TW200826333A - Organic opto-electronic devices - Google Patents

Abstract

The invention relates to an organic opto-electronic device comprising an organic layer between an anode and cathode, the organic layer comprising (a) 1-70 wt% of a dendritic compound, (b) 0-50 wt% of a compound for hole transport, (c) 0-50 wt% of a compound for electron transport and (d) 0-40 wt% of a compound for light emission, wherein the sum of elements (b), (c) and (d) is more than 20 wt% and the dendritic compound is inert. The invention also relates to organic opto-electronic single layer devices and a solution based process for making an organic opto-electronic device such as OLED's.

Description

200826333 IX. INSTRUCTIONS: The present invention relates to organic light-emitting devices, such as polymer light-emitting diodes, organic color displays, and in particular to a highly active organic light-emitting material based on a dendrimer.

L·iltr J Optoelectronic devices using organic materials have gradually met the requirements for a number of reasons. A variety of materials used to make such devices are relatively inexpensive, so organic photonic devices have the potential to outperform the cost advantages of inorganic devices. In addition, the unique properties of the organic 10 material, such as its flexibility, make the organic material suitable for use in special applications, such as on flexible substrates. Examples of the organic optoelectric device include, for example, an organic thin film transistor, an organic photovoltaic cell, an organic photodetector, and an organic light-emitting device such as an organic light-emitting device. The use of ◦LED' organic materials has a superior performance advantage over that of materials. For example, the emission wavelength of a 15 luminescent layer is easily adjusted using an appropriate dopant. The term "organic" is used here to include polymer materials and small molecular organic materials that can be used in the manufacture of organic optoelectronic devices. "Small molecule" means any organic material that is not a polymer, and "small molecule" may actually be quite large. In the case of a certain two, the small molecule includes a repeating unit. For example, the use of a long chain alkyl group as a 2 〇 substituent does not remove the molecule from the "small molecule" category. Small molecules can also be incorporated into the polymer, for example as a pendant group of the primary bond of the polymer, or as part of the main chain. Small molecules can also be used as a core part of the dendrimer, which consists of a series of chemical shells built on the core. The core of the dendrimer may be a fluorescent or fluorescent small molecule emitter and a group capable of transporting charge 5 200826333. When the LED is applied to a voltage across the device, the organic film emits light. OLEDs are used in applications such as flat panel displays, lighting, backlighting, etc., to become an interesting technology. The configuration of several 〇LED materials is described in U.S. Patent Nos. 5,844,363, 6, 303, 238 and 5, 707, 745, each of which is incorporated herein by reference. OLED devices are typically (but not infrequently) intended to illuminate via at least one of the electrodes, and one or more transparent electrodes can be used in the organic optoelectronic device. For example, a transparent electrode material such as indium tin oxide (IT〇) can be used as the bottom electrode. A transparent top electrode can also be used, such as disclosed in U.S. Patent Nos. 5,7,3,436 and 5,707,745, the entireties of each of For devices in which the sound image is illuminated only through the bottom electrode, the top electrode need not be transparent, but may comprise a thick reflective metal layer with high electrical conductivity. Similarly, for devices intended to emit light only through the top electrode, the bottom electrode can be opaque and/or reflective. When the electrode is not required to be transparent, a thicker layer is used to obtain better conductivity, and the use of a reflective electrode to reflect light toward the transparent electrode increases the amount of light emitted through the other electrode. It is also possible to manufacture a fully transparent device where both electrodes are transparent. Side-emitting OLEDs can also be fabricated, in which one or both of the electrodes can be opaque or reflective. 2 有机 Organic light-emitting diodes (OLEDs) based on low molecular weight materials and polymer materials are used in flat panel displays in advanced applications. After the initial reports of Tang and Van Slyke in 1987 and Burroughes et al. in 1990, rapid progress has been made in the optimization of device parameters such as efficiency and brightness. However, despite these successful developments, there is still a need for innovative oled with improved reliability and efficiency. In OLEDs, light is generated by recombination of electrons and holes by injecting an organic material as an active layer. Electrons and holes recombine in the active layer to produce a single or triple peak laser state at the center of the complex. The effective injection procedure requires that the molecule has a high-energy LUMO (lowest unoccupied molecular domain) and a low-energy HOMO (highest occupied molecular orbital domain). The organic active layer may be made of a conductive polymer such as poly-phenylene-vinylene (PPV), or may preferably be composed of "small" molecules, which have different functions, such as hole transport molecules, electron transport molecules, The wide band gap body is divided into 10, holes and exciton blocking molecules and effective fluorescent or phosphorescent molecules. The polymer layer can be prepared by spin coating, and the "small" molecules can be formed by thermal vacuum deposition or preferably by a solution-based method such as spin coating, using a doctor blade or ink jet printing. In order for the OLED to function properly, it is important that the organic layer be completely permeable, and that the film does not scatter incident light. When more than one small molecule is deposited using solution processing techniques such as spin coating, it is difficult to achieve this project. of. Therefore, OLEDs using small molecules having a specific function are usually prepared using a vapor deposition technique. The use of a hole-resisting layer in the multilayer OLED is performed to prevent the excess hole 20 from being lost to the cathode. In most cases, the hole blocking layer (HBL) also acts as a barrier to exciton migration, which can also act as an exciton blocking layer. The key characteristic