JP5265840B2 - 有機発光ダイオード類に基づく青色リン光用の材料および素子 - Google Patents
有機発光ダイオード類に基づく青色リン光用の材料および素子 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims description 236
- 239000002019 doping agent Substances 0.000 claims description 120
- 230000032258 transport Effects 0.000 claims description 54
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 17
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 16
- 230000005281 excited state Effects 0.000 claims description 11
- 230000005855 radiation Effects 0.000 claims description 11
- 238000001429 visible spectrum Methods 0.000 claims description 9
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002790 naphthalenes Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 6
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 4
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims 4
- 125000005580 triphenylene group Chemical group 0.000 claims 4
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 88
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
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- 238000000034 method Methods 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 9
- 230000008569 process Effects 0.000 description 7
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 6
- 230000006798 recombination Effects 0.000 description 6
- 238000005215 recombination Methods 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
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- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- FRROPLJDWOWWKV-UHFFFAOYSA-N 4-(4-tert-butylphenyl)oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CON=N1 FRROPLJDWOWWKV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
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- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation 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
- 238000005286 illumination Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- ZPQKWGRIAJXEFX-UHFFFAOYSA-N iridium;2-phenyl-1,3-benzothiazole Chemical compound [Ir].C1=CC=CC=C1C1=NC2=CC=CC=C2S1.C1=CC=CC=C1C1=NC2=CC=CC=C2S1 ZPQKWGRIAJXEFX-UHFFFAOYSA-N 0.000 description 1
- DBNYWRKRZTXMCU-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 DBNYWRKRZTXMCU-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000013212 metal-organic material Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003643 triphenylenes Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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Description
本発明は、例えば青色を発光できる高効率の有機発光素子(OLEDs)に関し、特に不活性ホスト物質中にドープしたリン光発光ドーパント材料および電荷運搬ドーパント材料を含んでいる発光層を有するOLEDsに関する。
電流で励起されると発光する薄膜材料を利用する有機発光素子(OLEDs)は平面パネルディスプレイ技術のますます一般的な様式になることが期待されている。これは、OLEDsは携帯電話、携帯情報端末(PDAs)、コンピュータディスプレイ、自動車内の情報ディスプレイ、テレビジョンモニター類と共に光源または一般的照明用光源を含んだ幅広い種類の潜在的応用性を有しているからである。それらの鮮明な色彩、広い視野角、フルモーションビデオの適応可能性、広範囲温度、薄型と適合性あるフォームファクター、低電力要求性および低価格での製造工程に関する可能性により、OLEDsは最近年に400億ドルまで成長するまでになった電子ディスプレイ市場にて優位を占めるブラウン管(CRTs)および液晶ディスプレイ(LCDs)の将来的後継技術として考えられている。それらの高照明効率により、エレクトロホスホレッセンスのOLEDsはある種の型の応用面では白熱灯および多分蛍光灯に取って代わる可能性を有していると見られている。
本発明は効率的に発光、特に好ましくは可視スペクトルの青色範囲に発光するOLED素子に関し、そして当該素子類を形成する方法に関する。本発明に従って作成したOLEDsには、好ましくは現行の緑色から赤色リン光発光OLEDsと効率レベルで同程度の青色リン光発光OLEDsが含まれる。
