JP5466005B2 - Oledアプリケーション用オキサゾール−三重項−発光体 - Google Patents
Oledアプリケーション用オキサゾール−三重項−発光体 Download PDFInfo
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- JP5466005B2 JP5466005B2 JP2009522153A JP2009522153A JP5466005B2 JP 5466005 B2 JP5466005 B2 JP 5466005B2 JP 2009522153 A JP2009522153 A JP 2009522153A JP 2009522153 A JP2009522153 A JP 2009522153A JP 5466005 B2 JP5466005 B2 JP 5466005B2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 62
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
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- UOFTVUCCJTXQDX-UHFFFAOYSA-N CCOC(=O)C#C[Pt]C1=C(C=2OC(OCC)=CN=2)C=CC=C1C1=NC=C(OCC)O1 Chemical compound CCOC(=O)C#C[Pt]C1=C(C=2OC(OCC)=CN=2)C=CC=C1C1=NC=C(OCC)O1 UOFTVUCCJTXQDX-UHFFFAOYSA-N 0.000 claims description 4
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
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- QDMZSULSKHNKNJ-UHFFFAOYSA-N 5-tert-butyl-2-phenyl-1,3-oxazole Chemical compound C(C)(C)(C)C1=CN=C(O1)C1=CC=CC=C1 QDMZSULSKHNKNJ-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- FBZUCWUBJYNILS-UHFFFAOYSA-N bis(1H-pyrazol-5-yloxy)borinic acid Chemical compound C=1C=NNC=1OB(O)OC1=CC=NN1 FBZUCWUBJYNILS-UHFFFAOYSA-N 0.000 description 1
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- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
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- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
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- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000012780 transparent material Substances 0.000 description 1
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- ZRAOLHHYMQLCAW-UHFFFAOYSA-N tris(1h-pyrazol-5-yl) borate Chemical compound C1=CNN=C1OB(OC1=NNC=C1)OC=1C=CNN=1 ZRAOLHHYMQLCAW-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
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- C—CHEMISTRY; METALLURGY
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Description
Xは、周期表の第15族元素または第16族元素のうちの1つの元素、および、特に酸素を示し、
R1〜R7は、それぞれ互いに独立して、水素、ハロゲン、R’、O−R’、または、N−R’R’’を示し、
ここで、R’は、場合によってはヘテロ原子を含有し得る炭化水素基を示し、R’’はHを表し、または、R’に与えられた意味を有するものであり、2つまたはそれ以上の基R1〜R7はまた、融合した環系を形成することが可能であり、
L1、L2、および、L3は、それぞれ互いに独立して、負に帯電したリガンドまたは中性のリガンドを示し、ここで、2つまたはそれ以上のリガンドL1、L2、および、L3は、互いに結合されていてもよい。
・5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物、
・5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物、
・2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)、
・2−(4−メトキシカルボニル−オキサゾール−2−イル)−6−(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)、
・(3−オキソ−3−エトキシプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)、
・(3−ヒドロキシルプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)、
・5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物、