of this layer is that its molecule has a lower HOMO energy than the molecule HOMO used to transport holes (positive charge), and a LUMO with a LUMO energy equal to or higher than the molecule used to transport electrons (negative charge). can. This point is indicated in the drawing (Fig. 1 7 200826333), which shows a schematic energy diagram of a high efficiency electroluminescent phosphor OLED. The hole system is transmitted along with the HOMO energy level transmission, and the electron system is transmitted along with the LUMO order. The excitons are represented by a luminescent pattern in the luminescent layer. US 2005/0017629 describes a multilayer OLED consisting of "small" molecules stacked into five separate layers. The OLED comprises a substrate (not shown), an anode (ITO material; (+)), a hole transport layer (HTL), an luminescent layer (EL), an electron transport layer (ETL), a metal (Cathode; (a)) and a protective layer (not shown). The hole h+ is transmitted from the anode to the luminescent layer, and the electron e· is transmitted from the cathode to the luminescent layer. In US 2005/0017629, the luminescent layer comprises a dendrimer having 10 镧 anions, and the dendrimer is active luminescent. If appropriate, OLED devices are manufactured in a standard high vacuum chamber of 1 (8 Torr). These types of OLEDs have reasonable performance, but are extremely expensive to manufacture, have low yields and can only be fabricated into small sizes. US 7,053,547 An example of a 〇 LED comprising a polymer, the 15 〇 LED is compared to a multilayer 〇 LED for fewer layers. The advantages of these categories of oled are that they can be simply fabricated by spin coating or inkjet technology, but are based on multiple layers of small molecules. The performance of the OLED is low. t OBJECT 3 The object of the present invention is to provide an improved OLed. The improved portion, such as 20, can be manufactured for improved performance, improved efficiency, or can be manufactured in a cost effective manner. In particular, the improvement can be good performance, high efficiency, and A combination of cost effective ways of preparation. It is also an object of the present invention to provide an OLED having high transparency such that the layer does not substantially scatter incident light or luminescence. The present invention comprises an at least one layer between an anode and a cathode. 200826333 Organic electro-optical device of the carrier layer, the at least one organic layer comprises a·1-70 wt% dendrimer b· 0-50 wt% hole transport compound c. 0-50 wt% electron transporting compound and 5 d·0.2-40 wt% of the luminescent compound, wherein the sum of the component parts b, c and d is more than 20 wt%, and at least a part of the dendrimer is inert. The weight percentage (wt%) is the final device, in other words, the weight percentage of the organic layer after the preparation step such as hardening, drying, etc. 10 The term inert is used herein to mean that the compound is not the main electron or hole transport. Factor, and the compound is not the main factor of luminescence. The dendrimer in the transition metal complex on which the transition metal is covalently bonded is typically not inert. It should also be noted that the term inert is not a chemical reaction. Thus, the inert dendrimer according to the invention is, for example, reactive with its species in the compound, such as may participate in subsequent hardening reactions to form a network system. The term at least partially dendrimer is inert means the invention Covers the presence of active dendrimers (ie, involved in hole transport or electron transport and/or luminescence) and inert dendrimers. 20 If present The components a, b, c and d are respectively composed of one or more compounds. In the main embodiment, the components b, c and d, that is, the weight transfer system of the hole transporting compound, the electron transporting compound and the luminescent compound are larger than 20 wt%, based on the total weight of the organic layer. Typically, the weights of the constituent parts b, c and d are less than 80%, preferably less than 70% such as less than 5%. 9 200826333 a, b, c and d Other components may also be present in the organic layer, such as organic fillers or inorganic fillers, solvents, crosslinking agents, and various additives known in the art. The apparatus according to the first aspect of the present invention typically comprises several layers, each negatively 5 Responsible for one or more functions such as transmission, electronic transmission, illumination, and blocking of holes. Preferably, at least one of the layers contains more than one of these functions, thus reducing the number of layers required. In another aspect, the invention comprises an organic optoelectric device comprising at least one organic layer between an anode and a cathode, the at least one organic layer 10 comprising a. 1-40 wt% dendrimer b. 10-50 Wt% hole transport compound c. 10-50 wt% electron transport compound and d. 0.2-40 wt% luminescent compound. An advantage of the apparatus of the present invention is that the apparatus has a simple structure containing (easy to access) small molecules, providing electron transport, hole transport, and illuminating functions. The manufacture of this device is also relatively easy compared to other multilayer systems. An advantage of the OLED of the present invention is that the electron transport molecules and the hole transport molecules are present in one layer and in the same layer, thereby forming an extremely simple structured 20 OLED. Preferably, the OLED of the present invention comprises an organic layer between the anode and the cathode, the organic layer comprising a. 5-40 wt% dendrimer b. 20-40 wt% hole transport compound 10 200826333 c. 20-40 wt% Electron transport compound and d. 1-10 wt% luminescent compound. A further embodiment of the present invention is an organic optoelectric device comprising an organic layer between an anode and a cathode, the organic layer comprising a. 5-40 wt% highly branched molecule b· 20-40 wt% hole transport compound c. 20-40 wt% electron transporting compound and d. 1_10 wt% luminescent compound. Another embodiment of the present invention is an organic optoelectronic device comprising an organic layer between an anode and a cathode, the organic layer comprising a. 5-40 wt% highly branched molecules b. 20-40 wt% holes Transfer compound c. 20-40 wt% electron transport compound and d. l_10 wt% luminescent compound, 15 wherein the south branch molecule has a structural formula according to the following formula

