Organic light-emitting devices and display devices
By adjusting the molecular stacking angle of the light extraction layer and using a light extraction layer material with a specific structure, the problem of poor light extraction performance in OLED devices was solved, achieving efficient light extraction in different wavelength ranges and improving luminous efficiency.
Patent Information
- Application Number
- CN202310181749.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-02-21
- Publication Date
- 2026-01-30
- Estimated Expiration
- 2043-02-21
AI Technical Summary
The light extraction layer material of existing OLED devices has a low refractive index, resulting in poor light extraction performance. Furthermore, there are significant deviations between the wavelength regions of blue, green, and red light, making it impossible to achieve high light extraction efficiency simultaneously.
By controlling the molecular stacking pattern of the light extraction layer, the angle between the direction of light emitted perpendicular to the substrate and the main plane of the first material molecules can be varied between 30° and 90°. The refractive index of the light extraction layer can be adjusted to be within the range of 1.7-2.2. By using light extraction layer materials with a bis(thiophene) or bis(furan) structure, the twist angle of the molecular structure can be increased to improve the light extraction efficiency.
It improves the light extraction efficiency of OLED devices, reduces internal light loss, enhances luminous efficiency, and achieves high light extraction rates in blue, green, and red light devices.
Smart Images

Figure CN116322135B_ABST
Abstract
Description
TECHNICAL FIELD
[0001] The present disclosure relates to the technical field of display, and in particular to an organic light-emitting device and a display device. BACKGROUND
[0002] Organic light-emitting diodes (OLED) refers to the phenomenon that organic electroluminescent material emits light under electric excitation. Compared with traditional LCD display, OLED, as the latest display technology, has the advantages of self-luminescence, wide viewing angle, low power consumption, full black display, full colorization, etc., and has wide commercial application potential.
[0003] The OLED device structure usually includes a substrate, a first electrode layer, an organic layer, a second electrode layer, and a light extraction layer outside the electrode surface. At present, the light extraction effect of the light extraction layer cannot meet the user's demand.
[0004] The above information disclosed in the background section is only used to strengthen the understanding of the background of the present disclosure, and therefore it can include information that does not constitute prior art known to those of ordinary skill in the art. SUMMARY
[0005] The purpose of the present disclosure is to provide an organic electroluminescent device that can effectively improve the light extraction efficiency of the organic light-emitting device.
[0006] To achieve the above-mentioned purpose of the application, the present disclosure adopts the following technical solutions:
[0007] According to a first aspect of the present disclosure, an organic light-emitting device is provided, comprising a substrate, a first electrode layer, a light-emitting functional layer, a second electrode layer and a light extraction layer arranged on one side of the substrate, the second electrode layer being located on the side of the first electrode layer away from the substrate, the light-emitting functional layer being located between the first electrode layer and the second electrode layer, and the light extraction layer being located on the side of the second electrode layer away from the first electrode layer.
[0008] The light extraction layer comprises first material molecules and second material molecules, the percentage of the number of first material molecules in the total number of molecules in the light extraction layer is a, and the percentage of the number of second material molecules in the total number of molecules in the light extraction layer is b, a > b, a > 50%.
[0009] The included angle between the main plane of the first material molecules and the light extraction direction of the organic light-emitting device perpendicular to the substrate is 30°-90°.
[0010] According to a second aspect of the present disclosure, a display device is provided, comprising the organic light-emitting device according to the first aspect.
[0011] The organic light emitting device provided by the present disclosure changes the angle between the direction of light emitted perpendicularly to the substrate and the main plane of the first material molecules by controlling the material molecular packing mode of the light extraction layer, thereby changing the variation of the refractive index of the light extraction layer. When the angle value gradually increases from 30° to 90°, the refractive index shows a gradually increasing trend, so that the refractive index of the light extraction layer changes within a certain range. In this way, the light extraction efficiency of the organic light emitting device can be effectively improved, thereby improving the light emitting efficiency of the device. BRIEF DESCRIPTION OF DRAWINGS
[0012] The above and other features and advantages of the present disclosure will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
[0013] Figure 1 is a schematic diagram of the structure of an organic light emitting device in an exemplary embodiment of the present disclosure;
[0014] Figure 2 is a schematic diagram of the material molecular packing in the light extraction layer in an exemplary embodiment of the present disclosure.
[0015] The main element reference signs in the drawings are explained as follows:
[0016] 100, first electrode layer; 200, second electrode layer; 300, light emitting functional layer; 310, hole injection layer; 321, hole transport layer; 322, electron blocking layer; 330, light emitting layer; 340, hole blocking layer; 350, electron transport layer; 360, electron injection layer; 400, light extraction layer. DETAILED DESCRIPTION
[0017] Example embodiments now will be described more fully hereinafter with reference to the accompanying drawings. Example embodiments, however, can be implemented in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of example embodiments to those skilled in the art. The features, structures, or characteristics described in connection with the embodiments can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present disclosure. The examples described herein are intended to achieve the best mode of the present disclosure.
[0018] In the drawings, the thickness of regions and layers can be exaggerated for clarity. Like reference numerals in different drawings denote like or similar structures, and thus their detailed descriptions will be omitted.
[0019] The described features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the disclosure. One skilled in the relevant art will recognize, however, that the techniques described can be practiced without one or more of the specific details, or with other methods, components, materials, etc. In other instances, well-known structures, materials, or operations are not shown or described in detail in order to avoid obscuring aspects of the disclosure.
[0020] When an element (e.g., a layer, region, or structure) is referred to as being "on" another element, it can be directly on the other element or intervening elements can also be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present. It will be understood that when an element is referred to as being "connected" to or "coupled" to another element, it can be directly connected or coupled or intervening elements can be present. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.
[0021] The terms "a," "an," "the" are used to mean one or more than one, at least one, or one or more than one, respectively. The term "or" is used to refer to a nonexclusive or, such that "A or B" means A, B, or both. The term "and / or" as used herein refers to and / or, meaning A, B, or both A and B. The terms "first," "second," "third," etc. are used to identify elements of a group and do not mean an ordering or a ranking of importance. The terms "coupled" and "connected" and the like are used broadly and encompass both direct and indirect coupling, connections, and the like.