・5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物、および、
−三座のリガンド金属結合を有する、全く新規の分子構造である点。
−分子のたわみ性を抑えることによる、より効率的且つより明るい発光体である点。
−置換によって、緑色から赤色までの発光色を制御する点。
−熱的安定性が高い点。
−昇華性が良好であり、従って、真空蒸着(vacuum vapor deposition)方法を用いた技術的アプリケーションに好適である点。
−長期に亘って安定性が高い点。
−酸素と水に対する、化学的安定性が高い点。
−化学的バリエーションが極めて多い点。
−可溶性が良好であり、従って、スピンコート法、または、インクジェット印刷法の場合に、異なるポリマーマトリクス材内へのドーピングに好適である(発光層内への組み入れが良好である)点。
−ポリマーとの化学結合に好適であり、スピンコート法またはインクジェット印刷法等を用いる場合のポリマーの官能基化に好適である点。
5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物(A)
5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物(B)
2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)
4.白金錯体D
2−(4−メトキシカルボニル−オキサゾール−2−イル)−6−(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)
(3−オキソ−3−エトキシプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)
(3−ヒロドキシルプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)
5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物
5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物
Claims (30)
- 一般式(I)または(II)の錯体であって、
Xは、酸素を示し、
R1〜R7は、それぞれ互いに独立して、水素、ハロゲン、R’、O−R’、または、N−R’R’’を示し、
R’は、炭化水素基若しくはヘテロ原子を含有した炭化水素基を示し、R’’はHを示すものであるか、または、R’に与えられた意味を有するものであり、ここで、R1〜R7のうちの2つまたはそれ以上の残基が共に、融合して環系を形成することが可能であり、
L1、L2、および、L3は、それぞれ互いに独立して、負に帯電したリガンドまたは中性のリガンドを示し、2つまたはそれ以上のリガンドL1、L2、および、L3は、互いに結合されていることが可能である錯体。 - 一般式(I)または(II)内のMは、Pt(II)、Pd(II)、Ir(III)、Ru(II)、または、Os(II)を示すことを特徴とする、請求項1に記載の錯体。
- R1〜R7、あるいは、R’またはR’’は、それぞれ互いに独立して、置換または非置換の、水素基、アルキル基、アリール基、ヘテロアリール基、アルケニル基、または、アルキニル基を示すことを特徴とする、請求項1または2に記載の錯体。
- R1〜R7、あるいは、R’またはR’’は、それぞれ互いに独立して、ハロゲン、および、1以上6以下のC原子を有するアルキル基から選択された、1つまたは複数の置換基を有することを特徴とする、請求項1〜3のいずれか1項に記載の錯体。
- L1、L2、および、L3は、それぞれ互いに独立して、ハロゲン、擬ハロゲン、および、リガンドから選択されたものであり、
上記リガンドは、周期表の第16族元素のうちの1つの元素を介して、周期表の第15族元素のうちの1つの元素を介して、若しくは、周期表の第14族元素のうちの1つの元素を介して、Mに結合されていることを特徴とする、請求項1〜4のいずれか1項に記載の錯体。 - 5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物、
5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物、
2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)、
2−(4−メトキシカルボニル−オキサゾール−2−イル)−6−(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)、
(3−オキソ−3−エトキシプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)、
(3−ヒドロキシルプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)、
5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物、
5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物、および、
- (i)アノードと、
(ii)カソードと、
(iii)上記アノードと上記カソードとの間に配置され、上記アノードと上記カソードとに直接的または間接的に接触した発光層とを備えた発光素子であって、
上記発光層は、一般式(I)または(II)の少なくとも1つの錯体を含み、
Xは、酸素を示し、
R1〜R7は、それぞれ互いに独立して、水素、ハロゲン、R’、O−R’、または、N−R’R’’を示し、
R’は、炭化水素基若しくはヘテロ原子を含有した炭化水素基を示し、R’’はHを示すものであるか、または、R’に与えられた意味を有するものであり、ここで、2つまたはそれ以上の基R1〜R7はまた、融合した環系を形成することが可能であり、
L1、L2、および、L3は、それぞれ互いに独立して、負に帯電したリガンドまたは中性のリガンドを示し、ここで、2つまたはそれ以上のリガンドL1、L2、および、L3は、互いに結合されていることが可能である発光素子。 - 正孔伝導層および/または電子伝導層をさらに含むことを特徴とする、請求項7に記載の発光素子。