among them

, Η, (C6-C1()) aryl or (CrC2〇)(cyclo)alkyl; B = (C2-C24), optionally substituted aryl or (cyclo)alkyl aliphatic 11 200826333 II R, R, R3, r4, r5 and r6 are each the same or different and are H, (CVCu)) aryl or (crC8) (cyclo) fluorenyl and each η is i_4, respectively. In general, the dendrimers utilized in accordance with the present invention may be chemically modified by 5 as needed. In particular, the hydrazine H functional group can be modified to be an ester, an ether, a decylamine, an amine, a thiol, a polyethylene oxide, a polypropylene oxide or a mixture thereof. The term mixture means that the modification of each modified hydrazine H group need not be the same, and for individual hydrazine H groups, may include a mixture of functional groups, such as a hydrazine H group modified to an amine functional group, the alkyl moiety is transesterified or etherically bonded. And the bond to the dendrimer. Other examples of modification 10 include reacting to an end cap group, such as an organic acid moiety (such as a guanidinium benzoate fatty acid), attached to a Cl_C24 (cyclo)alkyl moiety, a Ci_C24 (cyclo)aryl moiety, a polyepoxydene or a poly The propylene-acrylic moiety, containing other functional moiety, such as an amine-containing, phospho-, thio-, thiol-containing or polymer (such as itself or adjacent dendrimer or another polymeric component of the device). It has been found that the 15 modification of the 0H end group is particularly preferred for highly branched compounds and is preferred for highly branched polyester decylamines. Another embodiment of the present invention is an organic optoelectric device comprising an organic layer between an anode and a cathode, the organic layer comprising a·M〇wt°/0 dendrimer 20 b·10_5〇wt% hole transmission a compound c· 10-50 wt% electron transporting compound and d·0.2-40 wt°/〇 luminescent compound, wherein the device comprises a hole blocking component between the cathode and the organic layer, which is composed of the following molecules These molecules have a lower HOMO energy than the molecule used to transport the gemini 12 200826333 and a LUMO having a LUMO similar or higher than the molecule used to transport the negative charge. These OLEDs form a highly transparent film by adding appropriate dendrimers after evaporation to remove the solvent, by preventing phase separation and/or preventing crystallization of different molecules of 5 in the film, such OLEDs having a combination of low molecular weight molecules and having Special features such as hole transmission, electron transmission, and fluorescent or phosphorescent. BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a schematic energy diagram of a high efficiency electroluminescent phosphor OLED. Figure 2 is an example of the current density and light intensity of the 〇LED relative to the applied voltage and efficiency relative to the applied voltage. C. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The dendrimer is a three-dimensional space-synthesizing molecule that combines repeated branching sequences to form a unique architecture. Examples of dendrimers are dendrimers and highly branched polymers and highly branched molecules. Dendrimers are highly branched or highly branched polymers with perfect or near perfect structural symmetry, density gradients showing intramolecular minimums and well defined molecular weights and number of end groups. The dendrimer system is prepared by core synthesis in shell synthesis or from generation to generation. As a result, the product is expensive, and the options for fine-tuning the properties of the 20 village materials are limited. The synthetic procedure developed for dendrimer preparation allows complete control of critical molecular design parameters such as size, shape, surface/internal chemical structure, and surface topography. Synthetic technology provides an effective way to form dendritic structures, including ray divergence strategies (Tonlalia and colleagues), convergent growth strategies (Frechet and colleagues), and self-assembly strategies 13 200826333 (Zimmerman and colleagues) 〇 / highly branched polymers are dendritic A special example of a compound, a highly branched polymer has a more imperfect branching structure than a scorpion. Highly branched polymers can be prepared in a more unstructured manner than dendrimers, resulting in a more efficient high-elasticity synthesis with a high degree of improved ability to fine tune material properties. The combination of these characteristics forms an environment within the highly branched molecules that assists in the development and manufacture of unique economical and functional nanoscale materials that form the basis of novel nanoscale devices and novel technologies. Examples of suitable highly branched molecules and synthesis can be found, for example, in WO 99/16810, WO 00/58388, and WO 10 01/62865, each of which is incorporated herein in its entirety by reference. Preferred highly branched molecules are highly branched polyester guanamines because the highly branched polyester guanamine provides molecules with highly polar segments, which may include non-polar segments or low polarity segments for highly adjustable nature. In particular, the highly branched polyester guanamine polymer provides an excellent carrier for 15 parts of each of the dispersed solutions, thus avoiding premature phase transitions during the manufacture of photovoltaic devices. An example of a polymer of a suitably highly branched molecule is a polymer 20 having at least two groups according to formula (I).

