JP2013538242A - 有機発光デバイスおよび方法 - Google Patents
有機発光デバイスおよび方法 Download PDFInfo
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- JP2013538242A JP2013538242A JP2013515960A JP2013515960A JP2013538242A JP 2013538242 A JP2013538242 A JP 2013538242A JP 2013515960 A JP2013515960 A JP 2013515960A JP 2013515960 A JP2013515960 A JP 2013515960A JP 2013538242 A JP2013538242 A JP 2013538242A
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- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- ZOXHPDJMUUCKNR-UHFFFAOYSA-N anthracene;9h-fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1.C1=CC=CC2=CC3=CC=CC=C3C=C21 ZOXHPDJMUUCKNR-UHFFFAOYSA-N 0.000 description 1
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
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- 150000002390 heteroarenes Chemical class 0.000 description 1
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- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
2×T1A≧S1A>S1EまたはT1A+T1E≧S1A>S1Eであり
[式中、
T1Aは、三重項受容材料の三重項励起状態エネルギー準位を表し、
T1Eは、発光材料の三重項励起状態エネルギー準位を表し、
S1Aは、三重項受容材料の一重項励起状態エネルギー準位を表し、
S1Eは、発光材料の一重項励起状態エネルギー準位を表す]、
励起時に該組成物によって放出された光は、遅延蛍光を含む、組成物を提供する。
kT1E-T1A≧kT1E-S0E
であり、式中、
kT1E-T1Aは、発光材料上の三重項励起子が、三重項受容材料に移動する速度定数を表し、
kT1E-S0Eは、発光材料上の三重項励起子が、発光材料の基底状態に減衰する速度定数を表す。
kTTA>kT1A-S0A
であり、式中、
kTTAは、2つの三重項受容材料上の2つの三重項励起子間、または三重項受容材料上の三重項励起子と発光材料上の三重項励起子との間の三重項−三重項消滅の速度定数を表し、
kT1A-S0Aは、三重項受容材料上の三重項励起子が、三重項受容材料の基底状態に減衰する速度定数を表す。
TAU−Sp−TAU
(II)
式中、TAUは、三重項受容材料を表し、Spは、スペーサー基を表す。
TQ−Ar−TQ
(IIa)
式中、Arは、任意選択により置換されているアリーレン基を表す。
i)三重項吸収材料は、T1A上の三重項励起子が、相対的に長い寿命τTAを有するように選択することができる。相対的に長い寿命とは、S0Aへの減衰速度が相対的に緩慢であることを意味するだけでなく、TTAの確率が相対的に高いことを意味している。
ii)発光層における三重項吸収材料の濃度は、相対的に高く、例えば1mol%超、例えば0.1〜10mol%または1〜10mol%の範囲であってよい。
iii)2つ以上の三重項受容材料は、例えば式(II)の単位に関して以下に記載の通り、近接して提供することができる。
使用される三重項受容単位は、発光材料および1つまたは複数の電荷輸送材料(例えば、正孔輸送材料および電子輸送材料の一方または両方)などの発光組成物の任意の他の成分に化学的には結合しないが、物理的に混合される化合物であってよい。あるいは、三重項受容単位は、直接的にまたはスペーサー基を介して発光材料または組成物の別の成分に結合することができ、特に共有結合することができる。
PG−重合可能な単位−PG
|
三重項吸収単位
