Heterocyclic compounds and electronic devices
By using UV stabilized mixture in the thin film packaging part of the organic light emitting display, the device damage caused by UV penetration is solved, and higher durability and stability are achieved.
Patent Information
- Application Number
- CN201910043785.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2018-01-24
- Filing Date
- 2019-01-17
- Publication Date
- 2025-04-08
- Estimated Expiration
- 2039-01-17
AI Technical Summary
In the process of manufacturing an organic light emitting display, ultraviolet rays easily penetrate into the electronic device, causing damage to components such as the organic emitting layer and insulating film.
Using a thin film encapsulation portion containing a UV-stabilized mixture consisting of a UV absorber and a radical scavenger to reduce the penetration of UV light.
It effectively reduces the damage to organic light-emitting devices by ultraviolet rays and improves the durability and stability of electronic devices.
Smart Images

Figure CN110071095B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0008951 filed on January 24, 2018, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2018-0008952 filed on January 24, 2018, in the Korean Intellectual Property Office, the entire contents of each of which are incorporated herein by reference. Technical Field
[0002] One or more embodiments relate to a heterocyclic compound, an electronic device including an organic light emitting device, and a method of manufacturing the electronic device. Background Art
[0003] The electronic device may include an organic light-emitting device, which includes a hole injection electrode, an electron injection electrode, and an organic emission layer located between the hole injection electrode and the electron injection electrode. Compared with other devices in the art, the organic light-emitting device is a self-emitting device with wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage and response speed. For example, an organic light-emitting display device, which is a class (or a type) of electronic devices including an organic light-emitting device, is a self-emitting device in which holes injected from the hole injection electrode and electrons injected from the electron injection electrode recombine in the organic emission layer to generate excitons. These excitons transition (e.g., transition or relaxation) from an excited state to a ground state, thereby generating light.
[0004] Since an organic light emitting display device as a self-emitting display device does not require a separate light source, the organic light emitting display device can be driven at a low voltage, can be constructed to be lightweight and thin, and can have excellent characteristics in terms of viewing angle, contrast, and response time. Therefore, such an organic light emitting display device has applications ranging from personal portable devices such as MP3 players and mobile phones to televisions (TVs), but is not limited thereto.
[0005] In addition, as the outdoor use of information devices such as electronic devices including organic light-emitting devices increases, electronic devices including organic light-emitting devices are increasingly exposed to sunlight. In addition, in the process of manufacturing organic light-emitting devices, there are many cases where operations involving ultraviolet irradiation are required. Therefore, if ultraviolet rays are freely transmitted to the inside of the organic light-emitting device, the emission layer including organic materials, etc., may be seriously damaged. Summary of the invention
[0006] During the manufacturing process of electronic devices such as organic light emitting displays, when ultraviolet rays or the like are introduced into the device from outside the device or penetrate into the device from outside the device, an emission layer including organic materials, an insulating film, etc. may be severely damaged.
[0007] Aspects of embodiments of the present disclosure provide an electronic device capable of reducing the amount of ultraviolet rays transmitted into the electronic device. However, these aspects of the embodiments are illustrative, and the scope of the present disclosure is not limited thereto.
[0008] Additional aspects of the embodiments will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0009] An aspect of an embodiment provides an electronic device, the electronic device comprising:
[0010] substrate;
[0011] an organic light emitting device disposed on a substrate; and
[0012] Thin film encapsulation part, sealing organic light-emitting devices,
[0013] The film encapsulation part includes an ultraviolet (UV) stable mixture.
[0014] The UV stabilizing mixture includes a UV absorber and a free radical scavenger.
[0015] Another aspect of the embodiment provides a heterocyclic compound represented by formula B1:
[0016] Formula B1
[0017] (A 1 ) m1 -L 1 -(A 2 ) m2 .
[0018] In formula B1,
[0019] L 1 Can be connection A 1 and A 2 (m1+m2) price C 2 -C 20 Organic groups,
[0020] A 1 It can be a UV absorbing group,
[0021] A 2 Can be a free radical scavenging group,
[0022] m1 can be an integer from 1 to 3,
[0023] m2 can be an integer from 1 to 3.
[0024] Another aspect of the embodiment provides an electronic device including: a substrate; an organic light emitting device located on the substrate; and a thin film encapsulation portion sealing the organic light emitting device, wherein the thin film encapsulation portion includes a heterocyclic compound. BRIEF DESCRIPTION OF THE DRAWINGS
[0025] These and / or other aspects of the embodiments will become apparent and more easily understood through the following description of the embodiments in conjunction with the accompanying drawings, in which:
[0026] Figure 1-Figure 2 is a schematic cross-sectional view of an organic light emitting display device as an example of an electronic device according to an embodiment;
[0027] Figure 3 is a graph showing transmittance of a thin film encapsulation portion of the electronic device according to Example 1-1 and the electronic device according to Comparative Example 1-1 with respect to exposure time; and
[0028] Figure 4 is a graph showing transmittance of thin film encapsulation portions of the electronic device according to Example 2-1 and the electronic devices according to Comparative Examples 2-1 and 2-2 with respect to exposure time. DETAILED DESCRIPTION
[0029] The present disclosure will now be described more fully with reference to exemplary embodiments. However, the present disclosure may be implemented in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that the present disclosure will be thorough and complete and will fully convey the concepts of the disclosure to those skilled in the art. Figure 1 The features of the present disclosure and how to implement the features of the present disclosure will become apparent with reference to the embodiments that will be described in more detail herein. However, the subject matter of the present disclosure can be implemented in many different forms and should not be limited to the exemplary embodiments.
[0030] Hereinafter, the embodiments are described in more detail by referring to the accompanying drawings, in which like reference numerals denote like elements and redundant explanations thereof will not be provided herein.
[0031] It will be understood that when a layer, film, region, or plate is referred to as being "formed on" another layer, film, region, or plate, it may be directly or indirectly formed on the other layer, film, region, or plate, for example, there may be an intermediate layer, film, region, or plate. In addition, the size of the components in the drawings may be exaggerated for ease of explanation. In other words, since the size and thickness of the components in the drawings may be arbitrarily shown for ease of explanation, the following embodiments of the present disclosure are not limited thereto.
[0032] Hereinafter, the terms “first”, “second”, etc. are used only for the purpose of distinguishing one element from another element.
[0033] In the following embodiments, the x-axis, y-axis, and z-axis are not limited to the three axes on the orthogonal coordinate system, and can be interpreted as a broader meaning. For example, the x-axis, y-axis, and z-axis can be orthogonal to each other, but can indicate different directions that are not orthogonal to each other.
[0034] An aspect of an embodiment provides an electronic device comprising: a substrate; an organic light-emitting device located on the substrate; and a thin film encapsulation that seals the organic light-emitting device, wherein the thin film encapsulation comprises a UV stabilizing mixture comprising a UV absorber and a free radical scavenger.
[0035] For example, the electronic device may include: a substrate; an organic light emitting device included in a pixel definition region on the substrate; and a thin film encapsulation sealing the organic light emitting device, wherein the thin film encapsulation includes a UV stabilizing mixture.
[0036] Another aspect of the embodiment provides an electronic device including: a substrate; an organic light emitting device located on the substrate; and a thin film encapsulation sealing the organic light emitting device, wherein the thin film encapsulation includes a heterocyclic compound.
[0037] For example, the electronic device may include: a substrate; an organic light emitting device included in a pixel definition region on the substrate; and a thin film encapsulation member sealing the organic light emitting device, wherein the thin film encapsulation member includes a heterocyclic compound. The heterocyclic compound will be described below.
[0038] Figure 1 is a schematic cross-sectional view of an organic light emitting display device 10 according to an embodiment.
[0039] Reference Figure 1 , an organic light emitting display apparatus 10 according to an embodiment includes a substrate 100 , an organic light emitting device 200 , and a thin film encapsulation 300 .
[0040] The substrate 100 may be any of various suitable substrates used in organic light-emitting display devices in the related art, and may be an inorganic substrate or an organic substrate, both having high mechanical strength, thermal stability, transparency, surface flatness, easy handling, and waterproofness.
[0041] For example, the substrate 100 may be made of SiO 2 The inorganic substrate is made of a transparent glass material as a main component, but the embodiments of the present disclosure are not limited thereto.
[0042] In one embodiment, the substrate 100 may be an organic substrate including an insulating organic material. The insulating organic material may be selected from, for example, polyethersulfone (PES), polyacrylate (PAR), polyetherimide (PEI), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), polyphenylene sulfide (PPS), polyallylate, polyimide, polycarbonate (PC), triacetyl cellulose (TAC), and cellulose acetate propionate (CAP), but the embodiments of the present disclosure are not limited thereto.
[0043] The organic light emitting device 200 is disposed on the substrate 100. The organic light emitting device 200 may include a first electrode, an intermediate layer including an emission layer, and a second electrode.
[0044] For example, the first electrode may be formed by depositing or sputtering a material for forming the first electrode on the substrate 100. When the first electrode is an anode, the material for forming the first electrode may be selected from materials having a high work function to facilitate hole injection.
[0045] The first electrode may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode is a transmissive electrode, the material used to form the first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0046] The first electrode may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode is not limited thereto.
[0047] An intermediate layer may be disposed on the first electrode, the intermediate layer including an emission layer.
[0048] The intermediate layer may further include a hole transport region and an electron transport region, the hole transport region being located between the first electrode and the emission layer, and the electron transport region being located between the emission layer and the second electrode, but the embodiments of the present disclosure are not limited thereto.
[0049] The second electrode may be disposed on the intermediate layer. The second electrode may be a cathode as an electron injection electrode. In this regard, the metal used to form the second electrode may be a material having a low work function, such a material may be a metal, an alloy, a conductive compound, or a combination thereof.
