JP7531481B2 - 有機化合物、発光デバイス、発光装置、電子機器、および照明装置 - Google Patents
有機化合物、発光デバイス、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP7531481B2 JP7531481B2 JP2021513027A JP2021513027A JP7531481B2 JP 7531481 B2 JP7531481 B2 JP 7531481B2 JP 2021513027 A JP2021513027 A JP 2021513027A JP 2021513027 A JP2021513027 A JP 2021513027A JP 7531481 B2 JP7531481 B2 JP 7531481B2
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- MSCLVLGBAGCXEC-UHFFFAOYSA-N n-phenyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-9,9'-spirobi[fluorene]-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MSCLVLGBAGCXEC-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- FPOBXNYAWLLCGZ-UHFFFAOYSA-N nickel(2+);1,2,3,4,5-pentamethylcyclopenta-1,3-diene Chemical compound [Ni+2].CC=1C(C)=C(C)[C-](C)C=1C.CC=1C(C)=C(C)[C-](C)C=1C FPOBXNYAWLLCGZ-UHFFFAOYSA-N 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- PENAXHPKEVTBLF-UHFFFAOYSA-L palladium(2+);prop-1-ene;dichloride Chemical compound [Pd+]Cl.[Pd+]Cl.[CH2-]C=C.[CH2-]C=C PENAXHPKEVTBLF-UHFFFAOYSA-L 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- BZBAYMUKLAYQEO-UHFFFAOYSA-N phenylborane Chemical compound BC1=CC=CC=C1 BZBAYMUKLAYQEO-UHFFFAOYSA-N 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin 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
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- DKWSBNMUWZBREO-UHFFFAOYSA-N terbium Chemical compound [Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb] DKWSBNMUWZBREO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Description
図2Aは、発光装置について説明する図である。図2Bは、発光装置について説明する図である。図2Cは、発光装置について説明する図である。
図3Aは、発光装置について説明する上面図である。図3Bは、発光装置について説明する断面図である。
図4Aは、モバイルコンピュータについて説明する図である。図4Bは、携帯型の画像再生装置について説明する図である。図4Cは、デジタルカメラについて説明する図である。図4Dは、携帯情報端末について説明する図である。図4Eは、携帯情報端末について説明する図である。図4Fは、テレビジョン装置について説明する図である。図4Gは、携帯情報端末について説明する図である。
図5Aは、電子機器について説明する図である。図5Bは、電子機器について説明する図である。図5Cは、電子機器について説明する図である。
図6Aは、自動車について説明する図である。図6Bは、自動車について説明する図である。
図7Aは、照明装置について説明する図である。図7Bは、照明装置について説明する図である。