式中、PGは、前述の脱離基などの重合可能な基、または重合可能な二重結合を表す。
TAU−スペーサー−TAU
(II)
式中、「TAU」は、式(I)の三重項受容単位を表し、スペーサーは、共役しているか、または共役していないスペーサー基である。スペーサー基は、2つの三重項受容TAU基を分離し、好ましくはそれらの電子的な特徴を分離する(例えば、HOMOとLUMO)。共役および軌道の重なりの正確な性質に応じて、Spは、任意選択により、置換されているフェニル、ビフェニルまたはフルオレンなどの1つまたは複数のアリーレン基またはヘテロアリーレン基を含むことができる。あるいは、Spは、任意選択により、アルキルなどの共役していない連結基、またはTAU基とTAU基の間に共役経路を提供しない別の分子の連結を含むことができる。
(TAU−スペーサー)m
(IIb)
式中、mは、少なくとも2である。
層3において使用するのに適した発光材料には、小分子、ポリマー材料およびデンドリマー材料、ならびにその組成物が含まれる。層3における使用に適した発光ポリマーには、ポリ(p−フェニレンビニレン)などのポリ(アリーレンビニレン)、およびポリフルオレン、特に2,7−連結9,9ジアルキルポリフルオレンまたは2,7−連結9,9ジアリールポリフルオレンなどのポリアリーレン;ポリスピロフルオレン、特に2,7−連結ポリ−9,9−スピロフルオレン;ポリインデノフルオレン、特に2,7−連結ポリインデノフルオレン;ポリフェニレン、特にアルキルまたはアルコキシで置換されているポリ−1,4−フェニレンが含まれる。かかるポリマーは、例えば、Adv.Mater.2000年、12(23)1737〜1750頁およびその参考文献に開示されている。
伝導性有機材料または無機材料から形成することができる伝導性正孔注入層を、陽極2およびエレクトロルミネセント層3の間に提供して、陽極から半導体ポリマーの1つまたは複数の層に正孔を注入するのに役立てることができる。
正孔輸送層は、陽極およびエレクトロルミネセント層の間に提供することができる。同様に、電子輸送層は、陰極およびエレクトロルミネセント層の間に提供することができる。
陰極4は、エレクトロルミネセント層に電子を注入することができる仕事関数を有する材料から選択される。陰極とエレクトロルミネセント材料との間に有害な相互反応が生じる可能性があるなどの他の因子も、陰極の選択に影響を及ぼす。陰極は、アルミニウム層などの単一材料からなることができる。
光学デバイスは、湿気および酸素に感受性が高い傾向がある。したがって基板は、好ましくは、デバイスへの湿気および酸素の侵入を防止するための良好なバリア特性を有する。基板は、一般にガラスであるが、特にデバイスの可撓性が望ましい場合には、代替の基板を使用することができる。例えば、基板は、プラスチック層とバリア層が交互になった基板を開示している米国特許第6268695号にみられるようなプラスチック、または欧州特許第0949850号に開示されている薄いガラスおよびプラスチックのラミネートを含むことができる。
発光層3は、真空蒸着および溶媒中溶液からの堆積を含む任意の方法によって堆積させることができる。発光層が、ポリフルオレンなどのポリアリーレンを含む場合、溶液堆積に適した溶媒には、トルエンおよびキシレンなどのモノ−またはポリ−アルキルベンゼンが含まれる。特に好ましい溶液堆積技術には、印刷技術およびコーティング技術、好ましくはスピンコーティングおよびインクジェット印刷が含まれる。
アンタントレン化合物1を、以下の合成法に従って、市販のアンタントレンから出発して調製した。
以下の構造を有するデバイスを形成した。
ITO/HIL/HTL/EL/MF/Al
ITOは、酸化インジウムスズ陽極を表し、HILは、35nmの正孔注入層であり、HTLは、式(IV)のポリマーの15nmの正孔輸送層であり、ELは、式(VI)の三重項受容材料(DPVBi、1%mol比)とブレンドした、式(V)の発光ポリマーを含有する70nmのエレクトロルミネセント層であり(DPVBiを含まない対照デバイスも、比較のために製造した)、MFは、フッ化金属であり、MF/Alの二層は、デバイスの陰極を形成する。HIL、HTLおよびEL層は、溶液から組成物をスピンコーティングまたはインクジェット印刷し、溶媒を蒸発させることによって堆積させた。