[0022] An organic light emitting device (OLED) is an active light emitting device, which has the advantages of light emission, ultra-thin, wide viewing angle, high brightness, high contrast, low power consumption, and extremely high response speed, and has gradually become the next generation display technology with great development prospects. An OLED includes an anode, a cathode, and an organic light emitting functional layer disposed between the anode and the cathode. The light emitting principle of the OLED is that holes and electrons are injected into the organic light emitting functional layer from the anode and the cathode, respectively. When the holes and the electrons meet in the organic light emitting functional layer, the holes and the electrons recombine in the organic light emitting functional layer to generate excitons. The excitons emit light while changing from an excited state to a ground state.
[0023] In the related art, the addition of a light extraction layer in an OLED display device can significantly improve the light extraction mode of the display device, so that light that is originally limited inside the device can be emitted out of the display device, thereby achieving higher light extraction efficiency. However, the materials currently used in the light extraction layer also have many deficiencies, for example, the refractive index is relatively low, resulting in poor light extraction effect; the refractive index has a large deviation between the wavelength regions of blue light, green light, and red light, resulting in the inability to simultaneously obtain high light extraction efficiency in blue light, green light, and red light devices.
[0024] As Figure 1 and Figure 2As shown, this embodiment of the present disclosure provides an organic light-emitting device, including a substrate 10, a first electrode layer 100, a light-emitting functional layer 300, a second electrode layer 200, and a light extraction layer 400 disposed on one side of the substrate 10. The second electrode layer 200 is located on the side of the first electrode layer 100 away from the substrate 10, the light-emitting functional layer 300 is located between the first electrode layer 100 and the second electrode layer 200, and the light extraction layer 400 is located on the side of the second electrode layer 200 away from the first electrode layer 100. The light extraction layer 400 includes first material molecules 410 and second material molecules. The percentage of the number of first material molecules 410 in the total number of molecules in the light extraction layer 400 is a, and the percentage of the number of second material molecules 410 in the total number of molecules in the light extraction layer 400 is b, where a > b and a > 50%. The angle between the main plane of the first material molecules 410 and the light emission direction of the organic light-emitting device perpendicular to the substrate 10 is 30°-90°.
[0025] The organic light-emitting device provided in this disclosure changes the refractive index of the light-emitting layer 400 by controlling the molecular stacking pattern of the material in the light extraction layer 400, thereby altering the angle between the direction of light emitted perpendicular to the substrate 10 and the main plane of the first material molecules 410. As this angle gradually increases from 30° to 90°, the refractive index gradually increases, allowing the refractive index of the light extraction layer 400 to vary within a certain range. This effectively improves the light extraction efficiency of the organic light-emitting device, thereby increasing the device's luminous efficiency.
[0026] The components of the organic light-emitting device provided in this disclosure embodiment will be described in detail below with reference to the accompanying drawings:
[0027] like Figure 1 and Figure 2 As shown, the organic light-emitting device provided in this disclosure includes a substrate 10, a first electrode layer 100, a light-emitting functional layer 300, a second electrode layer 200 and a light extraction layer 400 disposed on one side of the substrate 10. The second electrode layer 200 is located on the side of the first electrode layer 100 away from the substrate 10, the light-emitting functional layer 300 is located between the first electrode layer 100 and the second electrode layer 200, and the light extraction layer 400 is located on the side of the second electrode layer 200 away from the first electrode layer 100.
[0028] The first electrode layer 100 can serve as an anode of the light emitting device. Alternatively, the anode includes an anode material, which is preferably a material having a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include a metal such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al or SnO2:Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but is not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as the anode is included.
[0029] The second electrode layer 200 can serve as a cathode of the light emitting device, and the cathode preferably has a material having a low work function to easily inject electrons into the light emitting layer 330, and also has good light transmittance and conductivity. Specific examples of the cathode material that can be used in the present disclosure include a metal, a metal oxide, a metal alloy, for example, aluminum (Al), silver (Ag), gold (Au), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium (Li), potassium (K), sodium (Na), tin (Sn), titanium (Ti), lead (Pb), samarium (Sm), yttrium (Y), indium tin oxide (ITO), a magnesium silver alloy (Mg:Ag), a ytterbium gold alloy (Yb:Au), a ytterbium silver alloy (Yb:Ag), a lithium aluminum alloy (Li:Al), a lithium calcium magnesium alloy (Li:Ca:Al), etc.; and a stacked material, for example, magnesium / aluminum (Mg / Al), magnesium / silver (Mg / Ag), aluminum / silver (Al / Ag), aluminum / gold (Al / Au), ytterbium / gold (Yb / Au), ytterbium / silver (Yb / Ag), calcium / magnesium (Ca / Mg), calcium / silver (Ca / Ag), barium / silver (Ba / Ag), etc., but is not limited thereto.
[0030] The light emitting functional layer 300 can include a hole transport layer 321, a light emitting layer 330, and an electron transport layer 350, which are sequentially stacked in a direction away from the first electrode layer 100. Holes are injected into the light emitting layer 330 by the anode and the hole transport layer 321, and electrons are injected into the light emitting layer 330 by the cathode and the electron transport layer 350, and when the electrons and the holes meet in the light emitting layer 330, the electrons and the holes recombine in the light emitting layer 330 to generate excitons, and the excitons emit light while transitioning from an excited state to a ground state.
[0031] The light extraction layer 400 is arranged on the side of the second electrode layer 200 away from the first electrode layer 100. The light extraction layer 400 includes first material molecules 410 and second material molecules, the percentage of the number of the first material molecules 410 in the total number of molecules of the light extraction layer 400 is a, the percentage of the number of the second material molecules in the total number of molecules of the light extraction layer 400 is b, a > b, and a > 50%. The angle between the main plane of the first material molecules 410 and the light extraction direction of the organic light-emitting device perpendicular to the substrate 10 is 30°-90°.