γ ^

OH _ Η 14 200826333 Η, (C6-C1()) aryl or (CrC2〇)(cyclo)alkyl; b = (c2-c24), optionally substituted aryl or (cyclo)alkyl Aliphatic diyl; R1, R2, R3, R4, R5 and R6 are each the same or different and are Η, 5 (C6-C1()) aryl or (CrC8)(cyclo)alkyl and each η respectively It is 1-4. At least one of the oxime groups can be modified, if desired, to an ester, ether, guanamine, amine, thiol, polyethylene oxide, polypropylene oxide or mixtures thereof, as described elsewhere herein. Another example of a suitable dendrimer is a highly branched polymer containing at least two groups according to formula 10 (II):

Ο 0 1 1!

I where R4 9.

, hydrazine, (CrQoX ring) alkyl, or (C6-C10) aryl; 15 B = (C2-C24), optionally substituted aryl or (cyclo)alkyl aliphatic diyl, and R1 R2, R3, R4, R5 and R6 are each the same or different and are respectively fluorene, (C6-C1())aryl or (CrC8)(cyclo)alkyl. Yet another example is a 20 polymer containing a hydroxyalkylguanamine group according to formula (III): 15 200826333 A.".: ΟI! iK ─ ─ ‘‘‘ Μ _ ! _ I Η _ where:

Η, (CrC2())(cyclo)alkyl, or (C6_C1Q) aryl# I.-y, T-M-niniwr Death foot: __聊·yw—诵T u 5 ¥ RH or OH, B = (C2-C24), an optionally substituted aryl or (cyclo)alkyl aliphatic diyl, Ο 0 R1 f II II |

I i, IY ir h X2 = H or X1 and ίο R1, R2, R3, R4, R5 and R6 are each the same or different and are Η, (C6-C1()) aryl or (CVC8) (ring Alkyl or CH2-OX2. In formulae (II) and (III), the R groups may together or together with adjacent carbon atoms form part of a cycloalkyl group. Another example of a suitable dendrimer is a polymer containing a hydroxyalkane 15 amide group according to formula (IV): 16 200826333 Ο

II

Squat

m where: 5

(CVGo) aryl

H, (Cl_c2〇) (cyclo-m-group, or OH, B-di(C2-C24), depending on the need of the two groups,

10 r3==h or ((VCl°) aryl or (LQ-based and R6=H or (CVCl.) aryl or (Ci-pyrylene). The weight average molecular weight of the I compound according to this month is usually _ to 5 〇〇, 〇 00 g / Mo * and fortunately the father is 1 gram / Moer to 25, _ gram, Moer. In this embodiment of the heart of the car, the dendrimer has The glass 15 conversion temperature (at least (10). The Tg of c. The dendritic sigma is used as a dispersing sword. Preferably, the dendrimer is compounded. 200826333 contains at least a southern branching molecule according to formula (I). , a highly branched polymer of two groups or

