WO2019185061A1 - Composé à base de bis(diméthylfluorène), son procédé de préparation et son utilisation - Google Patents

Composé à base de bis(diméthylfluorène), son procédé de préparation et son utilisation Download PDF

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WO2019185061A1
WO2019185061A1 PCT/CN2019/080634 CN2019080634W WO2019185061A1 WO 2019185061 A1 WO2019185061 A1 WO 2019185061A1 CN 2019080634 W CN2019080634 W CN 2019080634W WO 2019185061 A1 WO2019185061 A1 WO 2019185061A1
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compound
substituted
group
formula
unsubstituted
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赵四杰
李崇
张兆超
王芳
张小庆
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江苏三月光电科技有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • 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
    • 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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  • the invention relates to a compound based on bisdimethylhydrazine, a preparation method and application thereof, and belongs to the technical field of semiconductors.
  • OLED Organic Light Emission Diodes
  • the OLED light-emitting device is like a sandwich structure, including an electrode material film layer and an organic functional material sandwiched between different electrode film layers, and various functional materials are superposed on each other according to the purpose to form an OLED light-emitting device.
  • the OLED light-emitting device functions as a current device.
  • the positive and negative charges in the organic layer functional material film layer are applied by the electric field, the positive and negative charges are further recombined in the light-emitting layer, that is, the OLED electroluminescence is generated.
  • OLED display technology has been applied in the fields of smart phones, tablet computers, etc., and will further expand to large-size applications such as television, but the luminous efficiency and service life of OLED devices are compared with actual product application requirements. Further improvement is needed.
  • research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device.
  • the OLED optoelectronic functional materials applied to OLED devices can be divided into two categories from the use of charge injection transport materials and luminescent materials. Further, the charge injection transport material may be further classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the luminescent material may be further divided into a host luminescent material and a dopant material.
  • organic functional materials are required to have good photoelectric properties.
  • a charge transport material it is required to have good carrier mobility, high glass transition temperature, etc., as a main body of the light-emitting layer.
  • the material has good bipolarity, appropriate HOMO/LUMO energy levels, and the like.
  • the OLED photoelectric functional material film layer constituting the OLED device includes at least two layers or more, and the industrially applied OLED device structure includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron transport.
  • Layers, electron injection layers and other film layers, that is to say, the photoelectric functional materials applied to the OLED device include at least hole injection materials, hole transport materials, luminescent materials, electron transport materials, etc., and the material types and combinations are rich. And the characteristics of diversity.
  • the optoelectronic functional materials used have strong selectivity, and the performance of the same materials in different structural devices may be completely different.
  • the photoelectric characteristics of devices must be selected to be more suitable and higher performance OLED functional materials or material combinations in order to achieve high efficiency and long life of the device. And the comprehensive characteristics of low voltage.
  • the development of OLED materials is still far from enough. It is lagging behind the requirements of panel manufacturers, and it is especially important to develop higher performance organic functional materials as material enterprises.
  • One of the objects of the present invention is to provide a compound based on bisdimethylhydrazine.
  • the compound of the invention contains a bisdimethylhydrazine structure, has high glass transition temperature and molecular thermal stability, suitable HOMO and LUMO energy levels, high Eg, and can optimize the photoelectric performance of the OLED device through device structure optimization. And the lifetime of OLED devices.
  • L, L 1 or L 2 are each independently represented by a single bond, a C 6 -C 60 arylene group, a C 6 -C 60 aryl group or a C 5 -C 60 heteroaryl group. Any H atom of a C 6 -C 60 aryl or C 5 -C 60 heteroaryl group may be substituted with a C 1 -C 10 alkyl group;
  • R is represented by the structure represented by the general formula (II) or the general formula (III):
  • X represents one of an oxygen atom, a sulfur atom, an alkyl-substituted alkylene group, an aryl-substituted alkylene group, an alkyl-substituted imido group or an aryl-substituted imido group.
  • R 1 and R 2 are each independently represented by a hydrogen atom, a halogen, a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 heteroaryl group, a substitution or An unsubstituted C 6 -C 30 aryl group or one of the structures represented by the formula (IV), and at least one of R 1 and R 2 is represented by the structure represented by the formula (IV);
  • the compound of the present invention is an organic light-emitting functional layer material which has the characteristics of being incapable of crystallization, inhomogeneity, and good film formation, and the rigid group in the molecule of the compound of the present invention can improve the thermal stability of the material.