[0032] In the present disclosure, when as many atoms as possible in a material molecule are in the same plane, the plane is the main plane of the material molecule. The angle θ between the main plane of the first material molecules 410 and the light extraction direction of the organic light-emitting device perpendicular to the substrate 10 is 30°-90°. That is, the first material molecules 410 are stacked at an angle θ, the angle θ is the angle between the main plane of the first material molecules 410 and the light extraction direction of the organic light-emitting device perpendicular to the substrate 10, and the angle θ is 30°-90°. Specifically, the angle θ can be 30°, 35°, 40°, 45°, 50°, 55°, 60°, 65°, 70°, 75°, 80°, 85°, or 90°, but is not limited thereto. It should be noted that in the same light extraction layer 400, the angle between the main plane of each first material molecule 410 and the light extraction direction of the organic light-emitting device perpendicular to the substrate 10 is equal.
[0033] In some embodiments of the present disclosure, the first material molecules 410 and the second material molecules have the same molecular structure, and a + b = 100%. That is, the light extraction layer 400 is formed by the first material molecules 410 and the second material molecules, and the first material molecules 410 and the second material molecules have the same molecular structure. Preferably, a ≥ 60%.
[0034] In some embodiments of the present disclosure, the refractive index of the light extraction layer 400 is 1.7-2.2. When the angle between the main plane of the first material molecules 410 and the light extraction direction of the organic light-emitting device perpendicular to the substrate 10 changes from 30° to 90°, the refractive index of the light extraction layer 400 gradually increases, so that the refractive index of the light extraction layer 400 changes within a certain range, such as the range of 1.7-2.2. The light extraction layer within this range can obtain a higher light extraction rate in blue, green, and red devices. When the organic light-emitting device is used in a display device, it helps to improve the light extraction efficiency of the display device.
[0035] Further, the light extraction layer 400 has a refractive index n1 of 1.7-2.2 for blue light, a refractive index n2 of 1.7-2.2 for green light, and a refractive index n3 of 1.7-2.2 for red light. Specifically, the light extraction layer 400 has a refractive index n1 of 1.7-2.2 for light with a wavelength of 460 nm, a refractive index n2 of 1.7-2.2 for light with a wavelength of 530 nm, and a refractive index n3 of 1.7-2.2 for light with a wavelength of 620 nm.
[0036] In some embodiments of the present disclosure, the light extraction layer 400 has a light transmittance of not less than 80%. Preferably, the light transmittance can be not less than 90%. A higher light transmittance also helps to improve the light extraction efficiency of the organic light-emitting device.
[0037] In some embodiments of the present disclosure, the first material molecules 410 and the second material molecules have a glass transition temperature of 125-150°C.
[0038] In the present disclosure, the first material molecules 410 and the second material molecules have the same molecular structure. The molecular structure can affect the packing mode of the material molecules in the light extraction layer. In some embodiments of the present disclosure, the first material molecules 410 and the second material molecules have the structure shown in Chemical Formula 1:
[0039]
[0040] wherein, represents a chemical bond;
[0041] X1, Y1are each independently selected from O or S;
[0042] the group A1is selected from the structure shown in Chemical Formula 2;
[0043] R1, R2are each independently selected from substituted or unsubstituted alkyl having 1-12 carbon atoms, substituted or unsubstituted cycloalkyl having 3-12 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, and substituted or unsubstituted heteroaryl having 5-20 carbon atoms, and optionally, R5and R6are connected to each other to form a 5-18 membered ring together with the atoms to which they are commonly connected;
[0044] the substituents on R1, R2are each independently selected from deuterium, halogen, alkyl having 1-4 carbon atoms, aryl having 6-12 carbon atoms, and heteroaryl having 5-12 carbon atoms.
[0045] The light extraction layer material (the first material molecule and the second material molecule) provided by the present disclosure comprises a naphthyl group with multiple substitution sites as a connecting group between the at least two fluorene groups and the at least two benzoxazole or benzothiazole groups. The naphthyl group with multiple substitution sites and the symmetric rod-like structure of the naphthyl group and the benzoxazole or benzothiazole group increase the twist angle of the molecule structure, so that the angle between the main plane of the molecule and the light extraction direction of the device is reduced, thereby obtaining a light extraction layer material with low refractive index. In addition, the light extraction layer material provided by the present disclosure can significantly improve the light extraction efficiency of the light-emitting device, reduce the loss of light in the light-emitting device, and further improve the efficiency of the light-emitting device.
[0046] In the present disclosure, the description "each of … is independently" and "… is independently selected from" can be interchangeable, and should be interpreted broadly. It can mean that the specific options expressed by the same symbols in different groups do not affect each other, or it can mean that the specific options expressed by the same symbols in the same group do not affect each other.
[0047] In the present disclosure, the term "optionally" or "optionally" means that the subsequent described event or environment can occur but does not necessarily occur. The description includes the case where the event or environment occurs or does not occur. For example, "optionally, R1 and R2 are connected to each other to form a ring with the atom to which they are commonly connected" means that R1 and R2 can be connected to each other to form a ring with the atom to which they are commonly connected, but it is not necessary to form a ring, including the case where R1 and R2 form a ring and the case where R1 and R2 do not form a ring.
[0048] In the present application, the non-positioned connecting bond refers to a single bond extending from the ring system It means that one end of the connecting bond can be connected to any position in the ring system through which the bond passes, and the other end is connected to the rest of the compound molecule.
[0049] For example, as shown in the following formula (f), the structure represented by formula (f) is connected to other positions of the molecule through two non-positioned connecting bonds that pass through the ring, and the meaning it represents includes any possible connection mode as shown in formula (f-1) to formula (f-3).
[0050]
[0051] In the present application, the indefinite substituent group refers to a substituent group connected by a single bond extending from the center of a ring system, which means that the substituent group can be connected at any possible position in the ring system. For example, in formula (g), the group A1 represented by formula (g) and the structure By connecting with the naphthalene ring through an indefinite connecting bond extending through the bicyclic ring, the meaning represented thereby includes any possible connecting mode as shown in formula (g-1) to formula (g-9), but is not limited thereto.
[0052]
[0053] In the present disclosure, the number of carbon atoms of R1, R2 refers to the total number of carbon atoms. For example, if R1 is selected from a substituted aryl group having a carbon atom number of 12, the total number of carbon atoms of the aryl group and the substituents thereon is 12. For example, R1 is The number of carbon atoms is 7.