m m

^钱卜M

_ H 5 BH, (C6_Cl°) aryl or (CrC2.) (cyclo)alkyl; (c2 c24) 'optionally substituted aryl or (cyclo)alkylidene aliphatic diyl; RRR, R5 and Each of R6 is the same or different and is H, (6 1G) aryl or (CrC8) (ring) alkyl and each η is 1-4, respectively. Preferably at least one of the 10 oxime groups can be modified as desired, ether, amine, amine, thiol, polyepoxy, polyepoxy or wei compound, as elsewhere herein. Said. Based on the total weight of the solution used to prepare the organic layer, or based on the total weight of the final organic layer (ie, after the hardening of Ren Yao and/or the evaporation of the optional solvent), the quasi-tree compound inequality can be A very wide range of variation from 1 wt% to about 70 wt%. Typically, the dendrimer, when used alone as a dispersing agent, has a concentration of from 1 to 40 wt% 'such as from 2 to 30 wt% and especially from 5 to 20 wt%. In a preferred embodiment of the invention, the dendrimer is crosslinked after application. The mobility of the organic layer is reduced by cross-linking, resulting in a 20-long life of the device. Further, when the next organic layer is applied from a solvent, the crosslinked organic layer 18 200826333 does not dehydrate again. Limiting the mixing of the two organic layers results in improved device performance, predictability, and/or durability. The combination can be achieved by adding a suitable cross-linking agent. Appropriate chemistry can be used in the coatings or coatings industry where a cross-linking system can be used to achieve a combination of long enough storage life and sufficiently good reactive properties. After application, the organic layer is accelerated, e.g., by heating. It is possible to add a catalyst to further increase the reactivity. Examples are a combination of an alcohol and an isocyanate or a blocked isocyanate, a combination of an amine and a cyclic carbonate, a combination of a slow acid and an epoxide, an ethyl acetate and a (meth) A combination of acrylates. In a preferred embodiment 10, 5-20 wt% of the crosslinker is added to the formulation and is present in the hardening stage in the apparatus according to the present invention. In the preferred embodiment, the device or the solution from which the organic layer is prepared comprises a hardenable compound. In one embodiment, the hardenable compound is a separate resin system comprising a crosslinking agent which can bind or not incorporate a dendrimer during hardening. In another embodiment, at least a portion of the dendrimer can be hardened by incorporating a suitable reactive group and the reactive group is incorporated into the interior of the network during hardening. Thus the dendrimer contains at least one reactive group. The dendrimer can also be used as a cross-linking agent, which is particularly preferred because it has more than one function through the dendrimer, which reduces the number of components in the overall system by 20 mesh. Another way of crosslinking the dendrimer is to effect the reactive moiety on the dendrimer and then harden by Uv latent catalyst by irradiation of the group, anion or cation formed. An example of such a reactive group is acrylate, methyl acrylate, itaconate, 19 200826333 propyl groups for the group hardening system. The combination of an epoxide or a cyclic oxime with an alcohol is a suitable example of a cationic curing system. Examples of suitable _ sub-curing systems are combinations of liquid crystal vinegar and alcohols, combinations of epoxides and ketones, and combinations of acetoacetate vinegar and (meth) acrylates. Examples of electron-transporting compounds can be found in U.S. Patent Nos. 5,554,45, issued toU.S. Patent No. 5,061,569, the entire disclosure of which is incorporated herein by reference. Special cases are a-amine and alum, which are described in the book: "Organic Photoreceptors for Imaging Systems", Appendix 3, by paul Μ·Β〇_. and 10

David S. Weiss ’ Marc Dekker, Inc., New York, 1998. Examples of electron transporting compounds are azoles, diazoles, triazoles, guanidine, benzoxazoles, benzoxazoles and phenanthroline, each of which may be substituted as needed. Particularly preferred substituents are aryl groups, especially phenyl and oxadiazoles, especially those substituted by aryl groups. Specific examples of electron transport compounds are ruthenium 15 phenyl-porphyrin aluminum (A1Q3), 3-phenyl-4-(1-naphthyl)-5-phenyl-1,2,4-triazole and 2,9- Monomethyl-4,7-diphenyl-phenanthrene. An example of a 1 π-gap host compound is 4,4,_贰 (tattoo-9-yl)biphenyl, which is referred to as CBP and (4,4',4"·parameter (吟嗤_9_yl)triphenylamine, Called TCTA, disclosed in Ikai et al. (Appl. Phys. Lett., 79 no. 2, 2001, 156) 20 and diarylamines such as -4-(N_3_methylphenyl-N-phenyl) Aniline, referred to as MTDATA. An example of a hole blocking molecule and an exciton blocking molecule is BAlq (贰(2-methyl-8-porphyrinate) 4-phenylphenolic acid 4-biphenylalkoxy aluminum (in) ), BCP (bathocuproine) and TPBI (1,3,5-paran (2-N-phenylbenzimidazole 20 200826333) benzene) such as Adamovich et al. (Organic Electronics 4 (2003) Description of 77-87) An example of an effective fluorescent molecule or phosphorescent molecule is 4-(dicyanomethylidene) 2 methyl-6-(p-dimethylaminophenylidene)·4Η_σ辰(DCM) or ginseng (2-phenyl-5-pyridine) 。 (Η). The luminescent layer can emit monochromatic light (such as one of red, green or blue light), or the luminescent layer can emit multi-colored light, such as White light or light consisting of several separate wavelengths. This multi-color luminescence can be emitted by fluorescent molecules or light-filling molecules. Light of a wavelength is achieved, or by using a mixture of fluorescent molecules or phosphorescent molecules. The material may be present in the form of small molecules, or the repeating unit of the filament may be provided, especially in the polymer backbone. The repeating unit is provided as a substituent pendant from the polymer backbone. The OLED of the present invention may contain a polymeric material as long as the transparency of the coffee is not interfered by the presence of one or more polymers. The material can be bipolar, in other words, can transmit holes and electrons. Suitable bipolar materials preferably contain at least two ten-seat units (invasive