  • the structure of the compound of the invention makes the distribution of electrons and holes in the luminescent layer more balanced, and improves the hole injection/transport performance at the appropriate HOMO level; and at the appropriate LUMO level, it acts as an electron blocking.
  • Enhancing the recombination efficiency of the excitons in the light-emitting layer; when used as a light-emitting functional layer material of the OLED light-emitting device, the use of an aryl-substituted fluorene in combination with the branches within the scope of the invention can effectively improve the exciton utilization and high fluorescence radiation efficiency. Reduces efficiency roll-off at high current densities, reduces device voltage, and improves device current efficiency and lifetime.
  • the present invention can also be improved as follows.
  • the L, L 1 or L 2 are each independently represented by a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted naphthylene group, a substituted or not One of a substituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group.
  • the X represents an oxygen atom, a sulfur atom, a dimethyl-substituted alkylene group, a diphenyl-substituted alkylene group, a phenyl-substituted imido group, a biphenyl-substituted imido group, a fluorenyl group.
  • a substituted imino group a dibenzofuranyl substituted imido group, or an N-phenylcarbazolyl substituted imido group.
  • Another object of the present invention is to provide a process for the preparation of the above bisdimethylhydrazine-based compound.
  • the preparation method of the bisdimethylhydrazine-based compound of the invention is simple, has a broad market prospect, and is suitable for large-scale production.
  • the technical solution of the present invention to solve the above technical problems is as follows:
  • the preparation method of the above-mentioned bisdimethylhydrazine-based compound, the reaction equation occurring during the preparation process is:
  • the compound A and the compound B are weighed, dissolved in toluene, and then Pd 2 (dba) 3 , tri-tert-butylphosphine and sodium t-butoxide are added; the mixed solution of the above reactants is reacted at a reaction temperature of 95-110 under an inert atmosphere. °C, the reaction is 10-24 hours, the reaction solution is cooled and filtered, and the filtrate is steamed and passed through a silica gel column to obtain the target product;
  • the molar ratio of the compound A to the compound B is 1: (1.0-1.5)
  • the molar ratio of the Pd 2 (dba) 3 to the compound A is (0.004-0.01): 1
  • the tri-tert-butyl group The molar ratio of phosphine to compound A is (0.004-0.01): 1
  • the molar ratio of sodium t-butoxide to compound A is (1-1.5):1.
  • a third object of the present invention is to provide an organic electroluminescent device.
  • the compound of the invention has good application effects in OLED light-emitting devices and has good industrialization prospects.
  • An organic electroluminescent device at least one functional layer containing the above-mentioned didimethylfluorene-based compound.
  • the present invention can also be improved as follows.
  • the functional layer is a light-emitting layer and/or an electron blocking layer and/or a hole transport layer.
  • a fourth object of the invention is to provide an illumination or display element.
  • the organic electroluminescent device of the invention can be applied to illumination or display originals, so that the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; at the same time, the device lifetime is improved obviously, and the OLED light-emitting device has good performance.
  • the application effect has a good industrialization prospect.
  • an illumination or display element comprising the organic electroluminescent device as described above.
  • the compound of the invention contains a bisdimethylhydrazine structure, has a high glass transition temperature and molecular thermal stability, a suitable HOMO and LUMO energy level, a high Eg, and is optimized by device structure, which can effectively enhance the OLED device. Photoelectric properties and lifetime of OLED devices.
  • the compound of the present invention is an organic light-emitting functional layer material, which has the characteristics that it is difficult to crystallize, is difficult to aggregate, and has good film forming properties.
  • the rigid group in the molecule of the compound of the present invention can improve the thermal stability of the material. Sex.
  • the structure of the compound of the present invention makes the distribution of electrons and holes in the luminescent layer more balanced, and improves the hole injection/transport performance at the appropriate HOMO level; and at the appropriate LUMO level, it also acts as an electron blocking.
  • the effect of improving the recombination efficiency of the exciton in the luminescent layer; when used as the luminescent functional layer material of the OLED illuminating device, the use of the aryl-substituted hydrazine in combination with the branch within the scope of the invention can effectively improve the exciton utilization and high fluorescence radiation. Efficiency, reducing efficiency roll-off at high current densities, reducing device voltage, and improving device current efficiency and lifetime.
  • the preparation method of the bisdimethylhydrazine-based compound of the invention is simple, has a broad market prospect, and is suitable for large-scale production.
  • the compound of the invention has good application effect in OLED light-emitting devices, and has good industrialization prospects.
  • Figure 1 is a schematic view showing the structure of a device to which the compound of the present invention is applied, wherein the components represented by the respective numerals are as follows:
  • FIG. 2 is a graph showing current efficiency versus temperature for an OLED device of the present invention.
