JP4050300B2 - 有機発光素子及びその製造方法 - Google Patents
有機発光素子及びその製造方法 Download PDFInfo
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- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 22
- 239000002019 doping agent Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 11
- -1 naphthyl anthracene Chemical compound 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000001771 vacuum deposition Methods 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 claims description 4
- 238000007641 inkjet printing Methods 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 230000005525 hole transport Effects 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 239000010410 layer Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000000758 substrate Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 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
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 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 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- FMOZIATXSMLFJS-UHFFFAOYSA-N 1-[2-cyclohexyloxy-4-ethoxy-5-(2-methoxyphenoxy)-3-phenoxy-6-propan-2-yloxyphenoxy]naphthalene Chemical group COC1=C(C=CC=C1)OC1=C(C(=C(C(=C1OCC)OC1=CC=CC=C1)OC1CCCCC1)OC1=CC=CC2=CC=CC=C12)OC(C)C FMOZIATXSMLFJS-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 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 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 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
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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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
- H10K85/615—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
-
- 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
-
- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K2101/90—Multiple hosts in the emissive layer
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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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
- H10K85/30—Coordination compounds
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- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Description
前記アノードとカソードとの間に電圧を印加すれば、アノードから注入されたホールは、HTLを経てEMLに移動する。一方、電子は、カソードからETLを経てEMLに注入され、EML領域でキャリアが再結合してエキシトンを生成する。このエキシトンが励起状態から基底状態に変化し、これによって、EMLの分子が発光することによって画像が形成される。
前記有機発光素子において、不活性のホスト材料に正孔輸送材料及び電子輸送材料をドーピングしてEMLを形成することによって、有機発光素子の性能を改善しようとする試みが行われてきた(特許文献1、特許文献2及び特許文献3)。
ところが、このような有機発光素子は、色特性及び寿命特性が満足すべきレベルに到達しておらず、改善の余地が多い。
本発明では、EMLの形成時、ホストとしてナフチルアントラセン系化合物及びビアントラセン系化合物からなる混合ホストを使用して、EMLに注入された電荷をEML内に効果的に束縛することによって、デバイスの安定性を向上させつつ色特性も改善させ得る。特に、前記ナフチルアントラセン系化合物は、デバイスの安定性を優秀に維持させるように手伝い、前記ビアントラセン系化合物は、色特性を良好に維持させるのに寄与する。
Xは、ナフチル基、ビフェニル基、ナフチルフェニル基またはアントラセニルフェニル基である。
a及びbは、互いに独立的に0ないし5の整数であり、
c、d、e及びfは、互いに独立的に2ないし4の整数であり、
R1ないしR6によって表示される複数の群は、互いに同一であるか、または異なり、または結合を形成して環を形成し、
Lは、単一結合、−O−、−S−、−N(R’)−またはC6−C20のアリーレン基を表し、R’は、C1−C10のアルキル基、またはC6−C20のアリール基を表す。
[実施例1]
アノードは、コーニング 15Ω/cm2(1200Å)のITOガラス基板を50mmx50mmx0.7mmのサイズに切って、イソプロピルアルコール及び純水の中で各5分間超音波で洗浄した後、30分間UV、オゾンで洗浄して使用した。
発光層の形成時、化学式3の化合物及び化学式5の化合物の含量がそれぞれ50重量部及び50重量部であることを除いては、実施例1と同じ方法によって実施して有機発光素子を製造した。
Claims (17)
- 第1電極と第2電極との間に発光層を有する有機発光素子において、
前記発光層は、
ナフチルアントラセン系化合物及びビアントラセン系化合物からなる混合ホストとドーパントとを含み、