- CsF中間層またはLiF中間層をさらに含むことを特徴とする、請求項7または8に記載の発光素子。
- 基板上、特にガラス基板上に配置されることを特徴とする、請求項7〜9のいずれか1項に記載の発光素子。
- 上記発光層内に含まれる錯体は、三重項発光体であることを特徴とする、請求項7〜10のいずれか1項に記載の発光素子。
- Mは、酸化数0以上+4以下で存在することを特徴とする、請求項7〜11のいずれか1項に記載の発光素子。
- 上記発光層内には、一般式(I)および/または(II)の錯体が、上記発光層の全重量に対して1重量%以上100重量%以下の濃度で含まれていることを特徴とする、請求項7〜12のいずれか1項に記載の発光素子。
- 上記発光層における一般式(I)の錯体の割合は、上記発光層の全重量に対して80重量%よりも高く、特に90重量%よりも高いことを特徴とする、請求項7〜13のいずれか1項に記載の発光素子。
- 上記発光層における一般式(I)の錯体は、オリゴマーとして存在していることを特徴とする、請求項14に記載の発光素子。
- 上記発光層における一般式(I)の錯体の割合は、上記発光層の全重量に対して、10重量%よりも高く、特に20重量%よりも高く、且つ、80重量%未満、特に70重量%未満であることを特徴とする、請求項7〜13のいずれか1項に記載の発光素子。
- 上記発光層における一般式(I)の錯体は、モノマーおよびオリゴマーとして存在していることを特徴とする、請求項16に記載の発光素子。
- 上記発光層における一般式(I)および/または(II)の錯体の割合は、上記発光層の全重量に対して、2重量%よりも高く、特に4重量%よりも高く、且つ、10重量%未満、特に8重量%未満であることを特徴とする、請求項7〜13のいずれか1項に記載の発光素子。
- 上記発光層における一般式(I)または(II)の錯体は、モノマーとして存在していることを特徴とする、請求項18に記載の発光素子。
- 発光体として、少なくとも1つの以下の化合物
5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物、
5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−白金(II)臭化物、
2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)、
2−(4−メトキシカルボニル−オキサゾール−2−イル)−6−(5−エトキシ−オキサゾール−2−イル)フェニル−ブロモ白金(II)、
(3−オキソ−3−エトキシプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)、
(3−ヒドロキシルプロピニル)−[2,6−ビス(5−エトキシ−オキサゾール−2−イル)フェニル]−白金(II)、
5,5’−ジ−tert−ブチル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物、
5,5’−ジフェニル−2,2’−m−フェニレン−ビス−オキサゾール−2−パラジウム(II)臭化物、または、
- 一般式(I)または(II)の異なる少なくとも2つの錯体を含むことを特徴とする、請求項7に記載の発光素子。
- 上記発光層は、M=Ptである一般式(I)の少なくとも1つの錯体と、M=Pdである一般式(I)または(II)の少なくとも1つの錯体とを含むことを特徴とする、請求項7に記載の発光素子。
- 上記発光層において、M=Pd(II)である一般式(I)の錯体が、上記発光層の全重量に対して80重量%よりも高い割合で存在していると共に、M=Pt(II)である一般式(I)の錯体が、上記発光層の全重量に対して10重量%未満の割合で存在していることを特徴とする、請求項7〜13のいずれか1項に記載の発光素子。
- 一般式(I)の錯体を、結晶層および/または準結晶層として含むことを特徴とする、請求項7に記載の発光素子。
- OLEDであることを特徴とする、請求項7に記載の発光素子。
- ディスプレイおよび/または照明装置であることを特徴とする、請求項7に記載の発光素子。
- 発光素子における、請求項1に記載の一般式(I)または(II)の錯体の発光体としての使用。
- 三重項発光体としての請求項27に記載の使用。
- 上記発光層において、請求項1に記載の一般式(I)または(II)の少なくとも1つの錯体を、真空昇華法によって導入することを特徴とする、請求項7〜26のいずれか1項に係る発光素子の製造方法。
- 上記発光層において、請求項1に記載の一般式(I)または(II)の少なくとも1つの錯体を、湿式化学法によって導入することを特徴とする、請求項7〜26のいずれか1項に係る発光素子の製造方法。
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- 2007-07-27 JP JP2009522153A patent/JP5466005B2/ja not_active Expired - Fee Related
- 2007-07-27 US US12/375,220 patent/US8815413B2/en not_active Expired - Fee Related
- 2007-07-30 TW TW096127846A patent/TW200808814A/zh unknown
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US8815413B2 (en) | 2014-08-26 |
TW200808814A (en) | 2008-02-16 |
DE102006035018B4 (de) | 2009-07-23 |
JP2009544745A (ja) | 2009-12-17 |
EP2046916A1 (de) | 2009-04-15 |
WO2008012103A1 (de) | 2008-01-31 |
DE102006035018A1 (de) | 2008-04-17 |
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