Mater·Chem·, 2〇〇〇, 1〇, 125). The bipolar host material can be a material that includes a hole transport segment and electrons. An example of such a material is a polymer comprising a hole transport segment and a 2-inch electron transport segment, as disclosed in WO 〇〇/55927, wherein the hole: the transport system is repeated by a triarylamine located inside the polymer backbone The transmission by the unit is provided by a conjugated polyfluorene chain inside the polymer backbone. In addition, the nature of the electron transport and electron transport can be provided by repeating units that are adjacent to the main chain of the light or non-common vehicle. The homopolymers and copolymers include polyaromatic hydrocarbons such as polyfluorenes, polysulfoniums, polybenzazoles or polyphenylenes which may be substituted as desired, as previously described for the hole transport layer. 5 典型 is typically fabricated on a transparent substrate that is primarily coated with a hole injection electrode. Typically, antimony tin oxide (IT〇) is used as a hole injecting electrode to form a transparent conductive anode layer. The layer or layers of organic layer are then coated by thermal evaporation (in the case of small organic dye molecules), by spin coating in the case of a polymer, or preferably by ink jet printing techniques. In addition to the luminescent material active layer itself, other 10 organic layers can be used to enhance the injection and transport of electrons and/or holes. The hole blocking layer and the metal cathode (such as magnesium-silver alloy, lithium-aluminum or calcium) can be deposited on top of the multilayer structure using a high vacuum technique. These metals are selected with their low work function to provide efficient electron injection. The organic layer has a total thickness of about 100 nm. The two electrodes (ΙΤΟ anode and metal cathode) increased the total thickness of the device by approximately 15 200 nm. Therefore, most of the total thickness (and weight) of the OLED structure is determined by the substrate. OLEDs The OLED of the present invention is transparent in the visible wavelength range. Example 20 22 200826333 Abbreviation chemical name supplier Pedot:PSS or Baytron P poly(3,4-extended ethyl 'monooxyporphin), poly(styrenesulfonic acid) HC-Stark (HC -Starck) TPD N,N'-diphenyl-NH(3-methyl-phenyl)-[U'_biphenyl H,4'-diamine aliquot (Aldrich) tBu-PBD 2-(4 -biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazolidinide Ir(tpy)3 gins-tolylpyridinium (III) US dye source (American Dye Source) ΤΡΒΙ (1,3,5-para (2-N-phenylbenzoquinone _ °) phenyl) 杉惜:Sensient Imaging Technologies GmbH OLED manufacturing system for OLED manufacturing By spin coating a solution containing a hole transporting molecule, an electron transporting component, a luminescent agent (fluorescent or phosphorescent molecule), and a highly branched compound as a film forming additive on a pre-formed ITO glass plate, the glass plate is just The organic layer has been thoroughly cleaned prior to deposition using chemical methods and UV-ozone methods. In some cases, a hole injection layer is deposited prior to deposition of the luminescent layer, typically an aqueous solution of Beso-P (available from HC-Stark). 10 The thickness of the luminescent layer is usually about 80 nm, and the thickness of PEDOT: PSS is about 100 nm. In some cases, additional holes and exciton blocking layers may be added prior to deposition of the metal electrode. Such barrier layers are prepared by hot evaporation of the appropriate molecules to a typical thickness of 20-40 nm under high vacuum (less than 1 x 16 mbar). The metal counter electrode is used by thermal vacuum evaporation (basic pressure less than lxlO-6 mbar). In the larger part, the metal counter electrode consists of 5 nanometer 钡 and 80 nanometer silver double layer. The preparation of the OLED device was carried out in an inert atmosphere glove box (<〇" ppm 02 and 40) to reduce the effects of air and moisture. The current density and brightness were measured using a Keithley 2400 source meter and a light diode that was consumed by a snorkeling 6485 picoampere meter using Minolta 23 200826333 LS100 calibration photocurrent measurement. An Avantes brightness spectrometer was used to determine the EL spectrum. The device is characterized by an inert atmosphere. In a typical experiment, 300 mg of Hybrane PB2295 (from DSM Haibun BV) mixed 300 mg hole transport molecule N, N'-diphenyl 5 _N, N' 贰 (3-methyl -phenyl)_[1,1'-biphenyl]_4,4'-diamine (TPD), 350 mg electron transport molecule 2-(4-biphenyl)-5-(4-tert-butylbenzene Base)-1,3,4-oxadiazole (tBu-PBD) and 50 mg of phosphorescent ginseng-tolylpyridinium(III) (Ir(tpy)3). This mixture was dissolved in 3 ml of toluene to obtain a completely clear solution. The solvent was filtered through a 0.45 μm filter and spin-coated at 2000 rpm on a patterned ITO-coated substrate having a thickness of 1 Å Nai 10 m to obtain a luminescent layer of about 80 nm thick. When the thus obtained two-layer film was transferred to a high vacuum, vacuum was applied to a substrate pressure < lxl (T6 mbar, prepared by evaporation of the molecule TPBI (1,3,5-g (2)phenylbenzimidazolyl). The hole barrier layer is 20 nm thick. The preparation of the device is carried out by sequential vacuum evaporation of 5 nm 钡 and 8 〇 nano silver by thermal vacuum evaporation. The performance of the 15 LED device is typically obtained by the current density and brightness (light intensity). Relative to the applied voltage, the efficiency is directly derived from the voltage. The results obtained by the above device are shown in Figure 2, current density (solid square) and party (open circle) relative to the applied voltage ( The left side and the efficiency relative to the applied voltage (right) are shown for the aforementioned OLED device. 20 The OLED of the present invention achieves a brightness value of less than 12 volts of 100 s/m2 and a current efficiency of more than 1 s/amp. The preferred embodiment of the present invention will be described with reference to the accompanying drawings, and it is to be understood that the present invention is not limited to the five-disc embodiment, and that the skilled artisan may not deviate from the scope of the invention as defined by the accompanying patent. And Jing Zhao and made it in 24 200826333 A number of changes and modifications. L diagram simple description 3 Figure 1 is a schematic energy diagram of a high-efficiency electroluminescent phosphor OLED. Figure 2 is an example of the current density and light intensity of the OLED relative to the voltage applied by 5 Efficiency relative to the applied voltage. [Main component symbol description] (none) 25