添付した図面は本発明の更なる理解を供与するために付け、本明細書の構成部分に組み込んだが、本発明を説明するために本発明の幾つかの実施態様を説明と共に図解して供する。
本発明の実施態様は当該図面に関して説明される。これらの実施態様は本発明の説明的な例を意図し、本発明を制限するものではないことを理解されたい。
またはDexterのエネルギー転移プロセスによる当該ドーパントへのエネルギー転移が含まれていた。本プロセスは未だにリン光に基づくOLEDsにて生じると信じられているが、これらのエレクトロルミネッセンス素子の効率を向上するのを助ける際に重要であると信じられている二番目のプロセスが存在する。当該リン光発光ドーパントのHOMOエネルギーレベルは典型的にはエネルギーにおいて、それらがドープされているマトリックス材料のエネルギーレベルより高い。これはドーピングレベルが充分に高ければ当該ドーパントが正孔を捕集でき、当該マトリックスを通してそれらを輸送することができる。最終的結果では当該ドーパント自身は正孔−電子再結合の部位として動くことができる。これは当該励起子が当該ドーパント部位にて優先的に形成できれば
および/またはDexter型ホスト−ドーパントのエネルギー転移プロセスは、不活性で非電荷運搬ホスト材料においては不必要であることを意味する。
OLED'sを製造する際に当技術分野にて知られている材料および方法を用いれば、1つの例示的実施態様では本発明によるOLEDは不活性ホスト材料としてポリスチレンの薄膜を用いて製造する。当該ドーパント層は当該不活性ホスト材料を15%の正孔輸送リン光発光ドーパントおよび40%の電子輸送オキシジアゾールでドーピングして形成される。より具体的には、当該リン光発光ドーパント類は以下の化学構造を有するビス(フェニルピリジン)イリジウムアセチルアセトナート(PPIr):
および以下の化学構造を有するビス(2−フェニルベンゾチアゾール)イリジウムアセチルアセトナート(BTIr):
であり、当該オキシジアゾールは以下の化学構造を有する(4−ビフェニル)(4−三級ブチルフェニル)オキシジアゾール(PDB)である。当該素子は約7と9ボルトの間の電圧をかけると当該ドーパントからのみ発光した。当該ポリスチレンは当該ドーパントが担持されている不活性マトリックスとして働く。本素子は可視スペクトルの緑色領域の光を生じるが、同じ形態の異なるリン光体ドーパントが当該スペクトルの青色領域の光を生じるのに用いることができる。
Claims (12)
- アノード層;電荷運搬ドーパント材料およびリン光発光ドーパント材料の両方をドープした非電荷運搬材料を含む、前記アノード層上の発光層;および前記発光層上のカソード層;を含む有機発光素子であって、
前記電荷運搬ドーパント材料は正孔または電子を輸送でき、前記リン光発光ドーパント材料は前記電荷運搬ドーパント材料によって運ばれる電荷と逆の電荷を輸送することができ、
前記リン光発光ドーパント材料が、リン光発光ドーパント材料の有機分子の三重項励起状態から発光することができ、
前記電荷運搬ドーパント材料が正孔を輸送し、かつ前記リン光発光ドーパント材料が電子を輸送する場合には、前記非電荷運搬材料のHOMOレベルが前記正孔運搬ドーパント材料のHOMOレベルより低く、かつ前記非電荷運搬材料のLUMOレベルが前記電子輸送性リン光発光ドーパント材料のLUMOレベルよりも高く、また、
前記電荷運搬ドーパント材料が電子を輸送し、かつ前記リン光発光ドーパント材料が正孔を輸送する場合には、前記非電荷運搬材料のHOMOレベルが前記正孔輸送性リン光発光ドーパント材料のHOMOレベルより低く、かつ前記非電荷運搬材料のLUMOレベルが前記電子運搬ドーパント材料のLUMOレベルよりも高い、有機発光素子。 - 前記電荷運搬ドーパント材料が正孔運搬ドーパント材料であり、かつ前記リン光発光ドーパント材料が電子を輸送する請求項1記載の有機発光素子であって、
前記非電荷運搬材料の最低三重項状態エネルギーレベルおよび前記正孔運搬ドーパント材料の最低三重項状態エネルギーレベルが、各々前記リン光発光ドーパント材料の最低三重項状態エネルギーレベルより高い、有機発光素子。 - 前記非電荷運搬材料の最低三重項状態エネルギーレベルが、前記正孔運搬ドーパント材料の最低三重項状態エネルギーレベルより高い、請求項2に記載の有機発光素子。
- 前記非電荷運搬材料が、少なくとも3.5eVのエネルギー差を、HOMOおよびLUMOのエネルギーレベル間に有する、請求項3に記載の有機発光素子。
- 前記非電荷運搬材料が、ジフェニレン、置換ジフェニレン、トリフェニレン、置換トリフェニレン、ナフタレン、置換ナフタレン、テトラフェニルブタジエンおよび置換テトラフェニルブタジエンからなる群より選択した材料を含む、請求項1〜4のいずれか一項に記載の有機発光素子。
- 前記電荷運搬ドーパント材料が、トリアリールアミン、金属配位錯体および供与体置換ナフタレンからなる群より選択した材料を含む正孔輸送ドーパント材料である、請求項1〜5のいずれか一項に記載の有機発光素子。
- 前記電荷運搬ドーパント材料が電子運搬ドーパント材料であり、かつ前記リン光発光ドーパント材料が正孔を輸送し、
前記非電荷運搬材料の最低三重項状態エネルギーレベルおよび前記電子運搬ドーパント材料の最低三重項状態エネルギーレベルが、各々前記リン光発光ドーパント材料の最低三重項状態エネルギーレベルより高い、請求項1に記載の有機発光素子。 - 前記非電荷運搬材料の最低三重項状態エネルギーレベルが、前記電子運搬ドーパント材料の最低三重項状態エネルギーレベルより高い、請求項7に記載の有機発光素子。
- 前記非電荷運搬材料が、少なくとも3.5eVのエネルギー差を、HOMOおよびLUMOのエネルギーレベル間に有する、請求項7又は8に記載の有機発光素子。
- 前記非電荷運搬材料が、ジフェニレン、置換ジフェニレン、トリフェニレン、置換トリフェニレン、ナフタレン、置換ナフタレン、テトラフェニルブタジエンおよび置換テトラフェニルブタジエンからなる群より選択した材料を含む、請求項7〜9のいずれか一項に記載の有機発光素子。
- 前記電子運搬ドーパント材料が、オキシジアゾール、トライゾールおよびシクロオクタテトラエンからなる群より選択される材料を含む、請求項7〜10のいずれか一項に記載の有機発光素子。
- 前記発光層が可視スペクトルの青色領域において放射を放出する、請求項1〜11のいずれか一項に記載の有機発光素子。
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PCT/US2002/007492 WO2002074015A2 (en) | 2001-03-14 | 2002-03-13 | Materials and devices for blue phosphorescence based organic light emitting diodes |
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