  • FIG. 3 is a graph showing a leakage current test of a reverse voltage of a device fabricated in Device Example 1 and Device Comparative Example 1 of the present invention.
  • Elemental Analysis Structure (Molecular Formula C 46 H 35 NO): Theory C, 89.43; H, 5.71; N, 2.27; O, 2.59; Tests: C, 89.40; H, 5.69; N, 2.30; O, 2.61.
  • HPLC-MS The material had a molecular weight of 617.79 and a molecular weight of 618.65.
  • the synthesis step of the compound 24 is similar to the synthesis step of the compound 1, except that the compound A1 is replaced with the compound A2;
  • Elemental analysis structure (Molecular formula C 53 H 43 N): Theory C, 91.74; H, 6.25; N, 2.02; ⁇ / RTI> C, 91.71; H, 6.26; N, 2.04.
  • HPLC-MS The material had a molecular weight of 693.93 and a molecular weight of 694.28.
  • Elemental Analysis Structure (Molecular Formula C 56 H 42 N 2 ): Theory C, 90.53; H, 5.70; N, 3.77; Tests: C, 90.51; H, 5.71; N, 3.78.
  • HPLC-MS The material had a molecular weight of 742.97 and a molecular weight of 742.65.
  • the synthetic step of compound 46 is similar to the synthetic step of compound 1, except that compound A1 is replaced with compound A4;
  • Elemental analysis structure (Molecular formula C 61 H 49 N): Theory C, 92.04; H, 6.20; N, 1.76; Tests: C, 92.00; H, 6.21.; N, 1.79.
  • HPLC-MS The material had a molecular weight of 796.07 and a molecular weight of 795.67.
  • the synthetic step of compound 57 is similar to the synthetic step of compound 1, except that compound A1 is replaced with compound A5;
  • Elemental Analysis Structure (Molecular Formula C 52 H 39 NO): Theory C, 90.01; H, 5.67; N, 2.02; O, 2.31; Tests: C, 89.98; H, 5.66; N, 2.04; O, 2.33.
  • HPLC-MS The material had a molecular weight of 693.89 and a molecular weight of 694.23.
  • HPLC-MS The material had a molecular weight of 844.11 and a molecular weight of 843.09.
  • HPLC-MS The material had a molecular weight of 743.95 and a molecular weight of 743.65.
  • the synthetic step of compound 78 is similar to the synthetic step of compound 1, except that compound A1 is replaced with compound A8;
  • HPLC-MS The material had a molecular weight of 793.03 and a molecular weight of 792.86.
  • the synthesis procedure of Compound 80 is similar to the synthesis procedure of Compound 1, except that Compound A1 is replaced with Compound A9;
  • HPLC-MS The material had a molecular weight of 769.99 and a molecular weight of 769.78.
  • the synthetic step of the compound 95 is similar to the synthetic step of the compound 1, except that the compound A1 is replaced with the compound A10;
  • HPLC-MS The material had a molecular weight of 769.99 and a molecular weight of 769.
  • the synthetic step of the compound 101 is similar to the synthetic step of the compound 1, except that the compound A1 is replaced with the compound A11;
  • HPLC-MS The material had a molecular weight of 846.09 and a molecular weight of 845.17.
  • the synthetic step of the compound 115 is similar to the synthetic step of the compound 1, except that the compound A1 is replaced with the compound A12;
  • Elemental analysis structure (Molecular formula C 61 H 49 N): Theory C, 92.04; H, 6.20; N, 1.76; Tests: C, 91.99; H, 6.22; N, 1.79.
  • HPLC-MS The material had a molecular weight of 796.07 and a molecular weight of 795.26.
  • the synthetic step of the compound 125 is similar to the synthetic step of the compound 1, except that the compound A1 is replaced with the compound A13;
  • Elemental analysis structure (Molecular formula C 67 H 53 N): Theory C, 92.27; H, 6.13; N, 1.61; ⁇ / RTI> ⁇ /RTI> C, 92.23; H, 6.14; N, 1.64.
  • HPLC-MS The material had a molecular weight of 872.17 and a molecular weight of 871.06.
  • the synthetic step of compound 128 is similar to the synthetic step of compound 1, except that compound A1 is replaced with compound A14;
  • Elemental Analysis Structure (Molecular Formula C 64 H 48 N 2 ): Theory C, 90.96; H, 5.73; N, 3.31; ⁇ / RTI> C, 90.93; H, 5.73; N, 3.34.