Claims (1)

200826333 X. Patent Application Range: 1. An organic optoelectronic device comprising at least one organic layer between an anode and a cathode, the at least one organic layer comprising a. 1-70 wt% dendrimer 5 b. 0-50 wt % hole transport compound c. 0-50 wt% electron transport compound and d. 0.2-40 wt% luminescent compound, wherein the sum of elements b, c and d is greater than 20 wt%, and at least a part of the dendrimer is Inert, in other words, does not form part of the component b, 10 c or d. 2. The device of claim 1, wherein the organic layer comprises a. 1-40 wt% dendrimer b. 10-50 wt% hole transport compound c. 10_50 wt% electron transport compound and 15 d. 0.2 -40 wt% luminescent compound; preferably the organic layer comprises a. 5-40 wt% dendrimer b · 20-40 wt% hole transport compound c · 20-40 wt% electron transport compound and 20 d. 10 wt% luminescent compound. 3. The device of any one of claims 1 or 2 wherein the dendrimer is a highly branched polymer or molecule containing at least two groups according to formula (I), 26 200826333 R4 r6 /lx 1 γ ^ • 十 COH Un I RS H , H, (C6_C1()) aryl or (qC^oX ring) alkyl; B = (CVC24), optionally substituted aryl or Ring-based aliphatic dibasic group; R, R, R, R, R5 and r6 are each the same or different and are Η, (CVC1()) aryl or (crC8) (cyclo)alkyl and each n At least one of the 1-4 groups, respectively, may be modified to an ester, an ether, a guanamine, an amine, a thiol, a polyethylene oxide, a polypropylene oxide, or a mixture thereof. 4. The device of claim 3, wherein the dendrimer is a highly branched polymer or molecule comprising at least two groups according to formula (11): m γ , H, (Ci-C2〇)(^)alkyl, or (C6-Ci〇) 27 15 200826333 aryl; B = (c2-c24), optionally substituted aryl or (cyclo)alkyl The aliphatic diyl group, and R1, R2, R3, R4, R5 and R6 are each the same or different and 5 is fluorene, (C6-C1()) aryl or (CrC8)(cyclo)alkyl, OH group At least one of the groups may be modified to an ester, an ether, a guanamine, an amine, a thiol, a polyethylene oxide, a polypropylene oxide or a mixture thereof as needed. 5. The apparatus of any one of claims 1-4, wherein the dendrimer has a Tg of at least 100 ° C, preferably the dendrimer has a Tg of 10 to 130 ° C. 6. The device of any one of claims 1-5, wherein the device comprises a hole transport barrier between the cathode and the organic layer comprising highly branched molecules. 7. The device of any one of claims 1 to 6 comprising a hardenable compound, preferably the hardenable compound is a separate resin system, or at least one of the dendrimers is hardenable, More preferably, the dendrimer comprises at least one reactive group. 8. The device of any one of claims 1 to 7, wherein the device is an organic light-emitting device. 20 9. An organic optoelectric device comprising an organic layer between an anode and a cathode, the organic layer comprising a. 1-40 wt% dendrimer b. 10-50 wt% hole transport compound c. 10-50 Wt% electron transport compound and 28 200826333 d. 0.2-40 wt% luminescent compound, wherein the dendrimer is a highly branched polymer or molecule containing at least two groups according to formula (I), Y R2 Η , Η, (C6-C1(}) aryl or (CrC2〇)(cyclo)alkyl; B = (C2-C24), optionally substituted aryl or (cyclo)alkyl aliphatic diyl; R1, R2, R3, R4, R5 and R6 are each the same or different and are Η, (C6-C1()) aryl or (CrC8)(cyclo)alkyl and each η is 1_4, \10 ΟΗ At least one of the groups may be modified to an ester, an ether, a guanamine 'amine, a thiol, a polyethylene oxide, a polypropylene oxide or a mixture thereof as needed. 10. A device according to claim 9 Wherein the dendrimer is a highly branched polymer or molecule comprising at least two groups according to formula (II): 29 200826333 Η ring)alkyl, or (c6-c10) aryl; b = (c2-c24), optionally substituted aryl or (cyclo)alkyl aliphatic diyl, and 5 R1, R2, R3, R4, R5 and R6 are each the same or different and are fluorene, (C6-C1())aryl or (CrC8)(cyclo)alkyl, at least one of which may be modified to an ester as needed , ether, guanamine, amine, thiol, polyethylene oxide, polypropylene oxide or mixtures thereof. 