸送層／発光層／電子注入輸送層のような層構成とすることができる。 The layer structure of each light-emitting unit itself is not particularly limited, but includes at least one light-emitting layer, and other than that, the layer structure includes a hole transport layer and an electron transport layer. Moreover, it can also be set as the well-known layer structure also including a positive hole injection layer, a positive hole transport light emitting layer, an electron injection layer, an electron transport light emitting layer, etc. For example, one light emitting unit can have a layer configuration such as a hole injection transport layer / light emission layer / electron injection transport layer.
前記発光層、正孔注入層、正孔輸送層、正孔輸送性発光層、電子注入層、電子輸送層、電子輸送性発光層に用いられる材料は、特に限定されるものではなく、公知のものから適宜選択して用いることができ、低分子系または高分子系のいずれであってもよい。
なお、プロセス効率化の観点から、低温プロセスによる成膜が可能な材料を選択することが好ましい。
Materials used for the light-emitting layer, hole injection layer, hole transport layer, hole transport light-emitting layer, electron injection layer, electron transport layer, and electron transport light-emitting layer are not particularly limited. It can be appropriately selected from those used, and may be either low molecular or high molecular.
Note that, from the viewpoint of process efficiency, it is preferable to select a material that can be formed by a low-temperature process.
上記各層の形成は、真空蒸着法、スパッタリング法等などの乾式法、インクジェット法、キャスティング法、ディップコート法、バーコート法、ブレードコート法、ロールコート法、グラビアコート法、フレキソ印刷法、スプレーコート法等の湿式法により行うことができる。好ましくは、真空蒸着により膜形成を行う。
また、前記各層の膜厚は、各層同士の適応性や求められる全体の層厚さ等を考慮して、適宜状況に応じて定められるが、通常、５ｎｍ〜５μｍの範囲内であることが好ましい。
Each of the above layers is formed by a dry method such as a vacuum deposition method or a sputtering method, an inkjet method, a casting method, a dip coating method, a bar coating method, a blade coating method, a roll coating method, a gravure coating method, a flexographic printing method, or a spray coating. It can carry out by wet methods, such as a method. Preferably, the film is formed by vacuum deposition.
Further, the film thickness of each layer is appropriately determined depending on the situation in consideration of adaptability between the layers and the required total layer thickness, and it is usually preferably in the range of 5 nm to 5 μm. .
本発明に係る有機ＥＬ素子の電極は、透明基板上に透明導電性薄膜が形成されたものであることが好ましい。
前記基板は、有機エレクトロルミネッセンス素子の支持体となるものであり、基板側が発光面となる場合、可視光において透光性を有する透明基板を用いることが好ましい。光透過率は８０％以上であることが好ましく、８５％以上であることが好ましい。より好ましくは、９０％以上である。
前記透明基板としては、一般に、ＢＫ７、ＢａＫ１、Ｆ２等の光学ガラス、石英ガラス、無アルカリガラス、ホウケイ酸ガラス、アルミノケイ酸ガラス等のガラス基板、ＰＭＭＡ等のアクリル樹脂、ポリカーボネート、ポリエーテルスルホネート、ポリスチレン、ポリオレフィン、エポキシ樹脂、ポリエチレンテレフタレート等のポリエステル等のポリマー基板が用いられる。
前記基板の厚さは、通常、０．１〜１０ｍｍ程度のものが用いられるが、機械的強度、重量等を考慮して、０．３〜５ｍｍであることが好ましく、０．５〜２ｍｍであることがより好ましい。
The electrode of the organic EL device according to the present invention is preferably one in which a transparent conductive thin film is formed on a transparent substrate.
The substrate serves as a support for the organic electroluminescence element, and when the substrate side is a light emitting surface, it is preferable to use a transparent substrate having translucency in visible light. The light transmittance is preferably 80% or more, and preferably 85% or more. More preferably, it is 90% or more.
As the transparent substrate, generally, glass substrates such as optical glass such as BK7, BaK1, and F2, quartz glass, alkali-free glass, borosilicate glass, and aluminosilicate glass, acrylic resin such as PMMA, polycarbonate, polyether sulfonate, polystyrene Polymer substrates such as polyolefins, epoxy resins, polyesters such as polyethylene terephthalate are used.
The thickness of the substrate is usually about 0.1 to 10 mm, but preferably 0.3 to 5 mm in view of mechanical strength, weight, etc., and 0.5 to 2 mm. More preferably.