  • HPLC-MS The material had a molecular weight of 845.10 and a molecular weight of 844.03.
  • the synthetic step of the compound 137 is similar to the synthetic step of the compound 1, except that the compound A1 is replaced with the compound A15;
  • Elemental analysis structure (Molecular formula C 58 H 44 N 2 ): Theory C, 90.59; H, 5.77; N, 3.64; ⁇ / RTI> C, 90.55; H, 5.78; N, 3.67.
  • HPLC-MS The material had a molecular weight of 769.00 and a molecular weight of 768.34.
  • the organic compound of the present invention is used in a light-emitting device and can be used as a material for a hole transport layer.
  • the compounds 1, 24, 28, 46, 57, 62, 65, 78, 80, 95, 101, 115, 125, 128, 137 prepared in the examples of the present invention were tested for thermal properties and HOMO levels, respectively. Table 1 shows.
  • the triplet energy level T1 is tested by Hitachi's F4600 fluorescence spectrometer.
  • the test conditions of the material are 2 ⁇ 10 -5 toluene solution;
  • the glass transition temperature Tg is by differential scanning calorimetry (DSC, Germany NETZSCH DSC204F1 differential scanning)
  • the calorimeter was measured at a heating rate of 10 ° C/min;
  • the thermogravimetric temperature Td was a temperature at which the weight loss was 1% in a nitrogen atmosphere, and was measured on a TGA-50H thermogravimetric analyzer of Shimadzu Corporation, Japan, and the flow rate of nitrogen was 20 mL/ Min;
  • the highest occupied molecular orbital HOMO level is tested by the ionization energy test system (IPS3) and tested as the atmospheric environment.
  • IPS3 ionization energy test system
  • the organic compounds of the present invention have different HOMO energy levels and can be applied to different functional layers.
  • the compounds based on bisdimethylhydrazine of the present invention have higher triplet energy levels and higher heat.
  • the stability makes the efficiency and lifetime of the fabricated OLED device containing the organic compound of the present invention improved.
  • the application effects of the OLED material synthesized by the present invention in a device will be described in detail below by means of Device Examples 1-15 and Device Comparative Example 1.
  • the device embodiments 2-15, the device comparative example 1 of the present invention have the same fabrication process as the device embodiment 1, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also maintained. Consistently, the difference between device embodiments 2-8 is the use of the materials of the present invention as hole transport layer applications, and device embodiments 9-15 are applications using the materials of the present invention as electron blocking layers.
  • Table 2 The performance test results of the devices obtained in the respective examples are shown in Table 2.
  • transparent glass is used as the transparent substrate layer 1.
  • ITO was coated thereon to a thickness of 150 nm, and as an ITO anode layer 2, it was washed, that is, sequentially washed with alkali, washed with pure water, then dried, and then subjected to ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. .
  • HAT-CN having a thickness of 10 nm was deposited as a hole injecting layer 3 by a vacuum evaporation apparatus.
  • the compound 1 prepared in Preparation Example 1 having a thickness of 60 nm was deposited as the hole transport layer 4.
  • TAPC having a thickness of 20 nm was evaporated as the electron blocking layer 5.
  • vacuum evaporation was performed on the electron blocking layer to obtain a light-emitting layer 6 having a thickness of 30 nm, which used 90 parts by weight of CBP as a host material and 10 parts by weight of Ir(ppy) 3 as a dopant material. The total amount of the host material and the dopant material is 100 parts by weight.
  • TPBI having a thickness of 40 nm was vacuum-deposited on the light-emitting layer as the electron transport layer 7.
  • lithium fluoride (LiF) having a thickness of 1 nm was vacuum-deposited on the electron transport layer as the electron injection layer 8.
  • aluminum (Al) having a thickness of 100 nm was vacuum-deposited on the electron injecting layer as the cathode layer 9.
  • the molecular structure of the relevant material is as follows:
  • Example 1 The procedure of the above Example 1 was repeated except that the hole transport layer 4 used NPB as a hole transporting material; the electron blocking layer 5 used the compound 80 prepared in Preparation Example 9 as an electron blocking material.
  • Example 1 The procedure of the above Example 1 was repeated except that the hole transport layer 4 used NPB as a hole transporting material; the electron blocking layer 5 used the compound 95 prepared in Preparation Example 10 as an electron blocking material.
  • Example 1 The procedure of the above Example 1 was repeated except that the hole transport layer 4 used NPB as a hole transporting material; the electron blocking layer 5 used the compound 101 prepared in Preparation Example 11 as an electron blocking material.