[0054] In the present disclosure, when no specific definition is provided, "hetero" refers to including at least one N, O, S, etc. heteroatom in a functional group and the remaining atoms are carbon and hydrogen. The unsubstituted alkyl group can be a "saturated alkyl group" without any double bond or triple bond.
[0055] In the present disclosure, "alkyl" can include straight-chain alkyl or branched-chain alkyl. The alkyl group can have 1 to 12 carbon atoms, and in the present disclosure, a numerical range such as "1 to 12" means each integer in the given range; for example, "1 to 12 carbon atoms" means an alkyl group that can include 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, or 12 carbon atoms. The alkyl group can also be a lower alkyl group having 1 to 6 carbon atoms. In addition, the alkyl group can be substituted or unsubstituted.
[0056] Alternatively, the alkyl group is selected from an alkyl group having a carbon atom number of 1-6, and specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, and hexyl.
[0057] In the present disclosure, "alkenyl" refers to a hydrocarbon group containing one or more double bonds in a straight-chain or branched-chain hydrocarbon chain. The alkenyl group can be unsubstituted or substituted. The alkenyl group can have 2 to 10 carbon atoms, such as 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms. For example, the alkenyl group can be vinyl, butadiene, or propenyl, etc.
[0058] In the present disclosure, cycloalkyl refers to a radical derived from a saturated cyclic carbon chain structure. Cycloalkyl can have 3 to 12 carbon atoms, in the present disclosure, a numerical range such as "3 to 12" means each integer in the given range; for example, "3 to 12 carbon atoms" means a cycloalkyl group that can contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, or 12 carbon atoms. Cycloalkyl can be substituted or unsubstituted.
[0059] Optionally, specific embodiments of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, and the like.
[0060] In the present disclosure, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl, in other words, aryl can be a monocyclic aryl, a fused ring aryl, two or more monocyclic aryls connected by a carbon-carbon bond in conjugation, a monocyclic aryl and a fused ring aryl connected by a carbon-carbon bond in conjugation, two or more fused ring aryls connected by a carbon-carbon bond in conjugation. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond in conjugation can also be considered as aryl of the present disclosure. Among them, the fused ring aryl may, for example, include a bicyclic fused aryl (e.g., naphthyl), a tricyclic fused aryl (e.g., phenanthryl, fluorenyl, anthryl), and the like. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present disclosure, biphenyl, terphenyl, and the like are aryl. Examples of aryl can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene, benzopyrenyl, benzoperylenyl, benzophenanthryl, benzanthracenyl, benzocyclonaphthyl, and the like. The "aryl" of the present disclosure can contain 6-20 carbon atoms, in some embodiments, the number of carbon atoms in aryl can be 6-18, in other embodiments, the number of carbon atoms in aryl can be 6-12, in other embodiments, the number of carbon atoms in aryl can be 6-10. For example, in the present disclosure, the number of carbon atoms in aryl can be 6, 10, 12, 13, 14, 15, 18, 20, of course, the number of carbon atoms can also be other numbers, which are not listed here. In the present disclosure, biphenyl can be understood as aryl substituted with phenyl, and can also be understood as unsubstituted aryl.
[0061] In the present disclosure, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl, in other words, aryl can be a monocyclic aryl, a fused ring aryl, two or more monocyclic aryls connected by a carbon-carbon bond in conjugation, a monocyclic aryl and a fused ring aryl connected by a carbon-carbon bond in conjugation, two or more fused ring aryls connected by a carbon-carbon bond in conjugation. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond in conjugation can also be considered as aryl of the present disclosure. Among them, the fused ring aryl may, for example, include a bicyclic fused aryl (e.g., naphthyl), a tricyclic fused aryl (e.g., phenanthryl, fluorenyl, anthryl), and the like. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present disclosure, biphenyl, terphenyl, and the like are aryl. Examples of aryl can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene, benzopyrenyl, benzoperylenyl, benzophenanthryl, benzanthracenyl, benzocyclonaphthyl, and the like. The "aryl" of the present disclosure can contain 6-20 carbon atoms, in some embodiments, the number of carbon atoms in aryl can be 6-18, in other embodiments, the number of carbon atoms in aryl can be 6-12, in other embodiments, the number of carbon atoms in aryl can be 6-10. For example, in the present disclosure, the number of carbon atoms in aryl can be 6, 10, 12, 13, 14, 15, 18, 20, of course, the number of carbon atoms can also be other numbers, which are not listed here. In the present disclosure, biphenyl can be understood as aryl substituted with phenyl, and can also be understood as unsubstituted aryl.
[0062] In the present disclosure, substituted aryl can mean one or more hydrogen atoms in aryl is replaced by a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, alkyl group, cycloalkyl group, etc. Specific examples of heteroaryl-substituted aryl include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, pyridyl-substituted phenyl, etc. It should be understood that the number of carbon atoms in substituted aryl refers to the total number of carbon atoms in aryl and the substituents on aryl, for example, substituted aryl with 18 carbon atoms means the total number of carbon atoms in aryl and its substituents is 18.
[0063] In the present disclosure, as aryl as a substituent, specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, etc.
[0064] In the present disclosure, heteroaryl refers to a monovalent aromatic ring or its derivative containing at least one heteroatom in the ring, and the heteroatom can be at least one of O, N and S. Heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzotriazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), N-alkylcarbazolyl (such as N-methylcarbazolyl), etc., but not limited thereto. Among them, thienyl, furanyl, phenanthrolinyl, etc. are single aromatic ring system type heteroaryl, and N-arylcarbazolyl, N-heteroarylcarbazolyl are polycyclic system type heteroaryl connected by carbon-carbon bond conjugation. The "heteroaryl" of the present disclosure can contain 5-20 carbon atoms, in some embodiments, the number of carbon atoms in heteroaryl can be 5-18, and in other embodiments, the number of carbon atoms in aryl can be 5-12. For example, the number of carbon atoms can be 5, 6, 7, 10, 11, 12, 13, 18, 19, 20, of course, the number of carbon atoms can also be other numbers, which are not listed here.
[0065] In the present disclosure, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom from heteroaryl.