前記基板上には、通常、陽極が形成される。この陽極は、仕事関数の大きい（４ｅＶ以上）金属、合金、導電性化合物等により構成されるが、前記透明基板上に透明電極として形成されることが好ましい。
この透明電極には、酸化インジウム錫（ＩＴＯ）、酸化インジウム亜鉛、酸化亜鉛等の金属酸化物が一般的に用いられ、特に、透明性や導電性等の観点から、ＩＴＯが好適に用いられる。
この透明電極の膜厚は、透明性および導電性の確保のため、８０〜４００ｎｍであることが好ましく、１００〜２００ｎｍであることがより好ましい。
陽極の形成は、通常、スパッタリング法、真空蒸着法等により行われ、透明導電性薄膜として形成されることが好ましい。
An anode is usually formed on the substrate. The anode is composed of a metal, alloy, conductive compound or the like having a high work function (4 eV or more), and is preferably formed as a transparent electrode on the transparent substrate.
For the transparent electrode, metal oxides such as indium tin oxide (ITO), indium zinc oxide, and zinc oxide are generally used. In particular, ITO is preferably used from the viewpoint of transparency and conductivity.
The film thickness of the transparent electrode is preferably 80 to 400 nm, and more preferably 100 to 200 nm, in order to ensure transparency and conductivity.
The anode is usually formed by a sputtering method, a vacuum deposition method or the like, and is preferably formed as a transparent conductive thin film.
一方、前記陽極に対向する陰極は、仕事関数の小さい（４ｅＶ以下）金属、合金、導電性化合物により構成される。例えば、アルミニウム、アルミニウム−リチウム合金、マグネシウム−銀合金、フッ化リチウム等が挙げられ、単層であっても、あるいはまた、仕事関数の異なる材料を組み合わせた複層としてもよい。
前記陰極の膜厚は、１０〜５００ｎｍであることが好ましく、５０〜２００ｎｍであることがより好ましい。
On the other hand, the cathode facing the anode is made of a metal, alloy, or conductive compound having a small work function (4 eV or less). For example, aluminum, an aluminum-lithium alloy, a magnesium-silver alloy, lithium fluoride, and the like can be given. A single layer may be used, or a multilayer may be formed by combining materials having different work functions.
The film thickness of the cathode is preferably 10 to 500 nm, and more preferably 50 to 200 nm.
以下、本発明を実施例に基づきさらに具体的に説明するが、本発明は下記の実施例により制限されるものではない。
［比較例１］
（１ユニット素子の作製）
電子輸送材料として、下記（化３）に示すビス４，６−［３，５−（ジ−４−ピリジル）フェニル］−２−メチルピリミジン（以下、Ｂ４ＰＹＭＰＭと略称する）を用いて、ＩＴＯ／ＴＡＰＣ（７０ｎｍ）／ＴＣＴＡ：Ｉｒ（ｐｐｙ）3（５ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）3（５ｎｍ）／Ｂ４ＰＹＭＰＭ（７０ｎｍ）／ＬｉＦ（１ｎｍ）／Ａｌ（１００ｎｍ）の層構成からなる１ユニット素子を、比較基準のため作製した。
なお、ＴＡＰＣ（化４）、ＴＣＴＡ（化５）、Ｉｒ（ｐｐｙ）3（化６）の構造式を下記に示す。
EXAMPLES Hereinafter, although this invention is demonstrated more concretely based on an Example, this invention is not restrict | limited by the following Example.
[Comparative Example 1]
(Production of 1 unit element)
As an electron transport material,
The structural formulas of TAPC (Chemical Formula 4), TCTA (Chemical Formula 5), and Ir (ppy) 3 (Chemical Formula 6) are shown below.
具体的な素子の作製方法は、以下のとおりである。
まず、パターニング済みの透明導電膜（ＩＴＯ）が膜厚１３０ｎｍで成膜されたガラス基板を、純水と界面活性剤による超音波洗浄、純水による流水洗浄、純水とイソプロピルアルコールの１：１混合溶液による超音波洗浄、イソプロピルアルコールによる煮沸洗浄の順で洗浄処理した。この基板を沸騰中のイソプロピルアルコールからゆっくり引き上げ、イソプロピルアルコール蒸気中で乾燥させ、最後に、紫外線オゾン洗浄を行った。
この基板を陽極１とし、真空チャンバ内に配置し、１×１０-6Ｔｏｒｒまで真空排気し、該真空チャンバ内には、蒸着材料をそれぞれ充填した各モリブデン製ボートと、所定のパターンで成膜するための蒸着用マスクを設置しておき、前記ボートを通電加熱し、蒸着材料を蒸発させることにより、順次、上記層構成となるように成膜を行った。
A specific method for manufacturing the element is as follows.