前記ナフチルアントラセン系化合物は、下記化学式1で表示される化合物であり、
前記ビアントラセン系化合物は、下記化学式2で表示される化合物であり、
a及びbは、互いに独立的に0ないし5の整数であり、
c、d、e及びfは、互いに独立的に1ないし4の整数であり、
R 1 ないしR 6 によって表示される複数の群は、互いに同一であるか、または異なり、または結合を形成して環を形成し、
Lは、単一結合、−O−、−S−、−N(R’)−またはC6−C20のアリーレン基を表し、R’は、C1−C10のアルキル基、またはC6−C20のアリール基を表すことを特徴とする有機発光素子。 - 前記ドーパントは、青色ドーパントであることを特徴とする請求項1に記載の有機発光素子。
- 前記化学式8で表示される化合物は、
R1、R2、R5、R6は、何れもフェニル基であり、R3及びR4は、フェニレン基である化合物と、
R1及びR5は、フェニル基であり、R2及びR6は、ナフチル基であり、R3及びR4は、フェニレン基である化合物と、または
R1及びR5は、ナフチル基であり、R2及びR6は、何れもフェニル基であり、R3及びR4は、ナフチレン基である化合物であることを特徴とする請求項5に記載の有機発光素子。 - 前記ナフチルアントラセン系化合物とビアントラセン系化合物との混合重量比は、10:90ないし90:10であることを特徴とする請求項1に記載の有機発光素子。
- 前記発光層でドーパントの含量は、ホスト総重量100重量部に対して3ないし7重量部であることを特徴とする請求項1に記載の有機発光素子。
- 前記発光層でナフチルアントラセン系化合物とビアントラセン系化合物との混合重量比は、25:75ないし75:25であり、ドーパントの含量は、ホスト総重量100重量部に対して3ないし7重量部であることを特徴とする請求項1に記載の有機発光素子。
- 前記化学式3の化合物と化学式5の化合物との混合重量比は、75:25ないし25:75重量部であることを特徴とする請求項11に記載の有機発光素子。
- 前記発光層でドーパントの含量は、ホスト総重量100重量部に対して3ないし7重量部であることを特徴とする請求項11に記載の有機発光素子。
- 前記第1電極と発光層との間に、ホール注入層及びホール輸送層のうち選択された一つ以上がさらに備えられることを特徴とする請求項1に記載の有機発光素子。
- 前記発光層と第2電極との間に、ホールブロッキング層、電子輸送層及び電子注入層のうち選択された一つ以上がさらに備えられることを特徴とする請求項1に記載の有機発光素子。
- 第1電極と第2電極との間に発光層を有する有機発光素子の製造方法において、
前記発光層は、請求項1に記載のナフチルアントラセン系化合物及び請求項1に記載のビアントラセン系化合物からなる混合ホストとドーパントとを利用して形成されることを特徴とする有機発光素子の製造方法。 - 前記発光層は、真空蒸着、インクジェットプリンティングまたはレーザー転写によって
形成されることを特徴とする請求項16に記載の有機発光素子の製造方法。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005058557A1 (de) * | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
CN101374789B (zh) * | 2006-01-27 | 2014-04-30 | Lg化学株式会社 | 新的蒽衍生物、其制备方法以及采用该蒽衍生物的有机发光二极管 |
CN101279969B (zh) * | 2007-01-31 | 2011-03-30 | 北京维信诺科技有限公司 | 一种有机电致发光材料及其应用 |
EP2124270A4 (en) * | 2007-02-28 | 2010-08-25 | Idemitsu Kosan Co | ORGANIC EL-INSTALLATION |
KR100858816B1 (ko) * | 2007-03-14 | 2008-09-17 | 삼성에스디아이 주식회사 | 안트라센 유도체 화합물을 포함하는 유기막을 구비하는유기 발광 소자 |
US8471461B2 (en) * | 2007-03-29 | 2013-06-25 | Dai Nippon Printing Co., Ltd. | Organic electroluminescent device and method for producing the same |
KR100857024B1 (ko) * | 2007-04-13 | 2008-09-05 | (주)그라쎌 | 고성능의 전기 발광 화합물 및 이를 채용하는 유기발광소자 |
TW200920813A (en) * | 2007-07-07 | 2009-05-16 | Idemitsu Kosan Co | Organic electroluminescence device |
KR100974562B1 (ko) * | 2007-12-31 | 2010-08-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
TWI397152B (zh) | 2008-09-25 | 2013-05-21 | Nanya Technology Corp | 電阻式隨機存取記憶體結構及其製作方法 |
CN101728480B (zh) * | 2008-10-17 | 2013-05-08 | 南亚科技股份有限公司 | 电阻式随机存取存储器结构及其制作方法 |
KR100994118B1 (ko) | 2009-01-13 | 2010-11-15 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 및 그 제조 방법 |
KR101317511B1 (ko) * | 2009-04-30 | 2013-10-15 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 전자 소자 |
EP2430680A2 (en) * | 2009-05-12 | 2012-03-21 | E. I. du Pont de Nemours and Company | Organic electronic device with electron tunneling layer |
KR101097313B1 (ko) * | 2009-08-10 | 2011-12-23 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
CN102146090B (zh) * | 2010-02-09 | 2013-03-13 | 广东阿格蕾雅光电材料有限公司 | 芳环取代的双蒽类化合物发光材料 |
CN102225881B (zh) * | 2011-04-28 | 2014-12-10 | 西安近代化学研究所 | 9,9′-联蒽衍生物及其制备方法 |
CN102627524A (zh) * | 2012-03-20 | 2012-08-08 | 西安近代化学研究所 | 一种9,9’-联蒽衍生物 |
KR20150093440A (ko) * | 2014-02-07 | 2015-08-18 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