[0050] The second electrode may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments of the present disclosure are not limited thereto. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0051] The first electrode may have a single-layer structure or a multi-layer structure including two or more layers.
[0052] The organic light emitting display device 10 includes a thin film encapsulation 300 .
[0053] The thin film encapsulation 300 may have a UV stabilizing mixture, and the UV stabilizing mixture may include a UV absorber and a radical scavenger.
[0054] In one embodiment, the UV absorber may include at least one UV absorbing compound selected from:
[0055] Benzophenone-containing compounds, benzoquinone-containing compounds, anthraquinone-containing compounds, xanthone-containing compounds, benzotriazine-containing compounds, benzotriazine-containing compounds, benzotriazole-containing compounds, benzoate-containing compounds, cyanoacrylate-containing compounds, triazine-containing compounds, oxalylanilide-containing compounds, salicylate-containing compounds and pyrene-containing compounds, all of which are substituted with hydroxyl groups.
[0056] The benzophenone-containing compound may include, for example, 2-hydroxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octylbenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 4-benzyloxy-2-hydroxybenzophenone, 2,2′,4,4′-tetrahydroxybenzophenone, 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, and the like.
[0057] The benzoquinone-containing compound may include, for example, 2-hydroxybenzoquinone.
[0058] The anthraquinone-containing compound may include, for example, 1-hydroxyanthraquinone, 1,5-hydroxyanthraquinone, 1,8-hydroxyanthraquinone, and the like.
[0059] The benzotriazole-containing compound may include, for example, 2-(2-hydroxyphenyl)benzotriazole, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3,5-di-tert-butyl-2-hydroxyphenyl)benzotriazole, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-tert-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-tert-amyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, and the like.
[0060] The benzoate-containing compound may include, for example, phenyl 2-hydroxybenzoate, 2,4-di-tert-butylphenyl-3′,5′-di-tert-butyl-4-hydroxybenzoate, and the like.
[0061] The triazine-containing compound may include, for example, 2-(4,6-diphenyl-1,3,5-triazine-2-yl)phenol, 2-(4,6-diphenyl-1,3,5-triazine-2-yl)-5-(hexyl)oxy-phenol, 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, and the like.
[0062] The salicylate-containing compound may include, for example, phenyl salicylate, 4-tert-butylphenyl salicylate, and the like.
[0063] In one embodiment, the UV absorbing compound may be represented by one selected from Formula A1-1 to Formula A1-3:
[0064] Formula A1-1
[0065]
[0066] Formula A1-2
[0067]
[0068] Formula A1-3
[0069]
[0070] In Formula A1-1 to Formula A1-3,
[0071] CY 1 and CY 2 may be independently selected from phenyl, naphthyl, anthracenyl, pyrenyl and phenanthrenyl,
[0072] R 1 and R 2can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 60 Cycloalkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0073] R 1 and R 2 can be optionally connected to form -(Y 1 ) k1 - a linker,
[0074] Y 1 It can be -O-, -S- or -C(=O)-,
[0075] k1 can be an integer from 1 to 3,
[0076] Y 2 and Y 3 One of them can be N, Y 2 and Y 3 The other of may be a single bond, a double bond or -C(=O)-,
[0077] R 10 , R 20 , R 30 and R 40 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 60 Cycloalkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1) and -P(=O)(Q 1 )(Q 2 ),
[0078] a10 can be an integer from 1 to 18,
[0079] a20 can be an integer from 1 to 4,
[0080] a30 can be an integer from 1 to 5,
[0081] a40 can be an integer from 1 to 4,
[0082] a10 number of R 10 At least one of them may be a hydroxyl group,
[0083] a20 numbers of R 20 At least one of them may be a hydroxyl group,
[0084] a30 number of R 30 At least one of them may be a hydroxyl group,
[0085] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 60 Cycloalkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0086] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0087] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) of at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0088] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups;
[0089] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) of at least one of C 3 -C 10 Cycloalkyl, C 1 -C10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0090] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0091] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60Aryl, substituted with C 1 -C 60 Alkyl C 6 -C 60 Aryl, substituted with C 6 -C 60 Aryl C 6 -C 60 Aryl, terphenyl, C 1 -C 60 Heteroaryl, substituted with C 1 -C 60 Alkyl C 1 -C 60 Heteroaryl, substituted with C 6 -C 60 Aryl C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
[0092] In one embodiment, in Formula A1-1 to Formula A1-3,
[0093] R 1 and R 2 Can be independently selected from:
[0094] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0095] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,
[0096] Among them, R 1 and R 2 can be optionally connected to form -(Y 1 ) k1 -linking group, wherein -(Y 1 ) k1 - may be -O-, -S, - or -C(=O)-.
[0097] For example, R 1 and R 2 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,
[0098] Among them, R 1 and R 2 Can be connected to form -(Y 1 ) k1 -linking group, wherein -(Y 1 ) k1 - may be -O-, -S- or -C(=O)-.
[0099] In one embodiment, in Formula A1-1 to Formula A1-3,
[0100] R 10 , R 20 , R 30 and R 40 Can be independently selected from:
[0101] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0102] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy.
[0103] For example, R 10 , R 20 , R 30 and R 40 Can be independently selected from:
[0104] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0105] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy.
[0106] In one embodiment, the UV absorbing compound may be represented by one selected from Formula A2-1 to Formula A2-9:
[0107]
[0108]
[0109] In Formula A2-1 to Formula A2-9,
[0110] R 3 , R 4 and R 11 To R 18 Combined with R 10 Same as described,
[0111] a16 can be 1, 2, 3 or 4,
[0112] b16 can be 1 or 2,
[0113] b17 can be 1, 2, 3 or 4,
[0114] c15 can be 1 or 2,
[0115] c16 can be 1, 2 or 3,
[0116] c17 can be 1 or 2,
[0117] R 21 To R 24 Combined with R 20 Same as described,
[0118] R 31 To R 35 Combined with R 30 Same as described,
[0119] R 41 To R 44 Combined with R 40 Same as described,
[0120] R 11 To R 18 At least one of R 21 To R 24 At least one of R 31 To R 35 At least one of the groups may be a hydroxyl group.
[0121] In one embodiment, R in Formula A2-1 to Formula A2-7 11 , R 15 and R 18 At least one of them may be a hydroxyl group. 11 and R 18 At least one of the may be a hydroxyl group, but embodiments of the present disclosure are not limited thereto.
[0122] In one embodiment, R in Formula A2-8 21 It may be a hydroxyl group.
[0123] In one embodiment, R in Formula A2-9 31 and R 35 At least one of the groups may be a hydroxyl group.
[0124] In one embodiment, the UV absorbing compound can be represented by one selected from Formula A3-1 to Formula A3-9:
[0125]
[0126] In Formula A3-1 to Formula A3-9,
[0127] R 12 To R 17 Combined with R 10 Same as described,
[0128] R 21 To R 23 Combined with R 20 Same as described,
[0129] R 34 Combined with R 30 Same as described.
[0130] In one embodiment, the UV absorber may include a first UV absorbing compound and a second UV absorbing compound,
[0131] The first UV absorbing compound and the second UV absorbing compound may be independently selected from benzophenone-containing compounds, benzoquinone-containing compounds, anthraquinone-containing compounds, xanthone-containing compounds, benzotriazine-containing compounds, benzotriazinone-containing compounds, benzotriazole-containing compounds, benzoate-containing compounds, cyanoacrylate-containing compounds, triazine-containing compounds, oxalylanilide-containing compounds, salicylate-containing compounds and pyrene-containing compounds, all of which are substituted with hydroxyl groups.
[0132] The wavelength range of light absorbed by the first UV absorbing compound may be different from the wavelength range of light absorbed by the second UV absorbing compound.
[0133] The UV absorber can absorb ultraviolet rays and prevent ultraviolet rays from penetrating the organic light-emitting device 200 (or reduce the amount of ultraviolet rays penetrating the organic light-emitting device 200). Therefore, the organic light-emitting display device 10 including the UV absorber in the thin film package 300 can prevent the emission layer including organic materials, the insulating film, etc. from being damaged by ultraviolet rays (or can reduce the possibility or degree of such damage).
[0134] In one embodiment, the UV absorber may absorb wavelengths from about 280 nm to about 430 nm.
[0135] In one embodiment, the free radical scavenger may include at least one of the free radical scavenging compounds,
[0136] The free radical scavenging compound may be selected from phenol-containing compounds, hindered amine-containing compounds and phenylenediamine-containing compounds.