三重項受容材料を9,10−ジフェニルアントラセンにしたことを除き、さらなるデバイスを、実質的にデバイス実施例1に記載の通り調製した。図9aは、三重項クエンチャーを含まないデバイスの遅延発光、主鎖の三重項密度および主鎖の三重項密度の二乗を示す。直線は、遅延発光が、主鎖の三重項密度の二乗に比例することを示す指針である。図9bによって、三重項受容材料として9,10−ジフェニルアントラセンを含有するデバイスの遅延発光、三重項密度および三重項密度の二乗を示した。
また、三重項受容材料(アントラセン)を、50mol%のアントラセンおよびフルオレンモノマーを含むアントラセン−フルオレンランダムコポリマーの形態で発光ポリマーの主鎖中に提供して、さらなる一例を調製した。図10は、この材料を使用して得た遅延蛍光を示す。
Claims (30)
- 蛍光発光材料および三重項受容材料を含む有機発光デバイスにおいて使用するための組成物であって、
2×T1A≧S1A>S1EまたはT1A+T1E≧S1A>S1Eであり
式中、
T1Aは、三重項受容材料の三重項励起状態エネルギー準位を表し、
T1Eは、発光材料の三重項励起状態エネルギー準位を表し、
S1Aは、三重項受容材料の一重項励起状態エネルギー準位を表し、
S1Eは、発光材料の一重項励起状態エネルギー準位を表し、
励起時に該組成物によって放出された光が、遅延蛍光を含む、組成物。 - 励起時に該組成物によって放出された光の発光強度の少なくとも10%、任意選択により少なくとも20%は、遅延蛍光である、請求項1に記載の組成物。
- 組成物の発光強度が、初期の発光強度から50%だけ低下するのに十分な時間をかけて組成物を持続的に励起すると、組成物の初期の励起後、遅延蛍光の初期の発光の後の全期間にわたって、遅延蛍光が発光する、請求項1から2のいずれかに記載の組成物。
- kT1E-T1A≧kT1E-S0E
であり、
式中、
kT1E-T1Aは、発光材料上の三重項励起子が、三重項受容材料に移動する速度定数を表し、
kT1E-S0Eは、発光材料上の三重項励起子が、発光材料の基底状態に減衰する速度定数を表す、請求項1から3のいずれかに記載の組成物。 - kTTA>kT1A-S0A
であり、
式中、
kTTAは、2つの三重項受容材料上の2つの三重項励起子間、または三重項受容材料上の三重項励起子と発光材料上の三重項励起子との間の三重項−三重項消滅の速度定数を表し、
kT1A-S0Aは、三重項受容材料上の三重項励起子が、三重項受容材料の基底状態に減衰する速度定数を表す、請求項1から4のいずれかに記載の組成物。 - 三重項受容材料の少なくともいくつかは、式(II)を含み、
TAU−Sp−TAU
(II)
式中、
TAUは、三重項受容材料を表し、Spは、スペーサー基を表す、請求項1から5のいずれかに記載の組成物。 - Spは、アリーレン基を含む、請求項6に記載の組成物。
- 三重項受容材料の少なくともいくつかは、式(IIa)を含み、
TQ−Ar−TQ
(IIa)
式中、
Arは、任意選択により置換されているアリーレン基を表す、請求項7に記載の組成物。 - Arは、フェニル、ビフェニル、テルフェニルおよびフルオレンからなる群から選択される、請求項8に記載の組成物。
- 三重項受容材料が、発光材料および組成物の任意の他の1つまたは複数の成分と物理的に混合された三重項受容化合物である、請求項1から9のいずれかに記載の組成物。
- 三重項受容材料が、発光材料、または存在する場合、組成物の別の成分に結合している、請求項1から9のいずれかに記載の組成物。
- 正孔輸送材料および電子輸送材料の少なくとも1つを含み、三重項受容単位が、正孔輸送材料、電子輸送材料および発光材料、好ましくは発光材料の少なくとも1つに結合している、請求項11に記載の組成物。
- 発光材料が、発光ポリマーであり、三重項受容材料が、発光ポリマーの主鎖中の繰返し単位または発光ポリマーの側鎖基もしくは末端基である、請求項11または12に記載の組成物。
- 三重項受容材料が、1つまたは複数の可溶化基で置換されている、請求項1から13のいずれかに記載の組成物。
- 可溶化基が、アルキルおよびアルコキシから選択される、請求項14に記載の組成物。
- 発光材料が発光ポリマーである、請求項1から15のいずれかに記載の組成物。
- 発光ポリマーが、アリールアミン繰返し単位を含む、請求項16に記載の組成物。
- アリールアミン繰返し単位が、式(V)の単位であり、
Ar1およびAr2は、任意選択により置換されているアリール基またはヘテロアリール基であり、nは、1以上、好ましくは1または2であり、Rは、Hまたは置換基である、請求項17に記載の組成物。 - ポリマーが、アリールまたはヘテロアリール繰返し単位を含む、請求項16、17または18に記載の組成物。