JP5848480B1 (ja) | 2014-10-28 | 2016-01-27 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
CN106146343B (zh) * | 2015-04-23 | 2018-06-26 | 上海和辉光电有限公司 | 一种化合物及其合成方法和应用 |
US11991922B2 (en) * | 2018-10-12 | 2024-05-21 | Lg Chem, Ltd. | Organic light-emitting device |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6582837B1 (en) * | 1997-07-14 | 2003-06-24 | Nec Corporation | Organic electroluminescence device |
US5935721A (en) * | 1998-03-20 | 1999-08-10 | Eastman Kodak Company | Organic electroluminescent elements for stable electroluminescent |
EP1061112A4 (en) | 1998-12-28 | 2004-12-29 | Idemitsu Kosan Co | ORGANIC ELECTROLUMINESCENT ELEMENT |
US6392339B1 (en) * | 1999-07-20 | 2002-05-21 | Xerox Corporation | Organic light emitting devices including mixed region |
TW463520B (en) * | 1999-07-30 | 2001-11-11 | Sony Corp | Organic electroluminescent device |
DE60042010D1 (de) * | 1999-09-30 | 2009-05-28 | Idemitsu Kosan Co | Organisches electrolumineszenz-element mit einer amin-verbindung |
JP2001097897A (ja) * | 1999-09-30 | 2001-04-10 | Idemitsu Kosan Co Ltd | 有機化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP4255610B2 (ja) * | 1999-12-28 | 2009-04-15 | 出光興産株式会社 | 白色系有機エレクトロルミネッセンス素子 |
EP1182183B1 (en) * | 2000-03-29 | 2009-12-09 | Idemitsu Kosan Co., Ltd. | Anthracene derivatives and organic electroluminescent devices made by using the same |
JP4094203B2 (ja) * | 2000-03-30 | 2008-06-04 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び有機発光媒体 |
JP2001288377A (ja) * | 2000-04-06 | 2001-10-16 | Sony Corp | アミノスチリルアントラセン化合物及びその合成中間体、並びにこれらの製造方法 |
US6392250B1 (en) * | 2000-06-30 | 2002-05-21 | Xerox Corporation | Organic light emitting devices having improved performance |
JP4220669B2 (ja) * | 2000-12-26 | 2009-02-04 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US6846579B2 (en) * | 2002-02-15 | 2005-01-25 | Eastman Kodak Company | Multilayer with radiation absorber and touch screen |
US6933064B2 (en) * | 2002-02-15 | 2005-08-23 | Eastman Kodak Company | Multilayer with spacers, touch screen and method |
US6670053B2 (en) * | 2002-02-26 | 2003-12-30 | Eastman Kodak Company | Organic electroluminescent devices with high luminance |
US6824893B2 (en) * | 2002-02-28 | 2004-11-30 | Eastman Kodak Company | Organic element for electroluminescent devices |
JP4041816B2 (ja) * | 2002-08-23 | 2008-02-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及びアントラセン誘導体 |
US6967062B2 (en) * | 2003-03-19 | 2005-11-22 | Eastman Kodak Company | White light-emitting OLED device having a blue light-emitting layer doped with an electron-transporting or a hole-transporting material or both |
TWI224473B (en) * | 2003-06-03 | 2004-11-21 | Chin-Hsin Chen | Doped co-host emitter system in organic electroluminescent devices |
US6824895B1 (en) * | 2003-12-05 | 2004-11-30 | Eastman Kodak Company | Electroluminescent device containing organometallic compound with tridentate ligand |
US7576486B2 (en) * | 2004-04-02 | 2009-08-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element having two electroluminescent layers through electron barrier layer |
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KR100696505B1 (ko) | 2007-03-19 |
JP2006287218A (ja) | 2006-10-19 |
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