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WO2011053035A2 - Composé électroluminescent organique et élément électroluminescent organique comprenant un tel composé - Google Patents

Composé électroluminescent organique et élément électroluminescent organique comprenant un tel composé Download PDF

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WO2011053035A2
WO2011053035A2 PCT/KR2010/007512 KR2010007512W WO2011053035A2 WO 2011053035 A2 WO2011053035 A2 WO 2011053035A2 KR 2010007512 W KR2010007512 W KR 2010007512W WO 2011053035 A2 WO2011053035 A2 WO 2011053035A2
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light emitting
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WO2011053035A3 (fr
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김복영
안중복
이재성
강지승
안도환
진성민
박노길
한근희
이대균
시상만
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CS ELSOLAR CO LTD
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Definitions

  • the present invention relates to an organic light emitting compound and an organic light emitting device including the same, and more particularly, to an organic light emitting device employing an organic light emitting compound and an organic film containing the compound, which can realize excellent light emission efficiency and light emission luminance when the organic light emitting device is applied. It is about.
  • the light emitting device is a self-luminous device, and has a wide viewing angle, excellent contrast, and fast response time.
  • the light emitting device is classified into an inorganic light emitting device using an inorganic compound and an organic light emitting device (OLED) using an organic compound as an emitting layer.
  • OLED organic light emitting device
  • the organic light emitting device is a subject of many studies in that it is excellent in physical properties such as high luminance, low driving voltage, short response speed, and can be multicolored, compared to the inorganic light emitting device.
  • the organic light emitting device generally has a stacked structure of anode / organic light emitting layer / cathode, and includes anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode or anode / hole injection layer / hole transport layer / light emitting layer / It may have various structures such as a hole blocking layer / electron transport layer / electron injection layer / cathode.
  • a high performance organic light emitting compound is important.
  • blue and green light emitting compounds include ⁇ -ADN (compound A), C545T (compound B), quinacridone derivatives (compound C), DPT (compound D), and the like.
  • Japanese Patent Laid-Open No. 2001-131541 discloses a bis (2,6-diarylamino) -9,10-diphenylanthracene (Compound E) derivative
  • WO 2005-100506 discloses 2-aryl. -9- (2-naphthyl) -10-aryl-anthracene (compound F) derivatives are disclosed.
  • the organic light emitting compounds should be further improved in luminous efficiency, luminous brightness, and the like.
  • the first technical challenge is to provide new organic light emitting compounds.
  • the second technical problem is to provide an organic light emitting device having improved luminous efficiency and luminous brightness.
  • an organic light emitting compound represented by Formula A is provided.
  • CY1 and CY2 are independently of each other a C 6 -C 30 aromatic ring or C 2 -C 30 aromatic heterocycle;
  • R 1 , R 2 , R 3 and R 4 are each independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, or a substituted or unsubstituted C 2 -C 50 heteroaryl group; Provided that R 1 , R 2 , R 3 and R 4 are not simultaneously hydrogen,
  • X 1 and X 2 are each independently a chemical bond, a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 6 -C 50 arylene group, or a substituted or unsubstituted C 2 -C 50 hetero Arylene group
  • R 5 and R 6 are each independently a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group,- N (Z 1 ) (Z 2 ), or —Si (Z 3 ) (Z 4 ) (Z 5 ), wherein Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently of each other, substituted or unsubstituted A substituted C 1 -C 5 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, or a substituted or unsubstituted C 2 -C 50 heteroaryl group;
  • a and b are each independently an integer of 0 to 4; However, if a and b is 0, CY1 or CY2 is an aromatic ring or more C 7.
  • the first electrode Second electrode; And an organic light emitting device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film includes an organic light emitting compound as described above.
  • An organic light emitting device having a new organic light emitting compound according to one aspect improves luminous efficiency and luminous luminance.
  • FIGS. 1A to 1C are cross-sectional views schematically illustrating structures of one embodiment of an organic light emitting diode according to the present invention.
  • an organic light emitting compound is a compound used in an organic light emitting device, and is not necessarily limited to a compound capable of emitting light, and its application range is not limited to an organic light emitting layer, and a charge injection layer, a charge transport layer, and a hole injection It can be used in any layer constituting the organic light emitting device, such as a layer, a hole transport layer.
  • CY1 and CY2 are independently of each other a C 6 -C 30 aromatic ring or C 2 -C 30 aromatic heterocycle;
  • R 1 , R 2 , R 3 and R 4 are each independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, or a substituted or unsubstituted C 2 -C 50 heteroaryl group;
  • R 1 , R 2 , R 3 and R 4 are not hydrogen at the same time, and X 1 and X 2 are each independently a chemical bond, a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C A 6 -C 50 arylene group, or a substituted or unsubstituted C 2 -C 50 heteroarylene group;
  • R 5 and R 6 are each independently a substituted or unsubstituted C 1 -C
  • the compound represented by Chemical Formula A is suitable as a material forming an organic film interposed between the first electrode and the second electrode of the organic light emitting device.
  • the compound of Formula 1 is suitable for use in an organic layer, in particular a light emitting layer, a hole injection layer or a hole transport layer of the organic light emitting device and may be used as a dopant material as well as a host material.