11. The device of claim 9 or 10, wherein the organic layer comprises 10 a. 5-40 wt% dendrimer b. 20-40 wt% hole transport compound c. 20-40 wt% electron transport compound and d. 1-10 wt% luminescent compound. 12. The device of any one of claims 9-11, wherein the dendrimer compound has a Tg of at least 100 ° C, preferably the dendrimer has a Tg of at least 130 °C. 13. The device of any one of claims 9-12, wherein there is a compound comprising a hole transporting property and an electron transporting property in a molecule, the properties being a conjugated polymer backbone or non- The conjugated polymerization 20 is provided by the repeating unit of the main chain. 14. The device of any one of claims 9-13, wherein the device comprises a hole 30 200826333 transport barrier between the cathode and the organic layer comprising the highly branched molecules. The device of claim 14, wherein the hole transport barrier layer comprises a biphenyl group selected from the group consisting of BAlq (贰(2-methyl-8-porphyrinate) 4_phenylphenolic acid 4·biphenyl a group consisting of oxyspor (10)), BCP (bath〇cupr〇ine) 5 and TPBI (1,3,5-paran (2_N-phenylbenzimidazolyl)benzene) Compound. The device of any one of claims 9 to 15, comprising a hardenable compound, preferably the hardenable compound is a separate resin system, or at least one of the dendrimers is hardenable, preferably The dendrimer 10 comprises at least one reactive group. The device of any one of claims 9 to 16, wherein the device is an electroluminescent device, preferably the electroluminescent device is an organic light-emitting device. 18. A method of making an optoelectronic device, the method using a solution based method 15, preferably using a solution to spin coating a substrate. 19. The method of claim 18, wherein the solution comprises a hardenable compound, and the method comprises the steps of providing the solution to at least a portion of a substrate, followed by at least partially hardening the hardenable compound, and The sequence may be repeated as needed to provide a multilayer device. Preferably, the hardenable compound comprises a dendrimer. 20. The method of claim 19, wherein the hardenable compound comprises a highly branched polymer or molecule comprising at least two groups according to formula (I), 31 200826333 OH r4 m jl\\ y as . 十c-Bu C — OH , * Λ丨RS h , η, (C6-C10) aryl or (Cl_c2()) (ring) alkyl; 5 B = (C2_C: 24) an optionally substituted aryl or (cyclo)alkylidene aliphatic diyl; R1, R2, R3, R4, R5 and R6 are each the same or different and are Η, (CVC1()) aryl Or a (Q-C8)(cyclo)alkyl group and each n is 1-4, respectively, and at least one of the 〇H groups may be modified to an ester, an ether, a guanamine, an amine, a thiol, a poly ring, if necessary. Oxyethane, polypropylene oxide or a mixture thereof. 21. The use of a dendrimer as a dispersant in a method of making an optoelectronic device. 22. If the application of the application (10) is applied, the towel-transformed compound comprises a highly branched polymer or 〇 含有 containing at least two groups according to formula (1) _ OH γ m Η 32 200826333 r4 r6 , h, (cvc1())aryl or (crc2〇)(cyclo)alkyl; B = (C2-C24), optionally substituted aryl or (cyclo)alkyl aliphatic diyl; 5 R1 , R2, R3, R4, R5 and R6 are each the same or different and are Η, (C6-C1()) aryl or (CVC8) (cyclo)alkyl and each η is 1-4 At least one of the oxime groups can be modified to an ester, an ether, a guanamine, an amine, a thiol, a polyethylene oxide, a polypropylene oxide, or a mixture thereof as needed. 10 23 - A composition suitable for use in a method for producing an organic light-emitting diode (OLED), comprising a solvent and any one of the components of claims 1 to 17. An apparatus comprising an electroluminescent device according to any one of claims 1 to 17, preferably the electroluminescent device is an OLED. 33