図8は、構造式(100)に示す有機化合物の1H-NMRチャートである。
図9は、構造式(100)に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトルである。
図10は、構造式(100)に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトルである。
図11は、構造式(101)に示す有機化合物の1H-NMRチャートである。
図12は、構造式(101)に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトルである。
図13は、構造式(101)に示す有機化合物の紫外・可視吸収スペクトル及び発光スペクトルである。
図14は、発光デバイスについて説明する図である。
図15は、発光デバイス1、発光デバイス2、および比較発光デバイス3の電流密度-輝度特性を示す図である。
図16は、発光デバイス1、発光デバイス2、および比較発光デバイス3の電圧-輝度特性を示す図である。
図17は、発光デバイス1、発光デバイス2、および比較発光デバイス3の輝度-電流効率特性を示す図である。
図18は、発光デバイス1、発光デバイス2、および比較発光デバイス3の電圧-電流特性を示す図である。
図19は、発光デバイス1、発光デバイス2、および比較発光デバイス3の発光スペクトルを示す図である。
図20は、発光デバイス1、発光デバイス2、および比較発光デバイス3の信頼性を示す図である。
図21は、発光デバイス4および比較発光デバイス5の電流密度-輝度特性を示す図である。
図22は、発光デバイス4および比較発光デバイス5の電圧-輝度特性を示す図である。
図23は、発光デバイス4および比較発光デバイス5の輝度-電流効率特性を示す図である。
図24は、発光デバイス4および比較発光デバイス5の電圧-電流特性を示す図である。
図25は、発光デバイス4および比較発光デバイス5の発光スペクトルを示す図である。
図26は、発光デバイス4および比較発光デバイス5の信頼性を示す図である。
本実施の形態では、本発明の一態様である有機化合物について説明する。なお、本発明の一態様である有機化合物は、下記一般式(G1)で表される、ベンゾフロピリミジン誘導体またはベンゾチエノピリミジン誘導体である。なお、本発明の一態様である有機化合物は、下記一般式(G1)で表されるようにベンゾフロピリミジン骨格またはベンゾチエノピリミジン骨格の2位に第1のカルバゾール骨格の窒素原子が結合し、かつ第1のカルバゾール骨格が有するベンゼン環には第2のカルバゾール骨格が結合する構造を有する。
以下に、一般式(G1)で表されるベンゾフロピリミジン誘導体、またはベンゾチエノピリミジン誘導体の合成方法の一例について説明する。これらの有機化合物の合成には、種々の反応を適用することができる。例えば、合成スキーム(A)に示すように、ベンゾフロピリミジン骨格またはベンゾチエノピリミジン骨格を有するトリハロゲン化合物(A1)とR4のボロン酸化合物(A2)とを反応させることにより形成される中間体(A3)と、ビカルバゾール化合物(A4)とを反応させることにより、中間体(A5)を形成し、この中間体(A5)とAのボロン酸化合物(A6)とを反応させることによって、一般式(G1)で表される有機化合物を得ることができる。
本実施の形態では、本発明の一態様である発光デバイスについて説明する。
図1Aには、一対の電極間に発光層を含むEL層を有する発光デバイスの一例を示す。具体的には、第1の電極101と第2の電極102との間にEL層103が挟まれた構造を有する。なお、EL層103は、例えば、第1の電極101を陽極とした場合、正孔(ホール)注入層111、正孔(ホール)輸送層112、発光層113、電子輸送層114、電子注入層115が機能層として、順次積層された構造を有する。
第1の電極101および第2の電極102を形成する材料としては、上述した両電極の機能が満たせるのであれば、以下に示す材料を適宜組み合わせて用いることができる。例えば、金属、合金、電気伝導性化合物、およびこれらの混合物などを適宜用いることができる。具体的には、In-Sn酸化物(ITOともいう)、In-Si-Sn酸化物(ITSOともいう)、In-Zn酸化物、In-W-Zn酸化物が挙げられる。その他、アルミニウム(Al)、チタン(Ti)、クロム(Cr)、マンガン(Mn)、鉄(Fe)、コバルト(Co)、ニッケル(Ni)、銅(Cu)、ガリウム(Ga)、亜鉛(Zn)、インジウム(In)、スズ(Sn)、モリブデン(Mo)、タンタル(Ta)、タングステン(W)、パラジウム(Pd)、金(Au)、白金(Pt)、銀(Ag)、イットリウム(Y)、ネオジム(Nd)などの金属、およびこれらを適宜組み合わせて含む合金を用いることもできる。その他、上記例示のない元素周期表の第1族または第2族に属する元素(例えば、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、ストロンチウム(Sr))、ユウロピウム(Eu)、イッテルビウム(Yb)などの希土類金属およびこれらを適宜組み合わせて含む合金、その他グラフェン等を用いることができる。