  • the aromatic ring is an aromatic ring system, and may include two or more ring systems, and the two or more ring systems may exist in a bonded or fused form with each other.
  • the aromatic hetero ring refers to a group in which at least one carbon of the aromatic ring is arranged with at least one selected from the group consisting of N, S, O, and P.
  • the aryl group is a monovalent group having an aromatic ring system, and may include two or more ring systems, and the two or more ring systems may exist in a bonded or fused form with each other.
  • the heteroaryl group refers to a group in which at least one carbon in the aryl group is substituted with at least one selected from the group consisting of N, O, S, and P.
  • the arylene group corresponds to a divalent group of an aryl group
  • the heteroarylene group corresponds to a divalent group of a heteroaryl group
  • alkyl group, aryl group, heteroaryl group, alkylene group, arylene group, and heteroarylene group are C 1 -C 50 alkyl group; C 6 -C 50 aryl groups unsubstituted or substituted with C 1 -C 50 alkyl groups; C 2 -C 50 heteroaryl group unsubstituted or substituted with a C 1 -C 50 alkyl group; And -N (Z 5 ) (Z 6 ), Z 5 and Z 6 are each independently a C 6 -C 50 aryl group which is unsubstituted or substituted with a C 1 -C 50 alkyl group. It may be one or more selected from.
  • CY1 and CY2 may be independently selected from the following ring:
  • R 1 , R 2 , R 3 and R 4 are each independently hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, phenyl or biphenyl And pyridyl groups.
  • X 1 and X 2 are independently a chemical bond, a phenylene group, a pyridinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a thiophenylene group, an indolylene group, a furinylene group, a benzimidazolylene group, Quinolinylene group, benzothiophenylene group, parathiazinylene group, pyrroylene group, pyrazolylene group, imidazolylene group, imidazolinylene group, oxazolylene group, thiazolylene group, triazolylene group, tetrazoylene group, And it may be selected from the group consisting of oxadiazolylene group.
  • R 5 and R 6 may be independently selected from the following structures:
  • organic light emitting compound may be represented by the following Formula B:
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X 1 , X 2 , a and b are as defined above
  • the organic light emitting compound may have a structure of Formulas 1 to 89, but is not limited thereto:
  • the organic light emitting compound represented by Chemical Formula A may be synthesized using a conventional synthetic method, and for a more detailed synthetic route of the compound, see Scheme of Synthesis Example below.
  • an organic light emitting diode includes: a first electrode; Second electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one compound represented by Formula A below.
  • CY1 and CY2 are independently of each other a C 6 -C 30 aromatic ring or C 2 -C 30 aromatic heterocycle;
  • R 1 , R 2 , R 3 and R 4 are each independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, or a substituted or unsubstituted C 2 -C 50 heteroaryl group;
  • R 1 , R 2 , R 3 and R 4 are not hydrogen at the same time, and X 1 and X 2 are each independently a chemical bond, a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C A 6 -C 50 arylene group, or a substituted or unsubstituted C 2 -C 50 heteroarylene group;
  • R 5 and R 6 are each independently a substituted or unsubstituted C 1 -C
  • the compound of formula (A) is suitable for use in organic membranes of organic light emitting devices, especially light emitting layers, hole injection layers or hole transport layers.
  • the structure of the organic light emitting device according to another embodiment is very diverse.
  • One or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer and an electron injection layer may be further included between the first electrode and the second electrode.
  • the organic light emitting device of Figure 1a has a structure consisting of a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode
  • the organic light emitting device of Figure 1b has a first electrode / hole injection layer / hole transport layer / Light emitting layer / electron transport layer / electron injection layer / second electrode
  • the organic light emitting device of FIG. 1C has a structure of a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode.
  • one or more of the light emitting layer, the hole injection layer and the hole transport layer may include a compound represented by the formula (1) and / or 2.
  • the emission layer of the organic light emitting diode may include a phosphorescent or fluorescent dopant including red, green, blue, or white.
  • the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.
  • the compound represented by Formula A may be used as a fluorescent dopant in the emission layer.
  • a method of manufacturing an organic light emitting diode according to another embodiment will be described with reference to the organic light emitting diode illustrated in FIG. 1C.
  • a first electrode material having a high work function on the substrate is disposed by a deposition method or a sputtering method to form a first electrode.
  • the first electrode may be an anode.
  • a substrate used in a conventional organic light emitting device is used, but a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable.
  • the first electrode material indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.
  • a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 Pa / sec, and a film thickness are appropriately selected in the range of usually 100 Pa to 10 ⁇ m.
  • the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm.
  • the heat treatment temperature for removing the solvent is preferably selected from a temperature range of about 80 ° C to 200 ° C.
  • the hole injection layer material may be a compound represented by Formula A as described above.
  • phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or the starburst type amine derivatives described in Advanced Material, 6, p.677 (1994), TCTA, m-MTDATA, m- MTDAPB, 2-TNATA (4,4 ', 4 "-tris (N- (2-naphtyl) -N-phenylamino) triphenylamine: 4,4', 4" -tris (N- (naphthyl) -N-phenyl Amino) triphenylamine), soluble conductive polymer Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly(