[0066] In this disclosure, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, N-phenylcarbazoyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
[0067] In this disclosure, the heteroaryl group used as a substituent includes, but is not limited to, pyridyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzopyridyl, benzotriazolyl, etc.
[0068] In this disclosure, halogens may include fluorine, iodine, bromine, chlorine, etc.
[0069] In some embodiments, the first material molecule 410 and the second material molecule are selected from the following chemical...
[0070] The group consisting of formulas 1-1 to 1-2:
[0071]
[0072] In some embodiments, R1 and R2 are each independently selected from alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted phenyl groups, or substituted or unsubstituted biphenyl groups.
[0073] In some embodiments, group A1 is selected from the group consisting of the following structures:
[0074]
[0075] In some embodiments, group A1 is selected from the group consisting of the following structures:
[0076]
[0077] In some embodiments, the first material molecule 410 and the second material molecule are selected from the group consisting of the following structures:
[0078]
[0079]
[0080]
[0081]
[0082]
[0083]
[0084] In some embodiments of the present disclosure, the light-emitting functional layer 300 further comprises a hole injection layer 310, which is arranged between the first electrode layer 100 and the hole transport layer 321. The light-emitting functional layer 300 further comprises an electron blocking layer 322 and a hole blocking layer 340, the electron blocking layer 322 is arranged between the hole transport layer 321 and the light-emitting layer 330. The hole blocking layer 340 is arranged between the light-emitting layer 330 and the electron transport layer 350.
[0085] Specifically, the hole injection layer 310 can be inorganic oxide, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. It can also be a dopant of a strong electron-withdrawing system, such as F4TCNQ (2,3,5,6-tetrafluoro-7,7',8,8'-tetracyano-p-quinodimethane), HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) and the like. It can also be P-doped with a hole transport material, and the thickness of the hole injection layer 310 is 5-20 nm, and the hole injection layer 310 is formed by co-evaporation.
[0086] The hole transport layer 321 has good hole transport properties and can be an aromatic amine or a carbazole material, such as NPB (N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine), TPD (N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine), DFLDPBi (4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamine]biphenyl), TCTA (tris(4-carbazol-9-ylphenyl)amine), TAPC (4,4'-cyclohexyl di[N,N-di(4-methylphenyl) aniline]) and the like.
[0087] The electron blocking layer 322 also has good hole transport properties and can be a red electron blocking layer 322, a green electron blocking layer 322, and a blue electron blocking layer 322, which can be an aromatic amine or a carbazole material, such as CBP (4,4'-bis(N-carbazole)-1,1'-biphenyl), PCzPA (9-phenyl-3-[4-(10-phenyl-9-anthryl) phenyl]-9H-carbazole) and the like.
[0088] The light-emitting layer 330 can be composed of a single light-emitting material, or can include a host material and a dopant material. Alternatively, the light-emitting layer 330 is composed of a host material and a dopant material, and holes injected into the light-emitting layer 330 and electrons injected into the light-emitting layer 330 can recombine to form excitons in the light-emitting layer 330, the excitons transfer energy to the host material, the host material transfers energy to the dopant material, and the dopant material is capable of emitting light.
[0089] The light-emitting layer 330 can be a phosphorescent host and a phosphorescent dopant, or a fluorescent host and a fluorescent dopant. In addition, each host material can include one material, or two or more mixed materials.
[0090] Specifically, the blue light-emitting layer host material can be selected from anthracene derivatives ADN (9,10-di(2-naphthyl)anthracene), MADN (3-tert-butyl-9,10-di(2-naphthyl)anthracene), and the like; and the dopant material can be a pyrene derivative, a fluorene derivative, a perylene derivative, a styrylamine derivative, a metal complex, and the like, such as TBPe (potassium tetrabromophenolphthalein ethyl ester), BDAVBi (4,4"-bis[4-(diphenylamino)styryl]biphenyl), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), FIrpic (bis(4,6-difluorophenylpyridine-N,C2)picolinate iridium), and the like.
[0091] The green light-emitting layer host material can be selected from coumarin dyes, quinacridone copper derivatives, polycyclic aromatic hydrocarbons, anthracene derivatives, carbazole derivatives, such as DMQA (N,N'-dimethylquinacridone), BA-NPB (N,N'-di-1-naphthyl-N,N'-diphenyl-[9,9'-bianthracene]-10,10'-diamine; N1,N1'-diphenyl-N1,N1'-dinaphthyl-9,9'-bianthracene-1,1'-diamine), Alq3 (8-hydroxyquinoline aluminum), CBP (4,4'-bis(N-carbazole)-1,1'-biphenyl), and the like. The dopant material can be a metal complex, and the like, such as Ir(ppy)3 (tris(2-phenylpyridine)iridium | 94928-86-6), Ir(ppy)2(acac) (acetylacetonate di(2-phenylpyridine)iridium), and the like.
[0092] The red light-emitting layer host material can be selected from the DCM series materials, such as DCJTB (2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9-yl)vinyl]-4H-pyranyl-4-ylidene}propanedinitrile), DCJTI (2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9-yl)vinyl]-4H-pyranyl-4-ylidene}propanedinitrile), and the like, and the dopant material can be a metal complex, such as Ir(piq)2(acac) (iridium(III) bis(1-phenyl-isoquinoline)(acetylacetone)), PtOEP (platinum(II) octaethylporphyrin), Ir(btp)2(acac) (iridium bis(2-(2'-benzothienyl)pyridine-N,C3')(acetylacetone)), and the like.
[0093] The hole blocking layer 340 and the electron transport layer 350: Generally, an aromatic heterocyclic compound, such as a benzimidazole derivative, an imidazopyridine derivative, a benzimidazophenanthroline derivative, and the like imidazole derivative; a pyrimidine derivative, a triazine derivative, and the like azine derivative; a quinoline derivative, an isoquinoline derivative, a phenanthroline derivative, and the like compound containing a nitrogen-containing six-membered ring structure (also including a compound having a phosphine oxide group as a substituent on the heterocycle. For example: OXD-7 (2,2'-(1,3-phenyl)bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole]), TAZ (3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole), p-EtTAZ (3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole), BPhen (4,7-diphenyl-1,10-phenanthroline), TPBi (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene), and the like.