[0137] In one embodiment, the free radical scavenger may include at least one compound represented by one selected from Formula A4-1 to Formula A4-3:
[0138] Formula A4-1
[0139]
[0140] Formula A4-2
[0141]
[0142] Formula A4-3
[0143]
[0144] In Formula A4-1 to Formula A4-3,
[0145] Cyclic Ar 1 It can be a benzene ring or a naphthalene ring,
[0146] L 10 and L 20 may be independently -O-, -S-, S(=O) 2 -, -C(=O)-, -C(=O)O-, -C(=O)NH-,C 1 -C 30 Hydrocarbon, C 5 -C 60 Carbocyclic or C 2 -C 30 Heterocyclic group,
[0147] m10 and m20 may each independently be an integer from 0 to 5, wherein when m10 is two or more, two or more L 10 can be the same or different from each other. When m10 is 0, L 10 It may be a single bond, and when m20 is two or more, two or more L 20 can be the same or different from each other. When m20 is 0, L 20 Can be a single key,
[0148] R 50 , R 51 , R 60 , R 61 , R 62 and R 70 To R 74can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 60 Cycloalkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0149] a50 can be an integer from 1 to 6,
[0150] a60 can be an integer from 1 to 4,
[0151] a70 can be an integer from 1 to 4,
[0152] When a50 is two or more, two or more R 50can be the same or different from each other,
[0153] When a60 is two or more, two or more R 60 can be the same or different from each other,
[0154] When a70 is two or more, two or more R 70 can be the same or different from each other,
[0155] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 60 Cycloalkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0156] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0157] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) of at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0158] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups;
[0159] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) of at least one of C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0160] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0161] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, substituted with C 1 -C 60 Alkyl C 6 -C 60 Aryl, substituted with C 6 -C 60 Aryl C 6 -C 60 Aryl, terphenyl, C 1 -C 60 Heteroaryl, substituted with C 1 -C 60Alkyl C 1 -C 60 Heteroaryl, substituted with C 6 -C 60 Aryl C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
[0162] In one embodiment, in Formula A4-1 to Formula A4-3,
[0163] L 10 and L 20 Can be independently selected from:
[0164] -O-, -S-, S(=O) 2 -, -C(=O)-, -C(=O)O- and -C(=O)NH-;
[0165] C 1 -C 20 Alkylene, C 2 -C 20 Alkenylene, C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 Heteroarylene groups, divalent non-aromatic condensed polycyclic groups, and divalent non-aromatic condensed heteropolycyclic groups; and
[0166] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) of at least one of C 1 -C 20 Alkylene, C 2 -C 20 Alkenylene, C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 Heteroarylene groups, divalent non-aromatic condensed polycyclic groups and divalent non-aromatic condensed heteropolycyclic groups.
[0167] In one or more embodiments, in Formula A4-1 to Formula A4-3,
[0168] L 10 and L 20 One of can be selected from;
[0169] C 6 -C 30 Alkylene, C 6 -C 30 Alkenylene and C 6 -C 30 Alkyne; and
[0170] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl and -Si(Q 31 )(Q 32 )(Q33 ) in which at least one substituent is C 6 -C 30 Alkylene, C 6 -C 30 Alkenylene and C 6 -C 30 Alkyne, or
[0171] R 50 , R 51 , R 60 , R 61 and R 70 To R 74 One of can be selected from:
[0172] C 6 -C 30 Alkyl, C 6 -C 30 Alkoxy, C 6 -C 30 Alkenyl and C 6 -C 30 Alkynyl; and
[0173] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl and -Si(Q 31 )(Q 32 )(Q 33 ) in which at least one substituent is C 6 -C 30 Alkyl, C 6 -C 30 Alkoxy, C 6 -C 30 Alkenyl and C 6 -C 30 Alkynyl.
[0174] In one embodiment, from L 10 , L 20 , R 50 , R 51 , R 60 , R 61 and R 70 To R74 At least one selected therefrom may include a hydrocarbon chain consisting of six or more carbon atoms, thereby improving miscibility with other components in the thin film encapsulation 300 .
[0175] In one embodiment, the free radical scavenger may include at least one compound represented by one selected from Formula A5-1 to Formula A5-4:
[0176]
[0177] In Formula A5-1 to Formula A5-4,
[0178] R 51 To R 53 , R 61 To R 66 and R 71 To R 76 Can be independently selected from:
[0179] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0180] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,
[0181] L 10 and L 20 All are independently the same as described above.
[0182] The phenol-containing compound may be butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), tert-butylhydroquinone (TBHQ), propyl gallate (PG), catechol (1,2-benzenediol), 1,2-naphthalene diol, and the like.
[0183] The hindered amine-containing compound can be bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, bis-(N-methyl-2,2,6,6-tetramethyl-4-piperidinyl) sebacate, bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, 1,2,2,6,6-pentamethyl-4-piperidinyl-tridecyl-1,2,3,4-butanetetracarboxylate, tetrakis-(2,2,6,6-tetramethyl-4-piperidinyl)-1,2,3,4-butanetetracarboxylate, tetrakis-(N-methyl-2,2,6,6-tetramethyl-4-piperidinyl)-1,2,3,4-butanetetracarboxylate, and the like.
[0184] The phenylenediamine-containing compound may be o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, etc.; or the phenylenediamine-containing compound may be substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl and C 1 -C 20 At least one of the alkoxy groups is o-phenylenediamine, m-phenylenediamine or p-phenylenediamine.
[0185] In one embodiment, the amount of the radical scavenger may be in a range of about 0.5 parts by weight to about 20 parts by weight based on 100 parts by weight of the UV absorber. When the amount of the radical scavenger is within this range, the optical stability of the thin film encapsulation 300 is high due to the radical scavenger, so that the thin film encapsulation 300 effectively protects the organic light-emitting device 200 from ultraviolet rays. When the amount of the radical scavenger is less than about 0.5 parts by weight, it may not be enough to ensure the optical stability of the thin film encapsulation 300, and when the amount of the radical scavenger exceeds 20 parts by weight, the transmittance of the thin film encapsulation 300 in the visible light region may be hindered, and the luminous efficiency of the organic light-emitting device 200 (e.g., a blue organic light-emitting device having a maximum emission wavelength of about 430 nm to about 460 nm) may be hindered.
[0186] In one embodiment, the thin film encapsulation 300 may further include a matrix resin, and the UV absorber may be dispersed in the matrix resin. In this case, the UV absorber may be simply dispersed in the matrix resin. Alternatively, the UV absorber may be cross-linked with the matrix resin. For example, the UV absorber may include a polymerizable functional group, and the UV absorber may be cross-linked with the matrix resin.
[0187] In one embodiment, the thin film encapsulation 300 may further include a photopolymerization initiator. The photopolymerization initiator may use any suitable one available in the art without any particular limitation, and may use a photopolymerization initiator curable at a wavelength of, for example, about 360 nm to about 420 nm.
[0188] In one embodiment, the thin film encapsulation 300 may further include at least two types (or kinds) of photopolymerization initiators. For example, one of the at least two types (or kinds) of photopolymerization initiators may be curable in the UV region (e.g., at a wavelength of about 360 nm to about 420 nm), and the other may be curable in the visible ray region (e.g., at a wavelength of about 400 nm to about 770 nm). In one or more embodiments, the at least two types (or kinds) of photopolymerization initiators may be curable in both the UV region and the visible ray region.
[0189] In one embodiment, the thin film package 300 may further include at least one selected from metal, metal halide, metal nitride, metal oxide, metal oxynitride, silicon nitride, silicon oxide, and silicon oxynitride.
[0190] For example, the thin film package 300 may include MgF 2 、LiF、AlF 3 , NaF, silicon oxide, silicon nitride, silicon oxynitride, aluminum oxide, aluminum nitride, aluminum oxynitride, titanium oxide, titanium nitride, tantalum oxide, tantalum nitride, hafnium oxide, hafnium nitride, zirconium oxide, zirconium nitride, cerium oxide, cerium nitride, tin oxide, tin nitride and magnesium oxide, but the embodiments of the present disclosure are not limited thereto.
[0191] In one embodiment, the thin film encapsulation 300 may include at least one organic film. The at least one organic film may include a first organic film, and the UV stabilizing mixture may be included in the first organic film.
[0192] In one embodiment, the thin film encapsulation 300 (eg, first organic film) including the UV stable mixture may have a transmittance of about 10% or less (eg, 8%) with respect to light having a wavelength of about 400 nm to about 410 nm (eg, 405 nm).
[0193] In one or more embodiments, the thin film package 300 (e.g., the first organic film) including the UV-stable mixture can have a transmittance of about 80% or greater (e.g., 90% or greater) with respect to light having a wavelength of about 430 nm or greater, and can have a transmittance of about 10% or less with respect to light having a wavelength of about 405 nm or less.
[0194] In one embodiment, when the first organic film is exposed to about 52,000 Wh / m 2 When the exposure amount is 200 nm, the change in transmittance with respect to a wavelength range of about 400 nm to about 410 nm may be less than 5%.
[0195] In one or more embodiments, when the first organic film is exposed to about 52,000 Wh / m 2 When the exposure amount is 200 nm, the change in transmittance with respect to the wavelength range of about 400 nm to about 405 nm can be less than 3%.
[0196] In one or more embodiments, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a maximum emission wavelength of about 405 nm or light having a wavelength range of about 380 nm to about 410 nm, a change in transmittance relative to a wavelength range of about 400 nm to about 410 nm may be less than 5%.
[0197] In one or more embodiments, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a maximum emission wavelength of about 405 nm or light having a wavelength range of about 380 nm to about 410 nm, a change in transmittance relative to a wavelength range of about 400 nm to about 405 nm may be less than 3%.
[0198] The change in transmittance in the above wavelength range may be measured by, for example, exposing the first organic film through the use of an LED lamp emitting light in a wavelength range of about 380 nm to about 410 nm and having a maximum emission wavelength of about 405 nm.
[0199] In one embodiment, the first organic film may have a thickness in a range of about 10 nm to about 20 μm, for example, in a range of about 10 nm to about 10 μm.
[0200] In one embodiment, the amount of the UV stabilizing compound can be in a range of about 3 parts by weight to about 10 parts by weight based on 100 parts by weight of the first organic film. By controlling the amount of the UV stabilizing compound in the first organic film, the maximum absorption wavelength of the first organic film can be finely adjusted, and the UV absorption spectrum can be controlled.
[0201] For example, at least one organic film may consist of a UV-stabilizing mixture.
[0202] In one embodiment, in addition to the UV stabilizing mixture, at least one organic film may further include a matrix resin, and the UV stabilizing mixture may be dispersed in the matrix resin. In this case, the UV stabilizing mixture may be simply dispersed in the matrix resin, or the UV stabilizing mixture may be cross-linked with the matrix resin.
[0203] In one embodiment, the first organic film may further include a matrix resin.
[0204] The matrix resin may include at least one selected from acryl-based resin, methacryl-based resin, isoprene-based resin, vinyl-based resin, epoxy-based resin, urethane-based resin, cellulose resin, perylene-based resin, imide-based resin, and silicone-based resin.