  • the hole injection layer may have a thickness of about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.
  • a hole transport layer may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB.
  • the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from a range of conditions almost the same as that of the formation of the hole injection layer.
  • the hole transport layer material may include a compound of formula A as described above.
  • carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl ] 4,4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD), and other conventional amine derivatives having aromatic condensed rings
  • Known hole transport materials such as the like may be used.
  • the hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be degraded, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.
  • the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like.
  • the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.
  • the light emitting layer may include a compound represented by Formula A as described above. At this time, it may be used with a known host material suitable for the compound of formula A, or may be used with a known dopant material. It is also possible to use the compound of formula A alone.
  • host materials for example, Alq3 (tris (8-hydroxy-quinolatealuminium) or CBP (4,4'-N, N'-dicarbazole-biphenyl), or PVK (poly (n-vinylcarbazole) ) Can be used.
  • IDE102, IDE105, and C545T available from Hayashibara
  • green phosphorescent dopant can be used as the phosphorescent dopant.
  • Ir (PPy) 3 (PPy 2-phenylpyridine)
  • F 2 Irpic which is a blue phosphorescent dopant
  • MQD N-methylquinacridone
  • coumarin (Coumarine) derivative, etc. can also be used.
  • Doping concentration is not particularly limited, but the content of the dopant is generally 0.01 to 15 parts by weight based on 100 parts by weight of the host.
  • the thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa. This is because, when the thickness of the light emitting layer is less than 100 kW, the light emission characteristics may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.
  • a method such as vacuum deposition, spin coating, cast method, LB method, etc. is used on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer.
  • the hole blocking layer HBL can be formed.
  • the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer.
  • Known hole blocking materials include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and BCP.
  • the hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase.
  • the electron transport layer is formed using various methods such as vacuum deposition, spin coating, and casting.
  • the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer.
  • the electron transport layer material functions to stably transport electrons injected from an electron injection electrode (Cathode), and a quinoline derivative, particularly a known material such as tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, etc. Can also be used.
  • the electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.
  • an electron injection layer which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, which does not particularly limit the material.
  • any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO or the like can be used.
  • the deposition conditions of the electron injection layer vary depending on the compound used, they are generally selected from the range of conditions almost the same as the formation of the hole injection layer.
  • the electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 50 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.
  • the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method.
  • the second electrode may be used as a cathode.
  • a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned.
  • a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.
  • ADN (9,10-di (naphthalene-2-yl) anthracene) represented by the following Chemical Formula d is used as a light emitting layer material
  • 2-TNATA (4,4 ', 4 "-tris (N) represented by the following Chemical Formula a -naphthalen-2-yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material
  • ⁇ -NPD N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine
  • Alq3 represented by the following Chemical Formula c was used as the electron transport layer material to prepare an organic light emitting device having the following structure: ITO / 2-TNATA (80nm) / ⁇ NPD (30 nm) / compound d (30 nm) / Alq 3 (40 nm) / LiF (0.5 nm) / Al (50 nm).
  • Anode cuts Corning's 15 ⁇ / cm 2 (1000 ⁇ ) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing.
  • 2-TANATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm.
  • ⁇ -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm.
  • ADN represented by Chemical Formula d was vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm.
  • Comparative Sample 1 LiF 0.5 nm (electron injection layer) and Al 50 nm (cathode) were sequentially vacuum deposited on the electron transport layer to prepare an organic light emitting device as shown in FIG. 1B. This is called Comparative Sample 1.
  • the device was fabricated using an EL deposition machine manufactured by DIOB Corporation.
  • Comparative Example 1 In Comparative Example 1, except that Compounds 1 to 78 represented by Formulas 1 to 78 were used instead of Compound d as the light emitting layer compound, ITO / 2-TNATA (80nm) / ⁇ - in the same manner as in Comparative Example 1 An organic light emitting diode having a structure of NPD (30 nm) / [one of the light emitting layer compounds 1 to 78] (30 nm) / Alq 3 (40 nm) / LiF (0.5 nm) / Al (50 nm) was manufactured. These are called Samples 1 to 78, respectively.
  • ITO / 2-TNATA in the same manner as in Comparative Example 1 except that Compounds 1 to 17 disclosed in Synthesis Example were used instead of ⁇ -NPD represented by Formula d as the hole transport layer material.
  • samples 101 to 108 the driving voltage, emission luminance, emission efficiency, and emission peak were evaluated using Keithley SMU 235 and PR650, respectively, and the results are shown in Table 4 below.
  • the samples showed blue emission peak values in the range of 412-460 nm.
  • the organic light emitting device having the new organic light emitting compound has improved luminous efficiency and luminous brightness.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Luminescent Compositions (AREA)

