JP5458554B2 - 有機電界発光素子および表示装置 - Google Patents
有機電界発光素子および表示装置 Download PDFInfo
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- JP5458554B2 JP5458554B2 JP2008295118A JP2008295118A JP5458554B2 JP 5458554 B2 JP5458554 B2 JP 5458554B2 JP 2008295118 A JP2008295118 A JP 2008295118A JP 2008295118 A JP2008295118 A JP 2008295118A JP 5458554 B2 JP5458554 B2 JP 5458554B2
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- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 26
- -1 amine compounds Chemical class 0.000 claims description 23
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 21
- 125000001769 aryl amino group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
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- 125000000217 alkyl group Chemical group 0.000 claims description 11
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
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- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 150000004035 chlorins Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- OQENBJBTQPIZKA-UHFFFAOYSA-N chrysen-1-amine Chemical class C1=CC2=C3C=CC=CC3=CC=C2C2=C1C(N)=CC=C2 OQENBJBTQPIZKA-UHFFFAOYSA-N 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229920001109 fluorescent polymer Polymers 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
Description
本発明の第2の有機電界発光素子は、光反射性を有する陽極と、光透過性を有する陰極と、陽極と陰極との間に、発光層を含む有機層とを備え、有機層は、陽極と発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、n型ホスト化合物は、式(3)で表される化合物であり、発光層から発せられた光は陰極側から射出されるものである。
本発明の第3の有機電界発光素子は、光反射性を有する陽極と、光透過性を有する陰極と、陽極と陰極との間に、発光層を含む有機層とを備え、有機層は、陽極と発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、n型ドーパント化合物は、式(4)および式(5)で表されるアミン系化合物のうちの少なくとも1種であり、発光層から発せられた光は陰極側から射出されるものである。
また、本発明の第1,第2,第3の表示装置はそれぞれ、本発明の第1,第2,第3の有機電界発光素子を備えている。「nドープ」とは、ホストと、そのホストに対してドーピングするドーパントとの関係において、ドーパント分子の最高被占分子軌道(HOMO)エネルギーの絶対値がホスト分子の最低空軌道(LUMO)エネルギーの絶対値よりも高いことを表す。すなわち、(ドーパント分子のHOMOエネルギーの絶対値)>(ホスト分子のLUMOエネルギーの絶対値)を満たす。また、「nドープ層」とは、上記のnドープの関係を満たす、ホストとしてn型ホスト化合物を含むと共にドーパントとしてn型ドーパント化合物を含む層のことをいう。
1.第1の実施の形態
(1−1)有機電界発光素子(上面発光型の例)
(1−2)表示装置(有機電界発光素子の使用例)
2.第2の実施の形態(配線材料)
[(1−1)有機電界発光素子(上面発光型の例)]
図1は、本発明の第1の実施の形態に係る有機電界発光素子の断面構成を表している。この有機電界発光素子(有機EL素子)は、例えばカラーディスプレイなどの表示装置に用いられるものである。この有機電界発光素子は、陽極11および陰極31との間に有機層20を備えている。有機層20は、陽極11側から順に、nドープ層21、正孔輸送層22、発光層23および電子輸送層24を積層した構造を有している。ここでは、発光層23から発せられる光(以下、発光光という)が陰極31側から取り出される上面発光型の有機電界発光素子の場合について説明する。
図4は表示装置の断面構成を表している。この表示装置は、TFTなどの駆動回路(図示せず)を備えた駆動用基板10の上に絶縁層12および有機電界発光素子1R,1G,1Bを有する構成となっている。また、この表示装置では、有機電界発光素子1R,1G,1Bの上に、それらを覆うように保護層32が形成され、この保護層32上に設けられた接着層33により接着された封止用基板40により全面にわたって封止されている。すなわち、ここで説明する表示装置の駆動方式は、アクティブマトリックス方式である。
本発明の第2の実施の形態に係る配線材料は、表示装置などに搭載された回路基板などに用いられるものであり、上記したn型ホスト化合物およびn型ドーパント化合物を含む、nドープされた有機導電性材料である。これにより、低い電圧で通電することができる。
以下の手順により、図5に示した配線構造を作製した。
nドープ層52の代わりに、式(3−1)に示した化合物(HAT)からなる層を100nmの厚さで真空蒸着して形成したことを除き、実験例1−1と同様の手順を経た。
以下の手順により、図1に示した有機電界発光素子を作製した。
nドープ層21を形成する際に、n型ドーパント化合物としてm−MTDATA(式(1−1))に代えて、αNPD(式(2−1))を用いたことを除き、実験例2−1と同様の手順を経た。
nドープ層21の代わりに、式(3−1)に示した化合物からなる層を20nmの厚さで真空蒸着して形成したことを除き、実験例2−1と同様の手順を経た。