[0205] In one embodiment, at least one organic film may further include a photopolymerization initiator in addition to the UV stabilizing compound. The photopolymerization initiator is the same as described above.
[0206] In one embodiment, at least one organic film may include a matrix resin and a photopolymerization initiator in addition to the UV stabilizing mixture.
[0207] At least one organic film can be formed in a set or predetermined area by using various suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing or laser induced thermal imaging (LITI). The number and thickness of the organic film can be appropriately selected by considering productivity or device characteristics.
[0208] In one embodiment, the thin film package 300 may further include at least one inorganic film, and the at least one inorganic film may further include a first inorganic film.
[0209] In one embodiment, the inorganic film may include at least one selected from metal, metal halide, metal nitride, metal oxide, metal oxynitride, silicon nitride, silicon oxide, and silicon oxynitride.
[0210] For example, the inorganic film may include MgF 2 、LiF、AlF 3 , NaF, silicon oxide, silicon nitride, silicon oxynitride, aluminum oxide, aluminum nitride, aluminum oxynitride, titanium oxide, titanium nitride, tantalum oxide, tantalum nitride, hafnium oxide, hafnium nitride, zirconium oxide, zirconium nitride, cerium oxide, cerium nitride, tin oxide, tin nitride and magnesium oxide, but the embodiments of the present disclosure are not limited thereto.
[0211] At least one inorganic film may be formed in a set or predetermined area by using various suitable methods such as chemical vapor deposition (CVD), plasma enhanced chemical vapor deposition (PECVD), sputtering, atomic layer deposition (ALD) or thermal evaporation. The number and thickness of the inorganic film may be appropriately selected by considering productivity or device characteristics.
[0212] In one embodiment, at least one organic film may include a first organic film, at least one inorganic film may include a first inorganic film, and the first organic film may be disposed between the organic light-emitting device 200 and the first inorganic film. For example, at least one organic film may include a first organic film, at least one inorganic film may include a first inorganic film, and the first organic film and the second inorganic film may be sequentially stacked in the order of the statement from the organic light-emitting device 200. It should be understood that the term "sequentially stacked" does not exclude that another film is disposed between the organic light-emitting device 200 and the first organic film and / or between the first organic film and the first inorganic film.
[0213] In one or more embodiments, at least one organic film may include a first organic film, at least one inorganic film may include a first inorganic film, and the first inorganic film may be disposed between the organic light-emitting device 200 and the first organic film. For example, at least one organic film may include a first organic film, at least one inorganic film may include a first inorganic film, and the first inorganic film and the first organic film may be sequentially stacked from the organic light-emitting device 200 in the order stated.
[0214] In one or more embodiments, at least one organic film may include a first organic film, at least one inorganic film may include a first inorganic film and a second inorganic film, and the first inorganic film, the first organic film and the second inorganic film may be stacked sequentially from the organic light-emitting device 200 in the order stated.
[0215] In one or more embodiments, at least one organic film may include a first organic film and a second organic film, at least one inorganic film may include a first inorganic film, and the first organic film, the first inorganic film, and the second organic film may be stacked sequentially from the organic light-emitting device 200 in the order stated.
[0216] In one or more embodiments, at least one organic film may include a first organic film and a second organic film, at least one inorganic film may include a first inorganic film and a second inorganic film, and the first inorganic film, the first organic film, and the second inorganic film and the second organic film may be stacked sequentially from the organic light-emitting device 200 in the order of the statement.
[0217] In one or more embodiments, at least one organic film may include a first organic film and a second organic film, at least one inorganic film may include a first inorganic film and a second inorganic film, and the first organic film, the first inorganic film, the second organic film and the second inorganic film may be stacked sequentially from the organic light-emitting device 200 in the order of the statement.
[0218] In one or more embodiments, at least one organic film may include a first organic film and a second organic film, at least one inorganic film may include a first inorganic film and a second inorganic film, and the first inorganic film, the second inorganic film, the first organic film and the second organic film may be stacked sequentially from the organic light-emitting device 200 in the order of the statement.
[0219] In one or more embodiments, at least one organic film may include a first organic film and a second organic film, at least one inorganic film may include a first inorganic film and a second inorganic film, and the first organic film, the second organic film, the first inorganic film and the second inorganic film may be stacked sequentially from the organic light-emitting device 200 in the order of the statements.
[0220] In one or more embodiments, at least one organic film may include a first organic film and a second organic film, at least one inorganic film may include a first inorganic film, a second inorganic film, and a third inorganic film, and the first inorganic film, the first organic film, the second inorganic film, the second organic film, and the third inorganic film may be stacked sequentially from the organic light-emitting device 200 in the order of the statement.
[0221] In one or more embodiments, at least one organic film may include a first organic film, a second organic film, and a third organic film, at least one inorganic film may include a first inorganic film and a second inorganic film, and the first organic film, the first inorganic film, the second organic film, the second inorganic film, and the third organic film may be sequentially stacked in the order stated from the organic light emitting device 200, but the embodiments of the present disclosure are not limited thereto. The number of organic films and inorganic films and the stacking order of inorganic films and organic films may be appropriately modified according to design.
[0222] The organic light emitting display device 10 may include a plurality of organic light emitting devices 200. In one embodiment, the organic light emitting display device 10 may include: a substrate; an organic emission unit including a plurality of organic light emitting devices 200 located on the substrate; and a thin film encapsulation member 300 sealing the organic emission unit, wherein the thin film encapsulation member 300 includes a UV stabilizing mixture. The UV stabilizing mixture is the same as described above.
[0223] For example, the thin film encapsulation 300 may include a UV stabilizing mixture, and in addition to the UV stabilizing mixture, the thin film encapsulation 300 may further include a matrix resin. The matrix resin is the same as described above.
[0224] In one embodiment, the thin film encapsulation 300 may include metal, metal halide, metal nitride, metal oxide, metal oxynitride, silicon nitride, silicon oxide, and silicon oxynitride in addition to the UV stabilizing compound.
[0225] In one embodiment, the thin film package 300 may include at least one organic film and at least one inorganic film, and the at least one organic film may include a UV absorber. The at least one organic film and the at least one inorganic film are the same as described above.
[0226] Another aspect of the embodiment provides a method of manufacturing an electronic device, the method comprising:
[0227] forming an organic light emitting device on a substrate; and
[0228] forming a thin film package sealing the organic light emitting device on the substrate,
[0229] The formation of the thin film encapsulation member includes providing a thin film encapsulation composition for sealing the organic light-emitting device and curing the thin film encapsulation composition.
[0230] The thin film encapsulation composition comprises a UV stable mixture,
[0231] The UV stabilizing mixture includes a UV absorber and a free radical scavenger.
[0232] The thin film encapsulant, UV stabilizing mixture, UV absorber and free radical scavenger are the same as those described above. When the electronic device is manufactured according to the above method, external UV rays are blocked from reaching the organic light emitting device, thereby preventing damage to the organic light emitting device when it is continuously exposed to UV rays (or reducing the possibility or degree of such damage), and improving the durability of the organic light emitting device and the electronic device including the organic light emitting device.
[0233] In one embodiment, the thin film encapsulation composition may further include a matrix resin monomer and a photopolymerization initiator.
[0234] The matrix resin monomer may be photopolymerized to form the matrix resin included in the thin film encapsulation. For example, the matrix resin monomer may be photopolymerized by a photopolymerization initiator to form the matrix resin included in the thin film encapsulation. The photopolymerization initiator is the same as described above.
[0235] Figure 2 is a schematic cross-sectional view of an organic light emitting display device as one of the electronic devices according to an embodiment.
[0236] Reference Figure 2, forming a backplane. The backplane may be understood to include at least: a substrate 100; a plurality of first electrodes 210R, 210G, and 210B located on the substrate 100; and a pixel defining film 180 formed to expose at least a portion of the central portion including the first electrodes 210R, 210G, and 210B. The pixel defining film 180 may have a shape protruding from the first electrodes 210R, 210G, and 210B in the +z direction relative to the substrate 100.
[0237] The first electrode 210R, 210G and 210B can be understood as pixel electrodes. The pixel electrode 210R, the pixel electrode 210G and the pixel electrode 210B among the pixel electrodes can be understood as the first pixel electrode, the second pixel electrode and the third pixel electrode respectively. This is because the intermediate layer formed on the first pixel electrode to the third pixel electrode can be different. For convenience, the terms "pixel electrode 210R", "pixel electrode 210G" and "pixel electrode 210B" are used to replace the first pixel electrode, the second pixel electrode and the third pixel electrode. The pixel electrode is the same as described in conjunction with the first electrode.
[0238] The pixel defining film 180 may have an opening corresponding to each sub-pixel, that is, an opening exposing the central portion of the pixel electrodes 210R, 210G, and 210B or the entire pixel electrodes 210R, 210G, and 210B, thereby defining the pixel. In addition, the pixel defining film 180 may increase the distance between the end of the pixel electrodes 210R, 210G, and 210B and the second electrode 230 located on the pixel electrodes 210R, 210G, and 210B, thereby preventing arcs, etc. from being generated at the end of the pixel electrodes 210R, 210G, and 210B (or reducing the possibility or degree of such arcs).
[0239] If necessary, the back panel may also include other various suitable components. Figure 2 As shown in , the thin film transistor TFT or the capacitor Cap may be formed on the substrate 100. The backplane may include the following components: such as a buffer layer 110 for preventing impurities from penetrating the semiconductor layer of the thin film transistor TFT (or reducing the possibility or amount of impurities penetrating the semiconductor layer of the thin film transistor TFT); a gate insulating film 130 for insulating the semiconductor layer of the thin film transistor TFT from the gate electrode; an interlayer insulating film 150 for insulating the source electrode / drain electrode of the thin film transistor TFT from the gate electrode; and a planarizing film 170 covering the thin film transistor TFT and having a substantially flat upper surface.