  • Example 1 The procedure of the above Example 1 was repeated except that the hole transport layer 4 used NPB as a hole transporting material; the electron blocking layer 5 used the compound 115 prepared in Preparation Example 12 as an electron blocking material.
  • Example 1 The procedure of the above Example 1 was repeated except that the hole transport layer 4 used NPB as a hole transporting material; the electron blocking layer 5 used the compound 125 prepared in Preparation Example 13 as an electron blocking material.
  • Example 1 The procedure of the above Example 1 was repeated except that the hole transport layer 4 used NPB as a hole transporting material; the electron blocking layer 5 used the compound 128 prepared in Preparation Example 14 as an electron blocking material.
  • Example 1 The procedure of the above Example 1 was repeated except that the hole transport layer 4 used NPB as a hole transporting material; the electron blocking layer 5 used the compound 137 prepared in Preparation Example 15 as an electron blocking material.
  • Table 2 shows the test results of current efficiency, color, and LT95 lifetime at 5000 nit brightness of the prepared OLED device.
  • the life test system is the OLED device life tester jointly researched by the owner of the invention and Shanghai University.
  • the OLED device of the embodiment of the present invention has a great improvement in both efficiency and lifetime, and in particular, the driving life of the device is greatly improved.
  • Table 3 shows the test results of the efficiency attenuation coefficient ⁇ of the prepared OLED device.
  • Example number Efficiency attenuation coefficient ⁇ Example number Efficiency attenuation coefficient ⁇
  • Example 1 0.22
  • Example 9 0.12
  • Example 2 0.23
  • Example 10 0.13
  • Example 3 0.19
  • Example 11 0.17
  • Example 4 0.21
  • Example 12 0.17
  • Example 5 0.18
  • Example 13 0.16
  • Example 6 0.15
  • Example 14 0.19
  • Example 7 0.18
  • Example 15 0.18
  • Example 8 0.16 Comparative example 1 0.40
  • Table 4 shows the results of current efficiency tests of the OLED devices of Examples 1, 5, 9, and 13 and Comparative Example 1 in the range of -10 to 80 °C.
  • Table 4 The results of Table 4 are plotted as Figure 2. As can be seen from Table 4 and FIG. 2, compared with Comparative Example 1, the OLED device of the embodiment of the present invention has not only low temperature efficiency but also a gradual increase in efficiency during temperature rise.
  • the devices fabricated in Device Example 1 and Device Comparative Example 1 of the present invention were subjected to a reverse voltage leakage current test, and the test data is shown in FIG.
  • FIG. 3 compared with the device fabricated in the device example 1 and the device comparative example 1 of the compound of the present invention, the leakage current is small and the current curve is stable. Therefore, the material of the present invention is applied to the device after fabrication. Long service life.

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Abstract

La présente invention concerne un composé à base de bis(diméthylfluorène), son procédé de préparation et son utilisation, se rapportant au domaine technique des semi-conducteurs. La structure du composé fourni par la présente invention est représentée par la formule générale (I). La présente invention concerne en outre l'utilisation dudit composé. Le composé selon la présente invention a une structure de bis(diméthylfluorène), présente une température de transition vitreuse élevée et une stabilité thermique moléculaire supérieure, possède des niveaux d'énergie HOMO et LUMO appropriés, et a un Eg élevé. L'optimisation de la structure des dispositifs permet d'obtenir une grande amélioration dans les performances photoélectriques des dispositifs OLED et de la durée de vie de ceux-ci.
PCT/CN2019/080634 2018-03-29 2019-03-29 Composé à base de bis(diméthylfluorène), son procédé de préparation et son utilisation WO2019185061A1 (fr)

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CN201810273506.8 2018-03-29
CN201910146222.7 2019-02-27
CN201910146222.7A CN110317184A (zh) 2018-03-29 2019-02-27 一种基于双二甲基芴的化合物、制备方法及其应用

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WO2022050592A1 (fr) * 2020-09-04 2022-03-10 엘티소재주식회사 Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2022108141A1 (fr) * 2020-11-18 2022-05-27 엘티소재주식회사 Composé et dispositif électroluminescent organique le comprenant
EP4089073A1 (fr) * 2021-05-12 2022-11-16 Samsung Display Co., Ltd. Dispositif luminescent et composé contenant de l'azote pour un dispositif de luminescence
WO2023182836A1 (fr) * 2022-03-23 2023-09-28 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
WO2023199832A1 (fr) 2022-04-12 2023-10-19 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2024117003A1 (fr) * 2022-12-01 2024-06-06 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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