正孔注入層111は、陽極である第1の電極101や電荷発生層104からEL層(103、103a、103b)に正孔(ホール)を注入する層であり、有機アクセプタ材料(電子受容性材料)を含む層である。
正孔輸送層112は、正孔注入層111によって、第1の電極101から注入された正孔を発光層113に輸送する層である。
本発明の一態様である、発光デバイスにおいて、発光層113は、単層構造でも複数の発光層が積層された構造でも良い。なお、複数の発光層が積層される場合、各発光層が異なる機能を有するように発光層を形成することが好ましい。
電子輸送層114は、第2の電極102から注入された電子を発光層113に輸送する層であり、発光層113に接して設けられる。なお、電子輸送層114は、電子輸送性材料を含む層である。電子輸送層114に用いる電子輸送性材料は、1×10-6cm2/Vs以上の電子移動度を有する物質が好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、これら以外のものを用いることができる。また、電子輸送層114は、電子輸送性材料、およびアルカリ金属またはアルカリ土類金属の有機金属錯体を用いても良い。この場合、電子輸送性材料として、HOMO準位が-6.0eV以上の電子輸送性材料を用いることが好ましい。なお、HOMO準位が-6.0eV以上の電子輸送性材料としては、電界強度[V/cm]の平方根が600における電子移動度が、1×10-7cm2/Vs以上1×10-5cm2/Vs以下であると好ましいが、1×10-7cm2/Vs以上5×10-5cm2/Vs以下であるとより好ましい。
電子注入層115は、第2の電極(陰極)102からの電子の注入効率を高めるための層であり、第2の電極(陰極)102材料の仕事関数の値と、電子注入層115に用いる材料のLUMO準位の値とを比較した際、その差が小さい(0.5eV以下)材料を用いることが好ましい。従って、電子注入層115には、リチウム、セシウム、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、8-ヒドロキシキノリナト-リチウム(略称:Liq)、2-(2-ピリジル)フェノラトリチウム(略称:LiPP)、2-(2-ピリジル)-3-ピリジノラトリチウム(略称:LiPPy)、4-フェニル-2-(2-ピリジル)フェノラトリチウム(略称:LiPPP)リチウム酸化物(LiOx)、炭酸セシウム等のようなアルカリ金属、アルカリ土類金属、またはこれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。
なお、図1Bの発光デバイスにおける電荷発生層104は、第1の電極(陽極)101と第2の電極(陰極)102との間に電圧を印加したときに、陽極である第1の電極101側のEL層103aに電子を注入し、陰極である第2の電極102側のEL層103bに正孔を注入する機能を有する。なお、電荷発生層104は、正孔輸送性材料に電子受容体(アクセプタ)が添加された構成(P型層)であっても、電子輸送性材料に電子供与体(ドナー)が添加された構成(N型層)であってもよい。また、これらの両方の構成が積層されていても良い。また、上記P型層と、後述する電子リレー層および電子注入バッファ層のいずれか一又は両方を組み合わせて形成されていても良い。なお、上述した材料を用いて電荷発生層104を形成することにより、EL層が積層された場合における駆動電圧の上昇を抑制することができる。
本実施の形態で示した発光デバイスは、様々な基板上に形成することができる。なお、基板の種類は、特定のものに限定されることはない。基板の一例としては、半導体基板(例えば単結晶基板又はシリコン基板)、SOI基板、ガラス基板、石英基板、プラスチック基板、金属基板、ステンレス・スチル基板、ステンレス・スチル・ホイルを有する基板、タングステン基板、タングステン・ホイルを有する基板、可撓性基板、貼り合わせフィルム、繊維状の材料を含む紙、又は基材フィルムなどが挙げられる。