[0240] After forming the backplane, the intermediate layers 220R, 220G, and 220B are formed. The intermediate layers 220R, 220G, and 220B may have a multilayer structure including an emission layer. In this case, unlike those shown, some of the intermediate layers 220R, 220G, and 220B may be a common layer substantially corresponding to the entire surface of the substrate 100, and some of the intermediate layers 220R, 220G, and 220B may be pattern layers patterned corresponding to the pixel electrodes 210R, 210G, and 210B.
[0241] After the intermediate layers 220R, 220G, and 220B are formed, the second electrode 230 is formed on the intermediate layers 220R, 220G, and 220B.
[0242] After forming the second electrode 230 , the thin film encapsulation 300 is formed to protect the organic light emitting device 200 including the pixel electrodes 210R, 210G, and 210B, the intermediate layers 220R, 220G, and 220B, and the second electrode 230 from impurities such as external oxygen or moisture.
[0243] The thin film encapsulation 300 may extend to cover not only the upper surface of the organic light-emitting device 200 but also the side surfaces of the organic light-emitting device 200 and the contact portion of the substrate 100. Therefore, it is possible to effectively prevent external oxygen and moisture from penetrating the organic light-emitting device 200 (or reduce the possibility or amount of external oxygen and moisture penetrating the organic light-emitting device 200).
[0244] The thin film encapsulation 300 includes a UV stabilizing mixture.
[0245] [Heterocyclic compounds]
[0246] Another aspect of the embodiment provides a heterocyclic compound represented by Formula B1.
[0247] The heterocyclic compound is represented by formula B1:
[0248] Formula B1
[0249] (A 1 ) m1 -L 1 -(A 2 ) m2 .
[0250] L in Formula B1 1 For connection A 1 and A 2 (m1+m2) price C 2 -C 20 Organic group.
[0251] In one embodiment, L 1 It may be a group represented by formula B2:
[0252] Formula B2
[0253] *-(X 1 ) n1 -L 11 -(X 2 ) n2 -*′.
[0254] In formula B1, X 1 and X 2 may each independently be a single bond, -O-, -S-, -C(=O)-, -C(=O)O-, *-CONH- or -NHC(=O)NH-,
[0255] L 11 Can be selected from:
[0256] C 2 -C 12 Alkylene, C 2 -C 12 Alkenylene and C 2 -C 12 Alkyne; and
[0257] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 ) of at least one of C 2 -C 12 Alkylene, C 2 -C 12 Alkenylene and C 2 -C 12 Alkynylidene,
[0258] n1 and n2 may each independently be an integer from 1 to 3,
[0259] Q 31 To Q 33can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0260] * and *' both indicate the binding sites with adjacent atoms.
[0261] -NHC(=O)NH- has the following structure:
[0262]
[0263] In the above structures, * and *' both represent the binding sites with adjacent atoms.
[0264] In one embodiment, L 1 It may be a group represented by one selected from Formula B2-1 to Formula B2-5:
[0265] Formula B2-1
[0266]
[0267] Formula B2-2
[0268]
[0269] Formula B2-3
[0270] *-OL 11 -O-*′
[0271] Formula B2-4
[0272]
[0273] Formula B2-5
[0274] *-L 11 - * ′.
[0275] In Formula B2-1 to Formula B2-5,
[0276] L 11 Same as described here,
[0277] * and *' both indicate the binding sites with adjacent atoms.
[0278] In one embodiment, L 11 may be ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene and dodecylene; and
[0279] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 At least one substituent of the alkoxy group may be ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene or dodecylene.
[0280] In formula B1, A 1 It may be a UV absorbing group.
[0281] In one embodiment, A 1 It may include at least one group selected from a benzophenone-containing group, a benzoquinone-containing group, an anthraquinone-containing group, an xanthone-containing group, a benzotriazine-containing group, a benzotriazinone-containing group, a benzotriazole-containing group, a benzoate-containing group, a cyanoacrylate-containing group, a triazine-containing group, an oxalylanilide-containing group, a salicylate-containing group and a pyrene-containing group, all of which are substituted with hydroxyl groups.
[0282] The benzophenone-containing group may include, for example, a 2-hydroxybenzophenone group, a 2,4-dihydroxybenzophenone group, a 2-hydroxy-4-methoxybenzophenone group, a 2-hydroxy-4-octylbenzophenone group, a 4-dodecyloxy-2-hydroxybenzophenone group, a 4-benzyloxy-2-hydroxybenzophenone group, a 2,2′,4,4′-tetrahydroxybenzophenone group, a 2,2′-dihydroxy-4,4′-dimethoxybenzophenone group, and the like.
[0283] The benzoquinone-containing group may include, for example, a 2-hydroxybenzoquinone group.
[0284] The anthraquinone-containing group may include, for example, a 1-hydroxyanthraquinone group, a 1,5-hydroxyanthraquinone group, a 1,8-hydroxyanthraquinone group, and the like.
[0285] The benzotriazole-containing group may include, for example, 2-(2-hydroxyphenyl)benzotriazolyl, 2-(5-methyl-2-hydroxyphenyl)benzotriazolyl, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazolyl, 2-(3,5-di-tert-butyl-2-hydroxyphenyl)benzotriazolyl, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazolyl, 2-(3,5-di-tert-butyl-2-hydroxyphenyl)-5-chlorobenzotriazolyl, 2-(3,5-di-tert-butyl-2-hydroxyphenyl)-5-chlorobenzotriazolyl, 2-(3,5-di-tert-acyl-2-hydroxyphenyl)benzotriazolyl, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazolyl, and the like.
[0286] The benzoate-containing group may include, for example, 2-hydroxybenzoic acid phenyl ester group, 2,4-di-tert-butylphenyl-3',5'-di-tert-butyl-4-hydroxybenzoate group, and the like.
[0287] The triazine-containing group may include, for example, a 2-(4,6-diphenyl-1,3,5-triazine-2-yl)phenol group, a 2-(4,6-diphenyl-1,3,5-triazine-2-yl)-5-(hexyl)oxy-phenol group, and a 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine group.
[0288] The salicylate-containing group may include, for example, phenyl salicylate, 4-tert-butylphenyl salicylate, and the like.
[0289] In an embodiment, A 1 It may be a group represented by one selected from Formula B3-1 to Formula B3-3:
[0290] Formula B3-1
[0291]
[0292] Formula B3-2
[0293]
[0294] Formula B3-3
[0295]
[0296] In Formula B3-1 to Formula B3-3,
[0297] CY 1 and CY 2 may be independently selected from phenyl, naphthyl, anthracenyl, pyrenyl and phenanthrenyl,
[0298] R 1 and R 2can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 60 Cycloalkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0299] R 1 and R 2 can be optionally connected to form -(Y 1 ) k1 - a linker, wherein Y 1 can be -O-, -S- or -C(=O), k1 can be an integer from 1 to 3,
[0300] Y2 and Y 3 One of them can be N, Y 2 and Y 3 The other of may be a single bond, a double bond or -C(=O),
[0301] R 10 , R 20 , R 30 and R 40 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 60 Cycloalkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0302] b10 can be an integer from 1 to 17,
[0303] b20 can be an integer from 1 to 3,
[0304] b30 and b40 may each independently be an integer from 1 to 4,
[0305] At least one R 10 , at least one R 20 and at least one R 30 may all independently be hydroxyl groups,
[0306] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 60 Cycloalkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0307] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0308] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) of at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0309] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups;
[0310] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) of at least one of C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0311] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0312] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, substituted with C 1 -C 60 Alkyl C 6 -C 60 Aryl, substituted with C 6 -C 60 Aryl C 6 -C 60 Aryl, terphenyl, C1 -C 60 Heteroaryl, substituted with C 1 -C 60 Alkyl C 1 -C 60 Heteroaryl, substituted with C 6 -C 60 Aryl C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0313] *Indicates the binding site with the adjacent atom.
[0314] In one embodiment, in Formula B3-1 to Formula B3-3,
[0315] R 1 and R 2 Can be independently selected from:
[0316] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0317] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,
[0318] R 1 and R 2 Can be connected to form -(Y 1 ) k1 -linking group, wherein -(Y1 ) k1 - may be -O-, -S- or -C(=O)-.
[0319] For example, R 1 and R 2 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,
[0320] R 1 and R 2 Can be connected to form -(Y 1 ) k1 -linking group, wherein -(Y 1 ) k1 - may be -O-, -S- or -C(=O)-.
[0321] In one embodiment, in Formula B3-1 to Formula B3-3, R 10 , R 20 , R 30 and R 40 Can be independently selected from:
[0322] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0323] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1-C 20 Alkoxy.
[0324] For example, R 10 , R 20 , R 30 and R 40 Can be independently selected from:
[0325] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0326] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy.
[0327] In one embodiment, A 1 It may be a group represented by one selected from Formula B4-1 to Formula B4-30:
[0328]
[0329]
[0330]
[0331]
[0332] In Formula B4-1 to Formula B4-30,
[0333] R 3 , R 4 and R 11To R 18 Combined with R 10 Same as described,
[0334] a16 can be 1, 2, 3 or 4,
[0335] b16 can be 1 or 2,
[0336] b17 can be 1, 2, 3 or 4,
[0337] c15 can be 1 or 2,
[0338] c16 can be 1, 2 or 3,
[0339] c17 can be 1 or 2,
[0340] R 21 To R 23 Combined with R 20 Same as described,
[0341] R 31 To R 35 Combined with R 30 Same as described,
[0342] R 41 To R 44 Combined with R 40 Same as described,
[0343] R 11 To R 18 At least one of R 21 To R 23 At least one of R 31 To R 35 At least one of them may be a hydroxyl group,
[0344] *Indicates the binding site with the adjacent atom.