First, a glass substrate on which a patterned transparent conductive film (ITO) is formed to a thickness of 130 nm is subjected to ultrasonic cleaning with pure water and a surfactant, flowing water cleaning with pure water, and 1: 1 of pure water and isopropyl alcohol. Washing was performed in the order of ultrasonic washing with the mixed solution and boiling washing with isopropyl alcohol. The substrate was slowly pulled up from the boiling isopropyl alcohol, dried in isopropyl alcohol vapor, and finally subjected to ultraviolet ozone cleaning.
This substrate is used as the anode 1, placed in a vacuum chamber, evacuated to 1 × 10 −6 Torr, and each molybdenum boat filled with a vapor deposition material and a predetermined pattern are formed in the vacuum chamber. A vapor deposition mask was installed, and the boat was energized and heated to evaporate the vapor deposition material, so that the layers were sequentially formed to have the above layer structure.
最後に、真空チャンバを真空に保ったまま、マスクを交換し、陰極蒸着用のマスクを設置して、フッ化リチウム（ＬｉＦ）層およびアルミニウム（Ａｌ）層からなる２層陰極を形成した。
そして、真空チャンバを大気圧に戻し、上記により各層を蒸着させた基板を取り出し、窒素置換されたグローブボックスに移し、ＵＶ硬化樹脂を用いて、別のガラス板により封止し、１ユニット素子を得た。
Finally, while maintaining the vacuum chamber in a vacuum, the mask was exchanged and a mask for cathode deposition was installed to form a two-layer cathode composed of a lithium fluoride (LiF) layer and an aluminum (Al) layer.
Then, the vacuum chamber is returned to atmospheric pressure, the substrate on which each layer is deposited as described above is taken out, transferred to a nitrogen-substituted glove box, sealed with another glass plate using a UV curable resin, and one unit element is Obtained.
［実施例１］
（２ユニットＭＰＥ素子の作製）
上記の１ユニット素子から電極を除いた部分を１個の発光ユニットとし、電荷発生層（ＣＧＬ）は、ＨＡＴＣＮと発光ユニット中の１層目のＴＡＰＣとにより構成されるものとし、２個の発光ユニットを積層させ、ＩＴＯ（１３０ｎｍ）／ＥＬ−ｕｎｉｔ（１５０ｎｍ）／ＬｉＦ（１ｎｍ）／Ａｌ（１ｎｍ）／ＨＡＴＣＮ（５ｎｍ）／ＥＬ−ｕｎｉｔ（１５０ｎｍ）／ＬｉＦ（１ｎｍ）／Ａｌ（１００ｎｍ）の層構成からなる発光ユニット２個を有するＭＰＥ素子を作製した。
各層の成膜は、上記の１ユニット素子の作製の場合と同様にして、順次、行った。
[Example 1]
(Production of 2-unit MPE element)
The part obtained by removing the electrode from the one unit element is one light emitting unit, and the charge generation layer (CGL) is composed of HATCN and the first layer of TAPC in the light emitting unit. Units are stacked, ITO (130 nm) / EL-unit (150 nm) / LiF (1 nm) / Al (1 nm) / HATCN (5 nm) / EL-unit (150 nm) / LiF (1 nm) / Al (100 nm) layer An MPE element having two light emitting units having the configuration was produced.
The film formation of each layer was sequentially performed in the same manner as in the production of the one-unit element.
［実施例２］
（３ユニットＭＰＥ素子の作製）
実施例１と同様にして、ＩＴＯ（１３０ｎｍ）／ＥＬ−ｕｎｉｔ（１５０ｎｍ）／ＬｉＦ（１ｎｍ）／Ａｌ（１ｎｍ）／ＨＡＴＣＮ（５ｎｍ）／ＥＬ−ｕｎｉｔ（１５０ｎｍ）／ＬｉＦ（１ｎｍ）／Ａｌ（１ｎｍ）／ＨＡＴＣＮ（５ｎｍ）／ＥＬ−ｕｎｉｔ（１５０ｎｍ）／ＬｉＦ（１ｎｍ）／Ａｌ（１００ｎｍ）の層構成からなる発光ユニット３個を有するＭＰＥ素子を作製した。
[Example 2]
(Production of 3 unit MPE element)
In the same manner as in Example 1, ITO (130 nm) / EL-unit (150 nm) / LiF (1 nm) / Al (1 nm) / HATCN (5 nm) / EL-unit (150 nm) / LiF (1 nm) / Al (1 nm) ) / HATCN (5 nm) / EL-unit (150 nm) / LiF (1 nm) / MP (Equipment) having three light emitting units having a layer structure of Al (100 nm) was produced.