本実施の形態では、本発明の一態様である発光装置について説明する。なお、図2Aに示す発光装置は、第1の基板201上のトランジスタ(FET)202と発光デバイス(203R、203G、203B、203W)が電気的に接続されてなるアクティブマトリクス型の発光装置であり、複数の発光デバイス(203R、203G、203B、203W)は、共通のEL層204を有し、また、各発光デバイスの発光色に応じて、各発光デバイスの電極間の光学距離が調整されたマイクロキャビティ構造を有する。また、EL層204から得られた発光が第2の基板205に形成されたカラーフィルタ(206R、206G、206B)を介して射出されるトップエミッション型の発光装置である。
本実施の形態では、本発明の一態様である発光装置について説明する。
本実施の形態では、本発明の一態様である発光デバイス、本発明の一態様である発光デバイスを有する発光装置を適用して完成させた様々な電子機器や自動車の一例について、説明する。なお、発光装置は、本実施の形態で説明する電子機器において、主に表示部に適用することができる。
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光デバイスを適用して作製される照明装置の構成について図7を用いて説明する。
本実施例では、実施の形態1の構造式(100)で表される本発明の一態様である有機化合物、8-(2-ナフチル)-4-フェニル-2-(9’-フェニル-3,3’-ビ-9H-カルバゾール-9-イル)-[1]ベンゾフロ[3,2-d]ピリミジン(略称:4Ph-8βN-2PCCzBfpm)の合成方法について説明する。なお、4Ph-8βN-2PCCzBfpmの構造を以下に示す。
2,4,8-トリクロロ[1]ベンゾフロ[3,2-d]ピリミジン10g(37mmol)、フェニルボロン酸4.5g(371mmol)、2M炭酸カリウム水溶液37mL、トルエン180mL、エタノール18mLを500mLの三口フラスコに入れ、フラスコ内を脱気、窒素置換した。この混合物にビス(トリフェニルホスフィン)パラジウム(II)ジクロリド1.3g(1.8mmol)を加え、80℃で16時間撹拌した。
次に、ステップ1で得られた2,8-ジクロロ-4-フェニル-[1]ベンゾフロ[3,2-d]ピリミジン5.0g(16mmol)、9-フェニル-3,3’-ビ-9H-カルバゾール6.5g(16mmol)、tert-ナトリウムブトキシド3.1g(32mmol)、キシレン150mLを300mL三口フラスコに入れ、フラスコ内を窒素置換した。ここにジ-tert-ブチル(1-メチル-2,2-ジフェニルシクロプロピル)ホスフィン(略称:cBRIDP)224mg(0.64mmol)、アリルパラジウム(II)クロリドダイマー58mg(0.16mmol)を加え、90℃で7時間加熱撹拌した。
次に、上記ステップ2で得られた8-クロロ-4-フェニル-2-(9’-フェニル-3,3’-ビ-9H-カルバゾール-9-イル)-[1]ベンゾフロ[3,2-d]ピリミジン2.3g(3.3mmol)、2-ナフチルボロン酸0.62g(3.6mmol)、フッ化セシウム1.5g(9.81mmol)、キシレン35mLを三口フラスコに入れ、フラスコ内を窒素置換した。
次に、4Ph-8βN-2PCCzBfpmのトルエン溶液の紫外可視吸収スペクトル(以下、単に「吸収スペクトル」という)及び発光スペクトルを測定した。
本実施例では、実施の形態1の構造式(101)で表される本発明の一態様である有機化合物、8-(ジベンゾチオフェン-4-イル)-4-フェニル-2-(9’-フェニル-3,3’-ビ-9H-カルバゾール-9-イル)-[1]ベンゾフロ[3,2-d]ピリミジン(略称:4Ph-8DBt-2PCCzBfpm)の合成方法について説明する。なお、4Ph-8DBt-2PCCzBfpmの構造を以下に示す。
まず、実施例1のステップ2で得られた、8-クロロ-4-フェニル-2-(9’-フェニル-3,3’-ビ-9H-カルバゾール-9-イル)[1]ベンゾフロ[3,2-d]ピリミジン2.25g(3.3mmol)、4-ジベンゾチオフェンボロン酸0.82g(3.6mmol)、フッ化セシウム1.5g(9.8mmol)、キシレン35mLを三口フラスコに入れ、フラスコ内を窒素置換した。
次に、4Ph-8DBt-2PCCzBfpmのトルエン溶液の紫外可視吸収スペクトル(以下、単に「吸収スペクトル」という)及び発光スペクトルを測定した。
本実施例で示す発光デバイスは、図14に示すように基板900上に形成された第1の電極901上に正孔注入層911、正孔輸送層912、発光層913、電子輸送層914、電子注入層915が順次積層され、電子注入層915上に第2の電極903が積層された構造を有する。