nドープ層21の代わりに、式(3−1)に示した化合物と式(6)に示した化合物であるF4−TCNQを含む層(20nm厚)を形成したことを除き、実験例2−1と同様の手順を経た。この際、F4−TCNQの含有量が4体積%となるように共蒸着した。
Claims (11)
- 光反射性を有する陽極と、
光透過性を有する陰極と、
前記陽極と陰極との間に、発光層を含む有機層とを備え、
前記発光層から発せられた光は前記陰極側から射出され、
前記有機層は、前記陽極と前記発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、
前記n型ドーパント化合物の最高被占分子軌道(HOMO)エネルギーの絶対値と前記n型ホスト化合物の最低空軌道(LUMO)エネルギーの絶対値との差は、2eV以下である
有機電界発光素子。 - 光反射性を有する陽極と、
光透過性を有する陰極と、
前記陽極と陰極との間に、発光層を含む有機層とを備え、
前記発光層から発せられた光は前記陰極側から射出され、
前記有機層は、前記陽極と前記発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、
前記n型ホスト化合物は、式(3)で表される化合物である
有機電界発光素子。
- 光反射性を有する陽極と、
光透過性を有する陰極と、
前記陽極と陰極との間に、発光層を含む有機層とを備え、
前記発光層から発せられた光は前記陰極側から射出され、
前記有機層は、前記陽極と前記発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、
前記n型ドーパント化合物は、式(4)および式(5)で表されるアミン系化合物のうちの少なくとも1種である
有機電界発光素子。
- 前記陽極は、構成元素としてアルミニウムを含む
請求項1乃至3のうちいずれか1つに記載の有機電界発光素子。 - 前記有機層は、前記nドープ層と前記発光層との間に、正孔輸送層を有する
請求項1乃至3のうちいずれか1つに記載の有機電界発光素子。 - 前記n型ドーパント化合物は、式(1)および式(2)で表されるアミン系化合物のうちの少なくとも1種である
請求項1または2に記載の有機電界発光素子。
- 光反射性を有する陽極と、
光透過性を有する陰極と、
前記陽極と陰極との間に、発光層を含む有機層とを備え、
前記有機層は、前記陽極と前記発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、
前記n型ドーパント化合物の最高被占分子軌道(HOMO)エネルギーの絶対値と前記n型ホスト化合物の最低空軌道(LUMO)エネルギーの絶対値との差は、2eV以下であり、
前記発光層から発せられた光は前記陰極側から射出される
表示装置。 - 光反射性を有する陽極と、
光透過性を有する陰極と、
前記陽極と陰極との間に、発光層を含む有機層とを備え、
前記有機層は、前記陽極と前記発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、
前記n型ホスト化合物は、式(3)で表される化合物であり、
前記発光層から発せられた光は前記陰極側から射出される
表示装置。
- 光反射性を有する陽極と、
光透過性を有する陰極と、
前記陽極と陰極との間に、発光層を含む有機層とを備え、
前記有機層は、前記陽極と前記発光層との間に、n型ホスト化合物および2質量%以上10質量%以下のn型ドーパント化合物を含むnドープ層を有し、
前記n型ドーパント化合物は、式(4)および式(5)で表されるアミン系化合物のうちの少なくとも1種であり、
前記発光層から発せられた光は前記陰極側から射出される
表示装置。
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US7560175B2 (en) * | 1999-12-31 | 2009-07-14 | Lg Chem, Ltd. | Electroluminescent devices with low work function anode |
KR100377321B1 (ko) * | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
JP2004079413A (ja) * | 2002-08-21 | 2004-03-11 | Nec Corp | 有機エレクトロルミネッセント素子 |
JP2006294895A (ja) * | 2005-04-12 | 2006-10-26 | Sony Corp | 有機電界発光素子 |
JP5116992B2 (ja) * | 2005-05-27 | 2013-01-09 | 富士フイルム株式会社 | 有機el素子 |
JP4673279B2 (ja) * | 2005-12-20 | 2011-04-20 | 三星モバイルディスプレイ株式會社 | 有機発光表示素子及びその製造方法 |
JP5064482B2 (ja) * | 2006-03-14 | 2012-10-31 | エルジー・ケム・リミテッド | 高効率の有機発光素子およびその製造方法 |
WO2008069153A1 (en) * | 2006-12-04 | 2008-06-12 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and electronic device |
US7728512B2 (en) * | 2007-03-02 | 2010-06-01 | Universal Display Corporation | Organic light emitting device having an external microcavity |
-
2008
- 2008-11-19 JP JP2008295118A patent/JP5458554B2/ja active Active
-
2009
- 2009-11-13 WO PCT/JP2009/069338 patent/WO2010058737A1/ja active Application Filing
- 2009-11-13 US US13/124,424 patent/US20110210323A1/en not_active Abandoned
- 2009-11-13 CN CN2009801458211A patent/CN102217113A/zh active Pending
Also Published As
Publication number | Publication date |
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JP2010123704A (ja) | 2010-06-03 |
CN102217113A (zh) | 2011-10-12 |
US20110210323A1 (en) | 2011-09-01 |
WO2010058737A1 (ja) | 2010-05-27 |
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