[0094] Further, the light-emitting functional layer 300 can further include an electron injection layer 360, which is provided between the cathode and the electron transport layer 350. The electron injection layer 360 preferably has a substance having electron transportability, while having an effect of injecting electrons from the cathode, and has excellent thin film formation ability, and is generally an alkali metal or a metal, such as LiF, Yb, Mg, Ca, or a compound thereof, and the like.
[0095] The present disclosure also provides a display device including the aforementioned organic light-emitting device. The display device can be a mobile phone, a tablet, a television, a display, a notebook computer, a digital photo frame, or a navigator, or any other product or component having a display function.
[0096] The organic light-emitting device provided by the present disclosure will be described in detail below with reference to specific experimental data, etc.
[0097] Synthesis Example
[0098] Synthesis of Compound 1
[0099]
[0100] Synthesis of Intermediate M-1: Take 2,5-dibromothieno[3,2-b]thiophene (3.54 g, 12 mmol), (6-bromo-7-iodonaphthalen-2-yl)boronic acid (9.40 g, 25 mmol), Pd(PPh3)2Cl2(350 mg, 0.5 mmol), potassium carbonate (4.14 g, 30 mmol), toluene / ethanol / water (90 mL / 60 mL / 30 mL) into a round-bottom flask in turn, and warm to 90°C, and reflux the reaction under nitrogen protection for 24 h. Monitor the reaction process by TLC plate until the reaction is complete, and then cool the reaction solution to room temperature. Extract with dichloromethane and wash with deionized water, and then take the organic phase, dry with anhydrous sodium sulfate, spin dry the solvent, and mix the sample. Separate by column chromatography on silica gel, and dry to obtain the solid powder product 6.23 g with a yield of 65%. 1 H NMR (500 MHz, Chloroform) δ 8.53 (s, 2H), 8.44 (s, 2H), 8.31 (d, J = 5.0 Hz, 4H), 7.93 (s, 1H), 7.75 (s, 2H).
[0101] Synthesis of Intermediate M-2: Take M-1 (6 g, 7.5 mmol), benzoxazole (1.9 g, 16 mmol), (η 3 -C3H5)2Pd2Cl2(182 mg, 0.5 mmol), potassium acetate (2.9 g, 30 mmol), dimethylacetamide (120 mL) into a round-bottom flask in turn, and warm to 140°C, and reflux the reaction under nitrogen protection for 24 h. Monitor the reaction process by TLC plate until the reaction is complete, and then cool the reaction solution to room temperature. Extract with dichloromethane and wash with deionized water, and then take the organic phase, dry with anhydrous sodium sulfate, spin dry the solvent, and mix the sample. Separate by column chromatography on silica gel, and dry to obtain the solid powder product 4.93 g with a yield of 75%. 1 H NMR (500 MHz, Chloroform) δ 8.46 (s, 2H), 8.42 (s, 2H), 8.23 (d, J = 3.9 Hz, 4H), 7.93 (s, 2H), 7.75 (m, 6H), 7.38 (s, 4H).
[0102] Synthesis of compound 1 : M-2 (4.8 g, 5.5 mmol), (9, 9-dimethyl-9H-fluoren-2-yl)boronic acid (2.86 g, 12 mmol), Pd(PPh3)2Cl2(210 mg, 0.3 mmol), potassium carbonate (2.07 g, 15 mmol), toluene / ethanol / water (60 mL / 30 mL / 10 mL) were added into a round bottom flask in sequence, heated to 90 °C, and refluxed under nitrogen protection for 24 h. TLC thin plate was used to monitor the reaction process until completion, and then the reaction solution was cooled to room temperature. The organic phase was extracted with dichloromethane and washed with deionized water, dried with anhydrous sodium sulfate, and the solvent was rotary evaporated. The sample was mixed and separated by silica gel column chromatography to obtain the product 3.89 g of solid powder with a yield of 70%. 1 H NMR (500 MHz, Chloroform) δ 8.71 (s, 2H), 8.64 (s, 2H), 8.51 (s, 2H), 8.44 (s, 2H), 8.07 (m, 4H), 7.99 (s, 2H), 7.90 (s, 2H), 7.76 (m, 8H), 7.57 (s, 2H), 7.36 (m, 6H), 7.24 (s, 2H), 1.69 (s, 12H).
[0103] Synthesis of compound 4:
[0104]
[0105] Synthesis of intermediate M-3: The synthesis of intermediate M-3 was similar to that of intermediate M-1, except that (6-bromo-7-iodonaphthalen-2-yl)boronic acid was replaced by (6-bromo-8-iodonaphthalen-2-yl)boronic acid. The yield was 65%. 1 H NMR (500 MHz, Chloroform) δ 8.54 (s, 2H), 8.44 (s, 2H), 8.38 (s, 2H), 7.96 (s, 2H), 7.81 (s, 2H), 7.71 (s, 2H).
[0106] Synthesis of intermediate M-4: The synthesis of intermediate M-4 was similar to that of intermediate M-2, except that M-1 was replaced by M-3. The yield was 76%. 1 H NMR (500 MHz, Chloroform) δ 8.44 (s, 2H), 8.40 (s, 2H), 8.33 (s, 2H), 8.27 (s, 2H), 7.81 (s, 2H), 7.73 (d, J = 5.0 Hz, 6H), 7.38 (s, 4H).
[0107] Synthesis of compound 4: The synthesis of compound 4 was similar to that of compound 1, except that M-2 was replaced by M-4. The yield was 72%. 1H NMR (500 MHz, Chloroform) δ 8.51 (s, 2H), 8.43 (s, 2H), 8.27 (s, 2H), 8.07 (dd, J = 12.2, 2.8 Hz, 8H), 7.90 (s, 2H), 7.82 - 7.57 (m, 10H), 7.42 - 7.19 (m, 8H), 1.69 (s, 12H).