（素子評価）
上記において作製した各素子は、１０Ｖの直流電圧を印加したところ、いずれも、緑色燐光発光が得られた。
また、各素子について、電流効率および外部量子効率を求めた。
図２に、１ユニット素子（比較例１）、２ユニットＭＰＥ素子（実施例１）、３ユニットＭＰＥ素子（実施例２）の電流密度と電流効率の関係をグラフとして示す。
また、図３に、上記各素子の電流密度と外部量子効率の関係をグラフとして示す。
(Element evaluation)
Each of the devices prepared above was subjected to green phosphorescence emission when a DC voltage of 10 V was applied.
Moreover, the current efficiency and the external quantum efficiency were determined for each element.
FIG. 2 is a graph showing the relationship between the current density and the current efficiency of 1 unit element (Comparative Example 1), 2 unit MPE element (Example 1), and 3 unit MPE element (Example 2).
FIG. 3 is a graph showing the relationship between the current density of each element and the external quantum efficiency.
１ユニット素子（比較例１）については、１００ｃｄ／ｍ2時、電流効率８０ｃｄ／Ａ、外部量子効率２２．５％が得られた。
２ユニットＭＰＥ素子（実施例１）は、各発光ユニット中のＩｒ（ｐｐｙ）3からの発光が光学干渉により強め合う位置になるように膜厚を考慮した場合、１００ｃｄ／ｍ2時、電流効率１７０ｃｄ／Ａ、外部量子効率４６％であり、前記１ユニット素子の２倍以上の発光効率が得られた。
さらに、３ユニットＭＰＥ素子（実施例２）も、各発光ユニット中のＩｒ（ｐｐｙ）3からの発光が光学干渉により強め合う位置になるように膜厚を考慮した場合、１００ｃｄ／ｍ2時、電流効率２５０ｃｄ／Ａ、外部量子効率６４％であり、前記１ユニット素子の約３倍の発光効率が得られた。
For one unit element (Comparative Example 1), a current efficiency of 80 cd / A and an external quantum efficiency of 22.5% were obtained at 100 cd / m 2 .
The 2-unit MPE element (Example 1) has a current efficiency of 100 cd / m 2 when considering the film thickness so that the light emission from Ir (ppy) 3 in each light-emitting unit is intensified by optical interference. The light emission efficiency was 170 cd / A, the external quantum efficiency was 46%, and the light emission efficiency was twice or more that of the one unit element.
Further, the 3-unit MPE element (Example 2) also has a thickness of 100 cd / m 2 when considering the film thickness so that the light emission from Ir (ppy) 3 in each light-emitting unit is intensified by optical interference. The current efficiency was 250 cd / A, the external quantum efficiency was 64%, and the light emission efficiency about three times that of the one unit element was obtained.
１ 陽極
２ 発光ユニット
３ 電子注入層
４ 電荷発生層
５ 陰極
DESCRIPTION OF SYMBOLS 1
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Cited By (14)
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006173550A (en) * | 2004-02-18 | 2006-06-29 | Sony Corp | Display element |
| JP2006351398A (en) * | 2005-06-17 | 2006-12-28 | Sony Corp | Display element |
| JP2007035579A (en) * | 2005-07-29 | 2007-02-08 | Sanyo Electric Co Ltd | Organic electroluminescent device and organic electroluminescent display device |
| WO2007132704A1 (en) * | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| JP2010056077A (en) * | 2008-07-30 | 2010-03-11 | Panasonic Electric Works Co Ltd | Organic electroluminescent element and its manufacturing method |
-
2009
- 2009-02-19 JP JP2009036065A patent/JP2010192719A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006173550A (en) * | 2004-02-18 | 2006-06-29 | Sony Corp | Display element |
| JP2006351398A (en) * | 2005-06-17 | 2006-12-28 | Sony Corp | Display element |
| JP2007035579A (en) * | 2005-07-29 | 2007-02-08 | Sanyo Electric Co Ltd | Organic electroluminescent device and organic electroluminescent display device |
| WO2007132704A1 (en) * | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| JP2010056077A (en) * | 2008-07-30 | 2010-03-11 | Panasonic Electric Works Co Ltd | Organic electroluminescent element and its manufacturing method |
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| US9972802B2 (en) | 2012-04-20 | 2018-05-15 | Konica Minolta, Inc. | Organic electroluminescent element |
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