[0345] In one embodiment, R in Formula B4-1 to Formula B4-26 11 , R 15 and R 18 At least one of them may be a hydroxyl group. 11 It may be a hydroxyl group, but the embodiments of the present disclosure are not limited thereto.
[0346] In one or more embodiments, R in Formula B4-27 21 It may be a hydroxyl group.
[0347] In one or more embodiments, R in Formula B4-28 to Formula B4-30 31 and R 35 At least one of them may be a hydroxyl group. 31It may be a hydroxyl group, but the embodiments of the present disclosure are not limited thereto.
[0348] In one embodiment, A 1 It may be a group represented by one selected from Formula B5-1 and Formula B5-2:
[0349]
[0350] In Formula B5-1 and Formula B5-2,
[0351] R 14 , R 15 and R 16 are independently combined with R 10 Same as described,
[0352] *Indicates the binding site with the adjacent atom.
[0353] In formula B1, A 2 May be a free radical scavenging group.
[0354] In one embodiment, A 2 A group derived from at least one compound selected from a phenol-containing compound, a hindered amine-containing compound, and a phenylenediamine-containing compound may be included.
[0355] The phenol-containing compound may be BHA, BHT, TBHQ, PG, catechol (1,2-benzenediol), 1,2-naphthalene diol, and the like.
[0356] The hindered amine-containing compound can be bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, bis-(N-methyl-2,2,6,6-tetramethyl-4-piperidinyl) sebacate, bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, 1,2,2,6,6-pentamethyl-4-piperidinyl-tridecyl-1,2,3,4-butanetetracarboxylate, tetrakis-(2,2,6,6-tetramethyl-4-piperidinyl)-1,2,3,4-butanetetracarboxylate, tetrakis-(N-methyl-2,2,6,6-tetramethyl-4-piperidinyl)-1,2,3,4-butanetetracarboxylate, and the like.
[0357] The phenylenediamine-containing compound may be o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, etc.; or the phenylenediamine-containing compound may be substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl and C 1 -C 20 At least one of the alkoxy groups is o-phenylenediamine, m-phenylenediamine or p-phenylenediamine.
[0358] In one embodiment, A 2 It may be a group represented by one selected from Formula B6-1 to Formula B6-3:
[0359] Formula B6-1
[0360]
[0361] Formula B6-2
[0362]
[0363] Formula B6-3
[0364]
[0365] In Formula B6-1 to Formula B6-3,
[0366] Ar 1 It can be a benzene ring or a naphthalene ring,
[0367] R 50 , R 60 , R 61 and R 70 To R 74 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 60 Cycloalkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0368] b50 can be an integer from 1 to 6,
[0369] b60 can be an integer from 1 to 4,
[0370] b70 can be an integer from 1 to 3,
[0371] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 60 Cycloalkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0372] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0373] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) of at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0374] C 3 -C 10 Cycloalkyl, C1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups;
[0375] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22) of at least one of C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0376] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0377] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, substituted with C 1 -C 60 Alkyl C 6 -C 60 Aryl, substituted with C 6 -C 60 Aryl C 6 -C 60 Aryl, terphenyl, C 1 -C 60 Heteroaryl, substituted with C 1 -C 60 Alkyl C 1 -C 60 Heteroaryl, substituted with C 6 -C 60 Aryl C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0378] *Indicates the binding site with the adjacent atom.
[0379] In one embodiment, R 50 , R 60 , R 61 and R 70 To R 74 Can be independently selected from:
[0380] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0381] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy.
[0382] In one embodiment, R 50 , R 60 , R 61 and R 70 To R 74 Can be independently selected from:
[0383] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0384] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 1 -C 20 Alkoxy, C 3 -C 20 Cycloalkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, At least one of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 1 -C 20 Alkyl and C 1 -C 20 Alkoxy.
[0385] In one embodiment, A 2 It may be a group represented by one selected from Formula B7-1 to Formula B7-3:
[0386]
[0387] In Formula B7-1 to Formula B7-3,
[0388] R 51 , R52 and R 53 are independently combined with R 50 Same as described,
[0389] R 61 To R 66 are independently combined with R 60 Same as described,
[0390] R 71 To R 74 are independently combined with R 71 To R 74 Same as described,
[0391] R 75 and R 76 are independently combined with R 70 Same as described,
[0392] *Indicates the binding site with the adjacent atom.
[0393] In one embodiment, A 2 It may be a group represented by one selected from Formula B8-1 to Formula B8-12:
[0394]
[0395] In Formula B8-1 to Formula B8-12,
[0396] R 61 , R 75 and R 76 are independently combined with the above R 61 , R 75 and R 76 The description is the same, and * indicates the binding site with the adjacent atom.
[0397] In Formula B1, m1 may be an integer from 1 to 3, and m2 may be an integer from 1 to 3.
[0398] In one embodiment, in Formula B1, m1 may be 1, and m2 may be 1.
[0399] In one embodiment, the heterocyclic compound can be selected from Compound 1 to Compound 14:
[0400]
[0401]
[0402] In compounds 1 to 14,
[0403] R 81 To R 83can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy.
[0404] In one embodiment, the thin film encapsulation composition may include a heterocyclic compound.
[0405] The thin film encapsulation composition may include a heterocyclic compound, and may further include a solvent.
[0406] The solvent may include, for example, 10 -C 20 Alkyl, C 10 -C 20 Alkoxy, C 10 -C 20 Alkenyl and C 10 -C 20 At least one of alkynyl di(meth)acrylate, di(meth)acryl-terminated silicon and diepoxy-terminated silicon. In addition, the solvent may also include mono(meth)acrylate and monoepoxide as diluents.
[0407] In one or more embodiments, the solvent may have a visible light transmittance of about 70% or greater.
[0408] The solvent may have a viscosity of about 5 cP to about 10,000 cP.
[0409] The thin film encapsulation composition may further include a photoinitiator or a thermal initiator. As the photoinitiator or the thermal initiator, those available in the art may be used without any particular limitation.
[0410] In one embodiment, the thin film encapsulation composition may include at least two types (or species) of heterocyclic compounds.
[0411] For example, the thin film encapsulation may include a first heterocyclic compound represented by Formula B1 and a second heterocyclic compound represented by Formula B1, and a wavelength range of light absorbed by the first heterocyclic compound may be different from a wavelength range of light absorbed by the second heterocyclic compound.
[0412] In one embodiment, when the thin film encapsulation composition includes at least two types (or species) of heterocyclic compounds, a thin film encapsulation formed by using the thin film encapsulation composition can have an average transmittance of about 10% or less in a wavelength range of about 380nm to about 400nm, and can have an average transmittance of about 60% or more in a wavelength range of about 400nm to about 430nm.
[0413] In one embodiment, the thin film encapsulation composition may further include a matrix resin monomer, a photopolymerization initiator, and a solvent.
[0414] For example, the thin film encapsulation composition may further include a matrix resin monomer. The matrix resin monomer may be a monomer for forming at least one of an acryl resin, a methacryl resin, an isoprene resin, a vinyl resin, an epoxy resin, an urethane resin, a cellulose resin, a perylene resin, an imide resin, and a silicone resin.
[0415] In one embodiment, the matrix resin monomer may be a (meth)acryl-based monomer.
[0416] In one or more embodiments, the thin film encapsulation composition may further include a photopolymerization initiator. As the photopolymerization initiator, a suitable photopolymerization initiator available in the art may be used without any specific limitation. For example, a photopolymerization initiator curable at a wavelength of about 360 nm to about 420 nm may be used.
[0417] In one embodiment, the thin film encapsulation composition may also include at least two types (or kinds) of photopolymerization initiators. For example, one of the at least two types (or kinds) of photopolymerization initiators may be curable in the UV region (e.g., at a wavelength of about 360 nm to about 420 nm), and the other may be curable in the visible ray region (e.g., at a wavelength of about 400 nm to about 770 nm). In one or more embodiments, the at least two types (or kinds) of photopolymerization initiators may be curable in both the UV region and the visible ray region.
[0418] In one embodiment, the thin film encapsulation composition may further include a matrix resin monomer and a photopolymerization initiator.
[0419] The matrix resin monomer may be photopolymerized to form the matrix resin included in the thin film encapsulation. For example, the matrix resin monomer may be photopolymerized by a photopolymerization initiator to form the matrix resin included in the thin film encapsulation. The photopolymerization initiator is the same as described above.
[0420] In addition, as described above, another aspect of the embodiment provides an electronic device, the electronic device comprising:
[0421] substrate;
[0422] an organic light emitting device disposed on a substrate; and
[0423] Thin film encapsulation, sealing organic light emitting devices,
[0424] Wherein, the thin film encapsulation comprises a heterocyclic compound.
[0425] The electronic device in which the thin film encapsulation includes the heterocyclic compound may be, for example, an organic light emitting display device, but the embodiments of the present disclosure are not limited to the organic light emitting display device. Figure 1-Figure 2 The description is provided to understand the description of the electronic device and the organic light emitting display device. In this case, for example, a heterocyclic compound may be used instead of the UV stabilizing compound.
[0426] In one embodiment, the thin film encapsulation 300 may include at least two types (or species) of heterocyclic compounds.
[0427] For example, the thin film encapsulation may include a first heterocyclic compound represented by Formula B1 and a second heterocyclic compound represented by Formula B1, and a wavelength range of light absorbed by the first heterocyclic compound may be different from a wavelength range of light absorbed by the second heterocyclic compound.
[0428] In one embodiment, when the thin film encapsulation includes at least two types (or kinds) of heterocyclic compounds, the average transmittance within the wavelength range of about 380nm to about 400nm can be about 10% or less, and the average transmittance within the wavelength range of about 400nm to about 430nm can be about 60% or greater.