[0108] Synthesis of compound 7:
[0109]
[0110] Synthesis of compound 7 was similar to that of compound 1, except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was replaced by spiro[cyclohexane-l,9'-fluoren]-2'-ylboronic acid. Yield 70%. 1 H NMR (500 MHz, Chloroform) δ 8.70 (s, 2H), 8.50 (s, 2H), 8.43 (s, 2H), 8.09 (d, J = 2.8 Hz, 4H), 7.98 (s, 2H), 7.89 (s, 2H), 7.84 - 7.65 (m, 10H), 7.36 (m, 6H), 7.24 (s, 2H), 6.43 (s, 2H), 2.41 (s, 2H), 2.16 (s, 2H), 1.86 (s, 2H), 1.68 (s, 4H), 1.60 - 1.31 (m, 6H), 1.19 (s, 4H).
[0111] Synthesis of compound 10:
[0112]
[0113] Synthesis of compound 10 was similar to that of compound 4, except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was replaced by spiro[cyclohexane-l,9'-fluoren]-2'-ylboronic acid. Yield 72%. 1 H NMR (500 MHz, Chloroform) δ 8.14 - 8.03 (m, 6H), 8.00 (s, 2H), 7.91 (m, 4H), 7.81 - 7.65 (m, 8H), 7.48 (s, 2H), 7.43 - 7.28 (m, 8H), 7.23 (s, 2H), 6.64 (s, 2H), 2.41 (s, 2H), 2.16 (s, 2H), 1.86 (s, 2H), 1.68 (s, 4H), 1.61 - 1.31 (m, 6H), 1.19 (s, 4H).
[0114] Synthesis of compound 13:
[0115]
[0116] The synthesis of compound 13 was similar to that of compound 1, except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was replaced by (9,9-diphenyl-9H-fluoren-2-yl)boronic acid. Yield 77%. 1 H NMR (500 MHz, Chloroform) δ 8.71 (s, 2H), 8.51 (s, 2H), 8.44 (s, 2H), 8.25 (s, 2H), 8.09 (s, 2H), 7.99 (s, 2H), 7.90 (s, 2H), 7.76 (m, 8H), 7.45 - 7.02 (m, 30H), 6.53 (s, 2H).
[0117] Synthesis of compound 16:
[0118]
[0119] The synthesis of compound 16 was similar to that of compound 4, except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was replaced by (9,9-diphenyl-9H-fluoren-2-yl)boronic acid. Yield 70%. 1 H NMR (500 MHz, Chloroform) δ 9.27 (s, 2H), 8.56 (s, 2H), 8.48 (s, 2H), 8.08 (d, J = 5.0 Hz, 4H), 7.90 (s, 2H), 7.82 - 7.63 (m, 8H), 7.46 - 7.03 (m, 32H), 6.40 (s, 2H).
[0120] Synthesis of compound 19:
[0121]
[0122] The synthesis of compound 19 was similar to that of compound 1, except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was replaced by 9,9'-spirobi[fluoren]-2-ylboronic acid. Yield 72%. 1 H NMR (500 MHz, Chloroform) δ 8.71 (s, 2H), 8.51 (s, 2H), 8.44 (s, 2H), 8.23 (s, 4H), 8.08 (s, 2H), 7.99 (s, 2H), 7.89 (d, J = 5.0 Hz, 6H), 7.81 - 7.62 (m, 10H), 7.45 - 7.28 (m, 12H), 7.24 (d, J = 5.0 Hz, 8H).
[0123] Synthesis of compound 22:
[0124]
[0125] The synthesis of compound 22 was similar to that of compound 4, except that (9,9-dimethyl-9H-fluorene-2-yl)boronic acid was replaced with 9,9'-spirobis[fluorene]-2-ylboronic acid. Yield: 76%. ¹H NMR (500 MHz, Chloroform): δ 8.70 (s, 4H), 8.49 (s, 2H), 8.08 (s, 4H), 7.99 (s, 2H), 7.97–7.87 (m, 8H), 7.74 (s, 4H), 7.68 (d, J = 5.0 Hz, 4H), 7.64 (s, 2H), 7.44–7.29 (m, 10H), 7.24 (d, J = 5.0 Hz, 8H), 7.05 (s, 2H).
[0126] Device Examples
[0127] Example 1
[0128] like Figure 1 As shown, a glass plate with a first electrode layer 100 (ITO) is placed in a vacuum chamber, and the vacuum is evacuated to 1×10⁻⁶. -6 ~1×10 -7 Hole injection material is vacuum-deposited on the side of ITO away from the glass plate to form a hole injection layer 310.
[0129] Hole transport material is vapor-deposited on the side of hole injection layer 310 away from ITO to form hole transport layer 321.
[0130] An electron blocking material is vacuum-deposited on the side of the hole transport layer 321 away from the hole injection layer 310 to form an electron blocking layer 322.
[0131] A light-emitting material is vacuum-deposited on the side of the electron blocking layer 322 away from the hole transport layer 321 to form a light-emitting layer 330. The light-emitting material includes a host material and a guest material. The weight ratio of the host material to the guest material is 95:5 using a multi-source co-evaporation method.
[0132] Hole blocking material is vacuum-deposited on the side of the light-emitting layer 330 away from the electron blocking layer 322 to form a hole blocking layer 340.
[0133] An electron transport material is vacuum-deposited on the side of the hole blocking layer 340 away from the light-emitting layer 330 to form an electron transport layer 350.
[0134] An inorganic material (LiF) with a thickness of 1 nm is vacuum-deposited on the side of the electron transport layer 350 away from the hole blocking layer 340 as an electron injection material to form an electron injection layer 360.
[0135] An Al layer is deposited at the electron injection layer 360 degrees away from the evaporation electron transport layer as the cathode 200.
[0136] An organic compound 1 with a thickness of 65 nm was vacuum evaporated on the side of the cathode 200 away from the electron injection layer 360 as a light extraction layer material (first material molecule 410 and second material molecule) to form a light extraction layer 400.
[0137] The device structure is:
[0138] ITO / HAT-CN (20 nm) / NPB (50 nm) / TCTA (6 nm) / Host+5% Dopant (20 nm) / DPEPO (10 nm) / TmPyPB (30 nm) / LiF (1 nm) / Al (100 nm) / CPL (65 nm).
[0139] Examples 2-8
[0140] The light extraction layer material in Example 1 is replaced with the data in Table 4, and the others remain unchanged.
[0141] Comparative Example 1
[0142] The light extraction layer material in Example 1 is replaced with Ref in Table 1, and the others remain unchanged.