作製した各発光デバイスの動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。また、各発光デバイスの動作特性の結果として電流密度-輝度特性を図15、電圧-輝度特性を図16、輝度-電流効率特性を図17、電圧-電流特性を図18にそれぞれ示す。
作製した発光デバイス4および比較発光デバイス5の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
Claims (11)
- 一般式(G1)で表される有機化合物。
(式中、Qは酸素または硫黄を表す。Aは、置換もしくは無置換の、環を形成する炭素数が6乃至13の縮合芳香族炭化水素環、または置換もしくは無置換の、環を形成する炭素数が6乃至13のπ過剰型の縮合複素芳香環のいずれか一を表し、R1乃至R19は、それぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の、環を形成する炭素数が3乃至7のシクロアルキル基、または置換もしくは無置換の、環を形成する炭素数が6乃至13のアリール基、のいずれか一を表す。) - 一般式(G2)で表される有機化合物。
(式中、Qは酸素または硫黄を表す。Aは、置換もしくは無置換の、環を形成する炭素数が6乃至13の縮合芳香族炭化水素環、または置換もしくは無置換の、環を形成する炭素数が6乃至13のπ過剰型の縮合複素芳香環のいずれか一を表し、R1乃至R19は、それぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の、環を形成する炭素数が3乃至7のシクロアルキル基、または置換もしくは無置換の、環を形成する炭素数が6乃至13のアリール基、のいずれか一を表す。) - 一般式(G3)で表される有機化合物。
(式中、Qは酸素または硫黄を表す。R1乃至R23は、それぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の、環を形成する炭素数が3乃至7のシクロアルキル基、または置換もしくは無置換の、環を形成する炭素数が6乃至13のアリール基、のいずれかを表す。) - 一般式(G4)で表される有機化合物。
(式中、Qは酸素または硫黄を表す。R1乃至R19およびR24乃至R27は、それぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の、環を形成する炭素数が3乃至7のシクロアルキル基、または置換もしくは無置換の、環を形成する炭素数が6乃至13のアリール基、のいずれかを表す。) - 構造式(100)または構造式(101)で表される有機化合物。
- 請求項1乃至請求項5のいずれか一に記載の有機化合物と、燐光発光材料とを有する発光デバイス。
- 一対の電極間に、発光層を有し、
前記発光層は、請求項1乃至請求項5のいずれか一に記載の有機化合物と、燐光発光材料とを有する発光デバイス。 - 陽極と陰極との間に、発光層を有し、
前記陰極と前記発光層との間に、請求項1乃至請求項5のいずれか一に記載の有機化合物を有する発光デバイス。 - 請求項6乃至請求項8のいずれか一に記載の発光デバイスと、
トランジスタ、または基板の少なくとも一と、
を有する発光装置。 - 請求項9に記載の発光装置と、
マイク、カメラ、操作用ボタン、外部接続部、または、スピーカの少なくとも一と、
を有する電子機器。 - 請求項6乃至請求項8のいずれか一に記載の発光デバイスと、
筐体、カバー、または、支持台の少なくとも一と、
を有する照明装置。
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JP2017524707A (ja) | 2014-07-29 | 2017-08-31 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
JP6918068B2 (ja) | 2018-10-10 | 2021-08-11 | 株式会社半導体エネルギー研究所 | 発光デバイス、発光装置、電子機器および照明装置 |
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US20220173327A1 (en) | 2022-06-02 |
CN113710673A (zh) | 2021-11-26 |
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