- 式(IV)の繰返し単位を含み、
R1およびR2は、独立に、Hまたは置換基であり、R1およびR2は、連結されて、環を形成することができる、請求項19に記載の組成物。 - 三重項受容材料が、少なくとも0.1mol%の量で存在する、請求項1から20のいずれかに記載の組成物。
- 400〜500nmの範囲のフォトルミネセント発光ピーク波長を有する、請求項1から21のいずれかに記載の組成物。
- 三重項受容材料が、ペリレンを含まない、請求項1から22のいずれかに記載の組成物。
- 溶媒および請求項1から23のいずれかに記載の組成物を含む溶液。
- 陽極と、陰極と、陽極および陰極の間の、請求項1〜24のいずれか一項に記載の組成物を含む発光層とを含む、有機発光デバイス。
- 請求項25に記載の有機発光デバイスを形成する方法であって、
前記方法は、請求項24に記載の溶液を堆積させるステップおよび溶媒を蒸発させるステップを含む、方法。 - 三重項受容材料および蛍光発光材料を含む組成物における蛍光発光材料によって発生した三重項励起子を三重項−三重項消滅させることにより、遅延蛍光を媒介するための、三重項受容材料の使用。
- 三重項受容材料が、蛍光発光材料と物理的に混合されている、請求項27に記載の使用。
- 三重項受容材料が、蛍光発光材料に化学的に結合している、請求項27に記載の使用。
- 蛍光発光材料が、ポリマーであり、三重項受容材料が、ポリマー主鎖中の繰返し単位、ポリマー主鎖からペンダント状態にある側鎖基、またはポリマー末端基として提供される、請求項29に記載の使用。
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JP2016092417A (ja) * | 2014-10-31 | 2016-05-23 | 株式会社半導体エネルギー研究所 | ベンゾ[a]アントラセン化合物、発光素子、表示装置、電子機器、及び照明装置 |
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US11563177B2 (en) | 2014-10-31 | 2023-01-24 | Semiconductor Energy Laboratory Co., Ltd. | Benzo[a]anthracene compound, light-emitting element, display device, electronic device, and lighting device |
US11851594B2 (en) | 2014-10-31 | 2023-12-26 | Semiconductor Energy Laboratory Co., Ltd. | Benzo[a]anthracene compound, light-emitting element, display device, electronic device, and lighting device |
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JP6139405B2 (ja) | 2017-05-31 |
KR101888705B1 (ko) | 2018-08-14 |
DE112011102125B4 (de) | 2022-06-15 |
JP2013538438A (ja) | 2013-10-10 |
GB2515182B (en) | 2015-01-28 |
KR20140000660A (ko) | 2014-01-03 |
DE112011102125T5 (de) | 2013-04-25 |
KR101916480B1 (ko) | 2019-01-07 |
JP6018052B2 (ja) | 2016-11-02 |
JP5812302B2 (ja) | 2015-11-11 |
GB2515182A (en) | 2014-12-17 |
GB201408305D0 (en) | 2014-06-25 |
GB2499969A (en) | 2013-09-11 |
JP2013539198A (ja) | 2013-10-17 |
JP2013531100A (ja) | 2013-08-01 |
GB201101642D0 (en) | 2011-03-16 |
KR20130097708A (ko) | 2013-09-03 |
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