[0429] The heterocyclic compound can absorb ultraviolet rays and prevent ultraviolet rays from penetrating the organic light-emitting device 200 (or reduce the possibility or amount of ultraviolet rays penetrating the organic light-emitting device 200). Therefore, the organic light-emitting display device 10 in which the thin film encapsulation 300 includes the heterocyclic compound can prevent the emission layer, the insulating film, etc. including the organic material from being damaged by ultraviolet rays (or can reduce the possibility or degree of such damage).
[0430] In one embodiment, the thin film package 300 may include at least one organic film, the at least one organic film may include a first organic film, and the first organic film may include a heterocyclic compound.
[0431] In one embodiment, the thin film encapsulation (eg, the first organic film) including the heterocyclic compound may have a transmittance of about 10% or less (eg, 8%) with respect to light having a wavelength of about 400 nm to about 410 nm (eg, 405 nm).
[0432] In one or more embodiments, a thin film package including a heterocyclic compound (e.g., a first organic film) may have a transmittance of approximately 80% or greater (e.g., 90%) with respect to light having a wavelength of approximately 430 nm or greater, and may have a transmittance of approximately 10% or less with respect to light having a wavelength of approximately 405 nm or less.
[0433] In one embodiment, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a maximum emission wavelength of about 405 nm, a change in transmittance with respect to a wavelength range of about 400 nm to about 410 nm may be less than about 5%.
[0434] In one or more embodiments, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a maximum emission wavelength of about 405 nm, a change in transmittance with respect to a wavelength range of about 400 nm to about 405 nm may be less than about 3%.
[0435] In one or more embodiments, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a maximum emission wavelength of about 405 nm, a change in transmittance with respect to a wavelength range of about 400 nm to about 405 nm may be less than about 1%.
[0436] In one or more embodiments, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a wavelength range of about 380 nm to about 410 nm and a maximum emission wavelength of about 405 nm, a change in transmittance with respect to a wavelength range of about 400 nm to about 410 nm may be less than about 5%.
[0437] In one or more embodiments, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a wavelength range of about 380 nm to about 410 nm and a maximum emission wavelength of about 405 nm, a change in transmittance with respect to a wavelength range of about 400 nm to about 405 nm may be less than about 3%.
[0438] In one or more embodiments, when the first organic film is at about 52,000 Wh / m 2 When the exposure amount is exposed to light having a wavelength range of about 380 nm to about 410 nm and a maximum emission wavelength range of about 405 nm, a change in transmittance with respect to a wavelength range of about 400 nm to about 405 nm may be less than about 1%.
[0439] The change in transmittance with respect to the above wavelength range may be measured by, for example, exposing the first organic film through the use of an LED light emitting light in a wavelength range of about 380 nm to about 410 nm and having a maximum emission wavelength of about 405 nm.
[0440] In one embodiment, the first organic film may have a thickness in a range of about 10 nm to about 20 μm, for example, in a range of about 10 nm to about 10 μm.
[0441] In one embodiment, the amount of the heterocyclic compound may be in a range of about 3 parts by weight to about 10 parts by weight based on 100 parts by weight of the first organic film. By controlling the amount of the heterocyclic compound in the first organic film, the maximum absorption wavelength of the first organic film may be finely adjusted, and the UV absorption spectrum may be controlled.
[0442] For example, at least one organic film may be composed of a heterocyclic compound.
[0443] In one or more embodiments, in addition to the heterocyclic compound, at least one organic film may further include a matrix resin, and the heterocyclic compound may be dispersed in the matrix resin. In this case, the heterocyclic compound may be simply dispersed in the matrix resin, or the heterocyclic compound may be cross-linked with the matrix resin.
[0444] In one embodiment, the first organic film may further include a matrix resin.
[0445] The matrix resin may include at least one of an acryl-based resin, a methacryl-based resin, an isoprene-based resin, a vinyl-based resin, an epoxy-based resin, a urethane-based resin, a cellulose resin, a perylene-based resin, an imide-based resin, and a silicone-based resin.
[0446] In one or more embodiments, at least one organic film may further include a photopolymerization initiator in addition to the heterocyclic compound. The photopolymerization initiator is the same as described above.
[0447] In one or more embodiments, at least one organic film may further include a matrix resin and a photopolymerization initiator in addition to the heterocyclic compound.
[0448] Another aspect of the embodiment provides a method of manufacturing an electronic device, the method comprising:
[0449] forming an organic light emitting device on a substrate; and
[0450] forming a thin film package sealing the organic light emitting device on the substrate,
[0451] The formation of the thin film encapsulation comprises providing a thin film encapsulation composition for sealing the organic light-emitting device and curing the thin film encapsulation composition.
[0452] The thin film encapsulation composition includes a heterocyclic compound.
[0453] The thin film encapsulation member, the heterocyclic compound and the thin film encapsulation composition are the same as those described above. When an electronic device is manufactured according to the above method, external UV rays are blocked from reaching the organic light-emitting device, thereby preventing damage to the organic light-emitting device when it is continuously exposed to UV rays (or reducing the possibility or degree of such damage), and improving the durability of the organic light-emitting device and the electronic device including the organic light-emitting device.
[0454] As used herein, the term “C 1 -C 60 "Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to C 1 -C 60 The alkyl group has a divalent group having substantially the same structure.
[0455] As used herein, the term “C 2 -C 60 "Alkenyl" refers to 2 -C 60 Alkyl refers to a hydrocarbon group having at least one carbon-carbon double bond in the main chain (e.g., in the middle) or at the end, examples of which include ethenyl, propenyl, and butenyl. As used herein, the term “C 2 -C 60 "Alkenylene" refers to C 2 -C 60 An alkenyl group has a divalent group having substantially the same structure.
[0456] As used herein, the term “C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 An alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond in the main chain (e.g., in the middle) or at a terminal, examples of which include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl groups have substantially the same structure as divalent groups.
[0457] As used herein, the term “C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, examples of which include a methoxy group, an ethoxy group and an isopropoxy group.
[0458] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.
[0459] As used herein, the term “C 1 -C 10 "Heterocycloalkyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom and 1 to 10 carbon atoms, examples of which include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group having substantially the same structure.
[0460] As used herein, the term “C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity (e.g., the ring and / or the entire group is not aromatic), examples of which include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group is a divalent group having substantially the same structure.
[0461] As used herein, the term “C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C 10The heterocycloalkenyl group has a divalent group having substantially the same structure.
[0462] As used herein, the term “C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the plurality of rings may be fused to each other (eg, bonded together).
[0463] As used herein, the term “C 1 -C 60 "Heteroaryl" refers to a monovalent group having a carbocyclic aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a carbocyclic aromatic system having at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group includes two or more rings, the plurality of rings may be condensed with each other (eg, bonded together).
[0464] As used herein, the term “C 6 -C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C 6 -C 60 Aryl), C 6 -C 60 Arylthio refers to -SA 103 (Among them, A 103 C 6 -C60 aryl).
[0465] As used herein, the term "monovalent non-aromatic condensed polycyclic group" refers to a monovalent group having two or more rings condensed to each other (e.g., bound together), only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms, and no aromaticity in the entire molecular structure (e.g., the entire group is not aromatic). An example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed polycyclic group.
[0466] As used herein, the term "monovalent non-aromatic condensed heteropolycyclic group" refers to a monovalent group having two or more rings condensed with each other (e.g., bound together), at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and no aromaticity in the entire molecular structure (e.g., the entire molecule is not aromatic). An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. As used herein, the term "divalent non-aromatic condensed heteropolycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
[0467] As used herein, the term “C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In one or more embodiments, the carbonyl group is connected to the carbonyl group. 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group (eg, a tetravalent group).
[0468] As used herein, the term “C 1 -C 60 The term "heterocyclic group" refers to a group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom other than carbon (the number of carbon atoms may be in the range of 1 to 60) and C 1 -C 60 The carbocyclic group has a group having substantially the same structure.
[0469] Substituted C 5 -C60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 60 Cycloalkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0470] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60Alkoxy and C 3 -C 60 Cycloalkoxy;
[0471] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) of at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy and C 3 -C 60 Cycloalkoxy;
[0472] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0473] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) of at least one of C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0474] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0475] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
[0476] The term "Ph" as used herein refers to phenyl, the term "Me" as used herein refers to methyl, the term "Et" as used herein refers to ethyl, the term "ter-Bu" or "Bu" as used herein refers to ethyl. t ” means tert-butyl, and the term “OMe” as used herein means methoxy.
[0477] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". 6 -C 60 "substituted phenyl" having "aryl" as a substituent.
[0478] The term "terphenyl" as used herein refers to a phenyl group substituted with a biphenyl group. 6 -C 60 Aryl C 6 -C 60 "phenyl" having "aryl" as a substituent.
[0479] Unless otherwise defined, * and *' used herein refer to the binding sites to adjacent atoms in the corresponding formula.
[0480] Hereinafter, the compound according to the embodiment and the organic light emitting device according to the embodiment will be described in more detail with reference to the examples. The expression "using B instead of A" used when describing the synthesis example means using the same number (or substantially the same number) of molar equivalents of B instead of the same molar equivalent of A.
[0481] Example
[0482] Example 1-1
[0483] An electronic device including a thin film encapsulation sealing an organic light emitting device on a substrate is manufactured. The thin film encapsulation is formed by using a thin film encapsulation composition including benzophenone as a UV absorber and 1,2-naphthalene diol as a radical scavenger.
[0484] Comparison Example 1-1
[0485] A thin film encapsulation member sealing an organic light emitting device on a substrate was formed by using the thin film encapsulation composition in substantially the same manner as Example 1-1, except that benzophenone was used instead of the UV absorber and the radical scavenger was not used.