Abstract

L'invention concerne un composé représenté par la formule chimique A et un élément électroluminescent organique comprenant un tel composé. Dans la formule chimique A, CY1, CY2, R1, R2, R3, R4, X1, X2, R5, R6, a et b sont tels que définis dans la description de l'invention.
PCT/KR2010/007512 2009-11-02 2010-10-29 Composé électroluminescent organique et élément électroluminescent organique comprenant un tel composé Ceased WO2011053035A2 (fr)

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US20140239280A1 (en) * 2011-08-18 2014-08-28 Udc Ireland Limited Organic electroluminescent element, light-emitting material for organic electroluminescent element, and light-emitting device, display device, and illumination device using said element
WO2016109274A1 (fr) * 2014-12-30 2016-07-07 Dow Global Technologies Llc Dérivés de fluorène utilisables en tant qu'éléments émetteurs de lumière pour dispositifs électroluminescents
CN106008138A (zh) * 2016-05-23 2016-10-12 中节能万润股份有限公司 一种有机电致发光材料、应用及发光器件
CN106188026A (zh) * 2016-07-01 2016-12-07 中节能万润股份有限公司 一类非对称结构有机电致发光材料及其应用
WO2016192329A1 (fr) * 2015-06-02 2016-12-08 吉林奥来德光电材料股份有限公司 Composé hétérocyclique aromatique, son procédé de préparation, et composant électroluminescent organique
CN106800528A (zh) * 2016-12-14 2017-06-06 中节能万润股份有限公司 一种萘醌并9,9,10,10‑四甲基‑蒽类有机电致发光材料及其制备方法和应用
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JP4965914B2 (ja) * 2006-07-05 2012-07-04 キヤノン株式会社 有機化合物及び発光素子

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US9691988B2 (en) * 2011-08-18 2017-06-27 Udc Ireland Limited Organic electroluminescent element, light-emitting material for organic electroluminescent element, and light-emitting device, display device, and illumination device using said element
US20140239280A1 (en) * 2011-08-18 2014-08-28 Udc Ireland Limited Organic electroluminescent element, light-emitting material for organic electroluminescent element, and light-emitting device, display device, and illumination device using said element
CN103173211A (zh) * 2012-11-09 2013-06-26 吉林奥来德光电材料股份有限公司 含有二氢并五苯的有机光发光材料及其制备方法
WO2016109274A1 (fr) * 2014-12-30 2016-07-07 Dow Global Technologies Llc Dérivés de fluorène utilisables en tant qu'éléments émetteurs de lumière pour dispositifs électroluminescents
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WO2016192329A1 (fr) * 2015-06-02 2016-12-08 吉林奥来德光电材料股份有限公司 Composé hétérocyclique aromatique, son procédé de préparation, et composant électroluminescent organique
CN106008138A (zh) * 2016-05-23 2016-10-12 中节能万润股份有限公司 一种有机电致发光材料、应用及发光器件
CN106188026A (zh) * 2016-07-01 2016-12-07 中节能万润股份有限公司 一类非对称结构有机电致发光材料及其应用
CN106800528A (zh) * 2016-12-14 2017-06-06 中节能万润股份有限公司 一种萘醌并9,9,10,10‑四甲基‑蒽类有机电致发光材料及其制备方法和应用
CN106800528B (zh) * 2016-12-14 2019-06-28 中节能万润股份有限公司 一种萘醌并9,9,10,10-四甲基-蒽类有机电致发光材料及其制备方法和应用
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CN109535064B (zh) * 2018-12-26 2023-01-24 武汉天马微电子有限公司 化合物、显示面板以及显示装置
CN114478607A (zh) * 2021-12-30 2022-05-13 武汉尚赛光电科技有限公司 一种有机发光材料及其应用和器件
CN114478607B (zh) * 2021-12-30 2024-05-14 武汉尚赛光电科技有限公司 一种有机发光材料及其应用和器件

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KR101256204B1 (ko) 2013-04-19
KR20110048254A (ko) 2011-05-11

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