[0143] The structures of the compounds in the other film layers are shown in Table 1
[0144] Table 1
[0145]
[0146] HAT-CN is a hole injection layer, NPB is a hole transport layer, TCTA is an electron blocking layer, DPEPO is a hole blocking layer and TmPyPb is an electron transport layer, AND is a blue light host, DPAVBi is a blue light dopant, CBP is a green light host, Ir(ppy)3 is a green light dopant, DCJTI is a red light host, and (BTP)2Ir(acac) is a red light dopant.
[0147] Performance parameters of the light extraction layer material
[0148] The performance test of the compound is as follows:
[0149] The refractive index is an important physical parameter of the CPL (light extraction layer) material, and the size of the refractive index directly determines the light coupling efficiency of the light-emitting device. The refractive index can be measured by an ellipsometer. The scanning range of the instrument is 245-1000 nm. The glass substrate is evaporated with a thin film, and the thickness of the material thin film can be 60 nm. The light extraction layer material
[0150] Table 2
[0151]
[0152] The glass transition temperature was tested as follows:
[0153] The glass transition temperature (Tg) determines the thermal stability of the material in evaporation. The higher the Tg, the better the thermal stability of the material. The measuring instrument was a DSC differential scanning calorimeter. The test was carried out under a nitrogen atmosphere, the temperature raising rate was 10°C / min, and the temperature range was 50-300°C. The measured glass transition temperature (Tg) is shown in Table 3.
[0154] Table 3
[0155] Compound Tg (°C) Compound Tg (°C) 1 135 16 138 4 141 19 145 7 142 22 140 10 138 Ref. 131 13 141
[0156] Parameters of the organic electroluminescent devices of the device examples and the comparative examples
[0157] The luminous efficiency and stability of the organic light-emitting device were tested at a current density of 15 mA / cm 2 The results of each example are shown in Table 4 below.
[0158] Table 4
[0159]
[0160]
[0161] The values in Table 4 are percentages of the comparative examples relative to the comparative examples. Compared with the light-emitting device prepared in Comparative Example 1, the light-emitting device prepared in Examples 1 to 4 using the compound of the present disclosure as the light extraction layer has higher luminous efficiency.
[0162] It should be appreciated that the present disclosure is not limited to the detailed structure and arrangement of the components set forth in the specification. The present disclosure can have other embodiments and can be implemented and executed in various ways. The foregoing variations and modifications are within the scope of the present disclosure. It should be appreciated that the present disclosure disclosed and defined in the specification extends to all alternative combinations of two or more of the individual features mentioned or evident from the description and / or drawings. All these different combinations constitute various alternative aspects of the present disclosure. The embodiments of the specification illustrate the best mode presently known for carrying out the present disclosure and will enable one skilled in the art to utilize the present disclosure.
Claims
1. An organic light emitting device, characterized by, The organic light-emitting device comprises a substrate, a first electrode layer, a light-emitting functional layer, a second electrode layer and a light-extracting layer, the second electrode layer is located on the side of the first electrode layer away from the substrate, the light-emitting functional layer is located between the first electrode layer and the second electrode layer, and the light-extracting layer is located on the side of the second electrode layer away from the first electrode layer. The light-extracting layer is composed of first material molecules, or the light-extracting layer comprises first material molecules and second material molecules, the percentage of the number of molecules of the first material molecules in the total number of molecules of the light-extracting layer is a, the percentage of the number of molecules of the second material molecules in the total number of molecules of the light-extracting layer is b, a > b, and a > 50%. The included angle between the main plane of the first material molecules and the light-extracting direction of the organic light-emitting device perpendicular to the substrate is 30°-90°. The first material molecules and the second material molecules have the structure shown in the following Chemical Formula 1. wherein, represents a chemical bond; X1 and Y1 are each independently selected from O or S. Group A1 is selected from the structure shown in the following Chemical Formula 2. R1 and R2 are each independently selected from substituted or unsubstituted alkyl with 1-12 carbon atoms, substituted or unsubstituted cycloalkyl with 3-12 carbon atoms, substituted or unsubstituted aryl with 6-20 carbon atoms, and substituted or unsubstituted heteroaryl with 5-20 carbon atoms, and optionally, R1 and R2 are connected to each other to form a 5-18 membered ring together with the atoms to which they are commonly connected. The substituents on R1 and R2 are each independently selected from deuterium, halogen, alkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms, and heteroaryl with 5-12 carbon atoms.
2. The organic light emitting device according to claim 1, wherein The refractive index of the light-extracting layer is 1.7-2.
2.
3. The organic light-emitting device according to claim 1, characterized in that, a ≥ 60%, and a + b = 100%.
4. The organic light emitting device of claim 1, wherein, The light transmittance of the light-extracting layer is not less than 80%.
5. The organic light-emitting device according to claim 1, characterized in that, The glass transition temperature of the first material molecules and the second material molecules is 125°C-150°C.
6. The organic light emitting device of claim 1, wherein The first material molecules and the second material molecules are selected from the group consisting of the following Chemical Formulae 1-1 to 1-2: 。 7. The organic light emitting device according to claim 6, wherein R1 and R2 are each independently selected from substituted or unsubstituted alkyl with 1-6 carbon atoms, substituted or unsubstituted phenyl, and substituted or unsubstituted biphenyl.
8. The organic light-emitting device according to claim 6, characterized in that, Group A1 is selected from the group consisting of the following structures: 。 9. The organic light emitting device of claim 1, wherein The first material molecules and the second material molecules are selected from the group consisting of the following structures: 。 10. A display device, characterized by comprising: The organic light-emitting device comprises a substrate, a first electrode layer, a light-emitting functional layer, a second electrode layer and a light-extracting layer, the second electrode layer is located on the side of the first electrode layer away from the substrate, the light-emitting functional layer is located between the first electrode layer and the second electrode layer, and the light-extracting layer is located on the side of the second electrode layer away from the first electrode layer.
Citation Information
Patent Citations
Liquid crystal cured layer, production method therefor, optical film, polarizing plate, and display device
CN111684325A
Novel organic compound for capping layer, and organic light-emitting element comprising same
CN112745264A