[0486] Evaluation Example 1
[0487] The initial transmittance of the thin film package of each of the electronic devices manufactured according to Example 1-1 and Comparative Example 1-1 was measured, and the transmittance at 52,000 Wh / m 2The transmittance after exposure for 30 minutes ("transmittance after exposure") is shown in Figure 3 middle.
[0488] Reference Figure 3 , in the electronic device according to Example 1-1, the time required for the transmittance of the thin film encapsulation to increase is longer than that of Comparative Example 1-1, and therefore, it is confirmed that the light curing resistance is excellent. For example, with respect to a wavelength of 405nm, since the electronic device of Comparative Example 1-1 has an initial transmittance of approximately 2% and a transmittance after exposure of approximately 8%, the change in transmittance (the value obtained by subtracting the initial transmittance from the transmittance after exposure) is approximately 6%, and the transmittance is increased fourfold by 30 minutes of exposure. On the contrary, with respect to a wavelength of 405nm, since the electronic device of Example 1-1 has an initial transmittance of approximately 3% and a transmittance after exposure of approximately 6%, the transmittance change is small compared to Comparative Example 1-1.
[0489] Therefore, an organic light emitting display device including a UV stabilizing mixture in a thin film package can prevent an emission layer including an organic material, an insulating film, and the like from being damaged by ultraviolet rays (or can reduce the possibility or degree of such damage).
[0490] Synthesis Example 1: Synthesis of Compound 14
[0491]
[0492] As solvents and reagents used in the synthesis, commercially available reagents were purchased and used, and reagents not described were used as purchased. The results were performed using a 400 MHz NMR spectrometer at 25°C. 1 H-NMR analysis and DMSO-d 6 as solvent. Chemical shifts are referenced to δ H CHD of 2.50 2 (CD 3 ) is expressed in δ units (parts per million (ppm)) of SO.
[0493] 3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)propionic acid (2mmol), 4-hydroxy-1,2,2,6,6-pentamethylpiperidine (2.4mmol), N,N-diisopropylethylamine (4mmol), 1-hydroxybenzotriazole (HOBt, anhydrous) (2.88mmol) and diisopropylcarbodiimide (2.88mmol) were added to 50mL of dry dimethyl chloride solvent and stirred at room temperature. After the reaction was completed, water and ethyl acetate were added to the product to extract the organic layer. The organic layer was washed three times with a saturated sodium chloride aqueous solution. Only the extracted organic layer was collected and dried by using anhydrous magnesium sulfate. Then, the product was purified and separated by flash column chromatography (ethyl acetate: n-hexane = 9:1), and the solvent was removed by vacuum drying to obtain white solid compound 14 (final yield: 78%).
[0494] 1 H-NMR (400 MHz, DMSO-d 6 )δppm 11.25(br.S,1H),8.00~8.20(m,2H),7.95(d,J=2.1Hz,1H),7.50~7.67(m,2H),7.28(d,J=2.1Hz,1H),5.8(m, 1H), 2.87 (t, J = 7.5Hz, 2H), 2.56 (t, J = 7.5Hz, 2H), 2.35 (s, 3H), 1.80-1.96 (m, 4H), 1.45 (s, 9H), 1.27 (s, 12H).
[0495] Example 2-1
[0496] An electronic device including a thin film encapsulation sealing an organic light emitting device on a substrate was manufactured. The thin film encapsulation was formed by using a thin film encapsulation composition including Compound 14 synthesized in Synthesis Example 1.
[0497]
[0498] Comparison Example 2-1
[0499] A thin film encapsulation that seals an organic light emitting device on a substrate was formed in substantially the same manner as Example 2-1, except that Compound A was used instead of Compound 14.
[0500]
[0501] Comparison Example 2-2
[0502] A thin film encapsulation sealing an organic light emitting device on a substrate was formed in substantially the same manner as Example 2-1, except that a mixture of Compound A and Compound B mixed in an equivalent ratio of 1:1 was used instead of Compound 14.
[0503]
[0504] Evaluation Example 2
[0505] The initial transmittance (T 1 ) and 52,000Wh / m 2 The transmittance after exposure (T 2 )”), the results are shown in Figure 4 middle.
[0506] In addition, with respect to the initial transmittance (T 1 ) and the transmittance after exposure (T 2 ), the transmittance change (ΔT%) was calculated as expressed in Equation 1 and is shown in Table 1.
[0507] Equation 1
[0508] Transmittance change (ΔT%) = Transmittance after exposure (T 2 ) – initial transmittance (T 1 )
[0509] Table 1
[0510]
[0511] Reference Figure 4 As shown in Table 1, compared with the electronic devices according to Comparative Example 2-1 and Comparative Example 2-2, in the electronic device according to Example 2-1, the initial transmittance and the transmittance after exposure of the thin film encapsulation member hardly changed (change in transmittance: 0.15%), and the light curing resistance was excellent.
[0512] Therefore, an organic light-emitting display device including a heterocyclic compound in a thin film package can prevent an emission layer including an organic material, an insulating film, etc. from being damaged by ultraviolet rays and visible rays having a short wavelength (or can reduce the possibility or degree of such damage).
[0513] In one or more embodiments, the organic light emitting display device can prevent an emission layer including an organic material, an insulating film, and the like from being damaged by ultraviolet rays (or can reduce the possibility or degree of such damage).
[0514] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
[0515] It will be understood that when an element or layer is referred to as being “on,” “connected to,” or “coupled to” another element or layer, it can be directly on, directly connected to, or coupled to the other element or layer, or one or more intervening elements or layers may be present. Additionally, it will be understood that when an element or layer is referred to as being “between” two elements or layers, it can be the only element or layer between the two elements or layers, or one or more intervening elements or layers may also be present.
[0516] The terms used herein are only for the purpose of describing specific embodiments, and are not intended to limit the present disclosure. As used herein, unless the context clearly indicates otherwise, the singular forms "one" and "one (kind, person)" are also intended to include plural forms. It will also be understood that when the terms "include", "comprise" and their variations are used in this specification, the descriptions indicate the existence of stated features, wholes, actions, operations, elements and / or components, but do not exclude the existence or addition of one or more other features, wholes, actions, operations, elements, components and / or their groups. As used herein, the term "and / or" includes any combination and all combinations of one or more related listed items. When a statement such as "at least one (kind / person) of" is after a column of elements (or elements), the entire column of elements (or elements) is modified, rather than the individual elements (or elements) of the column being modified.
[0517] As used herein, the terms "substantially," "approximately," and similar terms are used as terms of approximation, rather than as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that would be recognized by one of ordinary skill in the art. Additionally, the use of "may" when describing embodiments of the present disclosure refers to "one or more embodiments of the present disclosure." As used herein, the term "use" and variations thereof may be considered synonymous with the term "utilizing" and variations thereof, respectively. Additionally, the term "exemplary" is intended to indicate an example or illustration.
[0518] In addition, any numerical range stated herein is intended to include all sub-ranges of the same numerical precision contained in the stated range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the stated minimum value 1.0 and the stated maximum value 10.0 (including the stated minimum value 1.0 and the stated maximum value 10.0), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all smaller numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all larger numerical limits contained therein. Therefore, the applicant reserves the right to modify this specification including the claims to explicitly state any sub-ranges contained in the scope explicitly stated herein.
[0519] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.
Claims
1. An electronic device, comprising: substrate; an organic light-emitting device, located on the substrate; as well as a thin film encapsulation part, sealing the organic light emitting device, wherein the thin film encapsulation portion comprises a UV stable mixture, The UV stabilizing mixture includes a UV absorber and a free radical scavenger, The UV absorber is represented by formula A2-1, Among them, R3, R4 and R 11 To R 18 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy, The free radical scavenger is represented by formula A5-2, Among them, R 52 is hydroxyl group, R 51 and R 53 are independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy, L 10 A straight chain bond.
2. The electronic device according to claim 1, wherein: R3, R4 and R 11 To R 18 are independently selected from hydrogen, deuterium and C1-C 20 alkyl.
3. The electronic device according to claim 2, wherein: R3, R4 and R 11 To R 18 are independently selected from hydrogen.
4. The electronic device according to claim 3, wherein: R 51 and R 53 Independently selected from: hydrogen, deuterium and C1-C 20 alkyl.
5. The electronic device according to claim 1, wherein: The UV absorber absorbs light having a wavelength of 280 nm to 430 nm.
6. The electronic device according to claim 1, wherein: R 51 and R 53 are independently selected from hydrogen.
7. The electronic device according to claim 1, wherein: The amount of the radical scavenger is in the range of 0.5 parts by weight to 20 parts by weight based on 100 parts by weight of the UV absorber.
8. The electronic device according to claim 1, wherein: The thin film encapsulation portion includes at least one organic film, The at least one organic film includes a first organic film, and The first organic film includes the UV stabilizing mixture.
9. The electronic device according to claim 8, wherein: The first organic film further comprises a matrix resin, and The matrix resin includes at least one of an acryl resin, a methacryl resin, an isoprene resin, a vinyl resin, an epoxy resin, an urethane resin, a cellulose resin, a perylene resin, an imide resin, and a silicone resin.
10. The electronic device according to claim 8, wherein: An amount of the UV stabilizing mixture is in a range of 3 parts by weight to 10 parts by weight based on 100 parts by weight of the first organic film.
11. The electronic device according to claim 8, wherein: The first organic film has a transmittance of 80% or more with respect to light having a wavelength of 430 nm or more, and has a transmittance of 10% or less with respect to light having a wavelength of 405 nm or less.
12. The electronic device according to claim 8, wherein: When the first organic film is exposed to 52,000Wh / m 2 When the amount of light is irradiated, the change in transmittance with respect to light with a wavelength of 400nm to 410nm is less than 5%.
13. The electronic device according to claim 8, wherein: The thickness of the first organic film is in the range of 10 nm to 20 μm.
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